JP5784739B2 - 熱安定化ポリアミド組成物 - Google Patents
熱安定化ポリアミド組成物 Download PDFInfo
- Publication number
- JP5784739B2 JP5784739B2 JP2013532130A JP2013532130A JP5784739B2 JP 5784739 B2 JP5784739 B2 JP 5784739B2 JP 2013532130 A JP2013532130 A JP 2013532130A JP 2013532130 A JP2013532130 A JP 2013532130A JP 5784739 B2 JP5784739 B2 JP 5784739B2
- Authority
- JP
- Japan
- Prior art keywords
- polyamide
- tris
- composition
- propane
- diol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 229920002647 polyamide Polymers 0.000 title claims description 71
- 239000004952 Polyamide Substances 0.000 title claims description 70
- 239000000203 mixture Substances 0.000 title claims description 59
- 239000004609 Impact Modifier Substances 0.000 claims description 23
- 150000005846 sugar alcohols Polymers 0.000 claims description 23
- 125000000524 functional group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 15
- -1 Fructo Chemical compound 0.000 claims description 12
- 229920001577 copolymer Polymers 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 5
- 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 claims description 5
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 230000006641 stabilisation Effects 0.000 claims description 5
- 238000011105 stabilization Methods 0.000 claims description 5
- 239000012745 toughening agent Substances 0.000 claims description 5
- 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 claims description 4
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 claims description 4
- UNXHWFMMPAWVPI-UHFFFAOYSA-N Erythritol Natural products OCC(O)C(O)CO UNXHWFMMPAWVPI-UHFFFAOYSA-N 0.000 claims description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 claims description 4
- PYMYPHUHKUWMLA-UHFFFAOYSA-N arabinose Natural products OCC(O)C(O)C(O)C=O PYMYPHUHKUWMLA-UHFFFAOYSA-N 0.000 claims description 4
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 claims description 4
- HEBKCHPVOIAQTA-UHFFFAOYSA-N meso ribitol Natural products OCC(O)C(O)C(O)CO HEBKCHPVOIAQTA-UHFFFAOYSA-N 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 claims description 3
- ZWVMLYRJXORSEP-UHFFFAOYSA-N 1,2,6-Hexanetriol Chemical compound OCCCCC(O)CO ZWVMLYRJXORSEP-UHFFFAOYSA-N 0.000 claims description 2
- WXSVCGWHWWPQKF-UHFFFAOYSA-N 2,3-bis(2-hydroxyethyl)cyclohexan-1-ol Chemical compound OCCC1CCCC(O)C1CCO WXSVCGWHWWPQKF-UHFFFAOYSA-N 0.000 claims description 2
- PLPYCSBZHKTQPB-UHFFFAOYSA-N 2-(2-hydroxyethoxy)hexane-1,2-diol Chemical compound CCCCC(O)(CO)OCCO PLPYCSBZHKTQPB-UHFFFAOYSA-N 0.000 claims description 2
- WUIXEIPAPIJUGW-UHFFFAOYSA-N 2-[1,1-bis(2-hydroxyphenyl)propyl]phenol Chemical compound C=1C=CC=C(O)C=1C(C=1C(=CC=CC=1)O)(CC)C1=CC=CC=C1O WUIXEIPAPIJUGW-UHFFFAOYSA-N 0.000 claims description 2
- SCYXIBCYTMZXAC-UHFFFAOYSA-N 2-[5,5-bis(2-hydroxyphenyl)-3-methylpentyl]phenol Chemical compound C=1C=CC=C(O)C=1C(C=1C(=CC=CC=1)O)CC(C)CCC1=CC=CC=C1O SCYXIBCYTMZXAC-UHFFFAOYSA-N 0.000 claims description 2
