US 2005O136021A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2005/0136021 A1 Perry et al. (43) Pub. Date: Jun. 23, 2005

(54) ACTIVE-RELEASING CYCLIC SILOXANES Publication Classification (76) Inventors: Robert J. Perry, Niskayuna, NY (US); (51) Int. Cl." ...... A61K 7/06; A61K 7/11; Mark D. Leatherman, Elmsford, NY CO7F 7/08 (US); Shahid Murtuza, Albany, NY (52) U.S. Cl...... 424/70.12; 556/437 (US) (57) ABSTRACT Correspondence Address: Kenneth S. Wheelock Cyclic Siloxanes that contain releasable active ingredients General Electric Company are described. The active ingredient can be an alcohol or One Plastics Avenue enolizable carbonyl-containing compound Such as a ketone, Pittsfield, MA 01201 (US) aldehyde, or ester. The product Siloxanes are useful in a variety of personal and household care products where slow (21) Appl. No.: 10/742,033 or controlled release of active ingredient is desired. A preferred embodiment utilizes substituents that when (22) Filed: Dec. 19, 2003 released as active ingredients are fragrant. US 2005/O136021 A1 Jun. 23, 2005

ACTIVE-RELEASING CYCLIC SILOXANES tization of actives to give hydrolyzable organic (i.e., not containing Silicon) molecules has also been well docu CROSS-REFERENCE TO RELATED mented in the literature. APPLICATIONS 0005 The marriage of silicon-containing molecules with 0001. Not Applicable active ingredients is of particular interest Since many active ingredients are highly functional organics and Suffer from STATEMENT REGARDING FEDERALLY incompatibility with the Silicones that are found in personal FUNDED RESEARCH and consumer care products, leading to Syneresis and other 0002) Not Applicable phase Separation phenomena. Derivatization of Silanes with long-chain alcoholic skin care actives to give alkoxytrim FIELD OF THE INVENTION ethysilanes (U.S. Pat. No. 5,847,179) and derivatization of Silanes with hydroxycarboxylic acid skin exfoliants to form 0003. The present invention relates to cyclic siloxanes (triorganosilyl)alkoxycarboxylates (U.S. Pat. No. 6,143,309; Suitable for use in a variety of applications including per U.S. Pat. No. 6.228,380; U.S. Pat. No. 6,267,977) have been Sonal care formulations, household products, automotive, described. Direct displacement of an alkoxy leaving group textiles and molding materials wherein the cyclic Siloxane on a Silicon atom by a fragrant alcohol was reported by has been chemically modified to release an active ingredient Allen, et al. to give fragrant Silicon esters or linear Silicate upon hydrolysis. The present invention further relates to esters (U.S. Pat. No. 3,215,719 and U.S. Pat. No. 3,271,305). Such molecules where the rate of active ingredient release is Several others also reported Similar alkoxy displacement sufficiently slow so that products formulated with the modi reaction to form linear fragrant Siloxane polymerS or copoly fied cyclic siloxane exhibit desirable effects for long periods mers (GB 2,041,964; GB 2,042.890; EP 273266). Reaction of time. of an alcohol, aldehyde, ketone or lactone with a silyl hydride in the presence of a metal carboxylate Salt and a BACKGROUND OF THE INVENTION reducing agent to form linear polymers and copolymers was 0004. The slow, Sustained release of an active ingredient also reported (WO 9628497). Other routes to fragrant sili is a highly desirable trait in many personal care, textile, cones using Silyl hydrides were disclosed by AnderSon, et al. automotive, plastic, laundry and household products. A (EP878497; JP 10330382: U.S. Pat. No. 6,262.287) and number of means have been proposed and implemented to Perry, et al. (U.S. Pat. No. 6,046,156; U.S. Pat. No. 6,077, achieve this goal. Among these means are dissolving or 923; U.S. Pat. No. 6,153,578; U.S. Pat. No. 6,054,547; U.S. Suspending fragrant compounds in personal care emulsions Pat. No. 6,075,111; U.S. Pat. No. 6,322,777; U.S. Pat. No. (U.S. Pat. No. 5,525,588; U.S. Pat. No. 5,525,555; U.S. Pat. 6,083,901). In these processes, hydrosilylation chemistry No. 5,490,982: U.S. Pat. No. 5,372,806; EP 0334490; WO was employed to join the active portion of the molecule to 0064497), encapsulation of a fragrant compound (U.S. Pat. the Silicone backbone. No. 5,500,223; U.S. Pat. No. 5,324.444; U.S. Pat. No. 5,185,155; U.S. Pat. No. 5,176,903; U.S. Pat. No. 5,130,171; SUMMARY OF THE INVENTION U.S. Pat. No. 6,325,859; U.S. Pat. No. 6,309,715; U.S. Pat. No. 6,325,274; U.S. Pat. No. 6,213,409; U.S. Pat. No. 0006 The present invention provides for an active ingre 6,200,949; U.S. Pat. No. 6,042,792; U.S. Pat. No. 5,867,755; dient-releasing cyclic Siloxane having formula I or II: U.S. Pat. No. 5,049,182, US patent applications 20020187221, 20020009522, and 20010008635; EP 1116515, EP 1061124, EP 1133929; WO 0179303, WO 0173188, WO 9815192, WO 02076514), dissolving a fra grant compound into a hydrophobic phase Such as a Silicone (U.S. Pat. No. 5,449,512; U.S. Pat. No. 5,160,494; U.S. Pat. No. 5,234,689; WO 024.1709), incorporation of a fragrant compound into crosslinked polymers (U.S. Pat. No. 6,435, 423: U.S. Pat. No. 5,139,864; U.S. Pat. No. 6,379,689; U.S. II Pat. No. 5,387,622; U.S. Pat. No. 5,387,411; WO 03032749; WO 02065858; JP 11047581), incorporation of fragrant compounds into permeable laminates (U.S. Pat. No. 6,500, 444; U.S. Pat. No. 5,071,704; U.S. Pat. No. 5,008,115), incorporation of fragrant compounds into matrices that soften at body temperature (U.S. Pat. No. 4,908,208; EP 1178.107; WO 0016643), incorporation of fragrant com pounds into matrices that biodegrade (U.S. Pat. No. 6,121, 0007) R', R'', R', and R' are each independently 343) or are bioactivated (U.S. Pat. No. 5,378,468), incor Selected from the group of monovalent C-C hydrocarbon poration of fragrant compounds into rate controlling radicals. AS used herein, the phrase monovalent hydrocarbon membranes (U.S. Pat. No. 6,063,365 and U.S. Pat. No. radical includes both aliphatic and aromatic monovalent 4,445,641), derivatization of Silanes with fragrant alcohols hydrocarbon radicals that may also include heteroatoms to form alkoxy silanes (U.S. Pat. No. 4,524,018 and U.S. Such as Oxygen, nitrogen, phosphorous, and Sulfur as well as Pat. No. 4,500,725), and derivatization of fragrances to form the halogens fluorine, chlorine, bromine, and iodine. The photoSensitive molecules that release the fragrance upon quantities n and q are each independently greater than or exposure to light (WO 02083620; JP2002020783A). Deriva equal to 1, and the quantities p, r, and S are each indepen US 2005/O136021 A1 Jun. 23, 2005 dently equal to or greater than 0 with the proviso that n+p where R', R and Rare independently monovalent hydro must be equal to or greater than 3 and that q+r--S must be carbon radicals having from four to one hundred carbon equal to or greater than 3. atoms, preferably five to one hundred carbon atoms, more preferably six to one hundred carbon atoms and most 0008) RF has the formula preferably Seven to one hundred carbon atoms that may also (RO),(RO),(RO),(R')(R) SiR with R' defined as a contain hetero-atoms Such as oxygen, Sulfur, nitrogen, phos C-C monovalent unsaturated hydrocarbon radical (which phorus and the halogens fluorine, chlorine, bromine and when having undergone hydrosilylation becomes a C-Co iodine. Group G is the group of carbonyl-containing actives, divalent hydrocarbon radical), where R, R and R are or carbonyl active ingredients, each independently having independently Selected or derived from group F or group G. the Structure: Group F is defined as the group of alcohols consisting of ROH, ROH, and ROH, wherein ROH, ROH, and ROH are alcoholic active ingredients, and group G is defined as 0014 wherein the carbonyl-containing active is capable the group of active ingredient esters, ketones, or aldehydes, of exhibiting the enol form of the carbonyl moiety under each independently having the Structure: reaction conditions as shown: 0009 with R" and Reach independently selected from 0015 and which will react through the enol hydroxyl the group consisting of monovalent hydrocarbon radicals group to form a carbon-oxygen-Silicon linkage (i.e. having from one to forty carbon atoms and monovalent R-C(R)=C(O-)-R) where the hyphen after the oxy alkoxy radicals having from one to forty carbon atoms, R gen in the formula indicates the Species is a monovalent a two to forty carbon atom monovalent unsaturated hydro radical and independently describes R', R and R), with R" carbon radical containing a terminal olefinic or acetylenic and R selected from the group consisting of monovalent moiety. The Subscript a has a value ranging from 1 to 3 and hydrocarbon radicals having from one to forty carbon atoms the Subscripts b, c, d, and e have values ranging from 0 to and monovalent alkoxy radicals having from one to forty 2 subject to the limitation that a +b+c+d+e=3. R7, R, and R' carbon atoms, R a C-Cao monovalent unsaturated hydro are each independently Selected from the group consisting of carbon radical containing a reactive olefinic or acetylenic hydrogen and monovalent hydrocarbon radicals having one moiety, which is preferably a terminal olefin or acetylene, to one hundred carbon atoms. where the Subscript a has a value ranging from 1 to 3 and the Subscripts b, c, d, and e have values ranging from 0 to 2 0.010 The present invention also provides for composi subject to the limitation that a+b+c+d+e=3; R", R, and R' tions that comprise an active ingredient releasing Siloxane. are each independently Selected from the group consisting of Of particular use are cosmetic compositions that comprise hydrogen and monovalent hydrocarbon radicals having from an active ingredient releasing Siloxane Such as perfumes, one to one hundred carbon atoms. It should be noted that the skin creams, makeup, foundations and the like, as well as Structure: laundry agents Such as detergent compositions, rinse addi tives, fabric Softeners and the like. 0016 is a conjugate structure that corresponds to the enol DETAILED DESCRIPTION OF THE Structure: INVENTION 0.011 The compounds of the present invention introduce 0017 but missing the hydroxyl hydrogen. In the struc active ingredient moieties via hydrosilylation of an olefinic ture: Silane molecule. These resulting Siloxane molecules are useful in a variety of consumer care compositions. The 0018 the hyphen after the oxygen atom indicates a present invention is directed to new compositions of matter univalent bonding site wherein the Structure is a monovalent that are siloxanes that release an alcoholic or carbonyl radical. AS used herein, the phrase from one to one hundred containing active ingredient upon hydrolysis, where the carbon atoms is chosen wherein the class of available active ingredient can be illustrated by but not limited to carbonyl-containing actives is Subtended by the formula adhesion promoters, adhesives, anti-aging agents, antioxi R-CH(R)(C=O)-R. As used herein, the phrase dants, antiperSpirants, antistatic agents, biocides, bittering monovalent hydrocarbon radical includes both aliphatic and agents, bleaching agents, brighteners, colorants, condition aromatic monovalent hydrocarbon radicals that may also ers, defoamers, detergents, disinfectants, dispersing agents, include heteroatoms Such as oxygen, nitrogen, phosphorous, fillers, foaming agents, foam Stabilizers, fragrances, humec Sulfur and the halogens fluorine, chlorine, bromine and tants, hydrotropes, insect repellants, liquid crystals, mois iodine. turizers, odor absorbers, opacifying agents, oral care addi tives, pharmaceuticals, preservatives, rheology modifiers, 0019. The following synthetic examples are intended to Screening agents, Sequestering or chelating agents, Solubi illustrate the general Synthetic reactions Schemes that a lizers, Solvents, SunScreens, Surfactants, Suspending agents, perSon having ordinary skill in the art of Silicone chemistry tanning agents, thickeners, Vitamins or other nutrients, or would typically employ in order to prepare the olefinic Whitening agents. Silanes used by the present invention. These reaction Schemes are thus illustrative only and do not represent the 0012. The olefinic silanes utilized by the present inven only Synthetic pathways that may be utilized. tion are described by the formula: 0020 When the starting material is an alcoholic active (RO), (RPO),(RO), (R), (R) SiR ingredient Such as phenethanol, olefinic halosilanes or ole 0013 where R'O, RO and RO are independently finic Silicon alkoxides may be employed as Starting materials derived from group F or group G. Group F is the group of to produce the active ingredient releasing Siloxanes of the alcohols consisting of ROH, ROH, and ROH, wherein present invention via active-bearing olefinic silanes (reac ROH, ROH, and ROH are alcoholic active ingredients, tion schemes I-III). US 2005/O136021 A1 Jun. 23, 2005

-continued Reaction scheme I: CH th CH=CHCH(CH)CH(CH)OSICH=CH CH CH CH (O)-cisco -- cu-ch--a He CH 0022 as will allyldimethylchlorosilane react with cit ronellol in a similar, reaction Scheme V: CH

