JPH0510385B2 - - Google Patents
Info
- Publication number
- JPH0510385B2 JPH0510385B2 JP27408984A JP27408984A JPH0510385B2 JP H0510385 B2 JPH0510385 B2 JP H0510385B2 JP 27408984 A JP27408984 A JP 27408984A JP 27408984 A JP27408984 A JP 27408984A JP H0510385 B2 JPH0510385 B2 JP H0510385B2
- Authority
- JP
- Japan
- Prior art keywords
- weight
- polymer
- methacrylic resin
- copolymer
- methyl methacrylate
- 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 - Lifetime
Links
- 229920000642 polymer Polymers 0.000 claims description 33
- 239000000203 mixture Substances 0.000 claims description 31
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 25
- 229920001577 copolymer Polymers 0.000 claims description 22
- 239000000113 methacrylic resin Substances 0.000 claims description 21
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 13
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 12
- 239000000178 monomer Substances 0.000 claims description 9
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical class CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 150000002430 hydrocarbons Chemical group 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 10
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 9
- 230000003287 optical effect Effects 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000008188 pellet Substances 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000002994 raw material Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 3
- 229920000297 Rayon Polymers 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000012662 bulk polymerization Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000001125 extrusion Methods 0.000 description 2
- 150000003949 imides Chemical group 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 239000006082 mold release agent Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N pentan-1-amine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- 238000005979 thermal decomposition reaction Methods 0.000 description 2
- 229940057054 1,3-dimethylurea Drugs 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- PSFDAYXWBWRTSM-UHFFFAOYSA-N 1-prop-2-enylpyrrole-2,5-dione Chemical compound C=CCN1C(=O)C=CC1=O PSFDAYXWBWRTSM-UHFFFAOYSA-N 0.000 description 1
- YAJYJWXEWKRTPO-UHFFFAOYSA-N 2,3,3,4,4,5-hexamethylhexane-2-thiol Chemical compound CC(C)C(C)(C)C(C)(C)C(C)(C)S YAJYJWXEWKRTPO-UHFFFAOYSA-N 0.000 description 1
- KWVPRPSXBZNOHS-UHFFFAOYSA-N 2,4,6-Trimethylaniline Chemical compound CC1=CC(C)=C(N)C(C)=C1 KWVPRPSXBZNOHS-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- DJXIXKMDAMPUBH-UHFFFAOYSA-N 3-(1-phenylprop-1-en-2-yl)furan-2,5-dione Chemical compound CC(=CC1=CC=CC=C1)/C/1=C/C(=O)OC1=O DJXIXKMDAMPUBH-UHFFFAOYSA-N 0.000 description 1
- 229920005507 ACRYPET® MF Polymers 0.000 description 1
- 229920005509 ACRYPET® VH Polymers 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 229920005497 Acrypet® Polymers 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- WJYIASZWHGOTOU-UHFFFAOYSA-N Heptylamine Chemical compound CCCCCCCN WJYIASZWHGOTOU-UHFFFAOYSA-N 0.000 description 1
- OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-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
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- MGJKQDOBUOMPEZ-UHFFFAOYSA-N N,N'-dimethylurea Chemical compound CNC(=O)NC MGJKQDOBUOMPEZ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N beta-monoglyceryl stearate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- NISGSNTVMOOSJQ-UHFFFAOYSA-N cyclopentanamine Chemical compound NC1CCCC1 NISGSNTVMOOSJQ-UHFFFAOYSA-N 0.000 description 1
- 238000005034 decoration Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 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
- 238000011156 evaluation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 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
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- FJDUDHYHRVPMJZ-UHFFFAOYSA-N nonan-1-amine Chemical compound CCCCCCCCCN FJDUDHYHRVPMJZ-UHFFFAOYSA-N 0.000 description 1
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 1
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 1
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 description 1
- 229940065472 octyl acrylate Drugs 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 229940100684 pentylamine Drugs 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pentâ4âenâ2âone Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920002959 polymer blend Polymers 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229920006027 ternary co-polymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000005341 toughened glass Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 230000002087 whitening effect Effects 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
