JP2013525595A - 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 - Google Patents
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 Download PDFInfo
- Publication number
- JP2013525595A JP2013525595A JP2013509509A JP2013509509A JP2013525595A JP 2013525595 A JP2013525595 A JP 2013525595A JP 2013509509 A JP2013509509 A JP 2013509509A JP 2013509509 A JP2013509509 A JP 2013509509A JP 2013525595 A JP2013525595 A JP 2013525595A
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- Prior art keywords
- alkyl
- composition
- group
- hydrogen
- phenyl
- Prior art date
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- Granted
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- 239000000203 mixture Substances 0.000 title claims abstract description 93
- 239000003063 flame retardant Substances 0.000 title claims abstract description 60
- 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 42
- JANXFQKMPZQVJR-UHFFFAOYSA-N NNC(N)=N.OP(=O)c1ccccc1 Chemical compound NNC(N)=N.OP(=O)c1ccccc1 JANXFQKMPZQVJR-UHFFFAOYSA-N 0.000 title claims description 27
- 150000002118 epoxides Chemical class 0.000 claims abstract description 6
- RRPUBFPVTPEUHJ-UHFFFAOYSA-N [PH2](OC1=CC=CC=C1)=O.NNC(=N)N Chemical compound [PH2](OC1=CC=CC=C1)=O.NNC(=N)N RRPUBFPVTPEUHJ-UHFFFAOYSA-N 0.000 claims abstract description 5
- -1 epoxide compounds Chemical class 0.000 claims description 85
- 239000001257 hydrogen Substances 0.000 claims description 35
- 229910052739 hydrogen Inorganic materials 0.000 claims description 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 30
- 239000000654 additive Substances 0.000 claims description 25
- 229920000307 polymer substrate Polymers 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 15
- 229910052757 nitrogen Inorganic materials 0.000 claims description 14
- 239000003381 stabilizer Substances 0.000 claims description 13
- 230000000996 additive effect Effects 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 229920000877 Melamine resin Polymers 0.000 claims description 9
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 8
- 239000004848 polyfunctional curative Chemical class 0.000 claims description 7
- 229920001169 thermoplastic Polymers 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 239000004114 Ammonium polyphosphate Substances 0.000 claims description 5
- 235000019826 ammonium polyphosphate Nutrition 0.000 claims description 5
- 229920001276 ammonium polyphosphate Polymers 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 229920000388 Polyphosphate Polymers 0.000 claims description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000004464 hydroxyphenyl group Chemical group 0.000 claims description 4
- 239000001205 polyphosphate Substances 0.000 claims description 4
