JPS62209117A - Novel copolymer and production thereof - Google Patents
Novel copolymer and production thereofInfo
- Publication number
- JPS62209117A JPS62209117A JP5147786A JP5147786A JPS62209117A JP S62209117 A JPS62209117 A JP S62209117A JP 5147786 A JP5147786 A JP 5147786A JP 5147786 A JP5147786 A JP 5147786A JP S62209117 A JPS62209117 A JP S62209117A
- Authority
- JP
- Japan
- Prior art keywords
- group
- carbon atoms
- hydrocarbon group
- hydrogen
- formulas
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 229920001577 copolymer Polymers 0.000 title abstract description 18
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 14
- 239000000178 monomer Substances 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 150000008282 halocarbons Chemical group 0.000 claims abstract description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 229920005684 linear copolymer Polymers 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 8
- 239000000126 substance Substances 0.000 claims 6
- 239000004215 Carbon black (E152) Substances 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract description 10
- -1 cyano, hydroxyl Chemical group 0.000 abstract description 10
- 150000003440 styrenes Chemical class 0.000 abstract description 6
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract description 4
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 abstract description 3
- 239000003063 flame retardant Substances 0.000 abstract description 3
- 238000006116 polymerization reaction Methods 0.000 abstract description 3
- 239000002131 composite material Substances 0.000 abstract description 2
- 229920001002 functional polymer Polymers 0.000 abstract description 2
- 239000003607 modifier Substances 0.000 abstract description 2
- MSCPNSQHFQIZDW-UHFFFAOYSA-N (4-ethenylphenyl)methyl-trimethylsilane Chemical compound C[Si](C)(C)CC1=CC=C(C=C)C=C1 MSCPNSQHFQIZDW-UHFFFAOYSA-N 0.000 abstract 1
- 125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 abstract 1
- 239000012528 membrane Substances 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000010703 silicon Substances 0.000 abstract 1
- 229920000642 polymer Polymers 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 238000000862 absorption spectrum Methods 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- LXLJJQUMSRUTQD-UHFFFAOYSA-N [(4-ethenylphenyl)-trimethylsilylmethyl]-trimethylsilane Chemical compound C[Si](C)(C)C([Si](C)(C)C)C1=CC=C(C=C)C=C1 LXLJJQUMSRUTQD-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000003708 ampul Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- FUSUHKVFWTUUBE-UHFFFAOYSA-N buten-2-one Chemical compound CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 229920006254 polymer film Polymers 0.000 description 2
- 150000003377 silicon compounds Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZWKNLRXFUTWSOY-QPJJXVBHSA-N (e)-3-phenylprop-2-enenitrile Chemical compound N#C\C=C\C1=CC=CC=C1 ZWKNLRXFUTWSOY-QPJJXVBHSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- SUTQSIHGGHVXFK-UHFFFAOYSA-N 1,2,2-trifluoroethenylbenzene Chemical compound FC(F)=C(F)C1=CC=CC=C1 SUTQSIHGGHVXFK-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- LFSHREXVLSTLFB-UHFFFAOYSA-N 1-cyanoethenyl acetate Chemical compound CC(=O)OC(=C)C#N LFSHREXVLSTLFB-UHFFFAOYSA-N 0.000 description 1
- UGMRKNAZEKUAQS-UHFFFAOYSA-N 1-ethenylphenanthrene Chemical compound C1=CC2=CC=CC=C2C2=C1C(C=C)=CC=C2 UGMRKNAZEKUAQS-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- CISIJYCKDJSTMX-UHFFFAOYSA-N 2,2-dichloroethenylbenzene Chemical compound ClC(Cl)=CC1=CC=CC=C1 CISIJYCKDJSTMX-UHFFFAOYSA-N 0.000 description 1
- SXZSFWHOSHAKMN-UHFFFAOYSA-N 2,3,4,4',5-Pentachlorobiphenyl Chemical compound C1=CC(Cl)=CC=C1C1=CC(Cl)=C(Cl)C(Cl)=C1Cl SXZSFWHOSHAKMN-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- PDELBHCVXBSVPJ-UHFFFAOYSA-N 2-ethenyl-1,3,5-trimethylbenzene Chemical group CC1=CC(C)=C(C=C)C(C)=C1 PDELBHCVXBSVPJ-UHFFFAOYSA-N 0.000 description 1
- KBKNKFIRGXQLDB-UHFFFAOYSA-N 2-fluoroethenylbenzene Chemical compound FC=CC1=CC=CC=C1 KBKNKFIRGXQLDB-UHFFFAOYSA-N 0.000 description 1
