JPS6366253A - Cast methacryl resin plate having excellent antistaticity and production thereof - Google Patents
Cast methacryl resin plate having excellent antistaticity and production thereofInfo
- Publication number
- JPS6366253A JPS6366253A JP21115886A JP21115886A JPS6366253A JP S6366253 A JPS6366253 A JP S6366253A JP 21115886 A JP21115886 A JP 21115886A JP 21115886 A JP21115886 A JP 21115886A JP S6366253 A JPS6366253 A JP S6366253A
- Authority
- JP
- Japan
- Prior art keywords
- weight
- monomer
- cast plate
- methacrylic resin
- polymer
- 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 17
- 239000011347 resin Substances 0.000 title description 8
- 229920005989 resin Polymers 0.000 title description 8
- 125000005641 methacryl group Chemical group 0.000 title 1
- 239000000178 monomer Substances 0.000 claims abstract description 50
- 229920001577 copolymer Polymers 0.000 claims abstract description 29
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims abstract description 23
- 239000000203 mixture Substances 0.000 claims abstract description 23
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 18
- 230000000379 polymerizing effect Effects 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 150000001450 anions Chemical class 0.000 claims abstract description 5
- 125000001424 substituent group Chemical group 0.000 claims abstract description 4
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 239000000113 methacrylic resin Substances 0.000 claims description 29
- 238000006116 polymerization reaction Methods 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 20
- 229920000642 polymer Polymers 0.000 claims description 14
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 229910052751 metal Inorganic materials 0.000 claims description 2
- 239000002184 metal Substances 0.000 claims description 2
- 229910001220 stainless steel Inorganic materials 0.000 claims description 2
- 239000010935 stainless steel Substances 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000013329 compounding Methods 0.000 abstract 1
- 230000000052 comparative effect Effects 0.000 description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 7
- 230000000704 physical effect Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 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 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 6
- -1 cationic quaternary ammonium salts Chemical class 0.000 description 6
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
- 239000002216 antistatic agent Substances 0.000 description 5
- 238000011156 evaluation Methods 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- 239000012298 atmosphere Substances 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 239000007870 radical polymerization initiator Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- 238000005266 casting Methods 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 230000003750 conditioning effect Effects 0.000 description 3
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- OFNISBHGPNMTMS-UHFFFAOYSA-N 3-methylideneoxolane-2,5-dione Chemical compound C=C1CC(=O)OC1=O OFNISBHGPNMTMS-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 description 2
- 150000001347 alkyl bromides Chemical class 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 238000000137 annealing Methods 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 2
- 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 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000003505 polymerization initiator Substances 0.000 description 2
- 230000003068 static effect Effects 0.000 description 2
- 150000003459 sulfonic acid esters Chemical class 0.000 description 2
- 238000009864 tensile test Methods 0.000 description 2
- NNNLYDWXTKOQQX-UHFFFAOYSA-N 1,1-di(prop-2-enoyloxy)propyl prop-2-enoate Chemical compound C=CC(=O)OC(CC)(OC(=O)C=C)OC(=O)C=C NNNLYDWXTKOQQX-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
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- VKDHHIOILCFABI-UHFFFAOYSA-N 2-(2,2-dihydroxyethylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNCC(O)O VKDHHIOILCFABI-UHFFFAOYSA-N 0.000 description 1
- STMDPCBYJCIZOD-UHFFFAOYSA-N 2-(2,4-dinitroanilino)-4-methylpentanoic acid Chemical compound CC(C)CC(C(O)=O)NC1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O STMDPCBYJCIZOD-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- QHVBLSNVXDSMEB-UHFFFAOYSA-N 2-(diethylamino)ethyl prop-2-enoate Chemical compound CCN(CC)CCOC(=O)C=C QHVBLSNVXDSMEB-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- OBMRSUNAEQGDLK-UHFFFAOYSA-N 2-(dipropylamino)ethyl 2-methylprop-2-enoate Chemical compound CCCN(CCC)CCOC(=O)C(C)=C OBMRSUNAEQGDLK-UHFFFAOYSA-N 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
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-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
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- WWJCRUKUIQRCGP-UHFFFAOYSA-N 3-(dimethylamino)propyl 2-methylprop-2-enoate Chemical compound CN(C)CCCOC(=O)C(C)=C WWJCRUKUIQRCGP-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- GJFDBYRHAZJJBP-UHFFFAOYSA-N 3-tert-butylpyrrole-2,5-dione Chemical compound CC(C)(C)C1=CC(=O)NC1=O GJFDBYRHAZJJBP-UHFFFAOYSA-N 0.000 description 1
- OAKUJYMZERNLLT-UHFFFAOYSA-N 4-(dimethylamino)butyl 2-methylprop-2-enoate Chemical compound CN(C)CCCCOC(=O)C(C)=C OAKUJYMZERNLLT-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 229920006353 Acrylite® Polymers 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 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
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- RJFAYQIBOAGBLC-BYPYZUCNSA-N Selenium-L-methionine Chemical compound C[Se]CC[C@H](N)C(O)=O RJFAYQIBOAGBLC-BYPYZUCNSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 239000004566 building material Substances 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000012986 chain transfer agent Substances 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000009749 continuous casting Methods 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000000593 degrading effect Effects 0.000 description 1
- 125000004386 diacrylate group Chemical group 0.000 description 1
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012760 heat stabilizer Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- QZIQJVCYUQZDIR-UHFFFAOYSA-N mechlorethamine hydrochloride Chemical compound Cl.ClCCN(C)CCCl QZIQJVCYUQZDIR-UHFFFAOYSA-N 0.000 description 1
- 229960003505 mequinol Drugs 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
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- 229920001281 polyalkylene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- 239000005341 toughened glass Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 1
- 238000004506 ultrasonic cleaning Methods 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
Landscapes
- Graft Or Block Polymers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
〔産業上の利用分野〕
本願の発明は、良好且つ恒久的な帯電防止性を有するメ
タクリル樹脂キャスト板及びその製法に関するものであ
る。DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention relates to a methacrylic resin cast plate having good and permanent antistatic properties and a method for producing the same.
メタクリル樹脂キャスト板はその優れた透明性、表面光
沢、美しい外観、良好な機械的性質等によシ、照明器具
、看板、建材、各種銘板、装飾品などに広く利用されて
いるが、(イ)表面抵抗値が高いため容易に帯電し、ゴ
ミ、はこり等を吸引して外観を損ねる、P)キズがつく
、(/9人体やエレクトロニクス部品に対して電撃を与
える等の問題を起こしている。Methacrylic resin cast plates are widely used for lighting equipment, signboards, building materials, various nameplates, decorations, etc. due to their excellent transparency, surface gloss, beautiful appearance, and good mechanical properties. ) Due to the high surface resistance value, it is easily charged and attracts dust, clumps, etc., damaging the appearance. P) It causes scratches. There is.
メククリル樹脂キャスト板に帯電防止性を付与する方法
としては
(1)界面活性剤の内部添加
(2)〃 の表面塗布
(3) シリコン系化合物の表面塗布(4) プラ
ズマ処理による表面改質があげられる。これらのうち(
3)、(4)はいずれもコスト的に高価となるので、一
般には(1)、(2)の方法が用いられる。Methods for imparting antistatic properties to Mekkrylic resin cast plates include (1) internal addition of surfactants, (2) surface coating, (3) surface coating of silicon compounds, and (4) surface modification by plasma treatment. It will be done. Among these (
Since both methods 3) and (4) are expensive, methods (1) and (2) are generally used.
