MXPA06007050A - Active ingredient-releasing cyclic siloxanes - Google Patents
Active ingredient-releasing cyclic siloxanesInfo
- Publication number
- MXPA06007050A MXPA06007050A MXPA/A/2006/007050A MXPA06007050A MXPA06007050A MX PA06007050 A MXPA06007050 A MX PA06007050A MX PA06007050 A MXPA06007050 A MX PA06007050A MX PA06007050 A MXPA06007050 A MX PA06007050A
- Authority
- MX
- Mexico
- Prior art keywords
- acetate
- methyl
- ethyl
- butyrate
- propionate
- Prior art date
Links
- 239000004480 active ingredient Substances 0.000 title claims abstract description 61
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 31
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 claims abstract description 30
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 22
- -1 hydrocarbon radicals Chemical class 0.000 claims description 144
- 229940022663 Acetate Drugs 0.000 claims description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-M acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 49
- 235000019441 ethanol Nutrition 0.000 claims description 47
- 239000004215 Carbon black (E152) Substances 0.000 claims description 31
- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 23
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- GLZPCOQZEFWAFX-JXMROGBWSA-N β-Geraniol Chemical compound CC(C)=CCC\C(C)=C\CO GLZPCOQZEFWAFX-JXMROGBWSA-N 0.000 claims description 13
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- 150000001298 alcohols Chemical class 0.000 claims description 12
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
- XBDQKXXYIPTUBI-UHFFFAOYSA-M propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 12
- HIGQPQRQIQDZMP-DHZHZOJOSA-N Geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 claims description 11
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-Phenylethanol Natural products OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 10
- 229930004021 citronellol Natural products 0.000 claims description 10
- 235000000484 citronellol Nutrition 0.000 claims description 10
- BAVONGHXFVOKBV-ZJUUUORDSA-N (-)-trans-carveol Natural products CC(=C)[C@@H]1CC=C(C)[C@@H](O)C1 BAVONGHXFVOKBV-ZJUUUORDSA-N 0.000 claims description 8
- HFNGYHHRRMSKEU-UHFFFAOYSA-N (4-methoxyphenyl)methyl acetate Chemical compound COC1=CC=C(COC(C)=O)C=C1 HFNGYHHRRMSKEU-UHFFFAOYSA-N 0.000 claims description 8
- OJEQSSJFSNLMLB-UHFFFAOYSA-N (4-methylphenyl) 2-phenylacetate Chemical compound C1=CC(C)=CC=C1OC(=O)CC1=CC=CC=C1 OJEQSSJFSNLMLB-UHFFFAOYSA-N 0.000 claims description 8
- OIGWAXDAPKFNCQ-UHFFFAOYSA-N (4-propan-2-ylphenyl)methanol Chemical compound CC(C)C1=CC=C(CO)C=C1 OIGWAXDAPKFNCQ-UHFFFAOYSA-N 0.000 claims description 8
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 8
- NEHNMFOYXAPHSD-JTQLQIEISA-N (S)-(-)-citronellal Natural products O=CC[C@@H](C)CCC=C(C)C NEHNMFOYXAPHSD-JTQLQIEISA-N 0.000 claims description 8
- MWKFXSUHUHTGQN-UHFFFAOYSA-N 1-Decanol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 8
- VSMOENVRRABVKN-MRVPVSSYSA-N 1-Octen-3-ol Natural products CCCCC[C@H](O)C=C VSMOENVRRABVKN-MRVPVSSYSA-N 0.000 claims description 8
- CIXAYNMKFFQEFU-UHFFFAOYSA-N 2-(4-methylphenyl)acetaldehyde Chemical compound CC1=CC=C(CC=O)C=C1 CIXAYNMKFFQEFU-UHFFFAOYSA-N 0.000 claims description 8
- QNVRIHYSUZMSGM-LURJTMIESA-N 2-Hexanol Natural products CCCC[C@H](C)O QNVRIHYSUZMSGM-LURJTMIESA-N 0.000 claims description 8
- JYVLIDXNZAXMDK-UHFFFAOYSA-N 2-Pentanol Chemical compound CCCC(C)O JYVLIDXNZAXMDK-UHFFFAOYSA-N 0.000 claims description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
- KVKKTLBBYFABAZ-UHFFFAOYSA-N 2-phenylethyl 2-methylbutanoate Chemical compound CCC(C)C(=O)OCCC1=CC=CC=C1 KVKKTLBBYFABAZ-UHFFFAOYSA-N 0.000 claims description 8
- WMBOCUXXNSOQHM-DHZHZOJOSA-N 3-Butylidenephthalide Natural products C1=CC=C2C(=C/CCC)\OC(=O)C2=C1 WMBOCUXXNSOQHM-DHZHZOJOSA-N 0.000 claims description 8
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-Methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 claims description 8
- NMRPBPVERJPACX-QMMMGPOBSA-N 3-Octanol Natural products CCCCC[C@@H](O)CC NMRPBPVERJPACX-QMMMGPOBSA-N 0.000 claims description 8
- YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 claims description 8
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-Heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 claims description 8
- RECUKUPTGUEGMW-UHFFFAOYSA-N Carvacrol Chemical compound CC(C)C1=CC=C(C)C(O)=C1 RECUKUPTGUEGMW-UHFFFAOYSA-N 0.000 claims description 8
- SVURIXNDRWRAFU-OGMFBOKVSA-N Cedrol Chemical compound C1[C@]23[C@H](C)CC[C@H]3C(C)(C)[C@@H]1[C@@](O)(C)CC2 SVURIXNDRWRAFU-OGMFBOKVSA-N 0.000 claims description 8
- JOZKFWLRHCDGJA-LLVKDONJSA-N Citronellyl acetate Natural products CC(=O)OCC[C@H](C)CCC=C(C)C JOZKFWLRHCDGJA-LLVKDONJSA-N 0.000 claims description 8
- KSMVZQYAVGTKIV-UHFFFAOYSA-N Decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 claims description 8
- AZOCECCLWFDTAP-RKDXNWHRSA-N Dihydrocarvone Natural products C[C@@H]1CC[C@@H](C(C)=C)CC1=O AZOCECCLWFDTAP-RKDXNWHRSA-N 0.000 claims description 8
- HCRBXQFHJMCTLF-ZCFIWIBFSA-N Ethyl 2-methyl butyrate Natural products CCOC(=O)[C@H](C)CC HCRBXQFHJMCTLF-ZCFIWIBFSA-N 0.000 claims description 8
- RRAFCDWBNXTKKO-UHFFFAOYSA-N Eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 8
- LHGVFZTZFXWLCP-UHFFFAOYSA-N Guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 8
- JARKCYVAAOWBJS-UHFFFAOYSA-N Hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 claims description 8
- BJIOGJUNALELMI-ONEGZZNKSA-N Isoeugenol Natural products COC1=CC(\C=C\C)=CC=C1O BJIOGJUNALELMI-ONEGZZNKSA-N 0.000 claims description 8
- HJOVHMDZYOCNQW-UHFFFAOYSA-N Isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 8
- KEVYVLWNCKMXJX-ZCNNSNEGSA-N Isophytol Natural products CC(C)CCC[C@H](C)CCC[C@@H](C)CCC[C@@](C)(O)C=C KEVYVLWNCKMXJX-ZCNNSNEGSA-N 0.000 claims description 8
- YGHRJJRRZDOVPD-UHFFFAOYSA-N Isovaleraldehyde Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 claims description 8
- UWKAYLJWKGQEPM-LBPRGKRZSA-N Linaloyl acetate Natural products CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 claims description 8
- FLIACVVOZYBSBS-UHFFFAOYSA-N Methyl palmitate Chemical compound CCCCCCCCCCCCCCCC(=O)OC FLIACVVOZYBSBS-UHFFFAOYSA-N 0.000 claims description 8
- OSWPMRLSEDHDFF-UHFFFAOYSA-N Methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 8
- RXBQNMWIQKOSCS-RKDXNWHRSA-N Myrtenol Natural products C1[C@H]2C(C)(C)[C@@H]1CC=C2CO RXBQNMWIQKOSCS-RKDXNWHRSA-N 0.000 claims description 8
- FQTLCLSUCSAZDY-QKXCFHHRSA-N Nerolidol Natural products CC(C)=CCC\C(C)=C/CC[C@](C)(O)C=C FQTLCLSUCSAZDY-QKXCFHHRSA-N 0.000 claims description 8
- GYHFUZHODSMOHU-UHFFFAOYSA-N Nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 claims description 8
- NUJGJRNETVAIRJ-UHFFFAOYSA-N Octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 claims description 8
- IWDCLRJOBJJRNH-UHFFFAOYSA-N P-Cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims description 8
- GGHMUJBZYLPWFD-MYYUVRNCSA-N Patchouli alcohol Natural products O[C@@]12C(C)(C)[C@H]3C[C@H]([C@H](C)CC1)[C@]2(C)CC3 GGHMUJBZYLPWFD-MYYUVRNCSA-N 0.000 claims description 8
- GHMLBKRAJCXXBS-UHFFFAOYSA-N Resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 8
- SMQUZDBALVYZAC-UHFFFAOYSA-N Salicylaldehyde Chemical compound OC1=CC=CC=C1C=O SMQUZDBALVYZAC-UHFFFAOYSA-N 0.000 claims description 8
- 235000009499 Vanilla fragrans Nutrition 0.000 claims description 8
- 240000006722 Vanilla planifolia Species 0.000 claims description 8
- 235000012036 Vanilla tahitensis Nutrition 0.000 claims description 8
- SRBFZHDQGSBBOR-SQOUGZDYSA-N Xylose Natural products O[C@@H]1CO[C@@H](O)[C@@H](O)[C@@H]1O SRBFZHDQGSBBOR-SQOUGZDYSA-N 0.000 claims description 8
- HRHOWZHRCRZVCU-AATRIKPKSA-N [(E)-hex-2-enyl] acetate Chemical compound CCC\C=C\COC(C)=O HRHOWZHRCRZVCU-AATRIKPKSA-N 0.000 claims description 8
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 claims description 8
- PSQYTAPXSHCGMF-BQYQJAHWSA-N beta-ionone Natural products CC(=O)\C=C\C1=C(C)CCCC1(C)C PSQYTAPXSHCGMF-BQYQJAHWSA-N 0.000 claims description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-M butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 8
- ZAJNGDIORYACQU-UHFFFAOYSA-N decan-2-one Chemical compound CCCCCCCCC(C)=O ZAJNGDIORYACQU-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N iso-propanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 8
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 claims description 8
- GWYFCOCPABKNJV-UHFFFAOYSA-M isovalerate Chemical compound CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 8
- IJXHLVMUNBOGRR-UHFFFAOYSA-N methyl nonanoate Chemical compound CCCCCCCCC(=O)OC IJXHLVMUNBOGRR-UHFFFAOYSA-N 0.000 claims description 8
- KWOLFJPFCHCOCG-UHFFFAOYSA-N methylphenylketone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 8
- VKCYHJWLYTUGCC-UHFFFAOYSA-N nonan-2-one Chemical compound CCCCCCCC(C)=O VKCYHJWLYTUGCC-UHFFFAOYSA-N 0.000 claims description 8
- KBPLFHHGFOOTCA-UHFFFAOYSA-N octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 claims description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 8
- UHEPJGULSIKKTP-UHFFFAOYSA-N sulcatone Chemical compound CC(C)=CCCC(C)=O UHEPJGULSIKKTP-UHFFFAOYSA-N 0.000 claims description 8
- CYIFVRUOHKNECG-UHFFFAOYSA-N tridecan-2-one Chemical compound CCCCCCCCCCCC(C)=O CYIFVRUOHKNECG-UHFFFAOYSA-N 0.000 claims description 8
- RJASFPFZACBKBE-UHFFFAOYSA-N 2-methylpropyl 2-phenylacetate Chemical compound CC(C)COC(=O)CC1=CC=CC=C1 RJASFPFZACBKBE-UHFFFAOYSA-N 0.000 claims description 7
- PRNCMAKCNVRZFX-UHFFFAOYSA-N 3,7-dimethyloctan-1-ol Chemical compound CC(C)CCCC(C)CCO PRNCMAKCNVRZFX-UHFFFAOYSA-N 0.000 claims description 7
- DTUQWGWMVIHBKE-UHFFFAOYSA-N Phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 claims description 7
- JAGZUIGGHGTFHO-UHFFFAOYSA-N ethyl 3-phenylpropanoate Chemical compound CCOC(=O)CCC1=CC=CC=C1 JAGZUIGGHGTFHO-UHFFFAOYSA-N 0.000 claims description 7
- IUSBVFZKQJGVEP-SNAWJCMRSA-N isoeugenol acetate Chemical compound COC1=CC(\C=C\C)=CC=C1OC(C)=O IUSBVFZKQJGVEP-SNAWJCMRSA-N 0.000 claims description 7
- AMQJEAYHLZJPGS-UHFFFAOYSA-N n-pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 7
- GJWGZSBNFSBUPX-UHFFFAOYSA-N pentyl octanoate Chemical compound CCCCCCCC(=O)OCCCCC GJWGZSBNFSBUPX-UHFFFAOYSA-N 0.000 claims description 7
- JDQVBGQWADMTAM-UHFFFAOYSA-N phenethyl isobutyrate Chemical compound CC(C)C(=O)OCCC1=CC=CC=C1 JDQVBGQWADMTAM-UHFFFAOYSA-N 0.000 claims description 7
- WAPNOHKVXSQRPX-UHFFFAOYSA-N 1-phenylethanol Chemical compound CC(O)C1=CC=CC=C1 WAPNOHKVXSQRPX-UHFFFAOYSA-N 0.000 claims description 6
- KYWIYKKSMDLRDC-UHFFFAOYSA-N 2-Undecanone Chemical compound CCCCCCCCCC(C)=O KYWIYKKSMDLRDC-UHFFFAOYSA-N 0.000 claims description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- FKRCODPIKNYEAC-UHFFFAOYSA-N Ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 6
- GYCKQBWUSACYIF-UHFFFAOYSA-N Ethyl salicylate Chemical compound CCOC(=O)C1=CC=CC=C1O GYCKQBWUSACYIF-UHFFFAOYSA-N 0.000 claims description 6
- XHXUANMFYXWVNG-ADEWGFFLSA-N Menthyl acetate Natural products CC(C)[C@@H]1CC[C@@H](C)C[C@H]1OC(C)=O XHXUANMFYXWVNG-ADEWGFFLSA-N 0.000 claims description 6
- KXKVLQRXCPHEJC-UHFFFAOYSA-N Methyl acetate Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 6
- MWOOGOJBHIARFG-UHFFFAOYSA-N Vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 claims description 6
- KGEKLUUHTZCSIP-HOSYDEDBSA-N [(1S,4S,6R)-1,7,7-trimethyl-6-bicyclo[2.2.1]heptanyl] acetate Chemical compound C1C[C@]2(C)[C@H](OC(=O)C)C[C@H]1C2(C)C KGEKLUUHTZCSIP-HOSYDEDBSA-N 0.000 claims description 6
- 239000004615 ingredient Substances 0.000 claims description 6
- KQNPFQTWMSNSAP-UHFFFAOYSA-M isobutyrate Chemical compound CC(C)C([O-])=O KQNPFQTWMSNSAP-UHFFFAOYSA-M 0.000 claims description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N n-butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 6
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical compound C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 claims description 5
- FLUWAIIVLCVEKF-UHFFFAOYSA-N (2-methyl-1-phenylpropan-2-yl) acetate Chemical compound CC(=O)OC(C)(C)CC1=CC=CC=C1 FLUWAIIVLCVEKF-UHFFFAOYSA-N 0.000 claims description 5
- RNLHVODSMDJCBR-VURMDHGXSA-N (Z)-3-methyl-5-(2,2,3-trimethylcyclopent-3-en-1-yl)pent-4-en-2-ol Chemical compound CC(O)C(C)\C=C/C1CC=C(C)C1(C)C RNLHVODSMDJCBR-VURMDHGXSA-N 0.000 claims description 5
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 1-butanal Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 5
- MSHFRERJPWKJFX-UHFFFAOYSA-N Anisyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 claims description 5
- OOCCDEMITAIZTP-QPJJXVBHSA-N Cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 claims description 5
- 239000005792 Geraniol Substances 0.000 claims description 5
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 claims description 5
- 229940017219 METHYL PROPIONATE Drugs 0.000 claims description 5
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 claims description 5
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 claims description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 229930008393 geraniol Natural products 0.000 claims description 5
- 229940113087 geraniol Drugs 0.000 claims description 5
- SSMBXPJYHMZLOJ-UHFFFAOYSA-N propan-2-yl 2-phenylacetate Chemical compound CC(C)OC(=O)CC1=CC=CC=C1 SSMBXPJYHMZLOJ-UHFFFAOYSA-N 0.000 claims description 5
- 239000001871 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol Substances 0.000 claims description 4
- HQMIYCYWQSHQLC-UHFFFAOYSA-N (2,5-dimethyl-3-oxofuran-2-yl) acetate Chemical compound CC(=O)OC1(C)OC(C)=CC1=O HQMIYCYWQSHQLC-UHFFFAOYSA-N 0.000 claims description 4
- BHJHPYFAYGAPLS-UHFFFAOYSA-N (2-methoxyphenyl) acetate Chemical compound COC1=CC=CC=C1OC(C)=O BHJHPYFAYGAPLS-UHFFFAOYSA-N 0.000 claims description 4
- DCXXKSXLKWAZNO-UHFFFAOYSA-N (2-methyl-6-methylideneoct-7-en-2-yl) acetate Chemical compound CC(=O)OC(C)(C)CCCC(=C)C=C DCXXKSXLKWAZNO-UHFFFAOYSA-N 0.000 claims description 4
- AMZORBZSQRUXNC-UHFFFAOYSA-N (2-methylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C AMZORBZSQRUXNC-UHFFFAOYSA-N 0.000 claims description 4
- 239000000260 (2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol Substances 0.000 claims description 4
- 239000001562 (3E)-3-propylidene-2-benzofuran-1-one Substances 0.000 claims description 4
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 claims description 4
- NPFVOOAXDOBMCE-PLNGDYQASA-N (3Z)-hex-3-en-1-yl acetate Chemical compound CC\C=C/CCOC(C)=O NPFVOOAXDOBMCE-PLNGDYQASA-N 0.000 claims description 4
- UPPSFGGDKACIKP-UHFFFAOYSA-N (4-methylphenyl) 2-methylpropanoate Chemical compound CC(C)C(=O)OC1=CC=C(C)C=C1 UPPSFGGDKACIKP-UHFFFAOYSA-N 0.000 claims description 4
- MBZRJSQZCBXRGK-UHFFFAOYSA-N (4-tert-butylcyclohexyl) acetate Chemical compound CC(=O)OC1CCC(C(C)(C)C)CC1 MBZRJSQZCBXRGK-UHFFFAOYSA-N 0.000 claims description 4
- QILMAYXCYBTEDM-IWQZZHSRSA-N (9Z)-17-oxacycloheptadec-9-en-1-one Chemical compound O=C1CCCCCCC\C=C/CCCCCCO1 QILMAYXCYBTEDM-IWQZZHSRSA-N 0.000 claims description 4
- BTSIZIIPFNVMHF-ARJAWSKDSA-N (E)-2-Penten-1-ol Chemical compound CC\C=C/CO BTSIZIIPFNVMHF-ARJAWSKDSA-N 0.000 claims description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N (E)-Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 4
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- 239000001178 (E)-dec-3-en-2-one Substances 0.000 claims description 4
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- 239000001449 ethyl (2R)-2-methylpentanoate Substances 0.000 claims description 3