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[Technical Field of the Invention] The present invention relates to a transparent heat-resistant methacrylic resin composition. [Technical background of the invention and its problems] Methacrylic resin whose main component is methyl methacrylate has excellent optical properties and weather resistance, and is also compared in terms of mechanical properties, thermal properties, moldability, etc. Due to its well-balanced performance, it is widely used in many fields such as signboards, lighting covers, nameplates, automobile parts, electrical equipment parts, decorations, and miscellaneous goods. Development of new uses is also underway. However, on one side, the heat distortion temperature is around 100â,
There are many fields in which the development of applications is restricted due to insufficient heat resistance, and there is a deep-rooted demand for improved heat resistance. Many proposals have already been made for methods of improving the heat resistance of methacrylic resins, such as a method of copolymerizing methyl methacrylate and α-methylstyrene, and a method of copolymerizing methyl methacrylate, α-methylstyrene, and maleic anhydride. (Special Publication No. 49-10156), a method for copolymerizing methyl methacrylate, styrene, and maleic anhydride (Special Publication No. 10156),
56-43242), method for copolymerizing methyl methacrylate, α-methylstyrene, styrene and maleic anhydride (JP-A-56-81322), polyα-
A method in which methyl styrene is dissolved in methyl methacrylate and then methyl methacrylate is polymerized (Tokuko Sho
43-1616, Japanese Patent Publication No. 49-8718), method for copolymerizing methyl methacrylate and N-allylmaleimide (Japanese Patent Publication No. 43-9753), copolymerization of methyl methacrylate, α-methylstyrene, and maleimide. A method of copolymerizing methyl methacrylate in the presence of a crosslinked polymer using a polyfunctional monomer, a method of copolymerizing methacrylic acid with methyl methacrylate, a method of copolymerizing methyl methacrylate, α-methylstyrene, and acrylonitrile. Polymerization methods have been proposed. However, since the polymerization rate of the above proposed method is extremely low, productivity is extremely low and it is not practical, mechanical properties, weather resistance, and optical properties are decreased, and the molded product is significantly colored. In either case, the heat resistance is improved to some extent, but the molding area is narrow and the molding processability is poor.
At present, many problems remain before it can be put into practical use. [Objective of the Invention] The object of the present invention is to solve the above-mentioned problems, which reduce the inherent excellent properties of methacrylic resin such as optical properties, mechanical properties, weather resistance, moldability, and productivity. It is an object of the present invention to provide a heat-resistant methacrylic resin composition that is free from heat and has excellent transparency. [Summary of the Invention] In view of the current situation, the present inventors have developed a transparent resin without deteriorating its inherent excellent optical properties, mechanical properties, weather resistance, moldability, productivity, etc. As a result of intensive research into heat-resistant methacrylic resin with excellent properties, we have developed methyl methacrylate-α- with a specific composition.
It was discovered that a resin mixture of a copolymer having a methyl styrene-maleic anhydride ternary copolymer structure and a polymer containing a methacrylimide ring structural unit can achieve the object, and in completing the present invention. It has been reached. That is, the heat-resistant methacrylic resin composition of the present invention consists of (A) 50-98% by weight of methyl methacrylate, (B) 1-25% by weight of Bα-methylstyrene, and (C) 1-25% by weight of maleic anhydride. Copolymer (I) obtained by polymerizing the mixture 1 to 99% by weight and general formula: (In the formula, R represents a hydrogen atom, an aliphatic group having 1 to 10 carbon atoms, or a hydrocarbon group having 5 to 10 carbon atoms including an alicyclic group or an aromatic group) It is characterized by consisting of 1 to 99% by weight of a polymer () containing 2% by weight or more of units. Methyl methacrylate (A) used to constitute the copolymer () in the composition of the present invention is:
This component maintains the original optical properties, weather resistance, or mechanical properties of the methacrylic resin and improves its compatibility with the polymer containing methacrylimide ring structural units. If the proportion of (A) in parentheses is less than 50% by weight, the above properties will be lost, and if it exceeds 98% by weight, no improvement in heat resistance can be expected. The preferred ratio is 60
~80% by weight. In addition, α-methylstyrene (B), which is a constituent component of the copolymer (), is a component that directly improves heat resistance. It is a component that indirectly improves heat resistance by increasing . If the proportion of (B) in parentheses is less than 1% by weight, productivity and heat resistance will be poor; if it exceeds 25% by weight, mechanical properties and optical properties will deteriorate, and boiling resistance will tend to deteriorate. show. The preferred ratio is 5-15
Weight%. Furthermore, maleic anhydride (C), which is a component of the copolymer (), is a copolymerized α-
