CN1791605A - 含具有季铵基的弹性硅烷和硅氧烷的乳液的制备方法 - Google Patents
含具有季铵基的弹性硅烷和硅氧烷的乳液的制备方法 Download PDFInfo
- Publication number
- CN1791605A CN1791605A CNA2004800133900A CN200480013390A CN1791605A CN 1791605 A CN1791605 A CN 1791605A CN A2004800133900 A CNA2004800133900 A CN A2004800133900A CN 200480013390 A CN200480013390 A CN 200480013390A CN 1791605 A CN1791605 A CN 1791605A
- Authority
- CN
- China
- Prior art keywords
- siloxanes
- emulsion
- microemulsion
- water
- chloro
- 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.)
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- -1 siloxanes Chemical class 0.000 title claims abstract description 123
- 239000000839 emulsion Substances 0.000 title claims abstract description 58
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims abstract description 28
- 150000004756 silanes Chemical class 0.000 title claims abstract description 18
- 238000000034 method Methods 0.000 title claims description 32
- 239000004530 micro-emulsion Substances 0.000 claims abstract description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 27
- 125000003700 epoxy group Chemical group 0.000 claims abstract description 18
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 239000000203 mixture Substances 0.000 claims description 53
- 239000003795 chemical substances by application Substances 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 17
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 15
- 229910000077 silane Inorganic materials 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 14
- 239000013543 active substance Substances 0.000 claims description 10
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 10
- 150000003867 organic ammonium compounds Chemical group 0.000 claims description 9
- 239000004593 Epoxy Substances 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 8
- XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 claims description 6
- 150000002894 organic compounds Chemical class 0.000 claims description 6
- PUVAFTRIIUSGLK-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1CO1 PUVAFTRIIUSGLK-UHFFFAOYSA-M 0.000 claims description 6
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 5
- 239000007762 w/o emulsion Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- CSPHGSFZFWKVDL-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-trimethylazanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC(O)CCl CSPHGSFZFWKVDL-UHFFFAOYSA-M 0.000 claims description 3
- 125000005908 glyceryl ester group Chemical group 0.000 claims description 3
- QIKIJFUVHGOQOK-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-dimethyl-octadecylazanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC(O)CCl QIKIJFUVHGOQOK-UHFFFAOYSA-M 0.000 claims description 2
- ZPNTYIBGYOQQSC-UHFFFAOYSA-M (3-chloro-2-hydroxypropyl)-trimethylazanium;bromide Chemical compound [Br-].C[N+](C)(C)CC(O)CCl ZPNTYIBGYOQQSC-UHFFFAOYSA-M 0.000 claims description 2
- 230000031709 bromination Effects 0.000 claims description 2
- 238000005893 bromination reaction Methods 0.000 claims description 2
- 238000005660 chlorination reaction Methods 0.000 claims description 2
- JMMAMAWBEJRFQN-UHFFFAOYSA-M trimethyl(oxiran-2-ylmethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1CO1 JMMAMAWBEJRFQN-UHFFFAOYSA-M 0.000 claims description 2
- 150000002924 oxiranes Chemical class 0.000 claims 2
- 150000003944 halohydrins Chemical group 0.000 abstract description 6
- 239000004094 surface-active agent Substances 0.000 abstract description 5
