JP2005187687A - Method for manufacturing of aqueous emulsion of organopolysiloxane - Google Patents
Method for manufacturing of aqueous emulsion of organopolysiloxane Download PDFInfo
- Publication number
- JP2005187687A JP2005187687A JP2003431967A JP2003431967A JP2005187687A JP 2005187687 A JP2005187687 A JP 2005187687A JP 2003431967 A JP2003431967 A JP 2003431967A JP 2003431967 A JP2003431967 A JP 2003431967A JP 2005187687 A JP2005187687 A JP 2005187687A
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- JP
- Japan
- Prior art keywords
- aqueous emulsion
- group
- parts
- producing
- emulsion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000000839 emulsion Substances 0.000 title claims abstract description 103
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 38
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 37
- 238000000034 method Methods 0.000 title abstract description 14
- 239000002685 polymerization catalyst Substances 0.000 claims abstract description 23
- 125000005375 organosiloxane group Chemical group 0.000 claims abstract description 3
- 239000003093 cationic surfactant Substances 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
- 150000002430 hydrocarbons Chemical group 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 150000001282 organosilanes Chemical class 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical group 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- 239000003921 oil Substances 0.000 abstract description 30
- 238000000926 separation method Methods 0.000 abstract description 29
- 238000006116 polymerization reaction Methods 0.000 abstract description 11
- 125000002091 cationic group Chemical group 0.000 abstract description 4
- 239000004094 surface-active agent Substances 0.000 abstract description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000010703 silicon Substances 0.000 abstract 1
- -1 siloxanes Chemical class 0.000 description 52
- 238000007720 emulsion polymerization reaction Methods 0.000 description 38
- 239000000203 mixture Substances 0.000 description 35
- 239000002245 particle Substances 0.000 description 29
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 description 27
- 235000019198 oils Nutrition 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 235000014113 dietary fatty acids Nutrition 0.000 description 21
- 239000000194 fatty acid Substances 0.000 description 21
- 229930195729 fatty acid Natural products 0.000 description 21
- XMSXQFUHVRWGNA-UHFFFAOYSA-N Decamethylcyclopentasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 XMSXQFUHVRWGNA-UHFFFAOYSA-N 0.000 description 20
- 239000004205 dimethyl polysiloxane Substances 0.000 description 15
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 15
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 125000001931 aliphatic group Chemical group 0.000 description 12
- 239000011734 sodium Substances 0.000 description 12
- 229910052708 sodium Inorganic materials 0.000 description 12
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 11
- 239000000243 solution Substances 0.000 description 11
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 10
- 229960003237 betaine Drugs 0.000 description 10
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000003240 coconut oil Substances 0.000 description 7
- 235000019864 coconut oil Nutrition 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 125000000524 functional group Chemical group 0.000 description 5
- IUMSDRXLFWAGNT-UHFFFAOYSA-N Dodecamethylcyclohexasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 IUMSDRXLFWAGNT-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- 239000000654 additive Substances 0.000 description 4
- 125000003277 amino group Chemical group 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 230000001804 emulsifying effect Effects 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 125000001153 fluoro group Chemical group F* 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 125000005641 methacryl group Chemical group 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 125000003396 thiol group Chemical group [H]S* 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 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
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000002537 cosmetic Substances 0.000 description 3
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229920002503 polyoxyethylene-polyoxypropylene Polymers 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 229940081974 saccharin Drugs 0.000 description 3
- 235000019204 saccharin Nutrition 0.000 description 3
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- HVYJSOSGTDINLW-UHFFFAOYSA-N 2-[dimethyl(octadecyl)azaniumyl]acetate Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)CC([O-])=O HVYJSOSGTDINLW-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerol Natural products OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 239000004166 Lanolin Substances 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000003973 alkyl amines Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000001099 ammonium carbonate Substances 0.000 description 2
- 239000002280 amphoteric surfactant Substances 0.000 description 2
- 230000002421 anti-septic effect Effects 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 229960000686 benzalkonium chloride Drugs 0.000 description 2
- 229940092714 benzenesulfonic acid Drugs 0.000 description 2
- 229960001950 benzethonium chloride Drugs 0.000 description 2
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 2
- LLEMOWNGBBNAJR-UHFFFAOYSA-N biphenyl-2-ol Chemical compound OC1=CC=CC=C1C1=CC=CC=C1 LLEMOWNGBBNAJR-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000004359 castor oil Substances 0.000 description 2
- 235000019438 castor oil Nutrition 0.000 description 2
- OSASVXMJTNOKOY-UHFFFAOYSA-N chlorobutanol Chemical compound CC(C)(O)C(Cl)(Cl)Cl OSASVXMJTNOKOY-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 2
- 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 2
- WLCFKPHMRNPAFZ-UHFFFAOYSA-M didodecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC WLCFKPHMRNPAFZ-UHFFFAOYSA-M 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- XGZRAKBCYZIBKP-UHFFFAOYSA-L disodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[Na+] XGZRAKBCYZIBKP-UHFFFAOYSA-L 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 235000011187 glycerol Nutrition 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 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 2
- 125000006038 hexenyl group Chemical group 0.000 description 2
- 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 2
- 230000001771 impaired effect Effects 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 229940039717 lanolin Drugs 0.000 description 2
- 235000019388 lanolin Nutrition 0.000 description 2
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 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 2
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 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 2
- 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 2
- 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 2
- 125000002958 pentadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 230000002940 repellent Effects 0.000 description 2
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 2
- 238000007142 ring opening reaction Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 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 2
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 2
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 2
- 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 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229940043810 zinc pyrithione Drugs 0.000 description 2
- PICXIOQBANWBIZ-UHFFFAOYSA-N zinc;1-oxidopyridine-2-thione Chemical compound [Zn+2].[O-]N1C=CC=CC1=S.[O-]N1C=CC=CC1=S PICXIOQBANWBIZ-UHFFFAOYSA-N 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- ORFPMGWJDWEAAQ-UHFFFAOYSA-N (4-ethenylphenyl)-triethoxysilane Chemical compound CCO[Si](OCC)(OCC)C1=CC=C(C=C)C=C1 ORFPMGWJDWEAAQ-UHFFFAOYSA-N 0.000 description 1
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 1
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- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 description 1
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- 239000003112 inhibitor Substances 0.000 description 1
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- 238000005342 ion exchange Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- BYURCDANQKFTAN-UHFFFAOYSA-N n'-(3-dimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[SiH](OC)CCCNCCN BYURCDANQKFTAN-UHFFFAOYSA-N 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- WNBWUMULCMJZPG-UHFFFAOYSA-N n,2-dimethyl-n-(3-trimethoxysilylpropyl)prop-2-enamide Chemical compound CO[Si](OC)(OC)CCCN(C)C(=O)C(C)=C WNBWUMULCMJZPG-UHFFFAOYSA-N 0.000 description 1
- ZLDHKBPNTHQRDM-UHFFFAOYSA-N n-[3-[diethoxy(methyl)silyl]propyl]-2-methyl-n-(2-methylprop-2-enoyl)prop-2-enamide Chemical compound CCO[Si](C)(OCC)CCCN(C(=O)C(C)=C)C(=O)C(C)=C ZLDHKBPNTHQRDM-UHFFFAOYSA-N 0.000 description 1
- NOBWIVABEULIHG-UHFFFAOYSA-N n-[3-[diethoxy(methyl)silyl]propyl]-n-methyldodecanamide Chemical compound CCCCCCCCCCCC(=O)N(C)CCC[Si](C)(OCC)OCC NOBWIVABEULIHG-UHFFFAOYSA-N 0.000 description 1
- ZYXJRZFYDQXUNG-UHFFFAOYSA-N n-[3-[dimethoxy(methyl)silyl]propyl]-2-methyl-n-(2-methylprop-2-enoyl)prop-2-enamide Chemical compound CO[Si](C)(OC)CCCN(C(=O)C(C)=C)C(=O)C(C)=C ZYXJRZFYDQXUNG-UHFFFAOYSA-N 0.000 description 1
- HHTDCEQODYJFHQ-UHFFFAOYSA-N n-[3-[dimethoxy(methyl)silyl]propyl]-n-methyldodecanamide Chemical compound CCCCCCCCCCCC(=O)N(C)CCC[Si](C)(OC)OC HHTDCEQODYJFHQ-UHFFFAOYSA-N 0.000 description 1
- IVGYGFFYFIXXQZ-UHFFFAOYSA-N n-dodecanoyl-n-(3-triethoxysilylpropyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CCC[Si](OCC)(OCC)OCC)C(=O)CCCCCCCCCCC IVGYGFFYFIXXQZ-UHFFFAOYSA-N 0.000 description 1
- ZPNANHXELPLBAO-UHFFFAOYSA-N n-dodecanoyl-n-(3-trimethoxysilylpropyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(CCC[Si](OC)(OC)OC)C(=O)CCCCCCCCCCC ZPNANHXELPLBAO-UHFFFAOYSA-N 0.000 description 1
- JXHZVHFODJSANQ-UHFFFAOYSA-N n-ethyl-n-methylethanamine;hydrochloride Chemical compound Cl.CCN(C)CC JXHZVHFODJSANQ-UHFFFAOYSA-N 0.000 description 1
- FGANXOZSRFNUFE-UHFFFAOYSA-N n-methyl-n-(3-triethoxysilylpropyl)prop-2-enamide Chemical compound CCO[Si](OCC)(OCC)CCCN(C)C(=O)C=C FGANXOZSRFNUFE-UHFFFAOYSA-N 0.000 description 1
- YDZUFQODBNNRLN-UHFFFAOYSA-N n-methyl-n-(3-trimethoxysilylpropyl)dodecanamide Chemical compound CCCCCCCCCCCC(=O)N(C)CCC[Si](OC)(OC)OC YDZUFQODBNNRLN-UHFFFAOYSA-N 0.000 description 1
- KEHPXLZVVHSDLW-UHFFFAOYSA-N n-methyl-n-(3-trimethoxysilylpropyl)prop-2-enamide Chemical compound CO[Si](OC)(OC)CCCN(C)C(=O)C=C KEHPXLZVVHSDLW-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- VUWDAOLDXOYMIZ-UHFFFAOYSA-N nonadecan-1-amine;hydrochloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCCC[NH3+] VUWDAOLDXOYMIZ-UHFFFAOYSA-N 0.000 description 1
- 125000001196 nonadecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- AZJXQVRPBZSNFN-UHFFFAOYSA-N octane-3,3-diol Chemical compound CCCCCC(O)(O)CC AZJXQVRPBZSNFN-UHFFFAOYSA-N 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 125000005386 organosiloxy group Chemical group 0.000 description 1
- 235000010292 orthophenyl phenol Nutrition 0.000 description 1
- 239000004306 orthophenyl phenol Substances 0.000 description 1
- 229960001257 oxyquinoline sulfate Drugs 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 229940090668 parachlorophenol Drugs 0.000 description 1
- HWGNBUXHKFFFIH-UHFFFAOYSA-I pentasodium;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O HWGNBUXHKFFFIH-UHFFFAOYSA-I 0.000 description 1
- 229960003742 phenol Drugs 0.000 description 1
- 229960005323 phenoxyethanol Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 235000011056 potassium acetate Nutrition 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- ZZPKZRHERLGEKA-UHFFFAOYSA-N resorcinol monoacetate Chemical compound CC(=O)OC1=CC=CC(O)=C1 ZZPKZRHERLGEKA-UHFFFAOYSA-N 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229940043230 sarcosine Drugs 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000011083 sodium citrates Nutrition 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- HWCHICTXVOMIIF-UHFFFAOYSA-M sodium;3-(dodecylamino)propanoate Chemical compound [Na+].CCCCCCCCCCCCNCCC([O-])=O HWCHICTXVOMIIF-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- SFVFIFLLYFPGHH-UHFFFAOYSA-M stearalkonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 SFVFIFLLYFPGHH-UHFFFAOYSA-M 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 1
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 1
- 229960000790 thymol Drugs 0.000 description 1
- SLYPOVJCSQHITR-UHFFFAOYSA-N tioxolone Chemical compound OC1=CC=C2SC(=O)OC2=C1 SLYPOVJCSQHITR-UHFFFAOYSA-N 0.000 description 1
- 229960003070 tioxolone Drugs 0.000 description 1
- ICUTUKXCWQYESQ-UHFFFAOYSA-N triclocarban Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC=C(Cl)C(Cl)=C1 ICUTUKXCWQYESQ-UHFFFAOYSA-N 0.000 description 1
- 229960001325 triclocarban Drugs 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
- PDSVZUAJOIQXRK-UHFFFAOYSA-N trimethyl(octadecyl)azanium Chemical compound CCCCCCCCCCCCCCCCCC[N+](C)(C)C PDSVZUAJOIQXRK-UHFFFAOYSA-N 0.000 description 1
- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
- 235000019798 tripotassium phosphate Nutrition 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
Landscapes
- Silicon Polymers (AREA)
Abstract
Description
本発明は、オルガノポリシロキサンの水性エマルジョンの製造方法に関し、詳しくは、環状オルガノシロキサン４量体と５量体以上の環状オルガノシロキサンの乳化重合によるオルガノポリシロキサンの水性エマルジョンの製造方法に関する。 The present invention relates to a method for producing an aqueous organopolysiloxane emulsion, and more particularly to a method for producing an aqueous organopolysiloxane emulsion by emulsion polymerization of a cyclic organosiloxane tetramer and a pentamer or higher cyclic organosiloxane.
