TW202140630A - 矽氧聚合物之製造方法 - Google Patents
矽氧聚合物之製造方法 Download PDFInfo
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- TW202140630A TW202140630A TW110108880A TW110108880A TW202140630A TW 202140630 A TW202140630 A TW 202140630A TW 110108880 A TW110108880 A TW 110108880A TW 110108880 A TW110108880 A TW 110108880A TW 202140630 A TW202140630 A TW 202140630A
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- Prior art keywords
- silicone polymer
- general formula
- compound
- silane
- compound represented
- Prior art date
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- 229920005573 silicon-containing polymer Polymers 0.000 title claims abstract description 89
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 44
- -1 silane compound Chemical class 0.000 claims abstract description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 36
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims abstract description 32
- 150000003856 quaternary ammonium compounds Chemical class 0.000 claims abstract description 32
- 229910000077 silane Inorganic materials 0.000 claims abstract description 30
- 239000003729 cation exchange resin Substances 0.000 claims abstract description 29
- 125000000962 organic group Chemical group 0.000 claims abstract description 26
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
- KIZQNNOULOCVDM-UHFFFAOYSA-M 2-hydroxyethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)CCO KIZQNNOULOCVDM-UHFFFAOYSA-M 0.000 claims description 19
- 125000003545 alkoxy group Chemical group 0.000 claims description 16
- 239000012295 chemical reaction liquid Substances 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- 239000000758 substrate Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 241000208340 Araliaceae Species 0.000 claims description 6
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 claims description 6
- 235000003140 Panax quinquefolius Nutrition 0.000 claims description 6
- RKTGAWJWCNLSFX-UHFFFAOYSA-M bis(2-hydroxyethyl)-dimethylazanium;hydroxide Chemical compound [OH-].OCC[N+](C)(C)CCO RKTGAWJWCNLSFX-UHFFFAOYSA-M 0.000 claims description 6
- 235000008434 ginseng Nutrition 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 5
- 229920005989 resin Polymers 0.000 claims description 5
- FBYBILSNSUSRGL-UHFFFAOYSA-N 2-hydroxyethyl(methyl)azanium hydroxide Chemical compound [OH-].C[NH2+]CCO FBYBILSNSUSRGL-UHFFFAOYSA-N 0.000 claims description 4
- 238000005341 cation exchange Methods 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims 1
- 125000001453 quaternary ammonium group Chemical group 0.000 claims 1
- 238000005406 washing Methods 0.000 abstract description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract description 2
- 101100237844 Mus musculus Mmp19 gene Proteins 0.000 abstract 1
- 239000000413 hydrolysate Substances 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000010408 film Substances 0.000 description 33
- 238000000576 coating method Methods 0.000 description 18
- 239000011248 coating agent Substances 0.000 description 16
- 239000000243 solution Substances 0.000 description 14
- 239000002904 solvent Substances 0.000 description 13
- 239000007864 aqueous solution Substances 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 8
- 239000007788 liquid Substances 0.000 description 7
- 229910052751 metal Inorganic materials 0.000 description 7
- 239000002184 metal Substances 0.000 description 7
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229920001429 chelating resin Polymers 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 6
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 229920002120 photoresistant polymer Polymers 0.000 description 5
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 4
- 238000001879 gelation Methods 0.000 description 4
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 4
- 238000005342 ion exchange Methods 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 4
