JP6328554B2 - 安定化剤としてのポリアミド鎖延長化合物の使用 - Google Patents
安定化剤としてのポリアミド鎖延長化合物の使用 Download PDFInfo
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- JP6328554B2 JP6328554B2 JP2014519506A JP2014519506A JP6328554B2 JP 6328554 B2 JP6328554 B2 JP 6328554B2 JP 2014519506 A JP2014519506 A JP 2014519506A JP 2014519506 A JP2014519506 A JP 2014519506A JP 6328554 B2 JP6328554 B2 JP 6328554B2
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- Prior art keywords
- polyamide
- composition
- chain extension
- weight
- polyamide chain
- Prior art date
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- 229920002647 polyamide Polymers 0.000 title claims description 130
- 239000004952 Polyamide Substances 0.000 title claims description 129
- 150000001875 compounds Chemical class 0.000 title claims description 47
- 239000003381 stabilizer Substances 0.000 title description 5
- 239000000203 mixture Substances 0.000 claims description 95
- 239000004970 Chain extender Substances 0.000 claims description 26
- 239000004609 Impact Modifier Substances 0.000 claims description 21
- 239000000654 additive Substances 0.000 claims description 17
- -1 bisoxazoline Chemical compound 0.000 claims description 16
- 230000032683 aging Effects 0.000 claims description 15
- 239000000945 filler Substances 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 12
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 claims description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 9
- 230000006641 stabilisation Effects 0.000 claims description 9
- 238000011105 stabilization Methods 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 230000014759 maintenance of location Effects 0.000 claims description 8
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 8
- 229920002292 Nylon 6 Polymers 0.000 claims description 7
- 229920002302 Nylon 6,6 Polymers 0.000 claims description 7
- 230000035882 stress Effects 0.000 claims description 7
- 230000000996 additive effect Effects 0.000 claims description 6
- 230000003014 reinforcing effect Effects 0.000 claims description 6
- ZBFCSRYSLRPAOY-UHFFFAOYSA-M sodium;hydroxy(phenyl)methanesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C(O)C1=CC=CC=C1 ZBFCSRYSLRPAOY-UHFFFAOYSA-M 0.000 claims description 4
- 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 claims description 3
- 229920000305 Nylon 6,10 Polymers 0.000 claims description 3
- 150000008064 anhydrides Chemical group 0.000 claims description 3
- 229920006111 poly(hexamethylene terephthalamide) Polymers 0.000 claims description 3
- AGEILULECXEYHO-UHFFFAOYSA-N 1,6-bis(7-oxoazepan-2-yl)hexane-1,6-dione Chemical compound C1CCCC(=O)NC1C(=O)CCCCC(=O)C1CCCCC(=O)N1 AGEILULECXEYHO-UHFFFAOYSA-N 0.000 claims description 2
- WTPYFJNYAMXZJG-UHFFFAOYSA-N 2-[4-(2-hydroxyethoxy)phenoxy]ethanol Chemical compound OCCOC1=CC=C(OCCO)C=C1 WTPYFJNYAMXZJG-UHFFFAOYSA-N 0.000 claims description 2
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 2
- 125000005442 diisocyanate group Chemical group 0.000 claims description 2
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 claims description 2
- 239000012530 fluid Substances 0.000 claims description 2
- ACCCMOQWYVYDOT-UHFFFAOYSA-N hexane-1,1-diol Chemical compound CCCCCC(O)O ACCCMOQWYVYDOT-UHFFFAOYSA-N 0.000 claims description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 2
- 230000000087 stabilizing effect Effects 0.000 claims description 2
- KCOPAESEGCGTKM-UHFFFAOYSA-N 1,3-oxazol-4-one Chemical compound O=C1COC=N1 KCOPAESEGCGTKM-UHFFFAOYSA-N 0.000 claims 1
