JP6360044B2 - 向上した絶縁抵抗を有するハロゲンを含まない難燃性の熱可塑性エラストマー組成物 - Google Patents
向上した絶縁抵抗を有するハロゲンを含まない難燃性の熱可塑性エラストマー組成物 Download PDFInfo
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- JP6360044B2 JP6360044B2 JP2015516105A JP2015516105A JP6360044B2 JP 6360044 B2 JP6360044 B2 JP 6360044B2 JP 2015516105 A JP2015516105 A JP 2015516105A JP 2015516105 A JP2015516105 A JP 2015516105A JP 6360044 B2 JP6360044 B2 JP 6360044B2
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- flame retardant
- polymer composition
- retardant polymer
- epoxy
- ester
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- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 0.000 title description 4
- 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 description 151
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- 125000003118 aryl group Chemical group 0.000 claims description 41
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- -1 ether ester Chemical class 0.000 claims description 35
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- 125000000524 functional group Chemical group 0.000 claims description 27
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- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims description 22
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- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinyl group Chemical group C1(O)=CC(O)=CC=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 claims description 12
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- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 11
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- GXURZKWLMYOCDX-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)propane-1,3-diol;dihydroxyphosphanyl dihydrogen phosphite Chemical group OP(O)OP(O)O.OCC(CO)(CO)CO GXURZKWLMYOCDX-UHFFFAOYSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
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- 229920000233 poly(alkylene oxides) Polymers 0.000 claims description 4
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- 239000003381 stabilizer Substances 0.000 claims description 4
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- 238000012545 processing Methods 0.000 claims description 3
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- 235000021317 phosphate Nutrition 0.000 description 32
- 230000000052 comparative effect Effects 0.000 description 25
- 238000012360 testing method Methods 0.000 description 17
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 13
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- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 9
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- 150000002334 glycols Chemical class 0.000 description 8
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- 125000001931 aliphatic group Chemical group 0.000 description 5
- 238000010292 electrical insulation Methods 0.000 description 5
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- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 5
- 239000012760 heat stabilizer Substances 0.000 description 5
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- 229920001707 polybutylene terephthalate Polymers 0.000 description 5