- RPPHDZQVFFWREW-UHFFFAOYSA-M 1-hydroxyethyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CC(O)[N+](C)(C)C RPPHDZQVFFWREW-UHFFFAOYSA-M 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001476 alcoholic effect Effects 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- ZZHNUBIHHLQNHX-UHFFFAOYSA-N butoxysilane Chemical compound CCCCO[SiH3] ZZHNUBIHHLQNHX-UHFFFAOYSA-N 0.000 description 3
- XGZGKDQVCBHSGI-UHFFFAOYSA-N butyl(triethoxy)silane Chemical compound CCCC[Si](OCC)(OCC)OCC XGZGKDQVCBHSGI-UHFFFAOYSA-N 0.000 description 3
- 238000005530 etching Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 125000005372 silanol group Chemical group 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 239000010409 thin film Substances 0.000 description 3
- 229910021642 ultra pure water Inorganic materials 0.000 description 3
- 239000012498 ultrapure water Substances 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 2
- FHVCZJGBXWNGIZ-UHFFFAOYSA-M 4-methylbenzenesulfonate;tetramethylazanium Chemical compound C[N+](C)(C)C.CC1=CC=C(S([O-])(=O)=O)C=C1 FHVCZJGBXWNGIZ-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- CXRFDZFCGOPDTD-UHFFFAOYSA-M Cetrimide Chemical compound [Br-].CCCCCCCCCCCCCC[N+](C)(C)C CXRFDZFCGOPDTD-UHFFFAOYSA-M 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 239000012494 Quartz wool Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- UDYGXWPMSJPFDG-UHFFFAOYSA-M benzyl(tributyl)azanium;bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 UDYGXWPMSJPFDG-UHFFFAOYSA-M 0.000 description 2
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 2
- UUZYBYIOAZTMGC-UHFFFAOYSA-M benzyl(trimethyl)azanium;bromide Chemical compound [Br-].C[N+](C)(C)CC1=CC=CC=C1 UUZYBYIOAZTMGC-UHFFFAOYSA-M 0.000 description 2
- KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 2
- NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- SXPLZNMUBFBFIA-UHFFFAOYSA-N butyl(trimethoxy)silane Chemical compound CCCC[Si](OC)(OC)OC SXPLZNMUBFBFIA-UHFFFAOYSA-N 0.000 description 2
- OGCNPMTZBJEZKT-UHFFFAOYSA-N butyl(triphenoxy)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(CCCC)OC1=CC=CC=C1 OGCNPMTZBJEZKT-UHFFFAOYSA-N 0.000 description 2
- GNRBSDIBKIHSJH-UHFFFAOYSA-N butyl(tripropoxy)silane Chemical compound CCCC[Si](OCCC)(OCCC)OCCC GNRBSDIBKIHSJH-UHFFFAOYSA-N 0.000 description 2
- OOWHVJAPAMPBEX-UHFFFAOYSA-N butyl-tri(propan-2-yloxy)silane Chemical compound CCCC[Si](OC(C)C)(OC(C)C)OC(C)C OOWHVJAPAMPBEX-UHFFFAOYSA-N 0.000 description 2
- ZOKYFXXILHWZHP-UHFFFAOYSA-N butyl-tris[(2-methylpropan-2-yl)oxy]silane Chemical compound CCCC[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C ZOKYFXXILHWZHP-UHFFFAOYSA-N 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- ZMAPKOCENOWQRE-UHFFFAOYSA-N diethoxy(diethyl)silane Chemical compound CCO[Si](CC)(CC)OCC ZMAPKOCENOWQRE-UHFFFAOYSA-N 0.000 description 2
- ZZNQQQWFKKTOSD-UHFFFAOYSA-N diethoxy(diphenyl)silane Chemical compound C=1C=CC=CC=1[Si](OCC)(OCC)C1=CC=CC=C1 ZZNQQQWFKKTOSD-UHFFFAOYSA-N 0.000 description 2
- JJQZDUKDJDQPMQ-UHFFFAOYSA-N dimethoxy(dimethyl)silane Chemical compound CO[Si](C)(C)OC JJQZDUKDJDQPMQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 229940116333 ethyl lactate Drugs 0.000 description 2
- SBRXLTRZCJVAPH-UHFFFAOYSA-N ethyl(trimethoxy)silane Chemical compound CC[Si](OC)(OC)OC SBRXLTRZCJVAPH-UHFFFAOYSA-N 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- JYVPKRHOTGQJSE-UHFFFAOYSA-M hexyl(trimethyl)azanium;bromide Chemical compound [Br-].CCCCCC[N+](C)(C)C JYVPKRHOTGQJSE-UHFFFAOYSA-M 0.000 description 2
- 229910010272 inorganic material Inorganic materials 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- RJMRIDVWCWSWFR-UHFFFAOYSA-N methyl(tripropoxy)silane Chemical compound CCCO[Si](C)(OCCC)OCCC RJMRIDVWCWSWFR-UHFFFAOYSA-N 0.000 description 2
- HLXDKGBELJJMHR-UHFFFAOYSA-N methyl-tri(propan-2-yloxy)silane Chemical compound CC(C)O[Si](C)(OC(C)C)OC(C)C HLXDKGBELJJMHR-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 2
- 229940073455 tetraethylammonium hydroxide Drugs 0.000 description 2
- LRGJRHZIDJQFCL-UHFFFAOYSA-M tetraethylazanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC LRGJRHZIDJQFCL-UHFFFAOYSA-M 0.000 description 2
