US 20160362631A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2016/0362631 A1 HOLLAND et al. (43) Pub. Date: Dec. 15, 2016
(54) FRAGRANCE FXATIVES AND Publication Classification COMPOSITIONS COMPRISING THEREOF (51) Int. Cl. (71) Applicant: The Procter & Gamble Company, CIIB 9/00 (2006.01) Cincinnati, OH (US) A61O 19/00 (2006.01) (72) Inventors: Lynette Anne Makins HOLLAND, A6IR 8/49 (2006.01) Abbots Langley (GB); Christelle Marie A61O 13/00 (2006.01) Sandrine BONNET, A6IR 8/37 (2006.01) Caillouet-Orgeville (FR); Fabienne A6IR 8/34 (2006.01) PASTOR, Meriel (FR); Jose Maria (52) U.S. Cl. VELAZQUEZ MENDOZA, Ascot CPC ...... CIIB 9/0015 (2013.01): CIIB 9/0061 (GB); Jonathan Richard (2013.01); CIIB 9/0092 (2013.01); CIIB STONEHOUSE, Windlesham (GB); 9/0034 (2013.01); CIIB 9/0019 (2013.01); William Eoghan STAITE, Egham A61K 8/37 (2013.01); A61K 8/34 (2013.01); (GB); David Thomas STANTON, A61K 8/342 (2013.01); A61K 8/492 (2013.01); Hamilton, OH (US); Oreste TODINI, A61O 13/00 (2013.01); A61O 19/007 Bruxelles (BE); Sarah Kyakyo (2013.01) Kanyunyuzi NYAKANA, Windsor (GB); Susana FERNANDEZ PRIETO, Benicassim (ES); Johan (57) ABSTRACT SMETS, Lubbeek (BE); Jeffrey John SCHEIBEL, Cincinnati, OH (US); Isabelle GUIMET, Brussels (BE) The present invention relates to Substantially non-odorous fragrance fixatives for extending the fragrance intensity or (21) Appl. No.: 15/183,353 character, of fragrance materials over time. The invention (22) Filed: Jun. 15, 2016 also covers compositions of fragrance materials and the Substantially non-odorous fragrance fixatives and methods Related U.S. Application Data ofuse of the compositions for perfuming suitable substrates, (60) Provisional application No. 62/175,439, filed on Jun. including hard Surfaces and body parts, particularly skin and 15, 2015. hair. Patent Application Publication Dec. 15, 2016 Sheet 1 of 25 US 2016/0362631 A1
Figure 1 - Fragrance Intensity Dimethyl Benzyl Carbino with or without Piperony butoxide (Fixative)
3 ras as Piperonylbutoxide : N as a Contro
Figure 2 - Fragrance intensity Eugenoi with or without Piperonyl butoxide (Fixative)
3
2
O ------() 2 3 4. 5 6 Time (Hours)
...... Patent Application Publication Dec. 15, 2016 Sheet 2 of 25 US 2016/0362631 A1
Figure 3 - Fragrance intensity Dimethyl Benzyl Carbinoi with or without Poly(PG)monobutyl ether (Fixative)
Figure 4 - Fragrance intensity Eugenol with or without Poly(PG)monobutyl ether (Fixative)
Patent Application Publication Dec. 15, 2016 Sheet 3 of 25 US 2016/0362631 A1
Figure 5 - Fragrance intensity Phenethyl Alcohol with or without Poly(PG) monobutyl ether (Fixative) 5 - -- Poly(PG)monobutyl 4 ...... ether V a Contro
O 2 3. 4 5 6 Time (Hours)
Figure 6 - Fragrance intensity Endole with or without Triglycol (i.e., Triethylene Glycoi? Fixative)
5
x-Triethylene Glycol 3
{inning
O --~ O 2 3 4. 5 6 Patent Application Publication Dec. 15, 2016 Sheet 4 of 25 US 2016/0362631 A1
Figure 7 - Fragrance intensit Eugenoi with or without Triglycol (i.e., Triethylene Glycolf Fixative)
8
3 Time (Hours)
Figure 8 - Evaporation Profile for Indole with or without Tergito 15-S-7 (Fixative)
------x ------
"'8" Profile forfergito.1655 S-7 (n=1)
-- Average Profile for Control (nl)
Time (Hours) Patent Application Publication Dec. 15, 2016 Sheet 5 of 25 US 2016/0362631 A1
Figure 9- Evaporation Profile for indole with or without PPG-7-Buteth- 0 (Fixative)
75 -- Average Profile for Control (n=9)
Figure 10 - Evaporation Profile for indole with or without Nikkoi PBC-33 (Fixative)
* ------& ------as: --a &Y-1 8 - & Profile for NIKKOL PBC-33 (n=1) a -- Average Profile for Control
O ...... N...... aaaaa as a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a a s 50 8 (n=9) t 8 8 8 d s 8 OC 25 -N- Patent Application Publication Dec. 15, 2016 Sheet 6 of 25 US 2016/0362631 A1
Figure 1 - Evaporation Profile for Indole with or without Neodol 45-7 Alcohol Ethoxylate (Fixative) OO 8 ------&
7 - 8 - Profile for Neodoi 45-7A coho Ethoxylate (n=1) -- Average Profile for Control (n=9) 5
2
Time (Hours) 2 er,
{} } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } } Figure 2- Evaporation Profile for indole with or without Bio-soft N25-7 (Fixative)
- & Profile for Bio-soft N25-7 (n=1) -- Average Profile for Control (n=9)
Time (Hours) 2 Patent Application Publication Dec. 15, 2016 Sheet 7 of 25 US 2016/0362631 A1
Figure 3 - Evaporation Profile for indole with or without BIO-SOFT N23-6.5 (Fixative) -as e.s -8-a---8-a-x.'''SSSI & - - - Profile for BIO-SOFT N23-6.5 (n=) -- Average Profile for Control (n=9)
Figure 14 - Evaporation Profile for Indole with or without Cremophor A 25 (Fixative)
a s - - -Profile for Cremophor A25 (n=1) ra O r -- Average Profile for Control (n=9) 2 : s 50 - N - ; : : s r s s 25 m Nogo. C O
Time (Hours) Patent Application Publication Dec. 15, 2016 Sheet 8 of 25 US 2016/0362631 A1
Figure 5 - Evaporation Profile for Indole with or without BIO-SOFT N9 I-8 (Fixative) OO
7 5 - x - Profile for BIO-SOFT N91-8 (n=1) -- Average Profile for Contro {n=9) s 5 O
2 5
O () Time (Hours) 2. 3 8
Figure 16 - Evaporation Profile for Indole with or without Genapo C-100 (Fixative) OO : N* - x - x - 8------: 8------&
- * - Profile for Genapol C-100 (n=1) -- Average Profile for Control (n=9)
s Patent Application Publication Dec. 15, 2016 Sheet 9 of 25 US 2016/0362631 A1
------Figure 7 - Evaporation Profile for indole with or without Rhodasurf LA 30 (Fixative) OO els---&------&-a------&------
7 5 s & Profile for RHODASURF LA 30 (n= } -- Average Profile for Control (n=9) 5 O
25
------Figure 8 - Evaporation Profile for indole with or without Poly(ethylene glycol) methyl ether (Fixative) 00 ...se.8...8...e. e.e...... w" as "axes - a ------...e...se...s.l...8.
: -
2 - 8 - Profile for Poly(ethylene glycol) S methyl ether (n=1) -- Average Profile for Control (n=9) 50 or nor :
ad 5g 25 pro-Nogo: C : O : : O --~ O Time (Hours) 2 3 ------Patent Application Publication Dec. 15, 2016 Sheet 10 of 25 US 2016/0362631 A1
Figure 19 - Evaporation Profile for Indole with or without ArlamolTM PS1 E (Fixative)
N3 - x - -x- - -x- Ye : 8 - - - - 75 irin r...8. - * - Profile for Arlamol PS1E (n=1) -- Average Profile for Control (n=9) 5 O
O Time (Hours) 2 3
Figure 20 - Evaporation Profile for Indole with or without Brij S100 (Fixative) OO
T - - - - - r &n are as - is a s& s75 on - x - Profile for Brij(E) S100 (n-1) re -- Average Profile for Control (n=9) s50 or nor. C2 s E 9 25 ------r------d O
O O Time (Hours) 2 3 Patent Application Publication Dec. 15, 2016 Sheet 11 of 25 US 2016/0362631 A1
Figure 21 - Evaporation Profile for Indole with or without Brij C-58 (Fixative) & - as&ne a - 8------a. & ^- 2 3 arre - x - Profile for Brij C58 (n=1) --- d s550
e 2
c 25 O
O Time (Hours) 2
Figure 22 - Evaporation Profile for indole with or without Piuronic F-127 (Fixative)
- & Profile for Puroic F-27 P2443 (n=1) -- Average Profile for Control
Time (Hours) 2 Patent Application Publication Dec. 15, 2016 Sheet 12 of 25 US 2016/0362631 A1
Figure 23 - Evaporation Profile for indole with or without Bio-Soft N 1-5 (Fixative)
- - - - & ------s 75 c. Nic - x - Profile for BIO-SOFT N 1-5 (n=1) s -- Average Profile for Control (n=9) 550
325 cc N O 0 iro. O Time (Hours) 2 3
Figure 24 - Evaporation Profile for Indole with or without Polyoxyethylene (10) lauryl ether (Fixative) OO .--&-..r.& MP - frritor"."------8-ror gr
75 - M ------*..&.: Profile fog. Decaethylene-glycol...... mono-dodecyl ether (nel) -- Average Profile for Control (n=9)
50 or Ner Patent Application Publication Dec. 15, 2016 Sheet 13 of 25 US 2016/0362631 A1
Figure 25 - Evaporation Profile for Indole with or without ArlamolTM PC () (Fixative) -as-a-ur-8-as--~~~~ 100 8 x-x- w se as s as T 8 ------&
- 8 - Profile for Arlamo PC10 (n=1) -- Average Profile for Control (n=9) 50 or No. 25 to No.
0 - () Time (Hours) 2 3
Figure 26 - Evaporation Profile for Indole with or without : Poly(ethylene glycol) (18) tridecyl ether (Fixative)
100 sisC& --&------r&e e& 4ts &s see ass ess as ess see see also as ess8------a&
75 or No. - * - Profile for Poly(ethylene glycol) (8) tridecyl ether (n=i) -- Average Profile for Control (n=9) 50 ...... N...... Patent Application Publication Dec. 15, 2016 Sheet 14 of 25 US 2016/0362631 A1
Figure 27 - Evaporation Profile for indole with or without ALFONIC 10-8 Ethoxylate (Fixative)
: ..e. sexe. --ar&r-r------: N& & e s -&- - - - - as as - - - as: s g 75 ...... n...... 3 : - &- - Profile for ALFONCGR 0-8 f Ethoxylate (n=1) t 50 -- Average Profile for Control (n=9)
E - 5 25
0 i O Time (Hours) ad 3
Figure 28 - Evaporation Profile for Indole with : or without Brij O20-SS (Fixative) 8 8 OO S.------
7 5 - & - Profile for Brij O20-SS (n-1) -- Average Profile for Control (n=9)
8 50 8 8 8 8 8 8 8 8 8 8 25 8irr-r- 8 8 8 8 8 8 8 8
O Time (Hours) 2 3 ------Patent Application Publication Dec. 15, 2016 Sheet 15 of 25 US 2016/0362631 A1
Figure 29 - Evaporation Profile for Indole with or without Diethylene glycol butyl ether (Fixative) 8 OC) rS--- a ------~sN-N-N-N-N-N-N-N-N-N- s N &
75 "N"--.p...- 8 - Profile forcravic Diethylene activiglycol butyl ether (n=1} -- Average Profile for Control (n=9) 50 or Noor. 25 - S --
O Time (Hours) 2 3
Figure 30 - Evaporation Profile for Indole with or without Ethylene glyco monohexadecyl ether (Fixative) i00 --~ NT 8 & ------r& role as as as a - - - &
s75 - N'- - 8--Profile for Ethylene glycol monohexadecyl ether (n=1) -- Average Profile for Control (n=9) 50 ...... N...... Patent Application Publication Dec. 15, 2016 Sheet 16 of 25 US 2016/0362631 A1
Figure 31 - Evaporation Profile for Indole with or without Poly(propylene glycol) monobutyl ether (Fixative) 100 tri-sm
- & Profile for Poly(propylene glycol) monobutyl ether (n=1} 50 -- Average Profile for Control (n=9)
O Time (Hours) 3
Figure 32 - Evaporation Profile for Indole with or without Dowano TPnB (Fixative) & 100 in-1..nr. & or * ------8 ------re is 8
- & Profile for DOWANOL(R) TPB (n=l)
50 )
2 5
O) ? a. O Time (Hours) Patent Application Publication Dec. 15, 2016 Sheet 17 of 25 US 2016/0362631 A1
------Figure 33 - Evaporation Profile for Indole with or without Tripropylene glycol (Fixative) OO
7 5 - « Profile for Tripropylene glycol (n=)
5 O AV e ag e P 3.fi S fo . Cent O -( o 9)
2 5
Figure 34 - Evaporation Profile for Indole with or without Cithro TM (Fixative)
* - - - - T w ------& Š75 u Sul. - x - Profile for Cithrol PG32IS-LQ (MV) (n-1) -- Average Profile for Control (n=9) 250 - Yat 3
s :
O 25 :irr-r O 0 iro. Patent Application Publication Dec. 15, 2016 Sheet 18 of 25 US 2016/0362631 A1
Figure 35 - Evaporation Profile for Indole with or without gepal CA-630 (Fixative)
100 x - -- 8 -&-- - 8------r&s-x- - - as- a- as------x-
g 75 - N'------x - Profile for igepa CA-630 (n=) s -- Average Profile for Control (n=9) s 50 ------: E 3 s 25 O : 0 - O Time (Hours) 2 3.
Figure 36 - Evaporation Profile for Indole with or without Nikkol Decaglyn 3-OV (Fixative) 8 OO &m as a& & - -x- - - - -
7 5 - 8- - Profile for Nikkol Decaglyn 3-OV (n=) -- Average Profile for Control (n=9) 5 O
2 5
------Patent Application Publication Dec. 15, 2016 Sheet 19 of 25 US 2016/0362631 A1
Figure 37 - Evaporation Profile for Indole with or without NEKKOL Hexaglyn i-L (Fixative)
T 8 - -x- - - - T -x- - - - - 75 or No.- - - & - & Profile for NEKKOL Hexaglyn l-L
-- Average Profile for Control (n=9)
2 5
O Time (Hours) av 3
Figure 38 - Evaporation Profile for Indole with or without Emalex CS-0 (Fixative) OO rox'w': 8------&
75 or Nir S E - & Profile for Emalex CS 30 (n=1)
st-Average Profile for Control (n=9) 5 50 rinri.r.
(3 25 or Nyr.
0 - () Time (Hours) 2 3. s & ------Patent Application Publication Dec. 15, 2016 Sheet 20 of 25 US 2016/0362631 A1
Figure 39 - Evaporation Profile for indole with or without Dioctyl ether (Fixative)
- x - Profile for Dioctyl ether (n=1) -- Average Profile for Control (n=9)
------
Figure 40 - Evaporation Profile for Indole with or without Jeeco CA-10 (Fixative) O) -x-g-x-x-rw-r : T -x------&
5 - 8 - Profile for eeco CA-10 (n=i) -- Average Profile for Contro. (nig)" '50is
5
O ~ O Time (Hours) 2 3 Patent Application Publication Dec. 15, 2016 Sheet 21 of 25 US 2016/0362631 A1
Figure 4 - Evaporation Profile for Indole with or without Steareth-10 (Fixative)
s - & Profile for Steareth-0 7 5 m Num(Polyoxyethylene (IO)" Stearyi Ether) (n=1) -- Average Profile for 5 O i"N", "Control (n=9"
4. 5
O ------O Time (Hours) 2 3 ------
Figure 42 - Evaporation Profile for Indole with or without Nonaethylene glycol monododecyl ether (Fixative)
100 : e.8.8- - & - 8 - & - g
75 *.x. Profile for. Nonaethylene. glycol monododecyl ether (n=1) -- Average Profile for Control (n=9) 5 O &
...... res...... Patent Application Publication Dec. 15, 2016 Sheet 22 of 25 US 2016/0362631 A1
Figure 43 - Evaporation Profile for indole with or without Glycero Propoxylate (Fixative)
OO S-ax-rurk or -8---x-sur------
T - x ------r - a x: s c - & Profile for Glycerol Propoxylate (n= } as -- Average Profile for Control (n=9) g50 -in-i- .9 :
se : 2a 25 : -N- O : : : : :
Figure 44 - Evaporation Profile for Indole with or without Glycerol ethoxylate (Fixative) OO Sissue ------...","...","...","...------
S7 5 - * - Profile for Glyceroi ethoxylate (n=1)
5 O Patent Application Publication Dec. 15, 2016 Sheet 23 of 25 US 2016/0362631 A1
& Figure 45 - Evaporation Profile for indole with or without Hexaethylene glycol monohexadecyl ether (Fixative)
: e - : is 8------& :
: :& : & : & S- &: S 2 75 ------n ------* - Profile for Hexaethylene glycol : 3 monohexadecyl ether (n=1) war -- Average Profile for Control & sO 50- -N- (n-r)...... &: 9. : : : : : : s &
------ass------& (325 - &: : &
: & : & : & : () ...... O Time (Hours) 2 3 &
Figure 46 - Evaporation Profile for Indole with or without AquaflexTM XL-30 (Fixative)
- - 8 - -x- as a & - is h t as s
7 5 s& S. - 8 - Profile for Aquaflex XL-30 (n=1} : -- Average Profile for Control 50 or NSr. (magy
2 5 &
O Time (Hours) 2 3 P t t A i ti P bi ti Dec. 15, 2016 Sheet 24 of 25 US 2016/0362631 A1
Figure 47 - Evaporation Profile for Indole with or without Piperony! Butoxide (Fixative)
-a s s'- w g - & Profile for Piperonyl Butoxide s c re (n= 1) a0m Ayerage Profile for Control - C s C s
se
g . s s c Q
Time (Hours) er,
Figure 48 - Evaporation Profile for indole with
s or without Diphenhydramine HC (Fixative)
8 :8 8 8 8 8 8 8 8 8 as & 8 Profile for Diphenhydramine HC 8 8 8 8 (n 1) 8 8 8 Average Profile for Control (n=9). 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8 8------Time (Hours) Patent Application Publication Dec. 15, 2016 Sheet 25 of 25 US 2016/0362631 A1
Figure 49 - Evaporation Profile for Indole with or without Di (propylene glycol) propyl ether (Fixative)
50 u Nui - 8 - Profile for Di (propylene glycol) propyl ether (n=1) -- Average Profile for Control (n=9) 25 ------has ------
O ...... O Time (Hours) 2 3
Figure 50 - Evaporation Profile for indole with or without Poly(melamine-co-formaldehyde) methylated (Fixative) 8 8 100 ksgum8
8 a : T 8------as as & 75 or norror 8 - « - Profile for Poly(melamine-co formaldehyde) methylated (n=) -- Average Profile for Control (n=9) 5 O
2 5 US 2016/0362631 A1 Dec. 15, 2016
FRAGRANCE FXATIVES AND 0008. These and other features of the present invention COMPOSITIONS COMPRISING THEREOF will become apparent to one skilled in the art upon review of the following detailed description when taken in conjunc FIELD OF THE INVENTION tion with the appended claims. 0001. The present invention concerns substantially non BRIEF DESCRIPTION OF THE DRAWINGS odorous fragrance fixatives and compositions comprising said Substantially non-odorous fragrance fixatives to extend 0009 While the specification concludes with claims par the fragrance profile, preferably the fragrance intensity and/ ticularly pointing out and distinctly claiming the invention, or fragrance character, of the fragrance materials over time. it is believed that the invention will be better understood from the following description of the accompanying figures BACKGROUND OF THE INVENTION wherein: 0010 FIG. 1 provides the panel test results of perceived 0002 Fragrances in some products, particularly (but not fragrance profile, particularly improved fragrance intensity exclusively) ethanol-based ones, tend to lose their fragrance of Composition A comprising Dimethyl Benzyl Carbinol profile (i.e., character and intensity) rapidly after applica fragrance material and Piperonylbutoxide Substantially non tion. Various materials have been used to make the fragrance odorous fragrance fixative as compared to Composition B, a profile last longer. These are known as fragrance fixatives. control absent of a Substantially non-odorous fragrance Some Substantially non-odorous examples include: (i) cap fixative (Piperonyl butoxide), and as a function of time Sules or complexes based on dextrines, melamines or elapsed since application of the composition. obtained by coacervation of anionic and cationic polymers, 0011 FIG. 2 provides the panel test results of perceived (ii) film-forming polymers, or (iii) perfume base notes Such fragrance profile, particularly improved fragrance intensi as musks. The drawbacks of capsules or complexes are that ty of Composition C comprising Eugenol fragrance material they are difficult to formulate into a fragrance composition and Piperonylbutoxide Substantially non-odorous fragrance and/or the release is little controlled but depends on variable fixative as compared to Composition D, a control absent of factors like moisture or sebum amount or Sweat intensity. a Substantially non-odorous fragrance fixative (Piperonyl The issue with film-forming polymers is that they produce butoxide), and as a function of time elapsed since applica very noticeable and undesirable films (both visual and tion of the composition. tactile). The disadvantage of perfume base notes is that they 0012 FIG. 3 provides the panel test results of perceived can negatively impact the fragrance character of the com fragrance profile, particularly improved fragrance intensity positions to which they are added. of Composition I comprising Dimethyl Benzyl Carbinol 0003. Thus, there is a need for new fragrance fixatives to fragrance material and Poly(PG)monobutyl ether substan extend the fragrance profile, preferably the intensity or tially non-odorous fragrance fixative as compared to Com character, of a fragrance material to maintain its intensity position J, a control absent of a Substantially non-odorous over time and particularly in retaining the initial character fragrance fixative (Poly(PG)monobutyl ether), and as a and intensity of the characters. It is also desirable that the function of time elapsed since application of the composi fragrance fixatives should not adversely affect the aromatic tion. and/or aesthetic character of the products to which they are 0013 FIG. 4 provides the panel test results of perceived added. fragrance profile, particularly improved fragrance intensity of Composition K comprising Eugenol fragrance material SUMMARY OF THE INVENTION and Poly(PG)monobutyl ether substantially non-odorous fragrance fixative as compared to Composition L, a control 0004. In one aspect, the present invention provides a absent of a Substantially non-odorous fragrance fixative Substantially non-odorous fragrance fixative comprising at (Poly(PG)monobutyl ether), and as a function of time least one material selected from the group consisting of the elapsed since application of the composition. materials in Table 1, as provided herein below. 0014 FIG. 5 provides the panel test results of perceived 0005. In another aspect, the present invention is directed fragrance profile, particularly improved fragrance intensity to a composition comprising a fragrance component present of Composition M comprising Phenethyl alcohol (PEA) in an amount of from about 0.04 wt % to about 30 wt %, fragrance material and Poly(PG)monobutyl ether substan relative to the total weight of the composition, and at least tially non-odorous fragrance fixative as compared to Com one Substantially non-odorous fragrance fixative, as position N, a control absent of a Substantially non-odorous described herein below, present in an amount of from about fragrance fixative (Poly(PG)monobutyl ether), and as a 0.1 wt % to about 20 wt %, relative to the total weight of the function of time elapsed since application of the composi composition. tion. 0006. In yet another aspect, the present invention is 0015 FIG. 6 provides the panel test results of perceived further directed to a method of modifying or enhancing the fragrance profile, particularly improved fragrance intensity odour properties of a surface with a composition of the of Composition Q comprising Indole fragrance material and present invention, by contacting or treating the Surface with Triglycol Substantially non-odorous fragrance fixative as the composition. compared to Composition R, a control absent of a Substan 0007. In yet another aspect, the present invention is tially non-odorous fragrance fixative (Triglycol), and as a further directed to a composition comprising fragrance function of time elapsed since application of the composi materials and a substantially non-odorous fragrance fixative tion. according to Table 1 for extending the fragrance profile of 0016 FIG. 7 provides the panel test results of perceived the fragrance materials vs. a control composition absent of fragrance profile, particularly improved fragrance intensity the Substantially non-odorous fragrance fixative. of Composition S comprising Eugenol fragrance material US 2016/0362631 A1 Dec. 15, 2016 and Triglycol Substantially non-odorous fragrance fixative and Genapol(R) C-100 substantially non-odorous fragrance as compared to Composition T, a control absent of a Sub fixative as compared to a control composition (REF), and as stantially non-odorous fragrance fixative (Triglycol), and as a function of time elapsed since application of the compo a function of time elapsed since application of the compo sition. sition. 