JP5631392B2 - フェニルホスホネート難燃性組成物 - Google Patents
フェニルホスホネート難燃性組成物 Download PDFInfo
- Publication number
- JP5631392B2 JP5631392B2 JP2012518890A JP2012518890A JP5631392B2 JP 5631392 B2 JP5631392 B2 JP 5631392B2 JP 2012518890 A JP2012518890 A JP 2012518890A JP 2012518890 A JP2012518890 A JP 2012518890A JP 5631392 B2 JP5631392 B2 JP 5631392B2
- Authority
- JP
- Japan
- Prior art keywords
- tetraalkylpiperidine
- alkyl
- bis
- group
- hydroxy
- 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
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- 239000000203 mixture Substances 0.000 title claims description 95
- QLZHNIAADXEJJP-UHFFFAOYSA-L dioxido-oxo-phenyl-$l^{5}-phosphane Chemical compound [O-]P([O-])(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-L 0.000 title claims description 18
- 239000003063 flame retardant Substances 0.000 title description 46
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$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 description 32
- -1 1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl Chemical group 0.000 claims description 96
- 239000001257 hydrogen Substances 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 54
- 229920001577 copolymer Polymers 0.000 claims description 54
- 125000001424 substituent group Chemical group 0.000 claims description 54
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 150000002431 hydrogen Chemical class 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 27
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 125000002252 acyl group Chemical group 0.000 claims description 23
- OEGSFELAUARXKF-UHFFFAOYSA-N guanidine;phenylphosphonic acid Chemical class NC(N)=N.OP(O)(=O)C1=CC=CC=C1 OEGSFELAUARXKF-UHFFFAOYSA-N 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 229920001169 thermoplastic Polymers 0.000 claims description 17
- 229920002554 vinyl polymer Polymers 0.000 claims description 16
- 239000000178 monomer Substances 0.000 claims description 13
- 238000000034 method Methods 0.000 claims description 12
- 229920000098 polyolefin Polymers 0.000 claims description 12
- 229920001519 homopolymer Polymers 0.000 claims description 11
- FUSRYQFNOAIOLF-UHFFFAOYSA-N phenylphosphonic acid;1,3,5-triazine-2,4,6-triamine Chemical compound NC1=NC(N)=NC(N)=N1.OP(O)(=O)C1=CC=CC=C1 FUSRYQFNOAIOLF-UHFFFAOYSA-N 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 10
- WKRUQZJUAPORKC-UHFFFAOYSA-N 2-[[4,6-bis[4-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butylamino]-1,3,5-triazin-2-yl]amino]ethanol Chemical compound C1C(C)(C)N(OC2CCCCC2)C(C)(C)CC1CCCCNC(N=1)=NC(NCCO)=NC=1NCCCCC(CC1(C)C)CC(C)(C)N1OC1CCCCC1 WKRUQZJUAPORKC-UHFFFAOYSA-N 0.000 claims description 8
- AYJOUNOHHNLBJP-UHFFFAOYSA-N 6-chloro-2-n,4-n-bis[4-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)butyl]-1,3,5-triazine-2,4-diamine Chemical compound C1C(C)(C)N(OC2CCCCC2)C(C)(C)CC1CCCCNC(N=1)=NC(Cl)=NC=1NCCCCC(CC1(C)C)CC(C)(C)N1OC1CCCCC1 AYJOUNOHHNLBJP-UHFFFAOYSA-N 0.000 claims description 8
- 150000001336 alkenes Chemical class 0.000 claims description 6
- RXFCIXRFAJRBSG-UHFFFAOYSA-N 3,2,3-tetramine Chemical compound NCCCNCCNCCCN RXFCIXRFAJRBSG-UHFFFAOYSA-N 0.000 claims description 5
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 5
- 125000006309 butyl amino group Chemical group 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 5
- FYQOHJWNKFULEZ-UHFFFAOYSA-N 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-ol Chemical compound CC(C)(O)CON1C(C)(C)CC(O)CC1(C)C FYQOHJWNKFULEZ-UHFFFAOYSA-N 0.000 claims description 4
