JP7421172B2 - Method for producing organic solvent-dispersed sol of surface-modified silica particles - Google Patents
Method for producing organic solvent-dispersed sol of surface-modified silica particles Download PDFInfo
- Publication number
- JP7421172B2 JP7421172B2 JP2022511689A JP2022511689A JP7421172B2 JP 7421172 B2 JP7421172 B2 JP 7421172B2 JP 2022511689 A JP2022511689 A JP 2022511689A JP 2022511689 A JP2022511689 A JP 2022511689A JP 7421172 B2 JP7421172 B2 JP 7421172B2
- Authority
- JP
- Japan
- Prior art keywords
- silica particles
- organic solvent
- dispersed sol
- modified silica
- sol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 title claims description 128
- 238000004519 manufacturing process Methods 0.000 title claims description 16
- 239000006087 Silane Coupling Agent Substances 0.000 claims description 41
- 150000007514 bases Chemical class 0.000 claims description 33
- 239000003729 cation exchange resin Substances 0.000 claims description 27
- 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 claims description 21
- -1 silane compound Chemical class 0.000 claims description 20
- 239000011164 primary particle Substances 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 229910000077 silane Inorganic materials 0.000 claims description 7
- 238000002156 mixing Methods 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 150000003973 alkyl amines Chemical class 0.000 claims description 3
- 150000001768 cations Chemical class 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 description 41
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 20
- 238000000034 method Methods 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 125000005372 silanol group Chemical group 0.000 description 14
- 239000002245 particle Substances 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000002378 acidificating effect Effects 0.000 description 11
- 239000006185 dispersion Substances 0.000 description 11
- 238000006460 hydrolysis reaction Methods 0.000 description 11
- 238000006482 condensation reaction Methods 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000000178 monomer Substances 0.000 description 8
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- 229940023913 cation exchange resins Drugs 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000011521 glass Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000009833 condensation Methods 0.000 description 4
- 230000005494 condensation Effects 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- QPRQEDXDYOZYLA-UHFFFAOYSA-N 2-methylbutan-1-ol Chemical compound CCC(C)CO QPRQEDXDYOZYLA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
- 229920001429 chelating resin Polymers 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- JSLCOZYBKYHZNL-UHFFFAOYSA-N isobutyric acid butyl ester Natural products CCCCOC(=O)C(C)C JSLCOZYBKYHZNL-UHFFFAOYSA-N 0.000 description 3
- WDAXFOBOLVPGLV-UHFFFAOYSA-N isobutyric acid ethyl ester Natural products CCOC(=O)C(C)C WDAXFOBOLVPGLV-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- NMRPBPVERJPACX-UHFFFAOYSA-N octan-3-ol Chemical compound CCCCCC(O)CC NMRPBPVERJPACX-UHFFFAOYSA-N 0.000 description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 3
- 239000011342 resin composition Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 2
- BBMCTIGTTCKYKF-UHFFFAOYSA-N 1-heptanol Chemical compound CCCCCCCO BBMCTIGTTCKYKF-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- RXGUIWHIADMCFC-UHFFFAOYSA-N 2-Methylpropyl 2-methylpropionate Chemical compound CC(C)COC(=O)C(C)C RXGUIWHIADMCFC-UHFFFAOYSA-N 0.000 description 2
- FZXRXKLUIMKDEL-UHFFFAOYSA-N 2-Methylpropyl propanoate Chemical compound CCC(=O)OCC(C)C FZXRXKLUIMKDEL-UHFFFAOYSA-N 0.000 description 2
- CETWDUZRCINIHU-UHFFFAOYSA-N 2-heptanol Chemical compound CCCCCC(C)O CETWDUZRCINIHU-UHFFFAOYSA-N 0.000 description 2
- SZNYYWIUQFZLLT-UHFFFAOYSA-N 2-methyl-1-(2-methylpropoxy)propane Chemical compound CC(C)COCC(C)C SZNYYWIUQFZLLT-UHFFFAOYSA-N 0.000 description 2
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 description 2
- IKYAJDOSWUATPI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propane-1-thiol Chemical compound CO[Si](C)(OC)CCCS IKYAJDOSWUATPI-UHFFFAOYSA-N 0.000 description 2
- MXLMTQWGSQIYOW-UHFFFAOYSA-N 3-methyl-2-butanol Chemical compound CC(C)C(C)O MXLMTQWGSQIYOW-UHFFFAOYSA-N 0.000 description 2
- YGHRJJRRZDOVPD-UHFFFAOYSA-N 3-methylbutanal Chemical compound CC(C)CC=O YGHRJJRRZDOVPD-UHFFFAOYSA-N 0.000 description 2
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- YVBCULSIZWMTFY-UHFFFAOYSA-N 4-Heptanol Natural products CCCC(O)CCC YVBCULSIZWMTFY-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- RZKSECIXORKHQS-UHFFFAOYSA-N Heptan-3-ol Chemical compound CCCCC(O)CC RZKSECIXORKHQS-UHFFFAOYSA-N 0.000 description 2
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- 238000001879 gelation Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
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- 238000005259 measurement Methods 0.000 description 2
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 2
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- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 2
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- QIOYHIUHPGORLS-UHFFFAOYSA-N n,n-dimethyl-3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN(C)C QIOYHIUHPGORLS-UHFFFAOYSA-N 0.000 description 1
- 229940017144 n-butyl lactate Drugs 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N n-butyl methyl ketone Natural products CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
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- SLYCYWCVSGPDFR-UHFFFAOYSA-N octadecyltrimethoxysilane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OC)(OC)OC SLYCYWCVSGPDFR-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- MSRJTTSHWYDFIU-UHFFFAOYSA-N octyltriethoxysilane Chemical compound CCCCCCCC[Si](OCC)(OCC)OCC MSRJTTSHWYDFIU-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 238000001139 pH measurement Methods 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- JZZRXECTAQPLNI-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O.CCCCC=O JZZRXECTAQPLNI-UHFFFAOYSA-N 0.000 description 1
- WCVRQHFDJLLWFE-UHFFFAOYSA-N pentane-1,2-diol Chemical compound CCCC(O)CO WCVRQHFDJLLWFE-UHFFFAOYSA-N 0.000 description 1
- RUOPINZRYMFPBF-UHFFFAOYSA-N pentane-1,3-diol Chemical compound CCC(O)CCO RUOPINZRYMFPBF-UHFFFAOYSA-N 0.000 description 1
- GLOBUAZSRIOKLN-UHFFFAOYSA-N pentane-1,4-diol Chemical compound CC(O)CCCO GLOBUAZSRIOKLN-UHFFFAOYSA-N 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- XHTWKNPMPDIELI-UHFFFAOYSA-N phenylmethoxysilane Chemical compound [SiH3]OCC1=CC=CC=C1 XHTWKNPMPDIELI-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- KIWATKANDHUUOB-UHFFFAOYSA-N propan-2-yl 2-hydroxypropanoate Chemical compound CC(C)OC(=O)C(C)O KIWATKANDHUUOB-UHFFFAOYSA-N 0.000 description 1
- GVIIRWAJDFKJMJ-UHFFFAOYSA-N propan-2-yl 3-oxobutanoate Chemical compound CC(C)OC(=O)CC(C)=O GVIIRWAJDFKJMJ-UHFFFAOYSA-N 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- DHGFMVMDBNLMKT-UHFFFAOYSA-N propyl 3-oxobutanoate Chemical compound CCCOC(=O)CC(C)=O DHGFMVMDBNLMKT-UHFFFAOYSA-N 0.000 description 1
- HUAZGNHGCJGYNP-UHFFFAOYSA-N propyl butyrate Chemical compound CCCOC(=O)CCC HUAZGNHGCJGYNP-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- MCSINKKTEDDPNK-UHFFFAOYSA-N propyl propionate Chemical compound CCCOC(=O)CC MCSINKKTEDDPNK-UHFFFAOYSA-N 0.000 description 1
- 229940116423 propylene glycol diacetate Drugs 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- SBYHFKPVCBCYGV-UHFFFAOYSA-N quinuclidine Chemical compound C1CC2CCN1CC2 SBYHFKPVCBCYGV-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011163 secondary particle Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-Butyl ethyl ether Natural products CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
- IXXMVXXFAJGOQO-UHFFFAOYSA-N tert-butyl 2-hydroxypropanoate Chemical compound CC(O)C(=O)OC(C)(C)C IXXMVXXFAJGOQO-UHFFFAOYSA-N 0.000 description 1
- KVWOTUDBCFBGFJ-UHFFFAOYSA-N tert-butyl 2-methylpropanoate Chemical compound CC(C)C(=O)OC(C)(C)C KVWOTUDBCFBGFJ-UHFFFAOYSA-N 0.000 description 1
- JKUYRAMKJLMYLO-UHFFFAOYSA-N tert-butyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OC(C)(C)C JKUYRAMKJLMYLO-UHFFFAOYSA-N 0.000 description 1
- WMOVHXAZOJBABW-UHFFFAOYSA-N tert-butyl acetate Chemical compound CC(=O)OC(C)(C)C WMOVHXAZOJBABW-UHFFFAOYSA-N 0.000 description 1
- TWBUVVYSQBFVGZ-UHFFFAOYSA-N tert-butyl butanoate Chemical compound CCCC(=O)OC(C)(C)C TWBUVVYSQBFVGZ-UHFFFAOYSA-N 0.000 description 1
- RUPAXCPQAAOIPB-UHFFFAOYSA-N tert-butyl formate Chemical compound CC(C)(C)OC=O RUPAXCPQAAOIPB-UHFFFAOYSA-N 0.000 description 1
- JAELLLITIZHOGQ-UHFFFAOYSA-N tert-butyl propanoate Chemical compound CCC(=O)OC(C)(C)C JAELLLITIZHOGQ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
- TXEYQDLBPFQVAA-UHFFFAOYSA-N tetrafluoromethane Chemical compound FC(F)(F)F TXEYQDLBPFQVAA-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- ALVYUZIFSCKIFP-UHFFFAOYSA-N triethoxy(2-methylpropyl)silane Chemical compound CCO[Si](CC(C)C)(OCC)OCC ALVYUZIFSCKIFP-UHFFFAOYSA-N 0.000 description 1
- FRGPKMWIYVTFIQ-UHFFFAOYSA-N triethoxy(3-isocyanatopropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCN=C=O FRGPKMWIYVTFIQ-UHFFFAOYSA-N 0.000 description 1
- HXOGQBSDPSMHJK-UHFFFAOYSA-N triethoxy(6-methylheptyl)silane Chemical compound CCO[Si](OCC)(OCC)CCCCCC(C)C HXOGQBSDPSMHJK-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- OYGYKEULCAINCL-UHFFFAOYSA-N triethoxy(hexadecyl)silane Chemical compound CCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC OYGYKEULCAINCL-UHFFFAOYSA-N 0.000 description 1
- WUMSTCDLAYQDNO-UHFFFAOYSA-N triethoxy(hexyl)silane Chemical compound CCCCCC[Si](OCC)(OCC)OCC WUMSTCDLAYQDNO-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- FZMJEGJVKFTGMU-UHFFFAOYSA-N triethoxy(octadecyl)silane Chemical compound CCCCCCCCCCCCCCCCCC[Si](OCC)(OCC)OCC FZMJEGJVKFTGMU-UHFFFAOYSA-N 0.000 description 1
