(12) Patent Application Publication (10) Pub. No.: US 2010/0143274 A1 Deshayes Et Al

US 2010.0143274A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0143274 A1 Deshayes et al. (43) Pub. Date: Jun. 10, 2010

(54) USE OF AMINES AND AMIDES FOR THE (86). PCT No.: PCT/EP2008/052336 STABILIZATION OF ORGANIC MCRONIZED UV ABSORBERS S371 (c)(1), (2), (4) Date: Jan. 21, 2010 (75) Inventors: Cyrille Deshayes, Rosenau (FR): (30) Foreign Application Priority Data Thomas Ehlis, Freiburg (DE); Julie Grumelard, Huningue (FR) Mar. 7, 2007 (EP) ...... O7103670.1 Publication Classification Correspondence Address: BASF Performance Products LLC (51) Int. Cl. Patent Department A6IR 8/35 (2006.01) 540 White Plains Road, P.O. Box 2005 A61O 1704 (2006.01) Tarrytown, NY 10591 (US) (52) U.S. Cl...... 424/59 (57) ABSTRACT (73) Assignee: CIBA CORPORATION, Disclosed is the use of amines and amides for the stabilization TARRYTOWN, NY (US) of a cosmetic composition comprising: (a) an organic micron ized UV absorber selected from a benzophenone derivative (21) Appl. No.: 12/529,573 and (b) a dibenzoylmethane derivative. The use of the amines and amides results in the stabilization of the end-product (22) PCT Filed: Feb. 27, 2008 formulations. US 2010/0143274 A1 Jun. 10, 2010

USE OF AMNES AND AMIDES FOR THE STABILIZATION OF ORGANIC MICRONIZED UV ABSORBERS (1a) (CH2)2 -k s 0001. The present invention relates to a method of stabili (CH2)2 Zation of organic micronized UV absorbers, specific cosmetic compositions and the use of these cosmetic composition for wherein preventing the human hair or skin from the harmful effect of 0014 n is a number from 1 to 3: UV radiation 0015 when n is 3, 0002 Cosmetic compositions comprising micronized 0016 R is an alkantriyl radical; amino substituted hydroxyphenylbenzophenone derivatives 0017 when n is 4, (as described for example in WO 2004/052837) and Butyl 0018 R is an alkanetetrayl radical; methoxydibenzoylmethane (AVobenzone) represent very 0019 A is —O—; or N(Rs)—; and effectual UV absorber compositions. 0020 Rs is hydrogen; C-C alkyl; or hydroxy-C- 0003. However, mixing together these specific UV actives Calkyl. results in the formation of new and larger scaled crystals 0021 C-Coalkyl denotes a linear or branched, unsubsti and/or particles. tuted or Substituted alkyl group such as, for example, methyl, 0004. This crystallization affects the efficacy of the UV ethyl, propyl, isopropyl. n-butyl, n-hexyl, cyclohexyl, n-de filter combination and the sensory aspect of the end-product cyl, n-dodecyl. noctadecyl, eicosyl, methoxyethyl, ethox 0005 Surprisingly it has been found that the crystalliza ypropyl, 2-ethylhexyl, hydroxyethyl, chloropropyl N,N-di tion can be slowed, limited and/or prevented by the use of ethylaminopropyl, cyanoethyl, phenethyl, benzyl, p-tert amines, amides, alkanolamides and more preferably alkano butylphenethyl, p-tert-octylphenoxyethyl, 3-(2,4-di-tert lamines in the micronized product or within the end-product amylphenoxy)-propyl. ethoxycarbonylmethyl-2-(2- formulation. As a result, a stabilization of the end-product hydroxyethoxy)ethyl or 2-furylethyl. formulation is achieved. 0022 C-Coalkenyl is for example allyl, methallyl, iso 0006. Therefore, the present invention refers to the use of propenyl, 2-butenyl, 3-butenyl, isobutenyl, n-penta-2,4-di amines and amides for the Stabilization of a cosmetic com enyl, 3-methyl-but-2-enyl, n-oct-2-enyl, n-dodec-2-enyl, iso position comprising dodecenyl, n-dodec-2-enyl or n-octadec-4-enyl. (a) an organic micronized UV absorber selected from a ben 0023 C-Cocycloalkyl is for example cyclopropyl, Zophenone derivative and cyclobutyl, cyclopentyl, cycloheptyl, cyclooctyl, cyclononyl (b) a dibenzoylmethane derivative. or cyclodecyl and preferably cyclohexyl. These radicals may be substituted, for example by one or more or equal or differ 0007. The benzophenone UV absorbers preferably corre ent C-C alkyl radicals, preferably by methyl, and/or spond to formula hydroxy. If cycloalkyl radicals are substituted by one or more radicals, they are preferably substituted by one, two or four, (1) preferably by one or two equal or radicals. O 0024 C-Cocycloalkenyl is for example cyclopropenyl, OH O A R3, cyclobutenyl, cyclopentenyl, cycloheptenyl, cycloocentyl, cyclononenyl or cyclodecenyl and preferably cyclohexenyl. R v N These radicals may be substituted with one or more equal or different C-C alkyl radical, preferably with methyl, and/or Nt hydroxy. If cycloalkenyl radicals are substituted with one or R 2 111 more radicals they are preferably substituted with one, two, three or four, preferably with one or two equal or different radicals. wherein 0025 Hydroxy-substituted C-C alkyl groups are for 0008 R and R independently from each other are: example hydroxymethyl, hydroxyethyl, hydroxypropyl. C-Coalkyl, C-Coalkenyl: Cs-Cocycloalkyl: hydroxybutyl or hydroxypenty1. Cs-Cocycloalkenyl; or RandR together with the linking 0026. An alkylene radical is preferably a C-C alkylene nitrogen atom form a 5- or 6-membered heterocyclic ring; radical, like for example methylene, ethylene, propylene, 0009 n is a number from 1 to 4: butylene, hexylene or octylene. 0010 when n=1, 0027. The alkylene radicals may optionally be substituted 0011 R is a saturated or unsaturated heterocyclic radical; by one or more C-Csalkyl radicals. hydroxy-C-C-alkyl, cyclohexyl optionally substituted 0028. If R and R are heterocyclic radicals, these com with one or more C-C alkyl; phenyl optionally substituted prise one, two, three or four equal or different ring hetero with a heterocyclic radical, aminocarbonyl or atoms. Special preference is given to heterocycles which con C-Csalkylcarboxy; tain one, two or three, especially one or two, identical or 0012 when n is 2, different hetero atoms. The heterocycles may be mono- or 0013 R is an alkylene-, cycloalkylene alkenylene orphe poly-cyclic, for example mono-, bi- or tri-cyclic. They are nylene radical which is optionally interrupted by —O—: preferably mono- or bicyclic, especially monocyclic. The —NH-; a carbonyl- or carboxy group; a radical of for rings preferably contain 5, 6 or 7 ring members. Examples of mula *—CH2—C=C CH * or R together with A monocyclic and bicyclic heterocyclic systems from which forms a bivalent radical of the formula radicals occurring in the compounds of formula (1) or (2) may US 2010/0143274 A1 Jun. 10, 2010

be derived are, for example, pyrrol, furan, thiophene, imida 0055 R is a radical of formula Zole, pyrazole, 1,2,3-triazole, 1,2,4-triazole, pyridine, pyridazine, pyrimidine, pyrazine, pyran, thiopyran, 1.4-diox ane, 1.2-oxazine, 1.3-oxazine, 1,4-oxazine, indole, ben Zothiophene, benzofuran, pyrrolidine, piperidine, piperazine, (1b) morpholine and thiomorpholine. 0029 Preference is given to compounds of formula (1), wherein 0030) RandR independently from each other are hydro gen; C1-Coalkyl, C2-Coalkenyl: Cs-Cocycloalkyl, wherein Cs-Cocycloalkenyl; or RandR together with the linking nitrogen atom form a 5- or 6-membered heterocyclic ring; 0056 R is hydrogen; or C-C alkyl. 0031 n is a number from 1 to 4: 0057. If n is 2, 0032 when n is 1, 0058 R is preferably a C-C alkylene radical, most 0033 R is a saturated or unsaturated heterocyclic radical; preferably a C-Csalkylene radical. hydroxy-C-C-alkyl: Cyclohexyl substituted with one or 0059 Mostly preferred are compounds of formula (1), more C-C alkyl; wherein 0034 when n is 2, 0035 R is an alkylene-, cycloalkylene- or alkenylene 0060 R is a radical of formula—CH2—(CH), CH radical which is optionally interrupted by a carbonyl- or ck. carboxy group; 0036) when n is 3, 0037 R is an alkantriyl radical; when n is 4. 0038 R is an alkanetetrayl radical; 0039 A is O—; or - N(R)-; and : ci-O)-cis- *: 0040 Rs is hydrogen; C-C alkyl; or hydroxy-C- Csalkyl. CH3 : N CH2 0041. Of preferred interest are compounds of formula (1), : ci-Hen- *: Nan- ne. wherein 0042 R and R are C-Coalkyl, preferably C-C alkyl; CH3 and most preferably ethyl. 0043 Preferably R and R in formula (1) have the same '" | t definition. : ci- C-O- cha-i-cis 0044) If in formula (1) n is 1, compounds are preferred, CH3 CH3 wherein 0045 R is a saturated or unsaturated heterocyclic radical, most preferably a Saturated heterocyclic radical. 0061 r is 0 or 1; and 0046 Among these compounds are those preferred, 0062 q is a number from 0 to 5. wherein 0063. If in formula (1) n is 3, 0047 R is a monocyclic radical of 5, 6 or 7 ring members with one or more heteroatoms, preferably wherein 0064 R is preferably a radical of formula 0048 R is morpholinyl; piperazinyl; piperidyl; pyrazo lidinyl; imidazolidinyl; or pyrrolidinyl. 0049. When n is 1 further compounds of formula (1) are : (1c) of interest wherein 0050 R is an unsaturated heterocyclic radical, preferably *-CH-CH-(CH2)-CH,- a polycyclic radical. (1d) 0051 Most preferred are compounds of formula (1), wherein 0052 R is a radical of formula number : CH-CH. or

