KR20220115562A - Cationic emulsion composition of polyorganosiloxane and method for preparing the same - Google Patents
Cationic emulsion composition of polyorganosiloxane and method for preparing the same Download PDFInfo
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- KR20220115562A KR20220115562A KR1020227019381A KR20227019381A KR20220115562A KR 20220115562 A KR20220115562 A KR 20220115562A KR 1020227019381 A KR1020227019381 A KR 1020227019381A KR 20227019381 A KR20227019381 A KR 20227019381A KR 20220115562 A KR20220115562 A KR 20220115562A
- Authority
- KR
- South Korea
- Prior art keywords
- polyorganosiloxane
- carbon atoms
- mass
- emulsion composition
- group
- Prior art date
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- 239000000839 emulsion Substances 0.000 title claims abstract description 109
- 239000000203 mixture Substances 0.000 title claims abstract description 74
- 125000002091 cationic group Chemical group 0.000 title claims abstract description 42
- 238000000034 method Methods 0.000 title claims description 13
- 239000003093 cationic surfactant Substances 0.000 claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 56
- 125000000962 organic group Chemical group 0.000 claims description 43
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 239000003054 catalyst Substances 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- 239000000835 fiber Substances 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 239000003513 alkali Substances 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 230000001804 emulsifying effect Effects 0.000 claims description 14
- 239000002537 cosmetic Substances 0.000 claims description 11
- 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 5
- 210000004209 hair Anatomy 0.000 claims description 5
- 239000002736 nonionic surfactant Substances 0.000 claims description 5
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000006116 polymerization reaction Methods 0.000 description 45
- -1 polysiloxane Polymers 0.000 description 35
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 17
- 229920001296 polysiloxane Polymers 0.000 description 15
- 239000004480 active ingredient Substances 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
- 239000000243 solution Substances 0.000 description 9
- 241000282320 Panthera leo Species 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 238000005406 washing Methods 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910052799 carbon Chemical group 0.000 description 5
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004094 surface-active agent Substances 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 150000001875 compounds Chemical class 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
- 239000006082 mold release agent Substances 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
- 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
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000003342 alkenyl group Chemical group 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 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
- 238000000576 coating method Methods 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
- 239000003995 emulsifying agent Substances 0.000 description 3
- 125000003700 epoxy group Chemical group 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
- 239000007791 liquid phase Substances 0.000 description 3
- 239000000463 material Substances 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
- 238000006386 neutralization reaction Methods 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
- 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
- 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
- CPZHPNSUWUBSQW-UHFFFAOYSA-M CCCCCCCCCCCCCCCCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.[Cl-] Chemical compound CCCCCCCCCCCCCCCCCCCCCC[N+](CCCCCCCC)(CCCCCCCC)CCCCCCCC.[Cl-] CPZHPNSUWUBSQW-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 125000003118 aryl group Chemical group 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
- 125000004122 cyclic group Chemical group 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000010556 emulsion polymerization method Methods 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000003676 hair preparation Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 235000011167 hydrochloric acid Nutrition 0.000 description 2
- 239000003456 ion exchange resin Substances 0.000 description 2
- 229920003303 ion-exchange polymer Polymers 0.000 description 2
- 239000007788 liquid Substances 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
- 230000000379 polymerizing 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
- 238000007142 ring opening reaction Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 2
- DFQPZDGUFQJANM-UHFFFAOYSA-M tetrabutylphosphanium;hydroxide Chemical compound [OH-].CCCC[P+](CCCC)(CCCC)CCCC DFQPZDGUFQJANM-UHFFFAOYSA-M 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
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-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
- PRKPGWQEKNEVEU-UHFFFAOYSA-N 4-methyl-n-(3-triethoxysilylpropyl)pentan-2-imine Chemical compound CCO[Si](OCC)(OCC)CCCN=C(C)CC(C)C PRKPGWQEKNEVEU-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 1
- WHCKIPKZERFOAS-UHFFFAOYSA-M CCCCCCCCCCCCCCCCCCCC[N+](C)(C)C.CC(=O)[O-] Chemical compound CCCCCCCCCCCCCCCCCCCC[N+](C)(C)C.CC(=O)[O-] WHCKIPKZERFOAS-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
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 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
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 229920002334 Spandex Polymers 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
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000008346 aqueous phase 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
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 229960003237 betaine Drugs 0.000 description 1
- 230000001680 brushing effect Effects 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
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000007423 decrease Effects 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
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
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- ZUZLIXGTXQBUDC-UHFFFAOYSA-N methyltrioctylammonium Chemical compound CCCCCCCC[N+](C)(CCCCCCCC)CCCCCCCC ZUZLIXGTXQBUDC-UHFFFAOYSA-N 0.000 description 1
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- 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
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- 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
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- 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
- 239000004753 textile Substances 0.000 description 1
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- 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
- 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
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- 210000002268 wool Anatomy 0.000 description 1
Classifications
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- 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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- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
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- 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
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- 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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- 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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- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
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- C08G77/06—Preparatory processes
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- C08K5/19—Quaternary ammonium compounds
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- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
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Abstract
본 발명은, (A)하기 평균조성식(1)로 표시되는, 25℃에 있어서의 점도가 300,000mPa·s 이상인 폴리오가노실록산: 100질량부, (B-1)양이온계 계면활성제: Q1 3(CH3)N+·X-: 0.1~30질량부, (B-2)양이온계 계면활성제: Q2(CH3)3N+·X-: 0.1~30질량부, (C)물: 30~3,000질량부를 함유하여 이루어지는 폴리오가노실록산의 양이온계 에멀전 조성물이다. 이에 따라, 점도가 300,000mP·s 이상으로 높고, 또한 안정성 및 내구성이 양호한 폴리오가노실록산의 양이온계 에멀전 조성물이 제공된다.
Description
본 발명은, 폴리오가노실록산의 양이온계 에멀전 조성물 및 그의 제조방법에 관한 것이다.The present invention relates to a cationic emulsion composition of polyorganosiloxane and a method for preparing the same.
폴리오가노실록산은, 기재에 처리함으로써 평활성이나 발수성을 부여할 수 있는 점에서, 섬유처리제, 이형제, 발수제, 화장료, 모발용 화장료 등에 사용되고 있다. 그 중에서도 고중합의 폴리실록산은, 평활성의 부여효과는 우수하다. 또한, 이들 폴리실록산을 유화할 때의 계면활성제로서, 4급 암모늄염과 같은 양이온계 계면활성제를 사용하면 폴리실록산의 기재에의 흡착성이 향상되는 것도 알려져 있다. 이 때문에, 고중합도의 폴리실록산을 양이온계 계면활성제로 유화한 에멀전의 요구가 높았다.Polyorganosiloxane is used for a fiber treatment agent, a mold release agent, a water repellent agent, cosmetics, hair cosmetics, etc. at the point which can provide smoothness and water repellency by treating a base material. Among them, highly polymerized polysiloxane is excellent in the effect of imparting smoothness. Moreover, it is also known that the adsorption property to the base material of polysiloxane improves when a cationic surfactant like a quaternary ammonium salt is used as surfactant at the time of emulsifying these polysiloxanes. For this reason, the demand for the emulsion which emulsified polysiloxane of high polymerization degree with a cationic surfactant was high.
폴리실록산의 에멀전화로 일반적인 방법은, 폴리실록산과 계면활성제를 유화기의 기계적인 쉐어(シェア)로 수중에 유화분산시키는 방법인데, 고중합도의 폴리실록산으로는 점도가 너무 높아 균일하게 기계적인 쉐어를 가할 수 없어, 안정된 에멀전을 얻을 수는 없다.The general method for emulsifying polysiloxane is to emulsify and disperse polysiloxane and surfactant in water with the mechanical shear of the emulsifier. , it is not possible to obtain a stable emulsion.
고중합도의 폴리실록산에멀전을 얻는 방법으로는, 실록산모노머의 에멀전을, 산 또는 알칼리촉매를 이용하여, 에멀전 중에서 중합시키는 유화중합법(특허문헌 1, 2)이 알려져 있다. 그러나, 이러한 유화중합법에 있어서는, 문헌에 기재된 염화세틸트리메틸암모늄으로 대표되는 4급 암모늄염과 같은 양이온계 계면활성제를 사용한 경우에는, 중합속도가 매우 느리기 때문에 고중합도화하기에 장시간을 요한다. 공업적으로 실용적 한계라고 생각되는 150시간 정도의 중합을 행해도, 폴리실록산은 추출 후의 점도가 수만mPa·s 레벨까지밖에 중합하지 않는다.As a method of obtaining a polysiloxane emulsion having a high degree of polymerization, an emulsion polymerization method in which an emulsion of a siloxane monomer is polymerized in the emulsion using an acid or an alkali catalyst (Patent Documents 1 and 2) is known. However, in such an emulsion polymerization method, when a cationic surfactant such as a quaternary ammonium salt represented by cetyltrimethylammonium chloride described in the literature is used, the polymerization rate is very slow, and thus a long time is required to achieve a high degree of polymerization. Even if polymerization is performed for about 150 hours, which is considered to be an industrially practical limit, polysiloxane only polymerizes to a level of tens of thousands of mPa·s in viscosity after extraction.
고중합도 폴리실록산의 양이온계 에멀전을 얻는 방법으로서, 실라놀레이트 촉매로 중합하는 방법(특허문헌 3), 암모늄하이드록사이드 촉매로 중합하는 방법(특허문헌 4)도 제안되어 있는데, 마찬가지로 중합도 레벨이 불충분하다.As a method of obtaining a cationic emulsion of high polymerization degree polysiloxane, a method of polymerization with a silanolate catalyst (Patent Document 3) and a method of polymerization with an ammonium hydroxide catalyst (Patent Document 4) have also been proposed, but similarly, the polymerization degree level is insufficient. do.
또한, 음이온계 계면활성제로 고중합 폴리실록산에멀전을 제조한 후에 양이온계 계면활성제를 첨가하는 방법(특허문헌 5, 6)도 제안되어 있는데, 음이온계 계면활성제를 병용하고 있으므로 안정성에 문제가 있다.In addition, a method of adding a cationic surfactant after preparing a highly polymerized polysiloxane emulsion with an anionic surfactant (Patent Documents 5 and 6) has also been proposed, but since the anionic surfactant is used in combination, there is a problem in stability.
나아가, 2단계의 온도조건으로 중합을 행하는 방법(특허문헌 7)도 제안되어 있는데, 고중합도화하려면 장시간의 중합시간을 요하는 것과 같은 문제가 있다.Furthermore, a method of performing polymerization under two-step temperature conditions (Patent Document 7) has also been proposed, but there is a problem that a long polymerization time is required to achieve a high degree of polymerization.
또한 최근, 섬유처리제 분야에 있어서, 고중합도 폴리실록산만으로는 달성이 곤란한 레벨의 세탁내구성이 요구되는 경우가 많아지고 있다. 고중합도 폴리실록산의 에멀전에 실리카 등의 피막보강제를 첨가함으로써 피막의 강도를 높여 내구성을 향상시키는 예도 있는데, 실리카의 첨가로 인해 안정성이 저하되는 일이나, 제조공정이 증가하는 등의 문제도 있다.In addition, in recent years, in the field of textile treatment agents, washing durability of a level that is difficult to achieve with only high polymerization polysiloxane is being required in many cases. There are also examples of improving durability by increasing the strength of the film by adding a film reinforcing agent such as silica to the emulsion of high polymerization degree polysiloxane.
본 발명은, 상기 사정을 감안하여 이루어진 것으로, 점도가 300,000mP·s 이상으로 높고, 또한 안정성 및 내구성이 양호한 폴리오가노실록산의 양이온계 에멀전 조성물을 제공하는 것을 목적으로 한다. 본 발명은, 그러한 에멀전 조성물을 비교적 단시간에 중합시킬 수 있는 제조방법을 제공하는 것을 목적으로 한다.The present invention has been made in view of the above circumstances, and an object of the present invention is to provide a cationic emulsion composition of polyorganosiloxane having a high viscosity of 300,000 mP·s or more, and good stability and durability. An object of the present invention is to provide a production method capable of polymerizing such an emulsion composition in a relatively short time.