- FHVAUDREWWXPRW-UHFFFAOYSA-N triethoxy(pentyl)silane Chemical compound CCCCC[Si](OCC)(OCC)OCC FHVAUDREWWXPRW-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- BJDLPDPRMYAOCM-UHFFFAOYSA-N triethoxy(propan-2-yl)silane Chemical compound CCO[Si](OCC)(OCC)C(C)C BJDLPDPRMYAOCM-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- SVKDNKCAGJVMMY-UHFFFAOYSA-N triethoxy(tetradecyl)silane Chemical compound CCCCCCCCCCCCCC[Si](OCC)(OCC)OCC SVKDNKCAGJVMMY-UHFFFAOYSA-N 0.000 description 1
- PADYPAQRESYCQZ-UHFFFAOYSA-N triethoxy-(4-methylphenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=C(C)C=C1 PADYPAQRESYCQZ-UHFFFAOYSA-N 0.000 description 1
- HUZZQXYTKNNCOU-UHFFFAOYSA-N triethyl(methoxy)silane Chemical compound CC[Si](CC)(CC)OC HUZZQXYTKNNCOU-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- UWSYCPWEBZRZNJ-UHFFFAOYSA-N trimethoxy(2,4,4-trimethylpentyl)silane Chemical compound CO[Si](OC)(OC)CC(C)CC(C)(C)C UWSYCPWEBZRZNJ-UHFFFAOYSA-N 0.000 description 1
- XYJRNCYWTVGEEG-UHFFFAOYSA-N trimethoxy(2-methylpropyl)silane Chemical compound CO[Si](OC)(OC)CC(C)C XYJRNCYWTVGEEG-UHFFFAOYSA-N 0.000 description 1
- ZSOVVFMGSCDMIF-UHFFFAOYSA-N trimethoxy(naphthalen-1-yl)silane Chemical compound C1=CC=C2C([Si](OC)(OC)OC)=CC=CC2=C1 ZSOVVFMGSCDMIF-UHFFFAOYSA-N 0.000 description 1
- RKLXSINPXIQKIB-UHFFFAOYSA-N trimethoxy(oct-7-enyl)silane Chemical compound CO[Si](OC)(OC)CCCCCCC=C RKLXSINPXIQKIB-UHFFFAOYSA-N 0.000 description 1
- NMEPHPOFYLLFTK-UHFFFAOYSA-N trimethoxy(octyl)silane Chemical compound CCCCCCCC[Si](OC)(OC)OC NMEPHPOFYLLFTK-UHFFFAOYSA-N 0.000 description 1
- HILHCDFHSDUYNX-UHFFFAOYSA-N trimethoxy(pentyl)silane Chemical compound CCCCC[Si](OC)(OC)OC HILHCDFHSDUYNX-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
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- LGROXJWYRXANBB-UHFFFAOYSA-N trimethoxy(propan-2-yl)silane Chemical compound CO[Si](OC)(OC)C(C)C LGROXJWYRXANBB-UHFFFAOYSA-N 0.000 description 1
- XQEGZYAXBCFSBS-UHFFFAOYSA-N trimethoxy-(4-methylphenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=C(C)C=C1 XQEGZYAXBCFSBS-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/113—Silicon oxides; Hydrates thereof
- C01B33/12—Silica; Hydrates thereof, e.g. lepidoic silicic acid
- C01B33/14—Colloidal silica, e.g. dispersions, gels, sols
- C01B33/146—After-treatment of sols
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/113—Silicon oxides; Hydrates thereof
- C01B33/12—Silica; Hydrates thereof, e.g. lepidoic silicic acid
- C01B33/14—Colloidal silica, e.g. dispersions, gels, sols
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B33/00—Silicon; Compounds thereof
- C01B33/113—Silicon oxides; Hydrates thereof
- C01B33/12—Silica; Hydrates thereof, e.g. lepidoic silicic acid
- C01B33/14—Colloidal silica, e.g. dispersions, gels, sols
- C01B33/145—Preparation of hydroorganosols, organosols or dispersions in an organic medium
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01P—INDEXING SCHEME RELATING TO STRUCTURAL AND PHYSICAL ASPECTS OF SOLID INORGANIC COMPOUNDS
- C01P2004/00—Particle morphology
- C01P2004/60—Particles characterised by their size
- C01P2004/64—Nanometer sized, i.e. from 1-100 nanometer
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Silicon Compounds (AREA)
Description
本発明は、表面修飾シリカ粒子の有機溶媒分散ゾルの製造方法に関する。 The present invention relates to a method for producing a sol of surface-modified silica particles dispersed in an organic solvent.
シリカ粒子はその高い機械的特性及び熱的特性のため、しばしば樹脂組成物の成分として利用される。シリカ粒子を有機樹脂に配合する場合、該有機樹脂との相溶性や硬化性を考慮して、該シリカ粒子の表面を、疎水性シランカップリング剤、反応性部位含有シランカップリング剤等のシランカップリング剤で処理、即ち表面修飾することが多い。このように表面修飾されたシリカ粒子は、通常、有機溶媒に分散した状態(オルガノゾル)又はモノマーに分散した状態(モノマーゾル)の形で用いられる。 Silica particles are often utilized as a component of resin compositions due to their high mechanical and thermal properties. When blending silica particles with an organic resin, the surface of the silica particles may be coated with a silane such as a hydrophobic silane coupling agent or a silane coupling agent containing a reactive moiety, taking into consideration compatibility and curability with the organic resin. It is often treated with a coupling agent, that is, surface modified. Such surface-modified silica particles are usually used in the form of being dispersed in an organic solvent (organosol) or in a monomer (monomer sol).
シランカップリング剤によるシリカ粒子の表面修飾は、加水分解工程と、該加水分解工程に続く縮合工程とを経て行われる。前記加水分解工程では、シランカップリング剤の加水分解反応によってシラノール基(Si―OH)が生じ、シリカ粒子表面のシラノール基と水素結合が形成される。前記縮合工程では、加水分解されたシランカップリング剤のシラノール基と、シリカ粒子表面のシラノール基との縮合反応によって共有結合が形成される。加水分解反応と縮合反応とが共存すると、シランカップリング剤がシリカ粒子表面のシラノール基と縮合する前に、シランカップリング剤同士が縮合反応する虞があるため、該加水分解工程と該縮合工程とをコントロールすることが、均一かつ効率的にシリカ粒子を表面修飾するために重要である。 Surface modification of silica particles with a silane coupling agent is performed through a hydrolysis step and a condensation step following the hydrolysis step. In the hydrolysis step, silanol groups (Si--OH) are generated by the hydrolysis reaction of the silane coupling agent, and hydrogen bonds are formed with the silanol groups on the surface of the silica particles. In the condensation step, a covalent bond is formed by a condensation reaction between the silanol groups of the hydrolyzed silane coupling agent and the silanol groups on the surface of the silica particles. If the hydrolysis reaction and the condensation reaction coexist, there is a risk that the silane coupling agents will undergo a condensation reaction with each other before the silane coupling agent condenses with the silanol groups on the surface of the silica particles. It is important to control the surface modification of silica particles uniformly and efficiently.
一般に、酸性条件では、シラノール基が安定であり、加水分解工程が促進され、一方、塩基性条件では、シラノール基が不安定で、縮合工程が促進されることが知られている。したがって、シリカ粒子を表面修飾する手順としては、シリカ粒子とシランカップリング剤とを酸性条件で反応させ、その後、酸性条件から塩基性条件に変更することが、上記の観点から望ましい。また、前記酸性条件から塩基性条件に変更する時に、アミン化合物を添加することが知られている。例えば特許文献1には、有機溶媒分散シリカゾルにアミン化合物を添加してpHを所定の範囲にすることで、該シリカゾルから安定なエポキシモノマーゾル及びアクリルモノマーゾルを得られることが記載されている。 It is generally known that under acidic conditions, silanol groups are stable and the hydrolysis process is accelerated, whereas under basic conditions, silanol groups are unstable and the condensation process is accelerated. Therefore, as a procedure for surface modifying silica particles, it is desirable from the above point of view to react the silica particles and the silane coupling agent under acidic conditions, and then change the acidic conditions to basic conditions. It is also known to add an amine compound when changing from the acidic conditions to basic conditions. For example, Patent Document 1 describes that by adding an amine compound to a silica sol dispersed in an organic solvent to adjust the pH to a predetermined range, stable epoxy monomer sols and acrylic monomer sols can be obtained from the silica sol.
しかしながら、特許文献1に記載されているような、塩基性化合物を含有する有機溶媒分散シリカゾルは、以下に説明する理由から、保存安定性が必ずしも良いとはいえない。 However, the organic solvent-dispersed silica sol containing a basic compound as described in Patent Document 1 does not necessarily have good storage stability for the reasons explained below.
通常、有機溶媒分散シリカゾルに添加されたシランカップリング剤の全てをシリカ粒子表面のシラノール基と反応させることは困難であり、該有機溶媒分散シリカゾル中に未反応のシランカップリング剤が残存してしまう。これら残存シランカップリング剤は、塩基性条件下で長期間保管すると該シランカップリング剤同士で縮合反応を起こし得るため、結果的に有機溶媒分散シリカゾルの白濁及びゲル化を助長し、保存安定性が悪化することがある。 Normally, it is difficult to react all of the silane coupling agent added to an organic solvent-dispersed silica sol with the silanol groups on the surface of the silica particles, and unreacted silane coupling agents may remain in the organic solvent-dispersed silica sol. Put it away. When these residual silane coupling agents are stored for a long period of time under basic conditions, a condensation reaction may occur between the silane coupling agents, resulting in clouding and gelation of the organic solvent-dispersed silica sol, resulting in poor storage stability. may worsen.
本発明はこれら事情を鑑みてなされたものであり、保存安定性が良好な表面修飾シリカ粒子の有機溶媒分散ゾルの製造方法を提供することを目的とする。 The present invention has been made in view of these circumstances, and an object of the present invention is to provide a method for producing an organic solvent-dispersed sol of surface-modified silica particles having good storage stability.
本発明者らは、縮合反応が塩基性条件下で促進されることに注目し、表面修飾シリカ粒子の有機溶媒分散ゾル中に未反応のシランカップリング剤が残存していても、酸性又は中性条件下であれば未反応のシランカップリング剤同士の縮合を抑制できると着想した。検討の結果、塩基性化合物を含む表面修飾シリカ粒子の有機溶媒分散ゾルに陽イオン交換樹脂を接触させて該塩基性化合物の一部又は全部を除去することで、表面修飾シリカ粒子の有機溶媒分散ゾルの保存安定性が極めて良好になることを見出した。 The present inventors focused on the fact that the condensation reaction is promoted under basic conditions, and found that even if unreacted silane coupling agent remains in the organic solvent dispersion sol of surface-modified silica particles, the condensation reaction is accelerated under basic conditions. The idea was that condensation between unreacted silane coupling agents could be suppressed under normal conditions. As a result of our study, we found that by bringing a cation exchange resin into contact with an organic solvent-dispersed sol of surface-modified silica particles containing a basic compound to remove part or all of the basic compound, surface-modified silica particles can be dispersed in an organic solvent. It has been found that the storage stability of the sol is extremely good.
すなわち、本発明は、下記(A)工程乃至(C)工程を含む、表面修飾シリカ粒子の有機溶媒分散ゾルの製造方法である。
(A)表面未修飾シリカ粒子の有機溶媒分散ゾルとシランカップリング剤とを混合する工程
(B)(A)工程で得られた結果物に対し、塩基性化合物を添加する工程
(C)(B)工程で得られた結果物に対し、陽イオン交換樹脂を接触させる工程That is, the present invention is a method for producing an organic solvent-dispersed sol of surface-modified silica particles, which includes the following steps (A) to (C).
(A) Step of mixing an organic solvent-dispersed sol of surface-unmodified silica particles and a silane coupling agent (B) Step of adding a basic compound to the resultant obtained in step (A) (C) ( B) A step of contacting the resultant obtained in step with a cation exchange resin
前記表面未修飾シリカ粒子の有機溶媒分散ゾル中のシリカ粒子の一次粒子径が、例えば1nm乃至100nmである。 The primary particle diameter of the silica particles in the organic solvent-dispersed sol of the surface-unmodified silica particles is, for example, 1 nm to 100 nm.
