TW201307372A - 矽氧烷單體的合成方法及其用途 - Google Patents
矽氧烷單體的合成方法及其用途 Download PDFInfo
- Publication number
- TW201307372A TW201307372A TW101121250A TW101121250A TW201307372A TW 201307372 A TW201307372 A TW 201307372A TW 101121250 A TW101121250 A TW 101121250A TW 101121250 A TW101121250 A TW 101121250A TW 201307372 A TW201307372 A TW 201307372A
- Authority
- TW
- Taiwan
- Prior art keywords
- decane
- group
- dimethyl
- methyl
- vinyl
- Prior art date
Links
- 239000000178 monomer Substances 0.000 title claims abstract description 46
- 238000000034 method Methods 0.000 title claims abstract description 25
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 title claims abstract description 21
- 230000002194 synthesizing effect Effects 0.000 title description 2
- 229920000642 polymer Polymers 0.000 claims abstract description 42
- 239000003054 catalyst Substances 0.000 claims abstract description 41
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 80
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 46
- -1 alkoxy decane Chemical compound 0.000 claims description 44
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 39
- 125000004432 carbon atom Chemical group C* 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 21
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 19
- BUEDBKYORKGOSS-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(O)(O)C1=CC=CC=C1)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(O)(O)C1=CC=CC=C1)CCCCCCCC BUEDBKYORKGOSS-UHFFFAOYSA-N 0.000 claims description 18
- 229910021529 ammonia Inorganic materials 0.000 claims description 17
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 238000004519 manufacturing process Methods 0.000 claims description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 9
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 claims description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 8
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 8
- ANBBCZAIOXDZPV-UHFFFAOYSA-N 1,1,1-trimethoxy-2-methyldecane Chemical compound CC(C(OC)(OC)OC)CCCCCCCC ANBBCZAIOXDZPV-UHFFFAOYSA-N 0.000 claims description 7
- 230000007062 hydrolysis Effects 0.000 claims description 7
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 claims description 6
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 claims description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 6
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 claims description 6
- 230000002378 acidificating effect Effects 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- AGGJWJFEEKIYOF-UHFFFAOYSA-N 1,1,1-triethoxydecane Chemical compound CCCCCCCCCC(OCC)(OCC)OCC AGGJWJFEEKIYOF-UHFFFAOYSA-N 0.000 claims description 4
- LEEANUDEDHYDTG-UHFFFAOYSA-N 1,2-dimethoxypropane Chemical compound COCC(C)OC LEEANUDEDHYDTG-UHFFFAOYSA-N 0.000 claims description 4
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 claims description 4
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 4
- JZHKIUBMQMDQRG-UHFFFAOYSA-N C(=C)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(=C)C(C(OC)(OC)OC)CCCCCCCC JZHKIUBMQMDQRG-UHFFFAOYSA-N 0.000 claims description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 4
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 235000019253 formic acid Nutrition 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 229910017604 nitric acid Inorganic materials 0.000 claims description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 4
- BHRZNVHARXXAHW-UHFFFAOYSA-N sec-butylamine Chemical compound CCC(C)N BHRZNVHARXXAHW-UHFFFAOYSA-N 0.000 claims description 4
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 4
- OTGGHZUEAWMAAK-UHFFFAOYSA-N (1,1-dimethoxy-1-phenyldecan-2-yl)benzene Chemical compound C1(=CC=CC=C1)C(C(OC)(OC)C1=CC=CC=C1)CCCCCCCC OTGGHZUEAWMAAK-UHFFFAOYSA-N 0.000 claims description 3
- WJMXTYZCTXTFJM-UHFFFAOYSA-N 1,1,1,2-tetraethoxydecane Chemical compound C(C)OC(C(OCC)(OCC)OCC)CCCCCCCC WJMXTYZCTXTFJM-UHFFFAOYSA-N 0.000 claims description 3
- KYUCWJRUVWJDOF-UHFFFAOYSA-N 1,1,1-trifluoro-4-(triethoxymethyl)dodecane Chemical compound FC(CCC(C(OCC)(OCC)OCC)CCCCCCCC)(F)F KYUCWJRUVWJDOF-UHFFFAOYSA-N 0.000 claims description 3
- DGZPBRFJRXDRDD-UHFFFAOYSA-N 1-chloro-4-(triethoxymethyl)dodecane Chemical compound ClCCCC(C(OCC)(OCC)OCC)CCCCCCCC DGZPBRFJRXDRDD-UHFFFAOYSA-N 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 3
- LBIHNTAFJVHBLJ-UHFFFAOYSA-N 3-(triethoxymethyl)undec-1-ene Chemical compound C(=C)C(C(OCC)(OCC)OCC)CCCCCCCC LBIHNTAFJVHBLJ-UHFFFAOYSA-N 0.000 claims description 3
- YVKNZKRTDFOBNO-UHFFFAOYSA-N 3-methoxy-2,2-dimethylundecane Chemical compound CC(C(OC)CCCCCCCC)(C)C YVKNZKRTDFOBNO-UHFFFAOYSA-N 0.000 claims description 3
- VEQDVXUGVMZXKQ-UHFFFAOYSA-N 4-(1,1-dimethoxyethyl)-1,1,1-trifluorododecane Chemical compound FC(CCC(C(OC)(OC)C)CCCCCCCC)(F)F VEQDVXUGVMZXKQ-UHFFFAOYSA-N 0.000 claims description 3
- GNPSQUCXOBDIDY-UHFFFAOYSA-N 4-(trimethoxymethyl)dodecane Chemical compound C(CCCCCCC)C(C(OC)(OC)OC)CCC GNPSQUCXOBDIDY-UHFFFAOYSA-N 0.000 claims description 3
- VXLHENRCUVMBIR-UHFFFAOYSA-N C(=C)C(C(OC)(OC)C)CCCCCCCC Chemical compound C(=C)C(C(OC)(OC)C)CCCCCCCC VXLHENRCUVMBIR-UHFFFAOYSA-N 0.000 claims description 3
- SPBOUQIQODHYHJ-UHFFFAOYSA-N C(=C)C(C(OCC)(C)C)CCCCCCCC Chemical compound C(=C)C(C(OCC)(C)C)CCCCCCCC SPBOUQIQODHYHJ-UHFFFAOYSA-N 0.000 claims description 3
- CYOXKCUGRLNSCA-UHFFFAOYSA-N C(=C)C(C(OCC)(OCC)C)CCCCCCCC Chemical compound C(=C)C(C(OCC)(OCC)C)CCCCCCCC CYOXKCUGRLNSCA-UHFFFAOYSA-N 0.000 claims description 3
- VSRNKQMSXIOSIB-UHFFFAOYSA-N C(=C)C1=CC=C(C=C1)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(=C)C1=CC=C(C=C1)C(C(OC)(OC)OC)CCCCCCCC VSRNKQMSXIOSIB-UHFFFAOYSA-N 0.000 claims description 3
- XEXSKPULSFMYGA-UHFFFAOYSA-N C(=C)C1=CC=C(C=C1)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(=C)C1=CC=C(C=C1)C(C(OCC)(OCC)OCC)CCCCCCCC XEXSKPULSFMYGA-UHFFFAOYSA-N 0.000 claims description 3
- UEYMLSDWUUKDND-UHFFFAOYSA-N C(C)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(C)C(C(OCC)(OCC)OCC)CCCCCCCC UEYMLSDWUUKDND-UHFFFAOYSA-N 0.000 claims description 3
- UNTLIHCGIBPNQR-UHFFFAOYSA-N C(C)OC(C(C)(C)C)CCCCCCCC Chemical compound C(C)OC(C(C)(C)C)CCCCCCCC UNTLIHCGIBPNQR-UHFFFAOYSA-N 0.000 claims description 3
- LLGHYVXTTIEZPZ-UHFFFAOYSA-N C(C)OC(CCCCCCCCC)(C)C Chemical compound C(C)OC(CCCCCCCCC)(C)C LLGHYVXTTIEZPZ-UHFFFAOYSA-N 0.000 claims description 3
- JSGRIFNBTXDZQU-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC JSGRIFNBTXDZQU-UHFFFAOYSA-N 0.000 claims description 3
- STJBWPMXSJHEFV-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(OCC)(OCC)C1=CC=CC=C1)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(OCC)(OCC)C1=CC=CC=C1)CCCCCCCC STJBWPMXSJHEFV-UHFFFAOYSA-N 0.000 claims description 3
- ZGTWPVZLICCPGQ-UHFFFAOYSA-N C1(=CC=CC=C1)CCC(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C1(=CC=CC=C1)CCC(C(OCC)(OCC)OCC)CCCCCCCC ZGTWPVZLICCPGQ-UHFFFAOYSA-N 0.000 claims description 3
- CGQUZJGQDZKSNG-UHFFFAOYSA-N CC(C(OC)(OC)C1=CC=CC=C1)CCCCCCCC Chemical compound CC(C(OC)(OC)C1=CC=CC=C1)CCCCCCCC CGQUZJGQDZKSNG-UHFFFAOYSA-N 0.000 claims description 3
- LWRMRQUUHFZTNI-UHFFFAOYSA-N CC(C(OCC)(OCC)C1=CC=CC=C1)CCCCCCCC Chemical compound CC(C(OCC)(OCC)C1=CC=CC=C1)CCCCCCCC LWRMRQUUHFZTNI-UHFFFAOYSA-N 0.000 claims description 3
- PZKBIVOXIFYDRI-UHFFFAOYSA-N CC(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound CC(C(OCC)(OCC)OCC)CCCCCCCC PZKBIVOXIFYDRI-UHFFFAOYSA-N 0.000 claims description 3
- GEQCBLRJKCCGSA-UHFFFAOYSA-N COC(C(C)(C)OC)CCCCCCCC Chemical compound COC(C(C)(C)OC)CCCCCCCC GEQCBLRJKCCGSA-UHFFFAOYSA-N 0.000 claims description 3
- UCRXYBJLTBJFHO-UHFFFAOYSA-N ClCC(C(OC)(C)C)CCCCCCCC Chemical compound ClCC(C(OC)(C)C)CCCCCCCC UCRXYBJLTBJFHO-UHFFFAOYSA-N 0.000 claims description 3
- LFRZICIZVKXFAB-UHFFFAOYSA-N ClCC(C(OC)(OC)C)CCCCCCCC Chemical compound ClCC(C(OC)(OC)C)CCCCCCCC LFRZICIZVKXFAB-UHFFFAOYSA-N 0.000 claims description 3
- PYBOUZPCXWOMJC-UHFFFAOYSA-N ClCC(C(OC)(OC)OC)CCCCCCCC Chemical compound ClCC(C(OC)(OC)OC)CCCCCCCC PYBOUZPCXWOMJC-UHFFFAOYSA-N 0.000 claims description 3
- VWDNKJZDHBQPGC-UHFFFAOYSA-N ClCC(C(OCC)(C)C)CCCCCCCC Chemical compound ClCC(C(OCC)(C)C)CCCCCCCC VWDNKJZDHBQPGC-UHFFFAOYSA-N 0.000 claims description 3
