JPH0832797B2 - Flame-retardant polymer composition - Google Patents
Flame-retardant polymer compositionInfo
- Publication number
- JPH0832797B2 JPH0832797B2 JP2265384A JP26538490A JPH0832797B2 JP H0832797 B2 JPH0832797 B2 JP H0832797B2 JP 2265384 A JP2265384 A JP 2265384A JP 26538490 A JP26538490 A JP 26538490A JP H0832797 B2 JPH0832797 B2 JP H0832797B2
- Authority
- JP
- Japan
- Prior art keywords
- flame
- polymer composition
- parts
- weight
- retardant polymer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 239000003063 flame retardant Substances 0.000 title claims description 38
- 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 description 37
- 239000000203 mixture Substances 0.000 title claims description 31
- 229920000642 polymer Polymers 0.000 title claims description 27
- 229920000620 organic polymer Polymers 0.000 claims description 19
- 150000002903 organophosphorus compounds Chemical class 0.000 claims description 19
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 16
- 229910052794 bromium Inorganic materials 0.000 claims description 16
- -1 hydroquinone compound Chemical class 0.000 claims description 16
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 15
- 239000003963 antioxidant agent Substances 0.000 claims description 11
- 230000003078 antioxidant effect Effects 0.000 claims description 10
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 claims description 6
- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 2
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 238000000034 method Methods 0.000 description 9
- 150000002484 inorganic compounds Chemical class 0.000 description 7
- 229910010272 inorganic material Inorganic materials 0.000 description 7
- 150000002896 organic halogen compounds Chemical class 0.000 description 7
- 150000001875 compounds Chemical class 0.000 description 6
- 230000000740 bleeding effect Effects 0.000 description 5
- 238000004040 coloring Methods 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000004383 yellowing Methods 0.000 description 5
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
- 238000002386 leaching Methods 0.000 description 4
- 238000010998 test method Methods 0.000 description 4
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 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 2
- VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004709 Chlorinated polyethylene Substances 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 239000004743 Polypropylene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- WHHGLZMJPXIBIX-UHFFFAOYSA-N decabromodiphenyl ether Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br WHHGLZMJPXIBIX-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- 150000005526 organic bromine compounds Chemical class 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 239000004417 polycarbonate Substances 0.000 description 2
- 229920000515 polycarbonate Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 229920001155 polypropylene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 229920005992 thermoplastic resin Polymers 0.000 description 2
- 229920001187 thermosetting polymer Polymers 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
- WESVFLQWZCBKSK-UHFFFAOYSA-N (1,1,3-tribromo-2,2-dimethylpropyl) dihydrogen phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(O)(O)=O WESVFLQWZCBKSK-UHFFFAOYSA-N 0.000 description 1
- XQKQZOLAVMIQHZ-UHFFFAOYSA-N 1,1-dibromo-3-(3,3-dibromopropoxy)propane Chemical compound BrC(Br)CCOCCC(Br)Br XQKQZOLAVMIQHZ-UHFFFAOYSA-N 0.000 description 1
- YATIGPZCMOYEGE-UHFFFAOYSA-N 1,3,5-tribromo-2-[2-(2,4,6-tribromophenoxy)ethoxy]benzene Chemical compound BrC1=CC(Br)=CC(Br)=C1OCCOC1=C(Br)C=C(Br)C=C1Br YATIGPZCMOYEGE-UHFFFAOYSA-N 0.000 description 1
- NZUPFZNVGSWLQC-UHFFFAOYSA-N 1,3,5-tris(2,3-dibromopropyl)-1,3,5-triazinane-2,4,6-trione Chemical compound BrCC(Br)CN1C(=O)N(CC(Br)CBr)C(=O)N(CC(Br)CBr)C1=O NZUPFZNVGSWLQC-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
- QVLXDGDLLZYJAM-UHFFFAOYSA-N 2,5-dioctylbenzene-1,4-diol Chemical compound CCCCCCCCC1=CC(O)=C(CCCCCCCC)C=C1O QVLXDGDLLZYJAM-UHFFFAOYSA-N 0.000 description 1
- FKWOGPPGVRDIRZ-UHFFFAOYSA-N 2-(2-methylbutan-2-yl)benzene-1,4-diol Chemical compound CCC(C)(C)C1=CC(O)=CC=C1O FKWOGPPGVRDIRZ-UHFFFAOYSA-N 0.000 description 1
- SQHCANCMDZVVHF-UHFFFAOYSA-N 2-chloroethyl bis(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OCCCl)OC(Br)(Br)C(C)(C)CBr SQHCANCMDZVVHF-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
- 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
- PZRWFKGUFWPFID-UHFFFAOYSA-N 3,9-dioctadecoxy-2,4,8,10-tetraoxa-3,9-diphosphaspiro[5.5]undecane Chemical compound C1OP(OCCCCCCCCCCCCCCCCCC)OCC21COP(OCCCCCCCCCCCCCCCCCC)OC2 PZRWFKGUFWPFID-UHFFFAOYSA-N 0.000 description 1