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- 229940021016 Vitamin IV solution additives Drugs 0.000 description 1
- UZJQQWFHPLYECS-SFECMWDFSA-N [(Z)-hex-3-enyl] (Z)-hex-3-enoate Chemical compound CC\C=C/CCOC(=O)C\C=C/CC UZJQQWFHPLYECS-SFECMWDFSA-N 0.000 description 1
- HTQLNWONIAXQKC-UHFFFAOYSA-N [4-(4-methylpent-3-enyl)cyclohex-3-en-1-yl]methyl acetate Chemical compound CC(C)=CCCC1=CCC(COC(C)=O)CC1 HTQLNWONIAXQKC-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- BVQHHUQLZPXYAQ-UHFFFAOYSA-N acetyl butanoate Chemical compound CCCC(=O)OC(C)=O BVQHHUQLZPXYAQ-UHFFFAOYSA-N 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive Effects 0.000 description 1
- 150000001336 alkenes Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminum Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000003712 anti-aging Effects 0.000 description 1
- 230000000111 anti-oxidant Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000004429 atoms Chemical group 0.000 description 1
- 230000003115 biocidal Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- FCDMDSDHBVPGGE-UHFFFAOYSA-N butyl 2,2-dimethylpropanoate Chemical compound CCCCOC(=O)C(C)(C)C FCDMDSDHBVPGGE-UHFFFAOYSA-N 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- KMVZWUQHMJAWSY-UHFFFAOYSA-N chloro-dimethyl-prop-2-enylsilane Chemical compound C[Si](C)(Cl)CC=C KMVZWUQHMJAWSY-UHFFFAOYSA-N 0.000 description 1
- 239000002781 deodorant agent Substances 0.000 description 1
- 239000000645 desinfectant Substances 0.000 description 1
- 230000000249 desinfective Effects 0.000 description 1
- 229930007026 dihydrocarveol Natural products 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005837 enolization reaction Methods 0.000 description 1
- 150000002085 enols Chemical class 0.000 description 1
- 229960001617 ethyl hydroxybenzoate Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000001747 exhibiting Effects 0.000 description 1
- 239000002979 fabric softener Substances 0.000 description 1
- 230000001815 facial Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000004872 foam stabilizing agent Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- GPRLSGONYQIRFK-UHFFFAOYSA-N hydron Chemical compound [H+] GPRLSGONYQIRFK-UHFFFAOYSA-N 0.000 description 1
- 230000002209 hydrophobic Effects 0.000 description 1
- 239000003752 hydrotrope Substances 0.000 description 1
- 238000009114 investigational therapy Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 235000011929 mousse Nutrition 0.000 description 1
- LZWFXVJBIZIHCH-UHFFFAOYSA-N oct-1-en-3-yl butanoate Chemical compound CCCCCC(C=C)OC(=O)CCC LZWFXVJBIZIHCH-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- URLKBWYHVLBVBO-UHFFFAOYSA-N p-xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002335 preservative Effects 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 239000011252 protective cream Substances 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- 230000036633 rest Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 150000003376 silicon Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 230000000475 sunscreen Effects 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000002459 sustained Effects 0.000 description 1
- 235000012976 tarts Nutrition 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DNBKBOHCTZPNEL-UHFFFAOYSA-N undec-1-en-1-one Chemical compound CCCCCCCCCC=C=O DNBKBOHCTZPNEL-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical compound CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
- 229940070710 valerate Drugs 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamins Natural products 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Cyclic siloxanes that contain releasable active ingredients are described. The active ingredient can be an alcohol or enolizable carbonyl-containing compound such as a ketone, aldehyde, or ester. The product siloxanes are useful in a variety of personal and household care products where slow or controlled release of active ingredient is desired. A preferred embodiment utilizes substituents that when released as active ingredients are fragrant.
Description
CYCLIC SILOXANES THAT RELEASE ACTIVE INGREDIENTS
Cross reference to related requests Not applicable
Declaration regarding federally founded investigation Not applicable
FIELD OF THE INVENTION The present invention relates to cyclic siloxanes suitable for use in a variety of applications including formulations for personal care, household products, automotive, textiles and molding materials, wherein the cyclic siloxane has been chemically modified to release a active ingredient on hydrolysis. The present invention further relates to such molecules wherein the rate of release of active ingredient is sufficiently slow, so that products formulated with the modified cyclic siloxane exhibit desirable effects for long periods.
BACKGROUND OF THE INVENTION The sustained, slow release of an active ingredient is a highly desirable trait in many personal care products, textiles, automotive, plastics, laundry and home. A variety of media have been proposed and implemented to achieve this goal. Among these means are to dissolve or suspend fragrant compounds in personal care emulsions (US 5,525,588, US 5,525,555, US 5,490,982, US 5,372,806, EP 0334490, WO 0064497), encapsulation of a fragrant compound (US 5,500,223, US 5,324,444, US 5,185,155). US 5,176,903, US 5,130,171, US 6,325,859, US 6,309,715, US 6,325,274, US 6,213,409, US 6,200,949, US 5,142,792, US 5,867,755, US 5,049,182, US patent applications 20020187221, 20020009522 and 20010008635, EP 1 1 16515. , EP 1061 124, EP 1 133929, WO 0179303, WO 01731 88, WO 9815192, WO 02076514), dissolving a fragrant compound in a hydrophobic phase, such as a silicone (US 5,449,512, US 5,160,494, US 5,234,689, WO 0241709 ), incorporation of a fragrant compound in cross-linked polymer (US 6,435,423, US 5, 139,864, US 6,379,689, US 5,387,622, US 5,387.41 1, WO 03032749, WO 02065858, JP 1 1047581), incorporation of fragrant compounds in permeable laminates ( US 6,500,444; US 5,071, 704; US 5,008.1 15), incorporation of fragrant compounds into matrices that soften at body temperature (US 4,908,208; EP 1 178107, WO 0016643), incorporation of fragrant compounds in matrices that biodegrade (US 6, 121, 343) or are bioactivated (US 5,378,468), incorporation of fragrant compounds in speed controlling membranes (US 6,063,365 and US 4,445,641), derivatizing silanes with fragrant alcohols to form alkoxy silanes (US 4,524,018 and US 4,500,725) and derivatizing fragrances to form photosensitive molecules that release the fragrance upon exposure to light (WO 02083620; JP2002020783A). The derivation of active to give organic molecules (ie, that do not contain silicon) hydrolyzables has also been well documented in the literature. The union of silicon-containing molecules with active ingredients is of particular interest because many active ingredients are highly functional organics and suffer from incompatibility with the silicones found in consumer and personal care products, leading to syneresis and other phenomena. phase separation. The derivation of silanes with long chain alcoholic skin care actives to give alkoxytrimethylsilanes (US 5,847,179) and derivation of silanes with skin exfoliants of hydroxycarboxylic acid to form (triorganosilyl) alkoxycarboxylates (US 6, 143,309; US 6,228,380; US 6,267,977) have been described. The direct displacement of a group leaving alkoxy on a silicon atom by a fragrant alcohol was reported by Alien, et al. to give silicon esters or fragrant linear silicate esters (US 3,215,719 and US 3,271, 305). Several others also reported similar alkoxy displacement reaction to form linear fragrant siloxane polymers or copolymers (GB 2,041,964; GB 2,042,890; EP 273266). The reaction of an alcohol, aldehyde, ketone or lactone with a silyl hydride in the presence of a metal carboxylate salt and a reducing agent to form linear polymers and copolymers was also reported (WO 9628497). Other routes of fragrant silicones using silyl hydrides were described by Anderson, et al. (EP 878497; JP 1 0330382; US 6,262,287) and Perry, et al. (US 6,046,154, US 6,077,923, US 6,153,578, US 6,054,547, US 6,075,111, US 6,322,777, US 6,083,901). In these processes, hydrosilylation chemistry was employed to bind the active portion of the molecule to the silicone backbone.
Brief description of the invention The present invention provides a cyclic siloxane that releases active ingredient having formula I or II:
I II
R10, R11, R12 and R3 are each independently selected from the group of monovalent C-α-C24 hydrocarbon radicals. As used herein, the phrase "monovalent hydrocarbon radical" includes both aliphatic and aromatic monovalent hydrocarbon radicals which may also include heteroatoms, such as, oxygen, nitrogen, phosphorus and sulfur, as well as halogens, fluoro, chloro, bromo and iodo. The quantities n and q are each independently more than or equal to 1, and the quantities p, r and s are each independently equal to or greater than 0, with the proviso that n + p must be equal to or greater than 3 and that q + r + s must be equal to or greater than 3. RF has the formula (R1O) a (R2O) b (R3O) c (R4) d (R5) eSiRu, with Ru defined as a monovalent unsaturated hydrocarbon radical of C2-C 0 (which when undergone hydrosilylation becomes a divalent hydrocarbon radical of C2-C40), wherein R1, R2 and R3 are independently selected or derivatives of group F or group G. The group F as defined is the group of alcohols consisting of R1OH, R2OH and R3OH, wherein R1OH, R2OH and R3OH are alcoholic active ingredients, and group G is defined as the group of active ingredients esters, ketones or aldehydes, each having independently the structure:
R7-C (R8) = C (O -) - R9
with R4 and R5 independently selected from the group consisting of monovalent hydrocarbon radicals having from one to forty carbon atoms and monovalent alkoxy radicals having from one to forty carbon atoms, R6 a monovalent saturated hydrocarbon radical of two to forty carbon atoms carbon containing a terminal acetylenic or olefinic portion. The subscript a has a value that varies from 1 to 3 and the subscripts b, c, d and e have values ranging from 0 to 2, subject to the limitation that a + b + c + d + e = 3. R7, R8 and R9 are each independently selected from the group consisting of hydrogen and monovalent hydrocarbon radicals having one to one hundred carbon atoms. The present invention also provides compositions comprising a siioxane that releases active ingredient. Of particular use are cosmetic compositions comprising a siloxane that releases active ingredient, such as perfumes, skin creams, make-up, bases and the like, as well as laundry agents, such as detergent compositions, rinse additives, fabric softeners and Similar.
DETAILED DESCRIPTION OF THE INVENTION The compounds of the present invention introduce portions of active ingredient via hydrosilylation of an olefinic silane molecule. These resulting siloxane molecules are useful in a variety of consumer care compositions. The present invention is directed to new compositions of matter that are siloxanes that release an active ingredient containing carbonyl or alcoholic upon hydrolysis, where the active ingredient can be illustrated by, but not limited to, adhesion promoters, adhesives, anti-aging agents, antioxidants, antiperspirants, antistatic agents, biocides, bitter agents, bleaching agents, brighteners, dyes, conditioners, defoamers, detergents, disinfectants, dispersing agents, fillers, foaming agents, foam stabilizers, fragrances, humectants, hydrotropes, insect repellents, crystals liquids, humectants, odor absorbers, opacifying agents, oral care additives, pharmaceuticals, preservatives, rheology modifiers, screen agents, sequestering or chelating agents, solubilizers, solvents, sunscreens, surfactants, suspending agents, tanning agents, thickeners , vitamins or other nutrients or bleaching agents. The olefinic silanes used by the present invention are described by the formula:
(R1O) a (R2O) b (R3O) c (R4) d (R5) eSYR6 wherein R1O, R2O and R3O are independently derived from the group F or group G. The group F is the group of alcohols consisting of R1OH, R2OH and R 3 OH, wherein R 1 OH, R 2 OH and R 3 OH are alcoholic active ingredients, wherein R 1, R 2 and R 3 are independently monovalent hydrocarbon radicals having from four to one hundred carbon atoms, preferably five to one hundred carbon atoms, more preferably six to one hundred atoms carbon and most preferably seven to one hundred carbon atoms which may also contain heteroatoms, such as, oxygen, sulfur, nitrogen, phosphorus and the halogens, fluorine, chlorine, bromine and iodine. Group G is the carbonyl-containing active group, or carbonyl active ingredients, each independently having the structure:
R7-CH (R8) (C = O) -R 9
wherein the carbonyl containing active is capable of exhibiting the enol form of the carbonyl portion under reaction conditions as shown:
R-CH (R) (C = O) -R? R7-C (R8) = C (OH) -R9
and which will react through the enol hydroxyl group to form a carbon-oxygen-silicon bond (ie, R7-C (R8) = C (O -) - R9), where the hifen after oxygen in the formula indicates that the species is a monovalent radical and independently describes R \ R2 and R3), with R4 and R5 selected from the group consisting of monovalent hydrocarbon radicals having from one to forty carbon atoms and monovalent alkoxy radicals having from one to forty carbon atoms , R6 a monovalent unsaturated hydrocarbon radical of C2-C40 containing an reactive olefinic or acetylenic portion, which is preferably a terminal olefin or acetylene, where the subscript a has a value ranging from 1 to 3 and the subscripts b, c , d and e have values that vary from 0 to 2 subject to the limitation that a + b + c + d + e = 3; R7, R8 and R9 are each independently selected from the group consisting of monovalent hydrocarbon radicals having from one to one hundred carbon atoms. It should be noted that the structure:
R7-C (R8) = C (O -) - R9
it is a conjugated structure that corresponds to the enol structure:
R7-C (R8) = C (OH) -R9
but lacking hydroxyl hydrogen. In the structure:
R7-C (R8) = C (O -) - R9
Hyphene after the oxygen atom indicates a univalent binding site, where the structure is a monovalent radical. As used herein, the phrase of one to one hundred carbon atoms is chosen wherein the class of available carbonyl containing active is subtended by the formula R7-CH (R8) (C = O) -R9. As used herein, the phrase "monovalent hydrocarbon radical" includes both aliphatic and aromatic monovalent hydrocarbon radicals which may also include heteroatoms, such as oxygen, nitrogen, phosphorus, sulfur and the halogens fluorine, chlorine, bromine and iodine. The following synthetic examples are intended to illustrate the general synthetic reaction schemes that a person having ordinary skill in the silicone chemistry art would normally employ in order to prepare the olefinic silanes used by the present invention. In this way, these reaction schemes are illustrative only and do not represent the only synthetic routes that can be used. When the starting material is an active alcoholic ingredient, such as, fenetanol, olefinic halosilanes or olefinic silicon alkoxides can be used as starting materials to produce the siloxanes that release active ingredient of the present invention via olefinic silanes bearing active (reaction schemes) l-ll l).