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 claims 1
- 150000002118 epoxides Chemical group 0.000 claims 1
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 21
- 125000000524 functional group Chemical group 0.000 description 18
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 14
- 150000001412 amines Chemical group 0.000 description 12
- 229920001971 elastomer Polymers 0.000 description 12
- 238000001125 extrusion Methods 0.000 description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 239000005977 Ethylene Substances 0.000 description 11
- 239000002253 acid Chemical group 0.000 description 11
- 239000000178 monomer Substances 0.000 description 10
- 229920001577 copolymer Polymers 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 125000001931 aliphatic group Chemical group 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 239000005060 rubber Substances 0.000 description 7
- 239000003365 glass fiber Substances 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 6
- 239000000155 melt Substances 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
- 150000005846 sugar alcohols Polymers 0.000 description 6
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 5
- 239000000806 elastomer Substances 0.000 description 5
- 239000004744 fabric Substances 0.000 description 5
- 238000000465 moulding Methods 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 4
- QHZOMAXECYYXGP-UHFFFAOYSA-N ethene;prop-2-enoic acid Chemical compound C=C.OC(=O)C=C QHZOMAXECYYXGP-UHFFFAOYSA-N 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000012763 reinforcing filler Substances 0.000 description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 229920000571 Nylon 11 Polymers 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 229920006018 co-polyamide Polymers 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 150000001993 dienes Chemical class 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- 150000003951 lactams Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229920006139 poly(hexamethylene adipamide-co-hexamethylene terephthalamide) Polymers 0.000 description 3
- 238000006068 polycondensation reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 2
- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
- PTJWCLYPVFJWMP-UHFFFAOYSA-N 2-[[3-hydroxy-2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)COCC(CO)(CO)CO PTJWCLYPVFJWMP-UHFFFAOYSA-N 0.000 description 2
- QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-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
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- 229920002943 EPDM rubber Polymers 0.000 description 2
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
- 229920000299 Nylon 12 Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 101000576320 Homo sapiens Max-binding protein MNT Proteins 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229920000271 Kevlar® Polymers 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- HEBKCHPVOIAQTA-IMJSIDKUSA-N L-arabinitol Chemical compound OC[C@H](O)C(O)[C@@H](O)CO HEBKCHPVOIAQTA-IMJSIDKUSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 229920000572 Nylon 6/12 Polymers 0.000 description 1
- 229920006154 PA11T Polymers 0.000 description 1
- 229920006155 PA13T Polymers 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920006121 Polyxylylene adipamide Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 description 1