従来より、低重合度の環状オルガノシロキサン、すなわち、環状オルガノシロキサンオリゴマーをカチオン系界面活性剤により水中に乳化し、塩基性重合触媒存在下で乳化重合することにより、より高重合度のジオルガノポリシロキサンの水性エマルジョンを製造する方法がいくつか提案されている。例えば特公昭３４−２０４１では、オクタメチルシクロテトラシロキサン、環状ジメチルシロキサン、または環状フェニルメチルシロキサンと環状ジメチルシロキサンの混合物をジドデシルジメチルアンモニウムクロライドやオクタデシルトリメチルアンモニウムクロライドのようなカチオン系界面活性剤により水中に乳化し、アンモニアのような塩基性重合触媒存在下で乳化重合してジメチルポリシロキサンやメチルフェニルポリシロキサンの水性エマルジョンを製造している。特公昭５６−３８６０９では、オクタメチルシクロテトラシロキサンとＮ−（２−アミノエチル）−３−アミノプロピルトリメトキシシランをヘキサデシルトリメチルアンモニウムクロライドにより水中に乳化し、塩基性重合触媒存在である水酸化カリウム存在下で乳化重合してオルガノポリシロキサンラッテクスを製造している。しかしながら、これらの製造方法では、乳化重合後、経時でクリーミングやオイル分離が発生し、エマルションが不均一化してしまい、長期間にわたって安定なジメチルポリシロキサンの水性エマルジョンを得ることはできないことに本発明者らは気付いた。
一方、特開２０００-７２８８０と特開２０００-２６４９６８には、環状ジメチルシロキサンオリゴマーの混合物をアルキルスルホン酸ナトリウムやアルキルベンゼンスルホン酸ナトリウムのような有機スルホン酸ナトリウムにより水中に乳化し、塩酸や硫酸のような鉱酸あるいはアルキルスルホン酸やアルキルベンゼンスルホン酸のような有機酸の存在下で乳化重合してオルガノポリシロキサンの水性エマルジョンの製造方法が開示されている。特開２０００-７２８８０は、水の使用量を低減して濃厚な直鎖状ジメチルポリシロキサンの水性エマルジョンを迅速に製造することを目的としており、特開２０００-２６４９６８は、小粒径のオルガノポリシロキサンの水性エマルジョンを製造することを目的としている。しかしながら、これらの製造方法は、経時でクリーミングやオイル分離が発生せず、長期間にわたって安定なジメチルポリシロキサンの水性エマルジョンを提供することを意図しておらず、しかも得られたジメチルポリシロキサンの水性エマルジョンは酸性が強いので、第４級アンモニウム塩系化合物を含有するカチオン性の化粧品やヘルスケア製品への配合に不適である。
Conventionally, a diorganopolysiloxane having a higher degree of polymerization is obtained by emulsifying a cyclic organosiloxane having a low degree of polymerization, i.e., a cyclic organosiloxane oligomer in water with a cationic surfactant, and emulsion polymerization in the presence of a basic polymerization catalyst. Several methods for producing aqueous emulsions of siloxanes have been proposed. For example, in Japanese Examined Patent Publication No. 34-2041, octamethylcyclotetrasiloxane, cyclic dimethylsiloxane, or a mixture of cyclic phenylmethylsiloxane and cyclic dimethylsiloxane is dissolved in water with a cationic surfactant such as didodecyldimethylammonium chloride or octadecyltrimethylammonium chloride. And then emulsion polymerization in the presence of a basic polymerization catalyst such as ammonia to produce an aqueous emulsion of dimethylpolysiloxane or methylphenylpolysiloxane. In Japanese Examined Patent Publication No. 56-38609, octamethylcyclotetrasiloxane and N- (2-aminoethyl) -3-aminopropyltrimethoxysilane are emulsified in water with hexadecyltrimethylammonium chloride, and hydroxylated in the presence of a basic polymerization catalyst. Organopolysiloxane latex is produced by emulsion polymerization in the presence of potassium. However, in these production methods, after emulsion polymerization, creaming and oil separation occur over time, the emulsion becomes non-uniform, and it is impossible to obtain a stable aqueous emulsion of dimethylpolysiloxane over a long period of time. They noticed.
On the other hand, in JP-A-2000-72880 and JP-A-2000-264968, a mixture of cyclic dimethylsiloxane oligomers is emulsified in water with an organic sodium sulfonate such as sodium alkylsulfonate or sodium alkylbenzenesulfonate, and the like, as hydrochloric acid or sulfuric acid. A method for producing an aqueous emulsion of an organopolysiloxane by emulsion polymerization in the presence of a mineral acid or an organic acid such as an alkyl sulfonic acid or an alkyl benzene sulfonic acid is disclosed. Japanese Patent Laid-Open No. 2000-72880 aims at rapidly producing a concentrated aqueous dimethylpolysiloxane emulsion by reducing the amount of water used, and Japanese Patent Laid-Open No. 2000-264968 discloses an organopolysiloxane having a small particle size. It is intended to produce an aqueous emulsion of siloxane. However, these production methods are not intended to provide an aqueous emulsion of dimethylpolysiloxane that does not cause creaming or oil separation over time, and is stable over a long period of time. Since emulsions are highly acidic, they are unsuitable for incorporation into cationic cosmetics and health care products containing quaternary ammonium salt compounds.
そこで、本発明者らはオクタメチルシクロテトラシロキサンのような環状オルガノシロキサンをカチオン系界面活性剤による水性エマルジョン状態で塩基性重合触媒により重合しても、乳化重合後、経時でクリーミングやオイル分離が発生せず、長期間にわたって安定なオルガノポリシロキサンの水性エマルジョンを得ることができる製造方法を鋭意検討した結果、本発明に至った。すなわち本発明の目的は、オクタメチルシクロテトラシロキサンのような環状オルガノシロキサンをカチオン系界面活性剤による水性エマルジョン状態で塩基性重合触媒により重合しても、乳化重合後長期間にわたってクリーミングやオイル分離を発生しない、オルガノポリシロキサンの安定な水性エマルジョンの製造方法を提供することにある。 Therefore, the present inventors can polymerize a cyclic organosiloxane such as octamethylcyclotetrasiloxane with a basic polymerization catalyst in an aqueous emulsion state with a cationic surfactant, but after the emulsion polymerization, creaming and oil separation may occur over time. As a result of intensive studies on a production method capable of obtaining an aqueous emulsion of organopolysiloxane that does not occur and is stable over a long period of time, the present invention has been achieved. That is, the object of the present invention is to form a cyclic organosiloxane such as octamethylcyclotetrasiloxane in a water-based emulsion state with a cationic surfactant using a basic polymerization catalyst, and to perform creaming and oil separation over a long period after emulsion polymerization. An object of the present invention is to provide a method for producing a stable aqueous emulsion of an organopolysiloxane that does not occur.
かかる目的は、環状オルガノシロキサン４量体と環状オルガノシロキサン５量体以上の混合物（該４量体１００重量部当たり該５量体以上５〜６５重量部である）を原料環状オルガノシロキサンとして使用することによって達成される。
本発明は、
[１]一般式（Ｒ１Ｒ２ＳｉＯ）４（式中Ｒ１、Ｒ２は同一種または異種の非置換または置換の１価炭化水素基である）で表される環状オルガノシロキサン４量体と一般式（Ｒ３Ｒ４ＳｉＯ）ｎ（式中Ｒ３、Ｒ４は同一種または異種の非置換または置換の１価炭化水素基であり、またｎは５以上の整数である）で表される環状オルガノシロキサン５量体以上（該４量体１００重量部当たり該５量体以上５〜６５重量部である）とをカチオン系界面活性剤による水性エマルジョン状態で塩基性重合触媒により重合することを特徴とする、Ｒ１Ｒ２ＳｉＯ単位とＲ３Ｒ４ＳｉＯ単位とからなるオルガノポリシロキサンの水性エマルジョンの製造方法。
[2]Ｒ１とＲ３がメチル基であり、Ｒ２とＲ４がアルキル基である[1]記載の水性エマルジョンの製造方法。
[3]アルキル基がメチル基である[2]記載の水性エマルジョンの製造方法。
[4]一般式（Ｒ３Ｒ４ＳｉＯ）ｎ（式中Ｒ３、Ｒ４、ｎは前記どおりである）で表される環状オルガノシロキサン５量体以上のうち、ｎが５または６で表されるものの合計が５０重量％以上であることを特徴とする、[1]記載の水性エマルジョンの製造方法。
[5]カチオン系界面活性剤が一般式Ｒ５Ｒ６（ＣＨ３）２Ｎ＋Ｃｌ−（式中Ｒ５、Ｒ６は同一種または異種の非置換または置換の１価炭化水素基であり、Ｒ５とＲ６のいずれかは水酸基であってもよい）で表される、[1]〜[4]のいずれか記載の水性エマルジョンの製造方法。
[6]塩基性重合触媒がアルカリ金属水酸化物であることを特徴とする、[1]〜[5]のいずれか記載の水性エマルジョンの製造方法。
[7]一般式（Ｒ１Ｒ２ＳｉＯ）４（式中Ｒ１、Ｒ２は同一種または異種の非置換または置換の１価炭化水素基である）で表される環状オルガノシロキサン４量体と一般式（Ｒ３Ｒ４ＳｉＯ）ｎ（式中Ｒ３、Ｒ４は同一種または異種の非置換または置換の１価炭化水素基であり、ｎは５以上の整数である）で表される環状オルガノシロキサン５量体以上とケイ素原子結合加水分解性基含有オルガノシランもしくはその加水分解物（該４量体１００重量部当たり該５量体以上５〜６５重量部、該オルガノシランもしくはその加水分解物０（０を含まない）〜３０重量部である）をカチオン系界面活性剤による水性エマルジョン状態で塩基性重合触媒により重合することを特徴とする、[1]記載の製造方法。
[8]Ｒ１とＲ３がメチル基であり、Ｒ２とＲ４がアルキル基である[7]記載の水性エマルジョンの製造方法。
[9]アルキル基がメチル基である[8]記載の水性エマルジョンの製造方法。
[10]一般式（Ｒ３Ｒ４ＳｉＯ）ｎ（式中Ｒ３、Ｒ４、ｎは前記どおりである）で表される環状オルガノシロキサン５量体以上のうち、ｎが５または６で表されるものの合計が５０重量％以上であることを特徴とする、[7]記載の水性エマルジョンの製造方法。
[11]カチオン系界面活性剤が一般式Ｒ５Ｒ６（ＣＨ３）２Ｎ＋Ｃｌ−（式中Ｒ５、Ｒ６は同一種または異種の非置換または置換の１価炭化水素基であり、Ｒ５とＲ６のいずれかは水酸基であってもよい）で表される、[7]〜[10]のいずれか記載の水性エマルジョンの製造方法。
[12]塩基性重合触媒がアルカリ金属水酸化物であることを特徴とする、[7]〜[11]のいずれか記載の水性エマルジョンの製造方法。に関する。
The purpose is to use a mixture of a cyclic organosiloxane tetramer and a cyclic organosiloxane pentamer or more (5 to 65 parts by weight of the pentamer per 100 parts by weight of the tetramer) as a raw material cyclic organosiloxane. Is achieved.