- XKZQKPRCPNGNFR-UHFFFAOYSA-N 2-(3-hydroxyphenyl)phenol Chemical compound OC1=CC=CC(C=2C(=CC=CC=2)O)=C1 XKZQKPRCPNGNFR-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 4
- 150000002118 epoxides Chemical class 0.000 description 4
- 238000001746 injection moulding Methods 0.000 description 4
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
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- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- ZJIPHXXDPROMEF-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite Chemical class OP(O)OP(O)O ZJIPHXXDPROMEF-UHFFFAOYSA-N 0.000 description 3
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- WBWXVCMXGYSMQA-UHFFFAOYSA-N 3,9-bis[2,4-bis(2-phenylpropan-2-yl)phenoxy]-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C=1C=C(OP2OCC3(CO2)COP(OC=2C(=CC(=CC=2)C(C)(C)C=2C=CC=CC=2)C(C)(C)C=2C=CC=CC=2)OC3)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 WBWXVCMXGYSMQA-UHFFFAOYSA-N 0.000 description 2
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- WUDDSDIHJHPJRP-UHFFFAOYSA-N 2-ethyloctanedioic acid Chemical compound CCC(C(O)=O)CCCCCC(O)=O WUDDSDIHJHPJRP-UHFFFAOYSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- QLIQIXIBZLTPGQ-UHFFFAOYSA-N 4-(2-hydroxyethoxy)benzoic acid Chemical compound OCCOC1=CC=C(C(O)=O)C=C1 QLIQIXIBZLTPGQ-UHFFFAOYSA-N 0.000 description 1
- UZXIJHSJEKWJHP-UHFFFAOYSA-N 4-(4-carboxycyclohexyl)cyclohexane-1-carboxylic acid Chemical compound C1CC(C(=O)O)CCC1C1CCC(C(O)=O)CC1 UZXIJHSJEKWJHP-UHFFFAOYSA-N 0.000 description 1
- SQJQLYOMPSJVQS-UHFFFAOYSA-N 4-(4-carboxyphenyl)sulfonylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1S(=O)(=O)C1=CC=C(C(O)=O)C=C1 SQJQLYOMPSJVQS-UHFFFAOYSA-N 0.000 description 1
- VTDMBRAUHKUOON-UHFFFAOYSA-N 4-[(4-carboxyphenyl)methyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CC1=CC=C(C(O)=O)C=C1 VTDMBRAUHKUOON-UHFFFAOYSA-N 0.000 description 1
- UHUUGQDYCYKQTC-UHFFFAOYSA-N 4-[2,2,2-tris(4-hydroxyphenyl)ethyl]phenol Chemical compound C1=CC(O)=CC=C1CC(C=1C=CC(O)=CC=1)(C=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 UHUUGQDYCYKQTC-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
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- KMTRUDSVKNLOMY-UHFFFAOYSA-N Ethylene carbonate Chemical compound O=C1OCCO1 KMTRUDSVKNLOMY-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 239000004609 Impact Modifier Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
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- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 235000009781 Myrtillocactus geometrizans Nutrition 0.000 description 1
- 240000009125 Myrtillocactus geometrizans Species 0.000 description 1
- 239000006057 Non-nutritive feed additive Substances 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical group CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 208000020329 Zika virus infectious disease Diseases 0.000 description 1
- OBNDGIHQAIXEAO-UHFFFAOYSA-N [O].[Si] Chemical class [O].[Si] OBNDGIHQAIXEAO-UHFFFAOYSA-N 0.000 description 1