- FUVBNYKKKZSBCG-UHFFFAOYSA-N 1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-one Chemical compound CC(C)(O)CON1C(C)(C)CC(=O)CC1(C)C FUVBNYKKKZSBCG-UHFFFAOYSA-N 0.000 claims description 4
- WICJDHJYOIJBDM-UHFFFAOYSA-N 1-[4-[butyl-[4-[butyl-[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl]amino]-6-(2-hydroxyethylamino)-1,3,5-triazin-2-yl]amino]-2,2,6,6-tetramethylpiperidin-1-yl]oxy-2-methylpropan-2-ol Chemical compound N=1C(NCCO)=NC(N(CCCC)C2CC(C)(C)N(OCC(C)(C)O)C(C)(C)C2)=NC=1N(CCCC)C1CC(C)(C)N(OCC(C)(C)O)C(C)(C)C1 WICJDHJYOIJBDM-UHFFFAOYSA-N 0.000 claims description 4
- OKELZJLBUAZSCL-UHFFFAOYSA-N 1-cyclohexyloxy-2,2,6,6-tetramethyl-n-octadecylpiperidin-4-amine Chemical compound CC1(C)CC(NCCCCCCCCCCCCCCCCCC)CC(C)(C)N1OC1CCCCC1 OKELZJLBUAZSCL-UHFFFAOYSA-N 0.000 claims description 4
- KTNPVRSKFWZJEZ-UHFFFAOYSA-N 2,2,6,6-tetramethylpiperidin-1-amine Chemical compound CC1(C)CCCC(C)(C)N1N KTNPVRSKFWZJEZ-UHFFFAOYSA-N 0.000 claims description 4
- VVISQEKWYPFFLK-UHFFFAOYSA-N 2-n,2-n,4-n,4-n-tetrabutyl-6-chloro-1,3,5-triazine-2,4-diamine Chemical compound CCCCN(CCCC)C1=NC(Cl)=NC(N(CCCC)CCCC)=N1 VVISQEKWYPFFLK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims description 4
- KGUHWHHMNQPSRV-UHFFFAOYSA-N [1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl] octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC1CC(C)(C)N(OCC(C)(C)O)C(C)(C)C1 KGUHWHHMNQPSRV-UHFFFAOYSA-N 0.000 claims description 4
- JLOAPAGFWFMZLD-UHFFFAOYSA-N bis(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl) hexanedioate Chemical compound CC1(C)CC(OC(=O)CCCCC(=O)OC2CC(C)(C)N(OC3CCCCC3)C(C)(C)C2)CC(C)(C)N1OC1CCCCC1 JLOAPAGFWFMZLD-UHFFFAOYSA-N 0.000 claims description 4
- OSIVCXJNIBEGCL-UHFFFAOYSA-N bis(2,2,6,6-tetramethyl-1-octoxypiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(OCCCCCCCC)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(OCCCCCCCC)C(C)(C)C1 OSIVCXJNIBEGCL-UHFFFAOYSA-N 0.000 claims description 4
- DVXRGUXKOSSOHV-UHFFFAOYSA-N bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl] decanedioate Chemical compound C1C(C)(C)N(OCC(C)(O)C)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(OCC(C)(C)O)C(C)(C)C1 DVXRGUXKOSSOHV-UHFFFAOYSA-N 0.000 claims description 4
- WUXGYZUOHKJTEY-UHFFFAOYSA-N bis[1-(2-hydroxy-2-methylpropoxy)-2,2,6,6-tetramethylpiperidin-4-yl] hexanedioate Chemical compound C1C(C)(C)N(OCC(C)(O)C)C(C)(C)CC1OC(=O)CCCCC(=O)OC1CC(C)(C)N(OCC(C)(C)O)C(C)(C)C1 WUXGYZUOHKJTEY-UHFFFAOYSA-N 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 4
- 239000000758 substrate Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000001735 carboxylic acids Chemical class 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 53
- 229920000642 polymer Polymers 0.000 description 44
- 239000000654 additive Substances 0.000 description 30
- 125000003118 aryl group Chemical group 0.000 description 22
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- 229920000307 polymer substrate Polymers 0.000 description 22
- 238000012360 testing method Methods 0.000 description 22
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 19
- 239000005977 Ethylene Substances 0.000 description 19
- 125000002947 alkylene group Chemical group 0.000 description 19
- 239000004417 polycarbonate Substances 0.000 description 19
- 239000003381 stabilizer Substances 0.000 description 17
- 239000004952 Polyamide Substances 0.000 description 16