使用される界面活性剤としては、アニオン系、カチオン
系、ノニオン系のものがあるが、特にカチオン系の第四
級アンモニウム塩を含んだ化合物が優れた帯電防止性能
を与えるものとして知られている。The surfactants used include anionic, cationic, and nonionic surfactants, but compounds containing cationic quaternary ammonium salts are particularly known to provide excellent antistatic performance. .
これらの界面活性剤を表面塗布処理する場合、メタクリ
ル樹脂キャスト板の表面状態を損わないようにするには
微妙な操作が請求され、且つこのように処理したメタク
リ/L’樹脂キャスト板においては、水洗や摩擦等によ
り表面に付着した帯電防止剤が容易に脱落し、帯電防止
性能が失われてしまう問題点がある。When applying these surfactants to the surface, delicate operations are required to avoid damaging the surface condition of the methacrylic resin cast board, and the methacrylic/L' resin cast board treated in this way has However, there is a problem in that the antistatic agent attached to the surface easily falls off due to washing with water, friction, etc., and the antistatic performance is lost.
界面活性剤を内部添加する方法は、重合前の樹脂原料に
帯電防止剤を混合又は分散するので製造工程が簡単とな
るが、充分な帯電防止性能を得るためには、一般に添加
歎を多くする必要がちり、そうするとメタクリル樹脂の
透明性や機械的物性を損い、且つ得られた帯電防止性能
が水洗や摩擦等によシ容易に失なわれてしまう問題点が
ある。The method of internally adding a surfactant simplifies the manufacturing process because the antistatic agent is mixed or dispersed into the resin raw material before polymerization, but in order to obtain sufficient antistatic performance, it is generally necessary to add more. If dusting occurs, the transparency and mechanical properties of the methacrylic resin will be impaired, and the antistatic properties obtained will be easily lost due to washing with water, friction, etc.
内部添加法の上記のような欠点を克服するために、帯電
防止剤として重合性の単量体を使用する試みがなされた
(特公昭4B−15471号、特公昭54−23395
号)。しかしながらこの種のものは、帯電防止性能が不
充分であったシ、キャスト重合によって得られた板と鋳
型の接着性が強くなシ、安定した製造が難かしくなる欠
点を有していた。In order to overcome the above-mentioned drawbacks of the internal addition method, attempts were made to use polymerizable monomers as antistatic agents (Japanese Patent Publication No. 4B-15471, Japanese Patent Publication No. 23395-1983).
issue). However, this type of product had the disadvantages of insufficient antistatic performance, strong adhesion between the plate obtained by cast polymerization and the mold, and difficulty in stable production.
〔発明が解決しようとする問題点0
以上のように、特別な製造工程を必要とせず、良好な帯
電防止性能を恒久的に示し、且つメタクリル樹脂本来の
物性を保持しているようなメグクリル樹脂キャスト板は
従来提案されていない。[Problem to be solved by the invention 0 As described above, a megacrylic resin that does not require any special manufacturing process, permanently exhibits good antistatic performance, and maintains the physical properties inherent to methacrylic resin. Cast boards have not been proposed so far.
本発明者等は、上記問題点について鋭意検討の結果、メ
チルメタクリレートをキャスト重合させる際にある種の
四級アンモニウム塩基を持つ(共)重合体を少量添加す
ることによシ良好で且つ恒久的な帯電防止性能を有し、
メタクリル樹脂本来の物性を保持しているような、メグ
クリル樹脂キャスト板が得られることを見出した。As a result of intensive studies on the above-mentioned problems, the present inventors have discovered that a good and permanent effect can be obtained by adding a small amount of a (co)polymer having a certain type of quaternary ammonium base during cast polymerization of methyl methacrylate. It has excellent antistatic performance,
It has been found that a megcryl resin cast plate that retains the original physical properties of methacrylic resin can be obtained.
すなわち本願の発明は、メチルメタクリレート又はメチ
μメタクリレート50重量−以上とこれと共重合可能な
少なくとも一種の単量体50重量−以下とからなる単量
体混合物或いは、それらの部分重合体(J) 100重
量部に対し、一般式
%式%
(R+は水素原子又はメチル基、R3−R4は水素原子
又は炭素数1〜9の置換基を含んでいてもよいアルキル
基、mは1〜10、Xは四級化剤のアニオン)
で表わされる四級アンモニウム塩基を有する単量体20
〜100重量%、好ましくは3o〜90重量%及びこれ
と共重合可能々少なくとも一種の単量体80〜0重量%
、好ましくは70〜10重量%からなる単量体又は単量
体混合物を重合させて得られた(共)重合体(III)
0.1〜2o重量部を混合して重合させることを特徴
とする帯電防止性に優れたメタクリ/I/樹脂キャスト
板の製法と、そのような製法によって得られるキャスト
板に関するものである。That is, the invention of the present application provides a monomer mixture consisting of 50 weight or more of methyl methacrylate or methyμ methacrylate and 50 weight or less of at least one monomer copolymerizable therewith, or a partial polymer thereof (J) With respect to 100 parts by weight, the general formula % formula % (R + is a hydrogen atom or a methyl group, R3-R4 is a hydrogen atom or an alkyl group that may contain a substituent having 1 to 9 carbon atoms, m is 1 to 10, X is an anion of a quaternizing agent) Monomer 20 having a quaternary ammonium base represented by
-100% by weight, preferably 30-90% by weight and 80-0% by weight of at least one monomer copolymerizable therewith
(co)polymer (III) obtained by polymerizing a monomer or monomer mixture, preferably consisting of 70 to 10% by weight.
The present invention relates to a method for producing a methacrylate/I/resin cast plate with excellent antistatic properties, which is characterized by mixing and polymerizing 0.1 to 20 parts by weight, and a cast plate obtained by such a production method.
本発明においてメチルメタクリレート単量体混合物又は
、それらの部分重合体に用いられる共重合可能な単量体
としては、エチルメタクリソート、メチルメタクリレー
ト、2−エチルヘキシルメタクリレート等のメタクリル
酸エステル類、メチルアクリレート、エチルアクリレー
ト、ブチルアクリレート、2−エチルへキシルアクリレ
ート等のアクリル酸エステル類、アクリル酸、メタクリ
ル酸、マレイン酸、イタコン酸等の不飽和カルボン酸、
無水マレイン酸、無水イタコン酸等の酸無水物、N−フ
ェニルマレイミド、N−シクロヘキシルマレイミド、N
−t−ブチルマレイミド等のマレイミド誘導体、2−ヒ
ドロキシエチルアクリレート、2−ヒドロキシプロピル
アクリレート、2−ヒドロキシエチルアクリレート、2
−ヒドロキシプロピμメタクリV−ト等のヒドロキシ基
含有単量体、アクリルアミド、メタクリルアミド、アク
リロニトリμ、メタクリレートリル、ジアセトンアクリ
ルアミド、ジメチルアミノエチルメタクリレート等の窒
素含有単量体、アリμグリシジμエーテμ、グリシジル
アクリレート、グリシジルメタクリソート等のエポキシ
基含有単量体、スチレン、α−メチルスチレン等のスチ
レン系単量体、エチレングリコ−!ジアクリレート、ア
リルアクリレート、エチレングリコールジメタクリレー
ト、アリルメタクリレート、ジビニルベンゼン、トリメ
チロ−μプロパントリアクリレート等の架橋剤等が挙げ
られる。In the present invention, the copolymerizable monomers used in the methyl methacrylate monomer mixture or their partial polymers include methacrylic acid esters such as ethyl methacrylate, methyl methacrylate, and 2-ethylhexyl methacrylate, methyl acrylate, Acrylic acid esters such as ethyl acrylate, butyl acrylate, and 2-ethylhexyl acrylate; unsaturated carboxylic acids such as acrylic acid, methacrylic acid, maleic acid, and itaconic acid;
Acid anhydrides such as maleic anhydride and itaconic anhydride, N-phenylmaleimide, N-cyclohexylmaleimide, N
- Maleimide derivatives such as t-butylmaleimide, 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 2-hydroxyethyl acrylate, 2-hydroxyethyl acrylate,
-Hydroxy group-containing monomers such as hydroxypropyl methacrylate, acrylamide, methacrylamide, acrylonitrium, methacrylateryl, diacetone acrylamide, dimethylaminoethyl methacrylate, etc., aliμ glycidiμ ether μ , epoxy group-containing monomers such as glycidyl acrylate and glycidyl methacrysate, styrene monomers such as styrene and α-methylstyrene, ethylene glyco! Examples include crosslinking agents such as diacrylate, allyl acrylate, ethylene glycol dimethacrylate, allyl methacrylate, divinylbenzene, and trimethylo-μ propane triacrylate.
