JPS6328921B2 - - Google Patents
Info
- Publication number
- JPS6328921B2 JPS6328921B2 JP22395983A JP22395983A JPS6328921B2 JP S6328921 B2 JPS6328921 B2 JP S6328921B2 JP 22395983 A JP22395983 A JP 22395983A JP 22395983 A JP22395983 A JP 22395983A JP S6328921 B2 JPS6328921 B2 JP S6328921B2
- Authority
- JP
- Japan
- Prior art keywords
- methacrylate
- tricyclo
- monomer
- dec
- polymerization
- 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.)
- Expired
Links
- 239000000178 monomer Substances 0.000 claims description 25
- 229920000642 polymer Polymers 0.000 claims description 21
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- -1 polypropylene Polymers 0.000 description 18
- 239000002245 particle Substances 0.000 description 9
- 238000006116 polymerization reaction Methods 0.000 description 9
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 238000010557 suspension polymerization reaction Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 239000004793 Polystyrene Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 229920002223 polystyrene Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000012778 molding material Substances 0.000 description 3
- 229920001955 polyphenylene ether Polymers 0.000 description 3
- 229920006380 polyphenylene oxide Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- MEBONNVPKOBPEA-UHFFFAOYSA-N 1,1,2-trimethylcyclohexane Chemical compound CC1CCCCC1(C)C MEBONNVPKOBPEA-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004372 Polyvinyl alcohol Substances 0.000 description 2
- 150000008360 acrylonitriles Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 239000001506 calcium phosphate Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- 229920006351 engineering plastic Polymers 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002451 polyvinyl alcohol Polymers 0.000 description 2
- 238000010526 radical polymerization reaction Methods 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 150000003440 styrenes Chemical class 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 2
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical group ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- JNPCNDJVEUEFBO-UHFFFAOYSA-N 1-butylpyrrole-2,5-dione Chemical compound CCCCN1C(=O)C=CC1=O JNPCNDJVEUEFBO-UHFFFAOYSA-N 0.000 description 1
- SXTILEHINBCKSS-UHFFFAOYSA-N 1-chloro-3-phenylpyrrole-2,5-dione Chemical compound O=C1N(Cl)C(=O)C=C1C1=CC=CC=C1 SXTILEHINBCKSS-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- SJLLJZNSZJHXQN-UHFFFAOYSA-N 1-dodecylpyrrole-2,5-dione Chemical compound CCCCCCCCCCCCN1C(=O)C=CC1=O SJLLJZNSZJHXQN-UHFFFAOYSA-N 0.000 description 1
- QCOLXFOZKYRROA-UHFFFAOYSA-N 1-methoxy-3-phenylpyrrole-2,5-dione Chemical compound O=C1N(OC)C(=O)C=C1C1=CC=CC=C1 QCOLXFOZKYRROA-UHFFFAOYSA-N 0.000 description 1