- 150000003856 quaternary ammonium compounds Chemical class 0.000 abstract description 2
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000003431 cross linking reagent Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 15
- 150000002118 epoxides Chemical group 0.000 description 14
- 125000000217 alkyl group Chemical group 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 229920001296 polysiloxane Polymers 0.000 description 11
- 239000003921 oil Substances 0.000 description 10
- 230000004087 circulation Effects 0.000 description 8
- 239000004033 plastic Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000002798 polar solvent Substances 0.000 description 7
- PLFJWWUZKJKIPZ-UHFFFAOYSA-N 2-[2-[2-(2,6,8-trimethylnonan-4-yloxy)ethoxy]ethoxy]ethanol Chemical compound CC(C)CC(C)CC(CC(C)C)OCCOCCOCCO PLFJWWUZKJKIPZ-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- HBXWUCXDUUJDRB-UHFFFAOYSA-N 1-octadecoxyoctadecane Chemical compound CCCCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCCCC HBXWUCXDUUJDRB-UHFFFAOYSA-N 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 235000014121 butter Nutrition 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- UYXTWWCETRIEDR-UHFFFAOYSA-N Tributyrin Chemical compound CCCC(=O)OCC(OC(=O)CCC)COC(=O)CCC UYXTWWCETRIEDR-UHFFFAOYSA-N 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 150000001721 carbon Chemical group 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 235000019197 fats Nutrition 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 238000007254 oxidation reaction Methods 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- FDCJDKXCCYFOCV-UHFFFAOYSA-N 1-hexadecoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOCCCCCCCCCCCCCCCC FDCJDKXCCYFOCV-UHFFFAOYSA-N 0.000 description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229960000583 acetic acid Drugs 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Polymers OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 235000011187 glycerol Nutrition 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 239000006210 lotion Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- HPILSDOMLLYBQF-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)butoxymethyl]oxirane Chemical compound C1OC1COC(CCC)OCC1CO1 HPILSDOMLLYBQF-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical class OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- 241000370738 Chlorion Species 0.000 description 2
- 241000282326 Felis catus Species 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- XJWSAJYUBXQQDR-UHFFFAOYSA-M dodecyltrimethylammonium bromide Chemical compound [Br-].CCCCCCCCCCCC[N+](C)(C)C XJWSAJYUBXQQDR-UHFFFAOYSA-M 0.000 description 2
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 2
- 230000001815 facial effect Effects 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 239000000976 ink Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- AHJCYBLQMDWLOC-UHFFFAOYSA-N n-methyl-n-silylmethanamine Chemical compound CN(C)[SiH3] AHJCYBLQMDWLOC-UHFFFAOYSA-N 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
- 239000002453 shampoo Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- MEIRRNXMZYDVDW-MQQKCMAXSA-N (2E,4E)-2,4-hexadien-1-ol Chemical compound C\C=C\C=C\CO MEIRRNXMZYDVDW-MQQKCMAXSA-N 0.000 description 1
- VTIBBOHXBURHMD-UHFFFAOYSA-N 1,2,3,4,4a,5,10,10a-octahydroanthracene Chemical compound C1=CCC2CC(CCCC3)C3=CC2=C1 VTIBBOHXBURHMD-UHFFFAOYSA-N 0.000 description 1
