JPH11343382A - 難燃性樹脂組成物 - Google Patents
難燃性樹脂組成物Info
- Publication number
- JPH11343382A JPH11343382A JP10162229A JP16222998A JPH11343382A JP H11343382 A JPH11343382 A JP H11343382A JP 10162229 A JP10162229 A JP 10162229A JP 16222998 A JP16222998 A JP 16222998A JP H11343382 A JPH11343382 A JP H11343382A
- Authority
- JP
- Japan
- Prior art keywords
- flame
- resin composition
- resin
- general formula
- formula
- 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.)
- Pending
Links
- 239000003063 flame retardant Substances 0.000 title claims abstract description 42
- 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 title claims abstract description 35
- 239000011342 resin composition Substances 0.000 title claims description 41
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 claims abstract description 16
- 239000005011 phenolic resin Substances 0.000 claims abstract description 13
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- -1 aromatic phosphate ester Chemical class 0.000 claims description 23
- 229910019142 PO4 Inorganic materials 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 19
- 239000010452 phosphate Substances 0.000 claims description 18
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229920005989 resin Polymers 0.000 abstract description 29
- 239000011347 resin Substances 0.000 abstract description 29
- 229920003986 novolac Polymers 0.000 abstract description 18
- 238000000465 moulding Methods 0.000 abstract description 8
- 238000010521 absorption reaction Methods 0.000 abstract description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 7
- 238000002485 combustion reaction Methods 0.000 abstract description 6
- 230000007062 hydrolysis Effects 0.000 abstract description 5
- 238000006460 hydrolysis reaction Methods 0.000 abstract description 5
- 239000002341 toxic gas Substances 0.000 abstract description 4
- 150000002148 esters Chemical class 0.000 abstract description 3
- 238000013329 compounding Methods 0.000 abstract description 2
- 229910052760 oxygen Inorganic materials 0.000 abstract description 2
- 230000015556 catabolic process Effects 0.000 abstract 1
- 238000006731 degradation reaction Methods 0.000 abstract 1
- 229920001971 elastomer Polymers 0.000 description 20
- 235000021317 phosphate Nutrition 0.000 description 16
- 239000000178 monomer Substances 0.000 description 12
- 239000005060 rubber Substances 0.000 description 12
- 229920002554 vinyl polymer Polymers 0.000 description 12
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- 229920001577 copolymer Polymers 0.000 description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 6
- 150000002367 halogens Chemical class 0.000 description 5
- 150000002736 metal compounds Chemical class 0.000 description 5
- 150000002903 organophosphorus compounds Chemical class 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- 229920005992 thermoplastic resin Polymers 0.000 description 5
- 239000005062 Polybutadiene Substances 0.000 description 4
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 4
- 239000000347 magnesium hydroxide Substances 0.000 description 4
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 4
- 229920002857 polybutadiene Polymers 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 230000001588 bifunctional effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000004898 kneading Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 3
- 229920001568 phenolic resin Polymers 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 229920003048 styrene butadiene rubber Polymers 0.000 description 3
- XZZNDPSIHUTMOC-UHFFFAOYSA-N triphenyl phosphate Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)(=O)OC1=CC=CC=C1 XZZNDPSIHUTMOC-UHFFFAOYSA-N 0.000 description 3