- RSROEZYGRKHVMN-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;oxirane Chemical compound C1CO1.CCC(CO)(CO)CO RSROEZYGRKHVMN-UHFFFAOYSA-N 0.000 claims description 2
- MQUMNTKHZXNYGW-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;propane-1,3-diol Chemical compound OCCCO.CCC(CO)(CO)CO MQUMNTKHZXNYGW-UHFFFAOYSA-N 0.000 claims description 2
- YHXNHYKKDRMEEH-UHFFFAOYSA-N 3-(2-hydroxyethoxy)propane-1,2-diol Chemical compound OCCOCC(O)CO YHXNHYKKDRMEEH-UHFFFAOYSA-N 0.000 claims description 2
- WQYPVEKEHDLOBS-UHFFFAOYSA-N 3-(2-hydroxypropoxy)propane-1,2-diol Chemical compound CC(O)COCC(O)CO WQYPVEKEHDLOBS-UHFFFAOYSA-N 0.000 claims description 2
- AGNTUZCMJBTHOG-UHFFFAOYSA-N 3-[3-(2,3-dihydroxypropoxy)-2-hydroxypropoxy]propane-1,2-diol Chemical compound OCC(O)COCC(O)COCC(O)CO AGNTUZCMJBTHOG-UHFFFAOYSA-N 0.000 claims description 2
- KQXMFSOXJUGYBW-UHFFFAOYSA-N 3-[4,4-bis(2,3-dihydroxyphenyl)butyl]benzene-1,2-diol Chemical compound OC1=CC=CC(CCCC(C=2C(=C(O)C=CC=2)O)C=2C(=C(O)C=CC=2)O)=C1O KQXMFSOXJUGYBW-UHFFFAOYSA-N 0.000 claims description 2
- BRPSWMCDEYMRPE-UHFFFAOYSA-N 4-[1,1-bis(4-hydroxyphenyl)ethyl]phenol Chemical compound C=1C=C(O)C=CC=1C(C=1C=CC(O)=CC=1)(C)C1=CC=C(O)C=C1 BRPSWMCDEYMRPE-UHFFFAOYSA-N 0.000 claims description 2
- NOEIYOLYKBVGGI-UHFFFAOYSA-N 4-[3,3-bis(2,4-dihydroxy-3-methylphenyl)propyl]-2-methylbenzene-1,3-diol Chemical compound CC1=C(O)C=CC(CCC(C=2C(=C(C)C(O)=CC=2)O)C=2C(=C(C)C(O)=CC=2)O)=C1O NOEIYOLYKBVGGI-UHFFFAOYSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FBXFSONDSA-N Allitol Chemical compound OC[C@H](O)[C@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-FBXFSONDSA-N 0.000 claims description 2
- 229920000858 Cyclodextrin Polymers 0.000 claims description 2
- SXZYCXMUPBBULW-LECHCGJUSA-N D-(-)-Gulono-gamma-lactone Chemical compound OC[C@@H](O)[C@@H]1OC(=O)[C@H](O)[C@@H]1O SXZYCXMUPBBULW-LECHCGJUSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims description 2
- FBPFZTCFMRRESA-ZXXMMSQZSA-N D-iditol Chemical compound OC[C@@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-ZXXMMSQZSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 2
- UNXHWFMMPAWVPI-QWWZWVQMSA-N D-threitol Chemical compound OC[C@@H](O)[C@H](O)CO UNXHWFMMPAWVPI-QWWZWVQMSA-N 0.000 claims description 2
- 239000004386 Erythritol Substances 0.000 claims description 2
- OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- HEBKCHPVOIAQTA-IMJSIDKUSA-N L-arabinitol Chemical compound OC[C@H](O)C(O)[C@@H](O)CO HEBKCHPVOIAQTA-IMJSIDKUSA-N 0.000 claims description 2
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 claims description 2
- TVXBFESIOXBWNM-UHFFFAOYSA-N Xylitol Natural products OCCC(O)C(O)C(O)CCO TVXBFESIOXBWNM-UHFFFAOYSA-N 0.000 claims description 2
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 2