CH- cit-i-ocial Reaction scheme V: CH t HO1 CH2 Yot?, CH CH CH + CHFCHCHSiCl -- Reaction scheme II: 1. CH2 Cl H CH C He CH-1 YCH, 2 (O)-cisco -- chi-ch-chCl tic O ) CH CHF CH-SiCH t CH2 1. CH OCHCH CH-CHCHSiCI1 SCH, St. CH3 CH2 t 1 CH-1 C NCH, Reaction scheme III: OR 0023 Representative alcohols that are precursors of the active-containing Silanes or Siloxanes of the present inven (O)- CH2CH2OH + CHRCH- jor tion may be illustrated by but not limited to acetovanillone, OEt allyl amylglycolate, allyl isoamylglycolate, C.-amylci nammyl alcohol, anisyl alcohol, benzoin, benzyl alcohol, OR benzyl Salicylate, 1-butanol, butylated hydroxytoluene, butyl lactate, 2-t-butyl-5-methylphenol, 2-t-butyl-6-meth CHECH-SiOR ylphenol, carvacrol, carveol, 4-carvomenthenol, cedrol, cetyl alcohol, cinnamic alcohol, citronellol, o-creSol, OCH2CH m-creSol, p-creSol, crotyl alcohol, decahydro-2-naphthol, 1-decanol, 1-decen-3-ol, 9-decen-1-ol, diethyl malate, diethyl tartrate, dihydrocarveol, dihydromyrcenol, 2,6-diiso propylphenol, dimethicone copolyol, 2,6-dimethoxyphenol, 0021 where the R groups for reaction III may be Et 1,1-dimethoxy-3,7-dimethyloctan-7-ol, 2,6-dimethyl-4-hep (CH-) or -CH2CH2CHs. Similarly, 3-methyl-5-(2.2, tanol, 2,6-dimethylheptan-2-ol, 6,8-dimethyl-2-nonanol, 3,-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol will react 3,7-dimethyl-2,6-octadien-1-ol, 3,7-dimethyl-1,6-octadien with chloromethylvinylsilane in a similar fashion (reaction 3-ol, 3,7-dimethyl-1-octanol, 3,7-dimethyl-3-octanol, 3,7- scheme IV): dimethyl-6-octen-1-ol, 3,7-dimethyl-7-octen-1-ol, dimetol, 2-ethylfenchol, 4-ethylguaiacol, 2-ethyl-1-hexanol, ethyl 2-hydroxybenzoate, ethyl 3-hydroxybutyrate, 3-ethyl-2-hy Reaction scheme IV: droxy-2-cyclopenten-1-one, ethyl 2-hydroxycaproate, ethyl 3-hydroxyhexanoate, ethyl lactate, ethyl maltol, p-ethylphe CHCH th nol, ethyl Salicylate, eugenol, farneSol, fenchyl alcohol, CH-CHCH(CH3)CH(CH3)O-H + CISiCH=CH geraniol, glucose petaacetate, glycerol, glyceryl monoStear CH ate, guaiacol, 1-heptanol, 2-heptanol, 3-heptanol, cis-4-hep \ CH tenol, cis-3-heptenol, n-hexanol, 2-hexanol, 3-hexanol, cis 2-hexenol, cis-3-hexenol, trans-3-hexenol, 4-hexenol, cis-3- hexenyl hydrocinnamyl alcohol, 2-hydroxybenzoate, 2-hydroxyacetophenone, 4-hydroxybenzyl alcohol, 3-hy droxy-2-butanone, hydroxycitronellal, 4-(4-hydroxy-3- US 2005/O136021 A1 Jun. 23, 2005 methoxyphenyl)-2-butanone, 2-hydroxy-3-methyl-2-cyclo penten-1-one, 4-(p-hydroxyphenyl)-2-butanone, 2-hydroxy -continued 3,5,5-trimethyl-2-cyclohexenone, 6-isoascorbic acid, CH2 || isoborneol, isoeugenol, isophytol, isopropyl alcohol, p-iso propylbenzyl alcohol, 4-isopropylcylcohexanol, 3-isopropy ti lphenol, 4-isopropylphenol, 2-isopropylphenol, isopulegol, CH3-N CH R y H. lauryl alcohol, linalool, maltol, menthol, 4-methoxybenzyl C YT u. alcohol, 2-methoxy-4-methylphenol, 2-methoxy-4-propy CH-1 YCH, ch=ct, lphenol, 2-methoxy-4-Vinylphenol, C.-methylbenzyl alcohol, CH 2-methylbutanol, 3-methyl-2-butanol, 3-methyl-2-buten-1- ol, 2-methyl-3-buten-2-ol, methyl 2,4-dihydroxy-3,6-dim ethylbenzoate, 4-methyl-2,6-dimethoxyphenol, methyl N-3, 0025 Note that DMF is dimethylformamide. This reac 7-dimethyl-7-hydroxyoctylideneanthranilate, methyl tion Scheme may also be used to prepare the 3-methyl-3- 3-hydroxyhexanoate, 6-methyl-5-hepten-2-ol, 2-methylpen (3-(1-methylethylphenyl)propanal derivative: tanol, 3-methyl-3-pentanol, 2-methyl-4-phenylbutan-2-ol, 2-methyl-3-phenylpropan-2-ol, methyl Salicylate, 3-methyl 5-(2,2,3,-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, CH 2-methyl-2-vinyl-5-(1-hydroxy-1-methyl ethyl)-3,4-dihy CH CH drofuran, myrtenol, neohesperidin dihydrochalcone, neom 2 th enthol, nerol, nerolidol, trans-2-cis-6-nonadienol, 1,3- No? Socil-ch, nonanediol acetate, nonadyl, 2-nonanol, cis-6-nonen-1-ol, CH trans-2-nonen-1-ol, nonyl alcohol, 1-octanol, 2-octanol, 3-octanol, cis-3-octen-1-ol, cis-2-octen-1-ol, trans-2-octen -CHS 1-ol, cis-6-octen-1-ol, cis-octen-1-ol, 1-octen-3-ol, oleyl CH CH alcohol, patchouli alcohol, 3-pentanol, n-pentanol, 2-pen tanol, 1-penten-1-ol, cis-2-penten-1-ol, perillyl alcohol, 2-phenoxyethanol arabinogalactan, B-phenethyl alcohol, 0026. The reaction of carbonyl-containing species, e.g. phenethyl Salicylate, phenol, phenylacetaldehyde glyceryl esters, ketones and aldehydes, requires the establishment of acetal, 3-phenyl-1-pentanol, 5-phenyl-1-pentanol, 1-phenyl the keto enol tautomeric equilibrium. 1-pentanol, 1-phenyl-2-pentanol, 1-phenyl-3-methyl-1-pen 0027 Tautomerism is the chemical phenomenon of the tanol, phytol, pinacol, polyalkylene glycols, polySorbate 20, establishment of an equilibrium between two or more Struc polySorbate 60, polySorbate 80, prenol, n-propanol, prope turally distinct compounds. In nearly all cases, the difference nyl guaethol, propylene glycol, 2-propylphenol, 4-propy between one tautomeric form of the equilibrium compounds lphenol, resorcinol, retinol, Salicylaldehyde, Sorbitan and the other is the isomeric placement of a hydrogen atom. monoStearate, Sorbitol, Stearyl alcohol, Syringealdehyde, A prevalent form of tautomerism is the tautomeric equilib C-terpineol, tetrahydrogeraniol, tetrahydrolinalool, tetrahy rium established between a carbonyl compound (i.e. one dromyrcenol, thymol, triethyl citrate, 1,2,6-trihydroxyheX containing a carbonyl group) and having a hydrogen atom ane, p-O.C.-trimethylbenzyl alcohol, 2-(5.5,6-trimethylbicy alpha to the carbonyl group, i.e. an O. hydrogen: clo2.2.1]hept-2-ylcyclohexanol, 5-(2,2,3-trimethyl-3- cyclopentenyl)-3-methylpentan-2-ol, 3,7,-11-trimethyl-2,6, 10-dodecatrien-1-ol, 3,7,11-trimethyl-1,6,10-dodecatrien-3- ol, 3.5,5-trimethyl-1-hexanol, 10-undecen-1-ol, undecyl alcohol, vanillin, o-vanillin, vanillylbutyl ether, 4-vinylphe nol, 2.5-Xylenol, 2,6-Xylenol, 3.5-Xylenol, 2,4-Xylenol, and | || f Xylose. H O H 0024. When the starting material is a carbonyl-containing Keto Form Enol Form active ingredient Such as 2-methyl-3-(4-t-butylphenyl)pro panal, olefinic haloSilanes or olefinic Silicon alkoxides may be employed as Starting materials to produce the active 0028 Generally the equilibrium constant favors the keto releasing siloxanes of the present invention via active ingre form and the equilibrium lies well to the left. The extent of enolization is greatly affected by Solvent, concentration and dient bearing olefinic Silanes. temperature. When a strong base is present, both the enol and the keto form can lose a hydrogen ion (a proton), CH2 CH forming an enolate anion: YCH CH ?HsYoH || + clich-ch, )e( 3 O CH CH CH US 2005/O136021 A1 Jun. 23, 2005