(1a) : (1e)

* -CH-CH and 0053 Rs is polycyclic heteroaromatic radical with one or 2 heteroatoms. and 0054 Of preferred interest are compounds of formula (1), 0065 p is a number from 0 to 3. wherein 0.066 R. R. and A are defined as in formula (1). US 2010/0143274 A1 Jun. 10, 2010

0067. If informula (1) n is 4, 0077 R is a C-C alkylene radical; or R together with A 0068 R is a radical of formula forms a bivalent radical of the formula

N N : : l \ / *-C-: or * cis--cis : CH 0078 Preferred are also compounds of formula

0069. R. R. and A are defined as in formula (1). (4) 0070 Preferred compounds of the present invention cor respond to formula Rin - R2

HO (2) rC O O O R-A O OH OH O A

NN R2 A wherein R2 0071 RandR independently from each other are hydro gen; or C-C alkyl: 0072 A is NH; or - O -; and wherein 0073 R is a saturated or unsaturated heterocyclic radical. 0079 RandR independently from each other are hydro 0074. Furthermore compounds of the present invention gen; or C-C alkyl; are preferred which correspond to formula 0080 A is NH; or - O : I0081 R is

(3) O O OH O A-R-A O OH : CH-CH-(CH2)-CH-* or

R n N O O O O N1 R1, A v R R

wherein 0075 RandR independently from each other are hydro gen; or C-C alkyl; and 0076 A is NH; or - O -; and I0082 p is a number from 0 to 3. US 2010/0143274 A1 Jun. 10, 2010

0083. Furthermore, compounds of formula

(5)

are preferred, wherein 0084 R is a radical of formula

: l : C *; or * cis--cis : CH

: and I0085 R. R. and A are defined as in formula (1). I0086 Exemplified compounds of the present invention are of formulae

(HPB1) (HPB2) H N

S O

1n O O H US 2010/0143274 A1 Jun. 10, 2010

-continued (HPB3) OH O O 'nu-1N1 n-1\ O O

(HPB4)

(HPB5)

(HPB6) (HPB7) US 2010/0143274 A1 Jun. 10, 2010

-continued (HPB8) (HPB9) - NS2 - OH O H H

1S C'.O O OH O O N O - 1n - c'ò 2 (HPB10) corp (HPB11) Ho-( ) Ho-( )

(HPB12)

- SS - O ( ) O US 2010/0143274 A1 Jun. 10, 2010 7

-continued HPB13 O O ( ) OH O

1n N1 - O ( ) O O

(HPB14)

O O O

O O 1N- N ro-( ) -\

(HPB15)

OH O O OH SSO 1.O O 't - OCO N

rN US 2010/0143274 A1 Jun. 10, 2010 8

-continued

(HPB16)

(HPB17)

(HPB18)

(HPB20)

(HPB21) US 2010/0143274 A1 Jun. 10, 2010

-continued (HPB22)

1a. N 5's (HPB23)

O O O OH

1n N O O O ( ) - O

N r (HPB24)

C.OH O O O OS.C. O O OH O X O OH O O OH

- CS t N US 2010/0143274 A1 Jun. 10, 2010 10

-continued (HPB25) (HPB26)

OH O O orxon. OH O O ON-O O O OH s

(HPB27) O 1N1)- O OH O O OH

1n r and (HPB28) O O1nean- O O OH OH O

1n 1n - N

0087. The compounds of formula (1) may be prepared 0093 Useful anionic, non-ionic or amphoteric surfactants according to known methods as described for example in are disclosed below in the sections entitled “specific dispers EP-1046,391. ing agents. 0088 Sparingly soluble organic compounds which are 0094 Preferred useful grinding aids for an aqueous dis used in the present invention are present in the micronized persion are anionic surfactants with a HLB (Hydrophile state. They may be prepared by any known process Suitable Lipophile Balance) value higher than 8, more preferably for the preparation of microparticles, for example wet-mill higher than 10. ing, wet-kneading, spray-drying from a suitable solvent, by 0.095 Any conventionally usable anionic, non-ionic or expansion according to the RESS process (Rapid Expansion amphoteric Surfactants can be used as dispersing agents. Such of Supercritical Solutions) of supercritical fluids (e.g. CO, Surfactant systems may comprise for example: carboxylic by reprecipitation from Suitable solvents, including Super acids and their salts: alkaline soap of sodium, potassium and critical fluids (GASR process-Gas Anti-Solvent Recrystalli ammonium, metallic Soap of calcium or magnesium, organic sation/PCA process-Precipitation with Compressed Anti basis soap Such as Lauric, myristic, palmitic, Stearic and oleic Solvents). acid etc., alkyl phosphates or phosphoric acid esters, acid 0089. As milling apparatus for the preparation of the spar phosphate, diethanolamine phosphate, potassium cetyl phos ingly soluble micronized organic compounds there may be phate, ethoxylated carboxylic acids or polyethyleneglycol used, for example, a jet mill, ball mill, vibratory mill or esters, PEG-n acylates. Fatty alcohol polyglycolether such as hammer mill, preferably a high-speed mixing mill. Even laureth-n, myreth-n, ceteareth-n, Steareth-n, oleth-n. fatty more preferable mills are modern ball mills; manufacturers of acid polyglycolether such as PEG-n stearate, PEG-n oleate, these types of mill are, for example, Netzsch (LMZ mill), PEG-n cocoate, monoglycerides and polyol esters, C-C, Drais (DCP-Viscoflow or Cosmo), Bühler AG (centrifugal fatty acid mono- and di-esters of addition products of from 1 mills) or Bachhofer. to 100 mol of ethylene oxide with polyols, fatty acid and 0090. Examples of kneading apparatus for the preparation polyglycerol ester Such as monostearate glycerol. diisos of the micronized organic UV absorbers are typical sigma tearoyl polyglyceryl-3-diisoStearates, polyglyceryl-3-diisos blade batch kneaders but also serial batch kneaders (IKA tearates, triglyceryl diisoStearates, polyglyceryl-2-sesqui Werke) or continuous kneaders (Continua from Werner and SoStearates or polyglyceryl dimerates. Mixtures of Pfleiderer). compounds from a plurality of those Substance classes are 0091. The grinding of the sparingly soluble organic com also Suitable. Fatty acid polyglycolesters such as monostear pounds used in the present invention is preferably carried out ate diethylene glycol, fatty acid and polyethylene glycol with a grinding aid. esters, fatty acid and saccharose esters such as Sucro esters, 0092. The dispersing agent is used as a low molecular glycerol and saccharose esters such as Sucroglycerides. Sor weightgrinding aid for all the above micronization processes. bitol and Sorbitan, Sorbitan mono- and diesters of Saturated US 2010/0143274 A1 Jun. 10, 2010