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 1
- NQDOCLXQTQYUDH-UHFFFAOYSA-N 1-propan-2-ylpyrrole-2,5-dione Chemical compound CC(C)N1C(=O)C=CC1=O NQDOCLXQTQYUDH-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical class ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- HRWRJUVJOLBMST-LXWZSJDBSA-N 27137-33-3 Chemical compound C1C[C@@H]2C3C(O)C=CC3[C@H]1C2 HRWRJUVJOLBMST-LXWZSJDBSA-N 0.000 description 1
- DXIJHCSGLOHNES-UHFFFAOYSA-N 3,3-dimethylbut-1-enylbenzene Chemical class CC(C)(C)C=CC1=CC=CC=C1 DXIJHCSGLOHNES-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-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 class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- HDFGOPSGAURCEO-UHFFFAOYSA-N N-ethylmaleimide Chemical compound CCN1C(=O)C=CC1=O HDFGOPSGAURCEO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical class ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium peroxydisulfate Substances [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 1
- VAZSKTXWXKYQJF-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)OOS([O-])=O VAZSKTXWXKYQJF-UHFFFAOYSA-N 0.000 description 1
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 description 1
- GCTPMLUUWLLESL-UHFFFAOYSA-N benzyl prop-2-enoate Chemical compound C=CC(=O)OCC1=CC=CC=C1 GCTPMLUUWLLESL-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- SQHOHKQMTHROSF-UHFFFAOYSA-N but-1-en-2-ylbenzene Chemical compound CCC(=C)C1=CC=CC=C1 SQHOHKQMTHROSF-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
- 235000011010 calcium phosphates Nutrition 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000006482 condensation reaction Methods 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
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- XZTWHWHGBBCSMX-UHFFFAOYSA-J dimagnesium;phosphonato phosphate Chemical compound [Mg+2].[Mg+2].[O-]P([O-])(=O)OP([O-])([O-])=O XZTWHWHGBBCSMX-UHFFFAOYSA-J 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- CIKJANOSDPPCAU-UHFFFAOYSA-N ditert-butyl cyclohexane-1,4-dicarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1CCC(C(=O)OOC(C)(C)C)CC1 CIKJANOSDPPCAU-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 229920006015 heat resistant resin Polymers 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- VHRYZQNGTZXDNX-UHFFFAOYSA-N methacryloyl chloride Chemical class CC(=C)C(Cl)=O VHRYZQNGTZXDNX-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 229920001707 polybutylene terephthalate Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920013716 polyethylene resin Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 1