- WEERVPDNCOGWJF-UHFFFAOYSA-N 1,4-bis(ethenyl)benzene Chemical compound C=CC1=CC=C(C=C)C=C1 WEERVPDNCOGWJF-UHFFFAOYSA-N 0.000 description 1
- UWFRVQVNYNPBEF-UHFFFAOYSA-N 1-(2,4-dimethylphenyl)propan-1-one Chemical compound CCC(=O)C1=CC=C(C)C=C1C UWFRVQVNYNPBEF-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- NVJZKEHLSSKFAS-UHFFFAOYSA-N 1-hexadecyl-2-phenylbenzene Chemical compound CCCCCCCCCCCCCCCCC1=CC=CC=C1C1=CC=CC=C1 NVJZKEHLSSKFAS-UHFFFAOYSA-N 0.000 description 1
- IVIDDMGBRCPGLJ-UHFFFAOYSA-N 2,3-bis(oxiran-2-ylmethoxy)propan-1-ol Chemical compound C1OC1COC(CO)COCC1CO1 IVIDDMGBRCPGLJ-UHFFFAOYSA-N 0.000 description 1
- HDPLHDGYGLENEI-UHFFFAOYSA-N 2-[1-(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COC(C)COCC1CO1 HDPLHDGYGLENEI-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 1
- AIDLAEPHWROGFI-UHFFFAOYSA-N 2-methylbenzene-1,3-dicarboxylic acid Chemical compound CC1=C(C(O)=O)C=CC=C1C(O)=O AIDLAEPHWROGFI-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- WVRNUXJQQFPNMN-VAWYXSNFSA-N 3-[(e)-dodec-1-enyl]oxolane-2,5-dione Chemical compound CCCCCCCCCC\C=C\C1CC(=O)OC1=O WVRNUXJQQFPNMN-VAWYXSNFSA-N 0.000 description 1
- FHYNZKLNCPUNEU-UHFFFAOYSA-N 4-[(3,4-dihydroxyphenyl)methyl]-3-[(4-hydroxyphenyl)methyl]oxolan-2-one Chemical compound C1=CC(O)=CC=C1CC1C(=O)OCC1CC1=CC=C(O)C(O)=C1 FHYNZKLNCPUNEU-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000195940 Bryophyta Species 0.000 description 1
- CEPPGLZZYCAXGZ-UHFFFAOYSA-N CCCCC.[O] Chemical compound CCCCC.[O] CEPPGLZZYCAXGZ-UHFFFAOYSA-N 0.000 description 1
- YWAJAJKSWBALGM-UHFFFAOYSA-N CCCCCC.[O] Chemical compound CCCCCC.[O] YWAJAJKSWBALGM-UHFFFAOYSA-N 0.000 description 1
- JAYKZPAAEDTMRI-UHFFFAOYSA-N CCCCCCCC.[O] Chemical compound CCCCCCCC.[O] JAYKZPAAEDTMRI-UHFFFAOYSA-N 0.000 description 1
- QGCJTHLZNYNUKO-UHFFFAOYSA-N CN(C)C.N[SiH3] Chemical compound CN(C)C.N[SiH3] QGCJTHLZNYNUKO-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
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- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
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- 241001446187 Kermes Species 0.000 description 1
- JOOMLFKONHCLCJ-UHFFFAOYSA-N N-(trimethylsilyl)diethylamine Chemical compound CCN(CC)[Si](C)(C)C JOOMLFKONHCLCJ-UHFFFAOYSA-N 0.000 description 1
- SUZRRICLUFMAQD-UHFFFAOYSA-N N-Methyltaurine Chemical compound CNCCS(O)(=O)=O SUZRRICLUFMAQD-UHFFFAOYSA-N 0.000 description 1
- BONDTMGRIMOWRZ-UHFFFAOYSA-N N-ethylsilyl-N-methylmethanamine Chemical compound CC[SiH2]N(C)C BONDTMGRIMOWRZ-UHFFFAOYSA-N 0.000 description 1
- QCEYBMNLGBUVTQ-UHFFFAOYSA-N N-methyl-N-methylsilylmethanamine Chemical class C[SiH2]N(C)C QCEYBMNLGBUVTQ-UHFFFAOYSA-N 0.000 description 1
- DMLSHGGAICSCEF-UHFFFAOYSA-N N-methyl-N-phenylsilylmethanamine Chemical compound CN(C)[SiH2]c1ccccc1 DMLSHGGAICSCEF-UHFFFAOYSA-N 0.000 description 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
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- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 1
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- RCEAADKTGXTDOA-UHFFFAOYSA-N OS(O)(=O)=O.CCCCCCCCCCCC[Na] Chemical compound OS(O)(=O)=O.CCCCCCCCCCCC[Na] RCEAADKTGXTDOA-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
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- 239000002202 Polyethylene glycol Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241001615463 Trichogenes Species 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SHGUVJPXKKRMRP-UHFFFAOYSA-N [O].CCCC Chemical compound [O].CCCC SHGUVJPXKKRMRP-UHFFFAOYSA-N 0.000 description 1