The present invention
[1] Cyclic organosiloxane tetramer represented by the general formula (R 1 R 2 SiO) 4 (wherein R 1 and R 2 are the same or different unsubstituted or substituted monovalent hydrocarbon group) And a general formula (R 3 R 4 SiO) n (wherein R 3 and R 4 are the same or different unsubstituted or substituted monovalent hydrocarbon groups, and n is an integer of 5 or more). The cyclic organosiloxane pentamer or more (the pentamer is 5 to 65 parts by weight per 100 parts by weight of the tetramer) is polymerized by a basic polymerization catalyst in an aqueous emulsion state with a cationic surfactant. A method for producing an aqueous emulsion of an organopolysiloxane comprising R 1 R 2 SiO units and R 3 R 4 SiO units.
[2] The method for producing an aqueous emulsion according to [1], wherein R 1 and R 3 are methyl groups, and R 2 and R 4 are alkyl groups.
[3] The method for producing an aqueous emulsion according to [2], wherein the alkyl group is a methyl group.
[4] Among cyclic organosiloxane pentamers or more represented by the general formula (R 3 R 4 SiO) n (wherein R 3 , R 4 and n are as defined above), n is 5 or 6 The method for producing an aqueous emulsion according to [1], wherein the total amount of the emulsion is 50% by weight or more.
[5] The cationic surfactant is represented by the general formula R 5 R 6 (CH 3 ) 2 N + Cl − , wherein R 5 and R 6 are the same or different unsubstituted or substituted monovalent hydrocarbon groups. Or any one of R 5 and R 6 may be a hydroxyl group). The method for producing an aqueous emulsion according to any one of [1] to [4].
[6] The method for producing an aqueous emulsion as described in any one of [1] to [5], wherein the basic polymerization catalyst is an alkali metal hydroxide.
[7] Cyclic organosiloxane tetramer represented by the general formula (R 1 R 2 SiO) 4 (wherein R 1 and R 2 are the same or different unsubstituted or substituted monovalent hydrocarbon groups) And a general formula (R 3 R 4 SiO) n (wherein R 3 and R 4 are the same or different unsubstituted or substituted monovalent hydrocarbon groups, and n is an integer of 5 or more). A cyclic organosiloxane pentamer or more and a silicon-bonded hydrolyzable group-containing organosilane or a hydrolyzate thereof (the pentamer or more per 5 parts by weight of the pentamer of 5 to 65 parts by weight, the organosilane or the hydrolyzate thereof). The production method according to [1], wherein the decomposition product 0 (excluding 0) to 30 parts by weight is polymerized with a basic polymerization catalyst in an aqueous emulsion state with a cationic surfactant.
[8] The method for producing an aqueous emulsion according to [7], wherein R 1 and R 3 are methyl groups, and R 2 and R 4 are alkyl groups.
[9] The method for producing an aqueous emulsion according to [8], wherein the alkyl group is a methyl group.
[10] Of cyclic organosiloxane pentamers or more represented by the general formula (R 3 R 4 SiO) n (wherein R 3 , R 4 and n are as defined above), n is 5 or 6. The method for producing an aqueous emulsion as set forth in [7], wherein the total amount of the emulsion is 50% by weight or more.
[11] The cationic surfactant is represented by the general formula R 5 R 6 (CH 3 ) 2 N + Cl − , wherein R 5 and R 6 are the same or different unsubstituted or substituted monovalent hydrocarbon groups. Or any one of R 5 and R 6 may be a hydroxyl group). The method for producing an aqueous emulsion according to any one of [7] to [10].
[12] The method for producing an aqueous emulsion as described in any one of [7] to [11], wherein the basic polymerization catalyst is an alkali metal hydroxide. About.
本発明の製造方法によると、環状オルガノシロキサン４量体と５量体以上の環状オルガノシロキサンの特定比率の混合物をカチオン系界面活性剤によるエマルジョン状態で塩基性重合触媒により重合するので、乳化重合後、経時でクリーミングやオイル分離が発生せず、長期間にわたって安定なオルガノポリシロキサンの水性エマルジョンを得ることができる。 According to the production method of the present invention, a mixture of a specific ratio of cyclic organosiloxane tetramer and pentamer or higher cyclic organosiloxane is polymerized by a basic polymerization catalyst in an emulsion state with a cationic surfactant. Thus, an aqueous emulsion of organopolysiloxane that does not cause creaming or oil separation with time and is stable over a long period of time can be obtained.
一般式（Ｒ１Ｒ２ＳｉＯ）４（式中Ｒ１、Ｒ２は同一種または異種の非置換または置換の１価炭化水素基である）で表される環状オルガノシロキサンと一般式（Ｒ３Ｒ４ＳｉＯ）ｎ（式中Ｒ３、Ｒ４は同一種または異種の非置換または置換の１価炭化水素基であり、ｎは５以上の整数である）で表される環状オルガノシロキサン４量体は乳化重合の主原料である。前記環状オルガノシロキサン４量体１００重量部当たり、前記環状オルガノシロキサン５量体以上５〜６５重量部、望ましくは１０〜４５重量部を使用する。環状オルガノシロキサン５量体以上が５重量部より少ないと、乳化重合してできたオルガノポリシロキサンの水性エマルジョンに経時でクリーミングが発生したり、オイル分離が発生したりするので好ましくない。逆に６５重量部より多いと、乳化重合してできたオルガノポリシロキサンの水性エマルジョンに多量のオイル分離が発生するとともに、前記環状オルガノシロキサン混合物の開環反応が平衡に達するまでに長時間を要するため好ましくない。この環状オルガノシロキサン５量体以上は、５量体、６量体、7量体以上、あるいはそれらの混合物であるが、５量体および６量体の合計量は好ましくは５０重量％以上であり、より好ましくは６５重量％以上である。５０重量％より低い割合では、乳化重合してできたオルガノポリシロキサンの水性エマルジョンにオイル分離が発生することがあり、前記環状オルガノシロキサン混合物の開環反応が平衡に達するまでに長時間を要しがちである。 Cyclic organosiloxanes represented by the general formula (R 1 R 2 SiO) 4 (wherein R 1 and R 2 are the same or different unsubstituted or substituted monovalent hydrocarbon groups) and the general formula (R 3 R 4 SiO) n (wherein R 3 and R 4 are the same or different unsubstituted or substituted monovalent hydrocarbon groups, and n is an integer of 5 or more) 4 amount of cyclic organosiloxane The body is the main raw material for emulsion polymerization. The cyclic organosiloxane pentamer is used in an amount of 5 to 65 parts by weight, preferably 10 to 45 parts by weight per 100 parts by weight of the cyclic organosiloxane tetramer. When the cyclic organosiloxane pentamer or more is less than 5 parts by weight, an aqueous emulsion of an organopolysiloxane obtained by emulsion polymerization may cause creaming or oil separation over time, which is not preferable. On the other hand, when the amount is more than 65 parts by weight, a large amount of oil separation occurs in the aqueous emulsion of organopolysiloxane formed by emulsion polymerization, and it takes a long time for the ring-opening reaction of the cyclic organosiloxane mixture to reach equilibrium. Therefore, it is not preferable. The cyclic organosiloxane pentamer or higher is a pentamer, hexamer, heptamer or higher, or a mixture thereof. The total amount of the pentamer and hexamer is preferably 50% by weight or higher. More preferably, it is 65% by weight or more. If the ratio is lower than 50% by weight, oil separation may occur in an aqueous emulsion of organopolysiloxane produced by emulsion polymerization, and it takes a long time for the ring-opening reaction of the cyclic organosiloxane mixture to reach equilibrium. Tend to.
一般式（Ｒ１Ｒ２ＳｉＯ）４で表される環状オルガノシロキサン４量体では、Ｒ１とＲ２は同一種または異種の非置換または置換の１価炭化水素基である。Ｒ１が好ましくはメチル基であり、Ｒ２が好ましくは１価飽和脂肪族炭化水素基、１価不飽和脂肪族炭化水素基、１価飽和脂肪族炭化水素基または１価飽和脂肪族炭化水素基の炭素原子結合水素原子が部分的にフッ素原子のようなハロゲン原子またはエポキシ基、アミノ基、メタクリル基、メルカプト基など有機官能基で置換された基であり、より好ましくはアルキル基であり、さらに好ましくはメチル基である。このような４量体の環状オルガノシロキサンとして、オクタメチルシクロテトラシロキサン、およびそのメチル基の一部が水素原子、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基、ノナデシル基などの１価飽和脂肪族炭化水素基；ビニル基、アリル基、ヘキセニル基などの１価不飽和脂肪族炭化水素基；シクロペンチル基、シクロヘキシル基などの１価飽和脂環式炭化水素基；フェニル基、トリル基、ナフチル基などの１価芳香族炭化水素基；ヒドロキシ基；メトキシ基、エトキシ基、プロポキシ基等のアルコキシ基；１価飽和脂肪族炭化水素基の炭素原子結合水素原子が部分的にフッ素原子のようなハロゲン原子またはエポキシ基、アミノ基、メタクリル基、メルカプト基など有機官能基で置換されたものが例示される。 In the cyclic organosiloxane tetramer represented by the general formula (R 1 R 2 SiO) 4 , R 1 and R 2 are the same or different unsubstituted or substituted monovalent hydrocarbon groups. R 1 is preferably a methyl group, and R 2 is preferably a monovalent saturated aliphatic hydrocarbon group, a monovalent unsaturated aliphatic hydrocarbon group, a monovalent saturated aliphatic hydrocarbon group or a monovalent saturated aliphatic hydrocarbon. The carbon atom-bonded hydrogen atom of the group is a group partially substituted with a halogen atom such as a fluorine atom or an organic functional group such as an epoxy group, amino group, methacryl group, mercapto group, more preferably an alkyl group, More preferred is a methyl group. As such a tetrameric cyclic organosiloxane, octamethylcyclotetrasiloxane, and a part of the methyl group is a hydrogen atom, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, Monovalent saturated aliphatic hydrocarbon groups such as nonyl group, decyl group, undecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, octadecyl group, nonadecyl group; vinyl group, allyl group, hexenyl Monovalent unsaturated aliphatic hydrocarbon group such as a group; monovalent saturated alicyclic hydrocarbon group such as cyclopentyl group and cyclohexyl group; monovalent aromatic hydrocarbon group such as phenyl group, tolyl group and naphthyl group; hydroxy group ; Alkoxy group such as methoxy group, ethoxy group, propoxy group; monovalent saturated aliphatic hydrocarbon; Halogen atom or an epoxy group such as carbon-bonded hydrogen atoms are partially fluorine atom, an amino group, methacryl group, those substituted by organofunctional groups and mercapto groups are exemplified.
