JP2012533527A - ヒドロキシアルキル(メタ)アクリレートの調製方法 - Google Patents
ヒドロキシアルキル(メタ)アクリレートの調製方法 Download PDFInfo
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- JP2012533527A JP2012533527A JP2012519916A JP2012519916A JP2012533527A JP 2012533527 A JP2012533527 A JP 2012533527A JP 2012519916 A JP2012519916 A JP 2012519916A JP 2012519916 A JP2012519916 A JP 2012519916A JP 2012533527 A JP2012533527 A JP 2012533527A
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- Prior art keywords
- meth
- compound
- acrylate
- reaction
- acid
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- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 title claims abstract description 28
- 125000002768 hydroxyalkyl group Chemical group 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 31
- -1 phenoxy- Chemical class 0.000 claims description 18
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 14
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 14
- 229940126062 Compound A Drugs 0.000 claims description 11
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims description 11
- 238000002156 mixing Methods 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 7
- 230000000269 nucleophilic effect Effects 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-M methacrylate group Chemical group C(C(=C)C)(=O)[O-] CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 238000010526 radical polymerization reaction Methods 0.000 claims description 4
- 230000003068 static effect Effects 0.000 claims description 4
- 238000009826 distribution Methods 0.000 claims description 3
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
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- 238000010924 continuous production Methods 0.000 abstract description 6
- 239000000126 substance Substances 0.000 description 19
- 239000000376 reactant Substances 0.000 description 11
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- 238000010438 heat treatment Methods 0.000 description 6
- 239000003381 stabilizer Substances 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 150000001735 carboxylic acids Chemical class 0.000 description 5
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- 239000012948 isocyanate Substances 0.000 description 4
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- ZODNDDPVCIAZIQ-UHFFFAOYSA-N (2-hydroxy-3-prop-2-enoyloxypropyl) 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCC(O)COC(=O)C=C ZODNDDPVCIAZIQ-UHFFFAOYSA-N 0.000 description 2
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
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- 238000004455 differential thermal analysis Methods 0.000 description 2
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- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
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- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 2
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- OBETXYAYXDNJHR-SSDOTTSWSA-M (2r)-2-ethylhexanoate Chemical compound CCCC[C@@H](CC)C([O-])=O OBETXYAYXDNJHR-SSDOTTSWSA-M 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/24—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran
- C07C67/26—Preparation of carboxylic acid esters by reacting carboxylic acids or derivatives thereof with a carbon-to-oxygen ether bond, e.g. acetal, tetrahydrofuran with an oxirane ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102009033831.4 | 2009-07-18 | ||
| DE102009033831A DE102009033831A1 (de) | 2009-07-18 | 2009-07-18 | Verfahren zur Herstellung von Hydroxyalkyl(meth)acrylaten |
| PCT/EP2010/004115 WO2011009526A1 (de) | 2009-07-18 | 2010-07-06 | Verfahren zur herstellung von hydroxyalkyl (meth) acrylaten |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012533527A true JP2012533527A (ja) | 2012-12-27 |
| JP2012533527A5 JP2012533527A5 (enExample) | 2013-08-15 |
Family
ID=42981021