- KOOADCGQJDGAGA-UHFFFAOYSA-N [amino(dimethyl)silyl]methane Chemical compound C[Si](C)(C)N KOOADCGQJDGAGA-UHFFFAOYSA-N 0.000 description 1
- GLQOALGKMKUSBF-UHFFFAOYSA-N [amino(diphenyl)silyl]benzene Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(N)C1=CC=CC=C1 GLQOALGKMKUSBF-UHFFFAOYSA-N 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003868 ammonium compounds Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
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- 229910052728 basic metal Inorganic materials 0.000 description 1
- 125000002511 behenyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CUBCNYWQJHBXIY-UHFFFAOYSA-N benzoic acid;2-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1.OC(=O)C1=CC=CC=C1O CUBCNYWQJHBXIY-UHFFFAOYSA-N 0.000 description 1
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- REZZEXDLIUJMMS-UHFFFAOYSA-M dimethyldioctadecylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCCCCCCCC REZZEXDLIUJMMS-UHFFFAOYSA-M 0.000 description 1
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- 230000013011 mating Effects 0.000 description 1
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- VLCAYQIMSMPEBW-UHFFFAOYSA-N methyl 3-hydroxy-2-methylidenebutanoate Chemical compound COC(=O)C(=C)C(C)O VLCAYQIMSMPEBW-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
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- ZHLULFBRTRVZTB-UHFFFAOYSA-N n-ethyl-n-triphenylsilylethanamine Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(N(CC)CC)C1=CC=CC=C1 ZHLULFBRTRVZTB-UHFFFAOYSA-N 0.000 description 1
- KAHVZNKZQFSBFW-UHFFFAOYSA-N n-methyl-n-trimethylsilylmethanamine Chemical compound CN(C)[Si](C)(C)C KAHVZNKZQFSBFW-UHFFFAOYSA-N 0.000 description 1
- WHBOEYVCMRSUPL-UHFFFAOYSA-N n-propan-2-yl-n-(2-trimethylsilylethyl)propan-2-amine Chemical compound CC(C)N(C(C)C)CC[Si](C)(C)C WHBOEYVCMRSUPL-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
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- JPMIIZHYYWMHDT-UHFFFAOYSA-N octhilinone Chemical compound CCCCCCCCN1SC=CC1=O JPMIIZHYYWMHDT-UHFFFAOYSA-N 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
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- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 125000005625 siliconate group Chemical group 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical compound O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- 239000000516 sunscreening agent Substances 0.000 description 1
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- 239000004753 textile Substances 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
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- UYPYRKYUKCHHIB-UHFFFAOYSA-N trimethylamine N-oxide Chemical compound C[N+](C)(C)[O-] UYPYRKYUKCHHIB-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YVWPNDBYAAEZBF-UHFFFAOYSA-N trimethylsilylmethanamine Chemical compound C[Si](C)(C)CN YVWPNDBYAAEZBF-UHFFFAOYSA-N 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
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
- WMYJOZQKDZZHAC-UHFFFAOYSA-H trizinc;dioxido-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]P([O-])([S-])=S.[O-]P([O-])([S-])=S WMYJOZQKDZZHAC-UHFFFAOYSA-H 0.000 description 1
- 229960004418 trolamine Drugs 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
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- 229930003231 vitamin Natural products 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
