WO2007119517A1 - 金属酸化物微粒子含有ポリシロキサン組成物およびその製造方法 - Google Patents
金属酸化物微粒子含有ポリシロキサン組成物およびその製造方法 Download PDFInfo
- Publication number
- WO2007119517A1 WO2007119517A1 PCT/JP2007/056287 JP2007056287W WO2007119517A1 WO 2007119517 A1 WO2007119517 A1 WO 2007119517A1 JP 2007056287 W JP2007056287 W JP 2007056287W WO 2007119517 A1 WO2007119517 A1 WO 2007119517A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- metal oxide
- polysiloxane
- oxide fine
- weight
- fine particles
- Prior art date
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- -1 polysiloxane Polymers 0.000 title claims abstract description 299
- 229920001296 polysiloxane Polymers 0.000 title claims abstract description 212
- 229910044991 metal oxide Inorganic materials 0.000 title claims abstract description 114
- 150000004706 metal oxides Chemical class 0.000 title claims abstract description 114
- 239000000203 mixture Substances 0.000 title claims abstract description 96
- 239000002245 particle Substances 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims description 14
- 239000004205 dimethyl polysiloxane Substances 0.000 claims abstract description 51
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims abstract description 51
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- 238000006243 chemical reaction Methods 0.000 claims abstract description 41
- 239000003960 organic solvent Substances 0.000 claims abstract description 40
- 229910052751 metal Inorganic materials 0.000 claims abstract description 34
- 239000002184 metal Substances 0.000 claims abstract description 34
- 150000007514 bases Chemical class 0.000 claims abstract description 32
- 239000013522 chelant Substances 0.000 claims abstract description 28
- 150000007513 acids Chemical class 0.000 claims abstract description 27
- 125000005702 oxyalkylene group Chemical group 0.000 claims abstract description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
- 238000002156 mixing Methods 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 9
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 5
- 239000010419 fine particle Substances 0.000 claims description 133
- 238000006460 hydrolysis reaction Methods 0.000 claims description 31
- 230000007062 hydrolysis Effects 0.000 claims description 30
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical compound [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 claims description 18
- 239000003054 catalyst Substances 0.000 claims description 17
- 238000009833 condensation Methods 0.000 claims description 16
- 230000005494 condensation Effects 0.000 claims description 15
- 239000004793 Polystyrene Substances 0.000 claims description 14
- 238000004587 chromatography analysis Methods 0.000 claims description 14
- 238000005227 gel permeation chromatography Methods 0.000 claims description 14
- 229920002223 polystyrene Polymers 0.000 claims description 14
- 239000011324 bead Substances 0.000 claims description 11
- 239000003566 sealing material Substances 0.000 claims description 5
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 3
- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 abstract description 9
- 239000000047 product Substances 0.000 description 33
- 239000007787 solid Substances 0.000 description 23
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- 239000000243 solution Substances 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000002253 acid Substances 0.000 description 17
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 17
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 150000002430 hydrocarbons Chemical group 0.000 description 16
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 239000006185 dispersion Substances 0.000 description 14
- 238000006482 condensation reaction Methods 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 12
- 230000014759 maintenance of location Effects 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 230000000052 comparative effect Effects 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 10
- 230000006750 UV protection Effects 0.000 description 10
- 238000002834 transmittance Methods 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- 239000011230 binding agent Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 8
- 230000015556 catabolic process Effects 0.000 description 8
- 238000006731 degradation reaction Methods 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000004062 sedimentation Methods 0.000 description 7
- 229910000077 silane Inorganic materials 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- 229910052719 titanium Inorganic materials 0.000 description 7
- 239000010936 titanium Substances 0.000 description 7
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 6
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
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- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 5
- 229940087646 methanolamine Drugs 0.000 description 5
- 125000000962 organic group Chemical group 0.000 description 5
- 150000002902 organometallic compounds Chemical class 0.000 description 5
- 239000003973 paint Substances 0.000 description 5
- 229910052726 zirconium Inorganic materials 0.000 description 5
- BLFRQYKZFKYQLO-UHFFFAOYSA-N 4-aminobutan-1-ol Chemical compound NCCCCO BLFRQYKZFKYQLO-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- 239000005046 Chlorosilane Substances 0.000 description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical compound Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000006386 neutralization reaction Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000001629 suppression Effects 0.000 description 4
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- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- MQPPCKJJFDNPHJ-UHFFFAOYSA-K aluminum;3-oxohexanoate Chemical compound [Al+3].CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O.CCCC(=O)CC([O-])=O MQPPCKJJFDNPHJ-UHFFFAOYSA-K 0.000 description 3
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- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 3
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- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 3
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- 238000000034 method Methods 0.000 description 3
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 229910001887 tin oxide Inorganic materials 0.000 description 3
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 3
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- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
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- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 2
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- GQNWJCQWBFHQAO-UHFFFAOYSA-N dibutoxy(dimethyl)silane Chemical compound CCCCO[Si](C)(C)OCCCC GQNWJCQWBFHQAO-UHFFFAOYSA-N 0.000 description 1
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- AHUXYBVKTIBBJW-UHFFFAOYSA-N dimethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)C1=CC=CC=C1 AHUXYBVKTIBBJW-UHFFFAOYSA-N 0.000 description 1
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- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- ZIDTUTFKRRXWTK-UHFFFAOYSA-N dimethyl(dipropoxy)silane Chemical compound CCCO[Si](C)(C)OCCC ZIDTUTFKRRXWTK-UHFFFAOYSA-N 0.000 description 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 description 1
- 239000002612 dispersion medium Substances 0.000 description 1
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- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
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- 239000003480 eluent Substances 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- DFJDZTPFNSXNAX-UHFFFAOYSA-N ethoxy(triethyl)silane Chemical compound CCO[Si](CC)(CC)CC DFJDZTPFNSXNAX-UHFFFAOYSA-N 0.000 description 1
- RSIHJDGMBDPTIM-UHFFFAOYSA-N ethoxy(trimethyl)silane Chemical compound CCO[Si](C)(C)C RSIHJDGMBDPTIM-UHFFFAOYSA-N 0.000 description 1
- QSCNLGHKALSYKF-UHFFFAOYSA-N ethoxymethanamine Chemical compound CCOCN QSCNLGHKALSYKF-UHFFFAOYSA-N 0.000 description 1
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- 238000001879 gelation Methods 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
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- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 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 1
- VRINOTYEGADLMW-UHFFFAOYSA-N heptyl(trimethoxy)silane Chemical compound CCCCCCC[Si](OC)(OC)OC VRINOTYEGADLMW-UHFFFAOYSA-N 0.000 description 1