Reaction scheme I:
Reaction scheme
Reaction scheme lll:
where the R groups for reaction III may be Et (C2H5-) or -CH2CH2C6H5. Similarly, 3-methyl-5- (2,2,3-trimethyl-3-cyclopenten-1-yl) -4-penten-2-ol will react with chloromethylvinylsilane in a similar manner (reaction scheme IV):
Reaction scheme IV:
how the allyldimethylchlorosilane will react with citronellol in a similar reaction scheme V:
Reaction scheme V:
Representative alcohols which are precursors of the silanes or siloxanes containing active compounds of the present invention can be illustrated, but not limited to acetovainillone, allyl amyl glycolate, allyl isoamyl glycolate, amyl amyl alcohol, anisole alcohol, benzoin, benzyl alcohol, sodium salicylate, benzyl, 1-butanol, butylated hydroxytoluene, butyl lactate, 2-t-butyl-5-methylphenol, 2-t-butyl-6-methylphenol, carvacrol, carveol, 4-carvomentenol, cedrol, cetyl alcohol, cinnamic alcohol, citronellol , o-cresol, m-cresol, p-cresol, crotyl alcohol, decahydro-2-naphthol, 1-decanol, 1-decen-3-ol, 9-decene-1-ol, diethyl malate, diethyl tartrate, dihydrocarveol, dihydromyrcenol, 2,6-diisopropylphenol, dimethicone copolyol, 2,6-dimethoxyphenol, 1,1-dimethoxy-3,7-dimethyloctane-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- octatnol, 3,7-dimethyl-6-octen-1-ol, 3,7-dimethyl-7-octen-1 -ol, dimethyl, 2-ethylphenol, 4-ethylguaiacol, 2-ethyl-1-hexanol, 2- ethyl hydroxybenzoate, ethyl 3-hydroxybutyrate, 3-ethyl-2-hydroxy-2-cyclopenten-1 -one, ethyl 2-hydroxycaproate, ethyl 3-hydroxyhexanoate, ethyl lactate, ethyl maltol, p-ethylphenol, salicylate ethyl, eugenol, farnesol, phenolic alcohol, geraniol, glucose pentaacetate, glycerol, glyceryl monostearate, guaiacol, 1-heptanol, 2-heptanol, 3-heptanol, cis-4-heptenol, cis-3-heptenol, n- hexanol, 2-hexanol, 3-hexanol, cis-2-hexenol, cis-3-hexenol, trans-3-hexenol, 4-hexenol, cis-3-hexeni-hydroxyamyl alcohol, 2-hydroxybenzoate, 2-hydroxyacetophenone, alcohol 4 -hydroxybenzyl, 3-hydroxy-2-butanone, hydroxycitronellal, 4- (4-hydroxy-3-methoxyphenyl) -2-butanone, 2-hydroxy-3-methyl-2-cyclopenten-1 -one, 4- (p- hydroxyphenyl) -2-butanone, 2-hydroxy-3,5, 5-trimethyl-2-cyclohexenone, d-isoascorbic acid, isoborneol, isoeugenol, isophytol, isopropyl alcohol, p-isopropylbenzyl alcohol, 4-isopropylcyclohexanol, 3-isopropylphenol, 4-isopropylphenol, 2-isopropylphenol, isopulegol, lauryl alcohol, linalool, maltol, menthol, 4-methoxybenzyl alcohol, 2-methoxy-4-methylphenol, 2-methoxy-4-propylphenol, 2-methoxy-4-vinylphenol, a-methylbenzyl alcohol, 2-methylbutanol, 3-methyl-2-butanol, 2-methyl-2-buten-1-ol, 2-methyl-3-buten-2-ol, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, 4-methyl-2,6-dimethoxyphenol, N- Methyl 3,7-dimethyl-7-hydroxyoctylidenantranilate, methyl 3-hydroxyhexanoate, 6-methyl-5-hepten-2-ol, 2-methylpentanol, 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-dihydrofuran, myrtenol, dihydrochalcone of noeperperidine, neomenthol, nerol, nerolidol, trans-2-cis-6-nonadienol , 1,3-nonanediol acetate, nonadil, 2-nonanol, cis-6-nonen-1 -ol, 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-1 -ol, cis-6-octen-1 -ol, cis-octen-1 -ol, 1 -octen -3-ol, oleyl alcohol, patchouli alcohol, 3-pentanol, n-pentanol, 2-pentanol, 1 -penten-1 -ol, cis-2-penten-1 -ol, perilylic alcohol, 2-phenoxyethanol arabinogalactan, ß-phenethyl alcohol, phenethyl salicylate, phenol, phenylacetaldehyde glyceryl acetal, 3-phenyl-1-pentanol, 5-phenyl-1-pentanol, 1-phenyl-1-pentanol, 1-phenyl-2-pentanol, 1-phenyl -3-methyl-1-pentano, phytol, pinacol, polyalkylene glycols, polysorbate 20, polysorbate 60, polysorbate 80, prenol, n-propanol, propenyl guaetol, propylene glycol, 2-propylphenol, 4-propylphenol, resorcinol, retinol, salicylaldehyde, sorbitan monostearate, sorbitol, stearyl alcohol, syringealdehyde, a-terpineol, tetrahydrogeraniol, tetrahydrolinalool, tetrahydromyrcenol, thymol, triethyl citrate, 1, 2,6-trihydroxyhexane, pa.a-trimethylbenzyl alcohol, 2- (5,5,6-trimethylbicyclo [2.2.1] hept-2-ylcyclohexanol, 5- (2,2, 3-trimethyl-3-cyclopentenyl) -3-methylpentan-2-ol, 3,7-1 1-trimethyl-2,6, 10-dodecatrien-1-ol, 3,7,1-trimeti-1, 6 , 10-dodecatrien-3-oI, 3,5,5-trimethyl-1-hexanol, 10-undecen-1 -ol, undecyl alcohol, vanilla, o-vanilla, vanillin butyl ether, 4-vinylphenol, 2,5- xylene, 2,6-xylene, 3,5-xylenol, 2,4-xylene and xylose When the starting material is an active ingredient containing carbonyl, such as 2-methyl-3- (4-t-butylphenyl) propanal olefinic halosilanes or olefinic silicon alkoxides, starting materials can be used to produce the siloxanes that release active compounds of the present invention via olefinic silanes that support active ingredients.
DMF (C2H5) 3N
Note that DMF is dimethylformamide. This reaction scheme can also be used to prepare the 3-methi-3- (3- (1-methylethylphenyl)) propanal derivative:
The reaction of carbonyl-containing species, for example, esters, ketones and aldehydes, requires the establishment of the tautomeric keto enol equilibrium. Tautomerism is the chemical phenomenon of establishing a balance between two or more structurally distinct compounds. In almost all cases, the difference between a tautomeric form of the equilibrium compounds and the other is the isomeric placement of a hydrogen atom. A prevalent form of tautomerism is the tautomeric equilibrium established between a carbonyl compound (ie, one containing a carbonyl group) and having an alpha hydrogen atom for the carbonyl group, i.e., a a hydrogen:
Form keto Form enol
In general, the equilibrium constant favors the keto form and the equilibrium rests on the left. The degree of enolization is affected mainly by solvent, concentration and temperature. When a strong base is present, both the enol and keto forms can lose a hydrogen ion (a proton), forming an enolate anion:
(") • Because both of these structures differ only in the placement of electrons, these are canonical forms of the same ion instead of tautomeric isomers.As oxygen is more electronegative than carbon, the predominant canonical form is one where the ionic charge is more localized in the oxygen atom Because the tautomeric equilibrium between enols and ketones or aldehydes is not normally a preparative reaction, equilibrium must occur because ketones and aldehydes often react through their forms of enol as they do instantaneously in the preparation of the compounds of the present invention.This tautomeric keto-enol equilibrium is also established for esters or organic acids, ie, in the above structures when R8 includes an oxygen binding to a group R appropriate, for example, OR ', the compound is an organic ester For a more detailed explanation of this chemical a, see J. March "Advanced Organic Chemistry", John Wiley & Sons, New York (1985), pp. 66-68 and 527-529 and references therein. Fragrant molecules, alcohols, ketones and aldehydes, can be reacted as the enol or alcohol tautomer to produce silicone or siloxanes that carry fragrant portions. The reaction involves reaction of the alcoholic or enolic form of the molecule with hydrogen, hydroxyl or halogen attached directly to a silicon atom to form the fragrant derivative. The reaction involves formation of the conjugate base related to the tautomeric form of enol or alcohol of the molecule:
RnOH is dissociated to H + and RpO "(conjugate base), n = 1, 2 or 3 (thus R1 etc, as previously defined);
where R "OH is a fragrant alcohol or the tautomeric form of enol of a fragrant ketone or aldehyde The aldehydes and ketones react with alcohol (s) R'OH to form hemiacetals (aldehyde derivatives) or hemicetals (ketone derivatives): RCH (O) + R'OH? RCH (OH) (OR ') hemiacetal, which has a conjugate base obtained by removing the hydroxyl hydrogen: RCH (O ") (OR') and RC (O) R" + R'OH? RC (OH) (R'O) R ", which has a conjugate base obtained in the same way by removing the hydroxyl hydrogen: RC (O") (R'O) R ". As used herein, Rn are fragrant portions, i.e., monovalent radicals, either as a neutrally charged monovalent radical (Rp or RnO) or as a charged monovalent radical, derived from the conjugated bases of fragrant molecules, for example, Rn + + O "2? R" O. "The representative carbonyl active ingredients which are precursors of the silanes containing active compounds of the present invention can be polished, but not limited to 4-acetoxy-3-pentyl-tetrahydropyran., allyl cinnamate, allyl 2-ethylbutyrate, allyl cyclohexanopropionate, allyl heptanoate, allyl hexanoate, allyl isovalerate, allyl nonanoate, allyl octanoate, allyl phenoxyacetate, allyl phenylacetate, allyl propionate, -amycinnamoyl, amyl octanoate, anisyl acetate, anisylphenyl acetate, benzyl acetate, benzyl acetoacetate, benzyl butyrate, benzyl cinnamate, benzyl isobutyrate, benzyl-soavalerate, benzyl phenylacetate, benzyl propionate, bornyl, bornyl isovalerate, bornyl valerate, butyl acetate, butyl butyrate, butyl butyllactate, 4-t-butylcyclohexyl acetate, butyl heptanoate, butyl hexanoate, butyl isobutyrate, butyl isovalerate, butyl laurate, butyl propionate, butyl stearate, 3-butylidenephthalide, butyl 2-methylbutyrate, butyl 10-undecenoate, β-butyrolactone, carvilo acetate, carvilo propionate, caryophyllene acetate, ace Caryl tart, trans-cinnamyl acetate, trans-cinnamyl butyrate, cinnamyl cinnamate, cinnamyl isobutyrate, citronellyl acetate, citronellyl butyrate, citronellyl isobutyrate, citronellyl propionate, citronellyl valerate, cyclohexanoethyl acetate, cyclohexyl, cyclohexyl butyrate, cyclohexyl isovalerate, cyclohexyl propionate, d-decalactone, e-decalactone,? -decalactone, 4-decanolide, decyl acetate, decyl butyrate, decylpropionate, diethyl malonate, diethyl sebacate, diethyl succinate, dihydrocarvyl acetate, dihydrocoumarin, dihydromyrcenyl acetate, dihydro-nor-dicyclopentadienyl acetate, dihydrotherminyl acetate, 3,7-dimethyl-1-6-octadien-3-yl acetate, 3,7-propionate dimethyl-1 -6-octadien-3-yl, 3,7-dimethyloctane-3-yl acetate, a, a-dimethylphenethyl acetate, a, a-dimethylphenethyl butyrate, 6,10-dimethyl-5-acetate, 9-undecadien-2-yl, d-dodecalactone, e-dodecalactone,? -dodecalactone, ethyl acetate, ethyl acetoacetate, ethyl 6-acetoxyhexanoate, ethyl 2-acetyl-3-phenylpropionate, ethyl benzoylacetate, 2-ethylbutyl acetate, ethyl butyrate, ethyl cinnamate, ethyl cyclohexanopropionate, ethyl decanoate, ethylene brasylate, ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate, ethyl 2,3-epoxybutyrate, ethyl 2-methyl-4-pentenoate, ethyl heptanoate, ethyl hexanoate, trans-3- ethyl hexenoate, 2-ethylhexyl acetate, ethyl isobutyrate, ethyl isovalerate, ethyl laurate, ethyl 2-mercaptopropionate, ethyl 3-mercaptopropionate, ethyl 2-methylbutyrate, ethyl 2-methylpentanoate, (methylthio) -acetate ethyl, (methylthio) methyl acetate, methyl 2- (methylthio) propionate, ethyl myristate, ethyl nonanoate, ethyl octanoate, ethyl palmitate, ethyl phenylacetate, ethyl 3-phenylpropionate, 3-phenyl-2 , Ethyl 3-epoxybutyrate, ethyl 3-phenylepropionate, ethyl propionate, ethyl stearate, 2,3,6,6-tetramethyl Ethyl-2-cyclohexencarboxylate, ethyl (p-tolyloxy) acetate, ethyl undecanoate, ethyl valerate, eugenyl acetate, phenol acetate, geranyl acetate, geranyl butyrate, geranyl phenylacetate, geranyl propionate, phenylacetate guaiacilo, guaicmadera acetate,? -heptalactone, heptyl acetate, heptyl butyrate, hypethyl isobutyrate,? -6-hexadecenlactone, d-hexalactone,? -hexalactone, 3-hexenyl acetate, cis-3-methylbutanoate hexenyl, cis-3-hexeno cis-3-hexenoate, cis-3-hexenyl phenylacetate, trans-2-hexenyl acetate, hexyl acetate, hexyl butyrate, hexyl hexanoate, hexyl isobutyrate, hexyl propionate, Hexyl 2-methylbutanoate, hexyl 3-methylbutanoate, hexyl phenylacetate, isoamyl acetate, isoamyl acetoacetate, isoamyl butyrate, isoamyl cinnamate, isoamyl hexanoate, isoamyl isobutyrate, isoamyl isovalerate, isoamyl laurate, isoamyl nonanoate, soamilo octanoate, f isoamyl enylacetate, isoamyl propionate, isobornyl acetate, isobornyl propionate, isobutyl acetate, isobutyl butyrate, isobutyl cinnamate, isobutyl hexanoate, isobutyl isobutyrate, isobutyl 2-methylbutyrate, isobutyl propionate, isoeugenyl acetate, cinnamate sopropyl, isobutyl phenylacetate, isopropyl acetate, isopropyl butyrate, isopropyl isobutyrate, isopropyl myristate, isopropyl palmitate, isopropyl phenylacetate, lauryl acetate, linalyl acetate, linalyl butyrate, linalyl isovalerate, mentalactone, Menthyl, Menthyl Cyclohexanecarboxylate, Menthyl Isovalerate, 4-Methoxybenzyl Acetate, 4-Methoxybenzyl Propionate, 2-Methoxyphenyl Acetate, 2-Methoxy-4- (1-Propenyl) Phenyl Acetate, Methyl Acetate, Acetate -methylbenzyl, a-methylbenzyl butyrate, a-methylbenzyl propionate, 2-methylbutyl acetate, 