0026 FIG. 17 provides the evaporation profile results for 0017 FIG. 8 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD10) comprising a volatile fragrance material mixture (MOD1) comprising a volatile fragrance material mixture and RhodasurfR LA 30 substantially non-odorous fragrance and Tergitol(R) 15-S-7 substantially non-odorous fragrance fixative as compared to a control composition (REF), and as fixative as compared to a control composition (REF), and as a function of time elapsed since application of the compo a function of time elapsed since application of the compo sition. sition. (0027 FIG. 18 provides the evaporation profile results for 0018 FIG. 9 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD11) comprising a volatile fragrance material mixture (MOD2) comprising a volatile fragrance material mixture and Poly(ethylene glycol) methyl ether substantially non and PPG-7-Buteth-10 substantially non-odorous fragrance odorous fragrance fixative as compared to a control com fixative as compared to a control composition (REF), and as position (REF), and as a function of time elapsed since a function of time elapsed since application of the compo application of the composition. sition. (0028 FIG. 19 provides the evaporation profile results for 0019 FIG. 10 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD12) comprising a volatile fragrance material mixture (MOD3) comprising a volatile fragrance material mixture and ArlamolTM PS11E substantially non-odorous fragrance and Nikkol PBC-33 substantially non-odorous fragrance fixative as compared to a control composition (REF), and as fixative as compared to a control composition (REF), and as a function of time elapsed since application of the compo a function of time elapsed since application of the compo sition. sition. (0029 FIG. 20 provides the evaporation profile results for 0020 FIG. 11 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD13) comprising a volatile fragrance material mixture (MOD4) comprising a volatile fragrance material mixture and Brij(R) S100 substantially non-odorous fragrance fixative and Neodol 45-7 Alcohol Ethoxylate substantially non as compared to a control composition (REF), and as a odorous fragrance fixative as compared to a control com function of time elapsed since application of the composi position (REF), and as a function of time elapsed since tion. application of the composition. 0030 FIG. 21 provides the evaporation profile results for 0021 FIG. 12 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD14) comprising a volatile fragrance material mixture (MOD5) comprising a volatile fragrance material mixture and Brij(R) C-58 substantially non-odorous fragrance fixative and Bio-soft N25-7 substantially non-odorous fragrance as compared to a control composition (REF), and as a fixative as compared to a control composition (REF), and as function of time elapsed since application of the composi a function of time elapsed since application of the compo tion. sition. 0031 FIG. 22 provides the evaporation profile results for 0022 FIG. 13 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD15) comprising a volatile fragrance material mixture (MOD6) comprising a volatile fragrance material mixture and Pluronic R) F-127 substantially non-odorous fragrance and Bio-soft N23-6.5 substantially non-odorous fragrance fixative as compared to a control composition (REF), and as fixative as compared to a control composition (REF), and as a function of time elapsed since application of the compo a function of time elapsed since application of the compo sition. sition. 0032 FIG. 23 provides the evaporation profile results for 0023 FIG. 14 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD16) comprising a volatile fragrance material mixture (MOD7) comprising a volatile fragrance material mixture and Bio-soft N1-5 substantially non-odorous fragrance fixa and Cremophor R A 25 Substantially non-odorous fragrance tive as compared to a control composition (REF), and as a fixative as compared to a control composition (REF), and as function of time elapsed since application of the composi a function of time elapsed since application of the compo tion. sition. 0033 FIG. 24 provides the evaporation profile results for 0024 FIG. 15 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD17) comprising a volatile fragrance material mixture (MODE) comprising a volatile fragrance material mixture and Polyoxyethylene (10) lauryl ether substantially non and Bio-soft N91-8 substantially non-odorous fragrance odorous fragrance fixative as compared to a control com fixative as compared to a control composition (REF), and as position (REF), and as a function of time elapsed since a function of time elapsed since application of the compo application of the composition. sition. 0034 FIG. 25 provides the evaporation profile results for 0025 FIG. 16 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD18) comprising a volatile fragrance material mixture (MOD9) comprising a volatile fragrance material mixture and ArlamolTM PC 10 substantially non-odorous fragrance US 2016/0362631 A1 Dec. 15, 2016 fixative as compared to a control composition (REF), and as as compared to a control composition (REF27), and as a a function of time elapsed since application of the compo function of time elapsed since application of the composi sition. tion. 0035 FIG. 26 provides the evaporation profile results for 0044 FIG. 35 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD19) comprising a volatile fragrance material mixture (MOD28) comprising a volatile fragrance material mixture and Poly(ethylene glycol) (18) tridecyl ether substantially and Igepal(R) CO-630 substantially non-odorous fragrance non-odorous fragrance fixative as compared to a control fixative as compared to a control composition (REF), and as composition (REF), and as a function of time elapsed since a function of time elapsed since application of the compo application of the composition. sition. 0036 FIG. 27 provides the evaporation profile results for 004.5 FIG. 36 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD20) comprising a volatile fragrance material mixture (MOD29) comprising a volatile fragrance material mixture and ALFONIC(R) 10-8 Ethoxylate substantially non-odorous and Nikkol Decaglyn 3-OV substantially non-odorous fra fragrance fixative as compared to a control composition grance fixative as compared to a control composition (REF), (REF), and as a function of time elapsed since application of and as a function of time elapsed since application of the the composition. composition. 0037 FIG. 28 provides the evaporation profile results for 0046 FIG. 37 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD21) comprising a volatile fragrance material mixture (MOD30) comprising a volatile fragrance material mixture and BrijR) 020-SS substantially non-odorous fragrance fixa and NIKKOL Hexaglyn 1-L substantially non-odorous fra tive as compared to a control composition (REF), and as a grance fixative as compared to a control composition (REF), function of time elapsed since application of the composi and as a function of time elapsed since application of the tion. composition. 0038 FIG. 29 provides the evaporation profile results for 0047 FIG.38 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD22) comprising a volatile fragrance material mixture (MOD31) comprising a volatile fragrance material mixture and Diethylene glycol butyl ether substantially non-odorous and Emalex CS-10 substantially non-odorous fragrance fragrance fixative as compared to a control composition fixative as compared to a control composition (REF), and as (REF), and as a function of time elapsed since application of a function of time elapsed since application of the compo the composition. sition. 0039 FIG. 30 provides the evaporation profile results for 0048 FIG. 39 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD23) comprising a volatile fragrance material mixture (MOD32) comprising a volatile fragrance material mixture and Ethylene glycol monohexadecyl ether Substantially non and Dioctyl ether Substantially non-odorous fragrance fixa odorous fragrance fixative as compared to a control com tive as compared to a control composition (REF), and as a position (REF), and as a function of time elapsed since function of time elapsed since application of the composi application of the composition. tion. 0040 FIG. 31 provides the evaporation profile results for 0049 FIG. 40 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD24) comprising a volatile fragrance material mixture (MOD33) comprising a volatile fragrance material mixture and Poly(propylene glycol) monobutyl ether substantially and Jeecol CA-10 Substantially non-odorous fragrance fixa non-odorous fragrance fixative as compared to a control tive as compared to a control composition (REF), and as a composition (REF), and as a function of time elapsed since function of time elapsed since application of the composi application of the composition. tion. 0041 FIG. 32 provides the evaporation profile results for 0050 FIG. 41 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD25) comprising a volatile fragrance material mixture (MOD34) comprising a volatile fragrance material mixture and DowanolTMTPnB substantially non-odorous fragrance and Steareth-10 substantially non-odorous fragrance fixative fixative as compared to a control composition (REF), and as as compared to a control composition (REF), and as a a function of time elapsed since application of the compo function of time elapsed since application of the composi sition. tion. 0042 FIG.33 provides the evaporation profile results for 0051 FIG. 42 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD26) comprising a volatile fragrance material mixture (MOD35) comprising a volatile fragrance material mixture and Tripropylene Glycol substantially non-odorous fra and Nonaethylene glycol monododecyl ether substantially grance fixative as compared to a control composition (REF), non-odorous fragrance fixative as compared to a control and as a function of time elapsed since application of the composition (REF), and as a function of time elapsed since composition. application of the composition. 0043 FIG. 34 provides the evaporation profile results for 0.052 FIG. 43 provides the evaporation profile results for a representative component (i.e., indole) of test composition a representative component (i.e., indole) of test composition (MOD27) comprising a volatile fragrance material mixture (MOD36) comprising a volatile fragrance material mixture and CithrolTM substantially non-odorous fragrance fixative and Glycerol propoxylate Substantially non-odorous fra US 2016/0362631 A1 Dec. 15, 2016 grance fixative as compared to a control composition (REF), the body splash is applied to the body after bathing and and as a function of time elapsed since application of the provides a subtle hint of scent to the body. Body splashes are composition. commonly used by consumers who prefer less strong fra 0053 FIG. 44 provides the evaporation profile results for grance compositions. A body splash may comprise an etha a representative component (i.e., indole) of test composition nol-free composition according to the present invention (MOD37) comprising a volatile fragrance material mixture which comprises from 0.2-8 wt %, relative to the total and Glycerol ethoxylate Substantially non-odorous fragrance weight of the composition, of a fragrance component. The fixative as compared to a control composition (REF), and as body Splash may further comprise alkyl polyglucosides as a function of time elapsed since application of the compo non-ionic Surfactants. sition. 0063 As used herein, the term “body spray” means a 0054 FIG. 45 provides the evaporation profile results for formulation comprising fragrance materials intended to be a representative component (i.e., indole) of test composition applied to the body to prevent or mask body odor caused by (MOD38) comprising a volatile fragrance material mixture the bacterial breakdown of perspiration on the body (e.g., and Hexaethylene glycol monohexadecyl ether Substantially armpits, feet, and other areas of the body). The body spray non-odorous fragrance fixative as compared to a control may also provide a fragrance expression to the consumers. composition (REF), and as a function of time elapsed since Typically, body spray compositions are applied as an aerosol application of the composition. spray in an effective amount on the skin of a consumer. 0055 FIG. 46 provides the evaporation profile results for 0064. As used herein, the term “composition' includes a a representative component (i.e., indole) of test composition fine fragrance composition intended for application to a (MOD39) comprising a volatile fragrance material mixture Surface. Such as for example, body Surface like skin or hair, and AquaflexTM XL-30 substantially non-odorous fragrance i.e., to impart a pleasant odour thereto, or cover a malodour fixative as compared to a control composition (REF), and as thereof. They are generally in the form of perfume concen a function of time elapsed since application of the compo trates, perfumes, parfums, eau de parfums, eau de toilettes, sition. aftershaves, or colognes. The fine fragrance compositions 0056 FIG. 47 provides the evaporation profile results for may be an ethanol-based composition. The term “composi a representative component (i.e., indole) of test composition tion may also include a cosmetic composition, which (MOD40) comprising a volatile fragrance material mixture comprises a fragrance material for the purposes of delivering and Piperonyl Butoxide Substantially non-odorous fragrance a pleasant Smell to drive consumer acceptance of the cos fixative as compared to a control composition (REF), and as metic composition. The term "composition” may also a function of time elapsed since application of the compo include body splashes or body sprays. The term "composi sition. tion may also include cleaning compositions. Such as fabric 0057 FIG. 48 provides the evaporation profile results for care composition or home care compositions, including air a representative component (i.e., indole) of test composition care compositions (e.g., air fresheners), for use on clothing (MOD41) comprising a volatile fragrance material mixture or other Substrates such as hard Surfaces (e.g., dishes, floors, and Diphenhydramine HCl substantially non-odorous fra countertops). Additional non-limiting examples of "compo grance fixative as compared to a control composition (REF), sition” may also include facial or body powder, foundation, and as a function of time elapsed since application of the deodorant, body/facial oil, mousse, creams (e.g., cold composition. creams), waxes, Sunscreens and blocks, bath and shower 0058 FIG. 49 provides the evaporation profile results for gels, lip balms, self-tanning compositions, masks and a representative component (i.e., indole) of test composition patches. (MOD42) comprising a volatile fragrance material mixture 0065. As used herein, the term “consumer” means both and Di(propylene glycol) propyl ether Substantially non the user of the composition and the observer nearby or odorous fragrance fixative as compared to a control com around the user. position (REF), and as a function of time elapsed since 0066. As used herein, the terms “fragrance' and “per application of the composition. fume’ are used interchangeably to designate the component 0059 FIG.50 provides the evaporation profile results for in the composition that is formed of fragrance materials, i.e., a representative component (i.e., indole) of test composition ingredients capable of imparting or modifying the odour of (MOD43) comprising a volatile fragrance material mixture and Poly(melamine-co-formaldehyde) methylated substan skin or hair or other substrate. 0067. As used herein, the term “fragrance material' and tially non-odorous fragrance fixative as compared to a "fragrance materials' relates to a perfume raw material, or control composition (REF), and as a function of time elapsed a mixture of perfume raw materials, that are used to impart since application of the composition. an overall pleasant odour or fragrance profile to a compo sition. "Fragrance materials' can encompass any Suitable DETAILED DESCRIPTION OF THE perfume raw materials for fragrance uses, including mate INVENTION rials such as, for example, alcohols, aldehydes, ketones, Definitions esters, ethers, acetates, nitriles, terpene hydrocarbons, nitrogenous or Sulfurous heterocyclic compounds and essen 0060. As used herein, articles such as “a” and “an when tial oils. However, naturally occurring plant and animal oils used in a claim, are understood to mean one or more of what and exudates comprising complex mixtures of various is claimed or described. chemical components are also know for use as "fragrance 0061. As used herein, the terms “include”, “includes” and materials'. The individual perfume raw materials which “including are meant to be non-limiting. comprise a known natural oil can be found by reference to 0062. As used herein, the term “body splash” means a Journals commonly used by those skilled in the art Such as body care formulation that is applied to the body. Typically, “Perfume and Flavourist' or “Journal of Essential Oil US 2016/0362631 A1 Dec. 15, 2016
Research', or listed in reference texts such as the book by S. 101.325 kPa) for a given chemical species. It defines a Arctander, Perfume and Flavor Chemicals, 1969, Montclair, chemical species desire to be in the gas phase rather than N.J., USA and more recently re-published by Allured Pub the liquid or solid state. The higher the vapor pressure the lishing Corporation Illinois (1994). Additionally, some per greater the proportion of the material that will, at equilib fume raw materials are Supplied by the fragrance houses rium, be found in a closed headspace. It is also related to the (Firmenich, International Flavors & Fragrances, Givaudan, rate of evaporation of a fragrance material which is defined Symrise) as mixtures in the form of proprietary speciality in an open environment where material is leaving the accords. Non-limiting examples of the fragrance materials system. The vapor pressure is determined according to the useful herein include pro-fragrances such as acetal pro reference program Advanced Chemistry Development fragrances, ketal pro-fragrances, ester pro-fragrances, (ACD/Labs) Software Version 14.02, or preferably the latest hydrolyzable inorganic-organic pro-fragrances, and mix version update). tures thereof. The fragrance materials may be released from 0072. It is understood that the test methods that are the pro-fragrances in a number of ways. For example, the disclosed in the Test Methods Section of the present appli fragrance may be released as a result of simple hydrolysis, cation must be used to determine the respective values of the or by a shift in an equilibrium reaction, or by a pH-change, parameters of Applicants inventions as described and or by enzymatic release. claimed herein. 0068. As used herein, the term “fragrance profile' means 0073. In all embodiments of the present invention, all the description of how the fragrance is perceived by the percentages are by weight of the total composition, as human nose at any moment in time. The fragrance profile evident by the context, unless specifically stated otherwise. may change over time. It is a result of the combination of the All ratios are weight ratios, unless specifically stated other low volatile fragrance materials and the Volatile fragrance wise, and all measurements are made at 25° C., unless materials, if present, of a fragrance. A fragrance profile is otherwise designated. composed of 2 characteristics: intensity and character. Substantially Non-Odorous Fragrance Fixatives The inven The intensity relates to the perceived strength whilst char tors have discovered new agents that can be used as Sub acter refers to the odour impression or quality of the stantially non-odorous fragrance fixatives, as described perfume, i.e., fruity, floral, woody, etc. herein below, to enhance or improve the fragrance profile, 0069. As used herein, the terms “fixative' and “fragrance preferably the intensity or character, of the fragrance mate fixative' are used interchangeably to designate an agent rial. Preferable examples of the substantially non-odorous having the capacity to affect the fragrance profile, such as for fragrance fixatives are provided in Table 1 below. example, by impacting the fragrance materials evaporation 0074 Preferably, the substantially non-odorous fragrance rate. The fixative may mediate its effect by lowering the fixative is present in an amount of from about 0.1 wt % to vapor pressure of the fragrance materials and increasing about 20 wt %, preferably from about 0.5 wt % to about 18 their adherence to the substrate (skin and/or hair) thus wt % or more preferably from about 2.5 wt % to about 15 ensuring a longer-lasting impression of the fragrance. Suit wt % or combinations thereof, relative to the total weight of able examples of the fixative are provided herein below, the composition. Alternatively, the Substantially non-odor particularly in Table 1. ous fragrance fixative is present in an amount of from about 0070. As used herein, the term “substantially non-odor 0.1 wt %, 0.5 wt % or 2.5 wt % to about 15 wt %, 18 wt % ous' means an agent that does not impart an odour of its own or 20 wt %, relative to the total weight of the composition. when added into a composition of the present invention. For If there is more than one substantially non-odorous fra example, a “substantially non-odorous fragrance fixative' grance fixatives, then the ranges provided hereinabove cover does not impart a new odour that alters the character of the the total of all of the substantially non-odorous fragrance fragrance profile of the composition to which it is added. The fixatives. term "substantially non-odorous” also encompasses an agent 0075. The substantially non-odorous fragrance fixatives that may impart a minimal or slight odour of its own when of the present invention may be a liquid at temperatures added into a composition of the present invention. However, lower than 100° C., preferably at ambient temperature. The the odour imparted by the “substantially non-odorous fra Substantially non-odorous fragrance fixatives may be fully grance fixative' is generally undetectable or tends to not miscible with the fragrance materials to form a single phase substantively alter the character of the fragrance profile of liquid. However, if the fragrance materials are not entirely the composition to which it is added initially or preferably miscible, or are immiscible, then co-solvents (e.g., dipro over time. Furthermore, the term “substantially non-odor pylene glycol (DPG), triethyl citrate, or others as well ous also includes materials that are perceivable only by a known to those skilled in the art) can be added to aid in the minority of people or those materials deemed anosmic to the solubility of the fragrance materials. majority of people. Furthermore, the term “substantially 0076 Preferably, the composition according to the pres non-odorous also includes materials that may, from par ent invention, wherein the Substantially non-odorous fra ticular Suppliers, contain an odour due to impurities, such as grance fixatives and fragrance component are present in a when the materials contain the impurities at not more than weight ratio from about 10:1 to about 1:10, preferably from about 5 wt %, preferably not more than 1 wt %, often even about 5:1 to about 1:5, or preferably from about 3:1 to about not more than 1 part per million (ppm). These impurities 1:3. maybe removed by purification techniques known in the art 0077. The inventors have discovered that the substan as required to make them Suitable for use in fragrance tially non-odorous fragrance fixatives can extend the fra compositions of the present invention. grance intensity of the fragrance material over time, pref 0071. As used herein, the term “vapor pressure” means erably over long periods of time Such as for example, 1 hour, the partial pressure in air at a defined temperature (e.g., 25° 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, C.) and standard atmospheric pressure (e.g., 760 mmHg or 10 hours, and possibly all the way up to 24 hrs after US 2016/0362631 A1 Dec. 15, 2016