一般式（Ｒ３Ｒ４ＳｉＯ）ｎで表される環状オルガノシロキサン５量体以上では、Ｒ３とＲ４は同一種または異種の非置換または置換の１価炭化水素基であるが、Ｒ３が好ましくはメチル基であり、Ｒ４が好ましくは１価飽和脂肪族炭化水素基、１価不飽和脂肪族炭化水素基、１価飽和脂肪族炭化水素基、または１価飽和脂肪族炭化水素基の炭素原子結合水素原子が部分的にフッ素原子のようなハロゲン原子またはエポキシ基、アミノ基、メタクリル基、メルカプト基など有機官能基で置換された基であり、より好ましくはアルキル基であり、さらに好ましくはメチル基である。ｎは５以上の整数であるが、５〜１０が好ましく、５と６がより好ましい。５量体以上の環状オルガノシロキサンとして、デカメチルシクロペンタシロキサン、ドデカメチルシクロヘキサシロキサン、テトラデカメチルシクロペンタシロキサン、ヘキサデカメチルシクロオクタシロキサン、オクタデカメチルシクロノナシロキサン、およびそのメチル基の一部が水素原子、エチル基、プロピル基、ブチル基、ペンチル基、ヘキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基、ノナデシル基などの１価飽和脂肪族炭化水素基；ビニル基、アリル基、ヘキセニル基などの１価不飽和脂肪族炭化水素基；シクロペンチル基、シクロヘキシル基などの１価飽和脂環式炭化水素基；フェニル基、トリル基、ナフチル基などの１価芳香族炭化水素基；ヒドロキシ基；メトキシ基、エトキシ基、プロポキシ基等のアルコキシ基；１価飽和脂肪族炭化水素基の炭素原子結合水素原子が部分的にフッ素原子のようなハロゲン原子またはエポキシ基、アミノ基、メタクリル基、メルカプト基など有機官能基で置換されたものが例示される。
入手の容易さ、乳化重合の容易性、乳化重合してできたオルガノポリシロキサンの水性エマルジョンの有用性などの点から、４量体としてオクタメチルシクロテトラシロキサン、環状オルガノシロキサン５量体以上としてデカメチルシクロペンタシロキサン、ドデカメチルシクロヘキサシロキサンが好ましい。
General formula (R 3 R 4 SiO) cyclic represented by n organosiloxane pentamer above is R 3 and R 4 is a monovalent hydrocarbon radical unsubstituted or substituted in the same species or different, R 3 Is preferably a methyl group, and R 4 is preferably a monovalent saturated aliphatic hydrocarbon group, a monovalent unsaturated aliphatic hydrocarbon group, a monovalent saturated aliphatic hydrocarbon group, or a monovalent saturated aliphatic hydrocarbon group. A carbon atom-bonded hydrogen atom is a group partially substituted with a halogen atom such as a fluorine atom or an organic functional group such as an epoxy group, amino group, methacryl group, mercapto group, more preferably an alkyl group, A methyl group is preferred. n is an integer of 5 or more, preferably 5 to 10, and more preferably 5 and 6. Decamethylcyclopentasiloxane, dodecamethylcyclohexasiloxane, tetradecamethylcyclopentasiloxane, hexadecamethylcyclooctasiloxane, octadecamethylcyclononasiloxane, and some of its methyl groups as cyclic organosiloxanes of pentamer or higher Is hydrogen, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl Monovalent saturated aliphatic hydrocarbon groups such as a vinyl group, an allyl group and a hexenyl group; monovalent saturated alicyclic rings such as a cyclopentyl group and a cyclohexyl group Formula hydrocarbon group; Monovalent aromatic hydrocarbon groups such as ruthel group, tolyl group and naphthyl group; hydroxy groups; alkoxy groups such as methoxy group, ethoxy group and propoxy group; carbon atoms bonded hydrogen atoms of monovalent saturated aliphatic hydrocarbon groups are partially Examples thereof include those substituted with a halogen atom such as a fluorine atom or an organic functional group such as an epoxy group, an amino group, a methacryl group or a mercapto group.
From the viewpoints of availability, ease of emulsion polymerization, and usefulness of aqueous emulsion of organopolysiloxane produced by emulsion polymerization, octamethylcyclotetrasiloxane as a tetramer and deca as a cyclic organosiloxane pentamer or higher. Methylcyclopentasiloxane and dodecamethylcyclohexasiloxane are preferred.
カチオン性界面活性剤は、前記環状オルガノシロキサン混合物を水中に乳化するための成分である。一般式Ｒ５Ｒ６（ＣＨ３）２Ｎ＋Ｃｌ−（式中Ｒ５、Ｒ６は同一種または異種の非置換または置換の１価炭化水素基であり、Ｒ５とＲ６のいずれかは水酸基であってもよい）で表されるものが一般的である。このような界面活性剤として、エチル硫酸ラノリン脂肪酸アミノプロピルエチルジメチルアンモニウム、塩化アルキルトリメチルアンモニウム、塩化アルキル（１６，１８）トリメチルアンモニウム、塩化オクタデシルトリメチルアンモニウム、塩化オクチルジヒドロキシエチルメチルアンモニウム、塩化γ−グルコンアミドプロピルジメチルヒドロキシエチルアンモニウム、塩化ジアルキル（１２〜１５）ジメチルアンモニウム、塩化ジアルキル（１４〜１８）ジメチルアンモニウム、塩化ジココイルジメチルアンモニウム、塩化ジステリルジメチルアンモニウム末、塩化ジステリルジメチルアンモニウム、塩化ジセチルジメチルアンモニウム液、塩化ジ（ポリオキシエチレン）オレイルメチルアンモニウム、塩化ジ（ポリオキシエチレン）オレイルメチルアンモニウム（２Ｅ．Ｏ．）、塩化ジポリオキシエチレンステアリルメチルアンモニウム、塩化ステアリルジヒドロキシエチルベタインナトリウム、塩化ステアリルジメチルベンジルアンモニウム、塩化ステアリルトリメチルアンモニウム、塩化ステアリルトリメチルアンモニウム液、塩化ステアロイルコラミノホルミルメチルピリジニウム、塩化セチルトリメチルアンモニウム、塩化セチルピリジニウム、塩化ドデシルジメチルエチルアンモニウム、塩化トリ（ポリオキシエチレン）ステアリルアンモニウム（５Ｅ．Ｏ．）、塩化ベヘニルトリメチルアンモニウム、塩化ベンザルコニウム、塩化ベンザルコニウム液、塩化ベンゼトニウム、塩化ベンゼトニウム液、塩化ポリオキシエチレン（１）ポリオキシプロピレン（２５）ジエチルメチルアンモニウム、塩化ポリオキシプロピレンメチルジエチルアンモニウム、塩化ミリスチルジメチルベンジルアンモニウム、塩化メチルベンゼトニウム、塩化ラウリルトリメチルアンモニウム、塩化ラウリルピリジニウム、塩化ラウロイルコラミノホルミルメチルピリジニウム、臭化アルキルイソキノリニウム液、臭化ステアリルトリメチルアンモニウム、臭化セチルトリメチルアンモニウム、臭化セチルトリメチルアンモニウム末、臭化ラウリルトリメチルアンモニウム、ステアリルトリメチルアンモニウムサッカリン、セチルトリメチルアンモニウムサッカリン、ラウリルイソキノリニウムサッカリンが例示される。 The cationic surfactant is a component for emulsifying the cyclic organosiloxane mixture in water. General formula R 5 R 6 (CH 3 ) 2 N + Cl − (wherein R 5 and R 6 are the same or different unsubstituted or substituted monovalent hydrocarbon groups, and one of R 5 and R 6 Is generally a hydroxyl group). Such surfactants include ethyl lanolin sulfate fatty acid aminopropylethyldimethylammonium chloride, alkyltrimethylammonium chloride, alkyl (16,18) trimethylammonium chloride, octadecyltrimethylammonium chloride, octyldihydroxyethylmethylammonium chloride, γ-gluconamide chloride. Propyldimethylhydroxyethylammonium chloride, dialkyl (12-15) dimethylammonium chloride, dialkyl (14-18) dimethylammonium chloride, dicocoyldimethylammonium chloride, disteryldimethylammonium powder, disteryldimethylammonium chloride, dicetyldimethylammonium chloride Liquid, di (polyoxyethylene) oleylmethylammonium chloride, di (polyoxyethylene chloride) Oleylmethylammonium (2EO), dipolyoxyethylene stearylmethylammonium chloride, sodium stearyldihydroxyethylbetaine chloride, stearyldimethylbenzylammonium chloride, stearyltrimethylammonium chloride, stearyltrimethylammonium chloride solution, stearoylcholaminoformylmethylpyridinium chloride , Cetyltrimethylammonium chloride, cetylpyridinium chloride, dodecyldimethylethylammonium chloride, tri (polyoxyethylene) stearylammonium chloride (5EO), behenyltrimethylammonium chloride, benzalkonium chloride, benzalkonium chloride solution, benzethonium chloride Benzethonium chloride solution, polyoxyethylene chloride (1) polyoxypropylene (25 ) Diethylmethylammonium chloride, polyoxypropylenemethyldiethylammonium chloride, myristyldimethylbenzylammonium chloride, methylbenzethonium chloride, lauryltrimethylammonium chloride, laurylpyridinium chloride, lauroylcolaminoformylmethylpyridinium chloride, alkylisoquinolinium bromide solution, odor Examples include stearyl trimethyl ammonium bromide, cetyl trimethyl ammonium bromide, cetyl trimethyl ammonium bromide, lauryl trimethyl ammonium bromide, stearyl trimethyl ammonium saccharin, cetyl trimethyl ammonium saccharin, and lauryl isoquinolinium saccharin.
これらのカチオン性界面活性剤は単独で使用してもよく、または２種以上を組み合わせて使用してもよい。その使用量は、前記環状オルガノシロキサン混合物を水中に乳化してエマルジョンにする量であれば特に制限されないが、前記環状オルガノシロキサン合計量１０５〜１６５重量部当たり１〜３００重量部が好ましく、１〜１６５重量部がさらに好ましい。１重量部未満では、前記環状オルガノシロキサン混合物を水中に乳化しにくく、乳化重合してできたオルガノポリシロキサンの水性エマルジョンの安定性が損なわれて分離を生じる恐れがあり、また３００重量部を超えると乳化重合してできたオルガノポリシロキサンの水性エマルジョンの流動性が低くなって取扱いにくくなる場合があり、また乳化重合してできたオルガノポリシロキサンの水性エマルジョンの安定性が損なわれて分離を生じがちになるからである。 These cationic surfactants may be used alone or in combination of two or more. The amount used is not particularly limited as long as it is an amount obtained by emulsifying the cyclic organosiloxane mixture in water to form an emulsion, but preferably 1 to 300 parts by weight per 105 to 165 parts by weight of the total amount of the cyclic organosiloxane. More preferably, 165 parts by weight. If the amount is less than 1 part by weight, it is difficult to emulsify the cyclic organosiloxane mixture in water, the stability of the aqueous emulsion of organopolysiloxane produced by emulsion polymerization may be impaired, and separation may occur, and the amount exceeds 300 parts by weight. The emulsion may be difficult to handle due to low fluidity of the aqueous emulsion of organopolysiloxane produced by emulsion polymerization, and the stability of the aqueous emulsion of organopolysiloxane produced by emulsion polymerization may be impaired, resulting in separation. Because it tends to be.
塩基性重合触媒は、水中に乳化した前記環状オルガノシロキサン混合物を重合してオルガノポリシロキサンにする為の触媒である。このような塩基性重合触媒として、水酸化カリウム、水酸化ナトリウムのようなアルカリ金属水酸化物；炭酸カリウム、炭酸ナトリウムのようなアルカリ金属塩；アンモニア；イソプロパノールアミン、ジイソプロパノールアミン、トリイソプロパノールアミン、ジエタノールアミン、トリエタノールアミンのようなアミノアルコール；テトラメチルアンモニウムヒドロキシド；テトラエチルアンモニウムヒドロキシド、ベンジルトリメチルアンモニウムヒドロキシド、ベンジルトリエチルアンモニウムヒドロキシドのような第４級アンモニウムヒドロキシドが例示される。これらのうちでは重合能の点でアルカリ金属水酸化物が好ましい。塩基性重合触媒の使用量は、水中に乳化した前記環状オルガノシロキサン混合物を重合するのに十分な量であればよく、特に制限されるものではないが、前記環状オルガノシロキサン合計量１０５〜１６５重量部当たり０．０１〜１０重量部が好ましく、０．０１〜５重量部がより好ましい。 The basic polymerization catalyst is a catalyst for polymerizing the cyclic organosiloxane mixture emulsified in water into an organopolysiloxane. Examples of such basic polymerization catalysts include alkali metal hydroxides such as potassium hydroxide and sodium hydroxide; alkali metal salts such as potassium carbonate and sodium carbonate; ammonia; isopropanolamine, diisopropanolamine, triisopropanolamine, Examples include amino alcohols such as diethanolamine and triethanolamine; tetramethylammonium hydroxide; quaternary ammonium hydroxides such as tetraethylammonium hydroxide, benzyltrimethylammonium hydroxide, and benzyltriethylammonium hydroxide. Of these, alkali metal hydroxides are preferred from the viewpoint of polymerization ability. The amount of the basic polymerization catalyst used is not particularly limited as long as it is sufficient to polymerize the cyclic organosiloxane mixture emulsified in water, but the total amount of the cyclic organosiloxane is 105 to 165 wt. 0.01 to 10 parts by weight per part is preferable, and 0.01 to 5 parts by weight is more preferable.
