CN1893910A - 用于活性成分释放的环硅氧烷合成物 - Google Patents
用于活性成分释放的环硅氧烷合成物 Download PDFInfo
- Publication number
- CN1893910A CN1893910A CNA2004800379826A CN200480037982A CN1893910A CN 1893910 A CN1893910 A CN 1893910A CN A2004800379826 A CNA2004800379826 A CN A2004800379826A CN 200480037982 A CN200480037982 A CN 200480037982A CN 1893910 A CN1893910 A CN 1893910A
- Authority
- CN
- China
- Prior art keywords
- acetate
- methyl
- acid
- ethyl
- alcohol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
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- -1 Cyclic siloxane Chemical class 0.000 title claims abstract description 246
- 239000000203 mixture Substances 0.000 title claims description 38
- 239000004480 active ingredient Substances 0.000 title abstract description 6
- 150000002148 esters Chemical class 0.000 claims abstract description 44
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- 150000001299 aldehydes Chemical class 0.000 claims abstract description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 76
- 239000002253 acid Substances 0.000 claims description 34
- 229910052799 carbon Inorganic materials 0.000 claims description 29
- 229940022663 acetate Drugs 0.000 claims description 24
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 23
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 claims description 22
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims description 22
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 21
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 150000002085 enols Chemical class 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 17
- 150000001721 carbon Chemical group 0.000 claims description 16
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 claims description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 15
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 14
- IGODOXYLBBXFDW-UHFFFAOYSA-N alpha-Terpinyl acetate Chemical compound CC(=O)OC(C)(C)C1CCC(C)=CC1 IGODOXYLBBXFDW-UHFFFAOYSA-N 0.000 claims description 14
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 claims description 14
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 14
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 13
- 229960003424 phenylacetic acid Drugs 0.000 claims description 13
- 239000003279 phenylacetic acid Substances 0.000 claims description 13
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 claims description 12
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 claims description 12
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims description 12
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 claims description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 11
- 235000000484 citronellol Nutrition 0.000 claims description 11
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 claims description 11
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 10
- CRBJBYGJVIBWIY-UHFFFAOYSA-N 2-isopropylphenol Chemical compound CC(C)C1=CC=CC=C1O CRBJBYGJVIBWIY-UHFFFAOYSA-N 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 claims description 10
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 10
- OBNCKNCVKJNDBV-UHFFFAOYSA-N butanoic acid ethyl ester Natural products CCCC(=O)OCC OBNCKNCVKJNDBV-UHFFFAOYSA-N 0.000 claims description 10
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims description 10
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 claims description 10
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 claims description 10
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 claims description 10
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 claims description 9
- MSHFRERJPWKJFX-UHFFFAOYSA-N 4-Methoxybenzyl alcohol Chemical compound COC1=CC=C(CO)C=C1 MSHFRERJPWKJFX-UHFFFAOYSA-N 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 9
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 claims description 9
- AYQPVPFZWIQERS-UHFFFAOYSA-N cis-2-octen-1-ol Natural products CCCCCC=CCO AYQPVPFZWIQERS-UHFFFAOYSA-N 0.000 claims description 9
- WDAXFOBOLVPGLV-UHFFFAOYSA-N ethyl isobutyrate Chemical compound CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 claims description 9
- IFYYFLINQYPWGJ-UHFFFAOYSA-N gamma-decalactone Chemical compound CCCCCCC1CCC(=O)O1 IFYYFLINQYPWGJ-UHFFFAOYSA-N 0.000 claims description 9
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 claims description 9
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 claims description 8
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 claims description 8
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 claims description 8
- VZWGRQBCURJOMT-UHFFFAOYSA-N Dodecyl acetate Chemical compound CCCCCCCCCCCCOC(C)=O VZWGRQBCURJOMT-UHFFFAOYSA-N 0.000 claims description 8
- JSLCOZYBKYHZNL-UHFFFAOYSA-N butylisobutyrate Chemical compound CCCCOC(=O)C(C)C JSLCOZYBKYHZNL-UHFFFAOYSA-N 0.000 claims description 8
- PWLNAUNEAKQYLH-UHFFFAOYSA-N butyric acid octyl ester Natural products CCCCCCCCOC(=O)CCC PWLNAUNEAKQYLH-UHFFFAOYSA-N 0.000 claims description 8
- PPXUHEORWJQRHJ-UHFFFAOYSA-N ethyl isovalerate Chemical compound CCOC(=O)CC(C)C PPXUHEORWJQRHJ-UHFFFAOYSA-N 0.000 claims description 8
- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 claims description 8
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 claims description 8
- VAMXMNNIEUEQDV-UHFFFAOYSA-N methyl anthranilate Chemical compound COC(=O)C1=CC=CC=C1N VAMXMNNIEUEQDV-UHFFFAOYSA-N 0.000 claims description 8
- RGFNRWTWDWVHDD-UHFFFAOYSA-N sec-butyl ester of butyric acid Natural products CCCC(=O)OCC(C)C RGFNRWTWDWVHDD-UHFFFAOYSA-N 0.000 claims description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 8
- UWKAYLJWKGQEPM-UHFFFAOYSA-N 3,7-dimethylocta-1,6-dien-3-yl acetate Chemical compound CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 claims description 7
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 claims description 7
