JP6179946B2 - ポリアリーレンスルフィドの製造方法 - Google Patents
ポリアリーレンスルフィドの製造方法 Download PDFInfo
- Publication number
- JP6179946B2 JP6179946B2 JP2013182443A JP2013182443A JP6179946B2 JP 6179946 B2 JP6179946 B2 JP 6179946B2 JP 2013182443 A JP2013182443 A JP 2013182443A JP 2013182443 A JP2013182443 A JP 2013182443A JP 6179946 B2 JP6179946 B2 JP 6179946B2
- Authority
- JP
- Japan
- Prior art keywords
- sulfide
- disulfide
- unsubstituted
- diphenyl
- substituted
- 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
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title claims description 53
- 229920000412 polyarylene Polymers 0.000 title claims description 23
- 238000000034 method Methods 0.000 title description 9
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical class C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 claims description 80
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 66
- 239000000178 monomer Substances 0.000 claims description 33
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical class C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 claims description 29
- 238000004519 manufacturing process Methods 0.000 claims description 17
- 150000003682 vanadium compounds Chemical class 0.000 claims description 17
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 239000007800 oxidant agent Substances 0.000 claims description 11
- 239000007789 gas Substances 0.000 claims description 10
- 150000007524 organic acids Chemical class 0.000 claims description 7
- IBYSTTGVDIFUAY-UHFFFAOYSA-N vanadium monoxide Chemical compound [V]=O IBYSTTGVDIFUAY-UHFFFAOYSA-N 0.000 claims description 5
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 description 28
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 27
- 229920000642 polymer Polymers 0.000 description 25
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- 238000006243 chemical reaction Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 15
- 239000002253 acid Substances 0.000 description 14
- 239000004734 Polyphenylene sulfide Substances 0.000 description 13
- 229920000069 polyphenylene sulfide Polymers 0.000 description 13
- 239000002994 raw material Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 230000008018 melting Effects 0.000 description 9
- 238000002844 melting Methods 0.000 description 9
- 125000001424 substituent group Chemical group 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 8
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 7
- 125000003118 aryl group Chemical group 0.000 description 7
- 238000002425 crystallisation Methods 0.000 description 7
- 230000008025 crystallization Effects 0.000 description 7
- 229910001882 dioxygen Inorganic materials 0.000 description 7
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- -1 sulfonium cation Chemical class 0.000 description 6