- VLONNSVCURZTOJ-UHFFFAOYSA-N [PH2](O)=O.C=C.C=C Chemical compound [PH2](O)=O.C=C.C=C VLONNSVCURZTOJ-UHFFFAOYSA-N 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 125000002015 acyclic group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- ZJKCITHLCNCAHA-UHFFFAOYSA-K aluminum dioxidophosphanium Chemical compound [Al+3].[O-][PH2]=O.[O-][PH2]=O.[O-][PH2]=O ZJKCITHLCNCAHA-UHFFFAOYSA-K 0.000 description 1
- XSAOTYCWGCRGCP-UHFFFAOYSA-K aluminum;diethylphosphinate Chemical compound [Al+3].CCP([O-])(=O)CC.CCP([O-])(=O)CC.CCP([O-])(=O)CC XSAOTYCWGCRGCP-UHFFFAOYSA-K 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
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- 238000000071 blow moulding Methods 0.000 description 1
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
- 239000004327 boric acid Substances 0.000 description 1
- LXIJGELKPWRBPD-UHFFFAOYSA-N boric acid 1,3,5-triazine-2,4,6-triamine Chemical compound OB(O)O.OB(O)O.NC1=NC(N)=NC(N)=N1 LXIJGELKPWRBPD-UHFFFAOYSA-N 0.000 description 1
- 150000001639 boron compounds Chemical class 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
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- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
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- 238000006243 chemical reaction Methods 0.000 description 1
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- 238000002485 combustion reaction Methods 0.000 description 1
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- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical compound OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 1
- PDXRQENMIVHKPI-UHFFFAOYSA-N cyclohexane-1,1-diol Chemical compound OC1(O)CCCCC1 PDXRQENMIVHKPI-UHFFFAOYSA-N 0.000 description 1
- XBZSBBLNHFMTEB-UHFFFAOYSA-N cyclohexane-1,3-dicarboxylic acid Chemical compound OC(=O)C1CCCC(C(O)=O)C1 XBZSBBLNHFMTEB-UHFFFAOYSA-N 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- YZFOGXKZTWZVFN-UHFFFAOYSA-N cyclopentane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CCCC1 YZFOGXKZTWZVFN-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- ZUUKAYQBTGMEPI-UHFFFAOYSA-N dihydroxyphosphanyl dihydrogen phosphite 2-[2-(2-hydroxyphenyl)propan-2-yl]phenol Chemical compound OP(O)OP(O)O.C(C)(C)(C1=C(C=CC=C1)O)C1=C(C=CC=C1)O ZUUKAYQBTGMEPI-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- SYLAFCZSYRXBJF-UHFFFAOYSA-N furan-3,4-dicarboxylic acid Chemical compound OC(=O)C1=COC=C1C(O)=O SYLAFCZSYRXBJF-UHFFFAOYSA-N 0.000 description 1
- 239000008202 granule composition Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010102 injection blow moulding Methods 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 150000002681 magnesium compounds Chemical class 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical compound C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical compound C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical group [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- XZTOTRSSGPPNTB-UHFFFAOYSA-N phosphono dihydrogen phosphate;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)OP(O)(O)=O XZTOTRSSGPPNTB-UHFFFAOYSA-N 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 150000008442 polyphenolic compounds Chemical class 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 0.000 description 1