and unsaturated fatty acids having from 6 to 22 carbonatoms 1000NI, Cosmowax, cetearyl alcohol and PEG-40 castor oil and ethylene oxide addition products, polysorbate-n series, Emulgade F Special, cetearyl alcohol and PEG-40 castor oil Sorbitan esters such as sesquisostearate, Sorbitan, PEG-(6)- and Sodium cetearyl Sulfate Emulgade F. Stearyl alcohol and isostearate sorbitan, PEG-(10)-sorbitan laurate, PEG-17-di steareth-7 and steareth-10Emulgator E2155, cetearyl alco oleate sorbitan, glucose derivatives, C8-C22 alkyl-mono and hol and Szeareth-7 and steareth-10 Emulsifying wax U.S.N. oligo-glycosides and ethoxylated analogues with glucose F. glyceryl Stearate and PEG-75 stearate Gelot 64, propy being preferred as the sugar component, O/W emulsifiers lene glycol ceteth-3 acetate. Hetester PCS, propylene glycol isoceth-3 acetate Hetester PHA), cetearyl alcohol and cet Such as methyl gluceth-20 sesquistearate, Sorbitan Stearate/ eth-12 and oleth-12 Lanbritol Wax N 21, PEG-6 stearate Sucrose cocoate, methylglucose sesquistearate, cetearyl alco and PEG-32 stearate Tefose 1500, PEG-6 stearate and cet hol/cetearyl glucoside, W/O emulsifiers such as methyl glu eth-20 and steareth-20 Tefose 2000, PEG-6 stearate and cose dioleate/methyl glucose isostearate. Sulfates and ceteth-20 and glyceryl Stearate and steareth-20 Tefose 2561. Sulfonated derivatives, dialkylsulfoSuccinates, dioctyl Succi glyceryl Stearate and ceteareth-20 Teginacid H. C. X. nate, alkyl lauryl Sulfonate, linear Sulfonated paraffins, Sul 0.098 Anionic emulsifiers such as PEG-2 stearate SE, fonated tetrapropylene Sulfonate, sodium lauryl Sulfates, glyceryl Stearate SE Monelgine, Cutina KD, propylene gly ammonium and ethanolamine lauryl Sulfates, lauryl ether col stearate Tegin P. cetearyl Alcohol and Sodium cetearyl sulfates, sodium laureth sulfates Texapon N70 or sodium sulfate Lanette N. Cutina LE, Crodacol GP, cetearylalcohol myreth Sulfates Texapon K14S. SulfoSuccinates, acetyl and sodium lauryl sulfate Lanette W. trilaneth-4 phopshate isothionates, alkanolamide Sulfates, taurines, methyl tau and glycol stearate and PEG-2 stearate Sedefos 75, glyceryl rines, imidazole Sulfates. Zwitterionic or amphoteric Surfac stearate and sodium lauryl Sulfate Teginacid Special. Cat tants that carry at least one quaternary ammonium group and ionic acid bases such as cetearyl alcohol and cetrimonium at least one carboxylate and/or Sulfonate group in the mol bromide. ecule. Zwitterionic surfactants that are especially suitable are 0099 Most preferred dispersing agents are sodium alkyl betaines, such as N-alkyl-N,N-dimethylammonium glyci Sulfates or Sodium alkyl ether Sulfates, such as Sodium laureth nates, cocoalkyldimethylammonium glycinate, N-acylami sulfate Texapon N70 from Cognis or sodium myreth sulfate nopropyl-N,N-dimethylammonium glycinates, cocoacy Texapon K14 S from Cognis. laminopropyldimethylammonium glycinate and 2-alkyl-3- 0100. The specific dispersing agents may be used in an carboxymethyl-3-hydroxyethylimidazolines each having amount of, for example, from 1 to 30% by weight, especially from 8 to 18 carbon atoms in the alkyl or acyl group and also from 2 to 20% by weight and preferably from 3 to 10% by cocoacylaminoethylhydroxyethylcarboxymethylglycinate, weight, based on the total weight of the composition. N-alkylbetaine, N-alkylaminobetaines. 0101 Useful solvents are water, brine, (poly-)ethylene 0096. Examples of suitable mild surfactants as dispersing glycol, glycerol or cosmetically acceptable oils. Other useful agents, that is to say Surfactants especially well tolerated by solvents are disclosed below in the sections entitled "Esters of the skin, include fatty alcohol polyglycol ether Sulfates, fatty acids”, “Natural and synthetic triglycerides, including monoglyceride Sulfates, mono- and/or di-alkyl Sulfo Succi glyceryl esters and derivatives”. “Pearlescent waxes’. nates, fatty acid isethionates, fatty acid sarcosinates, fatty “Hydrocarbon oils” and “Silicones or siloxanes”. acid taurides, fatty acid glutamates, C-olefin Sulfonates, ether 0102 The micronized sparingly soluble organic com carboxylic acids, alkyl oligoglucosides, fatty acid glucam pounds so obtained usually have an average particle size from ides, alkylamidobetaines and/or protein fatty acid condensa 0.02 to 2 micrometres, preferably from 0.03 to 1.5 microme tion products, the latter preferably being based on wheat tres and more especially from 0.05 to 1.0 micrometres. proteins. 0103) The aqueous dispersion used in the present inven 0097. Non ionic surfactants such as PEG-6 beeswax (and) tion generally comprises PEG-6 Stearate (and) polyglyceryl-2-isostearate Apifac. 30-60, preferably 35 to 55 parts of the sparingly soluble glyceryl Stearate (and) PEG-100 stearate. Arlacel 165, organic micronized substance; PEG-5 glyceryl Stearate Iarlatone 983.S. sorbitan oleate 2-20, preferably 2 to 20 parts of the dispersing agent; (and) polyglyceryl-3 ricinoleate. Arlacel 1689, sorbitan 0.1-1 part, preferably 0.1 to 0.5 parts of a thickening agent Stearate and Sucrose cocoate arlatone 2121, glyceryl Stear (for example Xanthan gum); and ate and laureth-23 Cerasynth945, cetearyl alcohol and cet 20-68 parts of water; eth-20 Cetomacrogol Wax, cetearyl alcohol and colysorbate 0104. The cosmetic formulations or pharmaceutical com 60 and PEG-150 and stearate-20Polawax GP 200, Polawax positions according to the present invention can also com NF, cetearyl alcohol and cetearyl polyglucoside Emulgade prise one or more than one further UV filter as listed in Table PL 1618), cetearyl alcohol and ceteareth-20 Emulgade 1:

TABLE 1 Suitable UV filter substances and adjuvants which can be additionally used with the UV absorbers according to the present invention No. Chemical Name CAS No. 1 (+/-)-1,7,7-trimethyl-3-(4-methylphenyl)methylenebicyclo- 36861-47-9 2.2.1]heptan-2-one; p-methylbenzylidene camphor 2 1,7,7-trimethyl-3-(phenylmethylene)bicyclo[2.2.1]heptan-2-one; ben- 15087-24-8 Zylidene camphor 3 (2-Hydroxy-4-methoxyphenyl)(4-methylphenyl)methanone 1641-17-4 4 2,4-dihydroxybenzophenone 131-56-6

US 2010/0143274 A1 Jun. 10, 2010 13

TABLE 1-continued

Suitable UV filter substances and adjuvants which can be additionally used with the UV absorbers according to the present invention

No. Chemical Name CAS No.

63 Anthralinic acid, p-menth-3-yl ester 134-09-8 64 2,2'-bis(1,4-phenylene)-1H-benzimidazole-4,6-disulphonic acid mo 349580-12-7, no sodium salt or Disodium phenyl dibenzimidazole tetrasulfonate (Neo Heliopan AP) 65 1,3,5-Triazine-2,4,6-triamine, N,N'-bis(4-5-(1,1-dimethylpropyl)-2- 288254-16-0 benzoxazolylphenyl)-N'-(2-ethylhexyl)- (Uvasorb k2A) 66 Merocyanine derivatives as described in WO 2004.006878, WO2006032741, IPCOMOOOO22279D and in IPCOM JOURNAL (2005), 5(7B), 18

O O N-CEC-C H. H. H. CN

68 Sterols (cholesterol, lanosterol, phytosterols), as described in WOO341675 69 mycosporines and/or mycosporine-like amino acids as described in WO2002039974, e.g. Helioguard 365 from Milbelle AG, isolated my cosporine like amino acids from the red alga porphyra umbilicalis (INCI: Porphyra Umbilicalis) that are encapsulated into liposomes.) 70 alpha-lipoc-acid as described in DE 10229995 71 synthetic organic polymers as described in EP 1371358, O033-0041 72 phyllosilicates as described in EP 1371357 0034-0037 73 silica compounds as described in EP1371356,0033-0041 74 inorganic particles as described in DE 10138496 0043-0055 75 latex particles as described in DE 10138496 0027-0040 76 1H-Benzimidazole-4,6-disulfonic acid, 2,2'-(1,4-phenylene)bis-, 18O898-37-7 disodium salt; Bisimidazylate (Neo Heliopan APC)

77 - “sO N-CEC-CF O r H. H. H. 1-1-1S-1N

N 2 Šs US 2010/0143274 A1 Jun. 10, 2010 14

TABLE 1-continued Suitable UV filter substances and adjuvants which can be additionally used with the UV absorbers according to the present invention

No. Chemical Name CAS No.

O O r| E or Z isomer or mixture of E.Z isomers

81 Di-2-ethylhexyl-3,5-dimethoxy-4-hydroxy-benzalmalonate (Oxynex ST, EMD Chemicals, as described in US 20040247536) 82 2.4.6-Tris-1,1',4',1"-terphenyl-4-yl-1,3,5-triazine 83 2,4,6-Tris(p-biphenylyl)-s-triazine 31274-51-8

0105 Preferred dibenzoylmethane derivative used in the 0109 Further preferred amines are selected from alkoxy present invention is the 4-(tert-butyl)-4'-methoxydibenzoyl lated amines which correspond to the formula methane (also called avobenzone, CAS No. 70356-09-1), which is commercialised by DSM under the brand name Parsol(R) 1789 and Merck under the brand name EuSolex(R) (4a) (CH-CH-O),-H; or 9020. Other dibenzoylmethane derivatives are described in A R-N U.S. Pa. Nos. 4,489,057, 4,387,089 and 4,562,067. V 0106 The amines as used in the present invention are (CH-CH-O-H preferably alkanolamines. (4b) (CH-CH-O).-H; 0107 Examples of these compounds are 2-aminobutanol, A 2-(2-aminoethoxy)ethanol, aminoethyl propanediol, ami R-- (CH-N nomethyl propanediol, aminomethyl propanol (AMP), ami (ÖH.CHO).-H. (CH2CH2O, H nopropanediol, bis-hydroxyethyl tromethamine, butyl diethanolamine, butylethanolamine, DEA PG-oleate, dibutyl ethanolamine, diethanolamine, diethyl ethanolamine (DEA), wherein dihydroxyethyl toluidine, diisopropanolamine, dimethy 0110 R is C-Coalkyl; and lamino methylpropanol, dimethyl isopropanolamine, dim 0111 X, y and Z independently from each other are a ethyl mea, ethanolamine (EA), ethyl ethanolamine, hydroxy number from 1 to 20. ethyl palmityl oxyhydroxypropyl palmitamide, 0112 A typical representative of this class is PEG-10 isopropanolamine, n-lauryl diethanolamine, MEA-Sulfite, Hydrogenated Tallow Amine. methylethanolamine (MEA), mixed isopropanolamines, 0113. Further preferred are amines are selected from PEG-2 tallowamide DEA, TEA-diricinoleate, TEA-lauryl amine oxides which correspond to the formula (6) RR'R"NO, ether, triethanolamine (TEA), triisopropanolamine, wherein tromethamine (Tris Amino). 0114 R is C-Coalkyl; and 0108 More preferred alkanolamines are aminomethyl 0115I R' and R" independently from each other are propanol (AMP), ethanolamine (EA), diethyl ethanolamine C-C alkyl. (DEA), tromethamine (Tris Amino) and triethanolamine 0116. A typical example is lauramine oxide, which chemi (TEA). cally is N,N-dimethyl lauramine oxide. US 2010/0143274 A1 Jun. 10, 2010