- HTDJPCNNEPUOOQ-UHFFFAOYSA-N hexamethylcyclotrisiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O1 HTDJPCNNEPUOOQ-UHFFFAOYSA-N 0.000 description 1
- 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 1
- JYTUFVYWTIKZGR-UHFFFAOYSA-N holmium oxide Inorganic materials [O][Ho]O[Ho][O] JYTUFVYWTIKZGR-UHFFFAOYSA-N 0.000 description 1
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- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
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- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
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- 229910003443 lutetium oxide Inorganic materials 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
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- 239000002609 medium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
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- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- RYPNVAIMJHBIQS-UHFFFAOYSA-N n'-butylbutane-1,4-diamine Chemical compound CCCCNCCCCN RYPNVAIMJHBIQS-UHFFFAOYSA-N 0.000 description 1
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- SCZVXVGZMZRGRU-UHFFFAOYSA-N n'-ethylethane-1,2-diamine Chemical compound CCNCCN SCZVXVGZMZRGRU-UHFFFAOYSA-N 0.000 description 1
- JJRGWIVWXMEKCL-UHFFFAOYSA-N n'-ethylmethanediamine Chemical compound CCNCN JJRGWIVWXMEKCL-UHFFFAOYSA-N 0.000 description 1
- ODGYWRBCQWKSSH-UHFFFAOYSA-N n'-ethylpropane-1,3-diamine Chemical compound CCNCCCN ODGYWRBCQWKSSH-UHFFFAOYSA-N 0.000 description 1
- KFIGICHILYTCJF-UHFFFAOYSA-N n'-methylethane-1,2-diamine Chemical compound CNCCN KFIGICHILYTCJF-UHFFFAOYSA-N 0.000 description 1
- QHJABUZHRJTCAR-UHFFFAOYSA-N n'-methylpropane-1,3-diamine Chemical compound CNCCCN QHJABUZHRJTCAR-UHFFFAOYSA-N 0.000 description 1
- GHQFRBNLAGNQOE-UHFFFAOYSA-N n'-propylbutane-1,4-diamine Chemical compound CCCNCCCCN GHQFRBNLAGNQOE-UHFFFAOYSA-N 0.000 description 1
- NTHFGDLJWMNYJT-UHFFFAOYSA-N n'-propylmethanediamine Chemical compound CCCNCN NTHFGDLJWMNYJT-UHFFFAOYSA-N 0.000 description 1
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- DNJDQMRARVPSHZ-UHFFFAOYSA-N n,n,n',n'-tetrabutylethane-1,2-diamine Chemical compound CCCCN(CCCC)CCN(CCCC)CCCC DNJDQMRARVPSHZ-UHFFFAOYSA-N 0.000 description 1
- DIHKMUNUGQVFES-UHFFFAOYSA-N n,n,n',n'-tetraethylethane-1,2-diamine Chemical compound CCN(CC)CCN(CC)CC DIHKMUNUGQVFES-UHFFFAOYSA-N 0.000 description 1
- HVBXZPOGJMBMLN-UHFFFAOYSA-N n,n,n',n'-tetrapropylethane-1,2-diamine Chemical compound CCCN(CCC)CCN(CCC)CCC HVBXZPOGJMBMLN-UHFFFAOYSA-N 0.000 description 1
- KRKPYFLIYNGWTE-UHFFFAOYSA-N n,o-dimethylhydroxylamine Chemical compound CNOC KRKPYFLIYNGWTE-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- QEFYFXOXNSNQGX-UHFFFAOYSA-N neodymium atom Chemical compound [Nd] QEFYFXOXNSNQGX-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910000484 niobium oxide Inorganic materials 0.000 description 1
- URLJKFSTXLNXLG-UHFFFAOYSA-N niobium(5+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[Nb+5].[Nb+5] URLJKFSTXLNXLG-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- MPARYNQUYZOBJM-UHFFFAOYSA-N oxo(oxolutetiooxy)lutetium Chemical compound O=[Lu]O[Lu]=O MPARYNQUYZOBJM-UHFFFAOYSA-N 0.000 description 1
- VTRUBDSFZJNXHI-UHFFFAOYSA-N oxoantimony Chemical compound [Sb]=O VTRUBDSFZJNXHI-UHFFFAOYSA-N 0.000 description 1
- UZLYXNNZYFBAQO-UHFFFAOYSA-N oxygen(2-);ytterbium(3+) Chemical compound [O-2].[O-2].[O-2].[Yb+3].[Yb+3] UZLYXNNZYFBAQO-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 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
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011164 primary particle Substances 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
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000005767 propoxymethyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])[#8]C([H])([H])* 0.000 description 1
- ILVGAIQLOCKNQA-UHFFFAOYSA-N propyl 2-hydroxypropanoate Chemical compound CCCOC(=O)C(C)O ILVGAIQLOCKNQA-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 229940032159 propylene carbonate Drugs 0.000 description 1
- RDRCCJPEJDWSRJ-UHFFFAOYSA-N pyridine;1h-pyrrole Chemical compound C=1C=CNC=1.C1=CC=NC=C1 RDRCCJPEJDWSRJ-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 229910001954 samarium oxide Inorganic materials 0.000 description 1
- 229940075630 samarium oxide Drugs 0.000 description 1
- FKTOIHSPIPYAPE-UHFFFAOYSA-N samarium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Sm+3].[Sm+3] FKTOIHSPIPYAPE-UHFFFAOYSA-N 0.000 description 1
- 229910052706 scandium Inorganic materials 0.000 description 1
- SIXSYDAISGFNSX-UHFFFAOYSA-N scandium atom Chemical compound [Sc] SIXSYDAISGFNSX-UHFFFAOYSA-N 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011163 secondary particle Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- VSSLEOGOUUKTNN-UHFFFAOYSA-N tantalum titanium Chemical compound [Ti].[Ta] VSSLEOGOUUKTNN-UHFFFAOYSA-N 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229910003451 terbium oxide Inorganic materials 0.000 description 1
- SCRZPWWVSXWCMC-UHFFFAOYSA-N terbium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[Tb+3].[Tb+3] SCRZPWWVSXWCMC-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 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
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000003698 tetramethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- ZQZCOBSUOFHDEE-UHFFFAOYSA-N tetrapropyl silicate Chemical compound CCCO[Si](OCCC)(OCCC)OCCC ZQZCOBSUOFHDEE-UHFFFAOYSA-N 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-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
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- UDUKMRHNZZLJRB-UHFFFAOYSA-N triethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OCC)(OCC)OCC)CCC2OC21 UDUKMRHNZZLJRB-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
- 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
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 239000011882 ultra-fine particle Substances 0.000 description 1
- 238000004383 yellowing Methods 0.000 description 1
- 229910003454 ytterbium oxide Inorganic materials 0.000 description 1
- 229940075624 ytterbium oxide Drugs 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 150000003755 zirconium compounds Chemical class 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L33/00—Semiconductor devices having potential barriers specially adapted for light emission; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/295—Organic, e.g. plastic containing a filler
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L23/00—Details of semiconductor or other solid state devices
- H01L23/28—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection
- H01L23/29—Encapsulations, e.g. encapsulating layers, coatings, e.g. for protection characterised by the material, e.g. carbon
- H01L23/293—Organic, e.g. plastic
- H01L23/296—Organo-silicon compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
- H01L2924/0001—Technical content checked by a classifier
- H01L2924/0002—Not covered by any one of groups H01L24/00, H01L24/00 and H01L2224/00
Definitions
- the present invention relates to a polysiloxane composition in which metal oxide fine particles are highly dispersed in an organic solvent containing a polyfunctional polysiloxane having a dimethylsiloxane chain, and a cured product thereof.
- siloxane binder a composite of a binder having a siloxane skeleton (hereinafter also referred to as “siloxane binder”) and various metal oxides has been used. It is being considered.
- Polydimethylsiloxane is known as one of these siloxane-based binders! This polydimethylsiloxane does not deteriorate unless it is usually at a high temperature of 200 ° C or higher, and is useful as a siloxane-based binder with excellent heat resistance and ultraviolet resistance. Used for.
- siloxane binder and a metal oxide are combined, they are often prepared in the form of a dispersion.
- siloxane-based binders are difficult to dissolve in water, it is necessary to use an organic solvent as a dispersion medium.
- metal oxide fine particles tend to aggregate in an organic solvent and are therefore often dispersed in an aqueous medium. . Therefore, in order to finely disperse metal oxide fine particles in an organic solvent, phosphoric acid, sulfonic acid or carboxylic acid having an organic group having 6 or more carbon atoms (see Patent Document 1), or oxyalkylene group is added. It is necessary to use an organic compound having an oxyalkylene group, an ester such as phosphoric acid (see Patent Document 2), or a silane compound having an oxyalkylene group (see Patent Document 3).