- WQTXLVDTVPBIFK-UHFFFAOYSA-N ClCC(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound ClCC(C(OCC)(OCC)OCC)CCCCCCCC WQTXLVDTVPBIFK-UHFFFAOYSA-N 0.000 claims description 3
- VKNUVQXIIBFCFO-UHFFFAOYSA-N ClCCCC(C(OC)(C)C)CCCCCCCC Chemical compound ClCCCC(C(OC)(C)C)CCCCCCCC VKNUVQXIIBFCFO-UHFFFAOYSA-N 0.000 claims description 3
- BGPRILKWLAIMJP-UHFFFAOYSA-N ClCCCC(C(OC)(OC)C)CCCCCCCC Chemical compound ClCCCC(C(OC)(OC)C)CCCCCCCC BGPRILKWLAIMJP-UHFFFAOYSA-N 0.000 claims description 3
- QHXUUOMFVVRUPK-UHFFFAOYSA-N ClCCCC(C(OCC)(C)C)CCCCCCCC Chemical compound ClCCCC(C(OCC)(C)C)CCCCCCCC QHXUUOMFVVRUPK-UHFFFAOYSA-N 0.000 claims description 3
- QWQCFZZGYARFRI-UHFFFAOYSA-N ClCCCC(C(OCC)(OCC)C)CCCCCCCC Chemical compound ClCCCC(C(OCC)(OCC)C)CCCCCCCC QWQCFZZGYARFRI-UHFFFAOYSA-N 0.000 claims description 3
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 3
- 239000011976 maleic acid Substances 0.000 claims description 3
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 claims description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 3
- DQGPWNBGAYGUPK-UHFFFAOYSA-N 1,1,1-trifluoro-4-(trimethoxymethyl)dodecane Chemical compound FC(CCC(C(OC)(OC)OC)CCCCCCCC)(F)F DQGPWNBGAYGUPK-UHFFFAOYSA-N 0.000 claims description 2
- CWZQYRJRRHYJOI-UHFFFAOYSA-N 1,1,1-trimethoxydecane Chemical compound CCCCCCCCCC(OC)(OC)OC CWZQYRJRRHYJOI-UHFFFAOYSA-N 0.000 claims description 2
- DIIIISSCIXVANO-UHFFFAOYSA-N 1,2-Dimethylhydrazine Chemical compound CNNC DIIIISSCIXVANO-UHFFFAOYSA-N 0.000 claims description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 claims description 2
- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 claims description 2
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
- JWUJQDFVADABEY-UHFFFAOYSA-N 2-methyltetrahydrofuran Chemical compound CC1CCCO1 JWUJQDFVADABEY-UHFFFAOYSA-N 0.000 claims description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- BAWKIVWMQSQMAX-UHFFFAOYSA-N C(=C)C(C(C)(C)OC)CCCCCCCC Chemical compound C(=C)C(C(C)(C)OC)CCCCCCCC BAWKIVWMQSQMAX-UHFFFAOYSA-N 0.000 claims description 2
- RLIKELSESIGUCU-UHFFFAOYSA-N C(=C)C1=CC=C(C=C1)C(C(OC)(OC)C)CCCCCCCC Chemical compound C(=C)C1=CC=C(C=C1)C(C(OC)(OC)C)CCCCCCCC RLIKELSESIGUCU-UHFFFAOYSA-N 0.000 claims description 2
- ZPDWPXIWIIHDBP-UHFFFAOYSA-N C(C)(C)C(C(O)(O)C(C)C)CCCCCCCC Chemical compound C(C)(C)C(C(O)(O)C(C)C)CCCCCCCC ZPDWPXIWIIHDBP-UHFFFAOYSA-N 0.000 claims description 2
- XDWOPHWUVJNQCA-UHFFFAOYSA-N C(CC)C(C(OC)(OC)OC)(CCCCCCCC)CCC Chemical compound C(CC)C(C(OC)(OC)OC)(CCCCCCCC)CCC XDWOPHWUVJNQCA-UHFFFAOYSA-N 0.000 claims description 2
- XRNDMACZMJPCRX-UHFFFAOYSA-N C(CC)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(CC)C(C(OCC)(OCC)OCC)CCCCCCCC XRNDMACZMJPCRX-UHFFFAOYSA-N 0.000 claims description 2
- IKEVUICGDJISMI-UHFFFAOYSA-N C(CCCCCCCCC)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C(CCCCCCCCC)C(C(OC)(OC)OC)CCCCCCCC IKEVUICGDJISMI-UHFFFAOYSA-N 0.000 claims description 2
- UDEQNDCZULOGLM-UHFFFAOYSA-N C(CCCCCCCCC)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C(CCCCCCCCC)C(C(OCC)(OCC)OCC)CCCCCCCC UDEQNDCZULOGLM-UHFFFAOYSA-N 0.000 claims description 2
- DNCRBGFIMXHPHB-UHFFFAOYSA-N C1(CCCCC1)C(C(O)(O)C1CCCCC1)CCCCCCCC Chemical compound C1(CCCCC1)C(C(O)(O)C1CCCCC1)CCCCCCCC DNCRBGFIMXHPHB-UHFFFAOYSA-N 0.000 claims description 2
- LNQMPZCNFIFRAW-UHFFFAOYSA-N C1(CCCCC1)CC(CCCCCCCCC)(O)O Chemical compound C1(CCCCC1)CC(CCCCCCCCC)(O)O LNQMPZCNFIFRAW-UHFFFAOYSA-N 0.000 claims description 2
- FOKPYQQOWKWTPE-UHFFFAOYSA-N ClCC(C(OCC)(OCC)C)CCCCCCCC Chemical compound ClCC(C(OCC)(OCC)C)CCCCCCCC FOKPYQQOWKWTPE-UHFFFAOYSA-N 0.000 claims description 2
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 claims description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-butylamine Natural products CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 2
- 229940043279 diisopropylamine Drugs 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 claims description 2
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 claims description 2
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 claims description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
- 229940090181 propyl acetate Drugs 0.000 claims description 2
- BJAARRARQJZURR-UHFFFAOYSA-N trimethylazanium;hydroxide Chemical compound O.CN(C)C BJAARRARQJZURR-UHFFFAOYSA-N 0.000 claims description 2
- ZASZWSTYEJKHIN-UHFFFAOYSA-N tripropylazanium;hydroxide Chemical compound [OH-].CCC[NH+](CCC)CCC ZASZWSTYEJKHIN-UHFFFAOYSA-N 0.000 claims description 2
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 4
- SMLNDVNTPWRZJH-UHFFFAOYSA-N 1-chloro-4-(trimethoxymethyl)dodecane Chemical compound ClCCCC(C(OC)(OC)OC)CCCCCCCC SMLNDVNTPWRZJH-UHFFFAOYSA-N 0.000 claims 2
- JDSQBDGCMUXRBM-UHFFFAOYSA-N 2-[2-(2-butoxypropoxy)propoxy]propan-1-ol Chemical compound CCCCOC(C)COC(C)COC(C)CO JDSQBDGCMUXRBM-UHFFFAOYSA-N 0.000 claims 2
- IIEWMRPKJCXTAD-UHFFFAOYSA-N 3-(trimethoxymethyl)undecane Chemical compound C(C)C(C(OC)(OC)OC)CCCCCCCC IIEWMRPKJCXTAD-UHFFFAOYSA-N 0.000 claims 2
- DKXTXMMXQHDILU-UHFFFAOYSA-N C(=C)C1=CC=C(C=C1)CC(CCCCCCCCC)(OCC)OCC Chemical compound C(=C)C1=CC=C(C=C1)CC(CCCCCCCCC)(OCC)OCC DKXTXMMXQHDILU-UHFFFAOYSA-N 0.000 claims 2
- KVNVCPNWYOHJFO-UHFFFAOYSA-N C(C)OC(C(C)(C)OCC)CCCCCCCC Chemical compound C(C)OC(C(C)(C)OCC)CCCCCCCC KVNVCPNWYOHJFO-UHFFFAOYSA-N 0.000 claims 2
- WMAZOIVUIWQRKU-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(OCC)(OCC)OCC)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(OCC)(OCC)OCC)CCCCCCCC WMAZOIVUIWQRKU-UHFFFAOYSA-N 0.000 claims 2
- SBHUYJPUGHEAOT-UHFFFAOYSA-N C1(=CC=CC=C1)CCC(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(=CC=CC=C1)CCC(C(OC)(OC)OC)CCCCCCCC SBHUYJPUGHEAOT-UHFFFAOYSA-N 0.000 claims 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims 2
- USGWKJVZWIQIFI-UHFFFAOYSA-N 1,2,3-trimethoxy-4-(3,3,3-trifluoropropyl)-9H-fluorene Chemical compound FC(CCC1=C(C(=C(C=2CC3=CC=CC=C3C12)OC)OC)OC)(F)F USGWKJVZWIQIFI-UHFFFAOYSA-N 0.000 claims 1
- WQHMEGBWNFRWDH-UHFFFAOYSA-N 2-methoxy-2-methylundecane Chemical compound CCCCCCCCCC(C)(C)OC WQHMEGBWNFRWDH-UHFFFAOYSA-N 0.000 claims 1
- ZLFNKHDEVFODHY-UHFFFAOYSA-N 4-(1,1-diethoxyethyl)-1,1,1-trifluorododecane Chemical compound FC(CCC(C(OCC)(OCC)C)CCCCCCCC)(F)F ZLFNKHDEVFODHY-UHFFFAOYSA-N 0.000 claims 1
- OWQNKYWWEHPMQC-UHFFFAOYSA-N 4-ethyldodecane-3,3-diol Chemical compound C(C)C(C(O)(O)CC)CCCCCCCC OWQNKYWWEHPMQC-UHFFFAOYSA-N 0.000 claims 1
- PLYXEAWBMTWKNK-UHFFFAOYSA-N 5-propyltridecane-4,4-diol Chemical compound C(CC)C(C(O)(O)CCC)CCCCCCCC PLYXEAWBMTWKNK-UHFFFAOYSA-N 0.000 claims 1
- BFHJNAYBGZPWIZ-UHFFFAOYSA-N 6-butyltetradecane-5,5-diol Chemical compound C(CCC)C(C(O)(O)CCCC)CCCCCCCC BFHJNAYBGZPWIZ-UHFFFAOYSA-N 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
- UDONGYJNVNQLFR-UHFFFAOYSA-N C(C)(C)(C)C(C(O)(O)C(C)(C)C)CCCCCCCC Chemical compound C(C)(C)(C)C(C(O)(O)C(C)(C)C)CCCCCCCC UDONGYJNVNQLFR-UHFFFAOYSA-N 0.000 claims 1
- OPJDRGHMZYVKGO-UHFFFAOYSA-N C(CC)C(C(OCC)(OCC)OCC)(CCCCCCCC)CCC Chemical compound C(CC)C(C(OCC)(OCC)OCC)(CCCCCCCC)CCC OPJDRGHMZYVKGO-UHFFFAOYSA-N 0.000 claims 1
- SLRKJPMJQXYOOZ-UHFFFAOYSA-N CC(C(OCC)(OCC)C)CCCCCCCC.[Cl] Chemical compound CC(C(OCC)(OCC)C)CCCCCCCC.[Cl] SLRKJPMJQXYOOZ-UHFFFAOYSA-N 0.000 claims 1
- XVGMAGFYZVXQBD-UHFFFAOYSA-N CCCCCCCCC(C(C)CC)C(C(C)CC)(O)O Chemical compound CCCCCCCCC(C(C)CC)C(C(C)CC)(O)O XVGMAGFYZVXQBD-UHFFFAOYSA-N 0.000 claims 1
- JRIKHZXVAQGQCF-UHFFFAOYSA-N CCCCCCCCC(C12CC3CC(C1)CC(C3)C2)C(O)(O)O Chemical compound CCCCCCCCC(C12CC3CC(C1)CC(C3)C2)C(O)(O)O JRIKHZXVAQGQCF-UHFFFAOYSA-N 0.000 claims 1
- HJAXZSXCMJKPHX-UHFFFAOYSA-N CCCCCCCCC(C1=CC=CC=C1)C(C=C)(O)O Chemical compound CCCCCCCCC(C1=CC=CC=C1)C(C=C)(O)O HJAXZSXCMJKPHX-UHFFFAOYSA-N 0.000 claims 1
- HXTPVPKHLQBAML-UHFFFAOYSA-N CCCCCCCCC(CC(C)C)C(CC(C)C)(O)O Chemical compound CCCCCCCCC(CC(C)C)C(CC(C)C)(O)O HXTPVPKHLQBAML-UHFFFAOYSA-N 0.000 claims 1
- ZXVJDQFSTCSDHI-UHFFFAOYSA-N CCCCCCCCCC(CC1=CC=C(C=C1)C=C)(OC)OC Chemical compound CCCCCCCCCC(CC1=CC=C(C=C1)C=C)(OC)OC ZXVJDQFSTCSDHI-UHFFFAOYSA-N 0.000 claims 1
- YXZVBQJJIIVAFT-UHFFFAOYSA-N CCCCCCCCCC(CCC1CCCCC1)(O)O Chemical compound CCCCCCCCCC(CCC1CCCCC1)(O)O YXZVBQJJIIVAFT-UHFFFAOYSA-N 0.000 claims 1
- PQBAWAQIRZIWIV-UHFFFAOYSA-N N-methylpyridinium Chemical compound C[N+]1=CC=CC=C1 PQBAWAQIRZIWIV-UHFFFAOYSA-N 0.000 claims 1
- 150000002009 diols Chemical class 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