- DDFYFBUWEBINLX-UHFFFAOYSA-M tetramethylammonium bromide Chemical compound [Br-].C[N+](C)(C)C DDFYFBUWEBINLX-UHFFFAOYSA-M 0.000 description 2
- PJLHNSWILUSPNO-UHFFFAOYSA-M tetramethylazanium;thiocyanate Chemical compound [S-]C#N.C[N+](C)(C)C PJLHNSWILUSPNO-UHFFFAOYSA-M 0.000 description 2
- LPSKDVINWQNWFE-UHFFFAOYSA-M tetrapropylazanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCC LPSKDVINWQNWFE-UHFFFAOYSA-M 0.000 description 2
- 229920001187 thermosetting polymer Polymers 0.000 description 2
- DEKZKCDJQLBBRA-UHFFFAOYSA-N tributoxy(butyl)silane Chemical compound CCCCO[Si](CCCC)(OCCCC)OCCCC DEKZKCDJQLBBRA-UHFFFAOYSA-N 0.000 description 2
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 2
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 2
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical group CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 2
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical group CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 2
- HADKRTWCOYPCPH-UHFFFAOYSA-M trimethylphenylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C1=CC=CC=C1 HADKRTWCOYPCPH-UHFFFAOYSA-M 0.000 description 2
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 description 1
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 description 1
- PKKOHHSZSAQSPU-UHFFFAOYSA-M 1-hydroxyethyl(tripropyl)azanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)C(C)O PKKOHHSZSAQSPU-UHFFFAOYSA-M 0.000 description 1
- DYICMSDYEXLWBI-UHFFFAOYSA-M 1-hydroxypropyl(tripropyl)azanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)C(O)CC DYICMSDYEXLWBI-UHFFFAOYSA-M 0.000 description 1
- BLXHKBMKKYCBBM-UHFFFAOYSA-M 2,2-dihydroxyethyl(trimethyl)azanium hydroxide Chemical compound [OH-].OC(C[N+](C)(C)C)O BLXHKBMKKYCBBM-UHFFFAOYSA-M 0.000 description 1
- IAQQDIGGISSSQO-UHFFFAOYSA-N 2-(4-fluorophenyl)piperidine Chemical compound C1=CC(F)=CC=C1C1NCCCC1 IAQQDIGGISSSQO-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- ZFDNAYFXBJPPEB-UHFFFAOYSA-M 2-hydroxyethyl(tripropyl)azanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCO ZFDNAYFXBJPPEB-UHFFFAOYSA-M 0.000 description 1
- SHAMRMCOVNDTCS-UHFFFAOYSA-M 2-hydroxypropyl(trimethyl)azanium;hydroxide Chemical compound [OH-].CC(O)C[N+](C)(C)C SHAMRMCOVNDTCS-UHFFFAOYSA-M 0.000 description 1
- YSDSJBOULHYPCB-UHFFFAOYSA-M 2-hydroxypropyl(tripropyl)azanium hydroxide Chemical compound [OH-].OC(C[N+](CCC)(CCC)CCC)C YSDSJBOULHYPCB-UHFFFAOYSA-M 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- AJEUSSNTTSVFIZ-UHFFFAOYSA-M 3-hydroxypropyl(trimethyl)azanium;hydroxide Chemical compound [OH-].C[N+](C)(C)CCCO AJEUSSNTTSVFIZ-UHFFFAOYSA-M 0.000 description 1
- FBUSDOJQYGVKGA-UHFFFAOYSA-M 3-hydroxypropyl(tripropyl)azanium;hydroxide Chemical compound [OH-].CCC[N+](CCC)(CCC)CCCO FBUSDOJQYGVKGA-UHFFFAOYSA-M 0.000 description 1
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 description 1
- JNTAPKSOXQRBOB-UHFFFAOYSA-N C(C)[Si](OC)(OC)CC.C(C)[Si](OCC)(OCC)CC Chemical compound C(C)[Si](OC)(OC)CC.C(C)[Si](OCC)(OCC)CC JNTAPKSOXQRBOB-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- BAVYZALUXZFZLV-UHFFFAOYSA-O Methylammonium ion Chemical compound [NH3+]C BAVYZALUXZFZLV-UHFFFAOYSA-O 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 description 1
- GZKPFPHTXXYDKV-UHFFFAOYSA-M [Cl].[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC Chemical compound [Cl].[Br-].C(CCC)[N+](CCCC)(CCCC)CCCC GZKPFPHTXXYDKV-UHFFFAOYSA-M 0.000 description 1
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- NCODAQVPIYEDJJ-UHFFFAOYSA-M [OH-].OC(C[N+](CCCC)(CCCC)CCCC)C Chemical compound [OH-].OC(C[N+](CCCC)(CCCC)CCCC)C NCODAQVPIYEDJJ-UHFFFAOYSA-M 0.000 description 1
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- 230000002194 synthesizing effect Effects 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- UQMOLLPKNHFRAC-UHFFFAOYSA-N tetrabutyl silicate Chemical compound CCCCO[Si](OCCCC)(OCCCC)OCCCC UQMOLLPKNHFRAC-UHFFFAOYSA-N 0.000 description 1