2-methylbutyl butyrate, 2-methylbutyl isovalerate, 3-methyl-2-methylbutanoate butyl, 2-methylbutyl 2-methylbutanoate, methyl pt-butylphenylacetate, methyl butyrate, methyl cinnamate, methyl decanoate, methyl heptanoate, methyl hexanoate, methyl isobutyrate, methyl sovalerate, methyl laurate, N Methyl 2-methyl-3- (4-t-butylphenylpropylidene) anthranilate, methyl myristate, methyl nonanoate, methyl octanoate, methyl palmitate, 4- (4-methyl-3-pentenyl) -3- acetate cyclohexenylmethyl, methyl 2-methylbutyrate, 2-methyl-6-methylene-7-octen-2-yl acetate, methyl 4-methylvalerate, methyl 2-methylpentanoate, methyl phenoxyacetate, 4-methylphenyl phenylacetate, ethyl acetate 2-methyl-3-phenylpropan-2-yl, methyl 3-phenylpropionate, methyl propionate, 2-methylpropyl phenylacetate, methyl phenylacetate, 2-methyl-3-phenylpropan-2-yl acetate, sodium stearate methyl, (p-tolyloxy) methyl acetate, methyl 9-undecentate, methyl valerate, mirtenyl acetate, neryl acetate, neryl butyrate, neryl isobutyrate, d- nonalactone,? -nonalactone, 1,3-nonanediol diacetate, nonyl acetate, nopyl acetate, octahydrocoumarin,? -octalactone, 1-octen-3-yl acetate, 1-octen-3-yl butyrate, octyl, acetyl butyrate, octyl isobutyrate, octyl isovalerate, octyl octanoate, octyl propionate, oxacycloheptadec-10-en-2-one,? -pentadecalactone, pentyl acetate, pentyl butyrate, pentyl hexanoate, octanoate pentyl, phenethyl acetate, phenethyl butyrate, phenethyl cinnamate, phenethyl hexanoate, phenethyl isobutyrate, phenethyl isovalerate, phenethyl 2-methylbutyrate, phenethyl 2-methylbutyrate, phenethyl 2-methylpropionate, phenethyl octanoate, phenylacetate phenethyl, phenethyl propionate phenoxyethyl propionate, 2-phenoxyethyl 2-methylpropionate, 3-phenyl-2-propenyl propionate, 3-phenylpropyl acetate, 2-phenylpropyl butyrate, 2-phenylpropyl isobutyrate, 2-phenylpropyl isovalerate , piperonyl acetate, p-isobutyrate iperonyl, prenyl acetate, propyl acetate, propyl butyrate, propyl heptanoate, propyl hexanoate, 3-propylidenephthalide, propyl sobutyrate, propyl propionate, propyl phenylacetate, sucrose octaacetate, terpinyl acetate, terpinyl butyrate , terpinyl isobutyrate, terpinyl propionate, tetrahydrofurfuryl acetate, tetrahydrofurfuryl butyrate, tetrahydrofurfuryl propionate, tetrahydrolinallyl acetate, 2,6,6,8-tetramethyltricyclo [5.3, 1.0 (1 .5 )] undecan-8-yl, p-tolyl acetate, p-tolyl isobutyrate, p-tolyl phenylacetate, triacetin, tributyl acetyl citrate, tributyrin, tripropionin, 3,5,5-trimethyhexyl acetate, d-undecalactone, ? -undecalactone,? -valerolactone, vanilla acetate, vanillin isobutyrate, 1-vinyl-2- (1-methylpropyl) cyclohexyl acetate, whiskey lactone, butyraldehyde, citronellal, decanal, cis-4-decenal, trans-4 -decenal, 2,4-dimethyl-3-cyclohexen-1 -carbaldehyde, 2,6-dimethyl-5- heptenal, 3,7-dimethyloctanal, 2-ethylbutyraldehyde, glutaraldehyde, heptanal, cis-4-heptenal, hexanal, hydrocinnamaldehyde, isobutyraldehyde, 3- (p-isopropylphenyl) -propionaldehyde, isovaleraldehyde, lauric aldehyde, 2-methylbutyraldehyde, 2-methyl -3- (p-isopropylphenol) propionaldehyde, 2- methylpentanal, 4- (4-methyl-3-pentenyl) -3-cyclohexen-1 -carbaldehyde, 4-methylphenylacetaldehyde, 3- (methylthio) butanal, 2-methyl -4- (2,6,6-trimethyl-2-cyclohexen-1-yl) butanal, 2-methylundecanal, nonanal, cis-6-nonenal, octanal, phenylacetaldehyde, 2-phenylpropionaldehyde, 3-phenylpropionaldehyde, propionaldehyde, p- tolylacetaldehyde, tridecanal, 2,4,6-trimethyl-3-cyclohexen-1 -carbaldehyde, 2,6,10-trimethyl-9-undecanal, 7-undecenal, 8-undecenal, 9-undecenal, 1-undecenal, valeraldehyde , acetanisol, 1'-acetonaphthone, 2'-acetonaphthone, acetone, acetophenone, 2-acetoxy-2,5-dimethyl-3 (2H) furanone, 2-acetylcyclopentanone, 4-acetyl-1,1-dimethyl-6-t -butylindane, 7-acetyl-1, 1, 3,4,4,6-hexanmethylindane, 2-ac ethyl-2-tizoiina, 6-acetil-1, 1, 2, 4,4,7-hexametil tetralina, alil a-ionone, bencilidenacetona, 2,3-butanedione, 2-sec-butilciclohexanona, 5-t-butiI- 3,5-dinitro-2,6-dimethylacetophenone, butyrophenone, camphor, 2-decanone, 3-decanone, 3-decen-2-one, dihydrocarvone, dihydro-β-ionone, dihydrojasmone, 4,5-dihydro-3 ( 2H) -thiophenone, 2 ', 4'-dimethylacetophenone, 3,4-dimethyl-1,2-cyclopentadione, 3,5-dimethyl-1,2-cyclopentadione, 2,6-dimethyl-4-heptanone, 1, 3 -diphenyl-2-propanone, 4- (1-ethoxyvinyl) -3,3,5,5-tetramethiichoxyhexanone, p-ethylacetophenone, ethyl vinyl ketone, geranylacetone, 2,3-heptanedione, 2-heptanone, 3-heptanone, 4 -heptanone, 3,4-hexanedione, 3-hexanone, 4-hexen-3-one, 2-hexyIidene cyclopentanone, α-ionone, β-ionone, 4-isobutyl-2,6-dimethyl-3,5-dinitroacetophenone, isophorone, 6-isopropyldehydro-2-naphthone, cis-jasmona, livescona, 4-methoxyacetophenone, 4- (p-methoxyphenyl) -2-butanone, 4'-methylacetophenone, 3-methyl-1,2-cyclohexanedione, 3-methyl -2-cyclohexen-1-one, 2- (2- (4-methyl-3-cyclohexe n-1 -yl) propyl) -cyclopentanone, 3-methyl-2-cyclopenten-1 -one, methyl dihydrojasmonate, methyl ethyl ketone, 2-methyl-3-heptanone, 5-methyl-2-hepten-4-one , 6-methyl-5-hepten-2-one, 5-methyl-a-ionone, 1- (2-methyl-5-isopropyl-2-cyclohexenyl) -1-propanone, 4-methyl-2-pentanone, 3 -methyl-2- (2-pentenyl) -2-cyclopenten-1 -one, 4-methyl-1-phenyl-2-pentanone, 2-methyltetrahydrofuran-3-one, 2-methyltetrahydrothiophen-3-one, 2-nonanone , 3-nonanone, 2-octanone, 3-octanone, 1-octen-3-one, 3-octen-2-one, 4-oxoisophorone, 2-pentadecanone, 2,3-pentanedione, 2-pentanone, 3-pentanone , 3-penten-2-one, 1-phenyl-1,2-propanedione, propiophenone, pulegone, 2-tridecanone, 2,2,6-trimethylcyclohexanone, 4- (2,6,6-trimethyl-2-cyclohexen- 1 -yl) -3-methyl-3-buten-2-one, 2-undecanone and 6-undecanone. The siloxanes that light active ingredients of the present invention are prepared from an organohydrogensiloxane via conventional hydrosilylation using the olefinic silane carrying active as the alkenyl source, an example of this reaction is:
y = 3-15 In this specific case, the siloxane species is actually a mixture of cyclic siloxanes with and ranging from 3-15. In this way, an organohydrogensiloxane having the formula III or IV:
111 IV
where R10, R1 1, R12 and R13 are each independently selected from the group of monovalent C1-C24 hydrocarbon radicals. The quantity t is greater than or equal to 3, the quantity u is greater than or equal to 1, and the quantity s is greater than or equal to 0, with the proviso that u + s must be equal to or greater than 3. The organohydrogenosiloxane is reacted under hydrosilylation conditions to produce an active-releasing siloxane having the formula I or II:
I II where the components and subscripts satisfy the definitions and previous requirements and RF has the formula
(R1O) a (R2O) b (R3O) c (R4) d (R5) eSiRu with Ru a divalent hydrocarbon radical of C2-C0, where the subscripts and components are as previously defined. This siloxane undergoes a slow hydrolysis under most conditions of use, whereby the siloxane releases an active ingredient containing carbonyl or alcoholic upon hydrolysis. This imparts a desirable effect to many different useful compositions, such as cosmetics and home-made products. The hydrosilylation reaction is conventionally carried out in the presence of a hydrosilylation catalyst selected from the group of hydrosilylation catalysts of ruthenium, osmium, rhodium, iridium, palladium and platinum. Examples of such catalysts are those described in U.S. Patents 2,823,218; 3, 159.601; 3, 159,662; and 3,775,452. The compositions of the present invention further provide that the siloxane releasing active ingredient have one or more substituents R1, R2 or R3, wherein each substituent is independently selected, whereby a carbonyl or alcohol-containing active ingredient resulting from the hydrolysis of said siloxane is selected from the group of alcohols consisting of acetovainillone, allyl amyl glycolate, allyl isoamyl glycolate, a-amyl cinnamyl alcohol, anisyl alcohol, benzoin, benzyl alcohol, benzyl salicylate, 1-butanol, butylated hydroxytoluene, butyl lactate, 2- t-butyl-5-methylphenol, 2-t-butyl-6-methylphenol, carvacrol, carveol, 4-carvomentenol, cedrol, cetyl alcohol, cinnamic alcohol, citronellol, o-cresol, m-cresol, p-cresol, crotyl alcohol , decahydro-2-naphthol, 1-decanol, 1-deen-3-ol, 9-deca-1-ol, diethyl malate, diethyl tartrate, dihydrocarvol, dihydromyrcenol, 2,6-diisopropylphenol, dimethicone copolyol, 6-Dimimeto xyphenol, 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-dlmethyl-1-octanol, 3,7-dimethyl-3- ocatnol, 3,7-dimethyl-6-octen-1 -ol, 3,7-dimeti! -7-octen-1 -ol, dimethyl, 2-ethylphenol, 4-ethylguaiacol, 2-ethyl-1-hexanol, 2 ethyl-hydroxybenzoate, ethyl 3-hydroxybutyrate, 3-ethyl-2-hydroxy-2-cyclopenten-1 -one, ethyl 2-hydroxycaproate, ethyl 3-hydroxyhexanoate, ethyl lactate, ethyl maltol, p-ethylphenol, ethyl salicylate, eugenol, farnesol, phenolic alcohol, geraniol, glucose pentaacetate, glycerol, glyceryl monostearate, guaiacol, 1-heptanol, 2-heptanol, 3-heptanol, cis-4-heptenol, cis-3-heptenol, n -hexanol, 2-hexanol, 3-hexanol, cis-2-hexenol, cis-3-hexenol, trans-3-hexenol, 4-hexenol, cis-3-hexenyl hydrocinnamic alcohol, 2-hydroxybenzoate, 2-hydroxyacetophenone, alcohol 4-hydroxybenzyl, 3-hydroxy-2-butanone, hydroxycitronellal, 4- (4-hydroxy-3-methoxyphenyl) -2-butanone, 2-hydroxy-3-methyl-2-cyclopenten-1 -one, 4- (p -hydroxyphenyl) -2-butanone, 2-hydroxy-3,5, 5-trimethyI-2-cyclohexenone, d-isoascorbic acid, isoborneol, isoeugenol, isophytol, isopropyl alcohol, p-isopropylbenzyl alcohol, 4-isopropylcyanohexanol, 3-isopropylphenol, 4-isopropylphenol, 2-isopropylphenol, isopulegol, lauryl alcohol, linalool, maltol, menthol, 4-methoxybenzyl alcohol, 2-methoxy-4-methylphenol, 2-methoxy-4-propylphenol, 2-methoxy-4-vinylphenol, a-methylbenzyl alcohol, 2-methylbutanol, 3-methyl-2-butanol , 2-methyl-2-buten-1 -oi, 2-methyl-3-buten-2-ol, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, 4-methyl-2,6-dimethoxyphenol, N Methyl -3,7-dimethyl-7-hydroxyoctylidenantranilate, methyl 3-hydroxyhexanoate, 6-methyl-5-hepten-2-ol, 2-methylpentanol, 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-dihydrofuran, myrtenol, dihydrochalcone of noeperperidine, neomentol, nerol, nerolidol, trans-2-cis-6 -nonadienol, 1,3-nonanediol acetate, nonadil, 2-nonanol, cis-6-nonen-1 -ol, 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-1 -ol, cis-6-octen-1 -ol, cis-octen-1 -ol, 1 -octen-3-ol, alcoholic oleic acid, patchouli alcohol, 3-pentanol, n-pentanol, 2-pentanol, 1 -penten-1 -ol, cis-2-penten-1 -ol, perilylic alcohol, 2-phenoxyethanol arabinogalactan, ß-phenethyl alcohol, phenethyl salicylate, phenol, phenylacetaldehyde glyceryl acetal, 3-phenyl-1-pentano, 5-phenyl-1-pentanol, 1-phenyl-1-pentanol, 1-phenyl-2-pentanol, 1-phenyl-3-methyl- 1-pentanol, phytol, pinacol, polyalkylene glycols, polysorbate 20, polysorbate 60, polysorbate 80, prenol, n-propanol, propenyl guaetol, propylene glycol, 2-propylphenol, 4-propylphenol, resorcinol, retinol, salicylaldehyde, sorbitan monostearate, sorbitol , stearyl alcohol, syringealdehyde, a-terpineol, tetrahydrogeraniol, tetrahydrolinalool, tetrahydromyrcenol, thymol, triethyl citrate, 1, 2,6-trihydroxyhexane, pa.a-trimethylbenzyl alcohol, 2- (5,5,6-trimethylbicyclo [2.2. 