Classifications
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
-
- 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
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/046—Aerosols; Foams
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
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- A—HUMAN NECESSITIES
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- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
- A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
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- 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
- C08G77/04—Polysiloxanes
- 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
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
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- 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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- C08J2383/00—Characterised by the use 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; Derivatives of such polymers
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Abstract
通常通过使具有环氧基或卤代醇基的有机季铵化合物与具有氨基的硅烷或硅氧烷反应制备水包油(O/W)和油包水(W/O)的乳液与微乳液,所述乳液和微乳液含有优选具有季铵基的弹性硅烷或硅氧烷。该反应在含有交联剂和表面活性剂的含水极性相中进行。该乳液和微乳液特别用于处理头发、皮肤或腋下。
Description
[0001]本发明涉及制备水包油型(O/W)乳液和微乳液以及油包水型(W/O)乳液和微乳液的方法,所述乳液和微乳液含有具有氮原子,优选季铵基的弹性硅烷或硅氧烷作为油相。特别地,通过使具有环氧基或卤代醇基的有机季铵化合物与具有氨基的硅烷或硅氧烷反应,获得优选的弹性硅烷或硅氧烷;和在交联剂与表面活性剂存在下,在含水极性相中进行所述反应。
[0002]2002年11月27日提交的标题为Method of MakingEmulsions Containing Quaternary Ammonium Functional Silanesand Siloxanes的悬而未决的美国申请序列No.10/306012;2001年10月24日提交的标题为Silicon Based Quaternary AmmoniumFunctional Compositions and Methods for Maaking Them的悬而未决的美国申请序列No.10/001760,后于2002年11月19日授权的美国专利6482969;和2001年10月24日提交的标题为Silicon BasedQuaternary Ammonium Functional Compositions and TheirApplications的美国申请序列No.10/001753全部受让于与本申请相同的受让人,且在此通过参考引入。
[0003]如10/306012申请、6482969专利和10/001753申请中所述,季铵官能的硅烷和季铵官能的硅氧烷在纺织品工业和在个人护理领域中具有各种商业应用。它们也可用作抗菌剂、用于改性填料、纤维和表面中;用作增稠剂;和用作调节剂。
[0004]在许多这些应用和用途中,常常需要提供乳液或微乳液形式的季铵官能的硅烷和季铵官能的硅氧烷。当要求乳液时,常规的常识表明,应当结合季铵官能的硅烷或季铵官能的硅氧烷与表面活性剂和水,并混合直到形成乳液。
[0005]对于季铵官能的硅烷和硅氧烷的最终用户来说,常常不便的是制备乳液和微乳液,因此提供新的和较简单的制备乳液的方法是有益的。
[0006]尽管10/001753申请公开了制备含季铵官能硅烷和季铵官能硅氧烷的乳液的方法,但该方法包括采用常规的常识,即使季铵官能的硅烷或硅氧烷结合表面活性剂和水,并混合,直到形成乳液。
[0007]然而,本申请的方法显著不同于在10/001753申请中所使用的方法在于,实际上使用一起反应形成季铵官能的硅烷或硅氧烷的单体作为起始材料来在乳液中合成季铵官能的硅烷或硅氧烷,而不是使用季铵官能的硅烷或硅氧烷。另外,存在于本发明乳液内的季铵官能的硅烷或硅氧烷是弹性,这与10/001753申请中的乳液内形成的流体不同。
[0008]本发明涉及制备一些水包油(O/W)或油包水(W/O)乳液和微乳液的方法,所述乳液和微乳液含有有机硅组分作为油相。特别地,这些乳液和微乳液含有弹性硅烷或硅氧烷,优选在其分子内具有季铵基团的弹性硅烷或硅氧烷作为油相。通过在分散于(v)含水极性相内的(iii)交联剂、(iv)表面活性剂存在下,使(i)在其分子内具有环氧基或卤代醇基的有机季铵化合物与(ii)在其分子内具有氨基的硅烷或硅氧烷反应,获得具有季铵基的弹性硅烷或硅氧烷。
[0009]具有环氧基和卤代醇基的合适季铵化合物的代表性实例分别是缩水甘油基三甲基氯化铵和(3-氯-2-羟基丙基)三甲基氯化铵。含水极性相可以是水或水和极性有机化合物如1,2-己二醇的混合物。这些乳液和微乳液可用作人体的头发、皮肤和腋下的处理剂。
[0010]根据下述详细说明,本发明的这些和其它特征将变得显而易见。
发明内容
[0011]如上所述,本发明涉及水包油型(O/W)和油包水(W/O)乳液和微乳液,所述乳液和微乳液含有弹性硅烷或硅氧烷,优选在其分子内具有季铵基的弹性硅烷或硅氧烷作为油相。通过在分散于(v)含水极性相内的(iii)交联剂、(iv)表面活性剂存在下,使(i)在其分子内具有环氧基或卤代醇基的有机季铵化合物与(ii)在其分子内具有氨基的硅烷或硅氧烷反应,获得具有季铵基的弹性硅烷或硅氧烷。根据另一不那么优选的方法,如实施例2所示,可使用仅仅组分(ii)-(v)并省去组分(i),获得含氮的弹性。
含季铵基的硅烷和硅氧烷
[0012]这些物质基本上是通过结合组分(i)和(ii)获得的反应产物。可在10/001753和10/001760申请中详细地找到就其结构而言的组成的详细描述。
[0013]一般来说,为了此处的目的,这些物质可描述为在其分子内具有至少一个含键合到硅上的基团(例如-R-Z-Q)的单元的硅烷或硅氧烷,其中:
R是二价烃基如亚乙基;
Z是基团例如-N(Q1);和
Q是基团例如-CH(R)CH(OH)YN+(R1)(R2)(R3)X-;
其中:
Q1是单价烃基如甲基;
Y是二价烃基如亚乙基;
X是抗衡离子如氯离子Cl-;
和R1-R3是单价烃基如甲基。
[0014]至少一个特别优选的-R-Z-Q基团的代表性实例是
CH2CH(OH)CH2N+(CH3)2(CH3)Cl-。
具有环氧基团的有机季铵化合物