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- HWCKGOZZJDHMNC-UHFFFAOYSA-M tetraethylammonium bromide Chemical compound [Br-].CC[N+](CC)(CC)CC HWCKGOZZJDHMNC-UHFFFAOYSA-M 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- UQFSVBXCNGCBBW-UHFFFAOYSA-M tetraethylammonium iodide Chemical compound [I-].CC[N+](CC)(CC)CC UQFSVBXCNGCBBW-UHFFFAOYSA-M 0.000 description 1
- RXMRGBVLCSYIBO-UHFFFAOYSA-M tetramethylazanium;iodide Chemical compound [I-].C[N+](C)(C)C RXMRGBVLCSYIBO-UHFFFAOYSA-M 0.000 description 1
- ADLSSRLDGACTEX-UHFFFAOYSA-N tetraphenyl silicate Chemical group C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 ADLSSRLDGACTEX-UHFFFAOYSA-N 0.000 description 1
- ZUEKXCXHTXJYAR-UHFFFAOYSA-N tetrapropan-2-yl silicate Chemical compound CC(C)O[Si](OC(C)C)(OC(C)C)OC(C)C ZUEKXCXHTXJYAR-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
- BGQMOFGZRJUORO-UHFFFAOYSA-M tetrapropylammonium bromide Chemical compound [Br-].CCC[N+](CCC)(CCC)CCC BGQMOFGZRJUORO-UHFFFAOYSA-M 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- HKALKJRBIYJXJT-UHFFFAOYSA-N tri(butan-2-yloxy)-butylsilane Chemical group CCCC[Si](OC(C)CC)(OC(C)CC)OC(C)CC HKALKJRBIYJXJT-UHFFFAOYSA-N 0.000 description 1
- MHQDJCZAQGWXBC-UHFFFAOYSA-N tri(butan-2-yloxy)-ethenylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C=C MHQDJCZAQGWXBC-UHFFFAOYSA-N 0.000 description 1
- SGHZCASSRKVVCL-UHFFFAOYSA-N tri(butan-2-yloxy)-ethylsilane Chemical compound CCC(C)O[Si](CC)(OC(C)CC)OC(C)CC SGHZCASSRKVVCL-UHFFFAOYSA-N 0.000 description 1
- RJNDDRZGJNVASH-UHFFFAOYSA-N tri(butan-2-yloxy)-methylsilane Chemical compound CCC(C)O[Si](C)(OC(C)CC)OC(C)CC RJNDDRZGJNVASH-UHFFFAOYSA-N 0.000 description 1
- PCFHEMOVRWHGSP-UHFFFAOYSA-N tri(butan-2-yloxy)-octylsilane Chemical compound C(CCCCCCC)[Si](OC(C)CC)(OC(C)CC)OC(C)CC PCFHEMOVRWHGSP-UHFFFAOYSA-N 0.000 description 1
- QSQGFMKPTBYFTM-UHFFFAOYSA-N tri(butan-2-yloxy)-propan-2-ylsilane Chemical compound CCC(C)O[Si](OC(C)CC)(OC(C)CC)C(C)C QSQGFMKPTBYFTM-UHFFFAOYSA-N 0.000 description 1
- ZARIZDBUWOPYMT-UHFFFAOYSA-N tri(butan-2-yloxy)-propylsilane Chemical compound CCC(C)O[Si](CCC)(OC(C)CC)OC(C)CC ZARIZDBUWOPYMT-UHFFFAOYSA-N 0.000 description 1
- MQVCTPXBBSKLFS-UHFFFAOYSA-N tri(propan-2-yloxy)-propylsilane Chemical compound CCC[Si](OC(C)C)(OC(C)C)OC(C)C MQVCTPXBBSKLFS-UHFFFAOYSA-N 0.000 description 1
- SGCFZHOZKKQIBU-UHFFFAOYSA-N tributoxy(ethenyl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C=C SGCFZHOZKKQIBU-UHFFFAOYSA-N 0.000 description 1
- GIHPVQDFBJMUAO-UHFFFAOYSA-N tributoxy(ethyl)silane Chemical compound CCCCO[Si](CC)(OCCCC)OCCCC GIHPVQDFBJMUAO-UHFFFAOYSA-N 0.000 description 1
- GYZQBXUDWTVJDF-UHFFFAOYSA-N tributoxy(methyl)silane Chemical compound CCCCO[Si](C)(OCCCC)OCCCC GYZQBXUDWTVJDF-UHFFFAOYSA-N 0.000 description 1
- INUOIYMEJLOQFN-UHFFFAOYSA-N tributoxy(phenyl)silane Chemical group CCCCO[Si](OCCCC)(OCCCC)C1=CC=CC=C1 INUOIYMEJLOQFN-UHFFFAOYSA-N 0.000 description 1
- LEZQEMOONYYJBM-UHFFFAOYSA-N tributoxy(propan-2-yl)silane Chemical compound CCCCO[Si](OCCCC)(OCCCC)C(C)C LEZQEMOONYYJBM-UHFFFAOYSA-N 0.000 description 1
- WAAWAIHPWOJHJJ-UHFFFAOYSA-N tributoxy(propyl)silane Chemical compound CCCCO[Si](CCC)(OCCCC)OCCCC WAAWAIHPWOJHJJ-UHFFFAOYSA-N 0.000 description 1
- MOQKEWDCYXOQBX-UHFFFAOYSA-M tributyl(1-hydroxyethyl)azanium;hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)C(C)O MOQKEWDCYXOQBX-UHFFFAOYSA-M 0.000 description 1
- RBMGCSAOUFVTQM-UHFFFAOYSA-M tributyl(3-hydroxypropyl)azanium;hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCO RBMGCSAOUFVTQM-UHFFFAOYSA-M 0.000 description 1
- BJDLPDPRMYAOCM-UHFFFAOYSA-N triethoxy(propan-2-yl)silane Chemical compound CCO[Si](OCC)(OCC)C(C)C BJDLPDPRMYAOCM-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- QYBKVVRRGQSGDC-UHFFFAOYSA-N triethyl methyl silicate Chemical compound CCO[Si](OC)(OCC)OCC QYBKVVRRGQSGDC-UHFFFAOYSA-N 0.000 description 1
- ZGKZQHAYPIDZLW-UHFFFAOYSA-M triethyl(1-hydroxypropyl)azanium;hydroxide Chemical compound [OH-].CCC(O)[N+](CC)(CC)CC ZGKZQHAYPIDZLW-UHFFFAOYSA-M 0.000 description 1