- FZYCEURIEDTWNS-UHFFFAOYSA-N prop-1-en-2-ylbenzene Chemical compound CC(=C)C1=CC=CC=C1.CC(=C)C1=CC=CC=C1 FZYCEURIEDTWNS-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical class C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
本発明は、耐熱性に優れた重合体の製造法に関
する。
従来、ポリエチレン系樹脂は成形材料や発泡材
料用の樹脂として汎用されているが、熱変形温度
が低く、耐熱性の要求される用途に用いることは
不適である。
そこでポリスチレン系樹脂の成形性を生かし
て、かつ、耐熱性のある樹脂を得るために、例え
ば、高密度ポリエチレンまたは結晶性ポリプロピ
レンを混合することが考えられるが、これらはポ
リスチレンと混合し難いこと、成形性が低下する
等問題が多い。また、これらの樹脂の他にスチレ
ン、無水マレイン酸共重合体が提案されている
（特開昭47−39186号公報）が、この共重合体の製
造を懸濁重合で行なう場合、無水マレイン酸の特
異な反応性のために非常に複雑な懸濁重合工程が
必要とされるとともに無水マレイン酸の多量の使
用が必要とされ、経済的でないことが特公昭47―
49831号公報に指摘されている。またメチルメタ
クリレートを主成分としα―メチルスチレンを従
成分とし、α―メチルスチレンの反応性が低い点
を第３成分のビニール化合物を併用し懸濁重合を
95〜130℃の高温で約20時間の重合時間で合成す
る発泡性ポリメチルメタクリレート共重合体粒子
の製造方法が特開昭57―182334号公報に提案され
ているが重合温度が高温で長時間の懸濁重合工程
が必要とされ経済的でない。
本発明は、このような問題を解決し、耐熱性に
優れた重合体を製造することを第１の目的とし、
そのような重合体を懸濁重合法により粒子状で製
造することを第２の目的とする。
すなわち、本発明は、メタクリル酸トリシクロ
〔5.2.1.02,6〕デカ―８―イル、アクリル酸トリシ
クロ〔5.2.1.02,6〕デカ―８―イルおよび他の重合
性モノマーからなるモノマー群から選ばれた少な
くとも１種のモノマー（）の重合体または他の
重合体の存在下に、該モノマー群から選ばれた少
なくとも１種のモノマー（）（ただし、モノマ
ー（）および／またはモノマー（）には必ず
メタクリル酸トリシクロ〔5.2.1.02,6〕デカ―８―
イルおよび／またはアクリル酸トリシクロ
〔5.2.1.02,6〕デカ―８―イルが含まれる）を重合
し、かつメタクリル酸トリシクロ〔5.2.1.02,6〕デ
カ―８―イルおよび／またはアクリル酸トリシク
ロ〔5.2.1.02,6〕デカ―８―イルのモノマーの総量
に対する混合比を５〜100重量％とすることを特
徴とする重合体の製造法に関する。
本発明において、他の重合性単量体としては、
不飽和脂肪酸エステル、芳香族ビニル化合物、シ
アン化ビニル化合物、Ｎ―置換マレイミドなどが
ある。不飽和脂肪酸エステルとしては、アクリル
酸メチル、アクリル酸エチル、アクリル酸ブチ
ル、アクリル酸―２―エチルヘキシル等のアクリ
ル酸アルキルエステル、アクリル酸シクロヘキシ
ル等のアクリル酸シクロアルキルエステル、アク
リル酸フエニル、アクリル酸ベンジル等のアクリ
ル酸芳香族エステル、アクリル酸グリシジルなど
のアクリル酸エステル、メタクリル酸メチル、メ
タクリル酸エチル、メタクリル酸プロピル、メタ
クリル酸ブチル、メタクリル酸ヘキシル、メタク
リル酸２―エチルヘキシル等のメタクリル酸アル
キルエステル、メタクリル酸シクロヘキシル等の
メタクリル酸シクロアルキルエステル、メタクリ
ル酸フエニル、メタクリル酸ベンジル等のメタク
リル酸芳香族エステル、メタクリル酸グリシジル
などのメタクリル酸エステルなどがある。
芳香族ビニル化合物としては、スチレンまたは
α―メチルスチレン、α―エチルスチレン等のα
―置換スチレン、クロロスチレン、ビニルトルエ
ン、ｔ―ブチルスチレン等の核置換スチレンがあ
る。シアン化ビニル化合物としてはアクリロニト
リル、メタクリロニトリル等がある。Ｎ―置換マ
レイミドとしては、Ｎ―メチルマレイミド、Ｎ―
エチルマレイミド、Ｎ―イソプロピルマレイミ
ド、Ｎ―ブチルマレイミド、Ｎ―ラウリルマレイ
ミド等の脂肪族Ｎ―置換マレイミド、Ｎ―シクロ
ヘキシルマレイミド等の脂環式Ｎ―置換マレイミ
ド、Ｎ―フエニルマレイミド、Ｎ―メチルフエニ
ルマレイミド、Ｎ―クロロフエニルマレイミド、
Ｎ―メトキシフエニルマレイミド等の芳香族Ｎ―
置換マレイミド等が挙げられる。その他、ビニル
アセテート、α―メチルエチレン、ジエチルマレ
ート等も使用できる。
上記モノマーの重合体としては、ポリエチレ
ン、ポリプロピレン等も含まれる。
本発明において他の重合体としては、ポリフエ
ニレンオキサイド、ポリエチレンテレフタレー
ト、ポリプチレンテレフタレート等の飽和ポリエ
ステル、不飽和ポリエステル等のビニル重合によ
つて得られない重合体がある。
本発明の重合体を製造する方法としては、ラジ
カル重合やイオン重合等の公知の方法が適用でき
る。例えば重合開始剤の存在下で塊状重合、溶液
重合、懸濁重合などの方法で製造できるが、特に
樹脂中の不純物の混入等を考慮する必要のある光
学素子用用途では、塊状重合又は懸濁重合法が好
ましい。この場合、上記したモノマー（）の重
合体または他の重合体の存在下に、モノマー
（）が重合されるが、これらの重合体は、該モ
ノマー（）に溶解させておいても、該モノマー
（）によつて含浸させられていてもよい。
重合に用いる開始剤としては、例えば過酸化ベ
ンゾイル、過酸化ラウロイル、ジ―ｔ―ブチルパ
ーオキシヘキサヒドロテレフタレート、ｔ―プチ
ルパーオキシ―２―エチルヘキサノエート、１，
１―ジ―ｔ―ブチルパーオキシ―３，３，５―ト
リメチルシルクロヘキサンなどの有機過酸化物、
アゾビスイソブチロニトリル、アゾビス―４―メ
トキシ―２，４―ジメチルバレロニトリル、アゾ
ビスシクロヘキサノン―１―カルボニトリル、ア
ゾジベンゾイルなどのアゾ化合物、過硫酸カリウ
ム、過硫酸アンモニウムに代表される水溶性触媒
及び過酸化物あるいは過硫酸塩と還元剤の組合せ
によるレドツクス触媒など通常のラジカル重合に
使用できるものはいずれも可能である。重合触媒
はモノマーの総量に対して0.01〜10重量％の範囲
で使用されるのが好ましい。重合調節剤としての