application as compared to controls, i.e., compositions con in an amount of from about 10 wt % to about 30 wt %, taining no substantially non-odorous fragrance fixatives. relative to the total weight of the fragrance component. 0078. Additionally, the inventors have discovered that the I0089 Preferably, the present invention relates to a fine Substantially non-odorous fragrance fixatives can extend the fragrance composition, preferably in the form of of a per fragrance character, preferably the portion of the fragrance fume concentrate, a perfume, a parfum, an eau de toilette, an profile attributable to the volatile fragrance materials. By eau de parfum, or a cologne. “extend it is meant that the fragrance profile of the com 0090 Preferably, the present invention relates to a com position, preferably the components contributed by the position, wherein the composition is in the form of a body Volatile fragrance materials, can be pereceived by the con Splash or a body spray. Sumer at later time points such as for example, 1 hour, 2 0091. Therefore, it goes without saying that the compo hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, sitions of the present invention encompasses any composi 10 hours, and possibly all the way up to 24 hrs after tion comprising any of the ingredients cited herein, in any application as compared to controls, i.e., compositions con embodiment wherein each Such ingredient is independently taining no substantially non-odorous fragrance fixatives. present in any appropriate amount as defined herein. Many Such compositions, than what is specifically set out herein, Compositions can be encompassed. 0079. In one aspect, the present invention provides for a composition comprising a fragrance component present in Entrapment Materials an amount of from about 0.04 wt % to 30 wt %, preferably 0092. In yet another aspect, compositions of the present 1 wt % to about 30 wt %, more preferably less than about invention may comprise an entrapment material at a level 25 wt %, yet more preferably less than about 20 wt %, yet such that the weight ratio of the entrapment material to the even more preferably less than about 15 wt %, yet even more fragrance materials is in the range of from about 1:20 to preferably less than about 10 wt % or most preferably less about 20:1. Preferably, the composition may comprise an than about 8 wt %, relative to the total weight of the entrapment material present in the amount of from about composition. Alternatively, the fragrance component is pres 0.001 wt % to about 40 wt %, from about 0.1 wt % to about ent in an amount of from about 0.04 wt %, 0.3 wt %, 1 wt 25 wt %, from about 0.3 wt % to about 20 wt %, from about %, 2 wt %, 5 wt %, 8 wt % or 10 wt %, to about 15 wt %, 0.5 wt % to about 10 wt %, or from about 0.75 wt % to about 20 wt %, 25 wt % or 30 wt %, relative to the total weight of 5 wt %, relative to the total weight of the composition. The the composition. compositions disclosed herein may comprise from 0.001 wt 0080 Preferably, the compositions of the present inven % to 40%, from 0.1 wt % to 25 wt %, from 0.3 wt % to 20 tion comprise: wt %, from 0.5 wt % to 10 wt % or from 0.75 wt % to 5 wt 0081 (i) a fragrance component present in an amount %, relative to the total weight of the composition, of a cyclic of from about 0.04 wt % to about 30 wt %, relative to oligosaccharide. the total weight of the composition; and I0082 (ii) at least one substantially non-odorous fra 0093 Suitable entrapment materials for use herein are grance fixative from the group consisting of the mate selected from polymers; capsules, microcapsules and nano rials in Table 1, wherein the substantially non-odorous capsules; liposomes, absorbents; cyclic oligosaccharides fragrance fixative is present in the amount of from and mixtures thereof. Preferred are absorbents and cyclic about 0.1 wt % to about 20 wt %, relative to the total oligosaccharides and mixtures thereof. Highly preferred are weight of the composition. cyclic oligosaccharides (see PCT Publication Nos. 0083 Preferably, the composition of the present inven WO2000/67721 (Procter & Gamble); and WO2000/67720 tion, wherein: (Procter & Gamble); and U.S. Pat. No. 6,893,647 (Procter & I0084 (i) fragrance component is present preferably Gamble)). from about 0.04 wt %, 0.1 wt %, 0.5 wt %, 1 wt % or 2 wt % to about 30 wt %, 25 wt %, 20 wt %, 15 wt %, Volatile Solvents 10 wt % or 8 wt %, relative to the total weight of the 0094. In yet another aspect, the present invention pro composition, and wherein the fragrance component vides the solution to the problem of extending the longevity comprises: of the fragrance profile of compositions, particularly fine I0085 (a) at least one low volatile fragrance material fragrance and cosmetic compositions, preferably fine fra having a vapor pressure less than 0.001 Torr grance compositions, which commonly contain high levels (0.000133 kPa) at 25° C.; and of a volatile solvent. Preferably, the composition according I0086 (b) the low volatile fragrance material is pres to the present invention, further comprising a volatile sol ent in an amount of less than about 30 wt %, or less vent present in the amount of from about 10 wt %, 20 wt %, than about 28 wt %, or less than about 25 wt %, 30 wt %, 40 wt % or 50 wt % to about 90 wt %, 80 wt %, relative to the total weight of the fragrance compo 70 wt % or 60 wt %, relative to the total weight of the nent; and composition, and wherein the solvent is a branch or I0087 (ii) at least one substantially non-odorous fra unbranched C to Co alkyl, akenyl or alkynyl having at least grance fixative present in the amount of preferably one alcohol moiety, preferably ethanol, or isopropanol, or from about 0.1 wt % to about 20 wt %, or preferably other alcohols (e.g., methanol, propanol, isopropanol, buta from about 0.5 wt % to about 18 wt %, or more nol, and mixtures thereof) commonly found in commercial preferably from about 2.5 wt % to about 15 wt %, fine fragrance products. relative to the total weight of the composition. 0.095 Accordingly, ethanol may be present in any of the 0088 Preferably, the composition of the present inven compositions of the present invention, and more specifically, tion, wherein the low volatile fragrance material is present it will form from about 10 wt % to about 80 wt %, or even US 2016/0362631 A1 Dec. 15, 2016
from about 25 wt % to about 75 wt % of the composition, 1-chloro-1,1-difluoro-2,2-trifluoroethane (propellant 115), or combinations thereof, relative to the total weight of the 1-chloro-1,1-difluoroethylene (propellant 142B), 1,1-difluo composition. Alternatively, ethanol may be present in an roethane (propellant 152A), monochlorodifluoromethane, amount of from about 10 wt % or 25 wt % to about 75 wt and mixtures thereof. Some other propellants suitable for % or 80 wt %, relative to the total weight of the composition. use include, but are not limited to, A-46 (a mixture of The ethanol useful in the present invention may be any isobutane, butane and propane), A-31 (isobutane), A-17 acceptable quality of ethanol, compatible and safe for the (n-butane), A-108 (propane), AP70 (a mixture of propane, specific intended use of the composition Such as, for isobutane and n-butane), AP40 (a mixture of propane, example, topical applications of fine fragrance or cosmetic isobutene and n-butane), AP30 (a mixture of propane, isobu compositions. tane and n-butane), and 152A (1.1 diflouroethane). The propellant may have a concentration from about 15%, 25%, Non-Volatile Solvents 30%, 32%, 34%, 35%, 36%, 38%, 40%, or 42% to about 0096. The composition may comprise a non-volatile sol 70%, 65%, 60%, 54%, 52%, 50%, 48%, 46%, 44%, or 42% vent or a mixture of non-volatile solvents. Non-limiting by weight of the total fill of materials stored within the examples of non-volatile solvents include benzyl benzoate, container. diethyl phthalate, isopropyl myristate, propylene glycol, dipropylene glycol, triethyl citrate, and mixtures thereof. Antiperspirant Active These solvents often are introduced to the product via the 0099. The compositions described herein may be free of, perfume oil as many perfume raw materials may be pur Substantially free of, or may include an antiperspirant active chased as a dilution in one of these solvents. Where non (i.e., any substance, mixture, or other material having anti volatile solvents are present, introduced either with the perspirant activity). Examples of antiperspirant actives perfume materials or separately, then for the purposes of include astringent metallic salts, like the inorganic and calculating the proportion of fragrance component having a organic salts of aluminum, Zirconium and Zinc, as well as vapor pressure of less than 0.001 Torr (0.000133 kPa) at 25° mixtures thereof. Such antiperspirant actives include, for C. the total fragrance components does not include non example, the aluminum and Zirconium salts, such as alumi volatile solvents. Where non-volatile solvents are present, num halides, aluminum hydroxyhalides, Zirconyl oxyha introduced either with the perfume materials or separately, lides, zirconyl hydroxyhalides, and mixtures thereof. then for the purposes of calculating the total level of fragrance component this does not include non-volatile Other Ingredients Solvents. In addition if present with cyclic oligosacchrides, the non-volatile solvent may be included at a weight ratio of 0100. In yet another aspect, the composition consists the non-volatile solvent to the cyclic oligosaccharide of less essentially of the recited ingredients but may contain Small than 1:1, less than 1:2, less than 1:10, or less than 1:100. amounts (not more than about 10 wt %, preferably no more than 5 wt %, or preferably no more than 2 wt % thereof, Water relative to the total weight of the composition) of other ingredients that do not impact on the fragrance profile, 0097. In yet another aspect, water may be present in any particularly the evaporation rate and release of the fragrance of the compositions of the present invention, and more materials. For example, a fine fragrance composition may specifically, it shall not exceed about 40 wt %, preferably comprise stabilizing or anti-oxidant agents, UV filters or about 20 wt % or less, or more preferably about 10 wt % or quenchers, or colouring agents, commonly used in perfum less, relative to the total weight of the composition. Alter natively, water may be present in an amount of from about ery. 10 wt % or about 20 wt % to about 40 wt %, relative to the 0101. In yet another aspect, the composition of the pres total weight of the composition. When the composition is a ent invention, depending on its intended use, is a mixture of cosmetic composition the level of water should not be so fragrance materials possibly together with other ingredients high that the product becomes cloudy thus negatively Such as, for example, perfume carriers. By the term “per impacting the product aesthetics. It is understood that the fume carrier, it is meant to include materials which are amount of water present in the composition may be from the practically neutral from a perfumery point of view, i.e., water present in the Volatile solvent (e.g., ethanol) used in which does not significantly alter the organoleptic properties the composition, as the case may be. of perfuming components. The perfume carrier may be a compatible liquid or solid fillers, diluents, and the like. The Propellants term "compatible’, as used herein, means that the compo nents of the compositions of this invention are capable of 0098. The compositions described herein may include a being combined with the primary actives of the present propellant. Some examples of propellants include com invention, and with each other, in a manner Such that there pressed air, nitrogen, inert gases, carbon dioxide, and mix is no interaction which would substantially reduce the tures thereof. Propellants may also include gaseous hydro efficacy of the composition under ordinary use situations. carbons like propane, n-butane, isobutene, cyclopropane, The type of carrier utilized in the present invention depends and mixtures thereof. Halogenated hydrocarbons like 1,1- on the type of product desired and may comprise, but are not difluoroethane may also be used as propellants. Some non limited to, Solutions, aerosols, emulsions (including oil-in limiting examples of propellants include 1.1.1.2.2-penta water or water-in-oil), gels, and liposomes. Preferably, the fluoroethane, 1,1,1,2-tetrafluoroethane, 1,1,1,2,3,3,3- carrier is a liquid and will be a solvent Such as, for example, heptafluoropropane, trans-1,3,3,3-tetrafluoroprop-1-ene, dipropyleneglycol, diethyl phthalate, isopropyl myristate, dimethyl ether, dichlorodifluoromethane (propellant 12), benzyl benzoate, 2-(2-ethoxyethoxy)-1-ethanol, or ethyl cit 1,1-dichloro-1,1,2,2-tetrafluoroethane (propellant 114), rate (triethyl citrate). US 2016/0362631 A1 Dec. 15, 2016
0102. In yet another aspect, the compositions for use in preferably hair or skin, comprising contacting or treating the the present invention may take any form Suitable for use, body Surface with a composition of the present invention. more preferably for perfumery or cosmetic use. These include, but are not limited to, Vapor sprays, aerosols, 0107 The present invention also relates to compositions emulsions, lotions, liquids, creams, gels, sticks, ointments, of the present invention that may be used as consumer pastes, mousses, powders, granular products, Substrates, products or articles selected from the group consisting of a cosmetics (e.g., semi-solid or liquid makeup, including fabric care product, an air care product, or a home care foundations) and the like. Preferably the compositions for product. Therefore, according to this embodiment, the pres use in the present invention take the form of a vapor spray. ent invention provides a method of modifying or enhancing Compositions of the present invention can be further added the odour properties of a substrate, preferably fabric, fur as an ingredient to other compositions, preferably fine nishings, dishes, hard Surfaces and related materials, com fragrance or cosmetic compositions, in which they are prising contacting or treating the Substrate with a composi compatible. As such they can be used within Solid compo tion of the present invention. sition or applied Substrates etc. 0108. In another aspect, the present invention is directed to a method of enhancing the fragrance profile of a compo sition, preferably by improving the longevity of a character Article of Manufacture of the composition. The method comprises bringing into contact or mixing at least one Substantially non-odorous 0103) The composition may be included in an article of fragrance fixative with the fragrance material according to manufacture comprising a spray dispenser. The spray dis the composition of the present invention. Preferably, the penser may comprise a vessel for containing the composi character is derived from the volatile fragrance materials in tion to be dispensed. The spray dispenser may comprise an the composition and is characterized by a floral character or aerosolized composition (i.e. a composition comprising a aromatic/spicy character. Non-limiting examples of floral propellant) within the vessel as well. Other non-limiting character include: lavender-type note, a rose-type note, a lily examples of spray dispensers include non-aerosol dispensers of the Valley-type note, a muguet-type note, a jasmine-type (e.g. vapor sprays), manually activated dispensers, pump note, a magnolia-type note, a cyclamen-type note, a hya spray dispensers, or any other Suitable spray dispenser cinth-type note, a lilac-type note, an orange blossom-type available in the art. note, a cherry blossom-type note, a peony-type note, a lotus-type note, a linden blossom-type note, an osmanthus Methods of Using the Compositions type note, a heliotrope-type note, a violet-type note, an orris-type note, a tiare-type, a patchouli-type note and the 0104. The composition of the present invention accord like. ing to any embodiments described herein is a useful per fuming composition, which can be advantageously used as 0109) Non-limiting examples of aromatic (or haerba consumer products intended to perfume any suitable Sub ceous) and spicy character include: cinnamon, cloves, cori strate or surface. As used herein, the term "substrate” means ander, ginger, Saffron, peppers of various kinds (e.g.: black any Surface to which the composition of the present inven pepper, pink pepper), caraway, cardamom, anise, tea, coffee, tion may be applied to without causing any undue adverse cumin, nutmeg, coumarin, basil, rosemary, thyme, mint, effect. For example, this can include a wide range of Surfaces tarragon, marjoram, fennel, Sage, and juniper. including human or animal skin or hair, paper (fragranced 0110 Preferably, the fragrance profile or character of the paper), air in a room (air freshener or aromatherapy com composition of the present invention is detectable by a position), fabric, furnishings, dishes, hard Surfaces and consumer at later time points such as, for example, 1 hour, related materials. Preferred substrates include body surfaces 2 hours, 3 hours, 4 hours, 5 hours, 6 hours, 7 hours, 8 hours, Such as, for example, hair and skin, most preferably skin. 10 hours, and possibly all the way up to 24 hours after 0105. The composition of the present invention may be application of the composition to a Substrate as compared to used in a conventional manner for fragrancing a substrate. controls. An effective amount of the composition, typically from 0111. In another aspect, the present invention is also about 1 uL to about 10,000 uL, preferably from about 10 ul directed to a method of producing a consumer product to about 1,000 uL, more preferably from about 25 uL to comprising bringing into contact or mixing into the product about 500 uL, or most preferably from about 50 uL to about an organoleptically active quantity of a composition of the 100 uL, or combinations thereof, is applied to the suitable present invention. Preferably, the present invention is also substrate. Alternatively, an effective amount of the compo directed to a perfuming consumer product or article com sition of the present invention is from about 1 uL. 10 uI, 25 prising a composition according to the present invention, uL or 50 uL to about 100 uL, 500 uL, 1,000 uL or 10,000 uL. wherein the perfuming consumer product is selected from The composition may be applied by hand or applied utilizing the group consisting of a fabric care product, an air care a delivery apparatus Such as, for example, vaporizer or product or a home care product. atomizer. Preferably, the composition is allowed to dry after its application to the Substrate. The scope of the present invention should be considered to cover one or more distinct Substantially Non-Odorous Fragrance Fixatives applications of the composition or the continuous release of 0112 In one aspect, compositions of the present inven a composition via a vaporizer or other type of atomizer. tion comprise at least one Substantially non-odorous fixative 0106 The present invention provides a method of modi selected from the group consisting of the materials disclosed fying or enhancing the odour properties of a body Surface, in Table 1. US 2016/0362631 A1 Dec. 15, 2016
TABLE 1. Substantially Non-Odorous Fragrance Fixatives
CAS No. Chemical or INCI Name Trade Name Number Supplier 1. C12-14 Sec-Pareth-3 Tergitol (R) 15-S-7 68131- Sigma Aldrich 40-8 (UK) 2. Poly(ethylene glycol-ran- PPG-7-Buteth-10 9038- Sigma Aldrich propylene glycol) monobutyl 95-3 (UK) ether 3. PPG-4-Ceteth-10 Nikko PBC-33 37311- Chemical Navi O1-6 4. Deceth-4 Ethal DA-4 5703- Ethox 94-6 Chemicals, Inc. 5. PPG-5-Ceteth-20 AECPPG-5-Ceteth-20 9087- A&E 53-0 Connock (Perfumery & Cosmetics) Ltd. 6. C14-15 Pareth-7 Neodol 45-7 alcohol 68951- Shell ethoxylate 67-7 Chemical Company 7. Linear alcohol (C12-15) Bio-Soft N25-7 68131- Stephan Pareth-3ethoxylate, POE-7 39-5 Company 8. Linear alcohol (C12-13) Bio-SoftN23-6.5 66455- (USA) Pareth-3ethoxylated, POE-6.5) 14-9 9. Polyethylene glycol 1100 Cremophor (R) A 25 68439- Sigma Aldrich mono (hexadecyloctadecyl) 49-6 UK) ether O. Linear alcohol (C9-11) Bio-Soft N91-8 68439- Stephan ethoxylated POE-8 Pareth-3 46-3 Company (USA) 1. Coceth-10 or Polyoxyethylene Genapol (R) C-100 61791-13-7 Sigma Aldrich (UK) (10) dodecyl ether 2. Alcohols, C12-14, ethoxylated Rhodasurf (R) LA 30 68439-50-9 Solvay Solutions Italia S.p.A 3. Poly(ethylene glycol) Poly(ethylene glycol) 9004-74-4 Sigma Aldrich (UK) methyl ether methyl ether 4. C10-16 Pareth-1 Neodol (R) PC 110 680O2-97-1 Shell Chemical Company 5. PPG-11 Stearyl Ether Ki Arano TM PS11E 25231-21-4 Croda (UK) 6. Steareth-100 Brij (R) S100 90OS-00-9 Sigma Aldrich (UK) 7. Polyethylene glycol Brij (R) C-58 9004-95-9 Sigma Aldrich (UK) hexadecyl ether 8. Pluronic (R) F-127 Pluronic (R) F-127 90O3-11-6 Sigma Aldrich (UK) 9. Linear Alcohol (C11) Bio-Soft N1-5 34398-01-1 Stepan Canada Inc. Elhoxylate, POE-5 20. Laureth-10 Intrasol FA 1218.10 6540-99-4 Evonik Industries AG 21. Decaethylene glycol Polyoxyethylene (10) 90O2-92-0 Sigma Aldrich (UK) mono-dodecyl ether lauryl ether 22. Ethylene glycol 2-Methoxyethanol 109-86-4 Sigma Aldrich (UK) monomethyl ether 23. Myreth-4 Homulgator 920 G 273O6-79-2 Grau Aromatics GmbH & Company KG 24. Oleth-16 Alkoxylated Alcohols Pegnol O-16A 2S19 O-OS-O Toho Chemical Industry Co., Ltd. 25. Isosteareth-5 Emalex 1805 S2292-17-8 Nihon Emulsion Company, Ltd. 26. PPG-10 Cetyl Ether Arano TM PC 10 9035-85-2 Croda (UK) 27. Polyoxy(ethylene glycol) Poly(ethylene glycol) 24938-91-8 Sigma-Aldrich (UK) (18) tridecyl ether (18) tridecyl ether 28. Poly(oxy-1,2-ethanediyl), ALFONIC (R) 10-8 26183-52-8 Sasol Chemicals a-decyl-w-hydroxy Ethoxylate (USA) LLC 29. Laureth-1 Mackam TM 2LSF 4536-30-5 Rhodia (DE) 30. PEG-5 Hydrogenated Ethox HTAM-5 61791-26–2 Ethox Chemicals, Inc. Tallow Amine 31. PEG-15 Oleamine Nikkol TAMNO-15 2663S-93-8 Nikko Chemicals Co., Ltd. 32. Polyoxyethylene (20) oleyl ether Brij (R) O20-SS 9004-98-2 Sigma Aldrich (UK) 33. Cetoleth-10 Brij (R) CO10 8065-81-4 Croda, Inc. 34. Talloweth-7 Emulmin 70 61791-28-4 Sanyo Chemical Industries Ltd. 35. Isobutoxypropanol Alcohols Isobutoxypropanol 341SO-3S-1 MolPort 36. Isobutoxypropanol Alcohols Isobutoxypropanol 23436-19-3 AKos Consulting & Solutions US 2016/0362631 A1 Dec. 15, 2016 10
TABLE 1-continued Substantially Non-Odorous Fragrance Fixatives
