TW321655B - - Google Patents
Download PDFInfo
- Publication number
- TW321655B TW321655B TW083111777A TW83111777A TW321655B TW 321655 B TW321655 B TW 321655B TW 083111777 A TW083111777 A TW 083111777A TW 83111777 A TW83111777 A TW 83111777A TW 321655 B TW321655 B TW 321655B
- Authority
- TW
- Taiwan
- Prior art keywords
- reaction
- patent application
- item
- phosphoric acid
- temperature
- Prior art date
Links
- 238000000034 method Methods 0.000 claims abstract description 38
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 26
- 150000002596 lactones Chemical class 0.000 claims abstract description 23
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 13
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical group O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000003112 inhibitor Substances 0.000 claims abstract description 8
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims abstract description 7
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims abstract description 6
- 150000003254 radicals Chemical class 0.000 claims abstract description 6
- -1 hydroxyalkyl acrylates Chemical class 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 3
- 238000006555 catalytic reaction Methods 0.000 claims description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 1
- HEFNNWSXXWATRW-UHFFFAOYSA-N Ibuprofen Chemical compound CC(C)CC1=CC=C(C(C)C(O)=O)C=C1 HEFNNWSXXWATRW-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 claims 1
- 235000021419 vinegar Nutrition 0.000 claims 1
- 239000000052 vinegar Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 2
- 229940095095 2-hydroxyethyl acrylate Drugs 0.000 abstract 1
- 229940044192 2-hydroxyethyl methacrylate Drugs 0.000 abstract 1
- 239000000047 product Substances 0.000 description 16
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000000376 reactant Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 5
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 2
- DDKMFQGAZVMXQV-UHFFFAOYSA-N (3-chloro-2-hydroxypropyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(O)CCl DDKMFQGAZVMXQV-UHFFFAOYSA-N 0.000 description 1
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 1
- OWPUOLBODXJOKH-UHFFFAOYSA-N 2,3-dihydroxypropyl prop-2-enoate Chemical compound OCC(O)COC(=O)C=C OWPUOLBODXJOKH-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- GWZMWHWAWHPNHN-UHFFFAOYSA-N 2-hydroxypropyl prop-2-enoate Chemical compound CC(O)COC(=O)C=C GWZMWHWAWHPNHN-UHFFFAOYSA-N 0.000 description 1
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- WYSWNNQINDOXCE-UHFFFAOYSA-N OCCCC(=O)O.CC(C(=O)O)=C Chemical compound OCCCC(=O)O.CC(C(=O)O)=C WYSWNNQINDOXCE-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 229920006037 cross link polymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- RKOKDYYBPOKUKF-UHFFFAOYSA-N phosphoric acid;hydrobromide Chemical compound Br.OP(O)(O)=O RKOKDYYBPOKUKF-UHFFFAOYSA-N 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/823—Preparation processes characterised by the catalyst used for the preparation of polylactones or polylactides
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/06—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from hydroxycarboxylic acids
- C08G63/08—Lactones or lactides
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
- Saccharide Compounds (AREA)
- Polyesters Or Polycarbonates (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pyrane Compounds (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9326511A GB9326511D0 (en) | 1993-12-29 | 1993-12-29 | Macromonomer preparation |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW321655B true TW321655B (Direct) | 1997-12-01 |
Family
ID=10747266
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW083111777A TW321655B (Direct) | 1993-12-29 | 1994-12-16 |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US5731406A (Direct) |
| EP (1) | EP0737218B1 (Direct) |
| JP (1) | JP3084485B2 (Direct) |
| KR (1) | KR100333407B1 (Direct) |
| AT (1) | ATE169942T1 (Direct) |
| AU (1) | AU692500B2 (Direct) |
| BR (1) | BR9408426A (Direct) |