- PYMYPHUHKUWMLA-WDCZJNDASA-N arabinose Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)C=O PYMYPHUHKUWMLA-WDCZJNDASA-N 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 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 claims description 2
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 2
- GPLRAVKSCUXZTP-UHFFFAOYSA-N diglycerol Chemical compound OCC(O)COCC(O)CO GPLRAVKSCUXZTP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002009 diols Chemical class 0.000 claims description 2
- UNXHWFMMPAWVPI-ZXZARUISSA-N erythritol Chemical compound OC[C@H](O)[C@H](O)CO UNXHWFMMPAWVPI-ZXZARUISSA-N 0.000 claims description 2
- 235000019414 erythritol Nutrition 0.000 claims description 2
- 229940009714 erythritol Drugs 0.000 claims description 2
- 229930182830 galactose Natural products 0.000 claims description 2
- 239000008103 glucose Substances 0.000 claims description 2
- 235000010355 mannitol Nutrition 0.000 claims description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 claims description 2
- 230000003647 oxidation Effects 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 229920005862 polyol Polymers 0.000 claims description 2
- 150000003077 polyols Chemical class 0.000 claims description 2
- 239000001294 propane Substances 0.000 claims description 2
- 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 claims description 2
- 229960002920 sorbitol Drugs 0.000 claims description 2
- 235000000346 sugar Nutrition 0.000 claims description 2
- 150000008163 sugars Chemical class 0.000 claims description 2
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 claims description 2
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 claims description 2
- 239000000811 xylitol Substances 0.000 claims description 2
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 claims description 2
- 235000010447 xylitol Nutrition 0.000 claims description 2
- 229960002675 xylitol Drugs 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 2
- RAEZDADOWHBDJK-UHFFFAOYSA-N 6-(2-hydroxypropoxy)hexane-1,2-diol Chemical compound CC(O)COCCCCC(O)CO RAEZDADOWHBDJK-UHFFFAOYSA-N 0.000 claims 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 claims 1
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
- KWSLGOVYXMQPPX-UHFFFAOYSA-N 5-[3-(trifluoromethyl)phenyl]-2h-tetrazole Chemical compound FC(F)(F)C1=CC=CC(C2=NNN=N2)=C1 KWSLGOVYXMQPPX-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229920000049 Carbon (fiber) Polymers 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229930091371 Fructose Natural products 0.000 description 1
- 239000005715 Fructose Substances 0.000 description 1
- RFSUNEUAIZKAJO-ARQDHWQXSA-N Fructose Chemical compound OC[C@H]1O[C@](O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-ARQDHWQXSA-N 0.000 description 1
- 101000576320 Homo sapiens Max-binding protein MNT Proteins 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 239000004594 Masterbatch (MB) Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 229920000305 Nylon 6,10 Polymers 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