- 238000004026 adhesive bonding Methods 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 238000005273 aeration Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 229920003231 aliphatic polyamide Polymers 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000009954 braiding Methods 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-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
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 125000006159 dianhydride group Chemical group 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 235000019414 erythritol Nutrition 0.000 description 1
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 description 1
- 229940009714 erythritol Drugs 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000010101 extrusion blow moulding Methods 0.000 description 1
- 238000009950 felting Methods 0.000 description 1
- 239000012765 fibrous filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000011990 functional testing Methods 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 229920000554 ionomer Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004761 kevlar Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- FLFJVPPJGJSHMF-UHFFFAOYSA-L manganese hypophosphite Chemical compound [Mn+2].[O-]P=O.[O-]P=O FLFJVPPJGJSHMF-UHFFFAOYSA-L 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 229920006119 nylon 10T Polymers 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- NAYYNDKKHOIIOD-UHFFFAOYSA-N phthalamide Chemical compound NC(=O)C1=CC=CC=C1C(N)=O NAYYNDKKHOIIOD-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920006115 poly(dodecamethylene terephthalamide) Polymers 0.000 description 1
- 229920006131 poly(hexamethylene isophthalamide-co-terephthalamide) Polymers 0.000 description 1
- 229920006128 poly(nonamethylene terephthalamide) Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001195 polyisoprene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 229920006012 semi-aromatic polyamide Polymers 0.000 description 1
- 229920006114 semi-crystalline semi-aromatic polyamide Polymers 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 239000006076 specific stabilizer Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 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
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G16/00—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00
- C08G16/02—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes
- C08G16/025—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds
- C08G16/0275—Condensation polymers of aldehydes or ketones with monomers not provided for in the groups C08G4/00 - C08G14/00 of aldehydes with heterocyclic organic compounds containing sulfur in the ring
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/48—Polymers modified by chemical after-treatment
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- 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
-
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K7/00—Use of ingredients characterised by shape
- C08K7/02—Fibres or whiskers
- C08K7/04—Fibres or whiskers inorganic
- C08K7/14—Glass
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyamides (AREA)
Description
− ビスフェノールAジグリシジルエーテルなどのビスエポキシドと、トリフェニルホスファイト又はカプロラクタムホスファイトなどの有機ホスファイト、及び
− エポキシド官能基を有するポリマーと、トリフェニルホスファイト又はカプロラクタムホスファイトなどの有機ホスファイト。
−少なくとも1つの、強化フィラー、耐衝撃性改良剤、及び/若しくは熱安定化に関与する別の添加剤を含み、且つ/又は
−少なくとも2つの鎖延長剤を含む
場合、
組成物は、ポリアミドの重量に対して1重量%を超える又はさらには2重量%のポリアミド鎖延長剤(複数可)の含量を備える。加えて、この含量は、ポリアミドの重量に対して1.1重量%〜8重量%、特に1.3重量%〜6重量%、又はさらには1.5重量%〜4重量%の範囲であってもよい。
− 強化フィラー、耐衝撃性改良剤、及び/又は熱安定化に関与する別の添加剤を含まず、かつ
− ただ1つの鎖延長剤を含む
場合、
組成物は、ポリアミドの重量に対して2重量%を超えるポリアミド鎖延長剤の含量を備える。加えて、この含量はポリアミドの重量に対して2.05重量%〜8重量%、特に2.1重量%〜6重量%、又はさらには2.1重量%〜4重量%の範囲であってもよい。