상기 목적을 해결하기 위해, 본 발명은,In order to solve the above object, the present invention,
(A)하기 평균조성식(1)로 표시되는, 25℃에 있어서의 점도가 300,000mPa·s 이상인 폴리오가노실록산: 100질량부,(A) Polyorganosiloxane having a viscosity of 300,000 mPa·s or more at 25°C, represented by the following average composition formula (1): 100 parts by mass;
[화학식 1][Formula 1]
(식 중, R1은, 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이며, R2는, 서로 독립적으로, 상기 R1의 선택지로부터 선택되는 기, 하이드록시기, 또는 탄소수 1~20의 알콕시기이며, a, b, c, d는 이 폴리오가노실록산의 25℃에 있어서의 점도가 300,000mPa·s 이상을 만족시키는 값이며, a≥2, c+d≥1이다.)(Wherein, R 1 is, independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and R 2 is, independently of each other, a group selected from the options of R 1 above, a hydroxyl group, Or it is a C1-C20 alkoxy group, a, b, c, and d are a value which the viscosity in 25 degreeC of this polyorganosiloxane satisfy|fills 300,000 mPa*s or more, a≥2, c+d≥1 to be.)
(B-1)양이온계 계면활성제: Q1 3(CH3)N+·X-: 0.1~30질량부,(B-1) cationic surfactant: Q 1 3 (CH 3 )N + ·X - : 0.1 to 30 parts by mass;
(여기서, Q1은, 동일 또는 이종의 탄소수 6~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)(Here, Q 1 is the same or different 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)양이온계 계면활성제: Q2(CH3)3N+·X-: 0.1~30질량부,(B-2) cationic surfactant: Q 2 (CH 3 ) 3 N + X - : 0.1 to 30 parts by mass,
(여기서, Q2는, 탄소수 17~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)(Here, Q 2 is 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.)
(C)물: 30~3,000질량부(C) Water: 30 to 3,000 parts by mass
를 함유하여 이루어지는 것을 특징으로 하는 폴리오가노실록산의 양이온계 에멀전 조성물을 제공한다.It provides a cationic emulsion composition of polyorganosiloxane, characterized in that it contains a.
이러한 폴리오가노실록산의 양이온계 에멀전 조성물은, 점도가 높은 고중합 폴리오가노실록산의 양이온계 에멀전 조성물이며, 또한, 안정성이 양호하며, 또한 내구성도 양호하다.Such a cationic emulsion composition of polyorganosiloxane is a cationic emulsion composition of highly polymerized polyorganosiloxane having a high viscosity, and has good stability and good durability.
이때, 본 발명의 에멀전 조성물은, 추가로 비이온계 계면활성제를 포함하는 것이 바람직하다.At this time, it is preferable that the emulsion composition of the present invention further contains a nonionic surfactant.
이와 같이, 양이온계 계면활성제 외에, 비이온계 계면활성제를 병용함으로써 에멀전의 소입경화가 용이해지고, 이로 인해 에멀전의 안정성의 향상으로 이어진다.As described above, small particle hardening of the emulsion is facilitated by using a nonionic surfactant in addition to the cationic surfactant, which leads to an improvement in the stability of the emulsion.
또한, 본 발명의 에멀전 조성물은, 건조 후에 피막을 형성하는 것이 바람직하다.Moreover, it is preferable that the emulsion composition of this invention forms a film after drying.
이와 같이, 본 발명의 에멀전 화합물은, 건조하여 피막을 형성하는 것이 가능하다.As described above, the emulsion compound of the present invention can be dried to form a film.
또한, 본 발명은, 상기의 폴리오가노실록산의 양이온계 에멀전 조성물을 포함하는 것을 특징으로 하는 섬유처리제를 제공한다.In addition, the present invention provides a fiber treatment agent comprising the above polyorganosiloxane cationic emulsion composition.
또한, 본 발명은, 상기의 폴리오가노실록산의 양이온계 에멀전 조성물을 포함하는 것을 특징으로 하는 이형제를 제공한다.In addition, the present invention provides a release agent comprising the above-described polyorganosiloxane cationic emulsion composition.
또한, 본 발명은, 상기의 폴리오가노실록산의 양이온계 에멀전 조성물을 포함하는 것을 특징으로 하는 발수제를 제공한다.In addition, the present invention provides a water repellent comprising the cationic emulsion composition of the polyorganosiloxane described above.
또한, 본 발명은, 상기의 폴리오가노실록산의 양이온계 에멀전 조성물을 포함하는 것을 특징으로 하는 화장료를 제공한다.In addition, the present invention provides a cosmetic comprising the above polyorganosiloxane cationic emulsion composition.
또한, 본 발명은, 상기의 폴리오가노실록산의 양이온계 에멀전 조성물을 포함하는 것을 특징으로 하는 모발용 화장료를 제공한다.In addition, the present invention provides a hair cosmetic comprising the above polyorganosiloxane cationic emulsion composition.
이와 같이, 본 발명의 폴리오가노실록산의 양이온계 에멀전 조성물은, 섬유처리제, 이형제, 발수제, 화장료, 모발용 화장료에 포함되는 성분으로서 호적하게 사용할 수 있다.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 mold release agent, a water repellent agent, a cosmetic, and a hair cosmetic.
또한, 본 발명은,In addition, the present invention,
(D)일반식: HO-[R1 2SiO]j-H로 표시되는 양말단 하이드록시폴리디오가노실록산(여기서, R1은, 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이며, j는 이 양말단 하이드록시폴리디오가노실록산의 25℃에 있어서의 점도가 2,000mPa·s 미만을 만족시키는 값이다.): 100질량부,(D) general formula: HO-[R 1 2 SiO] j -H both terminal hydroxypolydiorganosiloxane represented by -H (here, R 1 is, independently of each other, a hydrogen atom, or 1 having 1 to 20 carbon atoms) is an organic group, and j is a value with which the viscosity at 25°C of both terminal hydroxypolydiorganosiloxane satisfies less than 2,000 mPa·s.): 100 parts by mass;
(E)하기에 나타내는 어느 1개 또는 2개 이상의 오가노알콕시실란: 0~20질량부(E) any one or two or more organoalkoxysilanes shown below: 0 to 20 parts by mass
Si(OR3)4, R1Si(OR3)3, R1 2Si(OR3)2, R1 3Si(OR3)Si(OR 3 ) 4 , R 1 Si(OR 3 ) 3 , R 1 2 Si(OR 3 ) 2 , R 1 3 Si(OR 3 )
(여기서, R1은 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이며, R3은 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이다.),(Here, R 1 is, independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and R 3 is, independently of each other, a hydrogen atom, or a monovalent organic group having 1 to 20 carbon atoms.) ,
(B-1)양이온계 계면활성제: Q1 3(CH3)N+·X-: 0.1~30질량부,(B-1) cationic surfactant: Q 1 3 (CH 3 )N + ·X - : 0.1 to 30 parts by mass;
(여기서, Q1은 동일 또는 이종의 탄소수 6~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)(Here, Q 1 is the same or different 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)양이온계 계면활성제: Q2(CH3)3N+·X-: 0.1~30질량부,(B-2) cationic surfactant: Q 2 (CH 3 ) 3 N + X - : 0.1 to 30 parts by mass,
(여기서, Q2는 탄소수 17~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)(Here, Q 2 is 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.)
(C)물: 30~3,000질량부(C) Water: 30 to 3,000 parts by mass
를 유화분산시켜 얻어지는 에멀전을, 알칼리촉매존재하, 0~30℃에서 1~150시간 중합을 행하고, 추가로 중화를 행하는 것을 특징으로 하는 폴리오가노실록산의 양이온계 에멀전 조성물의 제조방법을 제공한다.It provides a method for producing a cationic emulsion composition of polyorganosiloxane, characterized in that the emulsion obtained by emulsifying and dispersing is polymerized for 1 to 150 hours at 0 to 30° C. in the presence of an alkali catalyst, and further neutralized.
이러한 에멀전 조성물의 제조방법이면, 점도가 높은 고중합 폴리오가노실록산의 양이온계 에멀전 조성물로서, 안정성이 양호하고, 또한 내구성도 양호한 것을, 비교적 단시간에 중합시킬 수 있다.According to the method for producing such an emulsion composition, a cationic emulsion composition of highly polymerized polyorganosiloxane having high viscosity, having good stability and good durability, can be polymerized in a relatively short time.
본 발명의 폴리오가노실록산의 양이온계 에멀전 조성물은, 점도가 높은 고중합 폴리오가노실록산의 양이온계 에멀전 조성물이며, 또한, 안정성이 양호하며, 또한 내구성도 양호하다. 또한, 이 에멀전 조성물은, 단독으로 피막을 형성가능하며, 나아가 그 피막의 내구성도 양호하게 할 수 있다. 이러한 에멀전 조성물은, 섬유처리제, 이형제, 발수제, 화장료, 모발용 화장료 등으로서 호적하게 이용할 수 있다.The cationic emulsion composition of polyorganosiloxane of the present invention is a cationic emulsion composition of highly polymerized polyorganosiloxane having high viscosity, and has good stability and good durability. In addition, this emulsion composition can form a film alone, and furthermore, the durability of the film can be improved. Such an emulsion composition can be suitably used as a fiber treatment agent, a mold release agent, a water repellent agent, cosmetics, cosmetics for hair, etc.
또한, 본 발명의 폴리오가노실록산의 양이온계 에멀전 조성물의 제조방법은, 그러한 에멀전 조성물을 비교적 단시간에 중합시킬 수 있으므로, 공업적으로도 유용하다.In addition, the method for producing a polyorganosiloxane cationic emulsion composition of the present invention is industrially useful because such an emulsion composition can be polymerized in a relatively short time.
본 발명자는, 상기 목적을 달성하기 위해 예의검토를 거듭한 결과,The present inventors, as a result of repeated intensive studies in order to achieve the above object,
(D)일반식: HO-[R1 2SiO]j-H로 표시되는 양말단 하이드록시폴리디오가노실록산(여기서, R1은, 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이며, j는 이 양말단 하이드록시폴리디오가노실록산의 25℃에 있어서의 점도가 2,000mPa·s 미만을 만족시키는 값이다.): 100질량부,(D) general formula: HO-[R 1 2 SiO] j -H both terminal hydroxypolydiorganosiloxane represented by -H (here, R 1 is, independently of each other, a hydrogen atom, or 1 having 1 to 20 carbon atoms) is an organic group, and j is a value with which the viscosity at 25°C of both terminal hydroxypolydiorganosiloxane satisfies less than 2,000 mPa·s.): 100 parts by mass;
(E)하기에 나타내는 어느 1개 또는 2개 이상의 오가노알콕시실란: 0~20질량부(E) any one or two or more organoalkoxysilanes shown below: 0 to 20 parts by mass
Si(OR3)4, R1Si(OR3)3, R1 2Si(OR3)2, R1 3Si(OR3)Si(OR 3 ) 4 , R 1 Si(OR 3 ) 3 , R 1 2 Si(OR 3 ) 2 , R 1 3 Si(OR 3 )
(여기서, R1은 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이며, R3은 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이다.),(Here, R 1 is, independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and R 3 is, independently of each other, a hydrogen atom, or a monovalent organic group having 1 to 20 carbon atoms.) ,
(B-1)양이온계 계면활성제: Q1 3(CH3)N+·X-: 0.1~30질량부,(B-1) cationic surfactant: Q 1 3 (CH 3 )N + ·X - : 0.1 to 30 parts by mass;
(여기서, Q1은 동일 또는 이종의 탄소수 6~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)(Here, Q 1 is the same or different 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)양이온계 계면활성제: Q2(CH3)3N+·X-: 0.1~30질량부,(B-2) cationic surfactant: Q 2 (CH 3 ) 3 N + X - : 0.1 to 30 parts by mass,
(여기서, Q2는 탄소수 17~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)(Here, Q 2 is 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.)