- these compounds are used to differentiate metal oxide fine particles into an organic solvent.
- the metal oxide fine particles and the siloxane binder are combined by a dispersion method, the dispersibility of the dispersion is good.
- the compatibility between the above compound and the siloxane binder is poor.
- the coating film could be whitened.
- phosphoric acid having an organic group having 6 or more carbon atoms or a compound having an oxyalkylene group remains in this coating film. For this reason, defects such as coloring of the coating film and occurrence of cracks may occur in harsh environments such as under ultraviolet irradiation or at high temperatures of 150 ° C or higher.
- the polysiloxane composition When a transparent coating film is formed using a conventional polysiloxane composition containing metal oxide fine particles, the polysiloxane composition usually contains 30 to 90% by weight of a dispersion solvent, Furthermore, in order to ensure the dispersion stability of the metal oxide fine particles, the viscosity at 25 ° C. and the rotor rotation speed of 5 rpm measured by an E-type viscometer is usually adjusted to a low viscosity of 15 mPa's or less. When a filler having a high specific gravity was added to such a low-viscosity metal oxide fine particle-containing polysiloxane composition, the filler sometimes settled and separated.
- organic thickeners such as polyethylene glycol have been added to increase the viscosity.
- coloring and cracks are generated by heat and ultraviolet rays, and durability such as heat resistance and ultraviolet resistance is improved. It was inferior.
- the viscosity can be increased even if the solid content concentration is increased.
- the siloxane-based binder is gelled or the metal oxide fine particles are formed. Sometimes settled.
- Patent Document 1 Japanese Patent Application Laid-Open No. 2004-283822
- Patent Document 2 Japanese Patent Laid-Open No. 2005-185924
- Patent Document 3 Japanese Patent Application Laid-Open No. 2004-99879
- the present invention is intended to solve the problems associated with the prior art as described above, and has excellent transparency, heat resistance, ultraviolet resistance, and moisture resistance, which are excellent in transparency and hardly yellow or decompose even at high temperatures. It is an object of the present invention to provide a polysiloxane-based cured product excellent in heat resistance, a polysiloxane composition in which metal oxide fine particles are highly dispersed, and a method for producing the same. Means for solving the problem
- the present inventor predealked a hydroxy-terminated polydimethylsiloxane and a high molecular weight alkoxy-terminated polyfunctional polysiloxane, or an alkoxy group-containing polydimethylsiloxane and a high-molecular weight silanol-terminated polyfunctional polysiloxane.
- a polyfunctional polysiloxane having a dimethylsiloxane chain and the metal oxide fine particles are treated in the presence of a basic compound, acidic compound or metal chelate compound in an organic solvent containing the polyfunctional polysiloxane.
- the metal oxide fine particle-containing polysiloxane composition according to the present invention in the presence of a basic compound, an acidic compound or a metal chelate compound in an organic solvent,
- R 1 is a monovalent hydrocarbon group having no hydrogen atom or Okishiarukiren group
- Yogu R 2 be different be the same as each other in the case where R 1 there are a plurality If there are multiple R 2 groups, they may be the same or different from each other.
- A is greater than 0 and less than 2
- b is greater than 0 and less than 2
- Alcohol-terminated polydimethylsiloxane (b4) in the range of 000 to 100,000 is subjected to a dealcoholization reaction with a weight ratio (b 3 / b4) in the range of 30Z70 to 95Z5 with respect to a total of 100 parts by weight.
- metal oxide fine particles ( ⁇ ) are dispersed in an organic solvent.
- the polyfunctional polysiloxane (B1) or ( ⁇ 2) is further hydrolyzed and condensed, It is preferable to mix with metal oxide fine particles (A).
- the catalyst in the hydrolysis' condensation is preferably a basic catalyst.
- the catalyst in the dealcoholization reaction is preferably a metal chelate compound.
- the metal oxide fine particles (A) and the polyfunctional polysiloxane (B1) or (B2) are mixed in the presence of a basic compound.
- the metal oxide fine particles (A) and the polyfunctional polysiloxane (B1) or (B2) are preferably mixed by a bead mill.
- the polyfunctional polysiloxane (B1) or (B2) is mixed with 100 parts by weight of the metal oxide fine particles (A) by 1 to LOOO parts by weight in terms of a complete hydrolyzed condensate. Is preferred
- the cured body according to the present invention is obtained from the metal oxide fine particle-containing polysiloxane composition.
- the LED sealing material according to the present invention is obtained by further mixing a phosphor with the metal oxide fine particle-containing polysiloxane composition.
- the method for producing the metal oxide fine particle-containing polysiloxane composition according to the present invention comprises the following average composition formula (1):
- R 1 is a monovalent hydrocarbon group having no hydrogen atom or Okishiarukiren group
- Yogu R 2 be different be the same as each other in the case where R 1 there are a plurality If there are multiple R 2 groups, they may be the same or different from each other.
- A is greater than 0 and less than 2
- b is greater than 0 and less than 2
- Alcohol-terminated polydimethylsiloxane (b4) in the range of 000 to 100,000 is subjected to a dealcoholization reaction with a weight ratio (b 3 / b4) in the range of 30Z70 to 95Z5 with respect to a total of 100 parts by weight.
- the polyfunctional polysiloxane (B1) or ( ⁇ 2) and the metal oxide fine particles ( ⁇ ) are mixed in an organic solvent in the presence of a basic compound, an acidic compound or a metal chelate compound.
- the polyfunctional polysiloxane (B1) or () 2) is further hydrolyzed and condensed and then mixed with the metal oxide fine particles ( ⁇ ).
- the catalyst in the hydrolysis' condensation is preferably a basic catalyst.
- the catalyst in the dealcoholization reaction is preferably a metal chelate compound.
- metal oxide fine particles ( ⁇ ) and the polyfunctional polysiloxane (B1) or ( ⁇ 2) are mixed in the presence of a basic compound.
- the metal oxide fine particles ( ⁇ ) and the polyfunctional polysiloxane (B1) or ( ⁇ 2) are mixed by a bead mill.
- a polysiloxane having a dimethylsiloxane chain is used without using a compound having an alkoxyalkylene group such as phosphoric acid having an organic group having 6 or more carbon atoms.
- a composition in which metal oxide fine particles are highly dispersed in an organic solvent is obtained.
- This composition is excellent in dispersion stability and can form a transparent cured product containing metal oxide fine particles and the polysiloxane.
- the polysiloxane power includes a polyfunctional polysiloxane having a dimethylsiloxane chain having an appropriate length and a three-dimensional structure or a ladder structure, it can form a thick cured film having excellent flexibility and can be used at high temperatures.
- a cured product excellent in heat resistance, ultraviolet resistance, and moist heat resistance, which is difficult to be yellowed and decomposed and deteriorated can be obtained.
- a cured product using highly refractive metal oxide fine particles as metal oxide fine particles can be used as a sealing material for LED elements using blue LED elements or ultraviolet LED elements as light emitting elements. It is useful as a sealing material for high-brightness LED elements.
- the metal oxide fine particle-containing polysiloxane composition according to the present invention comprises metal oxide fine particles.
- a and B) are used in an organic solvent without using a phosphoric acid having an organic group having 6 or more carbon atoms or a compound having an oxyalkylene group. It can be obtained by mixing in the presence of a basic compound, an acidic compound or a metal chelate compound and subjecting it to a dispersion treatment.
- metal oxide fine particles (A) used in the present invention is not particularly limited as long as they are metal element oxide fine particles.