CAS No. Chemical or INCI Name Trade Name Number Supplier 37. Dielhylene Glycol Twincide EDG 11-46-6 Roda 38. Methoxyethanol Hisolve MC O9-86-4 Toho Chemical Industry Co., Ltd. 39. Ethoxyethanol Alcohols 2-Ethoxyethanol 10-8O-5 Sigma-Aldrich (UK) 40. Methoxyisopropanol Alcohols Dowano TM PM O7-98-2 The Dow Chemical Company 41. Methoxyethanol Hisolve MC 32718-54-O Toho Chemical Industry Co., Ltd. 42. Methylal Ethers Dimethoxymelhane 09-87-5 Sigma-Aldrich (UK) 43. 3-Methoxybutanol Methoxybutanol 2517-43-3 Hans Schwarzkopf GmbH Co. KG 44. Butoxyethanol Butyl OXITOL 11-76-2 Shell Chemical Company 45. Propylene Glycoln-Butyl Ether Dowano TM PnB 5131-66-8, The Dow Chemical 29387-86-8 Company 46. Propylene Glycol Butyl Ether Propylene Glycol Butyl Ether 15821-83-7 Sigma Aldrich (UK) 47. 2-(2-butoxyethoxy)ethanol Diethylene glycol butyl ether 12-34-5 Sigma Aldrich (UK) 48. Deceth-4 Phosphate Crodafos TM D4A S2O19-36-0 Croda, Inc. 49. 2-(Hexadecyloxy)ethanol Ethylene glycol 2136-71-2 Sigma-Aldrich (UK) monohexadecyl ether SO. Poly(propylene glycol) Poly(propylene glycol) 9003-13-8 Sigma-Aldrich (UK) monobutyl ether monobutyl ether 51. Propylene Glycol Propyl Ether Dowano TM PIP 3O136-13-1 The Dow Chemical Company 52. Propylene Glycoln-Butyl Ether Dowano TM PnB 29387-86-8. The Dow Chemical 5131-66-8 Company 53. Dipropylene glycol Di (propylene glycol) methyl 34590-94-8 Sigma Aldrich (UK) monomethyl ether ether, mixture of isomers 54. Dipropylene Glycol Proglyde TM DMM 111109–77-4 The Dow Chemical Dimethyl Ether Company 55. PPG-2 Methyl Ether Dowano TM DPM 13429-07-7. The Dow Chemical Company 56. Methoxydiglycol Ethers OriStar DEGME 111-77-3 Orient Stars LLC 57. Diethylene glycol ethyl ether Di (ethylene glycol) ethyl ether 111-90-0 Sigma Aldrich (UK) S8. Dimethoxydiglycol Ethers Dimethyldiglycol 111-96- H&V Chemicals 59. PPG-3 Methyl Ether Dowano TM TPM 37286-64-9. The Dow Chemical Company 60. Methyl Morpholine 224286 ALDRICH 7529-22-8 Sigma-Aldrich (UK) Oxide Amine Oxides 4-Methylmorpholine N-oxide 61. Oleth-3 Brij (R) O3 S274-66-8 Croda Europe, Ltd. 62. Tri(propylene glycol) Dowano TM TPB 55934-93-5 Sigma-Aldrich (UK) n-butyl ether 63. Tripropylene Glycol Tripropylene Glycol 24800-44-0 Sigma-Aldrich (UK) 64. PPG-3 Methyl Ether Dowano TM TPM 25498- The Dow Alkoxylaled Alcohols 49-1 Chemical Company 65. Triethylene glycol Triglycol 112-27-6 Sigma Aldrich (UK) 66. PEG-3 Methyl Ether HymolTM 112-35-6 Toho Chemical Industry Co., Ltd. 67. Laureth-3 AEC Laureth-3 3OSS-94-5 A & E Connock (Perfumery & Cosmetics) Ltd. 68. Ethylhexylglycerin AG-G-7SOO8 70445-33-9 Angene Chemical 69. Tetra (ethylene glycol) Tetraethylene glycol 112-60-7 Sigma Aldrich (UK) 70. Steareth-3 Isoxal 5 4439-32-1 Vevy Europe SpA 71. Ceteth-3 Emalex 103 4484-59-7 Nihon Emulsion Company, Ltd. 72. Myreth-3 Isoxal 5 26826-30-2 Vevy Europe SpA 73. Trideceth-3 Alfonic (RTDA- Sasol North America. 3 Ethoxylate Inc. 74. Ceteth-2 Brij (R) C2 S274-61-3 Croda Europe, Ltd. 75. Oleth-2 Brij (R) O2 S274-65-7 Croda, Inc. 76. Steareth-2 Brij (R) S2 16057-43-5 Croda, Inc. 77. Cetoleth-10 Brij (R) CO10 8065-81-4 Croda, Inc. 78. Trimethyl Pentanol Trimethyl Pentanol 68959-25-1 Angene Chemical Hydroxyethyl Ether Alcohols Hydroxyethyl Ether 79. Steareth-10 Allyl Ether Salcare (R) SC80 109292-17-3 BASF 80. TEA-Lauryl Ether material ID-AG-J-99.109 1733-93-3 Angene Chemical 81. Polyglyceryl-2 Oleyl Ether Chimexane NB 71032-90-1 Chimex 82. Batyl Alcohol B4O2 ALDRICH 544-62-7 Sigma-Aldrich (UK) 83. Octaethylene Glycol 15879 ALDRICH S117-19-1 Sigma-Aldrich (UK) US 2016/0362631 A1 Dec. 15, 2016 11
TABLE 1-continued Substantially Non-Odorous Fragrance Fixatives
CAS No. Chemical or INCI Name Trade Name Number Supplier 84. Triglycerol diisostearate Citro TM 66082–42-6 Croda (UK) 85. Diglycerin Diglycerin 801 S9113-36-9 Sakamoto Yakuhin Kogyo Co., Ltd. 86. Polyglycerin #310 Polyglycerin #310 25618-55-7 Sakamoto Yakuhin Kogyo Co., Ltd. 87. Distearyl Ether Cosmacol (R) SE 6297-03-6 Sasol Germany GmbH 88. Caprylyl Glyceryl Ether Caprylyl Glyceryl Ether 10438-94-5 AKos Consulting & Solutions 89. Chimyl Alcohol Chimyl Alcohol 506-03-6 Nikko Chemicals Co., Ltd. 90. Dipentaerythrityl Liponate (R). DPC-6 68130-24-5 Lipo Chemicals, Inc. Hexacaprylate Hexacaprate 91. Morpholine 394.467 ALDRICH 110-91-8 Sigma-Aldrich (UK) 92. Dimethyl Oxazolidine OXABANTM-A 51200-87-4 The Dow Chemical Company 93. Ethyl Hydroxymethyl 4-Oxazolemethanol 68140-98-7 Angene Chemical Oleyl Oxazoline 94. Methyl Hydroxymethyl Adeka Nol GE-RF 14408-42-5 Adeka Corporation Oleyl Oxazoline 95. Pramoxine HCI OriStar PMHCL 637-58-1 Orient Stars LLC 96. Allantoin Ascorbate Allantoin Ascorbate 57448-83-6 ABI Chem 97. Stearamidopropyl Mackalene TM326 SS852-14-7 Rhodia Inc. Morpholine Lactate 98. Dioxolane Elcotal DX 646-06-0 Lambiotte & CIE S.A. 99. Glycerol Formal Glycerol Formal 5464-28-8 Sigma Aldrich (UK) 00. Stearamidopropyl Morpholine Mackine 321 SS852-13-6 Rhodia Inc. 01. 2,4,6-Tris(bis(methoxymethyl) Poly(melamine-co- 68.002-20-0 Sigma-Aldrich (UK) amino-1,3,5-triazine formaldehyde)methylated O2. Poloxamine 1307 Pluracare (R) 1307 11111-34-5 BASF O3. Nonoxynol-8 Igepal (R) CO-610 271 77-05-5 Rhodia Inc. 04. Nonoxynol-10 Igepal (R) CO-710 271 77- Rhodia Inc. O8-8 OS. Octoxynol-10 Nikkol OP-10 2315-66-4 Nikko Chemicals Co., Ltd. O6. Nonoxynol-9 Igepal (R) CO-630 68.987-90-6 Rhodia Inc. O7. Nonoxynol-9 Iodine Nonoxynol-9 iodine 94349-40-3 Angene Chemical O8. Octylphenoxy Igepal (R) CA-630 68.987-90-6 Rhodia Inc. poly(ethyleneoxy)ethanol, branche O9. Sodium Octoxynol-2 TritonTMX-200 55837-16-6 The Dow Chemical Ethane Sulfonate Company 10. Benzylhemiformal Prevento D2 14548-60-8 Lanxess Corporation 11. Nonoxynol-2 Igepal (R) CO-210 271 76-93-8 Rhodia Inc. 12. Octoxynol-3 Igepal (R) CA-420 231S-62-0 The Dow Chemical Company 13. Nonoxynol-3 Marlophen NP 3 2717.6-95-0 Sasol Germany GmbH 14. Alkoxylaled Alcohols Alkasurf NP-4 7311-27-5 Rhodia Inc. 1S. Nonoxynol-3 Triethylene Glycol 51437-95-7 Santa Cmz Mono (p-nonylphenyl)Ether Biotechnology 16. Nonoxynol-7 Lowenol 2689 271 77-03-3 Jos. H. Lowenstein & Sons, Inc. 17. Nonoxynol-6 Igepal (R) CO-530 271 77-01-1 Rhodia Inc. 18. Nonoxynol-5 Igepal (R) CO-520 2O636-48-O Rhodia Inc. 19. Nonoxynol-5 Igepal (R) CO-520 26264-O2-8 Rhodia Inc. 20. Nonoxynol-4 Alkasurf NP-4 271 76-97-2 Rhodia Inc. 21. Polyglyceryl-10 Trioleate Nikkol Decaglyn 3-OV 102051-OO-3 Nikko Chemicals Co., Ltd. 22. Polyglyceryl-10 Dioleate Nikkol Decaglyn 2-O 33940-99-7 Nikko Chemicals Co., Ltd 23. Polyglyceryl-10 Tetraoleale Caprol 10G40 34424-98-1 Abitec Corporation 24. Polyglyceryl-10 Stearate Nikkol Decaglyn 1-SV 79777- Nikko EX 30-3 Chemicals Co., Ltd. 25. Polyglyceryl-10 Oleate S-Face O-1001 P 7966S-93-3 Sakamoto Yakuhin Kogyo Co., Ltd. 26. Polyglyceryl-10 Myristale Nikkol Decaglyn 1-MV EX 87390-32-7 Nikko Chemicals Co., Ltd. 27. Dermofeel(R) G 10 L Dermofeel (R) G 10 L 344O6-66-1 Dr. Straetnians 28. Polyglyceryl-6 Laurate NIKKOL Hexaglyn 1-L 51033-38-6 Chemical Navi 29. Polyglyceryl-6 Isostearate S-Face IS-601 P 126928-07-2 Sakamoto Yakuhin Kogyo Co., Ltd. 30. Choleth-10 Emalex CS-10 27321-96-6 Nihon Emulsion Company, Ltd. US 2016/0362631 A1 Dec. 15, 2016 12
TABLE 1-continued Substantially Non-Odorous Fragrance Fixatives
CAS No. Chemical or INCI Name Trade Name Number Supplier 31. Steareth-10 Allyl Salcare (R) SC80 109292-17-3 BASF Ether/Acrylates Copolymer 32. Polyvinyl Stearyl Ether Giovarez (R) 1800 9003-90-7 Phoenix Chemical, Inc. 33. Dicetyl Ether Cosmacol Ether 16 Sasol Germany GmbH 34. PPG-23-Steareth-34 Unisafe 34S-23 9038-43-1 Pola Chemical Industries, Inc. 35. Stearoxypropyl Farmin DME-80 17517-01-0 Kao Corp. Dimethylamine 36. Dislearyl Ether Cosmacol SE 6297-03-6 Sasol Germany GmbH 37. Polyguaternium-10 AEC Polyguaternium-10 SS3S3-19-0 A & E Connock (Perfumery & Cosmetics) Ltd. 38. Octyl ether Dioctyl ether 629-82-3 Sigma Adlrich (UK) 39. Ethyl Ether Diethyl Ether 60-29-7 EMD Chemicals 40. Methyl Hexyl Ether Ethers methylhexyl ether 4747-07-3 TCIAMERICA 41. Ceteth-12 Emalex 112 941.59-75-8 Nihon Emulsion Company, Ltd. 42. Ceteth-10 or cetyl Jeecol CA-10 14529- Jeen alcohol POE-10 40-9 International 43. Steareth-10 Jeecol SA-10 13149-86-5 Jeen International 44. Nonaethylene glycol Nonaethylene glycol 3OSS-99-0 Sigma Aldrich (UK) monododecyl ether monododecyl ether 45. Oleth-10 Brij (R) O10 71976-OO-6 Croda, Inc. 46. Oleth-10 Brij (R) O10 24871-34-9 Croda, Inc. 47. PEG-12 Carbow axTMPEG 600 6790-09-6 The Dow Chemical Company 48. PEG-9 Sabopeg 400 3386-18-3 Sabo S.p.a. 49. PEG-10 DECAETHYLENE SS79-66-8 MolPort GLYCOL SO. PEG-6 Carbow axTMPEG 300 2615-1S-8 The Dow Chemical Company S1. Glycerol propoxylate Glycerol propoxylate 25791-96-2 Sigma Aldrich (UK) 52. Glycerol ethoxylate Glycerol ethoxylate 31694-55-0 Sigma Aldrich (UK) 53. Laureth-8 AEC Laureth-8 3OSS-98-9 A & E Connock (Perfumery & Cosmetics) Ltd. 54. Oleth-8 Emalex 508 2704O-O3-5 Nihon Emulsion Company, Ltd. 55. Laureth-7 Alfonic 1216CO-7 3OSS-97-8 Sasol North Ethoxylate America, Inc. 56. Steareth-7 Polyoxyethylene (7) 66146-84-7 Sigma Aldrich stearyl ether 57. Deceth-6 Alfonic 1012-6.0 Ethoxylate 5168-89-8 Sasol North America, Inc. S8. Steareth-6 Emalex 606 242O-29-3 Nihon Emulsion Company, Ltd. 59. Hexaethylene Hexaethylene glycol 3OSS-96-7 Sigma-Aldrich (UK) glycol monododecyl ether monododecyl ether 60. Hexaethylene glycol Hexaethylene glycol 51 68-91-2 Sigma-Aldrich (UK) monohexadecyl ether monohexadecyl ether 61. Beheneth-5 Nikkol BB-5 1362O7-49-3 Nikko Chemicals Co., Ltd. 62. Myreth-5 Isoxal 12 92669-01-7 Vevy Europe SpA 63. Steareth-5 Jeecol SA-5 71093-13-5 Jeen International Corporation 64. Ceteth-5 Emalex 105 4478-97-1 Nihon Emulsion Company, Ltd. 65. Oleth-5 Brij (R) O5 5353-27-5 Croda, Inc. 66. Laureth-5 Safol (R) 23E5 Ethoxylate 3OSS-95-6 Sasol North America, Inc. 67. Steareth-4 Jeecol SA-4 S9970-10-4 Jeen International Corporation 68. Laureth-4 Brij (R) L4 S274-68-0 Croda, Inc. 69. Myreth-4 Homulgator 920 G 39034-24-7 Grau Aromatics GmbH & Company KG 70. Ceteth-4 Procol CA-4 5274-63-5 Protameen Chemicals 71. Oleth-4 Chemial OA-4 S3S3-26-4 Chemax, Inc. 72. Oleth-4 Chemial OA-4 103622-85-1 Chemax, Inc. 73. Polyimide-1 Aquaflex TM XL-30 497926-97-3 Chemwill 74. Polymethoxy Bicyclic Caswell No. 494CA 56709-13-8 Angene Chemical Oxazolidine US 2016/0362631 A1 Dec. 15, 2016 13
TABLE 1-continued Substantially Non-Odorous Fragrance Fixatives
CAS No. Chemical or INCI Name Trade Name Number Supplier 75. Hydroxymethyl Zodine TMZT 6542-37-6 Angus Chemical Dioxoazabicyclooctane Company 76. Dihydro-7a-ethyloxazolo 5-Ethyl-1-aza-3,7- 7747-35-5 Sigma Aldrich (UK) 3,4-coxazole dioxabicyclo[3.3.0 octane 77. Dibenzylidene Sorbitol Disorbene (R) 32647-67-9 Roquette America, Inc. 78. Dimethyldilbenzylidene Millad (R) 3988 135861-S6-2 Milliken Chemicals Sorbitol 79. Laureth-2 Alfonic 1216CO-2 3OSS-93-4 Sasol North Ethoxylate America, Inc. 80. 2-(2-Butoxyethoxy)ethyl Piperonyl Butoxide 51-03-6 Sigma-Aldrich (UK) (6-propylpiperonyl) ether 81. Menthone Glycerin Acetal Frescolat (R) MGA 631.87-91-7 Symrise 82. Propylene Glycol Caprylate Mackaderm PGC 68332-79-6 Rhodia Inc. 83. Diethoxynonadiene SBBO16951 67674-36-6 Ambi liter 84. Menthoxypropanediol Coolact (R) 10 87O61-04-9 Takasago Alcohols International Corporation 85. 2-Diphenylmethoxy-N,N- Diphenhydramine HCI 147-24-O Sigma-Aldrich (UK) dimethylethylamine hydrochloride 86. 3-((2-ethylhexyl)oxy) 70445-33-9 propane-1,2-diol 87. 3-((2-propylheptyl)oxy) propane-1,2-diol 88. 1-amino-3-((2-ethylhexyl)oxy) 99509-00-9 propan-2-ol 89. 1-(1-Methyl-2- Di(propylene glycol) 29911-27-1 Sigma Aldrich (UK) propoxyelhoxy)-2-propanol propyl ether 90. propyl 4-2-(diethylamino)-2- Kolliphor (R) EL 61791-12-6 Sigma Aldrich (US) oxoethoxy-3-methoxyphenyl) acetate 91. Bis-methoxy PEG-13 Expert Gel (R) EG56 936645-35-1 PolymerExpert S.A. PEG-438.PPG-110 SMIDI (Pessac, France) Copolymer
0113. The compounds selected from the group consisting of clarity, when the fragrance materials refer to a single of Table 1 substantially non-odorous fragrance fixatives individual compound, its vapor pressure should be deter 1-190, 191, and mixtures thereof, act as a substantially mined according to the reference program cited above. In the non-odorous fragrance fixative of the present invention. For case that the fragrance materials are a natural oil, extract or example, the Substantially non-odorous fragrance fixatives, absolute, which comprises a mixture of several compounds, with a fragrance component act to prolong the duration the vapor pressure of the complete oil should be treated a during which the fragrance profile, preferably the characters mixture of the individual perfume raw material components attributable from the volatile fragrance materials, can be using the reference program cited above. The individual perceived as compared to a control composition in the components and their level, in any given natural oil or absence of the fixatives. As another example, the Substan tially non-odorous fragrance fixatives with a fragrance com extract, can be determined by direct injection of the oil into ponent, can improve the fidelity of the fragrance profile, a GC-MS column for analysis as known by one skilled in the preferably the fragrance component derived from the vola art. In the scenario that the fragrance materials are a pro tile fragrance materials, such that it remains significantly the prietary specialty accord, so called bases, the vapor pres same from initial impression to the end as compared to a Sure, using the reference program cited above, should pref control composition in the absence of the Substantially erably be obtained from the supplier. However, it is non-odorous fragrance fixatives. While not wishing to be understood by one skilled in the art that they can physically bound by theory, it is believed that the substantially non analyze the composition of a full fragrance oil available odorous fragrance fixatives associate to the fragrance mate commercially to identity the fragrance raw materials and rials and retard evaporation. This may be due to a combi their levels using standard GC-MS techniques. This would nation of both the functionality and the structure of the be irrespective of whether they had been added to the Substantially non-odorous fragrance fixatives and the fra fragrance oil as individual chemicals, as components of grance materials. naturals or from proprietary bases. Although proprietary bases and naturals are included in our examples, when Fragrance Materials analyzing a commercially available fragrance via GC-MS one could simply identify the components of the base or 0114 Preferably, the “fragrance materials” have been natural oil as part of the overall fragrance mixture and their classified as low volatile fragrance materials or volatile levels, without being able to identify which proprietary base fragrance materials by their vapor pressure. For the purpose or natural oil the fragrance had come from. US 2016/0362631 A1 Dec. 15, 2016 14
0115 The nature and type of fragrance materials in the 0116 (i) Low Volatile Fragrance Materials compositions according to the present invention can be 0117 Fragrance materials classified as “low volatile fra selected by the skilled person, on the basis of its general grance materials are ones having a vapor pressure less than 0.001 Torr (0.000133 kPa) at 25° C. Preferably, the low knowledge together with the teachings contained herein, volatile fragrance materials form the at most about 30 wt %, with reference to the intended use or application of the wherein the wt % is relative to the total weight of the composition and the desired fragrance profile effect. fragrance component. Preferably, the low volatile fragrance Examples of Suitable fragrance materials are disclosed in material is selected from at least 1 material, or at least 2 U.S. Pat. No. 4,145,184, U.S. Pat. No. 4,209,417, U.S. Pat. materials, or at least 3 materials, or at least 5 materials, or No. 4,515,705, and U.S. Pat. No. 4,152,272. at least 7 materials as disclosed in Table 2. TABLE 2 Low Volatile Fragrance Materials CAS Vapor Pressure No. Number IUPAC Name Common Name** (Torr at 25° C.)* 1. 1211-29-6 Cyclopentaneacetic acid, 3-oxo-2- Methyl jasmonate O.OOO96SOO (2Z)-2-penten-1-yl-, methyl ester, (1R,2R)- 2. 2821.9-60-5 2-Buten-1-ol, 2-methyl-4- Hindinol O.OOO961OO (2,2,3-trimethyl-3-cyclopenten-1-yl)- 3. 93-08-3 Ethanone, 1-(2-naphthalenyl)- Methyl beta- O.OOO957OO naphthyl ketone 4. 67633-95-8 3-Decanone, 1-hydroxy- Methyl Lavender O.OOO951OO Ketone 5. 1984.04-98-7 Cyclopropanemethanol, 1-methyl-2- Javanol (R) O.OOO902OO (1.2.2-trimethylbicyclo[3.1.0) hex-3-yl)methyl 6. 121-32-4 Benzaldehyde, 3-ethoxy-4-hydroxy- Ethyl vanillin O.OOO884OO 7. 724O3-67-9 3-Cyclohexene-1-methanol, 4- Myraldylacetate O.OOO87900 (4-methyl-3-penten-1-yl)-, 1-acetate 8. 28940-11-6 2H-1,5-Benzodioxepin-3 (4H)- Calone O.OOO831OO one, 7-methyl 9. 139504-68-0 2-Butanol, 1-2-(1,1-dimethylethyl) Amber core O.OOO8O3OO cyclohexyl)oxy O. SO2847-01-0 Spiro5.5undec-8-en-1-one, 2,2,7, Spiro5.5undec- O.OOO731OO 9-tetramethyl- 8-en-1-one, 2,2,7, 9-tetramethyl 1. 2570-03-8 Cyclopentaneacetic acid, 3-oxo-2-pentyl-, trans-Hedione O.OOO71OOO methyl ester, (1R,2R)-rel 2. 248S1-98-7 Cyclopentaneacetic acid, 3-oxo-2-pentyl-, Methyl O.OOO71OOO (or 128087-96-7) methyl ester dihydrolasmonate or alternatives' 3. 101-86-0 Octanal, 2-(phenylmethylene)- Hexyl O.OOO697OO cinnamic aldehyde 4. 365411-50-3 Indeno4,5-d-1,3-dioxin, Nebulone O.OOO692OO 44a,5,6,7,8,9.9b-octahydro-7,7,8,9.9- pentamethyl 5. 37172-53-5 Cyclopentanecarboxylic acid, Dihydro Iso O.OOO67SOO 2-hexyl-3-oxo-, methyl ester Jasmonate 6. 6S113-99-7 3-Cyclopentene-1-butanol, Sandalore (R) O.OOO62SOO C.B.,2,2,3-pentamethyl 7. 68133-79-9 Cyclopentanone, 2-(3,7- Apritone O.OOO62OOO dimethyl-2,6-Octadien-1-yl)- 8. 7212-44-4 1,6,10-Dodecatrien-3-ol, 3,7,11- Nerolidol O.OOO616OO trimethyl 9. S3243-59-7 2-Pentenenitrile, 3-methyl-5- Citronitril O.OOO61SOO phenyl-, (2Z)- 2O. 134123-93-6 Benzenepropanenitrile, Fleuranil O.OOOST600 4-ethyl-O.C.-dimethyl 21. 77-53-2 1H-3a,7-MethanoaZulen-6-ol, Cedro Crude O.OOO56900 octahydro-3,6,8,8-tetramethyl-, (3R,3aS,6R,7R,8aS)- 22. 681.SS-66-8 Ethanone, 1-(1,2,3,5,6,7,8,8a- Iso Gamma Super O.OOOS6SOO octahydro-2,3,8,8-tetramethyl-2- naphthalenyl)- 23. 54464-57-2 Ethanone, 1-(1,2,3,4,5,6,7,8- Iso-E Super (R) O.OOOS38OO tetramethyl-2-naphthalenyl)- 24. 774-55-0 Ethanone, 1-(5,6,7,8-tetrahydro- Florantone O.OOOS3OOO 2-naphthalenyl)- 25. 141-92-4 2-Octanol, 8,8-dimethoxy-2,6-dimethyl- Hydroxycitronellal O.OOOS2OOO Dimethyl Acetal 26. 2O665-85-4 Propanoic acid, 2-methyl-, Vanillin O.OOOS1200 4-formyl-2-methoxyphenyl ester isobutyrate
US 2016/0362631 A1 Dec. 15, 2016 17
TABLE 2-continued Low Volatile Fragrance Materials CAS Vapor Pressure No. Number IUPAC Name Common Name** (Torr at 25° C.)* 95. 183551-83-9 Naphtho2,1-bfuran-6(7H)- Myrrhone O.OOOOO977 one, 8,9-dihydro-1,5,8- trimethyl-, (8R)- 96. 102-17-O Benzeneacetic acid, (4- Para Anisyl O.OOOOO813 methoxyphenyl)methyl ester PhenylAcetate 97. 120-11-6 Benzene, 2-methoxy-1- Benzyl Iso O.OOOOO676 (phenylmethoxy)-4-(1-propen-1-yl)- Eugenol 98. 102-22-7 Benzeneacetic acid, (2E)- Geranyl O.OOOOO645 3,7-dimethyl-2,6-octadien-1-yl ester Phenylacetate 99. 111879-80-2 Oxacyclohexadec-12-en-2- Habanolide O.OOOOO431 one, (12E)- 100% OO. 87-22-9 Benzoic acid, 2-hydroxy-, Phenyl Ethyl O.OOOOO299 2-phenylethyl ester Salicylate O1. 78-37-5 2-Propenoic acid, 3-phenyl-, Linallyl O.OOOOO174 1-ethenyl-1,5-dimethyl Cinnamate 4-hexen-1-yl ester O2. 28.645-51-4 Oxacycloheptadec-10-en-2-one Ambrettolide O.OOOOO139 O3. 123-69-3 Oxacycloheptadec-8-en-2-one, Ambrettolide O.OOOOO136 (87)- 04. 3391-83-1 1,7-Dioxacycloheptadecan Musk RI O.OOOOOOST 8-one OS. 68527-79-7 7-Oclen-2-ol, 8-(1H-indol Indolene O.OOOOOO445 1-yl)-2,6-dimethyl O6. 89-43-0 Methyl 2-(7-hydroxy-3,7- Aurantinol O.OOOOOOO100 dimethyloctylidene)aminobenzoate O7. 54982-83-1 1,4-Dioxacyclohexadecane-5, 16-dione Zenolide O.OOOOOOOO834 O8. 105-95-3 1,4-Dioxacycloheptadecane-5,17-dione Ethylene O.OOOOOOOO313 Brassylate O9. 3681-73-O Hexadecanoic acid, (2E)-3,7- Hexarose O.OOOOOOOO3OO dimethyl-2,6-ocladien-1-yl ester 10. 4159-29-9 Phenol, 4-3-(benzoyloxy)-1- Coniferyl O.OOOOOOOO170 propen-1-yl)-2-methoxy benzoate 11. 144761-91-1 Benzoic acid, 2-(1-hydroxy Trifone O.OOOOOOOOO93 3-phenylbutyl)amino-, methyl ester DIPG Non-limiting examples of alternative qualities from various suppliers can be purchased under the following tradenames: Kharismal R. Super (IFF), Kharismal (R) (DFF), Hedione (R) (Firmenich), Hedione (RHC (Firmenich), Paradisone (Firmenich), Cepionate (Zenon), Super cepionate (Zenon), Claigeon R (Zenon), *Vapor Pressures are acquired as described in the Test Methods Section. **Origin: The low volatile fragrance materials may be obtained from one or more of the following companies: Firmenich (Geneva, Switzerland), Symrise AG (Holzminden, Germany), Givaudan (Argenleuil, France), DFF (Hazlet, New Jersey), Bedoukian (Danbury, Connecticut), Sigma Aldrich (St. Louis, Missouri), Millennium Speciality Chemicals (Olympia Fields, Illinois), Polarone International (Jersey City, New Jersey), and Aroma & Flavor Specialities (Danbury, Connecticut).
0118 (ii) Volatile Fragrance Materials preferably greater than about 80 wt %, or more preferably 0119 Fragrance materials classified as “volatile fra greater than about 88 wt %, relative to the total weight of the grance materials are ones having a vapor pressure greater fragrance component. Preferably, the volatile fragrance than or equal to 0.001 Torr (0.000133 kPa) at 25° C. material is selected from at least 1 material, or at least 2 Preferably, the volatile fragrance materials is present in an materials, or at least 3 materials, or at least 5 materials, or amount of from about 70 wt % to about 99.9 wt %, at least 7 materials as disclosed in Table 3. TABLE 3 Volatile Fragrance Materials CAS Vapor Pressure No. Number IUPAC Name Common Name** (Torr at 25° C.)* 1. 107-31-3 Formic acid, methyl ester Methyl Formate 732.OOOOOOOO 75-18-3 Methane, 1,1'-thiobis Dimethyl Sulfide 647.OOOOOOOO 1.0% In DEP 3. 141-78-6 Acetic acid ethyl ester Ethyl Acetate 112.OOOOOOOO 4. 105-37-3 Propanoic acid, ethyl Ethyl Propionate 44. SOOOOOOO ester 5. 110-19-0 Acetic acid, 2 Isobutyl Acetate 18.OOOOOOOO methylpropyl ester 6. 105-54-4 Butanoic acid, Ethyl Butyrate 13.90OOOOOO ethyl ester 7. 14765-30-1 1-Butanol Butyl Alcohol 8.52OOOOOO 8. 7452-79-1 Butanoic acid, 2- Ethyl-2-Methyl 7.8SOOOOOO methyl-, ethyl ester Butyrate
US 2016/0362631 A1 Dec. 15, 2016 31
TABLE 3-continued Volatile Fragrance Materials CAS Vapor Pressure No. Number IUPAC Name Common Name** (Torr at 25° C)* 441. 41199-2O-6 2-Naphthalenol, decahydro- Ambrinol O.OO140000 2.5,5-trimethyl 4.42 12262-03-2 indecanoic acid, 3- ISO Amyl O.OO140000 methylbutyl ester Undecylenate 443. 107-74-4 1,7-Octanediol, 3,7-dimethyl- Hydroxyol O.OO139000 444. 91-64-5 2H-1-Benzopyran-2-one Coumarin 445. 68901-32-6 1,3-Dioxolane. 2-6-methyl-8- Glycolierral (1-methylethyl) bicyclo[2.2.2 oct-5-en-2-yl)- 446. 68O39-44-1 Propanoic acid, 2,2-dimethyl-, Pivacyclene O.OO119000 3a,4,5,6,7,7a-hexahydro-4,7- methano-1H-inden-6-yl ester 447. 106-29-6 Butanoic acid, (2E)-3,7- Geranyl dimethyl-2,6-octadien-1-yl ester Butyrate 448. 5471-51-2 2-Butanone, 4-(4-hydroxyphenyl)- Raspberry ketone 449. 109-42-2 10-Undecenoic acid, butyl ester Butyl O.OO104000 Undecylenate *Vapor Pressures are acquired as described in the Test Methods Section. **Origin: Same as tor Table 2 hereinabove.
