JP2009185148A - 有機無機複合体の合成方法 - Google Patents
有機無機複合体の合成方法 Download PDFInfo
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- JP2009185148A JP2009185148A JP2008025207A JP2008025207A JP2009185148A JP 2009185148 A JP2009185148 A JP 2009185148A JP 2008025207 A JP2008025207 A JP 2008025207A JP 2008025207 A JP2008025207 A JP 2008025207A JP 2009185148 A JP2009185148 A JP 2009185148A
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- organic
- inorganic composite
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- synthesizing
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- 238000000034 method Methods 0.000 title claims abstract description 40
- 230000002194 synthesizing effect Effects 0.000 title claims abstract description 22
- 229910003471 inorganic composite material Inorganic materials 0.000 title abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 72
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 42
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 38
- 239000002994 raw material Substances 0.000 claims abstract description 37
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- 229910052751 metal Inorganic materials 0.000 claims abstract description 33
- 239000002184 metal Substances 0.000 claims abstract description 33
- 125000000962 organic group Chemical group 0.000 claims abstract description 25
- 239000010703 silicon Substances 0.000 claims abstract description 25
- 150000002736 metal compounds Chemical class 0.000 claims abstract description 24
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 7
- 238000011084 recovery Methods 0.000 claims abstract description 5
- 239000002131 composite material Substances 0.000 claims description 120
- 239000000243 solution Substances 0.000 claims description 96
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 24
- 239000011777 magnesium Substances 0.000 claims description 21
- 239000007864 aqueous solution Substances 0.000 claims description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 12
- 239000002798 polar solvent Substances 0.000 claims description 8
- 239000010936 titanium Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
- 229910052615 phyllosilicate Inorganic materials 0.000 claims description 6
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 5
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 239000010949 copper Substances 0.000 claims description 5
- 239000012046 mixed solvent Substances 0.000 claims description 5
- 238000003786 synthesis reaction Methods 0.000 claims description 5
- 229910052719 titanium Inorganic materials 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 229910052749 magnesium Inorganic materials 0.000 claims description 4
- 239000011572 manganese Substances 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 238000010979 pH adjustment Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
- 150000004703 alkoxides Chemical class 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- 230000003301 hydrolyzing effect Effects 0.000 claims description 3