- metal element oxide fine particles For example, antimony oxide, zirconium oxide, anatase-type titanium oxide, rutile-type oxide Titanium, brookite type acid titanium oxide, acid zinc oxide, acid titanium tantalum, indium oxide, acid hafnium, tin oxide, niobium oxide, acid medium, acid cerium, oxidation Scandium, yttrium oxide, lanthanum oxide, acid prasedium, acid neodymium, samarium oxide, gallium oxide, terbium oxide, dysprosium oxide, holmium oxide, erbium oxide , Yttrium oxide, ytterbium oxide, lutetium oxide, calcium oxide, gallium oxide, lithium oxide, striking oxide
- metal oxide fine particles such as oxides of two or more of the above-mentioned metals such as indium, tungsten oxide, barium oxide
- the metal oxide fine particles are used singly or in combination of two or more. May be used.
- the metal oxide fine particles (A) can be appropriately selected according to the function to be imparted. For example, when imparting high refractive properties, the TiO fine particles are preferred in the ultraviolet region.
- ZrO fine particles are preferable for achieving both transparency and high refractive index. UV cut function
- acid-cerium fine particles and acid-zinc fine particles are preferable.
- the primary average particle diameter of the metal oxide fine particles (A) is preferably 0.1 to: LOOnm, more preferably 0.1 to 70 nm, and particularly preferably 0.1 to 50 nm.
- LOOnm more preferably 0.1 to 70 nm, and particularly preferably 0.1 to 50 nm.
- Such metal oxide fine particles (A) are dispersed in a solvent! However, it may be added in the form of powder or may be added in the form of a dispersion dispersed in a polar solvent such as isopropyl alcohol or a nonpolar solvent such as toluene.
- the metal oxide fine particles (A) before addition may be aggregated to form secondary particles.
- it is preferable to use a powder because an appropriate organic solvent can be appropriately selected in consideration of the solubility of the polyfunctional polysiloxane (B).
- the production method of the present invention is particularly effective when added in the form of powder.
- the polyfunctional polysiloxane (B) used in the present invention is a polyfunctional polysiloxane having a dimethylsiloxane chain, and has a polystyrene-equivalent weight average molecular weight of 3,000 or more and 100,000 or less as measured by genorepermeation chromatography. And hydroxy-terminated polydimethylsiloxane (bl) having a polystyrene-reduced weight average molecular weight in the range of 2,000 to 100,000 as measured by genopermeation chromatography.
- Polysiloxane (B1) obtained by dealcoholization reaction with siloxane (b2) and polystyrene equivalent weight average molecular weight measured by gel permeation chromatography is in the range of 3,000 to 100,000.
- (bl) Alkoxy-terminated polyfunctional polysiloxane The alkoxy-terminated polyfunctional polysiloxane (bl) used in the present invention has the following average composition formula (1)
- R 1 is a monovalent hydrocarbon group having no hydrogen atom or oxyalkylene group, and when there are a plurality of R 1 s, they may be the same as or different from each other.
- R 2 is an alkyl group, and when two or more R 2 are present, they may be the same or different.
- a is greater than 0 and less than 2
- b is greater than 0 and less than 2
- c is greater than 0 and less than 4
- a + b X 2 + c 4.
- a is a ratio of a hydrogen atom and a monovalent hydrocarbon group having no oxyalkylene group to the total of the silicon atoms
- c is a silicon atom of the alkoxy group Represents the ratio to.
- the weight-average molecular weight of the above alkoxy-terminated polyfunctional polysiloxane (bl) is 3,000 or more and 100,000 or less, more preferably ⁇ 3,000 or more in terms of polystyrene measured by gel permeation chromatography. 80,000 or less, particularly preferred ⁇ 3,500 or more and 50,000 or less.
- an alkoxy-terminated polyfunctional polysiloxane (bl) having a weight average molecular weight within the above range is used, it is possible to achieve both suppression of crack generation during formation of a cured product and suppression of degradation and degradation under wet heat.
- the monovalent hydrocarbon group is not particularly limited as long as it does not have an oxyalkylene group.
- 1S substituted or unsubstituted monovalent hydrocarbon group examples include an alkyl group having 1 to 8 carbon atoms, a phenol group, a benzyl group, and a tolyl group.
- Examples of the alkyl group having 1 to 8 carbon atoms include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, and an octyl group.
- Examples of the monovalent substituted hydrocarbon group include substituted alkyl groups having 1 to 8 carbon atoms.
- Examples of the substituent of the substituted alkyl group include halogen, amino group, mercapto group, isocyanate group, glycidyl group, glycidoxy group, ureido group and the like.
- alkyl group represented by R 2 examples include a methyl group, an ethyl group, a propyl group, an isopropyl group, and a butyl group. Of these alkyl groups, a methyl group and an ethyl group are preferred.
- This alkoxy-terminated polyfunctional polysiloxane (bl) can be produced, for example, by subjecting the polyfunctional alkoxysilane or polyfunctional chlorosilane to an appropriate combination of hydrolysis and condensation so as to satisfy the above average composition formula. . However, hydrolysis / condensation with only tetraalkoxysilanes and hydrolysis / condensation with dialkoxysilanes only are excluded.
- an alkoxy-terminated polyhydride obtained by using 50% by weight or more of trifunctional alkoxysilane and Z or trifunctional chlorosilane is used.
- functional polysiloxanes are especially preferred.
- Examples of the polyfunctional alkoxysilane include tetraalkoxysilanes such as tetramethoxysilane, tetraethoxysilane, tetra-n-propoxysilane, tetra-i-propoxysilane, and tetra-n-butoxysilane.
- Dimethinoresimethoxysilane Dimethinoresetoxysilane, Getinoresimethoxymethoxysilane, Getinoresetoxysilane, Gn -propinoresimethoxymethoxysilane, Gn Propinolegetoxy Silane, G i Propinoresimethoxy silane, G i Propino letoxy silane, G n-Butyl dimethoxy silane, Di n-Butyl methoxy silane, Di n-Pentyl dimethoxy silane, G n Pentino-letoxy silane, G n carboxymethyl Norre dimethoxysilane, di -n- to carboxymethyl Honoré jet silane, di n- heptylene Honoré dimethoxysilane, Petit to di n- Honoré jet silane, di n - old Chi Honoré dimethoxysilane, di n- old Kuchinorejeto Examples thereof include dialkoxysilanes such as xys
- a monofunctional alkoxysilane may be used in combination.
- monofunctional alkoxysilanes include trimethylmethoxysilane, trimethylethoxysilane, triethylmethoxysilane, and triethylethoxysilane. These monofunctional alkoxysilanes are desirably used in an amount of 10% by weight or less, preferably 7% by weight or less, more preferably 5% by weight or less based on the total amount of alkoxysilane used.
- alkoxy-terminated polyfunctional polysiloxane (bl) satisfying the above molecular weight commercially available siloxane polymers such as XR31-B0270 and XR31-B2733 (trade name) manufactured by GE TOSHIBA Silicone Co., Ltd. are used. You can also.
- the alkoxy-terminated polyfunctional polysiloxane (bl) has a Si—OH bond in a range without impairing the effects of the present invention!
- the hydroxy-terminated polydimethylsiloxane (b2) used in the present invention has a polystyrene-equivalent weight average molecular weight of 2,000 to 100,000, more preferably ⁇ 2,000 to 80,000 as measured by gel permeation chromatography. 000 or less, especially preferred ⁇ is from 3,000 to 70,000.
- a polyfunctional polysiloxane (B1) having excellent flexibility can be obtained. Therefore, it is possible to increase the thickness of the cured body.