- GRNRCQKEBXQLAA-UHFFFAOYSA-M triethyl(2-hydroxyethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CCO GRNRCQKEBXQLAA-UHFFFAOYSA-M 0.000 description 1
- RBUVMOSJYGXQEK-UHFFFAOYSA-M triethyl(2-hydroxypropyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CC(C)O RBUVMOSJYGXQEK-UHFFFAOYSA-M 0.000 description 1
- RPMOERPGTQLCAT-UHFFFAOYSA-M triethyl(hydroxymethyl)azanium;hydroxide Chemical compound [OH-].CC[N+](CC)(CC)CO RPMOERPGTQLCAT-UHFFFAOYSA-M 0.000 description 1
- NLSFXUALGZKXNV-UHFFFAOYSA-N trimethoxy(3-propoxypropyl)silane Chemical compound CCCOCCC[Si](OC)(OC)OC NLSFXUALGZKXNV-UHFFFAOYSA-N 0.000 description 1
- LGROXJWYRXANBB-UHFFFAOYSA-N trimethoxy(propan-2-yl)silane Chemical compound CO[Si](OC)(OC)C(C)C LGROXJWYRXANBB-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-UHFFFAOYSA-N 0.000 description 1
- KKLAORVGAKUOPZ-UHFFFAOYSA-M trimethyl(phenyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)C1=CC=CC=C1 KKLAORVGAKUOPZ-UHFFFAOYSA-M 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-O trimethylammonium Chemical compound C[NH+](C)C GETQZCLCWQTVFV-UHFFFAOYSA-O 0.000 description 1
- IXJNGXCZSCHDFE-UHFFFAOYSA-N triphenoxy(phenyl)silane Chemical compound C=1C=CC=CC=1O[Si](C=1C=CC=CC=1)(OC=1C=CC=CC=1)OC1=CC=CC=C1 IXJNGXCZSCHDFE-UHFFFAOYSA-N 0.000 description 1
- FNNJGIKXHZZGCV-UHFFFAOYSA-N triphenoxy(propan-2-yl)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(C(C)C)OC1=CC=CC=C1 FNNJGIKXHZZGCV-UHFFFAOYSA-N 0.000 description 1
- AMUIJRKZTXWCEA-UHFFFAOYSA-N triphenoxy(propyl)silane Chemical compound C=1C=CC=CC=1O[Si](OC=1C=CC=CC=1)(CCC)OC1=CC=CC=C1 AMUIJRKZTXWCEA-UHFFFAOYSA-N 0.000 description 1
- KGOOITCIBGXHJO-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-phenylsilane Chemical compound CC(C)(C)O[Si](OC(C)(C)C)(OC(C)(C)C)C1=CC=CC=C1 KGOOITCIBGXHJO-UHFFFAOYSA-N 0.000 description 1
- MJIHPVLPZKWFBL-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-propan-2-ylsilane Chemical compound CC(C)(C)O[Si](C(C)C)(OC(C)(C)C)OC(C)(C)C MJIHPVLPZKWFBL-UHFFFAOYSA-N 0.000 description 1
- DIZPPYBTFPZSGK-UHFFFAOYSA-N tris[(2-methylpropan-2-yl)oxy]-propylsilane Chemical compound CCC[Si](OC(C)(C)C)(OC(C)(C)C)OC(C)(C)C DIZPPYBTFPZSGK-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002349 well water Substances 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G77/04—Polysiloxanes
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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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Abstract
本發明提供一種由於不需要水洗步驟而產率大幅改善,所得到之矽氧聚合物為安定之製造方法。矽氧聚合物之製造方法,係使選自通式(1)所示之化合物:Ra
Si(OR1
)4-a
…(1)(式中,R表示氫原子或1價有機基,R1
表示1價有機基,a表示1~2之整數)、及通式(2)所示之化合物:Si(OR2
)4
…(2)(式中,R2
表示1價有機基)的至少1種矽烷化合物,與四級銨化合物於水存在下水解後,與陽離子交換樹脂接觸。
Description
本發明係關於一種製造方法,其大幅改善產率,且所得到之矽氧聚合物為安定。
矽氧聚合物係將有機化合物及無機化合物以分子層級組合而成之有機-無機混成材料,由於係兼具柔軟性或加工性之有機材料的特長、及耐熱性・耐候性或耐化學性之無機材料的特長之素材,因此近年來被積極地研究。
其中,在製造半導體用元件等時之圖案成型中,已提出當應用微影技術、蝕刻技術等之反轉圖案形成時,使用矽氧聚合物作為光阻下層膜。在矽氧聚合物之中,尤其是包含大量源自四甲氧基矽烷或四乙氧基矽烷之結構的情況,已知對微細之光阻下層膜圖案之埋入性及藉由氧系氣體蝕刻等去除光阻下層膜圖案時的蝕刻耐性優良。
在以烷氧基矽烷作為原料,得到光阻下層膜用之矽氧聚合物的情況,一般係使用酸或鹼作為觸媒。鹼之中,尤其是使用四級銨化合物作為觸媒的情況,已知矽氧聚合物為安定,所得到的膜之機械強度優良(參照專利文獻1~3)。此等特性被認為與以下有關:四級銨化合物與酸觸媒或其他鹼觸媒不同,由於與烷氧基水解所產生之矽醇基形成離子對而達成平衡,故容易形成例如被稱為籠型結構的特異高級結構(參照專利文獻1~4)。
另一方面,在以四級銨化合物作為觸媒,得到矽氧聚合物的情況,需要四級銨化合物之中和、水洗。為了塗布於基材以得到膜,矽氧聚合物必須在某種程度上含有為縮合活性基的矽醇基,但在將四級銨化合物用於觸媒的情況,由於與矽醇基形成離子對,因此即使直接加熱也不會縮合。因此,必須用酸將四級銨化合物中和,並藉由水洗去除中和所生成的鹽等。
然而,尤其是含有大量源自四甲氧基矽烷或四乙氧基矽烷之結構的矽氧聚合物,由於極性高而容易溶解於水,即使水洗水層與油層亦不分離,有無法得到矽氧聚合物的情況。又,即使水層與油層分離,由於矽氧聚合物從油層分布至水層而被去除,因此矽氧聚合物之產率變得極差,有實質上在工業上無法使用的問題。尋求一種使用四級銨化合物作為觸媒,產率良好地得到含有大量源自四甲氧基矽烷或四乙氧基矽烷之結構的矽氧聚合物之方法。
[先前技術文獻]
[專利文獻]
[專利文獻1]日本專利第4530113號公報
[專利文獻2]日本專利第6256775號公報
[專利文獻3]日本特開2016-11411號公報
[專利文獻4]日本專利第4409397號公報
[發明欲解決之課題]
本發明之目的,係關於一種一邊以四級銨化合物作為觸媒,一邊大幅改善產率,且所得到之矽氧聚合物為安定之製造方法。
[用以解決課題之手段]
本發明之矽氧聚合物之製造方法,其特徵為使選自下述通式(1)所示之化合物、及下述通式(2)所示之化合物的至少1種矽烷化合物,與四級銨化合物於水存在下水解後,與陽離子交換樹脂接觸,
Ra
Si(OR1
)4-a
・・・・・(1)
(式中,R表示氫原子或1價有機基,R1
表示1價有機基,a表示1~2之整數)
Si(OR2
)4
・・・・・(2)
(式中,R2
表示1價有機基)
[發明之效果]
本發明之矽氧聚合物之製造方法,由於藉由使反應液與陽離子交換樹脂接觸而將四級銨化合物去除,所以不需要藉由酸的中和及水洗。因此,不會因水層與油層不分離而無法得到矽氧聚合物、或矽氧聚合物不會分布至水層而被去除,可提高產率。