前記塩基性化合物が、例えばアミン類である。 The basic compound is, for example, an amine.
前記塩基性化合物が、例えば下記式(1)で表されるアルキルアミン類である。
前記シランカップリング剤が、例えば下記式(2)で表されるシラン化合物である。
前記式(2)で表されるシラン化合物が、例えば下記式(2´)で表されるシラン化合物である。
前記(C)工程は、例えば、前記(B)工程で得られた結果物に前記陽イオン交換樹脂を添加し撹拌する工程、又は前記陽イオン交換樹脂が充填されたカラムに該(B)工程で得られた結果物を通液する工程である。前記(C)工程において、前記陽イオン交換樹脂に前記(B)工程で得られた結果物に含まれる塩基性化合物に由来する陽イオンを吸着させる。前記(C)工程で得られる表面修飾シリカ粒子の有機溶媒分散ゾルのpHが好ましくは2乃至6である。 The step (C) is, for example, a step of adding the cation exchange resin to the resultant obtained in the step (B) and stirring it, or adding the cation exchange resin to a column filled with the cation exchange resin in the step (B). This is a step in which the resultant product obtained in step 1 is passed through the solution. In the step (C), the cation exchange resin is made to adsorb cations derived from the basic compound contained in the product obtained in the step (B). The pH of the organic solvent-dispersed sol of surface-modified silica particles obtained in step (C) is preferably 2 to 6.
本発明の製造方法により得られた表面修飾シリカ粒子の有機溶媒分散ゾルは、保存安定性が良好であり、長期間保管してもゲル化することなく透明性及び流動性を保持し、粘度がほとんど上昇しない。さらに、本発明の製造方法により得られた表面修飾シリカ粒子の有機溶媒分散ゾルは、酸性又は中性条件下でシリカ粒子の分散性が維持される。 The organic solvent-dispersed sol of surface-modified silica particles obtained by the production method of the present invention has good storage stability, maintains transparency and fluidity without gelation even after long-term storage, and has a low viscosity. Almost no rise. Furthermore, in the organic solvent-dispersed sol of surface-modified silica particles obtained by the production method of the present invention, the dispersibility of the silica particles is maintained under acidic or neutral conditions.
以下、本発明に関して詳細を説明する。 The present invention will be explained in detail below.
本発明で使用する表面未修飾シリカ粒子の有機溶媒分散ゾルは特に限定されず、公知の方法により製造されたものを用い得る。例えば、水ガラス(ケイ酸ナトリウム)を原料として得られた水分散シリカゾルを有機溶媒置換する方法、粉末状態のシリカ粒子を有機溶媒又は有機溶媒/水混合液に分散させる方法が挙げられる。 The organic solvent-dispersed sol of surface-unmodified silica particles used in the present invention is not particularly limited, and those produced by known methods can be used. Examples include a method in which a water-dispersed silica sol obtained using water glass (sodium silicate) as a raw material is replaced with an organic solvent, and a method in which powdered silica particles are dispersed in an organic solvent or an organic solvent/water mixture.
前記表面未修飾シリカ粒子の有機溶媒分散ゾル中のシリカ粒子濃度は特に限定されないが、一般に60質量%以下が好ましい。 The concentration of silica particles in the organic solvent-dispersed sol of the surface-unmodified silica particles is not particularly limited, but is generally preferably 60% by mass or less.
前記表面未修飾シリカ粒子の有機溶媒分散ゾル中のシリカ粒子は、例えば一次粒子径が1nm乃至100nmのシリカ粒子である。ここで、一次粒子とは、粉体を構成する粒子であり、この一次粒子が凝集した粒子を二次粒子という。前記一次粒子径は、ガス吸着法(BET法)により測定される前記シリカ粒子の比表面積(単位質量あたりの表面積)S、該シリカ粒子の密度ρ、及び一次粒子径Dとの間に成り立つ関係式:D=6/(ρS)から算出することができる。該関係式から算出される一次粒子径は、平均粒子径であり、一次粒子の直径である。 The silica particles in the organic solvent-dispersed sol of surface-unmodified silica particles have, for example, a primary particle diameter of 1 nm to 100 nm. Here, primary particles are particles constituting powder, and particles in which these primary particles aggregate are called secondary particles. The primary particle diameter has a relationship between the specific surface area (surface area per unit mass) S of the silica particles measured by a gas adsorption method (BET method), the density ρ of the silica particles, and the primary particle diameter D. It can be calculated from the formula: D=6/(ρS). The primary particle diameter calculated from this relational expression is the average particle diameter, and is the diameter of the primary particles.
前記表面未修飾シリカ粒子の有機溶媒分散ゾル中のシリカ粒子の形状は特に限定されず、いずれの形状でもよい。例えば、球状、楕円球状、扁平状、細長い形状、歪な形状が挙げられる。 The shape of the silica particles in the organic solvent-dispersed sol of surface-unmodified silica particles is not particularly limited, and may be of any shape. Examples include a spherical shape, an ellipsoidal shape, a flat shape, an elongated shape, and a distorted shape.
前記表面未修飾シリカ粒子の有機溶媒分散ゾル中の溶媒は、シリカ粒子が分散できる限り特に限定されず、有機溶媒のみ、或いは有機溶媒/水混合液のいずれでもよい。有機溶媒のみを用いる場合、炭化水素類、ハロゲン化炭化水素類、エーテル類、アルコール類、アルデヒド類、ケトン類、エステル類、アミド類、ニトリル類等の全ての有機溶媒を使用することができる。有機溶媒/水混合液を用いる場合、水と混合可能な有機溶媒を使用することができる。 The solvent in the organic solvent dispersion sol of the surface-unmodified silica particles is not particularly limited as long as the silica particles can be dispersed therein, and may be either only an organic solvent or an organic solvent/water mixture. When only organic solvents are used, all organic solvents such as hydrocarbons, halogenated hydrocarbons, ethers, alcohols, aldehydes, ketones, esters, amides, and nitriles can be used. When using an organic solvent/water mixture, an organic solvent that is miscible with water can be used.
前記炭化水素類としては、例えば、n―ペンタン、シクロペンタン、メチルシクロペンタン、n―ヘキサン、イソヘキサン、シクロヘキサン、メチルシクロヘキサン、エチルシクロヘキサン、n―ヘプタン、ベンゼン、トルエン、о―キシレン、m―キシレン、p―キシレン及びメシチレンが挙げられる。 Examples of the hydrocarbons include n-pentane, cyclopentane, methylcyclopentane, n-hexane, isohexane, cyclohexane, methylcyclohexane, ethylcyclohexane, n-heptane, benzene, toluene, о-xylene, m-xylene, Mention may be made of p-xylene and mesitylene.
前記ハロゲン化炭化水素類としては、例えば、ジクロロメタン、クロロホルム、四塩化炭素、クロロエタン、ジクロロエタン、トリクロロエタン、テトラクロロエタン、ヘキサクロロエタン、ジクロロエチレン、トリクロロエチレン、テトラクロロエチレン、クロロベンゼン、ハイドロフルオロカーボン及びパーフルオロカーボンが挙げられる。 Examples of the halogenated hydrocarbons include dichloromethane, chloroform, carbon tetrachloride, chloroethane, dichloroethane, trichloroethane, tetrachloroethane, hexachloroethane, dichloroethylene, trichloroethylene, tetrachloroethylene, chlorobenzene, hydrofluorocarbon, and perfluorocarbon.
前記エーテル類としては、例えば、ジエチルエーテル、ジ―n―プロピルエーテル、ジイソプロピルエーテル、ジ―n―ブチルエーテル、ジイソブチルエーテル、ジ―tert―ブチルエーテル、ジ―n―ペンチルエーテル、ジイソペンチルエーテル、ジ―n―ヘキシルエーテル、メチル―n―プロピルエーテル、メチルイソプロピルエーテル、エチル―n―プロピルエーテル、エチルイソプロピルエーテル、n―ブチルメチルエーテル、イソブチルメチルエーテル、tert―ブチルメチルエーテル、n―ブチルエチルエーテル、イソブチルエチルエーテル、tert―ブチルエチルエーテル、メチル―n―ペンチルエーテル、シクロペンチルメチルエーテル、n―ヘキシルメチルエーテル、シクロヘキシルメチルエーテル、テトラヒドロフラン、1,3―ジオキサン、1,4―ジオキサン、エチレングリコールジメチルエーテル、エチレングリコールジエチルエーテル、エチレングリコールジブチルエーテル、ジエチレングリコールジメチルエーテル、ジエチレングリコールジエチルエーテル、ジエチレングリコールジブチルエーテル、トリエチレングリコールジメチルエーテル、トリエチレングリコールジエチルエーテル、トリエチレングリコールジブチルエーテル、プロピレングリコールジメチルエーテル、プロピレングリコールジエチルエーテル、プロピレングリコールジブチルエーテル、ジプロピレングリコールジメチルエーテル、ジプロピレングリコールジエチルエーテル、ジプロピレングリコールジブチルエーテル、トリプロピレングリコールジメチルエーテル、トリプロピレングリコールジエチルエーテル及びトリプロピレングリコールジブチルエーテルが挙げられる。 Examples of the ethers include diethyl ether, di-n-propyl ether, diisopropyl ether, di-n-butyl ether, diisobutyl ether, di-tert-butyl ether, di-n-pentyl ether, diisopentyl ether, di- n-hexyl ether, methyl-n-propyl ether, methyl isopropyl ether, ethyl-n-propyl ether, ethyl isopropyl ether, n-butyl methyl ether, isobutyl methyl ether, tert-butyl methyl ether, n-butyl ethyl ether, isobutyl Ethyl ether, tert-butyl ethyl ether, methyl-n-pentyl ether, cyclopentyl methyl ether, n-hexyl methyl ether, cyclohexyl methyl ether, tetrahydrofuran, 1,3-dioxane, 1,4-dioxane, ethylene glycol dimethyl ether, ethylene glycol Diethyl ether, ethylene glycol dibutyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol diethyl ether, triethylene glycol dibutyl ether, propylene glycol dimethyl ether, propylene glycol diethyl ether, propylene glycol dibutyl ether, Dipropylene glycol dimethyl ether, dipropylene glycol diethyl ether, dipropylene glycol dibutyl ether, tripropylene glycol dimethyl ether, tripropylene glycol diethyl ether and tripropylene glycol dibutyl ether.
