JP6313484B2 - ポリアリーレンスルフィド(pas)モノマーを調製する方法 - Google Patents
ポリアリーレンスルフィド(pas)モノマーを調製する方法 Download PDFInfo
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- JP6313484B2 JP6313484B2 JP2017002101A JP2017002101A JP6313484B2 JP 6313484 B2 JP6313484 B2 JP 6313484B2 JP 2017002101 A JP2017002101 A JP 2017002101A JP 2017002101 A JP2017002101 A JP 2017002101A JP 6313484 B2 JP6313484 B2 JP 6313484B2
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- formula
- cationic
- acid
- compound
- polyarylene sulfide
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- 238000000034 method Methods 0.000 title claims description 43
- 239000000178 monomer Substances 0.000 title claims description 34
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 title claims description 25
- 229920000412 polyarylene Polymers 0.000 title claims description 25
- -1 cationic sulfoxide Chemical class 0.000 claims description 49
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 30
- 150000001875 compounds Chemical class 0.000 claims description 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000003118 aryl group Chemical group 0.000 claims description 20
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 12
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 125000003944 tolyl group Chemical group 0.000 claims description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 10
- JXTGICXCHWMCPM-UHFFFAOYSA-N (methylsulfinyl)benzene Chemical compound CS(=O)C1=CC=CC=C1 JXTGICXCHWMCPM-UHFFFAOYSA-N 0.000 claims description 9
- 230000002378 acidificating effect Effects 0.000 claims description 8
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 claims description 8
- 229940098779 methanesulfonic acid Drugs 0.000 claims description 6
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 4
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 claims description 4
- 229940092714 benzenesulfonic acid Drugs 0.000 claims description 4
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 claims description 4
- BPMPBQHUHSDKAM-UHFFFAOYSA-N CC12C(C=CC=C1)(C1=CC=CC=C1)S2 Chemical compound CC12C(C=CC=C1)(C1=CC=CC=C1)S2 BPMPBQHUHSDKAM-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000000379 polymerizing effect Effects 0.000 claims description 3
- 230000001335 demethylating effect Effects 0.000 claims description 2
- 239000000543 intermediate Substances 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 27
- 239000004734 Polyphenylene sulfide Substances 0.000 description 18
- 229920000069 polyphenylene sulfide Polymers 0.000 description 18
- 238000005481 NMR spectroscopy Methods 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 230000003647 oxidation Effects 0.000 description 9
- 238000007254 oxidation reaction Methods 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 9
- 230000017858 demethylation Effects 0.000 description 8
- 238000010520 demethylation reaction Methods 0.000 description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 8
- 239000012038 nucleophile Substances 0.000 description 8
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium group Chemical group [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N 4-methylpyridine Chemical compound CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 0 CC**CC1C2C1CC(C1)C1*2 Chemical compound CC**CC1C2C1CC(C1)C1*2 0.000 description 5
- BWBGMRLCRAMKBC-UHFFFAOYSA-N Cl(=O)(=O)(=O)[O-].[SH3+].CC1=C(C=CC=C1)C1=C(C=CC(=C1)SC)C1=CC=CC=C1 Chemical compound Cl(=O)(=O)(=O)[O-].[SH3+].CC1=C(C=CC=C1)C1=C(C=CC(=C1)SC)C1=CC=CC=C1 BWBGMRLCRAMKBC-UHFFFAOYSA-N 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 4
- 239000004305 biphenyl Substances 0.000 description 4
- 235000010290 biphenyl Nutrition 0.000 description 4
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 4
- 238000007796 conventional method Methods 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 4
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 4
- 125000001041 indolyl group Chemical group 0.000 description 4
- PMSOVALSDXNWNR-UHFFFAOYSA-M methyl-(4-methylsulfanylphenyl)-phenylsulfanium;perchlorate Chemical compound [O-]Cl(=O)(=O)=O.C1=CC(SC)=CC=C1[S+](C)C1=CC=CC=C1 PMSOVALSDXNWNR-UHFFFAOYSA-M 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 239000007800 oxidant agent Substances 0.000 description 4
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 4
- 125000001544 thienyl group Chemical group 0.000 description 4
- 125000005023 xylyl group Chemical group 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 230000001590 oxidative effect Effects 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 125000000101 thioether group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 238000000113 differential scanning calorimetry Methods 0.000 description 2