A component that improves the heat resistance of the copolymer through interaction with methylstyrene. If the proportion of (C) in parentheses is less than 1% by weight, productivity and heat resistance will be poor; if it exceeds 25% by weight, mechanical properties will deteriorate and boiling resistance will further deteriorate. The preferred ratio is 5-25
Weight%. In the composition of the present invention, considering the overall balance of resin properties such as heat resistance, mechanical properties, optical properties, and moldability of the blended resin finally obtained, α in the copolymer () - When the number of moles of the structural unit derived from methylstyrene is α and the number of moles of the structural unit derived from maleic anhydride is β, it is most preferable that α/β is 0.9 to 1.7. When α/β is less than 0.9, water resistance and mechanical properties tend to decrease, and when it exceeds 1.7, optical properties and heat resistance tend to decrease. Second polymer () constituting the composition of the present invention
is for imparting the inherent heat resistance of methacrylimide resin. In other words, when placing emphasis on heat resistance, it is sufficient to increase the methacrylimide ring structural unit in the polymer (); when placing importance on mechanical properties, the methacrylimide ring structural unit may be reduced and other It is preferable to increase the number of structural units (for example, structural units derived from methyl methacrylate). In the above methacrylimide ring structural unit, examples of the aliphatic group having 1 to 10 carbon atoms represented by R include methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine,
Examples include linear and branched types such as heptylamine, octylamine, nonylamine, and decylamine. Examples of hydrocarbon groups having 5 to 10 carbon atoms containing alicyclic groups or aromatic groups include cyclopentylamine, cyclohexylamine, aniline, orthotoluidine, metatoluidine, paratoluidine, 2,4,6-trimethylaniline, and paratoluidine. Examples include ethylaniline. The proportion of methacrylimide ring structural units in the polymer () is
It is usually 2% by weight or more, preferably 10% by weight or more. If this proportion is less than 2% by weight, sufficient heat resistance cannot be expected. The weight average molecular weight of the polymer () is usually 40,000 to 500,000, preferably 40,000 to 100,000.
Ten thousand. If the molecular weight is less than 40,000, the mechanical strength will be poor, and if it exceeds 500,000, the moldability will be poor. Further, the degree of polymerization is usually 200 to 3000, preferably 400 to 2000. There are no particular restrictions on the method for producing the polymer () containing a methacrylimide ring structure component, but
A method of subjecting a methacrylic resin polymer to a thermal decomposition bonding reaction using at least one imidizing agent selected from the group consisting of ammonia, an ammonia generator, a primary amine, and a primary amine generator (for example,
US Patent No. 2146209, West German Patent No. 1077872,
No. 1242369). Polymer of methacrylimide ring structural unit with excellent transparency ()
To obtain the above, the above imidizing agent is introduced into a homogeneous solution system in which the raw material methacrylic resin is dissolved in a non-polymerizable solvent to cause a thermal decomposition condensation reaction, and then volatile substances are separated from the resulting reaction product. It is preferable to remove it. The raw material methacrylic resin is a copolymer containing a methacrylic acid derivative capable of forming a methacrylimide ring structural unit obtained by reacting with the imidizing agent. Examples of methacrylic acid derivatives include:
Methacrylic acid, methyl methacrylate, ethyl methacrylate, butyl methacrylate, methacrylic acid
Tert-butyl, hexyl methacrylate, octyl methacrylate, dodecyl methacrylate, etc. are used. Among these, methyl methacrylate is preferred. Examples of copolymerizable components include vinyl monomers that can be copolymerized with methacrylic acid derivatives.
For example, styrene derivatives such as styrene, vinyltoluene, α-methylstyrene, chlorostyrene; acrylic acid, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, hexyl acrylate, octyl acrylate,
Examples include acrylic acid derivatives such as dodecyl acrylate. Among these, styrene is preferred. Examples of the imidizing agent for forming the methacrylimide ring structural unit include ammonia, methylamine, butylamine, urea, and 1,3 dimethylurea. Among these, methylamine is preferred from the viewpoint of heat resistance. The non-polymerizable solvent may be any non-polymerizable solvent that can dissolve the raw material methacrylic resin and the product methacrylic imide ring structure component-containing polymer, such as benzene, methanol, a mixed solvent of tolumene/methanol, or a mixed solvent of xylene/methanol. Solvents etc. are used. The polymer () is usually 5000 ppm or less, preferably 5000 ppm or less, in order to prevent oxidative deterioration of the polymer.