前記アルコール類としては、例えば、メタノール、エタノール、1―プロパノール、2―プロパノール、1―ブタノール、2―ブタノール、2―メチル―1―プロパノール、tert―ブチルアルコール、1―ペンタノール、2―ペンタノール、3―ペンタノール、2―メチル―1―ブタノール、3―メチル―2―ブタノール、ネオペンチルアルコール、シクロペンタノール、メチルシクロペンタノール、1―ヘキサノール、2―ヘキサノール、3―ヘキサノール、シクロヘキサノール、メチルシクロヘキサノール、1―ヘプタノール、2―ヘプタノール、3―ヘプタノール、4―ヘプタノール、1―オクタノール、2―オクタノール、3―オクタノール、4―オクタノール、2―エチル―1―ヘキサノール、ベンジルアルコール、エチレングリコールモノメチルエーテル、エチレングリコールモノエチルエーテル、エチレングリコールモノプロピルエーテル、エチレングリコールモノブチルエーテル、ジエチレングリコールモノメチルエーテル、ジエチレングリコールモノエチルエーテル、ジエチレングリコールモノブチルエーテル、トリエチレングリコールモノメチルエーテル、トリエチレングリコールモノエチルエーテル、トリエチレングリコールモノプロピルエーテル、トリエチレングリコールモノブチルエーテル、プロピレングリコールモノメチルエーテル、プロピレングリコールモノエチルエーテル、プロピレングリコールモノブチルエーテル、ジプロピレングリコールモノメチルエーテル、ジプロピレングリコールモノエチルエーテル、ジプロピレングリコールモノブチルエーテル、トリプロピレングリコールモノメチルエーテル、トリプロピレングリコールモノエチルエーテル及びトリプロピレングリコールモノブチルエーテル等の1価アルコール、エチレングリコール、ジエチレングリコール、トリエチレングリコール、テトラエチレングリコール、1,3―プロパンジオール、プロピレングリコール、ジプロピレングリコール、トリプロピレングリコール、1,4―ブタンジオール、1,3―ブタンジオール、1,2―ブタンジオール、1,5―ペンタンジオール、1,4―ペンタンジオール、1,3―ペンタンジオール、1,2―ペンタンジオール、3―メチル―1,5―ペンタンジオール、2,2,4―トリメチル―1,3―ペンタンジオール及び1,2―ヘキサンジオール等の2価アルコール、グリセリン等の3価アルコールが挙げられる。 Examples of the alcohols include methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 2-methyl-1-propanol, tert-butyl alcohol, 1-pentanol, and 2-pentanol. , 3-pentanol, 2-methyl-1-butanol, 3-methyl-2-butanol, neopentyl alcohol, cyclopentanol, methylcyclopentanol, 1-hexanol, 2-hexanol, 3-hexanol, cyclohexanol, Methylcyclohexanol, 1-heptanol, 2-heptanol, 3-heptanol, 4-heptanol, 1-octanol, 2-octanol, 3-octanol, 4-octanol, 2-ethyl-1-hexanol, benzyl alcohol, ethylene glycol monomethyl Ether, ethylene glycol monoethyl ether, ethylene glycol monopropyl ether, ethylene glycol monobutyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, triethylene glycol monomethyl ether, triethylene glycol monoethyl ether, triethylene glycol monopropyl Ether, triethylene glycol monobutyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, propylene glycol monobutyl ether, dipropylene glycol monomethyl ether, dipropylene glycol monoethyl ether, dipropylene glycol monobutyl ether, tripropylene glycol monomethyl ether, Monohydric alcohols such as propylene glycol monoethyl ether and tripropylene glycol monobutyl ether, ethylene glycol, diethylene glycol, triethylene glycol, tetraethylene glycol, 1,3-propanediol, propylene glycol, dipropylene glycol, tripropylene glycol, 1, 4-butanediol, 1,3-butanediol, 1,2-butanediol, 1,5-pentanediol, 1,4-pentanediol, 1,3-pentanediol, 1,2-pentanediol, 3-methyl Examples include dihydric alcohols such as -1,5-pentanediol, 2,2,4-trimethyl-1,3-pentanediol and 1,2-hexanediol, and trihydric alcohols such as glycerin.
前記アルデヒド類としては、例えば、エタナール、プロパナール、2―メチル―1―プロパナール、ブタナール、3―メチルブタナール、ペンタナール及びベンズアルデヒドが挙げられる。 Examples of the aldehydes include ethanal, propanal, 2-methyl-1-propanal, butanal, 3-methylbutanal, pentanal, and benzaldehyde.
前記ケトン類としては、例えば、アセトン、2―ブタノン、2―ペンタノン、3―ペンタノン、シクロペンタノン、2,4―ペンタンジオン、4―メチル―2―ペンタノン、4―ヒドロキシ―4―メチル―2―ペンタノン、シクロヘキサノン及び2―ヘプタノンが挙げられる。 Examples of the ketones include acetone, 2-butanone, 2-pentanone, 3-pentanone, cyclopentanone, 2,4-pentanedione, 4-methyl-2-pentanone, 4-hydroxy-4-methyl-2 -pentanone, cyclohexanone and 2-heptanone.
前記エステル類としては、例えば、メチルホルマート、エチルホルマート、n―プロピルホルマート、イソプロピルホルマート、n―ブチルホルマート、イソブチルホルマート、tert―ブチルホルマート、n―ペンチルホルマート、イソペンチルホルマート、メチルアセタート、エチルアセタート、n―プロピルアセタート、イソプロピルアセタート、n―ブチルアセタート、イソブチルアセタート、tert―ブチルアセタート、n―ペンチルアセタート、イソペンチルアセタート、シクロペンチルアセタート、n―へキシルアセタート、イソへキシルアセタート、シクロヘキシルアセタート、n―ヘプチルアセタート、イソヘプチルアセタート、n―オクチルアセタート、イソオクチルアセタート、ベンジルアセタート、エチレングリコールモノメチルエーテルアセタート、エチレングリコールモノエチルエーテルアセタート、エチレングリコールモノブチルエーテルアセタート、エチレングリコールジアセタート、ジエチレングリコールモノメチルエーテルアセタート、ジエチレングリコールモノエチルエーテルアセタート、ジエチレングリコールモノブチルエーテルアセタート、トリエチレングリコールモノメチルエーテルアセタート、トリエチレングリコールモノエチルエーテルアセタート、トリエチレングリコールモノブチルエーテルアセタート、プロピレングリコールモノメチルエーテルアセタート、プロピレングリコールモノエチルエーテルアセタート、プロピレングリコールモノブチルエーテルアセタート、プロピレングリコールジアセタート、ジプロピレングリコールモノメチルエーテルアセタート、ジプロピレングリコールモノエチルエーテルアセタート、ジプロピレングリコールモノブチルエーテルアセタート、トリプロピレングリコールモノメチルエーテルアセタート、トリプロピレングリコールモノエチルエーテルアセタート、トリプロピレングリコールモノブチルエーテルアセタート、メチルプロピオナート、エチルプロピオナート、n―プロピルプロピオナート、イソプロピルプロピオナート、n―ブチルプロピオナート、イソブチルプロピオナート、tert―ブチルプロピオナート、メチルブチラート、エチルブチラート、n―プロピルブチラート、イソプロピルブチラート、n―ブチルブチラート、イソブチルブチラート、tert―ブチルブチラート、メチルイソブチラート、エチルイソブチラート、n―プロピルイソブチラート、イソプロピルイソブチラート、n―ブチルイソブチラート、イソブチルイソブチラート、tert―ブチルイソブチラート、メチルラクタート、エチルラクタート、n―プロピルラクタート、イソプロピルラクタート、n―ブチルラクタート、イソブチルラクタート、tert―ブチルラクタート、メチルアセトアセタート、エチルアセトアセタート、n―プロピルアセトアセタート、イソプロピルアセトアセタート、n―ブチルアセトアセタート、イソブチルアセトアセタート、tert―ブチルアセトアセタート、ジメチルマロナート、ジエチルマロナート、トリアセチン、γ―ブチロラクトン、γ―バレロラクトン、γ―カプロラクトン、δ―バレロラクトン、δ―カプロラクトン及びε―カプロラクトンが挙げられる。 Examples of the esters include methyl formate, ethyl formate, n-propyl formate, isopropyl formate, n-butyl formate, isobutyl formate, tert-butyl formate, n-pentyl formate, and isopentyl formate. Formate, methyl acetate, ethyl acetate, n-propyl acetate, isopropyl acetate, n-butyl acetate, isobutyl acetate, tert-butyl acetate, n-pentyl acetate, isopentyl acetate, cyclopentyl acetate tartate, n-hexyl acetate, isohexyl acetate, cyclohexyl acetate, n-heptyl acetate, isoheptyl acetate, n-octyl acetate, isooctyl acetate, benzyl acetate, ethylene glycol monomethyl ether acetate, ethylene glycol Monoethyl ether acetate, ethylene glycol monobutyl ether acetate, ethylene glycol diacetate, diethylene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, diethylene glycol monobutyl ether acetate, triethylene glycol monomethyl ether acetate, triethylene glycol mono Ethyl ether acetate, triethylene glycol monobutyl ether acetate, propylene glycol monomethyl ether acetate, propylene glycol monoethyl ether acetate, propylene glycol monobutyl ether acetate, propylene glycol diacetate, dipropylene glycol monomethyl ether acetate, Propylene glycol monoethyl ether acetate, dipropylene glycol monobutyl ether acetate, tripropylene glycol monomethyl ether acetate, tripropylene glycol monoethyl ether acetate, tripropylene glycol monobutyl ether acetate, methyl propionate, ethyl propionate , n-propyl propionate, isopropyl propionate, n-butyl propionate, isobutyl propionate, tert-butyl propionate, methyl butyrate, ethyl butyrate, n-propyl butyrate, isopropyl butyrate, n-butyl butyrate, isobutyl butyrate, tert-butyl butyrate, methyl isobutyrate, ethyl isobutyrate, n-propyl isobutyrate, isopropyl isobutyrate, n-butyl isobutyrate, isobutyl isobutyrate, tert-butyl isobutyrate, methyl lactate, ethyl lactate, n-propyl lactate, isopropyl lactate, n-butyl lactate, isobutyl lactate, tert-butyl lactate, methyl acetoacetate, ethyl acetoacetate , n-propylacetoacetate, isopropylacetoacetate, n-butylacetoacetate, isobutylacetoacetate, tert-butylacetoacetate, dimethylmalonate, diethylmalonate, triacetin, γ-butyrolactone, γ-valerolactone , γ-caprolactone, δ-valerolactone, δ-caprolactone and ε-caprolactone.
前記アミド類としては、例えば、N,N―ジメチルホルムアミド、N,N―ジメチルアセトアミド及びN―メチルピロリドンが挙げられる。 Examples of the amides include N,N-dimethylformamide, N,N-dimethylacetamide, and N-methylpyrrolidone.
前記ニトリル類としては、例えば、アセトニトリル、プロピオニトリル及びブチロニトリルが挙げられる。 Examples of the nitriles include acetonitrile, propionitrile, and butyronitrile.
これら有機溶媒は1種単独で、又は2種以上を組み合わせて使用することができる。なお、前記表面未修飾シリカ粒子の有機溶媒分散ゾルは、そのまま本発明に使用するだけでなく、これを用いて、モノマーゾルの製造を行うことができる。その場合、該表面未修飾シリカ粒子の有機溶媒分散ゾル中の有機溶媒をモノマーへと置換する工程を鑑み、該モノマーとの相溶性が高く、かつ減圧蒸留による除去性が高い有機溶媒を選択することで、均一なモノマーゾルを効率よく得ることができる。 These organic solvents can be used alone or in combination of two or more. Note that the organic solvent-dispersed sol of surface-unmodified silica particles can not only be used as is in the present invention, but also can be used to produce a monomer sol. In that case, in consideration of the step of replacing the organic solvent in the organic solvent-dispersed sol of the surface-unmodified silica particles with a monomer, select an organic solvent that has high compatibility with the monomer and is highly removable by vacuum distillation. By doing so, a uniform monomer sol can be efficiently obtained.
前記表面未修飾シリカ粒子の有機溶媒分散ゾルとして市販品を用いてもよく、具体的には、CHO―ST―M、DMAC―ST、DMAC―ST―ZL、EAC―ST、EG―ST、EG―ST―ZL、EG―ST―XL30、IPA―ST、IPA―ST―L、IPA―ST―ZL、IPA―ST―UP、メタノールシリカゾル、MA―ST―M、MA―ST―L、MA―ST―ZL、MA―ST―UP、MEK―ST、MEK―ST―40、MEK―ST―L、MEK―ST―ZL、MEK―ST―UP、MIBK―ST、MIBK―ST―L、NMP―ST、NPC―ST―30、PMA―ST、PGM―ST、PGM―ST―UP、TOL―ST、XBA―ST(以上、日産化学(株)製)、PL―1―IPA、PL―1―TOL、PL―2L―PGME及びPL―2L―MEK(以上、扶桑化学工業(株)製)等が挙げられる。 Commercial products may be used as the organic solvent dispersion sol of the surface-unmodified silica particles, and specifically, CHO-ST-M, DMAC-ST, DMAC-ST-ZL, EAC-ST, EG-ST, EG. -ST-ZL, EG-ST-XL30, IPA-ST, IPA-ST-L, IPA-ST-ZL, IPA-ST-UP, methanol silica sol, MA-ST-M, MA-ST-L, MA- ST-ZL, MA-ST-UP, MEK-ST, MEK-ST-40, MEK-ST-L, MEK-ST-ZL, MEK-ST-UP, MIBK-ST, MIBK-ST-L, NMP- ST, NPC-ST-30, PMA-ST, PGM-ST, PGM-ST-UP, TOL-ST, XBA-ST (manufactured by Nissan Chemical Co., Ltd.), PL-1-IPA, PL-1- Examples include TOL, PL-2L-PGME, and PL-2L-MEK (all manufactured by Fuso Chemical Industry Co., Ltd.).