- NVTNQIBQPLGHGE-UHFFFAOYSA-N n,n-dibutylbutan-1-amine;hydrate Chemical compound [OH-].CCCC[NH+](CCCC)CCCC NVTNQIBQPLGHGE-UHFFFAOYSA-N 0.000 claims 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 abstract description 64
- 229910052751 metal Inorganic materials 0.000 abstract description 10
- 239000002184 metal Substances 0.000 abstract description 10
- 238000006116 polymerization reaction Methods 0.000 abstract description 10
- 239000004065 semiconductor Substances 0.000 abstract description 7
- 230000015572 biosynthetic process Effects 0.000 abstract description 5
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- 238000005336 cracking Methods 0.000 abstract 1
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 abstract 1
- 238000010992 reflux Methods 0.000 description 18
- 239000007788 liquid Substances 0.000 description 14
- USASZQYWTDQJNO-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(O)(O)C1=CC=CC=C1)CCCCCCC Chemical compound C1(=CC=CC=C1)C(C(O)(O)C1=CC=CC=C1)CCCCCCC USASZQYWTDQJNO-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 11
- 239000000463 material Substances 0.000 description 10
- 238000004821 distillation Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 239000002245 particle Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 239000012535 impurity Substances 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- 230000009257 reactivity Effects 0.000 description 4
- 238000007086 side reaction Methods 0.000 description 4
- ZTEHOZMYMCEYRM-UHFFFAOYSA-N 1-chlorodecane Chemical compound CCCCCCCCCCCl ZTEHOZMYMCEYRM-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000006482 condensation reaction Methods 0.000 description 3
- DIOQZVSQGTUSAI-NJFSPNSNSA-N decane Chemical class CCCCCCCCC[14CH3] DIOQZVSQGTUSAI-NJFSPNSNSA-N 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 3
- JOLQKTGDSGKSKJ-UHFFFAOYSA-N 1-ethoxypropan-2-ol Chemical compound CCOCC(C)O JOLQKTGDSGKSKJ-UHFFFAOYSA-N 0.000 description 2
- OVSKIKFHRZPJSS-UHFFFAOYSA-N 2,4-D Chemical compound OC(=O)COC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-UHFFFAOYSA-N 0.000 description 2
- OXYZDRAJMHGSMW-UHFFFAOYSA-N 3-chloropropyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)CCCCl OXYZDRAJMHGSMW-UHFFFAOYSA-N 0.000 description 2
- PADYZFIAPBDLEJ-UHFFFAOYSA-N CC1(OC(C(OC1)(O)O)(C)C)C Chemical compound CC1(OC(C(OC1)(O)O)(C)C)C PADYZFIAPBDLEJ-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- 235000011054 acetic acid Nutrition 0.000 description 2
- 238000013019 agitation Methods 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- INSRQEMEVAMETL-UHFFFAOYSA-N decane-1,1-diol Chemical compound CCCCCCCCCC(O)O INSRQEMEVAMETL-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
- YYLGKUPAFFKGRQ-UHFFFAOYSA-N dimethyldiethoxysilane Chemical compound CCO[Si](C)(C)OCC YYLGKUPAFFKGRQ-UHFFFAOYSA-N 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 229940052303 ethers for general anesthesia Drugs 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000003682 fluorination reaction Methods 0.000 description 2
- 239000003517 fume Substances 0.000 description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- GUGNSJAORJLKGP-UHFFFAOYSA-K sodium 8-methoxypyrene-1,3,6-trisulfonate Chemical compound [Na+].[Na+].[Na+].C1=C2C(OC)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 GUGNSJAORJLKGP-UHFFFAOYSA-K 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- QQQSFSZALRVCSZ-UHFFFAOYSA-N triethoxysilane Chemical compound CCO[SiH](OCC)OCC QQQSFSZALRVCSZ-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- KECADNSZFNUZEZ-UHFFFAOYSA-N (1,2-dimethoxy-1-phenyldecyl)benzene Chemical compound COC(C(C1=CC=CC=C1)(C1=CC=CC=C1)OC)CCCCCCCC KECADNSZFNUZEZ-UHFFFAOYSA-N 0.000 description 1
- ILEOTNWQMPAFBH-UHFFFAOYSA-N (4-ethenylphenyl)-dihydroxy-phenylsilane Chemical compound C=1C=C(C=C)C=CC=1[Si](O)(O)C1=CC=CC=C1 ILEOTNWQMPAFBH-UHFFFAOYSA-N 0.000 description 1
- LTQBNYCMVZQRSD-UHFFFAOYSA-N (4-ethenylphenyl)-trimethoxysilane Chemical compound CO[Si](OC)(OC)C1=CC=C(C=C)C=C1 LTQBNYCMVZQRSD-UHFFFAOYSA-N 0.000 description 1
- FAYCDGVHQUZHQU-UHFFFAOYSA-N (4-ethenylphenyl)methyl-diethoxysilane Chemical compound CCO[SiH](Cc1ccc(C=C)cc1)OCC FAYCDGVHQUZHQU-UHFFFAOYSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- KDWQLICBSFIDRM-UHFFFAOYSA-N 1,1,1-trifluoropropane Chemical compound CCC(F)(F)F KDWQLICBSFIDRM-UHFFFAOYSA-N 0.000 description 1
- AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- FWNPMBVDSQMMPH-UHFFFAOYSA-N 1-adamantyl(trihydroxy)silane Chemical compound C1C(C2)CC3CC2CC1([Si](O)(O)O)C3 FWNPMBVDSQMMPH-UHFFFAOYSA-N 0.000 description 1
- VSTXCZGEEVFJES-UHFFFAOYSA-N 1-cycloundecyl-1,5-diazacycloundec-5-ene Chemical compound C1CCCCCC(CCCC1)N1CCCCCC=NCCC1 VSTXCZGEEVFJES-UHFFFAOYSA-N 0.000 description 1
- YNICHAOCDICNOT-UHFFFAOYSA-N 2,2-dimethoxyundecane Chemical compound CCCCCCCCCC(C)(OC)OC YNICHAOCDICNOT-UHFFFAOYSA-N 0.000 description 1
- WVXLLHWEQSZBLW-UHFFFAOYSA-N 2-(4-acetyl-2-methoxyphenoxy)acetic acid Chemical compound COC1=CC(C(C)=O)=CC=C1OCC(O)=O WVXLLHWEQSZBLW-UHFFFAOYSA-N 0.000 description 1
- MFAWEYJGIGIYFH-UHFFFAOYSA-N 2-[4-(trimethoxymethyl)dodecoxymethyl]oxirane Chemical compound C(C1CO1)OCCCC(C(OC)(OC)OC)CCCCCCCC MFAWEYJGIGIYFH-UHFFFAOYSA-N 0.000 description 1
- WBRFMGVGENZZQD-UHFFFAOYSA-N 2-cyclohexylethyl(dihydroxy)silane Chemical compound O[SiH](O)CCC1CCCCC1 WBRFMGVGENZZQD-UHFFFAOYSA-N 0.000 description 1
- 125000004398 2-methyl-2-butyl group Chemical group CC(C)(CC)* 0.000 description 1
- ALRXDIKPRCRYAU-UHFFFAOYSA-N 2-methylpropan-2-ol Chemical compound CC(C)(C)O.CC(C)(C)O ALRXDIKPRCRYAU-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 1
- KEZMLECYELSZDC-UHFFFAOYSA-N 3-chloropropyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(OCC)CCCCl KEZMLECYELSZDC-UHFFFAOYSA-N 0.000 description 1
- JTWDWVCNOLORBR-UHFFFAOYSA-N 3-chloropropyl-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)CCCCl JTWDWVCNOLORBR-UHFFFAOYSA-N 0.000 description 1
- DCQBZYNUSLHVJC-UHFFFAOYSA-N 3-triethoxysilylpropane-1-thiol Chemical compound CCO[Si](OCC)(OCC)CCCS DCQBZYNUSLHVJC-UHFFFAOYSA-N 0.000 description 1
- UUEWCQRISZBELL-UHFFFAOYSA-N 3-trimethoxysilylpropane-1-thiol Chemical compound CO[Si](OC)(OC)CCCS UUEWCQRISZBELL-UHFFFAOYSA-N 0.000 description 1
- LBQJFQVDEJMUTF-UHFFFAOYSA-N 9,10-dipropoxyanthracene Chemical compound C1=CC=C2C(OCCC)=C(C=CC=C3)C3=C(OCCC)C2=C1 LBQJFQVDEJMUTF-UHFFFAOYSA-N 0.000 description 1
- 241000234282 Allium Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- ZGVKQPUCUKEYRW-UHFFFAOYSA-N C(=C)C1=CC=C(C=C1)C(C(OCC)(OCC)C)CCCCCCCC Chemical compound C(=C)C1=CC=C(C=C1)C(C(OCC)(OCC)C)CCCCCCCC ZGVKQPUCUKEYRW-UHFFFAOYSA-N 0.000 description 1
- MZAQILUREVEOEI-UHFFFAOYSA-N C(C)C(C(OC)(OC)OC)(CCCCCCCC)CC Chemical compound C(C)C(C(OC)(OC)OC)(CCCCCCCC)CC MZAQILUREVEOEI-UHFFFAOYSA-N 0.000 description 1
- XCDIYMBIZPUAEA-UHFFFAOYSA-N C(C)OC(C(O)(C1=CC=CC=C1)C1=CC=CC=C1)CCCCCCC Chemical compound C(C)OC(C(O)(C1=CC=CC=C1)C1=CC=CC=C1)CCCCCCC XCDIYMBIZPUAEA-UHFFFAOYSA-N 0.000 description 1
- HCEDEDUGVPEVSI-UHFFFAOYSA-N C(C)OC(CCCC(CCCC)(C1=CC=CC=C1)C1=CC=CC=C1)OCC Chemical compound C(C)OC(CCCC(CCCC)(C1=CC=CC=C1)C1=CC=CC=C1)OCC HCEDEDUGVPEVSI-UHFFFAOYSA-N 0.000 description 1
- MUFWVXFDMRYPIH-UHFFFAOYSA-N C(C)OC(CCCCCCCCC)(OCC)OCC.C1=CC=CC=C1 Chemical compound C(C)OC(CCCCCCCCC)(OCC)OCC.C1=CC=CC=C1 MUFWVXFDMRYPIH-UHFFFAOYSA-N 0.000 description 1
- VUQDBNDSHRSBBD-UHFFFAOYSA-N COC(C(O)(C1=CC=CC=C1)C1=CC=CC=C1)CCCCCCC Chemical compound COC(C(O)(C1=CC=CC=C1)C1=CC=CC=C1)CCCCCCC VUQDBNDSHRSBBD-UHFFFAOYSA-N 0.000 description 1
- QHSBNVFIZWJSLM-UHFFFAOYSA-N COC(CCCC(CCCC)(C1=CC=CC=C1)C1=CC=CC=C1)OC Chemical compound COC(CCCC(CCCC)(C1=CC=CC=C1)C1=CC=CC=C1)OC QHSBNVFIZWJSLM-UHFFFAOYSA-N 0.000 description 1
- YBYBRXNPMTXCJL-UHFFFAOYSA-N COCC(C)OC(C)=O.COCC(C)OC(C)=O Chemical compound COCC(C)OC(C)=O.COCC(C)OC(C)=O YBYBRXNPMTXCJL-UHFFFAOYSA-N 0.000 description 1
- FPLDGTKQRKLJKA-UHFFFAOYSA-N CO[Si](O[Si](O[Si](C)(OC)OC)(C1=CC=CC=C1)C1=CC=CC=C1)(C)OC.CC1C(OCCC1)(C)C Chemical compound CO[Si](O[Si](O[Si](C)(OC)OC)(C1=CC=CC=C1)C1=CC=CC=C1)(C)OC.CC1C(OCCC1)(C)C FPLDGTKQRKLJKA-UHFFFAOYSA-N 0.000 description 1
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- VEUHPWRDBGGGBU-UHFFFAOYSA-N OB(O)O.I.I.I Chemical compound OB(O)O.I.I.I VEUHPWRDBGGGBU-UHFFFAOYSA-N 0.000 description 1
