JP6338584B2 - 淡い色を有する難燃性ポリアミド - Google Patents
淡い色を有する難燃性ポリアミド Download PDFInfo
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- JP6338584B2 JP6338584B2 JP2015532348A JP2015532348A JP6338584B2 JP 6338584 B2 JP6338584 B2 JP 6338584B2 JP 2015532348 A JP2015532348 A JP 2015532348A JP 2015532348 A JP2015532348 A JP 2015532348A JP 6338584 B2 JP6338584 B2 JP 6338584B2
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- 229920002647 polyamide Polymers 0.000 title claims description 37
- 239000004952 Polyamide Substances 0.000 title claims description 36
- 239000003063 flame retardant Substances 0.000 title description 10
- 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 8
- 239000012778 molding material Substances 0.000 claims description 45
- 150000001875 compounds Chemical class 0.000 claims description 42
- -1 trialkylphosphine Chemical compound 0.000 claims description 35
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 34
- 239000000203 mixture Substances 0.000 claims description 27
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- 229910052698 phosphorus Inorganic materials 0.000 claims description 17
- 239000011574 phosphorus Substances 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000009757 thermoplastic moulding Methods 0.000 claims description 15
- 239000003446 ligand Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 claims description 6
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 6
- 239000000654 additive Substances 0.000 claims description 6
- 239000000835 fiber Substances 0.000 claims description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 5
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
- 229910021607 Silver chloride Inorganic materials 0.000 claims description 5
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 claims description 5
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 claims description 4
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 4
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 4
- 150000008045 alkali metal halides Chemical class 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- ADZWSOLPGZMUMY-UHFFFAOYSA-M silver bromide Chemical compound [Ag]Br ADZWSOLPGZMUMY-UHFFFAOYSA-M 0.000 claims description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 claims description 3
- 239000004471 Glycine Substances 0.000 claims description 3
- 239000004609 Impact Modifier Substances 0.000 claims description 3
- 125000005595 acetylacetonate group Chemical group 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 229910052802 copper Inorganic materials 0.000 claims description 3
- PDZKZMQQDCHTNF-UHFFFAOYSA-M copper(1+);thiocyanate Chemical compound [Cu+].[S-]C#N PDZKZMQQDCHTNF-UHFFFAOYSA-M 0.000 claims description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 claims description 3
- 230000029142 excretion Effects 0.000 claims description 3
- 150000004820 halides Chemical class 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- RHUVFRWZKMEWNS-UHFFFAOYSA-M silver thiocyanate Chemical compound [Ag+].[S-]C#N RHUVFRWZKMEWNS-UHFFFAOYSA-M 0.000 claims description 3
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 claims description 2
- 229910021589 Copper(I) bromide Inorganic materials 0.000 claims description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 claims description 2
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 claims description 2