- 239000001191 butyl (2R)-2-hydroxypropanoate Substances 0.000 claims description 7
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 claims description 7
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 7
- LHGVFZTZFXWLCP-UHFFFAOYSA-N guaiacol Chemical compound COC1=CC=CC=C1O LHGVFZTZFXWLCP-UHFFFAOYSA-N 0.000 claims description 7
- 229940117955 isoamyl acetate Drugs 0.000 claims description 7
- 150000002596 lactones Chemical class 0.000 claims description 7
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 claims description 6
- RXBQNMWIQKOSCS-UHFFFAOYSA-N (7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)methanol Chemical compound C1C2C(C)(C)C1CC=C2CO RXBQNMWIQKOSCS-UHFFFAOYSA-N 0.000 claims description 6
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 claims description 6
- UFLHIIWVXFIJGU-ARJAWSKDSA-N (Z)-hex-3-en-1-ol Chemical compound CC\C=C/CCO UFLHIIWVXFIJGU-ARJAWSKDSA-N 0.000 claims description 6
- YGFGZTXGYTUXBA-UHFFFAOYSA-N (±)-2,6-dimethyl-5-heptenal Chemical compound O=CC(C)CCC=C(C)C YGFGZTXGYTUXBA-UHFFFAOYSA-N 0.000 claims description 6
- QPVRKFOKCKORDP-UHFFFAOYSA-N 1,3-dimethylcyclohexa-2,4-dien-1-ol Chemical class CC1=CC(C)(O)CC=C1 QPVRKFOKCKORDP-UHFFFAOYSA-N 0.000 claims description 6
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims description 6
- JLIDVCMBCGBIEY-UHFFFAOYSA-N 1-penten-3-one Chemical compound CCC(=O)C=C JLIDVCMBCGBIEY-UHFFFAOYSA-N 0.000 claims description 6
- IAIHUHQCLTYTSF-UHFFFAOYSA-N 2,2,4-trimethylbicyclo[2.2.1]heptan-3-ol Chemical compound C1CC2(C)C(O)C(C)(C)C1C2 IAIHUHQCLTYTSF-UHFFFAOYSA-N 0.000 claims description 6
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 claims description 6
- NGDNVOAEIVQRFH-UHFFFAOYSA-N 2-nonanol Chemical compound CCCCCCCC(C)O NGDNVOAEIVQRFH-UHFFFAOYSA-N 0.000 claims description 6
- PRNCMAKCNVRZFX-UHFFFAOYSA-N 3,7-dimethyloctan-1-ol Chemical compound CC(C)CCCC(C)CCO PRNCMAKCNVRZFX-UHFFFAOYSA-N 0.000 claims description 6
- XPCTZQVDEJYUGT-UHFFFAOYSA-N 3-hydroxy-2-methyl-4-pyrone Chemical compound CC=1OC=CC(=O)C=1O XPCTZQVDEJYUGT-UHFFFAOYSA-N 0.000 claims description 6
- XKWSWANXMRXDES-UHFFFAOYSA-N 3-methylbutyl octanoate Chemical compound CCCCCCCC(=O)OCCC(C)C XKWSWANXMRXDES-UHFFFAOYSA-N 0.000 claims description 6
- RHLVCLIPMVJYKS-UHFFFAOYSA-N 3-octanone Chemical compound CCCCCC(=O)CC RHLVCLIPMVJYKS-UHFFFAOYSA-N 0.000 claims description 6
- VLJSLTNSFSOYQR-UHFFFAOYSA-N 3-propan-2-ylphenol Chemical compound CC(C)C1=CC=CC(O)=C1 VLJSLTNSFSOYQR-UHFFFAOYSA-N 0.000 claims description 6
- CHWNEIVBYREQRF-UHFFFAOYSA-N 4-Ethyl-2-methoxyphenol Chemical compound CCC1=CC=C(O)C(OC)=C1 CHWNEIVBYREQRF-UHFFFAOYSA-N 0.000 claims description 6
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 claims description 6
- HCFAJYNVAYBARA-UHFFFAOYSA-N 4-heptanone Chemical compound CCCC(=O)CCC HCFAJYNVAYBARA-UHFFFAOYSA-N 0.000 claims description 6
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 claims description 6
- OIGWAXDAPKFNCQ-UHFFFAOYSA-N 4-isopropylbenzyl alcohol Chemical compound CC(C)C1=CC=C(CO)C=C1 OIGWAXDAPKFNCQ-UHFFFAOYSA-N 0.000 claims description 6
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 claims description 6
- PXRBWNLUQYZAAX-UHFFFAOYSA-N 6-Butyltetrahydro-2H-pyran-2-one Chemical compound CCCCC1CCCC(=O)O1 PXRBWNLUQYZAAX-UHFFFAOYSA-N 0.000 claims description 6
- QGFSQVPRCWJZQK-UHFFFAOYSA-N 9-Decen-1-ol Chemical compound OCCCCCCCCC=C QGFSQVPRCWJZQK-UHFFFAOYSA-N 0.000 claims description 6
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 claims description 6
- BAVONGHXFVOKBV-UHFFFAOYSA-N Carveol Chemical compound CC(=C)C1CC=C(C)C(O)C1 BAVONGHXFVOKBV-UHFFFAOYSA-N 0.000 claims description 6
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 6
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 claims description 6
- NUPSHWCALHZGOV-UHFFFAOYSA-N Decyl acetate Chemical compound CCCCCCCCCCOC(C)=O NUPSHWCALHZGOV-UHFFFAOYSA-N 0.000 claims description 6
- KRCZYMFUWVJCLI-UHFFFAOYSA-N Dihydrocarveol Chemical compound CC1CCC(C(C)=C)CC1O KRCZYMFUWVJCLI-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
- HPEUJPJOZXNMSJ-UHFFFAOYSA-N Methyl stearate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC HPEUJPJOZXNMSJ-UHFFFAOYSA-N 0.000 claims description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- DFYRUELUNQRZTB-UHFFFAOYSA-N apocynin Chemical group COC1=CC(C(C)=O)=CC=C1O DFYRUELUNQRZTB-UHFFFAOYSA-N 0.000 claims description 6
- XUPYJHCZDLZNFP-UHFFFAOYSA-N butyl butanoate Chemical compound CCCCOC(=O)CCC XUPYJHCZDLZNFP-UHFFFAOYSA-N 0.000 claims description 6
- NEHNMFOYXAPHSD-UHFFFAOYSA-N citronellal Chemical compound O=CCC(C)CCC=C(C)C NEHNMFOYXAPHSD-UHFFFAOYSA-N 0.000 claims description 6
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 claims description 6
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 claims description 6
- AZOCECCLWFDTAP-UHFFFAOYSA-N dihydrocarvone Chemical compound CC1CCC(C(C)=C)CC1=O AZOCECCLWFDTAP-UHFFFAOYSA-N 0.000 claims description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 6
- OMSUIQOIVADKIM-UHFFFAOYSA-N ethyl 3-hydroxybutyrate Chemical compound CCOC(=O)CC(C)O OMSUIQOIVADKIM-UHFFFAOYSA-N 0.000 claims description 6
- RGXWDWUGBIJHDO-UHFFFAOYSA-N ethyl decanoate Chemical compound CCCCCCCCCC(=O)OCC RGXWDWUGBIJHDO-UHFFFAOYSA-N 0.000 claims description 6
- XIRNKXNNONJFQO-UHFFFAOYSA-N ethyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OCC XIRNKXNNONJFQO-UHFFFAOYSA-N 0.000 claims description 6
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 claims description 6
- GAEKPEKOJKCEMS-UHFFFAOYSA-N gamma-valerolactone Chemical compound CC1CCC(=O)O1 GAEKPEKOJKCEMS-UHFFFAOYSA-N 0.000 claims description 6
- NGAZZOYFWWSOGK-UHFFFAOYSA-N heptan-3-one Chemical compound CCCCC(=O)CC NGAZZOYFWWSOGK-UHFFFAOYSA-N 0.000 claims description 6
- UFLHIIWVXFIJGU-UHFFFAOYSA-N hex-3-en-1-ol Natural products CCC=CCCO UFLHIIWVXFIJGU-UHFFFAOYSA-N 0.000 claims description 6