(C)물: 30~3,000질량부(C) Water: 30 to 3,000 parts by mass
를 유화분산시켜 얻어지는 에멀전을, 알칼리촉매존재하, 0~30℃에서 1~150시간 중합을 행하고, 추가로 중화를 행함으로써, 이 에멀전을 비교적 단시간에 중합시킬 수 있는 것을 발견하였다. 또한, 본 발명자들은, 이로 인해 (A)성분으로서, 하기 평균조성식(1)로 표시되는, 25℃에 있어서의 점도가 300,000mPa·s 이상인 폴리오가노실록산을 함유한 양이온계 에멀전 조성물이 얻어지고, 이 에멀전 조성물은, 안정성이 양호하며, 또한 내구성도 양호한 것을 발견하여, 본 발명을 완성하기에 이르렀다.It has been found that the emulsion obtained by emulsifying and dispersing is polymerized for 1 to 150 hours at 0 to 30° C. in the presence of an alkali catalyst, and further neutralized to polymerize the emulsion in a relatively short time. In addition, the present inventors thus obtained, as component (A), a cationic emulsion composition containing a polyorganosiloxane having a viscosity at 25°C of 300,000 mPa·s or more, represented by the following average composition formula (1), It was found that this emulsion composition had good stability and also had good durability, leading to the completion of the present invention.
[화학식 2][Formula 2]
(식 중, R1은, 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이며, R2는, 서로 독립적으로, 상기 R1의 선택지로부터 선택되는 기, 하이드록시기, 또는 탄소수 1~20의 알콕시기이며, a, b, c, d는 이 폴리오가노실록산의 25℃에 있어서의 점도가 300,000mPa·s 이상을 만족시키는 값이며, a≥2, c+d≥1이다.)(Wherein, R 1 is, independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and R 2 is, independently of each other, a group selected from the options of R 1 above, a hydroxyl group, Or it is a C1-C20 alkoxy group, a, b, c, and d are a value which the viscosity in 25 degreeC of this polyorganosiloxane satisfy|fills 300,000 mPa*s or more, a≥2, c+d≥1 to be.)
이러한 300,000mPa·s 이상의 고점도의 폴리오가노실록산은 일반적으로 고중합도인 것이다. 그 때문에, 본 발명의 설명시에, 고중합도 폴리오가노실록산의 양이온계 에멀전 조성물이라 칭하기도 한다.The polyorganosiloxane having a high viscosity of 300,000 mPa·s or more generally has a high degree of polymerization. Therefore, in the description of the present invention, it is also referred to as a cationic emulsion composition of a polyorganosiloxane having a high degree of polymerization.
이하, 본 발명에 대하여 실시의 형태를 설명하는데, 본 발명은 이것으로 한정되는 것은 아니다.EMBODIMENT OF THE INVENTION Hereinafter, although embodiment is described about this invention, this invention is not limited to this.
우선, 본 발명의 폴리오가노실록산의 양이온계 에멀전 조성물의 각 성분에 대하여 설명한다.First, each component of the cationic emulsion composition of polyorganosiloxane of the present invention will be described.
[(A)성분][(A) component]
(A)성분은, 하기 평균조성식(1)로 표시되는, 25℃에 있어서의 점도가 300,000mPa·s 이상인 폴리오가노실록산이다. 본 발명의 에멀전 조성물에 있어서, 이 (A)성분은, 100질량부 함유된다.(A) A component is polyorganosiloxane whose viscosity in 25 degreeC is 300,000 mPa*s or more represented by the following average composition formula (1). In the emulsion composition of this invention, 100 mass parts of this (A) component is contained.
[화학식 3][Formula 3]
(식 중, R1은, 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이며, R2는, 서로 독립적으로, 상기 R1의 선택지로부터 선택되는 기, 하이드록시기, 또는 탄소수 1~20의 알콕시기이며, a, b, c, d는 이 폴리오가노실록산의 25℃에 있어서의 점도가 300,000mPa·s 이상을 만족시키는 값이며, a≥2, c+d≥1이다.)(Wherein, R 1 is, independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and R 2 is, independently of each other, a group selected from the options of R 1 above, a hydroxyl group, Or it is a C1-C20 alkoxy group, a, b, c, and d are a value which the viscosity in 25 degreeC of this polyorganosiloxane satisfy|fills 300,000 mPa*s or more, a≥2, c+d≥1 to be.)
상기와 같이, R1은, 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이다. 탄소수 1~20의 1가 유기기로는, 직쇄, 분지쇄 또는 환상의 어느 것이어도 되고, 구체적으로는, 메틸, 에틸, 프로필, 부틸, 펜틸, 헥실, 헵틸, 옥틸, 노닐, 데실, 도데실, 테트라데실, 헥사데실, 옥타데실, 시클로펜틸, 시클로헥실, 시클로헵틸 등의 알킬기, 페닐, 톨릴, 나프틸 등의 아릴기, 비닐, 알릴 등의 알케닐기, 혹은 이들의 유기기구조 중의 수소원자의 일부를 할로겐원자나, 아미노, 아크릴옥시, 메타크릴옥시, 에폭시, 메르캅토 등의 극성기함유의 유기기로 치환한 것 등을 들 수 있다. 여기서, R1의 80% 이상은 메틸기인 것이 공업적 및 특성적으로 바람직하다.As described above, R 1 is, each independently, 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, methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, Alkyl groups such as tetradecyl, hexadecyl, octadecyl, cyclopentyl, cyclohexyl, and cycloheptyl; aryl groups such as phenyl, tolyl and naphthyl; alkenyl groups such as vinyl and allyl; and those in which a part is substituted with an organic group containing a polar group such as a halogen atom, amino, acryloxy, methacryloxy, epoxy, or mercapto. Here, it is industrially and characteristically preferable that 80% or more of R 1 is a methyl group.
또한, 상기와 같이, R2는, 서로 독립적으로, 상기의 R1의 선택지로부터 선택되는 기, 또는, 하이드록시기, 혹은 탄소수 1~20의 알콕시기이다. 탄소수 1~20의 알콕시기로는, 직쇄, 분지쇄 또는 환상의 어느 것이어도 되고, 구체적으로는, 메톡시기, 에톡시기, 프로파녹시기, 부톡시기, 펜틸옥시기, 헥실옥시기, 옥틸옥시기, 데실옥시기, 도데실옥시기, 2-에틸헥실옥시기 등을 들 수 있고, 메톡시기, 에톡시기, 프로파녹시기, 부톡시기, 펜틸옥시기가 바람직하고, 메톡시기, 에톡시기, 프로파녹시기가 더욱 바람직하다.In addition, as mentioned above, R< 2 > is mutually independently a group chosen from said R< 1 > option, a hydroxyl group, or a C1-C20 alkoxy group. The alkoxy group having 1 to 20 carbon atoms may be any of linear, branched or cyclic, and specifically, a methoxy group, an ethoxy group, a propanoxy group, a butoxy group, a pentyloxy group, a hexyloxy group, an octyloxy group, Decyloxy group, dodecyloxy group, 2-ethylhexyloxy group, etc. are mentioned, A methoxy group, an ethoxy group, a propanoxy group, a butoxy group, and a pentyloxy group are preferable, and a methoxy group, an ethoxy group, and a propanoxy group are more desirable.
상기 평균조성식(1) 중에, 반응성 관능기가 존재하는 경우, 그 반응성 관능기는 다른 화합물과 반응하고 있을 수도 있다. 구체적으로는, 상기 평균조성식(1) 중에 아미노기가 존재하는 경우, 에폭시기함유 폴리옥시알킬렌 화합물이나 에폭시기함유 알킬 화합물과의 개환반응을 하고 있을 수도 있고, 또한, 무수아세트산이나, 무수프로피온산, 무수옥살산, 무수석신산, 무수말레산, 무수프탈산, 무수안식향산과 같은 카르본산무수물과의 아세틸화 반응을 하고 있을 수도 있다. 또한, 상기 평균조성식(1) 중에 에폭시기가 존재하는 경우, 아미노기함유 화합물과 개환반응을 하고 있을 수도 있다. 한편, 상기에 나타낸 반응성 관능기와의 반응은 이들로 한정되는 것은 아니다.When a reactive functional group is present in the average composition formula (1), the reactive functional group may be reacting with another compound. Specifically, when an amino group is present in the above average composition formula (1), a ring-opening reaction with an epoxy group-containing polyoxyalkylene compound or an epoxy group-containing alkyl compound may be performed, and further, acetic anhydride, propionic anhydride, or oxalic anhydride , succinic anhydride, maleic anhydride, phthalic anhydride or benzoic anhydride may be undergoing an acetylation reaction with a carboxylic acid anhydride. Further, when an epoxy group is present in the above average composition formula (1), a ring-opening reaction with the amino group-containing compound may be carried out. In addition, the reaction with the reactive functional group shown above is not limited to these.
상기 평균조성식(1) 중의 a, b, c, d는, 폴리오가노실록산의 25℃에 있어서의 점도가 300,000mPa·s 이상을 만족시키는 값이며, 400,000mPa·s 이상을 만족시키는 값이 보다 바람직하고, 500,000mPa·s 이상을 만족시키는 값이 더욱 바람직하다. 한편, 이 점도는 절대점도로서, 액상으로 측정할 수 있는 것은 그대로, 점도가 너무 높아 측정할 수 없는 것은 톨루엔용해점도를, 회전점도계에 의해, 25℃에서 측정한 값이다. 또한, a≥2, c+d≥1이다.A, b, c, and d in the above average composition formula (1) are values that satisfy the viscosity at 25°C of the polyorganosiloxane of 300,000 mPa·s or more, and more preferably a value that satisfies 400,000 mPa·s or more. and a value satisfying 500,000 mPa·s or more is more preferable. On the other hand, this viscosity is an absolute viscosity, which can be measured in a liquid phase as it is, and a viscosity that is too high to be measured is a value measured at 25°C using a rotational viscometer at a toluene dissolution viscosity. Also, a≥2 and c+d≥1.
상기 평균조성식(1) 중의 b는, 전형적으로는 50 이상, 바람직하게는 100 이상의 값을 취할 수 있다. 단, c+d의 값이 큰 경우는 가교단위가 증가하므로, b가 50 이하여도 점도가 300,000mPa·s 이상이 되는 경우도 있다.b in the said average composition formula (1) is 50 or more typically, Preferably it can take a value of 100 or more. However, since the crosslinking unit increases when the value of c+d is large, even if b is 50 or less, the viscosity may become 300,000 mPa·s or more.
(A)성분의 구체예로는, 하기 평균조성식을 들 수 있는데, 이들로 한정되는 것은 아니다. 하기 평균조성식 중, a, b, c, d, e, f는, 폴리오가노실록산의 25℃에 있어서의 점도가 300,000mPa·s 이상을 만족시키는 값이며, a≥2, c+d≥1이다. 또한, 하기 평균조성식 중의 b+e+f는, 전형적으로는 50 이상, 바람직하게는 100 이상의 값을 취할 수 있다.(A) Although the following average compositional formula is mentioned as a specific example of a component, it is not limited to these. In the following average composition formula, a, b, c, d, e, and f are values satisfying the viscosity of polyorganosiloxane at 25°C of 300,000 mPa·s or more, and a≥2 and c+d≥1. . In addition, b+e+f in the following average composition formula is 50 or more typically, Preferably it can take a value of 100 or more.
[화학식 4][Formula 4]
[화학식 5][Formula 5]
[화학식 6][Formula 6]
[(B-1)성분 및 (B-2)성분][(B-1) component and (B-2) component]
(B-1)성분 및 (B-2)성분은 이하와 같다.(B-1) A component and (B-2) a component are as follows.