水は、前記環状オルガノシロキサン混合物、カチオン系界面活性剤および塩基性重合触媒の分散媒である。水の使用量は、前記環状オルガノシロキサン混合物をカチオン系界面活性剤により乳化でき、塩基性重合触媒を溶解するのに十分な量であれば特に制限されないが、前記環状オルガノシロキサン合計量１０５〜１６５重量部当たり、好ましくは３０〜２０００重量部、好ましくは５０〜１０００重量部である。 Water is a dispersion medium for the cyclic organosiloxane mixture, the cationic surfactant, and the basic polymerization catalyst. The amount of water used is not particularly limited as long as the cyclic organosiloxane mixture can be emulsified with a cationic surfactant and is sufficient to dissolve the basic polymerization catalyst, but the total amount of the cyclic organosiloxane is 105 to 165. It is preferably 30 to 2000 parts by weight, preferably 50 to 1000 parts by weight per part by weight.
本発明のオルガノポリシロキサンの水性エマルジョンは、例えば、次のような手順で製造できる。すなわち、前記環状オルガノシロキサン、カチオン系界面活性剤、水を予備混合し、ホモジナイザー、ナノマイザー、コロイドミル、ラインミキサー、ソノレーター等の乳化機を通した後、必要に応じてさらに水を添加する。次に得られた粗エマルジョンに塩基性重合触媒を添加し、所定の温度に調整して前記環状オルガノシロキサンの開環重合を行う。乳化重合温度は、前記環状オルガノシロキサンの開環重合を行うのに十分な温度であれば特に制限されないが、乳化重合時間と生成したオルガノポリシロキサンの重合度の点から６０〜９０℃であることが好ましい。その後目的の重合度となる温度に液温を調節し、目的の重合度に達したならば、塩酸、硫酸、リン酸、酢酸、脂肪族置換ベンゼンスルホン酸等の中和剤により塩基性重合触媒を中和して重合反応を停止し、室温付近まで冷却する。本発明のオルガノポリシロキサンの水性エマルジョンの製造方法は、上記に代表されるが、本発明の目的が妨げなければ、条件変更しても何ら差し支えない。 The aqueous emulsion of the organopolysiloxane of the present invention can be produced, for example, by the following procedure. That is, the cyclic organosiloxane, the cationic surfactant, and water are preliminarily mixed, passed through an emulsifier such as a homogenizer, nanomizer, colloid mill, line mixer, and sonolator, and then water is added as necessary. Next, a basic polymerization catalyst is added to the obtained crude emulsion, and the cyclic organosiloxane is subjected to ring-opening polymerization by adjusting to a predetermined temperature. The emulsion polymerization temperature is not particularly limited as long as the temperature is sufficient to perform the ring-opening polymerization of the cyclic organosiloxane, but is 60 to 90 ° C. from the viewpoint of the emulsion polymerization time and the degree of polymerization of the generated organopolysiloxane. Is preferred. Thereafter, the temperature of the liquid is adjusted to a temperature that achieves the desired degree of polymerization, and when the desired degree of polymerization is reached, a basic polymerization catalyst is added with a neutralizing agent such as hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid, aliphatic substituted benzenesulfonic acid, etc. Is neutralized to stop the polymerization reaction, and is cooled to around room temperature. The method for producing an aqueous emulsion of an organopolysiloxane of the present invention is typified above, but there is no problem even if the conditions are changed as long as the object of the present invention is not hindered.
乳化重合してできたオルガノポリシロキサンの水性エマルジョンの粒子径をさらに小さくしたり、他の組成物等への配合安定性をさらに向上させたり、オルガノポリシロキサンに有機官能基を導入したり、皮膜形成性を持たせたりするために、本発明の目的を損なわない範囲でオルガノポリシロキサンエマルジョンの添加剤として公知である他の成分を乳化前、乳化重合前、あるいは乳化重合後に添加・配合することが可能である。このような添加剤としては、乳化目的でないカチオン系界面活性剤、ノニオン系界面活性剤、両性界面活性剤、ケイ素原子結合加水分解性基含有オルガノシラン類、その加水分解物、ｐＨ調整剤、防腐剤、防カビ剤、防錆剤、増粘剤、凝固点降下剤、凍結融解安定化剤が例示される。これらの成分は、単独あるいは複数組み合わせて添加しても良い。 Reduce the particle size of the aqueous emulsion of organopolysiloxane produced by emulsion polymerization, further improve the compounding stability in other compositions, introduce organic functional groups into the organopolysiloxane, and coat In order to impart formability, other components known as additives for organopolysiloxane emulsions are added and blended before emulsification, before emulsion polymerization, or after emulsion polymerization within a range that does not impair the purpose of the present invention. Is possible. Such additives include non-emulsifying cationic surfactants, nonionic surfactants, amphoteric surfactants, silicon-bonded hydrolyzable group-containing organosilanes, hydrolysates thereof, pH adjusters, antiseptics Examples include agents, fungicides, rust inhibitors, thickeners, freezing point depressants, and freeze-thaw stabilizers. These components may be added alone or in combination.
このようなカチオン系界面活性剤として、前記したものが例示される。 Examples of such cationic surfactants include those described above.
ノニオン系界面活性剤例として、エチレングリコール脂肪酸エチル類、ポリエチレングリコール脂肪酸エステル類、プロピレングリコール脂肪酸エステル類、ポリプロピレングリコール脂肪酸エステル類、グリコール脂肪酸エステル類、トリメチロールプロパン脂肪酸エステル類、ペンタエリスリット脂肪酸エステル類、グルコシド誘導体類、グリセリンアルキルエーテル脂肪酸エステル類、トリメチロールプロパンオキシエチレンアルキルエーテル類、脂肪酸アミド類、アルキロールアミド類、アルキルアミンオキシド類、ラノリンおよびその誘導体類、ヒマシ油誘導体類、硬化ヒマシ油誘導体類、ステロールおよびその誘導体類、ポリオキシエチレンアルキルエーテル類、ポリオキシエチレンアルキルアリルエーテル類、ポリオキシエチレンアルキルアミン類、ポリオキシエチレン脂肪酸アミド類、ポリオキシエチレンアルキロールアミド類、ポリオキシエチレンジエタノールアミン脂肪酸エステル類、ポリオキシエチレントリメチロールプロパン脂肪酸エステル類、ポリオキシエチレンアルキルエーテル脂肪酸エステル類、ポリオキシエチレンポリオキシプロピレングリコール類、ポリオキシエチレンポリオキシプロピレンアルキルエーテル類、ポリオキシエチレンポリオキシプロピレン多価アルコールエーテル類、グリセリン脂肪酸エステル類、ポリグリセリン脂肪酸エステル類、ポリオキシエチレングリセリン脂肪酸エステル類、ソルビタン脂肪酸エステル類、ポリオキシエチレンソルビタン脂肪酸エステル類、ショ糖脂肪酸エステル類、メチル（ポリオキシエチレン）シロキサン・ジメチルシロキサン共重合体、メチル（ポリオキシプロピレン）シロキサン・ジメチルシロキサン共重合体が例示される。 Examples of nonionic surfactants include ethylene glycol fatty acid ethyls, polyethylene glycol fatty acid esters, propylene glycol fatty acid esters, polypropylene glycol fatty acid esters, glycol fatty acid esters, trimethylolpropane fatty acid esters, pentaerythritol fatty acid esters , Glucoside derivatives, glycerin alkyl ether fatty acid esters, trimethylolpropaneoxyethylene alkyl ethers, fatty acid amides, alkylolamides, alkylamine oxides, lanolin and its derivatives, castor oil derivatives, hydrogenated castor oil derivatives , Sterols and their derivatives, polyoxyethylene alkyl ethers, polyoxyethylene alkyl allyl ethers, polyoxyethylene Alkylamines, polyoxyethylene fatty acid amides, polyoxyethylene alkylolamides, polyoxyethylene diethanolamine fatty acid esters, polyoxyethylene trimethylolpropane fatty acid esters, polyoxyethylene alkyl ether fatty acid esters, polyoxyethylene Polyoxypropylene glycols, polyoxyethylene polyoxypropylene alkyl ethers, polyoxyethylene polyoxypropylene polyhydric alcohol ethers, glycerin fatty acid esters, polyglycerin fatty acid esters, polyoxyethylene glycerin fatty acid esters, sorbitan fatty acid esters , Polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, methyl (polyoxyethylene) Rokisan-dimethylsiloxane copolymer, methyl (polyoxypropylene) siloxane-dimethylsiloxane copolymers.
両性界面活性剤として、２−アルキル−Ｎ−カルボキシメチル−Ｎ−ヒドロキシエチルイミダゾリニウムベタイン、ウンデシルカルボキシメトキシエチルカルボキシメチルイミダゾリニウムベタインナトリウム、ウンデシルヒドロキシエチルイミダゾリニウムベタインナトリウム、ウンデシル−Ｎ−ヒドロキシエチル−Ｎ−カルボキシメチルイミダゾリニウムベタイン、塩酸アルキルジアミノエチルエチルグリシン液、ステアリルジヒドロキシエチルベタイン、ステアリルジメチルアミノ酢酸ベタイン、ステアリルジメチルベタインナトリウム、ステアリルジメチルベタインナトリウム液、ビス（ステアリル−Ｎ−ヒドロキシエチルイミダゾリン）クロル酢酸錯体、ヤシ油アルキル−Ｎ−カルボキシエチル−Ｎ−ヒドロキシエチルイミダゾリニウムベタインナトリウム、ヤシ油アルキル−Ｎ−カルボキシエトキシエチル−Ｎ−カルボキシエチルイミダゾリニウムジナトリウムヒドロキシド、ヤシ油アルキル−Ｎ−カルボキシメトキシエチル−Ｎ−カルボキシメチルイミダゾリニウムジナトリウムヒドロキシド、ヤシ油アルキル−Ｎ−カルボキシメトキシエチル−Ｎ−カルボキシメチルイミダゾリニウムジナトリウムラウリル硫酸、ヤシ油アルキルベタイン、ヤシ油脂肪酸アミドプロピルベタイン、ヤシ油脂肪酸−Ｎ−カルボキシメトキシエチル−Ｎ−カルボキシエチルイミダゾリニウムベタインナトリウム、ラウリルアミノプロピオン酸トリエタノールアミン、β−ラウリルアミノプロピオン酸ナトリウム、ラウリル−Ｎ−カルボキシメトキシエチル−Ｎ−カルボキシメチルイミダゾリニウムジナトリウムドデカノイルサルコシン、ラウリルジアミノエチルグリシンナトリウム、ラウリルジメチルアミノ酢酸ベタイン、ラウリン酸アミドプロピルベタイン液が例示される。 As amphoteric surfactants, 2-alkyl-N-carboxymethyl-N-hydroxyethylimidazolinium betaine, undecylcarboxymethoxyethylcarboxymethylimidazolinium betaine sodium, undecylhydroxyethyl imidazolinium betaine sodium, undecyl-N -Hydroxyethyl-N-carboxymethylimidazolinium betaine, alkyldiaminoethylethyl glycine hydrochloride, stearyl dihydroxyethyl betaine, stearyl dimethylamino acetate betaine, stearyl dimethyl betaine sodium, stearyl dimethyl betaine sodium solution, bis (stearyl-N-hydroxy Ethyl imidazoline) chloroacetic acid complex, coconut oil alkyl-N-carboxyethyl-N-hydroxyethyl imidazole Umbetaine sodium, coconut oil alkyl-N-carboxyethoxyethyl-N-carboxyethylimidazolinium disodium hydroxide, coconut oil alkyl-N-carboxymethoxyethyl-N-carboxymethylimidazolinium disodium hydroxide, coconut oil Alkyl-N-carboxymethoxyethyl-N-carboxymethylimidazolinium disodium lauryl sulfate, coconut oil alkylbetaine, coconut oil fatty acid amidopropyl betaine, coconut oil fatty acid-N-carboxymethoxyethyl-N-carboxyethylimidazolinium betaine Sodium, laurylaminopropionate triethanolamine, β-laurylaminopropionate sodium, lauryl-N-carboxymethoxyethyl-N-carboxymethylimidazo Examples include linium disodium dodecanoyl sarcosine, sodium lauryldiaminoethylglycine, lauryldimethylaminoacetic acid betaine, and lauric acid amidopropyl betaine solution.