[0015]关于这类化合物通式的详细描述,可参考10/001753和10/001760申请。可充分地说,为了此处的目的,这类有用化合物的具体实例是缩水甘油基三甲基氯化铵和缩水甘油基三甲基溴化铵。尽管也可使用非端基环氧化物,但端基环氧化物,如此处所述的化合物通常是优选的。也可使用环氧化物的结合以及环氧化物与如下所述的卤代醇的结合。
具有卤代醇基的有机季铵化合物
[0016]关于这类化合物通式的详细描述,可再次参考10/001753和10/001760申请。可充分地说,为了此处的目的,这类有用化合物的具体实例是:(3-氯-2-羟基丙基)三甲基氯化铵ClCH2CH(OH)CH2N(CH3)3Cl、(3-氯-2-羟基丙基)二甲基十二烷基氯化铵、(3-氯-2-羟基丙基)二甲基十八烷基氯化铵、(3-氯-2-羟基丙基)三甲基溴化铵和(3-氯-2-羟基丙基)二甲基十二烷基溴化铵和(3-氯-2-羟基丙基)二甲基十八烷基溴化铵。
[0017]尽管也可使用非端基的卤代醇,但端基卤代醇,如此处所述的化合物通常是优选的。也可使用卤代醇的结合以及卤代醇与以上所述的环氧化物的结合。
具有氨基的硅烷和硅氧烷
[0018]此处使用的含氨基的硅烷通常包括R3SiR类有机硅单体,其中在分子内的R基可由含1-6个碳原子的烷基组成,如甲基、乙基、丙基、异丙基、丁基和异丁基;芳基如苯基;或R基可包括氨基,如氨乙基、氨丙基、氨基异丁基、氨乙基氨丙基和氨乙基氨基异丁基;条件是在硅烷内的至少一个R是氨基。
[0019]适于此处使用的含氨基的硅烷的一些代表性实例包括氨甲基三甲基硅烷、氨基三甲基硅烷、(苄基甲基氨基)三乙基硅烷、二乙基氨基甲基三甲基硅烷、二乙基氨基三甲基硅烷、二乙基氨基三苯基硅烷、二异丙基氨基三甲基硅烷、二甲基氨基三乙基硅烷、二甲基氨基三甲基硅烷、苯基甲基双(二甲基氨基)硅烷、四(二甲基氨基)硅烷、三正己基甲硅烷基胺、三甲基氨基硅烷、三苯基氨基硅烷、三(二甲基氨基)乙基硅烷、三(二甲基氨基)甲基硅烷和三(二甲基氨基)苯基硅烷。
[0020]具有氨基的硅氧烷的一些实例包括数均分子量为1000-100000的那些硅氧烷聚合物和共聚物,特别是数均分子量为5000-50000的那些,如氨丙基封端的聚二甲基硅氧烷和三甲基甲硅烷基封端的二甲基硅氧烷共聚物。基于存在于硅氧烷内的伯和仲氨基的氨基氮,硅氧烷应当还平均含有0.1-2.0毫当量的氨基官能度/g硅氧烷。氨基可以以氨乙基、氨丙基、氨基异丁基、氨乙基氨丙基或氨乙基氨基异丁基的形式存在于硅氧烷内。关于此处可使用的含氨基的这些和类似硅氧烷的细节,可参考最近授权的美国专利6475974(2002年11月5日)。
交联剂
[0021]此处使用的交联剂是含至少两个环氧基的有机环氧化物,即二环氧化物,其中包括例如乙二醇二缩水甘油醚、二甘醇二缩水甘油醚、聚乙二醇二缩水甘油醚、甘油二缩水甘油醚、三缩水甘油醚、丙二醇二缩水甘油醚、丁二醇二缩水甘油醚;1,2,3,4-二环氧基丁烷、1,2,4,5-二环氧基戊烷、1,2,5,6-二环氧基己烷、1,2,7,8-二环氧基辛烷、1,3-二乙烯基苯二环氧化物、1,4-二乙烯基苯二环氧化物、4,4′-亚异丙基二苯酚二缩水甘油醚和氢醌二缩水甘油醚之类的组分。
[0022]此处也可使用其它烷烃多元醇的聚缩水甘油醚、聚(亚烷基二醇)的聚缩水甘油醚、二环氧烷烃、二环氧芳烷烃和聚苯酚聚缩水甘油醚。
[0023]以下示出了含至少两个环氧基的两种特别优选的有机环氧化物,其中n是决定环氧化物分子量的正整数。
丁二醇二缩水甘油醚
聚(丙二醇)二缩水甘油醚
[0024]当需要使用含至少两个环氧基的环氧官能的聚硅氧烷代替含至少两个环氧基的有机环氧化物时,可使用以下所示的通式结构的合适的环氧官能的聚硅氧烷,其中x表示1或更大的整数。视需要,可使用沿着聚硅氧烷聚合物链含有环氧侧基的环氧官能的聚硅氧烷。
环氧丙氧基丙基封端的聚二甲基硅氧烷
[0025]这种环氧官能的聚硅氧烷是本领域公知的且可商购于例如Dow Corning Corporation,Midland,Michigan USA之类的公司。典型地,这种聚硅氧烷的粘度范围为1至约200厘沲(mm2/s)和重均分子量为约300-6000。
[0026]可使用氯代醇来替代环氧化物或者与环氧化物结合使用。正如本领域所公知的,氯代醇是含有氯和羟基二者的化合物,和在一些情况下,氯代醇定义为在相邻碳原子上具有氯和羟基的化合物,即:
[0027]氯代醇可通过碱的作用转化成环氧化物。在氢氧根离子存在下,小量比例的醇以醇盐形式存在,所述醇盐从相邻碳原子上取代氯离子,产生环醚。
[0028]另外,有机环氧化物和含有一个环氧基的环氧官能的聚硅氧烷也可包括作为任选的组分,为的是控制交联密度和弹性的总分子量。
[0029]视需要,也可使用其它类型的交联剂,如丙烯酸羟烷酯,所述丙烯酸羟烷酯的一些实例是丙烯酸羟乙酯和甲基丙烯酸羟乙酯,以及异氰酸酯,如己二异氰酸酯。
表面活性剂
[0030]表面活性剂可包括非离子表面活性剂、阳离子表面活性剂、阴离子表面活性剂、两性表面活性剂或这些表面活性剂的混合物。然而,最优选非离子表面活性剂。
[0031]一般来说,非离子表面活性剂应当是含有非硅原子的非离子乳化剂。最优选的是乙氧化醇R4-(OCH2CH2)aOH,特别是乙氧化脂肪醇。乙氧化脂肪醇典型地含有连接到脂肪烃残基R4(其含有约8至约20个碳原子),如月桂基(C12)、鲸蜡基(C16)和硬脂基(C18)上的特征基团-(OCH2CH2)aOH。尽管“a”值范围可以是1至约100,但其数值典型地在约12至约40范围内。
[0032]合适的非离子表面活性剂的一些实例是聚氧乙烯(4)月桂醚、聚氧乙烯(5)月桂醚、聚氧乙烯(23)月桂醚、聚氧乙烯(2)鲸蜡醚、聚氧乙烯(10)鲸蜡醚、聚氧乙烯(20)鲸蜡醚、聚氧乙烯(2)硬脂醚、聚氧乙烯(10)硬脂醚、聚氧乙烯(20)硬脂醚、聚氧乙烯(21)硬脂醚、聚氧乙烯(100)硬脂醚、聚氧乙烯(2)油醚和聚氧乙烯(10)油醚。这些和其它的乙氧化脂肪醇可以商标和商品名如ALFONIC、BRIJ、GENAPOL、NEODOL、SURFONIC、TERGITOL和TRYCOL商购得到。也可使用乙氧化烷基苯酚,如以商标TRITON销售的乙氧化辛基苯酚。
[0033]可用于本发明的阳离子表面活性剂包括在分子内含荷正电的季铵亲水部分的化合物,如用R′R″RR′N+X-表示的季铵盐,其中R′、R″、R和R′是含1-30个碳原子的烷基,或者衍生于牛油、椰子油或大豆的烷基;和X是卤素,即氯或溴。最优选用R′R″N+(CH3)2X-表示的二烷基二甲基铵盐,其中R′和R″是含12-30个碳原子的烷基,或衍生于牛油、椰子油或大豆的烷基;和X是卤素。也可使用单烷基三甲基铵盐,且用R′N+(CH3)3X-表示,其中R′是含12-30个碳原子的烷基,或衍生于牛油、椰子油或大豆的烷基;和X是卤素。
[0034]一些代表性的季铵盐是十二烷基三甲基溴化铵(DTAB)、双十二烷基二甲基溴化铵、双十六烷基二甲基氯化铵、双十六烷基二甲基溴化铵、双十八烷基二甲基氯化铵、双二十烷基二甲基氯化铵、双二十二烷基二甲基氯化铵、双椰子油二甲基氯化铵、双牛油二甲基氯化铵和双牛油二甲基溴化铵。这些和其它季铵盐以商品名如ADOGEN、ARQUAD、TOMAH和VARIQUAT商购得到。
[0035]在可使用的各类阴离子表面活性剂当中,可提及磺酸及其盐衍生物;碱金属磺基琥珀酸盐;磺化的脂肪酸缩水甘油酯如磺化的椰子油酸单缩水甘油酯;磺化单价醇酯的盐如油基异硫羰酸酯钠;氨基磺酸的酰胺如油基甲基氨基乙磺酸的钠盐;脂肪酸腈的磺化产物如棕榈腈磺酸盐;磺化芳烃如α-萘单磺酸钠;萘磺酸与甲醛的缩合产物;八氢蒽磺酸钠;碱金属烷基硫酸盐如月桂(十二烷基)硫酸钠(SDS);具有8或更多个碳原子的烷基的醚硫酸盐;和具有8或更多个碳原子的一个或多个烷基的烷基芳基磺酸盐。
[0036]可用于本发明的商业阴离子表面活性剂的一些实例包括由Stepan公司,Northfield,Illinois以商标BIO-SOFT N-300销售的三乙醇胺直链烷基磺酸盐;由Stepan公司以商标POLYSTEP销售的硫酸盐;和由Dow Chemical Company,Midland,Michigan以商标DOWFAX8390销售的正十六烷基二苯基氧化物二磺酸钠。