共重合可能な単量体の種類と添加量は、目的とするキャ
スト板の性質によシ適宜選ぶことができる。The type and amount of the copolymerizable monomer can be appropriately selected depending on the properties of the intended cast plate.
本発明において(共)重合体(II)を構成する四級ア
ンモニウム塩基を有する単量体は、一般式0式%
(R1−R4及びmは前述した通シである)で表わされ
、これはアミノ基を有するアクリレートもしくはメタク
リレートを四級化剤によシ四級化することによシ得られ
る。アミノ基を有するメタクリレートもしくはアクリレ
ートとしてハ、ジメチμアミノエチμメタクリV−ト、
ジエチルアミノエチルメタクリレート、ジメチルアミノ
プロピルメタクリレート、ジメチルアミノエチルアクリ
レート、ジエチルアミノエチルアクリレート、ジメチル
アミノブチルメタクリレート、ジヒドロキシエチルアミ
ノエチルメククリv−ト、ジプロピルアミノエチルメタ
クリレート、ジブチルアミノエチルメタクリレート等が
挙げられる。In the present invention, the monomer having a quaternary ammonium base constituting the (co)polymer (II) is represented by the general formula 0 (R1-R4 and m are the same as above), and this can be obtained by quaternizing an acrylate or methacrylate having an amino group using a quaternizing agent. As the methacrylate or acrylate having an amino group, dimethylμ aminoethyl V-methacrylate;
Examples include diethylaminoethyl methacrylate, dimethylaminopropyl methacrylate, dimethylaminoethyl acrylate, diethylaminoethyl acrylate, dimethylaminobutyl methacrylate, dihydroxyethylaminoethyl methacrylate, dipropylaminoethyl methacrylate, and dibutylaminoethyl methacrylate.
四級化剤としては、ジメチル硫酸、ジエチル硫酸、ジプ
ロピル硫酸等のアルキル硫酸類、P−トルエンヌルホン
酸メチル、ベンゼンスルホン酸メチル等のスμホン酸エ
ステ〜、トリメチルホスフェイト等のアルキルリン酸、
アρキルベンジpクロライド、ベンジルクロフィト、ア
ルキルブロマイド、アルキルブロマイド等の各種ハライ
ドが用いられ、特にアルキル硫酸、スルホン酸エステル
が耐熱分解性の点より好址しい。一般式中のmは1〜1
0であるが、2〜6が特に好ましい。Examples of quaternizing agents include alkyl sulfates such as dimethyl sulfate, diethyl sulfate, and dipropyl sulfate, sulfonic acid esters such as methyl P-toluene sulfonate, and methyl benzenesulfonate, and alkyl phosphoric acids such as trimethyl phosphate. ,
Various halides such as alkyl bendi p chloride, benzyl chlorophyte, alkyl bromide, and alkyl bromide are used, and alkyl sulfates and sulfonic acid esters are particularly preferred from the viewpoint of heat decomposition resistance. m in the general formula is 1 to 1
0, but 2 to 6 are particularly preferred.
四級アンモニウム塩基を有する単量体と共重合可能な単
量体としては、公知の単量体が使用できる。例えばメチ
ルアクリレート、エチルメタクリレート等のメタクリl
し酸エステル類、メチルアクリレート、エチルアクリレ
ート等のアクリル酸エステル類、アクリル酸メククリル
酸等の不飽和カルボン酸、無水マレイン酸、無水イタコ
ン酸等の酸無水物、N−フェニルマレイミド等のマレイ
ミド誘導体、2−ヒドロキシエチルアクリソート、2−
ヒドロキシプロピμメタクリレート等のヒドロキシ基含
有単量体、アクリルアミド、アクリロニトリル等の窒素
含有単斌体、アリルグリシジルエーテル、グリシジルア
クリ1/ −)等のエポギシ基含有単量体がある。As the monomer copolymerizable with the monomer having a quaternary ammonium base, known monomers can be used. For example, methacrylate such as methyl acrylate, ethyl methacrylate, etc.
Acrylic acid esters such as phosphoric acid esters, methyl acrylate and ethyl acrylate, unsaturated carboxylic acids such as acrylic acid and meccrylic acid, acid anhydrides such as maleic anhydride and itaconic anhydride, maleimide derivatives such as N-phenylmaleimide, 2-hydroxyethylacrysate, 2-
Examples include hydroxy group-containing monomers such as hydroxypropyμ methacrylate, nitrogen-containing monomers such as acrylamide and acrylonitrile, and epoxy group-containing monomers such as allyl glycidyl ether and glycidyl acrylic 1/-).
これらのうち下記一般式
(′R6は水素原子又はメチル基、八は水素原子又は炭
素原子数1〜18のアμキμ基、アvrv基、アリール
基、アラルキル基、Aは炭素数2〜4のアルキレン基、
nは0〜500)
で表わされる化合物より選ばれたものを使用する。Among these, the following general formula ('R6 is a hydrogen atom or a methyl group, 8 is a hydrogen atom or an Aμ group having 1 to 18 carbon atoms, an Avrv group, an aryl group, an aralkyl group, and A is a C2 to C2 group) 4 alkylene group,
A compound selected from the following (n is 0 to 500) is used.
本発明における(共)重合体(n)の好ましい組成は、
四級アンモニウム塩基を有する単量体成分を30〜90
重量%と共重合可能でポリアルキレングリコ−μ成分を
有する単量体成分10〜70重量%を含むものである。The preferred composition of the (co)polymer (n) in the present invention is:
30 to 90 monomer components having a quaternary ammonium base
It contains 10 to 70% by weight of a monomer component copolymerizable with polyalkylene glyco-μ component.
(共)重合体0中の四級アンモニウム塩基を有する単量
体成分が30重量%未満、特に20重量%未満では、得
られるメタクリル樹脂キャスト板に良好な制電性が付与
できない場合があシ、90重量−以上ではメチルメタク
リレート単量体(混合物)又はその部分重合体CI)に
対する溶解性が不足する傾向がある。If the monomer component having a quaternary ammonium base in (co)polymer 0 is less than 30% by weight, especially less than 20% by weight, it may not be possible to impart good antistatic properties to the resulting methacrylic resin cast plate. , 90% by weight or more, the solubility for the methyl methacrylate monomer (mixture) or its partial polymer CI) tends to be insufficient.