- YJCPRZOLSNMRRP-UHFFFAOYSA-N 3-chloropropyl bis(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OCCCCl)OC(Br)(Br)C(C)(C)CBr YJCPRZOLSNMRRP-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
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- RFKRREOEDDXQES-UHFFFAOYSA-N CC(C)CCCCC(C1=CC=CC=C1)(C1=CC=CC=C1)P(O)(O)O Chemical compound CC(C)CCCCC(C1=CC=CC=C1)(C1=CC=CC=C1)P(O)(O)O RFKRREOEDDXQES-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- 239000004640 Melamine resin Substances 0.000 description 1
- CCVGTXWUPATNAJ-UHFFFAOYSA-N O1POC2=CC=CC=C2OPOC2=CC=CC=C12 Chemical compound O1POC2=CC=CC=C2OPOC2=CC=CC=C12 CCVGTXWUPATNAJ-UHFFFAOYSA-N 0.000 description 1
- OAQMERIIGXMPBA-UHFFFAOYSA-N P(=O)(OC(C(CBr)(C)C)(Br)Br)(OC(C(CBr)(C)C)(Br)Br)OC Chemical compound P(=O)(OC(C(CBr)(C)C)(Br)Br)(OC(C(CBr)(C)C)(Br)Br)OC OAQMERIIGXMPBA-UHFFFAOYSA-N 0.000 description 1
- SBDSTFRTBGLUTQ-UHFFFAOYSA-N P(=O)(OC(C(CBr)(C)C)(Br)Br)(OC(C(CBr)(C)C)(Br)Br)OC1=C(C(=C(C=C1)Br)Br)Br Chemical compound P(=O)(OC(C(CBr)(C)C)(Br)Br)(OC(C(CBr)(C)C)(Br)Br)OC1=C(C(=C(C=C1)Br)Br)Br SBDSTFRTBGLUTQ-UHFFFAOYSA-N 0.000 description 1
- KBHLFNMAWNHRJD-UHFFFAOYSA-N P(=O)(OC1=C(C(=C(C=C1)Br)Br)Br)(OC1=C(C(=C(C=C1)Br)Br)Br)OC(C(CBr)(C)C)(Br)Br Chemical compound P(=O)(OC1=C(C(=C(C=C1)Br)Br)Br)(OC1=C(C(=C(C=C1)Br)Br)Br)OC(C(CBr)(C)C)(Br)Br KBHLFNMAWNHRJD-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 229920001807 Urea-formaldehyde Polymers 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- KOUAXZBXYWNVHI-UHFFFAOYSA-N bis(3,3-dichloropropyl) (1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OCCC(Cl)Cl)OCCC(Cl)Cl KOUAXZBXYWNVHI-UHFFFAOYSA-N 0.000 description 1
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- GDVKFRBCXAPAQJ-UHFFFAOYSA-A dialuminum;hexamagnesium;carbonate;hexadecahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Al+3].[Al+3].[O-]C([O-])=O GDVKFRBCXAPAQJ-UHFFFAOYSA-A 0.000 description 1
- UJSSNDKVUQJEGE-UHFFFAOYSA-N dichloro propyl phosphate Chemical compound CCCOP(=O)(OCl)OCl UJSSNDKVUQJEGE-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- WRTUWJJNYUTLHN-UHFFFAOYSA-N ethyl bis(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound P(=O)(OC(C(CBr)(C)C)(Br)Br)(OC(C(CBr)(C)C)(Br)Br)OCC WRTUWJJNYUTLHN-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012757 flame retardant agent Substances 0.000 description 1
- CAYGQBVSOZLICD-UHFFFAOYSA-N hexabromobenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1Br CAYGQBVSOZLICD-UHFFFAOYSA-N 0.000 description 1
- 229920005669 high impact polystyrene Polymers 0.000 description 1
- 239000004797 high-impact polystyrene Substances 0.000 description 1
- 229960001545 hydrotalcite Drugs 0.000 description 1
- 229910001701 hydrotalcite Inorganic materials 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- GVYLCNUFSHDAAW-UHFFFAOYSA-N mirex Chemical compound ClC12C(Cl)(Cl)C3(Cl)C4(Cl)C1(Cl)C1(Cl)C2(Cl)C3(Cl)C4(Cl)C1(Cl)Cl GVYLCNUFSHDAAW-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 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
- 239000012188 paraffin wax Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- FKFQIJICWPMWAX-UHFFFAOYSA-N phenyl bis(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC1=CC=CC=C1 FKFQIJICWPMWAX-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920006380 polyphenylene oxide Polymers 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000004250 tert-Butylhydroquinone Substances 0.000 description 1
- 235000019281 tert-butylhydroquinone Nutrition 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-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
- QQBLOZGVRHAYGT-UHFFFAOYSA-N tris-decyl phosphite Chemical compound CCCCCCCCCCOP(OCCCCCCCCCC)OCCCCCCCCCC QQBLOZGVRHAYGT-UHFFFAOYSA-N 0.000 description 1
- BHYQWBKCXBXPKM-UHFFFAOYSA-N tris[3-bromo-2,2-bis(bromomethyl)propyl] phosphate Chemical compound BrCC(CBr)(CBr)COP(=O)(OCC(CBr)(CBr)CBr)OCC(CBr)(CBr)CBr BHYQWBKCXBXPKM-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
- 229920006305 unsaturated polyester Polymers 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Description
【発明の詳細な説明】 （産業上の利用分野） 本発明は、難燃性に優れ，かつブリード現象を生じる
ことのない成形体を形成し得る難燃性重合体組成物に関
する。特に，燃焼したときに溶融した樹脂の滴下（ドリ
ッピング）が生じることのない成形体を形成し得る難燃
性重合体組成物に関する。TECHNICAL FIELD The present invention relates to a flame-retardant polymer composition having excellent flame retardancy and capable of forming a molded article that does not cause a bleeding phenomenon. In particular, the present invention relates to a flame-retardant polymer composition capable of forming a molded body that does not cause dripping of molten resin when burned.
