GB1571014A - Graft copolymer and process for producing the same - Google Patents
Graft copolymer and process for producing the same Download PDFInfo
- Publication number
- GB1571014A GB1571014A GB4905/77A GB490577A GB1571014A GB 1571014 A GB1571014 A GB 1571014A GB 4905/77 A GB4905/77 A GB 4905/77A GB 490577 A GB490577 A GB 490577A GB 1571014 A GB1571014 A GB 1571014A
- Authority
- GB
- United Kingdom
- Prior art keywords
- styrene
- weight
- graft copolymer
- polyphenylene ether
- copolymer according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920000578 graft copolymer Polymers 0.000 title claims description 52
- 238000000034 method Methods 0.000 title claims description 37
- 230000008569 process Effects 0.000 title description 27
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 192
- 229920000642 polymer Polymers 0.000 claims description 87
- 229920001955 polyphenylene ether Polymers 0.000 claims description 76
- 239000000203 mixture Substances 0.000 claims description 58
- 239000004793 Polystyrene Substances 0.000 claims description 45
- 229920002223 polystyrene Polymers 0.000 claims description 45
- -1 2,6-disubstituted phenol units Chemical group 0.000 claims description 33
- 229920001577 copolymer Polymers 0.000 claims description 31
- 239000003999 initiator Substances 0.000 claims description 22
- 229920001519 homopolymer Polymers 0.000 claims description 19
- 238000010559 graft polymerization reaction Methods 0.000 claims description 18
- 238000006116 polymerization reaction Methods 0.000 claims description 16
- 150000001875 compounds Chemical class 0.000 claims description 14
- 239000000178 monomer Substances 0.000 claims description 12
- 239000002245 particle Substances 0.000 claims description 11
- 238000004898 kneading Methods 0.000 claims description 10
- 238000002844 melting Methods 0.000 claims description 10
- 230000008018 melting Effects 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 10
- 238000010008 shearing Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- 238000011065 in-situ storage Methods 0.000 claims description 5
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 229920007962 Styrene Methyl Methacrylate Polymers 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- ADFPJHOAARPYLP-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;styrene Chemical compound COC(=O)C(C)=C.C=CC1=CC=CC=C1 ADFPJHOAARPYLP-UHFFFAOYSA-N 0.000 claims description 4
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 3
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 3
- 229920001169 thermoplastic Polymers 0.000 claims description 3
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 claims description 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 claims description 2
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 2
- 238000001125 extrusion Methods 0.000 claims description 2
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 2
- 239000004416 thermosoftening plastic Substances 0.000 claims description 2
- GVLZQVREHWQBJN-UHFFFAOYSA-N 3,5-dimethyl-7-oxabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound CC1=C(O2)C(C)=CC2=C1 GVLZQVREHWQBJN-UHFFFAOYSA-N 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 239000007795 chemical reaction product Substances 0.000 description 30
- 239000002244 precipitate Substances 0.000 description 26
- 238000006243 chemical reaction Methods 0.000 description 21
- 230000000052 comparative effect Effects 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 150000003254 radicals Chemical class 0.000 description 20
- 239000000047 product Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 12
- 238000002156 mixing Methods 0.000 description 11
- 229920005989 resin Polymers 0.000 description 11
- 239000011347 resin Substances 0.000 description 11