- 235000011176 polyphosphates Nutrition 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 239000000758 substrate Substances 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- DZTVZTIWIQLJRV-UHFFFAOYSA-N NC(N)=N.OP(=O)c1ccccc1 Chemical class NC(N)=N.OP(=O)c1ccccc1 DZTVZTIWIQLJRV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- COAPBYURHXLGMG-UHFFFAOYSA-N azane;1,3,5-triazine-2,4,6-triamine Chemical compound N.NC1=NC(N)=NC(N)=N1 COAPBYURHXLGMG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 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 claims description 2
- ZZMPGNVAROSUSZ-UHFFFAOYSA-N triazanium;1,3,5-triazine-2,4,6-triamine;phosphate Chemical compound [NH4+].[NH4+].[NH4+].[O-]P([O-])([O-])=O.NC1=NC(N)=NC(N)=N1 ZZMPGNVAROSUSZ-UHFFFAOYSA-N 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 34
- 239000004417 polycarbonate Substances 0.000 abstract description 19
- 239000004952 Polyamide Substances 0.000 abstract description 17
- 229920002647 polyamide Polymers 0.000 abstract description 17
- 229920000515 polycarbonate Polymers 0.000 abstract description 13
- 238000004519 manufacturing process Methods 0.000 abstract description 10
- 229920000728 polyester Polymers 0.000 abstract description 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical class C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 53
- 229920001577 copolymer Polymers 0.000 description 42
- 229920003319 Araldite® Polymers 0.000 description 23
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 16
- 239000005977 Ethylene Substances 0.000 description 16
- 125000003118 aryl group Chemical group 0.000 description 15
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 13
- 229920001155 polypropylene Polymers 0.000 description 12
- 239000004743 Polypropylene Substances 0.000 description 11
- 125000000217 alkyl group Chemical group 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000003822 epoxy resin Substances 0.000 description 10
- 239000007788 liquid Substances 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 229920000647 polyepoxide Polymers 0.000 description 10
- 229920002857 polybutadiene Polymers 0.000 description 9
- 229920002554 vinyl polymer Polymers 0.000 description 9
- 239000004593 Epoxy Substances 0.000 description 8
- 239000005062 Polybutadiene Substances 0.000 description 8
- 239000004698 Polyethylene Substances 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 8
- 229920001684 low density polyethylene Polymers 0.000 description 8
- 239000004702 low-density polyethylene Substances 0.000 description 8
- 229910052698 phosphorus Inorganic materials 0.000 description 8
- 229920000573 polyethylene Polymers 0.000 description 8
- 229920006324 polyoxymethylene Polymers 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- HAFNTISAMWOSOH-UHFFFAOYSA-N O1P(=CCC1)=O Chemical compound O1P(=CCC1)=O HAFNTISAMWOSOH-UHFFFAOYSA-N 0.000 description 7
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 description 7
- DWSWCPPGLRSPIT-UHFFFAOYSA-N benzo[c][2,1]benzoxaphosphinin-6-ium 6-oxide Chemical compound C1=CC=C2[P+](=O)OC3=CC=CC=C3C2=C1 DWSWCPPGLRSPIT-UHFFFAOYSA-N 0.000 description 7
- 239000003054 catalyst Substances 0.000 description 7
- 150000001993 dienes Chemical class 0.000 description 7
- 229910052736 halogen Inorganic materials 0.000 description 7