Under an oxygen concentration atmosphere of 1000ppm or less, usually 150~
Produced at a temperature of 350°C, preferably 170-250°C. In addition, in order to prevent hydrolysis of the side chains of the polymer, it is usually 5000 ppm or less, preferably 1000 ppm or less.
Produced under anhydrous atmosphere: The composition of the present invention has a flow rate (FR) of 0.5 to 75 (according to ASTM D-1238 at 230°C, 10
It is particularly useful as a molding material using a 10 minute extrusion rate (g) under a load of Kg/ cm2 . The blending ratio of the methacrylic resin composition of the present invention is
In the composition, the amount of the copolymer () is usually 1 to 99% by weight, preferably 5 to 95% by weight. If this proportion is less than 1% by weight, heat resistance will be poor, and if it exceeds 99% by weight, no improvement in mechanical properties can be expected. There are no particular limitations on the method for producing the composition of the present invention, but for example, the copolymer () is produced by bulk polymerization, suspension polymerization, etc. in accordance with a conventional method, and the resulting copolymer () and polymer After mixing with coalescence (),
A method of producing a blended resin by melting, kneading, and extruding at a temperature of 200 to 300°C, and after dissolving the polymer in the monomer mixture used to produce the polymer, it contains a suspending and dispersing agent. Suspension polymerization or bulk polymerization in an aqueous medium can be employed. Additives such as ultraviolet absorbers, release agents, antioxidants, mold release agents, dyes and pigments may be added to the composition of the present invention, if necessary. EXAMPLES The present invention will be explained in more detail with reference to Examples and Comparative Examples below. [Examples of the Invention] Example 1, Comparative Examples 1 to 3 To 1000 g of a monomer mixture containing methyl methacrylate, α-methylstyrene, and maleic anhydride in the proportions shown in Table 1, t was added as a molecular weight regulator. - 2.5 g of dodecyl mercaptan were added and the mixture was placed in a separable flask of internal volume 2 equipped with a condenser, thermometer and stirring bar. Next, while stirring, nitrogen gas was blown in to drive out the air in the system, and then heated and when the temperature inside the flask reached 70°C, 0.2 g of 2,2'-azobis-(2,4-dimethylvaleronitrile) was added. and internal temperature 95
The mixture was kept at â for 15 minutes and cooled to room temperature to obtain a syrup-like partial polymer. For 1000 g of this partial polymer, 4 g of lauroyl peroxide, 3.0 g of t-dodecyl mercaptan as a molecular weight regulator, and ``tinuvin'' as an ultraviolet absorber.
Pâ (trade name, manufactured by Ciba Geigy) 0.3g, âJP-504â (trade name, manufactured by Johoku Kagaku Co., Ltd.) as a release agent 0.2
g, 1 g of "MarK 329" (trade name, manufactured by Adeka Argus Co., Ltd.) as a stabilizer, and 1 g of stearic acid monoglyceride as a mold release agent were added, and the mixture was sufficiently stirred to dissolve. This partial polymer mixture was injected through a polyvinyl chloride gasket into a mold consisting of a thermocouple set in a cell formed by two tempered glass plates spaced 3 mm apart, and heated to 80°C water. It was polymerized and cured inside. After 30 minutes had elapsed from the time the mold was immersed in the hot water until the internal temperature reached its peak, the mold was taken out of the hot water and heat treated in an air heating furnace at 130°C for 2 hours. After cooling, the glass plate was removed to obtain a resin plate with a thickness of approximately 3 mm. This plate was cut and crushed into pellets of about 3 to 4 mm.
A copolymer () was thus obtained.
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60ïŒ40ã®éåå²åã§æ··åããåŸãæŒåºæ©ãçšããŠ
200ã270âã§è³Šåœ¢ãããã¬ããåïŒæŒåºæž©åºŠ270
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ããè©ŠéšçïŒ110mmÃ110mmÃïŒmmåïŒããè¡šïŒã®
è©äŸ¡çµæãåŸãã
å°åºæ圢æ©ïŒ(æ ª)æ¥æ¬è£œéŒæ補ãâ17â65åã¹ã¯
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å§700KgïŒcm2éå枩床50â[Table] 1000 g of sufficiently dried raw material methacrylic resin polymer (manufactured by Mitsubishi Rayon Co., Ltd., trade name: AcryPets VH) and dry toluene were placed in the oaklave in Step 5.
