CN114787282A - Cationic emulsion composition of polyorganosiloxane and preparation method thereof - Google Patents
Cationic emulsion composition of polyorganosiloxane and preparation method thereof Download PDFInfo
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- CN114787282A CN114787282A CN202080085540.8A CN202080085540A CN114787282A CN 114787282 A CN114787282 A CN 114787282A CN 202080085540 A CN202080085540 A CN 202080085540A CN 114787282 A CN114787282 A CN 114787282A
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- polyorganosiloxane
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- 239000000839 emulsion Substances 0.000 title claims abstract description 111
- 239000000203 mixture Substances 0.000 title claims abstract description 80
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 44
- 238000002360 preparation method Methods 0.000 title description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000003093 cationic surfactant Substances 0.000 claims abstract description 34
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 65
- 125000000962 organic group Chemical group 0.000 claims description 48
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 238000000576 coating method Methods 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 239000011248 coating agent Substances 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 230000001804 emulsifying effect Effects 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 13
- 239000003513 alkali Substances 0.000 claims description 12
- 239000002537 cosmetic Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 239000005871 repellent Substances 0.000 claims description 8
- 230000002940 repellent Effects 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 210000004209 hair Anatomy 0.000 claims description 6
- 239000002736 nonionic surfactant Substances 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 4
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 239000006082 mold release agent Substances 0.000 claims 1
- 238000006116 polymerization reaction Methods 0.000 description 50
- -1 polysiloxanes Polymers 0.000 description 34
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 17
- 239000000835 fiber Substances 0.000 description 17
- 229920001296 polysiloxane Polymers 0.000 description 15
- 239000004480 active ingredient Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- XKBGEWXEAPTVCK-UHFFFAOYSA-M methyltrioctylammonium chloride Chemical compound [Cl-].CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC XKBGEWXEAPTVCK-UHFFFAOYSA-M 0.000 description 11
- 239000004744 fabric Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 241000282320 Panthera leo Species 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- SXPLZNMUBFBFIA-UHFFFAOYSA-N butyl(trimethoxy)silane Chemical compound CCCC[Si](OC)(OC)OC SXPLZNMUBFBFIA-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 125000003700 epoxy group Chemical group 0.000 description 5
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 125000002347 octyl 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])[H] 0.000 description 4
- 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 4
- 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 4
- 239000000758 substrate Substances 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000908 ammonium hydroxide Substances 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- 125000002704 decyl group Chemical group [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])* 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000001421 myristyl 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])[H] 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 125000001400 nonyl 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])[H] 0.000 description 3
- 125000005375 organosiloxane group Chemical group 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 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
- 239000002994 raw material Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 125000003944 tolyl group Chemical group 0.000 description 3
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- 229920002334 Spandex Polymers 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000010556 emulsion polymerization method Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 230000010534 mechanism of action Effects 0.000 description 2
- 239000000123 paper Substances 0.000 description 2
- 125000004115 pentoxy group Chemical group [*]OC([H])([H])C([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- NROKBHXJSPEDAR-UHFFFAOYSA-M potassium fluoride Chemical compound [F-].[K+] NROKBHXJSPEDAR-UHFFFAOYSA-M 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000010008 shearing Methods 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 239000004759 spandex Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 0.000 description 2
- 125000003396 thiol group Chemical group [H]S* 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 1
- DOYKFSOCSXVQAN-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CCO[Si](C)(OCC)CCCOC(=O)C(C)=C DOYKFSOCSXVQAN-UHFFFAOYSA-N 0.000 description 1
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 1
- LZMNXXQIQIHFGC-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propyl 2-methylprop-2-enoate Chemical compound CO[Si](C)(OC)CCCOC(=O)C(C)=C LZMNXXQIQIHFGC-UHFFFAOYSA-N 0.000 description 1
- URDOJQUSEUXVRP-UHFFFAOYSA-N 3-triethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCCOC(=O)C(C)=C URDOJQUSEUXVRP-UHFFFAOYSA-N 0.000 description 1
- LVNLBBGBASVLLI-UHFFFAOYSA-N 3-triethoxysilylpropylurea Chemical compound CCO[Si](OCC)(OCC)CCCNC(N)=O LVNLBBGBASVLLI-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- KBQVDAIIQCXKPI-UHFFFAOYSA-N 3-trimethoxysilylpropyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C=C KBQVDAIIQCXKPI-UHFFFAOYSA-N 0.000 description 1
- SPRIMNFMVQNFDZ-UHFFFAOYSA-N 4-methyl-N-(3-triethoxysilylpropyl)pent-2-en-2-amine Chemical compound C(C)O[Si](CCCNC(=CC(C)C)C)(OCC)OCC SPRIMNFMVQNFDZ-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- CPZHPNSUWUBSQW-UHFFFAOYSA-M CCCCCCCCCCCCCCCCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.[Cl-] CPZHPNSUWUBSQW-UHFFFAOYSA-M 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 1
- 229920002978 Vinylon Polymers 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000002318 adhesion promoter Substances 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000002518 antifoaming agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 125000001204 arachidyl 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])[H] 0.000 description 1
- 238000007611 bar coating method Methods 0.000 description 1
- YSJGOMATDFSEED-UHFFFAOYSA-M behentrimonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCCCCC[N+](C)(C)C YSJGOMATDFSEED-UHFFFAOYSA-M 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- KQAHMVLQCSALSX-UHFFFAOYSA-N decyl(trimethoxy)silane Chemical compound CCCCCCCCCC[Si](OC)(OC)OC KQAHMVLQCSALSX-UHFFFAOYSA-N 0.000 description 1
- 125000006612 decyloxy group Chemical group 0.000 description 1
- OTARVPUIYXHRRB-UHFFFAOYSA-N diethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](C)(OCC)CCCOCC1CO1 OTARVPUIYXHRRB-UHFFFAOYSA-N 0.000 description 1
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 1
- WHGNXNCOTZPEEK-UHFFFAOYSA-N dimethoxy-methyl-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](C)(OC)CCCOCC1CO1 WHGNXNCOTZPEEK-UHFFFAOYSA-N 0.000 description 1
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
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- 238000004090 dissolution Methods 0.000 description 1
- OROLQGYWJPKRJV-UHFFFAOYSA-M docosyl(trimethyl)azanium;acetate Chemical compound CC([O-])=O.CCCCCCCCCCCCCCCCCCCCCC[N+](C)(C)C OROLQGYWJPKRJV-UHFFFAOYSA-M 0.000 description 1
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- MRAPAFWHXSJNRN-UHFFFAOYSA-M icosyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCCC[N+](C)(C)C MRAPAFWHXSJNRN-UHFFFAOYSA-M 0.000 description 1
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- 239000010985 leather Substances 0.000 description 1
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- 125000002960 margaryl 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])[H] 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- MQWFLKHKWJMCEN-UHFFFAOYSA-N n'-[3-[dimethoxy(methyl)silyl]propyl]ethane-1,2-diamine Chemical compound CO[Si](C)(OC)CCCNCCN MQWFLKHKWJMCEN-UHFFFAOYSA-N 0.000 description 1
- KBJFYLLAMSZSOG-UHFFFAOYSA-N n-(3-trimethoxysilylpropyl)aniline Chemical compound CO[Si](OC)(OC)CCCNC1=CC=CC=C1 KBJFYLLAMSZSOG-UHFFFAOYSA-N 0.000 description 1
- PSIDVLNBMQXBFV-UHFFFAOYSA-N n-ethyl-3-triethoxysilylpropan-1-amine Chemical compound CCNCCC[Si](OCC)(OCC)OCC PSIDVLNBMQXBFV-UHFFFAOYSA-N 0.000 description 1
- 125000001196 nonadecyl 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])[H] 0.000 description 1
- 239000012875 nonionic emulsifier Substances 0.000 description 1
- 125000005064 octadecenyl group Chemical group C(=CCCCCCCCCCCCCCCCC)* 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- PFPYHYZFFJJQFD-UHFFFAOYSA-N oxalic anhydride Chemical compound O=C1OC1=O PFPYHYZFFJJQFD-UHFFFAOYSA-N 0.000 description 1
- 125000006353 oxyethylene group Chemical group 0.000 description 1
- 125000002958 pentadecyl 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])[H] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