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000003710 aryl alkyl group Chemical group 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 230000035484 reaction time Effects 0.000 description 4
- FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 description 3
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 3
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 150000002019 disulfides Chemical class 0.000 description 3
- 239000011572 manganese Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 239000002243 precursor Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229950011008 tetrachloroethylene Drugs 0.000 description 3
- FSJSYDFBTIVUFD-XHTSQIMGSA-N (e)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C/C(C)=O.C\C(O)=C/C(C)=O FSJSYDFBTIVUFD-XHTSQIMGSA-N 0.000 description 2
- KZWJWYFPLXRYIL-UHFFFAOYSA-N 1,1,2,2-tetrafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)F KZWJWYFPLXRYIL-UHFFFAOYSA-N 0.000 description 2
- ZSSCTTQONPHGRA-UHFFFAOYSA-N 1-methyl-2-(2-methylphenyl)disulfanylbenzene Chemical compound CC1=CC=CC=C1SSC1=CC=CC=C1C ZSSCTTQONPHGRA-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- 229940117389 dichlorobenzene Drugs 0.000 description 2
- 230000007613 environmental effect Effects 0.000 description 2
- 238000000605 extraction Methods 0.000 description 2
- 229910052748 manganese Inorganic materials 0.000 description 2
- 239000002685 polymerization catalyst Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 description 1
- RDMHXWZYVFGYSF-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;manganese Chemical compound [Mn].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O RDMHXWZYVFGYSF-LNTINUHCSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- GKNWQHIXXANPTN-UHFFFAOYSA-N 1,1,2,2,2-pentafluoroethanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)F GKNWQHIXXANPTN-UHFFFAOYSA-N 0.000 description 1
- XBWQFDNGNOOMDZ-UHFFFAOYSA-N 1,1,2,2,3,3,3-heptafluoropropane-1-sulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)F XBWQFDNGNOOMDZ-UHFFFAOYSA-N 0.000 description 1
- JTPNRXUCIXHOKM-UHFFFAOYSA-N 1-chloronaphthalene Chemical compound C1=CC=C2C(Cl)=CC=CC2=C1 JTPNRXUCIXHOKM-UHFFFAOYSA-N 0.000 description 1
- LWHDQPLUIFIFFT-UHFFFAOYSA-N 2,3,5,6-tetrabromocyclohexa-2,5-diene-1,4-dione Chemical group BrC1=C(Br)C(=O)C(Br)=C(Br)C1=O LWHDQPLUIFIFFT-UHFFFAOYSA-N 0.000 description 1
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 1
- NDKJATAIMQKTPM-UHFFFAOYSA-N 2,3-dimethylbenzenethiol Chemical compound CC1=CC=CC(S)=C1C NDKJATAIMQKTPM-UHFFFAOYSA-N 0.000 description 1
- NHAUBUMQRJWWAT-UHFFFAOYSA-N 2,5-dimethylbenzenethiol Chemical compound CC1=CC=C(C)C(S)=C1 NHAUBUMQRJWWAT-UHFFFAOYSA-N 0.000 description 1
- QCLJODDRBGKIRW-UHFFFAOYSA-N 2,6-dimethylbenzenethiol Chemical compound CC1=CC=CC(C)=C1S QCLJODDRBGKIRW-UHFFFAOYSA-N 0.000 description 1