(B-1)양이온계 계면활성제: Q1 3(CH3)N+·X-(여기서, Q1은, 동일 또는 이종의 탄소수 6~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)(B-1) Cationic surfactant: Q 1 3 (CH 3 )N + ·X - (here, Q 1 is the same or different monovalent organic group having 6 to 30 carbon atoms, and X is a halogen atom or carbon number 1 It is a monovalent carboxyl group of ~6.)
(B-2)양이온계 계면활성제: Q2(CH3)3N+·X-(여기서, Q2는, 탄소수 17~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)(B-2) Cationic surfactant: Q 2 (CH 3 ) 3 N + ·X - (wherein Q 2 is a monovalent organic group having 17 to 30 carbon atoms, X is a halogen atom or 1 having 1 to 6 carbon atoms) is a carboxyl group.)
본 발명의 에멀전 조성물에 있어서, (A)성분 100질량부에 대하여, (B-1)성분이 0.1~30질량부 함유되고, (B-2)성분이 0.1~30질량부 함유된다.The emulsion composition of this invention WHEREIN: With respect to 100 mass parts of (A) component, 0.1-30 mass parts of (B-1) component is contained, and 0.1-30 mass parts of (B-2) components are contained.
이들 (B-1)성분 및 (B-2)성분인 양이온계 계면활성제는, 폴리오가노실록산을 수중에 유화분산시키기 위한 것인데, 본 발명자들은 (B-1) 및 (B-2)성분의 작용기구에 대하여, 유화제로서의 작용기구 이외에도 다음과 같은 작용기구를 고려하고 있다. 본 발명의 폴리오가노실록산의 양이온계 에멀전 조성물의 제조방법에 있어서, 폴리오가노실록산을 수중에 유화분산한 후에, 알칼리촉매를 첨가했을 때에 수상에 발생하는 OH-와 (B-1) 및 (B-2)성분인 양이온계 계면활성제의 반대이온(對イオン)이 교환함으로써, 양이온계 계면활성제 자체도 촉매로서 작용하고, 그 결과, 보다 효율적으로 (A)성분의 폴리오가노실록산을 고중합도화할 수 있다고 생각된다.These (B-1) component and (B-2) component cationic surfactant are for emulsifying and dispersing polyorganosiloxane in water, but the present inventors have the action of (B-1) and (B-2) component Regarding the mechanism, in addition to the action mechanism as an emulsifier, the following action mechanism is considered. In the method for producing a cationic emulsion composition of polyorganosiloxane of the present invention, after emulsifying and dispersing the polyorganosiloxane in water, OH - and (B-1) and (B-) generated in the aqueous phase when an alkali catalyst is added 2) By exchanging the counterion of the component cationic surfactant, the cationic surfactant itself also acts as a catalyst, and as a result, the polyorganosiloxane of component (A) can be highly polymerized more efficiently. I think.
(B-1)성분인 양이온계 계면활성제는, 상기와 같이, Q1 3(CH3)N+·X-로 표시되는 양이온계 계면활성제이며, Q1은 동일 또는 이종의 탄소수 6~30의 1가 유기기이며, 바람직하게는 7~18의 1가 유기기이다. Q1의 탄소수가 6보다 작은 경우에는, 계면활성제의 친수성이 너무 강해 (A)성분의 폴리오가노실록산과의 접촉빈도가 적어지고, 폴리오가노실록산을 고중합도화하기에 장시간의 중합을 필요로 한다. 또한, Q1의 탄소수가 30보다 큰 경우에는 계면활성제로서의 유화력이 약하고, 안정된 에멀전을 얻을 수 없는 경우가 있다.(B-1) The cationic surfactant as a component is a cationic surfactant represented by Q 1 3 (CH 3 )N + ·X - as described above, and Q 1 is the same or different types of C6-30 It is a monovalent organic group, Preferably it is a monovalent organic group of 7-18. When the number of carbon atoms of Q 1 is less than 6, the hydrophilicity of the surfactant is too strong, the frequency of contact with the polyorganosiloxane of component (A) decreases, and a long polymerization is required to increase the degree of polymerization of the polyorganosiloxane. . Moreover, when carbon number of Q 1 is larger than 30, the emulsifying power as a surfactant is weak, and a stable emulsion may not be obtained.
Q1의 구체예로는, 헥실, 헵틸, 옥틸, 노닐, 데실, 운데실, 도데실, 트리데실, 테트라데실, 펜타데실, 헥사데실, 헵타데실, 옥타데실, 노나데실, 에이코실, 도코사닐(ドコサニル), 시클로펜틸, 시클로헥실, 시클로헵틸 등의 알킬기, 페닐, 벤질, 톨릴, 나프틸 등의 아릴기, 올레일 등의 알케닐기 등을 들 수 있다. 그 중에서도 옥틸, 도데실, 헥사데실, 옥타데실이 바람직하다.Specific examples of Q 1 include hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, docosanyl (docosanil), an alkyl group such as cyclopentyl, cyclohexyl, and cycloheptyl; an aryl group such as phenyl, benzyl, tolyl, and naphthyl; and an alkenyl group such as oleyl. Among them, octyl, dodecyl, hexadecyl and octadecyl are preferable.
또한, X-는, 할로겐이온 또는 탄소수 1~6의 1가 카르복실이온이며, 구체적으로는 Cl-, Br-, I- 등의 할로겐이온, HCOO-, CH3COO-, C2H5COO- 등의 카르복실이온을 들 수 있다. 그 중에서도 Cl-, HCOO-, CH3COO-가 바람직하다.In addition, X - is a halogen ion or a monovalent carboxyl ion having 1 to 6 carbon atoms, specifically, a halogen ion such as Cl - , Br - , I - , HCOO - , CH 3 COO - , C 2 H 5 COO and carboxyl ions such as - . Among them, Cl - , HCOO - , and CH 3 COO - are preferable.
(B-1)성분의 구체예로는, 트리헥실메틸암모늄클로라이드, 트리헵틸메틸암모늄클로라이드, 트리옥틸메틸암모늄클로라이드, 트리노닐메틸암모늄클로라이드, 트리데실메틸암모늄클로라이드, 트리라우릴메틸암모늄클로라이드, 트리옥틸메틸암모늄아세테이트, 트리라우릴메틸암모늄아세테이트 등을 들 수 있는데, 이들로 한정되는 것은 아니다.(B-1) Specific examples of the component include trihexylmethylammonium chloride, triheptylmethylammonium chloride, trioctylmethylammonium chloride, trinonylmethylammonium chloride, tridecylmethylammonium chloride, trilaurylmethylammonium chloride, tri Octylmethylammonium acetate, trilaurylmethylammonium acetate and the like may be mentioned, but are not limited thereto.
(B-1)성분의 양이온계 계면활성제의 사용량으로는, (A)성분 100질량부에 대하여, 0.1~30질량부 이용할 수 있고, 바람직하게는 0.5~20질량부, 보다 바람직하게는 1~15질량부이다. 0.1질량부보다 적은 경우에는, (A)성분이 중합과정에서 효율좋게 고중합도화할 수 없는 경우가 있으며, 또한, 30질량부보다 많은 경우에는 에멀전의 안정성이 불안정해지기 쉽다.(B-1) As usage-amount of cationic surfactant of component, 0.1-30 mass parts can be used with respect to 100 mass parts of (A) component, Preferably it is 0.5-20 mass parts, More preferably, 1- 15 parts by mass. When it is less than 0.1 mass part, (A) component may not be able to make high polymerization degree efficiently in the polymerization process, and when more than 30 mass parts, stability of an emulsion becomes unstable easily.
또한, (B-2)성분의 양이온계 계면활성제는, 상기와 같이, Q2(CH3)3N+·X-로 표시되는 양이온계 계면활성제이며 에멀전의 안정성을 향상시킬 수 있다. 여기서, Q2는, 탄소수 17~30의 1가 유기기이며, 바람직하게는 18~28의 1가 유기기이다. Q2의 탄소수가 17보다 작은 경우에는, (B-1)로 표시되는 양이온계 계면활성제와의 상용성이 나빠 에멀전의 안정성이 저하되는 경우가 있다. Q2의 탄소수가 30보다 큰 경우에는, Q1의 경우와 마찬가지로, 계면활성제로서의 유화력이 약하고, 안정된 에멀전을 얻을 수 없는 경우가 있다. Q2의 X-는, 상기 Q1의 X-와 동일하다.Moreover, the cationic surfactant of (B-2) component is a cationic surfactant represented by Q2 (CH3) 3N + * X- as mentioned above, and can improve the stability of an emulsion. Here, Q 2 is a monovalent organic group having 17 to 30 carbon atoms, preferably a monovalent organic group having 18 to 28 carbon atoms. When the carbon number of Q 2 is smaller than 17, compatibility with the cationic surfactant represented by (B-1) is poor, and the stability of the emulsion may be lowered. When carbon number of Q2 is larger than 30, similarly to the case of Q1 , the emulsifying power as a surfactant is weak, and a stable emulsion may not be obtained. X − in Q 2 is the same as X − in Q 1 above.
(B-2)성분의 구체예로는, 스테아릴트리메틸암모늄클로라이드, 이코실트리메틸암모늄클로라이드, 베헤닐트리메틸암모늄클로라이드, 스테아릴트리메틸암모늄아세테이트, 이코실트리메틸암모늄아세테이트, 베헤닐트리메틸암모늄아세테이트 등을 들 수 있는데, 이들로 한정되는 것은 아니다.(B-2) As a specific example of a component, stearyl trimethyl ammonium chloride, icosyl trimethyl ammonium chloride, behenyl trimethyl ammonium chloride, stearyl trimethyl ammonium acetate, icosyl trimethyl ammonium acetate, behenyl trimethyl ammonium acetate, etc. are mentioned can be, but is not limited thereto.
(B-2)성분의 양이온계 계면활성제의 사용량으로는, (A)성분 100질량부에 대하여, 0.1~30질량부 이용할 수 있고, 바람직하게는 0.5~20질량부, 보다 바람직하게는 1~15질량부이다. 0.1질량부보다 적은 경우에는 에멀전의 안정성이 불안정해지기 쉽고, 30질량부보다 많은 경우에는 (A)성분이 중합과정에서 효율좋게 고중합도화할 수 없는 경우가 있다.(B-2) As usage-amount of cationic surfactant of component, 0.1-30 mass parts can be used with respect to 100 mass parts of (A) component, Preferably it is 0.5-20 mass parts, More preferably, 1- 15 parts by mass. When it is less than 0.1 parts by mass, the stability of the emulsion tends to be unstable, and when it is more than 30 parts by mass, the component (A) may not be able to efficiently achieve a high degree of polymerization in the polymerization process.
(B-1)성분은 (B-2)성분에 비해 소수성이 높으므로, (A)성분의 폴리오가노실록산과의 접촉빈도가 높고, 보다 중합속도를 빠르게 하는 효과를 기대할 수 있는 한편, 소수성이 너무 높아 유화능이 뒤떨어지는 경우가 있다. 그 때문에, (B-1)만 사용하는 경우, 에멀전의 조성이나, 입경, 점도, pH 등의 조건에 따라서는 에멀전의 경시안정성이 나빠지는 경우가 있다. 이에, (B-1)성분과 비교하여 유화능이 높은 (B-2)성분을 병용함으로써 중합속도를 높인 채로, 에멀전의 안정성을 높일 수 있다.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 speeding up the polymerization rate more can be expected, while hydrophobicity is If it is too high, the emulsifying ability may be inferior. Therefore, when only (B-1) is used, the stability over time of the emulsion may deteriorate depending on conditions such as the composition of the emulsion, particle size, viscosity, and pH. Accordingly, the stability of the emulsion can be improved while the polymerization rate is increased by using the component (B-2) having high emulsification ability in combination with the component (B-1).
