JP2012513524A5 - - Google Patents
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- Publication number
- JP2012513524A5 JP2012513524A5 JP2011543517A JP2011543517A JP2012513524A5 JP 2012513524 A5 JP2012513524 A5 JP 2012513524A5 JP 2011543517 A JP2011543517 A JP 2011543517A JP 2011543517 A JP2011543517 A JP 2011543517A JP 2012513524 A5 JP2012513524 A5 JP 2012513524A5
- Authority
- JP
- Japan
- Prior art keywords
- glycol
- meth
- temperature
- ether
- poly
- 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
Links
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 36
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 229920000163 poly(trimethylene ether) Polymers 0.000 claims description 10
- -1 polytrimethylene Polymers 0.000 claims description 10
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000003112 inhibitor Substances 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000032050 esterification Effects 0.000 claims description 3
- 238000005886 esterification reaction Methods 0.000 claims description 3
- 150000007530 organic bases Chemical class 0.000 claims description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 claims description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 claims description 2
- 229940035437 1,3-propanediol Drugs 0.000 claims description 2
- 239000003377 acid catalyst Substances 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 239000000178 monomer Substances 0.000 claims description 2
- 238000006068 polycondensation reaction Methods 0.000 claims description 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- HFBMWMNUJJDEQZ-UHFFFAOYSA-N acryloyl chloride Chemical compound ClC(=O)C=C HFBMWMNUJJDEQZ-UHFFFAOYSA-N 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- CQRYARSYNCAZFO-UHFFFAOYSA-N o-hydroxybenzyl alcohol Natural products OCC1=CC=CC=C1O CQRYARSYNCAZFO-UHFFFAOYSA-N 0.000 description 1
- BVJSUAQZOZWCKN-UHFFFAOYSA-N p-hydroxybenzyl alcohol Chemical compound OCC1=CC=C(O)C=C1 BVJSUAQZOZWCKN-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US14023808P | 2008-12-23 | 2008-12-23 | |
| US61/140,238 | 2008-12-23 | ||
| PCT/US2009/062287 WO2010074805A1 (en) | 2008-12-23 | 2009-10-28 | Process for the production of acrylic and methacrylic esters of poly(trimethylene ether) glycol |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2012513524A JP2012513524A (ja) | 2012-06-14 |
| JP2012513524A5 true JP2012513524A5 (https=) | 2012-11-29 |
Family
ID=41667356
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011543517A Pending JP2012513524A (ja) | 2008-12-23 | 2009-10-28 | ポリ（トリメチレンエーテル）グリコールのアクリル酸エステルおよびメタクリル酸エステルを製造する方法 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8207372B2 (https=) |
| EP (1) | EP2370499B1 (https=) |
| JP (1) | JP2012513524A (https=) |
| KR (1) | KR20110114599A (https=) |
| CN (1) | CN102264797A (https=) |
| AU (1) | AU2009330625A1 (https=) |
| BR (1) | BRPI0914378A2 (https=) |
| CA (1) | CA2739566A1 (https=) |
| MX (1) | MX2011006737A (https=) |
| TW (1) | TW201024325A (https=) |
| WO (1) | WO2010074805A1 (https=) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP4638612A1 (en) | 2022-12-22 | 2025-10-29 | Allnex Belgium, S.A. | Actinic radiation curable coating composition comprising biobased monomer |
| EP4705364A1 (en) | 2023-05-05 | 2026-03-11 | Allnex Belgium, S.A. | A biobased radical curable composition for forming solid objects |
| CN121127508A (zh) | 2023-05-05 | 2025-12-12 | 湛新比利时股份有限公司 | 用于涂料的生物基可自由基固化的组合物 |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2892820A (en) * | 1956-03-29 | 1959-06-30 | California Research Corp | Oil soluble polymers containing polyalkylene glycol side-chains |