メルカプタン系化合物、チオグリコール、四臭化
炭素、α―メチルスチレンダイマーなどが分子量
調節のために必要に応じて添加しうる。
重合温度は０〜200℃の間で適宜選択するのが
好ましく、特に50〜120℃が好ましい。
溶液重合における溶媒としては、ベンゼン、ト
ルエン、キシレン、メチルエチルケトン、メチル
イソブチルケトン、酢酸エチル、酢酸ブチル、ジ
クロルエチレン等が使用できる。
懸濁重合は、水性媒体中で行なわれ、懸濁剤お
よび必要に応じ懸濁助剤が添加される。懸濁剤と
しては、ポリビニルアルコール、メチルセルロー
ス、ポリアクリルアミド等の水溶性高分子、燐酸
カルシウム、ピロ燐酸マグネシウム等の難溶性無
機物質等があり、水溶性高分子はモノマーの総量
に対して0.03〜１重量％及び難溶性無機物質はモ
ノマーの総量に対して0.05〜0.5重量％使用する
のが好ましい。
懸濁助剤としては、ドデシルベンゼンスルホン
酸ソーダ等の陰イオン界面活性剤があり、懸濁剤
として難溶性無機物質を使用する場合は、併用す
る方が好ましい。懸濁助剤はモノマーの総量に対
して0.001〜0.02重量％使用するのが好ましい。
本発明において使用されるメタクリル酸トリシ
クロ〔5.2.1.02,6〕デカ―８―イルまたはアクリル
酸トリシクロ〔5.2.1.02,6〕デカ―８―イルはメタ
クリル酸エステル又はアクリル酸エステルの合成
に関する一般公知の方法を用いて得られる。例え
ば、ジシクロペンタジエンにH2Oを付加してジ
シクロペンテニルアルコールとし、引き続き接触
水素添加反応により、トリシクロ〔5.2.1.02,6〕デ
カ―８―オールが得られる。このアルコールとメ
タクリル酸、アクリル酸又はメタクリル酸クロリ
ド、アクリル酸クロリドとの縮合反応やメタクリ
ル酸メチル、アクリル酸メチルとのエステル交換
反応等により得られる。
本発明により得られる重合体は、発泡性熱可塑
性樹脂粒子、射出成形材料、押出成形材料等に適
用することができる。
本発明により得られる重合体は、その使用にあ
たつて、成形性を改良したり、難燃性を付与した
りするための各種添加剤、例えば顔料、難燃剤、
酸化防止剤、可塑剤、帯電防止剤等の公知の添加
剤を含有させてもよい。
本発明から得られた樹脂粒子は、耐熱熱可塑性
樹脂として押出し、インジエクシヨン等に使用出
来、また発泡体原料として使用される。
次に、本発明の実施例を示す。
実施例 １
４の回転撹拌付オートクレーブにイオン交換
水1500ｇポリビニルアルコール（電気化学工業(株)
製Ｗ―24）4.5ｇとポリスチレン粒子（0.6〜0.8mm
径）500ｇを仕込み、かきまぜながら系内の温度
を80℃に昇温した。メタクリル酸トリシクロ
〔5.2.1.02,6〕デカ―８―イル500ｇを125ｇずつ20
分間隔で３回滴下した。つぎに残りの単量体に
１，１―ジ―ｔ―ブチルパーオキシ３，３，５―
トリメチルシクロヘキサン2.67ｇ、ｔ―ブチルパ
ーベンゾエート0.5ｇを溶解し、３回目の溶液添
加後30分後に同様に添加した。更に３時間同温度
で反応を続けた後、60分で120℃迄昇温し、以後
この温度で３時間撹拌をつづけた。この後30℃ま
で冷却し重合体粒子を得た。平均径、ガラス転移
温度を表１に示す。
実施例 ２
実施例１において使用するポリスチレン粒子
500ｇのかわりにポリフエニレンエーテル500ｇ
〔エンジニアリングプラスチツク製PPO〕を使用
して重合体粒子を得た平均径、ガラス転移温度を
表１に示す。
実施例 ３
４の回転撹拌機付オートクレーブにメタクリ
ル酸トリシクロ〔5.2.1.02,6〕デカ―８―イル500
ｇとスチレン250ｇを仕込み、かきまぜながらポ
リフエニレンエーテル〔エンジニアリングプラス
チツク製PPO〕250ｇを加え、窒素ガスで置換し
ながら２時間で完全に溶解させた。完全溶解後ベ
ンゾイルパーオキサイド2.3ｇ、ｔ―ブチルパー
ベンゾエート1.5ｇを溶解し、その後撹拌を止め
イオン交換水2000ｇを添加した後、撹拌を再開
し、燐酸三カルシウム５ｇ、ドデシルベンゼンス
ルフオン酸ソーダ0.5％溶液６ｇ、硫酸ソーダ
0.75ｇを添加し懸濁重合を開始した。以後、実施
例１と同様に行ない重合体粒子を製造した。平均
径、ガラス転移温度を表１に示す。
比較例 １
実施例３においてメタクリル酸トリシクロ
〔5.2.1.02,6〕デカ―８―イルを使用せずスチレン
モノマー750ｇにポリフエニレンエーテル250ｇを
溶解した以外は実施例３と同様に行ない重合体粒
子を得た。平均径、ガラス転移温度を表１に示
す。
The present invention relates to a method for producing a polymer with excellent heat resistance. Conventionally, polyethylene resins have been widely used as resins for molding materials and foaming materials, but their heat distortion temperature is low, making them unsuitable for use in applications requiring heat resistance. Therefore, in order to take advantage of the moldability of polystyrene-based resin and obtain a heat-resistant resin, it is possible to mix, for example, high-density polyethylene or crystalline polypropylene, but these are difficult to mix with polystyrene. There are many problems such as decreased moldability. In addition to these resins, a copolymer of styrene and maleic anhydride has been proposed (Japanese Unexamined Patent Publication No. 47-39186), but when producing this copolymer by suspension polymerization, maleic anhydride Due to the unique reactivity of
