JP6361324B2 - 環式ポリアリーレンスルフィド組成物 - Google Patents
環式ポリアリーレンスルフィド組成物 Download PDFInfo
- Publication number
- JP6361324B2 JP6361324B2 JP2014134153A JP2014134153A JP6361324B2 JP 6361324 B2 JP6361324 B2 JP 6361324B2 JP 2014134153 A JP2014134153 A JP 2014134153A JP 2014134153 A JP2014134153 A JP 2014134153A JP 6361324 B2 JP6361324 B2 JP 6361324B2
- Authority
- JP
- Japan
- Prior art keywords
- polyarylene sulfide
- copper
- cyclic polyarylene
- cyclic
- acid
- 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
- 125000004122 cyclic group Chemical group 0.000 title claims description 255
- 229920000412 polyarylene Polymers 0.000 title claims description 239
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title claims description 232
- 239000000203 mixture Substances 0.000 title claims description 149
- -1 carboxylic acid copper compound Chemical class 0.000 claims description 111
- 239000010949 copper Substances 0.000 claims description 53
- 229910052802 copper Inorganic materials 0.000 claims description 51
- 150000001923 cyclic compounds Chemical class 0.000 claims description 38
- 238000010438 heat treatment Methods 0.000 claims description 37
- 239000005749 Copper compound Substances 0.000 claims description 31
- 239000000155 melt Substances 0.000 claims description 26
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 23
- 239000012298 atmosphere Substances 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 230000004580 weight loss Effects 0.000 claims description 12
- 125000004434 sulfur atom Chemical group 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000002431 hydrogen Chemical group 0.000 claims description 8
- 230000001590 oxidative effect Effects 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- 125000000101 thioether group Chemical group 0.000 claims description 7
- 239000013585 weight reducing agent Substances 0.000 claims description 7
- 150000001735 carboxylic acids Chemical group 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 239000004734 Polyphenylene sulfide Substances 0.000 description 73
- 229920000069 polyphenylene sulfide Polymers 0.000 description 73
- 229920005989 resin Polymers 0.000 description 67
- 239000011347 resin Substances 0.000 description 67
- 238000000034 method Methods 0.000 description 40
- 239000011342 resin composition Substances 0.000 description 33
- 239000007787 solid Substances 0.000 description 28
- 230000000694 effects Effects 0.000 description 25
- 150000001875 compounds Chemical class 0.000 description 22
- 238000005259 measurement Methods 0.000 description 22
- 238000010128 melt processing Methods 0.000 description 20
- 229920005992 thermoplastic resin Polymers 0.000 description 20
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 238000002156 mixing Methods 0.000 description 17
- 230000006872 improvement Effects 0.000 description 16
- 229920006127 amorphous resin Polymers 0.000 description 14
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 13
- 150000001732 carboxylic acid derivatives Chemical group 0.000 description 13
- 239000007789 gas Substances 0.000 description 13
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
- 150000001880 copper compounds Chemical class 0.000 description 12
- OPQARKPSCNTWTJ-UHFFFAOYSA-L copper(ii) acetate Chemical compound [Cu+2].CC([O-])=O.CC([O-])=O OPQARKPSCNTWTJ-UHFFFAOYSA-L 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 11
- 238000000465 moulding Methods 0.000 description 11