- 229920002647 polyamide Polymers 0.000 description 16
- 239000002253 acid Substances 0.000 description 14
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
- 239000004743 Polypropylene Substances 0.000 description 13
- 230000000996 additive effect Effects 0.000 description 13
- 229920000515 polycarbonate Polymers 0.000 description 13
- 229920001155 polypropylene Polymers 0.000 description 13
- 125000001931 aliphatic group Chemical group 0.000 description 11
- 150000001412 amines Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 10
- 229920000877 Melamine resin Polymers 0.000 description 10
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 10
- 239000005062 Polybutadiene Substances 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- 229920002857 polybutadiene Polymers 0.000 description 9
- 0 **N(*)C(N(*)*)=N Chemical compound **N(*)C(N(*)*)=N 0.000 description 8
- KSSJBGNOJJETTC-UHFFFAOYSA-N COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC Chemical compound COC1=C(C=CC=C1)N(C1=CC=2C3(C4=CC(=CC=C4C=2C=C1)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC(=CC=C1C=1C=CC(=CC=13)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)N(C1=CC=C(C=C1)OC)C1=C(C=CC=C1)OC)C1=CC=C(C=C1)OC KSSJBGNOJJETTC-UHFFFAOYSA-N 0.000 description 8
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 8
- 125000003710 aryl alkyl group Chemical group 0.000 description 8
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 8
- 229920001684 low density polyethylene Polymers 0.000 description 8
- 239000004702 low-density polyethylene Substances 0.000 description 8
- 229920006324 polyoxymethylene Polymers 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 7
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- 229920000573 polyethylene Polymers 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- 229920000915 polyvinyl chloride Polymers 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- QLZHNIAADXEJJP-UHFFFAOYSA-N Phenylphosphonic acid Chemical compound OP(O)(=O)C1=CC=CC=C1 QLZHNIAADXEJJP-UHFFFAOYSA-N 0.000 description 6
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 238000002386 leaching Methods 0.000 description 6
- 125000003884 phenylalkyl group Chemical group 0.000 description 6
- 229920001707 polybutylene terephthalate Polymers 0.000 description 6
- 229920005629 polypropylene homopolymer Polymers 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical group C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 238000002485 combustion reaction Methods 0.000 description 5
- 239000013065 commercial product Substances 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 5
- 229910021641 deionized water Inorganic materials 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
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- 229920006380 polyphenylene oxide Polymers 0.000 description 5
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- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical group NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- 125000002723 alicyclic group Chemical group 0.000 description 4
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- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 4
- 239000004611 light stabiliser Substances 0.000 description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 4
- 229920002492 poly(sulfone) Polymers 0.000 description 4
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- 150000003839 salts Chemical class 0.000 description 4