This is pointed out in Publication No. 49831. In addition, methyl methacrylate is the main component and α-methylstyrene is the secondary component, and a vinyl compound as the third component is used in conjunction with suspension polymerization to take advantage of the low reactivity of α-methylstyrene.
A method for producing expandable polymethyl methacrylate copolymer particles synthesized at a high temperature of 95 to 130°C and a polymerization time of about 20 hours is proposed in JP-A-57-182334, but the polymerization temperature is high and the polymerization time is long. A suspension polymerization step is required and is not economical. The primary purpose of the present invention is to solve these problems and produce a polymer with excellent heat resistance.
The second objective is to produce such a polymer in particulate form by a suspension polymerization method. That is, the present invention provides a monomer group consisting of tricyclo[5.2.1.0 2,6 ]dec-8-yl methacrylate, tricyclo[5.2.1.0 2,6 ]dec-8-yl acrylate, and other polymerizable monomers. In the presence of a polymer of at least one selected monomer () or another polymer, at least one monomer () selected from the monomer group (provided that monomer () and/or monomer ()) is always tricyclomethacrylate [5.2.1.0 2,6 ] deca-8-
and/or tricyclo[5.2.1.0 2,6 ]dec-8-yl acrylate), and tricyclo[5.2.1.0 2,6 ]dec-8-yl methacrylate and/or acrylic acid. The present invention relates to a method for producing a polymer, characterized in that the mixing ratio of tricyclo[5.2.1.0 2,6 ]dec-8-yl to the total amount of monomers is 5 to 100% by weight. In the present invention, other polymerizable monomers include:
Examples include unsaturated fatty acid esters, aromatic vinyl compounds, vinyl cyanide compounds, and N-substituted maleimides. Examples of unsaturated fatty acid esters include acrylic acid alkyl esters such as methyl acrylate, ethyl acrylate, butyl acrylate, and 2-ethylhexyl acrylate, acrylic acid cycloalkyl esters such as cyclohexyl acrylate, phenyl acrylate, and benzyl acrylate. Aromatic acrylic esters such as glycidyl acrylate, acrylic esters such as glycidyl acrylate, methacrylic acid alkyl esters such as methyl methacrylate, ethyl methacrylate, propyl methacrylate, butyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, methacrylate Examples include cycloalkyl methacrylates such as cyclohexyl methacrylate, aromatic methacrylates such as phenyl methacrylate and benzyl methacrylate, and methacrylic esters such as glycidyl methacrylate. Examples of aromatic vinyl compounds include styrene, α-methylstyrene, α-ethylstyrene, etc.