(共)重合体(I[)を調製する方法は、特に限定され
ないが、通常のラジカル重合開始剤及び連鎖移動剤の存
在下、溶液重合、塊状重合等の手法を用いることができ
る。特に溶液重合が均一系のまま重合できるので好まし
い。又、溶液重合の場合、単量体の一括添加、分割添加
、滴下添加等種々の添加方法を採用できる。The method for preparing the (co)polymer (I[) is not particularly limited, but techniques such as solution polymerization and bulk polymerization in the presence of a usual radical polymerization initiator and chain transfer agent can be used. In particular, solution polymerization is preferable because polymerization can be carried out in a homogeneous system. In the case of solution polymerization, various addition methods such as bulk addition, divided addition, and dropwise addition of monomers can be employed.
本発明における(共)重合体(II)の分子量は、10
00以上であることが好ましい。1000未満であれば
、良好な恒久帯電防止性能が得られない場合があシ、又
可塑化効果によシメククリμ樹脂本来の耐熱性を低下さ
せる傾向がある。The molecular weight of the (co)polymer (II) in the present invention is 10
It is preferable that it is 00 or more. If it is less than 1,000, good permanent antistatic performance may not be obtained, and the heat resistance inherent to the Shimekuri μ resin tends to be lowered due to the plasticizing effect.
(共)重合体(II)のメチルメタクリレート単量体(
混合物)又はその部分重合物(I) 100重量部に対
する添加量は0.1〜20重量部が好ましく、特に好壕
しくはQ、5〜10重量部である。Methyl methacrylate monomer (co)polymer (II) (
The amount added is preferably from 0.1 to 20 parts by weight, particularly preferably from 5 to 10 parts by weight, per 100 parts by weight of the mixture) or its partial polymer (I).
この添加量が0.1重量部未満であると良好な帯電防止
性能を付与できず、20重量部を超えるとメタクリル樹
脂本来の物性を大きく損ねる上にコスト高となる。If the amount added is less than 0.1 part by weight, good antistatic performance cannot be imparted, and if it exceeds 20 parts by weight, the inherent physical properties of the methacrylic resin will be greatly impaired and the cost will increase.
本発明における帯電防止性の優れたメタクリル樹脂キャ
スト板は、当該業者によって普通に行われている鋳込重
合法によって製造するのが好ましい。すなわちメチルメ
タクリシート又はメチルメタクリレート50重量%以上
と、共重合可能な少なくとも一種類の単量体50重量−
以下とからなる単量体混合物或いはそれらの部分重合物
(I)に所定址の洪)重合体(II)を添加して均一に
溶解させ、得られた混合物にさらにラジカル重合開始剤
を添加して鋳込原料とする。The methacrylic resin cast plate with excellent antistatic properties in the present invention is preferably manufactured by a cast polymerization method commonly practiced by those skilled in the art. That is, 50% by weight or more of methyl methacrylate or methyl methacrylate and 50% by weight of at least one type of monomer that can be copolymerized.
Polymer (II) in a predetermined area is added to a monomer mixture consisting of the following or a partial polymer thereof (I) and dissolved uniformly, and a radical polymerization initiator is further added to the resulting mixture. and use it as casting raw material.
該原料を、周辺をガスケットでシールした対向させた2
枚の無機ガラス板又は、金属板の間に注入して加熱する
七μキャスト法か又は、同一方向に同一速度で進行する
片面鏡面研摩された2枚のステンレス製エンドレスベル
トとガスケットとでシールされた空間の上流から連続的
に上記の鋳込原料を注入して加熱する連続キャスト法が
具体的な重合方法として挙げられる。The raw materials were placed facing each other with the periphery sealed with a gasket.
A space sealed with a gasket and a 7μ casting method in which it is injected between two inorganic glass plates or metal plates and heated, or with two mirror-polished stainless steel endless belts that move in the same direction and at the same speed. A specific polymerization method is a continuous casting method in which the above-mentioned casting raw material is continuously injected and heated from upstream.
上述した本発明の重合性原料(I)を重合させるには、
アゾ化合物あるいは、有機過酸化物等のラジカル重合開
始剤を用いるのが好ましい。To polymerize the above-mentioned polymerizable raw material (I) of the present invention,
It is preferable to use a radical polymerization initiator such as an azo compound or an organic peroxide.
アゾ化合物の具体例としては、2.2′−アゾビス(イ
ソブチロニトリル)、2.2’−アゾビス(2,4−ジ
メチルパンロニトリル)、2.2′−アゾビス(2,4
−ジメチ/L/−4−メトキシパレロニトリ/L’)等
を挙げることができ、他方有機過酸化物の具体例として
は、ベンゾイルパーオキサイド、ラウロイルパーオキサ
イド等が挙げられる。又、ンドックス系の重合開始剤、
例えば有機過酸化物とアミン類との組み合わせも用いる
ことができる。Specific examples of azo compounds include 2,2'-azobis(isobutyronitrile), 2,2'-azobis(2,4-dimethylpanronitrile), 2,2'-azobis(2,4
Specific examples of organic peroxides include benzoyl peroxide, lauroyl peroxide, and the like. In addition, Ndox-based polymerization initiators,
For example, combinations of organic peroxides and amines can also be used.
本発明のメタクリル樹脂キャスト板を重合によって製造
する際の重合温度は、使用するラジカル重合開始剤の種
類によって異なるが、一般には10〜150℃である。The polymerization temperature when producing the methacrylic resin cast plate of the present invention by polymerization varies depending on the type of radical polymerization initiator used, but is generally 10 to 150°C.
鋳込重合法によって得られるキャスト板の厚さは特に制
限はないが通常市販されている厚み、すなわち0.2〜
65mの範囲内であることが好ましい。The thickness of the cast plate obtained by the cast polymerization method is not particularly limited, but it is usually the thickness that is commercially available, that is, 0.2 ~
Preferably, it is within a range of 65 m.
さらに本発明の好都合な工程のいずれかに着色剤、紫外
線吸収剤、熱安定剤、他の帯電防止剤、各稲光てん剤等
の添加剤を混合して用いることができる。Furthermore, additives such as colorants, ultraviolet absorbers, heat stabilizers, other antistatic agents, lightning protection agents, etc. can be mixed and used in any of the convenient steps of the invention.
次に、実施例によってさらに具体的に本発明を説明する
が、本発明は、これらによって限定されるものではない
。Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto.
なお、すべての試料の電気的性質は、23℃65%相対
湿度で1日間調湿した後測定した。The electrical properties of all samples were measured after being conditioned at 23° C. and 65% relative humidity for one day.
電荷半減時間は、スタティックオネヌトメータニ(去月
商会製)を使用し、印加電圧1ooo。For the charge half-life time, use a static one-meter meter (manufactured by Sagetsu Shokai) and apply an applied voltage of 1ooo.