- 150000002367 halogens Chemical class 0.000 description 7
- 239000011574 phosphorus Substances 0.000 description 7
- 239000004800 polyvinyl chloride Substances 0.000 description 7
- 229920000915 polyvinyl chloride Polymers 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 6
- 229920001519 homopolymer Polymers 0.000 description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
- 229920001707 polybutylene terephthalate Polymers 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 6
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 6
- 229920005989 resin Polymers 0.000 description 6
- 239000011347 resin Substances 0.000 description 6
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 5
- 229920000089 Cyclic olefin copolymer Polymers 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- MXRIRQGCELJRSN-UHFFFAOYSA-N O.O.O.[Al] Chemical compound O.O.O.[Al] MXRIRQGCELJRSN-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- 239000004433 Thermoplastic polyurethane Substances 0.000 description 5
- 239000007983 Tris buffer Substances 0.000 description 5
- 229920001971 elastomer Polymers 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 229920001903 high density polyethylene Polymers 0.000 description 5
- 239000004700 high-density polyethylene Substances 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 229920003986 novolac Polymers 0.000 description 5
- 229920000098 polyolefin Polymers 0.000 description 5
- 229920006380 polyphenylene oxide Polymers 0.000 description 5
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 5
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 5
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000005038 ethylene vinyl acetate Substances 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
- 239000012796 inorganic flame retardant Substances 0.000 description 4
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 4
- MLCHBQKMVKNBOV-UHFFFAOYSA-N phenylphosphinic acid Chemical compound OP(=O)C1=CC=CC=C1 MLCHBQKMVKNBOV-UHFFFAOYSA-N 0.000 description 4
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 4
- 229920002492 poly(sulfone) Polymers 0.000 description 4
- 229920000570 polyether Polymers 0.000 description 4
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 229920001897 terpolymer Polymers 0.000 description 4
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 3
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 3
- 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
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 description 3
- 229920002943 EPDM rubber Polymers 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Natural products CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 3
- 239000004793 Polystyrene Substances 0.000 description 3
- 229920002396 Polyurea Polymers 0.000 description 3
- 229920000147 Styrene maleic anhydride Polymers 0.000 description 3
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 3
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 229920001585 atactic polymer Polymers 0.000 description 3