- There are nuclear substituted styrenes such as substituted styrene, chlorostyrene, vinyltoluene, and t-butylstyrene. Examples of vinyl cyanide compounds include acrylonitrile and methacrylonitrile. Examples of N-substituted maleimide include N-methylmaleimide, N-
Aliphatic N-substituted maleimides such as ethylmaleimide, N-isopropylmaleimide, N-butylmaleimide, and N-laurylmaleimide; alicyclic N-substituted maleimides such as N-cyclohexylmaleimide; N-phenylmaleimide; enylmaleimide, N-chlorophenylmaleimide,
Aromatic N- such as N-methoxyphenylmaleimide
Examples include substituted maleimides. In addition, vinyl acetate, α-methylethylene, diethyl maleate, etc. can also be used. Polymers of the above monomers include polyethylene, polypropylene, and the like. In the present invention, other polymers include polymers that cannot be obtained by vinyl polymerization, such as saturated polyesters such as polyphenylene oxide, polyethylene terephthalate, and polybutylene terephthalate, and unsaturated polyesters. As a method for producing the polymer of the present invention, known methods such as radical polymerization and ionic polymerization can be applied. For example, it can be produced by methods such as bulk polymerization, solution polymerization, and suspension polymerization in the presence of a polymerization initiator. Polymerization methods are preferred. In this case, the monomer () is polymerized in the presence of the above-mentioned monomer () or other polymers, but even if these polymers are dissolved in the monomer (), the monomer It may be impregnated with (). Examples of initiators used in polymerization include benzoyl peroxide, lauroyl peroxide, di-t-butylperoxyhexahydroterephthalate, t-butylperoxy-2-ethylhexanoate, 1,
Organic peroxides such as 1-di-t-butylperoxy-3,3,5-trimethylsilclohexane,
Water-soluble azo compounds such as azobisisobutyronitrile, azobis-4-methoxy-2,4-dimethylvaleronitrile, azobiscyclohexanone-1-carbonitrile, azodibenzoyl, potassium persulfate, and ammonium persulfate Any catalyst that can be used in conventional radical polymerization can be used, such as a redox catalyst using a combination of a catalyst and a peroxide or a persulfate and a reducing agent. The polymerization catalyst is preferably used in an amount of 0.01 to 10% by weight based on the total amount of monomers. A mercaptan compound, thioglycol, carbon tetrabromide, α-methylstyrene dimer, etc. as a polymerization regulator may be added as necessary to control the molecular weight. The polymerization temperature is preferably selected appropriately between 0 and 200°C, particularly preferably 50 and 120°C. As a solvent for solution polymerization, benzene, toluene, xylene, methyl ethyl ketone, methyl isobutyl ketone, ethyl acetate, butyl acetate, dichloroethylene, etc. can be used. Suspension polymerization is carried out in an aqueous medium, with the addition of suspending agents and, if necessary, suspension aids. Examples of suspending agents include water-soluble polymers such as polyvinyl alcohol, methyl cellulose, and polyacrylamide, and sparingly soluble inorganic substances such as calcium phosphate and magnesium pyrophosphate. It is preferable to use 0.05 to 0.5% by weight of the poorly soluble inorganic substance based on the total amount of monomers. Suspending aids include anionic surfactants such as sodium dodecylbenzenesulfonate, and when a sparingly soluble inorganic substance is used as a suspending agent, it is preferable to use them together. The suspension aid is preferably used in an amount of 0.001 to 0.02% by weight based on the total amount of monomers. Tricyclo[5.2.1.0 2,6 ]dec-8-yl methacrylate or tricyclo[5.2.1.0 2,6 ]dec-8-yl acrylate used in the present invention relates to the synthesis of methacrylic ester or acrylic ester. Obtained using a generally known method. For example, by adding H 2 O to dicyclopentadiene to form dicyclopentenyl alcohol, followed by a catalytic hydrogenation reaction, tricyclo[5.2.1.0 2,6 ]dec-8-ol is obtained. It can be obtained by a condensation reaction between this alcohol and methacrylic acid, acrylic acid, methacrylic acid chloride, or acrylic acid chloride, or a transesterification reaction with methyl methacrylate or methyl acrylate. The polymer obtained by the present invention can be applied to expandable thermoplastic resin particles, injection molding materials, extrusion molding materials, and the like. When using the polymer obtained according to the present invention, various additives such as pigments, flame retardants,
Known additives such as antioxidants, plasticizers, and antistatic agents may also be included. The resin particles obtained from the present invention can be used as a heat-resistant thermoplastic resin for extrusion, injection, etc., and can also be used as a foam raw material. Next, examples of the present invention will be shown. Example 1 1500g of ion-exchanged water was placed in a 4-rotating autoclave with polyvinyl alcohol (Denki Kagaku Kogyo Co., Ltd.).