1000g was charged and dissolved with stirring. The resulting mixture was added to 387.5 g of a solution of 40% concentration by dissolving methylamine gas in dry methanol, heated, dissolved and stirred, and then dissolved in methacrylic acid at 230°C for 3 hours at a pressure of 50 kg/ cm2 . An imide ring formation reaction was performed.
The resulting clear syrup solution was placed in a hot air dryer.
After drying at 120° C. for one day and night to remove the solvent, the pellets were cut and ground into pellets of about 3 to 4 mm. N-methylmethacrylimide ring formation was determined by nuclear magnetic resonance absorption spectroscopy (FX-90-Q, manufactured by JEOL Ltd.,
The results were confirmed by the absorption at 2.95 ppm (ÎŽ value). Based on the area ratio, the N-methylmethacrylimidation rate was 60%. When this is heated and molded to create a test piece, it becomes a transparent test piece, and the practical heat resistance temperature (heat distortion temperature) (HDT) is
It was 125â. In this way, an N-methylmethacrylimide ring structure-containing polymer () was obtained. The above copolymer () and the above polymer ()
After mixing at a polymerization ratio of 60/40, using an extruder
Shape at 200-270â and pelletize (extrusion temperature 270â)
â). This pellet was injection molded under the following conditions, and the evaluation results shown in Table 2 were obtained from the resulting test piece (110 mm x 110 mm x 2 mm thickness). Injection molding machine: V-17-65 screw type automatic injection molding machine manufactured by Japan Steel Works, Ltd. Injection molding conditions: Cylinder temperature 250-260â, injection pressure 700Kg/cm 2 Mold temperature 50â
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žã¡ãã«ãαâã¡ãã«ã¹ãã¬ã³åã³
ç¡æ°Žãã¬ã€ã³é
žã®é
åçµæãMMAïŒÎ±â
MeStïŒMAHïŒ750ïŒ140ïŒ110ïŒééæ¯ïŒãšããŠ
åŸãããéåäœïŒïŒãšãå®æœäŸïŒã§äœ¿çšãã
âã¡ãã«ã¡ã¿ã¯ãªã«ã€ããç°æ§é å«æéåäœ
ïŒïŒãšãééæ¯80ïŒ20ã®æ··åå²åã«å€æŽãã以
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瀺ãã[Table] Example 2 The composition of methyl methacrylate, α-methylstyrene, and maleic anhydride was changed to MMA/α-
The polymer () obtained as MeSt/MAH=750/140/110 (weight ratio) and the N used in Example 1
A resin composition of the present invention was prepared by repeating the experiment in the same manner as in Example 1, except that the weight ratio of the methyl methacrylimide ring structure-containing polymer () was changed to 80/20. The results obtained are shown in Table 3.
ãè¡šããtableã
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ã§ããåéäœæ··åç©1000ïœãçšããŠéåäœïŒïŒ
ãå®æœäŸïŒãšåæ§ã«è£œé ããïŒmmåã®æ¿ãåŸãã
ãã®æ¿ãåæãç²ç ããåŸæŒåºæ©ã§è³Šåœ¢ããã¬ã
ãåãããâã¡ãã«ã¡ã¿ã¯ãªã«ã€ããç°å«æé
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çµæãè¡šïŒã«ç€ºãã[Table] Visually judge the degree of whitening.
Comparative Examples 4 to 6 Polymer () was prepared using 1000 g of a monomer mixture containing methyl methacrylate, α-methylstyrene, and maleic anhydride in the proportions shown in Table 4.
was produced in the same manner as in Example 1 to obtain a 6 mm thick plate.
This plate was cut and crushed, and then shaped into pellets using an extruder. The pellets alone were injection molded in the same manner as in Example 1 without blending the N-methylmethacrylimide ring-containing polymer (2), and the physical properties of the obtained test pieces were evaluated. The results are shown in Table 5.
ãè¡šããtableã
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å®æœäŸïŒãïŒãæ¯èŒäŸïŒãïŒ
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ãå転æ°250rpmã枩床260âã§è³Šåœ¢ããã¬ãããš
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çµæãè¡šïŒã«ç€ºãã[Table] Examples 3 to 5, Comparative Examples 7 and 8 A monomer mixture consisting of 560 g of methyl methacrylate, 240 g of α-methylstyrene, and 200 g of maleic anhydride was polymerized in the same manner as in Example 1, and a thickness of 3
A plate-like copolymer of mm was obtained. Cutting this copolymer,
After pulverization, the mixture was mixed with the methylmethacrylimide ring-containing polymer of Example 1 in the proportions shown in Table 6, and shaped into pellets using a twin-screw extruder at a rotation speed of 250 rpm and a temperature of 260°C. A test piece obtained by injection molding in the same manner as in Example 1 was evaluated. The results are shown in Table 7.