■、試料回転速度1300rpm、印加時間30秒、測
定湿度23℃、測定湿度65チの条件で測定し、電圧印
加時の試料電圧を初期電圧(V)、電圧印加後試料電圧
が初期電圧の半分になるまでの時間を電荷半減時間(s
ee )とした。表面抵抗値については、超絶縁抵抗計
(タヶダ理研製、TR−8601)を使用し、測定温度
23℃、測定湿度65%の条件で、印加電圧500■で
1分後の表面抵抗値(Ω)を測定した。洗浄は、30℃
の温水中で超音波洗浄を30分間行った。耐熱性につい
ては試料をア二−μ後、ASTM D648に準じて
HDT(6)を測定した。強度についてはASTM
D63Bに準じて引張試験を行い、引張弾性係数および
、引張破壊強度を測定した。透明性については、積分球
式ヘーズメーター(日本精密光学製、5EP−a−SS
)を使用して曇価を測定した。■ Measured under the conditions of sample rotation speed 1300 rpm, application time 30 seconds, measurement humidity 23℃, measurement humidity 65℃, sample voltage at the time of voltage application is initial voltage (V), sample voltage after voltage application is half of the initial voltage The time it takes for the charge to halve (s
ee). The surface resistance value was measured using a super insulation resistance meter (manufactured by TAGADA RIKEN, TR-8601) at a measurement temperature of 23℃ and a measurement humidity of 65%, and after 1 minute at an applied voltage of 500μ ) was measured. Wash at 30℃
Ultrasonic cleaning was performed in warm water for 30 minutes. Regarding heat resistance, the sample was subjected to annealing and HDT (6) was measured according to ASTM D648. ASTM for strength
A tensile test was conducted according to D63B, and the tensile elastic modulus and tensile breaking strength were measured. Regarding transparency, an integrating sphere haze meter (manufactured by Nippon Seimitsu Kogaku, 5EP-a-SS) was used.
) was used to measure the haze value.
実施例1
攪拌羽根付き3tガラス製フラスコに、ジェチμアミノ
エチμメタクリレート374重量部、ハイドロキノン七
ツメチルエーテル4重量部、メクノー/l’450重量
部を入れ、攪拌しながらジメチル硫酸252重量部、メ
タノ−/l/80重量部の混合物を30℃以下になるよ
うに滴下し、滴下終了後30分間攪拌を続けて四級アン
モニウム塩基を有する単量体(M−1)溶液を得た。Example 1 Into a 3t glass flask equipped with a stirring blade, 374 parts by weight of Jethi μ aminoethyl methacrylate, 4 parts by weight of hydroquinone methyl ether, and 450 parts by weight of Mekno/l' were added, and while stirring, 252 parts by weight of dimethyl sulfate and methanol were added. /l/80 parts by weight of the mixture was added dropwise at a temperature of 30° C. or below, and stirring was continued for 30 minutes after the completion of the addition to obtain a monomer (M-1) solution having a quaternary ammonium base.
この溶液に、アゾビスイソブチロニトリル6重量部、n
−オクチμメμカプタン4重量部、メタノ−/l/48
0重量部、ポリエチレングリコ−/l/(2!l)モノ
メタクリレートモノメチルエーテル620重量部を加え
、60℃窒素雰囲気下で4時間重合させた。重合後、そ
のまま真空乾燥して共重合体(P−1)を得た。メチル
メタクリレート部分重合体(粘度100センチポイズ、
重合率8%)100重量部に上記共重合体(P−1)を
[]、5重量部、重合開始剤としてス2′−アゾビスイ
ソブチロニトリルQ、05重量部を溶解させた後、減圧
にして溶存空気を除去し、ガスケット及び2枚の強化ガ
ラスによシ形成され、あらかじめ厚さ31!II+にな
るよう設定されたセル中に注いだ。重合は60℃におい
て10時間、110℃において4時間行った。このキャ
スト板は、表面抵抗率が2.0X10”Ω、電荷半減時
間五2秒、曇価2.5チであった。To this solution, 6 parts by weight of azobisisobutyronitrile, n
- Octime μcaptan 4 parts by weight, methanol/l/48
0 parts by weight and 620 parts by weight of polyethylene glyco/l/(2!l) monomethacrylate monomethyl ether were added, and the mixture was polymerized at 60°C under a nitrogen atmosphere for 4 hours. After polymerization, the mixture was directly vacuum-dried to obtain a copolymer (P-1). Methyl methacrylate partial polymer (viscosity 100 centipoise,
After dissolving 5 parts by weight of the above copolymer (P-1) in 100 parts by weight (polymerization rate 8%), and 05 parts by weight of 2'-azobisisobutyronitrile Q as a polymerization initiator. , vacuum is applied to remove dissolved air, the gasket and two pieces of tempered glass are formed, and the thickness is 31! Pour into a cell set to II+. Polymerization was carried out at 60°C for 10 hours and at 110°C for 4 hours. This cast plate had a surface resistivity of 2.0×10”Ω, a charge half-life time of 52 seconds, and a haze value of 2.5 inches.
又得られた板に水洗処理を行い、ただちに帯電防止性能
を評価したところ表面抵抗率1.5×10110、電荷
半減時間!Lo秒であった。In addition, the obtained board was washed with water and immediately evaluated for antistatic performance, and the surface resistivity was 1.5 x 10110, and the charge was halved in time! It was Lo seconds.
又、ASTM D648に準じてHDT試片を作成し
、アニール後HDTを測定したところ100℃であり、
ASTM D638に準じて引張試験を行ったところ
引張弾性係数3 X 10’(kg/の2)、引張破壊
強度750(ゆ/α2)であった。In addition, an HDT specimen was prepared according to ASTM D648, and the HDT was measured after annealing, and it was 100°C.
When a tensile test was conducted according to ASTM D638, the tensile modulus of elasticity was 3 x 10' (kg/2), and the tensile strength at break was 750 (y/α2).
比較例1
メチルメタクリレート部分重合体(粘度100センチポ
イズ、重合率8%)100重量部に2゜2′−アゾビス
イソブチロニトリル0.05重量部を溶解させた後、実
施例1と同様な方法で重合させて板厚3mのキャスト板
を得た。この板の表面抵抗率は10160以上であり、
電荷半減時間120 sec以上、曇価1.0チであっ
た。Comparative Example 1 After dissolving 0.05 parts by weight of 2゜2'-azobisisobutyronitrile in 100 parts by weight of methyl methacrylate partial polymer (viscosity 100 centipoise, polymerization rate 8%), the same procedure as in Example 1 was carried out. A cast plate with a thickness of 3 m was obtained by polymerization according to the method. The surface resistivity of this plate is 10160 or more,
The charge half-life time was 120 seconds or more, and the haze value was 1.0 chi.
又](DTは100℃であシ、引張弾性係数は3 X
10’ (kg/1yn2)、引張破壊強度は760(
k!9/6n2)であった。] (DT is 100℃, tensile modulus is 3
10' (kg/1yn2), tensile breaking strength is 760 (
k! 9/6n2).
実施例2〜4
メチルメタクリレート部分重合体(粘度100センチポ
イズ、重合率8%)100重量部に実施例1で得られた
共重合体P−1を1.0〜10.0重量部添加混合して
実施例1と同様の手法によシ厚さ3tllIHのメタク
リル樹脂キャスト板を得た。Examples 2 to 4 1.0 to 10.0 parts by weight of copolymer P-1 obtained in Example 1 were added and mixed to 100 parts by weight of methyl methacrylate partial polymer (viscosity 100 centipoise, polymerization rate 8%). By the same method as in Example 1, a methacrylic resin cast plate having a thickness of 3tllIH was obtained.