- This hydroxy-terminated polydimethylolsiloxane (b2) can be produced, for example, by hydrolyzing and condensing dimethylenoresinanoloxysilane or dimethyldichlorosilane.
- dimethyldialkoxysilane examples include dimethyldimethoxysilane, dimethyljetoxysilane, dimethyldipropoxysilane, dimethyldibutoxysilane, and the like. These dimethyl dialkoxysilanes can be used alone or in admixture of two or more.
- the hydroxy-terminated polydimethylsiloxane (b2) can also be produced by ring-opening condensation of a cyclic organosiloxane.
- Cyclic organosiloxanes include hexaphenylcyclotrisiloxane, octaphenylcyclotetrasiloxane, tetilavinyl tetramethylcyclotetrasiloxane, hexamethylcyclotrisiloxane, otamethylcyclotetrasiloxane, pentamethylcyclotetrasiloxane, hexamethyl. Examples thereof include cyclotetrasiloxane, tetramethylcyclotetrasiloxane, decamethylcyclopentasiloxane, and dodecamethylcyclohexasiloxane.
- hydroxy-terminated polydimethylsiloxane (b2) satisfying the above molecular weight YF-3057, YF-3800, YF-3802, YF-3807, YF-3389, and XF-3905 manufactured by GE Toshiba Corporation. It is possible to use commercially available hydroxy-terminated polydimethylsiloxane (such as the above).
- the hydroxy-terminated polyfunctional polysiloxane (b3) used in the present invention is:
- the polyfunctional polysiloxane having a hydroxy group represented by the formula (1) has a three-dimensional crosslinked structure.
- the hydroxy-terminated polyfunctional polysiloxane (b3) has a weight average molecular weight of -Polystyrene conversion value measured by chromatography, 3,000 to 100,000, more preferably ⁇ 3,000 to 80,000, particularly preferably ⁇ 3,500 to 50,000 is there.
- a weight average molecular weight of -Polystyrene conversion value measured by chromatography 3,000 to 100,000, more preferably ⁇ 3,000 to 80,000, particularly preferably ⁇ 3,500 to 50,000 is there.
- the monovalent hydrocarbon group is not particularly limited as long as it does not have an oxyalkylene group.
- substituted or unsubstituted monovalent hydrocarbon group examples include the same as the substituted or unsubstituted monovalent hydrocarbon group exemplified for the alkoxy-terminated polyfunctional polysiloxane (bi).
- This hydroxy-terminated polyfunctional polysiloxane (b3) is obtained by, for example, subjecting the above average yarn formula to hydrolysis and condensation by appropriately combining polyfunctional alkoxysilanes or polyfunctional chlorosilanes. Can be manufactured. However, hydrolysis / condensation with only tetraalkoxysilanes and hydrolysis / condensation with dialkoxysilanes only are excluded. In the present invention, since the decomposition resistance in the presence of the metal oxide fine particles (A) and water is excellent, 50% by weight or more of V-terminated hydroxy end groups obtained by using trifunctional alkoxysilane and Z or trifunctional chlorosilane. Especially preferred are functional polysiloxanes.
- Examples of the polyfunctional alkoxysilane may include the same polyfunctional alkoxysilanes exemplified for the alkoxy-terminated polyfunctional polysiloxane (bl), and may be used alone or in combination of two or more. Can be used.
- the monofunctional alkoxysilane exemplified in the above alkoxy-terminated polyfunctional polysiloxane (bl) is used in combination. May be.
- the monofunctional alkoxysilane is desirably used in an amount of 10% by weight or less, preferably 7% by weight or less, more preferably 5% by weight or less based on the total amount of the alkoxysilane used.
- the above alkoxy-terminated polyfunctional polysiloxane (b3) has a Si—OR bond in a range without impairing the effects of the present invention.
- the alkoxy-terminated polydimethylsiloxane (b4) used in the present invention is a gel permeant.
- the weight average molecular weight in terms of polystyrene measured by chromatography chromatography is 2,000 to 100,000, more preferably ⁇ is 2,000 to 80,000, particularly preferably ⁇ is 3,000 to 70,000 It is as follows.
- a polyfunctional polysiloxane (B2) having excellent flexibility can be obtained. Therefore, it is possible to increase the thickness of the cured body.
- This alkoxy-terminated polydimethylsiloxane (b4) can be produced, for example, by hydrolysis and condensation of dimethyldialkoxysilane or dimethyldichlorosilane.
- dialkoxysilane examples include those similar to the dialkoxysilane exemplified in the hydroxy-terminated polydimethylsiloxane (b2). These may be used alone or in combination of two or more. can do.
- the polyfunctional polysiloxane (B1) can be produced by subjecting the alkoxy-terminated polyfunctional polysiloxane (bl) and the hydroxy-terminated polydimethylsiloxane (b2) to a dealcoholization reaction.
- the polyfunctional polysiloxane (B2) can be produced by subjecting the hydroxy-terminated polyfunctional polysiloxane (b3) and the alkoxy-terminated polydimethylsiloxane (b4) to a dealcoholization reaction.
- These polyfunctional polysiloxanes (B1) and (B2) are usually preferably further hydrolyzed and condensed after adding water. As a result, the multifunctional polysiloxanes (B1) and (B2) have a high molecular weight, and the resulting cured product has improved transparency.
- Each of the above reactions is usually performed using a catalyst in an organic solvent.
- the mixing ratio of the alkoxy-terminated polyfunctional polysiloxane (bl) and the hydroxy-terminated polydimethylsiloxane (b2) is 30Z70 to 95Z5 in a weight ratio (blZb2) with respect to 100 parts by weight of the total. Preferably, it is 50 ⁇ 50 to 95 ⁇ ⁇ ⁇ ⁇ 5, more preferably 50,50 to 90/10.
- the mixing ratio of the hydroxy-terminated polyfunctional polysiloxane (b3) and the alkoxy-terminated polydimethylsiloxane (b4) is 30Z70 to 95Z5 in a weight ratio (b3Zb4) with respect to 100 parts by weight in total.
- the temperature of the dealcoholization reaction is preferably 30 to 150 ° C, more preferably 40 to 120 ° C, and particularly preferably 50 to 100 ° C.
- the reaction time is preferably 0.1 to 24 hours, more preferably 0.5 to 12 hours, and particularly preferably 1 to 8 hours.
- the dealcoholization reaction may be carried out by charging each component in a reaction vessel at once, or may be carried out while intermittently or continuously adding the other component to one component.
- a polyfunctional polysiloxane (B2) having a structure in which a hydroxy-terminated polyfunctional polysiloxane (b3) is bonded to both ends of the siloxane (b4) is formed.
- the amount of water added in the condensation reaction is usually 1 to 500 parts by weight, preferably 10 to 300 parts by weight, per 100 parts by weight of the polyfunctional polysiloxane (B1) or (B2). More preferably, it is 20 to 200 parts by weight. It is preferable that the amount of water added is in the above range because the hydrolysis and condensation reaction proceeds sufficiently and the amount of water removed after the reaction is small.
- the temperature of the hydrolysis' condensation reaction is preferably 20 to 150 ° C, more preferably 30 to: LO 0 ° C, particularly preferably 40 to 80 ° C.
- the reaction time is preferably 0.1 to 24 hours, more preferably 0.5 to 12 hours, and particularly preferably 1 to 8 hours.
- Examples of the organic solvent used in the above dealcoholization reaction and hydrolysis' condensation reaction include alcohols, aromatic hydrocarbons, ethers, ketones, and esters. And the like.