又,本發明之矽氧聚合物之製造方法,不進行凝膠化,能得到可溶於有機溶劑的聚合物。再者,安定性高,分子量不易變化。
藉由本發明之矽氧聚合物之製造方法所製造的矽氧聚合物,在形成塗膜時,可得到鉛筆硬度為4H以上之硬塗膜。硬塗膜係耐刮傷性高。
藉由本發明之矽氧聚合物之製造方法所製造的矽氧聚合物組成物,可藉由旋轉塗布等一般塗膜方法進行塗膜。又,藉由本發明之矽氧聚合物之製造方法所製造的矽氧聚合物組成物,在塗布於基板之情況,可於基板上形成薄膜,藉由加熱,可於基板上製成熱硬化薄膜。以此種方式所形成之熱硬化薄膜,由於具有透明性及耐熱性優良的特性,可使用於半導體或顯示器之保護膜及光阻下層膜等。
又,藉由本發明之矽氧聚合物之製造方法所製造的矽氧聚合物,由於原料中不含金屬,可適合使用於顯示器或半導體之電子資訊材料。
又,使用本發明之矽氧聚合物之製造方法所得到的矽氧聚合物,不限於電子資訊材料領域,而可應用於塗料或接著劑等廣泛的領域。
[用以實施發明的形態]
本發明之矽氧聚合物之製造方法,其特徵為使選自前述通式(1)所示之化合物、及前述通式(2)所示之化合物的至少1種矽烷化合物,與四級銨化合物於水存在下水解後,與陽離子交換樹脂接觸,
Ra
Si(OR1
)4-a
・・・・・(1)
(式中,R表示氫原子或1價有機基,R1
表示1價有機基,a表示1~2之整數)
Si(OR2
)4
・・・・・(2)
(式中,R2
表示1價有機基)
在上述通式(1)中,R為1價有機基時,R及R1
互相獨立,可為相同之有機基,亦可為相異之有機基。又,a為2時,R互相獨立,可為1種1價有機基或2種1價有機基。再者,2個以上之R1
互相獨立,可為1種1價有機基或2種以上的1價有機基。就通式(2)所示之化合物而言,作為R及R1
之1價有機基,可列舉烷基、芳基、乙烯基、烯丙基、環氧丙基等。又,在通式(1)中,R以1價有機基,尤其是烷基或芳基為較佳。
此處,就烷基而言,可列舉甲基、乙基、丙基、丁基、戊基等,較佳為碳數1~5之烷基,此等烷基可為鏈狀,亦可分枝,再者,氫原子可被氟原子等取代。
又,就芳基而言,可列舉苯基、萘基、甲基苯基、乙基苯基、氯苯基、溴苯基、氟苯基等。
就通式(1)所示之化合物的具體例而言,可列舉甲基三甲氧基矽烷、甲基三乙氧基矽烷、甲基三正丙氧基矽烷、甲基三異丙氧基矽烷、甲基三正丁氧基矽烷、甲基三-二級丁氧基矽烷、甲基三-三級丁氧基矽烷、甲基三苯氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、乙基三正丙氧基矽烷、乙基三異丙氧基矽烷、乙基三正丁氧基矽烷、乙基三-二級丁氧基矽烷、乙基三-三級丁氧基矽烷、乙基三苯氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基三正丙氧基矽烷、乙烯基三異丙氧基矽烷、乙烯基三正丁氧基矽烷、乙烯基三-二級丁氧基矽烷、乙烯基三-三級丁氧基矽烷、乙烯基三苯氧基矽烷、正丙基三甲氧基矽烷、正丙基三乙氧基矽烷、正丙基三正丙氧基矽烷、正丙基三異丙氧基矽烷、正丙基三正丁氧基矽烷、正丙基三-二級丁氧基矽烷、正丙基三-三級丁氧基矽烷、正丙基三苯氧基矽烷、異丙基三甲氧基矽烷、異丙基三乙氧基矽烷、異丙基三正丙氧基矽烷、異丙基三異丙氧基矽烷、異丙基三正丁氧基矽烷、異丙基三-二級丁氧基矽烷、異丙基三-三級丁氧基矽烷、異丙基三苯氧基矽烷、正丁基三甲氧基矽烷、正丁基三乙氧基矽烷、正丁基三正丙氧基矽烷、正丁基三異丙氧基矽烷、正丁基三正丁氧基矽烷、正丁基三-二級丁氧基矽烷、正丁基三-三級丁氧基矽烷、正丁基三苯氧基矽烷、二級丁基三甲氧基矽烷、二級丁基三乙氧基矽烷、二級丁基三正丙氧基矽烷、二級丁基三異丙氧基矽烷、二級丁基三正丁氧基矽烷、二級丁基三-二級丁氧基矽烷、二級丁基三-三級丁氧基矽烷、二級丁基-三苯氧基矽烷、三級丁基三甲氧基矽烷、三級丁基三乙氧基矽烷、三級丁基三正丙氧基矽烷、三級丁基三異丙氧基矽烷、三級丁基三正丁氧基矽烷、三級丁基三-二級丁氧基矽烷、三級丁基三-三級丁氧基矽烷、三級丁基三苯氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、苯基三正丙氧基矽烷、苯基三異丙氧基矽烷、苯基三正丁氧基矽烷、苯基三-二級丁氧基矽烷、苯基三-三級丁氧基矽烷、苯基三苯氧基矽烷、γ-胺基丙基三甲氧基矽烷、γ-胺基丙基三乙氧基矽烷、γ-環氧丙氧基丙基三甲氧基矽烷、γ-環氧丙氧基丙基三乙氧基矽烷、γ-三氟丙基三甲氧基矽烷、γ-三氟丙基三乙氧基矽烷、二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、二甲基-二正丙氧基矽烷、二甲基-二異丙氧基矽烷、二甲基-二正丁氧基矽烷、二甲基-二-二級丁氧基矽烷、二甲基-二-三級丁氧基矽烷、二甲基二苯氧基矽烷、二乙基二甲氧基矽烷、二乙基二乙氧基矽烷、二乙基-二正丙氧基矽烷、二乙基-二異丙氧基矽烷、二乙基-二正丁氧基矽烷、二乙基-二-二級丁氧基矽烷、二乙基-二-三級丁氧基矽烷、二乙基二苯氧基矽烷、二正丙基二甲氧基矽烷、二正丙基二乙氧基矽烷、二正丙基-二正丙氧基矽烷、二正丙基-二異丙氧基矽烷、二正丙基-二正丁氧基矽烷、二正丙基-二-二級丁氧基矽烷、二正丙基-二-三級丁氧基矽烷、二正丙基-二-苯氧基矽烷、二異丙基二甲氧基矽烷、二異丙基二乙氧基矽烷、二異丙基-二正丙氧基矽烷、二異丙基-二異丙氧基矽烷、二異丙基-二正丁氧基矽烷、二異丙基-二-二級丁氧基矽烷、二異丙基-二-三級丁氧基矽烷、二異丙基-二-苯氧基矽烷、二正丁基二甲氧基矽烷、二正丁基二乙氧基矽烷、二正丁基-二正丙氧基矽烷、二正丁基-二異丙氧基矽烷、二正丁基-二正丁氧基矽烷、二正丁基-二-二級丁氧基矽烷、二正丁基-二-三級丁氧基矽烷、二正丁基-二-苯氧基矽烷、二-二級丁基二甲氧基矽烷、二-二級丁基二乙氧基矽烷、二-二級丁基-二正丙氧基矽烷、二-二級丁基-二異丙氧基矽烷、二-二級丁基-二正丁氧基矽烷、二-二級丁基-二-二級丁氧基矽烷、二-二級丁基-二-三級丁氧基矽烷、二-二級丁基-二-苯氧基矽烷、二-三級丁基二甲氧基矽烷、二-三級丁基二乙氧基矽烷、二-三級丁基-二正丙氧基矽烷、二-三級丁基-二異丙氧基矽烷、二-三級丁基-二正丁氧基矽烷、二-三級丁基-二-二級丁氧基矽烷、二-三級丁基-二-三級丁氧基矽烷、二-三級丁基-二-苯氧基矽烷、二苯基二甲氧基矽烷、二苯基-二-乙氧基矽烷、二苯基-二正丙氧基矽烷、二苯基-二異丙氧基矽烷、二苯基-二正丁氧基矽烷、二苯基-二-二級丁氧基矽烷、二苯基-二-三級丁氧基矽烷、二苯基二苯氧基矽烷、二乙烯基三甲氧基矽烷等。
作為化合物(1)的較佳化合物,甲基三甲氧基矽烷、甲基三乙氧基矽烷、甲基三正丙氧基矽烷、甲基三異丙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、二乙基二甲氧基矽烷、二乙基二乙氧基矽烷、二苯基二甲氧基矽烷、二苯基二乙氧基矽烷等於工業上取得容易,而為較佳。此等可使用1種或同時使用2種以上。
在上述通式(2)中,就R2
所表示的1價有機基而言,可列舉與先前的通式(1)之R及R1
相同的有機基。又,4個R2
互相獨立,可為1種1價有機基、或2種以上的1價有機基。作為通式(2)所示之化合物,具體而言,可使用四甲氧基矽烷、甲氧基三乙氧基矽烷、二甲氧基二乙氧基矽烷、三甲氧基乙氧基矽烷、四乙氧基矽烷、四正丙氧基矽烷、四異丙氧基矽烷、四正丁氧基矽烷、四-二級丁氧基矽烷、四-三級丁氧基矽烷、四苯氧基矽烷等。其中四甲氧基矽烷、四乙氧基矽烷於工業上取得容易,而為較佳。
本發明之矽氧聚合物之製造方法中,若將選自前述通式(1)所示之化合物、及前述通式(2)所示之化合物的至少1種矽烷化合物之總量當作100莫耳%時,通式(2)所示之化合物以50~100莫耳%為較佳,以60~100莫耳%為更佳,以70~100莫耳%為進一步更佳。通式(2)所示之化合物若為50莫耳%以上,則由於可得到硬塗膜,故為較佳。
本發明之矽氧聚合物之製造方法,係於四級銨化合物存在下進行反應。四級銨化合物以含有羥基之四級銨化合物為較佳。
就四級銨化合物而言,例如,可列舉氫氧化羥基甲基三甲基銨、氫氧化1-羥基乙基三甲基銨、氫氧化2-羥基乙基三甲基銨、氫氧化1-羥基丙基三甲基銨、氫氧化2-羥基丙基三甲基銨、氫氧化3-羥基丙基三甲基銨、氫氧化羥基甲基三乙基銨、氫氧化1-羥基乙基三乙基銨、氫氧化2-羥基乙基三乙基銨、氫氧化1-羥基丙基三乙基銨、氫氧化2-羥基丙基三乙基銨、氫氧化3-羥基丙基三乙基銨、氫氧化羥基甲基三丙基銨、氫氧化1-羥基乙基三丙基銨、氫氧化2-羥基乙基三丙基銨、氫氧化1-羥基丙基三丙基銨、氫氧化2-羥基丙基三丙基銨、氫氧化3-羥基丙基三丙基銨、氫氧化羥基甲基三丁基銨、氫氧化1-羥基乙基三丁基銨、氫氧化2-羥基丙基三丁基銨、氫氧化1-羥基丙基三丁基銨、氫氧化2-羥基丙基三丁基銨、氫氧化3-羥基丙基三丁基銨、氫氧化二羥基甲基二甲基銨、氫氧化二甲基雙(2-羥基乙基)銨、氫氧化參(2-羥基乙基)甲基銨、氟化四丁基銨、氯化苄基三丁基銨、氯化苄基三乙基銨、氯化苄基三甲基銨、氯化四正丁基銨、氯化四乙基銨、氯化四甲基銨、溴化苄基三正丁基銨、溴化苄基三乙基銨、溴化苄基三甲基銨、溴化正辛基三甲基銨、溴化己基三甲基銨、溴化四丁基銨、溴化四乙基銨、溴化四癸基三甲基銨、溴化四甲基銨、溴化四正丙基銨、碘化四丁基銨、碘化四乙基銨、碘化四甲基銨、碘化四正丙基銨、碘化三甲基苯基銨、氫氧化苄基三甲基銨、氫氧化苯基三甲基銨、氫氧化四丁基銨、氫氧化四乙基銨、氫氧化四甲基銨、氫氧化四丙基銨、硫酸氫四丁基銨、四氟硼酸四丁基銨、硫氰酸四甲基銨、對甲苯磺酸四甲基銨等。
