JP2007530548A5 - - Google Patents
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- Publication number
- JP2007530548A5 JP2007530548A5 JP2007505052A JP2007505052A JP2007530548A5 JP 2007530548 A5 JP2007530548 A5 JP 2007530548A5 JP 2007505052 A JP2007505052 A JP 2007505052A JP 2007505052 A JP2007505052 A JP 2007505052A JP 2007530548 A5 JP2007530548 A5 JP 2007530548A5
- Authority
- JP
- Japan
- Prior art keywords
- och
- phenolic substrate
- reaction mixture
- product
- cyano
- 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.)
- Granted
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- 238000000034 method Methods 0.000 claims description 42
- 239000000758 substrate Substances 0.000 claims description 21
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 19
- 150000001412 amines Chemical class 0.000 claims description 16
- 239000003054 catalyst Substances 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 14
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 125000001475 halogen functional group Chemical group 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000003495 polar organic solvent Substances 0.000 claims description 6
- 238000006114 decarboxylation reaction Methods 0.000 claims description 5
- 239000012345 acetylating agent Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 2
- 230000002194 synthesizing effect Effects 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 238000006116 polymerization reaction Methods 0.000 description 10
- 239000003112 inhibitor Substances 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 4
- NGSWKAQJJWESNS-UHFFFAOYSA-N 4-coumaric acid Chemical compound OC(=O)C=CC1=CC=C(O)C=C1 NGSWKAQJJWESNS-UHFFFAOYSA-N 0.000 description 4
- UZFMOKQJFYMBGY-UHFFFAOYSA-N 4-hydroxy-TEMPO Chemical compound CC1(C)CC(O)CC(C)(C)N1[O] UZFMOKQJFYMBGY-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- -1 N-oxyl (nitroxide) Chemical class 0.000 description 4
- KSHJAFFDLKPUMT-UHFFFAOYSA-N dinitro-ortho-cresol Chemical group CC1=C(O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O KSHJAFFDLKPUMT-UHFFFAOYSA-N 0.000 description 4
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- NWVVVBRKAWDGAB-UHFFFAOYSA-N hydroquinone methyl ether Natural products COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 3
- JAMNSIXSLVPNLC-UHFFFAOYSA-N (4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1 JAMNSIXSLVPNLC-UHFFFAOYSA-N 0.000 description 2
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 description 2
- KSEBMYQBYZTDHS-HWKANZROSA-M (E)-Ferulic acid Natural products COC1=CC(\C=C\C([O-])=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-M 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N 1,4-Benzenediol Natural products OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 2
- BOBATFKNMFWLFG-UHFFFAOYSA-N 2-amino-2-cyano-n-methylacetamide Chemical compound CNC(=O)C(N)C#N BOBATFKNMFWLFG-UHFFFAOYSA-N 0.000 description 2
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 2
- YOMSJEATGXXYPX-UHFFFAOYSA-N 2-methoxy-4-vinylphenol Chemical compound COC1=CC(C=C)=CC=C1O YOMSJEATGXXYPX-UHFFFAOYSA-N 0.000 description 2