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- 239000004202 carbamide Substances 0.000 description 3
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 230000032798 delamination Effects 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000806 elastomer Substances 0.000 description 3
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- 229920005669 high impact polystyrene Polymers 0.000 description 3
- 239000004797 high-impact polystyrene Substances 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 239000004611 light stabiliser Substances 0.000 description 3
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 150000005673 monoalkenes Chemical class 0.000 description 3
- 125000004430 oxygen atom Chemical group O* 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
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- 239000011701 zinc Substances 0.000 description 3
- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 2
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 description 2
- BPXVHIRIPLPOPT-UHFFFAOYSA-N 1,3,5-tris(2-hydroxyethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound OCCN1C(=O)N(CCO)C(=O)N(CCO)C1=O BPXVHIRIPLPOPT-UHFFFAOYSA-N 0.000 description 2
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 2
- LEVFXWNQQSSNAC-UHFFFAOYSA-N 2-(4,6-diphenyl-1,3,5-triazin-2-yl)-5-hexoxyphenol Chemical compound OC1=CC(OCCCCCC)=CC=C1C1=NC(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=N1 LEVFXWNQQSSNAC-UHFFFAOYSA-N 0.000 description 2
- OLFNXLXEGXRUOI-UHFFFAOYSA-N 2-(benzotriazol-2-yl)-4,6-bis(2-phenylpropan-2-yl)phenol Chemical compound C=1C(N2N=C3C=CC=CC3=N2)=C(O)C(C(C)(C)C=2C=CC=CC=2)=CC=1C(C)(C)C1=CC=CC=C1 OLFNXLXEGXRUOI-UHFFFAOYSA-N 0.000 description 2
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-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
- 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 2
- PYSRRFNXTXNWCD-UHFFFAOYSA-N 3-(2-phenylethenyl)furan-2,5-dione Chemical compound O=C1OC(=O)C(C=CC=2C=CC=CC=2)=C1 PYSRRFNXTXNWCD-UHFFFAOYSA-N 0.000 description 2
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- 239000012188 paraffin wax Substances 0.000 description 1
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- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
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- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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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
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
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- FAUOSXUSCVJWAY-UHFFFAOYSA-N tetrakis(hydroxymethyl)phosphanium Chemical compound OC[P+](CO)(CO)CO FAUOSXUSCVJWAY-UHFFFAOYSA-N 0.000 description 1
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- 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
- 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
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- DXZMANYCMVCPIM-UHFFFAOYSA-L zinc;diethylphosphinate Chemical compound [Zn+2].CCP([O-])(=O)CC.CCP([O-])(=O)CC DXZMANYCMVCPIM-UHFFFAOYSA-L 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