1] hept-2-ylcyclohexanol, 5- (2,2,3-trimethyl-3-cyclopentenyl) -3-methylpentan-2-ol, 3,7-1 1 -trimethyl-2,6, 10-dodecatrien-1 -ol, 3.7, 1 1 -trimethyl-1, 6,10-dode catrien-3-ol, 3,5,5-trimethyl-1-hexanol, 10-undecen-1 -ol, undecyl alcohol, vanilla, o-vanilla, vanillin butyl ether, 4-vinylphenol, 2,5-xyleneol, 2 , 6-xylenol, 3,5-xylenol, 2,4-xylenol and xylose, or the group of carbonyl-containing compounds consisting of 4-acetoxy-3-pentyl-tetrahydropyran, allyl cinnamate, allyl 2-ethylbutyrate, allyl cyclohexanopropionate, allyl heptanoate, allyl hexanoate, allyl isovalerate, allyl nonanoate, allyl octanoate, allyl phenoxyacetate, allyl phenylacetate, allyl propionate, α-amylancinyl acetate, amyl octanoate, anisyl acetate, anisyl phenyl acetate, benzyl acetate, benzyl acetoacetate, benzyl butyrate, cinnamate, benzyl, benzyl isobutyrate, benzyl isovalerate, benzyl phenylacetate, benzyl propionate, bornyl acetate, bornyl isovalerate, bornyl valerate, acetate of butyl, butyl butyrate, butyl butyrylate, 4-t-butylcyclohexyl acetate, heptanoate butyl, butyl hexanoate, butyl isobutyrate, butyl isovalerate, butyl laurate, butyl propionate, butyl stearate, 3-butylidenephthalide, butyl 2-methylisobutyrate, butyl 10-undecenoate,? -butyroiactone, carvilo acetate , carvilo propionate, caryophyllene acetate, cedrilo acetate, trans-cinnamyl acetate, trans-cinnamyl butyrate, cinnamyl cinnamate, cinnamyl isobutyrate, citronellyl acetate, citronellyl butyrate, citronellyl isobutyrate, citronellyl propionate, valerate of citronellyl, cyclohexanoethyl acetate, cyclohexyl acetate, cyclohexyl butyrate, cyclohexyl isovalerate, cyclohexyl propionate, d-decalactone, e-decalactone,? -decalactone, 4-decanolide, decyl acetate, decylbutyrate, decylpropionate , diethyl malonate, diethyl sebacate, diethyl succinate, dihydrocarvyl acetate, dihydrocoumarin, dihydromyrcenyl acetate, dihydro-nor-dicyclopentadienyl acetate, dihydroacetate terpinyl, acetate 3, 7-dimethyl-1 -6-octadien-3-yl, 3,7-dimethyl-1 -6-octadien-3-yl propionate, 3,7-dimethyloctane-3-yl acetate, , α-dimethephenethyl, α-, α-dimethylphenethyl butyrate, 6,10-dimethyl-5,9-undecadien-2-yl acetate, d-dodecalactone, e-dodecalactone, β-dodecalactone, ethyl acetate, ethyl acetoacetate , Ethyl 6-acetoxyhexanoate, ethyl 2-acetyl-3-phenylpropionate, ethyl benzoylacetate, 2-ethylbutyl acetate, ethyl butyrate, ethyl cinnamate, ethyl cyclohexanopropionate, ethyl decanoate, ethylene brasylate, 2-ethyl Ethyl 6,6-dimethyl-2-cyclohexenecarboxylate, ethyl 2,3-epoxybutyrate, ethyl 2-methyl-4-pentenoate, ethyl heptanoate, ethyl hexanoate, ethyl trans-3-hexenoate, ethyl acetate. -ethylhexyl, ethyl isobutyrate, ethyl isovalerate, ethyl laurate, ethyl 2-mercaptopropionate, ethyl 3-mercaptopropionate, ethyl 2-methylbutyrate, ethyl 2-methylpentanoate, (methylthio) ethyl acetate, (methylthio) -acetate of methyl, 2- (methylthio) ) methyl propionate, ethyl myristate, ethyl nonanoate, ethyl octanoate, ethyl palmitate, ethyl phenylacetate, ethyl 3-phenylpropionate, ethyl 3-phenyl-2,3-epoxybutyrate, ethyl 3-phenylpropionate, propionate ethyl, ethyl stearate, ethyl 2,3,6,6-tetramethi-2-cyclohexencarboxylate, ethyl (p-tolyloxy) acetate, ethyl undecanoate, ethyl valerate, eugenyl acetate, phenol acetate, ethyl acetate geranyl, geranyl butyrate, geranyl phenylacetate, geranyl propionate, guaiacyl phenylacetate, guaiacone acetate,? -heptalactone, heptyl acetate, heptyl butyrate, hypethyl isobutyrate,? -6-hexadecenlactone, d-hexalactone,? hexalactone, 3-hexenyl acetate, cis-3-hexenyl 2-methylbutanoate, cis-3-hexenyl cis-3-hexenoate, cis-3-hexenyl phenylacetate, trans-2-hexenyl acetate, hexyl acetate, hexyl butyrate, hexyl hexanoate, hexyl isobutyrate, hexyl propionate, hexyl 2-methylbutanoate, 3-methylbut hexyl anoate, hexyl phenylacetate, isoamyl acetate, isoamyl acetoacetate, isoamyl butyrate, isoamyl cinnamate, isoamyl hexanoate, isoamyl isobutyrate, isoamyl isovalerate, isoamyl laurate, isoamyl nonanoate, isoamyl octanoate, phenylacetate isoamyl, isoamyl propionate, isobornyl acetate, sobornyl propionate, isobutyl acetate, isobutyl butyrate, isobutyl cinnamate, isobutyl hexanoate, isobutyl isobutyrate, isobutyl 2-methylbutyrate, isobutyl propionate, iso-eugenyl acetate , isopropyl cinnamate, isopropyl phenylacetate, isopropyl acetate, isopropyl butyrate, isopropyl isobutyrate, isopropyl myristate, isopropyl palmitate, isopropyl phenylacetate, lauryl acetate, linalyl acetate, linalyl butyrate, linalyl isvalerate , mentalactone, menthyl acetate, menthyl cyclohexanecarboxylate, menthyl isovalerate, 4-methoxybenzyl acetate, propionate 4-methoxybenzyl, 2-methoxyphenyl acetate, 2-methoxy-4- (1-propenyl) phenyl acetate, methyl acetate, α-methylbenzyl acetate, α-methylbenzyl butyrate, α-methylbenzyl propionate, 2-methoxybenzyl acetate, -methylbutyl, 2-methylbutyl butyrate, 2-methylbutyl isovalerate, 3-methylbutyl 2-methylbutanoate, 2-methylbutyl 2-methylbutanoate, methyl pt-butylphenylacetate, methyl butyrate, methyl cinnamate, methyl decanoate, heptanoate of methyl, methyl hexanoate, methyl isobutyrate, methyl isovalerate, methyl laurate, methyl N-2-methyl-3- (4-t-butylphenylpropylidene) anthralylate, methyl myristate, methyl nonanoate, methyl octanoate, methyl palmitate, 4- (4-methyl-3-pentenyl) -3-cyclohexenylmethyl acetate, methyl 2-methylbutyrate, 2-methyl-6-methylene-7-octen-2-yl acetate, 4-methylvalerate methyl, methyl 2-methylpentanoate, methyl phenoxyacetate, 4-methylphenyl phenylacetate, 2-methyl-3-phenylpropan-2-yl acetate, methyl 3-phenylpropionate, methyl propionate, 2-methylpropyl phenylacetate, methyl phenylacetate, 2-methyl-3-phenylpropan-2-yl acetate, methyl stearate, methyl (p-tolyloxy) acetate, methyl 9-undecentate, methyl valerate, mihenyl, neryl acetate, neryl butyrate, neryl isobutyrate, d-nonalactone,? -nonalactone, 1,3-nonanediol diacetate, nonyl acetate, nopyl acetate, octahydrocoumarin,? -octalactone, 1-octen-acetate 3-yl, 1-buttene-3-ylbutyrate, octyl acetate, butyl acetate, octyl isobutyrate, octyl isovalerate, octyl octanoate, octyl propionate, oxacycloheptadec-10-en-2-one,? pentadecalactone, pentyl acetate, pentyl butyrate, pentyl hexanoate, pentyl octanoate, phenethyl acetate, phenethyl butyrate, phenethyl cinnamate, phenethyl hexanoate, phenethyl isobutyrate, phenethyl isovalerate, phenethyl 2-methylbutyrate, 2- phenethyl methylbutyrate, phenethyl 2-methylpropionate, phenethyl octanoate, phenethyl phenylacetate phenoxy propionate phenoxyethyl propionate, 2-phenoxyethyl 2-methylpropionate, 3-phenyl-2-propenyl propionate, 3-phenylpropyl acetate, 2-phenylpropyl butyrate, 2-phenylpropyl isobutyrate, 2-phenylpropyl isovalerate , piperonyl acetate, piperonyl isobutyrate, prenyl acetate, propyl acetate, propyl butyrate, propyl heptanoate, propyl hexanoate, 3-propylidenephthalide, propyl isobutyrate, propyl propionate, propyl phenylacetate, sucrose octaacetate, acetate of terpinyl, terpinyl butyrate, terpinyl sobutyrate, terpinyl propionate, tetrahydrofurfuryl acetate, tetrahydrofurfuryl butyrate, tetrahydrofurfuryl propionate, tetrahydrolinallyl acetate, 2,6,6,8-tetramethyltricyclo [5.3] acetate, 1.0 (1.5)] undecan-8-yl, p-tolyl acetate, p-tolyl isobutyrate, p-tolyl phenylacetate, triacetin, tributyl acetylcitrate, tributyrin, tripropionin, 3,5,5 acetate -trimethylhexyl, d-undecalacto na,? -undecalactone,? -valerolactone, vanilla acetate, vanillyl isobutyrate, 1-vinyl-2- (1-methylpropyl) cyclohexyl acetate, whiskey lactone, butyraldehyde, citronellal, decanal, cis-4-decenal, trans -4-decane, 2,4-dimethyl-3-cyclohexen-1 -carbaldehyde, 2,6-dimethyl-5-heptenal, 3,7-dimethyloctanal, 2-ethylbutyraldehyde, glutaraldehyde, heptanal, cis-4-heptenal, hexanal, hydrocinnamaldehyde, isobutyraldehyde, 3- (p-isopropylphenyl) -propionaldehyde, isovaleraldehyde, lauric aldehyde, 2-methylbutyraldehyde, 2-methyl-3- (p-isopropylphenyl) propionaldehyde, 2-methylpentanal, 4- (4-methyl-3 -pentenyl) -3-cyclohexen-1 -carbaldehyde, 4-methylphenylacetaldehyde, 3- (methylthio) butanal, 2-methyl-4- (2,6,6-trimethyI-2-cyclohexen-1 -yl) butanal, 2- methylundecanaI, nonanal, cis-6-nonenal, octanal, phenylacetaldehyde, 2-phenylpropionaldehyde, 3-phenylpropionaldehyde, propionaldehyde, p-tolylacetaldehyde, tridecanal, 2,4,6-trimethyl-3-cyclohexen-1 -carbaldehyde, 2,6, 10-trimethyl-9-undecanal, 7-undecenal, 8-undecenal, 9-undecenal, 10-undecenal, valeraldehyde, acetanisol, 1'-acetonaphthone, 2'-acetonaphthone, acetone, acetophenone, 2-acetoxy-2,5-dimethyl-3 (2H) furanone, 2-acetylcyclopentanone, 4-acetyl-1,1-dimethyl-6-t-butyl indane, 7-acetyl-1,1, 3,4,4,6-hexanmethyl bildane, 2-acetyl-2-tizoline, 6-acetyl- 1, 1, 2, 4,4,7-hexamethyl tetralin, allyl-ionone, benzylidene ketone, 2,3-butanedione, 2-sec-butylcyclohexanone, 5-t-butyl-3,5-dinitro-2,6- dimethylacetophenone, butyrophenone, camphor, 2-decanone, 3-decanone, 3-decen-2-one, dihydrocarvone, dihydro-β-ionone, dihydrojasmone, 4,5-dihydro-3 (2H) -thiophenone, 2 ', 4' -dimethylacetophenone, 3,4-dimethyl-1,2-cyclopentadione, 3,5-dimethyl-1,2-cyclopentadione, 2,6-dimethyl-4-heptanone, 1,3-diphenyl-2-propanone, 4- ( 1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone, p-ethylacetophenone, ethyl vinyl ketone, geranylacetone, 2,3-heptanedione, 2-heptanone, 3-heptanone, 4-heptanone, 3,4-hexanedione, 3 -hexanone, 4-hexen-3-one, 2-hexylidene cyclopentanone, a-io nona, ß-ionone, 4-isobutyl-2, 6-dimethyl-3,5-dinitroacetophenone, isophorone, 6-isopropyldehydro-2-naphthone, cis-jasmona, livescona, 4-methoxyacetophenone, 4- (p-methoxyphenyl) -2-butanone, 4'-methylacetophenone, 3- methyl-1,2-cyclohexanedione, 3-methyl-2-cidohexen-1 -one, 2- (2- (4-methyl-3-cyclohexen-1 -yl) propyl) -cyclopentanone, 3-methyl-2-cyclopenten -1 -one, methyl dihydrojasmonate, methyl ethyl ketone, 2-methyl-3-heptanone, 5-methyl-2-hepten-4-one, 6-methyl-5-hepten-2-one, 5-methyl-a -ionone, 1- (2-methyl-5-isopropyl-2-cyclohexenyl) -1-propanone, 4-methyl-2-pentanone, 3-methyl-2- (2-pentenyl) -2-cyclopenten-1-one , 4-methyl-1-phenyl-2-pentanone, 2-methyltetrahydrofuran-3-one, 2-methyltetrahydrothiophen-3-one, 2-nonanone, 3-nonanone, 2-octanone, 3-octanone, 1-octen-3 -one, 3-octen-2-one, 4-oxoisophorone, 2-pentadecanone, 2,3-pentanedione, 2-pentanone, 3-pentanone, 3-penten-2-one, 1-phenyl-1,2-propandione , propiophenone, pulegone, 2-tridecanone, 2,2,6-trimethylcyclohexanone, 4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-methyl-3-buten-2-one, 2 -undecano na and 6-undecanone. The active releasing compounds of the present invention are particularly suitable for incorporation into personal care products to impart a desirable and lasting effect to the products. Suitable uses include, but are not limited to, deodorants, antiperspirants, insect repellents, skin creams, facial creams, hair care products such as shampoos, mousses, styling gels, protective creams, shaving creams, for after shaving, cologne, perfume, color cosmetics, such as lipsticks, mp foundations, blushes, mp and mascara for eyelashes; and other cosmetic formulations where other components containing silicon have been added and where it is desirable to impart a certain effect. The incorporation of small amounts of the compositions of the present invention into fragrance products such as shaving lotions, colognes, toilet water and perfumes, can impart a desirable lasting fragrance to these products. In addition, the siloxanes of the present invention can be incorporated into other products where it is desirable to mask unpleasant odors with a pleasant fragrance, for example, household cleaning products, such as waxes and polishes, automotive cleaning products, such as waxes and polishes, detergents, textile coatings, paints, varnishes and the like, subject to the limitation that the siloxane of the present invention may be compatible or capable of being made compatible with the product in which it is incorporated.
Experimental Example 1 In a round glass flask, silane V was charged (19.9 g,
0. 083 mol) and stirred for 15 min. A 10.9% solution of Pt (0) in divinyltetramethylsiloxane (15 mg of solution, 100 ppm Pt) was added.
Then tetramethylcyclotetrasiloxane (5.07 g, 0.083 mol of hydride) was added to the reaction mixture over 30 min. A slight exotherm was observed. The reaction mixture was then heated to 65 ° C and maintained at said temperature for 5 h. The volatiles were removed under vacuum (70 ° C, 0.5 mm Hg) for 1.5 h. The brown product was mixed with Celite and filtered to give 17.9 g of a straw-colored fluid (71.6%).
Example 2 In a round glass flask, silane VI (19.3 g, 0.093 mol) was charged and stirred. A 10.9% solution of Pt (0) in divinyltetramethylsiloxane (17 mg of solution, 74 ppm Pt) was added. Then tetramethylcyclotetrasiloxane (5.71 g, 0.093 mol of hydride) was added to the reaction mixture over 25 min. The reaction mixture was then heated to 65 ° C and maintained at said temperature for 6 h. The volatiles were removed under vacuum (70 ° C, 0.5 mm Hg) for 1.5 h. The product was mixed with Celite and filtered to give 15.2 g of pale brown fluid (60.8%).
Example 3 In a glass round bottom flask, Vil silane (9.80 g, 0.041 mol) was charged and stirred. A 10.9% solution of Pt (0) in divinyltetramethylsiloxane (14 mg of solution, 200 ppm Pt) was added. Then tetramethylcyclotetrasiloxane (2.51 g, 0.041 mol of hydride) was added to the reaction mixture over 25 min. A significant exotherm was observed. The reaction mixture was then heated to 70 ° C and maintained at that temperature for 2.5 h. The product was filtered to give 11.0 g of a straw colored fluid (89.4%).
Example 4 In a round glass bottom flask, Vil silane (16.41 g, 0.060 mol) was charged and stirred. A 0.9% solution of Pt (0) in divinyltetramethylsiloxane (21 mg of solution, 200 ppm Pt) was added and the mixture was stirred for 15 min. Then tetramethylcyclotetrasiloxane (3.61 g, 0.060 mol of hydride) was added to the reaction mixture over 25 min. The reaction mixture was heated to 70 ° C and maintained at that temperature for 2.5 h. The product was extracted (75 ° C, 0.5 mm Hg) for 1.5 hours then filtered to give 18.1 g of yellow fluid (90.5%).
