JP6634681B2 - ポリアリーレンスルフィド樹脂組成物及びその成形品、並びに電気自動車部品 - Google Patents
ポリアリーレンスルフィド樹脂組成物及びその成形品、並びに電気自動車部品 Download PDFInfo
- Publication number
- JP6634681B2 JP6634681B2 JP2015025265A JP2015025265A JP6634681B2 JP 6634681 B2 JP6634681 B2 JP 6634681B2 JP 2015025265 A JP2015025265 A JP 2015025265A JP 2015025265 A JP2015025265 A JP 2015025265A JP 6634681 B2 JP6634681 B2 JP 6634681B2
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- JP
- Japan
- Prior art keywords
- group
- polyarylene sulfide
- sulfide resin
- acid
- resin
- 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.)
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- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title claims description 99
- 229920000412 polyarylene Polymers 0.000 title claims description 99
- 239000011342 resin composition Substances 0.000 title claims description 36
- 229920005989 resin Polymers 0.000 claims description 105
- 239000011347 resin Substances 0.000 claims description 105
- -1 poly (arylene sulfonium salt Chemical class 0.000 claims description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 26
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 238000000034 method Methods 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 229920001971 elastomer Polymers 0.000 claims description 13
- 239000000806 elastomer Substances 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 12
- 150000003462 sulfoxides Chemical class 0.000 claims description 12
- 239000011256 inorganic filler Substances 0.000 claims description 11
- 229910003475 inorganic filler Inorganic materials 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 238000000465 moulding Methods 0.000 claims description 11
- 150000001491 aromatic compounds Chemical class 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 10
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 9
- 229920005992 thermoplastic resin Polymers 0.000 claims description 8
- 150000001450 anions Chemical class 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000003822 epoxy resin Substances 0.000 description 35
- 229920000647 polyepoxide Polymers 0.000 description 35
- 239000002904 solvent Substances 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- 150000001875 compounds Chemical class 0.000 description 29
- 239000007789 gas Substances 0.000 description 28
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 22
- 238000002844 melting Methods 0.000 description 21
- 230000008018 melting Effects 0.000 description 21
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 20
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 18
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 239000000203 mixture Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 239000003795 chemical substances by application Substances 0.000 description 14
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- 239000000126 substance Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 12
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 12
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 12