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- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
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- 235000019260 propionic acid Nutrition 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
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- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229940014800 succinic anhydride Drugs 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- VTHOKNTVYKTUPI-UHFFFAOYSA-N triethoxy-[3-(3-triethoxysilylpropyltetrasulfanyl)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCSSSSCCC[Si](OCC)(OCC)OCC VTHOKNTVYKTUPI-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- WDFCQTZXHUWJON-UHFFFAOYSA-M triheptyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCC[N+](C)(CCCCCCC)CCCCCCC WDFCQTZXHUWJON-UHFFFAOYSA-M 0.000 description 1
- RNPOWDKBFLNPNV-UHFFFAOYSA-M trihexyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCC[N+](C)(CCCCCC)CCCCCC RNPOWDKBFLNPNV-UHFFFAOYSA-M 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- ILLSOFGDDPNATO-UHFFFAOYSA-M trimethyl(octadecyl)azanium;acetate Chemical compound CC([O-])=O.CCCCCCCCCCCCCCCCCC[N+](C)(C)C ILLSOFGDDPNATO-UHFFFAOYSA-M 0.000 description 1
- BFPOZPZYPNVMHU-UHFFFAOYSA-M trimethyl-[3-(trifluoromethyl)phenyl]azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC(C(F)(F)F)=C1 BFPOZPZYPNVMHU-UHFFFAOYSA-M 0.000 description 1
- UMMDBKGUDMBUSR-UHFFFAOYSA-M tris-decyl(methyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCC[N+](C)(CCCCCCCCCC)CCCCCCCCCC UMMDBKGUDMBUSR-UHFFFAOYSA-M 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- 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
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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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- 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
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/41—Amines
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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
- A61K8/18—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
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
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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
- A61K8/18—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
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61K8/892—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a hydroxy group, e.g. dimethiconol
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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
- A61K8/18—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
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
-
- 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
- C08G77/04—Polysiloxanes
- C08G77/06—Preparatory processes
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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
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
- C08K5/19—Quaternary ammonium compounds
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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
- 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
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
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- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
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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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/521—Carboxylic amides (R1-CO-NR2R3), where R1, R2 and R3 are alkyl or alkenyl groups
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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
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/37—Polymers
- C11D3/3703—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- C11D3/373—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicones
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- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/46—Compounds containing quaternary nitrogen atoms
- D06M13/463—Compounds containing quaternary nitrogen atoms derived from monoamines
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- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
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Abstract
The present invention is a cationic emulsion composition of polyorganosiloxane, which contains: 100 parts by mass of (A) a polyorganosiloxane represented by the following average composition formula (1) and having a viscosity of 300,000 mPas or more at 25 ℃; 0.1 to 30 parts by mass of (B-1) a cationic surfactant Q1 3(CH3)N+·X‑(ii) a 0.1 to 30 parts by mass of (B-2) a cationic surfactant Q2(CH3)3N+·X‑(ii) a 30 to 3,000 parts by mass of (C) water. Thus, a polyorganosiloxane cationic emulsion composition having a high viscosity of 300,000 mPas or more and excellent stability and durability is provided.
Description
Technical Field
The invention relates to a cationic emulsion composition of polyorganosiloxane and a preparation method thereof.
Background
Since smoothness and water repellency can be imparted by treating a substrate with polyorganosiloxane, it is used in fiber treatment agents, release agents, water repellents, cosmetics, hair cosmetics, and the like. Among these, highly polymerized polysiloxanes are excellent in the effect of imparting smoothness. It is also known that when a cationic surfactant such as a quaternary ammonium salt is used as a surfactant in emulsifying these polysiloxanes, the adsorption of the polysiloxanes to a substrate is improved. Therefore, there is a high demand for an emulsion obtained by emulsifying a polysiloxane having a high polymerization degree with a cationic surfactant.
A common method for emulsifying polysiloxanes is to emulsify and disperse polysiloxanes and surfactants in water by using mechanical shearing force of an emulsifier, but polysiloxanes with high polymerization degree have too high viscosity, cannot uniformly apply mechanical shearing force, and cannot obtain stable emulsion.
As a method for obtaining a polysiloxane emulsion having a high polymerization degree, an emulsion polymerization method is known in which an emulsion of a siloxane monomer is polymerized in an emulsion using an acid or alkali catalyst (patent documents 1 and 2). However, when a cationic surfactant such as quaternary ammonium salt represented by cetyltrimethylammonium chloride described in the literature is used in such an emulsion polymerization method, the polymerization rate is extremely slow, and therefore, it takes a long time to increase the polymerization degree. Even when polymerization is carried out for about 150 hours, which is considered to be industrially practical, the polysiloxane can be polymerized only to a level such that the extracted viscosity is several tens of thousands mPas.
As a method for obtaining a cationic emulsion of a polysiloxane having a high degree of polymerization, a method of performing polymerization using a silicon alkoxide catalyst (patent document 3) and a method of performing polymerization using an ammonium hydroxide catalyst (patent document 4) have also been proposed, but the degree of polymerization is not sufficient in the same manner.
Further, there has been proposed a method of producing a highly polymerized silicone emulsion using an anionic surfactant and then adding a cationic surfactant (patent documents 5 and 6), but there is a problem in stability because an anionic surfactant is used together.
Further, a method of carrying out polymerization under a two-stage temperature condition has also been proposed (patent document 7), but there is a problem that a long polymerization time is required for increasing the polymerization degree.
In addition, in recent years, in the field of fiber treatment agents, there have been increasing demands for washing durability of a level that cannot be achieved by only high-polymerization-degree polysiloxane. There is also an example in which durability is improved by adding a coating film enhancer such as silica to an emulsion of a high-polymerization-degree polysiloxane to improve the strength of the coating film, but there is also a problem in that the stability is lowered and the number of production steps is increased by adding silica.
Documents of the prior art
Patent document
Patent document 1: japanese examined patent publication No. 41-13995
Patent document 2: japanese examined patent publication No. 56-38609
Patent document 3: japanese laid-open patent publication No. H08-104752
Patent document 4: japanese patent laid-open publication No. 2001-106787
Patent document 5: japanese laid-open patent publication No. H09-137062
Patent document 6: japanese patent laid-open publication No. H10-140480
Patent document 7: japanese unexamined patent application publication No. 09-278626
Disclosure of Invention
Technical problem to be solved by the invention
The present invention has been made in view of the above circumstances, and an object thereof is to provide a cationic emulsion composition of polyorganosiloxane having a viscosity of 300,000mP s or more and high stability and durability. The object of the present invention is to provide a preparation process which enables such emulsion compositions to be polymerized in a relatively short time.