0029. Since both of these structures differ only in the citronellyl acetate, citronellyl butyrate, citronellyl isobu placement of electrons, these are canonical forms of the tyrate, citronellyl propionate, citronellyl Valerate, cyclohex Same ion rather than tautomeric isomers. Because oxygen is aneethyl acetate, cyclohexyl acetate, cyclohexyl butyrate, more electronegative than carbon, the predominate canoni cyclohexyl isoValerate, cyclohexyl propionate, 6-decallac cal form is the one where the ionic charge is more localized tone, e-decalactone, y-decalactone, 4-decanolide, decyl on the oxygen atom. While the tautomeric equilibrium acetate, decylbutyrate, decyl propionate, diethyl malonate, between enols and ketones or aldehydes is not normally a diethyl Sebacate, diethyl Succinate, dihydrocarVyl acetate, preparative reaction, the equilibrium must occur Since dihydrocoumarin, dihydromyrcenyl acetate, dihydro-nor-di ketones and aldehydes often react through their enol forms cyclopentadienyl acetate, dihydroterpinyl acetate, 3,7-dim as they do instantly in the preparation of the compounds of ethyl-1,6-Octadien-3-yl acetate, 3,7-dimethyl-1,6-Octadien the present invention. This keto-enol tautomeric equilibrium 3-yl propionate, 3,7-dimethyloctan-3-yl acetate, C.C.- is also established for esters or organic acids, i.e. in the structures above when R includes an oxygen bound to an dimethylphenethyl acetate, C.C.-dimethylphenethylbutyrate, appropriate R group, e.g. OR", the compound is an organic 6,10-dimethyl-5.9-undecadien-2-yl acetate, 6-dodecallac tone, e-dodecalactone, Y-dodecalactone, ethyl acetate, ethyl ester. For a more detailed explanation of this chemistry See acetoacetate, ethyl 6-acetoxyhexanoate, ethyl 2-acetyl-3- J. March “Advanced Organic Chemistry,” John Wiley & phenylpropionate, ethyl benzoylacetate, 2-ethylbutyl Sons, New York (1985), pp. 66-68 and 527-529 and refer acetate, ethyl butyrate, ethyl cinnamate, ethyl cyclohex ences therein. anepropionate, ethyl decanoate, ethylene brassylate, ethyl 0030 Fragrant molecules, alcohols, ketones and alde 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate, ethyl 2,3- hydes, may be reacted as the alcohol or enol tautomer to epoxybutyrate, ethyl 2-methyl-4-penteneoate, ethyl hep produce Silicone or Siloxanes bearing fragrant moieties. The tanoate, ethyl hexanoate, ethyl trans-3-hexenoate, 2-ethyl reaction involves reaction of the alcoholic or enolic form of hexyl acetate, ethyl isobutyrate, ethyl isoValerate, ethyl the molecule with hydrogen, hydroxyl or halogen directly laurate, ethyl 2-mercaptopropionate, ethyl 3-mercaptopropi bonded to a silicon atom to form the fragrant derivative. The onate, ethyl 2-methylbutyrate, ethyl 2-methylpentanoate, reaction involves formation of the conjugate base related to ethyl (methylthio)acetate, methyl (methylthio)acetate, the alcohol or enol tautomeric form of the molecule: methyl 2-(methylthio) propionate, ethyl myristate, ethyl nonanoate, ethyl octanoate, ethyl palmitate, ethyl phenylac 0031) R'OH dissociates to H' and R"O (conjugate etate, ethyl 3-phenylpropionate, ethyl 3-phenyl-2,3-epoxy base), n=1, 2 or 3 (thus R' etc. as previously defined); butyrate, ethyl 3-phenylpropionate, ethyl propionate, ethyl 0032 where R"OH is a fragrant alcohol or the enol Stearate, ethyl 2,3,6,6-tetramethyl-2-cyclohexencarboxylate, tautomeric form of a fragrant ketone or aldehyde. Aldehydes ethyl (p-tolyloxy)acetate, ethyl undecanoate, ethyl Valerate, and ketones react with alcohol(s) R'OH to form hemiacetals eugenyl acetate, fenchyl acetate, geranyl acetate, geranyl (derived from aldehydes) or hemiketals (derived from butyrate, geranyl phenylacetate, geranyl propionate, guai ketones): RCH(O)+R'OH->RCH(OH)(OR") hemiacetal, acyl phenylacetate, guaicwood acetate, Y-heptalactone, hep which has a conjugate base obtained by removing the tyl acetate, heptylbutyrate, heptylisobutyrate, ()-6-hexade hydroxyl hydrogen: RCH(O)(OR") and RC(O)R"+R'OH-> cenlactone, 6-hexylactone, Y-hexylactone, 3-hexenyl RC(OH)(R'O)R" which has a conjugate base likewise acetate, cis-3-hexenyl 2-methylbutanoate, cis-3-hexenyl cis obtained by removing the hydroxyl hydrogen: RC(O 3-hexenoate, cis-3-hexenyl phenylacetate, trans-2-hexenyl )(R'O)R". As used herein the R" are fragrant moieties, i.e. acetate, hexyl acetate, hexyl butyrate, hexyl hexanoate, monovalent radicals, either as a neutrally charged monova hexyl isobutyrate, hexyl propionate, hexyl 2-methylbu lent radical (R" or R"O) or as a charged monovalent radical, tanoate, hexyl 3-methylbutanoate, hexyl phenylacetate, derived from the conjugate bases of fragrant molecules, e.g. isoamyl acetate, isoamyl acetoacetate, isoamyl butyrate, R*-O2-eRO. isoamyl cinnamate, isoamylhexanoate, isoamyl isobutyrate, isoamyl isoValerate, isoamyl laurate, isoamyl nonanoate, 0.033 Representative carbonyl-containing active ingredi isoamyl octanoate, isoamyl phenylacetate, isoamyl propi ents that are precursors of the active-containing Silanes of onate, isobornyl acetate, isobornyl propionate, isobutyl the present invention may be illustrated by but not limited to acetate, isobutylbutyrate, isobutyl cinnamate, isobutyl heX 4-acetoxy-3-pentyl-tetrahydropyran, allyl cinnamate, allyl anoate, isobutyl isobutyrate, isobutyl 2methylbutyrate, 2-ethylbutyrate, allyl cyclohexanepropionate, allyl hep isobutyl propionate, isoeugenyl acetate, isopropyl cin tanoate, allyl hexanoate, allyl isoValerate, allyl nonanoate, namate, isobutyl phenylacetate, isopropyl acetate, isopropyl allyl octanoate, allyl phenoxyacetate, allyl phenylacetate, butyrate, isopropyl isobutyrate, isopropyl myristate, isopro allyl propionate, C.-amylcinnamyl acetate, amyl octanoate, pyl palmitate, isopropyl phenylacetate, lauryl acetate, linallyl aniSyl acetate, anisylphenyl acetate, benzyl acetate, benzyl acetate, linallyl butyrate, linallyl isOValerate, menthalactone, acetoacetate, benzyl butyrate, benzyl cinnamate, benzyl menthyl acetate, menthyl cyclohexanecarboxylate, menthyl isobutyrate, benzyl isovalerate, benzyl phenylacetate, ben isovalerate, 4-methoxybenzyl acetate, 4-methoxybenzyl Zyl propionate, bornyl acetate, bornyl isoValerate, bornyl propionate, 2-methoxyphenyl acetate, 2-methoxy-4-(1-pro Valerate, butyl acetate, butylbutyrate, butylbutyrylactate, penyl)phenyl acetate, methyl acetate, C.-methylbenzyl 4-t-butylcyclohexyl acetate, butyl heptanoate, butyl hex acetate, C.-methylbenzyl butyrate, C.-methylbenzyl propi anoate, butyl isobutyrate, butyl isoValerate, butyl laurate, onate, 2-methylbutyl acetate, 2-methylbutylbutyrate, 2-me butyl propionate, butyl Stearate, 3-butylidenephthalide, thylbutyl isovalerate, 3-methylbutyl 2-methylbutanoate, butyl 2-methylbutyrate, butyl 10-undeceneoate, Y-butyrolac 2-methylbutyl 2-methylbutanoate, methyl p-t-butylpheny tone, carvyl acetate, carvyl propionate, caryophyllene lacetate, methyl butyrate, methyl cinnamate, methyl acetate, cedryl acetate, trans-cinnamyl acetate, trans-cin decanoate, methyl heptanoate, methyl hexanoate, methyl namylbutyrate, cinnamyl cinnamate, cinnamyl isobutyrate, isobutyrate, methyl isoValerate, methyl laurate, methyl N-2- US 2005/O136021 A1 Jun. 23, 2005 methyl-3-(4-t-butylphenylpropylidene) anthranilate, methyl none, 2-acetoxy-2,5-dimethyl-3(2H)furanone, 2-acetylcy myristate, methyl nonanoate, methyl octanoate, methyl clopentanone, 4-acetyl-1,1-dimethyl-6-t-butylindan, palmitate, 4-(4-methyl-3-pentenyl)-3-cyclohexenylmethyl 7-acetyl-1,1,3,4,4,6-hexamethylindan, 2-acetyl-2-thizoline, acetate, methyl 2-methylbutyrate, 2-methyl-6-methylen-7- 6-acetyl-1,1,2,4,4,7-hexamethyl tetralin, allyl C-ionone, octen-2-yl acetate, methyl 4-methylvalerate, methyl 2-me benzylideneacetone, 2,3-butanedione, 2-Sec-butylcyclohex thylpentanoate, methyl phenoxyacetate, 4-methylphenyl anone, 5-t-butyl-3,5-dinitro-2,6-dimethylacetophenone, butyrophenone, camphor, 2-decanone, 3-decanone, 3-decen phenylacetate, 2-methyl-3-phenylpropan-2-yl acetate, 2-one, dihydrocarvone, dihydro-3-ionone, dihydrojasmone, methyl 3-phenylpropionate, methyl propionate, 2-methyl 4,5-dihydro-3(2H)-thiophenone, 2',4'-dimethylacetophe propyl phenylacetate, methyl phenylacetate, 2-methyl-3- none, 3,4-dimethyl-1,2-cyclopentadione, 3,5-dimethyl-1,2- phenylpropan-2-yl acetate, methyl Stearate, methyl (p-toly cyclopentadione, 2,6-dimethyl-4-heptanone, 1,3-diphenyl loxy)acetate, methyl 9-undecenoate, methyl Valerate, 2-propanone, 4-(1-ethoxyvinyl)-3,3,5,5- myrtenyl acetate, neryl acetate, neryl butyrate, neryl isobu tetramethylcyclohexanone, p-ethylacetophenone, ethyl tyrate, Ö-nonalactone, Y-nomalactone, 1,3-nonanediol diac Vinyl ketone, geranylacetone, 2,3-heptanedione, 2-hep etate, nonyl acetate, nopyl acetate, octahydrocoumarin, Y-Oc tanone, 3-heptanone, 4-heptanone, 3,4-hexanedione, 3-hex talactone, 1-octen-3-yl acetate, 1-octen-3-yl butyrate, octyl anone, 4-hexen-3-one, 2-hexylidene cyclopentanone, C-ion One, B-ionone, 4-isobutyl-2,6-dimethyl-3,5- acetate, actyl butyrate, octyl isobutyrate, octyl isoValerate, dinitroacetophenone, isophorone, 6-isopropyldecahydro-2- octyl octanoate, octyl propionate, oxacycloheptadec-10-en naphthone, cis-jasmone, liveScone, 2-one, ()-pentadecalactone, pentyl acetate, pentylbutyrate, 4-methoxyacetophenone, 4-(p-methoxyphenyl)-2-butanone, pentylhexanoate, pentyl octanoate, phenethyl acetate, phen 4'-methylacetophenone, 3-methyl-1,2-cyclohexanedione, ethylbutyrate, phenethyl cinnamate, phenethyl hexanoate, 3-methyl-2-cyclohexen-1-one, 2-(2-(4-methyl-3-cylco phenethyl isobutyrate, phenethyl isoValerate, phenethyl hexen-1-yl)propyl)-cyclopentanone, 3-methyl-2-cyclo 2-methylbutyrate, phenethyl 2-methylbutyrate, phenethyl penten-1-one, methyl dihydrojasmonate, methyl ethyl ketone, 2-methyl-3-heptanone, 5-methyl-2-hepten-4-one, 2-methylpropionate, phenethyl octanoate, phenethyl pheny 6-methyl-5-hepten-2-one, 5-methyl-O-ionone, 1-(2-methyl lacetate, phenethyl propionate, phenoxyethyl propionate, 5-isopropyl-2-cyclohexenyl)-1-propanone, 4-methyl-2-pen 2-phenoxyethyl 2-methylpropionate, 3-phenyl-2-propenyl tanone, 3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one, propionate, 3-phenylpropyl acetate, 2-phenylpropyl 4-methyl-1-phenyl-2-pentanone, 2-methyltetrahydrofuran butyrate, 2-phenylpropyl isobutyrate, 2-phenylpropyl isov 3-one, 2-methyltetrahydrothiophen-3-one, 2-nonanone, alerate, piperonyl acetate, piperonyl isobutyrate, prenyl 3-nonanone, 2-octanone, 3-octanone, 1-octen-3-one, acetate, propyl acetate, propylbutyrate, propyl heptanoate, 3-octen-2-one, 4-oxoisophorone, 2-pentadecanone, 2,3-pen propyl hexanoate, 3-propylidenephthalide, propyl isobu tanedione, 2-pentanone, 3-pentanone, 3-penten-2-one, tyrate, propyl propionate, propyl phenylacetate, Sucrose 1-phenyl-1,2propandione, propiophenone, pullegone, octaacetate, terpinyl acetate, terpinyl butyrate, terpinyl 2-tridecanone, 2,2,6-trimethylcyclohexanone, 4-(2,6,6-trim isobutyrate, terpinyl propionate, tetrahydrofurfuryl acetate, ethyl-2-cylcohexen-1-yl)-3-methyl-3-buten-2-one, 2-unde tetrahydrofurfuryl butyrate, tetrahydrofurfuryl propionate, canone, and 6-undecanone. tetrahydrolinallyl acetate, 2,6,6,8-tetramethyl-tricyclo 0034. The active ingredient releasing siloxanes of the 5.3.1.0(1.5)udecan-8-yl acetate, p-tolyl acetate, p-tolyl present invention are prepared from an organohydrogen isobutyrate, p-tolyl phenylacetate, triacetin, tributyl acetyl Siloxane Via conventional hydrosilylation using the active citrate, tributyrin, tripropionin, 3.5,5-trimethylhexyl acetate, bearing olefinic Silane as the alkenyl Source, an example of 6-undecalactone, Y-undecalactone, Y-Valerolactone, Vanillin this reaction being: acetate, Vanillyl isobutyrate, 1-vinyl-2-(1-methylpropyl)cy clohexyl acetate, whiskey lactone, butyraldehyde, citronel lal, decanal, cis-4-decenal, trans-4-decenal, 2,4-dimethyl-3- cyclohexen-1-carbaldehyde, 2,6-dimethyl-5-heptenal, 3,7- dimethyloctanal, 2-ethylbutyraldehyde, glutaric dialdehyde, -- 2ns/ Pt heptanal, cis-4-heptenal, heXanal, hydrocinnamaldehyde,

isobutyraldehyde, 3-(p-isopropylphenyl)-propionaldehyde, isovaleraldehyde, lauric aldehyde, 2-methylbutyraldehyde, 2-methyl-3-(p-isopropylphenyl)propionaldehyde, 2-methyl pentanal, 4-(4-methyl-3-pentenyl)-3-cyclohexen-1-carbal dehyde, 4-methylphenylacetaldehyde, 3-(methylthio)buta nal, 2-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)butanal, 2-methylundecanal, nonanal, cis-6-nonenal, octanal, pheny lacetaldehyde, 2-phenylpropionaldehyde, 3-phenylpropi onaldehyde, propionaldehyde, p-tolylacetaldehyde, trideca nal, 2,4,6-trimethyl-3-cyclohexen-1-carbaldehyde, 2,6,10 trimethyl-9-undecanal, 7-undecenal, 8-undecenal, 0035) In this specific instance, the Siloxane Species is 9-undecenal, 10-undecenal, Valeraldehyde, acetanisole, actually a mixture of cyclic Siloxanes with y ranging from 1'-acetonaphthone, 2'-acetonaphthone, acetone, acetophe 3-15. US 2005/O136021 A1 Jun. 23, 2005