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 claims description 6
- QNVRIHYSUZMSGM-UHFFFAOYSA-N hexan-2-ol Chemical compound CCCCC(C)O QNVRIHYSUZMSGM-UHFFFAOYSA-N 0.000 claims description 6
- ZOCHHNOQQHDWHG-UHFFFAOYSA-N hexan-3-ol Chemical compound CCCC(O)CC ZOCHHNOQQHDWHG-UHFFFAOYSA-N 0.000 claims description 6
- JARKCYVAAOWBJS-UHFFFAOYSA-N hexanal Chemical compound CCCCCC=O JARKCYVAAOWBJS-UHFFFAOYSA-N 0.000 claims description 6
- NCDCLPBOMHPFCV-UHFFFAOYSA-N hexyl hexanoate Chemical compound CCCCCCOC(=O)CCCCC NCDCLPBOMHPFCV-UHFFFAOYSA-N 0.000 claims description 6
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 6
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 claims description 6
- 229940011051 isopropyl acetate Drugs 0.000 claims description 6
- 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 6
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 claims description 6
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 claims description 6
- UQDUPQYQJKYHQI-UHFFFAOYSA-N methyl laurate Chemical compound CCCCCCCCCCCC(=O)OC UQDUPQYQJKYHQI-UHFFFAOYSA-N 0.000 claims description 6
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- JGHZJRVDZXSNKQ-UHFFFAOYSA-N methyl octanoate Chemical compound CCCCCCCC(=O)OC JGHZJRVDZXSNKQ-UHFFFAOYSA-N 0.000 claims description 6
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- NPNUFJAVOOONJE-UHFFFAOYSA-N beta-cariophyllene Natural products C1CC(C)=CCCC(=C)C2CC(C)(C)C21 NPNUFJAVOOONJE-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
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- 230000036760 body temperature Effects 0.000 description 1
- 229910052796 boron Inorganic materials 0.000 description 1
- 238000005282 brightening Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052792 caesium Inorganic materials 0.000 description 1
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- 230000007774 longterm Effects 0.000 description 1
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- RPUSRLKKXPQSGP-UHFFFAOYSA-N methyl 3-phenylpropanoate Chemical compound COC(=O)CCC1=CC=CC=C1 RPUSRLKKXPQSGP-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
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- BKATZVAUANSCKN-UHFFFAOYSA-N myrtenyl acetate Natural products CC(=O)OCC1=CCC2C(C)(C)C1C2 BKATZVAUANSCKN-UHFFFAOYSA-N 0.000 description 1
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- 150000007524 organic acids Chemical class 0.000 description 1
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- 125000002524 organometallic group Chemical group 0.000 description 1
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
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- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- BDDWSAASCFBVBK-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 BDDWSAASCFBVBK-UHFFFAOYSA-N 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
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- 238000005070 sampling Methods 0.000 description 1
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- 239000002453 shampoo Substances 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000005987 sulfurization reaction Methods 0.000 description 1
- 230000000475 sunscreen effect 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
- 239000000725 suspension Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- NPNUFJAVOOONJE-ZIAGYGMSSA-N trans-caryophyllene Natural products C1CC(C)=CCCC(=C)[C@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-ZIAGYGMSSA-N 0.000 description 1
- 229940094989 trimethylsilane Drugs 0.000 description 1
- YZWRNSARCRTXDS-UHFFFAOYSA-N tripropionin Chemical compound CCC(=O)OCC(OC(=O)CC)COC(=O)CC YZWRNSARCRTXDS-UHFFFAOYSA-N 0.000 description 1
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N vinyl ethyl ether Natural products CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 1
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- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
- A61K8/585—Organosilicon compounds
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
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- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q13/00—Formulations or additives for perfume preparations
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/21—Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G77/38—Polysiloxanes modified by chemical after-treatment
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
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Abstract
本发明公开了含有可释放活性成分的环硅氧烷。活性成分可以为醇或含有可烯醇化羰基的化合物,例如酮、醛或酯。产品硅氧烷用于需要减缓或控制活性成分释放的各种个人和家庭护理产品中。优选实施方案使用取代基,使得当作为活性成分释放时为芳香的。
Description
相关申请的交叉引用
不适用
关于Federally Funded Research的声明
不适用
技术领域
本发明涉及环状硅氧烷,其适用于多种用途,所述多种用途包括个人护理制剂、香料、家用产品、洗涤剂、漂洗添加剂、汽车、纺织品和模具材料,其中环硅氧烷被化学改性为在水解时释放活性成分。本发明还涉及活性成分释放速率足够低的分子,以使利用改性环硅氧烷配制的产品长期表现出所期望的效果。
背景技术
活性成分的缓慢、持续释放在许多个人护理、纺织、汽车、塑料、洗衣和家用产品中都为非常理想的特性。多种方式已经建议或用于实现这个目标。这些方式包括在个人护理乳液中溶解或悬浮芳香化合物(US 5,525,588;US 5,525,555;US 5,490,982;US 5,372,806;EP0334490;WO 0064497)、芳香化合物的封装(US 5,500,223;US5,324,444;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 6,042,792;US 5,867,755;US 5,049,182;US 6,624,136;美国专利申请20020187221、20020009522和20010008635;EP 1116515、EP 1061124、EP 1133929;WO 0179303、WO 0173188A1、WO 9815192A1、WO 02076514)、将芳香化合物溶解于例如硅氧烷这样的疏水相中(US 5,449,512;US5,160,494;US 5,234,689;WO 0241709A1)、将芳香化合物引入交联聚合物中(US 6,435,423;US 5,139,864;US 6,379,689;US 5,387,622;US 5,387,411;WO 03032749;WO 02065858;JP 11047581)、将芳香化合物引入可透过的层压材料中(US 6,500,444;US 5,071,704;US5,008,115)、将芳香化合物引入在体温下软化的介质中(US 4,908,208;EP1178107;WO 0016643)、将芳香化合物引入生物降解的介质中(US6,121,343)或生物活化的介质中(US 5,378,468)、将芳香化合物引入速率控制膜中(US 6,063,365和US 4,445,641)、用芳香醇使硅烷衍生化以形成烷氧基硅烷(US 4,524,018和US 4,500,725)、香精衍生化以形成在曝光时释放香味的光敏分子(WO 02083620;JP2002020783A)。活性物衍生作用以得到可水解的有机(亦即不含硅的)分子也公开在文献中。