Means for solving the problems
In order to achieve the above object, the present invention provides a cationic polyorganosiloxane emulsion composition, comprising:
100 parts by mass of (A) a polyorganosiloxane represented by the average composition formula (1) below and having a viscosity of 300,000 mPas or more at 25 ℃,
[ chemical formula 1]
In the formula (1), R1Independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, R2Independently of one another are selected from the abovementioned radicals R1A, b, c and d are values such that the viscosity of the polyorganosiloxane at 25 ℃ satisfies 300,000 mPas or more, a is not less than 2, and c + d is not less than 1;
0.1 to 30 parts by mass of (B-1) a cationic surfactant Q1 3(CH3)N+·X-，
Wherein Q is1The same or different monovalent organic groups with 6-30 carbon atoms are used, and X is a halogen atom or monovalent carboxyl with 1-6 carbon atoms;
0.1 to 30 parts by mass of (B-2) a cationic surfactant Q2(CH3)3N+·X-，
Wherein Q2Is a monovalent organic group having 17 to 30 carbon atoms, and X is a halogen atom or a monovalent carboxyl group having 1 to 6 carbon atoms;
30 to 3,000 parts by mass of (C) water.
Such a cationic emulsion composition of polyorganosiloxane is a cationic emulsion composition of high-polymerization polyorganosiloxane having a high viscosity, and is excellent in stability and durability.
In this case, the emulsion composition of the present invention preferably further comprises a nonionic surfactant.
Thus, by using both a cationic surfactant and a nonionic surfactant, the emulsion can be easily made smaller in particle size, thereby improving the stability of the emulsion.
Further, the emulsion composition of the present invention preferably forms a coating film after drying.
In this way, the emulsion compound of the present invention can be dried to form a coating film.
The present invention also provides a fiber-treating agent, which is characterized by comprising the cationic emulsion composition of polyorganosiloxane described above.
The present invention also provides a release agent characterized by containing the cationic emulsion composition of polyorganosiloxane.
The present invention also provides a water repellent agent, which is characterized by containing the cationic emulsion composition of polyorganosiloxane.
The present invention also provides a cosmetic composition comprising the polyorganosiloxane as described above.
The present invention also provides a cosmetic for hair, which is characterized by containing the cationic emulsion composition of polyorganosiloxane.
As described above, the cationic emulsion composition of polyorganosiloxane of the present invention can be suitably used as a component contained in a fiber treatment agent, a release agent, a water repellent agent, a cosmetic, and a cosmetic for hair.
The present invention also provides a method for preparing a cationic emulsion composition of polyorganosiloxane, which is characterized in that the cationic emulsion composition is obtained by emulsifying and dispersing the following components in the presence of an alkali catalyst, and the method comprises polymerizing an emulsion at 0 to 30 ℃ for 1 to 150 hours, and further neutralizing the emulsion:
100 parts by mass of (D) a compound of the general formula HO- [ R ]1 2SiO]jA double-terminal hydroxy polydiorganosiloxane represented by the formula (I) wherein R is1Independently of one another, a monovalent organic group having 1 to 20 hydrogen atoms or carbon atoms, j being such that the polydiorganosiloxane having hydroxyl groups at both ends has a viscosity at 25 ℃ of less than 2,000 mPas;
0 to 20 parts by mass of (E) any one or two or more kinds of organoalkoxysilanes,
Si(OR3)4、R1Si(OR3)3、R1 2Si(OR3)2、R1 3Si(OR3)，
wherein R is1Independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, R3Independently represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms;
0.1 to 30 parts by mass of (B-1) a cationic surfactant Q1 3(CH3)N+·X-，
Wherein Q is1The organic group is a monovalent organic group with 6-30 carbon atoms of the same or different types, and X is a halogen atom or a monovalent carboxyl group with 1-6 carbon atoms;
0.1 to 30 parts by mass of (B-2) a cationic surfactantQ2(CH3)3N+·X-，
Wherein Q is2Is a monovalent organic group having 17 to 30 carbon atoms, and X is a halogen atom or a monovalent carboxyl group having 1 to 6 carbon atoms;
30 to 3,000 parts by mass of (C) water.
In the method for producing such an emulsion composition, a cationic emulsion composition of a high-polymerization polyorganosiloxane having a high viscosity can be polymerized in a relatively short time, and the emulsion composition has good stability and durability.
Effects of the invention
The cationic emulsion composition of polyorganosiloxane of the invention is a cationic emulsion composition of high-polymerization polyorganosiloxane with high viscosity, and has good stability and durability. In addition, the emulsion composition can form a coating film alone, and the durability of the coating film can be further improved. Such an emulsion composition can be suitably used as a fiber treatment agent, a release agent, a water repellent agent, a cosmetic, a hair cosmetic, and the like.
Further, the method for producing a cationic emulsion composition of polyorganosiloxane of the present invention enables such an emulsion composition to be polymerized in a relatively short time, and is therefore industrially useful.
Detailed Description
The present inventors have conducted extensive studies to achieve the above object, and as a result, have found that polymerization can be carried out in a relatively short period of time by carrying out polymerization for 1 to 150 hours at 0 to 30 ℃ in the presence of an alkali catalyst and further carrying out neutralization, and that the emulsion is obtained by emulsifying and dispersing:
100 parts by mass of (D) a compound of the formula HO- [ R ]1 2SiO]jA double-terminal hydroxy polydiorganosiloxane represented by the formula (I) wherein R is1Independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, j being such that the viscosity of the polydiorganosiloxane at both terminal ends at 25 ℃ satisfies a value of less than 2,000 mPas;
0 to 20 parts by mass of (E) any one or two or more kinds of organoalkoxysilanes,
Si(OR3)4、R1Si(OR3)3、R1 2Si(OR3)2、R1 3Si(OR3)，
wherein R is1Independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, R3Independently represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms;
0.1 to 30 parts by mass of (B-1) a cationic surfactant Q1 3(CH3)N+·X-，
Wherein Q is1The organic group is a monovalent organic group with 6-30 carbon atoms of the same or different types, and X is a halogen atom or a monovalent carboxyl group with 1-6 carbon atoms;
0.1 to 30 parts by mass of (B-2) a cationic surfactant Q2(CH3)3N+·X-，
Wherein Q is2Is a monovalent organic group having 17 to 30 carbon atoms, and X is a halogen atom or a monovalent carboxyl group having 1 to 6 carbon atoms;
30 to 3,000 parts by mass of (C).
The inventors of the present invention have also found that a cationic emulsion composition containing a polyorganosiloxane represented by the following average composition formula (1) and having a viscosity of 300,000mPa · s or more at 25 ℃ as component (a) can be obtained, and that the emulsion composition has good stability and good durability, and have completed the present invention.
[ chemical formula 2]
In the formula (1), R1Independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, R2Independently of one another are selected from the abovementioned radicals R1A group, hydroxyl group or carbon atom in the item of (1)Alkoxy groups having a sub-number of 1 to 20, a, b, c and d are values such that the viscosity of the polyorganosiloxane at 25 ℃ is 300,000 mPas or more, a is 2 or more, and c + d is 1 or more.