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910021432 inorganic complex Inorganic materials 0.000 claims description 2
- 229910052744 lithium Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 229910052759 nickel Inorganic materials 0.000 claims description 2
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 claims description 2
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims description 2
- 238000001308 synthesis method Methods 0.000 abstract description 9
- 230000007062 hydrolysis Effects 0.000 abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 5
- 238000009833 condensation Methods 0.000 abstract description 3
- 230000005494 condensation Effects 0.000 abstract description 3
- 230000018044 dehydration Effects 0.000 abstract description 3
- 238000006297 dehydration reaction Methods 0.000 abstract description 3
- 229910013504 M-O-M Inorganic materials 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 52
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- -1 acrylic silanes Chemical class 0.000 description 24
- 125000004429 atom Chemical group 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
- 239000004593 Epoxy Substances 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 13
- 229920000647 polyepoxide Polymers 0.000 description 12
- 239000003822 epoxy resin Substances 0.000 description 10
- 125000005395 methacrylic acid group Chemical group 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 239000008199 coating composition Substances 0.000 description 9
- 239000000945 filler Substances 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- 239000011259 mixed solution Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 5
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 5
- 238000002441 X-ray diffraction Methods 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 229910010272 inorganic material Inorganic materials 0.000 description 5
- 239000011147 inorganic material Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229910000077 silane Inorganic materials 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- WGECXQBGLLYSFP-UHFFFAOYSA-N 2,3-dimethylpentane Chemical compound CCC(C)C(C)C WGECXQBGLLYSFP-UHFFFAOYSA-N 0.000 description 3
- BZHMBWZPUJHVEE-UHFFFAOYSA-N 2,3-dimethylpentane Natural products CC(C)CC(C)C BZHMBWZPUJHVEE-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229940050906 magnesium chloride hexahydrate Drugs 0.000 description 3
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011368 organic material Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 2
- VLJXXKKOSFGPHI-UHFFFAOYSA-N 3-methylhexane Chemical compound CCCC(C)CC VLJXXKKOSFGPHI-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HUDWMOHBQSXTDN-UHFFFAOYSA-N CC(=C)C([Cu])=O Chemical compound CC(=C)C([Cu])=O HUDWMOHBQSXTDN-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000003172 aldehyde group Chemical group 0.000 description 2
- 150000001343 alkyl silanes Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