ãè¡šããtableã
ãè¡šããtableã
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å®æœäŸïŒãïŒãæ¯èŒäŸïŒã14
å®æœäŸïŒãšåæ§ã«ããŠå
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ããã¡ã¿ã¯ãªã«ã€ããå«æéåäœïŒïŒã¯ãå®æœ
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ã¡ãã«ã¢ãã³ä»èŸŒã¿ãå€ããŠåçš®ã¡ã¿ã¯ãªã«ã€ã
ãåçãå€åãããŠè£œé ãããåæã¡ã¿ã¯ãªã«æš¹
èéåäœã¯ããªã¡ãã«ã¡ã¿ã¯ãªã¬ãŒãïŒäžè±ã¬ã€
ãšã³(æ ª)補ãåååïŒã¢ã¯ãªãããVHïŒãã¡ãã«
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±éåäœïŒãã€ã»ã«(æ ª)
補ãåååïŒã»ãã¢ã³MAS30ïŒåã³ã¡ãã«ã¡ã¿
ã¯ãªã¬ãŒãã»ã¡ãã«ã¢ã¯ãªã¬ãŒãå
±éåäœïŒäžè±
ã¬ã€ãšã³(æ ª)補ãã¢ã¯ãªãããMFïŒã䜿çšããã
åæã¡ã¿ã¯ãªã«æš¹èéåäœãšããŠããªã¡ãã«ã¡ã¿
ã¯ãªã¬ãŒãæš¹èéåäœãã¡ãã«ã¡ã¿ã¯ãªã¬ãŒãâ
ã¹ãã¬ã³å
±éåäœãã¡ãã«ã¡ã¿ã¯ãªã¬ãŒãâã¡ã
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è©äŸ¡ãããçµæãè¡šïŒã«ç€ºãã[Table] Examples 6 to 9, Comparative Examples 9 to 14 Copolymers () were produced in the same manner as in Example 1. The methacrylimide-containing polymer (2) was produced in the same manner as in Example (2), but by changing the methylamine charge and varying the methacrylimidation rate as shown in Table 8. The raw material methacrylic resin polymers are polymethyl methacrylate (manufactured by Mitsubishi Rayon Co., Ltd., product name: Acrypet VH), methyl methacrylate-styrene copolymer (manufactured by Daicel Corporation)
(trade name: Sebian MAS30) and a methyl methacrylate/methyl acrylate copolymer (Acrypet MF, manufactured by Mitsubishi Rayon Co., Ltd.) were used.
Polymethyl methacrylate resin polymer, methyl methacrylate as raw material methacrylic resin polymer
A styrene copolymer and a methyl methacrylate-methyl acrylate copolymer were formed as they were and comparatively evaluated. The results are shown in Table 9.
ãè¡šããtableã
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çºæã®å¹æ
以äžã«è©³è¿°ããéããæ¬çºæã®ã¡ã¿ã¯ãªã«æš¹è
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質ãæ©æ¢°çæ§è³ªãèåæ§ãæ圢å å·¥æ§ãçç£æ§ãª
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倧ã§ããã[Table] [Effects of the Invention] As detailed above, the methacrylic resin composition of the present invention has excellent optical properties, mechanical properties, weather resistance, moldability, productivity, etc. inherent to methacrylic resin. It has good transparency and heat resistance while retaining its properties, and its industrial value is extremely large.