[0037]还可使用的两性表面活性剂通常包括例如烷基甜菜碱、烷基酰氨基甜菜碱和胺氧化物之类的表面活性剂组分,其具体实例是本领域已知的。
含水极性相
[0038]在该方法中使用的含水极性相最优选是由仅仅水组成的水相,或者含水和极性溶剂的水相。
[0039]此处特别优选的极性溶剂是测定为化妆品可接受的非水极性溶剂的那些化合物,尤其是单羟基醇如乙醇和异丙醇;二元醇和三元醇如丙二醇、1,2-己二醇CH3(CH2)3CH(OH)CH2OH、2-甲基-1,3-丙二醇HOCH2CH(CH3)CH2OH和甘油;甘油酯如甘油三乙酸酯(三醋精)、甘油三丙酸酯(三丙精)和甘油三丁酸酯(三丁精);和聚二元醇如聚乙二醇和聚丙二醇,尤其是PPG-14丁基醚C4H9[OCH(CH3)CH2]14OH。在除了个人护理以外的应用中,可使用这些和其它非水极性溶剂。
[0040]因此乳液或微乳液的含水极性相可由水,或水与极性溶剂的混合物组成,所述极性溶剂优选是极性有机化合物。一般来说,在考虑到配制合适组合物所使用的其它组分的用量之后,这一组分以提供组合物平衡到100%的用量存在于组合物内。然而,典型地,基于O/W或W/O乳液或微乳液组合物的总重量,这一组分占0.1-99.8wt%,优选10-95wt%。尽管可使用液体的混合物形成这一组合物的单相组分,但液体应当混溶且能形成基本上均匀的混合物。
任选的组分
[0041]由于乳液和微乳液容易受微生物污染,因此可要求防腐剂作为组合物的任选的组分,和可使用的一些代表性化合物包括甲醛、水杨酸、苯氧基乙醇、DMDM乙内酰脲(1,3-二羟甲基-5,5-二甲基乙内酰脲)、5-溴-5-硝基-1,3-二噁烷、对羟基苯甲酸甲酯、对羟基苯甲酸丙酯、山梨酸、由Sutton Laboratories,Chatham,New Jersey以名称GERMALLII销售的咪唑烷基脲、苯甲酸钠、由Rohm & HaasCompany,Philadelphia,Pennsylvania以名称KATHON CG销售的5-氯-2-甲基-4-异噻唑啉-3-酮,和由Lonza Incorporated,Fair Lawn,NewJersey以名称GLYCACILL销售的碘代丙炔基氨基甲酸丁酯。
[0042]冷冻/解冻稳定剂可作为组合物的另一任选的组分包括在内,其中包括例如乙二醇、丙二醇、甘油、三亚甲基二醇和聚氧乙烯醚醇,如由ICI Surfactants,Wilmington,Delaware销售的RENEX 30之类的化合物。
[0043]可包括在组合物内的另一任选组分是腐蚀抑制剂,如烷醇胺、无机磷酸盐如二硫代磷酸锌、无机膦酸盐、无机亚硝酸盐如亚硝酸钠、硅酸盐、siliconate、烷基磷酸胺、琥珀酸酐如十二碳烯基琥珀酸酐、胺琥珀酸盐或碱土金属磺酸盐如磺酸钠或磺酸钙。
[0044]可使用的额外的任选组分是低分子量的聚硅氧烷,如低分子量的直链或环状挥发性甲基硅氧烷,或低分子量的直链和环状挥发性和非挥发性烷基和芳基硅氧烷。最优选的是低分子量直链和环状挥发性甲基硅氧烷。这些组分是本领域公知的,和关于合适组分的具体实例,可参考美国专利6238657(2001年5月29日)。
可供替代的组分
[0045]当本发明的O/W或W/O乳液或微乳液组合物尤其在拟用于个人护理市场的产品上时,可配制该组合物包括一种或多种可供替代的组分,例如:
(A)调理剂,如阳离子聚合物、蛋白质、天然油、含氮原子的弹性硅烷和硅氧烷,除了蜡以外的烃,及其混合物;
(B)辅助表面活性剂,如甜菜碱、单烷基烷醇酰胺、二烷基烷醇酰胺、胺氧化物、胺氨基乙酸盐、胺丙酸盐、胺磺基甜菜碱,及其混合物;
(C)多元醇,如甘油和山梨醇。
[0046]含可供替代组分(A)的产物特别用作调理剂,含(A)和(B)的产物特别用作香波,和含(C)的产物特别用作保湿剂。
制剂
[0047]基于组合物的总重量,制备本发明的乳液和微乳液所使用的各种组分的用量为:
(i)0.01-90wt%的在其分子内具有环氧基或卤代醇基的有机季铵化合物;
(ii)0.01-90wt%的在其分子内具有氨基的硅烷或硅氧烷;
(iii)0.01-90wt%的交联剂;
(iv)0.01-90wt%的表面活性剂,优选2-40wt%,更优选5-20wt%;和
(v)平衡到100wt%的含水极性相。通过省去组分(i),即在其分子内具有环氧基或卤代醇基的有机机铵化合物,也可制备乳液和微乳液。
[0048]若包括任选的组分,则通常以0.01-0.1wt%的用量存在各种任选组分,即防腐剂、冷冻/解冻稳定剂或腐蚀抑制剂。
[0049]可通过一起简单混合所有组分,使反应发生,和这是在这一情况下获得反应,即进行“反应”步骤的最小要求。然而,通常优选一起混合所有反应物并加热它们。一般来说,不需要催化剂,但在一些情况下,可使用合适的催化剂。关于这一点,已发现,一般来说,叔胺不容易加成到环氧化物上。若酸化反应混合物,特别地以化学计量的比例酸化,则可得到改进,或者用酸预处理叔胺,以便将它转化成其酸式盐。
[0050]可使用简单的推进式混合器、涡流型混合器、布鲁克菲尔德逆向旋转混合器或均化混合器,来制备乳液和微乳液。通常不要求特殊的设备或处理条件。
[0051]列出下述实施例,为的是更详细地阐述本发明。
实施例1
[0052]在反应容器内放置200g三甲基甲硅烷氧基封端的氨基官能的硅氧烷,其聚合度(DP)为约300且含有约2mol%的氨乙基氨基异丁基甲基硅氧烷基。添加30g Tergitol TMN-6和30g Tergitol TMN-10非离子表面活性剂,并采用机械搅拌器混合10-15分钟的时间段。然后将40g水和0.95g冰醋酸加入到溶液中,并允许混合30分钟。在混合之后,加热溶液到75±5℃,和添加13.6g缩水甘油基三甲基氯化铵。然后,在75±5℃下,搅拌该混合物2小时。然后,将320g水快速加入到溶液中,并快速混合1小时。添加额外114g水,并混合30分钟。此刻,添加15.8g DP为约5且含有三个甲基(丙基-3-环氧丙氧基)硅氧烷基的三甲基甲硅烷氧基封端的硅氧烷,以使氨基官能的硅氧烷交联。在搅拌下,在75±5℃下保持该溶液2小时。然后使乳液冷却到室温。最终产物为具有可见的蓝色色调的清澈乳液,其含有弹性季铵官能的硅氧烷。
实施例2
[0053]在反应容器内放置200g三甲基甲硅烷氧基封端的氨基官能的硅氧烷,其聚合度(DP)为约300且含有约2mol%的氨乙基氨基异丁基甲基硅氧烷基。添加30g Tergitol TMN-6和30g Tergitol TMN-10非离子表面活性剂,并采用机械搅拌器混合10-15分钟的时间段。然后将40g水和0.37g冰醋酸加入到溶液中,然后混合30分钟。之后,将320g水快速添加到溶液中,并快速混合1小时。添加额外的114g水,并混合30分钟。此刻,添加14.6gDP为约5且含有三个甲基(丙基-3-环氧丙氧基)硅氧烷基的三甲基甲硅烷氧基封端的硅氧烷,以使氨基官能的硅氧烷交联。在搅拌下,在75±5℃下保持该溶液2小时。然后使乳液冷却到室温。最终产物为具有可见的蓝色色调的清澈乳液,其含有弹性胺官能的硅氧烷。
[0054]实施例2阐述了视需要可使用的制备水包油(O/W)和油包水(W/O)乳液与微乳液的另一方法,所述乳液或微乳液含有具有氮原子的弹性硅烷或硅氧烷作为乳液或微乳液的油相。它基本上包括下述步骤:
(i)制备仅仅含有在其分子内具有氨基的硅烷或硅氧烷和表面活性剂的第一混合物;
(ii)通过添加第一部分的含水极性相到第一混合物中,制备第二混合物;
(iii)通过添加剩余量的含水极性相到第二混合物中,制备第三混合物;
(iv)通过添加交联剂到第三混合物中,制备第四混合物;和
(v)加热第四混合物。
实施例3
[0055]称取80g实施例1的乳液(即与缩水甘油基三甲基氯化铵部分反应的氨基官能的硅氧烷的含水乳液)放入塑料杯内。向该乳液中逐滴添加0.26g丙烯酸2-羟乙酯,密封该杯子,并放入HaushildSpeedmixer Model TM DAC-150实验室混合装置内。混合杯子的内容物2个循环,其中每一个循环20秒。从混合器中取下杯子,并使之未受干扰地静置4小时,之后将3g该乳液倾倒入50mm塑料培养皿中,使在该培养皿内的乳液在实验室环境条件下蒸发16小时。得到在甲苯内不溶的弹性膜。
实施例4