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- 239000000805 composite resin Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- JZCCFEFSEZPSOG-UHFFFAOYSA-L copper(II) sulfate pentahydrate Chemical compound O.O.O.O.O.[Cu+2].[O-]S([O-])(=O)=O JZCCFEFSEZPSOG-UHFFFAOYSA-L 0.000 description 2
- 239000007771 core particle Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004093 cyano group Chemical group *C#N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- YGUFXEJWPRRAEK-UHFFFAOYSA-N dodecyl(triethoxy)silane Chemical compound CCCCCCCCCCCC[Si](OCC)(OCC)OCC YGUFXEJWPRRAEK-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethylcyclohexane Chemical compound CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 239000010419 fine particle Substances 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000011229 interlayer Substances 0.000 description 2
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 2
- QWTDNUCVQCZILF-UHFFFAOYSA-N isopentane Chemical compound CCC(C)C QWTDNUCVQCZILF-UHFFFAOYSA-N 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 229940091250 magnesium supplement Drugs 0.000 description 2
- 239000000463 material Substances 0.000 description 2
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- 239000000178 monomer Substances 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 239000006228 supernatant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
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- 125000003396 thiol group Chemical class [H]S* 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
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- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 1
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- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 1
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- SZMDWWICIPJEHQ-UHFFFAOYSA-N 1-triethoxysilylpropan-2-yl prop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CC(C)OC(=O)C=C SZMDWWICIPJEHQ-UHFFFAOYSA-N 0.000 description 1
- XTVNGRMJOGNDOG-UHFFFAOYSA-N 1-trimethoxysilylpropan-2-yl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CC(C)OC(=O)C(C)=C XTVNGRMJOGNDOG-UHFFFAOYSA-N 0.000 description 1
- OFTWZAMAJGNSKD-UHFFFAOYSA-N 1-trimethoxysilylpropan-2-yl prop-2-enoate Chemical compound CO[Si](OC)(OC)CC(C)OC(=O)C=C OFTWZAMAJGNSKD-UHFFFAOYSA-N 0.000 description 1
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- SJJMMZVIBLQHLI-UHFFFAOYSA-N 11-triethoxysilylundecanal Chemical compound CCO[Si](OCC)(OCC)CCCCCCCCCCC=O SJJMMZVIBLQHLI-UHFFFAOYSA-N 0.000 description 1
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- JSAWNNBNKSBJCB-UHFFFAOYSA-N 2-[ethoxy(dimethyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(C)C(C)CN JSAWNNBNKSBJCB-UHFFFAOYSA-N 0.000 description 1
- QMOCHTLIIWRLQV-UHFFFAOYSA-N 2-[methyl(3-trimethoxysilylpropyl)amino]ethanol Chemical compound CO[Si](OC)(OC)CCCN(C)CCO QMOCHTLIIWRLQV-UHFFFAOYSA-N 0.000 description 1