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- DYIZJUDNMOIZQO-UHFFFAOYSA-N 4,5,6,7-tetrabromo-2-[2-(4,5,6,7-tetrabromo-1,3-dioxoisoindol-2-yl)ethyl]isoindole-1,3-dione Chemical compound O=C1C(C(=C(Br)C(Br)=C2Br)Br)=C2C(=O)N1CCN1C(=O)C2=C(Br)C(Br)=C(Br)C(Br)=C2C1=O DYIZJUDNMOIZQO-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
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- MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 1
- AVIZTSRRMBGYCJ-UHFFFAOYSA-N tetraazanium phosphonato phosphate 1,3,5-triazine-2,4,6-triamine Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].NC1=NC(N)=NC(N)=N1.[O-]P([O-])(=O)OP([O-])([O-])=O AVIZTSRRMBGYCJ-UHFFFAOYSA-N 0.000 description 1
- FAUOSXUSCVJWAY-UHFFFAOYSA-N tetrakis(hydroxymethyl)phosphanium Chemical compound OC[P+](CO)(CO)CO FAUOSXUSCVJWAY-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 125000003944 tolyl group Chemical group 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
- 238000005809 transesterification reaction Methods 0.000 description 1
- 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 1
- JZZBTMVTLBHJHL-UHFFFAOYSA-N tris(2,3-dichloropropyl) phosphate Chemical compound ClCC(Cl)COP(=O)(OCC(Cl)CCl)OCC(Cl)CCl JZZBTMVTLBHJHL-UHFFFAOYSA-N 0.000 description 1
- AZSKHRTUXHLAHS-UHFFFAOYSA-N tris(2,4-di-tert-butylphenyl) phosphate Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(=O)(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 AZSKHRTUXHLAHS-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
- 229920001862 ultra low molecular weight polyethylene Polymers 0.000 description 1
- 229920001866 very low density polyethylene Polymers 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K21/00—Fireproofing materials
- C09K21/06—Organic materials
- C09K21/12—Organic materials containing phosphorus
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Fireproofing Substances (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP09164651.3 | 2009-07-06 | ||
| EP09164651 | 2009-07-06 | ||
| PCT/EP2010/059176 WO2011003773A1 (en) | 2009-07-06 | 2010-06-29 | Phenylphosphonate flame retardant compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2012532239A JP2012532239A (ja) | 2012-12-13 |
| JP2012532239A5 JP2012532239A5 (enExample) | 2013-02-28 |
| JP5631392B2 true JP5631392B2 (ja) | 2014-11-26 |
Family
ID=41319880
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012518890A Expired - Fee Related JP5631392B2 (ja) | 2009-07-06 | 2010-06-29 | フェニルホスホネート難燃性組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20120108712A1 (enExample) |
| EP (1) | EP2451869A1 (enExample) |
| JP (1) | JP5631392B2 (enExample) |
| CN (1) | CN102471533B (enExample) |
| TW (1) | TW201114826A (enExample) |
| WO (1) | WO2011003773A1 (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SG178353A1 (en) | 2009-08-27 | 2012-03-29 | Polymers Crc Ltd | Nano silver-zinc oxide composition |
| JP5562484B2 (ja) * | 2010-05-07 | 2014-07-30 | ビーエーエスエフ ソシエタス・ヨーロピア | アミノグアニジンフェニルホスフィナート難燃剤組成物 |
| US8629220B2 (en) | 2011-01-18 | 2014-01-14 | Basf Se | Hydrolysis-resistant polyamides |
| US8629206B2 (en) | 2011-01-20 | 2014-01-14 | Basf Se | Flame-retardant thermoplastic molding composition |
| EP2683727A1 (en) * | 2011-03-11 | 2014-01-15 | Basf Se | Condensation products of melamine and phenylphosphonic acid and their use as flame retardants |