- 238000012545 processing Methods 0.000 description 11
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
- 230000000052 comparative effect Effects 0.000 description 9
- 229920006038 crystalline resin Polymers 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 239000003708 ampul Substances 0.000 description 8
- 230000006866 deterioration Effects 0.000 description 8
- 239000000945 filler Substances 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000000654 additive Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- 239000000835 fiber Substances 0.000 description 7
- 238000001746 injection moulding Methods 0.000 description 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 6
- 150000001879 copper Chemical class 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 6
- 229920001225 polyester resin Polymers 0.000 description 6
- 239000004645 polyester resin Substances 0.000 description 6
- 229920000193 polymethacrylate Polymers 0.000 description 6
- 238000002411 thermogravimetry Methods 0.000 description 6
- XWUCFAJNVTZRLE-UHFFFAOYSA-N 7-thiabicyclo[2.2.1]hepta-1,3,5-triene Chemical compound C1=C(S2)C=CC2=C1 XWUCFAJNVTZRLE-UHFFFAOYSA-N 0.000 description 5
- ODPYDILFQYARBK-UHFFFAOYSA-N 7-thiabicyclo[4.1.0]hepta-1,3,5-triene Chemical group C1=CC=C2SC2=C1 ODPYDILFQYARBK-UHFFFAOYSA-N 0.000 description 5
- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- HFDWIMBEIXDNQS-UHFFFAOYSA-L copper;diformate Chemical compound [Cu+2].[O-]C=O.[O-]C=O HFDWIMBEIXDNQS-UHFFFAOYSA-L 0.000 description 5
- QYCVHILLJSYYBD-UHFFFAOYSA-L copper;oxalate Chemical compound [Cu+2].[O-]C(=O)C([O-])=O QYCVHILLJSYYBD-UHFFFAOYSA-L 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 230000001976 improved effect Effects 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- NKBWMBRPILTCRD-UHFFFAOYSA-N 2-Methylheptanoic acid Chemical compound CCCCCC(C)C(O)=O NKBWMBRPILTCRD-UHFFFAOYSA-N 0.000 description 4
- KUSYIGBGHPOWEL-UHFFFAOYSA-N 2-methyl nonaoic acid Chemical compound CCCCCCCC(C)C(O)=O KUSYIGBGHPOWEL-UHFFFAOYSA-N 0.000 description 4
- SAOSCTYRONNFTC-UHFFFAOYSA-N 2-methyl-decanoic acid Chemical compound CCCCCCCCC(C)C(O)=O SAOSCTYRONNFTC-UHFFFAOYSA-N 0.000 description 4
- VSAJTRPXXNCHGB-UHFFFAOYSA-N 9-methyl-decanoic acid Chemical compound CC(C)CCCCCCCC(O)=O VSAJTRPXXNCHGB-UHFFFAOYSA-N 0.000 description 4
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 4
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- IPRBZYAUMRDQHD-UHFFFAOYSA-N [Cu].CC(C(=O)O)(CCCCCC)C Chemical compound [Cu].CC(C(=O)O)(CCCCCC)C IPRBZYAUMRDQHD-UHFFFAOYSA-N 0.000 description 4
- PPFHTSXZVFATKE-UHFFFAOYSA-N [Cu].CC(CCCCCCC(=O)O)C Chemical compound [Cu].CC(CCCCCCC(=O)O)C PPFHTSXZVFATKE-UHFFFAOYSA-N 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 4
- 230000000996 additive effect Effects 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 4
- 230000008901 benefit Effects 0.000 description 4
- 239000000470 constituent Substances 0.000 description 4
- 229920001577 copolymer Polymers 0.000 description 4
- TWEDEFIZYXLAET-UHFFFAOYSA-N copper 2-methylnonanoic acid Chemical compound [Cu].CC(C(=O)O)CCCCCCC TWEDEFIZYXLAET-UHFFFAOYSA-N 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 239000003365 glass fiber Substances 0.000 description 4
- 230000009477 glass transition Effects 0.000 description 4
- 229920000587 hyperbranched polymer Polymers 0.000 description 4
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 4
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 4