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 1
- CTHJQRHPNQEPAB-UHFFFAOYSA-N 2-methoxyethenylbenzene Chemical compound COC=CC1=CC=CC=C1 CTHJQRHPNQEPAB-UHFFFAOYSA-N 0.000 description 1
- FCYVWWWTHPPJII-UHFFFAOYSA-N 2-methylidenepropanedinitrile Chemical compound N#CC(=C)C#N FCYVWWWTHPPJII-UHFFFAOYSA-N 0.000 description 1
- GHHGVSCQWPVENX-UHFFFAOYSA-N 2-methylpent-1-en-3-one Chemical compound CCC(=O)C(C)=C GHHGVSCQWPVENX-UHFFFAOYSA-N 0.000 description 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 1
- HKADMMFLLPJEAG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-enylbenzene Chemical compound FC(F)(F)C=CC1=CC=CC=C1 HKADMMFLLPJEAG-UHFFFAOYSA-N 0.000 description 1
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
- IWTYTFSSTWXZFU-UHFFFAOYSA-N 3-chloroprop-1-enylbenzene Chemical compound ClCC=CC1=CC=CC=C1 IWTYTFSSTWXZFU-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- IEPRKVQEAMIZSS-UHFFFAOYSA-N Di-Et ester-Fumaric acid Natural products CCOC(=O)C=CC(=O)OCC IEPRKVQEAMIZSS-UHFFFAOYSA-N 0.000 description 1
- IEPRKVQEAMIZSS-WAYWQWQTSA-N Diethyl maleate Chemical compound CCOC(=O)\C=C/C(=O)OCC IEPRKVQEAMIZSS-WAYWQWQTSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- XOBKSJJDNFUZPF-UHFFFAOYSA-N Methoxyethane Chemical compound CCOC XOBKSJJDNFUZPF-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- QZQAYMWKEUNFEH-UHFFFAOYSA-N [(4-ethenylphenyl)-triethylsilylmethyl]-triethylsilane Chemical compound CC[Si](CC)(CC)C([Si](CC)(CC)CC)C1=CC=C(C=C)C=C1 QZQAYMWKEUNFEH-UHFFFAOYSA-N 0.000 description 1
- 150000003926 acrylamides Chemical class 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 150000008360 acrylonitriles Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- KMKLIOQYUUPLMA-UHFFFAOYSA-N chloromethyl prop-2-enoate Chemical compound ClCOC(=O)C=C KMKLIOQYUUPLMA-UHFFFAOYSA-N 0.000 description 1
- 239000004020 conductor Substances 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- IEPRKVQEAMIZSS-AATRIKPKSA-N diethyl fumarate Chemical compound CCOC(=O)\C=C\C(=O)OCC IEPRKVQEAMIZSS-AATRIKPKSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- CMDXMIHZUJPRHG-UHFFFAOYSA-N ethenyl decanoate Chemical compound CCCCCCCCCC(=O)OC=C CMDXMIHZUJPRHG-UHFFFAOYSA-N 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- CTQAODRCOVPAEH-SNAWJCMRSA-N ethyl (e)-3-acetyloxyprop-2-enoate Chemical compound CCOC(=O)\C=C\OC(C)=O CTQAODRCOVPAEH-SNAWJCMRSA-N 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 1
- 150000002432 hydroperoxides Chemical class 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 238000006138 lithiation reaction Methods 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- QYZFTMMPKCOTAN-UHFFFAOYSA-N n-[2-(2-hydroxyethylamino)ethyl]-2-[[1-[2-(2-hydroxyethylamino)ethylamino]-2-methyl-1-oxopropan-2-yl]diazenyl]-2-methylpropanamide Chemical compound OCCNCCNC(=O)C(C)(C)N=NC(C)(C)C(=O)NCCNCCO QYZFTMMPKCOTAN-UHFFFAOYSA-N 0.000 description 1
- BPCNEKWROYSOLT-UHFFFAOYSA-N n-phenylprop-2-enamide Chemical compound C=CC(=O)NC1=CC=CC=C1 BPCNEKWROYSOLT-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- UCUUFSAXZMGPGH-UHFFFAOYSA-N penta-1,4-dien-3-one Chemical class C=CC(=O)C=C UCUUFSAXZMGPGH-UHFFFAOYSA-N 0.000 description 1
- FWGNVBNJIIHYAR-UHFFFAOYSA-N phenyl(3-phenylbut-2-en-2-yl)silane Chemical compound CC(=C([SiH2]C1=CC=CC=C1)C)C1=CC=CC=C1 FWGNVBNJIIHYAR-UHFFFAOYSA-N 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical group C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は、新規な共重合体およびその製造法に関するも
のであり、さらに詳しくは、側鎖に有機珪素を有するス
チレン誘導体の共重合体およびその製造法に関するもの
である。Detailed Description of the Invention (Industrial Application Field) The present invention relates to a novel copolymer and a method for producing the same, and more particularly to a copolymer of a styrene derivative having an organosilicon in the side chain and a method for producing the same. It concerns its manufacturing method.
（従来の技術）
従来からスチレン誘導体は数多く開発合成されてきてお
り、その重合性を利用し１機能性高分子の合成等に広（
利用されている。(Prior art) Many styrene derivatives have been developed and synthesized in the past, and their polymerizability has been used widely in the synthesis of monofunctional polymers.
It's being used.