0.036 Thus an organohydrogensiloxane having formula bonyl-containing active ingredient resulting from hydrolysis III or IV: of Said Siloxane is Selected from the group of alcohols consisting of acetovanillone, allyl amylglycolate, allyl isoamylglycolate, C.-amylcinammyl alcohol, anisyl alcohol, III benzoin, benzyl alcohol, benzyl Salicylate, 1-butanol, buty lated hydroxytoluene, butyl lactate, 2-t-butyl-5-methylphe nol, 2-t-butyl-6-methylphenol, carvacrol, carveol, 4-carvo menthenol, cedrol, cetyl alcohol, cinnamic alcohol, citronellol, o-creSol, m-creSol, p-creSol, crotyl alcohol, IV decahydro-2-naphthol, 1-decanol, 1-decen-3-ol, 9-decen-1- ol, diethyl malate, diethyl tartrate, dihydrocarveol, dihy dromyrcenol, 2,6-diisopropylphenol, dimethicone copolyol, 2,6-dimethoxyphenol, 1,1-dimethoxy-3,7-dimethyloctan-7- ol, 2,6-dimethyl-4-heptanol, 2,6-dimethylheptan-2-ol, 6,8- dimethyl-2-nonanol, 3,7-dimethyl-2,6-octadien-1-ol, 3,7- dimethyl-1,6-octadien-3-ol, 3,7-dimethyl-1-octanol, 3,7- dimethyl-3-octanol, 3,7-dimethyl-6-octen-1-ol, 3,7- 0037 where R', R', R', and R' are each indepen dimethyl-7-octen-1-ol, dimetol, 2-ethylfenchol, dently Selected from the group of monovalent C-C hydro 4-ethylguaiacol, 2-ethyl-1-hexanol, ethyl 2-hydroxyben carbon radicals. The quantity t is greater than or equal to 3, Zoate, ethyl 3-hydroxybutyrate, 3-ethyl-2-hydroxy-2-cyclo the quantity u is greater than or equal to 1, and the quantity penten-1-one, ethyl 2-hydroxycaproate, ethyl 3-hydroxy S is greater than or equal to 0, with the proviso that u+S must hexanoate, ethyl lactate, ethyl maltol, p-ethylphenol, ethyl be equal to or greater than 3. Salicylate, eugenol, farneSol, fenchyl alcohol, geraniol, glu cose petaacetate, glycerol, glyceryl monoStearate, guaiacol, 0.038. The organohydrogensiloxane is reacted under 1-heptanol, 2-heptanol, 3-heptanol, cis-4-heptenol, cis-3- hydrosilylation conditions to produce an active-releasing heptenol, n-hexanol, 2-hexanol, 3-hexanol, cis-2-hexenol, siloxane having formula I or II: cis-3-hexenol, trans-3-hexenol, 4-hexenol, cis-3-hexenyl hydrocinnamyl alcohol, 2-hydroxybenzoate, 2-hydroxyac etophenone, 4-hydroxybenzyl alcohol, 3-hydroxy-2-bu tanone, hydroxycitronellal, 4-(4-hydroxy-3-methoxyphe nyl)-2-butanone, 2-hydroxy-3-methyl-2-cyclopenten-1-one, 4-(p-hydroxyphenyl)-2-butanone, 2-hydroxy-3,5,5-trim ethyl-2-cyclohexenone, 6-isoascorbic acid, isoborneol, isoeugenol, isophytol, isopropyl alcohol, p-isopropylbenzyl alcohol, 4-isopropylcylcohexanol, 3-isopropylphenol, 4-iso II propylphenol, 2iSopropylphenol, isopulegol, lauryl alcohol, linalool, maltol, menthol, 4-methoxybenzyl alcohol, 2-meth oxy-4-methylphenol, 2-methoxy-4-propylphenol, 2-meth oxy-4-vinylphenol, C.-methylbenzyl alcohol, 2-methylbu tanol, 3-methyl-2-butanol, 3-methyl-2-buten-1-ol, 2-methyl-3-buten-2-ol, methyl 2,4-dihydroxy-3,6-dimethyl benzoate, 4-methyl-2,6-dimethoxyphenol, methyl N-3,7- dimethyl-7-hydroxyoctylideneanthranilate, methyl 3-hy 0.039 where the components and subscripts satisfy the droxyhexanoate, 6-methyl-5-hepten-2-ol, 2-methylpentanol, previous definitions and requirements and R has the for 3-methyl-3-pentanol, 2-methyl-4-phenylbutan-2-ol, 2-me mula (RO),(RO),(RO),(R").(R), SiR with R a C-C, thyl-3-phenylpropan-2-ol, methyl Salicylate, 3-methyl-5-(2, divalent hydrocarbon radical where the Subscripts and com 2,3,-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methyl ponents are as previously defined. This siloxane undergoes 2-vinyl-5-(1-hydroxy-1-methyl ethyl)-3,4-dihydrofuran, a slow hydrolysis under most conditions of use whereby the myrtenol, neohesperidin dihydrochalcone, neomenthol, Siloxane releases an alcoholic or carbonyl-containing active nerol, nerolidol, trans-2-cis-6-nonadienol, 1,3-nonanediol ingredient upon hydrolysis. This imparts a desirable effect to acetate, nonadyl, 2-nonanol, cis-6-nonen-1-ol, trans-2- many different useful compositions Such as cosmetics and nonen-1-ol, nonyl alcohol, 1-octanol, 2-octanol, 3-octanol, household products. cis-3-octen-1-ol, cis-2-octen-1-ol, trans-2-octen-1-ol, cis-6- octen-1-ol, cis-octen-1-ol, 1-octen-3-ol, oleyl alcohol, 0040. The hydrosilylation reaction is conventionally car patchouli alcohol, 3-pentanol, n-pentanol, 2-pentanol, ried out in the presence of a hydrosilylation catalyst Selected 1-penten-1-ol, cis-2-penten-1-ol, perillyl alcohol, 2-phe from the group of ruthenium, OSmium, rhodium, iridium, noxyethanol arabinogalactan, C.-phenethyl alcohol, phen palladium and platinum hydrosilylation catalysts. Exem ethyl Salicylate, phenol, phenylacetaldehyde glyceryl acetal, plary of such catalysts are those described in U.S. Pat. Nos. 3-phenyl-1-pentanol, 5-phenyl-1-pentanol, 1-phenyl-1-pen 2,823,218; 3,159,601; 3,159,662; and 3,775,452. tanol, 1-phenyl-2-pentanol, 1-phenyl-3-methyl-1-pentanol, 0041. The compositions of the present invention further phytol, pinacol, polyalkylene glycols, polySorbate 20, provide that the active ingredient releasing siloxane have polySorbate 60, polySorbate 80, prenol, n-propanol, prope one or more substituents R', R, or R where each substitu nyl guaethol, propylene glycol, 2-propylphenol, 4-propy ent is independently Selected whereby an alcoholic or car lphenol, resorcinol, retinol, Salicylaldehyde, Sorbitan US 2005/O136021 A1 Jun. 23, 2005 monoStearate, Sorbitol, Stearyl alcohol, Syringealdehyde, 2-methylbutanoate, cis-3-hexenyl cis-3-hexenoate, cis-3- C-terpineol, tetrahydrogeraniol, tetrahydrolinalool, tetrahy hexenyl phenylacetate, trans-2-hexenyl acetate, hexyl dromyrcenol, thymol, triethyl citrate, 1,2,6-trihydroxyheX acetate, hexylbutyrate, hexyl hexanoate, hexyl isobutyrate, ane, p-O.C.-trimethylbenzyl alcohol, 2-(5.5,6-trimethylbicy hexyl propionate, hexyl 2-methylbutanoate, hexyl 3-meth clo2.2.1]hept-2-ylcyclohexanol, 5-(2,2,3-trimethyl-3- ylbutanoate, hexyl phenylacetate, isoamyl acetate, isoamyl cyclopentenyl)-3-methylpentan-2-ol, 3,7,-11-trimethyl-2,6, acetoacetate, isoamylbutyrate, isoamyl cinnamate, isoamyl 10-dodecatrien-1-ol, 3,7,11-trimethyl-1,6,10-dodecatrien-3- hexanoate, isoamyl isobutyrate, isoamyl isOValerate, ol, 3.5,5-trimethyl-1-hexanol, 10undecen-1-ol, undecyl isoamyl laurate, isoamyl nonanoate, isoamyl octanoate, alcohol, vanillin, o-vanillin, vanillylbutyl ether, 4-vinylphe isoamyl phenylacetate, isoamyl propionate, isobornyl nol, 2.5-Xylenol, 2,6-Xylenol, 3.5-Xylenol, 2,4-Xylenol, and acetate, isobornyl propionate, isobutyl acetate, isobutyl Xylose or from the group of carbonyl-containing compounds butyrate, isobutyl cinnamate, isobutyl hexanoate, isobutyl consisting of 4-acetoxy-3-pentyl-tetrahydropyran, allyl cin isobutyrate, isobutyl 2-methylbutyrate, isobutyl propionate, namate, allyl 2-ethylbutyrate, allyl cyclohexanepropionate, isoeugenyl acetate, isopropyl cinnamate, isobutyl phenylac allyl heptanoate, allyl hexanoate, allyl isoValerate, allyl etate, isopropyl acetate, isopropylbutyrate, isopropyl isobu nonanoate, allyl octanoate, allyl phenoxyacetate, allyl phe tyrate, isopropyl myristate, isopropyl palmitate, isopropyl nylacetate, allyl propionate, C.-amylcinnamyl acetate, amyl phenylacetate, lauryl acetate, linallyl acetate, linallylbutyrate, octanoate, anisyl acetate, anisylphenyl acetate, benzyl linallyl isoValerate, menthalactone, menthyl acetate, menthyl acetate, benzyl acetoacetate, benzyl butyrate, benzyl cin cyclohexanecarboxylate, menthyl isoValerate, 4-methoxy namate, benzyl isobutyrate, benzyl isoValerate, benzyl phe benzyl acetate, 4-methoxybenzyl propionate, 2-methoX nylacetate, benzyl propionate, bornyl acetate, bornyl isov yphenyl acetate, 2-methoxy-4-(1-propenyl)phenyl acetate, alerate, bornyl Valerate, butyl acetate, butylbutyrate, butyl methyl acetate, C.-methylbenzyl acetate, C.-methylbenzyl butyryllactate, 4-t-butylcyclohexyl acetate, butyl hep butyrate, C.-methylbenzyl propionate, 2-methylbutyl acetate, tanoate, butyl hexanoate, butyl isobutyrate, butyl isoValer 2-methylbutylbutyrate, 2-methylbutyl isovalerate, 3-meth ate, butyl laurate, butyl propionate, butyl Stearate, 3-butyl ylbutyl 2-methylbutanoate, 2-methylbutyl 2-methylbu idenephthalide, butyl 2-methylbutyrate, butyl tanoate, methyl p-t-butylphenylacetate, methyl butyrate, 10-undeceneoate, Y-butyrolactone, carvyl acetate, carvyl methyl cinnamate, methyl decanoate, methyl heptanoate, propionate, caryophyllene acetate, cedryl acetate, trans methyl hexanoate, methyl isobutyrate, methyl isOValerate, cinnamyl acetate, trans-cinnamyl butyrate, cinnamyl cin methyl laurate, methyl N-2-methyl-3-(4-t-butylphenylpro namate, cinnamyl isobutyrate, citronellyl acetate, citronellyl pylidene) anthranilate, methyl (methylthio)acetate, methyl butyrate, citronellyl isobutyrate, citronellyl propionate, cit 2-(methylthio) propionate, methyl myristate, methyl ronellyl Valerate, cyclohexaneethyl acetate, cyclohexyl nonanoate, methyl octanoate, methyl palmitate, 4-(4-me acetate, cyclohexylbutyrate, cyclohexyl isoValerate, cyclo thyl-3-pentenyl)-3-cyclohexenylmethyl acetate, methyl hexyl propionate, 6-decalactone, e-decalactone, y-decallac 2-methylbutyrate, 2-methyl-6-methylen-7-octen-2-yl tone, 4-decanolide, decyl acetate, decyl butyrate, decyl acetate, methyl 4-methylvalerate, methyl 2-methylpen propionate, diethyl malonate, diethyl Sebacate, diethyl Suc tanoate, methyl phenoxyacetate, 4-methylphenyl phenylac cinate, dihydrocarvyl acetate, dihydrocoumarin, dihy etate, 2-methyl-3-phenylpropan-2-yl acetate, methyl 3-phe dromyrcenyl acetate, dihydro-nor-dicyclopentadienyl nylpropionate, methyl propionate, 2-methylpropyl acetate, dihydroterpinyl acetate, 3,7-dimethyl-1,6-Octadien phenylacetate, methyl phenylacetate, 2-methyl-3-phenyl 3-yl acetate, 3,7-dimethyl-1,6-octadien-3-yl propionate, 3,7- propan-2-yl acetate, methyl Stearate, methyl (p-tolyloxy)ac dimethyloctan-3-yl acetate, C.C.-dimethylphenethyl acetate, etate, methyl 9-undecenoate, methyl Valerate, myrtenyl O.C.-dimethylphenethylbutyrate, 6,10-dimethyl-5.9-undeca acetate, neryl acetate, neryl butyrate, neryl isobutyrate, dien-2-yl acetate, 6-dodecalactone, e-dodecalactone, Ö-nonalactone, C.-nonalactone, 1,3-nonanediol diacetate, Y-dodecalactone, ethyl acetate, ethyl acetoacetate, ethyl nonyl acetate, nopyl acetate, octahydrocoumarin, Y-Octalac 6-acetoxyhexanoate, ethyl 2-acetyl-3-phenylpropionate, tone, 1-octen-3-yl acetate, 1-octen-3-yl butyrate, octyl ethyl benzoylacetate, 2-ethylbutyl acetate, ethyl butyrate, acetate, octyl butyrate, octyl isobutyrate, octyl isoValerate, ethyl cinnamate, ethyl cyclohexanepropionate, ethyl octyl octanoate, octyl propionate, oxacycloheptadec-10-en decanoate, ethylene brassylate, ethyl 2-ethyl-6,6-dimethyl 2-one, ()-pentadecalactone, pentyl acetate, pentylbutyrate, 2-cyclohexenecarboxylate, ethyl 2,3-epoxybutyrate, ethyl pentylhexanoate, pentyl octanoate, phenethyl acetate, phen 2-methyl-4-penteneoate, ethylheptanoate, ethylhexanoate, ethylbutyrate, phenethyl cinnamate, phenethyl hexanoate, ethyl trans-3-hexenoate, 2-ethylhexyl acetate, ethyl isobu phenethyl isobutyrate, phenethyl isovalerate, phenethyl tyrate, ethyl isoValerate, ethyl laurate, ethyl 2-mercaptopro 2-methylbutyrate, phenethyl 2-methylbutyrate, phenethyl pionate, ethyl 3-mercaptopropionate, ethyl 2-methylbu 2-methylpropionate, phenethyl octanoate, phenethyl pheny tyrate, ethyl 2-methylpentanoate, ethyl (methylthio)acetate, lacetate, phenethyl propionate, phenoxyethyl propionate, ethyl myristate, ethyl nonanoate, ethyl octanoate, ethyl 2-phenoxyethyl 2-methylpropionate, 3-phenyl-2-propenyl palmitate, ethyl phenylacetate, ethyl 3-phenylpropionate, propionate, 3-phenylpropyl acetate, 2-phenylpropyl ethyl 3-phenyl-2,3-epoxybutyrate, ethyl 3-phenylpropi butyrate, 2-phenylpropyl isobutyrate, 2-phenylpropyl isov onate, ethyl propionate, ethyl Stearate, ethyl 2,3,6,6-tetram alerate, piperonyl acetate, piperonyl isobutyrate, prenyl ethyl-2-cyclohexencarboxylate, ethyl (p-tolyloxy)acetate, acetate, propyl acetate, propylbutyrate, propyl heptanoate, ethyl undecanoate, ethyl Valerate, eugenyl acetate, fenchyl propyl hexanoate, 3-propylidenephthalide, propyl isobu acetate, geranyl acetate, geranylbutyrate, geranyl phenylac tyrate, propyl propionate, propyl phenylacetate, Sucrose etate, geranyl propionate, guaiacyl phenylacetate, guaic octaacetate, terpinyl acetate, terpinyl butyrate, terpinyl Wood acetate, Y-heptalactone, heptyl acetate, heptyl isobutyrate, terpinyl propionate, tetrahydrofurfuryl acetate, butyrate, heptylisobutyrate, ()-6-hexadecenlactone, 6-hexy tetrahydrofurfuryl butyrate, tetrahydrofurfuryl propionate, lactone, Y-hexylactone, 3-hexenyl acetate, cis-3-hexenyl tetrahydrolinallyl acetate, 2,6,6,8-tetramethyl-tricyclo US 2005/O136021 A1 Jun. 23, 2005