- FGKJLKRYENPLQH-UHFFFAOYSA-N isocaproic acid Chemical compound CC(C)CCC(O)=O FGKJLKRYENPLQH-UHFFFAOYSA-N 0.000 description 4
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 4
- 239000001301 oxygen Substances 0.000 description 4
- 229910052760 oxygen Inorganic materials 0.000 description 4
- 229920006122 polyamide resin Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 238000001542 size-exclusion chromatography Methods 0.000 description 4
- 239000003381 stabilizer Substances 0.000 description 4
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 4
- GWYFCOCPABKNJV-UHFFFAOYSA-M 3-Methylbutanoic acid Natural products CC(C)CC([O-])=O GWYFCOCPABKNJV-UHFFFAOYSA-M 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 3
- CYKQZVNSCWCTPI-UHFFFAOYSA-L CC(C(=O)[O-])CCCCCC.[Cu+2].CC(C(=O)[O-])CCCCCC Chemical compound CC(C(=O)[O-])CCCCCC.[Cu+2].CC(C(=O)[O-])CCCCCC CYKQZVNSCWCTPI-UHFFFAOYSA-L 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 229920001400 block copolymer Polymers 0.000 description 3
- RFKZUAOAYVHBOY-UHFFFAOYSA-M copper(1+);acetate Chemical compound [Cu+].CC([O-])=O RFKZUAOAYVHBOY-UHFFFAOYSA-M 0.000 description 3
- OFSVVXIGTQSFLD-UHFFFAOYSA-M copper(1+);decanoate Chemical compound [Cu+].CCCCCCCCCC([O-])=O OFSVVXIGTQSFLD-UHFFFAOYSA-M 0.000 description 3
- SWMPRGJXLJWZLV-UHFFFAOYSA-M copper(1+);propanoate Chemical compound [Cu+].CCC([O-])=O SWMPRGJXLJWZLV-UHFFFAOYSA-M 0.000 description 3
- 239000007822 coupling agent Substances 0.000 description 3
- KHAVLLBUVKBTBG-UHFFFAOYSA-N dec-9-enoic acid Chemical compound OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000001125 extrusion Methods 0.000 description 3
- 238000005243 fluidization Methods 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 238000007429 general method Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000003993 interaction Effects 0.000 description 3
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 3
- 229920001230 polyarylate Polymers 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 3
- 229920005604 random copolymer Polymers 0.000 description 3
- 229940070710 valerate Drugs 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 2
- GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 2
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 2
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 2
- YTTWDTVYXAEAJA-UHFFFAOYSA-N 2,2-dimethyl-hexanoic acid Chemical compound CCCCC(C)(C)C(O)=O YTTWDTVYXAEAJA-UHFFFAOYSA-N 0.000 description 2
- VUAXHMVRKOTJKP-UHFFFAOYSA-N 2,2-dimethylbutyric acid Chemical compound CCC(C)(C)C(O)=O VUAXHMVRKOTJKP-UHFFFAOYSA-N 0.000 description 2
- QRMMMWOSHHVOCJ-UHFFFAOYSA-N 2,2-dimethylheptanoic acid Chemical compound CCCCCC(C)(C)C(O)=O QRMMMWOSHHVOCJ-UHFFFAOYSA-N 0.000 description 2
- IKNDGHRNXGEHTO-UHFFFAOYSA-N 2,2-dimethyloctanoic acid Chemical compound CCCCCCC(C)(C)C(O)=O IKNDGHRNXGEHTO-UHFFFAOYSA-N 0.000 description 2
- XMKDPSQQDXTCCK-UHFFFAOYSA-N 2,4-dimethylpentanoic acid Chemical compound CC(C)CC(C)C(O)=O XMKDPSQQDXTCCK-UHFFFAOYSA-N 0.000 description 2
- XZRHNAFEYMSXRG-UHFFFAOYSA-N 2,5-dimethylbenzoic acid Chemical compound CC1=CC=C(C)C(C(O)=O)=C1 XZRHNAFEYMSXRG-UHFFFAOYSA-N 0.000 description 2
- JNSSVMGPTZYYIW-UHFFFAOYSA-N 2-chloro-6-methyl-1-oxidopyridin-1-ium Chemical compound CC1=CC=CC(Cl)=[N+]1[O-] JNSSVMGPTZYYIW-UHFFFAOYSA-N 0.000 description 2
- YSEQNZOXHCKLOG-UHFFFAOYSA-N 2-methyl-octanoic acid Chemical compound CCCCCCC(C)C(O)=O YSEQNZOXHCKLOG-UHFFFAOYSA-N 0.000 description 2