前記表面未修飾シリカ粒子の有機溶媒分散ゾルとして、市販の水分散シリカゾルを減圧蒸留や限外濾過といった公知の方法で有機溶媒置換したもの、市販の粉末状シリカ粒子を有機溶媒或いは有機溶媒/水混合液に分散させたものを用いてもよい。 As the organic solvent-dispersed sol of the surface-unmodified silica particles, commercially available water-dispersed silica sol may be substituted with an organic solvent by a known method such as vacuum distillation or ultrafiltration, or commercially available powdered silica particles may be dissolved in an organic solvent or organic solvent/water. You may use what was dispersed in a liquid mixture.
これら表面未修飾シリカ粒子の有機溶媒分散ゾルは1種単独で、又は2種以上を組み合わせて使用することができる。 These organic solvent-dispersed sols of surface-unmodified silica particles can be used alone or in combination of two or more.
本発明で使用するシランカップリング剤は、分子内にケイ素原子を少なくとも1個有し、かつ該ケイ素原子の内の少なくとも1個に加水分解性基(加水分解によってシラノール基が形成され得る官能基であり、例えばアルコキシ基)が1個乃至3個結合した化合物である。 The silane coupling agent used in the present invention has at least one silicon atom in the molecule, and at least one of the silicon atoms has a hydrolyzable group (a functional group that can form a silanol group by hydrolysis). For example, it is a compound in which one to three alkoxy groups are bonded.
前記シランカップリング剤としては、例えば、メチルトリメトキシシラン、エチルトリメトキシシラン、n―プロピルトリメトキシシラン、イソプロピルトリメトキシシラン、n―ブチルトリメトキシシラン、イソブチルトリメトキシシラン、n―ペンチルトリメトキシシラン、シクロペンチルトリメトキシシラン、n―ヘキシルトリメトキシシラン、シクロヘキシルトリメトキシシラン、n―オクチルトリメトキシシラン、イソオクチルトリメトキシシラン、n―デシルトリメトキシシラン、n―ドデシルトリメトキシシラン、n―テトラデシルトリメトキシシラン、n―ヘキサデシルトリメトキシシラン、n―オクタデシルトリメトキシシラン、ビニルトリメトキシシラン、アリルトリメトキシシラン、7―オクテニルトリメトキシシラン、3―(メタ)アクリロイルオキシプロピルトリメトキシシラン、8―(メタ)アクリロイルオキシオクチルトリメトキシシラン、フェニルトリメトキシシラン、p―トリルトリメトキシシラン、p―スチリルトリメトキシシラン、ベンジルトリメトキシシラン、1―ナフチルトリメトキシシラン、トリメトキシ[3―(フェニルアミノ)プロピル]シラン、 [3―(N,N―ジメチルアミノ)プロピル]トリメトキシシラン、3―(2―アミノエチルアミノ)プロピルトリメトキシシラン、8―(2―アミノエチルアミノ)オクチルトリメトキシシラン、3―アミノプロピルトリメトキシシラン、3―メルカプトプロピルトリメトキシシラン、3―イソシアナトプロピルトリメトキシシラン、トリス[3―(トリメトキシシリル)プロピル]イソシアヌレート、メチルトリエトキシシラン、エチルトリエトキシシラン、n―プロピルトリエトキシシラン、イソプロピルトリエトキシシラン、n―ブチルトリエトキシシラン、イソブチルトリエトキシシラン、n―ペンチルトリエトキシシラン、シクロペンチルトリエトキシシラン、n―ヘキシルトリエトキシシラン、シクロヘキシルトリエトキシシラン、n―オクチルトリエトキシシラン、イソオクチルトリエトキシシラン、n―デシルトリエトキシシラン、n―ドデシルトリエトキシシラン、n―テトラデシルトリエトキシシラン、n―ヘキサデシルトリエトキシシラン、n―オクタデシルトリエトキシシラン、ビニルトリエトキシシラン、アリルトリエトキシシラン、3―(メタ)アクリロイルオキシプロピルトリエトキシシラン、8―(メタ)アクリロイルオキシオクチルトリエトキシシラン、フェニルトリエトキシシラン、p―トリルトリエトキシシラン、p―スチリルトリエトキシシラン、ベンジルトリエトキシシラン、3―アミノプロピルトリエトキシシラン、3―メルカプトプロピルトリエトキシシラン、3―イソシアナトプロピルトリエトキシシラン、トリス[3―(トリエトキシシリル)プロピル]イソシアヌレート等のトリアルコキシシラン類、ジメチルジメトキシシラン、ジエチルジメトキシシラン、ジイソブチルジメトキシシラン、シクロペンチルメチルジメトキシシラン、ジシクロペンチルジメトキシシラン、シクロヘキシルメチルジメトキシシラン、n―オクチルメチルジメトキシシラン、ビニルメチルジメトキシシラン、3―(メタ)アクリロイルオキシプロピルメチルジメトキシシラン、フェニルメチルジメトキシシラン、ジフェニルジメトキシシラン、ジ―p―トリルジメトキシシラン、3―アミノ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、ジメチルジエトキシシラン、ジエチルジエトキシシラン、ジイソブチルジエトキシシラン、シクロペンチルメチルジエトキシシラン、ジシクロペンチルジエトキシシラン、シクロヘキシルメチルジエトキシシラン、n―オクチルメチルジエトキシシラン、ビニルメチルジエトキシシラン、3―(メタ)アクリロイルオキシプロピルメチルジエトキシシラン、フェニルメチルジエトキシシラン、ジフェニルジエトキシシラン、ジ―p―トリルジエトキシシラン、3―(2―アミノエチルアミノ)プロピルメチルジメトキシシラン、3―アミノ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等のジアルコキシシラン類、トリメチルメトキシシラン、トリエチルメトキシシラン、n―オクチルジメチルメトキシシラン、n―オクタデシルジメチルメトキシシラン、ビニルジメチルメトキシシラン、3―(メタ)アクリロイルオキシプロピルジメチルメトキシシラン、フェニルジメチルメトキシシラン、ジフェニルメチルメトキシシラン、トリフェニルメトキシシラン等のモノアルコキシシラン類及び多官能基型シランカップリング剤が挙げられる。 Examples of the silane coupling agent include methyltrimethoxysilane, ethyltrimethoxysilane, n-propyltrimethoxysilane, isopropyltrimethoxysilane, n-butyltrimethoxysilane, isobutyltrimethoxysilane, and n-pentyltrimethoxysilane. , cyclopentyltrimethoxysilane, n-hexyltrimethoxysilane, cyclohexyltrimethoxysilane, n-octyltrimethoxysilane, isooctyltrimethoxysilane, n-decyltrimethoxysilane, n-dodecyltrimethoxysilane, n-tetradecyltrimethoxysilane Methoxysilane, n-hexadecyltrimethoxysilane, n-octadecyltrimethoxysilane, vinyltrimethoxysilane, allyltrimethoxysilane, 7-octenyltrimethoxysilane, 3-(meth)acryloyloxypropyltrimethoxysilane, 8- (meth)acryloyloxyoctyltrimethoxysilane, phenyltrimethoxysilane, p-tolyltrimethoxysilane, p-styryltrimethoxysilane, benzyltrimethoxysilane, 1-naphthyltrimethoxysilane, trimethoxy[3-(phenylamino)propyl ] Silane, [3-(N,N-dimethylamino)propyl]trimethoxysilane, 3-(2-aminoethylamino)propyltrimethoxysilane, 8-(2-aminoethylamino)octyltrimethoxysilane, 3- Aminopropyltrimethoxysilane, 3-mercaptopropyltrimethoxysilane, 3-isocyanatopropyltrimethoxysilane, tris[3-(trimethoxysilyl)propyl]isocyanurate, methyltriethoxysilane, ethyltriethoxysilane, n-propyl Triethoxysilane, isopropyltriethoxysilane, n-butyltriethoxysilane, isobutyltriethoxysilane, n-pentyltriethoxysilane, cyclopentyltriethoxysilane, n-hexyltriethoxysilane, cyclohexyltriethoxysilane, n-octyltriethoxy Silane, isooctyltriethoxysilane, n-decyltriethoxysilane, n-dodecyltriethoxysilane, n-tetradecyltriethoxysilane, n-hexadecyltriethoxysilane, n-octadecyltriethoxysilane, vinyltriethoxysilane, Allyltriethoxysilane, 3-(meth)acryloyloxypropyltriethoxysilane, 8-(meth)acryloyloxyoctyltriethoxysilane, phenyltriethoxysilane, p-tolyltriethoxysilane, p-styryltriethoxysilane, benzyl triethoxysilane Ethoxysilane, 3-aminopropyltriethoxysilane, 3-mercaptopropyltriethoxysilane, 3-isocyanatopropyltriethoxysilane, trialkoxysilanes such as tris[3-(triethoxysilyl)propyl]isocyanurate, dimethyldimethoxy Silane, diethyldimethoxysilane, diisobutyldimethoxysilane, cyclopentylmethyldimethoxysilane, dicyclopentyldimethoxysilane, cyclohexylmethyldimethoxysilane, n-octylmethyldimethoxysilane, vinylmethyldimethoxysilane, 3-(meth)acryloyloxypropylmethyldimethoxysilane, phenyl Methyldimethoxysilane, diphenyldimethoxysilane, di-p-tolyldimethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-mercaptopropylmethyldimethoxysilane, dimethyldiethoxysilane, diethyldiethoxysilane, diisobutyldiethoxysilane, cyclopentylmethyldimethoxysilane Ethoxysilane, dicyclopentyldiethoxysilane, cyclohexylmethyldiethoxysilane, n-octylmethyldiethoxysilane, vinylmethyldiethoxysilane, 3-(meth)acryloyloxypropylmethyldiethoxysilane, phenylmethyldiethoxysilane, diphenyldiethoxysilane Dialkoxysilanes such as ethoxysilane, di-p-tolyldiethoxysilane, 3-(2-aminoethylamino)propylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, 3-mercaptopropylmethyldiethoxysilane, Trimethylmethoxysilane, triethylmethoxysilane, n-octyldimethylmethoxysilane, n-octadecyldimethylmethoxysilane, vinyldimethylmethoxysilane, 3-(meth)acryloyloxypropyldimethylmethoxysilane, phenyldimethylmethoxysilane, diphenylmethylmethoxysilane, trimethylmethoxysilane Examples include monoalkoxysilanes such as phenylmethoxysilane and polyfunctional silane coupling agents.