Example 5 In a round glass bottom flask, silane IX (16.78 g, 0.054 mol) was charged together with a 10.9% solution of Pt (0) in divinyltetramethylsiloxane (14 mg of solution, 150 ppm Pt). The mixture was stirred for 15 min. Then tetramethylcyclotetrasiloxane (3.23 g, 0.054 mol of hydride) was added to the reaction mixture over 25 min; the solution increased in viscosity. The reaction mixture was heated to 60 ° C and maintained at that temperature for 80 min. The product was extracted (70 ° C, 3 mm Hg) for 1 h, then filtered to give 16.5 g of pale orange fluid (82.5%).
saw
VII HIV
Examples 6-10 (hydrolysis of products from Examples 1-5, respectively) The general procedure for hydrolysis is as follows: A solution of the active ingredient-functional silicone (1.0 g), tetrahydrofuran (10 g) was prepared and internal standard of bibencil (0.4 g). The solution was analyzed by means of gas chromatography, then 0.50 ml of 1% aqueous sodium hydroxide solution (weight) was added (except for example 9, in which 0.125 ml of sodium hydroxide aqueous solution was used). %). The mixture was stirred and sampled periodically for gas chromatography analysis. Tables 1-5 demonstrate the release profiles determined in Examples 6-10, respectively.
Table 1 . Hydrolysis of product of example 1. Time Relative concentration of citronellol 0.00 0.042 0.92 0.077 8.92 0.145 22.58 0.198 29.33 0.220 47.00 0.248 5.0 0.258 70.75 0.282 78.08 0.283 93.92 0.298
Table 2. Product hydrolysis of example 2 Time Relative concentration of phenethyl alcohol
0. 00 0.025 1 .33 0.102 9.33 0.253 23.00 0.418 29.75 0.450 47.50 0.532 55.50 0.557 71 .25 0.604 78.50 0.614 94.42 0.639
Table 3. Product hydrolysis of example 3 Time Relative concentration of geraniol 0.00 0.083 0.50 0.097 6.00 0.261 25.42 0.429 45.83 0.530 53.75 0.559 70.83 0.600 77.50 0.608 94.08 0.642
Table 4. Product hydrolysis of example 4 Time Relative concentration of 3-methyl-3- (meta-isopropylphenyl) propionaldehyde 0.00 0.1 1 1 1 -00 1 .142 6.42 1 .109 25.92 1 .007 46.33 0.954 54.25 0.932 71 .25 0.913 78.00 0.900 94.50 0.884
Table 5. Product hydrolysis of example 5 Time Relative concentration of phenethyl alcohol
0. 00 0.050 1 .42 0.344 6.92 0.791 26.42 1 .253 46.75 1 .368 54.83 1 .389 71 .75 1 .418 78.50 1 .439 95.00 1 .451
Examples 1 1-12 (hydrolysis of products from Examples 2 and 5, respectively) The general procedure for hydrolysis is as follows: A 3.3 cm by 3.3 cm sample of untreated cotton cloth was soaked with each material, from Thus, the molar equivalents of active ingredient were equal among all samples. Each sample was kept in a small aluminum tray and all trays were kept in a box with the upper part open in the same room at room temperature and humidity. The samples were smelled at time intervals and classified by strength of essence (0 = no essence), 5 = same strength as the pure active ingredient of the bottle). The data are presented in Tables 6 and 7. In Example 11 (Table 6), it can be seen that the fabric treated with the siloxane derivative of the present invention releases a stronger smell over a longer period. In Example 12 (Table 7), it can be seen that the fabric treated with the siloxane derivative exhibits a more consistent degree of odor over time.
Table 6. Relative smell of fabric samples (Example 1 1) Hours Siloxane Control of Ex. 2
~ T? (5 5 5.0 4 4 21.5 4 4 28.9 3 4 46.3 3 4 52.8 3 4 78.1 3 4 164.3 3 4 215.3 2 3 237.1 1 2
Table 7. Relative smell of fabric samples (Example 12) Hours Siloxane Control of Ex. 5
__ _ _
. 0 4 3 21 .5 4 3
28. 9 3 3
46. 3 3 3
52. 8 3 3
78. 1 3 3
164. 3 3 2
215. 3 2 2
237. 1 1 2
Claims (21)
- CLAIMS 1 . A cyclic siloxane that releases active ingredient selected from the group of siloxanes having the formulas: where R10, R1 1, R12 and R13 are each independently selected from the group of monovalent C? -C2 hydrocarbon radicals, the subscripts n and q are each independently greater than or equal to 1, the subscripts p, r and s are each independently equal to or greater than 0, with the proviso that n + p must be equal to or greater than 3 and that q + r + s must be equal to or greater than 3; where RF has the formula (R1O) a (R2O) b (R3O) c (R) d (R5) eSiRu, with Ru defined as a monovalent hydrocarbon radical of C2-C40 and R4 and R5 independently selected from the group consisting of monovalent hydrocarbon radicals having from one to forty carbon atoms, 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 subject to the limitation that a + b + c + d + e = 3, wherein each R 1 O, R 2 O and R 3 O are independently selected from the group of conjugated bases consisting of conjugate bases derived from the group of active alcohol ingredients consisting of R 1 OH, R 2 OH and R 3 OH, wherein R 1, R 2 and R 3 they are independently monovalent hydrocarbon radicals having from four to one hundred carbon atoms and the group of conjugated bases derived from the group of carbonyl active ingredients having the structure: R7-C (R8) = C (O -) - R9 wherein R7, R8 and R9 are each independently selected from the group consisting of hydrogen and monovalent hydrocarbon radicals having from one to one hundred carbon atoms.
- 2. The cyclic siloxane releasing active ingredient of claim 1, having the formula:
- 3. The cyclic siloxane releasing active ingredient of claim 2, wherein RF has the formula (R1O) a (R2O) b (R3O) 0 (R4) d (R5) eSiRu, with Ru a divalent hydrocarbon radical of C2-C 0 and R4 and R5 independently selected from the group consisting of monovalent hydrocarbon radicals having from one to forty carbon atoms, the subscript a has a value ranging from 1 to 3 and the subscripts b, c, d and e have values ranging from 0 up to 2 subjected to the limitation that a + b + c + d + e = 3, where each R1O, R2O and R3O are independently selected from the group of conjugated bases consisting of conjugate bases derived from the group of active ingredients of alcohol consisting of R1OH, R2OH and R3OH.
- 4. The cyclic siloxane that releases active ingredient of the claim 3, wherein the active alcohol ingredients R1OH, R2OH and R3OH are fragrant alcohols.
- 5. The cyclic siloxane that releases active ingredient of the claim 4, wherein the fragrant alcohols R1OH, R2OH and R3OH are selected from the group of fragrant alcohols consisting of acetovainillone, allyl amyl glycolate, allyl isoamyl glycolate, amyl amyl alcohol, anisole alcohol, benzoin, benzyl alcohol, benzyl salicylate, -butanol, butylated hydroxytoluene, butyl lactate, 2-t-butyl-5-methylphenol, 2-t-butyl-6-methylphenol, carvacrol, carveol, 4-carvomentenol, cedrol, cetyl alcohol, cinnamic alcohol, citronellol, o- cresol, m-cresol, p-cresol, crotyl alcohol, decahydro-2-naphthol, 1-decanol, 1-deen-3-ol, 9-decene-1-ol, diethyl malate, diethyl tartrate, dihydrocarvol, dihydromyrcenol , 2,6-diisopropylphenol, dimethicone copolyol, 2,6-dimethoxyphenol, 1,1-dimethoxy-3,7-dimethyloctane-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- octatnol, 3,7-dimethyl-6-octen-1 -ol, 3,7-dimethyl-7-octen-1 -ol, dimethyl, 2-ethylphenol, 4-ethylguaiacol, 2-ethyl-1-hexanol, 2- ethyl hydroxybenzoate, ethyl 3-hydroxybutyrate, 3-ethyl-2-hydroxy-2-cyclopenten-1 -one, ethyl 2-hydroxycaproate, ethyl 3-hydroxyhexanoate, ethyl lactate, ethyl maltol, p-ethylphenol, ethyl salicylate, eugenol, farnesol, phenolic alcohol, geraniol, glucose pentaacetate, glycerol, glyceryl monostearate, guaiacol, 1-heptanol, 2-heptanol, 3-heptanol, cis -4-heptenol, cis-3-heptenol, n-hexane !, 2-hexanol, 3-hexanol, cis-2-hexenol, cis-3-hexenol, trans-3-hexenol, 4-hexenol, cis-3 alcohol -hexenyl hydrocinnamyl, 2-hydroxybenzoate, 2-hydroxyacetophenone, 4-hydroxybenzyl alcohol, 3-hydroxy-2-butanone, hydroxycitronellal, 4- (4-hydroxy-3-methoxyphenyl) -2-butanone, 2-hydroxy-3-methyl -2-cyclopenten-1 -one, 4- (p-hydroxyphenyl) -2-butanone, 2-hydroxy-3,5,5-trimethyl-2-cyclohexenone, d-isoascorbic acid, isoborneol, isoeugenol, isophytol, isopropyl alcohol , p-isopropylbenzyl alcohol, 4-isopropylcyclohexanol, 3-isopropylphenol, 4-isopropylphenol, 2-isopropylphenol, isopulegol, lauryl alcohol, linalool, maltol, menthol, 4-methoxybenzyl alcohol, 2-methoxy-4-methylphenol, 2-methoxy -4-propylphenol, 2-methoxy-4-vinylphene l, α-methylbenzyl alcohol, 2-methylbutanol, 3-methyl-2-butanol, 2-methyl-2-buten-1-ol, 2-methyl-3-buten-2-ol, 2,4-dihydroxy-3 , Methyl 6-dimethylbenzoate, 4-methyl-2,6-dimethoxyphenol, methyl N-3,7-dimethyl-7-hydroxyoctiIidenanthranilate, methyl 3-hydroxyhexanoate, 6-methyl-5-hepten-2-ol, -methylpentanol, 3-methyl-3-pentanol, 2-methyl-4-phenylbutan-2-yl, 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-dihydrofuran, myrtenol, dihydrochalcone of noehesperidin, neomentol, nerol, nerolidol, trans-2-cis-6-nonadienol, 1,3-nonanediol acetate, nonadil, 2-nonanol, cis-6-nonen-1-ol, trans-2-nonen- 1 -ol, nonyl alcohol, 1-octanol, 2-octanol, 3-octanol, cis-3-octen-1 -oI, 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, patchouli alcohol, 3-pentanol, n-pentanol, 2-pentanol, 1 -penten-1 - ol, cis-2-penten-1 -ol, alcohol l perilylic, 2-phenoxyethanol arabinogalactan, ß-phenethyl alcohol, phenethyl salicylate, phenol, phenylacetaldehyde glyceryl acetal, 3-phenyl-1-pentanol, 5-phenyl-1-pentanol, 1-phenyl-1-pentanol, 1-phenyl -2-pentanol, 1-phenyl-3-methyl-1-pentanol, phytol, pinacol, polyalkylene glycols, polysorbate 20, polysorbate 60, polysorbate 80, prenol, n-propanol, propenyl guaetol, propylene glycol, 2-propylphenol, 4- propiIphenol, resorcinol, retinol, salicylaldehyde, sorbitan monostearate, sorbitol, stearyl alcohol, syringealdehyde, a-terpineol, tetrahydrogeraniol, tetrahydrolinalool, tetrahydromyrcenol, thymol, triethyl citrate, 1, 2,6-trihydroxyhexane, pa, a-trimethylbenzyl alcohol, 2- (5,5,6-trimethylbicyclo [2.2.1] hept-2-ylcyclohexanol, 5- (2,2,3-trimethyl-3-cyclopentenyl) -3-methylpentan-2-o !, 3,7- 1 1 -trimethyl-2,6, 10-dodecatrien-1 -ol, 3,7, 1 -trimethyl-1, 6, 10-dodecatrien-3-ol, 3,5,5-trimethyl-1-hexanol, 10-undecen-1 -ol, undecyl alcohol, vanilla, o-vanilla, vanilli l butyl ether, 4-vinylphenol, 2,5-xylenol, 2,6-xylenol, 3,5-xylenol, 2,4-xylenol and xylose.
- 6. The cyclic siloxane releasing active ingredient of claim 1, having the formula:
- 7. The cyclic siloxane releasing active ingredient of claim 6, wherein RF has the formula (R1O) a (R2O) b (R3O) c (R4) d (R5) eSiRu, with Ru a divalent hydrocarbon radical of C2-C40 and R4 and R5 independently selected from the group consisting of monovalent hydrocarbon radicals having from one to forty carbon atoms, 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 subject to the limitation that a + b + c + d + e = 3, where each R 1 O, R 2 O and R 3 O are independently selected from the group of conjugated bases consisting of conjugate bases derived from the group of active ingredients of alcohol consisting of R 1 OH , R 2 OH and R 3 OH.
- The cyclic siloxane releasing active ingredient of claim 7, wherein the active alcohol ingredients R1OH, R2OH and R3OH are fragrant alcohols.
- 9. The cyclic siloxane releasing active ingredient of claim 8, wherein the fragrant alcohols, R OH, R2OH and R3OH are selected from the group of fragrant alcohols consisting of acetovainillone, allyl amyl glycolate, allyl isoamyl glycolate, amyl cinnamyl alcohol , anisole alcohol, benzoin, benzyl alcohol, benzyl salicylate, 1-butanol, butylated hydroxytoluene, butyl lactate, 2-t-butyl-5-methylphenol, 2-t-butyl-6-methylphenol, carvacrol, carveol, 4- carvomentenol, cedrol, cetyl alcohol, cinnamic alcohol, citronellol, o-cresol, m-cresol, p-cresol, crotyl alcohol, decahydro-2-naphthol, 1-decanol, 1-decen-3-ol, 9-decen-1 -ol, diethyl malate, diethyl tartrate, dihydrocarvol, dihydromyrcenol, 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- octatnol, 3,7-dimethyl-6-octen-1 -ol, 3,7-dimethyl-7-octen-1 -ol, dimethyl, 2-ethylphenol, 4-ethylguaiacol, 2-ethyl-1-hexanol, 2- ethyl hydroxybenzoate, ethyl 3-hydroxybutyrate, 3-ethyl-2-hydroxy-2-cyclopenten-1 -one, ethyl 2-hydroxycaproate, ethyl 3-hydroxyhexanoate, ethyl lactate, ethyl maltol, p-ethylphenol, salicylate ethyl, eugenol, farnesol, phenolic alcohol, geraniol, glucose pentaacetate, glycerol, glyceryl monostearate, guaiacol, 1-heptanol, 2-heptanol, 3-heptanol, cis-4-heptenol, cis-3-heptenol, n- hexanol, 2-hexanol, 3-hexanol, cis-2-hexenol, cis-3-hexenol, trans-3-hexenol, 4-hexenol, cis-3-hexenyl hydrocinyl alcohol, 2-hydroxybenzoate, 2-hydroxyacetophenone, alcohol 4 -hydroxybenzyl, 3-hydroxy-2-butanone, hydroxycitronellal, 4- (4-hydroxy-3-methoxyphenyl) -2-butanone, 2-hydroxy-3-methyl-2-cyclopenten-1 -one, 4- (p- hydroxyphenyl) -2-butanone, 2-hydroxy-3,5 , 5-trimethyl-2-cyclohexenone, d-isoascorbic acid, isoborneol, isoeugenol, isophytol, isopropyl alcohol, p-isopropylbenzyl alcohol, 4-isopropylcyclohexanol, 3-isopropylphenol, 4-isopropylphenol, 2-isopropylphenol, isopulegol, lauryl alcohol, linalool , maltol, menthol, 4-methoxybenzyl alcohol, 2-methoxy-4-methylphenol, 2-methoxy-4-propylphenol, 2-methoxy-4-vinylphenol, a-methylbenzyl alcohol, 2-methylbutanol, 3-methyl-2-butanol , 2-methyl-2-buten-1-ol, 2-methyl-3-buten-2-ol, methyl 2,4-dihydroxy-3,6-dimethylbenzoate, 4-methyl-2,6-dimethoxyphenol, N Methyl -3,7-dimethyl-7-hydroxyoctylidenantranilate, methyl 3-hydroxyhexanoate, 6-methyl-5-hepten-2-ol, 2-methylpentanol, 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-dihydrofuran, myrtenol, dihydrochalcone of noeperperidine, neomentol, nerol, nerolidol, trans-2-cis-6- nonadienol, 1,3-nonanediol acetate, nonadil, 2-nonanol, cis-6-nonen-1 -ol, 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-1 -ol, cis-6-octen-1 -ol, cis-octen-1 -ol, 1-octen-3-ol, oleyl alcohol, patchouli alcohol, 3-pentanol, n- pentanol, 2-pentanol, 1 -penten-1-ol, cis-2-penten-1 -ol, perilylic alcohol, 2-phenoxyethanol arabinogalactan, β-phenethyl alcohol, phenethyl salicylate, phenol, phenylacetaldehyde glyceryl acetal, 3-phenyl -1-pentanol, 5-phenyl-1-pentanol, 1-phenyl-1-pentanol, 1-phenyl-2-pentanol, 1-phenyl-3-methyl-1-pentanol, phytol, pinacol, polyalkylene glycols, polysorbate , polysorbate 60, polysorbate 80, prenol, n-propanol, propenyl guaetol, propylene glycol, 2-propylphenol, 4-propylphenol, resorcinol, retinol, salicylaldehyde, sorbitan monostearate, sorbitol, stearyl alcohol, syringealdehyde, a-terpineol, tetrahydrogeraniol, tetrahydrolinalool , tetrahydromyrcenol, thymol, triethyl citrate, 1, 2,6-trihydroxyhexane, pa, a-trimethylbenzyl alcohol, 2- (5,5,6-trimethylbicyclo [2.2.1] hept-2-ylcyclohexanol, 5- (2, 2,3-trimethyl-3-cyclopentenyl) -3-methylpentan-2 -ol, 3,7-1 1 -trimethyl-2,6, 10-dodecatrien-1 -ol, 3,7, 1 1-trimethyl-1, 6, 10-dodecatrien-3-ol, 3,5,5 -trimethyl-1-hexanol, 10-undecen-1 -ol, undecyl alcohol, vanilla, o-vanilla, vanillin butyl ether, 4-vinylphenol, 2,5-xyleneol, 2,6-xyleneol, 3,5-xyleneol, 2,4-xylenol and xylose.