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 2
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 2
- 239000002216 antistatic agent Substances 0.000 description 2
- 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 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 230000001771 impaired effect Effects 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000000314 lubricant Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 239000011574 phosphorus Substances 0.000 description 2
- 229920002959 polymer blend Polymers 0.000 description 2
- 229920001955 polyphenylene ether Polymers 0.000 description 2
- 239000012779 reinforcing material Substances 0.000 description 2
- 239000000779 smoke Substances 0.000 description 2
- 239000003381 stabilizer Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- WVLBCYQITXONBZ-UHFFFAOYSA-N trimethyl phosphate Chemical compound COP(=O)(OC)OC WVLBCYQITXONBZ-UHFFFAOYSA-N 0.000 description 2
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 2
- 229920006163 vinyl copolymer Polymers 0.000 description 2
- QYOJZFBQEAZNEW-UHFFFAOYSA-N 1-(2-methylphenyl)pyrrole-2,5-dione Chemical compound CC1=CC=CC=C1N1C(=O)C=CC1=O QYOJZFBQEAZNEW-UHFFFAOYSA-N 0.000 description 1
- BQTPKSBXMONSJI-UHFFFAOYSA-N 1-cyclohexylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1CCCCC1 BQTPKSBXMONSJI-UHFFFAOYSA-N 0.000 description 1
- QWBBPBRQALCEIZ-UHFFFAOYSA-N 2,3-dimethylphenol Chemical compound CC1=CC=CC(O)=C1C QWBBPBRQALCEIZ-UHFFFAOYSA-N 0.000 description 1
- CZNRFEXEPBITDS-UHFFFAOYSA-N 2,5-bis(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=C(C(C)(C)CC)C=C1O CZNRFEXEPBITDS-UHFFFAOYSA-N 0.000 description 1
- JZODKRWQWUWGCD-UHFFFAOYSA-N 2,5-di-tert-butylbenzene-1,4-diol Chemical compound CC(C)(C)C1=CC(O)=C(C(C)(C)C)C=C1O JZODKRWQWUWGCD-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
- ZZXILYOBAFPJNS-UHFFFAOYSA-N 2-octylbenzene-1,4-diol Chemical compound CCCCCCCCC1=CC(O)=CC=C1O ZZXILYOBAFPJNS-UHFFFAOYSA-N 0.000 description 1
- LBBOQIHGWMYDPM-UHFFFAOYSA-N 2-tert-butylphenol;formaldehyde Chemical compound O=C.CC(C)(C)C1=CC=CC=C1O LBBOQIHGWMYDPM-UHFFFAOYSA-N 0.000 description 1
- AIBRSVLEQRWAEG-UHFFFAOYSA-N 3,9-bis(2,4-ditert-butylphenoxy)-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP1OCC2(COP(OC=3C(=CC(=CC=3)C(C)(C)C)C(C)(C)C)OC2)CO1 AIBRSVLEQRWAEG-UHFFFAOYSA-N 0.000 description 1
- ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-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
- ADRNSOYXKABLGT-UHFFFAOYSA-N 8-methylnonyl diphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OCCCCCCCC(C)C)OC1=CC=CC=C1 ADRNSOYXKABLGT-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- 229920000181 Ethylene propylene rubber Polymers 0.000 description 1
- PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004695 Polyether sulfone Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004734 Polyphenylene sulfide Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- YSMRWXYRXBRSND-UHFFFAOYSA-N TOTP Chemical compound CC1=CC=CC=C1OP(=O)(OC=1C(=CC=CC=1)C)OC1=CC=CC=C1C YSMRWXYRXBRSND-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- KVBYPTUGEKVEIJ-UHFFFAOYSA-N benzene-1,3-diol;formaldehyde Chemical compound O=C.OC1=CC=CC(O)=C1 KVBYPTUGEKVEIJ-UHFFFAOYSA-N 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical compound C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- UNKQPEQSAGXBEV-UHFFFAOYSA-N formaldehyde;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound O=C.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 UNKQPEQSAGXBEV-UHFFFAOYSA-N 0.000 description 1