由于很多活性成分为有非常高官能性的有机物并且不能与个人和日用护理产品中的硅氧烷相容,导致脱水收缩和其它相分离现象,因此含硅分子与活性成分的结合是人们所特别关心的。已经公开了使用长链醇皮肤护理活性物与硅烷的衍生作用,从而得到烷氧基三甲基硅烷(US 5,847,179)和使用羟基羧酸皮肤表皮脱落剂将硅烷衍生化形成(三有机甲硅烷基)烷氧基羧酸酯(US 6,143,309;US 6,228,380;US6,267,977)。Allen等人报道了用芳香醇直接置换硅原子上的烷氧基离去基团,得到芳香硅酯或线性硅酸酯(US 3,215,719和US 3,271,305)。他人也报道了形成线性芳香硅氧烷聚合物或共聚物的类似烷氧基置换反应(GB 2,041,964;GB 2,042,890;EP 273266)。还报道了醇、醛、酮或内酯在金属羧酸盐和还原剂的存在下与甲硅烷基氢化物反应生成线性聚合物和共聚物(WO 9628497)。Anderson等人(EP878497、JP10330382、US 6,262,287)和Perry等人(US 6,046,156;US 6,077,923;US 6,153,578;US 6,054,547;US 6,075,111;US 6,322,777;US 6,083,901)公开了使用甲硅烷基氢化物得到芳香硅氧烷的其它路线。在这些方法中,利用氢化硅烷化化学将分子的活性部分连接到硅氧烷骨架上。现有技术没有教导或提出的是,活性成分-官能环硅氧烷化合物的形成和其在个人护理、纺织、洗衣或塑料中的应用。在此我们公开了一种新化合物和由环甲硅烷基氢化物制备活性成分官能环硅氧烷物品的方法。该方法为醇或含羰基化合物与环甲硅烷基氢化物在催化剂存在下直接反应形成产物和氢气副产物。
发明内容
发明概述
本发明提供式I或II表示的活性释放环硅氧烷:
式I中,R1为氢或一价C1-C24烃基。此处使用的术语一价烃基包括脂肪族和芳香族一价烃基,其还可具有例如氧、氮、磷、硫这些杂原子以及卤素氟、氯、溴和碘。数量n至少为1,而p和q各自独立地为非负数,条件是n+p+q的总和大于或等于3。对于式II,R2选自氢或一价C1-C24烃基。R3和R4各自独立地为氢或一价C1-C24烃基。r和u各自独立且至少为1,s和t各自独立地为非负数,条件是r+s+t+u的总和大于或等于3。
标记为Ofrag的部分分别独立地为衍生自醇或含有可烯醇化羰基的活性成分的活性醇盐或烯醇化物部分,其中frag选自具有1-100个碳原子、优选4-100个碳原子、更优选5-100个碳原子、最优选6-100个碳原子的一价烃基。本发明还提供含有活性释放硅氧烷的组合物。特别应用为包括活性释放硅氧烷的化妆品组合物,例如香水、护肤霜、化妆品、粉底等,以及洗衣剂,例如洗衣剂组合物、漂洗添加剂、织物柔软剂等。
发明详述
本发明提供式I或II表示的活性释放环硅氧烷:
式I中,R1为氢或一价C1-C24烃基。此处使用的术语一价烃基包括脂肪族和芳香族一价烃基,其也可具有例如氧、氮、磷、硫和卤素氟、氯、溴和碘的杂原子。n至少为1,而p和q各自独立地为非负数,条件是n+p+q的总和大于或等于3。对于式II,R2选自氢或一价C1-C24烃基。R3和R4各自独立地为氢或一价C1-C24烃基。r和u各自独立,且至少为1,s和t各自独立地为非负数,条件是r+s+t+u的总和大于或等于3。
标记为Ofrag的部分分别独立地为衍生自醇或含有可烯醇化羰基的活性成分的活性醇盐或烯醇化物部分,其中frag选自具有1-100个碳原子、优选4-100个碳原子、更优选5-100个碳原子,最优选6-100个碳原子的一价烃基。本发明还提供含有活性释放硅氧烷的组合物。特别应用为含有活性释放硅氧烷的化妆品组合物,例如香水、护肤霜、化妆品、粉底等,以及洗衣剂,例如洗衣剂组合物、漂洗添加剂、织物柔软剂等。
本发明的化合物通过取代环甲硅烷基氢化物的氢引入活性成分。这些硅氧烷分子用于多种个人护理组合物中。本发明涉及重要的新组合物,其为在水解时释放醇或含可烯醇化羰基活性成分的环硅氧烷,即释放醇或羰基化合物的硅氧烷,其中活性成分包括但不限于增粘剂、粘合剂、防老化剂、抗氧化剂、止汗剂、抗静电剂、杀生物剂、苦味剂、漂白剂、抛光剂、着色剂、调节剂、消泡剂、洗涤剂、消毒剂、分散剂、填料、起泡剂、泡沫稳定剂、香料、湿润剂、水溶增溶剂、驱虫剂、液晶、增湿剂、去味剂、遮光剂、口腔护理添加剂、药物、防腐剂、流变改性剂、掩蔽剂、螯合剂、增溶剂、溶剂、防晒剂、表面活性剂、悬浮剂、鞣剂、增稠剂、维生素或其它营养素以及增白剂。
本发明使用的环氢化硅氧烷通过式III或IV表示:
其中R1和R2各自独立地选自氢或C1-C24一价烃基。v大于或等于3,w和u各自独立地至少为1,条件是w+u必须等于或大于3。R3和R4各自独立地选自H或C1-C24一价烃基。使用的环氢化物为各种大小和浓度的环的混合物。
以下合成实施例将用于说明硅氧烷化学领域技术人员为制备本发明使用的含活性的环硅氧烷通常使用的合成反应路线。因此这些反应路线仅仅为说明目的而并不代表可以使用的唯一合成路线。
反应路线I:
如反应流程I所示,当起始活性成分为醇时,优选在合适催化剂的存在下制备相应的烷氧基硅氧烷。
反应路线II:
反应路线III
如反应流程II和III所示,含羰基活性物的反应需要建立羰基-烯醇的互变异构平衡,这一平衡在例如三乙胺或硅醇盐这样的碱辅助下进行。
互变异构为在两种或多种不同结构化合物间建立平衡的化学现象。在几乎所有的情形,平衡化合物的一种互变异构体与另一种互变异构体的差别在于氢原子的异构位置。互变异构的常见形式为羰基化合物(亦即含有羰基的化合物)和在羰基α位具有氢原子、亦即α氢之间的互变异构平衡:
酮型 烯醇型
通常平衡常数有利于酮型并且平衡更有利于向左进行。烯醇化程度非常受溶剂、浓度和温度的影响。当强碱存在时,烯醇型和酮型都可失去氢离子(质子),形成烯醇负离子:
由于两种结构的区别仅仅在于电子的分布,这些为相同离子而不是互变异构体的典型形式。由于氧比碳更具电负性,优势形式为离子电荷更多位于氧原子上的那种。虽然烯醇和酮或醛之间的互变异构平衡通常不是制备性反应,但由于酮和醛通常通过它们的烯醇型反应,正如在本发明化合物制备中立即反应形成烯醇那样,因此这种平衡必然存在。酮-烯醇互变异构平衡还可建立于酯或有机酸,亦即上述结构中当R8具有键合于合适的R基的氧原子时,例如OR′,化合物为有机酯。这种化学机理的详细解释参见J.March《Advanced OrganicChemistry》,John Wiley & Sons,New York(1985),第66-68页和第527-529页以及其中的参考文献。
芳香分子,醇、酮和醛可作为醇或烯醇互变异构体反应以制备带有芳香部分的硅酮或硅氧烷。该反应涉及醇或烯醇形式的分子与直接键接于硅原子的氢、羟基或卤素反应生成芳香衍生物。反应包括与醇或分子的烯醇互变异构形式的共轭碱的形成。
FragOH离解成H+和FragO-(共轭碱)
其中FragOH为芳香醇或芳香酮或醛的烯醇型。醛和酮与醇R′OH反应生成半缩醛(得自醛)或半缩酮(得自酮): 半缩醛,其具有通过除去羟基氢原子得到的共轭碱:RCH(O-)(OR′),以及 ,同样,其也具有通过除去羟基氢原子得到的共轭碱:RC(O-)(R′O)R″。此处使用的各种Frag为芳香部分,亦即一价基团,其或为中性电荷一价基团(Frag或FragO),或为得自芳香分子共轭碱的带电一价基团,例如 ,其中一价基团为具有1-100个碳原子、优选4-100个碳原子、更优选5-100个碳原子、最优选6-100个碳原子的一价烃基,其中基团中还可含有杂原子,例如氧、硫、氮、磷、和卤素氟、氯、溴和碘。
虽然烯醇和其相应的含羰基化合物之间的互变异构平衡通常不是制备性反应,但由于含羰基化合物通常通过它们的烯醇型反应,如在本发明化合物制备中它们立即形成烯醇式,这种平衡必然存在。随着烯醇型反应生成所需产物,更多羰基型互变异构为烯醇型以保持平衡,直到全部含羰基化合物反应生成烯醇官能的硅氧烷。
上述合成优选在催化剂存在下进行。对于得自醇的含活性硅氧烷,可以使用几类催化剂。这些催化剂包括但不限于过渡金属催化剂、碱和路易斯酸。
可用于制备本发明含活性环硅氧烷的代表性过渡金属催化剂可列举但并不限于适于氢化硅烷化反应的催化剂。用于该反应(硅氢化作用和氢化硅烷化)的多种铂催化剂是已知的,并且此类铂催化剂可用于本发明的反应。以下例子仅仅用于说明性目的而不意图限制可使用的催化剂的范围。铂化合物可选自如US 3,159,601中所述的式(PtCl2烯烃)和H(PtCl3烯烃)表示的那些,引入此处作为参考。可用于本发明组合物的其它含铂材料为US 3,159,662中所述的氯化铂环丙烷络合物,引入此处作为参考。并且,含铂材料可为US 3,220,972中所述由氯铂酸与相对于每克铂多达2摩尔选自如下的一种所形成的络合物:醇、醚、醛和它们的混合物,引入此处作为参考。优选使用的催化剂公开在授予Karstedt的US 3,715,334、US 3,775,452和US 3,814,730中。其它铂的例子包括四氯铂酸二钾、铂金属和卤化铂。可能的铑催化剂包括但不限于三(二丁基硫化物)三氯化铑(III)、氯化三(三苯基膦)铑(I)、铑(0)、卤化铑,以及[(双烯烃)2RhCl]2型络合物,其中“双烯烃”指的是二烯烃或两个单烯烃。还可使用基于钯、镍、铼、钌、锇、铜、钴和铁的催化剂。另外可使用非均相催化剂,其是将如上所述的催化性金属或金属络合物担载在例如二氧化硅、氧化铝、碳、二氧化钛、氧化锆、硅藻土、粘土、沸石这样的固态有机或无机物或聚合基底上。其它相关背景可参照J.L.Spier,Homogeneous Catalysis of Hydrosilationby Transition Metals,in
Adyances in Organometallic Chemistry,第17卷,第407-447页,F.G.A.Stone和R.West编辑,Academic Press出版(New York,1979)。
可用于制备本发明含活性环硅氧烷的代表性碱催化剂可列举但并不限于离子化合物例如氢氧化物、含有一个或多个硅烷醇盐基的硅氧烷或聚硅氧烷、酰胺、具有锂、钠、钾、铷、铯、镁、钙、锶或钡反离子的醇盐。氨和胺这样的非离子碱也可用作催化剂。
可用于制备本发明含活性环硅氧烷的代表性路易斯酸催化剂可列举但并不限于:BF3、FeCl3、AlCl3、ZnCl2、ZnBr2或式(V)表示的路易斯酸催化剂,
MR9 sXt (V)
其中M为B、Al、Ga、In或Tl;R9相同或不同,独立地表示具有至少一个例如-CF3、-NO2或-CN的吸电子元素或基团、或具有至少两个卤素原子的6-14个碳原子的一价芳香族烃基;X为卤原子;s为1、2或3;并且t为0、1或2;条件是s+t=3,并且更优选式(VI)表示的路易斯酸
BR10 sXt (VI)
其中R10相同或不同,独立地表示具有至少一个例如-CF3、-NO2或-CN的吸电子元素或基团、或具有至少两个卤素原子的6-14个碳原子的一价芳香族烃基;X为卤原子;s为1、2或3;并且t为0、1或2;条件是s+t=3,最优选B(C6F5)3。
要指出的是,虽然起始环硅氧烷氢化物通常为没有支链的分子,在活性成分反应之前或在含活性硅氧烷生成后的水解可导致支链结构的形成,在式I和式II中分别通过下标q和t标出。
可用于形成本发明含活性环硅氧烷的代表性醇可列举但并不限于乙酰香兰酮、戊基乙醇酸烯丙酯、异戊基乙醇酸烯丙酯、α-戊基cinammyl醇、茴香醇、二苯乙醇酮、苄醇、水杨酸苄酯、1-丁醇、丁基化羟基甲苯、乳酸丁酯、2-叔丁基-5-甲基苯酚、2-叔丁基-6-甲基苯酚、香芹酚、香芹醇、4-香芹烯醇、雪松醇、鲸蜡醇、肉桂醇、香茅醇、邻甲酚、间甲酚、对甲酚、巴豆醇、十氢-2-萘酚、1-癸醇、1-癸烯-3-醇、9-癸烯-1-醇、苹果酸二乙酯、酒石酸二乙酯、二氢香芹醇、二氢月桂烯醇、2,6-二异丙基苯酚、聚二甲聚硅氧烷共聚多元醇、2,6-二甲氧基苯酚、1,1-二甲氧基-3,7-二甲基辛-7-醇、2,6-二甲基-4-庚醇、2,6-二甲基庚-2-醇、6,8-二甲基-2-壬醇、3,7-二甲基-2,6-辛二烯-1-醇、3,7-二甲基-1,6-辛二烯-3-醇、3,7-二甲基-1-辛醇、3,7-二甲基-3-辛醇、3,7-二甲基-6-辛烯-1-醇、3,7-二甲基-7-辛烯-1-醇、2,6-二甲基-2-庚醇(dimetol)、2-乙基葑醇、4-乙基愈创木酚、2-乙基-1-己醇、2-羟基苯甲酸乙酯、3-羟基丁酸乙酯、3-乙基-2-羟基-2-环戊-1-酮、2-羟基己酸乙酯、3-羟基己酸乙酯、乳酸乙酯、乙基麦芽酚、对乙基苯酚、水杨酸乙酯、丁香酚、法呢醇、小茴香醇、香叶醇、五乙酸葡萄糖酯、丙三醇、单硬脂酸甘油酯、愈创木酚、1-庚醇、2-庚醇、3-庚醇、顺式-4-庚烯醇、顺式-3-庚烯醇、正己醇、2-己醇、3-己醇、顺式-2-己烯醇、顺-3-己烯醇、反式-3-己烯醇、4-己烯醇、顺式-3-己烯基氢化肉桂基醇、2-羟基苯甲酸盐、2-羟基苯乙酮、4-羟基苄基醇、3-羟基-2-丁酮、羟基香茅醛、4-(4-羟基-3-甲氧基苯基)-2-丁酮、2-羟基-3-甲基-2-环戊烯-1-酮、4-对羟基苯基-2-丁酮、2-羟基-3,5,5-三甲基-2-环己烯酮、δ-异抗坏血酸、异冰片、异丁子香酚、异植醇、异丙醇、对异丙基苄醇、4-异丙基环己醇、3-异丙基苯酚、4-异丙基苯酚、2-异丙基苯酚、异蒲勒醇、月桂醇、芳樟醇、麦芽酚、薄荷醇、4-甲氧基苄基醇、2-甲氧基-4-甲基苯酚、2-甲氧基-4-丙基苯酚、2-甲氧基-4-乙烯基苯酚、α-甲基苄醇、2-甲基丁醇、3-甲基-2-丁醇、3-甲基-2-丁烯-1-醇、2-甲基-3-丁烯-2-醇、2,4-二羟基-3,6-二甲基苯甲酸甲酯、4-甲基-2,6-二甲氧基苯酚、N-3,7-二甲基-7-羟基亚辛基邻氨基苯甲酸甲酯、3-羟基己酸甲酯、6-甲基-5-庚烯-2-醇、2-甲基戊醇、3-甲基-3-戊醇、2-甲基-4-苯基丁-2-醇、2-甲基-3-苯基丙-2-醇、水杨酸甲酯、3-甲基-5-(2,2,3-三甲基-3-环戊烯-1-基)-4-戊烯-2-醇、2-甲基-2-乙烯基-5-(1-羟基-1-甲基乙基)-3,4-二氢呋喃、桃金娘烯醇、新橙皮苷二氢查耳酮、新薄荷醇、橙花醇、橙花叔醇、反式-2-顺式-6-壬二烯醇、1,3-壬二醇乙酸酯、nonadyl、2-壬醇、顺式-6-壬烯-1-醇、反式-2-壬烯-1-醇、壬醇、1-辛醇、2-辛醇、3-辛醇、顺式-3-辛烯-1-醇、顺式-2-辛烯-1-醇、反式-2-辛烯-1-醇、顺式-6-辛烯-1-醇、顺式-辛烯-1-醇、1-辛烯-3-醇、油醇、绿叶醇、3-戊醇、正戊醇、2-戊醇、1-戊烯-1-醇、顺式-2-戊烯-1-醇、紫苏子醇、2-苯氧乙醇阿拉伯半乳聚糖、β-苯乙醇、水杨酸苯乙酯、苯酚、苯乙醛甘油缩醛、3-苯基-1-戊醇、5-苯基-1-戊醇、1-苯基-1-戊醇、1-苯基-2-戊醇、1-苯基-3-甲基-1-戊醇、植醇、频哪醇、聚(亚烷基)二醇、聚山梨酸酯20、聚山梨酸酯60、聚山梨酸酯80、异戊烯醇、正丙醇、丙烯基乙基愈创木酚(propenyl guaethol)、丙二醇、2-丙基苯酚、4-丙基苯酚、间苯二酚、视黄醇、水杨醛、失水山梨糖醇单硬脂酸酯、山梨糖醇、硬脂醇、注射器醛(syringealdehyde)、α-萜品醇、四氢香叶醇、四氢芳樟醇、四氢月桂烯醇、百里酚、柠檬酸三乙酯、1,2,6-三羟基己烷、对-α,α-三甲基苄醇、2-(5,5,6-三甲基双环[2,2,1]庚-2-基)环己醇、5-(2,2,3-三甲基-3-环戊烯基)-3-甲基戊-2-醇、3,7,11-三甲基-2,6,10-十二碳三烯-1-醇、3,7,11-三甲基-1,6,10-十二碳三烯-3-醇、3,5,5-三甲基-1-己醇、10-十一碳烯-1-醇、十一醇、香草醛、邻香草醛、香草基丁基醚、4-乙烯基苯酚、2,5-二甲苯酚、2,6-二甲苯酚、3,5-二甲苯酚、2,4-二甲苯酚和木糖。