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- 150000007974 melamines Chemical class 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229920006345 thermoplastic polyamide Polymers 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims 3
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical group [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 claims 2
- 150000001734 carboxylic acid salts Chemical class 0.000 claims 1
- 239000000178 monomer Substances 0.000 description 38
- 229920001971 elastomer Polymers 0.000 description 34
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 19
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 19
- 239000005060 rubber Substances 0.000 description 18
- 239000010949 copper Substances 0.000 description 17
- 239000000806 elastomer Substances 0.000 description 16
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- 125000004432 carbon atom Chemical group C* 0.000 description 13
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 12
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 10
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 10
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 9
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 8
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 8
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 8
- 229920002302 Nylon 6,6 Polymers 0.000 description 8
- 125000003700 epoxy group Chemical group 0.000 description 8
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 7
- 239000001361 adipic acid Substances 0.000 description 7
- 235000011037 adipic acid Nutrition 0.000 description 7
- 150000001991 dicarboxylic acids Chemical class 0.000 description 7
- 229920000098 polyolefin Polymers 0.000 description 7
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 7
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 6
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 229920003023 plastic Polymers 0.000 description 6
- 239000004033 plastic Substances 0.000 description 6
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 6
- 229920002943 EPDM rubber Polymers 0.000 description 5
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 5
- 239000005977 Ethylene Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229920000877 Melamine resin Polymers 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000001257 hydrogen Substances 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 150000002989 phenols Chemical class 0.000 description 5
- 229920006123 polyhexamethylene isophthalamide Polymers 0.000 description 5
- 150000004756 silanes Chemical class 0.000 description 5
- 229910052709 silver Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 239000004908 Emulsion polymer Substances 0.000 description 4
- JHWNWJKBPDFINM-UHFFFAOYSA-N Laurolactam Chemical compound O=C1CCCCCCCCCCCN1 JHWNWJKBPDFINM-UHFFFAOYSA-N 0.000 description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229920000388 Polyphosphate Polymers 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 229920006097 Ultramide® Polymers 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 150000001993 dienes Chemical class 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
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- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 4
- 239000012764 mineral filler Substances 0.000 description 4