- XILZQVIJRBMVMY-UHFFFAOYSA-N formaldehyde;4-hydroxybenzonitrile Chemical compound O=C.OC1=CC=C(C#N)C=C1 XILZQVIJRBMVMY-UHFFFAOYSA-N 0.000 description 1
- BXCCKEJWQJEUMS-UHFFFAOYSA-N formaldehyde;4-nonylphenol Chemical compound O=C.CCCCCCCCCC1=CC=C(O)C=C1 BXCCKEJWQJEUMS-UHFFFAOYSA-N 0.000 description 1
- ZLSPCFYPYRYKNF-UHFFFAOYSA-N formaldehyde;4-octylphenol Chemical compound O=C.CCCCCCCCC1=CC=C(O)C=C1 ZLSPCFYPYRYKNF-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- SEEYREPSKCQBBF-UHFFFAOYSA-N n-methylmaleimide Chemical compound CN1C(=O)C=CC1=O SEEYREPSKCQBBF-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [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
- 230000002093 peripheral effect Effects 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 150000003018 phosphorus compounds Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001485 poly(butyl acrylate) polymer Polymers 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002285 poly(styrene-co-acrylonitrile) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920000069 polyphenylene sulfide Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920000346 polystyrene-polyisoprene block-polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 1
- 229960001755 resorcinol Drugs 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 229960001860 salicylate Drugs 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 1
- QLORRTLBSJTMSN-UHFFFAOYSA-N tris(2,6-dimethylphenyl) phosphate Chemical compound CC1=CC=CC(C)=C1OP(=O)(OC=1C(=CC=CC=1C)C)OC1=C(C)C=CC=C1C QLORRTLBSJTMSN-UHFFFAOYSA-N 0.000 description 1
- WGKLOLBTFWFKOD-UHFFFAOYSA-N tris(2-nonylphenyl) phosphite Chemical compound CCCCCCCCCC1=CC=CC=C1OP(OC=1C(=CC=CC=1)CCCCCCCCC)OC1=CC=CC=C1CCCCCCCCC WGKLOLBTFWFKOD-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Classifications
-
- 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
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/41—Compounds containing sulfur bound to oxygen
-
- 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
-
- 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
- C08K5/5317—Phosphonic compounds, e.g. R—P(:O)(OR')2
- C08K5/5333—Esters of phosphonic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L55/00—Compositions of homopolymers or copolymers, obtained by polymerisation reactions only involving carbon-to-carbon unsaturated bonds, not provided for in groups C08L23/00 - C08L53/00
- C08L55/02—ABS [Acrylonitrile-Butadiene-Styrene] polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
- C08L61/04—Condensation polymers of aldehydes or ketones with phenols only
- C08L61/06—Condensation polymers of aldehydes or ketones with phenols only of aldehydes with phenols
-
- 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
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)
- Phenolic Resins Or Amino Resins (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10162229A JPH11343382A (ja) | 1998-04-01 | 1998-06-10 | 難燃性樹脂組成物 |
| SG9805885A SG79244A1 (en) | 1998-04-01 | 1998-12-22 | Flame-retarded resin composition |
| TW087121483A TW561172B (en) | 1998-04-01 | 1998-12-23 | Flame-retarded resin composition |
| MYPI98005941A MY129163A (en) | 1998-04-01 | 1998-12-30 | Flame-retarded resin composition |
| ES99100236T ES2191373T3 (es) | 1998-04-01 | 1999-01-08 | Composicion de resina de llama retardada. |
| DE69906616T DE69906616T2 (de) | 1998-04-01 | 1999-01-08 | Flammhemmende Kunstharz-Zusammensetzung |
| EP99100236A EP0947547B1 (en) | 1998-04-01 | 1999-01-08 | Flame-retarded resin composition |
| KR1019990001851A KR100564920B1 (ko) | 1998-04-01 | 1999-01-22 | 난연성 수지 조성물 |
| CN99101399A CN1114661C (zh) | 1998-04-01 | 1999-01-28 | 阻燃性树脂组合物 |