前記シランカップリング剤として市販品を用いてもよく、具体的には、KBM―1003、KBE―1003、KBM―1083、KBM―1403、KBM―502、KBM―503、KBE―502、KBE―503、KBM―5803、KBM―5103、KBM―602、KBM―603、KBM―903、KBE―903、KBM―573、KBM―6803、KBE―9007、KBM―9659、KBE―9659、KBM―802、KBM―803、KBM―13、KBE―13、KBM―22、KBE―22、KBM―103、KBE―103、KBM―202SS、KBM―3033、KBE―3033、KBM―3063、KBE―3063、KBM―3103C、KBE―3083、X―12―1048、X―12―1050、X―12―1154、X―12―1156、X―12―972F、X―12―1159L、X―40―9296、KR―503、KR―511、KR―513、KR―518、KR―519及びKPN―3504(以上、信越化学工業(株)製)等が挙げられる。 Commercial products may be used as the silane coupling agent, and specifically, KBM-1003, KBE-1003, KBM-1083, KBM-1403, KBM-502, KBM-503, KBE-502, KBE-503. , KBM-5803, KBM-5103, KBM-602, KBM-603, KBM-903, KBE-903, KBM-573, KBM-6803, KBE-9007, KBM-9659, KBE-9659, KBM-802, KBM -803, KBM-13, KBE-13, KBM-22, KBE-22, KBM-103, KBE-103, KBM-202SS, KBM-3033, KBE-3033, KBM-3063, KBE-3063, KBM-3103C , KBE-3083, X-12-1048, X-12-1050, X-12-1154, X-12-1156, X-12-972F, X-12-1159L, X-40-9296, KR-503 , KR-511, KR-513, KR-518, KR-519, and KPN-3504 (all manufactured by Shin-Etsu Chemical Co., Ltd.).
前記シランカップリング剤の使用量は特に限定されないが、通常、前記表面未修飾シリカ粒子の有機溶媒分散ゾル中のシリカ粒子の表面積1nm2に対して0.1個乃至10個、好ましくは0.5個乃至5個となる量である。なお、“個”とは、シランカップリング剤の分子数を表す。The amount of the silane coupling agent used is not particularly limited, but is usually 0.1 to 10, preferably 0.1 to 10, per 1 nm 2 of surface area of the silica particles in the organic solvent-dispersed sol of the surface-unmodified silica particles. The amount is 5 to 5 pieces. Note that "piece" represents the number of molecules of the silane coupling agent.
これらシランカップリング剤は1種単独で、又は2種以上を組み合わせて使用することができる。使用するシランカップリング剤は特に限定されないが、重合性を有する官能基を分子内に含むシランカップリング剤を用いてシリカ粒子を表面修飾することで、該シリカ粒子を配合した重合性樹脂組成物を硬化させた際に、該シリカ粒子と樹脂マトリクスとの密着性を向上させることができる。具体的には、例えば、エチレン性不飽和基[“CH2=C(CH3)―”又は“CH2=CH―”]を分子内に含むシランカップリング剤を用いてシリカ粒子を表面修飾することで、該シリカ粒子を配合したラジカル重合性樹脂組成物を硬化させた際に、該シリカ粒子と樹脂マトリクスとの密着性を向上させることができる。These silane coupling agents can be used alone or in combination of two or more. The silane coupling agent to be used is not particularly limited, but by surface-modifying the silica particles using a silane coupling agent containing a polymerizable functional group in the molecule, a polymerizable resin composition containing the silica particles. When the silica particles are cured, the adhesion between the silica particles and the resin matrix can be improved. Specifically, for example, silica particles are surface-modified using a silane coupling agent containing an ethylenically unsaturated group ["CH 2 = C (CH 3 )-" or "CH 2 = CH-"] in the molecule. By doing so, when the radically polymerizable resin composition containing the silica particles is cured, the adhesion between the silica particles and the resin matrix can be improved.
本発明で使用する塩基性化合物は特に限定されず、アミン類、第4級アンモニウム類、無機塩基類等の全ての塩基性化合物を使用することができる。 The basic compound used in the present invention is not particularly limited, and all basic compounds such as amines, quaternary ammoniums, and inorganic bases can be used.
前記アミン類としては、例えば、エチルアミン、n―プロピルアミン、イソプロピルアミン、n―ブチルアミン、イソブチルアミン、n―ペンチルアミン、イソぺンチルアミン、シクロペンチルアミン、n―ヘキシルアミン、シクロヘキシルアミン、n―へプチルアミン、n―オクチルアミン、2―エチルへキシルアミン、アニリン、ベンジルアミン、エタノールアミン、プロパノールアミン、ブタノールアミン及びエチレンジアミン等の第1級アミン、ジエチルアミン、ジ―n―プロピルアミン、ジイソプロピルアミン、ジ―n―ブチルアミン、ジイソブチルアミン、ジシクロヘキシルアミン、ジベンジルアミン、ジエタノールアミン及びジブタノールアミン等の第2級アミン、トリエチルアミン、トリ―n―ブチルアミン、トリ―n―ペンチルアミン、トリ―n―オクチルアミン、N―エチルジイソプロピルアミン、N,N―ジメチルブチルアミン、N,N―ジメチルエタノールアミン、N,N―ジエチルエタノールアミン、N,N―ジブチルエタノールアミン、N―メチルジエタノールアミン、N―エチルジエタノールアミン、N―ブチルジエタノールアミン、トリエタノールアミン、トリイソプロパノールアミン及びテトラメチルエチレンジアミン等の第3級アミン、ピロリジン、メチルピロリジン、ピペリジン、メチルピペリジン、ピペラジン、キヌクリジン、1,4―ジアザビシクロ[2.2.2]オクタン、1,5―ジアザビシクロ[4.3.0]―5―ノネン、1,8―ジアザビシクロ[5.4.0]―7―ウンデセン、ピリジン及びイミダゾール等の複素環式アミンが挙げられる。 Examples of the amines include ethylamine, n-propylamine, isopropylamine, n-butylamine, isobutylamine, n-pentylamine, isopentylamine, cyclopentylamine, n-hexylamine, cyclohexylamine, n-heptylamine, Primary amines such as n-octylamine, 2-ethylhexylamine, aniline, benzylamine, ethanolamine, propanolamine, butanolamine and ethylenediamine, diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine , secondary amines such as diisobutylamine, dicyclohexylamine, dibenzylamine, diethanolamine and dibutanolamine, triethylamine, tri-n-butylamine, tri-n-pentylamine, tri-n-octylamine, N-ethyldiisopropylamine , N,N-dimethylbutylamine, N,N-dimethylethanolamine, N,N-diethylethanolamine, N,N-dibutylethanolamine, N-methyldiethanolamine, N-ethyldiethanolamine, N-butyldiethanolamine, triethanolamine , tertiary amines such as triisopropanolamine and tetramethylethylenediamine, pyrrolidine, methylpyrrolidine, piperidine, methylpiperidine, piperazine, quinuclidine, 1,4-diazabicyclo[2.2.2]octane, 1,5-diazabicyclo[4] Examples include heterocyclic amines such as .3.0]-5-nonene, 1,8-diazabicyclo[5.4.0]-7-undecene, pyridine and imidazole.
前記第4級アンモニウム類としては、例えば、水酸化テトラメチルアンモニウム、水酸化テトラエチルアンモニウム及び水酸化テトラブチルアンモニウムが挙げられる。 Examples of the quaternary ammoniums include tetramethylammonium hydroxide, tetraethylammonium hydroxide, and tetrabutylammonium hydroxide.
前記無機塩基類としては、例えば、アンモニア、水酸化ナトリウム及び水酸化カリウムが挙げられる。 Examples of the inorganic bases include ammonia, sodium hydroxide, and potassium hydroxide.
前記塩基性化合物として、(A)表面未修飾シリカ粒子の有機溶媒分散ゾルとシランカップリング剤とを混合する工程で得られた結果物との相溶性の観点から、特に前記式(1)で表されるアルキルアミン類を用いることが好ましい。 As the basic compound, from the viewpoint of compatibility with the resultant product obtained in the step of mixing (A) an organic solvent-dispersed sol of surface-unmodified silica particles and a silane coupling agent, in particular those of the formula (1). It is preferable to use the represented alkylamines.
前記塩基性化合物の添加量は、前記表面未修飾シリカ粒子の有機溶媒分散ゾルの分散性が損なわれない限り特に限定されないが、通常、表面未修飾シリカ粒子成分100質量部に対して0.01質量部乃至5質量部、好ましくは0.05質量部乃至3質量部である。 The amount of the basic compound added is not particularly limited as long as the dispersibility of the organic solvent-dispersed sol of the surface-unmodified silica particles is not impaired, but it is usually 0.01 parts by mass per 100 parts by mass of the surface-unmodified silica particle component. The amount is from 5 parts by weight, preferably from 0.05 parts by weight to 3 parts by weight.
前記塩基性化合物は1種単独で、又は2種以上を組み合わせて使用することができる。該塩基性化合物を(A)工程で得られた結果物に添加する際、その塩基性化合物を水、有機溶媒、或いは有機溶媒/水混合液に溶解させてから用いることが好ましい。なお、ここで用いられる有機溶媒としては、該(A)工程で得られた結果物と相溶する限り特に限定されず、オルガノゾル中に含まれる有機溶媒と同一であっても、異なっていてもよい。 The basic compounds can be used alone or in combination of two or more. When adding the basic compound to the resultant obtained in step (A), it is preferable to dissolve the basic compound in water, an organic solvent, or an organic solvent/water mixture before use. The organic solvent used here is not particularly limited as long as it is compatible with the resultant obtained in step (A), and may be the same or different from the organic solvent contained in the organosol. good.
本発明で使用する陽イオン交換樹脂は特に限定されず、交換基としてスルホン酸基を持つ強酸性の陽イオン交換樹脂及びカルボキシ基を持つ弱酸性の陽イオン交換樹脂、構造としてゲル型の陽イオン交換樹脂及びポーラス型の陽イオン交換樹脂等、各種公知の陽イオン交換樹脂を使用することができる。 The cation exchange resin used in the present invention is not particularly limited, and includes strongly acidic cation exchange resins having a sulfonic acid group as an exchange group, weakly acidic cation exchange resins having a carboxyl group, and gel-type cation exchange resins as an exchange group. Various known cation exchange resins such as exchange resins and porous cation exchange resins can be used.
該陽イオン交換樹脂として市販品を用いることができ、具体的には、IR120B、IR124、200CT、252、FPC3500、IRC76等のアンバーライト(登録商標)シリーズ、1020、1024、1060、1220等のアンバージェット(登録商標)シリーズ、15DRY、15JWET、16WET、33、35WET等のアンバーリスト(登録商標)シリーズ(以上、オルガノ(株)製)、SK104、SK1B、SK110、SK112、PK208、PK212L、PK216、PK218、PK220、PK228、UBK08、UBK10、UBK12、WK10、WK11、WK100及びWK40L等のダイヤイオン(登録商標)シリーズ(以上、三菱ケミカル(株)製)等が挙げられる。 Commercial products can be used as the cation exchange resin, and specifically, Amberlite (registered trademark) series such as IR120B, IR124, 200CT, 252, FPC3500, IRC76, etc., Amberite (registered trademark) series such as 1020, 1024, 1060, 1220, etc. Jet (registered trademark) series, Amberlyst (registered trademark) series such as 15DRY, 15JWET, 16WET, 33, 35WET (manufactured by Organo Co., Ltd.), SK104, SK1B, SK110, SK112, PK208, PK212L, PK216, PK218 , PK220, PK228, UBK08, UBK10, UBK12, WK10, WK11, WK100, and WK40L, and the Diamondion (registered trademark) series (manufactured by Mitsubishi Chemical Corporation).
これら市販品の陽イオン交換樹脂はそのまま用いてもよいし、交換基を金属イオン型から水素イオン型へ再生するような公知の処理を適宜実施してから用いてもよい。 These commercially available cation exchange resins may be used as they are, or may be used after appropriately performing a known treatment to regenerate the exchange group from the metal ion type to the hydrogen ion type.
続いて、本発明における各工程の詳細を説明する。 Next, details of each step in the present invention will be explained.