또한, 본 발명의 폴리오가노실록산의 양이온계 에멀전 조성물에 있어서는, 양이온계 계면활성제 외에, 비이온계 계면활성제를 병용함으로써 에멀전의 소입경화가 용이해지고, 이에 따라 에멀전의 안정성의 향상으로 이어진다. 비이온계 계면활성제로는, 폴리옥시알킬렌알킬에테르, 폴리옥시알킬렌알킬페닐에테르, 폴리옥시알킬렌알킬에스테르, 폴리옥시알킬렌솔비탄알킬에스테르, 폴리에틸렌글리콜, 폴리프로필렌글리콜, 디에틸렌글리콜 등이 예시되고, 1종 단독으로 또는 2종 이상을 적당히 선택하여 이용할 수 있다. 그 중에서도, 하기 일반식(2)In addition, in the cationic emulsion composition of polyorganosiloxane of the present invention, by using a nonionic surfactant in addition to the cationic surfactant, hardening of the emulsion to small particles is facilitated, thereby improving the stability of the emulsion. Examples of the nonionic surfactant include polyoxyalkylene alkyl ether, polyoxyalkylene alkylphenyl ether, polyoxyalkylene alkyl ester, polyoxyalkylene sorbitan alkyl ester, polyethylene glycol, polypropylene glycol, diethylene glycol, and the like. These are illustrated, and can be used individually by 1 type or selecting 2 or more types suitably. Among them, the following general formula (2)
R4O(EO)P(PO)qH (2)R 4 O(EO) P (PO) q H (2)
(식 중, R4는, 탄소원자수 8~30의 직쇄 또는 분지쇄의 알킬기이며, EO는 에틸렌옥사이드기, PO는 프로필렌옥사이드기를 나타내고, 그들의 배열은 블록상이어도 랜덤상이어도 된다. p 및 q는 독립적으로 0~100의 정수이며, 단, p+q>0이다.)로 표시되는 것이 바람직하다. 특히, 상기 일반식(2)에 있어서, R4는 탄소원자수 8~18의 직쇄 또는 분지쇄의 알킬기가 바람직하고, p, q는 독립적으로 0~25, 0<p+q≤50이 바람직하다.(Wherein, R 4 is a linear or branched alkyl group having 8 to 30 carbon atoms, EO is an ethylene oxide group, PO is a propylene oxide group, and their arrangement may be block or random. p and q are It is independently an integer from 0 to 100, provided that p+q>0). In particular, in the general formula (2), R 4 is preferably a straight-chain or branched alkyl group having 8 to 18 carbon atoms, and p and q are independently preferably 0 to 25, and 0<p+q≤50. .
또한, 에멀전의 안정성을 보충하는 등의 목적으로, (B-1)성분 및 (B-2)성분 이외의 제4급 암모늄염, 알킬아민아세트산염 등의 양이온계 계면활성제, 알킬베타인, 알킬이미다졸린 등의 양성 계면활성제를 첨가하는 것은 전혀 문제없다.In addition, for the purpose of supplementing the stability of the emulsion, quaternary ammonium salts other than component (B-1) and component (B-2), cationic surfactants such as alkylamine acetate, alkyl betaine, and alkyl There is no problem at all to add an amphoteric surfactant such as midazoline.
[(C)성분][(C)component]
본 발명의 에멀전 조성물은, (C)성분으로서 물을, (A)성분 100질량부에 대하여 30~3,000질량부, 바람직하게는 40~2,400질량부 배합한다. 물이 너무 적으면 유중수형 에멀전이 되지 않고, 너무 많으면 비경제적이다.The emulsion composition of this invention is 30-3,000 mass parts with respect to 100 mass parts of (A) component, Preferably it mix|blends 40-2,400 mass parts of water as (C)component. If there is too little water, a water-in-oil type emulsion will not work, and if there is too much water, it is uneconomical.
[에멀전 조성물의 제조방법][Method for preparing emulsion composition]
이어서, 본 발명의 에멀전 조성물의 제조방법은, 이하와 같다. 즉,Next, the manufacturing method of the emulsion composition of this invention is as follows. in other words,
(D)일반식: HO-[R1 2SiO]j-H로 표시되는 양말단 하이드록시폴리디오가노실록산(여기서, R1은, 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이며, j는 이 양말단 하이드록시폴리디오가노실록산의 25℃에 있어서의 점도가 2,000mPa·s 미만을 만족시키는 값이다.): 100질량부,(D) general formula: HO-[R 1 2 SiO] j -H both terminal hydroxypolydiorganosiloxane represented by -H (here, R 1 is, independently of each other, a hydrogen atom, or 1 having 1 to 20 carbon atoms) is an organic group, and j is a value with which the viscosity at 25°C of both terminal hydroxypolydiorganosiloxane satisfies less than 2,000 mPa·s.): 100 parts by mass;
(E)하기에 나타내는 어느 1개 또는 2개 이상의 오가노알콕시실란: 0~20질량부(E) any one or two or more organoalkoxysilanes shown below: 0 to 20 parts by mass
Si(OR3)4, R1Si(OR3)3, R1 2Si(OR3)2, R1 3Si(OR3)Si(OR 3 ) 4 , R 1 Si(OR 3 ) 3 , R 1 2 Si(OR 3 ) 2 , R 1 3 Si(OR 3 )
(여기서, R1은 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이며, R3은 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이다.),(Here, R 1 is, independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and R 3 is, independently of each other, a hydrogen atom, or a monovalent organic group having 1 to 20 carbon atoms.) ,
(B-1)양이온계 계면활성제: Q1 3(CH3)N+·X-: 0.1~30질량부,(B-1) cationic surfactant: Q 1 3 (CH 3 )N + ·X - : 0.1 to 30 parts by mass;
(여기서, Q1은 동일 또는 이종의 탄소수 6~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)(Here, Q 1 is the same or different 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)양이온계 계면활성제: Q2(CH3)3N+·X-: 0.1~30질량부,(B-2) cationic surfactant: Q 2 (CH 3 ) 3 N + X - : 0.1 to 30 parts by mass,
(여기서, Q2는 탄소수 17~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)(Here, Q 2 is 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.)
(C)물: 30~3,000질량부(C) Water: 30 to 3,000 parts by mass
를 유화분산시켜 얻어지는 에멀전을, 알칼리촉매존재하, 0~30℃에서 1~150시간 중합을 행하고, 추가로 중화를 행하는 것이다.The emulsion obtained by emulsifying and dispersing is subjected to polymerization for 1 to 150 hours at 0 to 30° C. in the presence of an alkali catalyst, followed by further neutralization.
[(D)성분][(D)component]
우선, (D)성분인 일반식: HO-[R1 2SiO]j-H로 표시되는 양말단 하이드록시폴리디오가노실록산(여기서, R1은, 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이며, j는 이 양말단 하이드록시폴리디오가노실록산의 25℃에 있어서의 점도가 2,000mPa·s 미만을 만족시키는 값이다.)은, (A)성분인 폴리오가노실록산의 원료가 되는 것이다.First, (D) component general formula: HO-[R 1 2 SiO] j -H both terminal hydroxypolydiorganosiloxane represented by (here, R 1 is, independently of each other, a hydrogen atom, or carbon number 1 -20 is a monovalent organic group, and j is a value satisfying the viscosity at 25°C of the hydroxypolydiorganosiloxane at both terminals of less than 2,000 mPa·s.) is the polyorganosiloxane which is the component (A) will be the raw material for
상기 일반식 중의 j는, 전형적으로는 1~400이라고 하는 값을 취할 수 있다.j in the said general formula can take the value of 1-400 typically.
(D)성분의 구체예로는, 하기 평균조성식을 들 수 있는데, 이들로 한정되는 것은 아니다. 하기 평균조성식 중의 j, k+l, k+l+m은 양말단 하이드록시폴리디오가노실록산의 25℃에 있어서의 점도가 2,000mPa·s 미만을 만족시키는 값이다. 또한, 하기 일반식 중의 j, k+l, k+l+m은, 전형적으로는 1~400이라고 하는 값을 취할 수 있다.(D) Although the following average compositional formula is mentioned as a specific example of a component, it is not limited to these. j, k+1, k+1+m in the following average compositional formula are values with which the viscosity at 25 degreeC of both terminal hydroxypolydiorganosiloxane satisfy|fills less than 2,000 mPa*s. In addition, j, k+1, k+1+m in the following general formula can take the value of 1-400 typically.
[화학식 7][Formula 7]
[(E)성분][(E) component]
(E)성분인 오가노알콕시실란은, (A)성분이 되는 폴리오가노실록산의 원료가 되는 것이며, 하기 일반식 중 어느 1개 또는 2개 이상의 오가노알콕시실란이다.(E) The organoalkoxysilane which is a component becomes a raw material of the polyorganosiloxane used as (A) component, It is any 1 or 2 or more organoalkoxysilanes in the following general formula.
Si(OR3)4, R1Si(OR3)3, R1 2Si(OR3)2, R1 3Si(OR3)Si(OR 3 ) 4 , R 1 Si(OR 3 ) 3 , R 1 2 Si(OR 3 ) 2 , R 1 3 Si(OR 3 )
여기서, R1은 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이다. 탄소수 1~20의 1가 유기기로는 메틸, 에틸, 프로필, 부틸, 펜틸, 헥실, 헵틸, 옥틸, 노닐, 데실, 도데실, 테트라데실, 헥사데실, 옥타데실, 시클로펜틸, 시클로헥실, 시클로헵틸 등의 알킬기, 페닐, 톨릴, 나프틸 등의 아릴기, 비닐, 알릴 등의 알케닐기, 혹은 이들의 유기기구조 중의 수소원자의 일부를 할로겐원자나, 아미노, 아크릴옥시, 메타크릴옥시, 에폭시, 메르캅토 등의 극성기함유의 유기기로 치환한 것 등을 들 수 있다. 여기서, R1의 80% 이상은 메틸기인 것이 공업적 및 특성적으로 바람직하다. 또한, R3은 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이다. R3의 탄소수 1~20의 1가 유기기로는 상기 R1과 동일하며, 메틸기, 에틸기, 프로필기, 부틸기가 바람직하고, 메틸기, 에틸기가 더욱 바람직하다.Here, R 1 is each independently a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms. Monovalent organic groups having 1 to 20 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, cyclopentyl, cyclohexyl, cycloheptyl. Alkyl groups such as phenyl, tolyl and naphthyl; alkenyl groups such as vinyl and allyl; What is substituted with organic groups containing polar groups, such as mercapto, etc. are mentioned. Here, it is industrially and characteristically preferable that 80% or more of R 1 is a methyl group. In addition, R 3 is each independently a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms. The monovalent organic group having 1 to 20 carbon atoms of R 3 is the same as that of R 1 above, and a methyl group, an ethyl group, a propyl group, and a butyl group are preferable, and a methyl group and an ethyl group are more preferable.
(E)성분의 사용량으로는, (D)성분인 양말단 하이드록시폴리디오가노실록산 100질량부에 대하여, 0~20질량부이며, 바람직하게는 0~15질량부이다. (E)성분의 배합량이 너무 많으면 피막화했을 때에 물러져 내구성이 저하되는 경우가 있다.(E) As usage-amount of component (D), it is 0-20 mass parts with respect to 100 mass parts of both terminal hydroxy polydiorganosiloxane which is (D)component, Preferably it is 0-15 mass parts. (E) When there are too many compounding quantities of a component, when it forms into a film, it may become brittle, and durability may fall.