Test Methods work through the slides at that time point. Their assessments are recorded. In the Subsequent analysis, the data for 0120. The following assays set forth must be used in strength and character comparisons are drawn from the order that the invention described and claimed herein may independent assessments carried out at a given time point. be more fully understood. Only when using the difference scale below are any two products physically directly compared to each other. Panel Test Method 1: Determining Vapor Pressure ists are selected from individuals who are either trained to 0121. In order to determine the vapor pressure for the evaluate fragrances according to the scales below or who fragrance materials, go to the website https://scifinder.cas. have experience with fragrance evaluation in the industry. org/scifinder/view/scifinder/scifinderExplore.jsfand follow Typically, around 6 to 10 panelists are used to evaluate a these steps to acquire the vapor pressure. given product and its control. 0122 1. Input the CAS registry number for the particular (a) Fragrance Intensity: fragrance material. 0128 0123 2. Select the vapor pressure from the search results. I0129. The panelists are asked to give a score on a scale 0.124 3. Record the vapor pressure (given in Torr at 25° of 0 to 5 for perceived fragrance intensity according to the C.). odour intensity scale set out in Table 4 herein below. 0.125 SciFinder uses Advanced Chemistry Development (ACD/Labs) Software Version 1402). If the CAS number TABLE 4 for the particular fragrance material is unknown or does not Odour Intensity Scale exist, you can utilize the ACD/Labs reference program to directly determine the vapor pressure. Vapor Pressure is Score Fragrance Intensity expressed in 1 Torr, which is equal to 0.133 kilopascal (kPa). O None 1 Very Weak Test Method 2: Olfactory Tests 2 Weak 3 Moderate 0126. In order to show the effect of the substantially 4 Strong non-odorous fragrance fixatives on the perception of fra 5 Very Strong grance profile in a composition of the present invention, test compositions are made, as described in the Example section, and given to panelists to evaluate. O130 (b) Fragrance Character: 0127. At the testing facility, 50 uL samples of the com I0131 The panelists are asked to assess the fragrance positions and the controls are applied to glass slides and character in one of 2 ways: placed on a hot plate at 32° C. to represent skin temperature 0132) i) a score on a scale of 0 to 3 for the dominance for varying durations. It is important that glass slides of of particular characters that are relevant to that particu samples that are to be later compared are prepared at the lar fragrance, e.g.: fresh, green, watery, floral, rose, same time. The panelists are asked to evaluate the perceived muguet, fruity, apple, berry, citrus, creamy, woody, fragrance profile (intensity and/or character) of each glass balsamic, amber, musk just to name a few, according to slide sample at a given time-point. Slides are presented the odour grading scale set out in Table 5(i) herein coded so that their identity is not known by the panelists. below: Within a given time point panelists evaluate the slides in a 0.133 ii) a score on a scale of 1 to 5 for changes in the random order and are able to revisit their assessment as they perceived fragrance profile change for the test compo US 2016/0362631 A1 Dec. 15, 2016 32
sitions versus the controls according to the odour in Tables 18(d), 19(b) and 19(c). All of the ingredients grading scale set out in Table 5(ii) herein below. are admixed until evenly distributed in the test com positions. TABLE 5(i) 0.137 2. A control composition to the test composition described in 1 above, without the substantially non Character Dominance Odour Grading Scale odorous fragrance fixative, is made in a similar manner Score Fragrance Character Dominance to Step 1, except that the missing Substantially non odorous fragrance fixative is replaced by deionized O Not noticeable 1 Slight presence of the character water. Sample control compositions are provided in 2 Moderate presence of the character Tables 18(d), 19(b) and 19(c). 3 Dominance of the character 0.138. 3. An internal standard is needed to correct for variations of the amount of composition dispensed in the evaporation test as well as loss during the GC analysis. The internal standard has a vapor pressure of TABLE 5(ii) less than 0.001 Torr (0.000133 kPa) at 25° C. and is Character Difference Odour Grading Scale Soluble in the composition or fragrance material. A Suitable non-limiting example of internal standard is Score Fragrance Character Change triethyl citrate. The internal standard and fragrance 1 Fragrance character is unchanged, i.e., no difference between the material are admixed until evenly distributed at a level sample vs. the control. of 90 to 95 parts by weight of fragrance material and 2 Slight fragrance character change when compared directly with the control. the required amount of internal standard to reach 100 3 Moderate fragrance change but similar character to the control. parts. This mixture is then use to prepare the sample 4 Large difference in fragrance character from the control. compositions in Step 1 and 2. Alternatively, the internal 5 Total difference in the fragrance character from the control. standard and test or control composition are admixed until evenly distributed at a level of 99 to 99.75 parts 0134. The results of the panelists are averaged and then by weight of composition and the required amount of analysed using Analysis of Variance methods. The model internal standard to reach 100 parts. This resultant treats the Subject as a random effect and looks at the impact Solution is used in Subsequent steps. of product, time and the interaction between product and 0139 4. A hotplate is set to a temperature of 32° C. An time. From the analysis the least square means for the aluminium container, such as TA instrument TzeroTM product and time interaction are obtained. These means (as pan is placed on the hotplate. 20 uL of the test or control well as their confidence intervals) are then plotted to enable composition is introduced in the aluminium container comparisons between products at each time point. It should using a micropipette. Alternatively, the aluminium con be noted that the confidence levels plotted are intended as a tainer may be filled with the test or control composition guide, and not as a statistical comparison, as they do not take to its full capacity. The time at which this takes place into account that multiple testing has been performed. As is determined to be time Zero (i.e., T=0). Multiple well as a graphical assessment, statistical comparisons aluminium containers are prepared and left at the set between the two products at each of the time points are temperature for pre-determined periods of time. Such as performed with a Tukey correction for multiple compari for example 30 mins, 1 hr. 2 hrs, 3 hrs, 4 hrs, 5 hrs, 6 sons. The p-values for the product differences were obtained, hrs, 8 hrs and up to 12 hrs. with p-values.<0.05 indicating a statistical difference 0140. 5. The aluminium container is removed from the between the two products at 5% significance (or 95% hotplate at the end of the pre-determined time period confidence). and its content transferred into a 4 mL glass vial already containing 2 mL of highly volatile solvent, Such as high Test Method 3: Analytical Evaporation Tests purity ethanol or hexane. 0.141 6. The glass vial is mixed using a Heidolph multi 0135 The following test is carried out to demonstrate the REAX shaker, or equivalent, for 5 to 10 mins to extract improved or enhanced longevity of a fragrance profile of a the fragrance materials into the solvent phase. 1.5 mL. composition of the present invention vs. a control. In par of the resultant solution is transferred to a 2 mL GC ticular, the test measures the effect of a substantially non vial. odorous fragrance fixative on the evaporation rate of one or 0.142 7. The GC vial is analysed on an Agilent GC more fragrance materials (e.g., 10 PRMs) formulated in a system 6890 equipped with an autosampler, or equiva composition. The evaporation response of the fragrance lent. A GC column such as a DB-5MS, Rxi-5 SilMS materials to the fixative, as a function of time, is measured model, with a length of 30 m, an inner diameter of 0.25 through the use of gas chromatography ("GC). mm and a film thickness of 1 Lum is used. The GC 0.136 1. A test composition may comprise a Substan parameters are set to the values indicated as follows: tially non-odorous fragrance fixative (as disclosed in Table 1) with either: (i) a fragrance material (any one TABLE 5(iii) of the fragrance materials disclosed in Table 3) or (ii) a blend of fragrance materials from Table 3 (as dis GC Parameters closed as Fragrance Example 6 in Table 11). The test Injector temperature: 270° C. composition may also comprise high purity ethanol, Initial gas velocity: 30 to 40 cm/sec (for Helium as the carrier such as Hayman 100% EP/BP grade, and (optionally) gas) deionised water. Sample test compositions are provided US 2016/0362631 A1 Dec. 15, 2016 33
TABLE 5(iii)-continued 0.148. 3. The glass capillary is then removed from the well and inverted or transferred onto a stable surface or GC Parameters into a holder and allowed to evaporate at ambient Injection type: Split conditions for a set period of time. A windshield may Initial oven temperature: 50° C. for 1 min be used to reduce high air turbulence. Temperature ramp: 8° C. min 0.149 4. The glass capillary is then introduced into an Final oven temperature: 310° C. empty 20 mL HS vial, which is immediately closed with a PTFE cap. The time at which this takes place is 0.143 Gas chromatography with flame ionisation determined to be time T-initial (i.e., T=10 mins) detection (“FID) or with mass spectrometry (“MS) 0.150 5. Multiple glass capillaries are prepared in the can be used for the identification and quantification same way and left to evaporate at ambient temperature of aroma chemicals in the compositions. Either for pre-determined periods of time, such as for example detection system can be used in conjunction with 10, 15, 30 mins, 1 hr., 2 hrs, 3 hrs, 4 hrs, 5 hrs, and up GC. The column dimensions as well as GC settings to 6 hrs, before being introduced to the headspace vial described in this method, such as injector tempera and sealed. ture, carrier gas Velocity, temperature ramp and final 0151. 6. The HS vial is then analysed on an Agilent GC oven temperature can be adjusted to optimize the system 6890 equipped with a Gerstel MPS 2 autosam response of the fragrance material and internal stan pler, or equivalent, capable of performing SPME injec dard being monitored. The detection system settings, tions. ASPME fiber assembly DVB/CAR/PDMS (50/ such as FID gas flows and temperature or MS 30 Jum, 1 cm length) is required. AGC column Such as parameters, should be optimized by a trained analyst a DB-5MS, ZB-SMSi models, or equivalent phase, to enable the precise detection and quantification of with a length of 30 m, an inner diameter of 0.25 mm the analytes of interest. and a film thickness of 1 Lum is used. 0144 8. The peak area of the fragrance material and 0152 7. The SPME HS parameters are set to the values internal standard are recorded. The peak area ratio of indicated as follows: the fragrance material and the internal standard is calculated at each time point for each sample compo TABLE 5(iv) sition. The % loss of non-evaporated fragrance material remaining from T=0 is calculated at each time point for SPME Parameters each sample composition. The % of non-evaporated Incubation chamber temperature: 40° C. fragrance material from T=0 calculated. The % fra Incubation time: 20 mins grance material remaining in each composition is plot Agitation of sample 250 RPM ted to give an evaporation profile over time. This is Extraction time 5 mins done for both the test and control compositions. Sig Desorption time 2 mins nificance is determined by comparison of the evapora tion profile for the same fragrance material or same 0.153 8. The GC parameters are set to the values fragrance mixture in the test and control compositions. indicated as follows: Test Method 4: Analytical Headspace Tests TABLE 5(v) 0145 The following test is carried out to demonstrate the GC Parameters character retention over time of a fragrance composition of Injector temperature: 270° C. the present invention vs. a control. It is necessary for the test Initial gas velocity: 20 to 40 cm/sec (for Helium as the carrier and control samples to be run at approximately the same gas) time to ensure that ambient conditions are the same. The test Initial oven temperature: 45 C with 2 mins Hold Time measures theh presence off one or more ffragrance materialsterials iin Temperature ramp1: 1: 30°80° C. min the headspace formed in a sealed vial by the test composi- Temperature ramp 2: 8° C. min tion, after set evaporation times. The fragrance profile in the Final temperature: 300° C. headspace is measured at specific time points through the use of headspace (“HS) gas chromatography (“GC). 0154 Gas chromatography with flame ionization 0146 1. The test and control compositions as detection (“FID) or with mass spectrometry (“MS) described in the Example section are used for the can be used for the identification and quantification evaluation. of fragrance material in the compositions. Either 0147 2. Capillaries of about 2 cm to 3.5 cm, with one detection system can be used in conjunction with sealed end are cut from a Sigma Aldrich “StuartTM GC. The column dimensions as well as GC settings melting point tube' product code Z673269, or equiva described in this method, such as injector tempera lent. A suitable fixed volume chosen between 50 and ture, carrier gas Velocity, temperature ramp and final 200 uL of the composition is pipetted into the well of oven temperature can be adjusted to optimize the a WVR Tissue Culture 96 F well plate, or equivalent. response of the fragrance material being monitored. The sealed end of the glass capillary is dipped into the The detection system settings, such as FID gas flows filled well and left for at least 15 secs to wet the surface and temperature or MS parameters, should be opti of the glass. Care must be taken not to contact the glass mized by a trained analyst to enable the precise capillary with the sides of the well by maintaining it detection and identification of the analytes of inter straight and approximately in the center of the well. eSt. US 2016/0362631 A1 Dec. 15, 2016 34
0155 9. A qualitative assessment of the chromato TABLE 6 grams obtained is performed by comparing the peak height of the fragrance materials and overall chromato Fragrance Example 1 (Fresh Floral Accord - 10 wt % of Low Volatile gram at time T-10 mins to other time points. A dotted Fragrance Materials line is drawn around an estimated retention time where Vapor Pressure Parts fragrance materials with a vapour pressure of 0.001 Ingredients CAS Number (Torr at 25° C.) (wt %) Torr or less (0.000133 kPa or less) elute during the Benzyl acetate 140-11-4 O.1640 10.8 analysis. The difference between the peaks present at Linalool 78-70-6 O.O905 9.8 each measured time point for the test and control Phenethyl alcohol 60-12-8 O.O741 15.7 compositions provides evidence of the retention of the Indole 120-72-9 O.O298 1.O C-Terpineol 98-55-5 O.O283 2.9 character of the fragrance over time. Geranyl acetate 105-87-3 O.O2S6 4.9 0156 10. This test set-up is designed to enable the Cymal 103-95-7 O.OO881 5.9 collection of the headspace in a manner that does not Hydroxycitronellal 107-75-5 O.OO318 22.4 Saturate the SPME fiber. If the fiber is Saturated it does Majantol 103694-68-4 O.OO224 16.6 not provide an accurate analysis of the headspace Hexyl cinnamic 101-86-O O.OOO697 1O.O composition. Therefore the quantity of liquid and the aldehyde evaporation surface area are very different from those in the olfactive evaluation of the same samples. For this Total 1OOOO reason it is not possible to compare directly the evapo ration time frames used in the 2 experiments. It is expected that the evaporation profile is much faster in TABLE 7 this headspace experiments compared to the olfactive Fragrance Example 2 (Fresh Male Accord - 13.51 wt % of Low Volatile evaluations. Fragrance Materials EXAMPLES Vapor Pressure Parts Ingredients CAS Number (Torr at 25° C.) (wt %) 0157. The following examples are provided to further d-Limonene S989-27-5 1.54OOOO 1O.O illustrate the present invention and are not to be construed as Dihydromyrcenol 18479-58-8 O.166OOO 1O.O limitations of the present invention, as many variations of Boisiris 68845-OO-1 O.O13SOO 6.5 the present invention are possible without departing from its Canthoxal 5462-06-6 O.010200 8.0 spirit or scope. Helional 1205-17-0 O.OO27OO 1O.O Kephalis 36306-87-3 O.OO2690 2O.O Majantol 103694-68-4 O.002240 15.5 Example 1 Javanol (R) 1984O4-98-7 O.OOO902 S.O Galaxolide (R* 1222-05-S OOOO414 7.5 Isopropyl 110-27-O 7.5 Fragrance Oils Myristate 0158 Fragrance examples 1, 2, 3, 4b and 5b are provided below in Tables 6, 7, 8, 9 and 10, respectively, as non Total 1OOOO limiting examples of formulations of fragrance materials *Supplied at 50% in Isopropyl myristate. intended to form the fragrance component of the composi tions of the present invention. The exemplary formulations of the fragrance materials span the range from “simple TABLE 8 accords' (less than 10 fragrance materials) to "complex Fragrance Example 3 (Sweet Dream 18 Fragrance - 11.15 wt % of fragrances' (greater than 30 fragrance materials). Typically, Low Volatile Fragrance Materials full bodied fragrance compositions do not comprise less than about 30 fragrance materials. Vapor Pressure Parts 0159 Fragrance examples 4a and 5a provided in Table 9 Ingredients CAS Number (Torr at 25° C.) (wt %) and 10, respectively, below are examples of traditional Prenyl acetate 1191-16-8 3.990OOOOO O.100 Manzanate 392SS-32-8 2.91OOOOOO O.200 formulations of fragrance materials that fall outside the Hexyl acetate 42-92-7 1.390OOOOO O.700 Scope of the present invention. cis-3-Hexenyl 3681-71-8 1.22OOOOOO O.200 0160 Fragrance example 6 provided in Table 11 below as acetate Benzaldehyde OO-52-7 O.974OOOOO O.200 an example of a formulation of Volatile fragrance materials. Liffarome 67633-96-9 O.721 OOOOO O.1SO 0161 Fragrance examples 7 and 8 are provided in Tables Hexyl isobutyrate 2349-07-7 O.413OOOOO 0.055 12 and 13 below as examples of a formulation of fragrance Dihydromyrcenol 18479-58-8 O.166OOOOO 2.500 Benzyl acetate 40-11-4 O.164OOOOO O.700 materials intended to form the fragrance component that fall Linallyl acetate 15-95-7 O.116OOOOO 2.500 outside the scope of the present invention. Verdox 88-41-5 O.1O3OOOOO 4.OOO 0162 Fragrance examples 9 to 16 are provided in Tables Phenethyl alcohol 60-12-8 O.O741OOOO 8.OOO Rossitol 21.5231-33-7 O.O299OOOO 1...SOO 14 and 15 below as examples of formulations of fragrance alpha-Terpineol 98-55-S O.O283OOOO 1...SOO materials containing higher than 30 wt % of the low volatile Geranyl acetate OS-87-3 O.O2S6OOOO 1...SOO fragrance materials. Rhodinol 41-25-3 O.O197OOOO O.700 Givescone S7934-97-1 O.O171OOOO O.700 0163 Fragrance examples 17 and 18 are provided in Methyl anthranilate 34-20-3 O.O158OOOO O.OSO Tables 16 and 17 below as comparative samples of formu Ysamber K 1541.71-77-4 O.O147OOOO 1.OOO lations of fragrance materials intended to form the fragrance alpha-Ionone 27-41-3 O.O144OOOO 3.OOO component. US 2016/0362631 A1 Dec. 15, 2016
TABLE 8-continued TABLE 8-continued Fragrance Example 3 (Sweet Dream 18 Fragrance - 11.15 wt % of Fragrance Example 3 (Sweet Dream 18 Fragrance - 11.15 wt % of Low Volatile Fragrance Materials Low Volatile Fragrance Materials Vapor Pressure Parts Vapor Pressure Parts Ingredients CAS Number (Torr at 25° C.) (wt %) Ingredients CAS Number (Torr at 25° C.) (wt %) Citronellyl acetate 1SO-84-5 O.O137OOOO OSOO Cherry base O.200 cis-3-hexenyl-cis-3- 61444-38-0 O.O122OOOO O.200 Cassis base O.300 hexenoate Bergamot Oil 6.OOO Cinnamic alcohol 104-54-1 O.O117OOOO O.100 Prunella base O.SOO delta-damascone 57378-68-4 O.O1 O2OOOO O.200 Hexyl cinnamic 101-86-0 O.OOO697OO 1. SOO Citronellyloxyacetal 7492-67-3 O.OO967OOO O.100 aldehyde dehyde Sandalore 6S 113-99-7 O.OOO62SOO 3.OOO Cymal 103-95-7 O.OO881OOO OSOO Dupical 3O168-23-1 O.OOO44100 O.OOS Floralozone 67634-15-S O.OO808OOO O.100 Galaxolide (R) 1222-05-S O.OOO41400 1. SOO Ethylmethylphenylg 77-83-8 O.OOST1000 O.200 Ebanol 678O1-20-1 O.OOO281 OO 2.OOO lycidate Helvetolide 141773-73-1 O.OOOOS/90 2.OOO Florosa Q 63SOO-71-0 0.00557OOO 3.OOO Warm Milk base O.200 Ethyl linalool 10339-55-6 O.OOS2OOOO 6.400 Vanilla Absolute 2 O.100 Pivarose 67662-96-8 O.OO484OOO 2.500 Isopropyl Myristate 1. SOO Hydroxycitronellal 107-75-5 O.OO318OOO 7.500 Dipropylene Glycol 6,040 Methyl Ionone 7779-30-8 O.OO286OOO 4.OOO propy y - - gamma- 104-67-6 O.OO271OOO OSOO Undecalactone Total 100.00 Kephalis 36306-87-3 O.OO269000 S.OOO Ox Cashmeran 33704-61-9 O.OO269000 1.OOO supplied its in M. Magnolan 27606-09-3 O.OO2S1OOO 3.OOO Supplied at 50% in DIPG. Majantol 103694-68-4 O.OO224OOO 6.900 Proprietary bases that contain a mixture of perfume raw materials, judged to be of high yolatility for the purposes of calculating % of low volatility PRMs. Brahmanol 72O89-08-8 O.OO154OOO 3.OOO 'Natural oils or extracts that contain a mixture of perfume raw materials, judged to be of Coumarin 91-64-5 O.OO13OOOO OSOO high volatility for the purposes of calculating % of low volatility PRMs. Glycolierral 68901-32-6 O.OO121OOO O.100 5 ERs: that cent Ef plus ES judged to be of low Raspberry ketone, S471-51-2 O.OO106OOO O.100 WOI811Natural oilsO ore extractspurposes that of containcalculating a mixture Wo or lowof perfume volatill raw materials,S, judged to be of Top Mango base OSOO low volatility for the purposes of calculating % of low volatility PRMs.
TABLE 9 Fragrance Examples 4a and 4b ("Traditional Floral Magnifica" Example 4a - 37 wt % of Low Volatile Fragrance Materials and "Reduced Low Volatile Floral Magnifica" Example 4b - 13 wt % of Low Volatile Fragrance Materials Parts (wt % Example 4b CAS Vapor Pressure Example 4a (Reduced Ingredients Number (Torr at 25° C.) (Traditional) Low Volatile) Beta Gamma Hexenol 928-96-1 2.126OOO O.20 O.2O Cis 3 HexenylAcetate 3681-71-8 1.219 OOO O.30 O.30 Benzyl Acetate 140-11-4 O.164OOOOO 3.01 3.01 Liffarome 67633-96-9 O.721 OOO O.20 O.2O Ligustral Or Triplal 68039-49-6 O.S78OOO O.10 O.10 Methyl Pamplemousse 67674-46-8 O.214000 O.40 O4O d-Limonene S989-27-5 1.54OOOOOO 3.01 3.01 PhenylAcetaldehyde 122-78-1 O.368OOO O.OOO2 O.OOO2 Precyclemone B 52475-86-2 O.OO3810 O.20 O.2O Ethyl 24- 3O2S-30-7 O.OO9540 O.20 O.2O Decadienoate Ambronat 6790-58-5 O.OO9340 2.00 2.0 Alpha Damascone 24720-09-0 O.OO8300 O.04 O.O6 Citronellol 106-22-9 O.O32900 4.01 4.0 Cyclemax 7775-00-0 O.O182OO O.40 O4O Cyclo Galbanate 68901-15-S O.OO3230 O.10 O.10 Cymal 103-95-7 O.OO8810 O.90 1.5 Dimethyl Benzyl 1OO94-34-5 O.OO1680 O.SO OSO Carbinyl Butyrate Ethyl Linalool 10339-55-6 O.OOS200 7.23 12.04 Florol 63SOO-71-0 0.005570 6.43 10.7 Gamma Decalactone 7O6-14-9 O.OO852O O.20 O.2O Geraniol 106-24-1 O.O13300 3.01 S.O2 Geranyl Acetate 105-87-3 O.OO9760 2.01 2.0 Helional 1205-17-0 O.OO2700 2.41 4.0 Heliotropin 120-57-O O.O10400 O.20 O.2O Hivernal 173445-65-3 O.OO392OOO O.20 O.2O Hydroxycitronellal 107-75-5 O.OO318O 2.41 4.0 Ionone Beta 14901-07-6 O.OO3O8O O.24 O4O US 2016/0362631 A1 Dec. 15, 2016 36
TABLE 9-continued Fragrance Examples 4a and 4b ("Traditional Floral Magnifica" Example 4a - 37 wt % of Low Volatile Fragrance Materials and "Reduced Low Volatile Floral Magnifica" Example 4b - 13 wt % of Low Volatile Fragrance Materials Parts (wt % Example 4b CAS Vapor Pressure Example 4a (Reduced Ingredients Number (Torr at 25° C.) (Traditional) Low Volatile) Ionone Gamma 127-51-5 O.OO282O 1.81 3.01 Methyl Jasmal 18871-14-2 O.004340 S.O2 S.O2 Jasmolactone 32764-98-0 O.OO3SSO O.20 O.2O Linallyl Propionate 144-39-8 O.O26300 1.20 1.2O Magnolan 690304 27606-09-3 O.OO2S10 3.01 S.O2 Majantol 103694-68-4 O.OO2240 2.41 4.01 Phenyl Ethyl Alcohol 60-12-8 O.O74100 3.01 S.O2 Phenyl Hexanol SSO66-48-3 O.OO6370 3.61 6.02 Undecavertol 81782-77-6 O.O107OO 2.01 2.01 Vanillin 121-33-5 O.OO1940 O.10 O.10 cis-3-Hexenyl cis-3- 61444-38-0 O.O12200 O.10 O.10 Hexenoate Phenoxy Ethyl Iso 103-60-6 O.OOS62O OSO OSO Butyrate 5-Cyclohexadecen-1- 37609-25-9 OOOOO33 1.00 1.OO One Ambrettolide 28.645-51-4 OOOOOO1 1.00 1.OO Cis-3-Hexenyl 6S4OS-77-8 OOOO246 1.51 OSO Salicylate Delta Muscenone 63314-79-4 O.OOO16S 1.00 1.OO 96.2191 Hedione (R) HC 248S1-98-7 O.OOO710 1054 3.51 Iso-E Super (R) 54464-57-2 0.000538 10.54 3.51 Para Hydroxy Phenyl 5471-51-2 O.OO1060 O.20 O.2O Butanone Polysantol 107898-54-4 O.OOO117 OSO OSO
Total 1OO 100
TABLE 10 Fragrance Examples 5a and 5b ("Traditional Muguesia Magnifica" Example 5a - 37 wt % of Low Volatile Fragrance Materials and "Reduced Low Volatile Muguesia Magnifica" Example Sb - 13 Wt 90 of Low Volatile Fragrance Materials
Parts (wt % Example 5b CAS Vapor Pressure Example 5a (Reduced Ingredients Number (Torr at 25° C.) (Traditional) Low Volatile) Benzyl Alcohol OO-51-6 O.158OOO O.10 O.10 Methyl Phenyl Carbinyl 93-92-5 O.2O3OOO O.32 O40 Acetate d-Limonene S989-27-5 1.54OOOOOO 1.OO 1.00 Benzyl Acetate 40-11-4 O.304OOO 5.86 7.32 Beta Gamma Hexenol 928-96-1 2.126000 O4O O40 Cis 3 HexenylAcetate 3681-71-8 1.219000 O.2O O.20 Linallyl Acetate 15-95-7 O.077400 1.OO 1.00 Jasmal 18871-14-2 O.OO4340 3.21 4.01 Indol 20-72-9 O.O298OO O.10 O.10 Hydroxycitronellal O7-75-5 O.OO318O 3.21 4.01 Helional 1205-17-0 O.OO2700 4.01 S.O2 Geranyl Acetate OS-87-3 O.OO9760 3.21 4.01 Geraniol 06-24-1 O.O13300 4.01 S.O2 Florosa Q 63SOO-71-0 0.005570 O 9.03 Cinnamic Alcohol O4-54-1 O.OOST20 O.2O O.20 Cinnamic Aldehyde O4-55-2 O.O26SOOOO O.O6 O.O6 Cis Jasmone 488-10-8 O.O2O100 OSO OSO Citronellol O6-22-9 O.O32900 4.01 S.O1 Citronellyl Acetate SO-84-5 O.O13700 3.21 4.01 Citronellyl 7492-67-3 O.OO9670 O.10 O.10 Oxyacetaldehyde US 2016/0362631 A1 Dec. 15, 2016 37
TABLE 10-continued Fragrance Examples 5a and 5b ("Traditional Muguesia Magnifica" Example 5a - 37 wt % of Low Volatile Fragrance Materials and "Reduced Low Volatile Muguesia Magnifica" Example 5b - 13 wt % of Low Volatile Fragrance Materials
Parts (wt % Example 5b CAS Vapor Pressure Example 5a (Reduced Ingredients Number (Torr at 25° C.) (Traditional) Low Volatile) Cyclemax 7775-00-0 O.O182OO O.32 O40 Cyclo Galbanate 68901-15-S O.OO3230 O.20 O.20 Cymal 103-95-7 O.OO8810 1.61 2.01 Ethyl Linalool 10339-55-6 O.OOS200 8.04 10.03 Florhydral 12S109-85-S O.O2O700 O16 O.20 Majantol 103694-68-4 O.OO2240 3.21 4.01 Phenyl Ethyl Acetate 103-45-7 O.OS6400 O40 O40 Phenyl Ethyl Alcohol 60-12-8 O.O74100 1445 18.06 Ambrettolide 28.645-51-4 O.OOOOO1 1.00 1.OO Cis-3-Hexenyl 6S4OS-77-8 O.OOO246 1.00 O.SO Salicylate Benzyl Salicylate 118-58-1 O.OOO17SOO 16.61 2.51 Hedione (R) HC 248S1-98-7 O.OOO710 8.03 4.01 Iso-E Super (R) 54464-57-2 O.OOOS38 10.03 S.O2 PhenylAcetaldehyde 101-48-4 O.SS600OOO O.20 O.10 Dimethyl Acetal
Total 1OO 100
TABLE 11 TABLE 12-continued Fragrance Example 6 (10 Volatile Fragrance Materials) Fragrance Example 7 (Fresh Floral GF 6-7 Accord - 40.14 wt % of Low Volatile Fragrance Materials Vapor Pressure Parts Ingredients CAS Number (Torr at 25° C.) (wt %) Vapor Pressure Parts Tetra-Hydro 78-69-3 O.115 9.85 Ingredients CAS Number (Torr at 25° C.) (wt %) Linalool Terpinyl acetate 80-26-2 O.O392 12.21 E. OS Dimethyl Benzyl 151-05-3 O.O139 11.96 alpha-irone ar. Carbinyl Acetate Vanillin 121-33-5 O.OO1940 6.15 Dimethyl Benzyl 100-86-7 O.O88844 9.35 Dimethyl benzyl 1OO94-34-5 O.OO1680 1.54 Carbinol carbinyl butyrate Phenyl Ethyl 60-12-8 O.O74100 7.60 Methyl beta- 93-08-3 O.OOO957 O.77 alcohol naphthyl ketone Laevo Carvone 6485-40-1 O.O656 9.35 Methyl 24851-98-7 O.OOO710 30.60 Indole 120-72-9 O.O298 7.29 dihydrojasmonate Ethyl Safranate 3SO44-59-8 O.O266 12.09 Benzyl Salicylate 118-58-1 O.OOO175 7.69 Indocolore 22O6-94-2 O.O255 10.09 Polysantol 107898-54-4 O.OOO117 O.77 Eugenol 97-53-0 O.O104 1021 Lrg 201 4707-47-5 OOOOO29 O.31
Total 1OOOO Total 1OOOO
TABLE 12 TABLE 13 Fragrance Example 7 (Fresh Floral GF 6-7 Accord - 40.14 wt % of Low Fragrance Example 8 (Traditional Floral Accord - 54.00 wt % of Low Volatile Fragrance Materials Volatile Fragrance Materials Vapor Pressure Parts Vapor Pressure Parts Ingredients CAS Number (Torr at 25° C.) (wt %) Ingredients CAS Number (Torr at 25° C.) (wt %) Ligustral or 68039-49-6 O.S78OOO O.15 Benzyl acetate 140-11-4 O.1640 5.5 Triplal Linalool 78-70-6 O.O905 S.O Benzyl acetate 140-11-4 O.164OOO O.31 Phenethyl alcohol 60-12-8 O.O741 8.0 Verdox 88-41-5 O.1O3OOO 5.38 Indole 120-72-9 O.O298 O.S Phenethyl alcohol 60-12-8 O.O74100 1.54 C-Terpineol 98-55-5 O.O283 1.5 Indole 120-72-9 O.O298OO O.O2 Geranyl acetate 105-87-3 O.O2S6 2.5 Heliotropin 120-57-O O.O104OO 1.23 Cymal 103-95-7 O.OO881 3.0 gamma- 7O6-14-9 O.OO852O O.38 Hydroxycitronellal 107-75-5 O.OO318 11.5 Decalactone Majantol 103694-68-4 O.OO224 8.5 Florosa Q 63SOO-71-0 0.005570 15.38 Hexyl cinnamic 101-86-O O.OOO697 4.0 Ethyl linalool 10339-55-6 O.OOS2OO 26.15 aldehyde US 2016/0362631 A1 Dec. 15, 2016 38
TABLE 13-continued TABLE 1.5 Fragrance Example 8 (Traditional Floral Accord - 54.00 wt % of Low Volatile Fragrance Materials Fragrance Examples 13, 14, 15 and 16 (Traditional Muguesia Magnifica - Greater than 30 wt % of Low Volatile Fragrance Vapor Pressure Parts Materials) Ingredients CAS Number (Torr at 25° C.) (wt %) 808S iso gamma Super 681.SS-66-8 O.OOOS6S 12.SO Fragrance Fragrance Fragrance Fragrance Sandalore 6S 113-99-7 O.OOO625 18.75 Habanolide 111879-80-2 OOOOOO431 18.75 Example Example Example Example 13 14 15 16 Total 1OOOO Ingredients Weight % Weight % Weight % Weight %
Muguesia Magnifica 86.96 83.33 74.07 68.97 TABLE 1.4 Ethylene 4.35 4.17 3.70 6.90 Fragrance Examples 9, 10, 11 and 12 (Traditional Flora Magnifica - Brassylate Greater than 30 wt % of Low Volatile Fragrance Materials Methyl Dihydro 4.35 8.33 14.82 13.79 Jasmonate Fragrance Fragrance Fragrance Fragrance Iso-E Super (R) 4.35 4.17 7.41 10.35 Example Example Example Example 9 10 11 12 Ingredients Weight % Weight % Weight % Weight % Total 1OO 1OO 1OO 100 Flora Magnifica 86.96 83.33 74.07 68.97 Wt 96 Low Wolatile 45 47 53 56 Ethylene 4.35 4.167 3.704 6.90 Brassylate Fragrance Materials Methyl Dihydro 4.35 8.33 14.82 13.79 Jasmonate Fragrance Example 5a, Iso-E Super (R) 4.35 4.167 7.407 10.35 Total 1OO 1OO 100 100 0164. Fragrance example 17 (as disclosed in Table 16) is Wt 96 Low Wolatile 45 47 53 56 composed of 68.51 wt % of volatile fragrance materials and Fragrance Materials 31.49 wt % of low volatile fragrance materials, wherein the Fragrance Example 4a, wt % is relative to the total weight of the fragrance com ponent. TABLE 16
Fragrance Example 17 (Comparative Fragrance 1 - 31.49 wt % of Low Volatile Fragance Materials)
Amount
CAS Vapor Pressure Parts by Parts Ingredients Number (Torr at 25° C.) Weight (wt %)
Limonene S989-27-5 1541 2576 30.04 Cis-3-Hexenol 928-96-1 1.039 21 O.24 Zestover 78-70-6 0.578 1 O.O1 Linalol 78-70-6 O.O905 553 6.45 Aphermate (10% DIPG) 7 25225-08-S OO678 7 O.08 Cyclosal S35-86-4 O.O311 35 O41 Coranol 83926-73-2 O.O210 371 4.33 Sclareolate (R)* ' 319002-92-1 O.O196 630 7.35 3-Methoxy-7,7-dimethyl-10- 21 6970-21-7 O.O196 371 4.33 methylene-bicyclo[4.3.1 decane Cedramber 19870-74-8 O.O128 1 OSO 12.24 Ambrox (R* 6790-58-5 O.OO934 1 O.O1 Decal 7O6-14-9 O.OO852 21 O.24 Damascone Alpha (10% DIPG) 24720-09-0 O.OO830 9.1 O.11 (Methoxymethoxy)Cyclododecane 42604-12-6 O.00686 182 2.12 Lilial (R) 80-54-6 O.OO444 26 O.30 Y-Undecalactone 104-67-6 O.OO271 21 O.24 Calone (R* 3 28.940-11-6 O.OOO831 50 O.S8 Paradisone (R)* 24851-98-7 O.OOO710 1OOO 11.66 US 2016/0362631 A1 Dec. 15, 2016 39
TABLE 16-continued Fragrance Example 17 (Comparative Fragrance 1 - 31.49 wt % of Low Volatile Fragance Materials
Amount CAS Vapor Pressure Parts by Parts Ingredients Number (Torr at 25° C.) Weight (wt %) Galaxolide (R) (70% MIP Extra) 7 1222-05-5 O.OOO414 700 8.16 Exaltenone 14595-54-1 OOOOO964 950 11.08
Total 8575..10 100 wt % *origin: Firmenich SA (Geneva, Switzerland). Propyl (S)-2-(1,1-dimethylpropxy)propanoate. 2 8-Methoxy-2,6,6,8-tetramethyl-tricyclo5.3.1.0(1.5)undecane. 3 7-Methyl-2H4H-1,5-benzodioxepin-3-one. 4. 1-(3,3-dimethyl-1-cyclohexyl)ethyl formate; origin: International Flavors & Fragrances. 5 Methyl dihydrojasmonate. Linalool. 7 Fragrance materials added as dilutions in a non-volatile solvent. For the purposes of calculating the fragrance oil composition actual fragrance materials levels added are used.