珪素原子を有するスチレン誘導体としては。As a styrene derivative containing silicon atoms.
パラ−トリメチルシリルスチレン、パラ−トリメチルシ
リルメチルスチレン、ジメチルフェニルシリルスチレン
等が知られている。これらの化合物の重合体は多数知ら
れているが、シリル基が２ケベンジル基に結合した形の
スチレン壽導体の共重合体はこれまで知られていない。Para-trimethylsilylstyrene, para-trimethylsilylmethylstyrene, dimethylphenylsilylstyrene, and the like are known. Although many polymers of these compounds are known, a copolymer of a styrene conductor in which a silyl group is bonded to two kebenzyl groups has not been known so far.
このような背景をふまえて検討を重ねた結果、本発明者
らは、シリル基が１ないし２ケベンジル基に結合した新
規なスチレン誘導体の共重合体を合成するに到った。As a result of repeated studies based on this background, the present inventors have synthesized a novel copolymer of a styrene derivative in which a silyl group is bonded to one or two kebenzyl groups.
（発明の構成）
本発明に係る共重合体は、構造式（Ｉ）と構造式■で示
される重合単位からなる分子［１，ｏｎ□ないし２，０
００，０００の線状共重合体である。(Structure of the Invention) The copolymer according to the present invention comprises a molecule [1, on □ to 2,0
00,000 linear copolymer.
（Ｉ）■
〔式中ｓ Ｒｔ ＋ Ｒ１＊ Ｒ１は水素または炭素数
１から１０のアルキル基、アリール基、アラルキル基を
表し、ｎ＋ｍはその和が３となるようなｌまたは２０組
合せ。ただし、Ｒ，、Ｒ，、Ｒ，がともにメチル基であ
り、ｎ＝２９ｍ＝１である場合を除（。Ｙおよび２は水
素、炭化水素基（炭素数１から１０）、ハロゲン化炭化
水素基（炭素数１から１０）、ハロゲン、シアノ基、水
酸基、Ｃ００Ｒ４（Ｒ４は水素または炭素数１から１０
の炭化水素基）、Ｃ０Ｒ５（Ｒｓは炭素数１から１０の
炭化水素基）、０ＣＯＲａ （Ｒｅ は炭素数１から
１０の炭化水素基）またはＣ０ＮＨＲｔ （Ｒｔは水素
または炭素数１から１０の炭化水素基）を表す、ＣＨｎ
（ＳｉＲ，Ｒ，Ｒ１）ｍはビニル基に対して、オルト
、メタ、パラいずれの位置であってもよいが、パラがよ
り好ましい。また、ｎとｍはその和が３となるよりなｌ
または２の組合せであるが、ｎ＝１．ｍ＝２の方がシリ
ル基の難燃化等への効果がより顕著となるため、より好
ましい。(I) ■ [In the formula, s Rt + R1* R1 represents hydrogen or an alkyl group having 1 to 10 carbon atoms, an aryl group, or an aralkyl group, and n+m is 1 or a combination of 20 such that the sum thereof is 3. However, except for the case where R,, R,, R, are both methyl groups and n=29m=1 (.Y and 2 are hydrogen, hydrocarbon group (1 to 10 carbon atoms), halogenated hydrocarbon group (having 1 to 10 carbon atoms), halogen, cyano group, hydroxyl group, C00R4 (R4 is hydrogen or having 1 to 10 carbon atoms)
), C0R5 (Rs is a hydrocarbon group having 1 to 10 carbon atoms), 0CORa (Re is a hydrocarbon group having 1 to 10 carbon atoms), or C0NHRt (Rt is hydrogen or a hydrocarbon group having 1 to 10 carbon atoms) CHn
(SiR,R,R1)m may be in any of the ortho, meta, and para positions with respect to the vinyl group, but the para position is more preferable. Also, since n and m have a sum of 3,
or a combination of 2, but n=1. It is more preferable that m=2 because the effect of the silyl group on flame retardation etc. becomes more pronounced.
Ｒ＋ 、 Ｒｔ 、Ｒｓは水素または炭素数１から１０
のアルキル基、アリール基、アラルキル基を表すが、シ
リル基の反応性から、メチル基、エチル基、フェニル基
のいずれかであることが好ましい。R+, Rt, Rs are hydrogen or have a carbon number of 1 to 10
represents an alkyl group, an aryl group, or an aralkyl group, but from the reactivity of the silyl group, it is preferably a methyl group, an ethyl group, or a phenyl group.
構造式（２）において、Ｙとしては水素またはメチル基
が、２としてはフェニル基、シアン基。In structural formula (2), Y is hydrogen or a methyl group, and 2 is a phenyl group or a cyan group.