（従来の技術） ポリプロピレン，ポリスチレン，アクリロニトリル・
ブタジエン・スチレン（ABS）樹脂などの熱可塑性樹
脂，およびポリウレタン，フェノールなどの熱硬化性樹
脂のような有機重合体は，比較的安価に得られかつ成形
が容易であるなどの優れた特性を有するため，電子部品
や自動車部品をはじめ生活用品全般にわたり広く利用さ
れている。しかし，これらの有機重合体は易燃性である
ため，ひとたび火災が発生すると簡単に燃焼・消失す
る。ケーブルの火災などは特に社会に大きな影響を与え
る。今日では電気製品，自動車内装品，繊維製品など，
これら有機重合体の利用分野の一部では，法律で難燃化
が義務づけられている。(Conventional technology) Polypropylene, polystyrene, acrylonitrile
Thermoplastic resins such as butadiene-styrene (ABS) resins and organic polymers such as thermosetting resins such as polyurethane and phenol have excellent properties such as being relatively inexpensive to obtain and easy to mold. Therefore, it is widely used in all kinds of daily necessities such as electronic parts and automobile parts. However, since these organic polymers are flammable, they easily burn and disappear once a fire occurs. Cable fires have a particularly great impact on society. Today, electrical products, automobile interior products, textile products,
In some of the fields of application of these organic polymers, flame retardation is obligatory.
有機重合体に難燃性を付与する方法としては，樹脂成
形品の調製時に難燃剤を添加する方法が挙げられる。難
燃剤としては，無機化合物，有機リン化合物，有機ハロ
ゲン化合物，ハロゲン含有有機リン化合物などがあり，
なかでも有機臭素化合物，臭素含有有機リン化合物が優
れた難燃効果を発揮する。しかし，このような有機臭素
化合物や臭素含有有機リン化合物を有機重合体に添加す
ると，配合した上記難燃剤が，成形時熱分解し成形体に
ヤケが生じたり，成形体の表面に浮き出るというブリー
ド現象が認められる。As a method of imparting flame retardancy to the organic polymer, a method of adding a flame retardant at the time of preparing a resin molded product can be mentioned. Flame retardants include inorganic compounds, organic phosphorus compounds, organic halogen compounds, halogen-containing organic phosphorus compounds, etc.
Above all, organic bromine compounds and bromine-containing organic phosphorus compounds exhibit excellent flame retardant effects. However, when such an organic bromine compound or bromine-containing organic phosphorus compound is added to an organic polymer, the blended flame retardant is thermally decomposed at the time of molding to cause bleeding of the molded body or bleeding on the surface of the molded body. The phenomenon is observed.
各種成形体の難燃性試験や難燃性規格としては,ASTM,
UL,MIL,JISなどの各種の規格が知られており，成形体の
用途に応じてそれぞれの試験法が適用されている。例え
ば,UL-94のＶ−０もしくはＶ−１グレードの判定基準を
満たす樹脂としては，燃焼したときに溶融した樹脂が滴
下（ドリッピング）しないような樹脂である。上記臭素
含有有機リン化合物，特に臭素含有脂肪族有機リン化合
物を使用した場合には，燃焼したときに該樹脂が溶融し
て滴下しやすくなる。このように，上記臭素含有有機リ
ン化合物を難燃剤とした場合には,UL-94のＶ−０もしく
はＶ−１の規格を充分に満たす難燃性を有する製品が得
られない。As flame retardancy tests and flame retardancy standards for various molded products, ASTM,
Various standards such as UL, MIL, JIS are known, and each test method is applied according to the intended use of the molded product. For example, a resin that meets the criteria for the UL-0 V-0 or V-1 grade is a resin that does not drip the molten resin when burned. When the bromine-containing organic phosphorus compound, particularly the bromine-containing aliphatic organic phosphorus compound, is used, the resin is melted and easily dropped when burned. As described above, when the above bromine-containing organophosphorus compound is used as a flame retardant, a product having flame retardancy sufficiently satisfying the UL-94 V-0 or V-1 standard cannot be obtained.
