JP2019048995A - ポリアリーレンスルフィド樹脂、及びポリ(アリーレンスルホニウム塩) - Google Patents
ポリアリーレンスルフィド樹脂、及びポリ(アリーレンスルホニウム塩) Download PDFInfo
- Publication number
- JP2019048995A JP2019048995A JP2018209838A JP2018209838A JP2019048995A JP 2019048995 A JP2019048995 A JP 2019048995A JP 2018209838 A JP2018209838 A JP 2018209838A JP 2018209838 A JP2018209838 A JP 2018209838A JP 2019048995 A JP2019048995 A JP 2019048995A
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- JP
- Japan
- Prior art keywords
- acid
- group
- polyarylene sulfide
- sulfide resin
- 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.)
- Pending
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- 229920005989 resin Polymers 0.000 title claims abstract description 90
- 239000011347 resin Substances 0.000 title claims abstract description 90
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title claims abstract description 75
- 229920000412 polyarylene Polymers 0.000 title claims abstract description 75
- -1 poly(arylene sulfonium salt Chemical class 0.000 title claims description 97
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 7
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims abstract description 4
- 125000004957 naphthylene group Chemical group 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 21
- 125000003118 aryl group Chemical group 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 17
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 13
- 125000000732 arylene group Chemical group 0.000 claims description 12
- 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 8
- 150000001450 anions Chemical class 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 23
- 238000000034 method Methods 0.000 abstract description 18
- 239000002904 solvent Substances 0.000 description 39
- 238000006243 chemical reaction Methods 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 22
- 150000003462 sulfoxides Chemical class 0.000 description 22
- 238000005160 1H NMR spectroscopy Methods 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 21
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 20
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 18
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 18
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 18
- 239000003822 epoxy resin Substances 0.000 description 18
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 18
- 229920000647 polyepoxide Polymers 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 17
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 16
- 238000005259 measurement Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 238000002844 melting Methods 0.000 description 14
- 230000008018 melting Effects 0.000 description 14
- 239000011342 resin composition Substances 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 13
- 239000002253 acid Substances 0.000 description 12
- 150000001491 aromatic compounds Chemical class 0.000 description 12
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 12
- 238000005406 washing Methods 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 125000000524 functional group Chemical group 0.000 description 11
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 10