| US09/886,276 US6462112B2 (en) | 1998-04-01 | 2001-06-22 | Flame-retarded acrylonitrile-butadiene-styrene resin |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP8883198 | 1998-04-01 | ||
| JP10-88831 | 1998-04-01 | ||
| JP10162229A JPH11343382A (ja) | 1998-04-01 | 1998-06-10 | 難燃性樹脂組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH11343382A true JPH11343382A (ja) | 1999-12-14 |
| JPH11343382A5 JPH11343382A5 (enExample) | 2005-09-29 |
Family
ID=26430173
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP10162229A Pending JPH11343382A (ja) | 1998-04-01 | 1998-06-10 | 難燃性樹脂組成物 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US6462112B2 (enExample) |
| EP (1) | EP0947547B1 (enExample) |
| JP (1) | JPH11343382A (enExample) |
| KR (1) | KR100564920B1 (enExample) |
| CN (1) | CN1114661C (enExample) |
| DE (1) | DE69906616T2 (enExample) |
| ES (1) | ES2191373T3 (enExample) |
| MY (1) | MY129163A (enExample) |
| SG (1) | SG79244A1 (enExample) |
| TW (1) | TW561172B (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100373211B1 (ko) * | 2000-09-05 | 2003-02-25 | 주식회사 엘지화학 | 비할로겐 스티렌계 열가소성 난연 수지 조성물 |
| WO2005017021A1 (en) * | 2003-08-14 | 2005-02-24 | Cheil Industries Inc. | Flameproof thermoplastic resin composition |
| US7772303B2 (en) | 2006-12-27 | 2010-08-10 | Cheil Industries Inc. | Flame retardant thermoplastic resin composition having excellent weatherability |
| JP2011084607A (ja) * | 2009-10-14 | 2011-04-28 | Toyo Ink Mfg Co Ltd | 難燃性樹脂組成物 |
| JP2014177596A (ja) * | 2013-03-15 | 2014-09-25 | Ricoh Co Ltd | 再生樹脂組成物、成形品、画像形成装置及び再生樹脂組成物の製造方法 |
| WO2019159540A1 (ja) * | 2018-02-16 | 2019-08-22 | 大八化学工業株式会社 | 芳香族リン酸エステルを含む難燃剤およびそれを含む熱可塑性樹脂組成物 |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60045341D1 (de) | 1999-07-09 | 2011-01-20 | Daihachi Chem Ind | Flammschutzmittel für harze und flammgeschützte harzzusammensetzung die diese enthalten |
| CN100365035C (zh) * | 2000-08-18 | 2008-01-30 | 长春人造树脂厂股份有限公司 | 具酚醛结构的含磷聚合物及其用途 |
| US7235597B2 (en) | 2001-09-27 | 2007-06-26 | Lg Chem, Ltd. | Styrenic thermoplastic resin composition containing an aromatic pentaerythrityl diphosphate |
| WO2004087811A1 (ja) * | 2003-03-27 | 2004-10-14 | Matsushita Electric Works, Ltd. | 難燃性エポキシ樹脂組成物、プリプレグおよび金属張り積層板 |
| US7087703B2 (en) * | 2004-07-26 | 2006-08-08 | Georgia-Pacific Resins, Inc. | Phenolic resin compositions containing etherified hardeners |
| DE102008038054A1 (de) * | 2008-08-16 | 2010-02-18 | Lanxess Deutschland Gmbh | Halogenfreie, flammgeschützte Polyurethanschaumstoffe mit geringem Scorch |
| CN102786767B (zh) * | 2012-05-15 | 2014-11-26 | 金发科技股份有限公司 | 一种超高流动无卤阻燃abs及其制备方法 |
| JP6360044B2 (ja) | 2012-06-06 | 2018-07-18 | イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ | 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 |
| EP3201263B1 (en) | 2014-10-01 | 2019-01-02 | E. I. du Pont de Nemours and Company | Low smoke halogen free flame retardant thermoplastic elastomer compositions |
| CN107974034A (zh) * | 2017-11-24 | 2018-05-01 | 广东威林工程塑料股份有限公司 | 一种高热稳定性的磷、卤、硅复合阻燃材料及其制备方法 |
| CN108623972A (zh) * | 2018-05-25 | 2018-10-09 | 安徽尼古拉电子科技有限公司 | 一种抗冲耐磨线缆护套材料及其制备方法 |
| EP4350758B1 (en) * | 2021-05-28 | 2025-07-02 | Sumitomo Bakelite Co., Ltd. | Sealing resin composition |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4526917A (en) * | 1980-06-20 | 1985-07-02 | General Electric Company | Flame retardant mixture of triaryl phosphates and resinous compositions thereof |
| DE3401835A1 (de) * | 1984-01-20 | 1985-07-25 | Basf Ag, 6700 Ludwigshafen | Halogenfreie, flammgeschuetzte thermoplastische formmasse |
| DE3506193A1 (de) * | 1985-02-22 | 1986-08-28 | Basf Ag, 6700 Ludwigshafen | Halogenfreie, selbstverloeschende thermoplastische formmasse |