（発明が解決しようとする課題） 本発明は上記従来の欠点を解決するものであり，その
目的とするところは，難燃性に優れ，かつブリード現象
を生じることのない成形体を形成し得る難燃性重合体組
成物を提供することにある。本発明の他の目的は，燃焼
したときに溶融した樹脂の滴下（ドリッピング）が生じ
ることのない成形体を形成し得る難燃性重合体組成物を
提供することにある。(Problems to be Solved by the Invention) The present invention is to solve the above-mentioned conventional drawbacks, and an object of the present invention is to form a molded article having excellent flame retardancy and free from bleeding phenomenon. It is to provide a flame-retardant polymer composition. Another object of the present invention is to provide a flame-retardant polymer composition capable of forming a molded body that does not cause dripping of molten resin when burned.
（課題を解決するための手段） 発明者らは，特定の構造を有する臭素含有有機リン化
合物と，ヘキサブロモシクロドデカンと酸化防止剤とを
含有する樹脂組成物が難燃性に優れ，ブリード現象を生
じることがなく，そして燃焼したときに溶融した樹脂の
滴下が生じることのない成形体を形成し得ることを見い
出し，本発明を完成するに至った。(Means for Solving the Problems) The inventors have found that a resin composition containing a bromine-containing organophosphorus compound having a specific structure, hexabromocyclododecane, and an antioxidant is excellent in flame retardancy and causes a bleed phenomenon. It has been found that a molded body can be formed which does not cause dripping and does not cause dripping of molten resin when burned, and completed the present invention.
本発明の難燃性重合体組成物は，下記式（Ｉ）で示さ
れる臭素含有有機リン化合物；ヘキサブロモシクロドデ
カン；酸化防止剤；および有機重合体を含有し，そのこ
とにより上記目的が達成される： ここで，R1は炭素原子数が１〜15の炭化水素基または
ハロゲン含有炭化水素基であり，そしてｎは２〜３の整
数である。The flame-retardant polymer composition of the present invention contains a bromine-containing organophosphorus compound represented by the following formula (I); hexabromocyclododecane; an antioxidant; and an organic polymer, whereby the above object is achieved. Done by: Here, R 1 is a hydrocarbon group having 1 to 15 carbon atoms or a halogen-containing hydrocarbon group, and n is an integer of 2 to 3.
本発明の組成物に含有され，上記（Ｉ）式で示される
臭素含有有機リン化合物の具体例としては，次の化合物
が挙げられる：トリス（トリブロモネオペンチル）ホス
フェート，ビス（トリブロモネオペンチル）ジクロロプ
ロピルホスフェート，ビス（トリブロモネオペンチル）
クロロプロピルホスフェート，ビス（トリブロモネオペ
ンチル）クロロエチルホスフェート，ビス（トリブロモ
ネオペンチル）メチルホスフェート，ビス（トリブロモ
ネオペンチル）エチルホスフェート，ビス（トリブロモ
ネオペンチル）フェニルホスフェート，ビス（トリブロ
モネオペンチル）クレジルホスフェート，ビス（トリブ
ロモネオペンチル）トリブロモフェニルホスフェート，
ビス（ジクロロプロピル）トリブロモネオペンチルホス
フェート，ビス（クロロプロピル）トリブロモネオペン
チルホスフェート，ビス（クロロエチル）トリブロモネ
オペンチルホスフェート，ジメチルトリブロモネオペン
チルホスフェート，ジエチルトリブロモネオペンチルホ
スフェート，ジフェニルトリブロモネオペンチルホスフ
ェート，ジクレジルトリブロモネオペンチルホスフェー
ト，ビス（トリブロモフェニル）トリブロモネオペンチ
ルホスフェート等。Specific examples of the bromine-containing organophosphorus compound represented by the above formula (I) contained in the composition of the present invention include the following compounds: tris (tribromoneopentyl) phosphate, bis (tribromoneopentyl). ) Dichloropropyl phosphate, bis (tribromoneopentyl)
Chloropropyl phosphate, bis (tribromoneopentyl) chloroethyl phosphate, bis (tribromoneopentyl) methyl phosphate, bis (tribromoneopentyl) ethyl phosphate, bis (tribromoneopentyl) phenyl phosphate, bis (tribromoneo) Pentyl) cresyl phosphate, bis (tribromoneopentyl) tribromophenyl phosphate,
Bis (dichloropropyl) tribromoneopentyl phosphate, bis (chloropropyl) tribromoneopentylphosphate, bis (chloroethyl) tribromoneopentylphosphate, dimethyltribromoneopentylphosphate, diethyltribromoneopentylphosphate, diphenyltribromoneo Pentyl phosphate, dicresyl tribromoneopentyl phosphate, bis (tribromophenyl) tribromoneopentyl phosphate, etc.