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 238000001175 rotational moulding Methods 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003504 terephthalic acids Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000003856 thermoforming Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- QUTZUATVZPXUJR-UHFFFAOYSA-N trinonyl phosphite Chemical group CCCCCCCCCOP(OCCCCCCCCC)OCCCCCCCCC QUTZUATVZPXUJR-UHFFFAOYSA-N 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 239000004034 viscosity adjusting agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
- C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
- C08L67/025—Polyesters derived from dicarboxylic acids and dihydroxy compounds containing polyether sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/0066—Flame-proofing or flame-retarding additives
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
- C08K5/523—Esters of phosphoric acids, e.g. of H3PO4 with hydroxyaryl compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/53—Phosphorus bound to oxygen bound to oxygen and to carbon only
- C08K5/5313—Phosphinic compounds, e.g. R2=P(:O)OR'
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/42—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes polyesters; polyethers; polyacetals
- H01B3/421—Polyesters
- H01B3/422—Linear saturated polyesters derived from dicarboxylic acids and dihydroxy compounds
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B7/00—Insulated conductors or cables characterised by their form
- H01B7/17—Protection against damage caused by external factors, e.g. sheaths or armouring
- H01B7/29—Protection against damage caused by extremes of temperature or by flame
- H01B7/295—Protection against damage caused by extremes of temperature or by flame using material resistant to flame
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/02—Flame or fire retardant/resistant
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2207/00—Properties characterising the ingredient of the composition
- C08L2207/04—Thermoplastic elastomer
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B3/00—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties
- H01B3/18—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances
- H01B3/30—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes
- H01B3/42—Insulators or insulating bodies characterised by the insulating materials; Selection of materials for their insulating or dielectric properties mainly consisting of organic substances plastics; resins; waxes polyesters; polyethers; polyacetals
- H01B3/427—Polyethers
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Insulated Conductors (AREA)
- Organic Insulating Materials (AREA)
- Polyesters Or Polycarbonates (AREA)
- Inorganic Insulating Materials (AREA)
Description
a)1つまたは複数のコポリエーテルエステル熱可塑性エラストマーと;
b)メラミンシアヌレートと;
c)少なくとも1つのエポキシ含有化合物と;
d)i)難燃性ポリマー組成物が芳香族ホスフェートエステル難燃剤およびホスファイトを含むときに、存在するエポキシ含有化合物の量が、全エポキシ官能基当量(total epoxy functional group equivalent weight)が1つまたは複数のコポリエーテルエステル熱可塑性エラストマーと芳香族ホスフェートエステル難燃剤との合計重量の1kg当たり少なくとも約32ミリ当量であるようなものである、そしてii)難燃性ポリマー組成物がホスファイトの不在下に芳香族ホスフェートエステル難燃剤を含むときに、存在するエポキシ含有化合物の量が、全エポキシ官能基当量が1つまたは複数のコポリエーテルエステル熱可塑性エラストマーと芳香族ホスフェートエステル難燃剤との合計重量の1kg当たり少なくとも約56ミリ当量であるようなものであるという条件で、