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 12
- 229920000642 polymer Polymers 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- 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 10
- 238000000862 absorption spectrum Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 10
- 230000009477 glass transition Effects 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 229910052708 sodium Inorganic materials 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000001361 adipic acid Substances 0.000 description 9
- 235000011037 adipic acid Nutrition 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 8
- 239000004305 biphenyl Substances 0.000 description 8
- 235000010290 biphenyl Nutrition 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 239000012380 dealkylating agent Substances 0.000 description 8
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 8
- 239000000155 melt Substances 0.000 description 8
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 229920003986 novolac Polymers 0.000 description 8
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 238000005406 washing Methods 0.000 description 8
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000004952 Polyamide Substances 0.000 description 7
- 239000004734 Polyphenylene sulfide Substances 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000011156 evaluation Methods 0.000 description 7
- 238000011049 filling Methods 0.000 description 7
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 7
- 229920002647 polyamide Polymers 0.000 description 7
- 229920000069 polyphenylene sulfide Polymers 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000004593 Epoxy Substances 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 6
- 238000005452 bending Methods 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 229940098779 methanesulfonic acid Drugs 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 6
- 229920002725 thermoplastic elastomer Polymers 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 230000006872 improvement Effects 0.000 description 5
- 229910017604 nitric acid Inorganic materials 0.000 description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 5
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 4
- RGVJIJUDVHOZCW-UHFFFAOYSA-N 1-methylsulfinyl-4-(4-methylsulfinylphenyl)sulfanylbenzene Chemical compound C1=CC(S(=O)C)=CC=C1SC1=CC=C(S(C)=O)C=C1 RGVJIJUDVHOZCW-UHFFFAOYSA-N 0.000 description 4
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 230000036961 partial effect Effects 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 238000002076 thermal analysis method Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 0 CC(CC1)(C=CC1S(c1ccc(CC*)cc1)=C)S(C)O Chemical compound CC(CC1)(C=CC1S(c1ccc(CC*)cc1)=C)S(C)O 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 150000004984 aromatic diamines Chemical class 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 230000020335 dealkylation Effects 0.000 description 3
- 238000006900 dealkylation reaction Methods 0.000 description 3