Such a polyorganosiloxane with a high viscosity of 300,000 mPas or more is usually a polyorganosiloxane with a high polymerization degree. Therefore, the cationic emulsion composition of polyorganosiloxane with high degree of polymerization may be referred to as "polyorganosiloxane with high degree of polymerization" in the description of the present invention.
Hereinafter, embodiments of the present invention will be described, but the present invention is not limited thereto.
First, the respective components of the cationic polyorganosiloxane emulsion composition of the present invention will be described.
[ (A) component ]
(A) The component (A) is a polyorganosiloxane expressed by the following average composition formula (1) and having a viscosity of 300,000 mPas or more at 25 ℃. The emulsion composition of the present invention contains the component (a) in an amount of 100 parts by mass.
[ chemical formula 3]
In the formula (1), R1Independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, R2Independently of one another are selected from the abovementioned radicals R1The group, hydroxyl group or alkoxy group having 1 to 20 carbon atoms, wherein a, b, c and d are values such that the viscosity of the polyorganosiloxane at 25 ℃ is 300,000 mPas or more, a is 2 or more, and c + d is 1 or more.
As mentioned above, R1Independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms. The monovalent organic group having 1 to 20 carbon atoms may be any of linear, branched, or cyclic, and specifically, includes: alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, cyclopentyl, cyclohexyl, and cycloheptyl; aryl groups such as phenyl, tolyl, and naphthyl; vinyl, allyl and the likeAlkenyl of (a); or a group in which a part of hydrogen atoms in the structure of these organic groups is substituted with a polar group-containing organic group such as a halogen atom, an amino group, an acryloyloxy group, a methacryloyloxy group, an epoxy group, a mercapto group, or the like. Here, R is preferable in terms of industrial and characteristic properties1More than 80% of the total amount of the compounds are methyl groups.
Further, as described above, R2Independently of one another are selected from the abovementioned radicals R1The group, hydroxyl group or alkoxy group having 1 to 20 carbon atoms in the above-mentioned group. The alkoxy group having 1 to 20 carbon atoms may be any of a linear, branched or cyclic group, and specifically includes a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, a hexoxy group, an octoxy group, a decyloxy group, a dodecyloxy group, a 2-ethylhexoxy group and the like, preferably a methoxy group, an ethoxy group, a propoxy group, a butoxy group, a pentoxy group, and more preferably a methoxy group, an ethoxy group, and a propoxy group.
When a reactive functional group is present in the above average composition formula (1), the reactive functional group may react with other compounds. Specifically, when an amino group is present in the average composition formula (1), the ring-opening reaction with an epoxy group-containing polyoxyalkylene compound or an epoxy group-containing alkyl compound may be carried out, and the acetylation reaction with a carboxylic anhydride such as acetic anhydride, propionic anhydride, oxalic anhydride, succinic anhydride, maleic anhydride, phthalic anhydride, or benzoic anhydride may be carried out. Further, when an epoxy group is present in the above average composition formula (1), a ring-opening reaction with an amino group-containing compound can be performed. The reaction with the reactive functional group shown above is not limited to these reactions.
In the average composition formula (1), a, b, c, and d are values at which the viscosity of the polyorganosiloxane at 25 ℃ is 300,000 mPas or more, more preferably values at which the viscosity of the polyorganosiloxane at 25 ℃ is 400,000 mPas or more, and still more preferably values at which the viscosity of the polyorganosiloxane at 25 ℃ is 500,000 mPas or more. The viscosity is an absolute viscosity, and is a value measured directly at 25 ℃ by a rotary viscometer when the viscosity can be measured in a liquid state, and is a value measured at 25 ℃ by a rotary viscometer when the viscosity is too high to be measured. Furthermore, a is not less than 2, and c + d is not less than 1.
B in the average composition formula (1) can typically take a value of 50 or more, and preferably a value of 100 or more. However, when the value of c + d is large, the number of crosslinking units increases, and therefore, even if b is 50 or less, the viscosity may be 300,000 mPas or more.
Specific examples of the component (a) include the following average composition formulae, but are not limited to these average composition formulae. In the following average composition formula, a, b, c, d, e, f are values such that the viscosity of the polyorganosiloxane at 25 ℃ satisfies 300,000 mPas or more, and a.gtoreq.2, and c + d.gtoreq.1. In addition, b + e + f in the average composition formula described below can typically take a value of 50 or more, and preferably a value of 100 or more.
[ chemical formula 4]
[ chemical formula 5]
[ chemical formula 6]
[ (B-1) component and (B-2) component ]
The components (B-1) and (B-2) are as follows.
(B-1) cationic surfactant: q1 3(CH3)N+·X-Wherein Q is1The organic group is a monovalent organic group having 6 to 30 carbon atoms, and X is a halogen atom or a monovalent carboxyl group having 1 to 6 carbon atoms.
(B-2) cationic surfactant: q2(CH3)3N+·X-Wherein Q is2Is a monovalent organic group having 17 to 30 carbon atoms, and X isA halogen atom or a monovalent carboxyl group having 1 to 6 carbon atoms.
The emulsion composition of the present invention contains 0.1 to 30 parts by mass of the component (B-1) and 0.1 to 30 parts by mass of the component (B-2) per 100 parts by mass of the component (A).
The cationic surfactants as the components (B-1) and (B-2) are used for emulsifying and dispersing polyorganosiloxane in water, but the present inventors considered that the following mechanism of action is available in addition to the mechanism of action as an emulsifier for the components (B-1) and (B-2). It is considered that in the method for producing a cationic emulsion composition of polyorganosiloxane according to the present invention, when the polyorganosiloxane is emulsified and dispersed in water and then the alkali catalyst is added, OH generated in the water phase-The polyorganosiloxane of component (A) can be more efficiently polymerized by exchanging the cationic surfactant itself with the counter ion (counter ion) of the cationic surfactants of component (B-1) and component (B-2) to function as a catalyst.
As mentioned above, the cationic surfactant as the component (B-1) is Q1 3(CH3)N+·X-Cationic surfactant represented by, Q1The same or different monovalent organic groups having 6 to 30 carbon atoms, preferably 7 to 18 carbon atoms. When Q is1When the number of carbon atoms of (2) is less than 6, the surfactant has excessively high hydrophilicity, the frequency of contact with the polyorganosiloxane of component (a) is low, and long-term polymerization is required to increase the polymerization degree of the polyorganosiloxane. In addition, when Q1When the number of carbon atoms of (2) is more than 30, the emulsifying power as a surfactant is weak, and a stable emulsion may not be obtained.
As Q1Specific examples of (3) include: alkyl groups such as hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, docosyl, cyclopentyl, cyclohexyl, and cycloheptyl;aryl groups such as phenyl, benzyl, tolyl, and naphthyl; alkenyl groups such as octadecenyl and the like. Among them, octyl, dodecyl, hexadecyl and octadecyl are preferable.
Further, X-Specifically, the halogen ion or the monovalent carboxylic acid ion having 1 to 6 carbon atoms includes: cl-、Br-、I-And the like; HCOO-、CH3COO-、C2H5COO-And the like. Among them, Cl is preferred-、HCOO-、CH3COO-。
Specific examples of the component (B-1) include, but are not limited to, trihexylmethylammonium chloride, triheptylmethylammonium chloride, trioctylmethylammonium chloride, trinonylmethylammonium chloride, tridecylmethylammonium chloride, trilaurylmethylammonium chloride, trioctylmethylammonium acetate, and trilaurylmethylammonium acetate.
