CN103189400A - (甲基)丙烯酸基阻燃剂共聚物以及制备其的方法 - Google Patents
(甲基)丙烯酸基阻燃剂共聚物以及制备其的方法 Download PDFInfo
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- CN103189400A CN103189400A CN2010800700032A CN201080070003A CN103189400A CN 103189400 A CN103189400 A CN 103189400A CN 2010800700032 A CN2010800700032 A CN 2010800700032A CN 201080070003 A CN201080070003 A CN 201080070003A CN 103189400 A CN103189400 A CN 103189400A
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- Prior art keywords
- methyl
- phenyl
- flame retardant
- acid
- acrylic
- 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
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- -1 acryl Chemical group 0.000 title claims abstract description 85
- 239000003063 flame retardant Substances 0.000 title claims abstract description 83
- 229920001577 copolymer Polymers 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title abstract description 12
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 239000000178 monomer Substances 0.000 claims abstract description 74
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 claims abstract description 14
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 70
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 56
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
- 239000011347 resin Substances 0.000 claims description 20
- 229920005989 resin Polymers 0.000 claims description 20
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 17
- 229910052698 phosphorus Inorganic materials 0.000 claims description 17
- 239000011574 phosphorus Substances 0.000 claims description 17
- 238000002834 transmittance Methods 0.000 claims description 17
- 239000003795 chemical substances by application Substances 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- LDHQCZJRKDOVOX-UHFFFAOYSA-N 2-butenoic acid Chemical compound CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 13
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 10
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 9
- 125000004799 bromophenyl group Chemical group 0.000 claims description 9
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
- 239000000463 material Substances 0.000 claims description 9
- 239000003381 stabilizer Substances 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 7
- 239000003963 antioxidant agent Substances 0.000 claims description 5
- 230000003078 antioxidant effect Effects 0.000 claims description 5
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 5
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 5
- 150000001735 carboxylic acids Chemical class 0.000 claims description 5
- 230000014509 gene expression Effects 0.000 claims description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004902 Softening Agent Substances 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 4
- 239000007822 coupling agent Substances 0.000 claims description 4
- 239000000975 dye Substances 0.000 claims description 4
- 239000000945 filler Substances 0.000 claims description 4
- 239000003112 inhibitor Substances 0.000 claims description 4
- 239000000314 lubricant Substances 0.000 claims description 4
- 239000000049 pigment Substances 0.000 claims description 4
- 230000003068 static effect Effects 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 239000005864 Sulphur Chemical group 0.000 claims description 3
- 150000008065 acid anhydrides Chemical class 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 2
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 2
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 claims description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000005456 glyceride group Chemical group 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 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
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 2
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 2
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 abstract description 2
- 238000006116 polymerization reaction Methods 0.000 description 15
- 239000012986 chain transfer agent Substances 0.000 description 11
- 229920006243 acrylic copolymer Polymers 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 9
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 7
- 230000006866 deterioration Effects 0.000 description 6
- 229920005668 polycarbonate resin Polymers 0.000 description 6
- 239000004431 polycarbonate resin Substances 0.000 description 6