- 229940098779 methanesulfonic acid Drugs 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 239000004305 biphenyl Substances 0.000 description 9
- 235000010290 biphenyl Nutrition 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 239000012380 dealkylating agent Substances 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 230000004580 weight loss Effects 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000000806 elastomer Substances 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 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
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- 239000011256 inorganic filler Substances 0.000 description 8
- 229910003475 inorganic filler Inorganic materials 0.000 description 8
- 239000000203 mixture 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
- 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
- 239000007787 solid Substances 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- 239000004734 Polyphenylene sulfide Substances 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 238000004458 analytical method Methods 0.000 description 7
- SXJVFQLYZSNZBT-UHFFFAOYSA-N nonane-1,9-diamine Chemical compound NCCCCCCCCCN SXJVFQLYZSNZBT-UHFFFAOYSA-N 0.000 description 7
- 239000004843 novolac epoxy resin Substances 0.000 description 7
- 229920000069 polyphenylene sulfide Polymers 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- 229920002725 thermoplastic elastomer Polymers 0.000 description 7
- 229920005992 thermoplastic resin 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
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-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
- 239000004952 Polyamide Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 235000011054 acetic acid Nutrition 0.000 description 6
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 6
- 229920001971 elastomer Polymers 0.000 description 6
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 229910017604 nitric acid Inorganic materials 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
- 125000003396 thiol group Chemical group [H]S* 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 235000002597 Solanum melongena Nutrition 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000006116 polymerization reaction Methods 0.000 description 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 5
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 4
- WFMUXJURBCTSJZ-UHFFFAOYSA-N 1-methylsulfinyl-4-(4-methylsulfinylphenoxy)benzene Chemical compound CS(=O)C1=CC=C(C=C1)OC1=CC=C(C=C1)S(=O)C WFMUXJURBCTSJZ-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-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 class 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
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 150000004985 diamines Chemical class 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 150000002367 halogens Chemical class 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
- 238000005342 ion exchange Methods 0.000 description 4
- 238000004898 kneading Methods 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- KIDHWZJUCRJVML-UHFFFAOYSA-N putrescine Chemical compound NCCCCN KIDHWZJUCRJVML-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- VSAISIQCTGDGPU-UHFFFAOYSA-N tetraphosphorus hexaoxide Chemical compound O1P(O2)OP3OP1OP2O3 VSAISIQCTGDGPU-UHFFFAOYSA-N 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