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- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 4
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- PBKONEOXTCPAFI-UHFFFAOYSA-N 1,2,4-trichlorobenzene Chemical compound ClC1=CC=C(Cl)C(Cl)=C1 PBKONEOXTCPAFI-UHFFFAOYSA-N 0.000 description 3
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- QHZLMUACJMDIAE-UHFFFAOYSA-N 1-monopalmitoylglycerol Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(O)CO QHZLMUACJMDIAE-UHFFFAOYSA-N 0.000 description 2
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- 150000008064 anhydrides Chemical class 0.000 description 2
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- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
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- OYACROKNLOSFPA-UHFFFAOYSA-N calcium;dioxido(oxo)silane Chemical compound [Ca+2].[O-][Si]([O-])=O OYACROKNLOSFPA-UHFFFAOYSA-N 0.000 description 2
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- FBCQUCJYYPMKRO-UHFFFAOYSA-N prop-2-enyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC=C FBCQUCJYYPMKRO-UHFFFAOYSA-N 0.000 description 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 description 1
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 description 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003873 salicylate salts Chemical class 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011265 semifinished product Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002379 silicone rubber Polymers 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- HHJJPFYGIRKQOM-UHFFFAOYSA-N sodium;oxido-oxo-phenylphosphanium Chemical compound [Na+].[O-][P+](=O)C1=CC=CC=C1 HHJJPFYGIRKQOM-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- LTURHSAEWJPFAA-UHFFFAOYSA-N sulfuric acid;1,3,5-triazine-2,4,6-triamine Chemical compound OS(O)(=O)=O.NC1=NC(N)=NC(N)=N1 LTURHSAEWJPFAA-UHFFFAOYSA-N 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical group CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- BPSKTAWBYDTMAN-UHFFFAOYSA-N tridecane-1,13-diamine Chemical compound NCCCCCCCCCCCCCN BPSKTAWBYDTMAN-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
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N urethane group Chemical group NC(=O)OCC JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- BNEMLSQAJOPTGK-UHFFFAOYSA-N zinc;dioxido(oxo)tin Chemical compound [Zn+2].[O-][Sn]([O-])=O BNEMLSQAJOPTGK-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/32—Phosphorus-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
- C08L23/04—Homopolymers or copolymers of ethene
- C08L23/08—Copolymers of ethene
- C08L23/0846—Copolymers of ethene with unsaturated hydrocarbons containing other atoms than carbon or hydrogen atoms
- C08L23/0869—Acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
- C08L77/06—Polyamides derived from polyamines and polycarboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
-
- 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
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/02—Elements
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Description
A) 熱可塑性ポリアミド 10〜99.8質量%、
B) 赤リン 0.1〜60質量%、
C) Cu(I)またはAg(I)の塩または酸化物または錯体またはそれらの混合物 0.01〜4質量%
D) 耐衝撃性改質剤 0〜40質量%、
E) さらなる添加剤 0〜60質量%
(ここで、A)〜E)の質量パーセントの合計は100%になる)
を含有する熱可塑性成形材料に関する。
PA4 ピロリドン
PA6 ε−カプロラクタム
PA7 エタノラクタム
PA8 カプリルラクタム