0117 Examples of amines that may be used in the present dibromopropamidine diisethionate, dicocamine, dicocodim invention: ethylamine dilinoleate, diethanolamine bisulfate, diethy 0118 Acetyl carnitine HCl, adenine, adenosine, adenos lamine, diethylaminoethyl cocoate, diethylaminoethyl Stear ine cyclic phosphate, almondamidopropyl dimethylamine, ate, diethylamino hydroxybenzoyl hexyl benzoate, N.N- amidinoproline, amino bispropyl dimethicone, 5-amino-4- diethyl-m-aminophenol, N,N-diethyl-m-aminophenol chloro-o-cresol. 5-amino-6-chloro-o-cresol, 2-amino-6- Sulfate, diethylenetriamine pentamethylene phosphonic acid, chloro-4-nitrophenol, 4-amino-m-cresol, 6-amino-m-cresol, diethylhexylamine, N,N-diethyl-p-phenylenediamine sul 6-amino-o-cresol, 3-amino-2,4-dichlorophenol. 5-amino-2, fate, N,N-diethyltoluene-2,5-diamine HCL, dihydrogenated 6-dimethoxy-3-hydroxypyridine, 2-amino-4,5-dimethylthi tallow methylamine, dihydroxyaluminum aminoacetate, azole HBr, aminoethanesulfinic acid, aminoethylaminopro dihydroxyethylamino hydroxypropyl oleate, 2,6-dihydroxy pyl dimethicone, aminoethyl Sulfate, 5-amino-4-fluoro-2- ethylaminotoluene, dihydroxyethyl cocamine dioleate, dihy methylphenol Sulfate, aminoguanidine bicarbonate, droxyethyl soyamine dioleate, dihydroxyethyl tallowamine aminoguanidine HCL, 2-amino-4-hydroxyethylaminoani dioleate, dihydroxyethyl tallowamine HCL, dihydroxyethyl sole, 2-amino-4-hydroxyethylaminoanisole Sulfate, tallowamine/ipdi copolymer, dihydroxyethyl tallowamine 2-amino-3-hydroxypyridine, 4-amino-2-hydroxytoluene, oleate, diisopropylamine, dilinoleamidopropyl dimethy 2-aminomethyl-p-aminophenol HCL, 4-amino-2-nitrodiphe lamine, dimethicone propylethylenediamine behenate, 2.6- nylamine-2-carboxylic acid, 2-amino-3-nitrophenol, dimethoxy-3,5-pyridinediamine HCL, dimethoxysilyl ethyl 2-amino-4-nitrophenol, 2-amino-5-nitrophenol, 4-amino-2- enediaminopropyl dimethicone, dimethylaminoethyl nitrophenol, 4-amino-3-nitrophenol, 2-amino-4-nitrophenol methacrylate, m-dimethylaminophenyl urea, dimethyl behe Sulfate, m-aminophenol HCL, p-aminophenol HCL, m-ami namine, dimethyl cocamine, dimethylhydrogenated tallowa nophenol, o-aminophenol, p-aminophenol, m-aminophenol mine, N,N-dimethyl-n-hydroxyethyl-3-nitro-p-phenylene Sulfate, o-aminophenol Sulfate, p-aminophenol Sulfate, diamine, dimethyl lauramine, dimethyl lauramine dimer 3-aminopropane Sulfonic acid, aminopropyl dehydrogenate dilinoleate, dimethyl lauramine isostearate, dimethyl lau phosphate, aminopropylkoyl phosphate, aminopropyl meth ramine oleate, dimethyl myristamine, dimethyl palmitamine, ylenedioxyphenyl phosphate, aminopropyl tocopheryl phos 2,6-dimethyl-p-phenylenediamine HCL, N,N-dimethyl-p- phate, aminotriazine pentane carboxamide mipa, aminotrim phenylenediamine, 2,6-dimethyl-p-phenylenediamine, N.N- ethylene phosphonic acid, amodimethicone, aspartame, dimethyl-p-phenylenediamine sulfate, N,N-dimethyl 2,6-py avocadamidopropyl dimethylamine, babasSuamidopropyl ridinediamine HCL, dimethyl soyamine, dimethyl dimethylamine, basic blue 3, basic red 118, behenamidopro Stearamine, dimethyl tallowamine, dimethyltolylamine, dio pyl dimethylamine, behenamidopropyl dimethylamine leoyl edetolmonium methosulfate, dipalmitamine, dipeptide behenate, behenamidopropyl dimethylamine lactate, ben diaminobutyroyl benzylamide diacetate, diphenhydramine Zoguanamine, bisamino PEG/PPG-4 1/3 aminoethyl pg-pro HCL, dipropylenetriamine, disodium bisethylphenyl triami pyl dimethicone, bis-aminopropyl dimethicone, bis(c13-15 notriazine stilbenedisulfonate, disodium cocaminopropyl alkoxy) pg-amodimethicone, 1,3-bis-(2,4-diaminophenoxy) iminodiacetate, disodium dicarboxyethyl cocopropylenedi propane, 4,6-bis(2-hydroxyethoxy)-m-phenylenediamine amine, disodium guanylate, disoyamidoethyl hydroxyethyl HCL, 2,6-bis(2-hydroxyethoxy)-3,5-pyridinediamine HCL, ammonium lactate, disoyamine, distearamidopropylmethy N,N'-bis(2-hydroxyethyl)-2-nitro-p-phenylenediamine, lamine, distearyldimethylamine dilinoleate, ditallowamido N,N-bis(2-hydroxyethyl)-p-phenylenediamine sulfate, bru ethylhydroxypropylamine, ethanolamine HCL, 4-ethoxy-m- cine sulfate, calcium disodium EDTA, c12-14 alkyl diamino phenylenediamine Sulfate, 3-ethylamino-p-cresol Sulfate, ethylglycine HCL, carnitine HCL, carnitine pica, carnosine, 7-ethylbicyclooxazolidine, ethyl dimethylaminobenzoate, cetylamine hydrofluoride, cetyldimethylamine hydrolyzed ethylhexyl bis-isopentylbenzoxazolylphenyl melamine, hempseedate, chloramine t, chlorhexidine, 4-chloro-2-ami n-ethyl-3-nitro papa, fluorescent brightener 230, 4-fluoro-6- nophenol, 2-chloro-6-ethylamino-4-nitrophenol, 2-chloro-5- methyl-m-phenylenediamine Sulfate, gerotine, glucamine, nitro-N-hydroxyethyl p-phenylenediamine, 2-chloro-p-phe glucosamine, glucosamine ascorbate, glucosamine HCL, nylenediamine, 2-chloro-p-phenylenediamine Sulfate, glucosamine Sulfate, glucosamine thioctate, guanidine HCL, cocamidopropyl dimethylamine, cocamidopropyl dimethy guanidine phosphate, HC blue no. 14, HC orange no. 5, HC lamine dihydroxy-methylpropionate, cocamidopropyl dim red no. 14, HC red no. 15, HC yellow no. 14, HC yellow no. ethylamine lactate, cocamidopropyl dimethylamine propi 15, hexamidine, hexamidine disethionate, hexamidine dipa onate, cocamidopropyl morpholine, cocamidopropyl rabene, hexamidine paraben, histidine dna, hydrogenated morpholine lactate, cocamine, cocoyl polyglyceryl-4 ditallowamine, hydrogenated tallowamine, hydroxyethy hydroxypropyl dihydroxyethylamine, cyclohexylamine, laminomethyl-p-aminophenol HCL, 2-hydroxyethylamino N-cyclopentyl-m-aminophenol, cytosine, DEA-C alkyl 5-nitroanisole, hydroxyethyl carboxymethyl cocamidopro sulfate, DEA-C is perfluoroalkylethyl phosphate, DEA pylamine, hydroxyethyl chitosan, 1-hydroxyethyl 4.5- PEG-4 laurate, DEA pg-propyl PEG/PPG-18/21 dimethi diamino pyrazole Sulfate, hydroxyethyl-2,6-dinitro-p- cone, DEA-polyperfluoroethoxymethoxy PEG-2 phosphate, anisidine, hydroxyethyl-3,4-methylenedioxyaniline HCL, dicarboxy carnosine HCL, 2,4-diaminodiphenylamine, 4,4'- hydroxyethyl-2-nitro-p-toluidine, hydroxyethyl-p-phe diaminodiphenylamine, 4,4'-diaminodiphenylamine Sulfate, nylenediamine Sulfate, 2-hydroxyethyl picramic acid, 4-hy 2,4-diamino-5-methylphenetole HCL, 2,4-diamino-5-meth droxypropylamino-3-nitrophenol, hydroxypropyl arginine ylphenoxyethanol HCL, 4,5-diamino-1-methylpyrazole lauryl/myristyl ether HCL, hydroxypropyl bis(n-hydroxy HCL, 2,4-diaminophenol. 2,4-diaminophenol HCL, 2,4-di ethyl-p-phenylenediamine) HCL, hydroxypropyl ethylenedi aminophenoxyethanol HCL, 2,4-diaminophenoxyethanol amine carbomer, hydroxyStearyl methylglucamine, imida Sulfate, 2,6-diaminopyridine, 2,6-diaminopyridine Sulfate, Zole, isopropylamine, n-isopropyl 4,5-diamino pyrazole 2,6-diamino-3-((pyridin-3-yl)aZo)pyridine, diaminopyrimi Sulfate, isostearamidopropyl dimethylamine, isostearami dine oxide, diammonium EDTA, dibehenyl methylamine, dopropyl dimethylamine gluconate, isostearamidopropyl US 2010/0143274 A1 Jun. 10, 2010 dimethylamine glycolate, isostearamidopropyl dimethy pica, polylysine HBR, potassium edtmp, potassium magne lamine lactate, isostearamidopropyl morpholine, isosteara sium aspartate, pyridoxine hydroxybenzoate, quinine, ricino midopropyl morpholine lactate, kinetin, lauramidobutyl leamidopropyl dimethylamine, ricinoleamidopropyl dim guanidine acetate, lauramidobutyl guanidine HCL, laurami ethylamine lactate, scordinine, Sesamidopropyl dopropyl dimethylamine, lauramidopropyl dimethylamine dimethylamine, sodium bischlorophenyl Sulfamine, sodium propionate, lauramine, lauraminopropylamine, laurimino carboxyethyl tallow polypropylamine, sodium carboxym dipropionic acid, laur/myrist/palmitamidobutyl guanidine ethyl cocopolypropylamine, Sodium carboxymethyl tallow acetate, lauroyl ethylenediamine triacetic acid, laurylamine polypropylamine, Sodium cocoyl methylaminopropionate, dipropylenediamine, lauryl aminopropylglycine, lauryl Sodium diethylenetriamine pentamethylene phosphonate, Sodium EDTMP, Sodium guanosine cyclic monophosphate, diethylenediaminoglycine, lauryl diethylenediaminoglycine Sodium hydroxylauryldimonium ethyl phosphate, Sodium HCL, lauryl dimethylamine cyclocarboxypropyloleate, lauroyl ethylenediamine triacetate, sodium lauryl diethylene lidocaine HCL, linoleamidopropyl dimethylamine, linolea diaminoglycinate, Sodium picramate, Sodium sulfanilate, midopropyl dimethylamine dimer dilinoleate, linoleami Soyamidopropyl dimethylamine, Soyamine, Soyaminopropy dopropyl diammonium lactate, lithium guanosine triphos lamine, spermidine HCL, sphinganine, starch diethylamino phate, lysine aZelate, lysine cocoate, mea-benzoate, mea ethyl ether, stearamidoethyl diethanolamine, stearamidoethyl borate, mea-iodine, melamine peroxide, methenamine, diethylamine, Stearamidoethyl diethylamine phosphate, methenammonium chloride, n-methoxyethyl-p-phenylene Stearamidoethyl ethanolamine, Stearamidoethyl ethanola diamine HCL, 2-methoxymethyl-p-aminophenol HCL, mine phosphate, Stearamidopropyl dimethylamine, Stearami 2-methoxy-p-phenylenediamine Sulfate, 6-methoxy-2,3-py dopropyl dimethylamine lactate, Stearamidopropyl dimethy ridinediamine HCL, 4-methoxytoluene-2,5-diamine HCL, lamine Stearate, Stearamidopropyl morpholine, methyl aminomethylcyclohexane carboxamide HCL, 3-me Stearamidopropyl morpholine lactate, Stearamine, StearoX thylamino-4-nitrophenoxyethanol, p-methylaminophenol, ypropyl dimethylamine, stearyl PG-dimethylamine, sunflow p-methylaminophenol Sulfate, methyl anthranilate, 4-meth erseedamidopropyl dimethylamine, SunflowerSeedami ylbenzyl 4,5-diamino pyrazole Sulfate, methyl dicocamine, dopropyl dimethylamine lactate, SunflowerSeedamidopropyl 2,2'-methylenebis 4-aminophenol. 2,2'-methylenebis-4-ami dimethylamine malate, SunflowerSeedamidopropyl morpho nophenol HCL, 3.4-methylenedioxyaniline, methylglucam line lactate, tallamidopropyl dimethylamine, tallowami ine, 2-methyl-5-hydroxyethylaminophenol, n-methyl-3-ni dopropyl dimethylamine, tallow amine, tallowaminopropy tro-p-phenylenediamine, methylthioadenosine, lamine, taurine, TEA-Css perfluoroalkylethyl phosphate, minkamidopropyl dimethylamine, mipa-borate, morpholine, TEA-EDTA, TEA-hydrochloride, TEA-hydroiodide, TEA myristamidobutyl guanidine acetate, myristamidopropyl lactate, TEA-lauroyl glutamate, TEA-pca, TEA-polyphos dimethylamine, myristamidopropyl dimethylamine phos phate, TEA-salicylate, TEA-sorbate, TEA-sulfate, tetrahy phate, myristaminopropionic acid, myrist/palmitamidobutyl droxyethyl ethylenediamine, tetrahydroxypropyl guanidine acetate, 3-nitro-4-aminophenoxyethanol, 2-nitro ethylenediamine, tetrahydroxypropyl ethylenediamine 5-glyceryl methylaniline, 3-nitro-p-hydroxyethylaminophe dioleate, tetrasodium EDTA, tetrasodium iminodisuccinate, nol, 2-nitro-n-hydroxyethyl-p-anisidine, 4-nitrophenyl ami thiamine diphosphate, thiamine HCL, thiamine nitrate, thio noethylurea, 4-nitro-o-phenylenediamine dihydrochloride, taurine, tocopheryl dimethylglycinate HCL, tolnaftate, tolu 2-nitro-p-phenylenediamine dihydrochloride, 4-nitro-ophe ene-2,5-diamine, toluene-2,6-diamine, toluene-3,4-diamine, nylenediamine HCL, 4-nitro-m-phenylenediamine, 4-nitro toluene-2,5-diamine Sulfate, o-tolyl biguanide, 2.5,6-tri o-phenylenediamine, 2-nitro-pphenylenediamine, 4-nitro-m- amino-4-pyrimidinol Sulfate, trilaurylamine, trimethylsi phenylenediamine Sulfate, 4-nitro-o-phenylenediamine loxyamodimethicone, tri-PABA panthenol, tripotassium Sulfate, 6-nitro-2,5-pyridinediamine, 6-nitro-o-toluidine, oatamidopropyl dimethylamine, olaflur, oleamidopropyl EDTA, trisodium dicarboxymethyl alaninate, trisodium dimethylamine, oleamidopropyl dimethylamine glycolate, EDTA, trisodium ethylenediamine disuccinate, trisodium oleamidopropyl dimethylamine lactate, oleamidopropyl dim hEDTA, trisodium NTA, tris-oleoyltromethamine ethane sul ethylamine propionate, oleamine, olivamidopropyl dimethy fate, tromethamine magnesium aluminum silicate, tyrosyl lamine, olivamidopropyl dimethylamine lactate, PABA, pal histidine HCL, uracil, wheat germamidopropyl dimethy mamine, palmitamidobutyl guanidine acetate, lamine, wheat germamidopropyl dimethylamine lactate, Zinc palmitamidopropyl diethylamine, palmitamidopropyl dim magnesium aspartate. ethylamine, palmitamidopropyl dimethylamine lactate, 0119 Preferred amides are compounds which correspond palmitamidopropyl dimethylamine propionate, palmitamine, to the formula (7) RCO NXY, wherein palmitoleamidopropyl dimethylamine lactate, palmitoleami I0120 RCO is a carboxylic acid or a fatty acid radical; dopropyl dimethylamine propionate, PEG-3 2,2'-di-p-phe and nylenediamine, PEI-7, PEI-10, PEI-15, PEI-30, PEI-35, PEI I0121 X and Y independently from each other are hydro 45, PEI-250, PEI-275, PEI-700, PEI-1000, PEI-1400, PEI gen; or any alkyl or aromatic radical. 