- FBTSUTGMWBDAAC-UHFFFAOYSA-N 3,4-Dihydroxystyrene Chemical compound OC1=CC=C(C=C)C=C1O FBTSUTGMWBDAAC-UHFFFAOYSA-N 0.000 description 2
- FUGYGGDSWSUORM-UHFFFAOYSA-N 4-hydroxystyrene Chemical group OC1=CC=C(C=C)C=C1 FUGYGGDSWSUORM-UHFFFAOYSA-N 0.000 description 2
- XESZUVZBAMCAEJ-UHFFFAOYSA-N 4-tert-butylcatechol Chemical compound CC(C)(C)C1=CC=C(O)C(O)=C1 XESZUVZBAMCAEJ-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical group CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- FMRHJJZUHUTGKE-UHFFFAOYSA-N Ethylhexyl salicylate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1O FMRHJJZUHUTGKE-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- SXPLGYBFGPYAHS-UHFFFAOYSA-N bis(1-hydroxy-2,2,6,6-tetramethylpiperidin-4-yl) decanedioate Chemical compound C1C(C)(C)N(O)C(C)(C)CC1OC(=O)CCCCCCCCC(=O)OC1CC(C)(C)N(O)C(C)(C)C1 SXPLGYBFGPYAHS-UHFFFAOYSA-N 0.000 description 2
- 235000004883 caffeic acid Nutrition 0.000 description 2
- 229940074360 caffeic acid Drugs 0.000 description 2
- QHJGZUSJKGVMTF-UHFFFAOYSA-N canolol Chemical compound COC1=CC(C=C)=CC(OC)=C1O QHJGZUSJKGVMTF-UHFFFAOYSA-N 0.000 description 2
- QAIPRVGONGVQAS-UHFFFAOYSA-N cis-caffeic acid Natural products OC(=O)C=CC1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-UHFFFAOYSA-N 0.000 description 2
- KSEBMYQBYZTDHS-HWKANZROSA-N ferulic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC=C1O KSEBMYQBYZTDHS-HWKANZROSA-N 0.000 description 2
- 235000001785 ferulic acid Nutrition 0.000 description 2
- 229940114124 ferulic acid Drugs 0.000 description 2
- KSEBMYQBYZTDHS-UHFFFAOYSA-N ferulic acid Natural products COC1=CC(C=CC(O)=O)=CC=C1O KSEBMYQBYZTDHS-UHFFFAOYSA-N 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 125000000687 hydroquinonyl group Chemical group C1(O)=C(C=C(O)C=C1)* 0.000 description 2
- 239000000395 magnesium oxide Substances 0.000 description 2
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 2
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- XVDBWWRIXBMVJV-UHFFFAOYSA-N n-[bis(dimethylamino)phosphanyl]-n-methylmethanamine Chemical compound CN(C)P(N(C)C)N(C)C XVDBWWRIXBMVJV-UHFFFAOYSA-N 0.000 description 2
- PMOWTIHVNWZYFI-UHFFFAOYSA-N o-Coumaric acid Natural products OC(=O)C=CC1=CC=CC=C1O PMOWTIHVNWZYFI-UHFFFAOYSA-N 0.000 description 2
- 229950000688 phenothiazine Drugs 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 235000011056 potassium acetate Nutrition 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- PCMORTLOPMLEFB-ONEGZZNKSA-N sinapic acid Chemical compound COC1=CC(\C=C\C(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-ONEGZZNKSA-N 0.000 description 2
- PCMORTLOPMLEFB-UHFFFAOYSA-N sinapinic acid Natural products COC1=CC(C=CC(O)=O)=CC(OC)=C1O PCMORTLOPMLEFB-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- QURCVMIEKCOAJU-UHFFFAOYSA-N trans-isoferulic acid Natural products COC1=CC=C(C=CC(O)=O)C=C1O QURCVMIEKCOAJU-UHFFFAOYSA-N 0.000 description 2
- AFVLVVWMAFSXCK-UHFFFAOYSA-N α-cyano-4-hydroxycinnamic acid Chemical compound OC(=O)C(C#N)=CC1=CC=C(O)C=C1 AFVLVVWMAFSXCK-UHFFFAOYSA-N 0.000 description 2