- 239000011342 resin composition Substances 0.000 description 8
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 6
- 238000005194 fractionation Methods 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- QQOMQLYQAXGHSU-UHFFFAOYSA-N 2,3,6-Trimethylphenol Chemical compound CC1=CC=C(C)C(O)=C1C QQOMQLYQAXGHSU-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 4
- 229920000265 Polyparaphenylene Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 229920000058 polyacrylate Polymers 0.000 description 3
- 238000007348 radical reaction Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- 229920005992 thermoplastic resin Polymers 0.000 description 3
- KUFFULVDNCHOFZ-UHFFFAOYSA-N 2,4-xylenol Chemical compound CC1=CC=C(O)C(C)=C1 KUFFULVDNCHOFZ-UHFFFAOYSA-N 0.000 description 2
- DMWVYCCGCQPJEA-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhexane Chemical compound CC(C)(C)OOC(C)(C)CCC(C)(C)OOC(C)(C)C DMWVYCCGCQPJEA-UHFFFAOYSA-N 0.000 description 2
- JDCCCHBBXRQRGU-UHFFFAOYSA-N 5-phenylpenta-2,4-dienenitrile Chemical class N#CC=CC=CC1=CC=CC=C1 JDCCCHBBXRQRGU-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920000800 acrylic rubber Polymers 0.000 description 2
- 150000001491 aromatic compounds Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000006229 carbon black Substances 0.000 description 2
- 239000004917 carbon fiber Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000001033 ether group Chemical group 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000003063 flame retardant Substances 0.000 description 2
- 239000003365 glass fiber Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- OXYKVVLTXXXVRT-UHFFFAOYSA-N (4-chlorobenzoyl) 4-chlorobenzenecarboperoxoate Chemical compound C1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1 OXYKVVLTXXXVRT-UHFFFAOYSA-N 0.000 description 1
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 1
- ODBCKCWTWALFKM-UHFFFAOYSA-N 2,5-bis(tert-butylperoxy)-2,5-dimethylhex-3-yne Chemical compound CC(C)(C)OOC(C)(C)C#CC(C)(C)OOC(C)(C)C ODBCKCWTWALFKM-UHFFFAOYSA-N 0.000 description 1
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- KNDAEDDIIQYRHY-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-3-(piperazin-1-ylmethyl)pyrazol-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)CN1CCNCC1 KNDAEDDIIQYRHY-UHFFFAOYSA-N 0.000 description 1
- BIISIZOQPWZPPS-UHFFFAOYSA-N 2-tert-butylperoxypropan-2-ylbenzene Chemical compound CC(C)(C)OOC(C)(C)C1=CC=CC=C1 BIISIZOQPWZPPS-UHFFFAOYSA-N 0.000 description 1
- CSKRBHOAJUMOKJ-UHFFFAOYSA-N 3,4-diacetylhexane-2,5-dione Chemical compound CC(=O)C(C(C)=O)C(C(C)=O)C(C)=O CSKRBHOAJUMOKJ-UHFFFAOYSA-N 0.000 description 1
- KFGFVPMRLOQXNB-UHFFFAOYSA-N 3,5,5-trimethylhexanoyl 3,5,5-trimethylhexaneperoxoate Chemical compound CC(C)(C)CC(C)CC(=O)OOC(=O)CC(C)CC(C)(C)C KFGFVPMRLOQXNB-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- MNVMYTVDDOXZLS-UHFFFAOYSA-N 4-methoxyguaiacol Natural products COC1=CC=C(O)C(OC)=C1 MNVMYTVDDOXZLS-UHFFFAOYSA-N 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021595 Copper(I) iodide Inorganic materials 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical group CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000006399 behavior Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 229920003244 diene elastomer Polymers 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- QZYRMODBFHTNHF-UHFFFAOYSA-N ditert-butyl benzene-1,2-dicarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)OOC(C)(C)C QZYRMODBFHTNHF-UHFFFAOYSA-N 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 229920005680 ethylene-methyl methacrylate copolymer Polymers 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000011953 free-radical catalyst Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- DEAKWVKQKRNPHF-UHFFFAOYSA-N methyl 2-methylprop-2-enoate;prop-2-enenitrile;styrene Chemical compound C=CC#N.COC(=O)C(C)=C.C=CC1=CC=CC=C1 DEAKWVKQKRNPHF-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000012778 molding material Substances 0.000 description 1