- 239000004926 polymethyl methacrylate Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 239000004925 Acrylic resin Substances 0.000 description 5
- 229920000178 Acrylic resin Polymers 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 125000004494 ethyl ester group Chemical group 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- QSKKMCIVGFSWJK-UHFFFAOYSA-N dimethoxyphosphorylmethyl 2-methylprop-2-enoate Chemical compound COP(=O)(OC)COC(=O)C(C)=C QSKKMCIVGFSWJK-UHFFFAOYSA-N 0.000 description 3
- 229940102838 methylmethacrylate Drugs 0.000 description 3
- 238000005502 peroxidation Methods 0.000 description 3
- 150000003008 phosphonic acid esters Chemical class 0.000 description 3
- 239000004417 polycarbonate Substances 0.000 description 3
- 229920000515 polycarbonate Polymers 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WGEHZQBNIFSXDP-UHFFFAOYSA-N diethoxyphosphorylmethyl 2-methylprop-2-enoate Chemical compound CCOP(=O)(OCC)COC(=O)C(C)=C WGEHZQBNIFSXDP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
- 229910000397 disodium phosphate Inorganic materials 0.000 description 2
- 235000019800 disodium phosphate Nutrition 0.000 description 2
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 230000006641 stabilisation Effects 0.000 description 2
- 238000011105 stabilization Methods 0.000 description 2
- 238000010557 suspension polymerization reaction Methods 0.000 description 2
- BOOBDAVNHSOIDB-UHFFFAOYSA-N (2,3-dichlorobenzoyl) 2,3-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC=CC(C(=O)OOC(=O)C=2C(=C(Cl)C=CC=2)Cl)=C1Cl BOOBDAVNHSOIDB-UHFFFAOYSA-N 0.000 description 1
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- ZRKMQKLGEQPLNS-UHFFFAOYSA-N 1-Pentanethiol Chemical compound CCCCCS ZRKMQKLGEQPLNS-UHFFFAOYSA-N 0.000 description 1
- ZQBWPISHKSLENR-UHFFFAOYSA-N 2-diethoxyphosphorylethyl 2-methylprop-2-enoate Chemical compound CCOP(=O)(OCC)CCOC(=O)C(C)=C ZQBWPISHKSLENR-UHFFFAOYSA-N 0.000 description 1
- QOOHUWULLQCUGG-UHFFFAOYSA-N 2-dimethoxyphosphorylethyl 2-methylprop-2-enoate Chemical compound COP(=O)(OC)CCOC(=O)C(C)=C QOOHUWULLQCUGG-UHFFFAOYSA-N 0.000 description 1
- YBMJTXXDDPOQPP-UHFFFAOYSA-N 2-dipropoxyphosphorylethyl 2-methylprop-2-enoate Chemical compound CCCOP(=O)(OCCC)CCOC(=O)C(C)=C YBMJTXXDDPOQPP-UHFFFAOYSA-N 0.000 description 1
- MUZDXNQOSGWMJJ-UHFFFAOYSA-N 2-methylprop-2-enoic acid;prop-2-enoic acid Chemical compound OC(=O)C=C.CC(=C)C(O)=O MUZDXNQOSGWMJJ-UHFFFAOYSA-N 0.000 description 1
- DBFMNODLDZJBTL-UHFFFAOYSA-N 2-methylprop-2-enoyloxymethyl(propan-2-yloxy)phosphinic acid Chemical compound C(C(=C)C)(=O)OCP(=O)(OC(C)C)O DBFMNODLDZJBTL-UHFFFAOYSA-N 0.000 description 1
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 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
- CUWJKUDBPCMCIZ-UHFFFAOYSA-N CCCCCCCCCCCCCCCCCC.C(CC)(=O)O Chemical compound CCCCCCCCCCCCCCCCCC.C(CC)(=O)O CUWJKUDBPCMCIZ-UHFFFAOYSA-N 0.000 description 1
- FQNBLAJEKBDTRT-UHFFFAOYSA-N CC[S].CC=CC(=O)O Chemical compound CC[S].CC=CC(=O)O FQNBLAJEKBDTRT-UHFFFAOYSA-N 0.000 description 1
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- ATMLPEJAVWINOF-UHFFFAOYSA-N acrylic acid acrylic acid Chemical compound OC(=O)C=C.OC(=O)C=C ATMLPEJAVWINOF-UHFFFAOYSA-N 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- NCPTYZLUYHXITE-UHFFFAOYSA-N benzyl but-2-enoate Chemical compound CC=CC(=O)OCC1=CC=CC=C1 NCPTYZLUYHXITE-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- SQHOHKQMTHROSF-UHFFFAOYSA-N but-1-en-2-ylbenzene Chemical class CCC(=C)C1=CC=CC=C1 SQHOHKQMTHROSF-UHFFFAOYSA-N 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- ZUMGBVSYIVKLDH-UHFFFAOYSA-N cyclohexyl but-2-enoate Chemical compound CC=CC(=O)OC1CCCCC1 ZUMGBVSYIVKLDH-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- XJOBOFWTZOKMOH-UHFFFAOYSA-N decanoyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(=O)CCCCCCCCC XJOBOFWTZOKMOH-UHFFFAOYSA-N 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- ZPRXNNUSHVQSSD-UHFFFAOYSA-N dipropoxyphosphorylmethyl 2-methylprop-2-enoate Chemical compound CCCOP(=O)(OCCC)COC(=O)C(C)=C ZPRXNNUSHVQSSD-UHFFFAOYSA-N 0.000 description 1
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 1
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 150000002366 halogen compounds Chemical class 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 150000002500 ions Chemical group 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Natural products OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000002932 luster Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940017219 methyl propionate Drugs 0.000 description 1