上記有機ハロゲン化合物は前述の臭素含有有機リン化
合物以外のハロゲン含有有機化合物をさしていう。この
具体的としては，次のような化合物が挙げられる：テト
ラブロモビスフェノールＡ（TBA），デカブロモビフェ
ニルエーテル，オクタブロモビフェニルエーテル，ヘキ
サブロモベンゼン，ヘキサブロモシクロドデカン，ブロ
ム化ポリスチレン,TBA−ポリカーボネートオリゴマー,T
BA−エポキシオリゴマー,TBA−ヒドロキシエチルエーテ
ル，ビス（トリブロモフェノキシ）エタン,TBA−2,3−
ジブロモプロピルエーテル，トリス（2,3−ジブロモプ
ロピル）イソシアヌレート，ペンタブロモベンジルポリ
アクリレートなどの臭素含有化合物；および塩素化パラ
フィン，ポリ塩化ビニル，塩素化ポリエチレン，デクロ
ラン（オキシデンタル社製）などの塩素含有化合物。The above organic halogen compound refers to a halogen-containing organic compound other than the above-mentioned bromine-containing organic phosphorus compound. Specific examples thereof include the following compounds: tetrabromobisphenol A (TBA), decabromobiphenyl ether, octabromobiphenyl ether, hexabromobenzene, hexabromocyclododecane, brominated polystyrene, and TBA-polycarbonate oligomer. , T
BA-epoxy oligomer, TBA-hydroxyethyl ether, bis (tribromophenoxy) ethane, TBA-2,3-
Bromine-containing compounds such as dibromopropyl ether, tris (2,3-dibromopropyl) isocyanurate and pentabromobenzyl polyacrylate; and chlorine such as chlorinated paraffin, polyvinyl chloride, chlorinated polyethylene and dechlorane (Oxydental) Contains compounds.
上記無機化合物としては，三酸化アンチモン，酸化ジ
ルコニウム，酸化亜鉛，酸化チタン，硫酸バリウム，水
酸化アルミニウム，水酸化マグネシウム，ハイドロタル
サイト，ホウ酸亜鉛，炭酸カルシウム，ホワイトカーボ
ンなどが挙げられる。Examples of the inorganic compound include antimony trioxide, zirconium oxide, zinc oxide, titanium oxide, barium sulfate, aluminum hydroxide, magnesium hydroxide, hydrotalcite, zinc borate, calcium carbonate, white carbon and the like.
本発明の組成物に含有される酸化防止剤としては下記
式（II）で示されるハイドロキノン化合物および／また
三価の有機リン化合物である。The antioxidant contained in the composition of the present invention is a hydroquinone compound represented by the following formula (II) and / or a trivalent organic phosphorus compound.
ここで，R2，R3，R4およびR5はそれぞれ，水素または
炭素原子数が１〜14のアルキル基である。 Here, R 2 , R 3 , R 4 and R 5 are each hydrogen or an alkyl group having 1 to 14 carbon atoms.
上記ハイドロキノン化合物の具体例としては，ハイド
ロキノン,2,5−ジ−tert−ブチルハイドロキノン,2,5−
ジ−tert−アミルハイドロキノン,2,5−ジオクチルハイ
ドロキノン,tert−アミルハイドロキノン,tert−ブチル
ハイドロキノン，オクチルハイドロキノン等が挙げら
れ，特に，耐熱性に優れたハイドロキノン化合物とし
て,2,5−ジ−tert−アミルハイドロキノン,2,5−ジ−te
rt−ブチルハイドロキノン等が挙げられる。Specific examples of the hydroquinone compound include hydroquinone, 2,5-di-tert-butylhydroquinone, 2,5-
Di-tert-amylhydroquinone, 2,5-dioctylhydroquinone, tert-amylhydroquinone, tert-butylhydroquinone, octylhydroquinone and the like are mentioned, and as a hydroquinone compound having excellent heat resistance, 2,5-di-tert- Amyl hydroquinone, 2,5-di-te
Examples include rt-butyl hydroquinone.
上記三価の有機リン化合物の具体例としては，トリフ
ェニルホスファイト，トリス（ノニルフェニル）ホスフ
ァイト，ジフェニルイソデシルホスファイト，ジフェニ
ルイソオクチルホスファイト，トリス（2,4−ジ−tert
−ブチルフェニル）ホスファイト，ジステアリルペンタ
エリスリトールジホスファイト，ジ（2,4−ジ−tert−
ブチルフェニル）ペンタエリスリトールジホスファイ
ト，テトラキス（2,4−ジ−tert−ブチルフェニル）4,4
−ジフェニレンジホスホナイト等のような化合物が挙げ
られる。Specific examples of the trivalent organic phosphorus compound include triphenylphosphite, tris (nonylphenyl) phosphite, diphenylisodecylphosphite, diphenylisooctylphosphite, tris (2,4-di-tert.
-Butylphenyl) phosphite, distearyl pentaerythritol diphosphite, di (2,4-di-tert-
Butylphenyl) pentaerythritol diphosphite, tetrakis (2,4-di-tert-butylphenyl) 4,4
-Compounds such as diphenylene diphosphonite and the like.