- SBFRPEOITPJYEV-UHFFFAOYSA-N O[SiH](O)C=CC1=CC=CC=C1 Chemical compound O[SiH](O)C=CC1=CC=CC=C1 SBFRPEOITPJYEV-UHFFFAOYSA-N 0.000 description 1
- XHVUVPDVZVTGLC-UHFFFAOYSA-N SCCC[Si](O[Si](O[SiH](OC)OC)(C1=CC=CC=C1)C1=CC=CC=C1)(OC)OC Chemical compound SCCC[Si](O[Si](O[SiH](OC)OC)(C1=CC=CC=C1)C1=CC=CC=C1)(OC)OC XHVUVPDVZVTGLC-UHFFFAOYSA-N 0.000 description 1
- 229910008051 Si-OH Inorganic materials 0.000 description 1
- 229910006358 Si—OH Inorganic materials 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- MNOJPFFLLFLLKV-UHFFFAOYSA-N [diphenyl(trimethoxysilyloxy)silyl] trimethyl silicate Chemical compound C=1C=CC=CC=1[Si](O[Si](OC)(OC)OC)(O[Si](OC)(OC)OC)C1=CC=CC=C1 MNOJPFFLLFLLKV-UHFFFAOYSA-N 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 1
- QYSDNYWGQPYMJZ-UHFFFAOYSA-N bis(4-ethenylphenyl)-dihydroxysilane Chemical compound C=1C=C(C=C)C=CC=1[Si](O)(O)C1=CC=C(C=C)C=C1 QYSDNYWGQPYMJZ-UHFFFAOYSA-N 0.000 description 1
- RWGVEDUVXPKCHH-UHFFFAOYSA-N bis(diethoxysilyloxy)-dimethylsilane Chemical compound CCO[SiH](OCC)O[Si](C)(C)O[SiH](OCC)OCC RWGVEDUVXPKCHH-UHFFFAOYSA-N 0.000 description 1
- DHEQAQHRKSCIFJ-UHFFFAOYSA-N bis[[dimethoxy(methyl)silyl]oxy]-di(propan-2-yl)silane Chemical compound CO[Si](C)(OC)O[Si](C(C)C)(C(C)C)O[Si](C)(OC)OC DHEQAQHRKSCIFJ-UHFFFAOYSA-N 0.000 description 1
- KCIRESFNRQNCDS-UHFFFAOYSA-N bis[[dimethoxy(phenyl)silyl]oxy]-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](OC)(OC)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](OC)(OC)C1=CC=CC=C1 KCIRESFNRQNCDS-UHFFFAOYSA-N 0.000 description 1
- LFTDLKIIVCWSLQ-UHFFFAOYSA-N bis[[ethenyl(dimethoxy)silyl]oxy]-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](O[Si](OC)(OC)C=C)(O[Si](OC)(OC)C=C)C1=CC=CC=C1 LFTDLKIIVCWSLQ-UHFFFAOYSA-N 0.000 description 1
- CEHAVUURMJBCRF-UHFFFAOYSA-N bis[[ethoxy(methyl)silyl]oxy]-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](O[SiH](C)OCC)(O[SiH](C)OCC)C1=CC=CC=C1 CEHAVUURMJBCRF-UHFFFAOYSA-N 0.000 description 1
- HPSAPUFZLRQINY-UHFFFAOYSA-N bis[[hydroxy(diphenyl)silyl]oxy]-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)O[Si](C=1C=CC=CC=1)(C=1C=CC=CC=1)O[Si](O)(C=1C=CC=CC=1)C1=CC=CC=C1 HPSAPUFZLRQINY-UHFFFAOYSA-N 0.000 description 1
- ZDOBWJOCPDIBRZ-UHFFFAOYSA-N chloromethyl(triethoxy)silane Chemical compound CCO[Si](CCl)(OCC)OCC ZDOBWJOCPDIBRZ-UHFFFAOYSA-N 0.000 description 1
- FPOSCXQHGOVVPD-UHFFFAOYSA-N chloromethyl(trimethoxy)silane Chemical compound CO[Si](CCl)(OC)OC FPOSCXQHGOVVPD-UHFFFAOYSA-N 0.000 description 1
- XGLLBUISUZEUMW-UHFFFAOYSA-N chloromethyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(CCl)OCC XGLLBUISUZEUMW-UHFFFAOYSA-N 0.000 description 1
- ZXZMFKUGAPMMCJ-UHFFFAOYSA-N chloromethyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(CCl)OC ZXZMFKUGAPMMCJ-UHFFFAOYSA-N 0.000 description 1
- IGMQAYXTTRYCPZ-UHFFFAOYSA-N chloromethyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)CCl IGMQAYXTTRYCPZ-UHFFFAOYSA-N 0.000 description 1
- ZCSLOBFDVTWIBL-UHFFFAOYSA-N chloromethyl-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)CCl ZCSLOBFDVTWIBL-UHFFFAOYSA-N 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- GEOCFEWLANXFHX-UHFFFAOYSA-N cyclohexyl-dihydroxy-methylsilane Chemical compound C[Si](O)(O)C1CCCCC1 GEOCFEWLANXFHX-UHFFFAOYSA-N 0.000 description 1
- MRQLGKPPFBQBPN-UHFFFAOYSA-N di(butan-2-yl)-dihydroxysilane Chemical compound CCC(C)[Si](O)(O)C(C)CC MRQLGKPPFBQBPN-UHFFFAOYSA-N 0.000 description 1
- CODXEBWJWBPKPQ-UHFFFAOYSA-N dibutyl(dihydroxy)silane Chemical compound CCCC[Si](O)(O)CCCC CODXEBWJWBPKPQ-UHFFFAOYSA-N 0.000 description 1
- NPPCDYNLOPEEJL-UHFFFAOYSA-N dicyclohexyl(dihydroxy)silane Chemical compound C1CCCCC1[Si](O)(O)C1CCCCC1 NPPCDYNLOPEEJL-UHFFFAOYSA-N 0.000 description 1
- 239000003989 dielectric material Substances 0.000 description 1
- 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 1
- GAURFLBIDLSLQU-UHFFFAOYSA-N diethoxy(methyl)silicon Chemical compound CCO[Si](C)OCC GAURFLBIDLSLQU-UHFFFAOYSA-N 0.000 description 1
- MNFGEHQPOWJJBH-UHFFFAOYSA-N diethoxy-methyl-phenylsilane Chemical compound CCO[Si](C)(OCC)C1=CC=CC=C1 MNFGEHQPOWJJBH-UHFFFAOYSA-N 0.000 description 1
- VKJWRHASAVFGPS-UHFFFAOYSA-N diethoxy-methyl-prop-2-enylsilane Chemical compound CCO[Si](C)(CC=C)OCC VKJWRHASAVFGPS-UHFFFAOYSA-N 0.000 description 1
- ROAUYIHROKAFJT-UHFFFAOYSA-N diethoxysilyloxy-[diethoxysilyloxy(dimethyl)silyl]oxy-dimethylsilane Chemical compound C(C)O[SiH](O[Si](O[Si](O[SiH](OCC)OCC)(C)C)(C)C)OCC ROAUYIHROKAFJT-UHFFFAOYSA-N 0.000 description 1
- DAKRXZUXJUPCOF-UHFFFAOYSA-N diethyl(dihydroxy)silane Chemical compound CC[Si](O)(O)CC DAKRXZUXJUPCOF-UHFFFAOYSA-N 0.000 description 1
- OLLFKUHHDPMQFR-UHFFFAOYSA-N dihydroxy(diphenyl)silane Chemical group C=1C=CC=CC=1[Si](O)(O)C1=CC=CC=C1 OLLFKUHHDPMQFR-UHFFFAOYSA-N 0.000 description 1
- BSNASBXELXDWSZ-UHFFFAOYSA-N dihydroxy(dipropyl)silane Chemical compound CCC[Si](O)(O)CCC BSNASBXELXDWSZ-UHFFFAOYSA-N 0.000 description 1
- UKSWSALBYQIBJN-UHFFFAOYSA-N dihydroxy-bis(2-methylpropyl)silane Chemical compound CC(C)C[Si](O)(O)CC(C)C UKSWSALBYQIBJN-UHFFFAOYSA-N 0.000 description 1
- ZXWUGCNBZZSJJN-UHFFFAOYSA-N dihydroxy-di(propan-2-yl)silane Chemical compound CC(C)[Si](O)(O)C(C)C ZXWUGCNBZZSJJN-UHFFFAOYSA-N 0.000 description 1
- RBSBUSKLSKHTBA-UHFFFAOYSA-N dihydroxy-methyl-phenylsilane Chemical compound C[Si](O)(O)C1=CC=CC=C1 RBSBUSKLSKHTBA-UHFFFAOYSA-N 0.000 description 1
- 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
- DIJRHOZMLZRNLM-UHFFFAOYSA-N dimethoxy-methyl-(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](C)(OC)CCC(F)(F)F DIJRHOZMLZRNLM-UHFFFAOYSA-N 0.000 description 1
- CVQVSVBUMVSJES-UHFFFAOYSA-N dimethoxy-methyl-phenylsilane Chemical compound CO[Si](C)(OC)C1=CC=CC=C1 CVQVSVBUMVSJES-UHFFFAOYSA-N 0.000 description 1
- WQTNGCZMPUCIEX-UHFFFAOYSA-N dimethoxy-methyl-prop-2-enylsilane Chemical compound CO[Si](C)(OC)CC=C WQTNGCZMPUCIEX-UHFFFAOYSA-N 0.000 description 1
- XZFXULUXIPPWEW-UHFFFAOYSA-N dimethoxy-methyl-propan-2-ylsilane Chemical compound CO[Si](C)(OC)C(C)C XZFXULUXIPPWEW-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N dimethyl sulfoxide Natural products CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- XCLIHDJZGPCUBT-UHFFFAOYSA-N dimethylsilanediol Chemical compound C[Si](C)(O)O XCLIHDJZGPCUBT-UHFFFAOYSA-N 0.000 description 1
- PXRMLPZQBFWPCV-UHFFFAOYSA-N dioxasilirane Chemical compound O1O[SiH2]1 PXRMLPZQBFWPCV-UHFFFAOYSA-N 0.000 description 1
- WLCHZGMNFDVFED-UHFFFAOYSA-N ditert-butyl(dihydroxy)silane Chemical compound CC(C)(C)[Si](O)(O)C(C)(C)C WLCHZGMNFDVFED-UHFFFAOYSA-N 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- MBGQQKKTDDNCSG-UHFFFAOYSA-N ethenyl-diethoxy-methylsilane Chemical compound CCO[Si](C)(C=C)OCC MBGQQKKTDDNCSG-UHFFFAOYSA-N 0.000 description 1
- ZLNAFSPCNATQPQ-UHFFFAOYSA-N ethenyl-dimethoxy-methylsilane Chemical compound CO[Si](C)(OC)C=C ZLNAFSPCNATQPQ-UHFFFAOYSA-N 0.000 description 1
- JEWCZPTVOYXPGG-UHFFFAOYSA-N ethenyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)C=C JEWCZPTVOYXPGG-UHFFFAOYSA-N 0.000 description 1
- NUFVQEIPPHHQCK-UHFFFAOYSA-N ethenyl-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)C=C NUFVQEIPPHHQCK-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- DRUOQOFQRYFQGB-UHFFFAOYSA-N ethoxy(dimethyl)silicon Chemical compound CCO[Si](C)C DRUOQOFQRYFQGB-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
- FEIZMBLMTCAJSQ-UHFFFAOYSA-N ethoxy-dimethyl-prop-2-enylsilane Chemical compound CCO[Si](C)(C)CC=C FEIZMBLMTCAJSQ-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- PFEAZKFNWPIFCV-UHFFFAOYSA-N hydroxy-[hydroxy(dimethyl)silyl]oxy-dimethylsilane Chemical compound C[Si](C)(O)O[Si](C)(C)O PFEAZKFNWPIFCV-UHFFFAOYSA-N 0.000 description 1
- MYZTUAOLAYIKSJ-UHFFFAOYSA-N hydroxy-[hydroxy(diphenyl)silyl]oxy-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](C=1C=CC=CC=1)(O)O[Si](O)(C=1C=CC=CC=1)C1=CC=CC=C1 MYZTUAOLAYIKSJ-UHFFFAOYSA-N 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000012770 industrial material Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- JMAHZWXTTITJER-UHFFFAOYSA-N iodoboronic acid Chemical compound IB(O)O JMAHZWXTTITJER-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- VJOOEHFQQLYDJI-UHFFFAOYSA-N methoxy(dimethyl)silane Chemical compound CO[SiH](C)C VJOOEHFQQLYDJI-UHFFFAOYSA-N 0.000 description 1