- LAIZPRYFQUWUBN-UHFFFAOYSA-L nickel chloride hexahydrate Chemical compound O.O.O.O.O.O.[Cl-].[Cl-].[Ni+2] LAIZPRYFQUWUBN-UHFFFAOYSA-L 0.000 description 1
- SRSFOMHQIATOFV-UHFFFAOYSA-N octanoyl octaneperoxoate Chemical compound CCCCCCCC(=O)OOC(=O)CCCCCCC SRSFOMHQIATOFV-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- SCUZVMOVTVSBLE-UHFFFAOYSA-N prop-2-enenitrile;styrene Chemical compound C=CC#N.C=CC1=CC=CC=C1 SCUZVMOVTVSBLE-UHFFFAOYSA-N 0.000 description 1
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000005060 rubber Substances 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000010183 spectrum analysis Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229920000638 styrene acrylonitrile Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F257/00—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00
- C08F257/02—Macromolecular compounds obtained by polymerising monomers on to polymers of aromatic monomers as defined in group C08F12/00 on to polymers of styrene or alkyl-substituted styrenes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
- C08F283/08—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals on to polyphenylene oxides
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP51059053A JPS5931534B2 (ja) | 1976-05-24 | 1976-05-24 | グラフト共重合体の製造方法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1571014A true GB1571014A (en) | 1980-07-09 |
Family
ID=13102187
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4905/77A Expired GB1571014A (en) | 1976-05-24 | 1977-02-07 | Graft copolymer and process for producing the same |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4097556A (enExample) |
| JP (1) | JPS5931534B2 (enExample) |
| CA (1) | CA1068847A (enExample) |
| DE (1) | DE2705656C3 (enExample) |
| FR (1) | FR2352844A1 (enExample) |
| GB (1) | GB1571014A (enExample) |
| NL (1) | NL162095C (enExample) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55112260A (en) * | 1979-02-23 | 1980-08-29 | Sumitomo Chem Co Ltd | Manufacture of graft copolymer |
| JPS55118945A (en) * | 1979-03-08 | 1980-09-12 | Sumitomo Chem Co Ltd | Preparation of graft copolymer |
| JPS55145752A (en) * | 1979-05-01 | 1980-11-13 | Asahi Chem Ind Co Ltd | Aromatic polyether resin composition |
| US4341879A (en) * | 1980-03-17 | 1982-07-27 | Mitsubishi Gas Chemical Company, Inc. | Polyphenylene ether resin composition having improved heat stability and impact strength |
| JPS5915352B2 (ja) * | 1980-09-16 | 1984-04-09 | 旭化成株式会社 | 射出成形用樹脂組成物 |
| JPS5959724A (ja) * | 1982-09-29 | 1984-04-05 | Unitika Ltd | 熱可塑性樹脂変性体の製造方法 |
| JPS5986653A (ja) * | 1982-11-08 | 1984-05-18 | Unitika Ltd | 樹脂組成物 |
| US5719233A (en) * | 1984-05-21 | 1998-02-17 | General Electric Company | Modified polyphenylene ether-polyamide compositions and process |
| DE3540118A1 (de) * | 1985-11-13 | 1987-05-14 | Basf Ag | Modifizierte polyphenylenetherharze mit carboxylgruppen |
| US4654405A (en) * | 1985-12-05 | 1987-03-31 | Borg-Warner Chemicals, Inc. | Carboxylated phenylene ether resins |
| US4923924A (en) * | 1985-12-06 | 1990-05-08 | Borg-Warner Chemicals, Inc. | Thermoplastic impact modified polyamide-polyphenylene ether composition |
| JPS62138552A (ja) * | 1985-12-12 | 1987-06-22 | Sumitomo Chem Co Ltd | 熱可塑性樹脂組成物 |
| DE3711620A1 (de) * | 1987-04-07 | 1988-10-27 | Basf Ag | Thermoplastische formmassen auf basis von polyphenylenether |
| DE3722502A1 (de) * | 1987-07-08 | 1989-01-19 | Basf Ag | Thermoplastische formmassen |