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 4
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- 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
- 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
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 150000004984 aromatic diamines Chemical class 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 150000001735 carboxylic acids Chemical class 0.000 description 3
- 239000007810 chemical reaction solvent Substances 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
- 238000013461 design Methods 0.000 description 3
- 125000003700 epoxy group Chemical group 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 239000000945 filler Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 229910001392 phosphorus oxide Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 229910000077 silane Inorganic materials 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-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
- KBUFAQCPRSBXMN-UHFFFAOYSA-N 1,4-bis(methylsulfinyl)benzene Chemical compound CS(=O)C1=CC=C(S(C)=O)C=C1 KBUFAQCPRSBXMN-UHFFFAOYSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
- YAWIAFUBXXPJMQ-UHFFFAOYSA-N 1-bromo-4-(4-bromophenoxy)benzene Chemical compound C1=CC(Br)=CC=C1OC1=CC=C(Br)C=C1 YAWIAFUBXXPJMQ-UHFFFAOYSA-N 0.000 description 2
- JRDVJUWGULNZLR-UHFFFAOYSA-N 1-methylsulfanyl-4-(4-methylsulfanylphenoxy)benzene Chemical compound C1=CC(SC)=CC=C1OC1=CC=C(SC)C=C1 JRDVJUWGULNZLR-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
- 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
- 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
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-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
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- 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
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Abstract
Description
(式(1)、(2)、(10)又は(20)中、R1は、炭素原子数1〜10のアルキル基又は炭素原子数1〜10のアルキル基を有していてもよいアリール基を表し、R2aは、水素原子、−Ar4、−S−Ar4、−O−Ar4、−CO−Ar4、−SO2−Ar4又は−C(CF3)2−Ar4を表し、R2bは、直接結合、−Ar6−、−S−Ar6−、−O−Ar6−、−CO−Ar6−、−SO2−Ar6−又は−C(CF3)2−Ar6−を表し、Ar1、Ar2、Ar3b及びAr6は、それぞれ独立に、置換基を有してもよいアリーレン基を表し、Ar3a及びAr4は、それぞれ独立に、置換基を有してもよいアリール基を表し、Zは、直接結合、−S−、−O−、−CO−、−SO2−又は−C(CF3)2−を表し、X−は、アニオンを表す。)
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
ジフェニルエーテル:和光純薬工業(株)製、和光特級
臭素:和光純薬工業(株)製、試薬特級
n−ブチルリチウム:関東化学(株)製、2.6mol/L、n−ヘキサン溶液
ジメチルジスルフィド:和光純薬工業(株)製、和光1級
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)(五酸化二リン):和光純薬工業(株)製、和光1級
1−1.同定方法(1H−NMR)
BRUKER製DPX−400の装置にて、各種重溶媒に溶解させて測定した。
島津製作所製GCMS−QP2010を用いて測定した。
TG−DTA装置(株式会社リガク TG−8120)を用いて、20mL/minの窒素流下、20℃/minの昇温速度で測定を行い、5%重量減少温度を測定した。
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40〜350℃まで測定を行い、融点を求めた。
センシュー科学製高温ゲルパーミエーションクロマトグラフSSC−7000を用いて測定した。平均分子量は標準ポリスチレン換算で算出した。
溶媒:1−クロロナフタレン
投入口:250℃
温度:210℃
検出器:UV検出器(360nm)
サンプル濃度:1g/L
流速:0.7mL/min
(実施例1)
10Lの3つ口フラスコに、ビス[4−(メチルチオ)フェニル]スルフィド20.0[g]、ジクロロメタン5[L]を加えて溶解させ、氷浴にて冷却した。硝酸(1.38)14[mL]を少しずつ滴下し、室温下で72時間攪拌した。炭酸カリウム水溶液で中和して、ジクロロメタンにて抽出/分液操作を行い、有機層を回収した。無水硫酸マグネシウムにて有機層を乾燥した。ろ過後、ロータリーエバポレーターで溶媒を除去し、減圧乾燥することで粗生成物を得た。酢酸エチルを展開溶媒として、カラムクロマトグラフィーによって分離し、目的生成物を回収し、ロータリーエバポレーターで溶媒を除去し、減圧乾燥することでビス[4−(メチルスルフィニル)フェニル]スルフィド6.7g(収率30%)を得た。1H−NMR測定及びGC−MS測定により目的物が得られたことを確認した。