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012519916A Withdrawn JP2012533527A (ja) | 2009-07-18 | 2010-07-06 | ヒドロキシアルキル(メタ)アクリレートの調製方法 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US20120271064A1 (enExample) |
| EP (1) | EP2456748A1 (enExample) |
| JP (1) | JP2012533527A (enExample) |
| CN (1) | CN102471225A (enExample) |
| DE (1) | DE102009033831A1 (enExample) |
| WO (1) | WO2011009526A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190091522A (ko) * | 2016-12-08 | 2019-08-06 | 아르끄마 프랑스 | (메트)아크릴산 에스테르의 제조 방법 |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011054818A2 (de) * | 2009-11-03 | 2011-05-12 | Bayer Materialscience Ag | Neue, nicht kristallisierende methacrylate, deren herstellung und verwendung |
| WO2021007441A1 (en) | 2019-07-10 | 2021-01-14 | Countertrace Llc | Contaminant remediation with functionalized (meth)acrylic polymer or copolymer macroparticulates and systems related thereto |
| CA3153629A1 (en) | 2019-09-10 | 2021-03-18 | Countertrace Llc | Fluid analyses and sensor constructs employing hexasubstituted benzenes |
| CA3153628A1 (en) | 2019-09-10 | 2021-03-18 | Countertrace Llc | Hexasubstituted benzenes, surfaces modified therewith, and associated methods |
| CN110922330B (zh) * | 2019-11-22 | 2022-08-26 | 广东新华粤石化集团股份公司 | 一种丙烯酸羟乙酯的制备方法 |
| US10807063B1 (en) * | 2019-12-31 | 2020-10-20 | Industrial Technology Research Institute | Device and method for continuously manufacturing acrylate compound |
| CN114292183B (zh) * | 2021-12-29 | 2024-06-25 | 徐州博康信息化学品有限公司 | 一种含羟基结构光刻胶树脂单体的制备方法 |
| CN119930978B (zh) * | 2025-04-03 | 2025-07-04 | 广州昊毅新材料科技股份有限公司 | 一种光固化聚氨酯树脂及其制备方法和应用 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2345394A1 (de) * | 1973-09-08 | 1975-03-27 | Roehm Gmbh | Verfahren zur herstellung von 2-hydroxyalkylestern der acryl- oder methacrylsaeure |
| AT368179B (de) | 1980-12-10 | 1982-09-27 | Vianova Kunstharz Ag | Verfahren zur herstellung von (meth)acrylsaeuremodifiziertenpolyerstern |
| DE3316593A1 (de) | 1983-05-06 | 1984-11-08 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von (meth)-acrylsaeureestern und deren verwendung |
| DE19834360A1 (de) | 1998-07-30 | 2000-02-03 | Bayer Ag | Verfahren zur Herstellung von Estern der (Meth)acrylsäure |
| DE10145229A1 (de) | 2001-09-13 | 2004-08-12 | Tesa Ag | Verarbeitung von Acrylat-Hotmelts mittels reaktiver Extrusion |
| CN1241899C (zh) * | 2002-05-31 | 2006-02-15 | 上海华谊丙烯酸有限公司 | (甲基)丙烯酸羟烷基酯的制备方法 |
| DE10235623A1 (de) * | 2002-08-02 | 2004-02-19 | Basf Ag | Verfahren zur Herstellung von Hydroxyalkylcarbonsäureestern |
| DE10357712A1 (de) * | 2003-12-09 | 2005-07-14 | Bayer Materialscience Ag | Härter |
| DE102005008032A1 (de) * | 2005-02-22 | 2006-08-31 | Bayer Materialscience Ag | Verfahren zur Herstellung von Hydroxyalkyl(meth)acrylaten und deren Verwendung |
| DE102005011231A1 (de) | 2005-03-11 | 2006-09-14 | Bayer Materialscience Ag | Spezielle Allophanate enthaltende, modifizierte Polyurethane |
-
2009
- 2009-07-18 DE DE102009033831A patent/DE102009033831A1/de not_active Withdrawn
-
2010
- 2010-07-06 CN CN2010800324284A patent/CN102471225A/zh active Pending
- 2010-07-06 JP JP2012519916A patent/JP2012533527A/ja not_active Withdrawn
- 2010-07-06 WO PCT/EP2010/004115 patent/WO2011009526A1/de not_active Ceased
- 2010-07-06 EP EP10745527A patent/EP2456748A1/de not_active Withdrawn
- 2010-07-06 US US13/378,585 patent/US20120271064A1/en not_active Abandoned
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20190091522A (ko) * | 2016-12-08 | 2019-08-06 | 아르끄마 프랑스 | (메트)아크릴산 에스테르의 제조 방법 |
| JP2020500904A (ja) * | 2016-12-08 | 2020-01-16 | アルケマ フランス | (メタ)アクリル酸エステルの製造方法 |
| JP7018446B2 (ja) | 2016-12-08 | 2022-02-10 | アルケマ フランス | (メタ)アクリル酸エステルの製造方法 |
| KR102537354B1 (ko) * | 2016-12-08 | 2023-05-25 | 아르끄마 프랑스 | (메트)아크릴산 에스테르의 제조 방법 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP2456748A1 (de) | 2012-05-30 |
| US20120271064A1 (en) | 2012-10-25 |
| DE102009033831A1 (de) | 2011-01-20 |
| CN102471225A (zh) | 2012-05-23 |
| WO2011009526A1 (de) | 2011-01-27 |
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