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/02—Guanidine; Salts, complexes or addition compounds thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
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Abstract
Description
本発明は、アミノグアニジンフェニルホスフィナートの塩とポリマー基材との混合物を含む、難燃剤組成物に関する。
a)以下の式
R1〜R5は互いに独立して水素又はC1〜C4アルキル、ヒドロキシ、ヒドロキシ−C1〜C4アルキル及びC1〜C4アルコキシからなる群から選択される置換基を表し;
R6〜R10は互いに独立して水素又はC1〜C4アルキル、フェニル、フェニル−C1〜C4アルキル、(C1〜C4アルキル)1〜3フェニル及び(C1〜C4アルキル)1〜2ヒドロキシフェニルからなる群から選択される置換基を表し;且つ
xは1.0〜2.0の間の数を表す)
のアミノグアニジンフェニルホスフィナート塩;
b)ポリマー基材
を含む組成物に関する。
R1〜R5が水素を表し;
R6〜R10が互いに独立して水素又はC1〜C4アルキルを表し;且つ
xが1.0〜2.0の間の数を表す、組成物に関する。
R1〜R5が水素を表し;
R6〜R10が水素を表し;且つ
xが1.0〜2.0の間の数を表す、組成物に関する。
成分a)
以下の式
R1〜R5は互いに独立して水素又はC1〜C4アルキル、例えば、メチル、エチル、n−又はイソプロピル、又はn−、イソ−又はtert−ブチル、ヒドロキシ、ヒドロキシ−C1〜C4アルキル、例えば、ヒドロキシメチル又は1−又は2−ヒドロキシエチル及びC1〜C4アルコキシ、例えば、メトキシ又はエトキシからなる群から選択される置換基を表し;
R6〜R10は互いに独立して水素又はC1〜C4アルキル、フェニル、フェニル−C1〜C4アルキル、例えば、ベンジル又は1−又は2−フェネチル、(C1〜C4アルキル)1〜3フェニル、例えば、トリル又はメシチル、及び(C1〜C4アルキル)1〜2ヒドロキシフェニル、例えば、4−ヒドロキシ−3,5−ジ−tert−ブチルフェニル又は3−tert−ブチル−4−ヒドロキシ−5−メチル−フェニルからなる群から選択される置換基を表し;
且つxは1.0〜2.0の間の数を表す。
R1〜R5は水素を表し;
R6〜R10は互いに独立して水素又はC1〜C12アルキルを表し;且つ
xは1.0〜2.0の間の数を表す。
R1〜R5は水素を表し;
R6〜R10は互いに独立して水素を表し;且つ
xは1.0〜2.0の間の数を表す。
ポリマー基材との用語は、その範囲内に熱可塑性ポリマー又は熱硬化物を含む。
1.モノオレフィン及びジオレフィンのポリマー、例えばポリプロピレン、ポリイソブチレン、ポリブト−1−エン、ポリ−4−メチルペント−1−エン、ポリビニルシクロヘキサン、ポリイソプレン又はポリブタジエン、並びにシクロオレフィンのポリマー、例えばシクロペンテン又はノルボルネン、ポリエチレン(場合により架橋されてよい)、例えば高密度ポリエチレン(HDPE)、高密度高分子量ポリエチレン(HDPE−HMW)、高密度超高分子量ポリエチレン(HDPE−UHMW)、中密度ポリエチレン(MDPE)、低密度ポリエチレン(LDPE)、直鎖状低密度ポリエチレン(LLDPE)、(VLDPE)及び(ULDPE)。
a)ラジカル重合(通常、高圧且つ高温下にて)
b)通常、周期表の第IVb族、第Vb族、第VIb族又は第VIII族の金属を1種以上含有する触媒を使用する触媒重合。これらの金属は通常、1つ以上の配位子、典型的にはオキシド、ハライド、アルコレート、エステル、エーテル、アミン、アルキル、アルケニル、及び/又はアリールを有し、これらはπ又はσ配位のいずれであってもよい。それらの金属錯体は遊離した形態であるか、あるいは基質、典型的には活性化塩化マグネシウム、塩化チタン(III)、アルミナ又はケイ素酸化物に固定されてよい。それらの触媒は重合媒体中で可溶性又は不溶性であってよい。重合において、該触媒をそれのみで使用するか、あるいは更なる活性剤、典型的には金属アルキル、金属水素化物、金属アルキルハライド、金属アルキルオキシド又は金属アルキルオキサンを使用してもよく、前記金属は周期律表のIa、IIa及び/又はIIIa族の元素である。活性剤は、更なるエステル、エーテル、及びアミン又はシリルエーテル基で都合良く改質されてよい。これらの触媒系は通常、フィリップス、スタンダードオイルインディアナ、チーグラー(−ナッタ)、TNZ(DuPont)、メタロセン又はシングルサイト触媒(SSC)と称される。
上記のホモポリマー及びコポリマーは、シンジオタクチック、アイソタクチック、ヘミアイソタクチック又はアタクチックを含む立体構造を有してよく、ここでアタクチックポリマーが好ましい。ステレオブロックポリマーも含まれる。
I)分子中に少なくとも2つのカルボキシル基を有する化合物とエピクロロヒドリン及び/又はグリセロールジクロロヒドリン及び/又はβ−メチルエピクロロヒドリンとの反応によって得られるポリグリシジルエステル及びポリ(β−メチルグリシジル)エステル。反応は塩基の存在下で行われる。
a)液体ビスフェノールAジグリシジルエーテル、例えば、ARALDITE GY240、ARALDITE GY250、ARALDITE GY260、ARALDITE GY266、ARALDITE GY2600、ARALDITE MY790;
b)固体ビスフェノールAジグリシジルエーテル、例えば、ARALDITE GT6071、ARALDITE GT7071、ARALDITE GT7072、ARALDITE GT6063、ARALDITE GT7203、ARALDITE GT6064、ARALDITE GT7304、ARALDITE GT7004、ARALDITE GT6084、ARALDITE GT1999、ARALDITE GT7077、ARALDITE GT6097、ARALDITE GT7097、ARALDITE GT7008、ARALDITE GT6099、ARALDITE GT6608、ARALDITE GT6609、ARALDITE GT6610;
c)液体ビスフェノールFジグリシジルエーテル、例えば、ARALDITE GY281、ARALDITE GY282、ARALDITE PY302、ARALDITE PY306;
d)テトラフェニルエタンの固体ポリグリシジルエーテル、例えば、CGエポキシ樹脂(登録商標)0163;