- 101000701286 Pseudomonas aeruginosa (strain ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1) Alkanesulfonate monooxygenase Proteins 0.000 description 1
- 101000983349 Solanum commersonii Osmotin-like protein OSML13 Proteins 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 229910021536 Zeolite Inorganic materials 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 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
- 150000001408 amides Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
- 230000001588 bifunctional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 230000000903 blocking effect Effects 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
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000004917 carbon fiber Substances 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000010949 copper Substances 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
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 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
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000010101 extrusion blow moulding Methods 0.000 description 1
- 239000012765 fibrous filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 238000011990 functional testing Methods 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 229920000554 ionomer Polymers 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
- 238000012423 maintenance Methods 0.000 description 1
- GQYGRYMNLHLHNK-UHFFFAOYSA-N manganese(2+);diphosphite Chemical compound [Mn+2].[Mn+2].[Mn+2].[O-]P([O-])[O-].[O-]P([O-])[O-] GQYGRYMNLHLHNK-UHFFFAOYSA-N 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002918 oxazolines Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- SDKTUKJXHDZWMB-UHFFFAOYSA-N phosphoric acid zirconium Chemical compound [Zr].P(O)(O)(O)=O SDKTUKJXHDZWMB-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920006139 poly(hexamethylene adipamide-co-hexamethylene 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
- 238000004313 potentiometry Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 238000001175 rotational moulding Methods 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
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910001379 sodium hypophosphite Inorganic materials 0.000 description 1
- 239000006076 specific stabilizer Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000002195 synergetic effect Effects 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
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 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
- 239000010457 zeolite Substances 0.000 description 1
Classifications
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- 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
- 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