1500, PEI-1750, PEI-2500, PEI-14m, pentasodium 0.122 The amide class may be part of a heterocyclic ring, aminotrimethylene phosphonate, pentasodium ethylenedi as in PCA. amine tetramethylene phosphonate, pentasodium pentetate, 0123 R can also represent a nitrogen atom, as in Urea. pentetic acid, PGg-amodimethicone, pphenetidine, p-phe Amides are hydrolyzable derivatives of carboxylic acids and nylenediamine HCL, m-phenylenediamine, p-phenylenedi are prepared via a number of synthetic and biological routes. amine, m-phenylenediamine Sulfate, p-phenylenediamine A typical representative includes Cocamide. Sulfate, n-phenyl-p-phenylenediamine HCL, n-phenyl-p- 0.124 Examples of amides as used in the present invention phenylenediamine, n-phenyl-p-phenylenediamine Sulfate, are acetamidocaproic acid, acetaminophen, acetaminosalol, phytosphingosine, phytosphingosine glycolate, phytosphin acetanilid, acetylarginine, acetylated cetylhydroxyprolinate, gosine HCL, phytosphingosine lactate, phytosphingosine n-acetyl dihydrosphingosine, acetyl glucosamine, acetyl US 2010/0143274 A1 Jun. 10, 2010 glutamic acid, acetyl hydroxyproline, acetyl methionine, hyaluronic acid, hydrogenated tallow amide, hydroxycaproyl acetylphytosphingosine, acetyl trifluoromethylphenyl phytosphingosine, hydroxycapryloyl phytosphingosine, valylglycine, adamantanylcarboxamidohydroxylbenzamide, hydroxyethyl carboxymethyl cocamidopropylamine, adamantanyl hydroxylterephthalamide, adamantylcarboxa hydroxyethyl urea, hydroxylauroyl phytosphingosine, mido methylhydroxylbenzamide, adamantyl dihydroxyben hydroxymethoxybenzyl pelargonamide, hydroxypalmitoyl Zamide, adamantyl methylhydroxylterephthalamide, ada sphinganine, hydroxyphenyl dihydroxybenzamide, hydrox mantyl trihydroxybenzamide, adipic acid dihydrazide, yproline palmitamide, illomastat, imidazolidinyl urea, inulin algaeoyl phytosphingosine, allantoin panthenol, aluminum lauryl carbamate, iodopropynylbutylcarbamate, isostearami hydrogenated tallow glutamate, aluminum PCA, aluminum domorpholine Stearate, isostearamidopropyl epoxypropyl Stearoyl glutamate, aminopropyl laurylglutamine, ammo morpholinium chloride, ketoconazole, laccaic acid, lacta nium polyacryloyldimethyl taurate, anserine, aspartame, mide, lactoyl phytosphingosine, lauramide, lauramidobutyl behenamide, benzisothiazolinone, benzylidenecamphor guanidine acetate, lauramidobutyl guanidine HCl, laur/ hydrolyzed collagen sulfonamide, bis(Cisalkoxy)hydrox myrist/palmitamidobutyl guanidine acetate, lauroyl glutamic ybutamidoamodimethicone, bis-hydroxyethyl biscetyl mal acid, lauroyl methyl beta-alanine, lauroyl methylglucamide, onamide, bis-hydroxyethyl tocopherylsuccinoylamido laurylgluconamide palmitates, lauryl methylglucamide, hydroxypropane, bis-methoxypropylamido isodocosane, lidocaine HCl, linoleamide, lysine PCA, MDM hydantoin, t-butylbenzamido hydroxylbenzamide, t-butylbenzamido melatonin, methoxycinnamidopropyl Os alkyldimonium hydroxylphenylacetamide, t-butylbenzamido methylhy tosylate, methoxy PEG-450 amidoglutaroyl succinimide, droxylbenzamide, butyl resorcinol bis-Succinoylphytosphin methoxy PEG-450 amido hydroxysuccinimidyl succi gosine, Oc acid amide MEA, calcium pantetheline Sul namate, methoxypropylgluconamide, methyl acetamide, fonate, calcium saccharin, caproyl sphingosine, caproyl methyl aminomethylcyclohexane carboxamide HCl, methyl tyrosine, capryloyl glycine, capryltyrosinamide, caprylyl diisopropyl propionamide, milkamidopropyl amine oxide, pyrrolidone, capsaicin, carboxymethyl chitosan myrista milkamidopropyl betaine, minkamidopropyl betaine, myris mide, carboxymethyl chitosan Succinamide, ceramide 1. tamidobutyl guanidine acetate, myristoyl glutamic acid, ceramide 2, ceramide 3, ceramide 4. ceramide 5, ceramide 1 myristoyl methyl beta-alanine, myristoyl/palmitoyl a, ceramide 6 II, cetyloxypropyl glyceryl methoxypropyl oxostearamide/arachamide MEA, myristoyl Succinoylatelo myristamide, cetyl-PG hydroxyethyl decanamide, cetyl-PG collagen, myrist/palmitamidobutyl guanidine acetate, myri hydroxyethyl palmitamide, chitosan lauramide Succinamide, styl-pg hydroxyethyl decanamide, neotame, niacinamide, chitosan succinamide, chloroacetamide, cholesteryl hexyl niacinamide ascorbate, niacinamide glycolate, niacinamide dicarbamate pullulan, cloflucarban, cocamide, cocamide hydroxycitrate, niacinamide lactate, niacinamide malate, methyl MEA, cocoylglutamic acid, cocoyl methyl beta-ala niacinamide mandelate, niacinamide Salicylate, niacinamide nine, coenzyme a, crotamiton, decarboxy carnosine HCl, thioctate, nicotinamide adenine dinucleotide, nylon-61 1, DEDM hydantoin, DEDM hydantoin dilaurate, diazolidinyl nylon-61 1/dimethicone copolymer, octylisothiazolinone, urea, dibelhenamidopropyldimethylamine dilinoleate, dibro oleamide, 2-oleamido-1,3-octadecanediol, oleoyl tyrosine, mocyanoacetamide, dibutyldecyl IPDI, dibutylhexyl IPDI, leyl palmitamide, palmitamide, palmitamidobutyl guanidine dibutyl lauroylglutamide, dibutyloctyl IPDI, dicapryloyl cys acetate, palmitamidohexadecanediol, palmitoyl glutamic tine, didecyltetradecyl IPDI, diethyl acetyl aspartate, diethyl acid, palmitoyl glycine, palmitoyl methoxytryptamine, caprylamide, diethylhexyl butamido triazone, diethylhexyl palmitoyl myristyl serinate, palmitoyl pg-linoleamide, pan IPDI, diethyl toluamide, Di-HEMA trimethylhexyl dicar tetheline Sulfonate, pantethine, panthenol, panthenyl ethyl bamate, dihexyldecyl IPDI, dihydrogenated tallow phthalic ether, panthenyl ethyl ether acetate, panthenyl ethyl ether acid amide, dihydroxyisopropyl capryloylcaprylamide, dihy benzoate, panthenyl hydroxypropyl Steardimonium chloride, droxyisopropyl palmoylpalmamide, dilinoleic acid/ethylene panthenyl triacetate, PCA, PCA dimethicone, PCA ethyl diamine copolymer, dimer dilinoleamidopropyl dibetaine, cocoyl arginate, palmitate. PEG-3 diethylenetriamine dipal dimethiconol panthenol, dimethoxybenzamido phenylhy mamide, PEG-2 dimeadowfoamamidoethylmonium metho droxylacetamide, m-dimethylaminophenyl urea, dimethyl Sulfate, PG-palmoylpalmamide, phenacetin, phthalimidoper capramide, dimethylol urea, dimethyl urea, dioctyldecyl oxycaproic acid, phytosphingosine acetamide, picolinamide, IPDI, dioctyldodecyl IPDI, dioctyldodecyl stearoyl polyacrylamide, polyacrylamidomethyl benzylidene cam glutamate, Di-PEG-2 soyamine IPDI, dipeptide diaminobu phor, polyamide-1, polyamide-2, polyamide-3, polybeta-ala tyroyl benzylamide diacetate, disodium cocoyl glutamate, nine, polyepsilon-lysine, polylysine, polymethacrylamide, disodium N-lauroylaspartate, disoyamidoethylhydroxyethyl polymethacryloyl lysine, polymethylglutamate, poly-p-phe ammonium lactate, distearamidopropylmethylamine, diste nylene terephthalamide, polyvinylcaprolactam, polyvinyl areth-75 IPDI, disteareth-100 IPDI, distearyl phthalic acid formamide, potassium azeloyl diglycinate, potassium amide, ditallowamidoethyl hydroxypropylimonium metho caproyl tyrosine, potassium cocoyl glutamate, potassium sulfate, di-TEAcocamide diacetate, dithiodiethyl bis-dihy cocoyl glycinate, potassium cocoyl PCA, potassium cocoyl droxydimethylbutyramide, dithiodiethyl bis-lactamide, taurate, potassium methyl cocoyl taurate, potassium PCA, dithiodiethyl bis-salicylamide, dithiomethylbenzamide, prolinamidoethyl imidazole, pyricarbate, quaternium-80, DMDM hydantoin, DMHF, DM hydantoin, erucamide, eth retinyl formylaspartamate, riboflavin, riboflavin tetraacetate, ylene dihydrogenated tallowamide, ethylene dilinoleamide, saccharin, salicylamide, salicylhydroxamic acid, Salicyloyl ethylene dioleamide, ethylene distearamide, ethylhexylben phytosphingosine, Salnacedin, S-lactoylglutathione, sodium Zyldioxopiperazyl acetate, ethylhexyl dimethoxyben cocoyl glycinate, sodium diethylaminopropyl cocoasparta Zylidene dioxoimidazolidine propionate, ethyl lauroyl argin mide, Sodium dilauramidoglutamide lysine, Sodium dimer ate HCl, ethyl menthane carboxamide, ethyl tosylamide, coenzyme a, sodium lauramido diacetate, Sodium lauroyl fluorosalan, fluridil, glycolamide Stearate, glycyl glycine, ethylenediamine triacetate, sodium methyltaurine cocoyl hexyldecyl myristoyl methylaminopropionate, hippuric acid, methyltaurate, Sodium palmitoyl proline, Sodium palm ker US 2010/0143274 A1 Jun. 10, 2010 nelamphopropionate, Sodium pantetheline Sulfonate, sodium palmitamide MEA, palm kernelamide DEA, palm kernela PCA, sodium PCAthylsilanol, Sodium PEG-6 cocamide car mide MEA, palm kernelamide MIPA, pantothenamide MEA, boxylate, sodium PEG-8 cocamide carboxylate, sodium nutamide MEA, peanutamide MIPA, PEG-20 pocamide PEG-3 lauramide carboxylate, Sodium peg-4 lauramide car boxylate, Sodium phenylacetyl glutamine, sodium pheny MEA, ricebranamide DEA, ricinoleamide DEA, ricinoleam lacetyl isoglutamine, sodium polyacryloyldimethyl taurate, ide MEA, ricinoleamide MIPA, sesamide DEA, sesamide Sodium polygamma-glutamate, sodium polyglutamate, DIPA, soyamide DEA, stearamide AMP stearamide DEA, Sodium Stearyl phthalamate, sodium taurine cocoyl methyl stearamide DEA-distearate, stearamide DIBA-stearate, taurate, sodium Zinc histidine dithiooctanamide, Stearamide, stearamide MEA, stearamide MEAStearate, stearamide Stearamidodihydroxyisobutyl Stearate, Stearic hydrazide, MIPA, tallamide DEA, tallowamide DEA, tallowamide N-Stearoyldihydrosphingosine, Stearoyl glutamic acid, MEA, trideceth-2 Carboxamide MEA, undecylenamide Stearyl acetylglutamate, Stearyl erucamide, Stearylglucona DEA, undecylenamide MEA or wheat germamide DEA. mide dilaurate. Succinoyl ascorbate pentapeptide-6. Succi I0131 Preferred amides are also selected from alkoxylated noyl atelocollagen, Succinoyl serum albumin, tallow amide, TDI/trimelitic anhydride copolymer, TEA-cocamide diac amides which correspond to the formula etate, TEA-hydrogenated tallowoyl glutamate, TEA-PCA, tetraacetylphytosphingosine, tetramethylolglycoluril, tetra (3a) Sodium disuccinoyl cystine, thenoyl methionate, thiodiglyco O R lamide, thymine, tococysteamide, tosylamide, triacetyl retin oyl phytosphingosine, triclocarban, R N trihydroxypalmitamidohydroxypropyl myristyl ether, tris 1. H ---pi O (PEG-2 Phenylalanylcarboxamido) cyclohexane, tyrosyl (3.b) Histidine HCl, undecylenoyl glycine, urea, urea Peroxide, O (CHR-CH-O)-X A yeast palmitate or zinc PCA. N 0.125 Further preferred amides are selected from alkano V lamides which correspond to formula R (CHR"-CH-O)-X