- POPACFLNWGUDSR-UHFFFAOYSA-N methoxy(trimethyl)silane Chemical compound CO[Si](C)(C)C POPACFLNWGUDSR-UHFFFAOYSA-N 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- JEUXZUSUYIHGNL-UHFFFAOYSA-N n,n-diethylethanamine;hydrate Chemical compound O.CCN(CC)CC JEUXZUSUYIHGNL-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- VWBWQOUWDOULQN-UHFFFAOYSA-N nmp n-methylpyrrolidone Chemical compound CN1CCCC1=O.CN1CCCC1=O VWBWQOUWDOULQN-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 238000006384 oligomerization reaction Methods 0.000 description 1
- NIFHFRBCEUSGEE-UHFFFAOYSA-N oxalic acid Chemical compound OC(=O)C(O)=O.OC(=O)C(O)=O NIFHFRBCEUSGEE-UHFFFAOYSA-N 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000003678 scratch resistant effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 239000012974 tin catalyst Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- VBSUMMHIJNZMRM-UHFFFAOYSA-N triethoxy(2-phenylethyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC1=CC=CC=C1 VBSUMMHIJNZMRM-UHFFFAOYSA-N 0.000 description 1
- ZLGWXNBXAXOQBG-UHFFFAOYSA-N triethoxy(3,3,3-trifluoropropyl)silane Chemical compound CCO[Si](OCC)(OCC)CCC(F)(F)F ZLGWXNBXAXOQBG-UHFFFAOYSA-N 0.000 description 1
- DENFJSAFJTVPJR-UHFFFAOYSA-N triethoxy(ethyl)silane Chemical compound CCO[Si](CC)(OCC)OCC DENFJSAFJTVPJR-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- UMFJXASDGBJDEB-UHFFFAOYSA-N triethoxy(prop-2-enyl)silane Chemical compound CCO[Si](CC=C)(OCC)OCC UMFJXASDGBJDEB-UHFFFAOYSA-N 0.000 description 1
- NBXZNTLFQLUFES-UHFFFAOYSA-N triethoxy(propyl)silane Chemical compound CCC[Si](OCC)(OCC)OCC NBXZNTLFQLUFES-UHFFFAOYSA-N 0.000 description 1
- RXJWOBGGPLEFEE-UHFFFAOYSA-N triethyl(propoxy)silane Chemical compound CCCO[Si](CC)(CC)CC RXJWOBGGPLEFEE-UHFFFAOYSA-N 0.000 description 1
- UBMUZYGBAGFCDF-UHFFFAOYSA-N trimethoxy(2-phenylethyl)silane Chemical compound CO[Si](OC)(OC)CCC1=CC=CC=C1 UBMUZYGBAGFCDF-UHFFFAOYSA-N 0.000 description 1
- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- LFRDHGNFBLIJIY-UHFFFAOYSA-N trimethoxy(prop-2-enyl)silane Chemical compound CO[Si](OC)(OC)CC=C LFRDHGNFBLIJIY-UHFFFAOYSA-N 0.000 description 1
- HQYALQRYBUJWDH-UHFFFAOYSA-N trimethoxy(propyl)silane Chemical compound CCC[Si](OC)(OC)OC HQYALQRYBUJWDH-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
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/0874—Reactions involving a bond of the Si-O-Si linkage
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
- C07F7/0872—Preparation and treatment thereof
- C07F7/089—Treatments not covered by a preceding group
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0896—Compounds with a Si-H linkage
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
-
- 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
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- 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
- C08G77/045—Polysiloxanes containing less than 25 silicon atoms
-
- 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
- C08G77/12—Polysiloxanes containing silicon bound to hydrogen
-
- 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
-
- 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
- C08G77/80—Siloxanes having aromatic substituents, e.g. phenyl side groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
Abstract
一種製備及聚合式I之矽氧烷單體的方法。合成包括在鹼性催化劑的存在下,含矽烷醇單元與含烷氧基單元之間的選擇反應。本發明的矽氧烷單體可用於製備具有好的可撓性及破裂臨界值,以及恰當之官能位置的矽氧烷聚合物,其有利於半導體工業中要求金屬含量低的應用。□
Description
本發明是有關於由矽氧烷單體衍生的聚合物。特別的是本發明是關於一種合成矽氧烷單體的方法,以及一種藉由聚合由前述方法獲得的所述單體來製造矽氧烷聚合物的方法。
可撓性聚矽氧烷樹脂(flexible polysiloxane resins)是有用的旋塗式介電質及封膠材料。這些材料通常以甲基三烷氧基矽烷(methyltrialkoxy-silane)與其他烷氧基矽烷之間的共水解反應(co-hydrolysis)及後續的縮合反應來製備。這些材料於半導體工業中用作絕緣材料及平坦化材料。通常,這些材料作為聚合物-溶劑溶液的形式旋轉成型(spin-cast)在矽晶圓上,接著在100℃至150℃下進行軟烤以移除溶劑,以及在200℃至400℃下進行最後固化,其中剩下的矽烷醇熱縮合以形成交聯、不溶的薄膜。
單獨使用甲基三烷氧基矽烷產生破裂臨界值只有2 μm的聚合物,故單獨使用甲基三烷氧基矽烷不適合用於製備厚膜。一般用來增加破裂臨界值的共聚單體為二苯基矽烷二醇(diphenylsilanediol)。然而,與甲基三烷氧基矽烷相比,二苯基矽烷二醇的反應性低,因此二苯基矽烷二醇不易共聚合成聚合物基質(polymer matrix)。在常態的水解條件下,一部分二苯基矽烷二醇保持不具反應性,且所述二苯基矽烷二醇單體易於從溶液中結晶出來。如果最
後的旋塗溶液包含未反應的二苯基矽烷二醇,則在烘烤期間,聚合物膜中之一部分未反應的二苯基矽烷二醇會發出煙氣(fume out),而導致製程設備有顆粒污染的風險。
文獻中有揭露一些描述如何促使反應性低的二苯基矽烷二醇及其他矽烷醇來反應得到聚合物基質的方法。一種方法是在使用或沒有使用催化劑(例如是鋁催化劑、鋯催化劑、錫催化劑或鈦催化劑)的情況下,增加反應溫度至超過100℃(參考文獻1及2)。然而,此方法使得聚合物中無法使用熱敏性共聚單體。金屬催化劑難以或甚至不可能從聚合物溶液中移除。這嚴重地限制上述聚合物在半導體應用中的使用,所述半導體應用通常需要總金屬量低於100 ppb的低金屬污染。
另一個可達到促使二苯基矽烷二醇與聚合物結合的方法是在作為氯化氫清除劑的胺鹼存在下,使二苯基矽烷二醇與例如是甲基三氯矽烷(methyltrichlorosilane)的氯矽烷反應(參考文獻3)。不幸地,氯矽烷對實驗室設備及生產設備具有極強腐蝕性。且副產物(胺鹽酸鹽(amine-hydrochloride salt))需要藉由過濾以從反應混合物中移除,然而由於濕敏性的氯矽烷,故藉由過濾移除副產物不容易達成。
直接使用二苯基矽烷二醇作為半導體工業材料的一個主要的問題是,商品級的二苯基矽烷二醇含有金屬雜質,且有時金屬雜質甚至以極小鐵銹顆粒(rust particle)的形式存在。金屬雜質為固體材料,故無法僅藉由蒸餾而
清除。此為許多具有高沸點或沒有沸點以及具有高熔點之含矽烷醇的矽烷單體的一種常見問題。
美國專利說明書第3,122,579號揭露一種製備矽烷單體的方法,其中將經乙醯氧基修飾或經氯修飾的單體與矽烷醇(Si-OH)進行反應。後者的反應產生難以處理的氫氯沉澱物(hydrochloro precipitate),而第一個反應使乙醯氧基矽烷增加,由於接著形成了等量的乙酸,所述乙醯氧基矽烷難以水解。因此,乙醯氧基矽烷很少用於聚合作用;乙醯氧基矽烷主要適合當作室溫硫化固化(RTV-cured)之矽材料的交聯劑。
本發明的目的為排除至少一部分關於先前技術的問題,並提供一種製造單體的方法,其可用於製造可撓性聚矽氧烷樹脂。
因此,本發明提供一種新的技術解決方法,其製造含矽烷醇單體,而避免發生本領域的問題。另外,本發明提供一種聚合含矽烷醇單體與烷氧基矽烷以得到具高選擇性及高產率之矽氧烷聚合物的方法。
令人驚訝地,發明人發現,在例如是氣態氨的鹼性催化劑存在下,例如是二苯基矽烷二醇的含矽烷醇單體可選擇性地與烷氧基矽烷反應,以產生具高選擇性及高產率的矽氧烷單體。藉此得到的矽氧烷單體可藉由水解及縮合聚
合反應用以製造矽氧烷聚合物。
更具體而言,根據本發明之方法的主要特徵在於申請專利範圍第1項之特徵部分中所陳述的內容。
本發明之用途的特徵在於申請專利範圍第7項所陳述的內容。
本發明提供相當多的優點。因此,在反應期間,不會發生矽烷醇與矽烷醇之間的自縮合作用。本發明不會產生為副產物的固體鹽。僅藉由蒸餾來完成產物的分離,且便於移除任何可能存在於矽烷醇起始材料中的金屬污染物。接著,得到的單體可獨自地聚合及水解或可與矽烷單體一起聚合及水解,以產生具高破裂臨界值的聚合矽氧烷樹脂。
將藉由詳細的說明及參照附圖以更仔細探究本發明。
如上文簡略地描述,本發明提供一種製備式I之矽氧烷單體的方法。
在式I中,n代表數值為在1至3範圍中的整數;R0是具有1個至6個碳原子之未取代或經取代的直鏈或分支鏈烷基;
R1是具有1個至20個碳原子之未取代或經取代的直鏈或分支鏈烷基、芳基、烯基;R2是具有1個至20個碳原子之未取代或經取代的直鏈或分支鏈烷基、芳基、烯基;R3、R4及R5獨立地代表氫或是具有1個至20個碳原子之未取代或經取代的直鏈或分支鏈烷基、芳基、烯基、具有1個至4個碳原子的烷氧基。
在上述定義中,「烷基」通常代表分支鏈或直鏈、選擇性經取代的飽和烴基(hydrocarbyl radical)(烷基)。
在R0的定義中,烷基代表含有1個至6個碳原子的低碳烷基,其選擇性地具有選自甲基及鹵素的1個至3個取代基。R0之特別較佳的實例包括甲基、乙基、正丙基或異丙基以及正丁基、叔丁基或異丁基。
R0連同鄰接的氧原子構成烷氧基,較佳是低碳烷氧基,例如選擇性經取代的甲氧基、乙氧基或異丙氧基。
在取代基R1、R2、R3、R4及R5的定義中,「烷基」較佳是代表具有1個至18個碳原子的烴基、更佳是1個至14個碳原子且特別是1個至12個碳原子。烷基可以是直鏈或分支鏈,而當烷基是分支鏈時,較佳是在α位置或β位置處有分支,且更進一步選擇性地以一或多個(特別是兩個)C1至C6的烷基取代,或是更進一步選擇性鹵化,特別是部分或完全氟化或是全氟化(per-fluorinated)。實例包括非氟化的、部分氟化的及全氟化的異丙基、叔丁基、2-丁基(but-2-yl)、2-甲基-2-丁基(2-methylbut-2-yl)以
及1,2-二甲基-2-丁基(1,2-dimethylbut-2-yl)。
芳基較佳是苯基,其在環上選擇性地具有選自鹵素、烷基或烯基的1個至5個取代基;或是萘基,其在環結構上選擇性地具有選自鹵素、烷基或烯基的1個至11個取代基,且所述取代基選擇性地氟化(包括全氟化或部分氟化)。
本說明書中所使用的「烯基」包括直鏈烯基及分支鏈烯基,例如乙烯基及烯丙基。通常「烯基」含有2個至18個碳原子、更佳是含有2個至14個碳原子且特別較佳是含有2個至12個碳原子。乙烯基(即,以雙鍵鍵結的兩個碳原子)較佳是位在大於或等於2的位置(從分子中的Si原子算起)上。分支鏈烯基較佳是在α位置或β位置處有一個及多個(特別是兩個)C1至C6的烷基、烯基或炔基的分支,特別較佳是氟化或全氟化的烷基、烯基或炔基。
根據本發明的合成包括在鹼性催化劑存在下,含矽烷醇單元與含烷氧基單元之間的選擇反應(參見以下反應式I)。
其中符號n以及R0、R1、R2、R3、R4及R5的定義與上文針對式I所定義的相同。
取決於組分的反應性,在-78℃至+60℃的溫度範圍下操作反應。如果反應在太低的溫度下操作,則在經濟上反應速率太慢。如果反應在太高的溫度下操作,則可能會發生副反應,例如矽烷醇組分的烷氧基化(alkoxylation)或低聚合作用,或是例如是Si-H與醇類之間形成烷氧基及氫氣的反應的其他反應。反應時間是從一分鐘到100小時。反應的過程可以氣相色層分析儀(gas chromatography)來監控。如果反應時間太短,則由於未反應之起始矽烷醇仍存在,故得到低的產率。如果反應時間太長,則反應器的產量將會受影響。
矽烷醇化合物具有通式II,
其中符號R1及R2的定義與上文針對式I所定義的相同。
矽烷醇化合物較佳選自包括二乙基矽烷二醇(diethylsilanediol)、二甲基矽烷二醇(dimethylsilanediol)、二丙基矽烷二醇(dipropylsilanediol)、二異丙基矽烷二醇(diisopropylsilanediol)、二丁基矽烷二醇(dibutylsilanediol)、二叔丁基矽烷二醇(di-tert-butylsilanediol)、二異丁基矽烷二醇(di-iso-butylsilanediol)、二仲丁基矽烷二醇(di-sec-butyl-silanediol)、二苯基矽烷二醇、二環己基矽烷二醇
(dicyclohexylsilanediol)、環己基甲基矽烷二醇(cyclohexylmethylsilanediol)、環己基乙基矽烷二醇(cyclohexylethylsilanediol)、1,1,3,3-四甲基-1,3-二矽氧烷二醇(1,1,3,3-tetramethyldisiloxane-1,3-diol)或1,1,3,3-四苯基-1,3-二矽氧烷二醇(1,1,3,3-tetraphenyldisiloxane-1,3-diol)、1,1,3,3,5,5-六苯基-1,5-三矽氧烷二醇(1,1,3,3,5,5-hexaphenyltrisiloxane-1,5-diol)、雙(對乙烯基苯基)矽烷二醇(bis(p-vinylphenyl)silanediol)、(對乙烯基苯基)苯基矽烷二醇((p-vinylphenyl)phenylsilanediol)、苯基乙烯基矽烷二醇(phenylvinylsilanediol)或1-金剛烷基矽烷三醇(1-adamantylsilanetriol)的族群。
反應的烷氧基矽烷具有通式III,
其中符號R3、R4及R5的定義與上文針對式I所定義的相同。
烷氧基矽烷化合物較佳選自包括四甲氧基矽烷(tetramethoxysilane)、四乙氧基矽烷(tetraethoxysilane)、三甲氧基矽烷(trimethoxysilane)、三乙氧基矽烷(triethoxysilane)、甲基三甲氧基矽烷(methyltrimethoxysilane)、甲基三乙氧基矽烷(methyltriethoxysilane)、乙基