5.3.1.0(1.5)udecan-8-yl acetate, p-tolyl acetate, p-tolyl limited to deodorants, antiperSpirants, insect repellants, skin isobutyrate, p-tolyl phenylacetate, triacetin, tributyl acetyl creams, facial creams, hair care products Such as Shampoos, citrate, tributyrin, tripropionin, 3.5,5-trimethylhexyl acetate, mousses, Styling gels, protective creams, shaving creams, Ö-undecalactone, Y-undecalactone, Y-Valerolactone, Vanillin after Shave, cologne, perfume, color cosmetics Such as acetate, Vanillyl isobutyrate, 1-vinyl-2-(1-methylpropyl)cy lipsticks, foundations, blushes, makeup, and mascara, and clohexyl acetate, whiskey lactone, butyraldehyde, citronel other cosmetic formulations where other Silicon-containing lal, decanal, cis-4-decenal, trans-4-decenal, 2,4-dimethyl-3- components have been added and where it is desirable to cyclohexen-1-carbaldehyde, 2,6-dimethyl-5-heptenal, 3,7- impart a certain effect. Incorporation of Small amounts of the dimethyloctanal, 2-ethylbutyraldehyde, glutaric dialdehyde, compositions of the present invention into fragrance prod heptanal, cis-4-heptenal, heXanal, hydrocinnamaldehyde, ucts Such as shaving lotions, colognes, toilet water, and isobutyraldehyde, 3-(p-isopropylphenyl)propionaldehyde, perfumes can impart a desirable long lasting fragrance to isovaleraldehyde, lauric aldehyde, 2-methylbutyraldehyde, these products. Further, the Siloxanes of the present inven 2-methyl-3-(p-isopropylphenyl)propionaldehyde, 2-methyl tion may be incorporated into other products where it is pentanal, 4-(4-methyl-3-pentenyl)-3-cyclohexen-1-carbal desirable to mask unpleasant odors with a pleasant fra dehyde, 4-methylphenylacetaldehyde, 3-(methylthio)buta grance, for example household cleaning products Such as nal, 2-methyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)butanal, waxes and polishes, automobile cleaning products Such as 2-methylundecanal, nonanal, cis-6-nonenal, octanal, pheny waxes and polishes, detergents, textile coatings, paints, lacetaldehyde, 2-phenylpropionaldehyde, 3-phenylpropi Varnishes and the like, Subject to the limitation that the onaldehyde, propionaldehyde, p-tolylacetaldehyde, trideca Siloxane of the present invention be compatible or capable of nal, 2,4,6-trimethyl-3-cyclohexen-1-carbaldehyde, 2,6,10 being rendered compatible with the product in which it is trimethyl-9-undecanal, 7undecenal, 8-undecenal, incorporated. 9-undecenal, 10-undecenal, Valeraldehyde, acetanisole, 1'-acetonaphthone, 2'-acetonaphthone, acetone, acetophe EXPERIMENTAL none, 2-acetoxy-2,5-dimethyl-3(2H)furanone, 2-acetylcy clopentanone, 4-acetyl-1,1-dimethyl-6-t-butylindan, Example 1 7-acetyl-1,1,3,4,4,6-hexamethylindan, 2-acetyl-2-thiazo 0043. In a glass roundbottom flask, silane V (19.9 g, line, 6-acetyl-1,1,2,4,4,7-hexamethyl tetralin, allyl C-ion 0.083 mol) was charged and stirred for 15 min. A 10.9% one, benzylideneacetone, 2,3-butanedione, 2-sec-butylcy solution of Pt(0) in divinyltetramethylsiloxane (15 mg of clohexanone, 5-t-butyl-3,5-dinitro-2,6- Solution, 100 ppm Pt) was added. Tetramethylcyclotetrasi dimethylacetophenone, butyrophenone, camphor, loxane (5.07 g., 0.083 mol hydride) was then added to the 2-decanone, 3-decanone, 3-decen-2-one, dihydrocarvone, dihydro-f-ionone, dihydrojasmone, 4,5-dihydro-3(2H)- reaction mixture over 30 min. A slight exotherm was thiophenone, 2',4'-dimethylacetophenone, 3,4-dimethyl-1,2- observed. The reaction mixture was then heated to 65 C. cyclopentadione, 3,5-dimethyl-1,2-cyclopentadione, 2,6- and maintained at said temperature for 5 h. The volatiles dimethyl-4-heptanone, 1,3-diphenyl-2-propanone, 4-(1- were then stripped under vacuum (70° C., 0.5 mm Hg) for ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone, 1.5 h. The brown product was mixed with Celite and filtered p-ethylacetophenone, ethyl vinyl ketone, geranylacetone, to give 17.9 g of a straw colored fluid (71.6%). 2,3-heptanedione, 2-heptanone, 3-heptanone, 4-heptanone, Example 2 3,4-hexanedione, 3-hexanone, 4-hexen-3-one, 2-hexylidene cyclopentanone, C.-ionone, B-ionone, 4-isobutyl-2,6-dim 0044) In a glass roundbottom flask, silane VI (19.3 g, ethyl-3,5-dinitroacetophenone, isophorone, 6-isopropyl 0.093 mol) was charged and stirred. A 10.9% solution of decahydro-2-naphthone, cis-jasmone, liveScone, 4-meth Pt(0) in divinyltetramethylsiloxane (17 mg of solution, 74 Oxyacetophenone, 4-(p-methoxyphenyl)-2-butanone, ppm Pt) was added. Tetramethylcyclotetrasiloxane (5.71 g, 4'-methylacetophenone, 3-methyl-1,2-cyclohexanedione, 0.093 mol hydride) was then added to the reaction mixture 3-methyl-2-cyclohexen-1-one, 2-(2-(4-methyl-3-cylco over 25 min. The reaction mixture was then heated to 65 C. hexen-1-yl)propyl)cyclopentanone, 3-methyl-2-cyclo and maintained at Said temperature for 6 h. The Volatiles penten-1-one, methyl dihydrojasmonate, methyl ethyl were then stripped under vacuum (70° C., 0.5 mm Hg) for ketone, 2-methyl-3-heptanone, 5-methyl-2-hepten-4-one, 1.5 h. The product was mixed with Celite and filtered to give 6-methyl-5-hepten-2-one, 5-methyl-O-ionone, 1-(2-methyl 15.2 g of pale brown fluid (60.8%). 5-isopropyl-2-cyclohexenyl)-1-propanone, 4-methyl-2-pen tanone, 3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one, Example 3 4-methyl-1-phenyl-2-pentanone, 2-methyltetrahydrofuran 0045. In a glass roundbottom flask, silane VII (9.80 g, 3-one, 2-methyltetrahydrothiophen-3-one, 2-nonanone, 0.041 mol) was charged and stirred. A 10.9% solution of 3-nonanone, 2-octanone, 3-octanone, 1-octen-3-one, Pt(0) in divinyltetramethylsiloxane (14 mg of solution, 200 3-octen-2-one, 4-oxoisophorone, 2-pentadecanone, 2,3-pen ppm Pt) was added. Tetramethylcyclotetrasiloxane (2.51 g, tanedione, 2-pentanone, 3-pentanone, 3-penten-2-one, 0.041 mol hydride) was then added to the reaction mixture 1-phenyl-1,2-propandione, propiophenone, pulegone, over 25 min. A significant exotherm was observed. The 2-tridecanone, 2.2,6trimethylcyclohexanone, 4-(2,6,6-trim reaction mixture was then heated to 70° C. and maintained ethyl-2-cylcohexen-1-yl)-3-methyl-3-buten-2-one, 2-unde at said temperature for 2.5 h. The product was filtered to give canone, and 6-undecanone. 11.0 g of a straw colored fluid (89.4%). 0042. The active-releasing compounds of the present invention are particularly Suited to incorporation into per Example 4 Sonal care products to impart a desirable and long lasting 0046) In a glass roundbottom flask, silane VIII (16.41 g, effect to the products. Suitable uses include but are not 0.060 mol) was charged and stirred. A 10.9% solution of US 2005/O136021 A1 Jun. 23, 2005

Pt(0) in divinyltetramethylsiloxane (21 mg of solution, 200 Solution was used). The mixture was stirred and periodically ppm Pt) was added, and the mixture was stirred for 15 min. Sampled for gas chromatography analysis. Tables 1-5 dem Tetramethylcyclotetrasiloxane (3.61 g, 0.060 mol hydride) onstrate the release profiles determined in examples 6-10, was then added to the reaction mixture over 25 min. The respectively. reaction mixture was then heated to 70° C. and maintained at said temperature for 2.5 h. The product was stripped (75 C., 0.5 mm Hg) for 1.5 h then filtered to give 18.1 g of TABLE 1. yellow fluid (90.5%). Hydrolyis of product from example 1. Example 5 Relative 0047. In a glass roundbottom flask, silane IX (16.78 g, 0.054 mol) was charged along with a 10.9% solution of Pt(0) citronellol in divinyltetramethylsiloxane (14 mg of solution, 150 ppm Time (h) concentration Pt). The mixture was stirred for 15 min. Tetramethylcy clotetrasiloxane (3.23 g, 0.054 mol hydride) was then added O.OO O.042 to the reaction mixture over 25 min; the Solution increased O.92 0.077 in viscosity. The reaction mixture was then heated to 60° C. 8.92 O.145 and maintained at Said temperature for 80 min. The product was stripped (70° C., 3 mm Hg) for 1 h then filtered to give 22.58 O.198 16.5 g of pale orange fluid (82.5%). 29.33 O.22O 47.OO O.248 55.00 O.258 V 70.75 O.282 al- N 78.08 O.283 93.92 O.298 VI -N- 0050

TABLE 2 VII Hydrolyis of product from example 2. al- N Relative phenethyl alcohol VIII Time (h) concentration O.OO O.O25 1.33 O.102 9.33 O.253 23.OO O.418 29.75 O.450 47.50 O.532 --O- IX 55.50 0.557 71.25 O. 604 78.50 O.614 94.42 O.639

0051) TABLE 3 Hydrolysis of product from example 3. Examples 6-10 Relative geraniol Hydrolysis of Products from Examples 1-5, Time (h) concentration Respectively O.OO O.083 OSO O.097 0.048. The general procedure for hydrolysis is as follows: 6.OO O.261 25.42 O.429 0049. A solution of the active ingredient-functional sili 45.83 O.S30 cone (1.0 g), tetrahydrofuran (10 g), and bibenzyl internal 53.75 0.559 70.83 O600 Standard (0.4 g) was prepared. The Solution was analyzed by 77.50 O608 gas chromatography, then 0.50 mL of 1% (wt.) aqueous 94.08 O642 Sodium hydroxide Solution was added (except for example 9, in which 0.125 mL of 1% aqueous sodium hydroxide US 2005/O136021 A1 Jun. 23, 2005

0052 TABLE 6-continued TABLE 4 Relative odor of fabric Swatches (Example 11). Hydrolysis of product from example 4. Siloxane Relative 3-methyl-3-(meta Hours Control from Ex. 2 ispropylphenyl)propionaldehyde Time (h) concentration 21.5 4 4 28.9 3 4 O.OO O-111 46.3 3 4 1.OO 1.142 52.8 3 4 6.42 1.109 78.1 3 4 25.92 1.OO7 1643 3 4 46.33 O.954 215.3 2 3 54.25 O.932 237.1 1. 2 71.25 O.913 78.OO O.900 94.50 O.884 0056)

0053) TABLE 7 Relative odor of fabric Swatches (Example 12). TABLE 5 Siloxane Hydrolysis of product from example S. Hours Control from Ex. 5 Relative phenethyl O.O 5 3 Time (h) alcohol concentration 5.0 4 3 21.5 4 3 28.9 3 3 1.42 O.344 46.3 3 3 6.92 0.791 52.8 3 3 26.42 1.253 78.1 3 3 46.75 1368 164.3 3 2 54.83 1389 215.3 2 2 71.75 1418 237.1 1. 2 78.50 1439 95.OO 1.451 Having described the invention that which is claimed is: Examples 11-12 1. An active ingredient-releasing cyclic Siloxane Selected Hydrolysis of Products from Examples 2 and 5, from the group of Siloxanes having the formulas: Respectively 0.054 The general procedure for hydrolysis is as follows: 0055. A 3.3 cm by 3.3 cm Swatch of untreated cotton cloth was Soaked with each material Such that the molar equivalents of active ingredient were equal between all of the Samples. Each Swatch was kept in a Small aluminum pan, and all of the pans were kept in an open-top box in the same room at ambient temperature and humidity. The Samples were Smelled at timed intervals and rated for Strength of Scent (0=no Scent, 5=same strength as pure active ingredient from the bottle). Data are presented in Tables 6 and 7. In example 11 (Table 6), it can be seen that the cloth treated with the Siloxane derivative of the present invention release a stronger odor for a longer period of time. In example 12 where R', R', R', and R' are each independently (Table 7), it can be seen that the cloth treated with the Selected from the group of monovalent C-C hydro Siloxane derivative exhibits a more consistent degree of odor carbon radicals, the Subscripts n and q are each inde over time. pendently greater than or equal to 1, the Subscripts p, r, and S are each independently equal to or greater than 0 TABLE 6 with the proviso that n+p must be equal to or greater Relative Odor of fabric Swatches (Example 11). than 3 and that q+r--S must be equal to or greater than 3; where RF has the formula Siloxane (RO),(RO),(RO) (R').(R), SiR with R a C-Co Hours Control from Ex. 2 divalent hydrocarbon radical and R' and R indepen O.O 5 5 dently Selected from the group consisting of monova 5.0 4 4 lent hydrocarbon radicals having from one to forty carbon atoms, the Subscript a has a value ranging from US 2005/O136021 A1 Jun. 23, 2005 12