(2) wherein O X (0132 R is C-Coalkyl: N V 0.133 R' and R" independently from each other are is RX-X Y, hydrogen; or C-C alkyl: 0.134 X and X" independently from each other are hydro wherein gen; or or Sulfo Succinyl: 0126 R is C-Coalkyl: 0135) n is a number from 2 to 60; 0127 X is the radical —CHR'CHOH: 0.136 n+m independently from each other are a number I0128 R' is hydrogen; or C-C alkyl; and from 1 to 60, and the sum of n+m23. 0129. Y is CHR'CH-OH: C-C alkyl; or 0.137. A typical representative of this group of compounds C-C hydroxyalkyl. is PEG-7 Oleamide. 0130. Examples of preferred alkanolamides are acetamide 0.138. Further preferred amides are selected from alkyla MEA, almondamide DEA, apricotamide DEA, avocadamide mido alkylamines which correspond to the formula DEA, avocadamide DIPA, azelamide MEA, babassuamide DEA, babassuamide MEA, behenamide DEA, behenamide MEA, c0apramide DEA, cocamide DEA, cocamide DIPA, cocamide MEA, cocamide MIPA, cocoyl sarcosinamide O Y (5) DEA, cornamide? cocamide DEA, cornamide DEA, dietha nolaminooleamide DEA, disodium cocamido MIPA PEG-4 ls N SulfoSuccinate, disodium lauramido MIPA, glycol Sulfo Suc R 1- a cinate, hydrogenated tallowamide DEA, hydroxycetyl hydroxyethylstearamide, hydroxyethyl ethylene dipalmita mide, hydroxyethyl stearamide-MIPA, hydroxylauroyl wherein phytosphingosine, hydroxypropyl bisisoStearamide MEA, I0139 R is C-Coalkyl: hydroxypropyl bislauramide MEA, hydroxypropyl bispalmi 0140 X is hydrogen; or —CHCOO. Na+ and tamide MEA, hydroxystearamide MEA, isostearamide DEA, 0141 Y is -CHCOO. Na+; CH-CHCOO. Na+, isostearamide MEA, isostearamide MIPA, lactamide MEA, —CHCHOHCHSO. Na+, O lanolinamide DEA, lauramide DEA, lauramide MEA, laura mide MIPA, lauramide/Myristamide DEA, lauryl Malamide, CHCHOHCHOPO, (H+/Na+). lecithinamide DEA, linoleamide DEA, linoleamide MEA, 0142. The commercially available compounds in this class linoleamide MIPA, minkamide DEA, myristamide DEA, are fairly complicated mixtures of chemically related mate myristamide MEA, myristamide MIPA, oatamide MEA, rials. oleamide DEA, oleamide DIPA, oleamide MEA, oleamide 0143. In a preferred embodiment of the present invention MIPA, olivamide DEA, oliveamide MEA, palmamide DEA, the amines are selected from mono-, di-, and triethanola palmamide MEA, palmamide MIPA, palmitamide DEA, mines, the micronized UV absorbers correspond to formula US 2010/0143274 A1 Jun. 10, 2010 19