23℃、65チ相対湿度雰囲気中で1日間調湿後の帯電
防止性能及びその他の物性の評価結果を表1に示す。Table 1 shows the evaluation results of antistatic performance and other physical properties after humidity conditioning for one day in an atmosphere of 23° C. and 65° relative humidity.
実施例5〜9
実施例1で得た四級アンモニウム塩基を含む単量体M−
1溶液を用い、表2に示す組成の単量体混合物を加えて
実施例1と同様の手法で重合させて共重合体(P−2〜
6)を得た。これらの共重合体をそれぞれ2.0重量部
使用して、実施例1と同様の手法によシ厚さ3閣のメタ
クリル樹脂キャスト板を得た。23℃、65チ相対湿度
雰囲気で1日間調湿後の帯電防止性能及びその他の物性
の評価結果を表3に示す。Examples 5 to 9 Monomer M- containing quaternary ammonium base obtained in Example 1
1 solution, add a monomer mixture having the composition shown in Table 2, and polymerize in the same manner as in Example 1 to obtain a copolymer (P-2~
6) was obtained. Using 2.0 parts by weight of each of these copolymers, a methacrylic resin cast plate having a thickness of 3 cm was obtained in the same manner as in Example 1. Table 3 shows the evaluation results of antistatic performance and other physical properties after humidity conditioning at 23° C. and 65° relative humidity for one day.
実施例10〜14
表4に示すアミノ基含有アクリレート又はメタクリレー
トと四級化剤の組み合せを用いた他は、実施例1と同様
の手法によシ四級アンモニウム塩基を有する共重合体(
P−7〜P−11)ヲ得り。これらをメチルメタクリレ
ート部分重合体(粘度100センチポイズ、重合率8チ
)100重量部に対して2.0重量部添加し、実施例1
と同様の手法によシ、厚さ3簡のメタクリル樹脂板を得
た。23℃、65相対湿度雰囲気で1日間調湿した後の
帯電防止性能及びその他の物性の評価結果を表5に示す
。Examples 10 to 14 A copolymer having a quaternary ammonium base (
P-7 to P-11) Obtained. 2.0 parts by weight of these were added to 100 parts by weight of methyl methacrylate partial polymer (viscosity 100 centipoise, polymerization rate 8 cm), and Example 1
A methacrylic resin plate with a thickness of 3 sheets was obtained using the same method as above. Table 5 shows the evaluation results of antistatic performance and other physical properties after conditioning the humidity in an atmosphere of 23° C. and 65 relative humidity for one day.
実施例15
メチルメタクリレート部分重合体(粘度1000センチ
ポイズ、重合率20%)100重量部に、実施例1で得
た共重合体P−1を20重量部、重合開始剤として2,
2′−アゾビスイソブチロニトリ/I10.05重量部
、離型剤としてジオクチルスルホサクシネート・ナトリ
ウム4 o、 o o s重承部を添加混合したものを
、特公昭52−30985号に示す如き連続製板装置で
重合させて、厚さ5111I+のメタクリル樹脂板を製
造した。重合は70℃の温水雰囲気下で60分、次いで
130℃の空気雰囲気下で15分間滞在させ重合を完結
させた。得られたメタクリル樹脂キャスト板を実施例1
と同様に評価したところ、表面抵抗率5.0X10’Ω
、電荷半減時間1.7秒、曇価4.0%であり、水洗処
理後の表面抵抗率は五6×1090であった。Example 15 To 100 parts by weight of methyl methacrylate partial polymer (viscosity 1000 centipoise, polymerization rate 20%), 20 parts by weight of copolymer P-1 obtained in Example 1, 2.
A mixture of 10.05 parts by weight of 2'-azobisisobutyronitrile/I and sodium dioctyl sulfosuccinate 4 o, o o s as a mold release agent is shown in Japanese Patent Publication No. 52-30985. A methacrylic resin plate having a thickness of 5111I+ was produced by polymerization using a continuous plate making apparatus such as the above. Polymerization was carried out in a warm water atmosphere at 70°C for 60 minutes, and then in an air atmosphere at 130°C for 15 minutes to complete the polymerization. Example 1 The obtained methacrylic resin cast plate
When evaluated in the same manner as above, the surface resistivity was 5.0×10'Ω
The charge half-life time was 1.7 seconds, the haze value was 4.0%, and the surface resistivity after washing with water was 56×1090.
又、引張弾性係数はl OX 1 o’IKg/crn
”、引張破壊強度は740 kg/cm2、HDTは1
00℃であった。Also, the tensile elastic modulus is l OX 1 o'IKg/crn
”, tensile breaking strength is 740 kg/cm2, HDT is 1
It was 00℃.
実施例16
共重合体P−1の代りにP−3を用いた他は実施例15
と同様にして、板厚3日のメタクリル樹脂キャスト板を
得た。表面抵抗率は2゜5×1010Ω、電荷半減時間
23秒、曇価五〇チであシ、水洗処理後の表面抵抗率は
ZOX1010Ωであった。Example 16 Example 15 except that P-3 was used instead of copolymer P-1
In the same manner as above, a methacrylic resin cast board with a thickness of 3 days was obtained. The surface resistivity was 2°5×1010Ω, the charge half-life time was 23 seconds, the haze value was 50°, and the surface resistivity after washing with water was ZOX1010Ω.
また引張弾性係数は五OX 10’ kg/lyn”、
引張破壊強度は740 kg/cm”であシ、HDTは
100℃であった。In addition, the tensile elastic modulus is 5OX 10'kg/lyn",
The tensile strength at break was 740 kg/cm'', and the HDT was 100°C.
比較例2〜4
実施例1で得だ四級アンモニウム塩基を含む単量体M−
1溶液を用い、表2に示す組成の単量体混合物を加え、
実施例1と同様の手法で重合させて共重合体(P−12
〜14)を得た。Comparative Examples 2 to 4 Monomer M- containing a quaternary ammonium base obtained in Example 1
1 solution, add a monomer mixture with the composition shown in Table 2,
Polymerization was performed in the same manner as in Example 1 to obtain a copolymer (P-12
-14) were obtained.
これらの共重合体をそれぞれ0.5重量部、2.0重量
部、2.0重量部使用して実施例1と同様の手法により
厚さ3露のメタクリル樹脂キャスト板を得た。得られた
キャスト板の性能評価結果を表6に示す。Using 0.5 parts by weight, 2.0 parts by weight, and 2.0 parts by weight of these copolymers, methacrylic resin cast plates having a thickness of 3 mm were obtained in the same manner as in Example 1. Table 6 shows the performance evaluation results of the obtained cast plate.
比較例5
メチルメタクリレート部分重合体(粘度100七ンチポ
イズ、重合率8%)100重量部に、グリセリンモノス
テアレートを5重量部添加混合し、実施例1と同様の手
法によシ、板厚3w11のメタクリル樹脂キャスト板を
得た。このキャスト板の性能、評価結果を表6に示す。Comparative Example 5 5 parts by weight of glycerin monostearate was added and mixed to 100 parts by weight of methyl methacrylate partial polymer (viscosity 1007 inch, polymerization rate 8%), and the same method as in Example 1 was used to prepare a plate with a thickness of 3W11. A methacrylic resin cast plate was obtained. Table 6 shows the performance and evaluation results of this cast board.