クロロメチルフェニル基、ハロゲンマタはＣＯＯＲ４゜
Ｃ０Ｒ５、０ＣＯＲａ 、Ｃ０ＮＨＲｙ （Ｒ４−ＲＩ
ｌ−Ｒａ −Ｒｔは水素または炭素数１から１０の炭化
水素基）等の電子吸引基が好ましい。勿論、複数種の重
合単位■を含む共重合体も本発明に含まれる。Chloromethylphenyl group, halogen group is COOR4゜C0R5, 0CORa, C0NHRy (R4-RI
l-Ra-Rt is preferably an electron-withdrawing group such as hydrogen or a hydrocarbon group having 1 to 10 carbon atoms. Of course, copolymers containing multiple types of polymerized units (2) are also included in the present invention.
重合単位（Ｉ）と卸のモル分率に制限はないが。There is no limit to the molar fraction of the polymerized unit (I) and the polymer.
）一般には、それぞれ１０モル係以上９８モル幅以下で
ある。さらに、好ましくは構造式（Ｉ）で示される部分
が２０モル係以上８０モル憾以下である。また、共重合
体の性質をほとんど変化させない範囲で、重合単位ＣＩ
）および■以外の少量の第３成分が共重合体に含まれる
ことはさしつかえない。) Generally, each has a molar width of 10 or more and 98 molar or less. Furthermore, preferably the moiety represented by structural formula (I) is 20 to 80 moles. In addition, within a range that hardly changes the properties of the copolymer, the polymerized unit CI
) and a small amount of a third component other than (■) may be included in the copolymer.
本発明における共重合体の分子量は１，０００ないし２
．０００．００（ＩＩ）であるが、より好ましくは１０
，０００ないし２．ｏｏｏ、ｏｏｏである。The molecular weight of the copolymer in the present invention is 1,000 to 2.
．． 000.00 (II), more preferably 10
,000 to 2. ooo, ooo.
本発明の共重合体は、構造式１１で示される単量体と構
造式１■で示される単量体を共重合することにより得る
ことができる。The copolymer of the present invention can be obtained by copolymerizing a monomer represented by Structural Formula 11 and a monomer represented by Structural Formula 1.
〔式中、Ｒ，、Ｒ，、Ｒ，は水素または炭素数１から１
０のアルキル基、アリール基、アラルキル基を表し、ｎ
ｓｍ はその和が３となるような１または２０組合せ。[In the formula, R,, R,, R, is hydrogen or has 1 to 1 carbon atoms]
0 alkyl group, aryl group, aralkyl group, n
sm is 1 or 20 combinations whose sum is 3.
ただし、Ｒ，、Ｒ，、Ｒ３がともにメチル基であり、ｎ
＝２．ｍ＝１である場合を除く。ＹおよびＺは水素、炭
化水素基（炭素数１から１０）、ハロゲン化炭化水素基
（炭素数１から１０）、ハロゲン、シアン基、水酸基、
ＣＯＯＲ４（Ｒ４は水素または炭素数１から１０の炭化
水素基） 、 ＣＯＲ，（Ｒ，は炭素数１から１０の炭
化水素基）、０ＣＯＲ６（Ｒ，は炭素数１から１０の炭
化水素基）またはＣ０ＮＨＲ，（Ｒ，は水素または炭素
数１から１０の炭化水素基）を表す。〕構造式（Ｒ１）
で示される単量体は、ビニルトルエンを特定の有機リチ
ウム化合物で予めメチル基をリチオ化した後、クロロシ
ラン化合物を系内に添加する方法で襄遺される。However, R,, R,, R3 are all methyl groups, and n
=2. Except when m=1. Y and Z are hydrogen, hydrocarbon group (1 to 10 carbon atoms), halogenated hydrocarbon group (1 to 10 carbon atoms), halogen, cyan group, hydroxyl group,
COOR4 (R4 is hydrogen or a hydrocarbon group having 1 to 10 carbon atoms), COR, (R, is a hydrocarbon group having 1 to 10 carbon atoms), 0COR6 (R, is a hydrocarbon group having 1 to 10 carbon atoms), or C0NHR, (R represents hydrogen or a hydrocarbon group having 1 to 10 carbon atoms). ] Structural formula (R1)
The monomer represented by is prepared by lithiation of the methyl group of vinyltoluene with a specific organic lithium compound and then adding a chlorosilane compound into the system.