可用于形成本发明芳香环硅氧烷的代表性含羰基活性物或羰基活性成分可列举但并不限于4-乙酰氧基-3-戊基-四氢吡喃、肉桂酸烯丙酯、2-乙基丁酸烯丙酯、环己基丙酸烯丙酯、庚酸烯丙酯、己酸烯丙酯、异戊酸烯丙酯、壬酸烯丙酯、辛酸烯丙酯、苯氧基乙酸烯丙酯、苯乙酸烯丙酯、丙酸烯丙酯、乙酸α-戊基肉桂酯、辛酸戊酯、乙酸茴香酯、乙酸茴香基苯基酯、乙酸苄酯、乙酰乙酸苄酯、丁酸苄酯、肉桂酸苄酯、异丁酸苄酯、异戊酸苄酯、苯乙酸苄酯、丙酸苄酯、乙酸冰片酯、异戊酸冰片酯、戊酸冰片酯、乙酸丁酯、丁酸丁酯、丁酰乳酸丁酯、乙酸4-叔丁基环己基酯、庚酸丁酯、己酸丁酯、异丁酸丁酯、异戊酸丁酯、月桂酸丁酯、丙酸丁酯、硬脂酸丁酯、3-亚丁基苯并呋喃酮、2-甲基丁酸丁酯、10-十一碳烯酸丁酯、γ-丁内酯、乙酸香芹酯、丙酸香芹酯、乙酸石竹烯酯、乙酸柏木酯、反式-乙酸肉桂酯、反式-丁酸肉桂酯、肉桂酸肉桂酯、异丁酸肉桂酯、乙酸香茅醇酯、丁酸香茅醇酯、异丁酸香茅醇酯、丙酸香茅醇酯、戊酸香茅醇酯、乙酸环己基乙酯、乙酸环己酯、丁酸环己酯、异戊酸环己酯、丙酸环己酯、δ-癸内酯、ε-癸内酯、γ-癸内酯、4-decanolide、乙酸癸酯、丁酸癸酯、丙酸癸酯、马来酸二乙酯、癸二酸二乙酯、琥珀酸二乙酯、乙酸二氢香芹酯、二氢香豆素、乙酸二氢月桂烯酯、乙酸二氢-正-二环戊二烯酯、乙酸二氢松油酯、乙酸-3,7-二甲基-1,6-辛二烯-3-基酯、丙酸-3,7-二甲基-1,6-辛二烯-3-基酯、乙酸-3,7-二甲基辛-3-基酯、乙酸-α,α-二甲基苯乙酯、丁酸-α,α-二甲基苯乙酯、乙酸-6,10-二甲基-5,9-十一碳二烯-2-基酯、δ-十二内酯、ε-十二内酯、γ-十二内酯、乙酸乙酯、乙酰乙酸乙酯、6-乙酰氧基己酸乙酯、2-乙酰基-3-苯基丙酸乙酯、苯甲酰乙酸乙酯、乙酸2-乙基丁酯、丁酸乙酯、肉桂酸乙酯、环己基丙酸乙酯、癸酸乙酯、巴西酸亚乙酯、2-乙基-6,6-二甲基-2-环己烯羧酸乙酯、2,3-环氧丁酸乙酯、2-甲基-4-戊烯酸乙酯、庚酸乙酯、己酸乙酯、反式-3-己烯酸乙酯、乙酸2-乙基己酯、异丁酸乙酯、异戊酸乙酯、月桂酸乙酯、2-巯基丙酸乙酯、3-巯基丙酸乙酯、2-甲基丁酸乙酯、2-甲基戊酸乙酯、(甲硫基)乙酸乙酯、肉豆蔻酸乙酯、壬酸乙酯、辛酸乙酯、棕榈酸乙酯、苯基乙酸乙酯、3-苯基丙酸乙酯、3-苯基-2,3-环氧丁酸乙酯、3-苯基丙酸乙酯、丙酸乙酯、硬脂酸乙酯、2,3,6,6-四甲基-2-环己烯羧酸乙酯、对甲苯氧基乙酸乙酯、十一酸乙酯、戊酸乙酯、乙酸丁子香酯、乙酸葑酯、乙酸香叶酯、丁酸香叶酯、苯基乙酸香叶酯、丙酸香叶酯、苯基乙酸愈创木酯、乙酸愈创木酯、γ-庚内酯、乙酸庚酯、丁酸庚酯、异丁酸庚酯、ω-6-十六烯酯内酯、δ-己内酯、γ-己内酯、乙酸3-己烯酯、2-甲基丁酸顺式-3-己烯酯、顺式-3-己烯酸顺式-3-己烯酯、苯基乙酸顺式-3-己烯酯、乙酸-反式-2-己烯酯、乙酸己酯、丁酸己酯、己酸己酯、异丁酸己酯、丙酸己酯、2-甲基丁酸己酯、3-甲基丁酸己酯、苯基乙酸己酯、乙酸异戊酯、乙酰乙酸异戊酯、丁酸异戊酯、肉桂酸异戊酯、己酸异戊酯、异丁酸异戊酯、异戊酸异戊酯、月桂酸异戊酯、壬酸异戊酯、辛酸异戊酯、苯基乙酸异戊酯、丙酸异戊酯、乙酸异冰片酯、丙酸异冰片酯、乙酸异丁酯、丁酸异丁酯、肉桂酸异丁酯、己酸异丁酯、异丁酸异丁酯、2-甲基丁酸异丁酯、丙酸异丁酯、乙酸异丁子香酯、肉桂酸异丙酯、苯基乙酸异丁酯、乙酸异丙酯、丁酸异丙酯、异丁酸异丙酯、肉豆蔻酸异丙酯、棕榈酸异丙酯、苯基乙酸异丙酯、乙酸月桂酯、乙酸里哪酯、丁酸里哪酯、异戊酸里哪酯、内酯、乙酸酯、环己基羧酸酯、异戊酸酯、乙酸-4-甲氧基苄酯、丙酸-4-甲氧基苄酯、乙酸-2-甲氧基苯基酯、乙酸-2-甲氧基-4-(1-丙烯基)苯基酯、乙酸甲酯、乙酸-α-甲基苄酯、丁酸-α-甲基苄酯、丙酸-α-甲基苄酯、乙酸2-甲基丁酯、丁酸-2-甲基丁酯、异戊酸-2-甲基丁酯、2-甲基丁酸-3-甲基丁酯、2-甲基丁酸-2-甲基丁酯、对叔丁基苯基乙酸甲酯、丁酸甲酯、肉桂酸甲酯、癸酸甲酯、庚酸甲酯、己酸甲酯、异丁酸甲酯、异戊酸甲酯、月桂酸甲酯、N-2-甲基-3-(4-叔丁基苯基亚丙基)邻氨基苯甲酸甲酯、(甲硫基)乙酸甲酯、2-(甲硫基)丙酸甲酯、肉豆蔻酸甲酯、壬酸甲酯、辛酸甲酯、棕榈酸甲酯、乙酸4-(4-甲基-3-戊烯基)-3-环己烯基甲酯、2-甲基丁酸甲酯、乙酸2-甲基-6-亚甲基-7-辛烯-2-基酯、4-甲基戊酸甲酯、2-甲基戊酸甲酯、苯氧基乙酸甲酯、苯基乙酸4-甲基苯酯、乙酸2-甲基-3-苯基丙-2-基酯、3-苯基丙酸甲酯、丙酸甲酯、苯基乙酸2-甲基丙酯、苯基乙酸甲酯、乙酸2-甲基-3-苯基丙-2-基酯、硬脂酸甲酯、对甲苯氧基乙酸甲酯、9-十一碳烯酸甲酯、戊酸甲酯、乙酸桃金娘烯酯、乙酸橙花酯、丁酸橙花酯、异丁酸橙花酯、δ-壬内酯、γ-壬内酯、二乙酸1,3-壬二醇酯、乙酸壬酯、乙酸诺卜醇酯、八氢香豆素、γ-辛内酯、乙酸1-辛烯-3-基酯、丁酸1-辛烯-3-基酯、乙酸辛酯、丁酸辛酯、异丁酸辛酯、异戊酸辛酯、辛酸辛酯、丙酸辛酯、氧杂环十七-10-烯-2-酮、ω-十五内酯、乙酸戊酯、丁酸戊酯、己酸戊酯、辛酸戊酯、乙酸苯基乙酯、丁酸苯乙酯、肉桂酸苯乙酯、己酸苯乙酯、异丁酸苯乙酯、异戊酸苯乙酯、2-甲基丁酸苯乙酯、2-甲基丁酸苯乙酯、2-甲基丙酸苯乙酯、辛酸苯乙酯、苯基乙酸苯乙酯、丙酸苯乙酯、丙酸苯氧基乙酯、2-甲基丙酸2-苯氧基乙酯、丙酸3-苯基-2-丙烯酯、乙酸3-苯基丙酯、丁酸2-苯基丙酯、异丁酸2-苯基丙酯、异戊酸2-苯基丙酯、乙酸胡椒酯、异丁酸胡椒酯、乙酸异戊烯酯、乙酸丙酯、丁酸丙酯、庚酸丙酯、己酸丙酯、3-亚丙基苯并呋喃酮、异丁酸丙酯、丙酸丙酯、苯基乙酸丙酯、蔗糖八乙酸酯、乙酸萜品酯、丁酸萜品酯、异丁酸萜品酯、丙酸萜品酯、δ-壬内酯、乙酸四氢糠酯、丁酸四氢糠酯、丙酸四氢糠酯、乙酸四氢里哪酯、乙酸2,6,6,8-四甲基-三环[5,3,1,0(1.5)十一(udecan)-8-基]酯、乙酸对甲苯酯、异丁酸对甲苯酯、苯基乙酸对甲苯酯、三醋精、乙酰柠檬酸三丁酯、甘油三丁酸酯、三丙酸甘油酯、乙酸3,5,5-三甲基己酯、δ-十一内酯、γ-十一内酯、γ-戊内酯、乙酸香兰酯、异丁酸香草酯、乙酸1-乙烯基-2-(1-甲基丙基)环己酯和威士忌内酯。
也可用于形成本发明芳香环硅氧烷的代表性含羰基活性物可列举但并不限于这些化合物:丁醛、香茅醛、癸醛、顺式-4-癸烯醛、反式-4-癸烯醛、2,4-二甲基-3-环己烯-1-甲醛、2,6-二甲基-5-庚烯醛、3,7-二甲基辛醛、2-乙基丁醛、戊二醛、庚醛、顺式-4-庚烯醛、己醛、氢化肉桂醛、异丁醛、3-(对异丙基苯基)丙醛、异戊醛、月桂醛、2-甲基丁醛、2-甲基-3-(对异丙基苯基)丙醛、2-甲基戊醛、4-(4-甲基-3-戊烯基)-3-环己烯-1-甲醛、4-甲基苯基乙醛、3-(甲硫基)丁醛、2-甲基-4-(2,6,6-三甲基-2-环己烯-1-基)丁醛、2-甲基十一醛、壬醛、顺式-6-壬醛、辛醛、苯基乙醛、2-苯基丙醛、3-苯基丙醛、丙醛、对甲苯基乙醛、十三醛、2,4,6-三甲基-3-环己烯-1-甲醛、2,6,10-三甲基-9-十一醛、7-十一烯醛、8-十一烯醛、9-十一烯醛、10-十一烯醛、和戊醛。
可用于形成本发明芳香环硅氧烷的代表性含羰基化合物可列举但不限于以下化合物:乙酰茴香醚、1′-乙酰萘、2′-乙酰萘、丙酮、苯乙酮、2-乙酰氧基-2,5-二甲基-3(2H)呋喃酮、2-乙酰基环戊酮、4-乙酰基-1,1-二甲基-6-叔丁基茚满、7-乙酰基-1,1,3,4,4,6-六甲基茚满、2-乙酰基-2-噻唑啉、6-乙酰基-1,1,2,4,4,7-六甲基萘满、烯丙基α-紫罗兰酮、亚苄基丙酮、2,3-丁二酮、2-仲丁基环己酮、5-叔丁基-3,5-二硝基-2,6-二甲基苯乙酮、丁酰苯、樟脑、2-癸酮、3-癸酮、3-癸烯-2-酮、二氢香芹酮、二氢-β-紫罗兰酮、二氢茉莉酮、4,5-二氢-3(2H)-噻吩酮、2′,4′-二甲基苯乙酮、3,4-二甲基-1,2-环戊二酮、3,5-二甲基-1,2-环戊二酮、2,6-二甲基-4-庚酮、1,3-二苯基-2-丙酮、4-(1-乙氧基乙烯基)-3,3,5,5-四甲基环己酮、对乙基苯乙酮、乙基乙烯基酮、香叶基丙酮、2,3-庚二酮、2-庚酮、3-庚酮、4-庚酮、3,4-己二酮、3-己酮、4-己烯-3-酮、2-亚己基环戊酮、α-紫罗兰酮、β-紫罗兰酮、4-异丁基-2,6-二甲基-3,5-二硝基苯乙酮、异佛尔酮、6-异丙基十氢化-2-酰萘、顺式-茉莉酮、livescone、4-甲氧基苯乙酮、4-(对甲氧基苯基)-2-丁酮、4′-甲基苯乙酮、3-甲基-1,2-环己二酮、3-甲基-2-环己烯-1-酮、2-(2-(4-甲基-3-环己烯-1-基)丙基)环戊酮、3-甲基-2-环戊烯-1-酮、二氢茉莉酮酸甲酯、甲乙酮、2-甲基-3-庚酮、5-甲基-2-庚烯-4-酮、6-甲基-5-庚烯-2-酮、5-甲基-α-紫罗兰酮、1-(2-甲基-5-异丙基-2-环己烯基)-1-丙酮、4-甲基-2-戊酮、3-甲基-2-(2-戊烯基)-2-环戊烯-1-酮、4-甲基-1-苯基-2-戊酮、2-甲基四氢呋喃-3-酮、2-甲基四氢噻吩-3-酮、2-壬酮、3-壬酮、2-辛酮、3-辛酮、1-辛烯-3-酮、3-辛烯-2-酮、4-氧代异佛尔酮、2-十五烷酮、2,3-戊二酮、2-戊酮、3-戊酮、3-戊烯-2-酮、1-苯基-1,2-丙二酮、苯基乙基酮、长叶薄荷酮、2-十三烷酮、2,2,6-三甲基环己酮、4-(2,6,6-三甲基-2-环己烯-1-基)-3-甲基-3-丁烯-2-酮、2-十一烷酮和6-十一烷酮。
本发明的活性释放硅氧烷通过取代环甲硅烷基氢化物的氢制备。有机氢化硅氧烷具有式III或IV表示的结构:
其中R1和R2各自独立,选自氢和C1-C24一价烃基。v大于或等于3,w和u各自独立,且至少为1,条件是w+u必须等于或大于3。R3和R4各自独立,选自H、C1-C24一价烃基。使用的环氢化物可为多种大小和浓度的环的混合物。
环硅氧烷氢化物在上述条件下反应得到式I或式II的活性释放硅氧烷:
其中组分和下标满足前述定义和要求。在大多数使用条件下硅氧烷进行缓慢水解,在水解时释放出活性成分。这给例如化妆品和家用产品的多种不同有用组合物带来满意的效果。
本发明的活性释放化合物特别适于加入至个人护理产品以对产品产生持久、满意的效果。合适的应用包括但不限于除臭剂;止汗剂;护肤霜;面霜;头发护理产品,例如洗发剂、摩丝和定型发胶;驱虫剂;防护膏;剃须膏;剃须后用品;古龙香水;香水;加色化妆品,例如唇膏、粉底、腮红、化妆品(makeup)和睫毛油;以及其它化妆品制剂,其中已经加入其它含硅组分并需要特定效果。
少量本发明组合物加入到例如剃须液、古龙香水、花露水和香水的香味产品中可为这些产品带来宜人的持久香味。并且本发明的芳香环硅氧烷还可加入到其它需要用令人愉快的香味掩盖不良气味产品中,例如蜡和上光剂的家用清洁产品,例如蜡和上光剂的汽车清洁产品;清洁剂;织物涂料、颜料和漆。
另外,本发明的活性释放环硅氧烷可用于洗衣用途中,例如清洗添加剂、软化剂等,条件是本发明的活性释放环硅氧烷与其所加入的产品相容或能够使得与其所加入的产品相容。
实施例
实施例1
将香茅醇(5.89克,0.038摩尔)与环硅氧烷氢化物的混合物(2.0克,0.033摩尔)一起加入、混合并用硅醇钾官能化的硅氧烷(0.02克,0.015毫摩尔)处理。搅拌15分钟后将溶液在60℃加热18小时。通过在80℃/6毫米汞柱真空汽提1小时除去挥发物,得到产品(6.5克,91%)。
实施例2
将环硅氧烷氢化物的混合物(6.50克,0.108摩尔氢化物)加入到圆底烧瓶中。将香茅醇(18.58克,0.119摩尔)和10.9%的Pt(0)二乙烯基四甲基硅氧烷(28.9毫克溶液,126ppm Pt)溶液混溶并用45分钟滴加到氢化物中。观察到气体产生。然后将烧瓶在70℃加热68小时,然后通过在70℃/2毫米汞柱真空汽提3小时从淡黄色溶液中除去挥发物,得到22.77克产品(98%)。