比較例6
四級アンモニウム塩基を有する塗布型帯電防止剤(スタ
チサイド、Analytical ChemicalL
aboratories 社製)の1.5チ水溶液に
板厚6■のメタクリル樹脂板(アクリライト、三菱レイ
ヨン製)を1分間浸析し、風乾後、実施例1と同様に評
価した。結果を表6に示す。Comparative Example 6 Coating type antistatic agent having quaternary ammonium base (Staticide, Analytical Chemical L
A methacrylic resin plate (Acrylite, manufactured by Mitsubishi Rayon) with a thickness of 6 cm was immersed in a 1.5 inch aqueous solution of Aboratories Co., Ltd. for 1 minute, and after air drying, it was evaluated in the same manner as in Example 1. The results are shown in Table 6.
本願の発明は、良好且つ恒久的な帯電防止性能を有し、
メタクリル樹脂本来の物性を低下させることのないメタ
クリル樹脂キャスト板及びその製造方法を提供するもの
である。このメタクリ/’ m 脂キャスト板は静電気
によるトラブルがないのでエレクトロニクス関連分野等
の高信頼性を必要とする産業にも使用できる。The invention of the present application has good and permanent antistatic performance,
The object of the present invention is to provide a methacrylic resin cast plate and a method for manufacturing the same without degrading the original physical properties of the methacrylic resin. This metal-acrylic resin cast plate does not cause problems due to static electricity, so it can be used in industries that require high reliability, such as electronics-related fields.
表 2
モノメタクリレートモノメチルエーテルPEG(500
):ポリエチvングリ=ff−fi/(500)モノメ
タクリレートモノメチルエーテルMMA :
メチルメタクリレート1幅
表 4
7’iJ:l,、DEMAニジエチルアミノエチルメタ
クリレートDMMA ニジメチルアミノエチルメタクリ
レートDEA ニジエチルアミノエチルアクリレート
DES ニジエチル硫酸
DMS ニジメチル〃
Ts−OMe:p−トμエンスμホン酸メチルM e
C L :メチルクロライド
手続補正書
1.事件の表示
昭和61年特許願第211158号
2、発明の名称
帯電防止性に優れたメタクリル樹脂キャスト板及びその
製法
3、補正をする者
事件との関係 特許出願人
東京都中央区京橋二丁目3番1g号
(603)三菱レイヨン株式会社
取締役社長 河崎晃夫
4、代理人
5、補正命令の日付
(1)明細書第15頁第16〜17行記載の「(共)重
合体(n)を添加して均一に溶解させ、」を「(共)重
合体(II)を添加して均一に溶解又は懸濁させ、」に
訂正する。Table 2 Monomethacrylate monomethyl ether PEG (500
): polyethylene v nguri = ff-fi/(500) monomethacrylate monomethyl ether MMA:
Methyl methacrylate 1 width table 4 7'iJ: l,, DEMA Ni-diethylaminoethyl methacrylate DMMA Ni-dimethylaminoethyl methacrylate DEA Ni-diethylaminoethyl acrylate DES Ni-diethyl sulfate DMS Nidimethyl〃 Ts-OMe: p-toμene methyl phonate
CL: Methyl chloride procedural amendment 1. Description of the case Patent Application No. 211158 of 1985 2 Name of the invention Methacrylic resin cast plate with excellent antistatic properties and its manufacturing method 3 Person making the amendment Relationship to the case Patent applicant 2-3 Kyobashi, Chuo-ku, Tokyo No. 1g (603) Mitsubishi Rayon Co., Ltd. President Akio Kawasaki 4, Agent 5, Date of amendment order (1) Addition of (co)polymer (n) described on page 15, lines 16-17 of the specification "(co)polymer (II) is added and uniformly dissolved or suspended" is corrected to "(co)polymer (II) is added and uniformly dissolved or suspended").
(2)明細書第19頁第7〜9行記載の「ポリエチレン
グリコール(23)モノメタクリレートモノメチルエー
テル620重量部」を「ポリエチレングリコール(23
)モノメタクリレートモノメチルエーテル[カッコ内は
ポリエヂレングリコールユニットの数1620重量部」
に訂正する。(2) "620 parts by weight of polyethylene glycol (23) monomethacrylate monomethyl ether" described on page 19, lines 7 to 9 of the specification.
) Monomethacrylate monomethyl ether [The number in parentheses is the number of polyethylene glycol units, 1620 parts by weight.”
Correct.
(3)明細書第24頁第4行記載の「比較例2〜袖 含」を「実施例17、比較例2〜3」に訂正する。(3) "Comparative Example 2 - Sleeve" described in page 24, line 4 of the specification "Contains" is corrected to "Example 17, Comparative Examples 2-3".
(4)同第14行記載の「比較例5」を「比較例4」に
訂正する。(4) "Comparative Example 5" written on line 14 is corrected to "Comparative Example 4".
(5)明細書第25頁第1行記載の「比較例6」を「比
較例5」に訂正する。(5) "Comparative Example 6" written in the first line of page 25 of the specification is corrected to "Comparative Example 5."
(6)明細書第27頁記載の表2及び第31頁記載の表
6を別紙の通り訂正する。(6) Table 2 on page 27 of the specification and Table 6 on page 31 are corrected as shown in the attached sheet.
表まTable
Claims (1)
0重量%以上とこれと共重合可能な少なくとも一種の単
量体50重量%以下とからなる(共)重合体100重量
部、と 一般式 ▲数式、化学式、表等があります▼ (R_1は水素原子又はメチル基、R_2〜R_4は水
素原子又は炭素数1〜9の置換基を含んでいてもよいア
ルキル基、mは1〜10、X^−は四級化剤のアニオン
) で表される四級アンモニウム塩基を有する単量体20〜
100重量%とこれと共重合可能な少なくとも一種の単
量体80〜0重量%からなる単量体(混合物)を重合さ
せて得られた(共)重合体(II)0.1〜20重量部か
らなる帯電防止性に優れたメタクリル樹脂キャスト板。 2、メチルメタクリレート又はメチルメタクリレート5
0重量%以上と、共重合可能な少なくとも一種の単量体
50重量%以下とからなる単量体混合物或いは、それら
の部分重合体( I )100重量部に対し、 一般式 ▲数式、化学式、表等があります▼ (R_1は水素原子又はメチル基、R_2〜R_4は水
素原子又は、炭素数1〜9の置換基を含んでいてもよい
アルキル基、mは1〜10、X^−は四級化剤のアニオ
ン) で表される四級アンモニウム塩基を有する単量体20〜
100重量%とこれと共重合可能な少なくとも一種類の
単量体80〜0重量%からなる単量体(混合物)を重合
させて得られた(共)重合体(II)0.1〜20重量部
を混合して重合させることを特徴とする帯電防止性に優
れたメタクリル樹脂キャスト板の製法。 3、四級アンモニウム塩基を有する単量体30〜90重
量%とこれと共重合可能な少なくとも一種の単量体70
〜10重量%からなる単量体混合物を重合させて得られ
た共重合体を使用する特許請求の範囲第2項記載の帯電
防止性に優れたメタクリル樹脂キャスト板の製法。 4、四級アンモニウム塩基を有する単量体と共重合可能
な単量体として、下記一般式 ▲数式、化学式、表等があります▼ (R_5は水素原子又はメチル基、R_6は水素原子又
は炭素数1〜18のアルキル基、アリル基、アリール基
、アラルキル基、Aは炭素数2〜4のアルキレン基、n
は0〜500) で表される化合物より選ばれたものを使用する特許請求
の範囲第2項記載の帯電防止性に優れたメタクリル樹脂
キャスト板の製法。 5、四級アンモニウム塩基のカウンターアニオンが一般
式 R_7SO_3^−又はR_7OSO_3^−(R_7
は水素原子又は炭素数1〜20のフェニル基を含んでい
てもよいアルキル基) で表されるものである特許請求の範囲第2項記載の帯電
防止性に優れたメタクリル樹脂キャスト板の製法。 6、キャスト板を製造する際の重合を、2枚の無機ガラ
ス板又は金属板とガスケットで構成された鋳型内で行な
う特許請求の範囲第2項記載の帯電防止性に優れたメタ
クリル樹脂キャスト板の製法。 7、キャスト板を製造する際の重合を、同一方向に同一
速度で進行する片面鏡面研摩された2枚のステンレス鋼
製エンドレスベルトとガスケットで構成された鋳型内で
連続的に行なう特許請求の範囲第2項記載の帯電防止性
に優れたメタクリル樹脂キャスト板の製法。[Claims] 1. Methyl methacrylate or methyl methacrylate 5
100 parts by weight of a (co)polymer consisting of 0% by weight or more and 50% by weight or less of at least one monomer copolymerizable with the polymer, and the general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (R_1 is hydrogen atom or methyl group, R_2 to R_4 are hydrogen atoms or alkyl groups that may contain substituents having 1 to 9 carbon atoms, m is 1 to 10, X^- is an anion of a quaternizing agent) Monomer 20 having a quaternary ammonium base
(Co)polymer (II) 0.1 to 20% by weight obtained by polymerizing a monomer (mixture) consisting of 100% by weight and 80 to 0% by weight of at least one monomer copolymerizable therewith. A methacrylic resin cast plate with excellent antistatic properties. 2. Methyl methacrylate or methyl methacrylate 5