構造式（ＩＶ）で示される単量体の例としては、スチレ
ン、メチルスチレン、ジフェニルエチレン、エチルスチ
レン、ジメチルスチレン、ビニルナフタリン、ビニルフ
ェナントレン、ビニルメシチレン、３ａ ４＊ ６
） ’Ｊメチルスチレン等ノ炭化水素化合物；クロルス
チレン、メトキシスチレン、ブロムスチレン、シアノス
チレン、フルオルスチレン、ジクロルスチレン、クロル
メチルスチレン、トリフルオルスチレン、トリフルオル
メチルスチレン等のスチレン誘導体；アクリロニトリル
、メタクリロニトリル、α−アセトキシアクリロニトリ
ル等のアクリロニトリル誘導体；アクリル酸、メタクリ
ル酸；アクリル酸メチル、アクリル酸ラウリル、アクリ
ル酸クロルメチル、アセトキシアクリル酸エチル等のア
クリル酸エステル；メタクリル酸シクロヘキシル等のメ
タクリル酸エステル；マレイン酸ジエチル、フマル酸ジ
エチル；メチルビニルケトン、エチルイソプロペニルケ
トン等のビニルケトン；塩化ビニリデン、臭化ビニリデ
ン、シアン化ビニリデン等のビニリデン化合物ニアクリ
ルアミド、メタクリルアミド、Ｎ−フェニルアクリルア
ミド等のアクリルアミド誘導体；酢酸ビニル、酪酸ビニ
ル、カプリン酸ビニル等の脂肪酸ビニル誘導体などであ
る。Examples of the monomer represented by structural formula (IV) include styrene, methylstyrene, diphenylethylene, ethylstyrene, dimethylstyrene, vinylnaphthalene, vinylphenanthrene, vinylmesitylene, 3a 4*6
) 'J Hydrocarbon compounds such as methylstyrene; Styrene derivatives such as chlorostyrene, methoxystyrene, bromstyrene, cyanostyrene, fluorostyrene, dichlorostyrene, chloromethylstyrene, trifluorostyrene, trifluoromethylstyrene; acrylonitrile, Acrylonitrile derivatives such as methacrylonitrile and α-acetoxyacrylonitrile; acrylic acid, methacrylic acid; acrylic acid esters such as methyl acrylate, lauryl acrylate, chloromethyl acrylate, and ethyl acetoxyacrylate; methacrylic acid esters such as cyclohexyl methacrylate; Diethyl maleate, diethyl fumarate; Vinyl ketones such as methyl vinyl ketone and ethyl isopropenyl ketone; Vinylidene compounds such as vinylidene chloride, vinylidene bromide, and vinylidene cyanide; Acrylamide derivatives such as niacrylamide, methacrylamide, and N-phenylacrylamide; Acetic acid These include fatty acid vinyl derivatives such as vinyl, vinyl butyrate, and vinyl caprate.
この中でも、Ｙおよび２が水素、シアン基。Among these, Y and 2 are hydrogen and cyan groups.
クロル基、メチル基、フェニル基、クロロメチルフェニ
ル基、 Ｃ０ＯＨ，ＣＯＯＭｅ 、 Ｃ００ＣａＨ１＋
、 ＣＯＭｅ。Chlor group, methyl group, phenyl group, chloromethylphenyl group, C0OH, COOMe, C00CaH1+
, COMe.
ＯＣＯＭｅ またはＣ０ＮＨ，であるものがより好ま
しい。OCOMe or CONH is more preferred.
本発明の共重合体を構造式（Ｉｌｌ）および（ＩＶ）で
示される単量体を用いて製造する場合の重合方法は特に
制限はな（、加熱による重合でも充分可能であるが、Ｎ
合開始剤を利用することが好ましい場合が多い。重合開
始剤として用いられるのは、過酸化ベンゾイル、過酸化
ラウロイル等の過酸化アシル類、アゾビスイソブチロニ
トリル、２．２’−アゾビス（２，４−ジメチルマレロ
ニトリル）等のアゾニトリル類、過酸化ジターシャリ−
ブチル、過酸化ジクミル、メチルエチルケトンパーオキ
シド等の過酸化物、クメンヒドロペルオキシド、ターシ
ャリ−ヒドロペルオキシド等のヒドロペルオキシド類で
ある。When producing the copolymer of the present invention using monomers represented by structural formulas (Ill) and (IV), the polymerization method is not particularly limited (although polymerization by heating is also possible,
It is often preferred to utilize a synthesis initiator. The polymerization initiators used include acyl peroxides such as benzoyl peroxide and lauroyl peroxide, azonitrile such as azobisisobutyronitrile and 2,2'-azobis(2,4-dimethylmaleronitrile), peroxide ditertiary
These include peroxides such as butyl, dicumyl peroxide, and methyl ethyl ketone peroxide, and hydroperoxides such as cumene hydroperoxide and tertiary hydroperoxide.
本発明における重合体は、不活性液体の召在下で重合を
行って製造することも可能である。The polymer in the present invention can also be produced by polymerizing in the presence of an inert liquid.
不活性液体としては、ノルマル−ペンタン、ノルマル−
ヘキサン、ノルマル−ヘプタン、ノルマルーオクタンを
始めとする脂肪族炭化水素類、メタノール、エタノール
、イソプロピルアルコールなどのアルコール類、アセト
ン、メチルエチルケトン、ジエチルケトンなどのケトン
類。Inert liquids include normal pentane, normal
Aliphatic hydrocarbons such as hexane, normal-heptane, and normal-octane; alcohols such as methanol, ethanol, and isopropyl alcohol; and ketones such as acetone, methyl ethyl ketone, and diethyl ketone.