The amount of the cationic surfactant as component (B-1) can be 0.1 to 30 parts by mass, preferably 0.5 to 20 parts by mass, and more preferably 1 to 15 parts by mass, based on 100 parts by mass of component (A). When the amount is less than 0.1 part by mass, the polymerization degree of the component (A) may not be efficiently increased during the polymerization, and when the amount is more than 30 parts by mass, the stability of the emulsion tends to be unstable.
Further, as described above, the cationic surfactant of the component (B-2) is Q2(CH3)3N+·X-The cationic surfactant can improve the stability of the emulsion. Here, Q2Is a monovalent organic group having 17 to 30 carbon atoms, preferably 18 to 28 carbon atoms. When Q is2When the number of carbon atoms of (2) is less than 17, the compatibility with the cationic surfactant represented by (B-1) is poor, and the stability of the emulsion may be lowered. When Q is2When the number of carbon atoms of (b) is more than 30, with Q1In the same manner as in the case of (3), the emulsifying power as a surfactant is weak, and a stable emulsion may not be obtained. Q2X of (2)-And the above Q1X of (2)-The same is true.
Specific examples of the component (B-2) include, but are not limited to, octadecyl trimethyl ammonium chloride, eicosyl trimethyl ammonium chloride, docosyl trimethyl ammonium chloride, octadecyl trimethyl ammonium acetate, eicosyl trimethyl ammonium acetate, docosyl trimethyl ammonium acetate, and the like.
The amount of the cationic surfactant as the component (B-2) can be 0.1 to 30 parts by mass, preferably 0.5 to 20 parts by mass, and more preferably 1 to 15 parts by mass, based on 100 parts by mass of the component (A). When the amount is less than 0.1 part by mass, the stability of the emulsion tends to become unstable, and when the amount is more than 30 parts by mass, the polymerization degree of the component (A) may not be efficiently increased during the polymerization.
Since the component (B-1) has higher hydrophobicity than the component (B-2), the contact frequency with the polyorganosiloxane of the component (A) is high, and the effect of increasing the polymerization rate can be expected. Therefore, when (B-1) alone is used, the stability of the emulsion with time may be deteriorated depending on the conditions such as the composition, particle diameter, viscosity and pH of the emulsion. Therefore, by using the component (B-2) having a higher emulsifying ability than the component (B-1), the stability of the emulsion can be improved at a higher polymerization rate.
In addition, in the cationic emulsion composition of polyorganosiloxane of the present invention, by using both a cationic surfactant and a nonionic surfactant, the emulsion can be easily made small in particle size, thereby improving the stability of the emulsion. Examples of the nonionic surfactant include polyoxyalkylene alkyl ether, polyoxyalkylene alkylphenyl ether, polyoxyalkylene alkyl ester, polyoxyalkylene sorbitol alkyl ester (polyoxyalkylene sorbitol alkyl ester), polyethylene glycol, polypropylene glycol, diethylene glycol, and one kind thereof may be used alone or two or more kinds thereof may be appropriately selected and used. Among them, nonionic surfactants represented by the following general formula (2) are preferable.
R4O(EO)P(PO)qH(2)
In the formula (2), R4Is C8-30Linear or branched alkyl, EO represents oxyethylene group, PO represents oxypropylene group, and these groups may be arranged in block or random form. p and q are independently integers of 0 to 100, and p + q > 0. In particular, in the above general formula (2), R4Preferably a linear or branched alkyl group having 8 to 18 carbon atoms, and p and q are preferably independently 0 to 25 and 0 < p + q.ltoreq.50.
Furthermore, the addition of the following surfactants for the purpose of complementing the stability of the emulsion and the like is not problematic: cationic surfactants such as quaternary ammonium salts and alkylamine acetates other than the components (B-1) and (B-2); amphoteric surfactants such as alkylbetaines and alkylimidazolines.
[ (C) ingredient ]
The emulsion composition of the present invention contains 30 to 3,000 parts by mass of water as component (C), preferably 40 to 2,400 parts by mass of water as component (C), per 100 parts by mass of component (A). If the amount of water is too small, the water-in-oil emulsion cannot be formed, and if it is too large, it is uneconomical.
[ method for producing emulsion composition ]
Next, the emulsion composition of the present invention is prepared as follows. That is, in the presence of an alkali catalyst, an emulsion obtained by emulsifying and dispersing the following components is polymerized at 0 to 30 ℃ for 1 to 150 hours and further neutralized:
100 parts by mass of (D) a compound of the general formula HO- [ R ]1 2SiO]jA double-terminal hydroxy polydiorganosiloxane represented by the formula (I) H, wherein R1Independently of one another, a monovalent organic group having 1 to 20 hydrogen atoms or carbon atoms, j being such that the polydiorganosiloxane having hydroxyl groups at both ends has a viscosity at 25 ℃ of less than 2,000 mPas;
0 to 20 parts by mass of (E) any one or two or more kinds of organoalkoxysilanes,
Si(OR3)4、R1Si(OR3)3、R1 2Si(OR3)2、R1 3Si(OR3)，
wherein R is1Independently of one another, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, R3Independently represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms;
0.1 to 30 parts by mass of (B-1) a cationic surfactant Q1 3(CH3)N+·X-，
Wherein Q1The same or different monovalent organic groups with 6-30 carbon atoms are used, and X is a halogen atom or monovalent carboxyl with 1-6 carbon atoms;
0.1 to 30 parts by mass of (B-2) a cationic surfactant Q2(CH3)3N+·X-，
Wherein Q is2Is a monovalent organic group having 17 to 30 carbon atoms, X is a halogen atom or a monovalent carboxyl group having 1 to 6 carbon atoms;
30 to 3,000 parts by mass of (C) water.
[ (D) component ]
First, the general formula HO- [ R ] as component (D)1 2SiO]jThe both terminal hydroxyl polydiorganosiloxane represented by the formula (H) is a raw material of the polyorganosiloxane as the component (A), wherein R is1Independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and j is a value such that the viscosity of the polydiorganosiloxane at both terminal ends at 25 ℃ satisfies a value of less than 2,000 mPas.
J in the above general formula can typically have a value of 1 to 400.
Specific examples of the component (D) include the following average composition formulas, but are not limited to these average composition formulas. J, k + l, and k + l + m in the average composition formula are values such that the viscosity of the both-terminal hydroxyl polydiorganosiloxane at 25 ℃ satisfies 2,000 mPas or less. In addition, j, k + l, and k + l + m in the following general formula can typically have values of 1 to 400.
[ chemical formula 7]
[ (E) ingredient ]
The organoalkoxysilane as the component (E) is a raw material of the polyorganosiloxane as the component (A), and is any one or two or more organoalkoxysilanes of the following general formula.