| JPH0645739B2 (ja) | 1985-06-19 | 1994-06-15 | 積水化学工業株式会社 | 難燃性ａｂｓ樹脂組成物 |
| JP2552780B2 (ja) | 1991-04-16 | 1996-11-13 | 大八化学工業株式会社 | 芳香族ジホスフェートの製造方法と用途 |
| EP0522653A1 (en) * | 1991-07-12 | 1993-01-13 | Dsm N.V. | Flame-retardant polymer composition |
| EP0538950B1 (en) * | 1991-10-25 | 1996-05-08 | Dsm N.V. | Flame-retardant polymer composition |
| US5455292A (en) | 1992-08-06 | 1995-10-03 | Asahi Kasei Kogyo Kabushiki Kaisha | Hydrolytically stable, halogen-free flame retardant resin composition |
| JPH06248160A (ja) * | 1993-02-26 | 1994-09-06 | Japan Synthetic Rubber Co Ltd | 難燃性樹脂組成物 |
| DE4328656A1 (de) * | 1993-08-26 | 1995-03-02 | Bayer Ag | Flammwidrige, spannungsrißbeständige Polycarbonat-ABS-Formmassen |
| JPH0748491A (ja) | 1994-02-25 | 1995-02-21 | Japan Synthetic Rubber Co Ltd | 難燃用ベース樹脂組成物および難燃熱可塑性樹脂組成物 |
| TW287181B (enExample) * | 1994-05-10 | 1996-10-01 | Taishl Kagaku Kogyo Kk | |
| KR0139249B1 (ko) | 1994-09-05 | 1998-05-01 | 유현식 | 난연성을 갖는 열가소성 수지 조성물 |
| US6066686A (en) * | 1996-07-05 | 2000-05-23 | Daicel Chemical Industries, Ltd. | Polycarbonate compositions |
| DE19547884A1 (de) * | 1995-12-21 | 1997-06-26 | Basf Ag | Formmassen auf der Basis von Polycarbonaten |
-
1998
- 1998-06-10 JP JP10162229A patent/JPH11343382A/ja active Pending
- 1998-12-22 SG SG9805885A patent/SG79244A1/en unknown
- 1998-12-23 TW TW087121483A patent/TW561172B/zh not_active IP Right Cessation
- 1998-12-30 MY MYPI98005941A patent/MY129163A/en unknown
-
1999
- 1999-01-08 EP EP99100236A patent/EP0947547B1/en not_active Expired - Lifetime
- 1999-01-08 DE DE69906616T patent/DE69906616T2/de not_active Expired - Lifetime
- 1999-01-08 ES ES99100236T patent/ES2191373T3/es not_active Expired - Lifetime
- 1999-01-22 KR KR1019990001851A patent/KR100564920B1/ko not_active Expired - Fee Related
- 1999-01-28 CN CN99101399A patent/CN1114661C/zh not_active Expired - Fee Related
-
2001
- 2001-06-22 US US09/886,276 patent/US6462112B2/en not_active Expired - Fee Related
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100373211B1 (ko) * | 2000-09-05 | 2003-02-25 | 주식회사 엘지화학 | 비할로겐 스티렌계 열가소성 난연 수지 조성물 |
| WO2005017021A1 (en) * | 2003-08-14 | 2005-02-24 | Cheil Industries Inc. | Flameproof thermoplastic resin composition |
| US7772303B2 (en) | 2006-12-27 | 2010-08-10 | Cheil Industries Inc. | Flame retardant thermoplastic resin composition having excellent weatherability |
| JP2011084607A (ja) * | 2009-10-14 | 2011-04-28 | Toyo Ink Mfg Co Ltd | 難燃性樹脂組成物 |
| JP2014177596A (ja) * | 2013-03-15 | 2014-09-25 | Ricoh Co Ltd | 再生樹脂組成物、成形品、画像形成装置及び再生樹脂組成物の製造方法 |
| WO2019159540A1 (ja) * | 2018-02-16 | 2019-08-22 | 大八化学工業株式会社 | 芳香族リン酸エステルを含む難燃剤およびそれを含む熱可塑性樹脂組成物 |
| KR20200120633A (ko) * | 2018-02-16 | 2020-10-21 | 다이하치 카가쿠 고교 가부시키가이샤 | 방향족 인산 에스테르를 포함하는 난연제 및 그것을 포함하는 열가소성 수지 조성물 |
| JPWO2019159540A1 (ja) * | 2018-02-16 | 2021-01-28 | 大八化学工業株式会社 | 芳香族リン酸エステルを含む難燃剤およびそれを含む熱可塑性樹脂組成物 |
| US11459446B2 (en) | 2018-02-16 | 2022-10-04 | Daihachi Chemical Industry Co., Ltd. | Flame retardant containing aromatic phosphoric acid ester, and thermoplastic resin composition containing same |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0947547A1 (en) | 1999-10-06 |
| CN1114661C (zh) | 2003-07-16 |
| KR19990082693A (ko) | 1999-11-25 |
| DE69906616T2 (de) | 2004-04-08 |
| SG79244A1 (en) | 2001-03-20 |
| US20010049407A1 (en) | 2001-12-06 |
| KR100564920B1 (ko) | 2006-03-30 |
| TW561172B (en) | 2003-11-11 |
| ES2191373T3 (es) | 2003-09-01 |
| MY129163A (en) | 2007-03-30 |
| EP0947547B1 (en) | 2003-04-09 |
| DE69906616D1 (de) | 2003-05-15 |
| CN1230569A (zh) | 1999-10-06 |
| US6462112B2 (en) | 2002-10-08 |
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