三甲氧基矽烷(ethyltrimethoxysilane)、乙基三乙氧基矽烷(ethyltriethoxysilane)、丙基三甲氧基矽烷(propyltrimethoxysilane)、丙基三乙氧基矽烷(propyltriethoxysilane)、乙烯基三甲氧基矽烷(vinyltrimethoxysilane)、乙烯基三乙氧基矽烷(vinyltriethoxysilane)、乙烯基甲基二甲氧基矽烷(vinylmethyldimethoxysilane)、乙烯基甲基二乙氧基矽烷(vinylmethyldiethoxysilane)、乙烯基二甲基甲氧基矽烷(vinyldimethylmethoxysilane)、乙烯基二甲基乙氧基矽烷(vinyldimethylethoxysilane)、烯丙基三甲氧基矽烷(allyltrimethoxysilane)、烯丙基三乙氧基矽烷(allyltriethoxysilane)、烯丙基甲基二甲氧基矽烷(allylmethyldimethoxysilane)、烯丙基甲基二乙氧基矽烷(allylmethyldiethoxysilane)、烯丙基二甲基甲氧基矽烷(allyldimethylmethoxysilane)、烯丙基二甲基乙氧基矽烷(allyldimethylethoxysilane)、苯基三甲氧基矽烷(phenyltrimethoxysilane)、苯基三乙氧基矽烷(phenyltriethoxysilane)、二苯基二甲氧基矽烷(diphenyldimethoxysilane)、二苯基二乙氧基矽烷(diphenyldiethoxysilane)、巰丙基三甲氧基矽烷(mercaptopropyltrimethoxysilane)、巰丙基三乙氧基矽烷(mercaptopropyltriethoxysilane)、3,3,3-三氟丙基三甲氧基矽烷(3,3,3-trifluoropropyltrimethoxysilane)、3,3,3-三氟丙基三乙氧基矽烷(3,3,3-trifluoropropyltriethoxysilane)、3,3,3-三氟丙基甲基二甲氧基矽烷(3,3,3-trifluoropropylmethyldimethoxysilane)、3,3,3-三氟丙基甲基二乙氧基矽烷
(3,3,3-trifluoropropylmethyldiethoxysilane)、3-氯丙基三甲氧基矽烷(3-chloropropyltrimethoxysilane)、3-氯丙基三乙氧基矽烷(3-chloropropyltriethoxysilane)、3-氯丙基甲基二甲氧基矽烷(3-chloropropylmethyldimethoxysilane)、3-氯丙基甲基二乙氧基矽烷(3-chloropropylmethyldiethoxysilane)、3-氯丙基二甲基甲氧基矽烷(3-chloropropyldimethylmethoxysilane)、3-氯丙基二甲基乙氧基矽烷(3-chloropropyldimethylethoxysilane)、氯甲基三甲氧基矽烷(chloromethyltrimethoxysilane)、氯甲基三乙氧基矽烷(chloromethyltriethoxysilane)、氯甲基甲基二甲氧基矽烷(chloromethylmethyldimethoxysilane)、氯甲基甲基二乙氧基矽烷(chloromethylmethyldiethoxysilane)、氯甲基二甲基甲氧基矽烷(chloromethyldimethylmethoxysilane)、氯甲基二甲基乙氧基矽烷(chloromethyldimethylethoxysilane)、二甲氧基二甲基矽烷(dimethoxydimethylsilane)、二乙氧基二甲基矽烷(diethoxydimethylsilane)、甲氧基二甲基矽烷(methoxydimethylsilane)、乙氧基二甲基矽烷(ethoxydimethylsilane)、甲氧基三甲基矽烷(methoxytrimethylsilane)、乙氧基三甲基矽烷(ethoxytrimethylsilane)、甲基苯基二甲氧基矽烷(methylphenyldimethoxysilane)、甲基苯基二乙氧基矽烷(methylphenyldiethoxysilane)、(對乙烯基苯基)三甲氧基矽烷((p-vinylphenyl)trimethoxysilane)、(對乙烯基苯基)三乙氧基矽烷((p-vinylphenyl)triethoxysilane)、(對乙烯基苯基)甲基二甲氧基矽
烷((p-vinylphenyl)methyldimethoxysilane)、(對乙烯基苯基)甲基二乙氧基矽烷((p-vinylphenyl)methyldiethoxysilane)、2-苯基乙基三甲氧基矽烷(2-phenylethyltri methoxysilane)、2-苯基乙基三乙氧基矽烷(2-phenylethyltriethoxysilane)的族群。
鹼性催化劑較佳選自氨及有機胺的族群。特別地,催化劑的pKb值約在1.5至10的範圍中,較佳地約在2.0至8的範圍中。
催化劑經選擇以使反應速率最佳化,而使副反應減到最少。如果鹼性催化劑太弱(意即,鹼性催化劑的pKb值大於10),則反應變得太緩慢(sluggish)。如果鹼性催化劑太強(意即,鹼性催化劑的pKb值小於1.5),則副反應易於發生。催化劑較佳的是具有足夠的揮發性,使得催化劑可在反應之後輕易地除去(strip out)。或者,催化劑也可以化學計量數量的酸(例如乙酸、甲酸或氯化氫,但不限於此)來中和。然而,使用太多的酸可能會導致矽氧鍵再分配(即亂序(scrambling)),因而降低產率。
鹼性催化劑是選自氨、吡啶(pyridine)、甲基比啶(picoline)、乙醇胺(ethanolamine)、甲胺(methylamine)、二甲胺(dimethylamine)、三甲胺(trimethylamine)、乙胺(ethylamine)、二乙胺(diethylamine)、三乙胺(triethylamine)、異丙胺(isopropylamine)、二異丙胺(diisopropylamine)、二異丙基乙胺(diisopropylethylamine)、丙胺
(propylamine)、丁胺(butylamine)、仲丁胺(sec-butylamine)。
較佳的是根據反應式I在溶劑中執行反應。特別較佳是選擇熔點太低,以致於在合成期間的低溫下溶劑仍是液體的溶劑。另一方面,溶劑的沸點較佳是低到足以輕易地藉由蒸餾來將其從產物中移除。最好是矽烷醇化合物可溶於或實質上可溶於溶劑。
溶劑較佳是不應與反應中所使用的化合物發生反應。
基於上述條件,溶劑選自環狀醚類或直鏈醚類或分支鏈醚類的族群,例如是四氫呋喃(tetrahydrofuran)、2-甲基四氫呋喃(2-methyltetrahydrofuran)、二乙醚(diethyl ether)、二異丙醚(diisopropyl ether)、二丁醚(dibutyl ether)、1,2-二甲氧乙烷(1,2-dimethoxyethane)、1,2-二甲氧丙烷(1,2-dimethoxypropane)、1,2-二乙氧乙烷(1,2-diethoxyethane)、1,2-二乙氧丙烷(1,2-diethoxypropane)、甲基叔丁基醚(methylt-butyl ether)、乙基叔丁基醚(ethylt-butyl ether);或選自脂肪族碳氫化合物的族群,例如戊烷、己烷、庚烷及辛烷;或選自極性溶劑的族群,例如n-甲基吡咯烷酮(n-methylpyrrolidone)、二甲基碸(dimethylsulfone)、二甲基甲醯胺(dimethylformamide)、二乙基甲醯胺(diethylformamide)、二甲基乙醯胺(dimethylacetamide)、四甲脲(tetramethylurea)及二甲基亞碸(dimethylsulfoxide),其中特別較佳是n-甲基吡咯烷酮及二甲基碸。溶劑也可以是溶劑的混合物,較佳是所列舉之
溶劑的混合物。
儘管反應也可在完全沒有溶劑的狀態下操作,但此可能會導致無法徹底攪拌及可能會降低反應速率。
含矽烷醇的矽烷與烷氧基矽烷的莫耳比經選擇以使烷氧基矽烷存在有至少與矽烷醇等量的量,較佳是超過含矽烷醇的矽烷之莫耳量的2到5倍。如果烷氧基矽烷對矽烷醇的比值小於1,則由於反應物的低聚合作用使得產率低。如果比值大於5,則反應變得不經濟。
溶劑與矽烷醇矽烷的質量比較佳是0.1至5。如果比值太小,由於反應溶液中有大量的不溶組分,故攪拌的問題可能會產生。如果比值大於5,則反應變得不經濟。
鹼性催化劑與矽烷醇矽烷的質量比較佳是0.001至1。如果比值太低,則反應組分的酸性雜質可能會使鹼完全中和,因而完全抑制反應性。如果比值大於1,則可能變得難以將鹼移除,且反應變得不經濟。
依據式I的數個單體具有新穎性。因此,本發明涵蓋式I之新穎單體,
其中,n代表數值為在1至3範圍中的整數;R0是具有1個至6個碳原子之未取代或經取代的直鏈
或分支鏈烷基;R1是具有1個至20個碳原子之未取代或經取代的直鏈或分支鏈烷基、芳基、烯基;R2是具有1個至20個碳原子之未取代或經取代的直鏈或分支鏈烷基、芳基、烯基;R3、R4及R5獨立地代表氫或是具有1個至20個碳原子之未取代或經取代的直鏈或分支鏈烷基、芳基、烯基或具有1個至4個碳原子的烷氧基,所述單體不包括式I之n為1、R3代表甲氧基、R4及R5代表氫且R1及R2皆代表苯基的化合物,也不包括式I之n為1、R3及R4代表甲氧基、R5代表氫以及R1及R2皆代表苯基的化合物外。
特別地,單體選自以下的族群:
根據反應式I得到的單體可用於製備具有好的可撓性及破裂臨界值,以及恰當之官能位置的矽氧烷聚合物,其有利於半導體工業中要求金屬含量低的應用。
上述矽氧烷聚合物通常具有在500 g/mol至1,000,000
g/mol範圍中的質量平均分子量。
因此,在有或沒有共聚單體的狀態下,得到的單體可以水及酸性催化劑或鹼性催化劑來進行水解聚合。本發明的單體佔單體混合物中的至少10莫耳%,較佳約為15莫耳%至95莫耳%。
本發明之含有乙烯基、烯丙基或Si-H的單體亦可使用鉑催化劑或鈀催化劑經矽氫化反應來聚合。
單體混合物之其他單體通常為其他的烷氧基矽烷,例如是四烷氧基矽烷或三烷氧基矽烷,其中烷氧基的定義與上文針對式III之烷氧基矽烷所定義的相同。因此,共聚單體可選自四甲氧基矽烷、四乙氧基矽烷、三甲氧基矽烷、三乙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基甲基二甲氧基矽烷、乙烯基甲基二乙氧基矽烷、乙烯基二甲基甲氧基矽烷、乙烯基二甲基乙氧基矽烷、烯丙基三甲氧基矽烷、烯丙基三乙氧基矽烷、烯丙基甲基二甲氧基矽烷、烯丙基甲基二乙氧基矽烷、烯丙基二甲基甲氧基矽烷、烯丙基二甲基乙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、二苯基二甲氧基矽烷、二苯基二乙氧基矽烷、巰丙基三甲氧基矽烷、巰丙基三乙氧基矽烷、3,3,3-三氟丙基三甲氧基矽烷、3,3,3-三氟丙基三乙氧基矽烷、3,3,3-三氟丙基甲基二甲氧基矽烷、3,3,3-三氟丙基甲基二乙氧基矽烷、3-氯丙基三甲氧基矽烷、3-
氯丙基三乙氧基矽烷、3-氯丙基甲基二甲氧基矽烷、3-氯丙基甲基二乙氧基矽烷、3-氯丙基二甲基甲氧基矽烷、3-氯丙基二甲基乙氧基矽烷、氯甲基三甲氧基矽烷、氯甲基三乙氧基矽烷、氯甲基甲基二甲氧基矽烷、氯甲基甲基二乙氧基矽烷、氯甲基二甲基甲氧基矽烷、氯甲基二甲基乙氧基矽烷、二甲氧基二甲基矽烷、二乙氧基二甲基矽烷、甲氧基二甲基矽烷、乙氧基二甲基矽烷、甲氧基三甲基矽烷、乙氧基三甲基矽烷、甲基苯基二甲氧基矽烷、甲基苯基二乙氧基矽烷、(對乙烯基苯基)三甲氧基矽烷、(對乙烯基苯基)三乙氧基矽烷、(對乙烯基苯基)甲基二甲氧基矽烷、(對乙烯基苯基)甲基二乙氧基矽烷、2-苯基乙基三甲氧基矽烷、2-苯基乙基三乙氧基矽烷的族群。
在聚合反應中,酸性催化劑可選自由氫氯酸(hydrochloric acid)、硝酸(nitric acid)、三氟乙酸(trifluoro acetic acid)、乙酸(acetic acid)、甲酸(formic acid)、乙二酸(oxalic acid)、順丁烯二酸(maleic acid)、檸檬酸(citric acid)、磷酸(phosphoric acid)所組成的族群。
在聚合反應中,鹼性催化劑可選自由氨、三甲基氫氧化銨(trimethylammonium hydroxide)、三乙基氫氧化銨(triethylammonium hydroxide)、三丙基氫氧化銨(tripropylammonium hydroxide)、三丁基氫氧化銨(tributylammonium hydroxide)所組成的族群。
可在由下述者組成之族群中選出的溶劑中執行聚合反應,例如丙酮(acetone)、甲基乙基酮(ethyl methyl
ketone)、四氫呋喃、甲醇(methanol)、乙醇(ethanol)、丙醇(propanol)、2-丙醇(2-propanol)、丁醇(butanol)、2-丁醇(2-butanol)、叔丁醇(tert-butanol)、2-甲基-2-丁醇(2-methyl-2-butanol)、乙酸甲酯(methyl acetate)、乙酸乙酯(ethyl acetate)、乙酸丙酯(propyl acetate)、乙酸丁酯(butyl acetate)、丙二醇甲醚(propylene glycol methyl ether,PGME)、丙二醇乙醚(propylene glycol ethyl ether,PGEE)、丙二醇丙醚(propylene glycol propyl ether,PnP)、丙二醇甲醚乙酸酯(propylene glycol methyl ether acetate,PGMEA)、1,2-二甲氧基乙烷(1,2-dimethoxyethane)、1,2-二甲氧基丙烷(1,2-dimethoxypropane)。
基於上述,在一實施例中,藉由添加1當量至5當量的水(通常為0.001M至0.1M的酸溶液)來完成水解聚合。酸選自氫氯酸、硝酸、三氟乙酸、乙酸、甲酸、乙二酸、順丁烯二酸、檸檬酸及磷酸。在0℃至150℃下執行聚合反應歷時1小時至24小時。
如果聚合反應時間太短且反應溫度太低,則不完全的水解可能會導致低分子量的聚合物。未反應的烷氧基可能會仍留在聚合物中。如果聚合反應時間太長且/或反應時間太高,則聚合物的膠凝化(gelling)可能會發生。
如果聚合物的分子量太低,則聚合物可在溶劑中有或沒有鹼性催化劑(例如三乙基胺)的狀態下於100℃至200℃下進一步加熱。加熱的持續時間由從溶液中取出之樣品經膠體滲透層析儀(Gel Permeation Chromatography,
GPC)量測後決定。當得到目標分子量時,即冷卻反應,且以稀酸並接著以去離子水進行沖洗來中和胺催化劑。
由上述程序得到的組成物通常可配製成含有如上文所描述的矽氧烷聚合物以及溶劑及添加物的矽氧烷聚合物組成物。
由於單體之特定的製造製程,故任何依照揭露內容所得到的矽氧烷聚合物組成物將具有低的金屬含量;特別的是已發現金屬雜質可低至100 ppb以下。
以下以非限制性的實例說明本發明。
將二苯基矽烷二醇(60 g)、四氫呋喃(THF,30 g)及甲基三甲氧基矽烷(MTMOS,180 g)放入有攪拌子及回流冷凝器(reflux condenser)的500 mL三頸圓底燒瓶中。使上述燒瓶冷卻至-20℃。在攪拌的同時,將氨氣(約8 g)緩慢吹入溶液中直到溶液變澄清為止。使反應在-20℃下進行18小時。接著,將反應加熱至70℃,並進行回流
一小時以移除氨。接著,將蒸餾冷凝器(distillation condenser)裝到燒瓶上,且緩慢抽真空以移除甲醇、THF及過量的MTMOS。在150℃~160℃/0.1 mbar下蒸餾剩下的液體,以得到為無色液體的1,1,5,5-四甲氧基-1,5-二甲基-3,3-二苯基三矽氧烷(1,1,5,5-tetramethoxy-1,5-dimethyl-3,3-diphenyltrisiloxane)(97 g,82%,由GC/MS測得純度>99%)。
將二苯基矽烷二醇(60 g)、四氫呋喃(THF,50 g)及苯基三甲氧基矽烷(phenyltrimethoxysilane,PhTMOS,300 g)放入有攪拌子及回流冷凝器的500 mL三頸圓底燒瓶中。使上述燒瓶冷卻至-20℃。在攪拌的同時,將氨氣(約8 g)緩慢吹入溶液中直到溶液變澄清為止。使反應在-20℃下進行18小時。接著,將反應加熱至70℃,並進行回流一小時以移除氨。接著,將蒸餾冷凝器裝到燒瓶上,且緩慢抽真空以移除甲醇及THF。在120℃/0.1 mbar下蒸餾剩下的液體,以移除過量的PhTMOS,並接著在210℃~230℃/0.1 mbar下進行蒸餾,以得到為無色、黏性液體的1,1,5,5-四甲氧基-1,3,3,5-四苯基三矽氧烷(1,1,5,5-tetramethoxy-1,3,3,5-tetraphenyltrisiloxane)(117 g,77%)。
將二苯基矽烷二醇(60 g)、四氫呋喃(THF,30 g)及三乙氧基矽烷(triethoxysilane,HTEOS,185 g)放入有攪拌子及回流冷凝器的500 mL三頸圓底燒瓶中。使上述
燒瓶冷卻至-10℃。將吡啶(約3 g)加入溶液中。使反應在-10℃下進行18小時。接著,將蒸餾冷凝器裝到燒瓶上,且緩慢抽真空以移除乙醇、THF、吡啶及過量的HTEOS。在140℃~170℃/0.1 mbar下蒸餾剩下的液體,以得到為無色液體的1,1,5,5-四乙氧基-3,3-二苯基三矽氧烷(1,1,5,5-tetraethoxy-3,3-diphenyltrisiloxane)(105 g,84%)。
將二苯基矽烷二醇(60 g)、四氫呋喃(THF,30 g)及乙烯基三甲氧基矽烷(VTMOS,200 g)放入有攪拌子及回流冷凝器的500 mL三頸圓底燒瓶中。使上述燒瓶冷卻至-20℃。在攪拌的同時,將氨氣(約8 g)緩慢吹入溶液中直到溶液變澄清為止。使反應在-20℃下進行18小時。接著,將反應加熱至70℃,並進行回流一小時以移除氨。接著,將蒸餾冷凝器裝到燒瓶上,且緩慢抽真空以移除甲醇、THF及過量的VTMOS。在150℃~170℃/0.1 mbar下蒸餾剩下的液體,以得到為無色液體的1,1,5,5-四甲氧基-1,5-二乙烯基-3,3-二苯基三矽氧烷(1,1,5,5-tetramethoxy-1,5-divinyl-3,3-diphenyltrisiloxane)(104.5 g,87%)。
將二異丙基矽烷二醇(10 g,以已知方法製備,參見參考文獻4)、四氫呋喃(THF,5 g)及甲基三甲氧基矽烷(MTMOS,60 g)放入有攪拌子及回流冷凝器的250 mL三頸圓底燒瓶中。使上述燒瓶冷卻至-20℃。在攪拌的同時,將氨氣(約3 g)緩慢吹入溶液中直到溶液變澄清為
止。使反應在-20℃下進行18小時。接著,將反應加熱至70℃,並進行回流一小時以移除氨。接著,將蒸餾冷凝器裝到燒瓶上,且緩慢抽真空以移除甲醇、THF及過量的MTMOS。在130℃~150℃/0.1 mbar下蒸餾剩下的液體,以得到為無色液體的1,1,5,5-四甲氧基-1,5-二甲基-3,3-二異丙基三矽氧烷(1,1,5,5-tetramethoxy-1,5-dimethyl-3,3-diisopropyltrisiloxane)(18 g,75%)。
將二苯基矽烷二醇(60 g)、四氫呋喃(THF,30 g)及四甲氧基矽烷(TMOS,200 g)放入有攪拌子及回流冷凝器的500 mL三頸圓底燒瓶中。使上述燒瓶冷卻至-20℃。在攪拌的同時,將氨氣(約8 g)緩慢吹入溶液中直到溶液變澄清為止。使反應在-20℃下進行18小時。接著,將反應加熱至70℃,並進行回流一小時以移除氨。接著,將蒸餾冷凝器裝到燒瓶上,且緩慢抽真空以移除甲醇、THF及過量的TMOS。在150℃~170℃/0.1 mbar下蒸餾剩下的液體,以得到為無色液體的1,1,1,5,5,5-六甲氧基-3,3-二苯基三矽氧烷(1,1,1,5,5,5-hexamethoxy-3,3-diphenyltrisiloxane)(115 g,90%)。