- BGDWDFVUSUCDHI-UHFFFAOYSA-N (2-acetyloxy-4-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=C(C=C)C=C1OC(C)=O BGDWDFVUSUCDHI-UHFFFAOYSA-N 0.000 description 1
- WRPYDXWBHXAKPT-UHFFFAOYSA-N (2-ethenylphenyl) acetate Chemical compound CC(=O)OC1=CC=CC=C1C=C WRPYDXWBHXAKPT-UHFFFAOYSA-N 0.000 description 1
- PAGUNWMOLOQVJA-UHFFFAOYSA-N (4-ethenyl-2,6-dimethoxyphenyl) acetate Chemical compound COC1=CC(C=C)=CC(OC)=C1OC(C)=O PAGUNWMOLOQVJA-UHFFFAOYSA-N 0.000 description 1
- FTBUUBIPWKNBRF-UHFFFAOYSA-N (4-ethenyl-2-methoxyphenyl) acetate Chemical compound COC1=CC(C=C)=CC=C1OC(C)=O FTBUUBIPWKNBRF-UHFFFAOYSA-N 0.000 description 1
- 0 *C=C(*)c1c(*)c(*)c(*)c(*)c1* Chemical compound *C=C(*)c1c(*)c(*)c(*)c(*)c1* 0.000 description 1
- DZKAISAHHPTWNO-UHFFFAOYSA-N 2-(4-hydroxyphenyl)prop-2-enenitrile Chemical compound OC1=CC=C(C(=C)C#N)C=C1 DZKAISAHHPTWNO-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- FMFHUEMLVAIBFI-UHFFFAOYSA-N 2-phenylethenyl acetate Chemical compound CC(=O)OC=CC1=CC=CC=C1 FMFHUEMLVAIBFI-UHFFFAOYSA-N 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 239000011929 di(propylene glycol) methyl ether Substances 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US55686104P | 2004-03-26 | 2004-03-26 | |
| US60/556,861 | 2004-03-26 | ||
| PCT/US2005/009290 WO2005097719A1 (en) | 2004-03-26 | 2005-03-21 | A method for preparing hydroxystyrenes and acetylated derivatives thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2007530548A JP2007530548A (ja) | 2007-11-01 |
| JP2007530548A5 true JP2007530548A5 (enExample) | 2008-05-08 |
| JP4764416B2 JP4764416B2 (ja) | 2011-09-07 |
Family
ID=35124980
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2007505052A Expired - Fee Related JP4764416B2 (ja) | 2004-03-26 | 2005-03-21 | ヒドロキシスチレンおよびそのアセチル化誘導体を製造する方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US7586013B2 (enExample) |
| JP (1) | JP4764416B2 (enExample) |
| CN (1) | CN1934061A (enExample) |
| DE (1) | DE112005000464T5 (enExample) |
| TW (1) | TW200600493A (enExample) |
| WO (1) | WO2005097719A1 (enExample) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007086559A1 (ja) * | 2006-01-27 | 2007-08-02 | Ube Industries, Ltd. | テトラヒドロピラン化合物の製造方法 |
| EP2049577A2 (en) | 2006-08-01 | 2009-04-22 | Dupont Electronic Polymers L.P. | Methods for preparing polymers from phenolic materials and compositions relating thereto |
| US7468415B2 (en) * | 2007-01-04 | 2008-12-23 | E. I. Du Pont De Nemours And Company | Method for preparing glycidyloxystyrene monomers and polymers thereof |
| JP5526948B2 (ja) * | 2010-03-31 | 2014-06-18 | ユーハ味覚糖株式会社 | ２，６−ジプレニル−４−ビニルフェノールの生成方法 |
| CN102001918B (zh) * | 2010-09-27 | 2013-12-18 | 常州大学 | 对羟基苯乙烯及其衍生物的制备方法 |
| CN103086884A (zh) * | 2012-12-14 | 2013-05-08 | 湖南科源生物制品有限公司 | 乙酰化白藜芦醇的半合成方法 |
| JP6008201B2 (ja) * | 2013-05-10 | 2016-10-19 | 東レ・ファインケミカル株式会社 | スチレン誘導体の製造方法 |
| JP6094969B2 (ja) * | 2013-06-24 | 2017-03-15 | 東レ・ファインケミカル株式会社 | ヒドロキシスチレン誘導体の製造方法 |
| CN108129318A (zh) * | 2018-01-30 | 2018-06-08 | 上海博栋化学科技有限公司 | 一种3，4-二乙酰氧基苯乙烯的制备方法 |