(E)성분의 구체예로는, 메틸트리메톡시실란, 디메틸디메톡시실란, 페닐트리메톡시실란, 메틸트리에톡시실란, 디메틸디에톡시실란, 페닐트리에톡시실란, 헥실트리메톡시실란, 헥실트리에톡시실란, 데실트리메톡시실란, 트리플루오로프로필트리메톡시실란, 비닐트리메톡시실란, 비닐트리에톡시실란, 2-(3,4-에폭시시클로헥실)에틸트리메톡시실란, 3-글리시독시프로필메틸디메톡시실란, 3-글리시독시프로필트리메톡시실란, 3-글리시독시프로필메틸디에톡시실란, 3-글리시독시프로필트리에톡시실란, p-스티릴트리메톡시실란, 3-메타크릴옥시프로필메틸디메톡시실란, 3-메타크릴옥시프로필트리메톡시실란, 3-메타크릴옥시프로필메틸디에톡시실란, 3-메타크릴옥시프로필트리에톡시실란, 3-아크릴옥시프로필트리메톡시실란, N-2-(아미노에틸)-3-아미노프로필메틸디메톡시실란, N-2-(아미노에틸)-3-아미노프로필트리메톡시실란, 3-아미노프로필트리메톡시실란, 3-아미노프로필트리에톡시실란, 3-트리에톡시실릴-N-(1,3-디메틸-부틸리덴)프로필아민, N-페닐-3-아미노프로필트리메톡시실란, 3-우레이도프로필트리에톡시실란, 3-메르캅토프로필메틸디메톡시실란, 3-메르캅토프로필트리메톡시실란, 비스(트리에톡시실릴프로필)테트라설파이드, 3-이소시아네이트프로필트리에톡시실란 등을 들 수 있는데, 이들로 한정되는 것은 아니다.(E) As a specific example of a component, methyl trimethoxysilane, dimethyldimethoxysilane, phenyl trimethoxysilane, methyl triethoxysilane, dimethyl diethoxysilane, phenyl triethoxysilane, hexyl trimethoxysilane, Hexyltriethoxysilane, decyltrimethoxysilane, trifluoropropyltrimethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, 3-Glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, p-styryltrimethyl Toxysilane, 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryl Oxypropyltrimethoxysilane, N-2-(aminoethyl)-3-aminopropylmethyldimethoxysilane, N-2-(aminoethyl)-3-aminopropyltrimethoxysilane, 3-aminopropyltrimethoxy Silane, 3-Aminopropyltriethoxysilane, 3-triethoxysilyl-N-(1,3-dimethyl-butylidene)propylamine, N-phenyl-3-aminopropyltrimethoxysilane, 3-ure Idopropyltriethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-mercaptopropyltrimethoxysilane, bis(triethoxysilylpropyl)tetrasulfide, 3-isocyanatepropyltriethoxysilane, etc. are mentioned. However, the present invention is not limited thereto.
[(B-1)성분, (B-2)성분, (C)성분][(B-1) component, (B-2) component, (C) component]
본 발명의 에멀전 조성물의 제조방법에서 이용하는 (B-1)성분, (B-2)성분, (C)성분에 대해서는 상기와 마찬가지이다.(B-1) component, (B-2) component, and (C) component used in the manufacturing method of the emulsion composition of this invention are the same as the above.
이들 (D)성분인 양말단 하이드록시폴리디오가노실록산, (E)성분인 오가노알콕시실란, 상술한 (B-1)성분 및 (B-2)성분인 양이온계 계면활성제 및 (C)성분인 물을 호모믹서, 호모지나이저, 콜로이드밀, 호모디스퍼, 라인믹서와 같은 유화기를 이용하여 균일한 에멀전으로 한 후, 알칼리촉매를 첨가하여, 0~30℃에서 1~150시간 중합을 행한다.Both terminal hydroxypolydiorganosiloxane as component (D), organoalkoxysilane as component (E), cationic surfactant as component (B-1) and component (B-2) described above, and component (C) The phosphorus is made into a uniform emulsion using an emulsifier such as a homomixer, homogenizer, colloid mill, homodisper, or line mixer, and then an alkali catalyst is added and polymerization is performed at 0-30°C for 1-150 hours. .
여기서, 알칼리촉매로는, 수산화나트륨, 수산화칼륨, 수산화리튬, 불화칼륨, 암모니아, 테트라메틸암모늄하이드록사이드, 테트라에틸암모늄하이드록사이드, 테트라프로필암모늄하이드록사이드, 테트라부틸암모늄하이드록사이드, 벤질트리메틸암모늄하이드록사이드, 테트라부틸포스포늄하이드록사이드, 트리플로로메틸페닐트리메틸암모늄하이드록사이드 등을 들 수 있다. 그 중에서도, 수산화나트륨, 수산화칼륨, 암모니아, 테트라메틸암모늄하이드록사이드, 테트라부틸암모늄하이드록사이드, 벤질트리메틸암모늄하이드록사이드, 테트라부틸포스포늄하이드록사이드가 바람직하다.Here, as the alkali catalyst, sodium hydroxide, potassium hydroxide, lithium hydroxide, potassium fluoride, ammonia, tetramethylammonium hydroxide, tetraethylammonium hydroxide, tetrapropylammonium hydroxide, tetrabutylammonium hydroxide, benzyl Trimethylammonium hydroxide, tetrabutylphosphonium hydroxide, trifluoromethylphenyl trimethylammonium hydroxide, etc. are mentioned. Among these, sodium hydroxide, potassium hydroxide, ammonia, tetramethylammonium hydroxide, tetrabutylammonium hydroxide, benzyltrimethylammonium hydroxide, and tetrabutylphosphonium hydroxide are preferable.
알칼리촉매의 사용량으로는, (D)성분인 양말단 하이드록시오가노실록산 100질량부에 대하여, 0.01~5질량부인 것이 바람직하고, 0.03~5질량부인 것이 더욱 바람직하다.As usage-amount of an alkali catalyst, it is preferable that it is 0.01-5 mass parts with respect to 100 mass parts of both terminal hydroxyorganosiloxane which is (D)component, and it is more preferable that it is 0.03-5 mass parts.
한편, (B-1) 및 (B-2)성분인 양이온계 계면활성제를, 이온교환수지를 이용하여 4급 암모늄하이드록사이드로 하면, 이것 자신이 알칼리촉매성분으로서 작용하므로 알칼리촉매를 별도 첨가할 필요는 없다. 이와 같이, (B-1)성분 또는 (B-2)성분 자체를 알칼리촉매성분으로서 작용시키는 경우도, 본 발명의 에멀전 조성물의 제조방법에 있어서의, 상기 (D), (E), (B-1), (B-2) 및 (C)성분을 유화분산시켜 얻어지는 에멀전을, 알칼리촉매존재하에서 중합을 행하는 것에 해당한다.On the other hand, if the cationic surfactant, which is the component (B-1) and (B-2), is quaternary ammonium hydroxide using an ion exchange resin, an alkali catalyst is added separately because it acts as an alkali catalyst component. You don't have to. In this way, even when component (B-1) or component (B-2) itself acts as an alkali catalyst component, in the method for producing the emulsion composition of the present invention, the above (D), (E), (B) -1), (B-2), and (C) correspond to polymerizing the emulsion obtained by emulsifying and dispersing in the presence of an alkali catalyst.
또한, 중합온도는 0~30℃이다. 0℃보다 낮은 경우에는 중합의 진행이 느려 실용적이지 않고, 30℃보다 높은 경우에는 에멀전의 안정성이 불안정한 것이 된다. 바람직하게는 5~25℃이다. 또한, 중합시간은 1~150시간이다. 1시간 미만인 경우에는 중합이 불충분하며, 150시간보다 길어지면 공업적이지 않게 된다. 이 중합시간은, 바람직하게는 5~120시간이다.In addition, the polymerization temperature is 0 ~ 30 ℃. When it is lower than 0 degreeC, the progress of polymerization is slow, and it is impractical, and when it is higher than 30 degreeC, the stability of an emulsion becomes unstable. Preferably it is 5-25 degreeC. In addition, the polymerization time is 1-150 hours. When it is less than 1 hour, the polymerization is insufficient, and when it is longer than 150 hours, it becomes unindustrial. The polymerization time is preferably 5 to 120 hours.
소정의 중합시간 후, 중화함으로써, 중합반응을 정지할 수 있다. 여기서의 중화는 산성 화합물로 행할 수 있다. 산성 화합물로는, 염산, 포름산, 아세트산, 프로피온산 등을 들 수 있고, 바람직하게는, 염산, 포름산, 아세트산이다. 한편, 산성 화합물을 사용하는 대신에 이온교환수지를 이용하여 중화하는 것도 가능하다.After a predetermined polymerization time, the polymerization reaction can be stopped by neutralization. Neutralization here can be performed with 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 preferred. On the other hand, it is also possible to neutralize using an ion exchange resin instead of using an acidic compound.
이상의 방법에 의해 얻어지는 본 발명의 고중합도 오가노실록산의 양이온계 에멀전 조성물은, 섬유처리제, 이형제, 발수제, 화장품원료 등으로서 호적하게 이용되고, 각종 섬유, 피혁, 종이, 모발 등에 처리함으로써 우수한 유연성, 윤활성, 발수성, 볼륨감 등을 부여할 수 있다. 한편, 섬유로는, 면, 마, 견, 양모와 같은 천연섬유, 폴리에스테르, 폴리아미드, 폴리아크릴로니트릴, 폴리에틸렌, 폴리프로필렌, 비닐론, 폴리염화비닐, 스판덱스 등의 합성섬유, 아세테이트 등의 반합성섬유 등을 들 수 있는데, 이들로 한정되는 것은 아니다.The cationic emulsion composition of high polymerization degree organosiloxane of the present invention obtained by the above method is suitably used as a fiber treatment agent, a mold release agent, a water repellent agent, a cosmetic raw material, etc., and excellent flexibility by treating various fibers, leather, paper, hair, etc. Lubricity, water repellency, volume, and the like can be imparted. On the other hand, as fibers, natural fibers such as cotton, hemp, silk, wool, polyester, polyamide, polyacrylonitrile, polyethylene, polypropylene, vinylon, polyvinyl chloride, synthetic fibers such as spandex, semi-synthetic such as acetate fiber, etc. are mentioned, but it is not limited to these.
본 발명의 고중합도 오가노실록산의 양이온계 에멀전 조성물에는, 각종의 증점제, 안료, 염료, 침투제, 대전방지제, 소포제, 난연제, 항균제, 방부제, 발수제, 가교제, 밀착향상제나, 다른 실리콘오일, 실리콘 수지, 실리카, 아크릴 수지, 우레탄 수지 등을 적당히 배합할 수 있다.In the cationic emulsion composition of high polymerization degree organosiloxane of the present invention, various thickeners, pigments, dyes, penetrants, antistatic agents, defoamers, flame retardants, antibacterial agents, preservatives, water repellents, crosslinking agents, adhesion improvers, other silicone oils, silicone resins , silica, an acrylic resin, a urethane resin, etc. can be mix|blended suitably.
본 발명의 고중합도 오가노실록산의 양이온계 에멀전 조성물은, 건조 후에 피막을 형성하는 것이 가능하며, 섬유, 종이, 금속, 목재, 고무, 플라스틱, 유리 등 각종 기재 표면에 처리하여 사용할 수 있다. 기재에의 도포방법으로는, 침지법, 스프레이법, 롤코트법, 바코트법, 브러싱법 등, 종래 공지의 각종 도포법이 가능하다.The cationic emulsion composition of high polymerization degree organosiloxane of the present invention can form a film after drying, and can be used by treating the surface of various substrates such as fibers, paper, metal, wood, rubber, plastic, glass, and the like. As a coating method to a base material, various conventionally well-known coating methods, such as a dipping method, a spraying method, a roll coating method, a bar coating method, and a brushing method, are possible.
실시예Example
이하, 실시예 및 비교예를 나타내고, 본 발명을 구체적으로 설명하는데, 본 발명은 하기의 실시예로 제한되는 것은 아니다. 한편, 하기의 예에 있어서, 「%」는 「질량%」를 나타낸다.Hereinafter, Examples and Comparative Examples are shown and the present invention will be specifically described, but the present invention is not limited to the following Examples. In addition, in the following example, "%" represents "mass %".