其中,較佳係以氫氧化2-羥基乙基三甲基銨、氫氧化2-羥基三乙基銨、氫氧化2-羥基甲基三丙基銨、氫氧化2-羥基甲基三丁基銨、氫氧化二甲基雙(2-羥基乙基)銨、氫氧化參(2-羥基乙基)甲基銨、氯化苄基三丁基銨、氯化苄基三甲基銨、氯化四正丁基銨、氯化四甲基銨、溴化苄基三正丁基銨、溴化苄基三甲基銨、溴化己基三甲基銨、溴化四丁基銨、溴化四癸基三甲基銨、溴化四甲基銨、氫氧化苄基三甲基銨、氫氧化苯基三甲基銨、氫氧化四丁基銨、氫氧化四乙基銨、氫氧化四甲基銨、氫氧化四丙基銨、硫酸氫四丁基銨、四氟硼酸四丁基銨、硫氰酸四甲基銨、對甲苯磺酸四甲基銨為較佳,再者,以氫氧化四甲基銨、氫氧化2-羥基乙基三甲基銨、氫氧化二甲基雙(2-羥基乙基)銨、氫氧化參(2-羥基乙基)甲基銨為較佳。氫氧化四甲基銨係廉價,且反應控制為容易,氫氧化2-羥基乙基三甲基銨、氫氧化二甲基雙(2-羥基乙基)銨、氫氧化參(2-羥基乙基)甲基銨,係一般可藉由三甲基胺、二甲基胺及甲基胺與環氧乙烷之加成反應而得到,由於原料中不使用金屬,金屬含量少的氫氧化2-羥基乙基三甲基銨、氫氧化二甲基雙(2-羥基乙基)銨、氫氧化參(2-羥基乙基)甲基銨,係工業品級容易,而為較佳。
四級銨化合物之使用量,相對於選自前述通式(1)所示之化合物、及前述通式(2)所示之化合物的至少1種矽烷化合物之烷氧基的總量1莫耳,以0.002~2莫耳為較佳,以0.005~1.0莫耳為進一步更佳。藉由將四級銨化合物之使用量,相對於1莫耳之矽烷化合物之烷氧基的總量,調至0.002~2莫耳,能得到可溶於溶劑的矽氧聚合物,而為較佳。
四級銨鹽之金屬含量,依照質量基準,以5ppm以下為較佳,更佳為1ppm以下,進一步更佳為500ppb以下。若四級銨化合物之金屬含量為5ppm以下,則可使用於顯示器或半導體的電子資訊材料用途。
四級銨化合物,從作業性之觀點,亦可形成容易添加的水溶液,進行添加。
本發明之矽氧聚合物之製造方法中,為了將選自通式(1)所示之化合物及(2)所示之化合物的矽烷化合物水解,可使用水。水之種類無特別限定,可使用工業用水、自來水、井水、蒸餾水、離子交換水及超純水等。水可為1種,亦可使用2種以上。
其中以電阻率高的離子交換水或超純水為較佳,再者,電阻率為15MΩ・cm以上之超純水,由於金屬含量少而為較佳。
水之使用量,相對於選自前述通式(1)所示之化合物、及前述通式(2)所示之化合物的至少1種矽烷化合物所具有的烷氧基之莫耳數,較佳為1.0~15.0莫耳倍,更佳為1.0~10.0莫耳倍。進一步更佳為1.0~5.0莫耳倍。在水量為1.0莫耳倍以上之情況,水解、縮聚合反應快速地進行,若為15.0莫耳倍以下,由於反應可被控制,不會凝膠化,而為較佳。
本發明之矽氧聚合物之製造方法,係使反應液與陽離子交換樹脂接觸。就陽離子交換樹脂而言,可為強酸性陽離子交換樹脂,亦可為弱酸性陽離子交換樹脂。通常所用者,例如市售品之氫型陽離子交換樹脂,具體而言,可使用例如Amberlyist(Organo股份有限公司製)、Lewatit(Lanxess股份有限公司製)、Diaion(三菱化學股份有限公司製)、Monosphere(Dow Chemical公司製)等。陽離子交換樹脂以強酸性陽離子交換樹脂為較佳。
就含有選自前述通式(1)所示之化合物、及前述通式(2)所示之化合物的至少1種矽烷化合物、四級銨化合物、及水之反應液,使該反應液與陽離子交換樹脂接觸的方法而言,可列舉使反應液流通於填充陽離子交換樹脂之管柱內的方法、或將陽離子交換樹脂添加於反應液中攪拌的方法等。在後者之情況,陽離子交換樹脂係於處理後藉由過濾等而去除。
本發明之矽氧聚合物之製造方法,以使含有選自前述通式(1)所示之化合物、及前述通式(2)所示之化合物的至少1種矽烷化合物、四級銨化合物、及水之反應液流通於填充陽離子交換樹脂之槽中,與陽離子交換樹脂接觸為較佳。
就陽離子交換樹脂之量而言,相對於1.0當量之所用的四級銨化合物,以1.0~10.0當量為較佳,更佳為1.1~8.0當量,進一步更佳為1.2~5.0當量。若陽離子交換樹脂之使用量為1.0當量以上,則可去除四級銨化合物,若為10.0當量以下,則所得到的矽氧聚合物為安定,又,使用陽離子交換樹脂之量少,經濟上為較佳。
就使反應液與陽離子交換樹脂接觸時之溫度而言,以0~60℃為較佳,進一步更佳為5~50℃。若溫度為0℃以上,則四級銨化合物可充分地去除,若為60℃以下,則矽氧聚合物為安定而較佳。
使反應液與陽離子交換樹脂接觸的時間,以5分鐘~6小時為較佳,更佳為10分鐘~3小時。若接觸時間為5分鐘以上,則可將四級銨化合物充分地去除,若為6小時以下,則矽氧聚合物為安定而較佳。
本發明之矽氧聚合物之製造方法中,使選自通式(1)所示之化合物、及通式(2)所示之化合物的矽烷化合物反應時,可添加沸點100℃以下之醇。就沸點100℃以下之醇而言,例如可列舉甲醇、乙醇、正丙醇、異丙醇。其中甲醇容易餾去,而為較佳。沸點100℃以下之醇,可使用2種以上。
沸點100℃以下之醇,相對於選自通式(1)所示之化合物、及通式(2)所示之化合物的矽烷化合物之質量,以1.0~10質量倍為較佳,更佳為1.2~8質量倍,進一步更佳為1.5~5質量倍。藉由使沸點100℃以下之醇存在1.0質量倍以上,選自通式(1)所示之化合物、及通式(2)所示之化合物的矽烷化合物與水變得容易混合,又可抑制矽氧聚合物之凝膠化而安定。若沸點100℃以下之醇為10質量倍以下,則經濟上為較佳。
本發明之矽氧聚合物之製造方法,除了沸點100℃以下之醇外,亦可添加溶劑。就溶劑而言,可使用甲苯、二甲苯等非質子性溶劑;甲基乙基酮、甲基異丁基酮等酮系溶劑;二乙基醚、四氫呋喃等醚系溶劑;丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、二乙二醇單甲基醚、丙二醇單乙基醚、乳酸乙酯等高沸點溶劑。溶劑可使用2種以上。
本發明之矽氧聚合物之製造方法中,矽氧聚合物之重量平均分子量以設為300~100,000為較佳,更佳為500~50,000,進一步更佳為1,000~20,000。若重量平均分子量為300以上,則可形成塗膜,若為100,000以下,則在有機溶劑中可溶,而為較佳。
又,將重量平均分子量(Mw)除以數量平均分子量(Mn)而得的分散度(Mw/Mn),以1~20為較佳,更佳為1~5。
在本說明書中,矽氧聚合物之重量平均分子量(Mw)及數量平均分子量(Mn)及Z平均分子量(Mz),可使用凝膠滲透層析(GPC)測定,並以標準聚苯乙烯換算而求得。
本發明之矽氧聚合物之製造方法中,矽氧聚合物之高級結構可為籠型。
藉由本發明之矽氧聚合物之製造方法所得到的矽氧聚合物,可溶解於溶劑。就溶劑而言,可使用醇系溶劑、高沸點溶劑。就醇系溶劑而言,可為甲醇、乙醇、異丙醇等醇系溶劑;就高沸點溶劑而言,可為丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、丙二醇單乙基醚、丙二醇單乙基醚乙酸酯、二乙二醇單甲基醚、乳酸乙酯等。
將以藉由本發明之矽氧聚合物之製造方法所得到的矽氧聚合物得到塗膜之一般方法記載於下。
塗膜之製作,係將矽氧聚合物旋轉塗布在基板上,形成薄膜,並將其加熱,而得到塗膜。就基板之材質而言,可列舉如玻璃、矽晶片、或聚乙烯、聚丙烯及聚對苯二甲酸丙二酯等樹脂。
藉由將基板上所形成的薄膜放入熱板或培養器中加熱,而去除溶劑,同時進行矽氧聚合物之水解、縮聚合反應,可製作塗膜。
一般在膜之製作中,藉由在較佳為80℃以上,更佳為100℃以上加熱,可製作塗膜。
以此種方式製作的塗膜,可得到鉛筆硬度為4H以上之非常硬的膜,耐刮傷性優良。
藉由本發明之矽氧聚合物之製造方法所得到的矽氧聚合物,如上述,由於可簡便地得到塗膜,適合使用於半導體或顯示器等。
[實施例]
以下顯示實施例及比較例,具體地說明本發明。在以下之實施例中,分析係使用下述裝置,原料在無特別明示的情況,使用從試藥製造商購入之一般試藥。分析係使用下述之方法。
・分子量測定
使用東曹公司製HLC-8220GPC系統,將東曹公司製TSKgel SuperHZ3000、TSKgel SuperHZ2000、TSKgel SuperHZ1000串聯地連接,進行分析。檢測係以RI(折射率計)進行,使用1支TSKgel SuperH-RC,作為參考管柱。展開溶劑係使用和光純藥公司製四氫呋喃,管柱及參考管柱之流速係以0.35mL/分鐘進行。測定溫度,於柱塞泵、管柱均以40℃進行。樣本之調製,係將約0.025g之矽氧聚合物用10mL之四氫呋喃稀釋者,以25μL打入設定而進行。分子量分布計算方面,使用東曹公司製TSK標準聚苯乙烯(A-500、A-1000、A-2500、A-5000、F-1、F-2、F-4、F-10、F-20、F-40、F-80)作為標準物質。
・固體成分濃度測定
在鋁杯中精秤1.0g之包含矽氧聚合物之溶液,使用熱板,在175℃燒成1小時,而測定相對於1.0g之包含矽氧聚合物之溶液的固體成分之質量,算出包含矽氧聚合物之溶液的固體成分濃度(質量%)。
・刮痕硬度測定
依照JIS K 5600-5-4刮痕硬度(鉛筆法)進行。但是,塗膜係藉由下列之方法製成。將1ml之包含矽氧聚合物之溶液滴下至矽晶片上,藉由旋轉塗布機(1000rpm)形成薄膜。將所得到之薄膜於130℃之熱板上燒成90秒後,放置於250℃之熱板上,蓋上金屬製之蓋後,燒成1小時,將所得到的塗膜供給至刮痕硬度試驗。塗膜之厚度,係使用光干涉式膜厚測定裝置(Lambda Ace,Screen Semiconductor Solutions股份有限公司製)測定。