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/16—Halogen-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
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/05—Alcohols; Metal alcoholates
- C08K5/053—Polyhydroxylic alcohols
-
- 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
- C08K5/04—Oxygen-containing compounds
- C08K5/06—Ethers; Acetals; Ketals; Ortho-esters
-
- 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
- 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
-
- 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
- C08L23/16—Elastomeric ethene-propene or ethene-propene-diene copolymers, e.g. EPR and EPDM rubbers
-
- 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
- C08L51/06—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 grafted on to homopolymers or copolymers of aliphatic hydrocarbons containing only one carbon-to-carbon double bond
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- Compositions Of Macromolecular Compounds (AREA)
Description
− 1つの熱可塑性ポリアミド樹脂と、
− 耐衝撃性改良剤3〜10重量%と、
− 2〜8個のヒドロキシル基を含む1つの多価アルコールとを含む組成物に関する。
− 1つの熱可塑性ポリアミド樹脂と、
− 耐衝撃性改良剤3〜10重量%と、
− 2〜8個のヒドロキシル基を含む1つの多価アルコールと、
− 1つの強化剤または増量剤と、
− 潤滑剤、難燃剤、可塑剤、成核剤、触媒、酸化防止剤、帯電防止剤、着色剤、マット化剤および成形用酸からなる群から選択された1つの添加剤とを含む。
− 熱可塑性ポリアミド樹脂と、
− 耐衝撃性改良剤3〜10重量%と、
− 2〜8個のヒドロキシル基を含む多価アルコールと、
− 強化剤または増量剤と、
− 潤滑剤、難燃剤、可塑剤、成核剤、触媒、酸化防止剤、帯電防止剤、着色剤、マット化剤および成形用酸からなる群から選択された添加剤とからなる。
特性決定
酸末端基(CEG)およびアミン末端基(AEG)含有量:電位差測定によって分析され、meq/kg単位で表される。試薬の初期量から計算された鎖ブロッキング基(TBG)の含有量。例えば、安息香酸または酢酸を鎖ブロッカーとして使用することができる。
N塩(ヘキサメチレンジアミンとアジピン酸との比1:1の塩)58.34kg(222.4モル)、テレフタル酸19.9kg(119.8モル)、32.34重量%のヘキサメチレンジアミンの水溶液44.06kg(122.6モル)、100%の酢酸340.5g(5.67モル)、脱イオン水56kgおよびSilcolapse 5020(登録商標)消泡剤6.4gを重合反応器中に導入する。ポリアミド66タイプの重合のための標準的な方法に従ってコポリアミド66/6T 65/35を製造し、290℃において15分間仕上げする。得られたポリマーを棒状体の形にキャストし、冷却し、棒状体を細断することによって粒体に形成する。
押出の前に、ポリアミド粒体を1000ppm未満の含水量に乾燥させる。40kg/hにおいておよび270rpmの速度において運転する二軸スクリュー同時回転Werner & Pleifeder ZSK 40押出機内で様々な成分および添加剤を溶融ブレンドすることによって調合物を調製する。8つの領域の温度設定はそれぞれ:250、255、260、260、265、270、275、280℃である。調合物中の全ての成分を押出機の開始時に添加する。押出機を出た棒状体を水槽中で冷却し、粗砕機を用いて粒体の形に切断し、粒体を熱封止バッグに包装する。射出成形する前に、1000ppm未満の湿分を得るために粒体を乾燥させる。
− DPEとして公知の、Sigma Aldrich社製のジペンタエリトリトール(工業銘柄)
− Ajay Europe社製のCuIおよびKI
− Owens Corning Vetrotex社製のOCV 983ガラス繊維(35重量%)
− 基準材料Exxelor VA1803を有するExxonMobil Chemical社製のエラストマー、すなわち、無水マレイン酸でグラフト化されたエチレン系の非晶質コポリマー(0.5重量%〜1重量%)
− マスターバッチとしてカーボンブラックおよびニグロシン顔料(0.7重量%)
ISO 527/1A標準に従って引張機械的性質(引張弾性率、降伏点応力、降伏点歪−5個の試料で得られた平均値)およびISO 179−1/1eU標準に従って衝撃機械的性質(ノッチなしシャルピー(Charpy)−10個の試料で得られた平均値)を空気中で熱老化の前と後に23℃において特性決定するために、調製された調合物を厚さ4mmの多機能試験片の形で、80℃の型温度を有する280℃のDemag 50Tプレス上に射出する。
Claims (7)
- 2〜8個のヒドロキシル基を含む多価アルコールを含むポリアミド組成物の耐熱酸化性を増加させるための方法であって、
耐衝撃性改良剤を組成物の全重量に対して4〜8重量%の量で使用することを含み、
前記耐衝撃性改良剤がポリアミドと反応する官能基を含み、
該耐衝撃性改良剤が無水マレイン酸でグラフト化されたエチレンのコポリマー及び無水マレイン酸でグラフト化されたエチレン/プロピレン/ジエンコポリマーより成る群から選択される、前記方法。 - 前記組成物が組成物の全重量に対して強化剤または増量剤5重量%〜60重量%を含むことを特徴とする、請求項1に記載の方法。
- 前記組成物が2〜8個のヒドロキシル基を含む多価アルコールだけからなる熱安定化系を含むことを特徴とする、請求項1または2に記載の方法。