ジエチルエーテル、メチルエチルエーテル、ジブチルエ
ーテル、ジオキサン、テトラヒドロフラン等のエーテル
類、ベンゼン、トルエン、キシレン等の芳香族炭化水素
類、ギ酸エチル、酢酸エチル、酢酸ブチル等のエステル
類、ジメチルホルムアミド、ジメチルアセトアミドを始
めとするアミド類、クロロホルム、塩化メチレン。Ethers such as diethyl ether, methyl ethyl ether, dibutyl ether, dioxane and tetrahydrofuran, aromatic hydrocarbons such as benzene, toluene and xylene, esters such as ethyl formate, ethyl acetate and butyl acetate, dimethylformamide and dimethylacetamide. Amides such as chloroform, methylene chloride.
ジクロルエタン等の脂肪族ハロゲン化物、クロルベンゼ
ンを始めとする芳香族ハロゲン化物。Aliphatic halides such as dichloroethane, aromatic halides such as chlorobenzene.
また、ジメチルスルホキシド等の極性液体も用いること
ができる。なお、これらの液体は単独ないしは二つ以上
の液体の混合物として用いることもできる。Furthermore, polar liquids such as dimethyl sulfoxide can also be used. Note that these liquids can be used alone or as a mixture of two or more liquids.
反応の４度に制限はないが、 ２０ｔｌ：から１２０
℃程度が好ましく、さらに好ましくは６ｏ℃から１００
℃程度である。There is no limit to the 4 degrees of reaction, but from 20 tl: to 120
The temperature is preferably about ℃, more preferably from 6o℃ to 100℃.
It is about ℃.
（発明の効果）
本発明の共重合体は、その珪素原子による難燃効果から
難燃剤への利用が考えられるとともに、側鎖の珪素原子
を利用して機能性高分子となり、酸素透過性膜への利用
やフォトレジスト。(Effects of the Invention) The copolymer of the present invention can be used as a flame retardant due to its flame retardant effect due to its silicon atoms, and it can also be used as a functional polymer by utilizing the silicon atoms in the side chain to form an oxygen permeable film. Application and photoresist.
電子線レジスト用ポリマーの一成分として有用である。It is useful as a component of a polymer for electron beam resist.
また、このポリマーを混入することにより、珪素化合物
であるシリコーンオイル、グラスファイバー等との密着
性が非常に良（なり。Also, by mixing this polymer, it has very good adhesion with silicone oil, which is a silicon compound, glass fiber, etc.
珪素化合物を使った複合材料の改質剤としても有用であ
る。It is also useful as a modifier for composite materials using silicon compounds.
（実施例）
以下１本発明の実施例を示すが、これらは本発明を制限
するものではない。(Example) One example of the present invention will be shown below, but these are not intended to limit the present invention.
実施例１
３０Ｗ１ｔのアンプル管に８．０１の４−ビス（トリメ
チルシリル）メチルスチレンと２．０２のスチレンおよ
び０．１１のアゾビスイソブチロニトリルを混合注入し
、アンプル管内を窒素パージした後、封管した。これを
８０℃の水浴中に２４時間浸漬した後、封管を割って固
化した内容物を取り出した。メタノールで洗浄後、真空
乾燥して重量を測定したところ、９．７ｔ（収率９７係
）であった。このものの元素分析値および赤外吸収スペ
クトルにおける主なピークは次のとおりである。Example 1 A mixture of 8.01% 4-bis(trimethylsilyl)methylstyrene, 2.02% styrene, and 0.11% azobisisobutyronitrile was injected into a 30W1t ampoule tube, and the inside of the ampoule tube was purged with nitrogen. The tube was sealed. After immersing this in a water bath at 80° C. for 24 hours, the sealed tube was broken and the solidified contents were taken out. After washing with methanol and vacuum drying, the weight was measured and was found to be 9.7 t (yield: 97). The elemental analysis values and main peaks in the infrared absorption spectrum of this product are as follows.
元素分析値（括弧内は理論値を表す）
Ｃニア３．４７（７３，３５）
Ｈ： ９．５８（９，５３）
Ｓｔ ：１６．９５（１７，１２）
赤外吸収スペクトル（ｃｌｎ−’）
３０６０．２９５０，２８３０，１６１０゜１５１０．
１４１０．１２５０．１２００゜１０３０．７７０．６
９０ｃｒｎ−’
赤外吸収スペクトルにおいて、炭素−炭素の二重結合に
起因するピークが全（消失したこと。Elemental analysis values (theoretical values are shown in parentheses) C near 3.47 (73,35) H: 9.58 (9,53) St: 16.95 (17,12) Infrared absorption spectrum (cln-' ) 3060.2950,2830,1610°1510.
1410.1250.1200゜1030.770.6
90crn-' In the infrared absorption spectrum, all peaks due to carbon-carbon double bonds (disappeared).
元素分析値および収量から、得られた固体は。Based on the elemental analysis values and yield, the obtained solid is.
４−ビス（トリメチルシリル）メチルスチレンとスチレ
ンの共重合体であると結論された。It was concluded that it was a copolymer of 4-bis(trimethylsilyl)methylstyrene and styrene.