- JLGIRMVCNXRIMN-UHFFFAOYSA-N 2-(2,6-dimethylphenyl)sulfanyl-1,3-dimethylbenzene Chemical compound CC1=CC=CC(C)=C1SC1=C(C)C=CC=C1C JLGIRMVCNXRIMN-UHFFFAOYSA-N 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical compound CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
- LXUNZSDDXMPKLP-UHFFFAOYSA-N 2-Methylbenzenethiol Chemical compound CC1=CC=CC=C1S LXUNZSDDXMPKLP-UHFFFAOYSA-N 0.000 description 1
- GZUIZWAZYRTOIL-UHFFFAOYSA-N 2-[2-[(2-hydroxyphenyl)methylideneamino]ethyliminomethyl]phenol oxovanadium Chemical compound O=[V].C(C=1C(O)=CC=CC1)=NCCN=CC=1C(O)=CC=CC1 GZUIZWAZYRTOIL-UHFFFAOYSA-N 0.000 description 1
- YNJSNEKCXVFDKW-UHFFFAOYSA-N 3-(5-amino-1h-indol-3-yl)-2-azaniumylpropanoate Chemical compound C1=C(N)C=C2C(CC(N)C(O)=O)=CNC2=C1 YNJSNEKCXVFDKW-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- WRXOZRLZDJAYDR-UHFFFAOYSA-N 3-methylbenzenethiol Chemical compound CC1=CC=CC(S)=C1 WRXOZRLZDJAYDR-UHFFFAOYSA-N 0.000 description 1
- QDRFIDSUGRGGAY-UHFFFAOYSA-N 4-(3,5-dimethyl-4-oxocyclohexa-2,5-dien-1-ylidene)-2,6-dimethylcyclohexa-2,5-dien-1-one Chemical compound C1=C(C)C(=O)C(C)=CC1=C1C=C(C)C(=O)C(C)=C1 QDRFIDSUGRGGAY-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 229920000557 Nafion® Polymers 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 229940092714 benzenesulfonic acid Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- ITZXULOAYIAYNU-UHFFFAOYSA-N cerium(4+) Chemical compound [Ce+4] ITZXULOAYIAYNU-UHFFFAOYSA-N 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- JEHCHYAKAXDFKV-UHFFFAOYSA-J lead tetraacetate Chemical compound CC(=O)O[Pb](OC(C)=O)(OC(C)=O)OC(C)=O JEHCHYAKAXDFKV-UHFFFAOYSA-J 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- LULAYUGMBFYYEX-UHFFFAOYSA-N metachloroperbenzoic acid Natural products OC(=O)C1=CC=CC(Cl)=C1 LULAYUGMBFYYEX-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- ZMCOOLAXVVKCHL-UHFFFAOYSA-N oxovanadium 5,10,15,20-tetraphenyl-21,23-dihydroporphyrin Chemical compound O=[V].c1cc2nc1c(-c1ccccc1)c1ccc([nH]1)c(-c1ccccc1)c1ccc(n1)c(-c1ccccc1)c1ccc([nH]1)c2-c1ccccc1 ZMCOOLAXVVKCHL-UHFFFAOYSA-N 0.000 description 1
- JGTNAGYHADQMCM-UHFFFAOYSA-N perfluorobutanesulfonic acid Chemical compound OS(=O)(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JGTNAGYHADQMCM-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- BHZOKUMUHVTPBX-UHFFFAOYSA-M sodium acetic acid acetate Chemical compound [Na+].CC(O)=O.CC([O-])=O BHZOKUMUHVTPBX-UHFFFAOYSA-M 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 0.000 description 1
- NLDYACGHTUPAQU-UHFFFAOYSA-N tetracyanoethylene Chemical group N#CC(C#N)=C(C#N)C#N NLDYACGHTUPAQU-UHFFFAOYSA-N 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- 229910052716 thallium Inorganic materials 0.000 description 1
- BKVIYDNLLOSFOA-UHFFFAOYSA-N thallium Chemical compound [Tl] BKVIYDNLLOSFOA-UHFFFAOYSA-N 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000005287 vanadyl group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Landscapes
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Description