- 239000012362 glacial acetic acid Substances 0.000 description 2
- QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 description 2
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- SHOMMGQAMRXRRK-UHFFFAOYSA-N C1C2CCCC1C2 Chemical compound C1C2CCCC1C2 SHOMMGQAMRXRRK-UHFFFAOYSA-N 0.000 description 1
- HKZCFDFRYBSALB-UHFFFAOYSA-N CC(C=CC=C1)=C1C(C=C(C=C1)SC)=C1C1=CC=CC=C1.S Chemical compound CC(C=CC=C1)=C1C(C=C(C=C1)SC)=C1C1=CC=CC=C1.S HKZCFDFRYBSALB-UHFFFAOYSA-N 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 238000007336 electrophilic substitution reaction Methods 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000002514 liquid chromatography mass spectrum Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 150000003222 pyridines Chemical class 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
- 238000009987 spinning Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000003375 sulfoxide group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
- C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/0227—Polyarylenethioethers derived from monomers containing two or more aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/025—Preparatory processes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/0204—Polyarylenethioethers
- C08G75/025—Preparatory processes
- C08G75/0272—Preparatory processes using other sulfur sources
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
本出願は、2016年1月11日に出願された米国仮特許出願第62/277,091号および2016年12月22日に出願された米国特許出願第15/388,215号の内容が参照として本出願に明示的に援用される。
Claims (12)
- Ar1およびAr2がフェニル基である、請求項1に記載の方法。
- Rがメチル基である、請求項1に記載の方法。
- 前記方法がハロゲンを用いない、請求項3に記載の方法。
- 前記式(5)を有する前記化合物がチオアニソールまたはメチルビフェニルスルフィドである、請求項2に記載の方法。
- 前記式(6)を有する前記化合物がメチルフェニルスルホキシドである、請求項2に記載の方法。
- 過酸化水素と前記式(2)を有する前記化合物とのモル比が2:1から4:1である、請求項1に記載の方法。
- 前記酸性条件が、メタンスルホン酸、ベンゼンスルホン酸、pトルエンスルホン酸、硫酸、またはトリフルオロメタンスルホン酸を加えることにより作り出される、請求項2に記載の方法。
- 過酸化水素と前記スルホン酸R’SO 3 Hとのモル比が2:1から4:1である、請求項1に記載の方法。
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US201662277091P | 2016-01-11 | 2016-01-11 | |
US62/277,091 | 2016-01-11 | ||
US15/388,215 US10377705B2 (en) | 2016-01-11 | 2016-12-22 | Method for preparing polyarylene sulfide (PAS) monomer |
US15/388,215 | 2016-12-22 |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2017125014A JP2017125014A (ja) | 2017-07-20 |
JP6313484B2 true JP6313484B2 (ja) | 2018-04-18 |
Family
ID=57914688
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2017002101A Active JP6313484B2 (ja) | 2016-01-11 | 2017-01-10 | ポリアリーレンスルフィド(pas)モノマーを調製する方法 |
Country Status (5)
Country | Link |
---|---|
US (1) | US10377705B2 (ja) |
EP (1) | EP3190142B1 (ja) |
JP (1) | JP6313484B2 (ja) |
CN (2) | CN106986803A (ja) |
TW (1) | TWI606997B (ja) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109320443B (zh) | 2017-08-01 | 2021-02-26 | 财团法人工业技术研究院 | 化合物的制备方法及包含其的聚合物的制备方法 |
JP6800920B2 (ja) * | 2017-08-01 | 2020-12-16 | 財團法人工業技術研究院Industrial Technology Research Institute | 化合物の作製方法およびそれを用いるポリマーの作製方法 |
CN109608638A (zh) * | 2018-11-19 | 2019-04-12 | 太原理工大学 | 一种高分子量线型聚苯硫醚的合成方法 |
KR20220084291A (ko) * | 2019-10-15 | 2022-06-21 | 솔베이 스페셜티 폴리머즈 유에스에이, 엘.엘.씨. | 폴리(아릴렌 설파이드) 중합체 및 상응하는 중합체 조성물 및 물품 |
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US2739991A (en) | 1952-07-30 | 1956-03-27 | Universal Oil Prod Co | Production of benzene |
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US3354129A (en) | 1963-11-27 | 1967-11-21 | Phillips Petroleum Co | Production of polymers from aromatic compounds |
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US3775485A (en) | 1970-09-14 | 1973-11-27 | Shell Oil Co | Production of hydroxyaryl thioethers |
JPS5029511A (ja) | 1973-07-11 | 1975-03-25 | ||
US3987016A (en) | 1975-01-16 | 1976-10-19 | The United States Of America As Represented By The Secretary Of The Air Force | Method for the preparation of polyarylene sulfides containing pendant cyano groups by polymerizing m-benzenedithiol, dibromobenzene, and 2,4-dichlorobenzonitrile |
DE2649590C3 (de) | 1975-11-05 | 1979-02-08 | Seitetsu Kagaku Co., Ltd., Hyogo (Japan) | Verfahren zur Herstellung von Alkylphenylsulfiden |
US4786713A (en) | 1987-11-06 | 1988-11-22 | Eastman Kodak Company | Copoly(arylene sulfidex-disulfide) |
JPH0178993U (ja) | 1987-11-16 | 1989-05-26 | ||
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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 |
JP6327616B2 (ja) | 2013-09-03 | 2018-05-23 | Dic株式会社 | ポリアリーレンスルフィド樹脂を含む樹脂組成物及びその製造方法、並びに成形品 |
CN104058911B (zh) * | 2014-07-10 | 2016-06-08 | 联化科技股份有限公司 | 一种利用微通道反应器制备亚砜或砜的方法 |
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