本発明の難燃性重合体組成物に含有される有機重合体
としては，例えば，塩素化ポリエチレン，ポリエチレ
ン，ポリプロピレン，ポリブタジエン，スチレン系樹
脂，耐衝撃性ポリスチレン，ポリ塩化ビニル,ACS樹脂,A
S樹脂,ABS樹脂，ポリフェニレンオキシド，ポリメチル
メタクリレート，ポリアミド，ポリエステル，ポリカー
ボネートなどの熱可塑性樹脂；ポリウレタン，フェノー
ル樹脂，エポキシ樹脂，メラミン樹脂，尿素樹脂，不飽
和ポリエステルなどの熱硬化性樹脂がある。上記樹脂
は,1種または２種以上が混合されて用いられ得る。Examples of the organic polymer contained in the flame-retardant polymer composition of the present invention include chlorinated polyethylene, polyethylene, polypropylene, polybutadiene, styrene resin, high impact polystyrene, polyvinyl chloride, ACS resin, A
Thermoplastic resins such as S resin, ABS resin, polyphenylene oxide, polymethylmethacrylate, polyamide, polyester and polycarbonate; thermosetting resins such as polyurethane, phenol resin, epoxy resin, melamine resin, urea resin and unsaturated polyester. The above resins may be used alone or in combination of two or more.
本発明の難燃性重合体組成物には，上記有機重合体10
0重量部に対して，臭素含有有機リン化合物が0.05〜80
重量部，好ましくは３〜30重量部の割合で含有される。
臭素含有有機リン化合物の含量が0.05重量部を下まわる
と、得られた難燃性重合体組成物に所望の難燃性が付与
されない。80重量部を上まわると，難燃性がそれほど向
上しないばかりか，得られる難燃性重合体組成物の物性
に好ましくない影響を与える。The flame-retardant polymer composition of the present invention includes the organic polymer 10
0 to 80 parts by weight of bromine-containing organophosphorus compound 0.05 to 80
It is contained in an amount of 3 parts by weight, preferably 3 to 30 parts by weight.
When the content of the bromine-containing organophosphorus compound is less than 0.05 part by weight, desired flame retardancy cannot be imparted to the obtained flame retardant polymer composition. If it exceeds 80 parts by weight, not only the flame retardancy is not improved so much, but also the physical properties of the obtained flame retardant polymer composition are adversely affected.
上記有機ハロゲン化合物は，上記有機重合体100重量
部に対して,0.05〜80重量部，好ましくは0.5〜50重量部
の割合で含有される。有機ハロゲン化合物の含量が0.05
重量部を下まわると，得られた難燃性重合体組成物に所
望の難燃性が付与されない。80重量部を上まわると難燃
性が向上しないばかりか，得られる難燃性重合体組成物
の物性に好ましくない影響を与える。The organic halogen compound is contained in an amount of 0.05 to 80 parts by weight, preferably 0.5 to 50 parts by weight, based on 100 parts by weight of the organic polymer. Organic halogen compound content is 0.05
When the amount is less than the weight part, desired flame retardancy is not imparted to the obtained flame retardant polymer composition. If it exceeds 80 parts by weight, not only the flame retardancy is not improved, but also the physical properties of the obtained flame retardant polymer composition are adversely affected.
上記無機化合物は，上記有機重合体100重量部に対し
て,1〜200重量部，好ましくは10〜100重量部の割合で含
有される。無機化合物の含量が１重量部を下まわると，
得られた難燃性重合体組成物に所望の難燃性が付与され
ない。200重量部を上まわると難燃性が向上しないばか
りか，得られる難燃性重合体組成物の物性に好ましくな
い影響を与える。The inorganic compound is contained in an amount of 1 to 200 parts by weight, preferably 10 to 100 parts by weight, based on 100 parts by weight of the organic polymer. When the content of the inorganic compound is less than 1 part by weight,
The desired flame retardancy is not imparted to the obtained flame retardant polymer composition. If it exceeds 200 parts by weight, not only the flame retardancy is not improved, but also the physical properties of the obtained flame retardant polymer composition are adversely affected.
上記有機ハロゲン化合物と無機化合物とを併用した場
合には，それぞれの性質を損なわない範囲の量で難燃性
重合体組成物に含有される。When the organic halogen compound and the inorganic compound are used in combination, they are contained in the flame-retardant polymer composition in an amount that does not impair the respective properties.
上記酸化防止剤は上記有機重合体100重量部に対し,0.
01〜10重量部，好ましくは0.1〜３重量部の割合で含有
される。酸化防止剤の含量が0.01重量部を下まわると，
得られた有機重合体組成物に所望の着色防止性が付与さ
れない。10重量部を上まわると着色防止性が向上しない
ばかりか，得られる難燃性重合体組成物の物性に好まし
くない影響を与える。The above-mentioned antioxidant was added in an amount of 0.
It is contained in a proportion of 01 to 10 parts by weight, preferably 0.1 to 3 parts by weight. When the content of antioxidant is less than 0.01 parts by weight,
The resulting organic polymer composition does not have desired anti-coloring properties. If it exceeds 10 parts by weight, not only the anti-coloring property is not improved, but also the physical properties of the obtained flame-retardant polymer composition are unfavorably affected.