ケイ素原子結合加水分解性基含有オルガノシラン類またはその加水分解物は、添加することにより生成したオルガノポリシロキサンに有機官能基やケイ素原子結合加水分解性基が導入され、皮膜形成性、架橋性を与えるものである。このようなケイ素原子結合加水分解性基含有オルガノシラン類として、オルガノトリアルコキシシラン、オルガノメチルジアルコキシシラン、例えば３−アミノプロピルジメトキシシラン、３−アミノプロピルトリメトキシシラン、Ｎ−（２−アミノエチル）−３−アミノプロピルトリメトキシシラン、Ｎ−（２−アミノエチル）−３−アミノプロピルジメトキシシラン、３−クロロプロピルトリメトキシシラン、３−クロロプロピルジメトキシシラン、３−メタクリロキシプロピルトリメトキシシラン、３−アクリロキシプロピルジメトキシシラン、３−グリシドキシプロピルトリメトキシシラン、３−グリシドキシプロピルメチルジメトキシシラン、３−メルカプトプロピルメチルジメトキシシラン、３−カルボキシプロピルメチルジメトキシシラン、ｐ−ビニルフェニルトリメトキシシラン、２−（ビニルフェニル）エチルトリメトキシシラン、３−（ｐ−イソプロペニルベンゾイルアミノ）プロピルトリメトキシシラン、Ｎ−メタクリロイル−Ｎ−メチル−３−アミノプロピルトリメトキシシラン、Ｎ−ラウロイル−Ｎ−メチル−３−アミノプロピルメチルジメトキシシラン、Ｎ−アクリロイル−Ｎ−メチル−３−アミノプロピルトリメトキシシラン、Ｎ−ラウロイル−Ｎ−メチル−３−アミノプロピルトリメトキシシラン、Ｎ，Ｎ−ビス（メタクリロイル）−３−アミノプロピルメチルジメトキシシラン、Ｎ，Ｎ−ビス（ラウロイル）−３−アミノプロピルトリメトキシシラン、３−アミノプロピルジエトキシシラン、３−アミノプロピルトリエトキシシラン、Ｎ−（２−アミノエチル）−３−アミノプロピルトリエトキシシラン、Ｎ−（２−アミノエチル）−３−アミノプロピルジエトキシシラン、３−クロロプロピルトリエトキシシラン、３−クロロプロピルジエトキシシラン、３−メタクリロキシプロピルトリエトキシシラン、３−アクリロキシプロピルジエトキシシラン、３−グリシドキシプロピルトリエトキシシラン、３−グリシドキシプロピルメチルジエトキシシラン、３−メルカプトプロピルメチルジエトキシシラン、３−カルボキシプロピルメチルジエトキシシラン、ｐ−ビニルフェニルトリエトキシシラン、２−（ビニルフェニル）エチルトリエトキシシラン、３−（ｐ−イソプロペニルベンゾイルアミノ）プロピルトリエトキシシラン、Ｎ−メタクリロイル−Ｎ−メチル−３−アミノプロピルトリエトキシシラン、Ｎ−ラウロイル−Ｎ−メチル−３−アミノプロピルメチルジエトキシシラン、Ｎ−アクリロイル−Ｎ−メチル−３−アミノプロピルトリエトキシシラン、Ｎ−ラウロイル−Ｎ−メチル−３−アミノプロピルトリエトキシシラン、Ｎ，Ｎ−ビス（メタクリロイル）−３−アミノプロピルメチルジエトキシシラン、Ｎ，Ｎ−ビス（ラウロイル）−３−アミノプロピルトリエトキシシランが例示される。その加水分解物は部分加水分解物であってもよい。これらは単独あるいは２種以上の混合物として添加される。その添加量は、本発明の目的を妨げなければ何ら制限されないが、前記環状オルガノシロキサン４量体１００重量部と前記環状オルガノシロキサン５量体以上５〜６５重量部当たり通常３０重量部以下であり、好ましくは１〜２０重量部である。 Silicone-bonded hydrolyzable group-containing organosilanes or hydrolysates thereof have an organic functional group or silicon-bonded hydrolyzable group introduced into the organopolysiloxane produced by the addition, thereby improving film formation and crosslinkability. Give. Examples of organosilanes containing such silicon-bonded hydrolyzable groups include organotrialkoxysilanes, organomethyl dialkoxysilanes such as 3-aminopropyldimethoxysilane, 3-aminopropyltrimethoxysilane, N- (2-aminoethyl). ) -3-aminopropyltrimethoxysilane, N- (2-aminoethyl) -3-aminopropyldimethoxysilane, 3-chloropropyltrimethoxysilane, 3-chloropropyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-acryloxypropyldimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, 3-carboxypropylmethyldimethyl Xysilane, p-vinylphenyltrimethoxysilane, 2- (vinylphenyl) ethyltrimethoxysilane, 3- (p-isopropenylbenzoylamino) propyltrimethoxysilane, N-methacryloyl-N-methyl-3-aminopropyltrimethoxy Silane, N-lauroyl-N-methyl-3-aminopropylmethyldimethoxysilane, N-acryloyl-N-methyl-3-aminopropyltrimethoxysilane, N-lauroyl-N-methyl-3-aminopropyltrimethoxysilane, N, N-bis (methacryloyl) -3-aminopropylmethyldimethoxysilane, N, N-bis (lauroyl) -3-aminopropyltrimethoxysilane, 3-aminopropyldiethoxysilane, 3-aminopropyltriethoxysilane, N- (2 Aminoethyl) -3-aminopropyltriethoxysilane, N- (2-aminoethyl) -3-aminopropyldiethoxysilane, 3-chloropropyltriethoxysilane, 3-chloropropyldiethoxysilane, 3-methacryloxypropyl Triethoxysilane, 3-acryloxypropyldiethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 3-mercaptopropylmethyldiethoxysilane, 3-carboxypropylmethyldiethoxy Silane, p-vinylphenyltriethoxysilane, 2- (vinylphenyl) ethyltriethoxysilane, 3- (p-isopropenylbenzoylamino) propyltriethoxysilane, N-methacryloyl-N-methyl-3-aminopropi Rutriethoxysilane, N-lauroyl-N-methyl-3-aminopropylmethyldiethoxysilane, N-acryloyl-N-methyl-3-aminopropyltriethoxysilane, N-lauroyl-N-methyl-3-aminopropyltri Examples include ethoxysilane, N, N-bis (methacryloyl) -3-aminopropylmethyldiethoxysilane, and N, N-bis (lauroyl) -3-aminopropyltriethoxysilane. The hydrolyzate may be a partial hydrolyzate. These are added alone or as a mixture of two or more. The amount of addition is not particularly limited as long as the object of the present invention is not hindered. The amount is preferably 1 to 20 parts by weight.
ｐＨ調整剤として、塩酸、硫酸、リン酸、リン酸水素ニアンモニウム、リン酸水素ニナトリウム、リン酸水素ニカリウム、リン酸ニ水素アンモニウム、リン酸ニ水素ナトリウム、リン酸ニ水素カリウム、リン酸三ナトリウム、リン酸三カリウム、酢酸、酢酸アンモニウム、酢酸ナトリウム、酢酸カリウム、クエン酸、クエン酸ナトリウム、クエン酸ニアンモニウム、炭酸ナトリウム、炭酸カリウム、炭酸アンモニウム、炭酸水素ナトリウム、炭酸水素アンモニウム、水酸化ナトリウム、水酸化カリウム、アンモニア、トリエタノールアミンが例示される。 pH adjusters include hydrochloric acid, sulfuric acid, phosphoric acid, diammonium hydrogen phosphate, disodium hydrogen phosphate, dipotassium hydrogen phosphate, ammonium dihydrogen phosphate, sodium dihydrogen phosphate, potassium dihydrogen phosphate, triphosphate Sodium, tripotassium phosphate, acetic acid, ammonium acetate, sodium acetate, potassium acetate, citric acid, sodium citrate, diammonium citrate, sodium carbonate, potassium carbonate, ammonium carbonate, sodium bicarbonate, ammonium bicarbonate, sodium hydroxide , Potassium hydroxide, ammonia, and triethanolamine.
防腐剤、防カビ剤、防錆剤として、安息香酸、安息香酸アルミニウム、安息香酸ナトリウム、イソプロピルメチルフェノール、エチルヘキサンジオール、塩化リゾチーム、塩酸クロルヘキシジン、オクチルフェノキシエタノール、オルトフェニルフェノール、過ホウ酸ナトリウム、感光素１０１号、感光素２０１号、感光素３０１号、感光素４０１号、グルコン酸クロルヘキシジン液、クレゾール、クロラミンＴ、クロルキシレノール、クロルクレゾール、クロルフェネシン、クロルヘキシジン、クロロブタノール、酢酸レゾルシン、サリチル酸、サリチル酸ナトリウム、臭化ドミフェン、ジンクピリチオン、ジンクピリチオン液、ソルビン酸、サオルビン酸カリウム、チアントール、チオキソロン、チモール、チラム、デヒドロ酢酸、デヒドロ酢酸ナトリウム、トリクロロカルバニリド、トリクロロヒドロキシジフェニルエーテル、パラオキシ安息香酸イソブチル、パラオキシ安息香酸イソプロピル、パラオキシ安息香酸エチル、パラオキシ安息香酸ブチル、パラオキシ安息香酸プロピル、パラオキシ安息香酸ベンジル、パラオキシ安息香酸メチル、パラオキシ安息香酸メチルナトリウム、パラクロルフェノール、パラフェノールスルホン酸ナトリウム（二水和物）、ハロカルバン、フェノキシエタノール、フェノール、ヘキサクロロファン、モノニトログアヤコール、モノニトログアヤコールナトリウム、ヨウ化パラジメチルアミノスチリルヘプチルメチルリアゾリニウム、ラウリルトリメチルアンモニウムトリクロロフェノキサイド、硫酸オキシキノリン、リン酸オキシキノリン、レゾルシン、亜硝酸ナトリウムが例示される。
増粘剤として、カルボキシビニルポリマー、キサンタンガム、アクリル酸・メタクリル酸アルキル共重合体、ケイ酸アルミニウム・マグネシウムが例示される。
Antiseptic, fungicide, rust preventive, benzoic acid, aluminum benzoate, sodium benzoate, isopropylmethylphenol, ethylhexanediol, lysozyme chloride, chlorhexidine hydrochloride, octylphenoxyethanol, orthophenylphenol, sodium perborate, photosensitive Element 101, photosensitive element 201, photosensitive element 301, photosensitive element 401, chlorhexidine gluconate solution, cresol, chloramine T, chlorxylenol, chlorcresol, chlorphenesin, chlorhexidine, chlorobutanol, resorcinol acetate, salicylic acid, salicylic acid Sodium, Domifene bromide, Zinc pyrithione, Zinc pyrithione solution, Sorbic acid, Potassium saorbate, Thianthol, Thioxolone, Thymol, Tyram, Dehydroacetic acid, Dehi Sodium croacetate, trichlorocarbanilide, trichlorohydroxydiphenyl ether, isobutyl paraoxybenzoate, isopropyl paraoxybenzoate, ethyl paraoxybenzoate, butyl paraoxybenzoate, propyl paraoxybenzoate, benzyl paraoxybenzoate, methyl paraoxybenzoate, paraoxybenzoate Methyl sodium, parachlorophenol, sodium paraphenol sulfonate (dihydrate), halocarban, phenoxyethanol, phenol, hexachlorophane, mononitroguaiacol, mononitroguaiacol sodium, paradimethylaminostyrylheptylmethylriazolinium iodide , Lauryltrimethylammonium trichlorophenoxide, oxyquinoline sulfate, oxyquinophosphate Emissions, resorcin, sodium nitrite and the like.
Examples of the thickener include carboxyvinyl polymer, xanthan gum, acrylic acid / alkyl methacrylate copolymer, and aluminum silicate / magnesium.