Claims (1)
ïŒã99ééïŒ äžŠã³ã« äžè¬åŒïŒ ïŒåŒäžãã¯æ°ŽçŽ ååãççŽ ååæ°ïŒã10ã®èèª
æåºãåã¯èç°æåºãããã¯è³éŠæåºãå«ãççŽ
æ°ïŒã10ã®çåæ°ŽçŽ åºãè¡šããïŒ ã§ç€ºãããã¡ã¿ã¯ãªã«ã€ããç°æ§é åäœãïŒéé
ïŒ ä»¥äžå«æããéåäœïŒïŒïŒã99ééïŒ ããæ
ãããšãç¹åŸŽãšããèç±æ§ã¡ã¿ã¯ãªã«æš¹èçµæ
ç©ã ïŒ å ±éåäœïŒïŒ©ïŒãæ§æããαâã¡ãã«ã¹ãã¬
ã³ç±æ¥ã®æ§é åäœã®ã¢ã«æ°ãαãç¡æ°Žãã€ã¬ã³é ž
ç±æ¥ã®æ§é åäœã®ã¢ã«æ°ãβãšãããšãαïŒÎ²ã
0.9ã1.7ã§ããç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®èç±
æ§ã¡ã¿ã¯ãªã«æš¹èçµæç©ã ïŒ éåäœïŒïŒããã¡ã¿ã¯ãªã«ã€ããç°æ§é å
äœïŒééïŒ ä»¥äžãšããã«åéäœåã¯ããã«åéäœ
ã®æ··åç©ã«ç±æ¥ããæ§é å98ééïŒ æªæºãšãããª
ãç¹èš±è«æ±ã®ç¯å²ç¬¬ïŒé èšèŒã®èç±æ§ã¡ã¿ã¯ãªã«
æš¹èçµæç©ã ïŒ ããã«åéäœããã¡ã¿ã¯ãªã«é žèªå°äœãã¹ã
ã¬ã³èªå°äœåã³ã¢ã¯ãªã«é žèªå°äœãããªã矀ãã
éžã°ããå°ãªããšãïŒçš®ã®ãã®ã§ããç¹èš±è«æ±ã®
ç¯å²ç¬¬ïŒé èšèŒã®èç±æ§ã¡ã¿ã¯ãªã«æš¹èçµæç©ã[Claims] 1. Obtained by polymerizing a mixture consisting of (A) 50-98% by weight of methyl methacrylate, (B) 1-25% by weight of α-methylstyrene, and (C) 1-25% by weight of maleic anhydride. Copolymer (I) I
1-99% by weight and general formula: (In the formula, R represents a hydrogen atom, an aliphatic group having 1 to 10 carbon atoms, or a hydrocarbon group having 5 to 10 carbon atoms including an alicyclic group or an aromatic group) A heat-resistant methacrylic resin composition comprising 1 to 99% by weight of a polymer () containing 2% by weight or more of units. 2 When α is the number of moles of the structural unit derived from α-methylstyrene constituting the copolymer (I) and β is the number of moles of the structural unit derived from maleic anhydride, α/β is
The heat-resistant methacrylic resin composition according to claim 1, which has a molecular weight of 0.9 to 1.7. 3. The heat resistance according to claim 1, wherein the polymer () comprises 2% by weight or more of methacrylimide ring structural units and less than 98% by weight of structural units derived from vinyl monomers or mixtures of vinyl monomers. methacrylic resin composition. 4. The heat-resistant methacrylic resin composition according to claim 3, wherein the vinyl monomer is at least one selected from the group consisting of methacrylic acid derivatives, styrene derivatives, and acrylic acid derivatives.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP27408984A JPS61152758A (en) | 1984-12-27 | 1984-12-27 | Heat-resistant methacrylic resin composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP27408984A JPS61152758A (en) | 1984-12-27 | 1984-12-27 | Heat-resistant methacrylic resin composition |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS61152758A JPS61152758A (en) | 1986-07-11 |
JPH0510385B2 true JPH0510385B2 (en) | 1993-02-09 |
Family
ID=17536824
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP27408984A Granted JPS61152758A (en) | 1984-12-27 | 1984-12-27 | Heat-resistant methacrylic resin composition |
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JP (1) | JPS61152758A (en) |
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JPS63117121A (en) * | 1986-11-05 | 1988-05-21 | Honda Motor Co Ltd | Controlling method for composite intake system of internal combustion engine |
JP2001270905A (en) * | 2000-01-21 | 2001-10-02 | Mitsubishi Rayon Co Ltd | Heat-resistant methacrylic copolymer, manufacturing method therefor and optical element therefrom |
JPWO2021125292A1 (en) * | 2019-12-20 | 2021-06-24 | ||
WO2021193521A1 (en) * | 2020-03-24 | 2021-09-30 | æ ªåŒäŒç€Ÿã¯ã©ã¬ | Methacrylic copolymer, composition, shaped object, method for producing film or sheet, and layered product |
-
1984
- 1984-12-27 JP JP27408984A patent/JPS61152758A/en active Granted
Also Published As
Publication number | Publication date |
---|---|
JPS61152758A (en) | 1986-07-11 |
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