实施例3
将环硅氧烷氢化物的混合物(7.75克,0.129摩尔氢化物)加入加热到70℃的圆底烧瓶中。将苯乙醇(17.32克,0.142摩尔)和10.9%的Pt(0)的二乙烯基四甲基硅氧烷(6.7毫克溶液,29ppm Pt)溶液混溶并用2小时滴加到氢化物中。观察到气体产生。淡黄色溶液在70℃搅拌5.5天,然后通过在80℃/1毫米汞柱真空汽提4小时从溶液中除去挥发物,得到23.14克产品(99.5%)。
实施例4
在圆底烧瓶中,将三(五氟苯基)硼烷(42.7毫克,83.4微摩尔)溶于丁子香酚(15.04克,0.092摩尔)中,得到嫩黄色溶液。滴加环硅氧烷氢化物的混合物(5克,0.083摩尔氢化物),使溶液浑浊。加入在7分钟完成,得到乳状混合物。搅拌30分钟后,观察到气体产生,在环境温度下总共搅拌14.5小时,混合物透明得到浅黄色溶液。在70℃/0.1毫米汞柱真空、5小时的系统下除去挥发物。过滤混合物,得到17.89浅黄色液体(97%)。
实施例5
在圆底烧瓶中,将2-异丙基苯酚(13.94克,0.102摩尔)和三(五氟苯基)硼烷(0.052克,101微摩尔)搅拌15分钟,得到淡黄绿色溶液。用1小时滴加硅氧烷氢化物的混合物(6.23克,0.102摩尔氢化物)。在加入过程中观察到氢气产生。将溶液在环境温度下搅拌40分钟,然后在50℃搅拌2.5小时。在70℃(3毫米汞柱)真空1.5小时的条件下除去挥发物,得到16.5克(82.5%)。
实施例6
在圆底烧瓶中,将苯乙醇(6.74克,0.055摩尔)和含Rh 1.36%的(″Bu2S)3RhCl3的乙醇(42毫克溶液,100ppm Rh)溶液在环境温度下一起搅拌。用75分钟滴加硅氧烷氢化物的混合物(3.37克,0.055摩尔氢化物),并再搅拌75分钟。将溶液加热到70℃,观察到气体产生。在70℃搅拌18.5小时后,溶液为深灰绿色。将烧瓶冷却到环境温度,并在70℃/1.2毫米汞柱真空、1.5小时条件下除去挥发物。滤出产品,得到7.65克产物(76.5%)。
实施例7
在圆底烧瓶中,将香茅醇(7.26克,0.046摩尔)和含1.36%Rh的(″Bu2S)3RhCl3的乙醇(35毫克溶液,100ppm Rh)溶液在环境温度下一起搅拌。用55分钟滴加硅氧烷氢化物的混合物(2.83克,0.046摩尔氢化物)。将溶液加热到70℃,并在几分钟内观察到气体生成。在70℃搅拌40小时后,将烧瓶冷却到环境温度,并在70℃/1-2毫米汞柱真空、1小时的条件下除去挥发物。滤出产品,得到7.85克暗灰色液态产物(78.5%)。
实施例8
在圆底烧瓶中,在环境温度下将苯乙酮(6.74克,0.056摩尔)和4.3%KOH当量的硅醇酸钾官能化的硅氧烷(0.073克,56微摩尔)溶于15毫升甲苯中。用30分钟滴加纯环硅氧烷氢化物1,3,5,7-四甲基环四硅氧烷(3.37克,0.056摩尔氢化物)。观察到气体生成。加入后,将溶液在环境温度搅拌2小时。然后将溶液加热到70℃并搅拌2小时。在70℃/5毫米汞柱用1.5小时除去挥发物。滤出产品,得到8.30克淡橙色液态产物(83%)。
实施例9
在圆底烧瓶中,将己醛(6.33克,0.063摩尔)、甲苯(15克)、三乙胺(0.012克,0.126毫摩尔)和10.9%的Pt(0)的二乙烯基四甲基硅氧烷(17毫克溶液,150ppm Pt)溶液在环境温度下搅拌10分钟。用15分钟滴加纯环硅氧烷氢化物1,3,5,7-四甲基环四硅氧烷。观察到气体生成,将混合物加热到70℃并保持在70℃24小时,然后再加入10.9%的Pt(0)在二乙烯基四甲基硅氧烷(加入17毫克溶液,合计300ppm Pt)溶液。将混合物在70℃再搅拌12小时,然后在70℃/3毫米汞柱汽提1.5小时,得到8.3克栗色液体(83%)。
实施例10-14(分别为实施例2、4、5、6和8的产物的水解)
水解的一般方法如下所示:
制备活性成分官能的硅氧烷(1.0克)、四氢呋喃(10克)和联苄内标(0.4克)的溶液。用气相色谱分析该溶液,然后加入0.50毫升1重量%的氢氧化钠水溶液(除了实施例9,其使用0.125毫升1%氢氧化钠水溶液)。将混合物搅拌,并定期取样进行气相色谱分析。表1-5分别示出实施例10-14测得的释放曲线。表1:得自实施例2产物的水解
表2:实施例4产物的水解
表3:实施例5产物的水解
表4:实施例6产物的水解
表5:实施例8产物的水解
时间(h) | 相对香茅醇浓度 |
0.055.2521.0029.5837.7645.6654.1178.05144.77219.80 | 0.3030.4320.5830.6210.6620.6630.6960.7230.7570.749 |
时间(h) | 相对丁子香酚浓度 |
0.001.586.1722.5047.00 | 0.2381.1541.1691.1631.189 |
时间(h) | 相对2-异丙基苯酚浓度 |
0.000.925.5021.8346.33 | 0.1631.3161.3511.3351.352 |
时间(h) | 相对苯乙醇浓度 |
0.002.256.8323.1727.3349.66 | 0.2300.9581.2051.3001.2261.302 |
时间(h) | 相对苯乙酮浓度 |
0.002.255.7520.6627.1749.7571.66140.92 | 0.3110.4480.5320.8990.9211.1211.1561.202 |
实施例15和16(分别为实施例3和8的产品的水解)
水解的一般方法如下所示:
将3.3厘米×3.3厘米的未处理棉布样本用每种材料浸透,以使得所有样本活性成分的摩尔当量相等。将每个样本放在小铝盘中,并将所有铝盘放在环境温度和湿度下同一房间内的无顶盒子中。每隔一定时间闻样品味道并评价味道强度(0=没有香味,5=与瓶中纯活性成分相同强度)。所得数据列于表6和7。在实施例15(表6)和实施例16(表7)中,均能够看出用本发明的硅氧烷衍生物处理的布在更长时间内释放出更强的气味。表6:织物样本的相对气味(实施例15)
表7:织物样品的相对气味(实施例16)
小时 | 对照组 | 实施例3的硅氧烷 |
0521.528.946.352.878.1164.3215.3237.1 | 5443333321 | 4444344231 |
小时 | 对照组 | 实施例8的硅氧烷 |
0.04.721.128.646.052.677.8164.0215.1236.8 | 5441100000 | 4433111111 |
Claims (21)
3.权利要求2的释放出醇或羰基化合物的硅氧烷,其中所述硅氧烷释放醇。
4.权利要求3的硅氧烷,其中所述释放的醇选自以下芳香醇:乙酰香兰酮、戊基乙醇酸烯丙酯、异戊基乙醇酸烯丙酯、α-戊基cinammyl醇、茴香醇、二苯乙醇酮、苄醇、水杨酸苄酯、1-丁醇、丁基化羟基甲苯、乳酸丁酯、2-叔丁基-5-甲基苯酚、2-叔丁基-6-甲基苯酚、香芹酚、香芹醇、4-香芹烯醇、雪松醇、鲸蜡醇、肉桂醇、香茅醇、邻甲酚、间甲酚、对甲酚、巴豆醇、十氢-2-萘酚、1-癸醇、1-癸烯-3-醇、9-癸烯-1-醇、苹果酸二乙酯、酒石酸二乙酯、二氢香芹醇、二氢月桂烯醇、2,6-二异丙基苯酚、聚二甲聚硅氧烷共聚多元醇、2,6-二甲氧基苯酚、1,1-二甲氧基-3,7-二甲基辛-7-醇、2,6-二甲基-4-庚醇、2,6-二甲基庚-2-醇、6,8-二甲基-2-壬醇、3,7-二甲基-2,6-辛二烯-1-醇、3,7-二甲基-1,6-辛二烯-3-醇、3,7-二甲基-1-辛醇、3,7-二甲基-3-辛醇、3,7-二甲基-6-辛烯-1-醇、3,7-二甲基-7-辛烯-1-醇、2,6-二甲基-2-庚醇、2-乙基葑醇、4-乙基愈创木酚、2-乙基-1-己醇、2-羟基苯甲酸乙酯、3-羟基丁酸乙酯、3-乙基-2-羟基-2-环戊烯-1-酮、2-羟基己酸乙酯、3-羟基己酸乙酯、乳酸乙酯、乙基麦芽酚、对乙基苯酚、水杨酸乙酯、丁香酚、法呢醇、小茴香醇、香叶醇、五乙酸葡萄糖酯、丙三醇、单硬脂酸甘油酯、愈创木酚、1-庚醇、2-庚醇、3-庚醇、顺式-4-庚烯醇、顺式-3-庚烯醇、正己醇、2-己醇、3-己醇、顺式-2-己烯醇、顺式-3-己烯醇、反式-3-己烯醇、4-己烯醇、顺式-3-己烯基氢化内桂基醇、2-羟基苯甲酸酯、2-羟基苯乙酮、4-羟基苄基醇、3-羟基-2-丁酮、羟基香茅醛、4-(4-羟基-3-甲氧基苯基)-2-丁酮、2-羟基-3-甲基-2-环戊烯-1-酮、4-对羟基苯基-2-丁酮、2-羟基-3,5,5-三甲基-2-环己烯酮、δ-异抗坏血酸、异冰片、异丁子香酚、异植醇、异丙醇、对异丙基苄醇、4-异丙基环己醇、3-异丙基苯酚、4-异丙基苯酚、2-异丙基苯酚、异蒲勒醇、月桂醇、芳樟醇、麦芽酚、薄荷醇、4-甲氧基苄基醇、2-甲氧基-4-甲基苯酚、2-甲氧基-4-丙基苯酚、2-甲氧基-4-乙烯基苯酚、α-甲基苄醇、2-甲基丁醇、3-甲基-2-丁醇、3-甲基-2-丁烯-1-醇、2-甲基-3-丁烯-2-醇、2,4-二羟基-3,6-二甲基苯甲酸甲酯、4-甲基-2,6-二甲氧基苯酚、N-3,7-二甲基-7-羟基亚辛基邻氨基苯甲酸甲酯、3-羟基己酸甲酯、6-甲基-5-庚烯-2-醇、2-甲基戊醇、3-甲基-3-戊醇、2-甲基-4-苯基丁-2-醇、2-甲基-3-苯基丙-2-醇、水杨酸甲酯、3-甲基-5-(2,2,3-三甲基-3-环戊烯-1-基)-4-戊烯-2-醇、2-甲基-2-乙烯基-5-(1-羟基-1-甲基乙基)-3,4-二氢呋喃、桃金娘烯醇、新橙皮苷二氢查耳酮、新薄荷醇、橙花醇、橙花叔醇、反式-2-顺式-6-壬二烯醇、1,3-壬二醇乙酸酯、nonadyl、2-壬醇、顺式-6-壬烯-1-醇、反式-2-壬烯-1-醇、壬醇、1-辛醇、2-辛醇、3-辛醇、顺式-3-辛烯-1-醇、顺式-2-辛烯-1-醇、反式-2-辛烯-1-醇、顺式-6-辛烯-1-醇、顺式-辛烯-1-醇、1-辛烯-3-醇、油醇、绿叶醇、3-戊醇、正戊醇、2-戊醇、1-戊烯-1-醇、顺式-2-戊烯-1-醇、紫苏子醇、2-苯氧基乙醇阿拉伯半乳聚糖、β-苯乙醇、水杨酸苯乙酯、苯酚、苯乙醛甘油缩醛、3-苯基-1-戊醇、5-苯基-1-戊醇、1-苯基-1-戊醇、1-苯基-2-戊醇、1-苯基-3-甲基-1-戊醇、植醇、频哪醇、聚(亚烷基)二醇、聚山梨酸酯20、聚山梨酸酯60、聚山梨酸酯80、异戊烯醇、正丙醇、丙烯基乙基愈创木酚、丙二醇、2-丙基苯酚、4-丙基苯酚、间苯二酚、视黄醇、水杨醛、失水山梨糖醇单硬脂酸酯、山梨糖醇、硬脂醇、注射器醛、α-萜品醇、四氢香叶醇、四氢芳樟醇、四氢月桂烯醇、百里酚、柠檬酸三乙酯、1,2,6-三羟基己烷、对-α,α-三甲基苄醇、2-(5,5,6-三甲基双环[2,2,1]庚-2-基)环己醇、5-(2,2,3-三甲基-3-环戊烯基)-3-甲基戊-2-醇、3,7,11-三甲基-2,6,10-十二碳三烯-1-醇、3,7,11-三甲基-1,6,10-十二碳三烯-3-醇、3,5,5-三甲基-1-己醇、10-十一碳烯-1-醇、十一醇、香草醛、邻香草醛、香草基丁基醚、4-乙烯基苯酚、2,5-二甲苯酚、2,6-二甲苯酚、3,5-二甲苯酚、2,4-二甲苯酚和木糖。
5.权利要求2的释放醇或羰基化合物的硅氧烷,其中所述硅氧烷释放羰基化合物。
6.权利要求5的硅氧烷,其中释放的羰基化合物选自4-乙酰氧基-3-戊基-四氢吡喃、肉桂酸烯丙酯、2-乙基丁酸烯丙酯、环己烷丙酸烯丙酯、庚酸烯丙酯、己酸烯丙酯、异戊酸烯丙酯、壬酸烯丙酯、辛酸烯丙酯、苯氧基乙酸烯丙酯、苯乙酸烯丙酯、丙酸烯丙酯、乙酸α-戊基肉桂酯、辛酸戊酯、乙酸茴香基酯、乙酸茴香基苯基酯、乙酸苄酯、乙酰乙酸苄酯、丁酸苄酯、肉桂酸苄酯、异丁酸苄酯、异戊酸苄酯、苯乙酸苄酯、丙酸苄酯、乙酸冰片酯、异戊酸冰片酯、戊酸冰片酯、乙酸丁酯、丁酸丁酯、丁酰乳酸丁酯、乙酸4-叔丁基环己基酯、庚酸丁酯、己酸丁酯、异丁酸丁酯、异戊酸丁酯、月桂酸丁酯、丙酸丁酯、硬脂酸丁酯、3-亚丁基苯并呋喃酮、2-甲基丁酸丁酯、10-十一碳烯酸丁酯、γ-丁内酯、乙酸香芹酯、丙酸香芹酯、乙酸石竹烯酯、乙酸柏木酯、反式-乙酸肉桂酯、反式-丁酸肉桂酯、肉桂酸肉桂酯、异丁酸肉桂酯、乙酸香茅醇酯、丁酸香茅醇酯、异丁酸香茅醇酯、丙酸香茅醇酯、戊酸香茅醇酯、乙酸环己基乙酯、乙酸环己酯、丁酸环己酯、异戊酸环己酯、丙酸环己酯、δ-癸内酯、ε-癸内酯、γ-癸内酯、4-decanolide、乙酸癸酯、丁酸癸酯、丙酸癸酯、马来酸二乙酯、癸二酸二乙酯、琥珀酸二乙酯、乙酸二氢香芹酯、二氢香豆素、乙酸二氢月桂烯酯、乙酸二氢-正-二环戊二烯酯、乙酸二氢松油酯、乙酸3,7-二甲基-1,6-辛二烯-3-基酯、丙酸3,7-二甲基-1,6-辛二烯-3-基酯、乙酸3,7-二甲基辛-3-基酯、乙酸α,α-二甲基苯乙酯、丁酸α,α-二甲基苯乙酯、乙酸6,10-二甲基-5,9-十一碳二烯-2-基酯、δ-十二内酯、ε-十二内酯、γ-十二内酯、乙酸乙酯、乙酰乙酸乙酯、6-乙酰氧基己酸乙酯、2-乙酰基-3-苯基丙酸乙酯、苯甲酰乙酸乙酯、2-乙基丁基乙酸酯、丁酸乙酯、肉桂酸乙酯、环己烷丙酸乙酯、癸酸乙酯、巴西酸亚乙酯、2-乙基-6,6-二甲基-2-环己烯羧酸乙酯、2,3-环氧丁酸乙酯、2-甲基-4-戊烯酸乙酯、庚酸乙酯、己酸乙酯、反式-3-己烯酸乙酯、乙酸2-乙基己基酯、异丁酸乙酯、异戊酸乙酯、月桂酸乙酯、2-巯基丙酸乙酯、3-巯基丙酸乙酯、2-甲基丁酸乙酯、2-甲基戊酸乙酯、(甲硫基)乙酸乙酯、肉豆蔻酸乙酯、壬酸乙酯、辛酸乙酯、棕榈酸乙酯、苯基乙酸乙酯、3-苯基丙酸乙酯、3-苯基-2,3-环氧丁酸乙酯、3-苯基丙酸乙酯、丙酸乙酯、硬脂酸乙酯、2,3,6,6-四甲基-2-环己烯羧酸乙酯、对甲苯氧基乙酸乙酯、十一酸乙酯、戊酸乙酯、乙酸丁子香酯、乙酸葑酯、乙酸香叶酯、丁酸香叶酯、苯基乙酸香叶酯、丙