W-24) 4.5g and polystyrene particles (0.6-0.8mm)
500g (diameter) was charged, and the temperature in the system was raised to 80°C while stirring. 500g of tricyclo[5.2.1.0 2,6 ]dec-8-yl methacrylate in 125g portions 20
It was dropped three times at minute intervals. Next, add 1,1-di-t-butylperoxy 3,3,5-
2.67 g of trimethylcyclohexane and 0.5 g of t-butyl perbenzoate were dissolved and added in the same manner 30 minutes after the third solution addition. After continuing the reaction at the same temperature for an additional 3 hours, the temperature was raised to 120°C in 60 minutes, and stirring was continued at this temperature for 3 hours. Thereafter, it was cooled to 30°C to obtain polymer particles. Table 1 shows the average diameter and glass transition temperature. Example 2 Polystyrene particles used in Example 1
500g of polyphenylene ether instead of 500g
Table 1 shows the average diameter and glass transition temperature of polymer particles obtained using [PPO manufactured by Engineering Plastics]. Example 3 Tricyclo[5.2.1.0 2,6 ]dec-8-yl methacrylate 500 was placed in an autoclave equipped with a rotary stirrer.
g and 250 g of styrene were added, and while stirring, 250 g of polyphenylene ether (PPO manufactured by Engineering Plastics) was added, and the mixture was completely dissolved in 2 hours while purging with nitrogen gas. After complete dissolution, 2.3 g of benzoyl peroxide and 1.5 g of t-butyl perbenzoate were dissolved, then stirring was stopped and 2000 g of ion-exchanged water was added, stirring was restarted, and 5 g of tricalcium phosphate and 0.5 g of sodium dodecylbenzenesulfonate were added. % solution 6g, sodium sulfate
Suspension polymerization was started by adding 0.75 g. Thereafter, polymer particles were produced in the same manner as in Example 1. Table 1 shows the average diameter and glass transition temperature. Comparative Example 1 A polymer was prepared in the same manner as in Example 3, except that tricyclo[5.2.1.0 2,6 ]dec-8-yl methacrylate was not used and 250 g of polyphenylene ether was dissolved in 750 g of styrene monomer. Particles were obtained. Table 1 shows the average diameter and glass transition temperature.
【表】
本発明により、耐熱性に優れた樹脂を得ること
ができる。また、本発明において、重合法として
懸濁重合を採用しても特に問題なく、安定して行
なうことができる。[Table] According to the present invention, a resin with excellent heat resistance can be obtained. Further, in the present invention, even if suspension polymerization is employed as the polymerization method, it can be carried out stably without any particular problem.
Claims (1)
８―イル、アクリル酸トリシクロ〔5.2.1.02,6〕デ
カ―８―イルおよび他の重合性モノマーからなる
モノマー群から選ばれた少なくとも１種のモノマ
ー（）の重合体または他の重合体の存在下に、
該モノマー群から選ばれた少なくとも１種のモノ
マー（）（ただし、モノマー（）および／ま
たはモノマー（）には必ずメタクリル酸トリシ
クロ〔5.2.1.0.2,6〕デカ―８―イルおよび／または
アクリル酸トリシクロ〔5.2.1.02,6〕デカ―８―イ
ルが含まれる）を重合し、かつメタクリル酸トリ
シクロ〔5.2.1.02,6〕デカ―８―イルおよび／また
はアクリル酸トリシクロ〔5.2.1.02,6〕デカ―８―
イルのモノマーの総量に対する混合比を５〜100
重量％とすることを特徴とする重合体の製造法。[Scope of Claims] 1. Tricyclo[5.2.1.0 2,6 ]decacrylate methacrylate
A polymer of at least one monomer selected from the monomer group consisting of 8-yl, tricyclo[5.2.1.0 2,6 ]dec-8-yl acrylate and other polymerizable monomers, or of other polymers. In the presence of
At least one monomer () selected from the monomer group (However, monomer () and/or monomer () must include tricyclo[5.2.1.0. 2,6 ]dec-8-yl methacrylate and/or acrylic acid. (including tricyclo[5.2.1.0 2,6 ]dec-8-yl), and tricyclo[5.2.1.0 2,6 ]dec-8-yl methacrylate and/or tricyclo[5.2.1.0 acrylate]. 2,6 〕Deca-8-
The mixing ratio of yl to the total amount of monomers is 5 to 100.