PA9 9−アミノペラルゴン酸
PA11 11−アミノウンデカン酸
PA12 ラウリンラクタム
AA/BB−ポリマー
PA46 テトラメチレンジアミン、アジピン酸
PA66 ヘキサメチレンジアミン、アジピン酸
PA69 ヘキサメチレンジアミン、アゼライン酸
PA610 ヘキサメチレンジアミン、セバシン酸
PA612 ヘキサメチレンジアミン、デカンジカルボン酸
PA613 ヘキサメチレンジアミン、ウンデカンジカルボン酸
PA1212 1,12−ドデカンジアミン、デカンジカルボン酸
PA1313 1,13−ジアミノトリデカン、ウンデカンジカルボン酸
PA6T ヘキサメチレンジアミン、テレフタル酸
PA9T 1,9−ノナンジアミン、テレフタル酸
PA MXD6 m−キシリレンジアミン、アジピン酸
PA6I ヘキサメチレンジアミン、イソフタル酸
PA6−3−T トリメチルヘキサメチレンジアミン、テレフタル酸
PA6/6T (PA6およびPA6Tを参照)
PA6/66 (PA6およびPA66を参照)
PA6/12 (PA6およびPA12を参照)
PA66/6/610 (PA66、PA6およびPA610を参照)
PA6I/6T (PA6IおよびPA6Tを参照)
PA PACM12 ジアミノジシクロヘキシルメタン、ラウリンラクタム
PA6I/6T/PACM PA6I/6Tと同様+ジアミノジシクロヘキシルメタン
PA12/MACMI ラウリンラクタム、ジメチルジアミノジシクロヘキシルメタン、イソフタル酸
PA12/MACMT ラウリンラクタム、ジメチルジアミノジシクロヘキシルメタン、テレフタル酸
PA PDA−T フェニレンジアミン、テレフタル酸。
B1) ポリアミドまたはエラストマー 30〜90質量%、有利には45〜70質量%、
B2) 赤リン 10〜70質量%、有利には30〜55質量%
である。
[Cu(PPh3)3X]、[Cu2X2(PPh3)3]、[Cu(PPh3)X]4並びに[Cu(PPh3)2X]、前記XはCl、Br、I、CN、SCNまたは2−メルカプトベンズイミダゾールから選択され、ここで、Cu(I)−(PPh3)2Iが特に好ましい。
エチレン 50〜98質量%、殊に55〜95質量%、
グリシジルアクリレートおよび/またはグリシジルメタクリレート、(メタ)アクリル酸および/または無水マレイン酸 0.1〜40質量%、殊に0.3〜20質量%、および
n−ブチルアクリレートおよび/または2−エチルヘキシルアクリレート 1〜45質量%、殊に5〜40質量%
からのコポリマーである。
R10は、水素またはC1〜C4−アルキル基であり、
R11は、水素、C1〜C8−アルキル基またはアリール基、殊にフェニルであり、
R12は、水素、C1〜C10−アルキル基、C6〜C12−アリール基または−OR13であり、
R13は、C1〜C8−アルキル基またはC6〜C12−アリール基であり、該基は、随意にO含有基またはN含有基で置換されていてよく、
Xは、化学結合、C1〜C10−アルキレン基またはC6〜C12−アリーレン基、または
Yは、O−ZまたはNH−Zであり、且つ
Zは、C1〜C10−アルキレン基またはC6〜C12−アリーレン基である。
Xは、
nは、2〜10の、好ましくは3〜4の整数であり、
mは、1〜5の、好ましくは1〜2の整数であり、
kは、1〜3の、好ましくは1の整数である。
の化合物が考慮に入れられる。
の化合物である。
2,2’−メチレン−ビス−(4−メチル−6−tert−ブチルフェノール)、1,6−ヘキサンジオール−ビス[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)−プロピオネート]、ペンタエリトリチル−テトラキス−[3−(3,5−ジ−tert−ブチル−4−ヒドロキシフェニル)−プロピオネート]、ジステアリル−3,5−ジ−tert−ブチル−4−ヒドロキシベンジルホスホネート、2,6,7−トリオキサ−1−ホスファビシクロ−[2.2.2]オクタ−4−イル−メチル−3,5−ジ−tert−ブチル−4−ヒドロキシヒドロシンナメート、3,5−ジ−tert−ブチル−4−ヒドロキシフェニル−3,5−ジステアリル−チオトリアジルアミン、2−(2’−ヒドロキシ−3’−ヒドロキシ−3’,5’−ジ−tert−ブチルフェニル)−5−クロロベンゾトリアゾール、2,6−ジ−tert−ブチル−4−ヒドロキシメチルフェノール、1,3,5−トリメチル−2,4,6−トリス−(3,5−ジ−tert−ブチル−4−ヒドロキシベンジル)−ベンゼン、4,4’−メチレン−ビス−(2,6−ジ−tert−ブチルフェノール)、3,5−ジ−tert−ブチル−4−ヒドロキシベンジル−ジメチルアミン。
成分A/1:
ISO 307に準拠し、25℃で、96質量%の硫酸中で0.5質量%の溶液として測定して、150ml/gの粘度数VZを有するポリアミド66(BASF SEのUltramid(登録商標)A27を使用した)。
125ml/gのVZを有するPA 66 (BASF SEのUltramid(登録商標)A24)
成分B/1:
溶融指数MFI(190/2.16)10g/10分を有し、エチレン59.8質量%、n−ブチルアクリレート35質量%、アクリル酸4.5質量%、およびマレイン酸無水物0.7質量%(成分D)からなるオレフィンポリマー中で平均粒径(d50)10〜30μmの赤リンからの50%濃縮物。該コポリマーは、高められた温度且つ高められた圧力でのモノマーの共重合によって製造された。
エラストマーD)を有さないP赤(上記参照)。
ヨウ化銅。
ビス(トリフェニルホスフィン)・ヨウ化銅錯体、CAS番号.: 16109−82−3。
ポリアミドのための標準的なチョップドガラス繊維、長さ=4.5mm、直径=10μm。
N,N’−ヘキサメチレン−ビス−3,5−ジ−tert−ブチル−4−ヒドロキシヒドロシンアミド (Irganox(登録商標) 1098)。
ステアリン酸カルシウム。
ZnO。
本発明により記載されるリン安定性の改善を証明するために、相応のプラスチック成形材料をコンパウンディングによって作製した。このために、個々の成分を二軸押出機ZSK26(Berstoff社)内で、スループット20kg/時間および約270℃で、平坦な温度プロファイルで混合し、ストランドとして押出し、顆粒化できるまで冷却し、そして顆粒化した。
プラスチックのロッド(125×12.5×1.6mm)を半分にし、且つ、半分ずつ10mlのガラスビーカーに添加した。銀からなるコンタクト材料(10×50×0.125mm)を短い試験管に装入した。引き続き、それら3つの試料を100mlのねじ蓋瓶に入れ、5mlの水をそこに加え、且つ、その閉じた系を70℃の乾燥棚内に入れた。28日後、前記試験管を取り出し、水で満たし、且つ、内容物全体をガラスビーカーに入れた。5mlの濃硫酸をそこに加え、ほぼ乾燥するまで蒸発させる。金属のロッドをここで取り出し、水で濯ぎ、その残りを1mlの硫酸で置き換え、再度、ほぼ乾燥するまで濃縮した。その際、20mlの水で希釈し、4mlの5%濃度のペルオキソ二硫酸カリウム溶液を添加し、且つ30分間加熱する。リンの測定はここで、測光法により、μgのリン/プラスチックのロッド中でモリブデンブルー法として行われた。
色の測定をDIN 53236:1983、方法Bによって行った。DIN 6174:1979、(ISO 7724−3、いわゆるCieLab法と一致)により計算された:
L*=明るさ; +はより白く、−はより黒い、
a*=色の成分; +はより赤く、−はより灰色である、
b*=色の成分; +はより黄色く、−はより青い、
ゼロの値は、色がない、無着色、無色を意味する、
C*ab=彩度(無着色/有色); h°ab=色相角(0〜360°)、
L*、a*およびb*を一緒に評価して、色差ΔE*が得られる。