- 238000005890 dearylation reaction Methods 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 239000003365 glass fiber Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 238000001746 injection moulding Methods 0.000 description 3
- OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical compound COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- 229920002050 silicone resin Polymers 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 150000003460 sulfonic acids Chemical class 0.000 description 3
- 125000004434 sulfur atom Chemical group 0.000 description 3
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 0.000 description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 3
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 3
- 239000004711 α-olefin Substances 0.000 description 3
- CFTSORNHIUMCGF-UHFFFAOYSA-N (1,1,1,3,3,3-hexafluoro-2-phenylpropan-2-yl)benzene Chemical compound C=1C=CC=CC=1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1 CFTSORNHIUMCGF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- GQUSUMUJMZGXSS-UHFFFAOYSA-N 1-methylsulfanyl-4-(4-methylsulfanylphenyl)sulfanylbenzene Chemical compound C1=CC(SC)=CC=C1SC1=CC=C(SC)C=C1 GQUSUMUJMZGXSS-UHFFFAOYSA-N 0.000 description 2
- PBLZLIFKVPJDCO-UHFFFAOYSA-N 12-aminododecanoic acid Chemical compound NCCCCCCCCCCCC(O)=O PBLZLIFKVPJDCO-UHFFFAOYSA-N 0.000 description 2
- SWTNRXKFJNGFRF-UHFFFAOYSA-N 14-aminotetradecanoic acid Chemical compound NCCCCCCCCCCCCCC(O)=O SWTNRXKFJNGFRF-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- DKKYOQYISDAQER-UHFFFAOYSA-N 3-[3-(3-aminophenoxy)phenoxy]aniline Chemical compound NC1=CC=CC(OC=2C=C(OC=3C=C(N)C=CC=3)C=CC=2)=C1 DKKYOQYISDAQER-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 229920000049 Carbon (fiber) Polymers 0.000 description 2
- 208000015943 Coeliac disease Diseases 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- PPPHYGCRGMTZNA-UHFFFAOYSA-M trifluoromethyl sulfate Chemical compound [O-]S(=O)(=O)OC(F)(F)F PPPHYGCRGMTZNA-UHFFFAOYSA-M 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- 239000000326 ultraviolet stabilizing agent Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
- 150000003952 β-lactams Chemical class 0.000 description 1
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- Compositions Of Macromolecular Compounds (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Description
ポリアリーレンスルフィド樹脂は、例えば、p−ジクロロベンゼンと、硫化ナトリウム、又は水硫化ナトリウム及び水酸化ナトリウムとを原料として、有機極性溶媒中で重合反応させる溶液重合により製造することができる(例えば、特許文献2、3参照)。現在市販されているポリフェニレンスルフィド樹脂は、一般にこの方法により生産されている。
しかし、この方法で得られる重合生成物は、一般に、塩化ナトリウムやオリゴマー等の副生成物を含むため、これらを除去するための精製処理が必要とされる。精製処理の工夫によって副生成物を減らす試みが行われている(特許文献4)。
また、ポリアリーレンスルフィド樹脂は、自動車の電子制御部品のケース部分に使用されることが多く、ケース内の空隙をエポキシ樹脂やシリコーン樹脂などで封止するため、それら樹脂や金属との接着力が強いほど、破壊の起点となりやすい剥離箇所(空隙)が生じ難く、部品寿命の向上に直結するため、耐トラッキング性の向上のみならず、金属との密着性(以下、金属密着性という)や、エポキシ樹脂やシリコーン樹脂との強い接着性(以下、エポキシ樹脂等接着性という)を兼備することが課題となっていた。
前記ポリ(アリーレンスルホニウム塩)を脱アルキル化又は脱アリール化し、下記一般式(20)で表される構成単位を有するポリアリーレンスルフィド樹脂を得る工程と、
を含む方法により得ることのできるものであり、