- 前記多価アルコールが3〜8個のヒドロキシル基を有することを特徴とする、請求項1〜3のいずれか一項に記載の方法。
- 前記多価アルコールが、1,5−ペンタンジオール、2,2−ジメチル−1,3プロパンジオール、トリエチレングリコール、ポリ(グリコールエーテル)から選択されるジオール;グリセロール、トリメチロールプロパン、2,3−ジ−(2’−ヒドロキシエチル)シクロヘキサン−1−オール、ヘキサン−1,2,6−トリオール、1,1,1−トリス−(ヒドロキシメチル)エタン、3−(2’−ヒドロキシエトキシ)プロパン−1,2−ジオール、3−(2’−ヒドロキシプロポキシ)プロパン−1,2−ジオール、2−(2’−ヒドロキシエトキシ)ヘキサン−1,2−ジオール、6−(2’−ヒドロキシプロポキシ)ヘキサン−1,2−ジオール、1,1,1−トリス−[(2’−ヒドロキシエトキシ)メチル]エタン、1,1,1−トリス−[(2’−ヒドロキシプロポキシ)メチル]プロパン、1,1,1−トリス−(4’−ヒドロキシフェニル)エタン、1,1,1−トリス−(ヒドロキシフェニル)プロパン、1,1,3−トリス−(ジヒドロキシ−3−メチルフェニル)プロパン、1,1,4−トリス−(ジヒドロキシフェニル)ブタン、1,1,5−トリス−(ヒドロキシフェニル)−3−メチルペンタン、ジ−トリメチロプロパン、トリメチロールプロパンエトキシレート、またはトリメチロールプロパンプロポキシレートから選択されるトリオール;ペンタエリトリトール、ジペンタエリトリトール、およびトリペンタエリトリトールから選択されるポリオール;およびシクロデキストリン、D−マンノース、グルコース、ガラクトース、スクロース、フルクトース、キシロース、アラビノース、D−マンニトール、D−ソルビトール、D−またはL−アラビトール、キシリトール、イジトール、タリトール、アリトール、アルトリトール、グリトール、エリトリトール、トレイトールおよびD−グロン酸−γ−ラクトンから選択される糖類:からなる群から選択されることを特徴とする、請求項1〜3のいずれか一項に記載の方法。
- 前記多価アルコールが少なくとも一対のヒドロキシル基を有し、それらがそれぞれ結合している炭素原子が少なくとも1個の原子によって割り込まれていることを特徴とする、請求項1〜5のいずれか一項に記載の方法。
- 前記多価アルコールが、ジグリセロール、トリグリセロール、ペンタエリトリトール、ジペンタエリトリトール、トリペンタエリトリトールおよびジ−トリメチロールプロパンからなる群から選択されることを特徴とする、請求項1〜6のいずれか一項に記載の方法。
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FR1058036A FR2965565B1 (fr) | 2010-10-05 | 2010-10-05 | Composition polyamide thermo-stabilisee |
FR1058036 | 2010-10-05 | ||
PCT/EP2011/066909 WO2012045636A1 (fr) | 2010-10-05 | 2011-09-28 | Composition polyamide thermo-stabilisee |
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EP (1) | EP2625224B1 (ja) |
JP (1) | JP5784739B2 (ja) |
KR (1) | KR101544286B1 (ja) |
CN (1) | CN103168076B (ja) |
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FR2974095B1 (fr) * | 2011-04-13 | 2014-08-22 | Rhodia Operations | Polyamide stabilise |
CN103073880A (zh) * | 2012-12-25 | 2013-05-01 | 广州鹿山新材料股份有限公司 | 一种增韧尼龙复合物及其制备方法 |
US9982133B2 (en) * | 2013-07-23 | 2018-05-29 | Rhodia Operations | Polyamide composition |
KR102078620B1 (ko) * | 2013-12-26 | 2020-02-18 | 코오롱플라스틱 주식회사 | 폴리아미드 수지 조성물 |
KR101451102B1 (ko) * | 2014-01-17 | 2014-10-15 | 주식회사 이노폴리 | 내충격성 폴리아미드 나노복합체 |
ES2857048T3 (es) * | 2014-04-02 | 2021-09-28 | Kuraray Co | Poliamida |
US9512300B2 (en) * | 2014-06-02 | 2016-12-06 | Samsung Sdi Co., Ltd. | Thermoplastic resin composition for automobiles and molded product produced from the same |
EP3006506B9 (de) * | 2014-10-08 | 2017-07-19 | Ems-Patent Ag | Fliessfähige Polyamide |
EP3115406A1 (de) * | 2015-07-10 | 2017-01-11 | LANXESS Deutschland GmbH | Thermoplastische formmassen |
WO2017155891A1 (en) * | 2016-03-08 | 2017-09-14 | Invista North America S.A R.L. | Polyamide copolymer and method of making the same |
BR112019002526B1 (pt) | 2016-08-08 | 2022-09-27 | Ticona Llc | Composição polimérica termicamente condutora para um dissipador de calor |
CN106700524A (zh) * | 2016-12-27 | 2017-05-24 | 上海长伟锦磁工程塑料有限公司 | 一种高耐热高冲击pa/abs合金材料 |
CN111344354B (zh) | 2017-11-23 | 2023-12-05 | 巴斯夫欧洲公司 | 用于制备可焊接模制体的聚酰胺组合物 |