from 10 to 35% by weight, based on the total weight of the composition, of at least one oil component, from 0 to 30% by (3) weight, especially from 1 to 30% by weight and preferably O O from 4 to 20% by weight, based on the total weight of the composition, of at least one emulsifier, from 10 to 90% by OH O A-R-A O OH weight, especially from 30 to 90% by weight, based on the total weight of the composition, of water, and from 0 to 88.9% by weight, especially from 1 to 50% by weight, of further OO OO. cosmetically acceptable adjuvants. A. R R 0154 The cosmetic or pharmaceutical compositions/ preparations according to the invention may also contain one or one more additional compounds as like fatty alcohols, wherein esters offatty acids, natural or synthetic triglycerides includ 0144. RandR independently from each other are hydro ing glyceryl esters and derivatives, pearlescent waxes, hydro gen; or C-C alkyl; carbon oils, silicones or siloxanes (organo-Substituted polysi (0145 A is NH; or - O -; and loxanes), fluorinated or perfluorinated oils, emulsifiers, 014.6 R is a C-C alkylene radical; or R together with A adjuvants and additives, Super-fatting agents, Surfactants, forms a bivalent radical of the formula) consistency regulators/thickeners and rheology modifiers, polymers, biogenic active ingredients, deodorising active ingredients, anti-dandruff agents, antioxidants, hydrotropic agents, preservatives, bacteria-inhibiting agents, perfume oils, colorants, polymeric beads or hollow spheres as SPF enhancers. and the dibenzoylmethane derivative is 4-(tert-butyl)-4- Cosmetic or Pharmaceutical Preparations methoxydibenzoylmethane. 0155 Cosmetic or pharmaceutical formulations are con 0147 The present invention is also directed to cosmetic or tained in a wide variety of cosmetic preparations. There come pharmaceutical compositions, comprising into consideration, for example, especially the following (a) 0.1 to 20% b.w. of a benzophenone UV absorber of for preparations: skin-care preparations, bath preparations, cos mula (1): metic personal care preparations, foot-care preparations, (b) 0.1 to 10% b.w. of a methoxydibenzoylmethane deriva light-protective preparations, skin-tanning preparations, tive; and depigmenting prepartitions, insect-repellents, deodorants, (c) 0.1 to 50% b.w. of an amine or amide. antiperspirants, preparations for cleansing and caring for 0148. The cosmetic or pharmaceutical preparations can be blemished skin, hair-removal preparations in chemical form prepared by physically mixing the UV absorber(s) with the (depilation), shaving preparations, fragrance preparations, adjuvant using customary methods, for example by simply cosmetic hair-treatment preparations, stirring together the individual components, especially by making use of the dissolution properties of already known Presentation Forms cosmetic UV absorbers, like octyl methoxy cinnamate, Sali cylic acid isooctyl ester, etc. The UV absorber can be used, for 0156 The final formulations listed may exist in a wide example, without further treatment, or in the micronized variety of presentation forms, for example: state, or in the form of a powder. (O157 in the form of liquid preparations as a W/O, O/W, 014.9 The amines and amides according to the present O/W/O, WFO/W or PIT emulsion and all kinds of micro invention are useful for eliminating the conversion of larger emulsions, scaled particles present in the composition. 0158 in the form of a gel, 0150. Furthermore, the amines and amides according to 0159 in the form of an oil, a cream, milk or lotion, the present invention are useful for eliminating the physic 0.160 in the form of a powder, a lacquer, a tablet or chemical interactions with dibenzoylmethane derivatives. make-up. 0151. The cosmetic composition according to the present 0.161 in the form of a stick, invention is preferably used for preventing the human hair or 0162 in the form of a spray (spray with propellant gas skin from the harmful effect of UV radiation. or pump-action spray) or an aerosol, in the form of a 0152 The cosmetic or pharmaceutical preparations may foam, or be, for example, creams, gels, lotions, alcoholic and aqueous/ 0.163 in the form of a paste. alcoholic solutions, emulsions, wax/fat compositions, Stick 0164. Of special importance as cosmetic preparations for preparations, powders or ointments. In addition to the above the skin are light-protective preparations, such as Sun milks, mentioned UV filters, the cosmetic or pharmaceutical prepa lotions, creams, oils, Sun blocks or tropicals, pretanning rations may contain further adjuvants as described below. preparations or after-Sun preparations, also skin-tanning 0153. As water- and oil-containing emulsions (e.g. W/O, preparations, for example self-tanning creams. Of particular O/W, O/W/O and W/O/W emulsions or microemulsions) the interest are Sun protection creams, Sun protection lotions, Sun preparations contain, for example, from 0.1 to 30% by protection milk and Sun protection preparations in the form of weight, preferably from 0.1 to 15% by weight and especially a Spray. from 0.5 to 10% by weight, based on the total weight of the 0.165 Of special importance as cosmetic preparations for composition, of one or more UV absorbers, from 1 to 60% by the hair are the above-mentioned preparations for hair treat weight, especially from 5 to 50% by weight and preferably ment, especially hair-washing preparations in the form of US 2010/0143274 A1 Jun. 10, 2010 20 shampoos, hair conditioners, hair-care preparations, e.g. pre silicon derivatives, emollients, emulsifiers or emulsifying treatment preparations, hair tonics, styling creams, styling Surfactants, Surfactants, dispersing agents, antioxidants, anti gels, pomades, hair rinses, treatment packs, intensive hair irritants and anti-inflammatory agents etc. treatments, hair-straightening preparations, liquid hair-set 0167. The cosmetic preparation according to the invention ting preparations, hair foams and hairsprays. Of special inter is distinguished by excellent protection of human skin against est are hair-washing preparations in the form of shampoos. the damaging effect of Sunlight. 0166 Other typical ingredients in such formulations are preservatives, bactericides and bacteriostatic agents, per EXAMPLES fumes, dyes, pigments, thickening agents, moisturizing B. Working Example agents, humectants, fats, oils, waxes or other typical ingredi ents of cosmetic and personal care formulations such as alco Examples 1 to 6 hols, poly-alcohols, polymers, electrolytes, organic solvents, (0168