[式(I)中、R1、R2、R3、R4、R5、R6、R7及びR8は、それぞれ独立に水素原子、炭素数1〜8のアルキル基、アラルキル基又はアリール基を表す。]
[式(II)中、R9、R10、R11及びR12は、それぞれ独立に水素原子、炭素数1〜8のアルキル基、アラルキル基又はアリール基を表す。]
[式(III)中、R13、R14、R15及びR16はそれぞれ独立に、炭素数1〜6のアルキル基、又は、炭素数6〜8のアリール基を表し、R17及びR18はそれぞれ独立に、水素原子、炭素数1〜6のアルキル基、又は、炭素数6〜8のアリール基を表す。]
[式(IV)中、Rfは炭素数1〜8のパーフルオロアルキル基を示す。]
[式(V)中、R21、R22、R23、R24、R25、R26、R27及びR28は、それぞれ独立に水素原子、炭素数1〜8のアルキル基、アラルキル基又はアリール基を表す。]
融点は、示差走査熱量計(DSC、セイコー電子工業(株)製)を用い、リファレンスとしてα−アルミナを使用して測定した。測定条件は、室温から20℃/分で310℃まで昇温した際の吸熱ピークの頂点を融点とした。また、310℃から室温まで20℃/分で降温した際の発熱ピークの頂点を結晶化温度とした。
高温GPC装置(ポリマーラボラトリーズ社製、商品名:PL−220)にカラム(PL gel 10μm MIXED−B LS)2本を連結し、示差屈折率検出器とした。試料10mgに1−クロロナフタレン溶媒5mlを加え、220℃で約30分加熱撹拌した。このように溶解した試料を、流速0.7ml/分で分析することで、分子量(数平均分子量Mn及び重量平均分子量Mw)を測定した。
50mlの三口フラスコに、ジフェニルジスルフィド(5.45g)を加え、さらに、バナジル(IV)アセチルアセトネート(VO(acac)2)及びトリフルオロメタンスルフォン酸(TfOH)を、モル比でジフェニルジスルフィド:VO(acac)2:TfOH=100:5:10となるように加えた。フラスコ内をスターラーチップで撹拌しながら、オイルバスにて100℃に加熱し、常圧の酸素ガスを10ml/分の流量で三口フラスコに導入した。20時間後に反応液を1g採取した。採取した反応液に対し、ジフェニルスルフィド(2ml)を加え、上記と同条件で、攪拌及び加熱をしながら再び酸素を導入した。トータル40時間後に酸素ガスの供給を止め、オイルバスをはずして室温まで冷却した。得られたポリマーを粉砕し、200mlのジクロロメタンに分散し、塩酸酸性メタノールで沈殿精製した。沈殿物をろ過、減圧乾燥することで、精製ポリフェニレンスルフィド(PPS)を得た。得られた精製PPSは、収率61%、Mn=700、Mw=1300であり、DSCにおいて、融点(Tm)=162℃であり、90℃に明確な結晶化温度(Tc)が現れた。DSCにおいて明確な結晶化温度が現れたことから、得られた精製PPSの結晶性が高いことが確認された。
50mlの三口フラスコに、ジフェニルジスルフィド(5.45g)を加え、さらに、バナジル(IV)アセチルアセトネート(VO(acac)2)及びトリフルオロメタンスルフォン酸(TfOH)を、モル比でジフェニルジスルフィド:VO(acac)2:TfOH=100:5:10となるように加えた。フラスコ内をスターラーチップで撹拌しながら、オイルバスにて100℃に加熱し、常圧の酸素ガスを10ml/分の流量で三口フラスコに導入した。20時間後に酸素ガスの供給を止め、オイルバスをはずして室温まで冷却した。得られたポリマーを粉砕し、200mlのジクロロメタンに分散し、塩酸酸性メタノールで沈殿精製した。沈殿物をろ過、減圧乾燥することで、精製ポリフェニレンスルフィド(PPS)を得た。得られた精製PPSは、収率60%、Mn=600、Mw=1200であり、DSCにおいて、融点(Tm)=138℃であったが、結晶化温度(Tc)は現れなかった。
Claims (4)
- 前記(A)バナジウム化合物が、オキソバナジウム化合物である、請求項1に記載のポリアリーレンスルフィドの製造方法。
- 前記(C)酸化剤が、酸素分子を含むガスである、請求項1又は2に記載のポリアリーレンスルフィドの製造方法。
- 前記(D)置換ジフェニルスルフィド及び/又は未置換ジフェニルスルフィドが、未置換ジフェニルスルフィドである、請求項1〜3のいずれか一項に記載のポリアリーレンスルフィドの製造方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013182443A JP6179946B2 (ja) | 2013-09-03 | 2013-09-03 | ポリアリーレンスルフィドの製造方法 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2013182443A JP6179946B2 (ja) | 2013-09-03 | 2013-09-03 | ポリアリーレンスルフィドの製造方法 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2015048442A JP2015048442A (ja) | 2015-03-16 |
JP6179946B2 true JP6179946B2 (ja) | 2017-08-16 |
Family
ID=52698724
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2013182443A Expired - Fee Related JP6179946B2 (ja) | 2013-09-03 | 2013-09-03 | ポリアリーレンスルフィドの製造方法 |
Country Status (1)
Country | Link |
---|---|
JP (1) | JP6179946B2 (ja) |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0674328B2 (ja) * | 1990-06-28 | 1994-09-21 | 出光石油化学株式会社 | ポリアリーレンスルフィドの製造法 |
-
2013
- 2013-09-03 JP JP2013182443A patent/JP6179946B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2015048442A (ja) | 2015-03-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA1311077C (en) | Preparation of poly(arylene ether ketones) | |