酸香叶酯、苯基乙酸愈创木酯、乙酸愈创木酯、γ-庚内酯、乙酸庚酯、丁酸庚酯、异丁酸庚酯、ω-6-十六烯酸内酯、δ-己内酯、γ-己内酯、乙酸3-己烯酯、顺式-2-甲基丁酸3-己烯酯、顺式-3-己烯酸顺式-3-己烯酯、苯基乙酸顺式-3-己烯酯、乙酸反式-2-己烯酯、乙酸己酯、丁酸己酯、己酸己酯、异丁酸己酯、丙酸己酯、2-甲基丁酸己酯、3-甲基丁酸己酯、苯基乙酸己酯、乙酸异戊酯、乙酰乙酸异戊酯、丁酸异戊酯、肉桂酸异戊酯、己酸异戊酯、异丁酸异戊酯、异戊酸异戊酯、月桂酸异戊酯、壬酸异戊酯、辛酸异戊酯、苯基乙酸异戊酯、丙酸异戊酯、乙酸异冰片酯、丙酸异冰片酯、乙酸异丁酯、丁酸异丁酯、肉桂酸异丁酯、己酸异丁酯、异丁酸异丁酯、2-甲基丁酸异丁酯、丙酸异丁酯、乙酸异丁子香酯、肉桂酸异丙酯、苯基乙酸异丁酯、乙酸异丙酯、丁酸异丙酯、异丁酸异丙酯、肉豆蔻酸异丙酯、棕榈酸异丙酯、苯基乙酸异丙酯、乙酸月桂酯、乙酸里哪酯、丁酸里哪酯、异戊酸里哪酯、内酯、乙酸酯、环己烷羧酸酯、异戊酸酯、乙酸4-甲氧基苄酯、丙酸4-甲氧基苄酯、乙酸2-甲氧基苯基酯、乙酸2-甲氧基-4-(1-丙烯基)苯基酯、乙酸甲酯、乙酸α-甲基苄酯、丁酸α-甲基苄酯、丙酸α-甲基苄酯、乙酸2-甲基丁酯、丁酸2-甲基丁酯、异戊酸2-甲基丁酯、2-甲基丁酸3-甲基丁酯、2-甲基丁酸2-甲基丁酯、对叔丁基苯基乙酸甲酯、丁酸甲酯、肉桂酸甲酯、癸酸甲酯、庚酸甲酯、己酸甲酯、异丁酸甲酯、异戊酸甲酯、月桂酸甲酯、N-2-甲基-3-(4-叔丁基苯基亚丙基)邻氨基苯甲酸甲酯、(甲硫基)乙酸甲酯、2-(甲硫基)丙酸甲酯、肉豆蔻酸甲酯、壬酸甲酯、辛酸甲酯、棕榈酸甲酯、乙酸4-(4-甲基-3-戊烯基)-3-环己烯基甲酯、2-甲基丁酸甲酯、乙酸2-甲基-6-亚甲基-7-辛烯-2-基酯、4-甲基戊酸甲酯、2-甲基戊酸甲酯、苯氧基乙酸甲酯、苯基乙酸4-甲基苯酯、乙酸2-甲基-3-苯基丙-2-基酯、3-苯基丙酸甲酯、丙酸甲酯、苯基乙酸2-甲基丙酯、苯基乙酸甲酯、乙酸2-甲基-3-苯基丙-2-基酯、硬脂酸甲酯、对甲苯氧基乙酸甲酯、9-十一碳烯酸甲酯、戊酸甲酯、乙酸桃金娘烯酯、乙酸橙花酯、丁酸橙花酯、异丁酸橙花酯、δ-壬内酯、γ-壬内酯、1,3-壬二醇二乙酸酯、乙酸壬酯、乙酸诺卜醇酯、八氢香豆素、γ-辛内酯、乙酸1-辛烯-3-基酯、丁酸1-辛烯-3-基酯、乙酸辛酯、丁酸辛酯、异丁酸辛酯、异戊酸辛酯、辛酸辛酯、丙酸辛酯、氧杂环十七-10-烯-2-酮、ω-十五内酯、乙酸戊酯、丁酸戊酯、己酸戊酯、辛酸戊酯、乙酸苯乙酯、丁酸苯乙酯、肉桂酸苯乙酯、己酸苯乙酯、异丁酸苯乙酯、异戊酸苯乙酯、2-甲基丁酸苯乙酯、2-甲基丁酸苯乙酯、2-甲基丙酸苯乙酯、辛酸苯乙酯、苯基乙酸苯乙酯、丙酸苯乙酯、丙酸苯氧基乙酯、2-甲基丙酸2-苯氧基乙酯、丙酸3-苯基-2-丙烯酯、乙酸3-苯基丙酯、丁酸2-苯基丙酯、异丁酸2-苯基丙酯、异戊酸2-苯基丙酯、乙酸胡椒酯、异丁酸胡椒酯、乙酸异戊烯酯、乙酸丙酯、丁酸丙酯、庚酸丙酯、己酸丙酯、3-亚丙基苯并呋喃酮、异丁酸丙酯、丙酸丙酯、苯基乙酸丙酯、蔗糖八乙酸酯、乙酸萜品酯、丁酸萜品酯、异丁酸萜品酯、丙酸萜品酯、δ-壬内酯、乙酸四氢糠酯、丁酸四氢糠酯、丙酸四氢糠酯、乙酸四氢里哪酯、乙酸2,6,6,8-四甲基-三环[5,3,1,0(1.5)十一-8-基]酯、乙酸对甲苯酯、异丁酸对甲苯酯、苯基乙酸对甲苯酯、三醋精、乙酰柠檬酸三丁酯、三丁酸甘油酯、甘油三丙酸酯、乙酸3,5,5-三甲基己酯、δ-十一内酯、γ-十一内酯、γ-戊内酯、乙酸香兰酯、异丁酸香草酯、乙酸1-乙烯基-2-(1-甲基丙基)环己酯和威士忌内酯、丁醛、香茅醛、癸醛、顺式-4-癸烯醛、反式-4-癸烯醛、2,4-二甲基-3-环己烯-1-甲醛、2,6-二甲基-5-庚烯醛、3,7-二甲基辛醛、2-乙基丁醛、戊二醛、庚醛、顺式-4-庚烯醛、己醛、氢化肉桂醛、异丁醛、3-(对异丙基苯基)丙醛、异戊醛、月桂醛、2-甲基丁醛、2-甲基-3-(对异丙基苯基)丙醛、2-甲基戊醛、4-(4-甲基-3-戊烯基)-3-环己烯-1-甲醛、4-甲基苯基乙醛、3-(甲硫基)丁醛、2-甲基-4-(2,6,6-三甲基-2-环己烯-1-基)丁醛、2-甲基十一醛、壬醛、顺式-6-壬醛、辛醛、苯基乙醛、2-苯基丙醛、3-苯基丙醛、丙醛、对甲苯基乙醛、十三醛、2,4,6-三甲基-3-环己烯-1-甲醛、2,6,10-三甲基-9-十一醛、7-十一烯醛、8-十一烯醛、9-十一烯醛、10-十一烯醛、和戊醛、乙酰茴香醚、1′-乙酰萘、2′-乙酰萘、丙酮、苯乙酮、2-乙酰氧基-2,5-二甲基-3(2H)呋喃酮、2-乙酰基环戊酮、4-乙酰基-1,1-二甲基-6-叔丁基茚满、7-乙酰基-1,1,3,4,4,6-六甲基茚满、2-乙酰基-2-噻唑啉、6-乙酰基-1,1,2,4,4,7-六甲基萘满、烯丙基α-紫罗兰酮、亚苄基丙酮、2,3-丁二酮、2-仲丁基环己酮、5-叔丁基-3,5-二硝基-2,6-二甲基苯乙酮、丁酰苯、樟脑、2-癸酮、3-癸酮、3-癸烯-2-酮、二氢香芹酮、二氢-β-紫罗兰酮、二氢茉莉酮、4,5-二氢-3(2H)-噻吩酮、2′,4′-二甲基苯乙酮、3,4-二甲基-1,2-环戊二酮、3,5-二甲基-1,2-环戊二酮、2,6-二甲基-4-庚酮、1,3-二苯基-2-丙酮、4-(1-乙氧基乙烯基)-3,3,5,5-四甲基环己酮、对乙基苯乙酮、乙基乙烯基酮、香叶基丙酮、2,3-庚二酮、2-庚酮、3-庚酮、4-庚酮、3,4-己二酮、3-己酮、4-己烯-3-酮、2-亚己基环戊酮、α-紫罗兰酮、β-紫罗兰酮、4-异丁基-2,6-二甲基-3,5-二硝基苯乙酮、异佛尔酮、6-异丙基十氢化-2-酰萘、顺式-茉莉酮、livescone、4-甲氧基苯乙酮、4-(对甲氧基苯基)-2-丁酮、4′-甲基苯乙酮、3-甲基-1,2-环己二酮、3-甲基-2-环己烯-1-酮、2-(2-(4-甲基-3-环己烯-1-基)丙基)环戊酮、3-甲基-2-环戊烯-1-酮、二氢茉莉酮酸甲酯、甲乙酮、2-甲基-3-庚酮、5-甲基-2-庚烯-4-酮、6-甲基-5-庚烯-2-酮、5-甲基-α-紫罗兰酮、1-(2-甲基-5-异丙基-2-环己烯基)-1-丙酮、4-甲基-2-戊酮、3-甲基-2-(2-戊烯基)-2-环戊烯-1-酮、4-甲基-1-苯基-2-戊酮、2-甲基四氢呋喃-3-酮、2-甲基四氢噻吩-3-酮、2-壬酮、3-壬酮、2-辛酮、3-辛酮、1-辛烯-3-酮、3-辛烯-2-酮、4-氧代异佛尔酮、2-十五烷酮、2,3-戊二酮、2-戊酮、3-戊酮、3-戊烯-2-酮、1-苯基-1,2-丙二酮、苯基乙基酮、长叶薄荷酮、2-十三烷酮、2,2,6-三甲基环己酮、4-(2,6,6-三甲基-2-环己烯-1-基)-3-甲基-3-丁烯-2-酮、2-十一烷酮和6-十一烷酮。
8.权利要求7的释放醇或羰基化合物的硅氧烷,其中所述硅氧烷释放醇。
9.权利要求8的硅氧烷,其中释放的醇选自以下芳香醇:乙酰香兰酮、戊基乙醇酸烯丙酯、异戊基乙醇酸烯丙酯、α-戊基cinammyl醇、茴香醇、二苯乙醇酮、苄醇、水杨酸苄酯、1-丁醇、丁基化羟基甲苯、乳酸丁酯、2-叔丁基-5-甲基苯酚、2-叔丁基-6-甲基苯酚、香芹酚、香芹醇、4-香芹烯醇、雪松醇、鲸蜡醇、肉桂醇、香茅醇、邻甲酚、间甲酚、对甲酚、巴豆醇、十氢-2-萘酚、1-癸醇、1-癸烯-3-醇、9-癸烯-1-醇、苹果酸二乙酯、酒石酸二乙酯、二氢香芹醇、二氢月桂烯醇、2,6-二异丙基苯酚、聚二甲聚硅氧烷共聚多元醇、2,6-二甲氧基苯酚、1,1-二甲氧基-3,7-二甲基辛-7-醇、2,6-二甲基-4-庚醇、2,6-二甲基庚-2-醇、6,8-二甲基-2-壬醇、3,7-二甲基-2,6-辛二烯-1-醇、3,7-二甲基-1,6-辛二烯-3-醇、3,7-二甲基-1-辛醇、3,7-二甲基-3-辛醇、3,7-二甲基-6-辛烯-1-醇、3,7-二甲基-7-辛烯-1-醇、2,6-二甲基-2-庚醇、2-乙基葑醇、4-乙基愈创木酚、2-乙基-1-己醇、2-羟基苯甲酸乙酯、3-羟基丁酸乙酯、3-乙基-2-羟基-2-环戊烯-1-酮、2-羟基己酸乙酯、3-羟基己酸乙酯、乳酸乙酯、乙基麦芽酚、对乙基苯酚、水杨酸乙酯、丁香酚、法呢醇、小茴香醇、香叶醇、五乙酸葡萄糖酯、丙三醇、单硬脂酸甘油酯、愈创木酚、1-庚醇、2-庚醇、3-庚醇、顺式-4-庚烯醇、顺式-3-庚烯醇、正己醇、2-己醇、3-己醇、顺式-2-己烯醇、顺-3-己烯醇、反式-3-己烯醇、4-己烯醇、顺式-3-己烯基氢化肉桂基醇、2-羟基苯甲酸酯、2-羟基苯乙酮、4-羟基苄基醇、3-羟基-2-丁酮、羟基香茅醛、4-(4-羟基-3-甲氧基苯基)-2-丁酮、2-羟基-3-甲基-2-环戊烯-1-酮、4-对羟基苯基-2-丁酮、2-羟基-3,5,5-三甲基-2-环己烯酮、δ-异抗坏血酸、异冰片、异丁子香酚、异植醇、异丙醇、对异丙基苄醇、4-异丙基环己醇、3-异丙基苯酚、4-异丙基苯酚、2-异丙基苯酚、异蒲勒醇、月桂醇、芳樟醇、麦芽酚、薄荷醇、4-甲氧基苄基醇、2-甲氧基-4-甲基苯酚、2-甲氧基-4-丙基苯酚、2-甲氧基-4-乙烯基苯酚、α-甲基苄醇、2-甲基丁醇、3-甲基-2-丁醇、3-甲基-2-丁烯-1-醇、2-甲基-3-丁烯-2-醇、2,4-二羟基-3,6-二甲基苯甲酸甲酯、4-甲基-2,6-二甲氧基苯酚、N-3,7-二甲基-7-羟基亚辛基邻氨基苯甲酸甲酯、3-羟基己酸甲酯、6-甲基-5-庚烯-2-醇、2-甲基戊醇、3-甲基-3-戊醇、2-甲基-4-苯基丁-2-醇、2-甲基-3-苯基丙-2-醇、水杨酸甲酯、3-甲基-5-(2,2,3-三甲基-3-环戊烯-1-基)-4-戊烯-2-醇、2-甲基-2-乙烯基-5-(1-羟基-1-甲基乙基)-3,4-二氢呋喃、桃金娘烯醇、新橙皮苷二氢查耳酮、新薄荷醇、橙花醇、橙花叔醇、反式-2-顺式-6-壬二烯醇、1,3-壬二醇乙酸酯、nonadyl、2-壬醇、顺式-6-壬烯-1-醇、反式-2-壬烯-1-醇、壬醇、1-辛醇、2-辛醇、3-辛醇、顺式-3-辛烯-1-醇、顺式-2-辛烯-1-醇、反式-2-辛烯-1-醇、顺式-6-辛烯-1-醇、顺式-辛烯-1-醇、1-辛烯-3-醇、油醇、绿叶醇、3-戊醇、正戊醇、2-戊醇、1-戊烯-1-醇、顺式-2-戊烯-1-醇、紫苏子醇、2-苯氧基乙醇阿拉伯半乳聚糖、β-苯乙醇、水杨酸苯乙酯、苯酚、苯乙醛甘油基缩醛、3-苯基-1-戊醇、5-苯基-1-戊醇、1-苯基-1-戊醇、1-苯基-2-戊醇、1-苯基-3-甲基-1-戊醇、植醇、频哪醇、聚(亚烷基)二醇、聚山梨酸酯20、聚山梨酸酯60、聚山梨酸酯80、异戊烯醇、正丙醇、丙烯基乙基愈创木酚、丙二醇、2-丙基苯酚、4-丙基苯酚、间苯二酚、视黄醇、水杨醛、失水山梨糖醇单硬脂酸酯、山梨糖醇、硬脂醇、注射器醛、α-萜品醇、四氢香叶醇、四氢芳樟醇、四氢月桂烯醇、百里酚、柠檬酸三乙酯、1,2,6-三羟基己烷、对-α,α-三甲基苄醇、2-(5,5,6-三甲基双环[2,2,1]庚-2-基)环己醇、5-(2,2,3-三甲基-3-环戊烯基)-3-甲基戊-2-醇、3,7,11-三甲基-2,6,10-十二碳三烯-1-醇、3,7,11-三甲基-1,6,10-十二碳三烯-3-醇、3,5,5-三甲基-1-己醇、10-十一碳烯-1-醇、十一醇、香草醛、邻香草醛、香草基丁基醚、4-乙烯基苯酚、2,5-二甲苯酚、2,6-二甲苯酚、3,5-二甲苯酚、2,4-二甲苯酚和木糖。
10.权利要求7的释放醇或羰基化合物的硅氧烷,其中所述硅氧烷释放羰基化合物。
11.权利要求10的硅氧烷,其中释放的羰基化合物选自4-乙酰氧基-3-戊基-四氢吡喃、肉桂酸烯丙酯、2-乙基丁酸烯丙酯、环己烷丙酸烯丙酯、庚酸烯丙酯、己酸烯丙酯、异戊酸烯丙酯、壬酸烯丙酯、辛酸烯丙酯、苯氧基乙酸烯丙酯、苯乙酸烯丙酯、丙酸烯丙酯、乙酸α-戊基肉桂酯、辛酸戊酯、乙酸茴香基酯、乙酸苯基茴香基酯、乙酸苄酯、乙酰乙酸苄酯、丁酸苄酯、肉桂酸苄酯、异丁酸苄酯、异戊酸苄酯、苯乙酸苄酯、丙酸苄酯、乙酸冰片酯、异戊酸冰片酯、戊酸冰片酯、乙酸丁酯、丁酸丁酯、丁酰乳酸丁酯、乙酸4-叔丁基环己基酯、庚酸丁酯、己酸丁酯、异丁酸丁酯、异戊酸丁酯、月桂酸丁酯、丙酸丁酯、硬脂酸丁酯、3-亚丁基苯并呋喃酮、2-甲基丁酸丁酯、10-十一碳烯酸丁酯、γ-丁内酯、乙酸香芹酯、丙酸香芹酯、乙酸石竹烯酯、乙酸柏木酯、反式-乙酸肉桂酯、反式-丁酸肉桂酯、肉桂酸肉桂酯、异丁酸肉桂酯、乙酸香茅醇酯、丁酸香茅醇酯、异丁酸香茅醇酯、丙酸香茅醇酯、戊酸香茅醇酯、乙酸环己烷乙酯、乙酸环己酯、丁酸环己酯、异戊酸环己酯、丙酸环己酯、δ-癸内酯、ε-癸内酯、γ-癸内酯、4-decanolide、乙酸癸酯、丁酸癸酯、丙酸癸酯、马来酸二乙酯、癸二酸二乙酯、琥珀酸二乙酯、乙酸二氢香芹酯、二氢香豆素、乙酸二氢月桂烯酯、乙酸二氢-正-二环戊二烯酯、乙酸二氢松油酯、乙酸3,7-二甲基-1,6-辛二烯-3-基酯、丙酸3,7-二甲基-1,6-辛二烯-3-基酯、乙酸3,7-二甲基辛-3-基酯、乙酸α,α-二甲基苯乙酯、丁酸α,α-二甲基苯乙酯、乙酸6,10-二甲基-5,9-十一碳二烯-2-基酯、δ-十二内酯、ε-十二内酯、γ-十二内酯、乙酸乙酯、乙酰乙酸乙酯、6-乙酰氧基己酸乙酯、2-乙酰基-3-苯基丙酸乙酯、苯甲酰乙酸乙酯、乙酸2-乙基丁酯、丁酸乙酯、肉桂酸乙酯、环己烷丙酸乙酯、癸酸乙酯、巴西酸亚乙酯、2-乙基-6,6-二甲基-2-环己烯羧酸乙酯、2,3-环氧丁酸乙酯、2-甲基-4-戊烯酸乙酯、庚酸乙酯、己酸乙酯、反式-3-己烯酸乙酯、乙酸2-乙基己酯、异丁酸乙酯、异戊酸乙酯、月桂酸乙酯、2-巯基丙酸乙酯、3-巯基丙酸乙酯、2-甲基丁酸乙酯、2-甲基戊酸乙酯、(甲硫基)乙酸乙酯、肉豆蔻酸乙酯、壬酸乙酯、辛酸乙酯、棕榈酸乙酯、苯基乙酸乙酯、3-苯基丙酸乙酯、3-苯基-2,3-环氧丁酸乙酯、3-苯基丙酸乙酯、丙酸乙酯、硬脂酸乙酯、2,3,6,6-四甲基-2-环己烯羧酸乙酯、对甲苯氧基乙酸乙酯、十一酸乙酯、戊酸乙酯、乙酸丁子香酯