| AT511509A1 (de) | 2011-04-18 | 2012-12-15 | Sunpor Kunststoff Gmbh | Expandierbare polymerisate aus celluloseacetatbutyrat und styrolpolymerisat |
| AT511090B1 (de) | 2011-04-18 | 2012-09-15 | Sunpor Kunststoff Gmbh | Flammgeschützte expandierbare polymerisate |
| US8653168B2 (en) | 2011-05-10 | 2014-02-18 | Basf Se | Flame-retardant thermoplastic molding composition |
| US8987357B2 (en) | 2011-05-27 | 2015-03-24 | Basf Se | Thermoplastic molding composition |
| JP6188734B2 (ja) * | 2012-03-16 | 2017-08-30 | ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ | 難燃剤としてのｎｏｒ−ｈａｌｓ化合物 |
| DK2825589T3 (da) * | 2012-03-16 | 2020-08-03 | Basf Se | Nor-hals-forbindelser som flammehæmmere |
| DE102012022482A1 (de) | 2012-11-19 | 2014-05-22 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Polymerzusammensetzung mit verbesserter Langzeitstabilität, hieraus hergestellte Formteile sowie Verwendungszwecke |
| DE102013005307A1 (de) | 2013-03-25 | 2014-09-25 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verwendung von organischen Oxyimiden als Flammschutzmittel für Kunststoffe sowie flammgeschützte Kunststoffzusammensetzung und hieraus hergestelltem Formteil |
| DE102014210214A1 (de) | 2014-05-28 | 2015-12-03 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verwendung von Oxyimid-enthaltenden Copolymeren oder Polymeren als Flammschutzmittel, Stabilisatoren, Rheologiemodifikatoren für Kunststoffe, Initiatoren für Polymerisations- und Pfropfprozesse, Vernetzungs- oder Kopplungsmittel sowie solche Copolymere oder Polymere enthaltende Kunststoffformmassen |
| DE102014211276A1 (de) | 2014-06-12 | 2015-12-17 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. | Verwendung von Hydroxybenzotriazol-Derivaten und/oder Hydroxy-Indazol-Derivaten als Flammschutzmittel für Kunststoffe sowie flammgeschützte Kunststoffformmasse |
| CN110678533B (zh) | 2017-06-01 | 2022-07-08 | 大八化学工业株式会社 | 木质材料用阻燃剂和阻燃性木质材料 |
| JP6809709B2 (ja) * | 2017-06-22 | 2021-01-06 | 大八化学工業株式会社 | 難燃剤組成物及び難燃性木質材料 |
| JP7241513B2 (ja) * | 2018-11-20 | 2023-03-17 | Ｐｓジャパン株式会社 | 難燃性スチレン系樹脂組成物、及び成形品 |
| JP7431436B2 (ja) * | 2020-01-14 | 2024-02-15 | 丸菱油化工業株式会社 | 難燃性ポリプロピレン系樹脂組成物 |
| US20240059867A1 (en) | 2022-08-12 | 2024-02-22 | Carl Freudenberg Kg | Flame-retardant molded articles for electrical devices |
| HUE071909T2 (hu) | 2022-08-12 | 2025-10-28 | Freudenberg Carl Kg | Lángálló térhálósított alifás poliketonok |
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| US4061605A (en) * | 1976-03-03 | 1977-12-06 | Eli Simon | Reaction products of benzenephosphonic acid and melamine as flame-retardant additives |
| DE2827867A1 (de) * | 1978-06-24 | 1980-01-17 | Hoechst Ag | Schwerentflammbare thermoplasten |
| US4263201A (en) | 1978-12-07 | 1981-04-21 | General Electric Company | Flame retardant polycarbonate composition |
| US4308197A (en) * | 1980-04-21 | 1981-12-29 | Mcdonnell Douglas Corporation | Fire resistant composites |
| AT369406B (de) * | 1981-02-17 | 1982-12-27 | Chemie Linz Ag | Verwendung von alkandiphosphonsaeuresalzen als flammhemmender zusatz zu kunststoffen |
| FR2620715A1 (fr) * | 1987-09-18 | 1989-03-24 | Sturtz Georges | Compositions de resines synthetiques ayant un comportement au feu ameliore renfermant une polyolefine, un additif ignifugeant phosphore associe a des composes bromes et oxyde d'antimoine ou bien associe ou combine avec un compose azote et eventuellement d'autres additifs et/ou charges et objets conformes produits a partir de ces compositions |