將二苯基矽烷二醇(5 g)、四氫呋喃(THF,4 g)及甲基二乙氧基矽烷(methyldiethoxysilane,MHDEOS,15 g)放入有攪拌子及回流冷凝器的50 mL三頸圓底燒瓶中。使上述燒瓶維持在+23℃下,而同時加入乙醇胺(0.1 mL)。
使反應在23℃~40℃下進行10分鍾,且在反應進行完後,操作GC/MS以進行量測。顯示出反應溶液的高沸點組分僅含有1,5-二甲基-1,5-二乙氧基-3,3-二苯基三矽氧烷(1,5-dimethyl-1,5-diethoxy-3,3-diphenyltrisiloxane)(圖1及圖2)。
將二苯基矽烷二醇(5 g)、四氫呋喃(THF,4 g)及巰丙基三甲氧基矽烷(MPTS,30 g)放入有攪拌子及回流冷凝器的100 mL三頸圓底燒瓶中。使上述燒瓶維持在+0℃下,而同時吹入氨(約1 g)。使反應在0℃下進行4小時,接著加溫至室溫(歷時18小時)。當操作GC/MS進行量測時,觀察到對應1,5-雙(巰丙基)-1,1,5,5-四甲氧基-3,3-二苯基三矽氧烷(1,5-bis(mercaptopropyl)-1,1,5,5-tetramethoxy-3,3-diphenyltrisiloxane)的波峰,以及未反應的過量MPTS。
將苯基甲基矽烷二醇(Phenylmethylsilanediol,4 g)、四氫呋喃(THF,4 g)及VTMOS(20 g)放入有攪拌子及回流冷凝器的50 mL三頸圓底燒瓶中。使上述燒瓶維持在-15℃下,而同時吹入氨(約1 g)。使反應在-15℃下進行2小時,接著在-20℃下進行18小時。當操作GC/MS進行量測時,觀察到對應1,5-二乙烯基-1,1,5,5-四甲氧基-3-苯基-3-甲基三矽氧烷(1,5-divinyl-1,1,5,5-tetramethoxy-3-phenyl-3-methyltrisiloxane)的單波峰,以及未反應的過量
VTMOS。
將環己基甲基矽烷二醇(4 g)、四氫呋喃(THF,4 g)及VTMOS(20 g)放入有攪拌子及回流冷凝器的50 mL三頸圓底燒瓶中。使上述燒瓶維持在-15℃下,而同時吹入氨(約1 g)。使反應在-15℃下進行1小時,接著在-20℃下進行18小時。當操作GC/MS進行量測時,觀察到對應1,5-二乙烯基-1,1,5,5-四甲氧基-3-環己基-3-甲基三矽氧烷(1,5-divinyl-1,1,5,5-tetramethoxy-3-cyclohexyl-3-methyltrisiloxane)的單波峰,以及未反應的過量VTMOS。
將1,1,3,3-四甲基-1,3-二矽氧烷二醇(4 g,以已知方法製備,參見參考文獻5)、四氫呋喃(THF,10g)及VTMOS(30 g)放入有攪拌子及回流冷凝器的100 mL三頸圓底燒瓶中,並將此燒瓶冷卻至-20℃。吹入氨(約1 g)。使反應在-20℃下進行18小時。以旋轉蒸發器(rotary evaporator)除去溶液中的低沸點材料,接著在100℃~135℃/<5 mbar下進行短程蒸餾(short path distillation)。蒸餾液(8 g)的GC/MS光譜顯示僅有兩個波峰,其對應於1,1,7,7-四甲氧基-1,7-二乙烯基-3,3,5,5-四甲基四矽氧烷(1,1,7,7-tetramethoxy-1,7-divinyl-3,3,5,5-tetramethyltetrasiloxane)(73.1%)以及1,1,5,5-四甲氧基-3,3-二甲基三矽氧烷(1,1,5,5-tetramethoxy-3,3-dimethyltrisiloxane)(26.9%)。以四甲基二矽氧烷二醇為基準,此反應的總產率等於
88.6%。
將1,1,3,3-四甲基-1,3-二矽氧烷二醇(2.4 g)、、四氫呋喃(THF,5 g)及HTEOS(16 g)放入有攪拌子及回流冷凝器的50 mL三頸圓底燒瓶中,並將此燒瓶冷卻至-25℃。加入三滴吡啶。使反應在-25℃下進行。在反應期間,沒有觀察到氫氣產生(no hydrogen evolution)。六小時之後,以旋轉蒸發器移除低沸點揮發物,且在60℃~80℃/<1 mbar下對剩餘液體進行真空蒸餾。操作GC/MS以量測蒸餾液(5.1 g),且僅觀察到兩個波峰,其對應於1,1,7,7-四乙氧基-3,3,5,5-四甲基四矽氧烷(1,1,7,7-tetraethoxy-3,3,5,5-tetramethyltetrasiloxane)(73.0%)以及1,1,5,5-四乙氧基-3,3-二甲基三矽氧烷(1,1,5,5-tetraethoxy-3,3-dimethyltrisiloxane)(27.0%)。以四甲基二矽氧烷二醇為基準,此反應的總產率等於93.1%。
將縮水甘油氧基丙基三甲氧基矽烷(glycidyloxypropyltrimethoxysilane,13.3 g)以及來自實例1的單體(31.8 g)與丙酮(55 g)一起放入250 mL圓底燒瓶中。接著,加入稀HCl(22 g,0.01 M),且在回流下使水解縮合反應進行五小時。在回流之後,溶液看起來是澄清的。將上述溶液以旋轉蒸發器進行蒸發,並加入PGMEA( )。持續蒸發直到聚合物溶液的固體含量達40%為止。在加入5%去離子水(DIW)後,使溶液進一步在100℃下加熱2
小時。GPC顯示出少量的低聚合物(圖3,圈起處),其分子量(Mw)為3,500 g/mol。當將作為光酸及感光劑(sensitizer)的2% Rhodorsil® 2074(由Rhodia Inc.生產的碘硼酸鹽(iodonium borate salt))及0.5% Anthracure® UVS-1221(由Kawasaki Kasei Chemicals Ltd.生產的9,10-二丙基蔥(9,10-dipropoxyanthracene))加入時,所述材料可以波長為365 nm的紫外光進行圖案化。製備出無破裂之厚度大於17 μm的厚膜。在150℃/5 min下的軟烤期間或在200℃/30 min下的固化期間,薄膜不會發出煙氣。
將來自實例3的1,1,5,5-四乙氧基-3,3-二苯基三矽氧烷(5 g)及1,4-環己烷二甲醇二乙烯醚(1,4-cyclohexyldimethanol divinyl ether,3.25 g)放入30 mL的乾淨玻璃瓶中。注入Karsted’s催化劑(10 μL之2%的二甲苯溶液),並使矽氫化反應進行24小時,在矽氫化反應後,紅外線光譜儀(FTIR)沒有觀測到有剩下的乙烯基波峰。藉由GPC量測之分子量Mw/Mn為4,962/1,753。以丙酮(25 g)來稀釋聚合物,且加入硝酸(0.01M,2.5 ekv)來水解聚合物的乙氧基。使反應在+23℃下再進行24小時,在完成反
應後,以旋轉蒸發器將溶劑置換成PGMEA。得到分子量Mw/Mn為11,512/2,211的聚合物。以16%的溶液將材料旋轉成型,溶液中含有PGMEA/MEK(60/40)以及1% BYK ®-306(由BYK-Chemie GmbH生產的界面活性劑)。在130℃/1 min下對薄膜進行軟烤,接著在200℃/60 min下進行固化。得到有彈性且防刮的透明薄膜(Tx為575 nm,RI為1.55,收縮率為1.8%)。
將二苯基矽烷二醇(60 g)、四氫呋喃(THF,30 g)及三乙氧基矽烷(HTEOS,180 g)放入有攪拌子及回流冷凝器的500 mL三頸圓底燒瓶中。在+23℃下,沒有氨催化劑存在時使反應進行24小時。GC/MS顯示,沒有發生所要的反應。僅發生矽烷二醇與HTEOS之間一部分的烷氧基/OH置換,從而得到乙氧基二苯基矽烷醇及二乙氧基二苯基矽烷。
將二苯基矽烷二醇(60 g)、四氫呋喃(THF,30 g)及甲基三甲氧基矽烷(MTMOS,180 g)放入有攪拌子及回流冷凝器的500 mL三頸圓底燒瓶中。在+23℃下,沒有
氨催化劑存在時使反應進行24小時。GC/MS顯示,沒有發生所要的反應。僅發生矽烷二醇與MTMOS之間一部分的烷氧基/OH置換,從而得到甲氧基二苯基矽烷醇及二甲氧基二苯基矽烷。
將二苯基矽烷二醇(60 g)、四氫呋喃(THF,30 g)及甲基三甲氧基矽烷(MTMOS,180 g)放入有攪拌子及回流冷凝器的500 mL三頸圓底燒瓶中。使上述燒瓶冷卻至-20℃。將1,8-二氮雜雙環-7-十一烯(1,8-Diazabicycloundec-7-ene,DBU,0.5 g)加入溶液中。使反應在-20℃下進行5小時,且在反應進行完後,操作GC/MS以量測反應混合物。GC/MS顯示雖然能形成所要產物(產率低),但超過80%的二苯基矽烷二醇轉變成二甲氧基二苯基矽烷。對於此反應而言,DBU(pKb為1.1)顯然是太強的鹼,而使得發生過多的副反應。
將縮水甘油氧基丙基三甲氧基矽烷(13.3 g)及二苯基矽烷二醇(16.2 g)以及MTMOS(20.5 g)與丙酮(50 g)一起放入250 mL圓底燒瓶中。接著,加入稀HCl(17 g,0.01 M),並在回流下使水解縮合反應進行五小時。在回流之後,溶液看起來是混濁的,且含有白色顆粒及棕色顆粒。白色顆粒有可能是未反應的二苯基矽烷二醇,而棕色顆粒是鐵銹,其為市售二苯基矽烷二醇中的汙染物。將聚合物以旋轉蒸發器進行蒸發,並加入PGMEA(3×100 g)。持
續蒸發直到溶液的固體含量達40%為止。在加入5% DIW後,使溶液在100℃下加熱2小時。GPC顯示出大量未反應的二苯基矽烷二醇(圖4)。當將作為光酸及感光劑的2% Rhodorsil® 2074(由Rhodia Inc.生產的碘硼酸鹽)及0.5% Anthracure® UVS-1221(由Kawasaki Kasei Chemicals Ltd.生產的9,10-二丙基蔥)加入時,所述材料可因光而圖案化。在150℃下進行軟烤及200℃下進行固化的期間,材料劇烈地發出煙氣。厚度大於10 μm的厚膜發生破裂。
本發明的矽氧烷單體可用於製備具有好的可撓性及破裂臨界值,以及具有有利於半導體工業中需要低金屬含量的應用之適當官能位置的矽氧烷聚合物。特別的是矽氧烷聚合物可用於半導體工業中之介電質的應用。
1. US 5883214
2. US 20110052890
3. EP 0725103A2
4. Buttrus, Nabeel H. et al., J. Organomet. Chem.
1986, 302(2), 159-63
5. Harris, G. I., J. Chem. Soc. 1963, 5978
圖1顯示實例7之反應溶液的氣相層析圖(GC)。
圖2顯示實例7之反應溶液在第15分鐘時的波峰質譜。
圖3顯示實例13之聚合物的膠體滲透層析曲線,其中在第28.5分鐘時僅觀察到少量的二苯基矽烷二醇。
圖4顯示比較實例3之聚合物的膠體層析曲線,其中在第28.5分鐘時觀察到對應於大量未反應之二苯基矽烷二醇的波峰。
Claims (16)
- 一種製備式I之矽氧烷單體的方法,包括:在鹼性催化劑存在且溶劑選擇性存在的狀況下,將式II之含矽烷醇的矽烷化合物與式III的烷氧基矽烷反應的步驟,所述鹼性催化劑的pKb為1.5至10,
- 如申請專利範圍第1項所述之製備式I之矽氧烷單體的方法,其中所述鹼性催化劑的pKb為2至8。
- 如申請專利範圍第1項或第2項所述之製備式I之矽氧烷單體的方法,其中所述鹼性催化劑選自由氨、吡啶、甲基比啶、乙醇胺、甲胺、二甲胺、三甲胺、乙胺、二乙胺、三乙胺、異丙胺、二異丙胺、二異丙基乙胺、丙胺、丁胺與仲丁胺所組成的族群。
- 如申請專利範圍第1項至第3項中任一項所述之製備式I之矽氧烷單體的方法,其中式II之含矽烷醇的矽烷選自由二乙基矽烷二醇、二甲基矽烷二醇、二丙基矽烷二醇、二異丙基矽烷二醇、二丁基矽烷二醇、二叔丁基矽烷二醇、二異丁基矽烷二醇、二仲丁基矽烷二醇、二苯基矽烷二醇、二環己基矽烷二醇、環己基甲基矽烷二醇、環己基乙基矽烷二醇、1,1,3,3-四甲基-1,3-二矽氧烷二醇或1,1,3,3-四苯基-1,3-二矽氧烷二醇、1,1,3,3,5,5-六苯基-1,5-三矽氧烷二醇、雙(對乙烯基苯基)矽烷二醇、(對乙烯基苯基)苯基矽烷 二醇、苯基乙烯基矽烷二醇或1-金剛烷基矽烷三醇所組成的族群。
- 如申請專利範圍第1項至第3項中任一項所述之製備式I之矽氧烷單體的方法,其中式III的烷氧基矽烷選自由四甲氧基矽烷、四乙氧基矽烷、三甲氧基矽烷、三乙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基甲基二甲氧基矽烷、乙烯基甲基二乙氧基矽烷、乙烯基二甲基甲氧基矽烷、乙烯基二甲基乙氧基矽烷、烯丙基三甲氧基矽烷、烯丙基三乙氧基矽烷、烯丙基甲基二甲氧基矽烷、烯丙基甲基二乙氧基矽烷、烯丙基二甲基甲氧基矽烷、烯丙基二甲基乙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、二苯基二甲氧基矽烷、二苯基二乙氧基矽烷、巰丙基三甲氧基矽烷、巰丙基三乙氧基矽烷、3,3,3-三氟丙基三甲氧基矽烷、3,3,3-三氟丙基三乙氧基矽烷、3,3,3-三氟丙基甲基二甲氧基矽烷、3,3,3-三氟丙基甲基二乙氧基矽烷、3-氯丙基三甲氧基矽烷、3-氯丙基三乙氧基矽烷、3-氯丙基甲基二甲氧基矽烷、3-氯丙基甲基二乙氧基矽烷、3-氯丙基二甲基甲氧基矽烷、3-氯丙基二甲基乙氧基矽烷、氯甲基三甲氧基矽烷、氯甲基三乙氧基矽烷、氯甲基甲基二甲氧基矽烷、氯甲基甲基二乙氧基矽烷、氯甲基二甲基甲氧基矽烷、氯甲基二甲基乙氧基矽烷、二甲氧基二甲基矽烷、二乙氧基二甲基矽烷、甲氧基二甲基矽 烷、乙氧基二甲基矽烷、甲氧基三甲基矽烷、乙氧基三甲基矽烷、甲基苯基二甲氧基矽烷、甲基苯基二乙氧基矽烷、(對乙烯基苯基)三甲氧基矽烷、(對乙烯基苯基)三乙氧基矽烷、(對乙烯基苯基)甲基二甲氧基矽烷、(對乙烯基苯基)甲基二乙氧基矽烷、2-苯基乙基三甲氧基矽烷、2-苯基乙基三乙氧基矽烷所組成的族群。
- 如上述任一申請專利範圍所述之製備式I之矽氧烷單體的方法,其中所述溶劑選自由四氫呋喃、2-甲基四氫呋喃、二乙醚、二異丙醚、二丁醚、1,2-二甲氧乙烷、1,2-二甲氧丙烷、1,2-二乙氧乙烷、1,2-二乙氧丙烷、甲基叔丁基醚、乙基叔丁基醚、戊烷、己烷、庚烷、辛烷、n-甲基吡咯烷酮、二甲基碸或其任何混合物所組成的族群。
- 一種申請專利範圍第1項至第6項中任一項所述之製備式I之矽氧烷單體的方法的用途,適於製造製造矽氧烷聚合物,其中,在酸性催化劑或鹼性催化劑存在且溶劑選擇性存在時,藉由使所述矽氧烷單體在共聚單體存在或共聚單體不存在的狀況下與水反應,使其經歷水解及縮合作用。
- 如申請專利範圍第7項所述之製造矽氧烷聚合物的方法,其中所述矽氧烷聚合物的質量平均分子量在500 g/mol至1,000,000 g/mol的範圍中。
- 如申請專利範圍第7項或第8項所述之製造矽氧烷聚合物的方法,其中所述矽氧烷單體選自由1,1,5,5-四甲氧基-1,5-二甲基-3,3-二苯基三矽氧烷、1,1,5,5-四甲氧基 -1,3,3,5-四苯基三矽氧烷、1,1,5,5-四乙氧基-3,3-二苯基三矽氧烷、1,1,5,5-四甲氧基-1,5-二乙烯基-3,3-二苯基三矽氧烷、1,1,5,5-四甲氧基-1,5-二甲基-3,3-二異丙基三矽氧烷、1,1,1,5,5,5-六甲氧基-3,3-二苯基三矽氧烷、1,5-二甲基-1,5-二乙氧基-3,3-二苯基三矽氧烷、1,5-雙(巰丙基)-1,1,5,5-四甲氧基-3,3-二苯基三矽氧烷、1,5-二乙烯基-1,1,5,5-四甲氧基-3-苯基-3-甲基三矽氧烷、1,5-二乙烯基-1,1,5,5-四甲氧基-3-環己基-3-甲基三矽氧烷、1,1,7,7-四甲氧基-1,7-二乙烯基-3,3,5,5-四甲基四矽氧烷、1,1,5,5-四甲氧基-3,3-二甲基三矽氧烷、1,1,7,7-四乙氧基-3,3,5,5-四甲基四矽氧烷、1,1,5,5-四乙氧基-3,3-二甲基三矽氧烷所組成的族群。
- 如申請專利範圍第7項至第9項中任一項所述之製造矽氧烷聚合物的方法,其中所述酸性催化物選自由氫氯酸、硝酸、三氟乙酸、乙酸、甲酸、乙二酸、順丁烯二酸、檸檬酸、磷酸所組成的族群。
- 如申請專利範圍第7項至第9項中任一項所述之製造矽氧烷聚合物的方法,其中所述鹼性催化物選自由氨、三甲基氫氧化銨、三乙基氫氧化銨、三丙基氫氧化銨、三丁基氫氧化銨所組成的族群。
- 如申請專利範圍第7項至第11項中任一項所述之製造矽氧烷聚合物的方法,其中所述溶劑選自由丙酮、乙基甲基酮、四氫呋喃、甲醇、乙醇、丙醇、2-丙醇、丁醇、2-丁醇、叔丁醇、2-甲基-2-丁醇、乙酸甲酯、乙酸乙酯、乙酸丙酯、乙酸丁酯、丙二醇甲醚(PGME)、丙二醇乙醚 (PGEE)、丙二醇丙醚(PnP)、丙二醇甲醚乙酸酯(PGMEA)、1,2-二甲氧基乙烷、1,2-二甲氧基丙烷所組成的族群。
- 如申請專利範圍第7項至第12項中任一項所述之製造矽氧烷聚合物的方法,其中所述共聚單體選自由四甲氧基矽烷、四乙氧基矽烷、三甲氧基矽烷、三乙氧基矽烷、甲基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧基矽烷、乙烯基甲基二甲氧基矽烷、乙烯基甲基二乙氧基矽烷、乙烯基二甲基甲氧基矽烷、乙烯基二甲基乙氧基矽烷、烯丙基三甲氧基矽烷、烯丙基三乙氧基矽烷、烯丙基甲基二甲氧基矽烷、烯丙基甲基二乙氧基矽烷、烯丙基二甲基甲氧基矽烷、烯丙基二甲基乙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、二苯基二甲氧基矽烷、二苯基二乙氧基矽烷、巰丙基三甲氧基矽烷、巰丙基三乙氧基矽烷、3,3,3-三氟丙基三甲氧基矽烷、3,3,3-三氟丙基三乙氧基矽烷、3,3,3-三氟丙基甲基二甲氧基矽烷、3,3,3-三氟丙基甲基二乙氧基矽烷、3-氯丙基三甲氧基矽烷、3-氯丙基三乙氧基矽烷、3-氯丙基甲基二甲氧基矽烷、3-氯丙基甲基二乙氧基矽烷、3-氯丙基二甲基甲氧基矽烷、3-氯丙基二甲基乙氧基矽烷、氯甲基三甲氧基矽烷、氯甲基三乙氧基矽烷、氯甲基甲基二甲氧基矽烷、氯甲基甲基二乙氧基矽烷、氯甲基二甲基甲氧基矽烷、氯甲基二甲基乙氧基矽烷、二甲 氧基二甲基矽烷、二乙氧基二甲基矽烷、甲氧基二甲基矽烷、乙氧基二甲基矽烷、甲氧基三甲基矽烷、乙氧基三甲基矽烷、甲基苯基二甲氧基矽烷、甲基苯基二乙氧基矽烷、(對乙烯基苯基)三甲氧基矽烷、(對乙烯基苯基)三乙氧基矽烷、(對乙烯基苯基)甲基二甲氧基矽烷、(對乙烯基苯基)甲基二乙氧基矽烷、2-苯基乙基三甲氧基矽烷、2-苯基乙基三乙氧基矽烷或其任何混合物所組成的族群。
- 一種矽氫化的方法,藉由鉑催化劑或鈀催化劑,使申請專利範圍第1項之所述矽氧烷單體的乙烯基、烯丙基或Si-H之官能基進行矽氫化反應。
- 一種矽氧烷單體,由式I表示:
- 如申請專利範圍第15項所述之矽氧烷單體,其選自以下族群:
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201161496584P | 2011-06-14 | 2011-06-14 | |
??20115591 | 2011-06-14 | ||
US61/496,584 | 2011-06-14 | ||
FI20115591A FI127433B (fi) | 2011-06-14 | 2011-06-14 | Menetelmä siloksaanimonomeerien syntetisoimiseksi sekä näiden käyttö |