實施例1
在100ml之螺旋小瓶中進料2.45g(0.018mol)之甲基三甲氧基矽烷、6.39g(0.042mol)之四甲氧基矽烷、26.52g(矽烷化合物之3.0質量倍)之甲醇、4.42g之離子交換水。再者,投入磁攪拌器之攪拌子,進行攪拌。繼而,滴下12.82g(0.232莫耳倍/烷氧基)之50%氫氧化2-羥基乙基三甲基銨水溶液。水之進料量,係合計事先進料之離子交換水、與伴隨50%氫氧化2-羥基乙基三甲基銨水溶液之量,為2.72莫耳倍/烷氧基。滴下後,使反應液於室溫熟成3小時。另外,在直徑13.5mm、長度200mm之SUS304製圓筒形管柱的一端,以不使離子交換樹脂流出之程度填充石英棉後,填充事先以甲醇置換之陽離子交換樹脂(Amberlyst 15JWET,Organo(股)製)。筒係2支串聯地連結,填充的陽離子交換樹脂之量為56cm3
。將熟成後之反應液藉由柱塞泵,以28cm3
/h之速度壓送至填充離子交換樹脂的管柱。將反應液全部移液後,進一步藉由輸送甲醇,將反應液從管柱擠出。在所得到的反應液中添加等量之丙二醇單乙基醚,藉由減壓濃縮,得到包含矽氧聚合物之無色透明液體。所得到的無色透明液體之固體成分濃度為10.2質量%。從其固體成分所求得的矽氧聚合物之產率為78%,矽氧聚合物之重量平均分子量(Mw)為5,090,分散度(Mw/Mn)為3.89。又,塗膜之刮痕硬度為6H。
實施例2
在100ml之螺旋小瓶中,進料5.18g(0.038mol)之甲基三甲氧基矽烷、8.68g(0.057mol)之四甲氧基矽烷、41.55g(矽烷化合物之3.0質量倍)之甲醇。再者,投入磁攪拌器之攪拌子,進行攪拌。繼而,滴下12.24g(0.144莫耳倍/烷氧基)之50%氫氧化2-羥基乙基三甲基銨水溶液。因此,水之進料量為1.02莫耳倍/烷氧基。滴下後,使反應液於室溫熟成3小時。另外,在直徑13.5mm、長度20mm之SUS304製圓筒形管柱的一端,以不使離子交換樹脂流出之程度填充石英棉後,填充事先以甲醇置換之陽離子交換樹脂(Amberlyst 15JWET,Organo(股)製)。管柱係2支串聯地連結,填充的陽離子交換樹脂之量為56cm3
。將熟成後之反應液藉由柱塞泵,以28cm3
/h之速度壓送至填充離子交換樹脂的管柱。將反應液全部移液後,進一步藉由輸送甲醇,將反應液從管柱擠出。在所得到的反應液中添加等量之丙二醇單乙基醚,藉由減壓濃縮,得到包含矽氧聚合物之無色透明液體。所得到的無色透明液體之固體成分濃度為17.9質量%。從其固體成分所求得的矽氧聚合物之產率為76%,矽氧聚合物之重量平均分子量(Mw)為4,660,分散度(Mw/Mn)為2.22。又,塗膜之刮痕硬度為6H。
實施例3
在實施例2中,除了將5.18g(0.038mol)之甲基三甲氧基矽烷、8.68g(0.057mol)之四甲氧基矽烷、41.55g(矽烷化合物之3.0質量倍)之甲醇、12.24g(0.144莫耳倍/烷氧基)之50%氫氧化2-羥基乙基三甲基銨水溶液,變更為6.42g(0.047mol)之甲基三甲氧基矽烷、7.29g(0.047mol)之四甲氧基矽烷、27.42g(矽烷化合物之2.0質量倍)之甲醇、11.91g(0.144莫耳倍/烷氧基)之50%氫氧化2-羥基乙基三甲基銨水溶液以外,以同樣方法合成矽氧聚合物時,得到包含矽氧聚合物的無色透明黏性液體。所得到的無色透明黏性液體之固體成分濃度為15.6質量%。從其固體成分所求得的矽氧聚合物之產率為82%,矽氧聚合物之重量平均分子量(Mw)為3,600,分散度(Mw/Mn)為2.00。又,塗膜之刮痕硬度為6H。
比較例1
在100ml之螺旋小瓶中進料2.45g(0.018mol)之甲基三甲氧基矽烷、6.39g(0.042mol)之四甲氧基矽烷、26.52g(矽烷化合物之3.0質量倍)之甲醇、4.42g之離子交換水。再者,投入磁攪拌器之攪拌子,進行攪拌。繼而,滴下12.82g(0.232莫耳倍/烷氧基)之50%氫氧化2-羥基乙基三甲基銨水溶液。水之進料量,係合計事先進料之離子交換水、與伴隨50%氫氧化2-羥基乙基三甲基銨水溶液之量,為2.72莫耳倍/烷氧基。滴下後,使反應液於室溫熟成3小時。另外,在200ml之螺旋小瓶中進料7.17g之馬來酸、13.26g之離子交換水、88.40g之乙酸乙酯,並用磁攪拌器攪拌,進一步藉由將熟成後之反應液滴下而添加,將反應液中作為觸媒添加的氫氧化2-羥基乙基三甲基銨中和。然而,即使相對於矽氧聚合物,添加10質量倍的乙酸乙酯,反應液仍變得均勻,無法進行分液,因此無法得到中和而去除鹽之狀態的矽氧聚合物。
比較例2
在比較例1中,除了將26.52g(矽烷化合物之3.0質量倍)之甲醇變更為4.42g(0.5質量倍/矽烷化合物)之甲醇以外,以同樣方法進行實驗,結果中和時矽氧聚合物凝膠化,無法得到可溶於有機溶劑中的矽氧聚合物。
比較例3
在實施例1中,除了不滴下12.82g(0.232莫耳倍/烷氧基)之50%氫氧化2-羥基乙基三甲基銨水溶液,因而水之進料量變更為只有事先進料的離子交換水,即為1.12莫耳倍/烷氧基以外,以同樣方法進行實驗,結果所得到的矽氧聚合物之重量平均分子量(Mw)為530,無法得到聚合至能塗膜程度的矽氧聚合物。
[表1]
合成條件 | 評價結果 | |||||||||
矽烷化合物 | 四級銨化合物 | 水 | 甲醇 | 陽離子 交換樹脂 | 分子量 | 固體成分濃度 | 產率 | 鉛筆硬度 | ||
式(1)之 矽烷化合物 | 式(2)之 矽烷化合物 | |||||||||
(莫耳%) | (莫耳%) | (莫耳倍/ 烷氧基) | (質量倍/ 矽烷化合物) | (Mw) | (質量%) | (%) | (-) | |||
實施例1 | 30 | 70 | 50%氫氧化2-羥基乙基 三甲基銨水溶液 | 2.72 | 3.0 | Amberlyst 15JWET | 5090 | 10.2 | 78 | 6H |
實施例2 | 40 | 60 | 50%氫氧化2-羥基乙基 三甲基銨水溶液 | 1.02 | 3.0 | Amberlyst 15JWET | 4660 | 17.9 | 76 | 6H |
實施例3 | 50 | 50 | 50%氫氧化2-羥基乙基 三甲基銨水溶液 | 1.02 | 2.0 | Amberlyst 15JWET | 3600 | 15.6 | 82 | 6H |
比較例1 | 30 | 70 | 50%氫氧化2-羥基乙基 三甲基銨水溶液 | 2.72 | 3.0 | - | 未分液 無法得到矽氧聚合物 | |||
比較例2 | 30 | 70 | 50%氫氧化2-羥基乙基 三甲基銨水溶液 | 2.72 | 0.5 | - | 中和時凝膠化 無法得到矽氧聚合物 | |||
比較例3 | 30 | 70 | - | 1.12 | 3.0 | Amberlyst 15JWET | 未聚合至能塗膜之程度 無法得到矽氧聚合物 |
無。
無。
無。
Claims (12)
- 一種矽氧聚合物之製造方法,其中使選自下述通式(1)所示之化合物、及下述通式(2)所示之化合物的至少1種矽烷化合物,與四級銨化合物於水存在下水解後,與陽離子交換樹脂接觸, Ra Si(OR1 )4-a ・・・・・(1) (式中,R表示氫原子或1價有機基,R1 表示1價有機基,a表示1~2之整數) Si(OR2 )4 ・・・・・(2) (式中,R2 表示1價有機基)。
- 如請求項1之矽氧聚合物之製造方法,其中使含有選自該通式(1)所示之化合物、及該通式(2)所示之化合物的至少1種矽烷化合物、四級銨化合物、及水的反應液,流通於填充陽離子交換樹脂之槽中,與陽離子交換樹脂接觸。
- 如請求項1或2之矽氧聚合物之製造方法,其中將選自該通式(1)所示之化合物、及該通式(2)所示之化合物的至少1種矽烷化合物之總量當作100莫耳%時,該通式(2)所示之化合物為50~100莫耳%。
- 如請求項1至3中任一項之矽氧聚合物之製造方法,其中相對於選自該通式(1)所示之化合物、及該通式(2)所示之化合物的至少1種矽烷化合物所具有之烷氧基的總量1莫耳,該四級銨化合物之使用量為0.002~2莫耳。
- 如請求項1至4中任一項之矽氧聚合物之製造方法,其中該四級銨化合物為含有羥基之四級銨化合物。
- 如請求項5之矽氧聚合物之製造方法,其中該含有羥基之四級銨化合物為氫氧化2-羥基乙基三甲基銨、氫氧化二甲基雙(2-羥基乙基)銨、或氫氧化參(2-羥基乙基)甲基銨。
- 如請求項1至6中任一項之矽氧聚合物之製造方法,其中該陽離子交換樹脂為強酸性陽離子交換樹脂。
- 如請求項1至7中任一項之矽氧聚合物之製造方法,其中相對於1.0當量之該四級銨化合物,使用1.0~10.0當量之該陽離子交換樹脂。
- 如請求項1至8中任一項之矽氧聚合物之製造方法,其中於沸點100℃以下之醇存在下,將選自該通式(1)所示之化合物、及該通式(2)所示之化合物的至少1種矽烷化合物水解。
- 如請求項9之矽氧聚合物之製造方法,其中相對於選自該通式(1)所示之化合物、及該通式(2)所示之化合物的至少1種矽烷化合物,該醇之使用量為1.0~10質量倍。
- 一種膜之形成方法,其特徵為將藉由如請求項1至10中任一項之製造方法所得到的矽氧聚合物塗布於基板上,進行加熱。
- 一種鉛筆硬度4H以上之膜,其係藉由如請求項11之膜之形成方法而得到。
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