- WLAMNBDJUVNPJU-UHFFFAOYSA-N 2-methylbutyric acid Chemical compound CCC(C)C(O)=O WLAMNBDJUVNPJU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 239000004925 Acrylic resin Substances 0.000 description 2
- BVEHSRXVCBOWCU-UHFFFAOYSA-L C(C#C)(=O)[O-].[Cu+2].C(C#C)(=O)[O-] Chemical compound C(C#C)(=O)[O-].[Cu+2].C(C#C)(=O)[O-] BVEHSRXVCBOWCU-UHFFFAOYSA-L 0.000 description 2
- LIHKIUQEWGSXFT-UHFFFAOYSA-N C(C)(=O)OC#C.[Cu] Chemical compound C(C)(=O)OC#C.[Cu] LIHKIUQEWGSXFT-UHFFFAOYSA-N 0.000 description 2
- RUWLIVIGHSYPPA-UHFFFAOYSA-L C1(=CC=CC=C1)C=1C=C(C(=O)[O-])C=CC1.[Cu+2].C1(=CC=CC=C1)C=1C=C(C(=O)[O-])C=CC1 Chemical compound C1(=CC=CC=C1)C=1C=C(C(=O)[O-])C=CC1.[Cu+2].C1(=CC=CC=C1)C=1C=C(C(=O)[O-])C=CC1 RUWLIVIGHSYPPA-UHFFFAOYSA-L 0.000 description 2
- JPFYFMOIGVYMNU-UHFFFAOYSA-L CC(C(=O)[O-])(CC)C.[Cu+2].CC(C(=O)[O-])(CC)C Chemical compound CC(C(=O)[O-])(CC)C.[Cu+2].CC(C(=O)[O-])(CC)C JPFYFMOIGVYMNU-UHFFFAOYSA-L 0.000 description 2
- DYLVYQPWZYSAMH-UHFFFAOYSA-L CC(C(=O)[O-])(CCCCC)C.[Cu+2].CC(C(=O)[O-])(CCCCC)C Chemical compound CC(C(=O)[O-])(CCCCC)C.[Cu+2].CC(C(=O)[O-])(CCCCC)C DYLVYQPWZYSAMH-UHFFFAOYSA-L 0.000 description 2
- FPVMVSJWDREWLJ-UHFFFAOYSA-M CC(C(=O)[O-])CC(C)C.[Cu+] Chemical compound CC(C(=O)[O-])CC(C)C.[Cu+] FPVMVSJWDREWLJ-UHFFFAOYSA-M 0.000 description 2
- REHUWXSLTREISJ-UHFFFAOYSA-L CC(C(=O)[O-])CCCCC.[Cu+2].CC(C(=O)[O-])CCCCC Chemical compound CC(C(=O)[O-])CCCCC.[Cu+2].CC(C(=O)[O-])CCCCC REHUWXSLTREISJ-UHFFFAOYSA-L 0.000 description 2
- 239000005635 Caprylic acid (CAS 124-07-2) Substances 0.000 description 2
- GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 239000004696 Poly ether ether ketone Substances 0.000 description 2
- 238000000944 Soxhlet extraction Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- KQRGPVDMOOUMFS-UHFFFAOYSA-L [Cu++].CCC(C)C([O-])=O.CCC(C)C([O-])=O Chemical compound [Cu++].CCC(C)C([O-])=O.CCC(C)C([O-])=O KQRGPVDMOOUMFS-UHFFFAOYSA-L 0.000 description 2
- XYHBOEHVIPDUMJ-UHFFFAOYSA-L [Cu+].C(CCCC(=O)[O-])(=O)[O-].[Cu+] Chemical compound [Cu+].C(CCCC(=O)[O-])(=O)[O-].[Cu+] XYHBOEHVIPDUMJ-UHFFFAOYSA-L 0.000 description 2
- TZOOVLYLZHTESA-UHFFFAOYSA-L [Cu+].C(CCCCC(=O)[O-])(=O)[O-].[Cu+] Chemical compound [Cu+].C(CCCCC(=O)[O-])(=O)[O-].[Cu+] TZOOVLYLZHTESA-UHFFFAOYSA-L 0.000 description 2
- IKCSATLHCPSIQE-UHFFFAOYSA-N [Cu].C(CCC=C)(=O)O Chemical compound [Cu].C(CCC=C)(=O)O IKCSATLHCPSIQE-UHFFFAOYSA-N 0.000 description 2
- TURHEKVYWAGWIV-UHFFFAOYSA-N [Cu].C(CCCC=C)(=O)O Chemical compound [Cu].C(CCCC=C)(=O)O TURHEKVYWAGWIV-UHFFFAOYSA-N 0.000 description 2
- GCZIOPFIJOQFBB-UHFFFAOYSA-N [Cu].C(CCCCCC(C)C)(=O)O Chemical compound [Cu].C(CCCCCC(C)C)(=O)O GCZIOPFIJOQFBB-UHFFFAOYSA-N 0.000 description 2
- YBNBSWYIHYIFSK-UHFFFAOYSA-N [Cu].C(CCCCCC=C)(=O)O Chemical compound [Cu].C(CCCCCC=C)(=O)O YBNBSWYIHYIFSK-UHFFFAOYSA-N 0.000 description 2
- 239000001361 adipic acid Substances 0.000 description 2
- 235000011037 adipic acid Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 2
- 239000003963 antioxidant agent Substances 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229910052786 argon Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 2
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| JP4983428B2 (ja) * | 2007-02-16 | 2012-07-25 | 東レ株式会社 | 非晶性樹脂組成物 |
| JP5585119B2 (ja) * | 2010-02-23 | 2014-09-10 | 東レ株式会社 | ポリアリーレンスルフィドの製造方法 |
| JP5978772B2 (ja) * | 2011-05-31 | 2016-08-24 | 東レ株式会社 | 環式ポリアリーレンスルフィド組成物 |
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