| CN108658731B (zh) * | 2018-06-01 | 2022-05-06 | 巨野现代精细化工有限公司 | 一种对羟基苯乙烯的合成方法 |
| CN120136704A (zh) | 2019-08-09 | 2025-06-13 | 三菱瓦斯化学株式会社 | 化合物、聚合物、组合物、膜形成用组合物、图案形成方法、绝缘膜的形成方法及化合物的制造方法 |
| CN115210208B (zh) * | 2020-06-18 | 2025-05-23 | 丸善石油化学株式会社 | 高纯度4-羟基苯乙烯溶液、其制造方法、及4-羟基苯乙烯系聚合物的制造方法 |
| CN114773191A (zh) * | 2022-04-29 | 2022-07-22 | 四川东材科技集团成都新材料有限公司 | 一种一锅法制备对乙酰氧基苯乙烯的方法 |
| KR20250126726A (ko) | 2022-12-20 | 2025-08-25 | 미쯔비시 가스 케미칼 컴파니, 인코포레이티드 | 화합물의 제조방법, 중합체, 조성물, 패턴 형성방법 |
| CN115974659B (zh) * | 2022-12-29 | 2024-08-09 | 徐州博康信息化学品有限公司 | 一种1-(1-乙氧基乙氧基)-4-乙烯基苯的合成方法 |
| CN116924907A (zh) * | 2023-06-05 | 2023-10-24 | 成都东凯芯半导体材料有限公司 | 一种一锅法制备3,4-二乙酰氧基苯乙烯的方法 |
| WO2025053121A1 (ja) * | 2023-09-08 | 2025-03-13 | 丸善石油化学株式会社 | 高純度ｏ－／ｍ－ヒドロキシスチレン溶液、その製造方法、およびｏ－／ｍ－ヒドロキシスチレン系重合体の製造方法 |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3100447C2 (de) * | 1981-01-09 | 1983-02-24 | Volker Dipl.-Chem. 6000 Frankfurt Genrich | Fensterzählrohr und Verfahren zu seiner Herstellung |
| US4316995A (en) * | 1981-02-05 | 1982-02-23 | International Flavors & Fragrances Inc. | Process for preparing vinyl phenol |
| US5151546A (en) * | 1988-07-19 | 1992-09-29 | Hoechst Celanese Corporation | Process for the production of 4-acetoxystyrene, its polymers and hydrolysis products |
| US5245074A (en) * | 1988-07-19 | 1993-09-14 | Shah Bakulesh N | Process for the production of 4-acetoxystyrene, its polymers and hydrolysis products |
| US5084533A (en) * | 1988-07-19 | 1992-01-28 | Hoechst Celanese Corporation | Neat (solventless) hydrogenation of 4-acetoxyacetophenone in the production of 4-acetoxystyrene and its polymers and hydrolysis products |
| US5041614A (en) * | 1990-07-03 | 1991-08-20 | Hoechst Celanese Corporation | Method for the preparation of 4-acetoxystyrene |
| US5136083A (en) * | 1990-08-30 | 1992-08-04 | Hoechst Celanese Corporation | Process for the purification of 4-acetoxystyrene |
| EP0502819A1 (de) * | 1991-03-01 | 1992-09-09 | Ciba-Geigy Ag | Säurekatalytisch vernetzbare Copolymere |
| TW304235B (enExample) * | 1992-04-29 | 1997-05-01 | Ocg Microelectronic Materials | |
| US5453481A (en) * | 1995-03-01 | 1995-09-26 | Hoechst Celanese Corporation | Process for preparing vinylphenol polymers and copolymers |
| US5563289A (en) * | 1995-10-13 | 1996-10-08 | Hoechst Celanese Corporation | Process for preparing acetoxystyrene |
| US5578687A (en) * | 1995-10-13 | 1996-11-26 | Hoechst Celanese Corporation | Process for preparing poly(4-hydroxystyrene) |
| JP4284423B2 (ja) * | 2003-01-28 | 2009-06-24 | 和歌山県 | スチレン誘導体の製造方法 |
-
2005
- 2005-03-17 US US11/082,258 patent/US7586013B2/en not_active Expired - Fee Related
- 2005-03-21 CN CNA2005800095674A patent/CN1934061A/zh active Pending
- 2005-03-21 WO PCT/US2005/009290 patent/WO2005097719A1/en not_active Ceased
- 2005-03-21 JP JP2007505052A patent/JP4764416B2/ja not_active Expired - Fee Related
- 2005-03-21 DE DE112005000464T patent/DE112005000464T5/de not_active Withdrawn
- 2005-03-25 TW TW094109225A patent/TW200600493A/zh unknown
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