乳化重合してできたオルガノポリシロキサンの水性エマルジョンは、Ｒ１Ｒ２ＳｉＯ単位とＲ３Ｒ４ＳｉＯ単位とからなるジオルガノポリシロキサンが水中に乳化したエマルジョン、あるいは、Ｒ１Ｒ２ＳｉＯ単位とＲ３Ｒ４ＳｉＯ単位とからなるジオルガノポリシロキサン中に水が乳化したエマルジョンである。後者の場合は水で稀釈することにより前者のエマルジョンになる。乳化重合してできたエマルジョン中のオルガノポリシロキサンは、Ｒ１Ｒ２ＳｉＯ単位とＲ３Ｒ４ＳｉＯ単位が通常ランダムに配列しており、両末端は通常水酸基である。ただし、ヘキサメチルジシロキサンのような末端封鎖剤を添加して乳化重合した場合は、トリメチルシロキシ基のようなオルガノシロキシ基も末端基となる。このオルガノポリシロキサン中のＲ１、Ｒ２、Ｒ３、Ｒ４は既に例示されたものと同様である。ただし、乳化重合前や乳化重合時にケイ素原子結合加水分解性基含有オルガノシラン類またはその加水分解物を添加した場合は、分岐した鎖状オルガノポリシロキサンとなったり、ケイ素原子結合加水分解性基を含有するオルガノポリシロキサンになることがある。乳化重合してできたオルガノポリシロキサンの水性エマルジョンの平均粒子径は、重合条件により異なるが通常５０〜３００ｎｍである。 An aqueous emulsion of an organopolysiloxane obtained by emulsion polymerization is an emulsion in which a diorganopolysiloxane composed of R 1 R 2 SiO units and R 3 R 4 SiO units is emulsified in water, or R 1 R 2 SiO units It is an emulsion in which water is emulsified in a diorganopolysiloxane composed of R 3 R 4 SiO units. In the latter case, the former emulsion is obtained by diluting with water. In the organopolysiloxane in the emulsion formed by emulsion polymerization, R 1 R 2 SiO units and R 3 R 4 SiO units are usually randomly arranged, and both ends are usually hydroxyl groups. However, when an end-blocking agent such as hexamethyldisiloxane is added and emulsion polymerization is performed, an organosiloxy group such as a trimethylsiloxy group also becomes a terminal group. R 1 , R 2 , R 3 and R 4 in this organopolysiloxane are the same as those already exemplified. However, when silicon-bonded hydrolyzable group-containing organosilanes or hydrolysates thereof are added before or during emulsion polymerization, branched chain organopolysiloxanes or silicon-bonded hydrolyzable groups are added. May contain organopolysiloxane. The average particle size of the organopolysiloxane aqueous emulsion obtained by emulsion polymerization is usually 50 to 300 nm, although it varies depending on the polymerization conditions.
本発明を実施例により詳細に説明する。実施例と比較例中、「部」は「重量部」を、「％」は「重量％」を表す。また、調製したエマルジョンは、以下の方法により評価した。 The present invention will be described in detail with reference to examples. In Examples and Comparative Examples, “part” represents “part by weight” and “%” represents “% by weight”. The prepared emulsion was evaluated by the following method.
＜クリーミング発生量＞
オルガノポリシロキサンの水性エマルジョンを２００ｃｃガラス瓶に計りとり、調製直後、および室温で３月間静置後のクリーミング発生量を目視した。評価結果は以下の４水準とした。
◎ ： クリーミング発生なし
○ ： 微量のクリーミング発生（層の厚さ１ｍｍ以下）
△ ： 少量のクリーミング発生（層の厚さ１〜３ｍｍ程度）
× ： 多量のクリーミング発生（層の厚さ５ｍｍ以上）
<Creaming amount>
The aqueous emulsion of organopolysiloxane was weighed into a 200 cc glass bottle, and the amount of creaming generated immediately after preparation and after standing at room temperature for 3 months was visually observed. The evaluation results are the following four levels.
◎: No creaming occurred ○: A small amount of creaming occurred (layer thickness 1mm or less)
Δ: A small amount of creaming (layer thickness of about 1 to 3 mm)
X: Generation of a large amount of creaming (layer thickness of 5 mm or more)
＜オイル分離発生量＞
オルガノポリシロキサンの水性エマルジョンを２００ｃｃガラス瓶に計りとり、調製直後、および室温で３月間静置後のエマルション表面に発生するオイル分離量を目視した。評価結果は以下の４水準とした。
◎ ： オイル分離なし
○ ： 微量のオイル分離（ごく薄い層が表面に認められる）
△ ： 少量のオイル分離（少量のオイルスポットが認められる）
× ： 多量のオイル分離（多量のオイルスポットまたはオイル層が認められる）
<Oil separation generation amount>
An aqueous emulsion of organopolysiloxane was weighed into a 200 cc glass bottle, and the amount of oil separation generated on the emulsion surface immediately after preparation and after standing at room temperature for 3 months was visually observed. The evaluation results are the following four levels.
◎: No oil separation ○: Trace amount of oil separation (a very thin layer is observed on the surface)
Δ: Small amount of oil separation (a small amount of oil spot is observed)
×: Large amount of oil separation (a large amount of oil spot or oil layer is observed)
＜環状オルガノシロキサンの反応率＞
オルガノポリシロキサンの水性エマルジョン５容量部に、メタノール５０容量部、ｎ−ヘキサン１００容量部を添加し、強く振とうした。これを２４時間以上室温で静置したところ、ｎ−ヘキサン層と水層に完全に分離した。ｎ−ヘキサン層をマイクロシリンジで採取し、ガスクロマトグラフで測定して環状オルガノシロキサンの反応率（％）を求めた。
＜エマルジョン粒子の平均粒子径＞
ＣＯＵＬＴＥＲ ＥＬＥＣＴＲＯＮＩＣＳ社（米国）製の「ＣＯＵＬＴＥＲ ＭＯＤＥＬ Ｎ４」を用いて測定した。
<Reaction rate of cyclic organosiloxane>
50 parts by volume of methanol and 100 parts by volume of n-hexane were added to 5 parts by volume of an aqueous organopolysiloxane emulsion and shaken vigorously. When this was allowed to stand at room temperature for 24 hours or more, it was completely separated into an n-hexane layer and an aqueous layer. The n-hexane layer was collected with a microsyringe and measured with a gas chromatograph to determine the reaction rate (%) of the cyclic organosiloxane.
<Average particle diameter of emulsion particles>
It measured using "COULTER MODEL N4" by COULTER ELECTRONICS (USA).
［実施例１］
容器にオクタメチルシクロテトラシロキサン９０．０部とデカメチルシクロペンタシロキサン１０．０部の混合物、塩化ステアリルトリメチルアンモニウム（２８％水溶液）１８．５部、塩化ジラウリルジメチルアンモニウム（２８％水溶液）２７．５部、イオン交換水９１．０部を加え、よく混合した。この混合液を４００ｋｇ／ｃｍ２の圧力下でナノマイザーを１回通過させることにより、粗エマルションを得た。この粗エマルションを温度計、攪拌器、冷却管を備えた別の容器に取り、攪拌をしながら２０％アミノエチルアミノプロピルトリメトキシシラン水溶液１３．０部、２０％水酸化ナトリウム水溶液 １．５部を添加した。攪拌を継続しながら８５℃まで昇温し、そのまま４時間保持した後、５５℃まで冷却し、ポリオキシエチレン（２０）セチルエーテル１．５部、１７．５％酢酸水溶液４．５部を添加することにより、重合反応を停止した。さらに、室温付近まで冷却することにより、ジメチルポリシロキサンの水性エマルジョン（サンプル−１）を得た。クリーミング発生量、オイル分離量、環状オルガノシロキサンの反応率およびエマルジョン粒子の平均粒子径を評価して、それらの結果を表１に示した。
[Example 1]
In a container, a mixture of 90.0 parts of octamethylcyclotetrasiloxane and 10.0 parts of decamethylcyclopentasiloxane, 18.5 parts of stearyltrimethylammonium chloride (28% aqueous solution), dilauryldimethylammonium chloride (28% aqueous solution) 27. 5 parts and 91.0 parts of ion exchange water were added and mixed well. This mixed solution was passed through a nanomizer once under a pressure of 400 kg / cm 2 to obtain a crude emulsion. This crude emulsion is put in another container equipped with a thermometer, a stirrer, and a cooling tube, and while stirring, 13.0 parts of a 20% aminoethylaminopropyltrimethoxysilane aqueous solution and 1.5 parts of a 20% aqueous sodium hydroxide solution are added. Was added. While continuing stirring, the temperature was raised to 85 ° C., kept for 4 hours, then cooled to 55 ° C., and 1.5 parts of polyoxyethylene (20) cetyl ether and 4.5 parts of 17.5% acetic acid aqueous solution were added As a result, the polymerization reaction was stopped. Furthermore, the aqueous emulsion (sample-1) of dimethylpolysiloxane was obtained by cooling to near room temperature. The amount of creaming, the amount of oil separation, the reaction rate of the cyclic organosiloxane, and the average particle size of the emulsion particles were evaluated, and the results are shown in Table 1.
［実施例２］
実施例１において、オクタメチルシクロテトラシロキサン９０．０部とデカメチルシクロペンタシロキサン１０．０部の混合物を、オクタメチルシクロテトラシロキサン８０．０部とデカメチルシクロペンタシロキサン２０．０部の混合物に置き換えた以外は同様の手順で乳化重合を行ってジメチルポリシロキサンの水性エマルジョン（サンプル−２）を得た。クリーミング発生量、オイル分離量、環状オルガノシロキサンの反応率およびエマルジョン粒子の平均粒子径を評価して、それらの結果を表１に示した。
[Example 2]
In Example 1, a mixture of 90.0 parts of octamethylcyclotetrasiloxane and 10.0 parts of decamethylcyclopentasiloxane was converted to a mixture of 80.0 parts of octamethylcyclotetrasiloxane and 20.0 parts of decamethylcyclopentasiloxane. Except for the replacement, emulsion polymerization was performed in the same procedure to obtain an aqueous emulsion of dimethylpolysiloxane (Sample-2). The amount of creaming, the amount of oil separation, the reaction rate of the cyclic organosiloxane, and the average particle size of the emulsion particles were evaluated, and the results are shown in Table 1.
［実施例３］
実施例１において、オクタメチルシクロテトラシロキサン９０．０部とデカメチルシクロペンタシロキサン１０．０部の混合物を、オクタメチルシクロテトラシロキサン７０．０部とデカメチルシクロペンタシロキサン３０．０部の混合物に置き換えた以外は同様の手順で乳化重合を行ってジメチルポリシロキサンの水性エマルジョン（サンプル−３）を得た。クリーミング発生量、オイル分離量、環状オルガノシロキサンの反応率およびエマルジョン粒子の平均粒子径を評価して、それらの結果を表１に示した。
[Example 3]
In Example 1, a mixture of 90.0 parts of octamethylcyclotetrasiloxane and 10.0 parts of decamethylcyclopentasiloxane was converted to a mixture of 70.0 parts of octamethylcyclotetrasiloxane and 30.0 parts of decamethylcyclopentasiloxane. Except for the replacement, emulsion polymerization was performed in the same procedure to obtain an aqueous emulsion of dimethylpolysiloxane (Sample-3). The amount of creaming, the amount of oil separation, the reaction rate of the cyclic organosiloxane, and the average particle size of the emulsion particles were evaluated, and the results are shown in Table 1.
［実施例４］
実施例１において、オクタメチルシクロテトラシロキサン９０．０部とデカメチルシクロペンタシロキサン１０．０部の混合物を、オクタメチルシクロテトラシロキサン９０．０部とドデカメチルシクロヘキサシロキサン１０．０部の混合物に置き換えた以外は同様の手順で乳化重合を行ってジメチルポリシロキサンの水性エマルジョン（サンプル−４）を得た。クリーミング発生量、オイル分離量、環状オルガノシロキサンの反応率およびエマルジョン粒子の平均粒子径を評価して、それらの結果を表１に示した。
[Example 4]
In Example 1, a mixture of 90.0 parts of octamethylcyclotetrasiloxane and 10.0 parts of decamethylcyclopentasiloxane was converted to a mixture of 90.0 parts of octamethylcyclotetrasiloxane and 10.0 parts of dodecamethylcyclohexasiloxane. Except for the replacement, emulsion polymerization was carried out in the same procedure to obtain an aqueous emulsion of dimethylpolysiloxane (Sample-4). The amount of creaming, the amount of oil separation, the reaction rate of the cyclic organosiloxane, and the average particle size of the emulsion particles were evaluated, and the results are shown in Table 1.