<(A)工程>
(A)工程は、シランカップリング剤のアルコキシシリル基(加水分解性基)を、加水分解によってシラノール基へと変換することを目的とする工程である。前述のように、シランカップリング剤の加水分解反応は酸性条件で促進される。前記表面未修飾シリカ粒子の有機溶媒分散ゾルは通常シラノール基の存在により酸性条件となっているため、該表面未修飾シリカ粒子の有機溶媒分散ゾルとシランカップリング剤とを混合し、撹拌することで該加水分解反応を行うことができる。なお、反応促進の目的で適宜酸性化合物を添加してもよい。用いる表面未修飾シリカ粒子の有機溶媒分散ゾルは、シリカ粒子の凝集物等、大粒径の不純物を除去するため、メッシュフィルター等でろ過してから使用してもよい。前記表面未修飾シリカ粒子の有機溶媒分散ゾルとシランカップリング剤とを混合した後に撹拌する方法としては特に限定されないが、通常、前記有機溶媒分散ゾルの有機溶媒の融点乃至沸点の範囲すなわち液体である温度下、30分間乃至24時間、好ましくは1時間乃至10時間行う。この時、前記有機溶媒の沸点を超えない範囲で可能な限り高温下で撹拌することで、加水分解反応を促進することができる。<(A) Process>
Step (A) is a step whose purpose is to convert the alkoxysilyl group (hydrolyzable group) of the silane coupling agent into a silanol group by hydrolysis. As mentioned above, the hydrolysis reaction of the silane coupling agent is promoted under acidic conditions. Since the organic solvent-dispersed sol of the surface-unmodified silica particles is usually under acidic conditions due to the presence of silanol groups, the organic-solvent-dispersed sol of the surface-unmodified silica particles and the silane coupling agent are mixed and stirred. The hydrolysis reaction can be carried out with. Note that an acidic compound may be added as appropriate for the purpose of promoting the reaction. The organic solvent-dispersed sol of surface-unmodified silica particles used may be used after being filtered with a mesh filter or the like in order to remove large particle size impurities such as aggregates of silica particles. The method of stirring after mixing the organic solvent-dispersed sol of the surface-unmodified silica particles and the silane coupling agent is not particularly limited, but usually, it is within the melting point to boiling point range of the organic solvent of the organic solvent-dispersed sol, that is, the liquid. The treatment is carried out at a certain temperature for 30 minutes to 24 hours, preferably for 1 hour to 10 hours. At this time, the hydrolysis reaction can be promoted by stirring at as high a temperature as possible within a range that does not exceed the boiling point of the organic solvent.
<(B)工程>
(B)工程は、(A)工程で得られた結果物、すなわち加水分解されたシランカップリング剤を含む酸性の表面未修飾シリカ粒子の有機溶媒分散ゾルを、塩基性下に置くことで、シリカ粒子表面のシラノール基と、加水分解されたシランカップリング剤のシラノール基とを縮合させることを目的とする工程である。前述のように、シラノール基同士の縮合反応は塩基性条件で促進されるため、(A)工程で得られた結果物に対して塩基性化合物を添加することで、シランカップリング剤によるシリカ粒子の表面修飾率を向上させることができる。塩基性化合物を添加する際は、該塩基性化合物を水、有機溶媒又は有機溶媒/水混合液に溶解させてから添加することが好ましい。塩基性化合物を添加後に撹拌する方法としては特に限定されないが、通常、前記有機溶媒分散ゾルの有機溶媒の融点乃至沸点の範囲の温度下、1分間乃至24時間、好ましくは10分間乃至10時間行う。この時、前記有機溶媒の沸点を超えない範囲で可能な限り高温下で撹拌することで、縮合反応を促進することができる。<(B) Process>
Step (B) is to place the resultant obtained in step (A), that is, an organic solvent dispersion sol of acidic surface-unmodified silica particles containing a hydrolyzed silane coupling agent, under basic conditions. This step aims to condense the silanol groups on the surface of the silica particles and the silanol groups of the hydrolyzed silane coupling agent. As mentioned above, the condensation reaction between silanol groups is promoted under basic conditions, so by adding a basic compound to the resultant obtained in step (A), silica particles can be formed by the silane coupling agent. The surface modification rate can be improved. When adding a basic compound, it is preferable to dissolve the basic compound in water, an organic solvent, or an organic solvent/water mixture before adding it. The method of stirring after adding the basic compound is not particularly limited, but it is usually carried out at a temperature within the melting point to boiling point of the organic solvent of the organic solvent-dispersed sol for 1 minute to 24 hours, preferably 10 minutes to 10 hours. . At this time, the condensation reaction can be promoted by stirring at the highest possible temperature within a range that does not exceed the boiling point of the organic solvent.
<(C)工程>
(C)工程は、(B)工程で得られた結果物、すなわち塩基性の表面修飾シリカ粒子の有機溶媒分散ゾルを、陽イオン交換樹脂に接触させることで、(B)工程で添加された塩基性化合物の一部又は全部を除去し、酸性又は中性の表面修飾シリカ粒子の有機溶媒分散ゾルを得ることを目的とする工程である。前記塩基性化合物としてアミン類を用いる場合、該アミン類がプロトン化された陽イオンであるアンモニウムカチオンが前記陽イオン交換樹脂に吸着する。その結果、前記アミン類は除去された状態となる。(B)工程で得られた結果物を陽イオン交換樹脂に接触させる方法としては特に限定されないが、例えば、前記表面未修飾シリカ粒子の有機溶媒分散ゾル中の表面未修飾シリカ粒子成分100質量部に対して1質量部乃至200質量部、好ましくは10質量部乃至100質量部の陽イオン交換樹脂を該結果物に添加し、前記有機溶媒分散ゾルの有機溶媒の融点乃至沸点の範囲の温度下、1分間乃至24時間、好ましくは5分間乃至5時間撹拌する方法や、陽イオン交換樹脂が充填されたカラムに該結果物を通液する方法が挙げられる。<(C) Process>
In the step (C), the resultant obtained in the step (B), that is, the organic solvent-dispersed sol of basic surface-modified silica particles, is brought into contact with a cation exchange resin, thereby removing the sol added in the step (B). This step aims to remove part or all of the basic compound and obtain an organic solvent-dispersed sol of acidic or neutral surface-modified silica particles. When amines are used as the basic compound, ammonium cations, which are protonated cations of the amines, are adsorbed on the cation exchange resin. As a result, the amines are removed. The method of bringing the resultant obtained in step (B) into contact with the cation exchange resin is not particularly limited, but for example, 100 parts by mass of the surface-unmodified silica particles in the organic solvent-dispersed sol of the surface-unmodified silica particles. 1 to 200 parts by mass, preferably 10 to 100 parts by mass, of a cation exchange resin is added to the resulting product, and the mixture is heated at a temperature within the range of the melting point to boiling point of the organic solvent of the organic solvent-dispersed sol. , a method of stirring for 1 minute to 24 hours, preferably 5 minutes to 5 hours, and a method of passing the resulting product through a column packed with a cation exchange resin.
(B)工程で得られた結果物を陽イオン交換樹脂に接触させる方法として、該(B)工程で得られた結果物に該陽イオン交換樹脂を添加し、撹拌する方法を採用する場合、撹拌後、該陽イオン交換樹脂をろ過により除去することが望ましい。 (B) When adopting a method of bringing the resultant obtained in step (B) into contact with a cation exchange resin, adding the cation exchange resin to the resultant obtained in step (B) and stirring; After stirring, it is desirable to remove the cation exchange resin by filtration.
(C)工程で得られる表面修飾シリカ粒子の有機溶媒分散ゾルのpHは1乃至7、好ましくは2乃至6である。(C)工程では、表面修飾シリカ粒子の有機溶媒分散ゾルのpHが1乃至7となるように、好ましくは2乃至6となるように、(B)工程で得られた結果物を陽イオン交換樹脂に接触させる。 The pH of the organic solvent-dispersed sol of surface-modified silica particles obtained in step (C) is 1 to 7, preferably 2 to 6. In step (C), the resultant obtained in step (B) is cation-exchanged so that the pH of the organic solvent-dispersed sol of surface-modified silica particles is 1 to 7, preferably 2 to 6. Contact with resin.
以下、実施例を挙げて、本発明をより具体的に説明するが、本発明は下記の実施例に限定されるものではない。なお、下記実施例及び比較例において、試料の物性の分析に用いた装置は、以下の通りである。 EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples, but the present invention is not limited to the following Examples. In addition, in the following Examples and Comparative Examples, the following devices were used to analyze the physical properties of the samples.
(1)pH測定
装置:(株)堀場アドバンステクノ製 ポータブル型pHメータ D―72
(2)粘度測定
装置:柴田化学(株)製 オストワルド粘度計(1) pH measuring device: Portable pH meter D-72 manufactured by Horiba Advance Techno Co., Ltd.
(2) Viscosity measuring device: Ostwald viscometer manufactured by Shibata Chemical Co., Ltd.
下記実施例及び比較例において使用した材料の供給元は以下の通りである。
MA―ST―M:日産化学(株)製 商品名:MA―ST―M
メタノールシリカゾル:日産化学(株)製 商品名:メタノールシリカゾル
PGM―ST:日産化学(株)製 商品名:PGM―ST
MEK―ST―40:日産化学(株)製 商品名:MEK―ST―40
KBM―5803:信越化学工業(株)製 商品名:KBM―5803
KBM―5103:信越化学工業(株)製 商品名:KBM―5103
TEA:東京化成工業(株)製 商品名:トリエチルアミン
TPA:東京化成工業(株)製 商品名:トリペンチルアミン
DiPEA:東京化成工業(株)製 商品名:N,N―ジイソプロピルエチルアミン
PA:東京化成工業(株)製 商品名:プロピルアミン
TOcA:シグマアルドリッチジャパン(同)製 商品名:トリオクチルアミン
15JWET:オルガノ(株)製 商品名:アンバーリスト(登録商標)15JWETThe suppliers of materials used in the following Examples and Comparative Examples are as follows.
MA-ST-M: Manufactured by Nissan Chemical Co., Ltd. Product name: MA-ST-M
Methanol silica sol: manufactured by Nissan Chemical Co., Ltd. Product name: Methanol silica sol PGM-ST: manufactured by Nissan Chemical Co., Ltd. Product name: PGM-ST
MEK-ST-40: Manufactured by Nissan Chemical Co., Ltd. Product name: MEK-ST-40
KBM-5803: Manufactured by Shin-Etsu Chemical Co., Ltd. Product name: KBM-5803
KBM-5103: Manufactured by Shin-Etsu Chemical Co., Ltd. Product name: KBM-5103
TEA: Manufactured by Tokyo Kasei Kogyo Co., Ltd. Product name: Triethylamine TPA: Manufactured by Tokyo Kasei Kogyo Co., Ltd. Product name: Tripentylamine DiPEA: Manufactured by Tokyo Kasei Kogyo Co., Ltd. Product name: N,N-Diisopropylethylamine PA: Tokyo Kasei Manufactured by Kogyo Co., Ltd. Product name: Propylamine TOcA: Manufactured by Sigma-Aldrich Japan (same) Product name: Trioctylamine 15JWET: Manufactured by Organo Co., Ltd. Product name: Amberlyst (registered trademark) 15JWET
<実施例1>
200mLナスフラスコに、表面未修飾シリカゾル有機溶媒分散体としてMA―ST―M(メタノール分散シリカゾル、一次粒子径22nm、シリカ粒子濃度40質量%、水分2質量%)を100g、及びシランカップリング剤としてKBM―5803を9.5g(シリカ粒子の表面積1nm2に対して約4個となる量)秤量し、室温下で撹拌して溶解させた。該ナスフラスコを65℃のオイルバスに浸漬させ、反応液を5時間加熱撹拌した。続いて、10mLガラスバイアル瓶に、塩基性化合物としてTEAを0.06g、及び2―ブタノン(以下、本明細書ではMEKと略称する。)を3.0g秤量し、撹拌して溶解させた。該TEAのMEK溶液を、前記反応液に滴下して溶解させた後、65℃にて1時間加熱撹拌した。次に、該反応液に、陽イオン交換樹脂として15JWETを20g添加し、室温下で3時間撹拌した後、メッシュフィルターでろ過して15JWETを取り除くことで、表面修飾されたシリカ粒子のメタノール分散ゾルを得た。<Example 1>
In a 200 mL eggplant flask, 100 g of MA-ST-M (methanol-dispersed silica sol, primary particle diameter 22 nm, silica particle concentration 40% by mass, water 2% by mass) as a surface-unmodified silica sol organic solvent dispersion, and as a silane coupling agent. 9.5 g of KBM-5803 (approximately 4 particles per 1 nm 2 of surface area of silica particles) was weighed out and dissolved by stirring at room temperature. The eggplant flask was immersed in a 65° C. oil bath, and the reaction solution was heated and stirred for 5 hours. Subsequently, 0.06 g of TEA as basic compounds and 3.0 g of 2-butanone (hereinafter abbreviated as MEK) were weighed into a 10 mL glass vial, and the mixture was stirred and dissolved. The MEK solution of TEA was added dropwise to the reaction solution to dissolve it, and then heated and stirred at 65° C. for 1 hour. Next, 20g of 15JWET as a cation exchange resin was added to the reaction solution, stirred at room temperature for 3 hours, and filtered through a mesh filter to remove 15JWET, resulting in a methanol-dispersed sol of surface-modified silica particles. I got it.