前記ポリアリーレンスルフィド樹脂が、FT−IR分光法で測定される赤外吸収スペクトルにおいて、2910cm−1〜2930cm−1の範囲に吸収ピークを有するものである、電気自動車部品用ポリアリーレンスルフィド樹脂組成物に関する。
また、上記ガスに関しては、発生するガスの量だけでなく質に関しても本発明は優れている。本発明によれば、ポリアリーレンスルフィドの主鎖の末端がアルキル基で封鎖されているため、従来の重合法のように末端がSH等になることはない。このため、重合のメカニズム上、チオフェノールやクロロ化合物等が発生せず、作業環境の改善につながる。
また、ポリアリーレンスルフィドの主鎖の末端がアルキル基であることにより、従来の重合法のようなSHである場合に比べて分極率が低いため、洗浄工程時にガス発生の要因となる成分が除去されやすい。このため、新たな設備導入などのコスト低減に寄与する。
さらに、本発明によれば、樹脂中のナトリウム含有量を顕著に抑制でき、エポキシ接着性や耐熱水性に優れた成形品を作製することができる。
(20)の構成単位の割合は、ポリアリーレンスルフィド樹脂の結晶化度及び耐熱性の低下を抑制する観点から、ポリアリーレンスルフィド樹脂全体の10質量%以下の範囲であることが好ましく、5質量%以下であることがより好ましい。
以下に示す実施例では、下記の試薬を使用した。
ビス[4−(メチルチオ)フェニル]スルフィド:シグマアルドリッチ製 製品番号S203815−25MG
硝酸(1.38):和光純薬工業(株)製、試薬特級、含量60〜61%、密度1.38g/mL
ジフェニルスルフィド:和光純薬工業(株)製、和光特級
ジフェニルエーテル:和光純薬工業(株)製、和光特級
ビフェニル:和光純薬工業(株)製、和光特級
トリフルオロメタンスルホン酸:和光純薬工業(株)製、和光特級
メタンスルホン酸:和光純薬工業(株)製、和光特級
酸化リン(V):和光純薬工業(株)製、和光1級
ピリジン:和光純薬工業(株)製、試薬特級
N−メチルピロリドン:和光純薬工業(株)製、和光一級
1.モノマーの評価法
1−1.同定方法(1H−NMR、13C−NMR)
BRUKER製DPX−400の装置にて、各種重溶剤に溶解させて測定した。
1H−NMR(溶媒CDCl3):2.75、7.49、7.61[ppm]
3−1.ガラス転移温度及び融点
パーキンエルマー製DSC装置 Pyris Diamondを用いて、50mL/minの窒素流下、20℃/minの昇温条件で40〜400℃まで測定を行い、ガラス転移温度及び融点を求めた。
3−2.赤外吸収スペクトル
得られたPPS樹脂を融点+50℃でプレスしたのち、急冷することによって非晶性を示すフィルムを作成し、フーリエ変換赤外分光装置(以下「FT−IR装置」と略記する。日本分光製FTIR―6100を用いた)で測定した。
3−3.ポリアリーレンスルフィド樹脂の溶融粘度
ポリアリーレンスルフィド樹脂を島津製作所製フローテスター、CFT−500Cを用い、融点+20℃の温度で、荷重:1.96×106Pa、L/D=10/1にて、6分間保持した後に溶融粘度を測定した。
3−4.Mw及びMtop(分子量分布)
ポリアリーレンスルフィド樹脂の重量平均分子量及びピーク分子量を、ゲル浸透クロマトグラフィーを用いて、下記の測定条件により測定した。得られたMw及びMtopからMw/Mtopを算出した。6種類の単分散ポリスチレンを校正に用いた。
装置:超高温ポリマー分子量分布測定装置(株式会社センシュー科学製「SSC−7000」)
カラム:UT−805L(昭和電工株式会社製)
カラム温度:210℃
溶媒:1−クロロナフタレン
測定方法:UV検出器(360nm)
3−5.発生ガス量
ガスクロマトグラフ質量分析装置(島津製作所製、GC-2010)を用いて、ポリアリーレンスルフィド樹脂の所定量のサンプルを325℃で15分間加熱し、そのときの発生ガス量を質量%として定量した。
3−6.ナトリウム含有量
白金製のるつぼに、試料約0.5gを秤量し、これに97%濃硫酸約2mlを添加した後ヒーター上で加熱分解を行った。分解終了後、500℃の電気炉内で灰化した後に残渣を蒸留水に溶解させ、メスアップしたものをサンプルとして、パーキンエルマー製Optima 4300DVにて定量した。
合成例1
分析用にサンプルの少量を分取し、重DMSOに溶解させたものについて1H−NMR測定を行うことにより、目的物が合成されていることを確認した。
1H−NMR(溶媒重DMSO):3.27、3.93、7.76、8.19[ppm]
赤外吸収スペクトルを測定したところ、図1のように2917cm−1の位置に吸収ピークの存在が認められた。
このポリマーの溶融粘度は1430Pa・sであり、Mtopは57000、Mwは60000であった。
発生ガス量は0.1[wt%]と少なかった。
ナトリウム含有量は50ppm以下であった。
分析用にサンプルの少量を分取し、過剰のメタンスルホン酸によってイオン交換後、重酢酸に溶解させたものについて1H−NMR測定を行うことにより、目的物が合成されていることを確認した。
1H−NMR(溶媒重酢酸):3.17、3.92、7.61、7.87、8.08、8.18[ppm]
得られた樹脂について熱分析を行った結果、ガラス転移温度(Tg)96℃、融点229℃であった。
赤外吸収スペクトルを測定したところ、図2のように2918cm−1の位置に吸収ピークの存在が認められた。
このポリマーの溶融粘度は100Pa・sであり、Mtopは10000、Mwは12000であった。
発生ガス量は0.05[wt%]と少なかった。
ナトリウム含有量は50ppm以下であった。
分析用にサンプルの少量を分取し、過剰のメタンスルホン酸によってイオン交換後、重アセトニトリルに溶解させたものについて1H−NMR測定を行うことにより、目的物が合成されていることを確認した。
1H−NMR(重アセトニトリル):3.32、3.58、7.45、7.66、7.78、7.95[ppm]
得られた樹脂について熱分析を行った結果、ガラス転移温度(Tg)127℃、融点325℃であった。
赤外吸収スペクトルを測定したところ、図3のように2917cm−1の位置に吸収ピークの存在が認められた。
このポリマーの溶融粘度は330Pa・sであり、Mtopは16000、Mwは18000であった。
発生ガス量は0.1[wt%]と少なかった。
ナトリウム含有量は50ppm以下であった。
圧力計、温度計、コンデンサ−、デカンタ−を連結した撹拌翼付きジルコニウムライニングの1リットルオートクレーブにp−ジクロロベンゼン(以下、「p−DCB」と略記する。)220.5g(1.5モル)、NMP29.7g(0.3モル)、47.43質量%NaSH水溶液177.29g(1.5モル)、及び48.71質量%NaOH水溶液123.18g(1.5モル)を仕込み、撹拌しながら窒素雰囲気下で173℃まで2時間掛けて昇温して、水177.98gを留出させた後、釜を密閉した。その際、共沸により留出したp−DCBはデカンタ−で分離して、随時釜内に戻した。脱水終了後、内温を160℃に冷却し、NMP267.65g(2.7モル)を仕込み、230℃まで昇温し、230℃で5時間撹拌した後、250℃まで40分で昇温し、250℃で1時間撹拌した。冷却後、得られたスラリーを3リットルの水に注いで80℃で1時間撹拌した後、濾過した。このケーキを再び3リットルの温水で1時間撹拌し、洗浄した後、濾過した。この操作を4回繰り返し、濾過後、熱風乾燥機を用いて120℃で一晩乾燥して白色の粉末状のPPS(表1においてPPS−4と表記) 154gを得た。