任意選択的に、ホスファイト、芳香族ホスフェートエステル難燃剤およびそれらの混合物からなる群から選択される少なくとも1つの化合物と
を含む難燃性ポリマー組成物を指向する。
a)1つまたは複数のコポリエーテルエステル熱可塑性エラストマーと、
b)難燃性ポリマー組成物の総重量を基準として少なくとも10重量パーセントからであるかまたは10重量パーセントに等しい量のメラミンシアヌレートと;
c)1つまたは複数のエポキシ含有化合物と;任意選択的に
d)難燃性ポリマー組成物の総重量を基準として0〜2重量パーセントのホスファイトと、
e)i)難燃性ポリマー組成物が芳香族ホスフェートエステル難燃剤およびホスファイトを含むときに、存在するエポキシ含有化合物の量が、全エポキシ官能基当量が1つまたは複数のコポリエーテルエステル熱可塑性エラストマーと芳香族ホスフェートエステル難燃剤との合計重量の1kg当たり少なくとも約32ミリ当量であるようなものである、そしてii)難燃性ポリマー組成物がホスファイトの不在下に芳香族ホスフェートエステル難燃剤を含むときに、存在するエポキシ含有化合物の量が、全エポキシ官能基当量が1つまたは複数のコポリエーテルエステル熱可塑性エラストマーと芳香族ホスフェートエステル難燃剤との合計重量の1kg当たり少なくとも約56ミリ当量であるようなものであるという条件で、難燃性ポリマー組成物の総重量を基準として0〜15重量パーセントの芳香族ホスフェートエステル難燃剤と、
f)難燃性ポリマー組成物の総重量を基準として0.05〜10重量パーセントの添加剤と
からなり、
ここで、成分a)〜f)の合計は100重量パーセントになる。
式中、
Gは、約400〜約6000、または好ましくは約400〜約3000の数平均分子量を有するポリ(アルキレンオキシド)グリコールからの末端ヒドロキシル基の除去後に残る二価ラジカルであり;
Rは、約300未満の分子量を有するジカルボン酸からのカルボキシル基の除去後に残る二価ラジカルであり;
Dは、約250未満の分子量を有するジオールからのヒドロキシル基の除去後に残る二価ラジカルである。
本発明は、本明細書に記載される組成物、使用および方法についてさらなる詳細を提供する以下の実施例におけるある種の実施形態によってさらに例示される。
以下の原材料を、本明細書に記載される難燃性ポリマー組成物および比較例の組成物を調製するために使用した。
本発明の難燃性ポリマー組成物および比較組成物は、次の通り調製した:表1および2にリストされる量の、上記の原材料を二軸スクリュー押出機で溶融ブレンドした。比較例C4、C5のおよび全実施例の配合された溶融ブレンド混合物を、レースまたはストランドの形態で押し出し、水浴中で冷却し、切り刻んで顆粒にし、水分吸収を防ぐために密封アルミニウム内張バッグに入れた。
燃焼性試験は、UL 94試験標準、20mm垂直燃焼試験に従って行った。試験検体は、125mm長さ×13mm幅および0.8mmの厚さの寸法を有する試験片の形態に組成物を射出成形することによって本発明の組成物(試料E1〜E22)からおよび比較組成物(試料C4)から形成した。射出成形前に、上記の方法に従って調製された難燃性組成物の顆粒を乾燥させて0.08パーセントよりも下の水分レベルを有する顆粒組成物を提供した。比較組成物C6〜C8については、試験検体は、125mm長さ×13mm幅および1.8mmの厚さの寸法を有する試験片の形態に押し出された平らなストリップから試験検体をカットすることによって形成した。測定前に、試験検体を23℃および50%相対湿度で48時間順化させた。試験検体を、検体の下端が乾燥した吸収性脱脂綿の水平層の上方300mmにあるように、垂直方向に検体の縦軸で固定した。20mm高さの青炎を生成するバーナーを中心で、炎が10秒間検体の底縁の中間点に適用されるように置いた。炎を検体に10秒間適用した後、バーナーを試料から引き離し、残炎時間、t1を測定した。試験検体の残炎が終わったとき、バーナーを再び追加の10秒間検体の下方に置いた。炎を次に試験検体から引き離し、第二の残炎時間、t2を測定した。材料を、燃焼中の材料の挙動に基づいて、試験仕様書に従ってV−0、V−1またはV−2に分類し、V−2は最低要求分類である。組成物がこの最低要求分類(V−2)についての判断基準を満たすことができなかったとき、それは、表中で「不合格」と報告される。
(i)23℃での空気中の体積抵抗率:プラークを、成形後に室温で少なくとも16時間そのままにしておいた。そのようなプラークからの体積抵抗率は、各読み取りの前に60秒間500VのDC電位を加えることによってIEC 60093に従って室温で空気中で測定した。各読み取りの継続時間は60秒であった。
Claims (16)
- a)1つまたは複数のコポリエーテルエステル熱可塑性エラストマーと;
b)難燃性ポリマー組成物の総重量を基準として少なくとも10重量パーセントのメラミンシアヌレートと;
c)少なくとも1つのエポキシ含有化合物と;
d)芳香族ホスフェートエステル難燃剤と;
任意選択的に、ホスファイトと
を含む難燃性ポリマー組成物であって、
前記ホスファイトの量は、前記難燃性ポリマー組成物の総重量を基準として0〜2重量パーセントであり、
但し、i)前記難燃性ポリマー組成物が芳香族ホスフェートエステル難燃剤およびホスファイトを含む場合に、前記エポキシ含有化合物は、全エポキシ官能基当量が前記1つまたは複数のコポリエーテルエステル熱可塑性エラストマーと前記芳香族ホスフェートエステル難燃剤との合計重量の1kg当たり少なくとも32ミリ当量であるような量で存在しており、そしてii)前記難燃性ポリマー組成物がホスファイトの不在下に芳香族ホスフェートエステル難燃剤を含む場合に、前記エポキシ含有化合物は、前記全エポキシ官能基当量が前記1つまたは複数のコポリエーテルエステル熱可塑性エラストマーと前記芳香族ホスフェートエステル難燃剤との合計重量の1kg当たり少なくとも56ミリ当量であるような量で存在しているとする、難燃性ポリマー組成物。 - a)1つまたは複数のコポリエーテルエステル熱可塑性エラストマーと;
b)難燃性ポリマー組成物の総重量を基準として少なくとも10重量パーセントのメラミンシアヌレートと;
c)1つまたは複数のエポキシ含有化合物と;
d)前記難燃性ポリマー組成物の総重量を基準として0〜2重量パーセントのホスファイトと、
e)前記難燃性ポリマー組成物の総重量を基準として2〜15重量パーセントの芳香族ホスフェートエステル難燃剤と、
f)前記難燃性ポリマー組成物の総重量を基準として0.05〜10重量パーセントの添加剤と
からなる難燃性ポリマー組成物であって、