Publications (2)
Publication Number | Publication Date |
---|---|
TW201307372A true TW201307372A (zh) | 2013-02-16 |
TWI610934B TWI610934B (zh) | 2018-01-11 |
Family
ID=44206802
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
TW101121250A TWI610934B (zh) | 2011-06-14 | 2012-06-14 | 矽氧烷單體的合成方法及其用途 |
Country Status (4)
Country | Link |
---|---|
US (2) | US9458183B2 (zh) |
FI (1) | FI127433B (zh) |
TW (1) | TWI610934B (zh) |
WO (1) | WO2012172176A2 (zh) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI611838B (zh) * | 2016-10-05 | 2018-01-21 | 汕頭市駿碼凱撒有限公司 | 以固態鈀觸媒進行矽氫加成反應之方法 |
TWI765320B (zh) * | 2019-08-22 | 2022-05-21 | 美商艾德凡斯化學公司 | 具有表面活性性質之胺基酸的矽氧烷衍生物 |
US11427760B2 (en) | 2020-02-05 | 2022-08-30 | Advansix Resins & Chemicals Llc | Surfactants for electronics |
US11525105B2 (en) | 2019-12-20 | 2022-12-13 | Advansix Resins & Chemicals Llc | Surfactants for cleaning products |
US11542428B2 (en) | 2019-12-31 | 2023-01-03 | Advansix Resins & Chemicals Llc | Surfactants for oil and gas production |
US11571377B2 (en) | 2019-12-19 | 2023-02-07 | Advansix Resins & Chemicals Llc | Surfactants for use in personal care and cosmetic products |
US11633481B2 (en) | 2019-12-20 | 2023-04-25 | Advansix Resins & Chemicals Llc | Surfactants for use in healthcare products |
US11905304B2 (en) | 2019-12-19 | 2024-02-20 | Advansix Resins & Chemicals Llc | Surfactants for agricultural products |
US12054663B2 (en) | 2019-12-19 | 2024-08-06 | Advansix Resins & Chemicals Llc | Surfactants for inks, paints, and adhesives |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL235415A0 (en) | 2014-10-30 | 2015-01-29 | Univ Ramot | Energetic substances and mixtures containing them |
JP6603115B2 (ja) * | 2015-11-27 | 2019-11-06 | 信越化学工業株式会社 | ケイ素含有縮合物、ケイ素含有レジスト下層膜形成用組成物、及びパターン形成方法 |
JP6621226B2 (ja) * | 2016-02-15 | 2019-12-18 | 国立研究開発法人産業技術総合研究所 | シロキサン及びその製造方法 |
FI127462B (en) * | 2016-07-14 | 2018-06-29 | Inkron Oy | Siloxane monomers, their polymerization and uses |
DE102016117519A1 (de) * | 2016-09-16 | 2018-03-22 | Osram Opto Semiconductors Gmbh | Verfahren zur Herstellung eines Siloxans, Verfahren zur Herstellung eines Polysiloxans, Verfahren zum Vergießen von optoelektronischen Bauelementen |
JP7157998B2 (ja) * | 2017-04-24 | 2022-10-21 | 国立研究開発法人産業技術総合研究所 | シロキサン化合物の製造方法、新規なシロキサン化合物、およびそれらの用途 |
WO2018216807A1 (ja) * | 2017-05-25 | 2018-11-29 | 国立研究開発法人産業技術総合研究所 | オルガノシロキサン及びその製造方法 |
JP7178105B2 (ja) * | 2017-09-15 | 2022-11-25 | 国立研究開発法人産業技術総合研究所 | オルガノシロキサン及びオルガノシロキサンの製造方法 |
TW202116879A (zh) * | 2019-10-30 | 2021-05-01 | 日商陶氏東麗股份有限公司 | 有機聚矽氧烷、其製造方法以及導熱性矽組成物 |
CN111286034A (zh) * | 2020-04-03 | 2020-06-16 | 苏州天山新材料技术有限公司 | 有机硅聚合物、包含其的混合物和有机硅胶粘剂 |
CN114805426B (zh) * | 2022-01-07 | 2024-03-19 | 山东硅科新材料有限公司 | 一种改性乙烯基硅烷及其制备方法和应用 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2611774A (en) | 1950-01-09 | 1952-09-23 | Dow Corning | Diphenylsiloxane copolymers and methods of preparation thereof |
US3122579A (en) | 1960-10-17 | 1964-02-25 | Dow Corning | Mixed trisiloxanes |
NL131010C (zh) | 1965-02-04 | 1900-01-01 | ||
US3523131A (en) * | 1968-10-15 | 1970-08-04 | Siegfried Sliwinski | Process for the production of methyl phenyl trisiloxanes |
DE59402555D1 (de) | 1993-08-24 | 1997-05-28 | Siemens Ag | Verfahren zur herstellung von epoxysiloxanen |
JP3453863B2 (ja) | 1994-07-22 | 2003-10-06 | 信越化学工業株式会社 | α,ω−ジアルコキシオルガノハイドロジェンポリシロキサン及びその製造方法 |
JP3542185B2 (ja) | 1995-02-02 | 2004-07-14 | ダウ コーニング アジア株式会社 | シリコーンレジン、これを含む組成物およびその硬化方法 |
US20020111417A1 (en) * | 2000-12-13 | 2002-08-15 | Lauren International, Inc. | Fluoroelastomer films prepared by peroxide curing a water-borne fluoroelastomer coating |
ATE359323T1 (de) * | 2003-09-04 | 2007-05-15 | 3M Espe Ag | Allylsilan enthaltende zusammensetzung |
JP4801320B2 (ja) | 2003-12-19 | 2011-10-26 | 東レ・ダウコーニング株式会社 | 付加反応硬化型オルガノポリシロキサン樹脂組成物 |
DE102004058000A1 (de) * | 2004-12-01 | 2006-06-08 | Wacker Chemie Ag | Verfahren zur kontinuierlichen Hydrosilylierung |
JP5137295B2 (ja) | 2005-02-24 | 2013-02-06 | 株式会社Adeka | ケイ素含有硬化性組成物及びその硬化物 |
US8039049B2 (en) * | 2005-09-30 | 2011-10-18 | Tokyo Electron Limited | Treatment of low dielectric constant films using a batch processing system |
US8445108B2 (en) | 2007-10-18 | 2013-05-21 | Lg Chem, Ltd. | Composite materials, composite film manufactured by using the same and method for manufacturing composite film |
US20120052309A1 (en) | 2008-03-04 | 2012-03-01 | Carl Fairbank | Silicone Composition, Silicone Adhesive, Coated and Laminated Substrates |
-
2011
- 2011-06-14 FI FI20115591A patent/FI127433B/fi active IP Right Grant
-
2012
- 2012-06-14 TW TW101121250A patent/TWI610934B/zh active
- 2012-06-14 US US14/126,446 patent/US9458183B2/en active Active
- 2012-06-14 WO PCT/FI2012/050601 patent/WO2012172176A2/en active Application Filing
-
2016
- 2016-09-30 US US15/281,162 patent/US9884879B2/en active Active
Cited By (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
TWI611838B (zh) * | 2016-10-05 | 2018-01-21 | 汕頭市駿碼凱撒有限公司 | 以固態鈀觸媒進行矽氫加成反應之方法 |
TWI796996B (zh) * | 2019-08-22 | 2023-03-21 | 美商艾德凡斯化學公司 | 合成具有表面活性性質之胺基酸的矽氧烷衍生物之方法 |
TWI765320B (zh) * | 2019-08-22 | 2022-05-21 | 美商艾德凡斯化學公司 | 具有表面活性性質之胺基酸的矽氧烷衍生物 |
US11952394B2 (en) | 2019-08-22 | 2024-04-09 | Advansix Resins & Chemicals Llc | Siloxane derivatives of amino acids having surface-active properties |
US11905304B2 (en) | 2019-12-19 | 2024-02-20 | Advansix Resins & Chemicals Llc | Surfactants for agricultural products |
US11571377B2 (en) | 2019-12-19 | 2023-02-07 | Advansix Resins & Chemicals Llc | Surfactants for use in personal care and cosmetic products |
US12054663B2 (en) | 2019-12-19 | 2024-08-06 | Advansix Resins & Chemicals Llc | Surfactants for inks, paints, and adhesives |
US11633481B2 (en) | 2019-12-20 | 2023-04-25 | Advansix Resins & Chemicals Llc | Surfactants for use in healthcare products |
US11525105B2 (en) | 2019-12-20 | 2022-12-13 | Advansix Resins & Chemicals Llc | Surfactants for cleaning products |
US11542428B2 (en) | 2019-12-31 | 2023-01-03 | Advansix Resins & Chemicals Llc | Surfactants for oil and gas production |
US11891568B2 (en) | 2019-12-31 | 2024-02-06 | Advansix Resins & Chemicals Llc | Surfactants for oil and gas production |
US12049589B2 (en) | 2019-12-31 | 2024-07-30 | Advansix Resins & Chemicals Llc | Surfactants for oil and gas production |
US11427760B2 (en) | 2020-02-05 | 2022-08-30 | Advansix Resins & Chemicals Llc | Surfactants for electronics |
Also Published As
Publication number | Publication date |
---|---|
WO2012172176A2 (en) | 2012-12-20 |
FI20115591A0 (fi) | 2011-06-14 |
WO2012172176A3 (en) | 2013-04-25 |
WO2012172176A9 (en) | 2013-02-07 |
TWI610934B (zh) | 2018-01-11 |
US20140249326A1 (en) | 2014-09-04 |
US20170088565A1 (en) | 2017-03-30 |
FI127433B (fi) | 2018-05-31 |
US9884879B2 (en) | 2018-02-06 |
FI20115591L (fi) | 2012-12-15 |
US9458183B2 (en) | 2016-10-04 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
TWI610934B (zh) | 矽氧烷單體的合成方法及其用途 | |
JP5627458B2 (ja) | エポキシ官能性有機シランの制御された加水分解及び縮合並びに該エポキシ官能性有機シランと他の有機官能性アルコキシシランとの共縮合のための方法 | |
US8053173B2 (en) | Multi-functional linear siloxane compound, a siloxane polymer prepared from the compound, and a process for forming a dielectric film by using the polymer | |
KR101512529B1 (ko) | 폴리실록산 및 그의 제조 방법 및 경화물의 제조 방법 | |
KR101054569B1 (ko) | 규소 함유 고분자 화합물 및 그의 제조 방법 및 내열성수지 조성물 및 내열성 피막 | |
JP5692736B2 (ja) | 絶縁膜形成用塗布液、それを用いた絶縁膜 | |
TWI709595B (zh) | 聚矽氧聚合物之製造方法 | |
KR102611310B1 (ko) | 규소 함유층 형성 조성물 및 그것을 이용한 패턴을 가지는 기판의 제조 방법 | |
TWI720067B (zh) | 含有氟聚醚基之聚合物改質矽烷、表面處理劑及物品 | |
TW201938572A (zh) | 含六氟異丙醇基之矽化合物及其製造方法 | |
CN1626537A (zh) | 多官能环状硅酸盐(或酯)化合物,由该化合物制得的基于硅氧烷的聚合物和使用该聚合物制备绝缘膜的方法 | |
TW201422684A (zh) | 含二氧化矽粒子之硬化性組合物與其硬化物,及使用彼等之半導體密封材 | |
JP2016060816A (ja) | 被膜形成用組成物及びその製造方法、並びに被膜 | |
KR101877599B1 (ko) | 폴리실록산의 제조 방법 | |
JP2019070071A (ja) | 硬化性組成物及びその利用 | |
KR101869982B1 (ko) | 나노임프린트 몰드용 이형제, 표면 처리 방법 및 나노임프린트용 몰드 | |
JP3519871B2 (ja) | 硬化性組成物、及びその製造方法 | |
JP3908509B2 (ja) | ゲルマニウム原子ならびにシリコン原子含有ラダー型耐熱性樹脂およびその製造方法 | |
JP7397558B2 (ja) | 撥水撥油膜組成物及びその利用 | |
KR101621576B1 (ko) | 옥세타닐기를 갖는 규소 화합물의 제조 방법 | |
JP5454761B2 (ja) | オキセタニル基を有するケイ素化合物の製造方法 | |
JPWO2021186994A5 (zh) | ||
JP2019178277A (ja) | 硬化性樹脂組成物、及びその製造方法 | |
JP2009203215A (ja) | ケイ素化合物の製造方法 | |
JP2009203216A (ja) | ケイ素化合物の製造方法 |