このものをゲルパーミエイションクロマトグラフイーに
より、ポリスチレンを検量線として用いることによって
分子量を測定したところ、分子量は１．２００．００
ｎであった。The molecular weight of this product was measured by gel permeation chromatography using polystyrene as a calibration curve, and the molecular weight was 1.200.00.
It was n.
実施例２
４−ビス（トリメチルシリル）メチルスチレンの代ワり
に４−ビス（トリエチルシリル）メチルスチレンを用い
た以外は、実施例１とまった（同様に反応、操作を行っ
た。得られた固体の収量は９．８ｆ（９８％）であり、
その元素分析値および赤外吸収スペクトルにおける王な
ピークは次のとおりである。Example 2 Same as Example 1 except that 4-bis(triethylsilyl)methylstyrene was used instead of 4-bis(trimethylsilyl)methylstyrene (the reaction and operation were carried out in the same manner. The obtained solid The yield is 9.8f (98%),
Its elemental analysis values and major peaks in the infrared absorption spectrum are as follows.
元素分析値（括弧内は理論値を表す）
Ｃニア６．４２（７６，６５）
Ｈ：１０．７４（１０，３９）
Ｓｉ ：１２．８４（１２，９６）
赤外吸収スペクトル（ｔ−Ｉｎ−’）
３０６０．２９５０．２８０ｏ、１６１０゜１５１０．
１４１０，１２５０、ｌ ０３０゜７７０．６９０ ｃ
Ｗｔ−’
また１分子量を実施例１と同様に測定したところ、分子
量は１．１ｏ ｏ、 ｏ ｏ ｏであった、実施例３〜
１２
実施例１と同様の手法により、構造式（■１）で示され
る単量体と構造式ＧＶ）で示される単量体の共重合を行
い、得られた共重合体について元素分析および赤外吸収
スペクトルの測定を行った。結果を第１表に示す。Elemental analysis values (theoretical values are shown in parentheses) C near 6.42 (76,65) H: 10.74 (10,39) Si: 12.84 (12,96) Infrared absorption spectrum (t-In -') 3060.2950.280o, 1610°1510.
1410,1250,l 030°770.690c
Wt-' In addition, when the molecular weight was measured in the same manner as in Example 1, the molecular weight was 1.1 o o, o o o.
12 Copolymerize the monomer represented by the structural formula (■1) and the monomer represented by the structural formula GV) using the same method as in Example 1, and perform elemental analysis and red color analysis of the obtained copolymer. The external absorption spectrum was measured. The results are shown in Table 1.
これらの結果によれば、得られた共重合体は、いずれも
特許請求の範囲第１項に含まれるものであった。According to these results, all of the obtained copolymers were included in claim 1.
実施例１３
実施例１で合成したポリマー１１をテトラヒドロフラン
２０−に溶解させた後、洗浄なガラス表面に、この溶液
を塗り、ポリマーフィルムを作った。溶媒のテトラヒド
ロフランを２０℃で２４時間乾燥して除去した後、水に
ガラスを浸漬してポリマーフィルムを剥離した後、フィ
ルムを４８時間真空乾燥した。Example 13 Polymer 11 synthesized in Example 1 was dissolved in 20-tetrahydrofuran, and this solution was applied to a clean glass surface to form a polymer film. After removing the solvent tetrahydrofuran by drying at 20° C. for 24 hours, the polymer film was peeled off by immersing the glass in water, and then the film was vacuum-dried for 48 hours.
このフィルムの一方の側から空気を加え、反対側へ通過
してくるガスクロマトグラフィー法により測定したとこ
ろ、酸素の選択透過性（通過後の酸素分率／初期酸素分
率）は３．１であった。When air was added from one side of this film and measured by gas chromatography, the oxygen permselectivity (oxygen fraction after passing/initial oxygen fraction) was 3.1. there were.
Claims (4)
単位から成り、分子量が１，０００ないし２，０００，
０００である線状共重合体。 ▲数式、化学式、表等があります▼（ I ）▲数式、化
学式、表等があります▼（II） 〔式中、Ｒ＿１、Ｒ＿２、Ｒ＿３は水素または炭素数１
から１０のアルキル基、アリール基、アラルキル基を表
し、ｎ、ｍはその和が３となるような１または２の組合
せ。ただし、Ｒ＿１、Ｒ＿２、Ｒ＿３がともにメチル基
であり、ｎ＝２、ｍ＝１である場合を除く。ＹおよびＺ
は水素、炭化水素基（炭素数１から１０）、ハロゲン化
炭化水素基（炭素数１から１０）、ハロゲン、シアノ基
、水酸基、ＣＯＯＲ＿４（Ｒ＿４は水素または炭素数１
から１０の炭化水素基）、ＣＯＲ＿５（Ｒ＿５は炭素数
１から１０の炭化水素基）、ＯＣＯＲ＿６（Ｒ＿６は炭
素数１から１０の炭化水素基）またはＣＯＮＨＲ＿７（
Ｒ＿７は水素または炭素数１から１０の炭化水素基）を
表す。〕(1) Consisting of polymerized units represented by the following structural formulas (I) and (II), with a molecular weight of 1,000 to 2,000,
000 linear copolymer. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) [In the formula, R_1, R_2, R_3 are hydrogen or carbon number 1
represents an alkyl group, aryl group, or aralkyl group of 10, and n and m are a combination of 1 or 2 such that the sum thereof is 3. However, the case where R_1, R_2, and R_3 are all methyl groups, and n=2 and m=1 is excluded. Y and Z
is hydrogen, hydrocarbon group (1 to 10 carbon atoms), halogenated hydrocarbon group (1 to 10 carbon atoms), halogen, cyano group, hydroxyl group, COOR_4 (R_4 is hydrogen or carbon number 1
to 10 hydrocarbon groups), COR_5 (R_5 is a hydrocarbon group having 1 to 10 carbon atoms), OCOR_6 (R_6 is a hydrocarbon group having 1 to 10 carbon atoms), or CONHR_7 (
R_7 represents hydrogen or a hydrocarbon group having 1 to 10 carbon atoms. ]
求の範囲第１項記載の化合物。(2) The compound according to claim 1, wherein n=1 and m=2 in structural formula (I).