但し、i)前記難燃性ポリマー組成物が芳香族ホスフェートエステル難燃剤およびホスファイトを含む場合に、前記エポキシ含有化合物は、全エポキシ官能基当量が前記1つまたは複数のコポリエーテルエステル熱可塑性エラストマーと前記芳香族ホスフェートエステル難燃剤との合計重量の1kg当たり少なくとも32ミリ当量であるような量で存在しており、そしてii)前記難燃性ポリマー組成物がホスファイトの不在下に芳香族ホスフェートエステル難燃剤を含む場合に、前記エポキシ含有化合物は、前記全エポキシ官能基当量が前記1つまたは複数のコポリエーテルエステル熱可塑性エラストマーと前記芳香族ホスフェートエステル難燃剤との合計重量の1kg当たり少なくとも56ミリ当量であるような量で存在しているとし、
成分a)〜f)の合計が100重量パーセントになる難燃性ポリマー組成物。 - 前記1つまたは複数のコポリエーテルエステル熱可塑性エラストマーが、エステル結合によって頭尾結合した多数の繰り返し長鎖エステル単位および短鎖エステル単位を有するコポリエーテルエステルエラストマーであって、前記長鎖エステル単位が式(A):
式中、
Gは、400〜6000の数平均分子量を有するポリ(アルキレンオキシド)グリコールからの末端ヒドロキシル基の除去後に残る二価ラジカルであり;
Rは、300未満の分子量を有するジカルボン酸からのカルボキシル基の除去後に残る二価ラジカルであり;そして
Dは、250未満の分子量を有するジオールからのヒドロキシル基の除去後に残る二価ラジカルであるコポリエーテルエステルエラストマーである、請求項1または2に記載の難燃性ポリマー組成物。 - 前記1つまたは複数のコポリエーテルエステル熱可塑性エラストマーが、(1)ポリ(テトラメチレンオキシド)グリコールまたはポリ(トリメチレンオキシド)グリコールおよびそれらの混合物と;(2)イソフタル酸、テレフタル酸およびそれらの混合物からなる群から選択されるジカルボン酸と;(3)1,4−ブタンジオール、1,3−プロパンジオールおよびそれらの混合物からなる群から選択されるジオールとを含むモノマーから製造されるコポリエーテルエステルエラストマーである、請求項1〜3のいずれか一項に記載の難燃性ポリマー組成物。
- 前記少なくとも1つのコポリエーテルエステル熱可塑性エラストマーが、(1)ポリ(テトラメチレンオキシド)グリコールと;(2)テレフタル酸からなる群から選択されるジカルボン酸と;(3)1,4−ブタンジオール、1,3−プロパンジオールおよびそれらの混合物からなる群から選択されるジオールとを含むモノマーから製造されるコポリエーテルエステルエラストマーであり、そしてここで、ポリ(テトラメチレンオキシド)グリコールのレベルが、コポリエーテルエステルエラストマーの総重量を基準として25重量パーセント未満である、請求項1〜4のいずれか一項に記載の難燃性ポリマー組成物。
- (1)ポリ(テトラメチレンオキシド)グリコールと;(2)イソフタル酸およびテレフタル酸の混合物からなる群から選択されるジカルボン酸と;(3)1,4−ブタンジオール、1,3−プロパンジオールおよびそれらの混合物からなる群から選択されるジオールとを含むモノマーから製造される少なくとも1つのコポリエーテルエステル熱可塑性エラストマーをさらに含み、そしてここで、前記コポリエーテルエステルエラストマーのレベルが、コポリエーテルエステルエラストマーの総重量を基準として5〜50重量パーセントである、請求項5に記載の難燃性ポリマー組成物。
- 前記添加剤が、安定剤、加工剤、金属不活性化剤、酸化防止剤、UV安定剤、熱安定剤、染料および/または顔料からなる群から選択される、請求項2に記載の難燃性ポリマー組成物。
- メラミンシアヌレートb)の量が、前記難燃性ポリマー組成物の総重量を基準として10〜30重量パーセントである請求項1〜7のいずれか一項に記載の難燃性ポリマー組成物。
- エポキシ含有化合物c)の量が、エポキシ含有化合物c)が前記難燃性ポリマー組成物の総重量の百グラムを基準として2.4〜10ミリ当量の全エポキシ官能性を提供するような量である請求項1〜8のいずれか一項に記載の難燃性ポリマー組成物。
- ホスファイトの量が、前記難燃性ポリマー組成物の総重量を基準として0.1〜1重量パーセントである請求項1〜9のいずれか一項に記載の難燃性ポリマー組成物。
- 芳香族ホスフェートエステルの量が、前記難燃性ポリマー組成物の総重量を基準として2〜12重量パーセントである請求項1〜10のいずれか一項に記載の難燃性ポリマー組成物。
- 前記エポキシ含有化合物c)が、2,2−ビス(4−ヒドロキシフェニル)プロパン−エピクロロヒドリンコポリマーおよびテトラフェノールエタンのテトラグリシジルエーテルならびのそれらの組み合わせからなる群から選択される請求項1〜11のいずれか一項に記載の難燃性ポリマー組成物。
- 前記ホスファイトがペンタエリスリトールジホスファイトである請求項1〜12のいずれか一項に記載の難燃性ポリマー組成物。
- 前記芳香族ホスフェートエステルが、レゾルシノールビス(ジ−2,6−ジメチルフェニルホスフェート)およびビスフェノールビス(ジ−2,6−ジメチルフェニルホスフェート)ならびにそれらの組み合わせからなる群から選択される請求項1〜13のいずれか一項に記載の難燃性ポリマー組成物。
- 請求項1〜12のいずれか一項に記載された前記難燃性ポリマー組成物でできたコーティングを含むワイヤーまたはケーブル。
- 絶縁ワイヤーおよび/またはケーブルを製造するための請求項1または12のいずれか一項に記載の難燃性ポリマー組成物の使用。
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2013
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- 2013-06-04 KR KR1020147036960A patent/KR102070206B1/ko active IP Right Grant
- 2013-06-04 CN CN201380029986.9A patent/CN104334636B/zh active Active
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EP2859042A2 (en) | 2015-04-15 |
KR20150016985A (ko) | 2015-02-13 |
CN104334636B (zh) | 2017-01-18 |
US20130327558A1 (en) | 2013-12-12 |
US20180197654A1 (en) | 2018-07-12 |
US10319492B2 (en) | 2019-06-11 |
JP2015525272A (ja) | 2015-09-03 |
US9934883B2 (en) | 2018-04-03 |
JP6721632B2 (ja) | 2020-07-15 |
EP2859042B1 (en) | 2020-09-23 |
CN104334636A (zh) | 2015-02-04 |
US20190139672A1 (en) | 2019-05-09 |
KR102070206B1 (ko) | 2020-01-29 |
JP2018166109A (ja) | 2018-10-25 |
WO2013184631A2 (en) | 2013-12-12 |
WO2013184631A3 (en) | 2014-02-20 |
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