1 to 3 and the Subscripts b, c, d, and e have values droxy-2-cyclopenten-1-one, ethyl 2-hydroxycaproate, ethyl ranging from 0 to 2. Subject to the limitation that 3-hydroxyhexanoate, ethyl lactate, ethyl maltol, p-ethylphe a+b+c+d+e=3, where each R'O, RO and RO are nol, ethyl Salicylate, eugenol, farneSol, fenchyl alcohol, independently Selected from the group of conjugate geraniol, glucose petaacetate, glycerol, glyceryl monoStear bases consisting of conjugate bases derived from the ate, guaiacol, 1-heptanol, 2-heptanol, 3-heptanol, cis-4-hep group of alcohol active ingredients consisting of ROH, tenol, cis-3-heptenol, n-hexanol, 2-hexanol, 3-hexanol, cis 2-hexenol, cis-3-hexenol, trans-3-hexenol, 4-hexenol, cis-3- ROH, and ROH where R, R and R are indepen hexenyl hydrocinnamyl alcohol, 2-hydroxybenzoate, dently monovalent hydrocarbon radicals having from 2-hydroxyacetophenone, 4-hydroxybenzyl alcohol, 3-hy four to one hundred carbon atoms and the group of droxy-2-butanone, hydroxycitronellal, 4-(4-hydroxy-3- conjugate bases derived from the group of carbonyl methoxyphenyl)-2-butanone, 2-hydroxy-3-methyl-2-cyclo active ingredients having the Structure: penten-1-one, 4-(p-hydroxyphenyl)-2-butanone, 2-hydroxy 3,5,5-trimethyl-2-cyclohexenone, 6-isoascorbic acid, isoborneol, isoeugenol, isophytol, isopropyl alcohol, p-iso propylbenzyl alcohol, 4-isopropylcylcohexanol, 3-isopropy R", R, and Rare each independently selected from the lphenol, 4-isopropylphenol, 2-isopropylphenol, isopulegol, group consisting of hydrogen and monovalent hydro lauryl alcohol, linalool, maltol, menthol, 4-methoxybenzyl carbon radicals having from one to one hundred carbon alcohol, 2-methoxy-4-methylphenol, 2-methoxy-4propy atOmS. lphenol, 2-methoxy-4-Vinylphenol, C.-methylbenzyl alcohol, 2. The active ingredient-releasing cyclic Siloxane of claim 2-methylbutanol, 3-methyl-2-butanol, 3-methyl-2-buten-1- ol, 2-methyl-3-buten-2-ol, methyl 2,4-dihydroxy-3,6-dim 1 having the formula: ethylbenzoate, 4-methyl-2,6-dimethoxyphenol, methyl N-3, 7-dimethyl-7-hydroxyoctylideneanthranilate, methyl 3-hydroxyhexanoate, 6-methyl-5-hepten-2-ol, 2-methylpen tanol, 3-methyl-3-pentanol, 2-methyl-4-phenylbutan-2-ol, 2-methyl-3-phenylpropan-2-ol, methyl Salicylate, 3-methyl 5-(2,2,3,-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, 2-methyl-2-vinyl-5-(1-hydroxy-1-methyl ethyl)-3,4-dihy drofuran, myrtenol, neohesperidin dihydrochalcone, neom enthol, nerol, nerolidol, trans-2-cis-6-nonadienol, 1,3- nonanediol acetate, nonadyl, 2-nonanol, cis-6-nonen-1-ol, 3. The active ingredient-releasing cyclic Siloxane of claim trans-2-nonen-1-ol, nonyl alcohol, 1-octanol, 2-octanol, 2 wherein RF has the formula 3-octanol, cis-3-octen-1-ol, cis-2-octen-1-ol, trans-2-octen (RO),(R’O) (RO) (R'), (R). SiR with R a C-C diva 1-ol, cis-6-octen-1-ol, cis-octen-1-ol, 1-octen-3-ol, oleyl lent hydrocarbon radical and R' and R independently alcohol, patchouli alcohol, 3-pentanol, n-pentanol, 2-pen Selected from the group consisting of monovalent hydrocar tanol, 1-penten-1-ol, cis-2-penten-1-ol, perillyl alcohol, 2-phenoxyethanol arabinogalactan, B-phenethyl alcohol, bon radicals having from one to forty carbon atoms, the phenethyl Salicylate, phenol, phenylacetaldehyde glyceryl Subscript a has a value ranging from 1 to 3 and the Subscripts acetal, 3-phenyl-1-pentanol, 5-phenyl-1-pentanol, 1-phenyl b, c, d, and e have values ranging from 0 to 2. Subject to the 1-pentanol, 1-phenyl-2-pentanol, 1-phenyl-3-methyl-1-pen limitation that a+b+c+d+e=3, where each R'O, RO and tanol, phytol, pinacol, polyalkylene glycols, polySorbate 20, RO are independently selected from the group of conjugate polySorbate 60, polySorbate 80, prenol, n-propanol, prope bases consisting of conjugate bases derived from the group nyl guaethol, propylene glycol, 2-propylphenol, 4-propy of alcohol active ingredients consisting of ROH, ROH, lphenol, resorcinol, retinol, Salicylaldehyde, Sorbitan and ROH. monoStearate, Sorbitol, Stearyl alcohol, Syringealdehyde, 4. The active ingredient-releasing cyclic Siloxane of claim C-terpineol, tetrahydrogeraniol, tetrahydrolinalool, tetrahy 3 wherein the alcohol active ingredients ROH, ROH, and dromyrcenol, thymol, triethyl citrate, 1,2,6-trihydroxyheX ROH are fragrant alcohols. ane, p-O.C.-trimethylbenzyl alcohol, 2-(5.5,6-trimethylbicy 5. The active ingredient-releasing cyclic Siloxane of claim clo2.2.1]hept-2-ylcyclohexanol, 5-(2,2,3-trimethyl-3- 4 wherein the fragrant alcohols, ROH, ROH, and ROH cyclopentenyl)-3-methylpentan-2-ol, 3,7,-11-trimethyl-2,6, are Selected from the group of fragrant alcohols consisting of 10-dodecatrien-1-ol, 3,7,11-trimethyl-1,6,10-dodecatrien-3- acetovanillone, allyl amylglycolate, allyl isoamylglycolate, ol, 3.5,5-trimethyl-1-hexanol, 10-undecen-1-ol, undecyl C.-amylcinammyl alcohol, anisyl alcohol, benzoin, benzyl alcohol, vanillin, o-vanillin, vanillylbutyl ether, 4-vinylphe alcohol, benzyl Salicylate, 1-butanol, butylated hydroxytolu nol, 2.5-Xylenol, 2,6-Xylenol, 3.5-Xylenol, 2,4-Xylenol, and ene, butyl lactate, 2-t-butyl-5-methylphenol, 2-t-butyl-6- Xylose. methylphenol, carvacrol, carveol, 4-carvomenthenol, cedrol, 6. The active ingredient-releasing cyclic Siloxane of claim cetyl alcohol, cinnamic alcohol, citronellol, o-creSol, m-creSol, p-creSol, crotyl alcohol, decahydro-2-naphthol, 1 having the formula: 1-decanol, 1-decen-3-ol, 9-decen-1-ol, diethyl malate, diethyl tartrate, dihydrocarveol, dihydromyrcenol, 2,6-diiso propylphenol, dimethicone copolyol, 2,6-dimethoxyphenol, 1,1-dimethoxy-3,7-dimethyloctan-7-ol, 2,6-dimethyl-4-hep tanol, 2,6-dimethylheptan-2-ol, 6,8-dimethyl-2-nonanol, 3,7-dimethyl-2,6-octadien-1-ol, 3,7-dimethyl-1,6-octadien 3-ol, 3,7-dimethyl-1-octanol, 3,7-dimethyl-3-octanol, 3,7- dimethyl-6-octen-1-ol, 3,7-dimethyl-7-octen-1-ol, dimetol, 2-ethylfenchol, 4-ethylguaiacol, 2-ethyl-1-hexanol, ethyl 2-hydroxybenzoate, ethyl 3-hydroxybutyrate, 3-ethyl-2-hy US 2005/O136021 A1 Jun. 23, 2005