<実施例2>
塩基性化合物としてTOcAを0.18g使用する以外は実施例1と同様の手順にて、表面修飾されたシリカ粒子のメタノール分散ゾルを得た。<Example 2>
A methanol-dispersed sol of surface-modified silica particles was obtained in the same manner as in Example 1 except that 0.18 g of TOcA was used as the basic compound.
<実施例3>
塩基性化合物としてDiPEAを0.07g使用する以外は実施例1と同様の手順にて、表面修飾されたシリカ粒子のメタノール分散ゾルを得た。<Example 3>
A methanol-dispersed sol of surface-modified silica particles was obtained in the same manner as in Example 1 except that 0.07 g of DiPEA was used as the basic compound.
<実施例4>
塩基性化合物としてPAを0.03g使用する以外は実施例1と同様の手順にて、表面修飾されたシリカ粒子のメタノール分散ゾルを得た。<Example 4>
A methanol-dispersed sol of surface-modified silica particles was obtained in the same manner as in Example 1 except that 0.03 g of PA was used as the basic compound.
<実施例5>
塩基性化合物としてTPAを0.80g使用する以外は実施例1と同様の手順にて、表面修飾されたシリカ粒子のメタノール分散ゾルを得た。<Example 5>
A methanol-dispersed sol of surface-modified silica particles was obtained in the same manner as in Example 1 except that 0.80 g of TPA was used as the basic compound.
<実施例6>
シランカップリング剤としてKBM―5803を4.8g(シリカ粒子の表面積1nm2に対して約2個となる量)を使用し、塩基性化合物としてTPAを0.31g使用する以外は実施例1と同様の手順にて、表面修飾されたシリカ粒子のメタノール分散ゾルを得た。<Example 6>
Same as Example 1 except that 4.8 g of KBM-5803 (approximately 2 particles per 1 nm 2 surface area of silica particles) was used as the silane coupling agent and 0.31 g of TPA was used as the basic compound. A methanol-dispersed sol of surface-modified silica particles was obtained using the same procedure.
<実施例7>
表面未修飾シリカゾル有機溶媒分散体としてメタノールシリカゾル(メタノール分散シリカゾル、一次粒子径12nm、シリカ粒子濃度30質量%)を100g使用し、シランカップリング剤としてKBM―5803を13.0g(シリカ粒子の表面積1nm2に対して約4個となる量)を使用し、塩基性化合物としてTPAを0.23g使用する以外は実施例1と同様の手順にて、表面修飾されたシリカ粒子のメタノール分散ゾルを得た。<Example 7>
100 g of methanol silica sol (methanol-dispersed silica sol, primary particle diameter 12 nm, silica particle concentration 30% by mass) was used as a surface-unmodified silica sol organic solvent dispersion, and 13.0 g of KBM-5803 was used as a silane coupling agent (surface area of silica particles). A methanol-dispersed sol of surface-modified silica particles was prepared in the same manner as in Example 1 , except that 0.23 g of TPA was used as the basic compound. Obtained.
<実施例8>
表面未修飾シリカゾル有機溶媒分散体としてPGM―ST[プロピレングリコールモノメチルエーテル(以下、本明細書ではPGMEと略称する。)分散シリカゾル、一次粒子径12nm、シリカ粒子濃度30質量%]を100g使用し、シランカップリング剤としてKBM―5803を13.0g(シリカ粒子の表面積1nm2に対して約4個となる量)を使用し、塩基性化合物としてTPAを0.23g使用する以外は実施例1と同様の手順にて、表面修飾されたシリカ粒子のPGME分散ゾルを得た。<Example 8>
100 g of PGM-ST [propylene glycol monomethyl ether (hereinafter abbreviated as PGME) dispersed silica sol, primary particle diameter 12 nm, silica particle concentration 30% by mass] was used as a surface-unmodified silica sol organic solvent dispersion, Same as Example 1 except that 13.0 g of KBM-5803 (approximately 4 particles per 1 nm 2 surface area of silica particles) was used as the silane coupling agent and 0.23 g of TPA was used as the basic compound. A PGME dispersion sol of surface-modified silica particles was obtained in the same manner.
<実施例9>
表面未修飾シリカゾル有機溶媒分散体としてMEK―ST―40(MEK分散シリカゾル、一次粒子径12nm、シリカ粒子濃度40質量%)100gに純水1gを添加したものを使用し、シランカップリング剤としてKBM―5103を6.5g(シリカ粒子の表面積1nm2に対して約2個となる量)を使用し、塩基性化合物としてTPAを0.31g使用する以外は実施例1と同様の手順にて、表面修飾されたシリカ粒子のMEK分散ゾルを得た。<Example 9>
As a surface-unmodified silica sol organic solvent dispersion, 1 g of pure water was added to 100 g of MEK-ST-40 (MEK-dispersed silica sol, primary particle diameter 12 nm, silica particle concentration 40% by mass), and KBM was used as a silane coupling agent. -5103 was used in the same manner as in Example 1, except that 6.5 g (approximately 2 particles per 1 nm 2 of surface area of silica particles) and 0.31 g of TPA were used as the basic compound. A MEK dispersion sol of surface-modified silica particles was obtained.
<比較例1>
15JWETを添加しない以外は実施例1と同様の手順にて、表面修飾されたシリカ粒子のメタノール分散ゾルを得た。<Comparative example 1>
A methanol-dispersed sol of surface-modified silica particles was obtained in the same manner as in Example 1 except that 15JWET was not added.
[pH測定]
ガラスバイアル瓶に、前記実施例1乃至実施例9及び比較例1で得られた表面修飾シリカ粒子の有機溶媒分散ゾル、メタノール及び純水をそれぞれ同質量ずつ混合し、撹拌することで試料液を調製した。該試料液に対し、前記pHメータを用いて、液温23℃にてpHを測定した。測定結果を下記表1に示す。[pH measurement]
In a glass vial, the same mass of the organic solvent dispersion sol of the surface-modified silica particles obtained in Examples 1 to 9 and Comparative Example 1, methanol, and pure water were mixed, and the sample solution was mixed by stirring. Prepared. The pH of the sample solution was measured using the pH meter at a solution temperature of 23°C. The measurement results are shown in Table 1 below.
[粘度測定]
前記オストワルド粘度計に純水10mLを充填し、25℃にて毛管を通過するのに要した時間(流下時間)を計測した。同様の手順で、前記実施例1乃至実施例9及び比較例1で得られた表面修飾シリカ粒子の有機溶媒分散ゾルについて、作製直後及び該ゾルを50℃恒温槽にて20日間保管した後の流下時間をそれぞれ計測した。下記式より、それぞれのゾルの粘度を算出した。
(ゾル粘度)=
{(ゾル流下時間)×(ゾル密度)}/{(純水流下時間)×(純水密度)}×(純水粘度)
なお、25℃における純水粘度を0.89cPとした。算出結果を下記表1に示す。[Viscosity measurement]
The Ostwald viscometer was filled with 10 mL of pure water, and the time required for the water to pass through the capillary (flow time) at 25° C. was measured. Using the same procedure, the organic solvent-dispersed sols of surface-modified silica particles obtained in Examples 1 to 9 and Comparative Example 1 were prepared immediately after preparation and after the sol was stored in a thermostat at 50°C for 20 days. The flow time was measured for each. The viscosity of each sol was calculated from the following formula.
(Sol viscosity) =
{(Sol flow time) x (Sol density)} / {(Pure water flow time) x (Pure water density)} x (Pure water viscosity)
Note that the viscosity of pure water at 25° C. was 0.89 cP. The calculation results are shown in Table 1 below.
[透明性評価]
直径3cmの円筒型30mLガラスバイアル瓶に、前記実施例1乃至実施例9及び比較例1で得られた表面修飾シリカ粒子の有機溶媒分散ゾルを充填し、該ガラスバイアル瓶を介して向こう側の文字を視認できる場合を○、視認できない場合を×とした。また、前記ガラスバイアル瓶を50℃の恒温槽にて20日間保管した後、同様に評価した。評価結果を下記表1に記す。[Transparency evaluation]
A cylindrical 30 mL glass vial with a diameter of 3 cm is filled with the organic solvent-dispersed sol of the surface-modified silica particles obtained in Examples 1 to 9 and Comparative Example 1, and the sol of the surface-modified silica particles dispersed in an organic solvent is passed through the glass vial. The case where the characters were visible was rated as ○, and the case where the letters were not visible was rated as ×. Further, the glass vial was stored in a constant temperature bath at 50° C. for 20 days, and then evaluated in the same manner. The evaluation results are shown in Table 1 below.
実施例1乃至実施例9から得られた表面修飾シリカ粒子の有機溶媒分散ゾルは、50℃にて20日間保管しても透明性を維持し、粘度上昇も見られなかった。一方、比較例1から得られた表面修飾シリカ粒子の有機溶媒分散ゾルは、50℃にて20日間保管したところ白色不透明となり、粘度上昇が見られた。したがって、本発明の製造方法によれば、保存安定性の良好な表面修飾シリカ粒子の有機溶媒分散ゾルを得られることが示された。
The organic solvent-dispersed sols of surface-modified silica particles obtained from Examples 1 to 9 maintained transparency even when stored at 50° C. for 20 days, and no increase in viscosity was observed. On the other hand, when the organic solvent-dispersed sol of surface-modified silica particles obtained from Comparative Example 1 was stored at 50° C. for 20 days, it became white and opaque, and an increase in viscosity was observed. Therefore, it was shown that according to the production method of the present invention, a sol of surface-modified silica particles dispersed in an organic solvent with good storage stability can be obtained.
Claims (9)
(A)表面未修飾シリカ粒子の有機溶媒分散ゾルとシランカップリング剤とを混合する工程
(B)(A)工程で得られた結果物に対し、塩基性化合物を添加する工程
(C)(B)工程で得られた結果物に対し、陽イオン交換樹脂を接触させる工程A method for producing an organic solvent-dispersed sol of surface-modified silica particles, including the following steps (A) to (C).
(A) Step of mixing an organic solvent-dispersed sol of surface-unmodified silica particles and a silane coupling agent (B) Step of adding a basic compound to the resultant obtained in step (A) (C) ( B) A step of contacting the resultant obtained in step with a cation exchange resin
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