0.165 Fragrance example 18 (as disclosed in Table 17) is composed of 90.63 wt % of volatile fragrance materials and 9.37 wt % of low volatile fragrance materials, wherein the wt % is relative to the total weight of the fragrance com ponent. TABLE 17 Fragrance Example 18 (Comparative Fragrance 2 - 9.37 wt % of Low Volatile Fragance Materials)
Amount
CAS Vapor Pressure Parts by Parts Ingredients Number (Torr at 25° C.) Weight (wt %)
D-Limonene S989-27-5 1540 SO.OO S.21 cis-3-Hexenol (10% in DPG) 928-96-1 1040 O.S O.OS Acetophenone (10% in DPG) ' 98-86-2 O.299 1.OO O.10 MethylphenylAcetate 101-41-7 O.176 1O.OO 1.04 Dihydromyrcenol 18479-58-8 O.166 SO.OO S.21 Benzyl acetate 140-11-4 O.164 6O.OO 6.25 Tetra-Hydro Linalool na O. 115 SO.OO S.21 n-Undecanal na O. 102 S.OO O.S2 Linalool 78-70-6 O.O905 40.OO 4.17 Phenylethyl Alcohol na 0.0559 24S.OO 25.53 Allyl amylglycolate 67634-OO-8 O.O4(OOO 2.OO O.21 (10% in DPG) Indole (10% in DPG) ' 120-72-9 O.O298O 1.OO O.10 Alpha-Terpineol 98-55-5 O.O2830 3O.OO 3.13 Diphenyl Oxide 101-84-8 O.O2230 S.OO O.S2 L-Citronellol 7540-51-4 O.O1830 8O.OO 8.34 Beta-Ionone 14901-07-6 O.O1690 S.OO O.S2 Alpha-Ionone 127-41-3 O.O1440 1S.OO 1.56 Dimethyl benzyl carbinyl acetate 151-05-3 O.O1390 3O.OO 3.13 Geraniol 106-24-1 O.O1330 40.OO 4.17 Nerol na O.O1330 2O.OO 2.08 Lilial (R) 80-54-6 O.OO444 6O.OO 6.25 Gamma-Undecalactone 104-67-6 O.OO271 1S.OO 1.56 Amyl salicylate 2OSO-08-0 O.OO144 2S.OO 2.61 Galaxolide (R) 1222-05-S O.OOO414 2O.OO 2.08 cis-3-Hexenyl salicylate 6S4OS-77-8 O.OOO246 2O.OO 2.08 Ethylene Brassylate 105-95-3 O.OOOOOOOO313 3O.OO 3.13 Styrolyl Acetate na na 2O.OO 2.08 US 2016/0362631 A1 Dec. 15, 2016 40
TABLE 17-continued Fragrance Example 18 (Comparative Fragrance 2 - 9.37 wt % of Low Volatile Fragance Materials
Amount CAS Vapor Pressure Parts by Parts Ingredients Number (Torr at 25° C.) Weight (wt %) Decenol trans-9 na na 1S.OO 1.56 Geranium oil na na 1S.OO 1.56
Total 959.S 100 wt % Benzenepropanal, 4-(1,1-dimethylethyl)-O-methyl-, *Natural oil that isjudged to be of moderate volatility for the purposes of calculating levels of the volatile fragrance materials, 3 Proprietary oil that is judged to be of moderate volatile for the purposes of calculating levels of the volatile fragrance materials, Fragrance materials added as dilutions in a non-volatilee solvent. For the purposes of calculating the fragrance gil composition actual fragrance materials levels added are used. Unknown oil that is judged to be of low volatility for the purposes of calculating levels of the volatile fragrance materials,
Example 2 Single Fragrance Material Compositions Containing Fragrance Oils and Substantially Non-Odorous Fragrance Fixatives 0166 Compositions A, C, E, G, I, K, M, O, Q, S, U. W. Y. AA, and CC are examples of compositions according to the present invention, made with single fragrance materials and the Substantially non-odorous fragrance fixatives, respectively. In parallel, control Compositions B, D, F. H. J. L. N. P. R. T. V. X, Z, BB, and DD are prepared without a Substantially non-odorous fragrance fixative as a control. They are prepared by admixture of the components in Tables 18(a) and 18(b), in the proportions indicated.
TABLE 18(a)
Single Fragrance Material Compositions
Single Fragrance Material Composition (wt %')
ngredients A B C D E F G H I J. K. L. M. N. O
Dimethyl Benzyl 1 1 — — — — — — 1 1 — — — — — Carbinol Eugenol 1 1 — — — — — — 1 1 — — — Phenylethyl — — — — 1 1 — — — — — — 1 1 — Alchol Fragrance A — — — — — — 1 1 — — — — — — 1 Piperonyl butoxide 2.2 O 2.0 O 2.2 O 0.5-5 () — — — — — — — Poly(PG)monobutyl — — — — — — — — 2.2 O 2.0 0 1.8 O 0.5-5 O ether Ethanol to 100
Wt % is relative to the total weight of the composition, *Can be any one of the single fragrance materials of Table 2 or 3. US 2016/0362631 A1 Dec. 15, 2016
TABLE 18(b) Single Fragrance Material Compositions Single Fragrance Material Composition (wt %'. Ingredients Q R S T U V W X Y. Z. AA BB CC DD Indole 1 1 — — — — — — 1 1 Eugenol — — 1 1 — — — — — — 1 1 Dimethyl — — — — 1 1 Benzyl Carbinol Phenylethyl — — — — — — 1 1 — — — — Alchol Triglycol 1.3 O.9 1.O 1.2 Ethanol To 100 Wt % is relative to the total weight of the composition,
0167 Composition EE is an example of a composition Example 3 according to the present invention, made with single fra grance material and the Substantially non-odorous fragrance Compositions Comprising Substantially fixative, respectively, that are particularly suited to olfactive Non-Odorous Fragrance Fixatives evaluation. In parallel, control Composition FF is prepared without a substantially non-odorous fragrance fixative as a 0169 Composition A1 is an example of a fragrance control. All the compositions are prepared by admixture of composition according to the present invention, made with the components in Table 18(c), in the proportions indicated. any of the fragrance examples 1-3, 4b, 5b and 18, respec tively. Composition B1 is an example of a fragrance com TABLE 18(c) position containing traditional or higher levels of low vola Single Fragrance Material Compositions tile fragrance materials, made with any of the fragrance examples 4a, 5a, and 7-17, respectively. In parallel, a control Single Fragrance Material Composition (wt %) composition C1 is prepared by replacing the different Sub Ingredients EE FF stantially non-odorous fragrance fixative by the same amount of deionized water. All of the compositions are Fragrance A? 1-7 1-7 Modulator 1-15.O O.O prepared by admixture of the components described in Table Ethanol to 100 19(a) in the proportions indicated. Wt % is relative to the total weight of the composition, TABLE 19(a) * Can be any one of the fragrance materials disclosed in Tables 2 and 3. Can be any one of the substantially non-odorous fragrance fixatives not already disclosed Fragrance Composition in Tables 18(a) and 18(b). Fragrance Composition 0168 Tables 18(d) provides test compositions compris ing the a single Volatile fragrance material (as disclosed in Table 3) with a substantially non-odorous fragrance fixative Ingredients A1 B1 C1 (as disclosed in Table 1) that are particularly suited to Fragrance A1 2-15 analytical measurements. All of the compositions are pre Fragrance B 2-15 Fragrance A1 or B 2-15 pared by admixture of the components described in Table Ethanol 60-99.99 18(d) in the proportions indicated. Butylated Hydroxy O-O.O7 Toluene TABLE 18(d) Modulator A O.1-20 O.1-20 Deionized water to 100.00 Single Volatile Fragrance Material Compositions Wt % is relative to the total weight of the composition, Test Composition Reference Composition * Can be any one of fragrance examples 1-3, 4b, 5b, and 18. Ingredients (wt % ) (wt % ) Can be any one of fragrance examples 4a, 5a, and 7-17. Can be any one of the substantially non-odorous fragrance fixative as disclosed in Table Volatile Fragrance Material 1.0-3.0 1.0-3.0 1. Triethyl citrate O.25 to 2.0 O.25 to 2.0 Ethanol 75.0 75.0 Fixative O.1-10.O O.O (0170 Tables 19(b) provides test compositions (MOD1 to Water qsp qSp MOD43) comprising the volatile fragrance formulation of fragrance example 6 (as disclosed in Table 11) with a Total 1OO.O 1OOO Substantially non-odorous fragrance fixative (as disclosed in Wt% is relative to the total weight of the composition, Table 1) that are particularly suited to analytical measure * Can be any one of the volatile fragrance material as disclosed in Table 3. ments. All of the compositions are prepared by admixture of Can be any one of the substantially non-odorous fragrance fixative as disclosed in Table 1. the components described in Table 19(b) in the proportions indicated. US 2016/0362631 A1 Dec. 15, 2016 42
TABLE 19(b) TABLE 20-continued Compositions comprising fragrance with 10 Volatile Body Spray Compositions Fragrance Materials CAS Compositions (wt % Test composition Reference composition (wt %) (wt %) Ingredients Number I II III IV Ingredients MOD 1 to 43 REF Dipropylene Glycol 25265-71-8 1S.OO 1S.OO 1S.OO Fragrance A? 7.0 7.0 Isopropyl Myristate 110-27-0 1.00 1.OO 1.00 Triethyl citrate O.25 to 1.0 O.25 to 1.0 Zinc 127-82-2 O.SO O.SO OSO Ethanol 75.O 75.0 Phenosulphonate Fixative 1S.O O.O Cavasol (R) W7 128446-36-6 1.OO Water qsp qSp methylated Beta-cyclodextrin Total 1OO.O 1OOO Fragrance 120 1.2O 1.20 1.20 Fragrance Fixative 2.60 2.60 2.60 2.60 Wt % is relative to the total weight of the composition, Propane 74-98-6 4.86 4.86 4.86 2 Fragrance Example 6 (as disclosed in Table 11). Isobutane 72-28-5 27.14 27.14, 27.14 Can be any one of the substantially non-odorous fragrance fixative no. 1-3, 6-10, 12-13, 1,1-Difluoroethane 75-37-6 8.00 35.00 8.OO 8.00 15-19, 21, 26-28, 32, 47,49-50, 52,63, 84, 101, 106, 121, 128, 130, 138,142,143,144, 151, 152, 159, 173, 180, and 189 as disclosed in Table 1. (HFC-152a) Total 1OO.OO 100.OO 100.OO 100.00 0171 Tables 19(c) provides test compositions compris ing the Volatile fragrance formulation of fragrance example wt % relative to the total weight of the composition, * Can be any one of Fragrances Examples 1, 2, 3, 4a, 4b, 5a, 5b, and 7-17. 6 (as disclosed in Table 11) with a substantially non-odorous Can be any one of the substantially non-odorous fragrance fixatives disclosed in Table fragrance fixative (as disclosed in Table 1) that are particu 1. larly Suited to analytical measurements. All of the compo 0173 Composition V, VI and VII are examples of body sitions are prepared by admixture of the components lotion compositions according to the present invention. They described in Table 19(c) in the proportions indicated. are prepared by admixture of the components as described in Table 21, in the proportions indicated. TABLE 19(c) Compositions comprising fragrance with 10 Volatile TABLE 21 Fragrance Materials Body Lotion Composition Test composition Reference composition Ingredients (wt % ) (wt % ) CAS Compositions (wt % Fragrance A O4-7.O O.4-7.O Ingredients Number V VI VII Triethyl citrate O.25 to 2.0 O.25 to 2.0 Water 7732-18-5 qSp qsp qsp Ethanol 75.O 75.0 100% 100% 100% Fixative 1-15.O O.O Trilon (R) B 64-O2-8 O.OS O.OS O.OS Water qsp qSp Carbopol (R) ETD 2050 9003-01-4 O.2 O.2 O.2 Pemulen TM TR1 9063-87-0 O.2 O.2 O.2 Total 1OO.O 1OOO Nexbase (R) 2008 68037-01-4 8 8 8 Wt% is relative to the total weight of the composition, Silicone V100 63148-62-9 6 6 6 2 Fragrance Example 6 (as disclosed in Table 11). Fragrance Fixative 3 3 3 Can be any one of the substantially non-odorous fragrance fixative no. 4-5, 11, 14, 20, Tris Amino TM Ultra 102-71-6 0.4 0.4 0.4 22-25, 29-31, 33-46, 48, 51, 53-62, 64-83, 85-100, 102-105, 107-120, 122-127, 129, Pur 131-137, 139-141, 145-150, 153-158, 160-172,174-179, 181-188, and 190 as disclosed in Fragrance 3 3 3 Table 1. Preservatives qs qs qs
Total 1OOOO 1OOOO 1OOOO Example 4 wt % relative to the total weight of the composition, *Can be any one of the Fragrances Examples 1, 2, 3, 4a, 4b, 5a, 5b, and 7-17. Can be any one of the substantially non-odorous fragrance fixatives disclosed in Table Exemplary Product Compositions 1. 0172 Compositions I, II, III and IV are examples of body Example 5 spray compositions according to the present invention. They are prepared by admixture of the components described in Olfactive Test Results Table 20, in the proportions indicated. 0.174 Compositions disclosed in Tables 18(a)-18(c), and 19(a) are applied to glass slides in accordance with the TABLE 20 protocol described in the Method Section and a panel of 6-11 experienced panelists evaluated the perceived fragrance Body Spray Compositions profile at initial time 0, then at various time points, typically CAS Compositions (wt % 1 hour, 2 hours, 3 hours, 4 hours and 6 hours post applica tion. Panelists are asked to score the compositions for the Ingredients Number I II III IV longevity on a scale of 0 to 5, wherein 0 represents a no Denatured Ethanol 64-17-5 39.7O 59.45 39.7O 39.70 fragrance is detected and 5 represents a very strong fra Water 7732-18-5 0.75 grance intensity is detected; and for fragrance profile fidelity on a scale of 0 to 3 wherein 0 represents not detectable and US 2016/0362631 A1 Dec. 15, 2016
3 represents it being the dominant character. The results of 0180 FIG. 5 shows the fragrance intensity profile of the panelists are then averaged and discussed below. Composition M as evaluated by 10 panelists, which com (0175 (a) Effects of the Substantially Non-Odorous Fra prises the Substantially non-odorous fragrance fixative Poly grance Fixatives on Single Fragrance Material Composi (PG)monobutyl ether, on the single fragrance material, tions phenethyl alcohol (PEA). Addition of the fixative (Poly(PG) 0176 FIG. 1 shows the fragrance intensity profile of monobutyl ether) maintains the intensity of the fragrance Composition A as evaluated by 10 panelists, which com material whilst the control, Composition N, in the absence of prises the Substantially non-odorous fragrance fixative Pip the Substantially non-odorous fragrance fixative, drops in eronyl butoxide, on the single fragrance material, Dimethyl fragrance intensity profile over the 6 hours. The substantially Benzyl Carbinol. Addition of the fixative maintains the non-odorous fragrance fixative acts to maintain the contin intensity of the fragrance material whilst the control, Com ued evaporation over time of the fragrance material. Statis position B, in the absence of the Substantially non-odorous tical analysis using the Tukey correction for multiple com fragrance fixative, drops in fragrance intensity profile over parisons confirms the statistically significant difference at 0 the 6 hours. The Substantially non-odorous fragrance fixa hours (p=0.0530) at 90% significance level (i.e., p<0.1) and tive acts to maintain the continued evaporation over time of at 1 hour (p<0.0034) and at 3 hours (p<0.0034) at 95% the fragrance material. Statistical analysis using the Tukey significance level (i.e., p<0.05). correction for multiple comparisons confirms the statisti 0181 FIG. 6 shows the fragrance intensity profile of cally significant difference at 1 hour (p=0.0061) at 95% Composition Q as evaluated by 11 panelists, which com significance level (i.e., p<0.05). prises the Substantially non-odorous fragrance fixative Tri 0177 FIG. 2 shows the fragrance intensity profile of glycol, on the single fragrance material Indole. Addition of Composition C as evaluated by 10 panelists, which com the fixative (Triglycol) maintains the intensity of the fra prises the Substantially non-odorous fragrance fixative Pip grance material whilst the control, Composition R, in the eronyl butoxide, on the single fragrance material, Eugenol. absence of the Substantially non-odorous fragrance fixative, Addition of the fixative (Piperonyl butoxide) maintains the drops in fragrance intensity profile over the 6 hours. The intensity of the fragrance material whilst the control, Com Substantially non-odorous fragrance fixative acts to maintain position D. in the absence of the Substantially non-odorous the continued evaporation over time of the fragrance mate fragrance fixative, drops in fragrance intensity profile over rial. Statistical analysis using the Tukey correction for the 6 hours. The Substantially non-odorous fragrance fixa multiple comparisons confirms the statistically significant tive acts to maintain the continued evaporation over time of difference at 1 hour (p<0.0014) at 95% significance level the fragrance material. Statistical analysis using the Tukey (i.e., p<0.05). correction for multiple comparisons confirms the statisti 0182 FIG. 7 shows the fragrance intensity profile of cally significant difference at 1 hour (p<0.0001) and at 3 Composition S as evaluated by 11 panelists, which com hours (p=0.0231) at 95% significance level (i.e., p<0.05). prises the Substantially non-odorous fragrance fixative Tri 0.178 FIG. 3 shows the fragrance intensity profile of glycol, on the single fragrance material Eugenol. Addition of Composition I as evaluated by 10 panelists, which com the fixative (Triglycol) maintains the intensity of the fra prises the Substantially non-odorous fragrance fixative Poly grance material whilst the control, Composition T. in the (PG)monobutyl ether, on the single fragrance material, Dim absence of the Substantially non-odorous fragrance fixative, ethyl Benzyl Carbinol. Addition of the fixative (Poly(PG) drops in fragrance intensity profile over the 6 hours. The monobutyl ether) maintains the intensity of the fragrance Substantially non-odorous fragrance fixative acts to maintain material whilst the control, Composition J, in the absence of the continued evaporation over time of the fragrance mate the Substantially non-odorous fragrance fixative, drops in rial. Statistical analysis using the Tukey correction for fragrance intensity profile over the 6 hours. The substantially multiple comparisons confirms the statistically significant non-odorous fragrance fixative acts to maintain the contin difference at 1 hour (p<0.0144) at 95% significance level ued evaporation over time of the fragrance material. Statis (i.e., p<0.05). tical analysis using the Tukey correction for multiple com 0183 (b) Effects of Substantially Non-Odorous Fra parisons confirms the statistically significant difference at 0 grance Fixatives on the Fragrance Profile Longevity of hours (p=0.0060) and 1 hour (p=0.0443) at 95% significance Compositions Having Reduced Levels of Low Volatile Fra level (i.e., p<0.05) and at 3 hours (p=0.0873) at 90% grance Materials (Between 10 to 30 wt % Relative to the significance (i.e., p<0.1). Total Weight of the Fragrance Component) Vs. Composi 0179 FIG. 4 shows the fragrance intensity profile of tions Having Traditional Levels of Low Volatile Fragrance Composition K as evaluated by 10 panelists, which com Materials (Greater than 30 wt.% Relative to the Total Weight prises the Substantially non-odorous fragrance fixative Poly of the Fragrance Component) and No Substantially Non (PG)monobutyl ether, on the single fragrance material, Odorous Fragrance Fixative Eugenol. Addition of the fixative (Poly(PG)monobutyl 0.184 Panelists are asked to score the compositions for ether) maintains the intensity of the fragrance material the intensity of the fragrance on a scale of 0 to 5, wherein whilst the control, Composition L, in the absence of the 0 represents no fragrance intensity is detected and 5 repre Substantially non-odorous fragrance fixative, drops in fra sents a very strong fragrance intensity is detected. The grance intensity profile over the 6 hours. The substantially results of the panel test are then averaged. The results show non-odorous fragrance fixative acts to maintain the contin the effect of the substantially non-odorous fragrance fixative ued evaporation over time of the fragrance material. Statis and reduced levels of low volatile fragrance materials for tical analysis using the Tukey correction for multiple com any one of the inventive Compositions A1 on fragrance parisons confirms the statistically significant difference at 1 profile longevity versus control Compositions C1 in the hour (p<0.0001), at 3 hours (p<0.0001) and at 6 hours absence of the Substantially non-odorous fragrance fixatives. (p=0.0067) at 95% significance level (i.e., p<0.05). Alternatively, the results show the effect of the substantially US 2016/0362631 A1 Dec. 15, 2016 44 non-odorous fragrance fixative and reduced levels of low plotted against the individual profile for the indole compo Volatile fragrance materials for any one of the inventive nent from the test composition containing the 10 PRMs Compositions A1 on fragrance profile longevity versus mixture of Table 11 with the substantially non-odorous traditional Compositions B1 in the presence of the substan fragrance fixatives. The error associated with the method is tially non-odorous fragrance fixative. determined by running replicate evaporation experiments on 0185. Fragrance profile longevity, particularly intensity the control composition. An average evaporation profile of of the characters attributable to the volatile fragrance mate the control composition as well as the 95% confidence rials, are maintained for up to at least 6 hours in the presence interval at each time point are calculated from the replicates. of the substantially non-odorous fragrance fixative whilst it (0191). It is useful to consider the difference (A) in the % drops in the absence of the Substantially non-odorous fra of remaining fragrance material between each of the test grance fixative. composition (MOD) and their respective control composi 0186 (c) Effects of the Substantially Non-Odorous Fra tion (REF) at each experimental time points (e.g., 30 mins, grance Fixatives on the Fragrance Profile Fidelity of Com 60 mins and 180 mins) to determine the effect of the positions Having Reduced Levels of Low Volatile Fragrance Substantially non-odorous fragrance fixative on the volatile Materials (Between 10 to 30 wt % Relative to the Total PRMs in a mixture. The difference (A) in the '% of remaining Weight of the Fragrance Component) Vs. Compositions of a given fragrance material is calculated as follows: Having Traditional Levels of Low Volatile Fragrance Mate A% remaining of given fragrance material in test rials (Greater than 30 wt % Relative to the Total Weight of composition (MOD)-% remaining of same fra the Fragrance Component) and No Substantially Non-Odor grance material in control composition (REF) ous Fragrance Fixative The difference (A) can then be plotted (data not shown) for 0187 Panelists are also asked to score the composition each of the perfume materials in the mixture at each of the for the fragrance profile fidelity. In particular, the panelists time points. For ease of reference, the applicant has sum are asked to score the dominance of the floral character marize the effect of the Substantially non-odorous fragrance attributable to the volatile fragrance materials on a scale of fixative on only one volatile fragrance component (e.g., 0 to 3 wherein 0 represents not detectable and 3 represents indole) of the mixture, to serve as a representative of all of it being the dominant character. The results of the panel test the volatile fragrance materials. are then averaged. The results show the effect of the sub (0192 (a) Effects of Tergitol(R) 15-S-7 on Composition stantially non-odorous fragrance fixative for the inventive Having Volatile Fragrance Materials Compositions A1 on fragrance profile fidelity versus control (0193 FIG. 8 shows the effect of the substantially non Compositions C1 in the absence of the substantially non odorous fragrance fixative Tergitol(R) 15-S-7 on the evapo odorous fragrance fixative. ration profile for a representative component (i.e., indole) of 0188 Fragrance profile fidelity are maintained by the the test composition (MOD1). With reference to FIG. 8, Substantially non-odorous fragrance fixative over time for up indole has a difference (A) of 14% after 30 mins, 24% after to 6 hours in the presence of the substantially non-odorous 60 mins, and 80% after 3 hours. Addition of the Tergitol(R) fragrance fixative whilst it drops in the absence of the 15-S-7 in the test composition (MOD1) maintains the con Substantially non-odorous fragrance fixative (data not centration of the volatile fragrance material indole from 0 shown). hour up to 3 hours whilst the control composition (REF), in the absence of Tergitol(R) 15-S-7, drops in fragrance concen Example 6 tration over the 3 hours. Thus, Tergitol(R) 15-S-7 acts to maintain the continued evaporation of the Volatile fragrance Analytical Evaporation Test Results material over time. Similar results are observed for the other 0189 Using the analytical evaporation Test Method 3, it Volatile fragrance materials in the mixture (data not shown). is possible to measure the amount of a Volatile fragrance (0194 (b) Effects of PPG-7-Buteth-10 on Composition material or each component of a perfume mixture that Having Volatile Fragrance Materials remains as the fragrance mixture evaporates. Test composi (0195 FIG. 9 shows the effect of the substantially non tions may comprise any one of the Volatile fragrance mate odorous fragrance fixative PPG-7-Buteth-10 on the evapo rial as disclosed in Table 3 and a substantially non-odorous ration profile for a representative component (i.e., indole) of fragrance fixative, as disclosed in Table 1. Alternatively, test the test composition (MOD2). With reference to FIG. 9, compositions may comprise a mixture of 10 volatile per indole has a difference (A) of 21% after 30 mins, 33% after fume materials, as disclosed in Table 11 (Fragrance Example 60 mins, and 80% after 3 hours. Addition of the Tergitol(R) 6), and a substantially non-odorous fragrance fixative, as in the test composition (MOD2) maintains the concentration disclosed in Table 1. Examples of suitable test compositions of the volatile fragrance material indole from 0 hour up to 3 include the compositions disclosed in Table 18(d), and hours whilst the control composition (REF), in the absence Compositions MOD1 to MOD43 in Table 19(b) and Com of PPG-7-Buteth-10, drops in fragrance concentration over positions in Table 19(c). The test compositions are intro the 3 hours. Thus, PPG-7-Buteth-10 acts to maintain the duced in the aluminum containers at the set temperature for continued evaporation of the volatile fragrance material over pre-determined periods of time in accordance with the time. Similar results are observed for the other volatile protocol described in Test Method 3. fragrance materials in the mixture (data not shown). (0190. For Compositions MOD1 to MOD43, indole is one (0196) (c) Effects of Nikkol PBC-33 on Composition of the components of the 10 PRMs mixture of Table 11. Having Volatile Fragrance Materials Control compositions containing the full 10 PRMs, or one (0.197 FIG. 10 shows the effect of the substantially non component (e.g., indole), without the Substantially non odorous fragrance fixative Nikkol PBC-33 on the evapora odorous fragrance fixative are run alongside the test com tion profile for a representative component (i.e., indole) of positions. The average profile for the control composition is the test composition (MOD3). With reference to FIG. 10, US 2016/0362631 A1 Dec. 15, 2016