本発明の難燃性重合体組成物には，物性を損なわない
範囲内で，他の難燃剤，酸化防止剤，または充填剤，顔
料，紫外線吸収剤などの添加剤が含有されてもよい。The flame-retardant polymer composition of the present invention may contain other flame-retardant agents, antioxidants, or additives such as fillers, pigments, and ultraviolet absorbers within a range that does not impair the physical properties.
本発明の難燃性重合体組成物は，臭素含有有機リン化
合物，有機ハロゲン化合物，無機化合物および酸化防止
剤の少なくとも１種，および有機重合体を，公知の方法
により混和させて得られる。この方法には，例えば，有
機重合体の重合時において，臭素含有有機リン化合物，
有機ハロゲン化合物，無機化合物，および酸化防止剤の
少なくとも１種を単量体とともに添加する方法；有機重
合体の重合反応終了前にこれらの化合物を添加する方
法；これらの化合物を有機重合体の成形時に添加する方
法；上記方法を組合わせた方法などがある。The flame-retardant polymer composition of the present invention is obtained by mixing at least one of a bromine-containing organic phosphorus compound, an organic halogen compound, an inorganic compound and an antioxidant, and an organic polymer by a known method. This method includes, for example, a bromine-containing organophosphorus compound during the polymerization of an organic polymer,
A method of adding at least one of an organic halogen compound, an inorganic compound, and an antioxidant together with a monomer; a method of adding these compounds before the completion of a polymerization reaction of an organic polymer; a molding of these compounds into an organic polymer. A method of adding at times; a method of combining the above methods, and the like.
（実施例） 以下の本発明の実施例について述べる。実施例中にお
いて，全ての部は重量部である。(Example) The following examples of the present invention will be described. In the examples, all parts are parts by weight.
実施例１ ABS樹脂100部に，トリス（トリブロモネオペンチル）
ホスフェート８部，デカブロモビフェニルエーテル８
部，三酸化アンチモン４部，およびトリデシルホスファ
イト0.5部を配合し，混練した。この混練物を射出成形
機に入れて成形し，下記に示す試験片を得た。この試験
片を用いて，難燃性，溶融滴下物による着火性，難燃剤
のブリード性，および着色度を測定した。各試験方法は
次のとおりである。これらの結果を下表に示す。Example 1 Tris (tribromoneopentyl) was added to 100 parts of ABS resin.
Phosphate 8 parts, decabromobiphenyl ether 8
Parts, 4 parts of antimony trioxide, and 0.5 parts of tridecyl phosphite were mixed and kneaded. This kneaded product was put into an injection molding machine and molded to obtain a test piece shown below. Using this test piece, the flame retardancy, the ignitability by the molten drop, the bleeding property of the flame retardant, and the degree of coloring were measured. Each test method is as follows. The results are shown in the table below.
難燃性 UL-94の試験法に準拠して，試験片（厚さ1/16イン
チ）の難燃性を判定する。UL-94規格における難燃性の
度合は,V−0,V−1,V−2,HBの順である。Flame retardance Judge the flame retardancy of the test piece (1/16 inch thickness) in accordance with the UL-94 test method. The degree of flame retardancy in the UL-94 standard is V-0, V-1, V-2, HB in that order.
溶融滴下物による着火性 UL-94の試験法に準拠して，試験片を燃焼した際に，
溶融した樹脂の滴下物が生じ，かつ試験片の下に敷いた
脱脂綿に着火するか否かを観察する。Ignition due to molten drips In accordance with the test method of UL-94, when burning the test piece,
Observe whether a drop of molten resin occurs and the absorbent cotton laid under the test piece ignites.
ブリード性 試験片を80℃のオーブン中に,24時間放置した後，該
試験片からの難燃剤の浸出を目視により評価する。Bleedability After allowing the test piece to stand in an oven at 80 ° C for 24 hours, the leaching of the flame retardant from the test piece is evaluated visually.
○：難燃剤の浸出が認められない。◯: No leaching of flame retardant is observed.
△：難燃剤の浸出がやや認められる。Δ: Some leaching of the flame retardant is recognized.
×：難燃剤の浸出がかなりの度合で認められる。X: Leaching of the flame retardant is recognized to a considerable degree.
着色度 成形により得られた試験片の着色黄変度，焦げ具合を
目視により評価する。Coloring degree The yellowing degree and the degree of charring of the test piece obtained by molding are visually evaluated.
○：試験片に黄変，焦げが認められない。◯: No yellowing or charring is observed on the test piece.
△：試験片にやや黄変，焦げが認められる。Δ: Some yellowing and charring are observed on the test piece.
×：試験片にかなり黄変，焦げが認められる。X: Significant yellowing and charring are observed on the test piece.
実施例２〜10,および比較例１〜４ 難燃性重合体組成物の各構成成分の重量比を，下表に
示すように変えたこと以外は，実施例１と同様である。
その結果を下表に示す。Examples 2 to 10 and Comparative Examples 1 to 4 The same as Example 1 except that the weight ratio of each component of the flame retardant polymer composition was changed as shown in the table below.