Si(OR3)4、R1Si(OR3)3、R1 2Si(OR3)2、R1 3Si(OR3)，
Wherein R is1Independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms. Examples of the monovalent organic group having 1 to 20 carbon atoms include: alkyl groups such as methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, cyclopentyl, cyclohexyl, and cycloheptyl; aryl groups such as phenyl, tolyl, and naphthyl; alkenyl groups such as vinyl and allyl; or a group in which a part of hydrogen atoms in the structure of these organic groups is substituted with a halogen atom or a polar group-containing organic group such as an amino group, an acryloyloxy group, a methacryloyloxy group, an epoxy group, a mercapto group, or the like. Here, R is preferable in terms of industrial and characteristic properties1More than 80% of the total amount of the compounds are methyl groups. Furthermore, R3Independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms. R is3A monovalent organic group having 1 to 20 carbon atoms and the above R1Similarly, methyl, ethyl, propyl, and butyl are preferable, and methyl and ethyl are more preferable.
The amount of the component (E) used is 0 to 20 parts by mass, preferably 0 to 15 parts by mass, per 100 parts by mass of the both-terminal hydroxy polydiorganosiloxane as the component (D). If the amount of the component (E) is too large, the coating film may become brittle and the durability may be reduced.
Specific examples of the component (E) include methyltrimethoxysilane, dimethyldimethoxysilane, phenyltrimethoxysilane, methyltriethoxysilane, dimethyldiethoxysilane, phenyltriethoxysilane, hexyltrimethoxysilane, hexyltriethoxysilane, decyltrimethoxysilane, trifluoropropyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2- (3, 4-epoxycyclohexyl) ethyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-vinyltrimethoxysilane, 3-methacryloxypropylmethyldimethoxysilane, p-methacryloxypropylmethyldimethoxysilane, and, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, N-2- (aminoethyl) -3-aminopropylmethyldimethoxysilane, N-2- (aminoethyl) -3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-triethoxysilyl-N- (1, 3-dimethyl-butenyl) propylamine, N-phenyl-3-aminopropyltrimethoxysilane, 3-ureidopropyltriethoxysilane, 3-mercaptopropylmethyldimethoxysilane, N-methyl-N-propyltrimethoxysilane, N-ethyl-3-aminopropyltriethoxysilane, N-methyl-N-propyltrimethoxysilane, N-propyl-3-ethylmethyldimethoxysilane, N-ethyltrimethoxysilane, N-butyltrimethoxysilane, N-butyltrimethoxysilane, N-butyltrimethoxysilane, N-butyltrimethoxysilane, N-butyltrimethoxysilane, N-butyltrimethoxysilane, N-N, 3-mercaptopropyltrimethoxysilane, bis (triethoxysilylpropyl) tetrasulfide, 3-isocyanatopropyltriethoxysilane, etc., but is not limited to these examples.
[ (B-1) component, (B-2) component, and (C) component ]
The components (B-1), (B-2) and (C) used in the method for producing the emulsion composition of the present invention are the same as described above.
These hydroxyl-terminated polydiorganosiloxanes as the component (D), organoalkoxysilanes as the component (E), the cationic surfactants as the components (B-1) and (B-2), and water as the component (C) are made into a uniform emulsion by using an emulsifying machine such as a homomixer (homomixer), a homogenizer (homogenerizer), a colloid mill (colloid mill), a homodisperser (homodisper), and a line mixer, and then an alkali catalyst is added thereto to carry out polymerization at 0 to 30 ℃ for 1 to 150 hours.
Examples of the alkali catalyst include sodium hydroxide, potassium hydroxide, lithium hydroxide, potassium fluoride, ammonia, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, tetrabutylphosphonium hydroxide, trifluoromethylphenyltrimethylammonium hydroxide, and the like. Among them, preferred are sodium hydroxide, potassium hydroxide, ammonia, tetramethylammonium hydroxide, tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, and tetrabutylphosphonium hydroxide.
The amount of the base catalyst used is preferably 0.01 to 5 parts by mass, more preferably 0.03 to 5 parts by mass, based on 100 parts by mass of the both-terminal hydroxyorganosiloxane as the component (D).
Further, when the cationic surfactants as the components (B-1) and (B-2) are made into quaternary ammonium hydroxide by using an ion exchange resin, the quaternary ammonium hydroxide itself functions as an alkali catalyst component, and thus it is not necessary to separately add an alkali catalyst. When the component (B-1) or the component (B-2) itself is used as the alkali catalyst component in this manner, it also corresponds to the polymerization of the emulsion obtained by emulsifying and dispersing the components (D), (E), (B-1), (B-2) and (C) in the presence of the alkali catalyst in the method for producing the emulsion composition of the present invention.
In addition, the polymerization temperature is 0 to 30 ℃. When the temperature is lower than 0 ℃, the polymerization proceeds slowly and is not practical, and when the temperature is higher than 30 ℃, the stability of the emulsion becomes unstable. The polymerization temperature is preferably 5 to 25 ℃. In addition, the polymerization time is 1 to 150 hours. When the time is less than 1 hour, the polymerization is insufficient, and when it is longer than 150 hours, it becomes unsuitable for industrial use. The polymerization time is preferably 5 to 120 hours.
The polymerization reaction can be stopped by neutralizing after a predetermined polymerization time. Neutralization here can be carried out using an acidic compound. Examples of the acidic compound include hydrochloric acid, formic acid, acetic acid, and propionic acid, and hydrochloric acid, formic acid, and acetic acid are preferable. Instead of using an acidic compound, an ion exchange resin may be used for neutralization.
The cationic emulsion composition of the high-polymerization organosiloxane obtained by the above method can be suitably used as a fiber treatment agent, a release agent, a water repellent, a cosmetic raw material, and the like, and can impart excellent softness, lubricity, water repellency, volume feeling, and the like by treating various fibers, leather, paper, hair, and the like. Further, examples of the fibers include: natural fibers such as cotton, hemp, silk, and wool; synthetic fibers of polyester, polyamide, polyacrylonitrile, polyethylene, polypropylene, vinylon, polyvinyl chloride, spandex (spandex), and the like; and semi-synthetic fibers such as acetate fibers, but are not limited to these fibers.
Various thickeners, pigments, dyes, penetrants, antistatic agents, antifoaming agents, flame retardants, antibacterial agents, preservatives, water repellents, crosslinking agents, adhesion promoters, or other silicone oils, silicone resins, silica, acrylic resins, urethane resins, and the like can be appropriately blended into the cationic emulsion composition of high-polymerization-degree organosiloxane of the present invention.
The cationic emulsion composition of the high-polymerization organosiloxane of the present invention can form a coating film after drying, and can be used for treating the surface of various substrates such as fibers, paper, metal, wood, rubber, plastic, glass, and the like. The coating method for the substrate may be any of various conventionally known coating methods such as a dipping method, a spraying method, a roll coating method, a bar coating method, and a brush coating method.
Examples
The present invention will be specifically described below by way of examples and comparative examples, but the present invention is not limited to the following examples. In the following examples, "%" represents "% by mass".