- Examples of the alcohols include methanol, ethanol, n-propyl alcohol, i-propyl alcohol, i-butyl alcohol, n-butyl anolenoconole, sec-butinoreanoreconole, tert-butenoreanoreconole, n-hexino.
- aromatic hydrocarbons include benzene, toluene, and xylene.
- ethers include tetrahydrofuran and dioxane.
- ketones include acetone, methyl ethyl ketone, methyl isobutyl ketone, and dioxane.
- esters ethyl acetate, propyl acetate, butyl acetate, propylene carbonate, methyl lactate, ethyl lactate, normal propyl lactate, isopropyl lactate, methyl 3-ethoxypropionate, 3-ethoxypropion.
- acids ethyl may be used alone or in combination of two or more.
- organic solvents in the dealcoholization reaction, it is preferable to use an organic solvent other than alcohol, for example, methyl ethyl ketone, methyl isobutyl ketone, toluene, xylene, etc., from the viewpoint of promoting the reaction.
- organic solvents are preferably used in a state where moisture has been removed by performing a dehydration treatment in advance.
- the above organic solvent is used for the control of dealcoholization reaction and hydrolysis' condensation reaction, adjustment of the concentration or viscosity of the resulting polyfunctional polysiloxane (B1) or (B2) -containing solution, or thickness at the time of producing a cured product. It can be used as appropriate for the purpose of adjustment.
- the amount used can be set as appropriate according to the desired conditions. For example, the concentration of the polyfunctional polysiloxane (B1) or (B2) obtained.
- the amount is preferably 5 to 99% by weight, more preferably 7 to 95% by weight, and particularly preferably 10 to 90% by weight.
- Examples of the catalyst used in the dealcoholization reaction or hydrolysis / condensation reaction include basic compounds, acidic compounds and metal chelate compounds. [0066] (Basic compounds)
- Examples of the basic compound include ammonia (including aqueous ammonia solution), organic amine compound, sodium hydroxide, hydroxide of alkaline earth metal such as potassium hydroxide, sodium methoxide, and the like. And alkali metal alkoxides such as sodium ethoxide. Of these, ammonia and organic amine compounds are preferred.
- organic amines examples include alkylamines, alkoxyamines, alkanolamines, arylamines and the like.
- alkylamine examples include methylamine, ethylamine, propylamine, butylamine, hexylamine, octylamine, N, N dimethylamine, N, N jettilamine, N, N dipropylamine, N, N dibutylamine, trimethylamine, triethylamine, tripropylamine.
- alkylamine having an alkyl group having 1 to 4 carbon atoms such as tributylamine.
- alkoxyamine examples include methoxymethylamine, methoxyethylamine, methoxypropylamine, methoxybutylamine, ethoxymethylamine, ethoxyethylamine, ethoxypropylamine, ethoxybutylamine, propoxymethyl.
- Alkoxy groups having an alkoxy group having 1 to 4 carbon atoms such as amines, propoxychetylamines, propoxypropylamines, propoxybutylamines, butoxymethylamines, butoxysethylamines, butoxypropylamines, butoxybutylamines. Min etc. are mentioned.
- alkanolamines include methanolamine, ethanolamine, propanolamine, butanolamine, N-methylmethanolamine, N-ethylmethanolamine, N-propylmethanolamine, and N-butylmethanol.
- arylamine examples include aline and N-methylaline.
- organic amines include tetramethylammonumno, idroxide, tetraethylammonium hydroxide, tetrapropylammonum hydroxide.
- Tetraalkylammonium hydroxide such as tetrabutylethylenediamine; tetraalkylethylenediamine such as tetramethylethylenediamine, tetraethylethylenediamine, tetrapropylethylenediamine, tetrabutylethylenediamine Methylaminomethylamine, methylaminoethylamine, methylaminopropylamine, methylaminobutyramine, ethylaminomethylamine, ethylaminoethylamine, ethylaminopropylamine, Tilaminobutylamine, propylaminomethylamine, propyl Alkylaminoalkylamines such as aminoethylamine, propylaminopropylamine, propylaminobutylamine, butylaminomethylamine, butylaminoethylamine, butylaminopropylamine, butylaminobuty
- Such basic compounds may be used singly or in combination of two or more. Of these, triethylamine, tetramethylammonium hydroxide and pyridine are particularly preferable.
- Examples of the acidic compound include organic acids and inorganic acids.
- Examples of organic acids include acetic acid, propionic acid, butanoic acid, pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, decanoic acid, oxalic acid, maleic acid, maleic anhydride, and methylmalonic acid.
- the inorganic acid include hydrochloric acid, nitric acid, sulfuric acid, hydrofluoric acid, and phosphoric acid.
- Such acidic compounds may be used singly or in combination of two or more.
- maleic acid maleic anhydride, methanesulfonic acid, and acetic acid are particularly preferred.
- metal chelate compound examples include organometallic compounds and Z or partial hydrolysates thereof (hereinafter referred to as “organic metal compounds” t, which are collectively referred to as organometallic compounds and Z or partial hydrolysates thereof). Can be mentioned.
- organometallic compounds include, for example, the following formula (a)
- M represents at least one metal atom selected from the group consisting of zirconium, titanium, and aluminum
- R 7 and R 8 independently represent a methyl group, an ethyl group, N-propyl group, i-propyl group, n-butyl group, sec-butyl group, t-butyl group, n-pentyl group, n-hexyl group, cyclohexyl group, phenol group, etc. having 1 to 6 carbon atoms
- R 9 represents a monovalent hydrocarbon group having 1 to 6 carbon atoms, or a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, or an n-butoxy group.
- organic compound (a) (Hereinafter referred to as “organometallic compound (a)”)
- organic metal compound of tetravalent tin in which 1 to 2 alkyl groups having 1 to 10 carbon atoms are bonded to one tin atom hereinafter referred to as “organic tin compound”.
- organometallic compound (a) for example, tetra-n-butoxyzirconium, tri-n-butoxy.
- Ethinoreacetoacetate dinoreconium, di- n -butoxy'bis (ethenoreacetoacetate) zirconium, n- Organic zirconium compounds such as butoxy 'tris (ethinoreacetoacetate) dinoleconium, tetrakis (n-propylacetoacetate) zirconium, tetrakis (acetinoreacetoacetate) zirconium, tetrakis (ethinoreacetoacetate) zirconium;
- Organics such as tetra-i-propoxy titanium, di-i-propoxy 'bis (ethinoreacetoacetate) titanium, di-i-propoxy'bis (acetyl acetate) titanium, di-i-propoxy'bis (acetylacetone) titanium Titanium compound;
- Tree i-propoxyaluminum, di-i-propoxy-ethylacetoacetate aluminum yuum, zi i-propoxy-acetylacetonate aluminum, i-propoxy 'bis (ethinoreacetoacetate) anoleminium, i-propoxy' Bis (acetinoreacetonate) Aluminum, Tris (ethyl acetoacetate) Aluminum, Tris (Acetyl acetonate) Aluminum, Monoacetyl acetonate 'bis (ethyl acetoacetate) aluminum And organoaluminum compounds.
- organic tin compound for example,
- Carboxylic acid type organotin compounds such as;
- Mercaptide-type organotin compounds such as (C 4 H g ) 2 Sn (SCH 2 COOC 8 H l7 );
- Chloride-type organotin compounds such as;
- Organic tin oxides such as (C H) SnO and (C H) SnO, and these organic tin oxides
- Reaction products of id with silicates, ester compounds such as dimethyl maleate, jetyl maleate, dioctyl phthalate;
- Such metal chelate compounds may be used singly or in combination of two or more. Of these, tri-n-butoxyethyl acetate acetate zirconium, diipropoxy bis (acetinoreacetonate) titanium, diipropoxy ethenoreacetoacetate aluminum, tris (ethylacetoacetate) aluminum, or These partial hydrolysates are preferred.