The results are shown in the table below.
（発明の効果） 本発明によれば，このように，得られる成形体の難燃
性に優れた難燃性重合体組成物が提供される。この組成
物を用いて得られる成形体では，成形体の樹脂表面に難
燃剤が浸出することがなく，また燃焼したときに溶融し
た樹脂の滴下が生じることがなく，かつ着色による黄変
が生じない。したがって，本発明の難燃性重合体組成物
は，電気製品，自動車用内装品などに広く利用され得
る。 (Effects of the Invention) According to the present invention, a flame-retardant polymer composition excellent in flame retardancy of the obtained molded article is thus provided. In the molded product obtained by using this composition, the flame retardant does not leach to the resin surface of the molded product, the molten resin does not drip when burned, and yellowing due to coloring occurs. Absent. Therefore, the flame-retardant polymer composition of the present invention can be widely used in electric products, automobile interior parts and the like.
Claims (6)
化合物；ヘキサブロモシクロドデカン；および有機重合
体を含有する難燃性重合体組成物： ここで，R1は炭素原子数が１〜15の炭化水素基またはハ
ロゲン含有炭化水素基であり，そしてｎは２〜３の整数
である。1. A flame-retardant polymer composition containing a bromine-containing organic phosphorus compound represented by the following formula (I); hexabromocyclododecane; and an organic polymer: Here, R 1 is a hydrocarbon group having 1 to 15 carbon atoms or a halogen-containing hydrocarbon group, and n is an integer of 2 to 3.
載の難燃性重合体組成物。2. The flame-retardant polymer composition according to claim 1, further comprising an antioxidant.
臭素含有有機リン化合物が0.05〜80重量部の割合で含有
される請求項１または２に記載の難燃性重合体組成物。3. The flame-retardant polymer composition according to claim 1, wherein the bromine-containing organic phosphorus compound is contained in a proportion of 0.05 to 80 parts by weight with respect to 100 parts by weight of the organic polymer.
ヘキサブロモシクロドデカンが０より大きく５重量部以
下の割合で含有される請求項１または２に記載の難燃性
重合体組成物。4. The flame-retardant polymer composition according to claim 1, wherein the hexabromocyclododecane is contained in a ratio of more than 0 and 5 parts by weight or less based on 100 parts by weight of the organic polymer. .
酸化防止剤が0.01〜10重量部の割合で含有される請求項
２に記載の難燃性重合体組成物。5. The flame-retardant polymer composition according to claim 2, wherein the antioxidant is contained in a proportion of 0.01 to 10 parts by weight with respect to 100 parts by weight of the organic polymer.
ハイドロキノン化合物および／または三価の有機リン化
合物である請求項２に記載の難燃性重合体組成物： ここで，R2，R3，R4およびR5は，それぞれ水素または炭
素原子数が１〜14のアルキル基である。6. The flame-retardant polymer composition according to claim 2, wherein the antioxidant is a hydroquinone compound represented by the following formula (II) and / or a trivalent organic phosphorus compound: Here, R 2 , R 3 , R 4 and R 5 are each hydrogen or an alkyl group having 1 to 14 carbon atoms.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP32780989 | 1989-12-18 | ||
| JP1-327809 | 1989-12-18 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH03227368A JPH03227368A (en) | 1991-10-08 |
| JPH0832797B2 true JPH0832797B2 (en) | 1996-03-29 |
Family
ID=18203231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2265384A Expired - Fee Related JPH0832797B2 (en) | 1989-12-18 | 1990-10-02 | Flame-retardant polymer composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0832797B2 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH07102137A (en) * | 1993-09-30 | 1995-04-18 | Dai Ichi Kogyo Seiyaku Co Ltd | Flame-retardant styrene resin composition |
| AU4911997A (en) * | 1996-10-22 | 1998-05-15 | Fmc Corporation | Flame resistant polyolefin compositions |
| US20030153656A1 (en) * | 2002-01-11 | 2003-08-14 | Rinus Sjerps | Flame retardant polyurethanes and polyisocyanurates, and additives therefor |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046719A (en) | 1975-04-17 | 1977-09-06 | Tenneco Chemicals, Inc. | Flame-retardant resinous compositions containing trihaloneopentyl haloalkyl phosphates |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1085867A (en) * | 1976-02-23 | 1980-09-16 | James A. Albright | Haloalkyl phosphates with increased hydrolytic stability |
| JPS6411164A (en) * | 1987-07-03 | 1989-01-13 | Daihachi Chem Ind | Flame-retardant organic polymer composition |
| JPH01239166A (en) * | 1988-03-18 | 1989-09-25 | Meisei Kagaku Kogyo Kk | Processing agent for synthetic fiber product and processing using the same |
-
1990
- 1990-10-02 JP JP2265384A patent/JPH0832797B2/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4046719A (en) | 1975-04-17 | 1977-09-06 | Tenneco Chemicals, Inc. | Flame-retardant resinous compositions containing trihaloneopentyl haloalkyl phosphates |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH03227368A (en) | 1991-10-08 |
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