− 特に組成物の全重量に対して30重量%〜80重量%の範囲の含量であるポリアミド、特にPA6、PA66、PA610、及び/又はPA66/6T
− 特にポリアミドの重量に対して1重量%を超える含量の鎖延長剤、特にビスエポキシドを含み、任意選択により有機ホスファイトと組み合わされた鎖延長剤、
− 特に組成物の全重量に対して10重量%〜40重量%の範囲の含量である任意選択の強化フィラー、特にガラス繊維
− 特に組成物の全重量に対して5重量%〜20重量%の範囲の含量である任意選択の耐衝撃性改良剤、特にポリアミドと反応する官能基を含む耐衝撃性改良剤、
− 特に組成物の全重量に対して0.01重量%〜5重量%の範囲の含量である、組成物の熱安定化に関与する任意選択の別の添加剤、特に多価アルコール又はCuI/KI、CuO/KBr若しくはCu2O/KBrの組み合わせ、
− 特に組成物の全重量に対して0.01%〜8重量%の範囲の含量である、潤滑剤、難燃剤、可塑剤、核剤、抗紫外線剤、触媒、抗酸化剤、静電防止剤、染料、マット化剤及び離型剤から選択される、任意選択の少なくとも1つの添加剤、
を含むか、又はこれらから成る。
押出成形の前に、153ml/gのVI(ISO規格307による、ギ酸中のポリアミドの溶液における粘度指数(VI、mL/g))を有するポリアミド66顆粒を、1000ppm未満の水分含量となるまで乾燥させる。配合物は、40kg/hにて230〜250rpmの速度で作動するWerner&Pfleiderer ZSK 40二軸同方向回転押出機において様々な成分及び添加剤を溶融ブレンドすることにより調製される。8つの区画における温度設定はそれぞれ245、245、245、250、255、260、260、265℃である。配合物中のすべての成分を、押出機の始動時に加える。押出機から出てきたロッドを水槽中で冷却し、造粒機を用いて顆粒の形態に切断し、顆粒をヒートシールされる袋で包装する。射出成形される前に、顆粒は1000ppm未満の水分含量を得るように乾燥される。
− 1.5重量%の鎖延長化合物:Araldite(登録商標)GT7071(Huntsman)
− 15重量%の耐衝撃性改良剤:Exxelor VA1801(無水マレイン酸でグラフト化されたエチレン系コポリマー)
− 0.2重量%のCuI及びKI(Ajay Europe社)
− 15重量%のOCV 983ガラス繊維(Owens Corning Vetrotex社)
重量パーセントは、組成物の全重量に対する重量により表される。
Claims (7)
- 熱、光、及び/又は悪天候に対してポリアミドを安定化させるための薬剤としてのポリアミド鎖延長化合物の使用であって、
少なくともポリアミド及びポリアミド鎖延長化合物を含有する組成物が、空気中での210℃、1000時間のエージング試験後に、エージング試験前の同じ組成物と比較して、ISO規格527/1Aに準拠して4mm厚の試験片について測定して、50%以上の引張り破断応力の保持率を有すること、及び
ポリアミド鎖延長化合物が、エチレングリコール、プロパンジオール、ブタンジオール、ヘキサンジオール、又はヒドロキノンビス(ヒドロキシエチル)エーテルなどのジアルコール、ビスフェノールAジグリシジルエーテルなどのビスエポキシド、エポキシド官能基を有するポリマー、無水物官能基を有するポリマー、イソフタロイルビスカプロラクタム(IBC)、アジポイルビスカプロラクタム(ABC)又はテレフタロイルビスカプロラクタム(TBC)などのビス−N−アシルビスカプロラクタム、ジフェニルカーボネート、ビスオキサゾリン、オキサゾリノン、ジイソシアナート、トリフェニルホスファイト又はカプロラクタムホスファイトなどの有機ホスファイト、ビスケテンイミン、及びジアンヒドリドから成る群から選択されることを特徴とし、
少なくともポリアミド及びポリアミド鎖延長化合物を含む組成物から作られる物品が、高温、特に80℃以上の温度にさらされる用途のために作られる物品であることを特徴とする、使用。 - 少なくともポリアミド及びポリアミド鎖延長化合物を含む組成物が、組成物の全重量に対して0.01重量%〜5重量%のポリアミド鎖延長化合物を含むことを特徴とする、請求項1に記載の使用。
- ポリアミドが、ポリアミド6、ポリアミド610、ポリアミド66及びポリアミド66/6Tを含む群から選択されることを特徴とする、請求項1又は2に記載の使用。
- 少なくともポリアミド及びポリアミド鎖延長化合物を含む組成物が、少なくとも1つの強化又は増量フィラーを含むことを特徴とする、請求項1から3のいずれか一項に記載の使用。
- 少なくともポリアミド及びポリアミド鎖延長化合物を含む組成物が、少なくとも1つの耐衝撃性改良剤を含むことを特徴とする、請求項1から4のいずれか一項に記載の使用。
- 少なくともポリアミド及びポリアミド鎖延長化合物を含む組成物が、組成物の熱安定化に関与する少なくとも1つの他の添加剤を含むことを特徴とする、請求項1から5のいずれか一項に記載の使用。
- 物品が、流体を収容又は輸送するために製造される物品であることを特徴とする、請求項6に記載の使用。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR1156263A FR2970970B1 (fr) | 2011-07-11 | 2011-07-11 | Composition polyamide stabilisee |
FR1156263 | 2011-07-11 | ||
PCT/EP2012/063279 WO2013007644A1 (fr) | 2011-07-11 | 2012-07-06 | Utilisation d'un composé extenseur de chaine du polyamide en tant qu'agent stabilisant |
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JP2017196645A Division JP2018035364A (ja) | 2011-07-11 | 2017-10-10 | 安定化剤としてのポリアミド鎖延長化合物の使用 |
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JP2014522897A JP2014522897A (ja) | 2014-09-08 |
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JP2014519506A Active JP6328554B2 (ja) | 2011-07-11 | 2012-07-06 | 安定化剤としてのポリアミド鎖延長化合物の使用 |
JP2017196645A Pending JP2018035364A (ja) | 2011-07-11 | 2017-10-10 | 安定化剤としてのポリアミド鎖延長化合物の使用 |
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US (1) | US20140309367A1 (ja) |
EP (1) | EP2731996B2 (ja) |
JP (2) | JP6328554B2 (ja) |
KR (1) | KR20140053173A (ja) |
CN (1) | CN103781849B (ja) |
BR (1) | BR112014000676A2 (ja) |
FR (1) | FR2970970B1 (ja) |
WO (1) | WO2013007644A1 (ja) |
Families Citing this family (15)
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HUE047680T2 (hu) * | 2013-11-28 | 2020-05-28 | Lanxess Deutschland Gmbh | Poliamid-kompozíciók |