- 229940045641 monobasic sodium phosphate Drugs 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- RPBCDDTWDKYNQY-UHFFFAOYSA-N o-dodecyl propanethioate Chemical compound CCCCCCCCCCCCOC(=S)CC RPBCDDTWDKYNQY-UHFFFAOYSA-N 0.000 description 1
- KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005990 polystyrene resin Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- VVWRJUBEIPHGQF-UHFFFAOYSA-N propan-2-yl n-propan-2-yloxycarbonyliminocarbamate Chemical compound CC(C)OC(=O)N=NC(=O)OC(C)C VVWRJUBEIPHGQF-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229920003169 water-soluble polymer Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/14—Macromolecular materials
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims (13)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2010-0109991 | 2010-11-05 | ||
KR1020100109991A KR20120048384A (ko) | 2010-11-05 | 2010-11-05 | 난연 아크릴계 공중합체 및 그의 제조 방법 |
PCT/KR2010/009532 WO2012060514A1 (ko) | 2010-11-05 | 2010-12-29 | (메타)아크릴계 난연 공중합체 및 그의 제조 방법 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN103189400A true CN103189400A (zh) | 2013-07-03 |
CN103189400B CN103189400B (zh) | 2016-09-07 |
Family
ID=46024616
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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CN201080070003.2A Expired - Fee Related CN103189400B (zh) | 2010-11-05 | 2010-12-29 | (甲基)丙烯酸基阻燃剂共聚物以及制备其的方法 |
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US (1) | US8921480B2 (zh) |
KR (1) | KR20120048384A (zh) |
CN (1) | CN103189400B (zh) |
WO (1) | WO2012060514A1 (zh) |
Cited By (1)
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CN111171234A (zh) * | 2020-02-13 | 2020-05-19 | 中国科学技术大学 | 一种聚合型阻燃增效相容剂及其制备方法和应用 |
Families Citing this family (11)
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KR101293787B1 (ko) | 2010-07-28 | 2013-08-06 | 제일모직주식회사 | 난연성 및 내열성이 우수한 투명 열가소성 수지 조성물 |
KR20120048384A (ko) | 2010-11-05 | 2012-05-15 | 제일모직주식회사 | 난연 아크릴계 공중합체 및 그의 제조 방법 |
KR101351614B1 (ko) | 2010-11-05 | 2014-02-17 | 제일모직주식회사 | 난연 내스크래치성 폴리카보네이트 수지 조성물 |
KR101374360B1 (ko) | 2010-12-14 | 2014-03-18 | 제일모직주식회사 | 난연 내스크래치성 폴리카보네이트 수지 조성물 |
KR101411004B1 (ko) * | 2010-12-23 | 2014-06-23 | 제일모직주식회사 | 아크릴계 공중합체 수지 조성물 |
KR20130002789A (ko) | 2011-06-29 | 2013-01-08 | 제일모직주식회사 | 컬러필터용 감광성 수지 조성물 및 이를 이용한 컬러필터 |
KR101674990B1 (ko) | 2012-12-07 | 2016-11-10 | 제일모직 주식회사 | 컬러필터용 감광성 수지 조성물 및 이를 이용한 컬러필터 |
KR101714744B1 (ko) * | 2015-04-17 | 2017-03-09 | 부림케미칼 주식회사 | 친환경 인계 난연 점착제 조성물 및 이의 제조 방법 |
JP6929293B2 (ja) * | 2016-09-30 | 2021-09-01 | 株式会社クラレ | ホスホネート基を有する共重合体組成物 |
CN112480302A (zh) * | 2019-09-11 | 2021-03-12 | 广东广山新材料股份有限公司 | 一种阻燃型聚甲基丙烯酸甲酯及其制备方法和应用 |
CN112480306A (zh) * | 2019-09-11 | 2021-03-12 | 广东广山新材料股份有限公司 | 一种丙烯酸酯共聚物及其制备方法和应用 |
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US3985831A (en) * | 1975-06-30 | 1976-10-12 | Borg-Warner Corporation | Flame retardant graft polymer compositions prepared from phosphinyl-substituted acrylonitriles |
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JPS5789613A (en) * | 1980-11-26 | 1982-06-04 | Kanegafuchi Chem Ind Co Ltd | Flame-retardant acrylic synthetic fiber |
AU2668188A (en) * | 1987-12-10 | 1989-07-06 | Ppg Industries, Inc. | Water-based coating compositions containing aluminum pigments and antigassing agents |
KR100885819B1 (ko) | 2007-12-18 | 2009-02-26 | 제일모직주식회사 | 굴절률이 우수한 분지형 아크릴계 공중합체 및 그 제조방법 |
KR20120048384A (ko) | 2010-11-05 | 2012-05-15 | 제일모직주식회사 | 난연 아크릴계 공중합체 및 그의 제조 방법 |
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2010
- 2010-11-05 KR KR1020100109991A patent/KR20120048384A/ko active Application Filing
- 2010-12-29 WO PCT/KR2010/009532 patent/WO2012060514A1/ko active Application Filing
- 2010-12-29 CN CN201080070003.2A patent/CN103189400B/zh not_active Expired - Fee Related
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2013
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US5773533A (en) * | 1996-04-01 | 1998-06-30 | Hoechst Aktiengesellschaft | Epoxy resin reacted with carboxy-functional phosphinic or phosphonic acid and hardener |
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CN111171234A (zh) * | 2020-02-13 | 2020-05-19 | 中国科学技术大学 | 一种聚合型阻燃增效相容剂及其制备方法和应用 |
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US8921480B2 (en) | 2014-12-30 |
CN103189400B (zh) | 2016-09-07 |
US20130234084A1 (en) | 2013-09-12 |
WO2012060514A1 (ko) | 2012-05-10 |
KR20120048384A (ko) | 2012-05-15 |
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