A method for producing a polymer, characterized in that it is expressed as % by weight.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22395983A JPS60115609A (en) | 1983-11-28 | 1983-11-28 | Production of polymer |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP22395983A JPS60115609A (en) | 1983-11-28 | 1983-11-28 | Production of polymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60115609A JPS60115609A (en) | 1985-06-22 |
| JPS6328921B2 true JPS6328921B2 (en) | 1988-06-10 |
Family
ID=16806373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP22395983A Granted JPS60115609A (en) | 1983-11-28 | 1983-11-28 | Production of polymer |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60115609A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11341496B2 (en) | 2020-06-03 | 2022-05-24 | Fiserv, Inc. | Hardware device for entering a PIN via tapping on a touch screen display |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3684110D1 (en) * | 1985-12-03 | 1992-04-09 | Hitachi Chemical Co Ltd | COATING RESIN COMPOSITION. |
| JPH0717713B2 (en) * | 1985-12-17 | 1995-03-01 | 三井石油化学工業株式会社 | Poly (meth) acrylate polymer |
| JPH0717719B2 (en) * | 1985-12-17 | 1995-03-01 | 三井石油化学工業株式会社 | Poly (meth) acrylate copolymer |
| JPH0717718B2 (en) * | 1985-12-17 | 1995-03-01 | 三井石油化学工業株式会社 | Poly (meth) acrylate copolymer |
| JP2564273B2 (en) * | 1986-04-01 | 1996-12-18 | 日立化成工業 株式会社 | Casting optical resin material |
| JP2000104747A (en) | 1998-07-29 | 2000-04-11 | Nsk Ltd | Capped rolling bearing |
| US7226980B2 (en) | 2003-08-07 | 2007-06-05 | General Electric Company | Thermoset composition, method for the preparation thereof, and articles prepared therefrom |
-
1983
- 1983-11-28 JP JP22395983A patent/JPS60115609A/en active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11341496B2 (en) | 2020-06-03 | 2022-05-24 | Fiserv, Inc. | Hardware device for entering a PIN via tapping on a touch screen display |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60115609A (en) | 1985-06-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU595837B2 (en) | Method for in-mold polymerization of unsaturated compound | |
| JPS6328921B2 (en) | ||
| HRP920442A2 (en) | Compositions based on unsaturated polyester resins and new antishrink additives | |
| US4663357A (en) | Higher molecular weight thermoplastics having multimodal molecular weight distribution | |
| EP1123324B1 (en) | Process using dialkylperoxide compounds for initiating a chemical reaction | |
| JPS6390515A (en) | Production of heat-resistant resin composition | |
| JPS6090204A (en) | Production of polymer | |
| US5344902A (en) | Polymerization with initiator and quaternary ammonium salt | |
| US3673129A (en) | Synthetic resin multicellular product whose main component is acrylonitrile and process for preparation thereof | |
| US3635852A (en) | Process of making a general purpose expandable alkenyl aromatic polymer containing di-alkyl polysiloxane internally | |
| US3553112A (en) | Expandable alkenyl aromatic polymers containing incorporated expandable alkenyl aromatic polymers | |
| JPH07100726B2 (en) | Method for producing styrene-methacrylic acid copolymer | |
| JPS5951906A (en) | Production of graft copolymer | |
| US5190984A (en) | Photodegradable expanded polymeric foam | |
| JPS60206849A (en) | Preparation of expandable thermoplastic copolymer particle | |
| JPH0527643B2 (en) | ||
| JPS59215307A (en) | Production of particulate modified polyester | |
| JPH02193958A (en) | Methacrylic acid ester and production thereof | |
| JP2716928B2 (en) | Method for producing high molecular weight styrenic polymer particles | |
| US5216036A (en) | Photodegradable expanded polymeric foam | |
| JP2670402B2 (en) | Method for producing high molecular weight styrenic polymer | |
| JPS6137098B2 (en) | ||
| JPS63191812A (en) | Production of high refractive index resin | |
| KR940003363B1 (en) | Method for in-mold polymerization of unsaturated compounds | |
| JPH05222282A (en) | Low-shrinkage unsaturated polyester resin composition |