ル基、エチル基、フェニル基のいずれかである特許請求
の範囲第１項または第２項記載の化合物。(3) The compound according to claim 1 or 2, wherein in structural formula (I), R_1, R_2, and R_3 are any one of a methyl group, an ethyl group, and a phenyl group.
構造式（ I ）および（II）で示される重合単位から成
り、分子量が１，０００ないし２，０００，０００であ
る線状共重合体の製造法。 ▲数式、化学式、表等があります▼（ I ）▲数式、化
学式、表等があります▼（II） 〔式中、Ｒ＿１、Ｒ＿２、Ｒ＿３は水素または炭素数１
から１０のアルキル基、アリール基、アラルキル基を表
し、ｎ、ｍはその和が３となるような１または２の組合
せ。ただし、Ｒ＿１、Ｒ＿２、Ｒ＿３がともにメチル基
であり、ｎ＝２、ｍ＝１である場合を除く。ＴおよびＺ
は水素、炭化水素基（炭素数１から１０）、ハロゲン化
炭化水素基（炭素数１から１０）、ハロゲン、シアノ基
、水酸基、ＣＯＯＲ＿４（Ｒ＿４は水素または炭素数１
から１０の炭化水素基）、ＣＯＲ＿５（Ｒ＿５は炭素数
１から１０の炭化水素基）、ＯＣＯＲ＿６（Ｒ＿６は炭
素数１から１０の炭化水素基）またはＣＯＮＨＲ＿７（
Ｒ＿７は水素または炭素数１から１０の炭化水素基）を
表す。〕(4) The monomer shown by the following structural formula (III) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(III) and the following structural formula (IV) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (IV) A linear copolymer comprising polymerized units represented by the following structural formulas (I) and (II) and having a molecular weight of 1,000 to 2,000,000, characterized by copolymerizing the following monomers: manufacturing method. ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (I) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (II) [In the formula, R_1, R_2, R_3 are hydrogen or carbon number 1
represents an alkyl group, aryl group, or aralkyl group of 10, and n and m are a combination of 1 or 2 such that the sum thereof is 3. However, the case where R_1, R_2, and R_3 are all methyl groups, and n=2 and m=1 is excluded. T and Z
is hydrogen, hydrocarbon group (1 to 10 carbon atoms), halogenated hydrocarbon group (1 to 10 carbon atoms), halogen, cyano group, hydroxyl group, COOR_4 (R_4 is hydrogen or carbon number 1
to 10 hydrocarbon groups), COR_5 (R_5 is a hydrocarbon group having 1 to 10 carbon atoms), OCOR_6 (R_6 is a hydrocarbon group having 1 to 10 carbon atoms), or CONHR_7 (
R_7 represents hydrogen or a hydrocarbon group having 1 to 10 carbon atoms. ]
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5147786A JPS62209117A (en) | 1986-03-11 | 1986-03-11 | Novel copolymer and production thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5147786A JPS62209117A (en) | 1986-03-11 | 1986-03-11 | Novel copolymer and production thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62209117A true JPS62209117A (en) | 1987-09-14 |
| JPH0441687B2 JPH0441687B2 (en) | 1992-07-09 |
Family
ID=12888031
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5147786A Granted JPS62209117A (en) | 1986-03-11 | 1986-03-11 | Novel copolymer and production thereof |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62209117A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0301099A1 (en) * | 1987-01-28 | 1989-02-01 | MITSUI TOATSU CHEMICALS, Inc. | Processes for preparing organosilicon compounds and silicon carbide |
-
1986
- 1986-03-11 JP JP5147786A patent/JPS62209117A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0301099A1 (en) * | 1987-01-28 | 1989-02-01 | MITSUI TOATSU CHEMICALS, Inc. | Processes for preparing organosilicon compounds and silicon carbide |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0441687B2 (en) | 1992-07-09 |
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