- 10. The cyclic siloxane releasing active ingredient of claim 2, wherein RF has the formula (R1O) a (R2O) b (R3O) c (R4) d (R5) eSiRu, with Ru a divalent hydrocarbon radical of C2 -C40 and R4 and R5 independently selected from the group consisting of monovalent hydrocarbon radicals having from one to forty carbon atoms, 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 subjected to the limitation that a + b + c + d + e = 3, where each R1O, R2O and R3O are independently selected from the group of conjugated bases consisting of conjugate bases derived from the group of conjugated bases derived from the group of carbonyl active ingredients having the structure: R7-C (R8) = C (O -) - R9 where R7, R8 and R9 are each independently selected from the group consisting of hydrogen and monovalent hydrocarbon radicals having one to one hundred carbon atoms. eleven .
- The siloxane releasing active ingredient of claim 10, wherein the active carbon ingredients are fragrant carbonyl active ingredients.
- The cyclic siloxane releasing active ingredient of claim 1, wherein the fragrant carbonyl active ingredients are selected from the group consisting of 4-acetoxy-3-pentiI-tetrahydropyran, allyl cinnamate, allyl 2-ethylbutyrate, cyclohexanopropionate allyl, allyl heptanoate, allyl hexanoate, allyl isovalerate, allyl nonanoate, allyl octanoate, allyl phenoxyacetate, allyl phenylacetate, allyl propionate, α-amylcinnamyl acetate, amyl octanoate, anisyl acetate, acetate of anisilyphenyl, benzyl acetate, benzyl acetoacetate, benzyl butyrate, benzyl cinnamate, benzyl isobutyrate, benzyl isovalerate, benzyl phenylacetate, benzyl propionate, bornyl acetate, bornyl isovalerate, bornyl valerate, butyl acetate , butyl butyrate, butyl butyrylate, 4-t-butylcyclohexyl acetate, butyl heptanoate, butyl hexanoate, butyl isobutyrate, butyl isovalerate, laurat or of butyl, butyl propionate, butyl stearate, 3-butylidenephthalide, butyl 2-methylbutyrate, butyl 10-undecenoate, β-butyrolactone, carvilo acetate, carvilo propionate, caryophyllene acetate, cedryl acetate, trans-cinnamyl, trans-cinnamyl butyrate, cinnamyl cinnamate, cinnamyl isobutyrate, citronellyl acetate, citronellyl butyrate, citronellyl isobutyrate, citronellyl propionate, citronellyl valerate, cyclohexanoethyl acetate, cyclohexyl acetate, cyclohexyl butyrate, cyclohexyl isovalerate, cyclohexyl propionate, d-decalactone, e-decalactone,? -decalactone, 4-decanolide, decyl acetate, decyl butyrate, decyl propionate, diethyl malonate, diethyl sebacate, diethyl succinate, dihydrocarvyl, dihydrocoumarin, dihydromyrcenyl acetate, dihydro-nor-dicyclopentadienyl acetate, dihydroterpynyl acetate, 3,7-dimethyl-1 -6-octadien-3-yl acetate, 3,7-dimethyl-1-propionate 6-Octadien-3-yl, 3,7-dimethyloctane-3-yl acetate, a, a-dimethylphenethyl acetate, a, a-dimethylphenethyl butyrate, 6,10-dimethyl-5,9-undecadiene acetate 2-yl, d-dodecalactone, e-dodecalactone,? -dodecalactone, ethyl acetate, ethyl acetoacetate, ethyl 6-acetoxyhexanoate, ethyl 2-acetyl-3-phenylpropionate, ethyl benzoylacetate, 2-ethylbutyl acetate, ethyl butyrate, ethyl cinnamate, ethyl cyclohexanopropionate, ethyl decanoate, ethylene brasilate, ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate, ethyl 2,3-epoxybutyrate, 2-methyl-4- ethyl pentenoate, ethyl heptanoate, ethyl hexanoate, ethyl trans-3-hexenoate, 2-ethylhexyl acetate, ethyl sobutyrate, ethyl isovalerate, ethyl laurate, ethyl 2-mercaptopropionate, ethyl 3-mercaptopropionate , Ethyl 2-methylbutyrate, ethyl 2-methylpentanoate, (methylthio) ethyl acetate, methyl (methylthio) acetate, methyl 2- (methylthio) propionate, ethyl myristate, ethyl nonanoate or, ethyl octanoate, ethyl palmitate, ethyl phenylacetate, ethyl 3-phenylpropionate, ethyl 3-phenyl-2,3-epoxybutyrate, ethyl 3-phenylpropionate, ethyl propionate, ethyl stearate, 2,3, Ethyl 6,6-tetramethyl-2-cyclohexencarboxylate, ethyl (p-tolyloxy) acetate, ethyl undecanoate, ethyl valerate, eugenyl acetate, phenol acetate, geranyl acetate, geranyl butyrate, geranyl phenylacetate, propionate of geranyl, guaiacyl phenylacetate, guaicamide acetate,? -heptalactone, heptyl acetate, heptyl butyrate, hypethyl isobutyrate,? -6-hexadecenlactone, d-hexalactone,? -hexalactone, 3-hexenyl acetate, cis-3-hexenyl 2-methylbutanoate, cis-3-hexenoxy cis-3-hexenoate, cis-3-hexenyl phenylacetate, trans-2-hexenyl acetate, hexyl acetate, butyrate of hexyl, hexyl hexanoate, hexyl isobutyrate, hexyl propionate, hexyl 2-methylbutanoate, hexyl 3-methylbutanoate, hexyl phenylacetate, isoamyl acetate, isoamyl acetoacetate, isoamyl butyrate, isoamyl cinnamate, isoamyl hexanoate isoamyl isobutyrate, isoamyl isovalerate, isoamyl laurate, isoamyl nonanoate, isoamyl octanoate, isoamyl phenylacetate, isoamyl propionate, isobornyl acetate, isobornyl propionate, isobutyl acetate, isobutyl butyrate, isobutyl cinnamate, isobutyl hexanoate, isobutyl isobutyrate, isobutyl 2-methylbutyrate, isobutyl propionate, isoeugenyl acetate, isopropyl cinnamate, isobutyl phenylacetate, isopropyl acetate, isopropyl butyrate, isopropyl isobutyrate, miri isopropyl ester, isopropyl palmitate, isopropyl phenylacetate, lauryl acetate, linalyl acetate, linalyl butyrate, linalyl isovalerate, mentalactone, menthyl acetate, menthyl cyclohexanecarboxylate, menthyl isovalerate, 4-methoxybenzyl acetate, propionate 4-methoxybenzyl, 2-methoxyphenyl acetate, 2-methoxy-4- (1-propenyl) phenyl acetate, methyl acetate, α-methylbenzyl acetate, α-methylbenzyl butyrate, α-methylbenzyl propionate, 2-methoxybenzyl acetate, -methylbutyl, 2-methylbutyl butyrate, 2-methylbutyl isovalerate, 3-methylbutyl 2-methylbutanoate, 2-methylbutyl 2-methylbutanoate, methyl pt-butylphenylacetate, methyl butyrate, methyl cinnamate, methyl decanoate, heptanoate of methyl, methyl hexanoate, methyl isobutyrate, methyl isovalerate, methyl laurate, methyl N-2-methyl-3- (4-t-butylphenylpropylidene) anthralylate, methyl myristate, methyl nonanoate, methyl octanoate, methyl palmitate, acetate 4 - (4-Methyl-3-pentenyl) -3-cyclohexenylmethyl, methyl 2-methylbutyrate, 2-methyl-6-methylene-7-octen-2-yl acetate, methyl 4-methylvalerate, methyl 2-methylpentanoate , methyl phenoxyacetate, 4-methylphenyl phenylacetate, 2-methyl-3-phenylpropan-2-yl acetate, methyl 3-phenylpropionate, methyl propionate, 2-methylpropyl phenylacetate, methyl phenylacetate, 2-methyl acetate -3-phenylpropan-2-yl, methyl stearate, methyl (p-tolyloxy) acetate, methyl 9-undecentate, methyl valerate, mirtenyl acetate, neryl acetate, neryl butyrate, neryl isobutyrate, d- nonalactone,? -nonalactone, 1,3-nonanediol diacetate, nonyl acetate, nopyl acetate, octahydrocoumarin,? -octalactone, 1-octen-3-yl acetate, 1-keten-3-yl butyrate, octyl, actyl butyrate, octyl isobutyrate, octyl isovalerate, octyl octanoate, octyl propionate, oxacycloheptadec-10-en-2-one,? -pentadecalactone, pentyl acetate, pentyl butyrate, pentyl hexanoate, pentyl octanoate, phenethyl acetate, phenethyl butyrate, phenethyl cinnamate, phenethyl hexanoate, phenethyl isobutyrate, phenethyl isovalerate, phenethyl 2-methylbutyrate, phenethyl 2-methylbutyrate, phenethyl 2-methylpropionate, phenethyl octanoate, phenethyl phenylacetate, phenethyl propionate phenoxyethyl propionate, 2-phenoxyethyl 2-methylpropionate, 3-phenyl-2-propenyl propionate, 3-phenylpropyl acetate, 2-phenylpropyl butyrate, 2-phenylpropyl isobutyrate , 2-phenylpropyl isovalerate, piperonyl acetate, piperonyl isobutyrate, prenyl acetate, propyl acetate, propyl butyrate, propyl heptanoate, propyl hexanoate, 3-propylidenephthalide, propyl isobutyrate, propyl propionate, propyl phenylacetate , sucrose octaacetate, terpinyl acetate, terpinyl butyrate, terpinyl isobutyrate, terpinyl propionate, tetrahydrofurfuryl acetate, tetrahydrofurfuryl butyrate, own tetrahydrofurfuryl nate, tetrahydrolinallyl acetate, 2,6,6,8-tetramethyltricyclo [5.3, 1.0 (1.5)] undecan-8-yl acetate, p-tolyl acetate, p-tolyl isobutyrate, p-tolyl phenylacetate, triacetin, tributyl acetyl citrate, tributyrin, tripropionin, 3,5,5-trimethylhexyl acetate, d-undecalactone,? -undecalactone,? -valerolactone, vanilla acetate, vanillin-sobutyrate, acetate-1 -vinyl-2- (1-methylpropyl) cyclohexyl, whiskey lactone, butyraldehyde, citronellal, decanal, cis-4-decane, trans-4-decane, 2,4-dimetiI-3-cyclohexen-1 -carbaldehyde, 2, 6-dimethyl-5-heptenal, 3,7-dimethyloctanal, 2-ethylbutyraldehyde, glutaraldehyde, heptanal, cis-4-heptenal, hexanal, hydrocinnamaldehyde, isobutyraldehyde, 3- (p-isopropylphenyl) -propionic acid, isovaleraldehyde, lauric aldehyde, 2-methylbutyraldehyde, 2-methyl-3- (p-isopropylphenyl) propionaldehyde, 2-methylpentanal, 4- (4-methyl-3-pentenyl) -3-cyclohexen-1 -carbaldehyde, 4-methylphenylacetaldehyde, 3- (methylthio) butanal, 2-methyl-4- ( 2,6,6-trimethyl-2-cyclohexen-1-yl) butanal, 2-methylundecanal, nonanal, cis-6-nonenal, octanal, phenacetaldehyde, 2-phenylpropionaldehyde, 3-phenylpropionaldehyde, propionaldehyde, p-tolylacetaldehyde, tridecanal, 2,4,6-trimethyl-3-cyclohexen-1 -carbaldehyde, 2,6,10-trimethyl-9-undecanal, 7-undecenal, 8-undecenal, 9-undecenal, 10-undecenal, valeraldehyde, acetanisol, 1 ' -acetonaphthone, 2'-acetonaphthone, acetone, acetophenone, 2-acetoxy-2,5-dimethyl-3 (2H) furanone, 2-acetylcyclopentanone, 4-acetyl-1,1-dimethyl-6-t-butylindane, 7- acetyl-1, 1, 3,4,4,6-hexanmethylindane, 2-acetyl-2-tizoline, 6-acetyl-1,1, 2,4,4,7-hexamethyl tetralin, allyl-ionone, benzylidene ketone, 2,3-butanedione, 2-sec-butylcyclohexanone, 5-t-butyl-3,5-dinitro-2,6-dimethylacetophenone, butyrophenone, camphor, 2-decanone, 3-decanone, 3-decen-2-one, dihydrocarvone, dihydro-β-ionone, dihydrojasmone, 4,5-dihydro-3 (2H) -thiophenone, 2 ', 4'-dimethylacetophenone, 3,4-dimethyl-1,2-cyclopentadione, 3,5-dimethyl-1 , 2-cyclopentadione, 2,6-dimethyl-4-heptanone, 1,3-diphenyl-2-propanone, 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone, p-ethylacetophenone, ethyl vinyl ketone, geranylacetone, 2, 3-heptanedione, 2-heptanone, 3-heptanone, 4-heptanone, 3,4-hexanedione, 3-hexanone, 4-hexen-3-one, 2-hexylidene cyclopentanone, α-ionone, β-ionone, 4-isobutyl -2,6-dimethyl-3,5-dinitroacetophenone, isophorone, 6-isopropyl-aldehydro-2-naphthone, cis-jasmona, livescona, 4-methoxyacetophenone, 4- (p-methoxyphenyl) -2-butanone, 4'-methylacetophenone, 3-methyl-1,2-cyclohexanedione, 3-methyl-2-cyclohexen-1 -one, 2- (2- (4-methyl-3-cyclohexen-1-yl) propyl) -cyclopentanone, 3-methyl-2 -cyclopenten-1 -one, methyl dihydrojasmonate, methyl ethyl ketone, 2-methyl-3-heptanone, 5-methyl-2-hepten-4-one, 6-methyl-5-hepten-2-one, 5-methyl -a-ionone, 1 - (2-methyl-5-isopropyI-2-cyclohexenyl) -1-propanone, 4-methyl-2-pentanone, 3-methyl-2- (2-penteniI) -2-cyclopenten-1 -one, 4-methyl-1-phenyl-2-pentanone, 2-methyltetrahydrofuran-3-one, 2-methyltetrahydrothiophen-3-one, 2-nonanone, 3-n onanone, 2-octanone, 3-octanone, 1-octen-3-one, 3-octen-2-one, 4-oxoisophorone, 2-pentadecanone, 2,3-pentanedione, 2-pentanone, 3-pentanone, 3- penten-2-one, 1-phenyl-1,2-propanedione, propiophenone, pulegone, 2-tridecanone, 2,2,6-trimethycyclohexanone, 4- (2,6,6-trimethyl-2-cyclohexen-1-yl) ) -3-methyl-3-buten-2-one, 2-undecanone and 6-undecanone.