得られた固体について熱分析を行った結果、ガラス転移温度(Tg)92℃、融点277℃であったことから、ポリフェニレンスルフィドが生成していることを確認した。
赤外吸収スペクトルを測定したところ、図4のように、2910cm−1〜2930cm−1の範囲に吸収ピークの存在は認めらなかった。
このポリマーの溶融粘度は220Pa・s、Mtopは45000、Mwは44000であった。
発生ガス量は0.5[wt%]だった。
ナトリウム含有量は600ppmであった。
<原料>
ポリアリーレンスルフィド樹脂組成物を調製するため、以下の材料を準備した。
(熱可塑性エラストマー)
ELA:エチレン/グリシジルメタクリル酸(3質量%)/アクリル酸メチル(27質量%)の共重合体(住友化学工業社製、「ボンドファースト7L」)
(シランカップリング剤)
エポキシシラン:3−グリシジルオキシプロピルトリメトキシシラン
(無機質充填剤)
GF:ガラス繊維チョップドストランド(繊維径10μm、長さ3mm)
[曲げ特性]
・準拠試験方法…ASTM D−790
・試験片…3.2mm(厚)×12.7mm(幅)×127mm(長)
・試験結果…試験数n=10の平均値
試験片を95℃の熱水に浸漬し、曲げ強さの経時変化を調べた。
・試験片…3.2mm(厚)×12.7mm(幅)×127mm(長)
・曲げ強さの試験方法…ASTM D−790
・評価項目…1000時間、3000時間後の曲げ強さの初期強さに対する保持率
・試験結果…試験数n=5の平均値
金型にセットした4×10×49mmの金属片(SUS304)に、同寸法分のポリアリーレンスルフィド樹脂組成物を射出、成形したものについて、チャック間20mm、引張速度1mm/minの条件で引張試験を実施し、金属密着強さを測定した。
3mm(厚)×25mm(幅)×75mm(長さ)の試験片を成形し、試験片上に接着面積25mm×10mmとなるようにエポキシ樹脂(主剤:XNR−5002(ナガセケムテックス製)、硬化剤:XNH−5002(ナガセケムテックス製)、主剤/硬化剤=100/90(質量比))を厚さ40〜50μmで塗布した。これらをクリップで固定後、130℃で3時間加熱し、さらに徐冷させることによってエポキシ樹脂を硬化させた。その後、5mm/分の引張速度にて引張せん断強度を測定し、実荷重を記録した。
40個分のキャビティーを有するワッシャー金型を用いて、一次スプルーに最も近い位置のキャビティー(C1)が完全に充填される限りで最低の成形条件でポリアリーレンスルフィド樹脂組成物を射出成形した。成形条件は75トン成形機、シリンダー温度:融点+40℃、金型温度:ガラス転移温度+50℃、保圧無しとした。
AA:100〜90質量%の範囲
A:89〜80質量%の範囲
B:79〜70質量%の範囲
C:69〜60質量%の範囲
D:59%質量以下の範囲
ガスクロマトグラフ質量分析装置(島津製作所製、GC-2010)を用いて、ポリアリーレンスルフィド樹脂組成物の所定量のサンプルを325℃で15分間加熱し、そのときのガス発生量を質量%として定量した。
2mm(厚み)×50mm(幅)×100mm(長)の試験片を成形し、ASTM D3638に準拠した方法で、樹脂流動方向に沿って測定し、破壊電圧と滴下数をプロットし、50滴の電圧を読み取った。
表1に示す配合組成で各原料をタンブラーによって均一に混合した後、2軸混練押出機(TEM−35B、東芝機械)を用いて融点+30℃で溶融混練して、ペレット状のコンパウンドを得た。得られたコンパウンドをシリンダー温度:融点+20℃、金型温度:金型温度:ガラス転移温度+50℃の条件で射出成形し、曲げ特性、金属密着強さ、キャビティーバランス及び耐熱水性試験に用いる試験片を作製し、各種評価を行った。また、コンパウンドについてガス発生量を測定した。結果を表1に示す。
Claims (4)
- ポリアリーレンスルフィド樹脂と、
無機質充填剤、前記ポリアリーレンスルフィド樹脂以外の熱可塑性樹脂、エラストマー、及び2以上の架橋性官能基を有する架橋性樹脂からなる群より選ばれる、少なくとも1種の他の成分と、を含有する、電気自動車部品用ポリアリーレンスルフィド樹脂組成物の製造方法であって、
前記ポリアリーレンスルフィド樹脂を、下記一般式(1)で表されるスルホキシドと下記一般式(2)で表される芳香族化合物とを反応させ、下記一般式(10)で表される構成単位を有するポリ(アリーレンスルホニウム塩)を得る工程と、
前記ポリ(アリーレンスルホニウム塩)を脱アルキル化又は脱アリール化し、下記一般式(20)で表される構成単位を有するポリアリーレンスルフィド樹脂を得る工程と、
を含む方法により得ること、
前記ポリアリーレンスルフィド樹脂が、−S−R 1 を有するものである、電気自動車部品用ポリアリーレンスルフィド樹脂組成物の製造方法。
- 前記R 1 は、メチル基である、請求項1に記載の電気自動車部品用ポリアリーレンスルフィド樹脂組成物の製造方法。
- 請求項1又は2に記載の製造方法により製造されたポリアリーレンスルフィド樹脂組成物を成形する、電気自動車部品用成形品の製造方法。
- 請求項3に記載の製造方法により製造された成形品を備えつける、電気自動車部品の製造方法。
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JP3145324B2 (ja) * | 1996-12-27 | 2001-03-12 | 科学技術振興事業団 | ポリ(チオアリーレン)化合物の製造法 |
JP4269198B2 (ja) * | 1998-07-30 | 2009-05-27 | Dic株式会社 | ポリアリーレンサルファイド樹脂組成物 |
JP2010077347A (ja) * | 2008-09-29 | 2010-04-08 | Toray Ind Inc | ポリアリーレンスルフィド樹脂の製造方法 |
JP6357731B2 (ja) * | 2013-04-17 | 2018-07-18 | 東ソー株式会社 | ポリアリーレンスルフィド組成物 |
JP2014224198A (ja) * | 2013-05-16 | 2014-12-04 | 東ソー株式会社 | ポリアリーレンスルフィド組成物 |
JP6489459B2 (ja) * | 2013-09-03 | 2019-03-27 | Dic株式会社 | ポリアリーレンスルフィドの製造方法、ポリ(アリーレンスルホニウム塩)の製造方法、並びに、スルホキシド |
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