Ex. 1 Ex. 2 Ex. 3 Ex. 4 Ex. S Ex. 6 OW formula % % % % % %

INCI-Name ww ww ww ww ww ww Part A. Butyl Methoxydibenzoylmethane 4.OO 4.OO 4.OO 4.OO 4.OO 4.OO Polysorbate 80 1.13 1.13 1.13 1.13 1.13 1.13 Dibutyl Adipate 2O.OO 2O.OO 2O.OO 2O.OO 2O.OO 2O.OO Part B Aqua QS. to 100 QS. to 100 QS. to 100 QS. to 100 QS. to 100 QS. to 100 Xanthan Gum O.2O O.20 O.2O O.20 O.2O O.20 Part C Sodium Acrylates Copolymer (and) 3.75 3.75 3.75 3.75 3.75 3.75 Mineral Oil (and) PPG-1 Trideceth-6 Part D Propylene Glycol (and) Diazolidinyl O.8O O.80 O.8O O.80 O.8O O.80 Urea (and) Methylparaben (and) Propylparaben Part E. Triethanolamine O.OO 4.OO 2.OO O.OO O.OO O.OO Ethanolamine O.OO O.OO O.OO 4.OO O.OO O.OO Diethanolamine O.OO O.OO O.OO O.OO O.OO 4.00 Aminomethyl Propanol O.OO O.OO O.OO O.OO 4.OO O.OO Part F Dispersion 1 or dispersion 2 as described 8.OO 8.00 8.OO 8.00 8.OO 8.00 in Table 1

Manufacturing Instruction: (0169. Heat part A and B separately to 75° C. Add part A to part Bunder continuous stirring. Add part Cimmediately. Let cool down to 50° C. and add part D, add part E under stirring during 5 minutes and add part Fat room temperature. Characterization Methods: (0170 Storage at RT and 50° C. during 3 weeks. Micros copy (under polarized light) with Leitz, Diaplan microscope, MPF curves from 290 nm to 400 nm with Labsphere UV Transmittance analyzer and Sensory testing. TABLE 1 Composition of micronized amino substituted hydroxyphenylbenzophenone derivatives Dispersion 1 Ingredients Dispersion 2

SO% 45-50% OH - 9 R / \ /- N N N N - / \ / Y, { \- HO

10% aqueous formulation of 51-55% Decyl Glucoside 1.5% Potassium Cetyl Phosphate aqueous formulation of 26-28% Sodium Myreth Sulfate 18.5% US 2010/0143274 A1 Jun. 10, 2010 21

TABLE 1-continued Composition of micronized amino substituted hydroxyphenylbenzophenone derivatives Dispersion 1 Ingredients Dispersion 2 O.1% Xanthan Gum O.1% O.2% 1.3 Butanediol O.2% O.S.-19. anti-foam emulsion containing 20% Simethicone. O.S.-19. ad 100% Water deion. ad 100% 120-140 Particle size (d50) in nm 120-140

Results: (c) 0.1 to 50% b.w. of an amine or an amide, Microscopy Examples 2, 3, 4 and 6 (1) O 0171 Crystal needles (1-200 um) may be observed under OH O A R3 polarized light within the formulations. R 0172 Speed and intensity of the formations of large par v N ticles are summarized in the Table 2. R2At 2 pi Example 5 wherein (0173 No particle growth observed after 3 weeks at 50° C. RandR independently from each other are C-Coalkyl: C-Coalkenyl: Cs-Cocycloalkyl, C-Clocycloalkenyl: TABLE 2 or R and R together with the linking nitrogen atom form a 5- or 6-membered heterocyclic ring: Microscopy investigation of formulas of Examples 1 to 6 n is a number from 1 to 4. when n=1. OW formulation Ex. 1 Ex. 2 Ex. 3 Ex. 4 Ex. 5 Ex. 6 R is a saturated or unsaturated heterocyclic radical; hydroxy-C-C-alkyl, cyclohexyl optionally substituted RT 1 day with one or more C-Csalkyl; or phenyl optionally Sub stituted with a heterocyclic radical, aminocarbonyl or 3 weeks ------C-C alkylcarboxy; 50° C. 1 day ------when n is 2. 3 weeks ------R is an alkylene-, cycloalkylene, alkenylene or phenylene radical which is optionally interrupted by —O—, +++: strong (many crystal needles) —NH-, a carbonyl- or a carboxy group; a radical of ++: crystal needles formula CH C=C CH *; or R together with +: few crystal needles A forms a bivalent radical of the formula -: no particle growth observed

(CH2) (1a) 2n Sensory Aspect N A 0.174. After 3 weeks at 50° C. (CH2),

wherein Examples 4 and 5: shiny and fluid n is a number from 1 to 3: Examples 2, 3 and 6: less shiny and less fluid when n is 3. Example 1: mat, grainy and viscous R is an alkantriyl radical; when n is 4. R is an alkanetetrayl radical; A is —O—, or —N(Rs)—, and 1. A cosmetic composition comprising Rs is hydrogen; C-Csalkyl, or hydroxy-C-Csalkyl. 2. (canceled) (a) 0.1 to 20% b.w. of a micronized benzophenone UV 3. A composition according to claim 1, where in formula absorber of formula (1), (1) (b) 0.1 to 10% b.w. of a methoxydibenzoylmethane deriva R and R2 independently from each other are hydrogen; tive and C-Coalkyl, C-Coalkenyl: Cs-Cocycloalkyl, US 2010/0143274 A1 Jun. 10, 2010 22

Cs-Cocycloalkenyl; or RandR together with the link 8. A composition according to claim 1, wherein the ben ing nitrogenatom form a 5- or 6-membered heterocyclic Zophenone UV absorber corresponds to formula (3) r1ng, n is a number from 1 to 4: when n is 1. (3) R is a saturated or unsaturated heterocyclic radical; hydroxy-C-C-alkyl; or Cyclohexyl substituted with OH O A-R-A O OH one or more C-C alkyl: when n is 2. R is an alkylene-, cycloalkylene- or alkenylene radical In N OO OO, which is optionally interrupted by a carbonyl- or car A boxy group; R R when n is 3. R is an alkantriyl radical; wherein when n is 4. RandR independently from each other are hydrogen; or R is an alkanetetrayl radical; C-C alkyl, A is —O—, or —N(Rs)—, and A is —NH; or —O—; and Rs is hydrogen; C-Csalkyl, or hydroxy-C-Csalkyl. R is a C-C alkylene radical; or R together with A forms 4. A composition according to claim 1, where in formula a bivalent radical of the formula (1) R and R are C-Coalkyl. 5. A composition according to claim 1, where in formula (1) R and R have the same definition. 6. A composition according to claim 1, where in formula (1) 9. A composition according to claim 1, wherein the meth n is 2 and oxydibenzoylmethane is 4-(tert-butyl)-4'-methoxydiben R is a C-C alkylene radical. Zoylmethane. 7. A composition according to claim 1, where in formula 10. A composition according to claim 1, comprising (1) amines selected from mono-, di-, and triethanolamines. n is 2. 11. A composition according to claim 1, comprising R is a radical of formula amines selected from aminomethyl Propanol (AMP), ethano lamine (EA), diethyl ethanolamine (DEA), tromethamine (Tris Amino) and triethanolamine (TEA). 12. A composition according to claim 1, comprising CH amines selected from amine oxides of formula (6) RR'R"NO, wherein -cis-O)-cis- -cis--ch R is C-Coalkyl, and CH3 R" and R" independently from each other are C-C alkyl. 13. A composition according to claim 1, comprising amines selected from alkoxylated amines of formula (4a) or nin-"s. (4b)

(4a) (CH-CH-O)-H " I t / R-N '-ch- C-O- cha-i-ch V CH3 CH3 (CH-CH-O)-H (4b) (CH-CH-O).-H or R together with A forms a bivalent radical of the formula /

(CH2CH2O), (CH-CH-O)-H

wherein R is C-Coalkyl; and r is 0; or 1; and X, y and Z independently from each other are a number q is a number from 0 to 5. from 1 to 20. US 2010/0143274 A1 Jun. 10, 2010

14. A composition according to claim 1, comprising wherein amines selected from alkylamido alkylamines of formula (5) R is C-Coalkyl; R" and R" independently from each other are hydrogen; or (5) C-C alkyl: O Y X and X" independently from each other are hydrogen; or ul N SulfoSuccinyl: R 1- YH.CHOX n is a number from 2 to 60; in and m independently from each other are a number wherein from 1 to 60, and the sum of n+m23. R is C-Coalkyl, 17. A composition according to claim 1, comprising X is hydrogen; or —CHCOO. Na+ and amines selected from mono-, di-, and triethanolamines, and Y is -CHCOO. Na+. CHCHCOO. Na+, where —CHCHOHCHSO, Na+, O CHCHOHCHOPOH+Na+. the micronized UV absorber corresponds to formula (3) 15. A composition according to claim 1, comprising amides selected from alkanolamides of formula (2) (3) (2) O X OH O A-R-A O OH N X-XV R Y

A OO OO w wherein R is C-Coalkyl: R2 R2 X is CHR'CH-OH: R" is hydrogen; or C-Calkyl; and Y is CHRCHOH: C-Calkyl, O wherein C-Chydroxyalkyl. 16. A composition according to claim 1, comprising RandR independently from each other are hydrogen; or amides selected from alkoxylated amides of formula (3a) or C-C alkyl, (3b) A is —NH; or —O—; and R is a C-C alkylene radical; or R together with A forms a bivalent radical of the formula) (3a) O R

R N H 1. ---14 (3.b) (CHR-CH-O)-X and the methoxydibenzoylmethane derivative is 4-(tert-bu tyl)-4'-methoxydibenzoylmethane. 18-21. (canceled)