For 100 parts by weight of a monomer mixture consisting of 0% by weight or more and 50% by weight or less of at least one copolymerizable monomer, or a partial polymer thereof (I), the general formula ▲ mathematical formula, chemical formula, There are tables, etc. ▼ (R_1 is a hydrogen atom or a methyl group, R_2 to R_4 are hydrogen atoms or an alkyl group that may contain a substituent having 1 to 9 carbon atoms, m is 1 to 10, and X^- is a Anion of a grading agent) A monomer having a quaternary ammonium base represented by 20~
(Co)polymer (II) obtained by polymerizing a monomer (mixture) consisting of 100% by weight and 80 to 0% by weight of at least one type of monomer copolymerizable with the monomer (co)polymer (II) 0.1 to 20% A method for producing a methacrylic resin cast plate with excellent antistatic properties, which is characterized by mixing and polymerizing parts by weight. 3. 30 to 90% by weight of a monomer having a quaternary ammonium base and at least one monomer copolymerizable with the monomer 70
A method for producing a methacrylic resin cast plate with excellent antistatic properties according to claim 2, which uses a copolymer obtained by polymerizing a monomer mixture consisting of ~10% by weight. 4. Monomers that can be copolymerized with monomers having a quaternary ammonium base include the following general formula ▲ mathematical formula, chemical formula, table, etc. ▼ (R_5 is a hydrogen atom or a methyl group, R_6 is a hydrogen atom or the number of carbon atoms) 1 to 18 alkyl group, allyl group, aryl group, aralkyl group, A is an alkylene group having 2 to 4 carbon atoms, n
0 to 500) A method for manufacturing a methacrylic resin cast plate having excellent antistatic properties according to claim 2, wherein a compound selected from the following is used. 5. The counter anion of the quaternary ammonium base has the general formula R_7SO_3^- or R_7OSO_3^-(R_7
3. The method for producing a methacrylic resin cast plate having excellent antistatic properties according to claim 2, wherein is a hydrogen atom or an alkyl group which may contain a phenyl group having 1 to 20 carbon atoms. 6. A methacrylic resin cast plate with excellent antistatic properties as set forth in claim 2, wherein polymerization during production of the cast plate is carried out in a mold composed of two inorganic glass plates or metal plates and a gasket. manufacturing method. 7. The claim that the polymerization during production of the cast plate is carried out continuously in a mold consisting of two single-sided mirror-polished stainless steel endless belts and gaskets that proceed in the same direction and at the same speed. 2. A method for producing a methacrylic resin cast plate with excellent antistatic properties as described in item 2.
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP21115886A JPH0798884B2 (en) | 1986-09-08 | 1986-09-08 | Manufacturing method of methacrylic resin cast board with excellent antistatic property |
DE8787112988T DE3784202T2 (en) | 1986-09-08 | 1987-09-04 | MOLDED METHACRYL RESIN PLATE WITH GOOD ANTISTATIC PROPERTIES AND METHOD FOR THE PRODUCTION THEREOF. |
CA000546195A CA1318064C (en) | 1986-09-08 | 1987-09-04 | Methacrylic resin cast plate having excellent antistatic property and process for preparation thereof |
EP87112988A EP0259802B1 (en) | 1986-09-08 | 1987-09-04 | Methacrylic resin cast plate having excellent antistatic property and process for preparation thereof |
KR1019870009857A KR910003737B1 (en) | 1986-09-08 | 1987-09-07 | Methacrylic resin cast plate having excellent antistatic property and process for preparation thereof |
US07/423,596 US5086106A (en) | 1986-09-08 | 1989-10-17 | Methacrylic resin cast plate having excellent antistatic property |
US07/498,547 US5118744A (en) | 1986-09-08 | 1990-03-26 | Process for the preparation of a methacrylic resin cast plate having excellent antistatic property |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP21115886A JPH0798884B2 (en) | 1986-09-08 | 1986-09-08 | Manufacturing method of methacrylic resin cast board with excellent antistatic property |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6366253A true JPS6366253A (en) | 1988-03-24 |
JPH0798884B2 JPH0798884B2 (en) | 1995-10-25 |
Family
ID=16601352
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP21115886A Expired - Lifetime JPH0798884B2 (en) | 1986-09-08 | 1986-09-08 | Manufacturing method of methacrylic resin cast board with excellent antistatic property |
Country Status (1)
Country | Link |
---|---|
JP (1) | JPH0798884B2 (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100677032B1 (en) | 2005-10-10 | 2007-02-01 | 박한표 | Antistatic acryl plate employing antistatic surfactant, and antistatic surfactant composition thereof |
JP2008201068A (en) * | 2007-02-22 | 2008-09-04 | Seiko Epson Corp | Stamping device |
CN111499795A (en) * | 2020-05-07 | 2020-08-07 | 浙江展宇新材料有限公司 | Production process of PMMA monomer copolymerized organic glass |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100758656B1 (en) * | 2006-05-19 | 2007-09-13 | 장학섭 | Flameproof acryl sheet and method preparing same |
-
1986
- 1986-09-08 JP JP21115886A patent/JPH0798884B2/en not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100677032B1 (en) | 2005-10-10 | 2007-02-01 | 박한표 | Antistatic acryl plate employing antistatic surfactant, and antistatic surfactant composition thereof |
JP2008201068A (en) * | 2007-02-22 | 2008-09-04 | Seiko Epson Corp | Stamping device |
CN111499795A (en) * | 2020-05-07 | 2020-08-07 | 浙江展宇新材料有限公司 | Production process of PMMA monomer copolymerized organic glass |
Also Published As
Publication number | Publication date |
---|---|
JPH0798884B2 (en) | 1995-10-25 |
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