EP3746510B1 (de) * | 2018-02-02 | 2024-01-31 | Basf Se | Verwendung von mehrwertigen alkoholen zur erhöhung der bindenahtfestigkeit nach wärmealterung in polyamiden |
CN109504080A (zh) * | 2018-12-13 | 2019-03-22 | 沈阳科通塑胶有限公司 | 一种耐水解的增强尼龙及其制备方法 |
JPWO2020230805A1 (ja) | 2019-05-16 | 2020-11-19 | ||
JP2021050323A (ja) * | 2019-09-19 | 2021-04-01 | 旭化成株式会社 | ポリアミド組成物及びその製造方法、並びに、成形品 |
EP3914649A1 (en) | 2019-10-24 | 2021-12-01 | INVISTA Textiles (U.K.) Limited | Polyamide compositions and articles made therefrom |
JPWO2021241471A1 (ja) | 2020-05-29 | 2021-12-02 | ||
EP4159790A4 (en) | 2020-05-29 | 2023-11-22 | Mitsubishi Gas Chemical Company, Inc. | POLYAMIDE RESIN, POLYAMIDE RESIN COMPOSITION AND MOLDED PRODUCT |
WO2022038865A1 (ja) | 2020-08-20 | 2022-02-24 | 三菱瓦斯化学株式会社 | ポリアミド樹脂 |
EP4201978A4 (en) | 2020-08-20 | 2024-02-14 | Mitsubishi Gas Chemical Co | POLYAMIDE RESIN |
JPWO2022195979A1 (ja) | 2021-03-15 | 2022-09-22 | ||
CN115746549A (zh) * | 2022-11-30 | 2023-03-07 | 江苏金发科技新材料有限公司 | 一种聚酰胺组合物及其制备方法和应用 |
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JPH0657787B2 (ja) * | 1985-09-20 | 1994-08-03 | 旭化成工業株式会社 | 耐衝撃性ポリアミド組成物 |
JPH0741657A (ja) * | 1993-07-26 | 1995-02-10 | Mitsubishi Gas Chem Co Inc | 樹脂組成物 |
EP1223185B1 (fr) | 1995-12-29 | 2006-05-03 | Rhodia Engineering Plastics Srl | Polyamide et son procédé de fabrication |
JPH11189673A (ja) * | 1997-12-26 | 1999-07-13 | Ajinomoto Co Inc | 熱可塑性樹脂組成物 |
JPH11236472A (ja) * | 1997-12-18 | 1999-08-31 | Chisso Corp | 難燃性熱可塑性樹脂組成物 |
FR2779730B1 (fr) | 1998-06-11 | 2004-07-16 | Nyltech Italia | Polyamides a fluidite elevee, son procede de fabrication, compositions comprenant ce copolyamide |
KR100448115B1 (ko) * | 2000-11-30 | 2004-09-10 | 현대자동차주식회사 | 폴리아미드 수지 조성물 |
EP2277675B1 (en) * | 2003-08-19 | 2012-04-04 | Solvay Specialty Polymers USA, LLC. | Impact-modified polyamide hollow body |
DE102004022963A1 (de) * | 2004-05-10 | 2005-12-08 | Ems-Chemie Ag | Thermoplastische Polyamid-Formmassen |
CN102112527B (zh) * | 2008-07-30 | 2013-07-31 | 纳幕尔杜邦公司 | 包含共稳定剂的耐热热塑性制品 |
US20110028621A1 (en) * | 2009-07-30 | 2011-02-03 | E. I. Du Pont De Nemours And Company | Heat aging resistant polyamide compositions including polyhydroxy polymers |
JP5776368B2 (ja) * | 2010-06-30 | 2015-09-09 | 東レ株式会社 | ポリアミド樹脂組成物およびその製造方法 |
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FR2965565A1 (fr) | 2012-04-06 |
CN103168076A (zh) | 2013-06-19 |
BR112013008169A2 (pt) | 2016-06-21 |
FR2965565B1 (fr) | 2014-05-02 |
CN103168076B (zh) | 2017-07-28 |
KR20130043231A (ko) | 2013-04-29 |
KR101544286B1 (ko) | 2015-08-12 |
BR112013008169B1 (pt) | 2020-03-17 |
JP2013538927A (ja) | 2013-10-17 |
WO2012045636A1 (fr) | 2012-04-12 |
EP2625224B1 (fr) | 2019-04-10 |
US9018292B2 (en) | 2015-04-28 |
US20130253115A1 (en) | 2013-09-26 |
EP2625224A1 (fr) | 2013-08-14 |
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