| US4038264A (en) * | 1974-01-07 | 1977-07-26 | National Patent Development Corporation | Hema copolymers having high oxygen permeability |
| ES2077811T3 (es) * | 1990-11-09 | 1995-12-01 | Nippon Catalytic Chem Ind | Inhibidor de polimerizacion y metodo de inhibicion de polimerizacion para un compuesto de vinilo. |
| DE4222708A1 (de) * | 1992-07-10 | 1994-01-13 | Degussa | Verfahren zur Herstellung von 1,3-Propandiol |
| US5686276A (en) * | 1995-05-12 | 1997-11-11 | E. I. Du Pont De Nemours And Company | Bioconversion of a fermentable carbon source to 1,3-propanediol by a single microorganism |
| US5633362A (en) * | 1995-05-12 | 1997-05-27 | E. I. Du Pont De Nemours And Company | Production of 1,3-propanediol from glycerol by recombinant bacteria expressing recombinant diol dehydratase |
| FR2797265B1 (fr) * | 1999-08-02 | 2004-06-18 | Essilor Int | Compositions polymerisables pour la fabrication de substrats polymeres transparents, substrats polymeres transparents obtenus et leurs applications dans l'optique |
| CN1238317C (zh) * | 1999-12-17 | 2006-01-25 | 纳幕尔杜邦公司 | 制备聚三亚甲基醚二醇的连续方法 |
| US6977291B2 (en) * | 1999-12-17 | 2005-12-20 | E.I. Du Pont De Nemours And Company | Production of polytrimethylene ether glycol and copolymers thereof |
| DE10125237A1 (de) * | 2001-05-22 | 2002-11-28 | Basf Ag | Wasserlösliche Polymerisate von Estern aus Acrylsäure und Alkylpolyalkylenglykolen |
| CN1435823A (zh) * | 2002-02-01 | 2003-08-13 | 日本胜利株式会社 | 光盘 |
| US20040030095A1 (en) * | 2002-08-09 | 2004-02-12 | Sunkara Hari B. | Poly(trimethylene-ethylene ether) glycols |
| US20040225107A1 (en) * | 2003-05-06 | 2004-11-11 | Sunkara Hari Babu | Polytrimethylene ether glycol with excellent quality from biochemically-derived 1,3-propanediol |
| US7323539B2 (en) * | 2003-05-06 | 2008-01-29 | E. I. Du Pont De Nemours And Company | Polytrimethylene ether glycol and polytrimethylene ether ester with excellent quality |
| US7084311B2 (en) * | 2003-05-06 | 2006-08-01 | E. I. Du Pont De Nemours And Company | Hydrogenation of chemically derived 1,3-propanediol |
| DE10331450A1 (de) | 2003-07-10 | 2005-01-27 | Basf Ag | (Meth)acrylsäureester monoalkoxilierter Polyole und deren Herstellung |
| US6972143B2 (en) | 2003-10-27 | 2005-12-06 | Kyle Baldwin | Protective U.V. curable cover layer for optical media |
| US20080108845A1 (en) | 2006-11-07 | 2008-05-08 | Hari Babu Sunkara | Polytrimethylene ether glycol esters |
| US20100069532A1 (en) * | 2006-12-08 | 2010-03-18 | Basf Se | Process for preparing polymerizable carboxylic esters with alkoxy groups |
-
2009
- 2009-10-28 WO PCT/US2009/062287 patent/WO2010074805A1/en not_active Ceased
- 2009-10-28 US US12/607,157 patent/US8207372B2/en not_active Expired - Fee Related
- 2009-10-28 EP EP09741178A patent/EP2370499B1/en not_active Not-in-force
- 2009-10-28 BR BRPI0914378A patent/BRPI0914378A2/pt not_active IP Right Cessation
- 2009-10-28 KR KR1020117017205A patent/KR20110114599A/ko not_active Withdrawn
- 2009-10-28 CN CN2009801523371A patent/CN102264797A/zh active Pending
- 2009-10-28 JP JP2011543517A patent/JP2012513524A/ja active Pending
- 2009-10-28 TW TW098136509A patent/TW201024325A/zh unknown
- 2009-10-28 MX MX2011006737A patent/MX2011006737A/es unknown
- 2009-10-28 AU AU2009330625A patent/AU2009330625A1/en not_active Abandoned
- 2009-10-28 CA CA2739566A patent/CA2739566A1/en not_active Abandoned
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