indole has a difference (A) of 12% after 30 mins, 24% after ration profile for a representative component (i.e., indole) of 60 mins, and 76% after 3 hours. Addition of the Nikkol the test composition (MOD7). With reference to FIG. 14, PBC-33 in the test composition (MOD3) maintains the indole has a difference (A) of 18% after 30 mins, 32% after concentration of the volatile fragrance material indole from 60 mins, and 68% after 3 hours. Addition of the Cremo 0 hour up to 3 hours whilst the control composition (REF), phor R A 25 in the test composition (MOD7) maintains the in the absence of Nikkol PBC-33, drops in fragrance con concentration of the Volatile fragrance material indole from centration over the 3 hours. Thus, Nikkol PBC-33 acts to 0 hour up to 3 hours whilst the control composition (REF), maintain the continued evaporation of the Volatile fragrance in the absence of Cremophor R A 25, drops in fragrance material over time. Similar results are observed for the other concentration over the 3 hours. Thus, Cremophor R A 25 acts Volatile fragrance materials in the mixture (data not shown). to maintain the continued evaporation of the volatile fra (0198 (d) Effects of Neodol 45-7 Alcohol Ethoxylate on grance material over time. Similar results are observed for Composition Having Volatile Fragrance Materials the other volatile fragrance materials in the mixture (data not (0199 FIG. 11 shows the effect of the substantially non shown). odorous fragrance fixative Neodol 45-7 Alcohol Ethoxylate (0206 (h) Effects of Bio-Soft N91-8 on Composition on the evaporation profile for a representative component Having Volatile Fragrance Materials (i.e., indole) of the test composition (MOD4). With refer ence to FIG. 11, indole has a difference (A) of 15% after 30 0207 FIG. 15 shows the effect of the substantially non mins, 28% after 60 mins, and 76% after 3 hours. Addition of odorous fragrance fixative Bio-soft N91-8 on the evapora the Neodol 45-7 Alcohol Ethoxylate in the test composition tion profile for a representative component (i.e., indole) of (MOD4) maintains the concentration of the volatile fra the test composition (MOD8). With reference to FIG. 15, grance material indole from 0 hour up to 3 hours whilst the indole has a difference (A) of 11% after 30 mins, 25% after control composition (REF), in the absence of Neodol 45-7 60 mins, and 71% after 3 hours. Addition of the Bio-soft Alcohol Ethoxylate, drops in fragrance concentration over N91-8 in the test composition (MOD8) maintains the con the 3 hours. Thus, Neodol 45-7 Alcohol Ethoxylate acts to centration of the volatile fragrance material indole from 0 maintain the continued evaporation of the Volatile fragrance hour up to 3 hours whilst the control composition (REF), in material over time. Similar results are observed for the other the absence of Bio-soft N91-8, drops in fragrance concen Volatile fragrance materials in the mixture (data not shown). tration over the 3 hours. Thus, Bio-soft N91-8 acts to (0200 (e) Effects of Bio-Soft N25-7 on Composition maintain the continued evaporation of the Volatile fragrance Having Volatile Fragrance Materials material over time. Similar results are observed for the other 0201 FIG. 12 shows the effect of the substantially non volatile fragrance materials in the mixture (data not shown). odorous fragrance fixative Bio-soft N25-7 on the evapora (0208 (i) Effects of GenapolR) C-100 on Composition tion profile for a representative component (i.e., indole) of Having Volatile Fragrance Materials the test composition (MOD5). With reference to FIG. 12, (0209 FIG. 16 shows the effect of the substantially non indole has a difference (A) of 16% after 30 mins, 24% after odorous fragrance fixative Genapolr) C-100 on the evapo 60 mins, and 76% after 3 hours. Addition of the Bio-soft ration profile for a representative component (i.e., indole) of N25-7 in the test composition (MOD5) maintains the con the test composition (MOD9). With reference to FIG. 16, centration of the volatile fragrance material indole from 0 indole has a difference (A) of 13% after 30 mins, 28% after hour up to 3 hours whilst the control composition (REF), in 60 mins, and 72% after 3 hours. Addition of the Genapolr) the absence of Bio-soft N25-7, drops in fragrance concen C-100 in the test composition (MOD9) maintains the con tration over the 3 hours. Thus, Bio-soft N25-7 acts to centration of the volatile fragrance material indole from 0 maintain the continued evaporation of the Volatile fragrance hour up to 3 hours whilst the control composition (REF), in material over time. Similar results are observed for the other the absence of Genapolr C-100, drops in fragrance con Volatile fragrance materials in the mixture (data not shown). centration over the 3 hours. Thus, Genapolr) C-100 acts to (0202 (f) Effects of Bio-Soft N23-6.5 on Composition maintain the continued evaporation of the Volatile fragrance Having Volatile Fragrance Materials material over time. Similar results are observed for the other 0203 FIG. 13 shows the effect of the substantially non Volatile fragrance materials in the mixture (data not shown). odorous fragrance fixative Bio-soft N23-6.5 on the evapo ration profile for a representative component (i.e., indole) of 0210 (i) Effects of RhodasurfR LA 30 on Composition the test composition (MOD6). With reference to FIG. 13, Having Volatile Fragrance Materials indole has a difference (A) of 15% after 30 mins, 28% after 0211 FIG. 17 shows the effect of the substantially non 60 mins, and 77% after 3 hours. Addition of the Bio-soft odorous fragrance fixative RhodasurfR LA 30 on the evapo N23-6.5 in the test composition (MOD6) maintains the ration profile for a representative component (i.e., indole) of concentration of the volatile fragrance material indole from the test composition (MOD10). With reference to FIG. 17, 0 hour up to 3 hours whilst the control composition (REF), indole has a difference (A) of 15% after 30 mins, 28% after in the absence of Bio-soft N23-6.5, drops in fragrance 60 mins, and 75% after 3 hours. Addition of the Rhodasurf R concentration over the 3 hours. Thus, Bio-soft N23-6.5 acts LA 30 in the test composition (MOD10) maintains the to maintain the continued evaporation of the volatile fra concentration of the Volatile fragrance material indole from grance material over time. Similar results are observed for 0 hour up to 3 hours whilst the control composition (REF), the other volatile fragrance materials in the mixture (data not in the absence of RhodasurfR LA 30, drops in fragrance shown). concentration over the 3 hours. Thus, RhodasurfR LA 30 0204 (g) Effects of Cremophor R A 25 on Composition acts to maintain the continued evaporation of the volatile Having Volatile Fragrance Materials fragrance material over time. Similar results are observed for 0205 FIG. 14 shows the effect of the substantially non the other volatile fragrance materials in the mixture (data not odorous fragrance fixative Cremophor R A 25 on the evapo shown). US 2016/0362631 A1 Dec. 15, 2016 46
0212 (k) Effects of Poly(Ethylene Glycol) Methyl Ether continued evaporation of the volatile fragrance material over on Composition Having Volatile Fragrance Materials time. Similar results are observed for the other volatile 0213 FIG. 18 shows the effect of the substantially non fragrance materials in the mixture (data not shown). odorous fragrance fixative Poly(ethylene glycol) methyl 0220 (o) Effects of Pluronic(R) F-127 on Composition ether on the evaporation profile for a representative compo Having Volatile Fragrance Materials nent (i.e., indole) of the test composition (MOD11). With 0221 FIG. 22 shows the effect of the substantially non reference to FIG. 18, indole has a difference (A) of 15% after odorous fragrance fixative Pluronic R) F-127 on the evapo 30 mins, 31% after 60 mins, and 84% after 3 hours. Addition ration profile for a representative component (i.e., indole) of of the Poly(ethylene glycol) methyl ether in the test com the test composition (MOD15). With reference to FIG. 22, position (MOD11) maintains the concentration of the vola indole has a difference (A) of 7% after 30 mins, 20% after tile fragrance material indole from 0 hour up to 3 hours 60 mins, and 62% after 3 hours. Addition of the Pluronic(R) whilst the control composition (REF), in the absence of F-127 in the test composition (MOD15) maintains the Poly(ethylene glycol) methyl ether, drops in fragrance con concentration of the Volatile fragrance material indole from centration over the 3 hours. Thus, Poly(ethylene glycol) 0 hour up to 3 hours whilst the control composition (REF), methyl ether acts to maintain the continued evaporation of in the absence of Pluronic R) F-127, drops in fragrance the volatile fragrance material over time. Similar results are concentration over the 3 hours. Thus, Pluronic(R) F-127 acts observed for the other volatile fragrance materials in the to maintain the continued evaporation of the volatile fra mixture (data not shown). grance material over time. Similar results are observed for 0214) (1) Effects of ArlamolTM PS11E on Composition the other volatile fragrance materials in the mixture (data not Having Volatile Fragrance Materials shown). 0215 FIG. 19 shows the effect of the substantially non 0222 (p) Effects of Bio-Soft N1-5 on Composition Hav odorous fragrance fixative ArlamolTM PS11E on the evapo ing Volatile Fragrance Materials ration profile for a representative component (i.e., indole) of 0223 FIG. 23 shows the effect of the substantially non the test composition (MOD12). With reference to FIG. 19, odorous fragrance fixative Bio-soft N1-5 on the evaporation indole has a difference (A) of 9% after 30 mins, 23% after profile for a representative component (i.e., indole) of the 60 mins, and 59% after 3 hours. Addition of the ArlamolTM test composition (MOD16). With reference to FIG. 23, PS11E in the test composition (MOD12) maintains the indole has a difference (A) of 16% after 30 mins, 28% after concentration of the volatile fragrance material indole from 60 mins, and 80% after 3 hours. Addition of the Bio-soft 0 hour up to 3 hours whilst the control composition (REF), N1-5 in the test composition (MOD16) maintains the con in the absence of ArlamolTM PS11E, drops in fragrance centration of the volatile fragrance material indole from 0 concentration over the 3 hours. Thus, ArlamolTM PS11E acts hour up to 3 hours whilst the control composition (REF), in to maintain the continued evaporation of the volatile fra the absence of Bio-soft N1-5, drops in fragrance profile grance material over time. Similar results are observed for concentration over the 3 hours. Thus, Bio-soft N1-5 acts to the other volatile fragrance materials in the mixture (data not maintain the continued evaporation of the Volatile fragrance shown). material over time. Similar results are observed for the other 0216 (m) Effects of Brij(R) S100 on Composition Having Volatile fragrance materials in the mixture (data not shown). Volatile Fragrance Materials 0224 (q) Effects of Polyoxyethylene (10) Lauryl Ether 0217 FIG. 20 shows the effect of the substantially non on Composition Having Volatile Fragrance Materials odorous fragrance fixative Brij(R) S100 on the evaporation 0225 FIG. 24 shows the effect of the substantially non profile for a representative component (i.e., indole) of the odorous fragrance fixative Polyoxyethylene (10) lauryl ether test composition (MOD13). With reference to FIG. 20, on the evaporation profile for a representative component indole has a difference (A) of 7% after 30 mins, 18% after (i.e., indole) of the test composition (MOD17). With refer 60 mins, and 61% after 3 hours. Addition of the Brij(R) S100 ence to FIG. 24, indole has a difference (A) of 16% after 30 in the test composition (MOD13) maintains the concentra mins, 31% after 60 mins, and 80% after 3 hours. Addition of tion of the volatile fragrance material indole from 0 hour up the Polyoxyethylene (10) lauryl ether in the test composition to 3 hours whilst the control composition (REF), in the (MOD17) maintains the concentration of the volatile fra absence of Brij(R) S100, drops in fragrance concentration grance material indole from 0 hour up to 3 hours whilst the over the 3 hours. Thus, Brij(R) S100 acts to maintain the control composition (REF), in the absence of Polyoxyeth continued evaporation of the volatile fragrance material over ylene (10) lauryl ether, drops in fragrance concentration over time. Similar results are observed for the other volatile the 3 hours. Thus, Polyoxyethylene (10) lauryl ether acts to fragrance materials in the mixture (data not shown). maintain the continued evaporation of the Volatile fragrance 0218 (n) Effects of Brij(R) C-10 on Composition Hav material over time. Similar results are observed for the other ing Volatile Fragrance Materials Volatile fragrance materials in the mixture (data not shown). 0219 FIG. 21 shows the effect of the substantially non 0226 (r) Effects of ArlamolTM PC10 on Composition odorous fragrance fixative BrijR C-58 on the evaporation Having Volatile Fragrance Materials profile for a representative component (i.e., indole) of the 0227 FIG. 25 shows the effect of the substantially non test composition (MOD14). With reference to FIG. 21, odorous fragrance fixative ArlamolTM PC 10 on the evapo indole has a difference (A) of 9% after 30 mins, 25% after ration profile for a representative component (i.e., indole) of 60 mins, and 73% after 3 hours. Addition of the BrijR C-58 the test composition (MOD18). With reference to FIG. 25, in the test composition (MOD14) maintains the concentra indole has a difference (A) of 15% after 30 mins, 26% after tion of the volatile fragrance material indole from 0 hour up 60 mins, and 68% after 3 hours. Addition of the ArlamolTM to 3 hours whilst the control composition (REF), in the PC10 in the test composition (MOD18) maintains the con absence of BrijR C-58, drops in fragrance concentration centration of the volatile fragrance material indole from 0 over the 3 hours. Thus, BrijR C-58 acts to maintain the hour up to 3 hours whilst the control composition (REF), in US 2016/0362631 A1 Dec. 15, 2016 47 the absence of ArlamolTM PC10, drops in fragrance concen Diethylene glycol butyl ether in the test composition tration over the 3 hours. Thus, ArlamolTM PC10 acts to (MOD22) maintains the concentration of the volatile fra maintain the continued evaporation of the Volatile fragrance grance material indole from 0 hour up to 3 hours whilst the material over time. Similar results are observed for the other control composition (REF), in the absence of Diethylene Volatile fragrance materials in the mixture (data not shown). glycol butyl ether, drops in fragrance concentration over the 0228 (s) Effects of Poly(Ethylene Glycol) (18) Tridecyl 3 hours. Thus, Diethylene glycol butyl ether acts to maintain Ether on Composition Having Volatile Fragrance Materials the continued evaporation of the Volatile fragrance material 0229 FIG. 26 shows the effect of the substantially non over time. Similar results are observed for the other volatile odorous fragrance fixative Poly(ethylene glycol) (18) tride cyl ether on the evaporation profile for a representative fragrance materials in the mixture (data not shown). component (i.e., indole) of the test composition (MOD19). 0236 (w) Effects of Ethylene Glycol Monohexadecyl With reference to FIG. 26, indole has a difference (A) of 13% Ether on Composition Having Volatile Fragrance Materials after 30 mins, 25% after 60 mins, and 76% after 3 hours. 0237 FIG. 30 shows the effect of the substantially non Addition of the Poly(ethylene glycol) (18) tridecyl ether in odorous fragrance fixative Ethylene glycol monohexadecyl the test composition (MOD19) maintains the concentration ether on the evaporation profile for a representative compo of the volatile fragrance material indole from 0 hour up to 3 nent (i.e., indole) of the test composition (MOD23). With hours whilst the control composition (REF), in the absence reference to FIG.30, indole has a difference (A) of 10% after of Poly(ethylene glycol) (18) tridecyl ether, drops in fra 30 mins, 21% after 60 mins, and 77% after 3 hours. Addition grance concentration over the 3 hours. Thus, Poly(ethylene of the Ethylene glycol monohexadecyl ether in the test glycol) (18) tridecyl ether acts to maintain the continued composition (MOD23) maintains the concentration of the evaporation of the Volatile fragrance material over time. volatile fragrance material indole from 0 hour up to 3 hours Similar results are observed for the other volatile fragrance whilst the control composition (REF), in the absence of materials in the mixture (data not shown). Ethylene glycol monohexadecyl ether, drops in fragrance 0230 (t) Effects of ALFONIC(R) 10-8 Ethoxylate on concentration over the 3 hours. Thus, Ethylene glycol mono Composition Having Volatile Fragrance Materials hexadecyl ether acts to maintain the continued evaporation 0231 FIG. 27 shows the effect of the substantially non odorous fragrance fixative ALFONIC(R) 10-8 Ethoxylate on of the volatile fragrance material over time. Similar results the evaporation profile for a representative component (i.e., are observed for the other volatile fragrance materials in the indole) of the test composition (MOD20). With reference to mixture (data not shown). FIG. 27, indole has a difference (A) of 14% after 30 mins, 0238 (x) Effects of Poly(Propylene Glycol) Monobutyl 30% after 60 mins, and 79% after 3 hours. Addition of the Ether on Composition Having Volatile Fragrance Materials Poly(ethylene glycol) (18) tridecyl ether in the test compo 0239 FIG. 31 shows the effect of the substantially non sition (MOD20) maintains the concentration of the volatile odorous fragrance fixative Poly(propylene glycol) monobu fragrance material indole from 0 hour up to 3 hours whilst tyl ether on the evaporation profile for a representative the control composition (REF), in the absence of ALFO component (i.e., indole) of the test composition (MOD24). NIC(R) 10-8 Ethoxylate, drops in fragrance concentration With reference to FIG. 31, indole has a difference (A) of 11% over the 3 hours. Thus, ALFONIC(R) 10-8 Ethoxylate acts to after 30 mins, 24% after 60 mins, and 72% after 3 hours. maintain the continued evaporation of the Volatile fragrance Addition of the Poly(propylene glycol) monobutyl ether in material over time. Similar results are observed for the other the test composition (MOD24) maintains the concentration Volatile fragrance materials in the mixture (data not shown). of the volatile fragrance material indole from 0 hour up to 3 0232 (u) Effects of Brij(R) O20-SS on Composition Hav hours whilst the control composition (REF), in the absence ing Volatile Fragrance Materials of Poly(propylene glycol) monobutyl ether, drops in fra 0233 FIG. 28 shows the effect of the substantially non grance concentration over the 3 hours. Thus, Poly(propylene odorous fragrance fixative Brij(R) O20-SS on the evaporation glycol) monobutyl ether acts to maintain the continued profile for a representative component (i.e., indole) of the evaporation of the Volatile fragrance material over time. test composition (MOD21). With reference to FIG. 28, Similar results are observed for the other volatile fragrance indole has a difference (A) of 15% after 30 mins, 32% after materials in the mixture (data not shown). 60 mins, and 83% after 3 hours. Addition of the Brij(R) O20-SS in the test composition (MOD21) maintains the 0240 (y) Effects of DowanolTM TPnB on Composition concentration of the volatile fragrance material indole from Having Volatile Fragrance Materials 0 hour up to 3 hours whilst the control composition (REF), 0241 FIG. 32 shows the effect of the substantially non in the absence of Brij(RO20-SS, drops in fragrance concen odorous fragrance fixative DowanolTMTPnB on the evapo tration over the 3 hours. Thus, BrijR O20-SS acts to ration profile for a representative component (i.e., indole) of maintain the continued evaporation of the Volatile fragrance the test composition (MOD25). With reference to FIG. 32, material over time. Similar results are observed for the other indole has a difference (A) of 20% after 30 mins, 24% after Volatile fragrance materials in the mixture (data not shown). 60 mins, and 69% after 3 hours. Addition of the DowanolTM 0234 (v) Effects of Diethylene Glycol Butyl Ether on TPnB in the test composition (MOD25) maintains the con Composition Having Volatile Fragrance Materials centration of the volatile fragrance material indole from 0 0235 FIG. 29 shows the effect of the substantially non hour up to 3 hours whilst the control composition (REF), in odorous fragrance fixative Diethylene glycol butyl ether on the absence of DowanolTM TPnB, drops in fragrance con the evaporation profile for a representative component (i.e., centration over the 3 hours. Thus, DowanolTMTPnB acts to indole) of the test composition (MOD22). With reference to maintain the continued evaporation of the Volatile fragrance FIG. 29, indole has a difference (A) of 13% after 30 mins, material over time. Similar results are observed for the other 28% after 60 mins, and 72% after 3 hours. Addition of the Volatile fragrance materials in the mixture (data not shown). US 2016/0362631 A1 Dec. 15, 2016 48