1H−NMR(溶媒CDCl3):2.75、7.49、7.61[ppm]
GC−MS:m/z 310
5Lの3つ口フラスコに、ジフェニルエーテル80.0[g]を入れ、ジクロロメタン2[L]を溶媒として溶解させた。氷浴にて冷却した後、臭素129[mL]をゆっくりと滴下した。滴下後、室温下で72時間攪拌した。反応溶媒に亜硫酸水素ナトリウム水溶液を加えて中和し反応を停止させた。有機相をジクロロメタンで抽出/分液操作を行い、有機層を回収した。後に無水硫酸マグネシウムにて乾燥した。ろ過後、ロータリーエバポレーターにて溶媒を除いた後、減圧乾させることで4,4’−ジブロモジフェニルエーテル80.2[g](収率52%)を得た。
1H−NMR(溶媒CDCl3):6.88、7.44[ppm]
GC−MS:m/z 328
1H−NMR(溶媒CDCl3):2.48、6.94、7.26[ppm]
1H−NMR(溶媒CD3CN):2.76、7.18、7.68[ppm]
GC−MS:m/z 294
(実施例3)
500mLのセパラブルフラスコにビス[4−(メチルスルフィニル)フェニル]スルフィド0.932[g]を入れ、窒素雰囲気下にし、ジフェニルスルフィド0.560[g]を加え、氷浴にて冷却後、トリフルオロメタンスルホン酸5[mL]をゆっくり滴下した。室温まで昇温し、20時間攪拌した。反応溶液を水に入れて、10分攪拌した後、ろ過した後、水洗後ろ過し、固体を回収した。ロータリーエバポレーターで溶媒を除去し、減圧乾燥することで、ポリ[トリフルオロメタンスルホン酸メチル(4−フェニルチオフェニル)スルホニウム]2.25[g](収率99%)を得た。
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]
ジフェニルスルフィドに代えて、ジフェニルエーテル0.511[g]を用いた以外は、実施例3と同様にして、ポリ[トリフルオロメタンスルホン酸メチル(4−フェニルオキシフェニル)スルホニウム−4’−メチル(4−フェニルチオフェニル)スルホニウム]2.19[g](収率98%)を得た。
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]
ジフェニルスルフィドに代えて、ビフェニル0.463[g]を用いた以外は、実施例3と同様にして、ポリ[トリフルオロメタンスルホン酸メチル(4−フェニルチオフェニル)スルホニウム−4’−メチル(4−ビフェニル)スルホニウム]2.08[g](収率95%)を得た。
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]
トリフルオロメタンスルホン酸に代えて、メタンスルホン酸5[mL]と酸化リン1[g]を用いた以外は実施例3と同様にして、ポリ[メタンスルホン酸メチル(4−フェニルチオフェニル)スルホニウム]1.76[g](収率90%)を得た。
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(重DMSO):3.27,3.93,7.76,8.19[ppm]
ビス[4−(メチルスルフィニル)フェニル]スルフィドに代えて、ビス[4−(メチルスルフィニル)フェニル]エーテル0.885[g]を用いた以外は実施例3と同様にして、ポリ[トリフルオロメタンスルホン酸メチル(4−フェニルオキシフェニル)スルホニウム−4’−メチル(4−フェニルチオフェニル)スルホニウム]2.15[g](収率95%)を得た。
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投入してイオン交換後、重酢酸に溶解させたものについて1H−NMR測定し、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]
ビス[4−(メチルスルフィニル)フェニル]スルフィド及びジフェニルスルフィドに代えて、ビス[4−(メチルスルフィニル)フェニル]エーテル0.885[g]、ジフェニルエーテル0.511[g]を用いた以外は実施例3と同様にして、ポリ[トリフルオロメタンスルホン酸メチル(4−フェニルオキシフェニル)スルホニウム]2.15[g](収率98%)を得た。
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投入してイオン交換後、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(溶媒CD3CN):3.33、3.58、7.36、7.94[ppm]
500mLセパラブルフラスコに1,4−ビス(メチルスルフィニル)ベンゼン2.00[g]を入れ、窒素雰囲気下、ジフェニルスルフィド1.84[g]と五酸化二リン3.0[g]を加えて、氷浴にて冷却した。その後、トリフルオロメタンスルホン酸30[mL]をゆっくり滴下した。0℃で1時間滴下した後、室温で24時間攪拌した。反応溶液にジエチルエーテルを添加し、ろ過することでポリ[メチルスルフォニオ−1,4−フェニレンメチルスルフォニオ−1,4−フェニレンオキシ−1,4−フェニレンビストリフラート]5.5[g](収率85%)を得た。
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(重DMSO):3.27、3,83、7.83、8.35[ppm]
Claims (2)
- 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。
(式中、R2bは、直接結合、−Ar6−、−CO−Ar6−又は−C(CF3)2−Ar6−を表し、Ar1、Ar2、Ar3b及びAr6は、それぞれ独立に、フェニレン、ナフチレン、及びビフェニレンから選ばれるいずれか1つを表し、Zは、直接結合、−S−、−O−又は−C(CF3)2−を表し、
Ar1、Ar2及びAr3bが1,4−フェニレン基、且つR2bが直接結合であるとき、Zは、直接結合又は−C(CF3)2−であり、
Ar1、Ar2及びAr3bが1,4−フェニレン基、R2bが−Ar6−、且つAr6が1,4−フェニレン基であるとき、Zは、−S−、−O−又は−C(CF3)2−である。) - 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)。
(式中、R1は、炭素原子数1〜10のアルキル基又は炭素原子数1〜10のアルキル基を有していてもよいアリール基を表し、R2bは、直接結合、−Ar6−、−CO−Ar6−、−SO2−Ar6−又は−C(CF3)2−Ar6−を表し、Ar1、Ar2、Ar3b及びAr6は、それぞれ独立に、置換基を有してもよいアリーレン基を表し、Zは、直接結合、−S−、−O−、−CO−、−SO2−又は−C(CF3)2−を表し、X−は、アニオンを表し、
Ar1、Ar2及びAr3bが1,4−フェニレン基、且つR2bが直接結合であるとき、Zは、直接結合、−CO−、−SO2−又は−C(CF3)2−であり、
Ar1、Ar2及びAr3bが1,4−フェニレン基、R2bが−Ar6−、且つAr6が1,4−フェニレン基であるとき、Zは、−S−、−O−、−CO−、−SO2−又は−C(CF3)2−である。)
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