DSM社のMicro15押出機を用いた小規模押出によって試料の混入を行った。その処理を280℃で行った。
DIN EN ISO 11341 方法2に従って露光: 340nmで0.35W/m2×nm、露光時間 24時間、露光温度38℃(±2℃)、露光湿度50%(±10%)。
熱可塑性材料の処理を、Leistritz社のツインスクリュー押出機ZSK 25−F41を用い、スループット30kg/時間で行った。押出温度は300℃であった。ポリマーストランドを、水浴を用いて冷却し、引き続き造粒し且つ乾燥させた。使用される試験体への射出成形を320℃で行った。
引張弾性率: DIN EN ISO 527−1/−2
破断点伸び: DIN EN ISO 527−1/−2
破壊応力: DIN EN ISO 527−1/−2
シャルピー衝撃強さ: DIN EN ISO 179。
Claims (13)
- A) 熱可塑性ポリアミド 10〜99.8質量%、
B) 赤リン 0.1〜60質量%、
C) Cu(I)の塩もしくはCu(I)の錯体、またはAg(I)の酸化物、AgSCN、AgCl、AgBr、AgIおよびAg(I)のカルボン酸塩から選択されるAg(I)の塩もしくはAg(I)の錯体、またはそれらの混合物 0.01〜4質量%、
D) 耐衝撃性改質剤 0〜40質量%、および
E) さらなる添加剤 0〜60質量%
(ここで、A)〜E)の質量パーセントの合計は100%になる)
を含有する熱可塑性成形材料であって、0質量%のメラミン化合物を含有し、かつ前記成分C)のないポリアミド(PA)成形材料と比較してΔL色値が少なくとも15%低い(DIN53236およびISO7724−3、CieLab法による)、前記熱可塑性成形材料を製造するための、Cu化合物および/またはAg化合物であるC)の使用。 - 前記熱可塑性成形材料が、
A) 20〜98質量%
B) 0.5〜40質量%
C) 0.1〜3質量%
D) 1〜30質量%
E) 0〜50質量%
を含有する、請求項1に記載の使用。 - 成分C)がアルカリ金属ハロゲン化物と混合されて使用される、請求項1または2に記載の使用。
- アルカリ金属ハロゲン化物が臭化カリウムまたはヨウ化カリウムまたはそれらの混合物である、請求項3に記載の使用。
- 成分C)は、Ag(I)錯体またはCu(I)錯体であり、前記錯体が配位子としてトリフェニルホスフィン、トリアルキルホスフィン、メルカプトベンズイミダゾール、EDTA、アセチルアセトナト、グリシン、エチレンジアミン、オキサレート、ジエチレントリアミン、トリエチレンテトラミン、ピリジン、ジホスホン、ジピリジルまたはそれらの混合物を含有する、請求項1から4までのいずれか1項に記載の使用。
- 成分C)が、Ag2O、Cu(I)ハロゲン化物、AgCl、AgBr、AgI、CuSCN、AgSCN、Cu(I)カルボン酸塩またはAg(I)カルボン酸塩から構成されている、請求項1から5までのいずれか1項に記載の熱可塑性成形材料の使用。
- ハロゲン化物であるC)が、CuF、CuI、CuBr、AgI、AgBr、AgCl、CuClから、且つ、カルボン酸塩であるC)が、酢酸塩、シュウ酸塩、ステアリン酸塩、プロピオン酸塩、酪酸塩、安息香酸塩、またはそれらの混合物からなる、請求項6に記載の使用。
- 成分C)がアルカリ金属ハロゲン化物との1:10〜1:1の混合比で存在する、請求項1から7までのいずれか1項に記載の使用。
- 繊維、フィルム、または成形体を製造するための、請求項1から8までのいずれか1項に記載の熱可塑性成形材料の使用。
- 請求項1から8までのいずれか1項に記載の熱可塑性成形材料から得られる繊維、フィルムまたは成形体。
- 請求項1に記載の成分C)のないポリアミド(PA)成形材料と比較してΔa色値が少なくとも35%低い(DIN53236およびISO7724−3、CieLab法による)、請求項1に記載の熱可塑性成形材料または請求項10に記載の成形体を製造するための、請求項1に記載のCu化合物および/またはAg化合物であるC)の使用。
- 請求項1に記載の成分C)のないポリアミド(PA)成形材料と比較してΔb色値が少なくとも35%低い(DIN53236およびISO7724−3、CieLab法による)、請求項1に記載の熱可塑性成形材料または請求項10に記載の成形体を製造するための、請求項1に記載のCu化合物および/またはAg化合物であるC)の使用。
- モリブデンブルー法により200μg未満のリン/試料であるリン排出値(28日/70℃)を有する、請求項1に記載の熱可塑性成形材料または請求項10に記載の成形体を製造するための、請求項1に記載のCu化合物および/またはAg化合物であるC)の使用。
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EP12184935 | 2012-09-19 | ||
EP12184935.0 | 2012-09-19 | ||
PCT/EP2013/066876 WO2014044471A1 (de) | 2012-09-19 | 2013-08-13 | Flammgeschützte polyamide mit heller farbe |
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WO2024104965A1 (en) * | 2022-11-17 | 2024-05-23 | Basf Se | Mixed metal-oxide compositions as stabilizer for flame retardant polyamides |
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BR112015005915A2 (pt) | 2018-04-17 |
CA2884863C (en) | 2020-07-21 |
JP2015529270A (ja) | 2015-10-05 |
CA2884863A1 (en) | 2014-03-27 |
PL2898009T3 (pl) | 2017-06-30 |
PT2898009T (pt) | 2017-01-23 |
AU2013320577A1 (en) | 2015-04-02 |
KR20150056850A (ko) | 2015-05-27 |
KR102111422B1 (ko) | 2020-06-08 |
WO2014044471A1 (de) | 2014-03-27 |
RU2015114339A (ru) | 2016-11-10 |
HUE032830T2 (en) | 2017-11-28 |
ZA201502580B (en) | 2017-04-26 |
EP2898009B1 (de) | 2016-10-12 |
CN104640915A (zh) | 2015-05-20 |
AU2013320577B2 (en) | 2016-06-16 |
BR112015005915B1 (pt) | 2021-04-13 |
MX2015003546A (es) | 2015-06-22 |
IL237552A0 (en) | 2015-04-30 |
PH12015500462B1 (en) | 2015-04-20 |
DK2898009T3 (en) | 2017-01-30 |
EP2898009A1 (de) | 2015-07-29 |
CN104640915B (zh) | 2018-06-05 |
RU2632010C2 (ru) | 2017-10-02 |
ES2612356T3 (es) | 2017-05-16 |
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