0242 (Z) Effects of Tripropylene Glycol on Composition evaporation of the Volatile fragrance material over time. Having Volatile Fragrance Materials Similar results are observed for the other volatile fragrance 0243 FIG. 33 shows the effect of the substantially non materials in the mixture (data not shown). odorous fragrance fixative Tripropylene Glycol on the (0250 (dd) Effects of NIKKOL Hexaglyn 1-L on Com evaporation profile for a representative component (i.e., position Having Volatile Fragrance Materials indole) of the test composition (MOD26). With reference to (0251 FIG. 37 shows the effect of the substantially non FIG. 33, indole has a difference (A) of 11% after 30 mins, odorous fragrance fixative NIKKOL Hexaglyn 1-L on the 23% after 60 mins, and 69% after 3 hours. Addition of the evaporation profile for a representative component (i.e., Tripropylene Glycol in the test composition (MOD26) main indole) of the test composition (MOD30). With reference to tains the concentration of the volatile fragrance material FIG. 37, indole has a difference (A) of 10% after 30 mins, indole from 0 hour up to 3 hours whilst the control com 20% after 60 mins, and 62% after 3 hours. Addition of the position (REF), in the absence of Tripropylene Glycol, drops NIKKOL Hexaglyn 1-L in the test composition (MOD30) in fragrance concentration over the 3 hours. Thus, Tripro maintains the concentration of the volatile fragrance mate pylene Glycol acts to maintain the continued evaporation of rial indole from 0 hour up to 3 hours whilst the control the volatile fragrance material over time. Similar results are composition (REF), in the absence of NIKKOL Hexaglyn observed for the other volatile fragrance materials in the 1-L, drops in fragrance concentration over the 3 hours. Thus, mixture (data not shown). NIKKOL Hexaglyn 1-L acts to maintain the continued 0244 (aa) Effects of CithrolTM on Composition Having evaporation of the Volatile fragrance material over time. Volatile Fragrance Materials Similar results are observed for the other volatile fragrance 0245 FIG. 34 shows the effect of the substantially non materials in the mixture (data not shown). odorous fragrance fixative CithrolTM on the evaporation (0252) (ee) Effects of Emalex CS-10 on Composition profile for a representative component (i.e., indole) of the Having Volatile Fragrance Materials test composition (MOD27). With reference to FIG. 34, (0253 FIG. 38 shows the effect of the substantially non indole has a difference (A) of 12% after 30 mins, 22% after odorous fragrance fixative Emalex CS-10 on the evaporation 60 mins, and 68% after 3 hours. Addition of the CithrolTM in profile for a representative component (i.e., indole) of the the test composition (MOD27) maintains the concentration test composition (MOD31). With reference to FIG. 38, of the volatile fragrance material indole from 0 hour up to 3 indole has a difference (A) of 14% after 30 mins, 24% after hours whilst the control composition (REF), in the absence 60 mins, and 72% after 3 hours. Addition of the Emalex of CithrolTM, drops in fragrance concentration over the 3 CS-10 in the test composition (MOD31) maintains the hours. Thus, CithrolTM acts to maintain the continued evapo concentration of the Volatile fragrance material indole from ration of the volatile fragrance material over time. Similar 0 hour up to 3 hours whilst the control composition (REF), results are observed for the other volatile fragrance materials in the absence of Emalex CS-10, drops in fragrance con in the mixture (data not shown). centration over the 3 hours. Thus, Emalex CS-10 acts to 0246 (bb) Effects of Igepal(R) CO-630 on Composition maintain the continued evaporation of the Volatile fragrance Having Volatile Fragrance Materials material over time. Similar results are observed for the other 0247 FIG. 35 shows the effect of the substantially non Volatile fragrance materials in the mixture (data not shown). odorous fragrance fixative Igepal(R) CO-630 on the evapo (0254 (f) Effects of Dioctyl Ether on Composition Hav ration profile for a representative component (i.e., indole) of ing Volatile Fragrance Materials the test composition (MOD28). With reference to FIG. 35, (0255 FIG. 39 shows the effect of the substantially non indole has a difference (A) of 21% after 30 mins, 34% after odorous fragrance fixative Dioctyl ether on the evaporation 60 mins, and 85% after 3 hours. Addition of the Igepal(R) profile for a representative component (i.e., indole) of the CO-630 in the test composition (MOD28) maintains the test composition (MOD32). With reference to FIG. 39, concentration of the volatile fragrance material indole from indole has a difference (A) of 7% after 30 mins, 14% after 0 hour up to 3 hours whilst the control composition (REF), 60 mins, and 40% after 3 hours. Addition of the Dioctyl in the absence of Igepal(R) CO-630, drops in fragrance ether in the test composition (MOD32) maintains the con concentration over the 3 hours. Thus, Igepal(R) CO-630 acts centration of the volatile fragrance material indole from 0 to maintain the continued evaporation of the volatile fra hour up to 3 hours whilst the control composition (REF), in grance material over time. Similar results are observed for the absence of Dioctyl ether, drops in fragrance concentra the other volatile fragrance materials in the mixture (data not tion over the 3 hours. Thus, Dioctyl ether acts to maintain shown). the continued evaporation of the Volatile fragrance material 0248 (cc) Effects of Nikkol Decaglyn 3-OV on Compo over time. Similar results are observed for the other volatile sition Having Volatile Fragrance Materials fragrance materials in the mixture (data not shown). 0249 FIG. 36 shows the effect of the substantially non 0256 (gg) Effects of Jeecol CA-10 on Composition Hav odorous fragrance fixative Nikkol Decaglyn 3-OV on the ing Volatile Fragrance Materials evaporation profile for a representative component (i.e., (0257 FIG. 40 shows the effect of the substantially non indole) of the test composition (MOD29). With reference to odorous fragrance fixative Jeecol CA-10 on the evaporation FIG. 36, indole has a difference (A) of 12% after 30 mins, profile for a representative component (i.e., indole) of the 23% after 60 mins, and 62% after 3 hours. Addition of the test composition (MOD33). With reference to FIG. 40, Nikkol Decaglyn 3-OV in the test composition (MOD29) indole has a difference (A) of 13% after 30 mins, 29% after maintains the concentration of the Volatile fragrance mate 60 mins, and 77% after 3 hours. Addition of the Jeecol rial indole from 0 hour up to 3 hours whilst the control CA-10 in the test composition (MOD33) maintains the composition (REF), in the absence of Nikkol Decaglyn concentration of the Volatile fragrance material indole from 3-OV. drops in fragrance concentration over the 3 hours. 0 hour up to 3 hours whilst the control composition (REF), Thus, Nikkol Decaglyn 3-OV acts to maintain the continued in the absence of Jeecol CA-10, drops in fragrance concen US 2016/0362631 A1 Dec. 15, 2016 49 tration over the 3 hours. Thus, Jeecol CA-10 acts to maintain concentration of the Volatile fragrance material indole from the continued evaporation of the Volatile fragrance material 0 hour up to 3 hours whilst the control composition (REF), over time. Similar results are observed for the other volatile in the absence of Glycerol ethoxylate, drops in fragrance fragrance materials in the mixture (data not shown). concentration over the 3 hours. Thus, Glycerol ethoxylate 0258 (hh) Effects of Steareth-10 on Composition Having acts to maintain the continued evaporation of the volatile Volatile Fragrance Materials fragrance material over time. Similar results are observed for 0259 FIG. 41 shows the effect of the substantially non the other volatile fragrance materials in the mixture (data not odorous fragrance fixative Steareth-10 on the evaporation shown). profile for a representative component (i.e., indole) of the test composition (MOD34). With reference to FIG. 41, 0266 (11) Effects of Hexaethylene Glycol Monohexade indole has a difference (A) of 12% after 30 mins, 26% after cyl Ether on Composition Having Volatile Fragrance Mate 60 mins, and 72% after 3 hours. Addition of the Steareth-10 rials in the test composition (MOD34) maintains the concentra 0267 FIG. 45 shows the effect of the substantially non tion of the volatile fragrance material indole from 0 hour up odorous fragrance fixative Hexaethylene glycol monohexa to 3 hours whilst the control composition (REF), in the decyl ether on the evaporation profile for a representative absence of Steareth-10, drops in fragrance concentration component (i.e., indole) of the test composition (MOD38). over the 3 hours. Thus, Steareth-10 acts to maintain the With reference to FIG. 45, indole has a difference (A) of 19% continued evaporation of the volatile fragrance material over after 30 mins, 29% after 60 mins, and 77% after 3 hours. time. Similar results are observed for the other volatile Addition of the Hexaethylene glycol monohexadecyl ether fragrance materials in the mixture (data not shown). in the test composition (MOD38) maintains the concentra 0260 (ii) Effects of Nonaethylene Glycol Monododecyl tion of the volatile fragrance material indole from 0 hour up Ether on Composition Having Volatile Fragrance Materials to 3 hours whilst the control composition (REF), in the 0261 FIG. 42 shows the effect of the substantially non absence of Hexaethylene glycol monohexadecyl ether, drops odorous fragrance fixative Nonaethylene glycol monodode in fragrance concentration over the 3 hours. Thus, Hexaeth cyl ether on the evaporation profile for a representative ylene glycol monohexadecyl ether acts to maintain the component (i.e., indole) of the test composition (MOD35). continued evaporation of the volatile fragrance material over With reference to FIG. 42, indole has a difference (A) of 17% time. Similar results are observed for the other volatile after 30 mins, 31% after 60 mins, and 78% after 3 hours. Addition of the Nonaethylene glycol monododecyl ether in fragrance materials in the mixture (data not shown). the test composition (MOD35) maintains the concentration 0268 (mm) Effects of AquaflexTM XL-30 on Composi of the volatile fragrance material indole from 0 hour up to 3 tion Having Volatile Fragrance Materials hours whilst the control composition (REF), in the absence 0269 FIG. 46 shows the effect of the substantially non of Nonaethylene glycol monododecyl ether, drops in fra odorous fragrance fixative AquaflexTMXL-30 on the evapo grance concentration over the 3 hours. Thus, Nonaethylene ration profile for a representative component (i.e., indole) of glycol monododecyl ether acts to maintain the continued the test composition (MOD39). With reference to FIG. 46, evaporation of the Volatile fragrance material over time. indole has a difference (A) of 4% after 30 mins, 20% after Similar results are observed for the other volatile fragrance 60 mins, and 60% after 3 hours. Addition of the AquaflexTM materials in the mixture (data not shown). XL-30 in the test composition (MOD39) maintains the 0262 (ii) Effects of Glycerol Propoxylate on Composi concentration of the Volatile fragrance material indole from tion Having Volatile Fragrance Materials 0 hour up to 3 hours whilst the control composition (REF), 0263 FIG. 43 shows the effect of the substantially non in the absence of AquaflexTM XL-30, drops in fragrance odorous fragrance fixative Glycerol propoxylate on the concentration over the 3 hours. Thus, AquaflexTM XL-30 evaporation profile for a representative component (i.e., acts to maintain the continued evaporation of the volatile indole) of the test composition (MOD36). With reference to fragrance material over time. Similar results are observed for FIG. 43, indole has a difference (A) of 14% after 30 mins, the other volatile fragrance materials in the mixture (data not 28% after 60 mins, and 71% after 3 hours. Addition of the shown). Glycerol propoxylate in the test composition (MOD36) maintains the concentration of the Volatile fragrance mate 0270 (nn) Effects of Piperonyl Butoxide on Composition rial indole from 0 hour up to 3 hours whilst the control Having Volatile Fragrance Materials composition (REF), in the absence of Glycerol propoxylate, (0271 FIG. 47 shows the effect of the substantially non drops in fragrance concentration over the 3 hours. Thus, odorous fragrance fixative Piperonyl Butoxide on the evapo Glycerol propoxylate acts to maintain the continued evapo ration profile for a representative component (i.e., indole) of ration of the volatile fragrance material over time. Similar the test composition (MOD40). With reference to FIG. 47, results are observed for the other volatile fragrance materials indole has a difference (A) of 6% after 30 mins, 18% after in the mixture (data not shown). 60 mins, and 58% after 3 hours. Addition of the Piperonyl 0264 (kk) Effects of Glycerol Ethoxylate on Composi Butoxide in the test composition (MOD40) maintains the tion Having Volatile Fragrance Materials concentration of the Volatile fragrance material indole from 0265 FIG. 44 shows the effect of the substantially non 0 hour up to 3 hours whilst the control composition (REF), odorous fragrance fixative Glycerol ethoxylate on the evapo in the absence of Piperonyl Butoxide, drops in fragrance ration profile for a representative component (i.e., indole) of concentration over the 3 hours. Thus, Piperonyl Butoxide the test composition (MOD37). With reference to FIG. 44, acts to maintain the continued evaporation of the volatile indole has a difference (A) of 12% after 30 mins, 29% after fragrance material over time. Similar results are observed for 60 mins, and 80% after 3 hours. Addition of the Glycerol the other volatile fragrance materials in the mixture (data not ethoxylate in the test composition (MOD37) maintains the shown). US 2016/0362631 A1 Dec. 15, 2016 50
0272 (oo) Effects of Diphenhydramine HCl on Compo profile in the headspace are measured at specific time points sition Having Volatile Fragrance Materials through the use of headspace gas chromatography. (0273 FIG. 48 shows the effect of the substantially non (0279 (a) Effects of the Substantially Non-Odorous Fra odorous fragrance fixative Diphenhydramine HC1 on the grance Fixatives on Character Retention of Compositions evaporation profile for a representative component (i.e., Having Reduced Levels of Low Volatile Fragrance Materi indole) of the test composition (MOD41). With reference to als (Between 10 to 30 wt.% Relative to the Total Weight of FIG. 48, indole has a difference (A) of 11% after 30 mins, the Fragrance Component) Vs. Compositions Having Tra 23% after 60 mins, and 70% after 3 hours. Addition of the ditional Levels of Low Volatile Fragrance Materials (Greater Diphenhydramine HCl in the test composition (MOD41) than 30 wt % Relative to the Total Weight of the Fragrance maintains the concentration of the Volatile fragrance mate Component) rial indole from 0 hour up to 3 hours whilst the control 0280. The test demonstrates the character retention over composition (REF), in the absence of Diphenhydramine time of a fragrance composition. The results show the effect HCl, drops in fragrance concentration over the 3 hours. of the Substantially non-odorous fragrance fixative and Thus, Diphenhydramine HCl acts to maintain the continued reduced levels of low volatile fragrance materials for any evaporation of the Volatile fragrance material over time. one of the inventive Compositions A1 on fragrance profile Similar results are observed for the other volatile fragrance longevity versus control Compositions C1 in the absence of materials in the mixture (data not shown). the substantially non-odorous fixative. Alternatively, results (0274 (pp) Effect of Di(Propylene Glycol) Propyl Ether show the effect of the substantially non-odorous fragrance on Composition Having Volatile Fragrance Materials fixative and reduced levels of low volatile fragrance mate (0275 FIG. 49 shows the effect of the substantially non rials for any one of the inventive Compositions A1 on odorous fragrance fixative Di(propylene glycol) propyl ether fragrance profile longevity versus traditional Compositions on the evaporation profile for a representative component B1 in the presence of the substantially non-odorous fra (i.e., indole) of the test composition (MOD42). With refer grance fixative. Fragrance profile fidelity, particularly char ence to FIG. 49, indole has a difference (A) of 8% after 30 acters attributable to the volatile fragrance materials are mins, 21% after 60 mins, and 50% after 3 hours. Addition of maintained for up to at least 1 hour in the presence of the the DiCpropylene glycol) propyl ether in the test composition Substantially non-odorous fragrance fixative whilst it drops (MOD42) maintains the concentration of the volatile fra in the absence of the Substantially non-odorous fragrance grance material indole from 0 hour up to 3 hours whilst the fixative. control composition (REF), in the absence of Di(propylene 0281. It should be understood that every maximum glycol) propyl ether, drops in fragrance concentration over numerical limitation given throughout this specification the 3 hours. Thus, Di(propylene glycol) propyl ether acts to includes every lower numerical limitation, as if such lower maintain the continued evaporation of the Volatile fragrance numerical limitations were expressly written herein. Every material over time. Similar results are observed for the other minimum numerical limitation given throughout this speci Volatile fragrance materials in the mixture (data not shown). fication will include every higher numerical limitation, as if 0276 (qq) Effects of Poly(Melamine-Co-Formaldehyde) Such higher numerical limitations were expressly written Methylated on Composition Having a Volatile Fragrance herein. Every numerical range given throughout this speci Materials fication will include every narrower numerical range that (0277 FIG. 50 shows the effect of the substantially non falls within Such broader numerical range, as if such nar odorous fragrance fixative Poly(melamine-co-formalde rower numerical. hyde) methylated on the evaporation profile for a represen 0282. The dimensions and values disclosed herein are not tative component (i.e., indole) of the test composition to be understood as being strictly limited to the exact (MOD43). With reference to FIG.50, indole has a difference numerical values recited. Instead, unless otherwise speci (A) of 9% after 30 mins, 20% after 60 mins, and 62% after fied, each Such dimension is intended to mean both the 3 hours. Addition of the Poly(melamine-co-formaldehyde) recited value and a functionally equivalent range Surround methylated in the test composition (MOD43) maintains the ing that value. For example, a dimension disclosed as “40 concentration of the volatile fragrance material indole from mm is intended to mean “about 40 mm.” 0 hour up to 3 hours whilst the control composition (REF), 0283 Every document cited herein, including any cross in the absence of Poly(melamine-co-formaldehyde) methyl referenced or related patent or application and any patent ated, drops in fragrance concentration over the 3 hours. application or patent to which this application claims prior Thus, Poly(melamine-co-formaldehyde) methylated acts to ity or benefit thereof, is hereby incorporated herein by maintain the continued evaporation of the Volatile fragrance reference in its entirety unless expressly excluded or other material over time. Similar results are observed for the other wise limited. The citation of any document is not an admis Volatile fragrance materials in the mixture (data not shown). sion that it is prior art with respect to any invention disclosed or claimed herein or that it alone, or in any combination with Example 7 any other reference or references, teaches, Suggests or discloses any such invention. Further, to the extent that any Analytical Headspace Test Results meaning or definition of a term in this document conflicts with any meaning or definition of the same term in a 0278. Using the analytical headspace Test Method 4, it is document incorporated by reference, the meaning or defi possible to demonstrate the character retention over time of nition assigned to that term in this document shall govern. a perfume mixture of a fragrance composition of the present 0284 While particular embodiments of the present invention vs. a control. Compositions disclosed in Table invention have been illustrated and described, it would be 19(a) are added to sealed vials in accordance with the obvious to those skilled in the art that various other changes procotol described in the Method Section, and the fragrance and modifications can be made without departing from the US 2016/0362631 A1 Dec. 15, 2016
spirit and scope of the invention. It is therefore intended to group of Volatile Fragrance Materials 1-449, IUPAC Names, cover in the appended claims all Such changes and modifi of Table 3 and mixtures thereof. cations that are within the Scope of this invention. 8. The composition according to claim 7, wherein the What is claimed is: Volatile fragrance material is selected from the group of 1. A composition comprising: Table 3 Volatile Fragrance Materials 4, 6, 18, 54, 60, 77,92, (i) a fragrance component present in an amount of from 105, 107, 119, 122, 134, 138, 141, 144, 148, 152, 155, 158, about 0.04 wt % to about 30 wt %, relative to the total 167, 173, 175, 176, 182, 186, 189, 193, 195, 196, 202, 205, weight of the composition; and 206, 207,210, 212, 225, 235, 238,243, 245, 257, 271, 273, (ii) at least one substantially non-odorous fragrance fixa 274, 279-280, 282, 285, 289, 293, 297, 302, 305-306, 314, tive from the group consisting of the materials in Table 315, 318, 354-355, 410, 416, and mixtures thereof. 1, wherein the Substantially non-odorous fragrance 9. The composition according to claim 6, wherein the fixative is present in the amount of from about 0.1 wt Volatile fragrance material is selected from the group con % to about 20 wt %, relative to the total weight of the sisting of: composition. (f) a high volatile fragrance material having a vapor 2. The composition according to claim 1, wherein: pressure greater than 0.1 Torr (0.0133 kPa) at 25°C., (i) the fragrance component is present from about 0.04 wit present in an amount of from about 1 wt % to about 30 % to about 30 wt %, relative to the total weight of wt %, relative to the total weight of the fragrance composition, and wherein the fragrance component component; comprises: (g) a moderate volatile fragrance material having a vapor (a) at least one low volatile fragrance material having pressure in the range of 0.1 Torr (0.0133 kPa) to 0.001 a vapor pressure less than 0.001 Torr (0.000133 kPa) Torr (0.000133 kPa) at 25°C., present in an amount of at 25° C.; and from about 40 wt % to about 80 wt %, relative to the (b) the low volatile fragrance material is present in an total weight of the fragrance component; and amount of less than about 30 wt %, relative to the (h) mixtures thereof. total weight of the fragrance component; and 10. The composition according to claim 1, further com (ii) at least one substantially non-odorous fragrance fixa prising a volatile solvent present in the amount of from about tive present in the amount of from about 0.1 wt % to 10 wt % to about 90 wt %, relative to the total weight of the about 20 wt %, relative to the total weight of the composition, and wherein the solvent is a branch or composition. unbranched C to Co alkyl, akenyl or alkynyl group having 3. The composition according to claim 2, wherein the low at least one alcohol moiety. Volatile fragrance material is present in an amount of from 11. The composition according to claim 1, wherein the about 10 wt % to about 30 wt %, relative to the total weight composition is a fine fragrance composition, preferably in of the fragrance component. the form of a perfume concentrate, a perfume, a parfum, an 4. The composition according to claim 2, wherein the low eau de toilette, an eau de parfum or a cologne. Volatile fragrance material is selected from at least 1 mate 12. The composition according to claim 1, wherein the rial, or at least 2 materials, or at least 3 materials from the composition is in the form of a body splash or a body spray. group of Low Volatile Fragrance Materials 1-111. IUPAC 13. The composition according to claim 1, wherein the Names, of Table 2 and mixtures thereof. Substantially non-odorous fragrance fixative and fragrance 5. The composition according to claim 4, wherein the low component are present in a weight ratio from about 10:1 to Volatile fragrance material is selected from the group of about 1:10. Table 2 Low Volatile Fragrance Materials 1, 4-6, 8, 12-16, 14. The composition according to claim 1, wherein the 18, 22-28, 31, 34-37, 41, 45, 47, 52-55, 57, 60, 61, 63, 65, 68, 69-73, 75, 78,80, 83-84, 89, 94, 99, 102, 104, 106-108, Substantially non-odorous fragrance fixative is selected from and mixtures thereof. the group consisting of Table 1 substantially non-odorous 6. The composition according to claim 2, wherein: fragrance fixatives 1-190, 191 and mixtures thereof. (i) the fragrance component further comprising one or 15. A method of modifying or enhancing the odour more volatile fragrance materials, wherein: properties of a Substrate, comprising contacting or treating (c) the Volatile fragrance material has a vapor pressure the Substrate with a composition according to claim 1. greater than or equal to 0.001 Torr (0.000133 kPa) at 16. A substantially non-odorous fragrance fixative for 250 C. fragrance materials, wherein the Substantially non-odorous (d) the Volatile fragrance material is present in an fragrance fixative comprises at least one material selected amount of from about 70 wt % to about 99.9 wt %, from the group consisting of the materials in Table 1. relative to the total weight of the fragrance compo 17. A perfuming consumer product or article comprising nent; and a composition according to claim 1, wherein the perfuming (e) mixtures thereof. consumer product is selected from the group consisting of a 7. The composition according to claim 6, wherein the fabric care product, an air care product or a home care Volatile fragrance material is selected from at least 1 mate product. rial, or at least 3 materials, or at least 5 materials from the