- FGSFVBRPCKXYDI-UHFFFAOYSA-N 2-triethoxysilylethyl 2-methylprop-2-enoate Chemical compound CCO[Si](OCC)(OCC)CCOC(=O)C(C)=C FGSFVBRPCKXYDI-UHFFFAOYSA-N 0.000 description 1
- RDCTZTAAYLXPDJ-UHFFFAOYSA-N 2-trimethoxysilylethyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCOC(=O)C(C)=C RDCTZTAAYLXPDJ-UHFFFAOYSA-N 0.000 description 1
- BUJVPKZRXOTBGA-UHFFFAOYSA-N 2-trimethoxysilylethyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCOC(=O)C=C BUJVPKZRXOTBGA-UHFFFAOYSA-N 0.000 description 1
- GXDMUOPCQNLBCZ-UHFFFAOYSA-N 3-(3-triethoxysilylpropyl)oxolane-2,5-dione Chemical compound CCO[Si](OCC)(OCC)CCCC1CC(=O)OC1=O GXDMUOPCQNLBCZ-UHFFFAOYSA-N 0.000 description 1
- HUPGCAGBHBJUJC-UHFFFAOYSA-N 3-(3-trimethoxysilylpropoxy)aniline Chemical compound CO[Si](OC)(OC)CCCOC1=CC=CC(N)=C1 HUPGCAGBHBJUJC-UHFFFAOYSA-N 0.000 description 1
- ZADOWCXTUZWAKL-UHFFFAOYSA-N 3-(3-trimethoxysilylpropyl)oxolane-2,5-dione Chemical compound CO[Si](OC)(OC)CCCC1CC(=O)OC1=O ZADOWCXTUZWAKL-UHFFFAOYSA-N 0.000 description 1
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Images
Classifications
-
- 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
- C08G79/00—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule
- C08G79/10—Macromolecular compounds obtained by reactions forming a linkage containing atoms other than silicon, sulfur, nitrogen, oxygen, and carbon with or without the latter elements in the main chain of the macromolecule a linkage containing aluminium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
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Abstract
【解決手段】M−O−M(Mは珪素原子または金属原子をそれぞれ独立に示す)で表される結合を含む珪素および金属の酸化物からなるとともに少なくとも一部の珪素原子に結合している有機基をもつ有機無機複合体の合成方法であって、
1以上のアルコキシ基をもち有機基と共有結合で結合した珪素原子を有するオルガノアルコキシシランおよび金属原子を含む金属化合物を極性溶媒である第一溶媒に溶解して原料溶液を調製する調製工程と、
オルガノアルコキシシランと金属化合物とを加水分解するとともに脱水縮合させて有機無機複合体を合成する反応工程と、
反応工程後の溶液に該溶液と相溶しない第二溶媒を加えて有機無機複合体を第二溶媒に溶解させた後、第二溶媒と相溶しない溶液を除去する除去工程と、
を含むことを特徴とする。
【選択図】なし
Description
1以上のアルコキシ基をもち前記有機基と共有結合で結合した前記珪素原子を有するオルガノアルコキシシランおよび前記金属原子を含む金属化合物を極性溶媒である第一溶媒に溶解して原料溶液を調製する調製工程と、
前記オルガノアルコキシシランと前記金属化合物とを加水分解するとともに脱水縮合させて前記有機無機複合体を合成する反応工程と、
前記反応工程後の溶液に該溶液と相溶しない第二溶媒を加えて前記有機無機複合体を該第二溶媒に溶解させた後、該第二溶媒と相溶しない溶液を除去する除去工程と、
を含むことを特徴とする。
調製工程は、オルガノアルコキシシランおよび金属化合物を第一溶媒に溶解して原料溶液を調製する工程である。なお、ここでの溶解は、オルガノアルコキシシランおよび/または金属化合物が粒子として第一溶媒に分散した状態も含む。
反応工程は、オルガノアルコキシシランと金属化合物とを加水分解するとともに脱水縮合させて有機無機複合体を合成する工程である。調製工程で調製した原料溶液に水が存在すると、オルガノアルコキシシランと金属化合物とが加水分解とともに脱水縮合する。特に、金属化合物として金属無機塩および/または金属有機塩を使用する場合、反応工程は、原料溶液のpHをアルカリ性に調整してオルガノアルコキシシランと金属化合物との反応を促進させるpH調整工程を含むとよい。pH調整工程では、原料溶液にアルカリを添加するとよい。添加するアルカリの種類に特に限定はなく、水酸化ナトリウム、水酸化カリウム、アンモニア等を水溶液で添加するとよい。アルカリ添加によって調整されるpHは、所望の程度以上の速度で結晶化が起こるpHであり、かつ有機基が損なわれるような強アルカリ性でなければよい。オルガノアルコキシシランと金属化合物の種類に依存するため一律には規定できないが、層状有機無機複合体の合成であれば、たとえばpH8〜10程度であるのが望ましい。オルガノアルコキシシランと金属化合物は、水もしくは水とアルカリとの存在により、金属化合物が先に加水分解され、もしくは、金属水酸化物となり、どちらの場合においても−M’−OHを生ずる。この−M’−OHがオルガノアルコキシシランの加水分解を促してさらに結合することで,R−Si−O−M’であらわされる結合をもつ有機無機複合体が合成される。層状の有機無機複合体が形成される場合には、金属原子M’を中心原子とする8面体構造層の結晶構造が先行して成長しつつ、これに追従してオルガノアルコキシシランの珪素がアルコキシ基の加水分解の後の脱水縮合により8面体構造層に結合し、この珪素を中心に4面体構造層の結晶構造も成長して行くものと推定される。