7. The active ingredient-releasing cyclic Siloxane of claim drofuran, myrtenol, neohesperidin dihydrochalcone, neom 6 1. wherein RF has the formula enthol, nerol, nerolidol, trans-2-cis-6-nonadienol, 1,3- (RO),(RO),(RO),(R')(R) SiR with R a C-C diva nonanediol acetate, nonadyl, 2-nonanol, cis-6-nonen-1-ol, lent hydrocarbon radical and R' and R independently trans-2-nonen-1-ol, nonyl alcohol, 1-octanol, 2-octanol, Selected from the group consisting of monovalent hydrocar 3-octanol, cis-3-octen-1-ol, cis-2-octen-1-ol, trans-2-octen bon radicals having from one to forty carbon atoms, the 1-ol, cis-6-octen-1-ol, cis-octen-1-ol, 1-octen-3-ol, oleyl Subscript a has a value ranging from 1 to 3 and the Subscripts alcohol, patchouli alcohol, 3-pentanol, n-pentanol, 2-pen b, c, d, and e have values ranging from 0 to 2. Subject to the tanol, 1-penten-1-ol, cis-2-penten-1-ol, perillyl alcohol, limitation that a+b+c+d+e=3, where each R'O, RO and 2-phenoxyethanol arabinogalactan, B-phenethyl alcohol, RO are independently selected from the group of conjugate phenethyl Salicylate, phenol, phenylacetaldehyde glyceryl bases consisting of conjugate bases derived from the group acetal, 3-phenyl-1-pentanol, 5-phenyl-1-pentanol, 1-phenyl of alcohol active ingredients consisting of ROH, ROH, 1-pentanol, 1-phenyl-2-pentanol, 1-phenyl-3-methyl-1-pen and ROH. tanol, phytol, pinacol, polyalkylene glycols, polySorbate 20, polySorbate 60, polySorbate 80, prenol, n-propanol, prope 8. The active ingredient-releasing cyclic Siloxane of claim nyl guaethol, propylene glycol, 2-propylphenol, 4-propy 7 wherein the alcohol active ingredients ROH, ROH, and lphenol, resorcinol, retinol, Salicylaldehyde, Sorbitan ROH are fragrant alcohols. monoStearate, Sorbitol, Stearyl alcohol, Syringealdehyde, 9. The active ingredient-releasing cyclic Siloxane of claim C-terpineol, tetrahydrogeraniol, tetrahydrolinalool, tetrahy 8 wherein the fragrant alcohols, ROH, ROH, and ROH dromyrcenol, thymol, triethyl citrate, 1,2,6-trihydroxyheX are Selected from the group of fragrant alcohols consisting of ane, p-O.C.-trimethylbenzyl alcohol, 2-(5.5,6-trimethylbicy acetovanillone, allyl amylglycolate, allyl isoamylglycolate, clo2.2.1]hept-2-ylcyclohexanol, 5-(2,2,3-trimethyl-3- C.-amylcinammyl alcohol, anisyl alcohol, benzoin, benzyl cyclopentenyl)-3-methylpentan-2-ol, 3,7,-11-trimethyl-2,6, alcohol, benzyl Salicylate, 1-butanol, butylated hydroxytolu 10-dodecatrien-1-ol, 3,7,11-trimethyl-1,6,10-dodecatrien-3- ene, butyl lactate, 2-t-butyl-5-methylphenol, 2-t-butyl-6- ol, 3.5,5-trimethyl-1-hexanol, 10-undecen-1-ol, undecyl methylphenol, carvacrol, carveol, 4-carvomenthenol, cedrol, alcohol, vanillin, o-vanillin, vanillylbutyl ether, 4-vinylphe cetyl alcohol, cinnamic alcohol, citronellol, o-creSol, nol, 2.5-Xylenol, 2,6-Xylenol, 3.5-Xylenol, 2,4-Xylenol, and m-creSol, p-creSol, crotyl alcohol, decahydro-2-naphthol, Xylose. 1-decanol, 1-decen-3-ol, 9-decen-1-ol, diethyl malate, diethyl tartrate, dihydrocarveol, dihydromyrcenol, 2,6-diiso 10. The active ingredient-releasing cyclic Siloxane of propylphenol, dimethicone copolyol, 2,6-dimethoxyphenol, claim 2 wherein RF has the formula 1,1-dimethoxy-3,7-dimethyloctan-7-ol, 2,6-dimethyl-4-hep (RO),(R’O) (RO) (R'),(R) SiR with Ra C-C diva tanol, 2,6-dimethylheptan-2-ol, 6,8-dimethyl-2-nonanol, lent hydrocarbon radical and R' and R independently 3,7-dimethyl-2,6-octadien-1-ol, 3,7-dimethyl-1,6-octadien Selected from the group consisting of monovalent hydrocar 3-ol, 3,7-dimethyl-1-octanol, 3,7-dimethyl-3-octanol, 3,7- bon radicals having from one to forty carbon atoms, the dimethyl-6-octen-1-ol, 3,7-dimethyl-7-octen-1-ol, dimetol, Subscript a has a value ranging from 1 to 3 and the Subscripts 2-ethylfenchol, 4-ethylguaiacol, 2-ethyl-1-hexanol, ethyl b, c, d, and e have values ranging from 0 to 2. Subject to the 2-hydroxybenzoate, ethyl 3-hydroxybutyrate, 3-ethyl-2-hy limitation that a+b+c+d+e=3, where each R'O, RO and droxy-2-cyclopenten-1-one, ethyl 2-hydroxycaproate, ethyl RO are independently selected from the group of conjugate 3-hydroxyhexanoate, ethyl lactate, ethyl maltol, p-ethylphe bases consisting of conjugate bases derived from the group nol, ethyl Salicylate, eugenol, farneSol, fenchyl alcohol, of conjugate bases derived from the group of carbonyl active geraniol, glucose petaacetate, glycerol, glyceryl monoStear ingredients having the Structure: ate, guaiacol, 1-heptanol, 2-heptanol, 3-heptanol, cis-4-hep tenol, cis-3-heptenol, n-hexanol, 2-hexanol, 3-hexanol, cis 2-hexenol, cis-3-hexenol, trans-3-hexenol, 4-hexenol, cis-3- hexenyl hydrocinnamyl alcohol, 2-hydroxybenzoate, R", R, and Rare each independently selected from the 2-hydroxyacetophenone, 4-hydroxybenzyl alcohol, 3-hy group consisting of hydrogen and monovalent hydro droxy-2-butanone, hydroxycitronellal, 4-(4-hydroxy-3- carbon radicals having from one to one hundred carbon methoxyphenyl)-2-butanone, 2-hydroxy-3-methyl-2-cyclo atOmS. penten-1-one, 4-(p-hydroxyphenyl)-2-butanone, 2-hydroxy 11. The active ingredient-releasing cyclic Siloxane of 3,5,5-trimethyl-2-cyclohexenone, 6-isoascorbic acid, claim 10 wherein the carbonyl active ingredients are fragrant isoborneol, isoeugenol, isophytol, isopropyl alcohol, p-iso carbonyl active ingredients. propylbenzyl alcohol, 4-isopropylcylcohexanol, 3-isopropy 12. The active ingredient-releasing cyclic Siloxane of lphenol, 4-isopropylphenol, 2-isopropylphenol, isopulegol, claim 11 where the fragrant carbonyl active ingredients are lauryl alcohol, linalool, maltol, menthol, 4-methoxybenzyl Selected from the group consisting of 4-acetoxy-3-pentyl alcohol, 2-methoxy-4-methylphenol, 2-methoxy-4-propy tetrahydropyran, allyl cinnamate, allyl 2-ethylbutyrate, allyl lphenol, 2-methoxy-4-Vinylphenol, C.-methylbenzyl alcohol, cyclohexanepropionate, allyl heptanoate, allyl hexanoate, 2-methylbutanol, 3-methyl-2-butanol, 3-methyl-2-buten-1- allyl isoValerate, allyl nonanoate, allyl octanoate, allyl phe ol, 2-methyl-3-buten-2-ol, methyl 2,4-dihydroxy-3,6-dim noxyacetate, allyl phenylacetate, allyl propionate, C.-amyl ethylbenzoate, 4-methyl-2,6-dimethoxyphenol, methyl N-3, cinnamyl acetate, amyl octanoate, anisyl acetate, anisylphe 7-dimethyl-7-hydroxyoctylideneanthranilate, methyl nyl acetate, benzyl acetate, benzyl acetoacetate, benzyl 3-hydroxyhexanoate, 6-methyl-5-hepten-2-ol, 2-methylpen butyrate, benzyl cinnamate, benzyl isobutyrate, benzyl isov tanol, 3-methyl-3-pentanol, 2-methyl-4-phenylbutan-2-ol, alerate, benzyl phenylacetate, benzyl propionate, bornyl 2-methyl-3-phenylpropan-2-ol, methyl Salicylate, 3-methyl acetate, bornyl isoValerate, bornyl Valerate, butyl acetate, 5-(2,2,3,-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol, butyl butyrate, butyl butyrylactate, 4-t-butylcyclohexyl 2-methyl-2-vinyl-5-(1-hydroxy-1-methyl ethyl)-3,4-dihy acetate, butyl heptanoate, butylhexanoate, butyl isobutyrate, US 2005/O136021 A1 Jun. 23, 2005 butylisovalerate, butyl laurate, butyl propionate, butyl Stear ylbutyl 2-methylbutanoate, 2-methylbutyl 2-methylbu ate, 3-butylidenephthalide, butyl 2-methylbutyrate, butyl tanoate, methyl p-t-butylphenylacetate, methyl butyrate, 10-undeceneoate, Y-butyrolactone, carvyl acetate, carvyl methyl cinnamate, methyl decanoate, methyl heptanoate, propionate, caryophyllene acetate, cedryl acetate, trans methyl hexanoate, methyl isobutyrate, methyl isOValerate, cinnamyl acetate, trans-cinnamyl butyrate, cinnamyl cin methyl laurate, methyl N-2-methyl-3-(4-t-butylphenylpro namate, cinnamyl isobutyrate, citronellyl acetate, citronellyl pylidene) anthranilate, methyl (methylthio)acetate, methyl butyrate, citronellyl isobutyrate, citronellyl propionate, cit 2-(methylthio) propionate, methyl myristate, methyl ronellyl Valerate, cyclohexaneethyl acetate, cyclohexyl nonanoate, methyl octanoate, methyl palmitate, 4-(4-me acetate, cyclohexylbutyrate, cyclohexyl isoValerate, cyclo thyl-3-pentenyl)-3-cyclohexenylmethyl acetate, methyl hexyl propionate, 6-decalactone, e-decalactone, y-decallac 2-methylbutyrate, 2-methyl-6-methylen-7-octen-2-yl tone, 4-decanolide, decyl acetate, decyl butyrate, decyl acetate, methyl 4-methylvalerate, methyl 2-methylpen propionate, diethyl malonate, diethyl Sebacate, diethyl Suc tanoate, methyl phenoxyacetate, 4-methylphenyl phenylac cinate, dihydrocarvyl acetate, dihydrocoumarin, dihy etate, 2-methyl-3-phenylpropan-2-yl acetate, methyl 3-phe dromyrcenyl acetate, dihydro-nor-dicyclopentadienyl nylpropionate, methyl propionate, 2-methylpropyl acetate, dihydroterpinyl acetate, 3,7-dimethyl-1,6-Octadien phenylacetate, methyl phenylacetate, 2-methyl-3-phenyl 3-yl acetate, 3,7-dimethyl-1,6-octadien-3-yl propionate, 3,7- propan-2-yl acetate, methyl Stearate, methyl (p-tolyloxy)ac dimethyloctan-3-yl acetate, C.C.-dimethylphenethyl acetate, etate, methyl 9-undecenoate, methyl Valerate, myrtenyl O.C.-dimethylphenethylbutyrate, 6,10-dimethyl-5.9-undeca acetate, neryl acetate, neryl butyrate, neryl isobutyrate, dien-2-yl acetate, 6-dodecalactone, e-dodecalactone, Ö-nonalactone, Y-nonalactone, 1,3-nonanediol diacetate, Y-dodecalactone, ethyl acetate, ethyl acetoacetate, ethyl nonyl acetate, nopyl acetate, octahydrocoumarin, Y-Octalac 6-acetoxyhexanoate, ethyl 2-acetyl-3-phenylpropionate, tone, 1-octen-3-yl acetate, 1-octen-3-yl butyrate, octyl ethyl benzoylacetate, 2-ethylbutyl acetate, ethyl butyrate, acetate, octyl butyrate, octyl isobutyrate, octyl isoValerate, ethyl cinnamate, ethyl cyclohexanepropionate, ethyl octyl octanoate, octyl propionate, oxacycloheptadec-10-en decanoate, ethylene brassylate, ethyl 2-ethyl-6,6-dimethyl 2-one, ()-pentadecalactone, pentyl acetate, pentylbutyrate, 2-cyclohexenecarboxylate, ethyl 2,3-epoxybutyrate, ethyl pentylhexanoate, pentyl octanoate, phenethyl acetate, phen 2-methyl-4-penteneoate, ethylheptanoate, ethylhexanoate, ethylbutyrate, phenethyl cinnamate, phenethyl hexanoate, ethyl trans-3-hexenoate, 2-ethylhexyl acetate, ethyl isobu phenethyl isobutyrate, phenethyl isovalerate, phenethyl tyrate, ethyl isoValerate, ethyl laurate, ethyl 2-mercaptopro 2-methylbutyrate, phenethyl 2-methylbutyrate, phenethyl pionate, ethyl 3-mercaptopropionate, ethyl 2-methylbu 2-methylpropionate, phenethyl octanoate, phenethyl pheny tyrate, ethyl 2-methylpentanoate, ethyl (methylthio)acetate, lacetate, phenethyl propionate, phenoxyethyl propionate, ethyl myristate, ethyl nonanoate, ethyl octanoate, ethyl 2-phenoxyethyl 2-methylpropionate, 3-phenyl-2-propenyl palmitate, ethyl phenylacetate, ethyl 3-phenylpropionate, propionate, 3-phenylpropyl acetate, 2-phenylpropyl ethyl 3-phenyl-2,3-epoxybutyrate, ethyl 3-phenylpropi butyrate, 2-phenylpropyl isobutyrate, 2-phenylpropyl isov onate, ethyl propionate, ethyl Stearate, ethyl 2,3,6,6-tetram alerate, piperonyl acetate, piperonyl isobutyrate, prenyl ethyl-2-cyclohexencarboxylate, ethyl (p-tolyloxy)acetate, acetate, propyl acetate, propylbutyrate, propyl heptanoate, ethyl undecanoate, ethyl Valerate, eugenyl acetate, fenchyl propyl hexanoate, 3-propylidenephthalide, propyl isobu acetate, geranyl acetate, geranylbutyrate, geranyl phenylac tyrate, propyl propionate, propyl phenylacetate, Sucrose etate, geranyl propionate, guaiacyl phenylacetate, guaic octaacetate, terpinyl acetate, terpinyl butyrate, terpinyl Wood acetate, Y-heptalactone, heptyl acetate, heptyl isobutyrate, terpinyl propionate, Ö-nonalactone, tetrahydro butyrate, heptylisobutyrate, ()-6-hexadecenlactone, 6-hexy furfuryl acetate, tetrahydrofurfuryl butyrate, tetrahydrofur lactone, Y-hexylactone, 3-hexenyl acetate, cis-3-hexenyl furyl propionate, tetrahydrolinallyl acetate, 2,6,6,8-tetram 2-methylbutanoate, cis-3-hexenyl cis-3-hexenoate, cis-3- ethyl-tricyclo5.3.1.0(1.5)udecan-8-yl acetate, p-tolyl hexenyl phenylacetate, trans-2-hexenyl acetate, hexyl acetate, p-tolyl isobutyrate, p-tolyl phenylacetate, triacetin, acetate, hexylbutyrate, hexylhexanoate, hexyl isobutyrate, tributyl acetylcitrate, tributyrin, tripropionin, 3.5,5-trimeth hexyl propionate, hexyl 2-methylbutanoate, hexyl 3-meth ylhexyl acetate, 6-undecalactone, Y-undecalactone, Y-Vale ylbutanoate, hexyl phenylacetate, isoamyl acetate, isoamyl rolactone, Vanillin acetate, Vanillyl isobutyrate, 1-vinyl-2- acetoacetate, isoamylbutyrate, isoamyl cinnamate, isoamyl (1-methylpropyl)cyclohexyl acetate, whiskey lactone, hexanoate, isoamyl isobutyrate, isoamyl isoValerate, butyraldehyde, citronellal, decanal, cis-4-decenal, trans-4- isoamyl laurate, isoamyl nonanoate, isoamyl octanoate, decenal, 2,4-dimethyl-3-cyclohexen-1-carbaldehyde, 2,6- isoamyl phenylacetate, isoamyl propionate, isobornyl dimethyl-5-heptenal, 3,7-dimethyloctanal, 2-ethylbutyralde acetate, isobornyl propionate, isobutyl acetate, isobutyl hyde, glutaric dialdehyde, heptanal, cis-4-heptenal, heXanal, butyrate, isobutyl cinnamate, isobutyl hexanoate, isobutyl hydrocinnamaldehyde, isobutyraldehyde, 3-(p-isopropy isobutyrate, isobutyl 2-methylbutyrate, isobutyl propionate, lphenyl)propionaldehyde, isovaleraldehyde, lauric alde isoeugenyl acetate, isopropyl cinnamate, isobutyl phenylac hyde, 2-methylbutyraldehyde, 2-methyl-3-(p-isopropylphe etate, isopropyl acetate, isopropylbutyrate, isopropyl isobu nyl)propionaldehyde, 2-methylpentanal, 4-(4-methyl-3- tyrate, isopropyl myristate, isopropyl palmitate, isopropyl pentenyl)-3-cyclohexen-1-carbaldehyde, phenylacetate, lauryl acetate, linallyl acetate, linallylbutyrate, 4-methylphenylacetaldehyde, 3-(methylthio)butanal, 2-me linallyl isoValerate, menthalactone, menthyl acetate, menthyl thyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)butanal, 2-me cyclohexanecarboxylate, menthyl isoValerate, 4-methoxy thylundecanal, nonanal, cis-6-nonenal, octanal, phenylac benzyl acetate, 4-methoxybenzyl propionate, 2-methoX etaldehyde, 2-phenylpropionaldehyde, yphenyl acetate, 2-methoxy-4-(1-propenyl)phenyl acetate, 3-phenylpropionaldehyde, propionaldehyde, p-tolylacetal methyl acetate, C.-methylbenzyl acetate, C.-methylbenzyl dehyde, tridecanal, 2,4,6-trimethyl-3-cyclohexen-1-carbal butyrate, C.