US5869599A (en) | Free radical ring opening for polymerization of cyclic oligomers containing an aromatic sulfide linkage | |
Teasley et al. | Synthesis and characterization of poly (oxy-1, 3-phenylenecarbonyl-1, 4-phenylene) and related polymers | |
Ueda et al. | Synthesis of poly (2, 5-dialkoxyphenylene) | |
JP6531985B2 (ja) | 成形材料及びその製造方法、並びに、光学部材及びその製造方法 | |
JP6052630B2 (ja) | ポリアリーレンスルフィドの製造方法 | |
JP6241881B2 (ja) | 成形材料及びそれを用いた光学部材、並びに、成形材料の製造方法 | |
JP6179946B2 (ja) | ポリアリーレンスルフィドの製造方法 | |
JP6179945B2 (ja) | ポリアリーレンスルフィドの製造方法 | |
JP6052631B2 (ja) | ポリアリーレンスルフィドの製造方法 | |
JP6286773B2 (ja) | ポリアリーレンスルフィドの製造方法 | |
JPH0428732B2 (ja) | ||
EP3441393B1 (en) | New cycloadduct precursors of dihalodiphenylsulfones and preparations thereof | |
Chen et al. | The preparation and characterization of novel cocylic (arylene disulfide) oligomers | |
WO2006126415A1 (ja) | 含硫黄環状オレフィン樹脂およびその製造方法 | |
JPH07116288B2 (ja) | 新規芳香族ポリエーテルスルホン共重合体及びその製造方法 | |
JP7113480B2 (ja) | 共重合体の製造方法 | |
CN109320443A (zh) | 化合物的制备方法及包含其的聚合物的制备方法 | |
JP6021002B2 (ja) | ポリエーテルケトン及びその製造方法 | |
JPS6040454B2 (ja) | ポリアリ−レンポリエ−テルスルホンの改良重合方法 | |
JP4377026B2 (ja) | 結晶性ポリ(2,5−ジ置換−1,4−フェニレンオキサイド)の製造方法とそれに用いる触媒 | |
CN116120539A (zh) | 一种含酮亚胺结构的聚芳醚类聚合物及其制备方法 | |
JPS5974123A (ja) | ポリアリ−レンエ−テルの製造法 | |
JP3160244B2 (ja) | ポリ(アリーレンセレノニウム塩)化合物とその製造方法 | |
JP3990470B2 (ja) | ポリ−1,4−フェニレンエーテルの製造方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A621 | Written request for application examination |
Free format text: JAPANESE INTERMEDIATE CODE: A621 Effective date: 20160316 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A821 Effective date: 20160316 |
|
A131 | Notification of reasons for refusal |
Free format text: JAPANESE INTERMEDIATE CODE: A131 Effective date: 20170307 |
|
A521 | Request for written amendment filed |
Free format text: JAPANESE INTERMEDIATE CODE: A523 Effective date: 20170501 |
|
TRDD | Decision of grant or rejection written | ||
A01 | Written decision to grant a patent or to grant a registration (utility model) |
Free format text: JAPANESE INTERMEDIATE CODE: A01 Effective date: 20170704 |
|
A61 | First payment of annual fees (during grant procedure) |
Free format text: JAPANESE INTERMEDIATE CODE: A61 Effective date: 20170712 |
|
R150 | Certificate of patent or registration of utility model |
Ref document number: 6179946 Country of ref document: JP Free format text: JAPANESE INTERMEDIATE CODE: R150 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
S533 | Written request for registration of change of name |
Free format text: JAPANESE INTERMEDIATE CODE: R313533 |
|
R350 | Written notification of registration of transfer |
Free format text: JAPANESE INTERMEDIATE CODE: R350 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
R250 | Receipt of annual fees |
Free format text: JAPANESE INTERMEDIATE CODE: R250 |
|
LAPS | Cancellation because of no payment of annual fees |