| US5019613A (en) | 1989-03-21 | 1991-05-28 | Ciba-Geigy Corporation | N-hydrocarbyloxy derivatives of hindered amine-substituted S-triazines |
| US5214085A (en) * | 1992-02-03 | 1993-05-25 | General Electric Company | Abrasion-resistant coating compositions with improved weatherability |
| US5393812A (en) * | 1993-08-31 | 1995-02-28 | Hercules Incorporated | Flame retardant, light stable composition |
| JP3804096B2 (ja) * | 1996-03-27 | 2006-08-02 | 東ソー株式会社 | エチレンジアミン−フェニルホスホン酸塩、その製造法及びそれを配合してなる難燃性樹脂組成物 |
| JP2000109705A (ja) * | 1998-10-02 | 2000-04-18 | Tokuyama Corp | 難燃性樹脂組成物 |
| US6271377B1 (en) | 1999-02-25 | 2001-08-07 | Ciba Specialty Chemicals Corporation | Hydroxy-substituted N-alkoxy hindered amines and compositions stabilized therewith |
| ES2361171T3 (es) | 2000-05-19 | 2011-06-14 | Basf Se | Proceso para el incremento controlado del peso molecular de polietileno o mezclas de polietileno. |
| US6730720B2 (en) | 2000-12-27 | 2004-05-04 | General Electric Company | Method for reducing haze in a fire resistant polycarbonate composition |
| JP2002212432A (ja) * | 2001-01-12 | 2002-07-31 | Polyplastics Co | 難燃性樹脂組成物 |
| US6727302B2 (en) | 2001-04-03 | 2004-04-27 | General Electric Company | Transparent, fire-resistant polycarbonate |
| JP2004530785A (ja) * | 2001-06-29 | 2004-10-07 | チバ スペシャルティ ケミカルズ ホールディング インコーポレーテッド | ナノスケール充填剤立体障害性とアミン系光安定剤との相乗的組み合わせ |
| US6660787B2 (en) | 2001-07-18 | 2003-12-09 | General Electric Company | Transparent, fire-resistant polycarbonate compositions |
| EP1466946B1 (en) * | 2001-11-30 | 2011-11-09 | Polyplastics Co., Ltd. | Flame-retardant resin composition |
| KR100873719B1 (ko) * | 2001-12-10 | 2008-12-12 | 시바 홀딩 인코포레이티드 | 난연제 조성물 |
| ITMI20012598A1 (it) * | 2001-12-11 | 2003-06-11 | 3V Sigma Spa | Hals macromolecolari a peso molecolare definito |
| JP4016123B2 (ja) * | 2002-07-22 | 2007-12-05 | 平岡織染株式会社 | 難燃化ポリプロピレン系樹脂膜材 |
| US7138448B2 (en) * | 2002-11-04 | 2006-11-21 | Ciba Specialty Chemicals Corporation | Flame retardant compositions |
| JP2004210882A (ja) * | 2002-12-27 | 2004-07-29 | Polyplastics Co | 難燃性樹脂組成物 |
| CN1950436B (zh) * | 2004-05-13 | 2012-09-05 | 西巴特殊化学品控股有限公司 | 阻燃剂 |
| BRPI0511525A (pt) * | 2004-05-26 | 2007-12-26 | Ciba Sc Holding Ag | retardantes de chama |
| ATE539059T1 (de) * | 2007-02-21 | 2012-01-15 | Basf Se | Symmetrische azoverbindungen in flammverzögerungszusammensetzungen |
| ES2435468T3 (es) * | 2009-02-04 | 2013-12-19 | Basf Se | Estabilizadores macrocíclicos de triazina-HALS N-sustituidos |
| US20110237715A1 (en) * | 2010-03-25 | 2011-09-29 | Basf Se | Flame retardant compositions of phosphinic acid salts and nitroxyl derivatives |
-
2010
- 2010-06-29 WO PCT/EP2010/059176 patent/WO2011003773A1/en not_active Ceased
- 2010-06-29 US US13/376,727 patent/US20120108712A1/en not_active Abandoned
- 2010-06-29 JP JP2012518890A patent/JP5631392B2/ja not_active Expired - Fee Related
- 2010-06-29 CN CN201080030590.2A patent/CN102471533B/zh not_active Expired - Fee Related
- 2010-06-29 EP EP10726512A patent/EP2451869A1/en not_active Withdrawn
- 2010-07-05 TW TW099122048A patent/TW201114826A/zh unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN102471533B (zh) | 2014-07-02 |
| WO2011003773A1 (en) | 2011-01-13 |
| US20120108712A1 (en) | 2012-05-03 |
| EP2451869A1 (en) | 2012-05-16 |
| TW201114826A (en) | 2011-05-01 |
| JP2012532239A (ja) | 2012-12-13 |
| CN102471533A (zh) | 2012-05-23 |
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