除去工程では、反応工程後の溶液に第二溶媒を加えて、有機無機複合体を第二溶媒に溶解させる。第二溶媒は反応工程後の溶液と相溶しないため、両者は分離する。その後、第二溶媒と相溶しない溶液を除去する。なお、反応工程後の溶液は、通常、反応工程において多量の水が添加されるため、実質的に水溶液である。すなわち、第二溶媒は少なくとも水と相溶せず有機無機複合体を溶解する溶媒であればよい。以下の説明では、反応工程後の溶液を「水溶液」として説明する。
250mlのメタノールに9.9g(0.05mol)の塩化鉄(II)四水和物を加えて撹拌した。塩化鉄(II)四水和物が溶解した後、24.8g(0.1mol)の3−メタクリロキシプロピルトリメトキシシランを加えて30分撹拌して原料溶液を得た。
250mlのメタノールに12.1g(0.05mol)の塩化アルミニウム(III)六水和物を加えて撹拌した。塩化アルミニウム(III)六水和物が溶解した後、24.8g(0.1mol)の3−メタクリロキシプロピルトリメトキシシランを加えて30分撹拌して原料溶液を得た。
250mlのメタノールに122.5g(0.05mol)の硫酸銅(II)五水和物を加えて撹拌した。硫酸銅(II)五水和物がメタノールに分散させた後、24.8g(0.1mol)の3−メタクリロキシプロピルトリメトキシシランを加えて30分撹拌して原料溶液を得た。
500mlのメタノールに51.1g(0.25mol)の塩化マグネシウム六水和物を加えて撹拌した。塩化マグネシウム六水和物が溶解した後、118g(0.5mol)の3−グリシドキシプロピルトリメトキシシラン(チッソ株式会社製サイラエースS510)を加えて撹拌して原料溶液を得た。
エポキシ系Mg層状複合体/クロロホルム溶液の固形分濃度を測定後、エポキシ系Mg層状複合体/クロロホルム溶液にエポキシ樹脂(ジャパンエポキシレジン株式会社製エピコート604)を加えて溶解させた。エポキシ樹脂の配合量は、エポキシ系Mg層状複合体とエポキシ樹脂との質量比がエポキシ系Mg層状複合体:エポキシ樹脂=1:2、2:10および1:10の3種類とした。次に、それぞれの溶液からロータリーエバポレータ(バス温:40℃)でクロロホルムを除去し、60℃の油浴で加熱しながらロータリーポンプで脱気を行い、エポキシ系Mg層状複合体/エポキシ樹脂混合物を得た。いずれの混合物も透明であった。つまり、本実施例の方法により得られたエポキシ系Mg層状複合体は、微細で有機溶媒への分散性に富む。
実施例4と同様の手順で原料溶液を調製した後、得られた原料溶液に、実施例4と同様の手順で水酸化ナトリウム溶液を加えて攪拌して混合した。
2:8面体シート
3:珪素原子
4:4面体シート
Claims (11)
- M−O−M(Mは珪素原子または金属原子をそれぞれ独立に示す)で表される結合を含む珪素および金属の酸化物からなるとともに少なくとも一部の珪素原子に結合している有機基をもつ有機無機複合体の合成方法であって、
1以上のアルコキシ基をもち前記有機基と共有結合で結合した前記珪素原子を有するオルガノアルコキシシランおよび前記金属原子を含む金属化合物を極性溶媒である第一溶媒に溶解して原料溶液を調製する調製工程と、
前記オルガノアルコキシシランと前記金属化合物とを加水分解するとともに脱水縮合させて前記有機無機複合体を合成する反応工程と、
前記反応工程後の溶液に該溶液と相溶しない第二溶媒を加えて前記有機無機複合体を該第二溶媒に溶解させた後、該第二溶媒と相溶しない溶液を除去する除去工程と、
を含むことを特徴とする有機無機複合体の合成方法。 - 前記反応工程は、前記原料溶液に水を添加して前記有機無機複合体を合成する工程であって、
前記除去工程は、前記反応工程後の水溶液に少なくとも水と相溶しない前記第二溶媒を加えた後、該水溶液を除去する工程である請求項1記載の有機無機複合体の合成方法。 - 前記第一溶媒は、無機系および有機系の極性溶媒から選ばれる1種あるいは2種以上の混合溶媒である請求項1記載の有機無機複合体の合成方法。
- 前記第一溶媒は、水、低級アルコールおよびアセトンから選ばれる1種あるいは2種以上の混合溶媒である請求項3記載の有機無機複合体の合成方法。
- 前記第二溶媒は、酢酸エチル、トルエンおよびクロロホルムから選ばれる1種以上である請求項1記載の有機無機複合体の合成方法。
- 前記反応工程は、前記原料溶液のpHをアルカリ性に調整して前記オルガノアルコキシシランと前記金属化合物との反応を促進させるpH調整工程を含む請求項1記載の有機無機複合体の合成方法。
- 前記除去工程後、さらに、前記第二溶媒を除去して前記有機無機複合体を回収する回収工程を含む請求項1記載の有機無機複合体の合成方法。
- 前記金属原子は、マグネシウム(Mg)、アルミニウム(Al)、ニッケル(Ni)、コバルト(Co)、銅(Cu)、マンガン(Mn)、鉄(Fe)、リチウム(Li)、バナジウム(V)、ジルコニウム(Zr)およびチタン(Ti)から選ばれる少なくとも一種である請求項1記載の有機無機複合体の合成方法。
- 前記金属化合物は、前記金属原子の無機塩、有機塩またはアルコキシドである請求項1記載の有機無機複合体の合成方法。
- 前記有機無機複合体は、前記珪素原子を中心原子とする4面体面構造が構成する4面体構造層と前記金属原子を中心原子とする8面体面構造が構成する8面体構造層との2:1型または1:1型の積層体からなるフィロ珪酸塩鉱物型の層状構造を有する層状有機無機複合体である請求項1記載の有機無機複合体の合成方法。
- 前記層状有機無機複合体は、一般式:{RnSiO(4−n)/2}X〔M’OZ/2〕〔H2O〕W(ここでRは前記有機基、M’は前記金属原子、nは1〜3のいずれかの整数であり、xは0.5以上で2以下の整数に限定されない任意の数であり、zは金属原子M’の価数であって2または3の整数であり、wは(z/2)−1〜(z+1)/2の整数に限定されない構造水の分子数)で表される請求項10記載の有機無機複合体の合成方法。
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JP2009185149A (ja) * | 2008-02-05 | 2009-08-20 | Toyota Central R&D Labs Inc | 塗料組成物の製造方法および塗料組成物 |
WO2013065638A1 (ja) | 2011-10-31 | 2013-05-10 | 株式会社豊田中央研究所 | 2価-3価金属系有機無機層状複合体およびその製造方法 |
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JP5626594B2 (ja) * | 2011-10-31 | 2014-11-19 | 株式会社豊田中央研究所 | 2価−3価金属系有機無機層状複合体およびその製造方法 |
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