[실시예 1][Example 1]
일반식: HO-[(CH3)2SiO]n-H로 표시되는 양말단 하이드록시폴리디메틸실록산((D)성분) 300g(여기서, n은 약 310이며, 25℃에 있어서의 점도가 1,500mPa·s이다), 트리에톡시페닐실란((E)성분) 4.3g, 트리옥틸메틸암모늄클로라이드((B-1)성분)의 유효성분 75%의 IPA(이소프로필알코올)용액(TOMAC-75: 라이온·스페셜리티·케미칼즈사제) 24.0g, 베헤닐트리옥틸암모늄클로라이드((B-2)성분)의 유효성분 80%의 에탄올품(品)(리포카드 22-80: 라이온·스페셜리티·케미칼즈사제) 18.0g, 이온교환수((C)성분) 239.3g을 호모믹서, 디스퍼를 이용하여 균일하게 유화분산함으로써 에멀전을 얻었다. 이 에멀전에 30% 암모니아수용액 6.6g을 첨가하였다(알칼리촉매). 그 후, 액온도를 15℃로 낮추고, 24시간 중합을 행하여, 아세트산 7.8g으로 중화함으로써 에멀전A를 얻었다.General formula: HO-[(CH 3 ) 2 SiO] 300 g of both terminal hydroxypolydimethylsiloxane (component (D)) represented by n -H (here, n is about 310, and the viscosity at 25°C is 1,500 mPa s), triethoxyphenylsilane (component (E)) 4.3 g, trioctylmethylammonium chloride (component (B-1)) 75% of the active ingredient in IPA (isopropyl alcohol) solution (TOMAC-75) : Lion Specialty Chemicals Co., Ltd.) 24.0 g, ethanol product of 80% active ingredient of behenyltrioctylammonium chloride ((B-2) component) (Lipocard 22-80: Lion Specialty Chemicals) The emulsion was obtained by emulsifying and dispersing 18.0 g of company) and 239.3 g of ion-exchange water ((C)component) uniformly using a homomixer and a disper. To this emulsion, 6.6 g of a 30% aqueous ammonia solution was added (alkali catalyst). Then, the liquid temperature was lowered|hung to 15 degreeC, polymerization was performed for 24 hours, and emulsion A was obtained by neutralizing with 7.8 g of acetic acid.
[실시예 2][Example 2]
실시예 1의 이온교환수를 215.3g으로 대신하고, 추가로 비이온계 유화제로서, 폴리옥시에틸렌알킬에테르인 에멀겐 109P(카오사제) 24.0g을 추가한 것 이외는 실시예 1과 동일하게 하여 에멀전B를 얻었다.In the same manner as in Example 1, except that 215.3 g of the ion-exchanged water in Example 1 was replaced, and 24.0 g of Emulgen 109P (manufactured by Kaos), which is a polyoxyethylene alkyl ether, was added as a nonionic emulsifier. Emulsion B was obtained.
[실시예 3][Example 3]
실시예 2의 트리옥틸메틸암모늄클로라이드의 유효성분 75%의 IPA용액(TOMAC-75: 라이온·스페셜리티·케미칼즈사제)을 3.0g으로, 이온교환수를 236.3g으로 대신한 것 이외는 실시예 2와 동일하게 하여 에멀전C를 얻었다.Example 2 except that an IPA solution of 75% of the active ingredient of trioctylmethylammonium chloride of Example 2 (TOMAC-75: manufactured by Lion Specialty Chemicals) was replaced with 3.0 g and ion-exchanged water was replaced with 236.3 g Emulsion C was obtained in the same manner as
[실시예 4][Example 4]
실시예 2의 트리옥틸메틸암모늄클로라이드의 유효성분 75%의 IPA용액(TOMAC-75: 라이온·스페셜리티·케미칼즈사제)을 12.0g으로, 이온교환수를 227.3g으로 대신한 것 이외는 실시예 2와 동일하게 하여 에멀전D를 얻었다.Example 2 except that 12.0 g of an IPA solution (TOMAC-75, manufactured by Lion Specialty Chemicals) containing 75% of the active ingredient of trioctylmethylammonium chloride of Example 2 was replaced with 227.3 g of ion-exchanged water Emulsion D was obtained in the same manner as
[실시예 5][Example 5]
실시예 4에 있어서의 중합조건을 15℃에서 48시간으로 하여 중합한 것 이외는, 실시예 4와 동일하게 하여 에멀전E를 얻었다.Emulsion E was obtained in the same manner as in Example 4, except that polymerization was carried out under the polymerization conditions in Example 4 at 15°C for 48 hours.
[실시예 6][Example 6]
실시예 4의 이온교환수를 231.6g으로 변경하고, 30% 암모니아수용액 대신에 85%의 KOH를 2.3g을 첨가한 것 이외는 실시예 4와 동일하게 하여 에멀전F를 얻었다.Emulsion F was obtained in the same manner as in Example 4 except that the ion-exchanged water of Example 4 was changed to 231.6 g, and 2.3 g of 85% KOH was added instead of 30% aqueous ammonia solution.
[비교예 1][Comparative Example 1]
실시예 1의 트리에톡시페닐실란을 1.1g으로, 이온교환수를 258.7g으로 대신하고, 추가로 트리옥틸메틸암모늄클로라이드의 유효성분 75%의 IPA용액(TOMAC-75: 라이온·스페셜리티·케미칼즈사제), 및, 베헤닐트리옥틸암모늄클로라이드의 유효성분 80%의 에탄올품(리포카드 22-80: 라이온·스페셜리티·케미칼즈사제)을 세틸트리메틸암모늄클로라이드의 유효성분 30%의 수용액(코타민 60W: 카오사제) 25.8g으로 대신한 것 이외는 실시예 1과 동일하게 하여 에멀전G를 얻었다.The triethoxyphenylsilane of Example 1 was replaced with 1.1 g and ion-exchanged water was replaced with 258.7 g, and an IPA solution containing 75% of the active ingredient of trioctylmethylammonium chloride (TOMAC-75: Lion Specialty Chemicals) ), and an ethanol product (Lipocard 22-80: Lion Specialty Chemicals Co., Ltd.) containing 80% of the active ingredient of behenyltrioctylammonium chloride as an aqueous solution of 30% of the active ingredient of cetyltrimethylammonium chloride (Cotamine 60W) : Emulsion G was obtained in the same manner as in Example 1 except that it was replaced with 25.8 g (manufactured by Kao Corporation).
[비교예 2][Comparative Example 2]
비교예 1에 있어서의 중합조건을 15℃에서 96시간으로 하여 중합한 것 이외는, 비교예 1과 동일하게 하여 에멀전H를 얻었다.Emulsion H was obtained in the same manner as in Comparative Example 1, except that polymerization was carried out under the polymerization conditions in Comparative Example 1 at 15°C for 96 hours.
[비교예 3][Comparative Example 3]
비교예 1의 트리에톡시페닐실란을 4.3g으로, 이온교환수를 255.5g으로 대신한 것 이외는 비교예 1과 동일하게 하여 에멀전I를 얻었다.Emulsion I was obtained in the same manner as in Comparative Example 1 except that triethoxyphenylsilane of Comparative Example 1 was replaced with 4.3 g and ion-exchanged water was replaced with 255.5 g.
[비교예 4][Comparative Example 4]
비교예 3의 세틸트리메틸암모늄클로라이드의 유효성분 30%의 수용액(코타민 60W: 카오사제)을 트리옥틸메틸암모늄클로라이드의 유효성분 75%의 IPA용액(TOMAC-75: 라이온·스페셜리티·케미칼즈사제) 24.0g으로, 이온교환수를 257.3g으로 대신한 것 이외는 비교예 3과 동일하게 하여 에멀전J를 얻었다.An aqueous solution of 30% of the active ingredient of cetyltrimethylammonium chloride of Comparative Example 3 (Cotamine 60W: manufactured by Kaos) was mixed with an IPA solution of 75% of the active ingredient of trioctylmethylammonium chloride (TOMAC-75: manufactured by Lion Specialty Chemicals) Emulsion J was obtained in the same manner as in Comparative Example 3 except that 24.0 g of ion-exchanged water was replaced with 257.3 g.
[비교예 5][Comparative Example 5]
비교예 4에 세틸트리메틸암모늄클로라이드의 유효성분 30%의 수용액(코타민 60W: 카오사제) 25.8g을 추가하고, 이온교환수를 231.5g으로 대신한 것 이외는 비교예 4와 동일하게 하여 제조하였으나, 본 조성으로는 에멀전K를 제조할 수는 없었으므로 물성, 특성평가는 행하지 않았다.It was prepared in the same manner as in Comparative Example 4 except that 25.8 g of an aqueous solution of 30% of the active ingredient of cetyltrimethylammonium chloride (Cotamine 60W: manufactured by Kaos) was added to Comparative Example 4, and 231.5 g of ion-exchanged water was replaced. , Since emulsion K could not be prepared with this composition, physical properties and characteristics were not evaluated.
[비교예 6][Comparative Example 6]
25℃에 있어서의 점도가 800,000mPa·s인 직쇄디메틸실리콘을 300g, 세틸트리메틸암모늄클로라이드의 유효성분 30%의 수용액(코타민 60W: 카오사제) 21.6g, 이온교환수 235.2g을 호모믹서, 디스퍼를 이용하여 균일하게 유화분산함으로써 에멀전L을 얻었다.300 g of straight-chain dimethyl silicone having a viscosity of 800,000 mPa·s at 25° C., 21.6 g of an aqueous solution of 30% cetyltrimethylammonium chloride as an active ingredient (Cotamine 60W: manufactured by Kaos Corporation), and 235.2 g of ion-exchanged water were mixed with a homomixer and disc Emulsion L was obtained by uniformly emulsifying and dispersing using fur.
상기 실시예 1~6, 비교예 1~6에서 얻어진 에멀전의 물성, 특성을 하기 평가방법에 의해 측정하고, 결과를 표 1, 2에 나타냈다.The physical properties and characteristics of the emulsions obtained in Examples 1 to 6 and Comparative Examples 1 to 6 were measured by the following evaluation method, and the results are shown in Tables 1 and 2.
(추출한 실리콘의 점도)(Viscosity of extracted silicone)
에멀전A~L 300g을 2L의 IPA 중에 교반하면서 첨가함으로써 에멀전을 파괴시켜 폴리디오가노실록산을 추출하고, 이 폴리디오가노실록산을 105℃에서 3시간 건조한 후, 25℃에 있어서 BH형 회전점도계로 점도를 측정하였다. 한편, 이 점도는 액상으로 측정할 수 있는 것은 그대로, 점도가 너무 높아 측정할 수 없는 것은 10% 톨루엔용해점도를 측정하였다. 점도가 너무 높아 액상으로 측정할 수 없는 것의 점도는 모두 300,000mPa·s 이상이다.By adding 300 g of emulsions A to L in 2 L of IPA while stirring, the emulsion is destroyed to extract polydiorganosiloxane, and after drying the polydiorganosiloxane at 105° C. for 3 hours, the viscosity at 25° C. with a BH-type rotational viscometer was measured. On the other hand, this viscosity was measured as it is in the liquid phase, and the viscosity in 10% toluene was measured for the one that could not be measured because the viscosity was too high. The viscosity of all the things that are too high to be measured in a liquid phase are 300,000 mPa·s or more.
(피막형성의 유무)(Presence or absence of film formation)
에멀전A~L 20g을 PP(폴리프로필렌)트레이에 분취하고, 25℃에서 48시간 건조시킨 후, 추가로 105℃에서 1시간 건조시켜, 피막이 형성되었는지 평가하였다.20 g of emulsions A to L were aliquoted on a PP (polypropylene) tray, dried at 25° C. for 48 hours, and further dried at 105° C. for 1 hour to evaluate whether a film was formed.