EP3083245A1 (fr) * | 2013-12-19 | 2016-10-26 | Hutchinson | Élément d'un compartiment moteur d'un véhicule automobile et procédé de protection de l'élément contre des agressions chimiques d'un halogénure métallique |
WO2016052351A1 (ja) * | 2014-09-30 | 2016-04-07 | 富士フイルム株式会社 | ポリアミド樹脂組成物及びポリアミド樹脂成形体 |
JP6817940B2 (ja) * | 2014-12-12 | 2021-01-20 | パフォーマンス・ポリアミデス,エスアエス | ポリアミド6,6および少なくとも1種の高鎖長ポリアミドのブレンドとステアリン酸Alとを含むポリアミド組成物、その使用、ならびにそれから得られる物品 |
CN105504801B (zh) * | 2015-12-14 | 2018-09-21 | 中广核三角洲(江苏)塑化有限公司 | 一种用于3d打印的高强度低收缩尼龙材料及其制备方法 |
TW201811976A (zh) | 2016-08-08 | 2018-04-01 | 美商堤康那責任有限公司 | 用於散熱器之導熱聚合物組合物 |
EP3354682B1 (en) * | 2017-01-31 | 2022-06-15 | Solvay Specialty Polymers USA, LLC. | Filled composition containing polyphenylene sulphide (pps) and polyamide 6 (pa6) |
CN106977918A (zh) * | 2017-03-24 | 2017-07-25 | 南通威得塑料制品有限公司 | 一种超韧尼龙材料 |
MX2020006574A (es) * | 2017-12-20 | 2020-11-13 | Basf Se | Compuesto de moldeo de poliamida de alta resistencia al calor. |
CN108659347A (zh) * | 2018-06-11 | 2018-10-16 | 全椒祥瑞塑胶有限公司 | 一种聚酰胺-亚麻酸共混物增强的聚丙烯材料 |
EP3587085A1 (de) * | 2018-06-27 | 2020-01-01 | Basf Se | Sinterpulver enthaltend einen mehrwertigen alkohol zur herstellung von formkörpern |
CA3154604C (en) * | 2019-10-24 | 2024-01-30 | Chee Sern LIM | Polyamide compositions and articles made therefrom |
EP4105270A1 (de) * | 2021-06-15 | 2022-12-21 | LANXESS Deutschland GmbH | Polyamidzusammensetzungen |
CN113429496A (zh) * | 2021-07-09 | 2021-09-24 | 贵州大学 | 一种改性无水β-环糊精作为聚丙烯发泡成核剂的应用 |
CN115181416B (zh) * | 2022-07-15 | 2023-12-22 | 华润化学材料科技股份有限公司 | 一种聚酰胺工程塑料及其制备方法与应用 |
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AU4404693A (en) * | 1992-06-03 | 1993-12-30 | Allied-Signal Inc. | Process for producing polyester or polyamide compositions comprising lactamyl phosphites as chain extending agents |
JP3449483B2 (ja) | 1995-12-29 | 2003-09-22 | ニルテク イタリア | ポリアミド及びその製造法並びにそれを含有する組成物 |
FR2762610B1 (fr) * | 1997-04-25 | 1999-07-02 | Nyltech Italia | Composition polyamide pour procede de fabrication d'articles par extrusion-soufflage et articles obtenus |
FR2779730B1 (fr) | 1998-06-11 | 2004-07-16 | Nyltech Italia | Polyamides a fluidite elevee, son procede de fabrication, compositions comprenant ce copolyamide |
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-
2011
- 2011-07-11 FR FR1156263A patent/FR2970970B1/fr not_active Expired - Fee Related
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2012
- 2012-07-06 EP EP12733695.6A patent/EP2731996B2/fr active Active
- 2012-07-06 BR BR112014000676A patent/BR112014000676A2/pt not_active Application Discontinuation
- 2012-07-06 JP JP2014519506A patent/JP6328554B2/ja active Active
- 2012-07-06 KR KR1020147003114A patent/KR20140053173A/ko active Search and Examination
- 2012-07-06 CN CN201280043888.6A patent/CN103781849B/zh active Active
- 2012-07-06 WO PCT/EP2012/063279 patent/WO2013007644A1/fr active Application Filing
- 2012-07-06 US US14/232,025 patent/US20140309367A1/en not_active Abandoned
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Also Published As
Publication number | Publication date |
---|---|
FR2970970A1 (fr) | 2012-08-03 |
JP2018035364A (ja) | 2018-03-08 |
FR2970970B1 (fr) | 2015-04-03 |
BR112014000676A2 (pt) | 2017-02-14 |
EP2731996B2 (fr) | 2022-06-29 |
US20140309367A1 (en) | 2014-10-16 |
EP2731996A1 (fr) | 2014-05-21 |
JP2014522897A (ja) | 2014-09-08 |
KR20140053173A (ko) | 2014-05-07 |
EP2731996B1 (fr) | 2018-04-04 |
CN103781849A (zh) | 2014-05-07 |
CN103781849B (zh) | 2016-12-21 |
WO2013007644A1 (fr) | 2013-01-17 |
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