、乙酸葑酯、乙酸香叶酯、丁酸香叶酯、苯基乙酸香叶酯、丙酸香叶酯、苯基乙酸愈创木酯、乙酸愈创木酯、γ-庚内酯、乙酸庚酯、丁酸庚酯、异丁酸庚酯、ω-6-十六烯酸内酯、δ-己内酯、γ-己内酯、乙酸3-己烯酯、2-甲基丁酸顺式-3-己烯酯、顺式-3-己烯酸顺式-3-己烯酯、苯基乙酸顺式-3-己烯酯、乙酸反式-2-己烯酯、乙酸己酯、丁酸己酯、己酸己酯、异丁酸己酯、丙酸己酯、2-甲基丁酸己酯、3-甲基丁酸己酯、苯基乙酸己酯、乙酸异戊酯、乙酰乙酸异戊酯、丁酸异戊酯、肉桂酸异戊酯、己酸异戊酯、异丁酸异戊酯、异戊酸异戊酯、月桂酸异戊酯、壬酸异戊酯、辛酸异戊酯、苯基乙酸异戊酯、丙酸异戊酯、乙酸异冰片酯、丙酸异冰片酯、乙酸异丁酯、丁酸异丁酯、肉桂酸异丁酯、己酸异丁酯、异丁酸异丁酯、2-甲基丁酸异丁酯、丙酸异丁酯、乙酸异丁子香酯、肉桂酸异丙酯、苯基乙酸异丁酯、乙酸异丙酯、丁酸异丙酯、异丁酸异丙酯、肉豆蔻酸异丙酯、棕榈酸异丙酯、苯基乙酸异丙酯、乙酸月桂酯、乙酸里哪酯、丁酸里哪酯、异戊酸里哪酯、内酯、乙酸酯、环己基羧酸酯、异戊酸酯、乙酸4-甲氧基苄酯、丙酸4-甲氧基苄酯、乙酸2-甲氧基苯基酯、乙酸2-甲氧基-4-(1-丙烯基)苯基酯、乙酸甲酯、乙酸α-甲基苄酯、丁酸α-甲基苄酯、丙酸α-甲基苄酯、乙酸2-甲基丁酯、丁酸2-甲基丁酯、异戊酸2-甲基丁酯、2-甲基丁酸3-甲基丁酯、2-甲基丁酸2-甲基丁酯、对叔丁基苯基乙酸甲酯、丁酸甲酯、肉桂酸甲酯、癸酸甲酯、庚酸甲酯、己酸甲酯、异丁酸甲酯、异戊酸甲酯、月桂酸甲酯、N-2-甲基-3-(4-叔丁基苯基亚丙基)邻氨基苯甲酸甲酯、(甲硫基)乙酸甲酯、2-(甲硫基)丙酸甲酯、肉豆蔻酸甲酯、壬酸甲酯、辛酸甲酯、棕榈酸甲酯、乙酸4-(4-甲基-3-戊烯基)-3-环己烯基甲酯、2-甲基丁酸甲酯、乙酸2-甲基-6-亚甲基-7-辛烯-2-基酯、4-甲基戊酸甲酯、2-甲基戊酸甲酯、苯氧基乙酸甲酯、苯基乙酸4-甲基苯酯、乙酸2-甲基-3-苯基丙-2-基酯、3-苯基丙酸甲酯、丙酸甲酯、苯基乙酸2-甲基丙酯、苯基乙酸甲酯、乙酸2-甲基-3-苯基丙-2-基酯、硬脂酸甲酯、对甲苯氧基乙酸甲酯、9-十一碳烯酸甲酯、戊酸甲酯、乙酸桃金娘烯酯、乙酸橙花酯、丁酸橙花酯、异丁酸橙花酯、δ-壬内酯、γ-壬内酯、1,3-壬二醇二乙酸酯、乙酸壬酯、乙酸诺卜醇酯、八氢香豆素、γ-辛内酯、乙酸1-辛烯-3-基酯、丁酸1-辛烯-3-基酯、乙酸辛酯、丁酸辛酯、异丁酸辛酯、异戊酸辛酯、辛酸辛酯、丙酸辛酯、氧杂环十七-10-烯-2-酮、ω-十五内酯、乙酸戊酯、丁酸戊酯、己酸戊酯、辛酸戊酯、乙酸苯乙酯、丁酸苯乙酯、肉桂酸苯乙酯、己酸苯乙酯、异丁酸苯乙酯、异戊酸苯乙酯、2-甲基丁酸苯乙酯、2-甲基丁酸苯乙酯、2-甲基丙酸苯乙酯、辛酸苯乙酯、苯基乙酸苯乙酯、丙酸苯乙酯、丙酸苯氧基乙酯、2-甲基丙酸2-苯氧基乙酯、丙酸3-苯基-2-丙烯酯、乙酸3-苯基丙酯、丁酸2-苯基丙酯、异丁酸2-苯基丙酯、异戊酸2-苯基丙酯、乙酸胡椒酯、异丁酸胡椒酯、乙酸异戊烯酯、乙酸丙酯、丁酸丙酯、庚酸丙酯、己酸丙酯、3-亚丙基苯并呋喃酮、异丁酸丙酯、丙酸丙酯、苯基乙酸丙酯、蔗糖八乙酸酯、乙酸萜品酯、丁酸萜品酯、异丁酸萜品酯、丙酸萜品酯、δ-壬内酯、乙酸四氢糠酯、丁酸四氢糠酯、丙酸四氢糠酯、乙酸四氢里哪酯、乙酸2,6,6,8-四甲基-三环[5,3,1,0(1.5)十一-8-基]酯、乙酸对甲苯酯、异丁酸对甲苯酯、苯基乙酸对甲苯酯、三醋精、乙酰柠檬酸三丁酯、甘油三丁酸酯、三丙酸甘油酯、乙酸3,5,5-三甲基己酯、δ-十一内酯、γ-十一内酯、γ-戊内酯、乙酸香兰酯、异丁酸香草酯、乙酸1-乙烯基-2-(1-甲基丙基)环己酯和威士忌内酯、丁醛、香茅醛、癸醛、顺式-4-癸烯醛、反式-4-癸烯醛、2,4-二甲基-3-环己烯-1-甲醛、2,6-二甲基-5-庚烯醛、3,7-二甲基辛醛、2-乙基丁醛、戊二醛、庚醛、顺式-4-庚烯醛、己醛、氢化肉桂醛、异丁醛、3-(对异丙基苯基)丙醛、异戊醛、月桂醛、2-甲基丁醛、2-甲基-3-(对异丙基苯基)丙醛、2-甲基戊醛、4-(4-甲基-3-戊烯基)-3-环己烯-1-甲醛、4-甲基苯基乙醛、3-(甲硫基)丁醛、2-甲基-4-(2,6,6-三甲基-2-环己烯-1-基)丁醛、2-甲基十一醛、壬醛、顺式-6-壬烯醛、辛醛、苯基乙醛、2-苯基丙醛、3-苯基丙醛、丙醛、对甲苯基乙醛、十三醛、2,4,6-三甲基-3-环己烯-1-甲醛、2,6,10-三甲基-9-十一醛、7-十一烯醛、8-十一烯醛、9-十一烯醛、10-十一烯醛、和戊醛、乙酰茴香醚、1′-乙酰萘、2′-乙酰萘、丙酮、苯乙酮、2-乙酰氧基-2,5-二甲基-3(2H)呋喃酮、2-乙酰基环戊酮、4-乙酰基-1,1-二甲基-6-叔丁基茚满、7-乙酰基-1,1,3,4,4,6-六甲基茚满、2-乙酰基-2-噻唑啉、6-乙酰基-1,1,2,4,4,7-六甲基萘满、烯丙基α-紫罗兰酮、亚苄基丙酮、2,3-丁二酮、2-仲丁基环己酮、5-叔丁基-3,5-二硝基-2,6-二甲基苯乙酮、丁酰苯、樟脑、2-癸酮、3-癸酮、3-癸烯-2-酮、二氢香芹酮、二氢-β-紫罗兰酮、二氢茉莉酮、4,5-二氢-3(2H)-噻吩酮、2′,4′-二甲基苯乙酮、3,4-二甲基-1,2-环戊二酮、3,5-二甲基-1,2-环戊二酮、2,6-二甲基-4-庚酮、1,3-二苯基-2-丙酮、4-(1-乙氧基乙烯基)-3,3,5,5-四甲基环己酮、对乙基苯乙酮、乙基乙烯基酮、香叶基丙酮、2,3-庚二酮、2-庚酮、3-庚酮、4-庚酮、3,4-己二酮、3-己酮、4-己烯-3-酮、2-亚己基环戊酮、α-紫罗兰酮、β-紫罗兰酮、4-异丁基-2,6-二甲基-3,5-二硝基苯乙酮、异佛尔酮、6-异丙基十氢化-2-酰萘、顺式-茉莉酮、livescone、4-甲氧基苯乙酮、4-(对甲氧基苯基)-2-丁酮、4′-甲基苯乙酮、3-甲基-1,2-环己二酮、3-甲基-2-环己烯-1-酮、2-(2-(4-甲基-3-环己烯-1-基)丙基)环戊酮、3-甲基-2-环戊烯-1-酮、二氢茉莉酮酸甲酯、甲乙酮、2-甲基-3-庚酮、5-甲基-2-庚烯-4-酮、6-甲基-5-庚烯-2-酮、5-甲基-α-紫罗兰酮、1-(2-甲基-5-异丙基-2-环己烯基)-1-丙酮、4-甲基-2-戊酮、3-甲基-2-(2-戊烯基)-2-环戊烯-1-酮、4-甲基-1-苯基-2-戊酮、2-甲基四氢呋喃-3-酮、2-甲基四氢噻吩-3-酮、2-壬酮、3-壬酮、2-辛酮、3-辛酮、1-辛烯-3-酮、3-辛烯-2-酮、4-氧代异佛尔酮、2-十五烷酮、2,3-戊二酮、2-戊酮、3-戊酮、3-戊烯-2-酮、1-苯基-1,2-丙二酮、苯基乙基酮、长叶薄荷酮、2-十三烷酮、2,2,6-三甲基环己酮、4-(2,6,6-三甲基-2-环己烯-1-基)-3-甲基-3-丁烯-2-酮、2-十一烷酮和6-十一烷酮
12.作为反应产物的选自下式表示的硅氧烷的释放醇或羰基化合物的硅氧烷,
其中R1和R2各自独立地选自氢或一价C1-C24烃基,下标n至少为1或更大,而下标p和q各自独立地为0或正数,条件是n+p+q大于或等于3;R3和R4各自独立地选自氢或一价C1-C24烃基;下标r和u各自独立地至少为1或更大,而下标s和t各自独立地为0或正数,条件是r+s+t+u大于或等于3;并且Frag独立地为具有1-100个碳原子的一价烃基,其中所述反应产物具有权利要求1的硅氧烷的结构。
13.包括权利要求1硅氧烷的组合物。
14.包括权利要求2硅氧烷的组合物。
15.包括权利要求3硅氧烷的组合物。
16.包括权利要求5硅氧烷的组合物。
17.包括权利要求7硅氧烷的组合物。
18.包括权利要求8硅氧烷的组合物。
19.包括权利要求10硅氧烷的组合物。
20.包括权利要求1硅氧烷的产品。
21.基本上由权利要求1硅氧烷组成的组合物。
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DE102017123282A1 (de) | 2017-10-06 | 2019-04-11 | Henkel Ag & Co. Kgaa | Hydrolyselabile Silylenolether von Riechstoffketonen oder -aldehyden |
DE102017124612A1 (de) | 2017-10-20 | 2019-04-25 | Henkel Ag & Co. Kgaa | Hydrolyselabile Dienolsilylether von Riechstoffketonen oder -aldehyden |
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-
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-
2004
- 2004-12-01 WO PCT/US2004/040157 patent/WO2005066186A2/en not_active Application Discontinuation
- 2004-12-01 MX MXPA06006842A patent/MXPA06006842A/es active IP Right Grant
- 2004-12-01 EP EP10011306A patent/EP2281545A1/en not_active Withdrawn
- 2004-12-01 JP JP2006545697A patent/JP5128819B2/ja not_active Expired - Fee Related
- 2004-12-01 CN CN2013100965861A patent/CN103319521A/zh active Pending
- 2004-12-01 CA CA002548996A patent/CA2548996A1/en not_active Abandoned
- 2004-12-01 EP EP04812626A patent/EP1716159B1/en not_active Not-in-force
- 2004-12-01 BR BRPI0416716-3A patent/BRPI0416716A/pt not_active Application Discontinuation
- 2004-12-01 KR KR1020067011934A patent/KR101248700B1/ko not_active IP Right Cessation
- 2004-12-10 KR KR1020137000070A patent/KR20130018975A/ko not_active Application Discontinuation
- 2004-12-10 CN CNA2004800379826A patent/CN1893910A/zh active Pending
-
2007
- 2007-04-27 HK HK07104558.9A patent/HK1098159A1/xx not_active IP Right Cessation
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103717721A (zh) * | 2011-07-26 | 2014-04-09 | 花王株式会社 | 香料释放剂 |
CN103717721B (zh) * | 2011-07-26 | 2017-01-18 | 花王株式会社 | 香料释放剂 |
CN105900980A (zh) * | 2012-06-15 | 2016-08-31 | 大日本除虫菊株式会社 | 飞翔害虫驱避制品、及飞翔害虫驱避方法 |
CN105900980B (zh) * | 2012-06-15 | 2018-08-24 | 大日本除虫菊株式会社 | 飞翔害虫驱避制品、及飞翔害虫驱避方法 |
CN107432497A (zh) * | 2016-05-25 | 2017-12-05 | 浙江中烟工业有限责任公司 | 一种适用于加热非燃烧型烟草制品的功能香精 |
Also Published As
Publication number | Publication date |
---|---|
WO2005066186A2 (en) | 2005-07-21 |
JP2007514784A (ja) | 2007-06-07 |
HK1098159A1 (en) | 2007-07-13 |
EP1716159A2 (en) | 2006-11-02 |
EP2281545A1 (en) | 2011-02-09 |
JP5128819B2 (ja) | 2013-01-23 |
EP1716159B1 (en) | 2011-07-13 |
CA2548996A1 (en) | 2005-07-21 |
WO2005066186A3 (en) | 2005-08-25 |
WO2005066186A8 (en) | 2006-08-17 |
MXPA06006842A (es) | 2006-08-23 |
US7576170B2 (en) | 2009-08-18 |
CN103319521A (zh) | 2013-09-25 |
KR101248700B1 (ko) | 2013-03-29 |
KR20130018975A (ko) | 2013-02-25 |
KR20070003792A (ko) | 2007-01-05 |
BRPI0416716A (pt) | 2007-01-16 |
US20050136022A1 (en) | 2005-06-23 |
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