e)フェノール−ホルムアルデヒドノボラック(登録商標)の固体及び液体のポリグリシジルエーテル、例えば、EPN1138、EPN1139、GY1180、PY307;
f)o−クレゾール−ホルムアルデヒドノボラックの固体及び液体のポリグリシジルエーテル、例えば、ECN1235、ECN1273、ECN1280、ECN1299;
g)アルコールの液体グリシジルエーテル、例えば、Shell(登録商標)グリシジルエーテル162、ARALDITE DY0390、ARALDITE DY0391;
h)カルボン酸の液体グリシジルエーテル、例えば、シェル(登録商標)カルデュラ(Cardura)Eテレフタル酸エステル、トリメリット酸エステル、ARALDITE PY284;
i)固体複素環エポキシ樹脂(トリグリシジルイソシアヌレート)、例えば、ARALDITE PT810;
k)液体脂環式エポキシ樹脂、例えば、ARALDITE CY179;
l)p−アミノフェノールの液体N,N,O−トリグリシジルエーテル、例えば、ARALDITE MY 0510;
m)テトラグリシジル−4,4’−メチレンベンズアミン又はN,N,N’,N−テトラグリシジルジアミノフェニル−メタン、例えば、ARALDITE MY720、ARALDITE MY721。
Y1は直接結合又は基−O−、−S−又は−C(=O)−O−であり;
Y2は直接結合又は基−SO2−、−CO−、−S−、−SO−、CH2−、−C(CH3)2−又は−C(CF3)2−であり:
且つnは1〜10である)
の基である。
a)約0.05〜30.0質量%のアミノグアニジンフェニルホスフィナート塩(I);
b)約30.0〜95.0質量%の多官能エポキシド化合物;及び0〜60.0質量%の硬化剤化合物
を含む、組成物に関する。
本発明は更に、上で定義される、成分a)及びb)に加えて、任意の成分として、追加の難燃剤並びにいわゆるドリップ防止剤及びポリマー安定剤からなる群から選択される更なる添加剤を含む、組成物に関する。
以下の式
その際、Raは水素又はC1〜C4アルキルを表すか;又はアルコキシアルキル、例えば、以下の式:
アリール、例えば、以下の式:
又はRはアリールアルキル、例えば、以下の式
又はその際、Rはヒドロキシで置換されたアルコキシアルキル、例えば、以下の式
テトラフェニルレソルシノールジホスフェート(Fyrolflex(登録商標)RDP、アクゾノーベル社)、レソルシノールジホスフェートオリゴマー(RDP)、トリフェニルホスフェート、エチレンジアミンジホスフェート(EDAP)、ジエチル−N,N−ビス(2−ヒドロキシエチル)−アミノメチルホスホネート、リン酸のヒドロキシアルキルエステル、カチオンとして例えば、Ca2+、Zn2+、又はAl3+を含む次リン酸(H3PO2)の塩、テトラキス(ヒドロキシメチル)ホスホニウムスルフィド、アンモニウムポリホスフェート及びホスファゼン難燃剤。
ポリ臭化ジフェニルオキシド(DE−60F、Great Lakes社)、デカブロモジフェニルオキシド(DBDPO;Saytex(登録商標)102E)、トリス[3−ブロモ−2,2−ビス(ブロモメチル)プロピル]ホスフェート(PB370(登録商標)、FMC社)、トリス(2,3−ジブロモプロピル)ホスフェート、トリス(2,3−ジクロロプロピル)ホスフェート、クロレンド酸、テトラクロロフタル酸、テトラブロモフタル酸、ポリ−β−クロロエチルトリホスホネート混合物、テトラブロモビスフェノールAビス(2,3−ジブロモプロピルエーテル)(PE68)、臭素化エポキシ樹脂、エチレン−ビス(テトラブロモフタルイミド)(Saytex(登録商標)BT−93)、ビス(ヘキサクロロシクロペンタジエノ)シクロオクタン(Declorane Plus(登録商標))、塩素化パラフィン、オクタブロモジフェニルエーテル、ヘキサクロロシクロペンタジエン誘導体、1,2−ビス(トリブロモフェノキシ)エタン(FF680)、テトラブロモ−ビスフェノールA(Saytex(登録商標)RB100)、エチレンビス−(ジブロモ−ノルボルナンジカルボキシミド)(Saytex(登録商標)BN−451)、ビス(ヘキサクロロシクロペンタジエノ)シクロオクタン、PTFE、トリス−(2,3−ジブロモプロピル)−イソシアヌレート、及びエチレン−ビス−テトラブロモフタルイミド。
アミノグアニジンフェニルホスフィナート塩(I)(式中、
R1〜R5は互いに独立して水素又はC1〜C4アルキル、ヒドロキシ、ヒドロキシ−C1〜C4アルキル及びC1〜C4アルコキシからなる群から選択される置換基を表し;且つ
R6〜R10は互いに独立して水素又はC1〜C4アルキル、フェニル、フェニル−C1〜C4アルキル、(C1〜C4アルキル)1〜3フェニル及び(C1〜C4アルキル)1〜2ヒドロキシフェニルからなる群から選択される置換基を表す)を;
追加の難燃剤、特にリン含有難燃剤、窒素含有難燃剤、ハロゲン化難燃剤及び無機難燃剤からなる群から選択される難燃剤と組み合わせて含む、混合物に関する。
アミノグアニジンフェニルホスフィナート:
380.2g(2.68モル)のフェニルホスフィン酸(アルドリッチ社、独国)を、室温で1.25リットルのエタノールに溶解させ、この溶液を65℃に加熱する。364.2g(2.68モル)のアミノグアニジン炭酸水素塩(アルドリッチ社、独国)を、二酸化炭素の発生がそれぞれ停止した後に、35分間にわたり少量ずつ添加する。添加完了後に、混合物を65℃で更に90分間撹拌する。透明で無色の溶液を、回転蒸発器で濃縮乾固させる。形成された固体残留物を、空気循環乾燥炉にて60℃で一晩乾燥させ、その後、真空炉にて130℃で17時間乾燥させる。578g(2.68モル、99.8%)の上記生成物が無色の結晶性固体として得られる。
C7H13N4O2P(Mw:216.17);%−P:14.2%実測値(14.3%理論値)、融点:70℃、TGA(開始):259℃。
o−クレゾールノボラックエポキシ樹脂:Araldite(登録商標)ECN1280、Huntsman Advanced Materials社、バーゼル、スイス;
硬化剤:ジシアンジアミド(DICY)、
促進剤:2−メチルイミダゾール、共にアルドリッチ社製、独国;
溶媒:メトキシ−2−プロパノール及びジメチルホルムアミド、Merck Eurolab社、独国;
三水酸化アルミニウム(ATH):Martinal(登録商標)OL104WE、Martinswerk社、独国;
メラミンポリホスフェート:Melapur(登録商標)200、BASF Schweiz AG社、スイス;
ガラス布:7628型、P−D Interglas Technologies AG社、独国。
「素子及び電化製品の部品のためのプラスチック材料の可燃性(Flammability of Plastic Materials for Parts in Devices and Appliances)」に関するUL94試験、第5版、1996年10月29日。UL94V試験による等級を以下の表にまとめる(時間周期は1つの試験片について示す):