[0056]称取80g实施例1的乳液(即与缩水甘油基三甲基氯化铵部分反应的氨基官能的硅氧烷的含水乳液)放入塑料杯内。向该乳液中逐滴添加0.18g己二异氰酸酯,密封该杯子,并放入HaushildSpeedmixer Model TM DAC-150实验室混合装置内。混合杯子的内容物2个循环,其中每一个循环20秒。从混合器中取下杯子,并使之未受干扰地静置1小时,之后将3g该乳液倾倒入50mm塑料培养皿中,使在该培养皿内的乳液在实验室环境条件下蒸发16小时。得到在甲苯内不溶的弹性膜。
实施例5
[0057]在反应容器内放置200g三甲基甲硅烷氧基封端的氨基硅氧烷,其聚合度(DP)为约300且含有约2mol%的氨乙基氨基异丁基甲基硅氧烷基。添加30g Tergitol TMN-6和30g Tergitol TMN-10非离子表面活性剂,并采用机械搅拌器混合10-15分钟的时间段。然后将40g水和0.37g冰醋酸加入到溶液中,混合该溶液30分钟。然后,将320g水快速加入到溶液中,并快速混合该溶液1小时。添加额外的114g水,混合该溶液30分钟。称取30g该乳液放入塑料杯内,接着添加0.20g丙烯酸2-羟乙酯。密封该杯子,并放入HaushildSpeedmixer Model TM DAC-150实验室混合装置内。混合杯子的内容物2个循环,其中每一个循环20秒。从混合器中取下杯子,并使之未受干扰地静置1小时,之后将3g该乳液倾倒入50mm塑料培养皿中,使在该培养皿内的乳液在实验室环境条件下蒸发16小时。得到在甲苯内不溶的弹性膜。
实施例6
[0058]称取30g实施例5中制备的氨基官能的乳液放入塑料杯内,接着添加0.34g己二异氰酸酯。密封该杯子,并放入HaushildSpeedmixer Model TM DAC-150实验室混合装置内。混合杯子的内容物2个循环,其中每一个循环20秒。从混合器中取下杯子,并使之未受干扰地静置1小时,之后将3g该乳液倾倒入50mm塑料培养皿中,使在该培养皿内的乳液在实验室环境条件下蒸发16小时。得到在甲苯内不溶的弹性膜。
[0059]此处制备的乳液和微乳液可用于个人护理,例如制备例如止汗剂和除味剂之类的组合物。它们可用于皮肤脂膏、皮肤护理洗剂、保湿剂、面部处理剂如粉刺或皱纹除去剂、个人和面部清洁剂、沐浴油、香水、古龙香水、香囊、防晒剂、剃须前洗剂和剃须后洗剂、剃须皂和剃须泡沫。它们可用于头发香波、头发调理剂、头发着色剂、头发松弛剂、喷发剂、摩丝、长效剂(permanent)、脱毛剂和指甲油。在化妆品中,该组合物可加入到美容用品、彩妆、粉底、胭脂、唇膏、眼线、睫毛膏、除油剂、卸彩妆剂和粉末中。在这种应用中,组合物可包括油溶性、极性溶剂可溶的和水溶性成分如维生素。
[0060]该乳液和微乳液还能功能化作为药物载体、杀虫剂和其它生物活性物质;和这种组合物用作在湿类清洁擦巾如湿纸巾、卫生纸和毛巾(其通常作为个人卫生和家庭清洁任务而销售)中使用的纤维素或合成非织造载体基质的添加剂。
[0061]可对此处所述的化合物、组合物和方法作出其它各种变化,且没有脱离本发明的基本特征。此处具体地描述的本发明的实施方案仅仅是例举和除了所附权利要求限制本发明范围以外,这些实施方案不打算限制本发明范围。
Claims (16)
1.一种制备水包油(O/W)和油包水(W/O)乳液和微乳液的方法,所述乳液和微乳液含有在其分子内具有季铵基的弹性硅烷或硅氧烷作为该乳液或微乳液的油相,该方法包括在分散于(v)含水极性相内的(iii)交联剂和(iv)表面活性剂存在下,使(i)在其分子内具有环氧基或卤代醇基的有机季铵化合物与(ii)在其分子内具有氨基的硅烷或硅氧烷反应。
2.权利要求1的方法,其中具有环氧基的有机季铵化合物是缩水甘油基三甲基氯化铵或缩水甘油基三甲基溴化铵。
3.权利要求1的方法,其中具有卤代醇基的有机季铵化合物选自(3-氯-2-羟基丙基)三甲基氯化铵、(3-氯-2-羟基丙基)二甲基十二烷基氯化铵、(3-氯-2-羟基丙基)二甲基十八烷基氯化铵、(3-氯-2-羟基丙基)三甲基溴化铵、(3-氯-2-羟基丙基)二甲基十二烷基溴化铵和(3-氯-2-羟基丙基)二甲基十八烷基溴化铵。
4.权利要求1的方法,其中含水极性相由水组成。
5.权利要求1的方法,其中含水极性相包括水和极性有机化合物。
6.权利要求5的方法,其中极性有机化合物选自单羟基醇、二元醇、三元醇、甘油酯和多元醇。
7.权利要求1的方法,其中交联剂选自含至少两个环氧基的有机环氧化物、含至少两个环氧基的环氧官能的硅氧烷、氯代醇、丙烯酸羟烷酯和异氰酸酯。
8.通过权利要求1的方法制备的乳液或微乳液。
9.通过权利要求1的方法制备的在其分子内具有季铵基的弹性硅烷或硅氧烷。
10.一种制备水包油(O/W)和油包水(W/O)乳液和微乳液的方法,所述乳液和微乳液含有具有氮原子的弹性硅烷或硅氧烷作为该乳液或微乳液的油相,该方法按序包括下述步骤:
(i)制备仅仅含有在其分子内具有氨基的硅烷或硅氧烷和表面活性剂的第一混合物;
(ii)通过添加第一部分的含水极性相到第一混合物中,制备第二混合物;
(iii)通过添加剩余量的含水极性相到第二混合物中,制备第三混合物;
(iv)通过添加交联剂到第三混合物中,制备第四混合物;和
(v)加热第四混合物。
11.权利要求10的方法,其中含水极性相由水组成。
12.权利要求10的方法,其中含水极性相包括水和极性有机化合物。
13.权利要求12的方法,其中极性有机化合物选自单羟基醇、二元醇、三元醇、甘油酯和多元醇。
14.权利要求10的方法,其中交联剂选自含至少两个环氧基的有机环氧化物、含至少两个环氧基的环氧官能的硅氧烷、氯代醇、丙烯酸羟烷酯和异氰酸酯。
15.通过权利要求10的方法制备的乳液或微乳液。
16.通过权利要求10的方法制备的弹性硅烷或硅氧烷。
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CN116606383A (zh) * | 2023-04-27 | 2023-08-18 | 牡丹江恒源生化有限责任公司 | 一种改性淀粉乳化剂及其制备方法 |
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CN101386678B (zh) * | 2007-09-13 | 2013-03-13 | 道康宁(上海)有限公司 | 制备包含具有季铵基团的弹性体聚硅氧烷的有机硅乳液的方法 |
CN115003784A (zh) * | 2019-12-30 | 2022-09-02 | 美国陶氏有机硅公司 | 阳离子表面活性剂泡沫稳定组合物 |
CN116606383A (zh) * | 2023-04-27 | 2023-08-18 | 牡丹江恒源生化有限责任公司 | 一种改性淀粉乳化剂及其制备方法 |
CN116606383B (zh) * | 2023-04-27 | 2023-12-05 | 牡丹江恒源生化有限责任公司 | 一种改性淀粉乳化剂及其制备方法 |
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EP1625132A1 (en) | 2006-02-15 |
JP2007508411A (ja) | 2007-04-05 |
US7902293B2 (en) | 2011-03-08 |
DE602004015771D1 (de) | 2008-09-25 |
CN100445290C (zh) | 2008-12-24 |
EP1625132B1 (en) | 2008-08-13 |
KR101094086B1 (ko) | 2011-12-15 |
WO2004104013A1 (en) | 2004-12-02 |
US20060193805A1 (en) | 2006-08-31 |
JP5404998B2 (ja) | 2014-02-05 |
ATE404570T1 (de) | 2008-08-15 |
KR20060009348A (ko) | 2006-01-31 |
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