- hydrolysis compounds in which metal chelate compounds are preferred in the dealcoholization reaction and basic compounds are preferred in the condensation.
- the metal chelate compound is superior in dealcoholization reactivity compared to other compounds, and when a basic compound is used as a catalyst in the presence of moisture, the hydrolysis reaction rate is faster than the condensation reaction rate.
- the remaining alkoxy groups can be reduced, and the volume shrinkage of the resulting polysiloxane can be reduced, so that a cured product having excellent crack resistance can be formed.
- the basic compound, acidic compound or metal chelate compound is a total of 100 of polyfunctional polysiloxane (bl) or (b3) and polydimethylsiloxane (b2) or (b4).
- the amount is usually 0.001 to 20 parts by weight, preferably 0.05 to 10 parts by weight, more preferably 0.01 to 5 parts by weight based on the parts by weight.
- the basic compound, acidic compound or metal chelate compound is the sum of polyfunctional polysiloxane (bl) or (b3) and polydimethylsiloxane (b2) or (b4).
- 1 to 50 parts by weight, preferably 2 to 40 parts by weight, more preferably 3 to 30 parts by weight are added to 100 parts by weight.
- a decatalyzing step after hydrolysis condensation is performed. It is preferable to perform washing with water. In particular, when a basic compound is used as a hydrolysis-condensation catalyst, it is more preferable to carry out water washing after neutralization with an acidic compound after the reaction.
- the acidic compound used for neutralization the acidic compounds exemplified above can be used.
- the amount of the acidic compound used is usually 0.5 to 2.0 mol, preferably 0.8 to 1.5 mol, more preferably 0.9 to 1., per 1 mol of the basic compound used for the hydrolysis condensation. 3 moles.
- the acidic compound is usually 1 per 100 parts by weight of the total of polyfunctional polysiloxane (bl) or (b3) and polydimethylsiloxane (b2) or (b4).
- 0-500 parts by weight preferably ⁇ is 20-300 parts, more preferably ⁇ is dissolved in 30-200 parts of water. After neutralization, stir and mix thoroughly, and let stand, and after confirming phase separation between the aqueous phase and the organic solvent phase, remove the water in the lower layer.
- the water used for washing after neutralization is usually 10 to 500 per 100 parts by weight of the total of the polyfunctional polysiloxane (bl) or (b3) and the polydimethylsiloxane (b2) or (b4). Parts by weight
- the amount is preferably 20 to 300 parts, more preferably 30 to 200 parts.
- Washing with water is performed by adding water and stirring sufficiently, and then allowing to stand, and after confirming phase separation between the aqueous phase and the organic solvent phase, removing water in the lower layer.
- the number of washings is preferably 1 or more times, more preferably 2 or more times.
- the weight average molecular weights of the polyfunctional polysiloxanes (B1) and (B2) obtained by the above method are usually expressed in terms of polystyrene measured by gel permeation chromatography.
- the metal oxide fine particle-containing polysiloxane composition according to the present invention comprises metal oxide fine particles.
- a polyfunctional polysiloxane having a dimethylsiloxane chain (B1) or (B2) can be used without using a phosphoric acid having an organic group having 6 or more carbon atoms or a compound having an oxyalkylene group. It can be obtained by mixing and dispersing in an organic solvent in the presence of a basic compound, acidic compound or metal chelate compound.
- organic solvent examples include the organic solvents exemplified in the dealcohol reaction and hydrolysis / condensation reaction during the production of the polyfunctional polysiloxane (B1) or (B2).
- organic solvents other than alcohols such as methyl ethyl ketone, methyl isobutyl ketone, diisoptyl ketone are preferable in that the dispersion stability and viscosity of the metal oxide-containing polysiloxane composition can be increased.
- Toluene, xylene, ethyl acetate, butyl acetate, and mixtures thereof are preferred.
- These organic solvents are preferably used in a state where moisture has been removed by performing a dehydration treatment in advance.
- the amount of the organic solvent used is not particularly limited as long as the metal oxide fine particles (A) can be uniformly dispersed, but the solid content concentration of the resulting metal oxide fine particle-containing polysiloxane composition is not limited. However, the amount is preferably 5 to 80% by weight, more preferably 7 to 70% by weight, and particularly preferably 10 to 60% by weight.
- Examples of the basic compound, acidic compound, and metal chelate compound include the compounds exemplified in the dealcoholization reaction and hydrolysis / condensation reaction during the production of the polyfunctional polysiloxane (B1) or (B2).
- these basic compounds, acidic compounds, and metal chelate compounds basic compounds that are preferred by basic compounds and acidic compounds are more preferred by organic amine compounds that are more preferred by triethylamine, tetramethyl. Ammonium hydroxide and pyridine are particularly preferred.
- the basic compound, acidic compound, or metal chelate compound is added to the metal oxide fine particle-containing polysiloxane composition of the present invention with respect to 100 parts by weight of the metal oxide fine particles (A).
- the metal oxide fine particles (A) Usually, 0.001 to 20 parts by weight, preferably 0.005 to 10 parts by weight, more preferably 0.01 to 5 parts by weight, still more preferably 0.01 to 1 part by weight, particularly preferably 0.01 to 10 parts by weight. 0.5 weight It is desirable that the part is contained. Within the above range, the dispersion stability of the metal oxide fine particles (A) and the viscosity of the polysiloxane composition containing the metal oxide fine particles can be easily controlled.
- the metal oxide fine particle-containing polysiloxane composition includes a metal oxide fine particle (A) and a polyfunctional polysiloxane (B1) or (B2) having a dimethylsiloxane chain in an organic solvent, a basic compound, an acidic compound, or a metal. It can be prepared by adding a chelate compound, mixing them well and dispersing the metal oxide fine particles (A) in an organic solvent. At this time, it is particularly preferable to use a known disperser such as a ball mill, a sand mill (bead mill, a high shear bead mill), a homogenizer, an ultrasonic homogenizer, a nanomizer, a propeller mixer, a high shear mixer, or a paint shaker.
- a known disperser such as a ball mill, a sand mill (bead mill, a high shear bead mill), a homogenizer, an ultrasonic homogenizer, a nanomizer, a propeller mixer
- the fine particle dispersion ball mill and sand mill (bead mill, high shear bead mill) are preferably used.
- the metal oxide fine particles (A) and the polyfunctional polysiloxane (B1) or (B2) are mixed in the presence of the basic compound, acidic compound or metal chelate compound, the basic compound, acidic compound or The polyfunctional polysiloxane (B1) or (B2) condensation reaction proceeds on the surface of the metal oxide fine particles (A) due to the catalytic action of the metal chelate compound, and the surface of the metal oxide fine particles (A) becomes hydrophobic. Therefore, it is presumed that it becomes easy to finely disperse in an organic solvent.
- the polysiloxane composition containing metal oxide fine particles of the present invention is a product obtained by completely hydrolyzing polyfunctional polysiloxane (B1) or (B2) with respect to 100 parts by weight of metal oxide fine particles (A).
- B1 or B2 polyfunctional polysiloxane
- A metal oxide fine particles
- the polysiloxane composition containing metal oxide fine particles is a composition in which metal oxide fine particles (A) are highly dispersed with a volume average dispersed particle size of 300 nm or less, preferably 200 nm or less. .
- the oxide fine particle-containing polysiloxane composition of the present invention can be increased in viscosity by extending the dispersion treatment time without using an organic thickener such as polyethylene glycol, Neither gelation nor sedimentation of oxide fine particles (A) occurred, and high specific gravity additive was mixed Even in this case, sedimentation separation can be suppressed.