| US4814393A (en) * | 1987-10-26 | 1989-03-21 | General Electric Company | Composition of graft modified polyphenylene ether and polycarbonate |
| US5191031A (en) * | 1987-12-02 | 1993-03-02 | Asahi Kasei Kogyo Kabushiki Kaisha | Thermoplastic resin polymer having improved moldability and heat resistance and composition |
| DE3831348A1 (de) * | 1988-09-15 | 1990-03-29 | Huels Chemische Werke Ag | Schlagzaehe thermoplastische formmassen auf basis von polyphenylenether-pfropfcopolymeren und polyamiden sowie verfahren zu ihrer herstellung |
| US5159027A (en) * | 1989-01-27 | 1992-10-27 | Asahi Kasei Kogyo Kabushiki Kaisha | Stabilized polyphenylene ether resin and process for the preparation of the same |
| JPH0314855A (ja) * | 1989-06-13 | 1991-01-23 | Sumitomo Chem Co Ltd | 熱可塑性樹脂組成物 |
| US5369173A (en) * | 1989-06-13 | 1994-11-29 | Sumitomo Chemical Company, Limited | Glass fiber-reinforced resin composition |
| US6417274B1 (en) | 1999-02-05 | 2002-07-09 | General Electric Co. | Process for the manufacture of functionalized polyphenylene ether resins |
| US6211327B1 (en) | 1999-02-05 | 2001-04-03 | General Electric Company | Process for the manufacture of low molecular weight polyphenylene ether resins |
| US7114296B2 (en) * | 2001-10-30 | 2006-10-03 | Arxx Building Products, Inc. | Temporary bracing system for insulated wall form and method |
| CN101649032B (zh) * | 2008-08-14 | 2011-04-13 | 张发饶 | 一种聚苯醚为基材的相容剂体系制备方法 |
| US20120097220A1 (en) * | 2009-04-30 | 2012-04-26 | Mitsubishi Plastics, Inc. | Sheet for solar cell, and solar cell module |
| US9815946B2 (en) * | 2013-08-16 | 2017-11-14 | Exxonmobil Chemical Patents Inc. | Stabilized poly(arylene ether) compositions and methods of making them |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA785834A (en) * | 1964-01-13 | 1968-05-21 | W. Fox Daniel | Thermoplastic resins containing polyphenylene ether |
| GB1125620A (en) * | 1965-01-06 | 1968-08-28 | Gen Electric | Improvements in polymeric blends |
| US3487127A (en) * | 1965-12-13 | 1969-12-30 | Dart Ind Inc | Rubber-modified resinous polymers prepared in the presence of a polyphenylene oxide |
| US3356761A (en) * | 1967-04-12 | 1967-12-05 | Gen Electric | Melt processable polyphenylene ether and process |
| US3522326A (en) * | 1967-10-05 | 1970-07-28 | Gen Electric | Graft copolymers of polyphenylene ethers |
| US3862263A (en) * | 1969-11-29 | 1975-01-21 | Sumitomo Chemical Co | Production of modified polyphenylene oxide |
| US3700750A (en) * | 1970-01-07 | 1972-10-24 | Sumitomo Chemical Co | Stabilized polyphenylene oxide composition |
| JPS4916777B1 (enExample) * | 1970-02-19 | 1974-04-24 | ||
| JPS5420537B1 (enExample) * | 1971-04-30 | 1979-07-24 | ||
| JPS5238596B2 (enExample) * | 1973-09-06 | 1977-09-29 | ||
| JPS5139914B2 (enExample) * | 1973-09-06 | 1976-10-30 |
-
1976
- 1976-05-24 JP JP51059053A patent/JPS5931534B2/ja not_active Expired
-
1977
- 1977-02-07 US US05/766,515 patent/US4097556A/en not_active Expired - Lifetime
- 1977-02-07 GB GB4905/77A patent/GB1571014A/en not_active Expired
- 1977-02-09 CA CA271,447A patent/CA1068847A/en not_active Expired
- 1977-02-10 NL NL7701422.A patent/NL162095C/xx not_active IP Right Cessation
- 1977-02-10 FR FR7703763A patent/FR2352844A1/fr active Granted
- 1977-02-10 DE DE2705656A patent/DE2705656C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE2705656C3 (de) | 1983-12-15 |
| JPS52142799A (en) | 1977-11-28 |
| US4097556A (en) | 1978-06-27 |
| CA1068847A (en) | 1979-12-25 |
| FR2352844A1 (fr) | 1977-12-23 |
| DE2705656B2 (de) | 1979-09-20 |
| JPS5931534B2 (ja) | 1984-08-02 |
| NL162095C (nl) | 1980-04-15 |
| DE2705656A1 (de) | 1977-12-01 |
| FR2352844B1 (enExample) | 1980-12-26 |
| NL7701422A (nl) | 1977-11-28 |
| NL162095B (nl) | 1979-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19950207 |