- 13. The cyclic siloxane releasing active ingredient of claim 6, wherein RF has the formula (R1O) a (R2O) b (R3O) c (R4) d (R5) eSiRu, with Ru a divalent hydrocarbon radical of C2 -C40 and R4 and R5 independently selected from the group consisting of monovalent hydrocarbon radicals having from one to forty carbon atoms, 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 subjected to the limitation that a + b + c + d + e = 3, where each R1O, R2O and R3O are independently selected from the group of conjugated bases consisting of conjugate bases derived from the group of conjugated bases derived from the group of carbonyl active ingredients having the structure: R7-C (R8) = C (O -) - R9 where R7, R8 and R9 are each independently selected from the group consisting of hydrogen and monovalent hydrocarbon radicals having one to one hundred carbon atoms.
- The cyclic siloxane releasing active ingredient of claim 13, wherein the active carbon ingredients are fragrant carbonyl active ingredients.
- 15. The cyclic siloxane releasing active ingredients of claim 14, wherein the fragrant carbonyl active ingredients are selected from the group consisting of 4-acetoxy-3-pentyl-tetrahydropyran, allyl cinnamate, allyl 2-ethylbutyrate, cyclohexanopropionate allyl, allyl heptanoate, allyl hexanoate, allyl isovalerate, allyl nonanoate, allyl octanoate, allyl phenoxyacetate, allyl phenylacetate, allyl propionate, α-amylancinyl acetate, amyl octanoate, anisyl acetate, anisylphenyl, benzyl acetate, benzyl acetoacetate, benzyl butyrate, benzyl cinnamate, benzyl isobutyrate, benzyl isovalerate, benzyl phenylacetate, benzyl propionate, bornyl acetate, bornyl isovalerate, bornyl valerate, butyl acetate, butyl butyrate, butylbutyrillactate, 4-t-butylcyclohexyl acetate, butyl heptanoate, butyl hexanoate, butyl isobutyrate, butyl isovalerate, laurate butyl, butyl propionate, butyl stearate, 3-butylidenephthalide, butyl 2-methylbutyrate, butyl 10-undecenoate,? -butyrolactone, carvilo acetate, carvilo propionate, caryophyllene acetate, cedril acetate, trans acetate -cinamyl, trans-cinnamyl butyrate, cinnamyl cinnamate, cinnamyl isobutyrate, citronellyl acetate, citronellyl butyrate, citronellyl isobutyrate, citronellyl propionate, citronellyl valerate, cyclohexanoethyl acetate, cyclohexyl acetate, cyclohexyl butyrate,! cyclohexyl sovalerate, cyclohexyl propionate, d-decalactone, e-decalactone,? -decalactone, 4-decanolide, decyl acetate, decyl butyrate, decyl propionate, diethyl malonate, diethyl sebacate, diethyl succinate, dihydrocarvyl, dihydrocoumarin, dihydromyrcenyl acetate, dihydro-nor-dicyclopentadienyl acetate, dihydrotherminyl acetate, 3,7-dimethyl-1-6-octadien-3-yl acetate, 3,7-dimethyl-1-propionate 6-Octadien-3-yl, 3,7-dimethyloctane-3-yl acetate, a, a-dimethylphenethyl acetate, a, a-dimethylphenethyl butyrate, 6,10-dimethyl-5,9-undecadiene acetate 2-yl, d-dodecalactone, e-dodecalactone,? -dodecalactone, ethyl acetate, ethyl acetoacetate, ethyl 6-acetoxyhexanoate, ethyl 2-acetyl-3-phenylpropionate, ethyl benzoylacetate, 2-ethylbutyl acetate, ethyl butyrate, ethyl cinnamate, ethyl cyclohexanopropionate, ethyl decanoate, ethylene brasilate, ethyl 2-ethyl-6,6-dimethyl-2-cyclohexenecarboxylate, ethyl 2,3-epoxybutyrate, 2-methyl-4- ethyl pentenoate, ethyl heptanoate, ethyl hexanoate, ethyl trans-3-hexenoate, 2-ethylhexyl acetate, ethyl isobutyrate, ethyl isovalerate, ethyl laurate, ethyl 2-mercaptopropionate, ethyl 3-mercaptopropionate, Ethyl 2-methylbutyrate, ethyl 2-methipentenoate, (methylthio) ethyl acetate, methyl (methylthio) acetate, methyl 2- (methylthio) propionate, ethyl myristate, ethyl nonanoate , ethyl octanoate, ethyl palmitate, ethyl phenylacetate, ethyl 3-phenylpropionate, ethyl 3-phenyl-2,3-epoxybutyrate, ethyl 3-phenylpropionate, ethyl propionate, ethyl stearate, 2,3,6 , Ethyl 6-tetramethyl-2-cyclohexencarboxylate, ethyl (p-tolyloxy) ethyl acetate, ethyl undecanoate, ethyl valerate, eugenyl acetate, phenol acetate, geranyl acetate, geranyl butyrate, geranyl phenylacetate, propionate geranyl, guaiacyl phenylacetate, guaicamide acetate,? -heptalactone, heptyl acetate, heptyl butyrate, hypethyl isobutyrate,? -6-hexadecenlactone, d-hexalactone,? -hexalactone, 3-hexenyl acetate, cis-3-hexenyl 2-methylbutanoate, cis-3-hexenoxy cis-3-hexenoate, cis-3-hexenyl phenylacetate, trans-2-hexenyl acetate, hexyl acetate, butyrate of hexyl, hexyl hexanoate, hexyl isobutyrate, hexyl propionate, hexyl 2-methylbutanoate, hexyl 3-methylbutanoate, hexyl phenylacetate, isoamyl acetate, isoamyl acetoacetate, isoamyl butyrate, isoamyl cinnamate, isoamyl hexanoate isoamyl isobutyrate, isoamyl isovalerate, isoamyl laurate, isoamyl nonanoate, isoamyl octanoate, isoamyl phenylacetate, isoamyl propionate, isobornyl acetate, isobornyl propionate, isobutyl acetate, isobutyl butyrate, isobutyl cinnamate, hexanoate of isobutyl, isobutyl isobutyrate, isobutyl 2-methylbutyrate, sobutyl propionate, sodium soeugenyl acetate, isopropyl cinnamate, isobutyl phenylacetate, isopropyl acetate, isopropyl butyrate, isopropyl sobutyrate, isopropyl myristate, isopropyl palmitate, isopropyl phenylacetate, lauryl acetate, linalyl acetate, linalyl butyrate, linalyl sovalerate, mentalactone, menthyl acetate, menthyl cyclohexanecarboxylate, menthyl isovalerate, 4-methoxybenzyl acetate, 4-methoxybenzyl propionate, 2-methoxyphenyl acetate, 2-methoxy-4- (1-propenyl) phenyl acetate, methyl acetate, a-methylbenzyl acetate, a-methylbenzyl butyrate, a-methylbenzyl propionate, acetate of 2-methylbutyl, 2-methylbutyl butyrate, 2-methylbutyl isovalerate, 3-methylbutyl-2-methylbutanoate, 2-methylbutyl-2-methylbutanoate, methyl pt-butylphenylacetate, methyl butyrate, methyl cinnamate, methyl decanoate , methyl heptanoate, methyl hexanoate, methyl isobutyrate, methyl isovalerate, methyl laurate, methyl N-2-methyl-3- (4-t-butylphenylpropylidene) anthranilate, methyl myristate, methyl nonanoate, octanoate methyl, methyl palmitate, aceta 4- (4-methyl-3-pentenyl) -3-cyclohexenylmethyl, methyl 2-methylbutyrate, 2-methyl-6-methylene-7-octen-2-yl acetate, methyl 4-methylvalerate, 2- methyl methylpentanoate, methyl phenoxyacetate, 4-methylphenyl phenylacetate, 2-methyl-3-phenylpropan-2-yl acetate, methyl 3-phenylpropionate, methyl propionate, 2-methylpropyl phenylacetate, methyl phenylacetate, ethyl acetate 2-methyl-3-phenylpropan-2-yl, methyl stearate, methyl (p-tolyloxy) acetate, methyl 9-undecentate, methyl valerate, mirtenyl acetate, neryl acetate, neryl butyrate, sodium butyrate neryl, d-nonalactone,? -nonalactone, 1,3-nonanediol diacetate, nonyl acetate, nopyl acetate, octahydrocoumarin,? -octalactone, 1-octen-3-yl acetate, 1-keten-3-butyrate ilo, octyl acetate, actyl butyrate, octyl isobutyrate, octyl isovalerate, octyl octanoate, octyl propionate, oxacycloheptadec-10-en-2-one,? -pentadecalactone, pentyl acetate, butyrate pentyl, pentyl hexanoate, pentyl octanoate, phenethyl acetate, phenethyl butyrate, phenethyl cinnamate, phenethyl hexanoate, phenethyl isobutyrate, phenethyl isovalerate, phenethyl 2-methylbutyrate, phenethyl 2-methylbutyrate, 2-methylpropionate, phenethyl, phenethyl octanoate, phenethyl phenylacetate, phenethyl propionate phenoxyethyl propionate, 2-phenoxyethyl 2-methylpropionate, 3-phenyl-2-propenyl propionate, 3-phenylpropyl acetate, 2-phenylpropyl butyrate, isobutyrate 2 phenylpropyl, 2-phenylpropyl isovalerate, piperonyl acetate, piperonyl isobutyrate, prenyl acetate, propyl acetate, propyl butyrate, propyl heptanoate, propyl hexanoate, 3-propylidenephthalide, propyl isobutyrate, propyl propionate, phenylacetate of propyl, sucrose octaacetate, terpinyl acetate, terpinyl butyrate, terpinyl isobutyrate, terpinyl propionate, tetrahydrofurfuryl acetate, tetrahydrofurfuryl butyrate, tetrahydrofurfuryl propionate, tetrahydrolinallyl acetate, 2,6,6,8-tetramethyltricyclo [5.3, 1.0 (1.5)] undecan-8-yl acetate, p-tolyl acetate, p-tolyl isobutyrate, p-tolyl phenylacetate, triacetin, tributyl acetyl citrate, tributyrin, tripropionin, 3,5,5-trimethylhexyl acetate, d-undecalactone,? -undecalactone,? -valerolactone, vanilla acetate, vanillin isobutyrate, acetate 1 vinyl-2- (1-methylpropyl) cyclohexyl, whiskey lactone, butyraldehyde, citronellal, decanal, cis-4-decane, trans-4-decane, 2,4-dimethyl-3-cyclohexen-1 -carbaldehyde, 2,6 -dimethyl-5-heptenal, 3,7-dimethyloctanal, 2-ethylbutyraldehyde, glutaraldehyde, heptanal, cis-4-heptenal, hexanal, hydrocinnamaldehyde, isobutyraldehyde, 3- (p-isopropylphenyl) -propionaldehyde, isovaleraldehyde, lauric aldehyde, - methylbutyraldehyde, 2-methyl-3- (p-isopropylphenyl) propionaldehyde, 2-methylpentanal, 4- (4-methyl-3-pentenyl) -3-cyclohexen-1 -carbaldehyde, 4-methylphenylacetaldehyde, 3- (methylthio) butanal 2-methyl-4- (2 , 6,6-trimethyl-2-cyclohexen-1-yl) butanal, 2-methylundecanal, nonanal, cis-6-nonenal, octanal, phenylacetaldehyde, 2-phenylpropionaldehyde, 3-phenylpropionaldehyde, propionaldehyde, p-tolylacetaldehyde, tridecanal, 2 , 4,6-trimethyl-3-cyclohexen-1 -carbaldehyde, 2,6, 10-trimethyl-9-undecanal, 7-undecenal, 8-undecenal, 9-undecenal, 10-undecenal, valeraldehyde, acetanisol, 1 '- acetonaphthone, 2'-acetonaphthone, acetone, acetophenone, 2-acetoxy-2,5-dimethyl-3 (2H) furanone, 2-acetylcyclopentanone, 4-acetyl-1,1-dimethyl-6-t-butyl-indane, 7-acetyl - 1, 1, 3,4,4,6-hexanmethylindane, 2-acetyl-2-tizoline, 6-acetyl-1,1, 2,4,4,7-hexamethyl tetralin, allyl-ionone, benzylidene ketone, , 3-butanedione, 2-sec-butylcyclohexanone, 5-t-butyl-3,5-dinitro-2,6-dimethylacetophenone, butyrophenone, camphor, 2-decanone, 3-decanone, 3-decen-2-one, dihydrocarvone , dihydro-ß-ionone, dihydrojasmone, 4,5-dihydro-3 (2H) -thiophenone, 2 ', 4'-dimethylacetophenone, 3,4-dimethyl-1,2-cyclopentadione, 3,5-dimethyl-1, 2-cyclopentadione , 2,6-dimethyl-4-heptanone, 1,3-diphenyl-2-propanone, 4- (1-ethoxyvinyl) -3,3,5,5-tetramethylcyclohexanone, p-ethylacetophenone, ethyl vinyl ketone, geranylacetone, , 3-heptanedione, 2-heptanone, 3-heptanone, 4-heptanone, 3,4-hexanedione, 3-hexanone, 4-hexen-3-one, 2-hexylidene cyclopentanone, α-ionone, β-ionone, 4- isobutyl-2,6-dimethyl-3,5-dinitroacetophenone, isophorone, 6-isopropyl-aldehydro-2-naphthone, cis-jasmona, livescona, 4-methoxyacetophenone, 4- (p-methoxyphenyl) -2-butanone, 4'-methylacetophenone , 3-methyl-1,2-cyclohexanedione, 3-methyl-2-cyclohexen-1 -one, 2- (2- (4-methyl-3-cyclohexen-1 -yl) propyl) -cyclopentanone, 3 m? <; ethyl-2-cyclopenten-1-one, methyl dihydrojasmonate, methyl ethyl ketone, 2-m? < ethyl-3-heptanone, 5-methyl-2-hepten-4-one, 6-methyl-5-hepten-2-one, 5-m í < ethyl-a-ionone, 1- (2-methyl-5-isopropyl-2-cyclohexenyl) -1-propanone, 4-methyl-2-pentanone, 3-methyl-2- (2-pentenyl) -2-cyclopenten -1 -one, 4-methyl-1-phenyl-2-pentanone, 2-methyltetrahydrofuran-3-one, 2-methyltetrahydrothiophen-3-one, 2-nonanone, 3-nonanone, 2-octanone, 3-octanone, 1 -octen-3-one, 3-octen-2-one, 4-oxoisophorone, 2-pentadecanone, 2,3-pentanedione, 2-pentanone, 3-pentanone, 3-penten-2-one, 1-phenyl-1 , 2-propandione, propiophenone, pulegone, 2-tridecanone, 2,2,6-trimethylcyclohexanone, 4- (2,6,6-trimethyl-2-cyclohexen-1-yl) -3-methyl-3-buten-2 -one, 2-undecanone and 6-undecanone.
- 16. A composition comprising the siloxane releasing active ingredient of claim 1.
- 17. A composition comprising the siloxane releasing active ingredient of claim 2.
- 18. A composition comprising the siloxane releasing active ingredient of claim 6.
- 19 A composition comprising the siloxane releasing active ingredient of claim 10.
- 20. A composition comprising the siloxane releasing active ingredient of claim 13.
- 21. A composition consisting essentially of the siloxane releasing active ingredient of claim 1.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10742033 | 2003-12-19 |
Publications (1)
Publication Number | Publication Date |
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MXPA06007050A true MXPA06007050A (en) | 2006-12-13 |
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