[ example 1]
300g of HO- [ (CH) was added by using a homomixer or disperser3)2SiO]nBoth terminal hydroxypolydimethylsiloxane represented by (H) (component (D)), wherein n is about 310 and the viscosity at 25 ℃ is 1,500 mPas, (E) component, 4.3g of triethoxyphenylsilane, 24.0g of trioctylmethylammonium chloride, component (B-1), as an active ingredient, is a 75% IPA (isopropyl alcohol) solution (TOMAC-75: Lion Specialty Chemicals Co., Ltd.), 18.0g of behenyltrioctylammonium chloride, component (B-2), as an active ingredient, is 80% ethanol product (LIPOQUAD 22-80: Lion Specialty Chemicals Co., Ltd.), 2393g of ion-exchanged water (component (C)) was uniformly emulsified and dispersed, thereby obtaining an emulsion. To this emulsion was added 6.6g of a 30% aqueous ammonia solution (base catalyst). Then, the liquid temperature was lowered to 15 ℃ and polymerization was carried out for 24 hours, and neutralization was carried out with 7.8g of acetic acid, thereby obtaining emulsion a.
[ example 2]
Emulsion B was obtained in the same manner as in example 1, except that the ion exchange water of example 1 was changed to 215.3g, and 24.0g of polyoxyethylene alkyl ether EMULGEN 109P (manufactured by Kao Corporation) as a nonionic emulsifier was further added.
[ example 3]
Emulsion C was obtained in the same manner as in example 2, except that the IPA solution (TOMAC-75: manufactured by Lion Specialty Chemicals co., ltd.) containing 75% as an active ingredient of the trioctylmethylammonium chloride in example 2 was changed to 3.0g, and the ion-exchanged water was changed to 236.3 g.
[ example 4]
Emulsion D was obtained in the same manner as in example 2, except that the IPA solution (TOMAC-75: Lion Specialty Chemicals co., ltd. manufactured) containing 75% of the active ingredient of trioctylmethylammonium chloride in example 2 was changed to 12.0g, and ion-exchanged water was changed to 227.3 g.
[ example 5]
Emulsion E was obtained in the same manner as in example 4, except that the polymerization conditions in example 4 were set to polymerization carried out at 15 ℃ for 48 hours.
[ example 6]
Emulsion F was obtained in the same manner as in example 4, except that the ion-exchanged water of example 4 was changed to 231.6g, and 2.3g of 85% KOH was added instead of the 30% aqueous ammonia solution.
Comparative example 1
Emulsion G was obtained in the same manner as in example 1 except that the amount of triethoxyphenylsilane in example 1 was changed to 1.1G, the amount of ion-exchanged water was changed to 258.7G, and further an IPA solution (TOMAC-75: manufactured by Lion Specialty Chemicals Co., Ltd.) containing 75% as the active ingredient of trioctylmethylammonium chloride and an ethanol product (LIPOQUAD 22-80: Ligon Specialty Chemicals Co., Ltd.) containing 80% as the active ingredient of docosyltrimethyleneammonium chloride were changed to 25.8G of an aqueous solution (QUARTAMIN 60W: manufactured by KaARTO Corporation) containing 30% as the active ingredient of cetyltrimethylammonium chloride were changed to 258.1G.
Comparative example 2
Emulsion H was obtained in the same manner as in comparative example 1, except that the polymerization conditions in comparative example 1 were set to carry out polymerization at 15 ℃ for 96 hours.
Comparative example 3
Emulsion I was obtained in the same manner as in comparative example 1, except that the amount of triethoxyphenylsilane in comparative example 1 was changed to 4.3g, and the amount of ion-exchanged water was changed to 255.5 g.
Comparative example 4
Emulsion J was obtained in the same manner as in comparative example 3, except that the 30% aqueous solution of cetyltrimethylammonium chloride as the active ingredient (QUARTAMIN 60W: manufactured by Kao Corporation) in comparative example 3 was changed to a 75% IPA solution of trioctylmethylammonium chloride as the active ingredient (TOMAC-75: Lion Specialty Chemicals Co., manufactured by Ltd.) in an amount of 24.0g, and the ion-exchanged water was changed to 257.3 g.
Comparative example 5
The production was carried out in the same manner as in comparative example 4 except that 25.8g of an aqueous solution (QUARTAMIN 60W: manufactured by Kao Corporation) containing 30% of cetyltrimethylammonium chloride as an active ingredient was added to comparative example 4 and the amount of ion-exchanged water was changed to 231.5g, but since emulsion K could not be produced with this composition, evaluation of physical properties and characteristics was not carried out.
Comparative example 6
300g of a linear dimethylsilicone oil having a viscosity of 800,000 mPas at 25 ℃, 21.6g of an aqueous solution (QUARTAMIN 60W: manufactured by Kao Corporation) containing 30% of an active ingredient of cetyltrimethylammonium chloride, and 235.2g of ion-exchanged water were uniformly emulsified and dispersed by a homomixer and a disperser to obtain emulsion L.
The physical properties and properties of the emulsions obtained in examples 1 to 6 and comparative examples 1 to 6 were measured by the following evaluation methods, and the results are shown in tables 1 and 2.
(viscosity of extracted polysiloxane)
The emulsion was broken by adding 300g of the emulsions A to L to 2L of IPA under stirring to extract the polydiorganosiloxane, and after drying the polydiorganosiloxane at 105 ℃ for 3 hours, the viscosity was measured at 25 ℃ using a BH type rotational viscometer. The viscosity can be measured directly when measured in a liquid state, and when the viscosity is too high to be measured, the 10% toluene dissolution viscosity is measured. The viscosity was 300,000 mPas or more in all cases when the viscosity was too high to be measured.
(whether or not to form a coating film)
20g of each of the emulsions A to L was dispensed onto a PP (polypropylene) tray, and the resultant was dried at 25 ℃ for 48 hours, and then further dried at 105 ℃ for 1 hour to evaluate whether or not a coating film was formed.
O: a coating film is formed
X: no coating film was formed (kept in liquid state)
(storage stability)
The appearance after standing at 25 ℃ for 1 month was visually evaluated.
O: without separation
And (delta): slightly separated from each other
X: complete separation
(texture of treatment cloth)
Treatment liquids were prepared by diluting emulsions A to L with ion-exchanged water so that the polyorganosiloxane concentration became 1%. A polyester cotton plain cloth (T/C broadcloth) was immersed in the treatment solution for 10 seconds, then padded with a roller at a padding ratio of 100%, and dried at 150 ℃ for 2 minutes. The treated cloth was then evaluated for hand and was more flexible and smooth than the untreated cloth.
O: is good
X: grade of untreated cloth
(washing durability of treatment cloth)
Treatment liquids were prepared by diluting emulsions A to L with ion-exchanged water so that the polyorganosiloxane concentration became 1%. After immersing the polyester cotton plain cloth in the treatment solution for 10 seconds, the cloth was subjected to padding using a roller at a padding ratio of 100%, and dried at 150 ℃ for 2 minutes. Then, the treated cloths were cut in half, and one of them was washed once by a method based on JIS L0217103 using a washing machine, and then dried at room temperature for one day. The amount of residual polysiloxane on the fiber surface of the treated cloth before and after washing was measured by an X-ray fluorescence analysis apparatus (manufactured by Rigaku Corporation), and the residual rate (%) after washing was calculated.
[ Table 1]
[ Table 2]
As shown in tables 1 and 2, the cationic emulsion composition of polyorganosiloxane with high degree of polymerization of the present invention can polymerize in a relatively short time even at high viscosity, and has the ability to form a coating film, so that the cationic emulsion composition has excellent durability when it is used for treating fibers, and the treated fabric has good texture. Further, the cationic emulsion composition of a polyorganosiloxane with a high polymerization degree of the present invention is also excellent in storage stability. On the other hand, the cationic emulsion composition obtained from the composition of comparative example had no film-forming ability although it had high stability, and had poor durability when subjected to fiber treatment, or had a film-forming ability but had low emulsion stability and separated quickly.