-methylbenzyl propionate, 2-methylbutyl acetate, dehyde, 2,6,10-trimethyl-9-undecanal, 7-undecenal, 8-unde 2-methylbutylbutyrate, 2-methylbutyl isovalerate, 3-meth cenal, 9-undecenal, 10-undecenal, Valeraldehyde, US 2005/O136021 A1 Jun. 23, 2005 acetanisole, 1'-acetonaphthone, 2'-acetonaphthone, acetone, tetrahydropyran, allyl cinnamate, allyl 2-ethylbutyrate, allyl acetophenone, 2-acetoxy-2,5-dimethyl-3(2H)furanone, cyclohexanepropionate, allyl heptanoate, allyl hexanoate, 2-acetylcyclopentanone, 4-acetyl-1,1-dimethyl-6-t-butylin allyl isoValerate, allyl nonanoate, allyl octanoate, allyl phe dan, 7-acetyl-1,1,3,4,4,6-hexamethylindan, 2-acetyl-2-thia noxyacetate, allyl phenylacetate, allyl propionate, C.-amyl Zoline, 6-acetyl-1,1,2,4,4,7-hexamethyl tetralin, allyl C-ion cinnamyl acetate, amyl octanoate, anisyl acetate, anisylphe one, benzylideneacetone, 2,3-butanedione, 2-Sec nyl acetate, benzyl acetate, benzyl acetoacetate, benzyl butylcyclohexanone, 5-t-butyl-3,5-dinitro-2,6- butyrate, benzyl cinnamate, benzyl isobutyrate, benzyl isov dimethylacetophenone, butyrophenone, camphor, alerate, benzyl phenylacetate, benzyl propionate, bornyl 2-decanone, 3-decanone, 3-decen-2-one, dihydrocarvone, dihydro-f-ionone, dihydrojasmone, 4,5-dihydro-3(2H)- acetate, bornyl isoValerate, bornyl Valerate, butyl acetate, thiophenone, 2',4'-dimethylacetophenone, 3,4-dimethyl-1,2- butyl butyrate, butyl butyrylactate, 4-t-butylcyclohexyl cyclopentadione, 3,5-dimethyl-1,2-cyclopentadione, 2,6- acetate, butyl heptanoate, butylhexanoate, butyl isobutyrate, dimethyl-4-heptanone, 1,3-diphenyl-2-propanone, 4-(1- butyl isoValerate, butyl laurate, butyl propionate, butyl Stear ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone, ate, 3-butylidenephthalide, butyl 2-methylbutyrate, butyl p-ethylacetophenone, ethyl vinyl ketone, geranylacetone, 10-undeceneoate, Y-butyrolactone, carvyl acetate, carvyl 2,3-heptanedione, 2-heptanone, 3-heptanone, 4-heptanone, propionate, caryophyllene acetate, cedryl acetate, trans 3,4-hexanedione, 3-hexanone, 4-hexen-3-one, 2-hexylidene cinnamyl acetate, trans-cinnamyl butyrate, cinnamyl cin cyclopentanone, C.-ionone, B-ionone, 4-isobutyl-2,6-dim namate, cinnamyl isobutyrate, citronellyl acetate, citronellyl ethyl-3,5-dinitroacetophenone, isophorone, 6-isopropyl butyrate, citronellyl isobutyrate, citronellyl propionate, cit decahydro-2-naphthone, cis-jasmone, liveScone, 4-meth ronellyl Valerate, cyclohexaneethyl acetate, cyclohexyl Oxyacetophenone, 4-(p-methoxyphenyl)-2-butanone, acetate, cyclohexylbutyrate, cyclohexyl isoValerate, cyclo 4'-methylacetophenone, 3-methyl-1,2-cyclohexanedione, hexyl propionate, 6-decalactone, e-decalactone, y-decallac 3-methyl-2-cyclohexen-1-one, 2-(2-(4-methyl-3-cylco tone, 4-decanolide, decyl acetate, decyl butyrate, decyl hexen-1-yl)propyl)cyclopentanone, 3-methyl-2-cyclo propionate, diethyl malonate, diethyl Sebacate, diethyl Suc penten-1-one, methyl dihydrojasmonate, methyl ethyl cinate, dihydrocarvyl acetate, dihydrocoumarin, dihy ketone, 2-methyl-3-heptanone, 5-methyl-2-hepten-4-one, dromyrcenyl acetate, dihydro-nor-dicyclopentadienyl 6-methyl-5-hepten-2-one, 5-methyl-O-ionone, 1-(2-methyl acetate, dihydroterpinyl acetate, 3,7-dimethyl-1,6-Octadien 5-isopropyl-2-cyclohexenyl)-1-propanone, 4-methyl-2-pen 3-yl acetate, 3,7-dimethyl-1,6-Octadien-3-yl propionate, 3,7- tanone, 3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one, dimethyloctan-3-yl acetate, C.C.-dimethylphenethyl acetate, 4-methyl-1-phenyl-2-pentanone, 2-methyltetrahydrofuran C.C.-dimethylphenethylbutyrate, 6,10-dimethyl-5.9-undeca 3-one, 2-methyltetrahydrothiophen-3-one, 2-nonanone, dien-2-yl acetate, 6-dodecalactone, e-dodecalactone, 3-nonanone, 2-octanone, 3-octanone, 1-octen-3-one, Y-dodecalactone, ethyl acetate, ethyl acetoacetate, ethyl 3-octen-2-one, 4-oxoisophorone, 2-pentadecanone, 2,3-pen 6-acetoxyhexanoate, ethyl 2-acetyl-3-phenylpropionate, tanedione, 2-pentanone, 3-pentanone, 3-penten-2-one, ethyl benzoylacetate, 2-ethylbutyl acetate, ethyl butyrate, 1-phenyl-1,2-propandione, propiophenone, pulegone, ethyl cinnamate, ethyl cyclohexanepropionate, ethyl decanoate, ethylene brassylate, ethyl 2-ethyl-6,6-dimethyl 2-tridecanone, 2,2,6-trimethylcyclohexanone, 4-(2,6,6-trim 2-cyclohexenecarboxylate, ethyl 2,3-epoxybutyrate, ethyl ethyl-2-cylcohexen-1-yl)-3-methyl-3-buten-2-one, 2-unde 2-methyl-4-penteneoate, ethylheptanoate, ethylhexanoate, canone, and 6-undecanone. ethyl trans-3-hexenoate, 2-ethylhexyl acetate, ethyl isobu 13. The active ingredient-releasing cyclic Siloxane of tyrate, ethyl isoValerate, ethyl laurate, ethyl 2-mercaptopro claim 6 wherein RF has the formula pionate, ethyl 3-mercaptopropionate, ethyl 2-methylbu (RO),(RO),(RO),(R')(R) SiR with R a C-C diva tyrate, ethyl 2-methylpentanoate, ethyl (methylthio)acetate, lent hydrocarbon radical and R' and R independently ethyl myristate, ethyl nonanoate, ethyl octanoate, ethyl Selected from the group consisting of monovalent hydrocar palmitate, ethyl phenylacetate, ethyl 3-phenylpropionate, bon radicals having from one to forty carbon atoms, the ethyl 3-phenyl-2,3-epoxybutyrate, ethyl 3-phenylpropi Subscript a has a value ranging from 1 to 3 and the Subscripts onate, ethyl propionate, ethyl Stearate, ethyl 2,3,6,6-tetram b, c, d, and e have values ranging from 0 to 2. Subject to the ethyl-2-cyclohexencarboxylate, ethyl (p-tolyloxy)acetate, limitation that a+b+c+d+e=3, where each RO, RO and ethyl undecanoate, ethyl Valerate, eugenyl acetate, fenchyl RO are independently selected from the group of conjugate acetate, geranyl acetate, geranylbutyrate, geranyl phenylac bases consisting of conjugate bases derived from the group etate, geranyl propionate, guaiacyl phenylacetate, guaic of conjugate bases derived from the group of carbonyl active Wood acetate, Y-heptalactone, heptyl acetate, heptyl ingredients having the Structure: butyrate, heptylisobutyrate, ()-6-hexadecenlactone, 6-hexy lactone, Y-hexylactone, 3-hexenyl acetate, cis-3-hexenyl 2-methylbutanoate, cis-3-hexenyl cis-3-hexenoate, cis-3- hexenyl phenylacetate, trans-2-hexenyl acetate, hexyl R7, R, and R are each independently selected from the acetate, hexylbutyrate, hexyl hexanoate, hexyl isobutyrate, group consisting of hydrogen and monovalent hydro hexyl propionate, hexyl 2methylbutanoate, hexyl 3-meth carbon radicals having from one to one hundred carbon ylbutanoate, hexyl phenylacetate, isoamyl acetate, isoamyl atOmS. acetoacetate, isoamylbutyrate, isoamyl cinnamate, isoamyl 14. The active ingredient-releasing cyclic Siloxane of hexanoate, isoamyl isobutyrate, isoamyl isOValerate, claim 13 wherein the carbonyl active ingredients are fragrant isoamyl laurate, isoamyl nonanoate, isoamyl octanoate, carbonyl active ingredients. isoamyl phenylacetate, isoamyl propionate, isobornyl 15. The active ingredient-releasing cyclic Siloxane of acetate, isobornyl propionate, isobutyl acetate, isobutyl claim 14 where the fragrant carbonyl active ingredients are butyrate, isobutyl cinnamate, isobutyl hexanoate, isobutyl Selected from the group consisting of 4-acetoxy-3-pentyl isobutyrate, isobutyl 2-methylbutyrate, isobutyl propionate, US 2005/O136021 A1 Jun. 23, 2005 isoeugenyl acetate, isopropyl cinnamate, isobutyl phenylac hyde, 2-methylbutyraldehyde, 2-methyl-3-(p-isopropylphe etate, isopropyl acetate, isopropylbutyrate, isopropyl isobu nyl)propionaldehyde, 2-methylpentanal, 4-(4-methyl-3- tyrate, isopropyl myristate, isopropyl palmitate, isopropyl pentenyl)-3-cyclohexen-1-carbaldehyde, phenylacetate, lauryl acetate, linallyl acetate, linallylbutyrate, 4-methylphenylacetaldehyde, 3-(methylthio)butanal, 2-me linallyl isoValerate, menthalactone, menthyl acetate, menthyl thyl-4-(2,6,6-trimethyl-2-cyclohexen-1-yl)butanal, 2-me cyclohexanecarboxylate, menthyl isoValerate, 4-methoxy thylundecanal, nonanal, cis-6-nonenal, octanal, phenylac benzyl acetate, 4-methoxybenzyl propionate, 2-methoX etaldehyde, 2-phenylpropionaldehyde, yphenyl acetate, 2-methoxy-4-(1-propenyl)phenyl acetate, 3-phenylpropionaldehyde, propionaldehyde, p-tolylacetal methyl acetate, C.-methylbenzyl acetate, C.-methylbenzyl dehyde, tridecanal, 2,4,6-trimethyl-3-cyclohexen-1-carbal butyrate, C.-methylbenzyl propionate, 2-methylbutyl acetate, dehyde, 2,6,10-trimethyl-9-undecanal, 7-undecenal, 8-unde 2-methylbutylbutyrate, 2-methylbutyl isovalerate, 3-meth cenal, 9-undecenal, 10-undecenal, Valeraldehyde, ylbutyl 2-methylbutanoate, 2-methylbutyl 2-methylbu acetanisole, 1'-acetonaphthone, 2'-acetonaphthone, acetone, tanoate, methyl p-t-butylphenylacetate, methyl butyrate, acetophenone, 2-acetoxy-2,5-dimethyl-3(2H)furanone, methyl cinnamate, methyl decanoate, methyl heptanoate, 2-acetylcyclopentanone, 4-acetyl-1,1-dimethyl-6-t-butylin methyl hexanoate, methyl isobutyrate, methyl isoValerate, dan, 7-acetyl-1,1,3,4,4,6-hexamethylindan, 2-acetyl-2-thia methyl laurate, methyl N-2-methyl-3-(4-t-butylphenylpro Zoline, 6-acetyl-1,1,2,4,4,7-hexamethyl tetralin, allyl C-ion pylidene) anthranilate, methyl (methylthio)acetate, methyl one, benzylideneacetone, 2,3-butanedione, 2-Sec 2-(methylthio) propionate, methyl myristate, methyl butylcyclohexanone, 5-t-butyl-3,5-dinitro-2,6- nonanoate, methyl octanoate, methyl palmitate, 4-(4-me dimethylacetophenone, butyrophenone, camphor, thyl-3-pentenyl)-3-cyclohexenylmethyl acetate, methyl 2-decanone, 3-decanone, 3-decen-2-one, dihydrocarvone, 2-methylbutyrate, 2-methyl-6-methylen-7-octen-2-yl dihydro-f-ionone, dihydrojasmone, 4,5-dihydro-3(2H)- acetate, methyl 4-methylvalerate, methyl 2-methylpen thiophenone, 2',4'-dimethylacetophenone, 3,4-dimethyl-1,2- tanoate, methyl phenoxyacetate, 4-methylphenyl phenylac cyclopentadione, 3,5-dimethyl-1,2-cyclopentadione, 2,6- etate, 2-methyl-3-phenylpropan-2-yl acetate, methyl 3-phe dimethyl-4-heptanone, 1,3-diphenyl-2-propanone, 4-(1- nylpropionate, methyl propionate, 2-methylpropyl ethoxyvinyl)-3,3,5,5-tetramethylcyclohexanone, phenylacetate, methyl phenylacetate, 2-methyl-3-phenyl p-ethylacetophenone, ethyl vinyl ketone, geranylacetone, propan-2-yl acetate, methyl Stearate, methyl (p-tolyloxy)ac 2,3-heptanedione, 2-heptanone, 3-heptanone, 4-heptanone, etate, methyl 9-undecenoate, methyl Valerate, myrtenyl 3,4-hexanedione, 3-hexanone, 4-hexen-3-one, 2-hexylidene acetate, neryl acetate, neryl butyrate, neryl isobutyrate, cyclopentanone, C.-ionone, B-ionone, 4-isobutyl-2,6-dim Ö-nonalactone, Y-nonalactone, 1,3-nonanediol diacetate, ethyl-3,5-dinitroacetophenone, isophorone, 6-isopropyl nonyl acetate, nopyl acetate, octahydrocoumarin, Y-octalac decahydro-2-naphthone, cis-jasmone, liveScone, 4-meth tone, 1-octen-3-yl acetate, 1-octen-3-yl butyrate, octyl Oxyacetophenone, 4-(p-methoxyphenyl)-2-butanone, acetate, octyl butyrate, octyl isobutyrate, octyl isoValerate, 4'-methylacetophenone, 3-methyl-1,2-cyclohexanedione, octyl octanoate, octyl propionate, oxacycloheptadec-10-en 3-methyl-2-cyclohexen-1-one, 2-(2-(4-methyl-3-cylco 2-one, ()-pentadecalactone, pentyl acetate, pentylbutyrate, hexen-1-yl)propyl)cyclopentanone, 3-methyl-2-cyclo pentylhexanoate, pentyl octanoate, phenethyl acetate, phen penten-1-one, methyl dihydrojasmonate, methyl ethyl ethylbutyrate, phenethyl cinnamate, phenethyl hexanoate, ketone, 2-methyl-3-heptanone, 5-methyl-2-hepten-4-one, phenethyl isobutyrate, phenethyl isoValerate, phenethyl 6-methyl-5-hepten-2-one, 5-methyl-O-ionone, 1-(2-methyl 2-methylbutyrate, phenethyl 2-methylbutyrate, phenethyl 5-isopropyl-2-cyclohexenyl)-1-propanone, 4-methyl-2-pen 2-methylpropionate, phenethyl octanoate, phenethyl pheny tanone, 3-methyl-2-(2-pentenyl)-2-cyclopenten-1-one, lacetate, phenethyl propionate, phenoxyethyl propionate, 4-methyl-1-phenyl-2-pentanone, 2-methyltetrahydrofuran 2-phenoxyethyl 2-methylpropionate, 3-phenyl-2-propenyl 3-one, 2-methyltetrahydrothiophen-3-one, 2-nonanone, propionate, 3-phenylpropyl acetate, 2-phenylpropyl 3-nonanone, 2-octanone, 3-octanone, 1-octen-3-one, butyrate, 2-phenylpropyl isobutyrate, 2-phenylpropyl isov 3-octen-2-one, 4-oxoisophorone, 2-pentadecanone, 2,3-pen alerate, piperonyl acetate, piperonyl isobutyrate, prenyl tanedione, 2-pentanone, 3-pentanone, 3-penten-2-one, acetate, propyl acetate, propylbutyrate, propyl heptanoate, 1-phenyl-1,2-propandione, propiophenone, pulegone, propyl hexanoate, 3-propylidenephthalide, propyl isobu 2-tridecanone, 2,2,6-trimethylcyclohexanone, 4-(2,6,6-trim tyrate, propyl propionate, propyl phenylacetate, Sucrose ethyl-2-cylcohexen-1-yl)-3-methyl-3-buten-2-one, 2-unde octaacetate, terpinyl acetate, terpinyl butyrate, terpinyl canone, and 6-undecanone. isobutyrate, terpinyl propionate, Ö-nonalactone, tetrahydro 16. A composition comprising the active ingredient furfuryl acetate, tetrahydrofurfuryl butyrate, tetrahydrofur releasing Siloxane of claim 1. furyl propionate, tetrahydrohnalyl acetate, 2,6,6,8-tetram 17. A composition comprising the active ingredient ethyl-tricyclo5.3.1.0(1.5)udecan-8-yl acetate, p-tolyl releasing Siloxane of claim 2. acetate, p-tolyl isobutyrate, p-tolyl phenylacetate, triacetin, 18. A composition comprising the active ingredient tributyl acetylcitrate, tributyrin, tripropionin, 3.5,5-trimeth releasing Siloxane of claim 6. ylhexyl acetate, 6-undecalactone, Y-undecalactone, Y-Vale rolactone, Vanillin acetate, Vanillyl isobutyrate, 1-vinyl-2- 19. A composition comprising the active ingredient (1-methylpropyl)cyclohexyl acetate, whiskey lactone, releasing Siloxane of claim 10. butyraldehyde, citronellal, decanal, cis-4-decenal, trans-4- 20. A composition comprising the active ingredient decenal, 2,4-dimethyl-3-cyclohexen-1-carbaldehyde, 2,6- releasing Siloxane of claim 13. dimethyl-5-heptenal, 3,7-dimethyloctanal, 2-ethylbutyralde 21. A composition consisting essentially of the active hyde, glutaric dialdehyde, heptanal, cis-4-heptenal, heXanal, ingredient releasing Siloxane of claim 1. hydrocinnamaldehyde, isobutyraldehyde, 3-(p-isopropy lphenyl)propionaldehyde, isovaleraldehyde, lauric alde