○: 피막형성 ○: film formation
×: 피막형성 없음(액상 그대로) ×: No film formation (as it is in liquid state)
(보존안정성)(Storage stability)
25℃에서 1개월 정치한 후의 외관을 육안으로 평가하였다.The external appearance after standing still at 25 degreeC for 1 month was evaluated visually.
○: 분리 없음 ○: No separation
△: 약간 분리 △: slightly separated
×: 완전히 분리 ×: completely separated
(처리포의 감촉)(Tactile of processed cloth)
에멀전A~L을, 폴리오가노실록산농도가 1%가 되도록 이온교환수로 희석하여 처리액을 제작하였다. 처리액에 T/C브로드포(ブロ-ド布)를 10초간 침지시킨 후에 드로잉률(絞り率) 100%의 조건으로 롤을 이용하여 드로잉하고, 150℃에서 2분간 건조하였다. 그 후, 처리포를 손에 닿는 감촉으로 평가하고, 미처리포와 유연성 및 평활성을 비교하였다.)Emulsions A to L were diluted with ion-exchanged water so that the polyorganosiloxane concentration was 1% to prepare a treatment solution. After immersing the T/C broad cloth in the treatment solution for 10 seconds, drawing was performed using a roll under the condition of a draw rate of 100%, and dried at 150° C. for 2 minutes. After that, the treated fabric was evaluated for the hand feel, and the flexibility and smoothness were compared with the untreated fabric.)
○: 양호 ○: good
×: 미처리포 레벨 ×: Untreated gun level
(처리포의 세탁내구성)(Washing durability of treated cloth)
에멀전A~L을, 폴리오가노실록산농도가 1%가 되도록 이온교환수로 희석하여 처리액을 제작하였다. 처리액에 T/C브로드포를 10초간 침지시킨 후에 드로잉률 100%의 조건으로 롤을 이용하여 드로잉하고, 150℃에서 2분간 건조하였다. 그 후, 처리포를 반으로 재단하고, 편방의 처리포를 JIS LO217 103에 준거한 수법에 의해, 세탁기에 의한 세탁을 1회 실시한 후에 실온에서 1일간 건조하였다. 세탁 전후의 처리포의 섬유표면의 실리콘잔존량을 형광X선 분석장치(Rigaku사제)로 측정하고, 세탁 후의 잔존율(%)을 산출하였다.Emulsions A to L were diluted with ion-exchanged water so that the polyorganosiloxane concentration was 1% to prepare a treatment solution. After immersing the T/C broad cloth in the treatment solution for 10 seconds, drawing was performed using a roll under the condition of a draw rate of 100%, and dried at 150° C. for 2 minutes. Thereafter, the treated fabric was cut in half, and the one-sided treated fabric was washed with a washing machine once by a method conforming to JIS LO217 103, and then dried at room temperature for 1 day. The amount of silicone remaining on the fiber surface of the treated fabric before and after washing was measured with a fluorescent X-ray analyzer (manufactured by Rigaku), and the residual ratio (%) after washing was calculated.
[표 1][Table 1]
[표 2][Table 2]
표 1, 2에 나타내는 바와 같이, 본 발명의 고중합도 폴리오가노실록산의 양이온계 에멀전 조성물은 고점도여도 비교적 단시간에 중합할 수 있음과 함께, 피막형성능을 갖고 있는 점에서 섬유에 처리했을 때의 내구성이 우수하고, 또한, 처리포의 감촉도 양호하다. 나아가, 본 발명의 고중합도 폴리오가노실록산의 양이온계 에멀전 조성물은 보존안정성도 우수하다. 이에 반해 비교예의 조성에 의해 얻어진 양이온계 에멀전 조성물은, 안정성은 높지만, 피막형성능이 없는 것이나, 또한 섬유처리했을 때의 내구성이 뒤떨어져 있거나, 피막형성능은 있지만, 에멀전의 안정성이 낮아 바로 분리되어 버린다.As shown in Tables 1 and 2, the cationic emulsion composition of the high polymerization degree polyorganosiloxane of the present invention can polymerize in a relatively short time even at high viscosity, and has a film-forming ability, so the durability when treated on fibers is improved. It is excellent, and the feel of the processed cloth is also favorable. Furthermore, the cationic emulsion composition of the high polymerization degree polyorganosiloxane of the present invention has excellent storage stability. On the other hand, the cationic emulsion composition obtained by the composition of the comparative example has high stability but lacks film-forming ability, is inferior in durability when treated with fibers, or has film-forming ability, but the stability of the emulsion is low and separates immediately.
본 발명의 고중합도 폴리오가노실록산의 양이온계 에멀전 조성물을 섬유처리제로서 이용함으로써, 섬유에 대하여 양호한 유연성을 부여할 수 있고, 내구성도 우수한 점에서, 세탁처리 후도 양호한 유연성을 유지하는 것이 가능하다. 나아가, 본 발명의 고중합도 폴리오가노실록산의 양이온계 에멀전 조성물을 처리하여 건조시켰을 때에 형성되는 피막은 내구성이 높은 점에서, 범용성도 우수하고, 섬유처리제 이외에도, 이형제나 발수제, 화장료, 모발용 화장료 등에 널리 응용이 가능하다.By using the cationic emulsion composition of the high polymerization degree polyorganosiloxane of the present invention as a fiber treatment agent, good flexibility can be imparted to the fiber and excellent durability, it is possible to maintain good flexibility even after washing treatment. Furthermore, the film formed when the cationic emulsion composition of the high polymerization degree polyorganosiloxane of the present invention is treated and dried has high durability and is excellent in versatility, and is widely used as a release agent or water repellent agent, cosmetics, hair cosmetics, etc. in addition to fiber treatment agents. application is possible.
Claims (9)
[화학식 1]
(식 중, R1은, 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이며, R2는, 서로 독립적으로, 상기 R1의 선택지로부터 선택되는 기, 하이드록시기, 또는 탄소수 1~20의 알콕시기이며, a, b, c, d는 이 폴리오가노실록산의 25℃에 있어서의 점도가 300,000mPa·s 이상을 만족시키는 값이며, a≥2, c+d≥1이다.)
(B-1)양이온계 계면활성제: Q1 3(CH3)N+·X-: 0.1~30질량부,
(여기서, Q1은, 동일 또는 이종의 탄소수 6~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)
(B-2)양이온계 계면활성제: Q2(CH3)3N+·X-: 0.1~30질량부,
(여기서, Q2는, 탄소수 17~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)
(C)물: 30~3,000질량부
를 함유하여 이루어지는 것을 특징으로 하는 폴리오가노실록산의 양이온계 에멀전 조성물.(A) Polyorganosiloxane having a viscosity of 300,000 mPa·s or more at 25°C, represented by the following average composition formula (1): 100 parts by mass;
[Formula 1]
(Wherein, R 1 is, independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and R 2 is, independently of each other, a group selected from the options of R 1 above, a hydroxyl group, Or it is a C1-C20 alkoxy group, a, b, c, and d are a value which the viscosity in 25 degreeC of this polyorganosiloxane satisfy|fills 300,000 mPa*s or more, a≥2, c+d≥1 to be.)
(B-1) cationic surfactant: Q 1 3 (CH 3 )N + ·X - : 0.1 to 30 parts by mass,
(Here, Q 1 is the same or different 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: Q 2 (CH 3 ) 3 N + X - : 0.1 to 30 parts by mass,
(Here, Q 2 is 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.)
(C) Water: 30 to 3,000 parts by mass
A cationic emulsion composition of polyorganosiloxane, characterized in that it contains a.
비이온계 계면활성제를 추가로 포함하는 것을 특징으로 하는 폴리오가노실록산의 양이온계 에멀전 조성물.According to claim 1,
Cationic emulsion composition of polyorganosiloxane, characterized in that it further comprises a nonionic surfactant.
건조 후에 피막을 형성하는 것을 특징으로 하는 폴리오가노실록산의 양이온계 에멀전 조성물.3. The method of claim 1 or 2,
A cationic emulsion composition of polyorganosiloxane, characterized in that it forms a film after drying.
(E)하기에 나타내는 어느 1개 또는 2개 이상의 오가노알콕시실란: 0~20질량부
Si(OR3)4, R1Si(OR3)3, R1 2Si(OR3)2, R1 3Si(OR3)
(여기서, R1은 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이며, R3은 서로 독립적으로, 수소원자, 또는, 탄소수 1~20의 1가 유기기이다.),
(B-1)양이온계 계면활성제: Q1 3(CH3)N+·X-: 0.1~30질량부,
(여기서, Q1은 동일 또는 이종의 탄소수 6~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)
(B-2)양이온계 계면활성제: Q2(CH3)3N+·X-: 0.1~30질량부,
(여기서, Q2는 탄소수 17~30의 1가 유기기, X는 할로겐원자 또는 탄소수 1~6의 1가 카르복실기이다.)
(C)물: 30~3,000질량부
를 유화분산시켜 얻어지는 에멀전을, 알칼리촉매존재하, 0~30℃에서 1~150시간 중합을 행하고, 추가로 중화를 행하는 것을 특징으로 하는 폴리오가노실록산의 양이온계 에멀전 조성물의 제조방법.(D) general formula: HO-[R 1 2 SiO] j -H both terminal hydroxypolydiorganosiloxane represented by -H (here, R 1 is, independently of each other, a hydrogen atom, or 1 having 1 to 20 carbon atoms) is an organic group, and j is a value with which the viscosity at 25°C of both terminal hydroxypolydiorganosiloxane satisfies less than 2,000 mPa·s.): 100 parts by mass;
(E) any one or two or more organoalkoxysilanes shown below: 0 to 20 parts by mass
Si(OR 3 ) 4 , R 1 Si(OR 3 ) 3 , R 1 2 Si(OR 3 ) 2 , R 1 3 Si(OR 3 )
(Here, R 1 is, independently of each other, a hydrogen atom or a monovalent organic group having 1 to 20 carbon atoms, and R 3 is, independently of each other, a hydrogen atom, or a monovalent organic group having 1 to 20 carbon atoms.) ,
(B-1) cationic surfactant: Q 1 3 (CH 3 )N + ·X - : 0.1 to 30 parts by mass,
(Here, Q 1 is the same or different 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: Q 2 (CH 3 ) 3 N + X - : 0.1 to 30 parts by mass,
(Here, Q 2 is 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.)
(C) Water: 30 to 3,000 parts by mass
A method for producing a cationic emulsion composition of polyorganosiloxane, characterized in that the emulsion obtained by emulsifying and dispersing is polymerized for 1 to 150 hours at 0 to 30° C. in the presence of an alkali catalyst, and further neutralized.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5638609A (en) | 1979-09-05 | 1981-04-13 | Toshiba Corp | Monitoring method for plant |
| JPH08104752A (en) | 1994-08-25 | 1996-04-23 | Dow Corning Corp | Emulsion polymerization process |
| JPH09137062A (en) | 1995-07-28 | 1997-05-27 | Toshiba Silicone Co Ltd | Cationic stable silicone emulsion and its production |
| JPH09278626A (en) | 1995-08-07 | 1997-10-28 | Toshiba Silicone Co Ltd | Silicone emulsion, cosmetic and production of 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 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1239419A (en) * | 1996-11-04 | 1999-12-22 | 普罗克特和甘保尔公司 | Hair conditioning compsn. comprising silicone emulsion |
| EP0916690B1 (en) * | 1997-11-17 | 2002-02-06 | 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 |
| 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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Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5638609A (en) | 1979-09-05 | 1981-04-13 | Toshiba Corp | Monitoring method for plant |
| JPH08104752A (en) | 1994-08-25 | 1996-04-23 | Dow Corning Corp | Emulsion polymerization process |
| JPH09137062A (en) | 1995-07-28 | 1997-05-27 | Toshiba Silicone Co Ltd | Cationic stable silicone emulsion and its production |
| JPH09278626A (en) | 1995-08-07 | 1997-10-28 | Toshiba Silicone Co Ltd | Silicone emulsion, cosmetic and production of 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 |
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