Industrial applicability
When the cationic emulsion composition of a polyorganosiloxane with a high polymerization degree of the present invention is used as a fiber treatment agent, good flexibility can be imparted to fibers and the fibers are excellent in durability, and thus good flexibility can be maintained even after washing treatment. Further, when the cationic emulsion composition of polyorganosiloxane with high polymerization degree of the present invention is treated and dried, the formed coating film has high durability and therefore is excellent in versatility, and can be widely used for a release agent, a water repellent agent, a cosmetic, a hair cosmetic, and the like, in addition to a fiber treatment agent.
Claims (9)
1. A cationic emulsion composition of polyorganosiloxane, characterized in that it contains:
100 parts by mass of (A) a polyorganosiloxane represented by the average composition formula (1) below and having a viscosity of 300,000 mPas or more at 25 ℃,
[ chemical formula 1]
In the formula (1), R1Independently of one another, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, R2Independently of one another are selected from the abovementioned radicals R1A, b, c and d are values such that the viscosity of the polyorganosiloxane at 25 ℃ satisfies 300,000 mPas or more, a is not less than 2, and c + d is not less than 1;
0.1 to 30 parts by mass of (B-1) a cationic surfactant Q1 3(CH3)N+·X-，
Wherein Q1The organic group is a monovalent organic group with 6-30 carbon atoms of the same or different types, and X is a halogen atom or a monovalent carboxyl group with 1-6 carbon atoms;
0.1 to 30 parts by mass of (B-2) a cationic surfactant Q2(CH3)3N+·X-，
Wherein Q2Is a monovalent organic group having 17 to 30 carbon atoms, X is a halogen atom or a monovalent carboxyl group having 1 to 6 carbon atoms;
30 to 3,000 parts by mass of (C) water.
2. Cationic emulsion composition of polyorganosiloxanes according to claim 1, characterized in that it further comprises a nonionic surfactant.
3. The cationic polyorganosiloxane emulsion composition according to claim 1 or 2, wherein a coating film is formed after drying.
4. A fiber-treating agent comprising the cationic emulsion composition of polyorganosiloxane according to any one of claims 1 to 3.
5. A mold release agent comprising the cationic emulsion composition of the polyorganosiloxane according to any one of claims 1 to 3.
6. A water repellent agent comprising a cationic emulsion composition of the polyorganosiloxane according to any one of claims 1 to 3.
7. A cosmetic composition comprising the polyorganosiloxane according to any one of claims 1 to 3.
8. A cosmetic for hair, characterized by comprising a cationic emulsion composition of the polyorganosiloxane according to any one of claims 1 to 3.
9. A method for producing a cationic emulsion composition of polyorganosiloxane, characterized by polymerizing an emulsion obtained by emulsifying and dispersing the following components at 0 to 30 ℃ for 1 to 150 hours in the presence of an alkali catalyst, and further neutralizing the emulsion:
100 parts by mass of (D) a compound of the general formula HO- [ R ]1 2SiO]jA double-terminal hydroxy polydiorganosiloxane represented by the formula (I) wherein R is1Independently of one another, a monovalent organic group having 1 to 20 hydrogen atoms or carbon atoms, j being such that the polydiorganosiloxane having hydroxyl groups at both ends has a viscosity at 25 ℃ of less than 2,000 mPas;
0 to 20 parts by mass of (E) any one or two or more kinds of organoalkoxysilanes,
Si(OR3)4、R1Si(OR3)3、R1 2Si(OR3)2、R1 3Si(OR3)，
wherein R is1Independently of one another, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, R3Independently represents a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms;
0.1 to 30 parts by mass of (B-1) a cationic surfactant Q1 3(CH3)N+·X-，
Wherein Q is1The organic group is a monovalent organic group with 6-30 carbon atoms of the same or different types, and X is a halogen atom or a monovalent carboxyl group with 1-6 carbon atoms;
0.1 to 30 parts by mass of (B-2) a cationic surfactant Q2(CH3)3N+·X-，
Wherein Q2Is a monovalent organic group having 17 to 30 carbon atoms, X is a halogen atom or a monovalent carboxyl group having 1 to 6 carbon atoms;
30 to 3,000 parts by mass of (C) water.
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| JP2019225634A JP7368217B2 (en) | 2019-12-13 | 2019-12-13 | Cationic emulsion composition of polyorganosiloxane and method for producing the same |
| JP2019-225634 | 2019-12-13 | ||
| PCT/JP2020/044236 WO2021117508A1 (en) | 2019-12-13 | 2020-11-27 | Cationic emulsion composition of polyorganosiloxane, and method for producing same |
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| US5973066A (en) * | 1997-11-17 | 1999-10-26 | Shin-Etsu Chemical Co., Ltd. | Oil-in-water aqueous organopolysiloxane emulsion and method for the preparation thereof |
| CN1239419A (en) * | 1996-11-04 | 1999-12-22 | 普罗克特和甘保尔公司 | Hair conditioning compsn. comprising silicone emulsion |
| JP2005089372A (en) * | 2003-09-18 | 2005-04-07 | Lion Corp | Hair cosmetic |
| JP2005179337A (en) * | 2003-11-28 | 2005-07-07 | Kose Corp | Hair cosmetic |
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| JPS5638609A (en) | 1979-09-05 | 1981-04-13 | Toshiba Corp | Monitoring method for plant |
| US5504149A (en) | 1994-08-25 | 1996-04-02 | Dow Corning Corporation | Method of emulsion polymerization |
| GB2303857B (en) | 1995-07-28 | 1999-05-26 | Gen Electric | Cationic surfactant compatible anionic emulsion polymerized silicone emulsions |
| JP3335842B2 (en) | 1995-08-07 | 2002-10-21 | ジーイー東芝シリコーン株式会社 | Method for producing silicone emulsion |
| JPH10140480A (en) | 1996-11-07 | 1998-05-26 | Toshiba Silicone Co Ltd | Textile treating agent |
| JP2001106787A (en) | 1999-10-05 | 2001-04-17 | Shin Etsu Chem Co Ltd | Method for producing organopolysiloxane emulsion |
| JP4683203B2 (en) * | 2005-05-31 | 2011-05-18 | 信越化学工業株式会社 | Cationic emulsion composition of highly polymerized organosiloxane and process for producing the same |
| DE102007030642A1 (en) * | 2007-07-02 | 2009-01-08 | Momentive Performance Materials Gmbh | Process for the preparation of polyorganosiloxanes having (C6-C60) -alkylmethylsiloxy groups and dimethylsiloxy groups |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1239419A (en) * | 1996-11-04 | 1999-12-22 | 普罗克特和甘保尔公司 | Hair conditioning compsn. comprising silicone emulsion |
| US5973066A (en) * | 1997-11-17 | 1999-10-26 | Shin-Etsu Chemical Co., Ltd. | Oil-in-water aqueous organopolysiloxane emulsion and method for the preparation thereof |
| JP2005089372A (en) * | 2003-09-18 | 2005-04-07 | Lion Corp | Hair cosmetic |
| JP2005179337A (en) * | 2003-11-28 | 2005-07-07 | Kose Corp | Hair cosmetic |
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