［実施例５］
実施例１において、オクタメチルシクロテトラシロキサン９０．０部とデカメチルシクロペンタシロキサン１０．０部の混合物を、オクタメチルシクロテトラシロキサン９０．０部とデカメチルシクロペンタシロキサン５．０部とドデカメチルシクロヘキサシロキサン５．０部の混合物に置き換えた以外は同様の手順で乳化重合を行ってジメチルポリシロキサンの水性エマルジョン（サンプル−５）を得た。クリーミング発生量、オイル分離量、環状オルガノシロキサンの反応率およびエマルジョン粒子の平均粒子径を評価して、それらの結果を表１に示した。
[Example 5]
In Example 1, a mixture of 90.0 parts of octamethylcyclotetrasiloxane and 10.0 parts of decamethylcyclopentasiloxane was mixed with 90.0 parts of octamethylcyclotetrasiloxane, 5.0 parts of decamethylcyclopentasiloxane and dodecamethyl. Emulsion polymerization was carried out in the same procedure except that the mixture was replaced with 5.0 parts of cyclohexasiloxane to obtain an aqueous emulsion of dimethylpolysiloxane (Sample-5). The amount of creaming, the amount of oil separation, the reaction rate of the cyclic organosiloxane, and the average particle size of the emulsion particles were evaluated, and the results are shown in Table 1.
［比較例１］
実施例１において、オクタメチルシクロテトラシロキサン９０．０部、デカメチルシクロペンタシロキサン１０．０部の混合物を、オクタメチルシクロテトラシロキサン１００．０部に置き換えた以外は同様の手順で乳化重合を行ってジメチルポリシロキサンの水性エマルジョン（サンプル−６）を得た。クリーミング発生量、オイル分離量、環状オルガノシロキサンの反応率およびエマルジョン粒子の平均粒子径を評価して、それらの結果を表２に示した。
[Comparative Example 1]
In Example 1, emulsion polymerization was carried out in the same manner except that 90.0 parts of octamethylcyclotetrasiloxane and 10.0 parts of decamethylcyclopentasiloxane were replaced with 100.0 parts of octamethylcyclotetrasiloxane. Thus, an aqueous emulsion of dimethylpolysiloxane (Sample-6) was obtained. The amount of creaming, the amount of oil separation, the reaction rate of cyclic organosiloxane, and the average particle size of the emulsion particles were evaluated, and the results are shown in Table 2.
［比較例２］
実施例１において、オクタメチルシクロテトラシロキサン９０．０部とデカメチルシクロペンタシロキサン１０．０部の混合物を、オクタメチルシクロテトラシロキサン５０．０部とデカメチルシクロペンタシロキサン５０．０部の混合物に置き換えた以外は同様の手順で乳化重合を行ってジメチルポリシロキサンの水性エマルジョン（サンプル−７）を得た。クリーミング発生量、オイル分離量、環状オルガノシロキサンの反応率およびエマルジョン粒子の平均粒子径を評価して、それらの結果を表２に示した。
[Comparative Example 2]
In Example 1, a mixture of 90.0 parts of octamethylcyclotetrasiloxane and 10.0 parts of decamethylcyclopentasiloxane was converted to a mixture of 50.0 parts of octamethylcyclotetrasiloxane and 50.0 parts of decamethylcyclopentasiloxane. Except for the replacement, emulsion polymerization was carried out in the same procedure to obtain an aqueous emulsion of dimethylpolysiloxane (Sample-7). The amount of creaming, the amount of oil separation, the reaction rate of cyclic organosiloxane, and the average particle size of the emulsion particles were evaluated, and the results are shown in Table 2.
［比較例３］
実施例１において、オクタメチルシクロテトラシロキサン９０．０部とデカメチルシクロペンタシロキサン１０．０部の混合物を、オクタメチルシクロテトラシロキサン２５．０部とデカメチルシクロペンタシロキサン７５．０部の混合物に置き換えた以外は同様の手順で乳化重合を行ってジメチルポリシロキサンの水性エマルジョン（サンプル−８）を得た。クリーミング発生量、オイル分離量、環状オルガノシロキサンの反応率およびエマルジョン粒子の平均粒子径を評価して、それらの結果を表２に示した。
[Comparative Example 3]
In Example 1, a mixture of 90.0 parts of octamethylcyclotetrasiloxane and 10.0 parts of decamethylcyclopentasiloxane was converted to a mixture of 25.0 parts of octamethylcyclotetrasiloxane and 75.0 parts of decamethylcyclopentasiloxane. Except for the replacement, emulsion polymerization was carried out in the same procedure to obtain an aqueous emulsion of dimethylpolysiloxane (Sample-8). The amount of creaming, the amount of oil separation, the reaction rate of cyclic organosiloxane, and the average particle size of the emulsion particles were evaluated, and the results are shown in Table 2.
［比較例４］
実施例１において、オクタメチルシクロテトラシロキサン９０．０部とデカメチルシクロペンタシロキサン１０．０部の混合物を、デカメチルシクロペンタシロキサン１００部に置き換えた以外は同様の手順で乳化重合を行ってジメチルポリシロキサンの水性エマルジョン（サンプル−９）を得た。クリーミング発生量、オイル分離量、環状オルガノシロキサンの反応率およびエマルジョン粒子の平均粒子径を評価して、それらの結果を表２に示した。
[Comparative Example 4]
In Example 1, emulsion polymerization was carried out in the same procedure except that a mixture of 90.0 parts of octamethylcyclotetrasiloxane and 10.0 parts of decamethylcyclopentasiloxane was replaced with 100 parts of decamethylcyclopentasiloxane, followed by emulsion polymerization. An aqueous emulsion of polysiloxane (Sample-9) was obtained. The amount of creaming, the amount of oil separation, the reaction rate of cyclic organosiloxane, and the average particle size of the emulsion particles were evaluated, and the results are shown in Table 2.
［実施例６］
塩化セチルトリメチルアンモニウム（３０％水溶液）２５．０部にイオン交換水１１２．５部を加え、さらに２０％水酸化ナトリウム水溶液２．０部を加え、よく攪拌した。次に、この混合液にオクタメチルシクロテトラシロキサン９０．０部とデカメチルシクロペンタシロキサン１０．０部の混合物、３−グリシドキシプロピルトリメトキシシラン０．５部を加えてよく混合した。その後、３００ｋｇ／ｃｍ２の圧力下でホモジナイザーを１回通過させた。得られたエマルションにポリオキシエチレン（２１）ラウリルエーテル２．５部を添加し、さらにもう一度３００ｋｇ／ｃｍ２の圧力下でホモジナイザーを１回通過させた。得られた粗エマルジョンを温度計、攪拌器、冷却管を備えた別の容器に取り、８５℃まで昇温し、そのまま５時間保持した。４０℃以下に冷却後、２０％酢酸水溶液３．０部を添加することにより重合反応を停止して、ジメチルポリシロキサンの水性エマルジョン（サンプル−１０）を得た。クリーミング発生量、オイル分離量、環状オルガノシロキサンの反応率およびエマルジョン粒子の平均粒子径を評価して、それらの結果を表３に示した。
[Example 6]
112.5 parts of ion-exchanged water was added to 25.0 parts of cetyltrimethylammonium chloride (30% aqueous solution), and 2.0 parts of 20% aqueous sodium hydroxide solution was further added, followed by thorough stirring. Next, a mixture of 90.0 parts of octamethylcyclotetrasiloxane and 10.0 parts of decamethylcyclopentasiloxane and 0.5 part of 3-glycidoxypropyltrimethoxysilane were added to this mixed solution and mixed well. Then, the homogenizer was passed once under a pressure of 300 kg / cm 2 . To the obtained emulsion, 2.5 parts of polyoxyethylene (21) lauryl ether was added, and the mixture was once again passed through a homogenizer under a pressure of 300 kg / cm 2 . The obtained crude emulsion was put in another container equipped with a thermometer, a stirrer, and a cooling tube, heated to 85 ° C., and kept as it was for 5 hours. After cooling to 40 ° C. or lower, the polymerization reaction was stopped by adding 3.0 parts of a 20% aqueous acetic acid solution to obtain an aqueous emulsion of dimethylpolysiloxane (Sample-10). The amount of creaming generated, the amount of oil separation, the reaction rate of the cyclic organosiloxane, and the average particle size of the emulsion particles were evaluated, and the results are shown in Table 3.
[実施例７]
実施例３において、オクタメチルシクロテトラシロキサン９０．０部とデカメチルシクロペンタシロキサン１０．０部の混合物を、オクタメチルシクロテトラシロキサン８５．０部とデカメチルシクロペンタシロキサン１５．０部の混合物に置き換えた以外は同様の手順で乳化重合を行ってジメチルポリシロキサンの水性エマルジョン（サンプル−１１）を得た。クリーミング発生量、オイル分離量、環状オルガノシロキサンの反応率およびエマルジョン粒子の平均粒子径を評価して、それらの結果を表３に示した。
[Example 7]
In Example 3, a mixture of 90.0 parts of octamethylcyclotetrasiloxane and 10.0 parts of decamethylcyclopentasiloxane was converted to a mixture of 85.0 parts of octamethylcyclotetrasiloxane and 15.0 parts of decamethylcyclopentasiloxane. Except for the replacement, emulsion polymerization was performed in the same procedure to obtain an aqueous emulsion of dimethylpolysiloxane (Sample-11). The amount of creaming generated, the amount of oil separation, the reaction rate of the cyclic organosiloxane, and the average particle size of the emulsion particles were evaluated, and the results are shown in Table 3.
[比較例５]
実施例２において、オクタメチルシクロテトラシロキサン８５．０部とデカメチルシクロペンタシロキサン１５．０部の混合物を、オクタメチルシクロテトラシロキサン１００．０部に置き換えた以外は同様の手順で乳化重合を行ってジメチルポリシロキサンの水性エマルジョン（サンプル−１２）を得た。クリーミング発生量、オイル分離量、環状オルガノシロキサンの反応率およびエマルジョン粒子の平均粒子径を評価して、それらの結果を表３に示した。
[Comparative Example 5]
In Example 2, emulsion polymerization was performed in the same procedure except that a mixture of 85.0 parts of octamethylcyclotetrasiloxane and 15.0 parts of decamethylcyclopentasiloxane was replaced with 100.0 parts of octamethylcyclotetrasiloxane. Thus, an aqueous emulsion of dimethylpolysiloxane (Sample-12) was obtained. The amount of creaming generated, the amount of oil separation, the reaction rate of the cyclic organosiloxane, and the average particle size of the emulsion particles were evaluated, and the results are shown in Table 3.
本発明の製造方法により製造されたオルガノポリシロキサンの水性エマルジョンは、液状、ペースト状、エマルジョン状、デイスパージョン状、ゲル状などの化粧料、ヘルスケア製品、離型剤、撥水剤、繊維処理剤、表面処理剤などの添加剤として、また、それ自体が離型剤、撥水剤、繊維処理剤、表面処理剤、コーテイング剤、有機繊維織物やガラスクロスのバインダーなどとして有用である。特に第４級アンモニウム塩系化合物ような塩基性化合物を含有するカチオン性の化粧料、特には毛髪化粧料や毛髪洗浄剤の添加剤として有用である。
The aqueous emulsion of organopolysiloxane produced by the production method of the present invention is a liquid, paste-like, emulsion-like, dispersion-like, gel-like cosmetic, health care product, release agent, water repellent, fiber It is useful as an additive such as a treating agent and a surface treating agent, and as such as a release agent, a water repellent, a fiber treating agent, a surface treating agent, a coating agent, an organic fiber woven fabric and a glass cloth binder. In particular, it is useful as an additive for cationic cosmetics containing basic compounds such as quaternary ammonium salt compounds, especially hair cosmetics and hair cleansing agents.
Claims (12)
The method for producing an aqueous emulsion according to any one of claims 7 to 11, wherein the basic polymerization catalyst is an alkali metal hydroxide.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011524426A (en) * | 2008-04-16 | 2011-09-01 | ダウ・コーニング・コーポレイション | Preparation of silicone microemulsion |
| CN104141225A (en) * | 2014-07-29 | 2014-11-12 | 王会丽 | Wig softener formula and preparing technology thereof |
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2003
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011524426A (en) * | 2008-04-16 | 2011-09-01 | ダウ・コーニング・コーポレイション | Preparation of silicone microemulsion |
| US9694214B2 (en) | 2008-04-16 | 2017-07-04 | Dow Corning Corporation | Preparation of silicone microemulsions |
| CN104141225A (en) * | 2014-07-29 | 2014-11-12 | 王会丽 | Wig softener formula and preparing technology thereof |
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