- the acid oxide fine particle-containing polysiloxane composition is preferably a viscosity at 25 ° C, rotor rotational speed 5 rpm, solid content concentration 20 wt% as measured by a RE80 viscometer manufactured by Toki Sangyo Co., Ltd. Is at least 20 mPa's, more preferably at least 30 mPa's, particularly preferably at least 50 mPa's.
- a thick film cured body can be easily produced without separation even when a high specific gravity filler is blended.
- the metal oxide fine particle-containing polysiloxane composition includes a metal oxide fine particle (A) and a polysiloxane (B1) containing polysiloxane (B1) or (B2) having a dimethylsiloxane chain. Or, since the polyfunctional polysiloxane (bl) or (b3) contained in (B2) is present on the surface of the metal oxide fine particles, contact between the dimethylsiloxane chain and the metal oxide fine particles can be suppressed. It is estimated that the cured product, in which the decomposition reaction of the dimethylsiloxane chain hardly occurs even under high temperature and high humidity, is excellent in heat resistance and moist heat resistance. In addition, since the above polysiloxane is excellent in flexibility, a cured product having a thickness of 10 m to 500 nm can be formed.
- the metal oxide fine particles (A) in the composition are organic having 6 or more carbon atoms. Highly dispersed without using phosphoric acid having a group or a compound having an oxyalkylene group. This makes it possible to form a cured product that does not deteriorate even when exposed to harsh environments and has excellent transparency.
- this cured body has no carbon-carbon bond in the cross-linked structure and is excellent in ultraviolet resistance. For example, the cured body is It should not turn yellow (yellow) even after 200 hours of ultraviolet irradiation.
- the oxide fine particle-containing polysiloxane composition of the present invention can further contain a phosphor, and the cured product can be used as an LED sealing material.
- the oxide fine particle-containing polysiloxane composition of the present invention may contain glass fibers in order to relieve the shrinkage-expansion of the cured product.
- a composition containing glass fiber is used, a thick film cured body can be formed.
- the difference in refractive index between the polyfunctional polysiloxane (B1) or (B2) and the glass fiber is preferably 0.01 or less.
- the weight average molecular weight of siloxane was shown as a polystyrene conversion value measured by gel permeation chromatography under the following conditions.
- the appearance of the obtained composition was visually observed.
- the volume average dispersed particle size of the composition having no sedimentation of fine particles was measured with a microtrack ultrafine particle size distribution meter ("UPA150" manufactured by Nikkiso Co., Ltd.) and evaluated according to the following criteria.
- the resulting composition was applied on a quartz glass plate so that the dry film thickness was 50 m, then dried and cured at 100 ° C for 1 hour, and then dried and cured at 200 ° C for 1 hour.
- a cured product having a thickness of 50 ⁇ m was prepared on the plate. The appearance of this cured product was visually observed and evaluated according to the following criteria.
- the obtained dispersion was coated on a quartz glass plate so that the dry film thickness was 20 m, then dried and cured at 100 ° C for 1 hour, and then dried and cured at 200 ° C for 1 hour.
- a cured body having a thickness of 20 m was prepared on the plate.
- the light transmittance of the cured product at a wavelength of 450 nm was measured with an ultraviolet-visible spectrophotometer and evaluated according to the following criteria.
- the obtained composition was applied on a quartz glass plate so as to have a dry film thickness of 20 m, and then dried and cured at 100 ° C. for 1 hour. Next, it was dried and cured at 200 ° C. for 1 hour to form a cured body having a thickness of 200 m on a quartz glass plate.
- This cured product was irradiated with UV light for 200 hours under the condition of UV irradiation at a wavelength of 365 nm and 5000 mW Zcm 2 using a spot UV irradiation device (“SP-V” manufactured by Usio Electric Co., Ltd.). Eye? Observed and evaluated according to the following criteria.
- Weight retention ratio (%) cured body weight after storage Z cured body weight before storage X 100 The weight retention ratio was calculated and evaluated according to the following criteria.
- Weight retention is 90% or more and less than 95%.
- Weight retention is 70% or more and less than 90%.
- Weight retention ratio (%) cured body weight after storage Z cured body weight before storage X 100 The weight retention ratio was calculated and evaluated according to the following criteria.
- Weight retention is 90% or more and less than 95%.
- Weight retention is 70% or more and less than 90%.
- Mw 25,000 as in Preparation Example 1, except that the amount of alkoxy-terminated polysiloxane (XR31-B2733) was changed to 80 parts by weight and the amount of hydroxy-terminated polydimethylsiloxane (YF-3800) was changed to 20 parts by weight.
- alkoxy-terminated polysiloxane (XR31—B2733) was changed to 95 parts by weight.
- hydroxy-terminated polydimethylsiloxane (YF—3800)
- hydroxy-terminated polydimethylsiloxane (GE Toshiba Silicone (GE Co., Ltd., trade name:? -3905)
- Polysiloxane with a solid content of 50% by weight containing a polyfunctional polysiloxane with Mw 22,000 in the same manner as Preparation Example 1 except that 5 parts by weight was used.
- Solution (III) was obtained.
- Mw 33,000 in the same manner as in Preparation Example 1 except that the amount of alkoxy-terminated polysiloxane (XR31—B2733) was changed to 40 parts by weight and the amount of hydroxy-terminated polydimethylsiloxane (YF—3800) was changed to 60 parts by weight.
- each of the polysiloxane solutions (II) to (V) was used in the same manner as in Example 1 except that 160 parts by weight (80 parts by weight in terms of solid content) was used.
- Polysiloxane compositions (2) to (5) containing metal oxide fine particles having a weight percentage of 2% were prepared. Table 1 shows the results of evaluating the properties of these compositions.
- a metal oxide fine particle-containing polysiloxane composition (6) having a solid content concentration of 20% by weight was prepared in the same manner as in Example 2 except that 0.1 part by weight of methanesulfonic acid was used instead of triethylamine.
- the results of evaluating the properties of this composition are shown in Table 1. [Example 7]
- a polysiloxane composition (7) containing fine particles was prepared. Table 1 shows the results of evaluating the properties of this composition.
- a polysiloxane composition (8) containing metal oxide fine particles was prepared. Table 1 shows the results of the evaluation of the properties of this composition.
- a metal oxide fine particle-containing polysiloxane composition (C2) having a solid content concentration of 20% by weight was prepared in the same manner as in Example 1 except that 160 parts by weight (80 parts by weight in terms of solid content) was used. .
- the results of evaluating the properties of this composition are shown in Table 2.
- a polysiloxane composition (C4) containing metal oxide fine particles having a solid content concentration of 20% by weight was prepared in the same manner as in Example 3 except that triethylamine was used. Table 2 shows the results of evaluating the properties of this composition.
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JP2011097024A (ja) * | 2009-09-29 | 2011-05-12 | Jsr Corp | 光半導体素子の製造方法、及び、光半導体素子保護層形成用組成物 |
WO2018047760A1 (ja) * | 2016-09-07 | 2018-03-15 | 住友化学株式会社 | 硬化物、波長変換シート、発光装置、封止用部材および半導体発光装置 |
CN109689790A (zh) * | 2016-09-07 | 2019-04-26 | 住友化学株式会社 | 固化物、波长转换片材、发光装置、密封用构件及半导体发光装置 |
Also Published As
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US20090050852A1 (en) | 2009-02-26 |
KR20090017495A (ko) | 2009-02-18 |
CN101443418A (zh) | 2009-05-27 |
JP2007270056A (ja) | 2007-10-18 |
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