樹脂配合物を、95℃の37.5部のメトキシ−2−プロパノール、0.04部の2−メチルイミダゾール及び特定量の表1によるアミノグアニジンフェニルホスフィナートにおいて、異なる量のAraldite(登録商標)ECN1280樹脂を用いて調製する。それぞれ95℃で15分間混合した後、透明な溶液が得られる。DICY(DMFとメトキシ−2−プロパノールの溶媒混合物の溶液)を、表に記載された量で添加する。
・ 圧力をかけずに170℃で1分間、
・ 約3バールの圧力をかけて170℃で120分間。
Claims (14)
- 成分a)のアミノグアニジンフェニルホスフィナート塩(I)において、
R1〜R5が水素を表し;
R6〜R10が互いに独立して水素又はC1〜C4アルキルを表し;且つ
xが1.0〜2.0の間の数を表す、請求項1に記載の組成物。 - 成分a)のアミノグアニジンフェニルホスフィナート塩(I)において、
R1〜R5が水素を表し;
R6〜R10が水素を表し;且つ
xが1.0〜2.0の間の数を表す、請求項1に記載の組成物。 - 成分b)として、多官能エポキシド化合物、硬化剤化合物及び熱可塑性ポリマーからなる群から選択されるポリマー基材を含む、請求項1に記載の組成物。
- 成分b)として、多官能エポキシド化合物、並びに少なくとも2つのアミノ基又は2つのヒドロキシ基を有する硬化剤化合物からなる群から選択されるポリマー基材を含む、請求項4に記載の組成物。
- ポリマー安定剤及び追加の難燃剤からなる群から選択される更なる添加剤を更に含む、請求項1に記載の組成物。
- 追加の難燃剤として、メラミンポリホスフェート、アンモニウムポリホスフェート、メラミンアンモニウムホスフェート、メラミンアンモニウムポリホスフェート、メラミンアンモニウムピロホスフェート、メラミンとリン酸との縮合物及びメラミンとリン酸との他の反応生成物並びにそれらの混合物からなる群から選択される窒素含有化合物を含む、請求項7に記載の組成物。
- 更なるポリマー基材を含む、請求項1に記載の組成物。
- 難燃性を硬化した多官能エポキシド組成物に付与する方法であって、該組成物に請求項1に記載のアミノグアニジンフェニルホスフィナート塩(I)を添加することを含む、方法。
- R1〜R5が水素を表し;
R6〜R10が互いに独立して水素又はC1〜C4アルキルを表し;且つ
xが1.0〜2.0の間の数を表す、請求項11に記載のアミノグアニジンフェニルホスフィナート(I)。 - R1〜R5が水素を表し;
R6〜R10が互いに独立して水素を表し;且つ
xが1.0〜2.0の間の数を表す、請求項11に記載のアミノグアニジンフェニルホスフィナート(I)。 - 硬化剤としての請求項11に記載のグアニジンフェニルホスフィナート塩(I)。
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US33221410P | 2010-05-07 | 2010-05-07 | |
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EP10162285.0 | 2010-05-07 | ||
PCT/EP2011/057236 WO2011138410A1 (en) | 2010-05-07 | 2011-05-05 | Aminoguanidinephenylphosphinate flame retardant compositions |
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EP (1) | EP2566846A1 (ja) |
JP (1) | JP5562484B2 (ja) |
KR (1) | KR20130026520A (ja) |
CN (1) | CN102884042A (ja) |
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Cited By (1)
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JP2015117323A (ja) * | 2013-12-19 | 2015-06-25 | 横浜ゴム株式会社 | 天然ゴムを含有するゴム組成物および天然ゴムの恒粘度化および臭気抑制方法 |
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JP6322651B2 (ja) * | 2012-12-27 | 2018-05-09 | ダウ グローバル テクノロジーズ エルエルシー | 異方向回転押出によるtpo屋根膜の製造 |
TWI490264B (zh) * | 2013-06-25 | 2015-07-01 | Ind Tech Res Inst | 聚酯組合物、及由其製備而得之聚酯製品 |
WO2018088729A2 (ko) * | 2016-11-10 | 2018-05-17 | (주) 엘지화학 | 비할로겐 난연수지 조성물 |
KR102092131B1 (ko) | 2016-11-10 | 2020-03-23 | 주식회사 엘지화학 | 비할로겐 난연수지 조성물 |
US11001554B2 (en) * | 2018-03-29 | 2021-05-11 | Ut-Battelle, Llc | Lipophilic guanidinium compounds for removal of oxyanions from aqueous solutions |
WO2019194620A1 (ko) * | 2018-04-06 | 2019-10-10 | 주식회사 엘지화학 | 열가소성 수지 조성물 |
KR102257969B1 (ko) * | 2018-04-06 | 2021-05-28 | 주식회사 엘지화학 | 열가소성 수지 조성물 |
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Also Published As
Publication number | Publication date |
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US8771561B2 (en) | 2014-07-08 |
JP5562484B2 (ja) | 2014-07-30 |
WO2011138410A1 (en) | 2011-11-10 |
EP2566846A1 (en) | 2013-03-13 |
TW201144416A (en) | 2011-12-16 |
CN102884042A (zh) | 2013-01-16 |
KR20130026520A (ko) | 2013-03-13 |
US20130105745A1 (en) | 2013-05-02 |
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