| DE (1) | DE69412645T2 (Direct) |
| DK (1) | DK0737218T3 (Direct) |
| ES (1) | ES2123230T3 (Direct) |
| GB (1) | GB9326511D0 (Direct) |
| MY (1) | MY114255A (Direct) |
| TW (1) | TW321655B (Direct) |
| WO (1) | WO1995018170A1 (Direct) |
| ZA (1) | ZA9410313B (Direct) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ249770A (en) | 1992-02-28 | 1996-09-25 | Univ Texas | Biodegradable, polymerisable, substantially water soluble macromer comprising at least one water soluble region, at least one degradable region and at least two free radical polymerisable regions separated by at least one degradable region |
| JPH0995643A (ja) * | 1995-07-27 | 1997-04-08 | Mazda Motor Corp | ポリオレフィン系樹脂成形品の塗料用樹脂組成物、それを用いた塗料組成物、及びその塗装方法 |
| JP2001192421A (ja) * | 2000-01-07 | 2001-07-17 | Nippon Paint Co Ltd | 反応性重合体の製造方法およびそれを含む硬化性樹脂組成物 |
| US6916547B2 (en) * | 2002-02-01 | 2005-07-12 | Awi Licensing Company | Multi-functional unsaturated polyester polyols |
| US20040242831A1 (en) * | 2003-05-30 | 2004-12-02 | Dong Tian | Enzyme catalyzed polyesters and polyol polymers |
| US20080138284A1 (en) * | 2006-09-26 | 2008-06-12 | Lipid Sciences, Inc. | Novel Peptides That Promote Lipid Efflux |
| FR2953523B1 (fr) * | 2009-12-08 | 2013-02-15 | Arkema France | Procede de preparation d'un polymere d'au moins un monomere cyclique |
| EP3061781B1 (en) | 2013-10-24 | 2020-03-18 | Nippon Soda Co., Ltd. | Polyol composition |
| WO2020214089A1 (en) * | 2019-04-15 | 2020-10-22 | Agency For Science, Technology And Research | Synthesis of polyester based polymers without use of organic solvents |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1257638A (Direct) * | 1968-11-20 | 1971-12-22 | ||
| US4683287A (en) * | 1982-11-02 | 1987-07-28 | Union Carbide Corporation | Compositions containing a reactive monomer derived from a lactone |
| CA1237239A (en) * | 1982-11-02 | 1988-05-24 | Joseph V. Koleske | Compositions containing a reactive monomer derived from a lactone |
-
1993
- 1993-12-29 GB GB9326511A patent/GB9326511D0/en active Pending
-
1994
- 1994-12-16 AU AU12478/95A patent/AU692500B2/en not_active Ceased
- 1994-12-16 KR KR1019960703283A patent/KR100333407B1/ko not_active Expired - Fee Related
- 1994-12-16 ES ES95903426T patent/ES2123230T3/es not_active Expired - Lifetime
- 1994-12-16 BR BR9408426A patent/BR9408426A/pt not_active IP Right Cessation
- 1994-12-16 WO PCT/GB1994/002748 patent/WO1995018170A1/en not_active Ceased
- 1994-12-16 TW TW083111777A patent/TW321655B/zh active
- 1994-12-16 DK DK95903426T patent/DK0737218T3/da active
- 1994-12-16 JP JP07517840A patent/JP3084485B2/ja not_active Expired - Fee Related
- 1994-12-16 DE DE69412645T patent/DE69412645T2/de not_active Expired - Fee Related
- 1994-12-16 MY MYPI94003376A patent/MY114255A/en unknown
- 1994-12-16 US US08/663,206 patent/US5731406A/en not_active Expired - Fee Related
- 1994-12-16 AT AT95903426T patent/ATE169942T1/de not_active IP Right Cessation
- 1994-12-16 EP EP95903426A patent/EP0737218B1/en not_active Expired - Lifetime
- 1994-12-27 ZA ZA9410313A patent/ZA9410313B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0737218A1 (en) | 1996-10-16 |
| ES2123230T3 (es) | 1999-01-01 |
| KR100333407B1 (ko) | 2002-11-20 |
| AU692500B2 (en) | 1998-06-11 |
| MY114255A (en) | 2002-09-30 |
| JP3084485B2 (ja) | 2000-09-04 |
| DE69412645D1 (de) | 1998-09-24 |
| AU1247895A (en) | 1995-07-17 |
| DE69412645T2 (de) | 1999-04-15 |
| ZA9410313B (en) | 1995-08-14 |
| KR960706520A (ko) | 1996-12-09 |
| BR9408426A (pt) | 1997-08-26 |
| JPH09507255A (ja) | 1997-07-22 |
| GB9326511D0 (en) | 1994-03-02 |
| DK0737218T3 (da) | 1999-05-25 |
| US5731406A (en) | 1998-03-24 |
| ATE169942T1 (de) | 1998-09-15 |
| EP0737218B1 (en) | 1998-08-19 |
| WO1995018170A1 (en) | 1995-07-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5371148A (en) | Reactive polymers having pendant flexible side chains prepared from ethylenically unsaturated carbodiimides | |
| US4213837A (en) | Vinyl ester urethanes | |
| Pellis et al. | Enzymatic synthesis of unsaturated polyesters: Functionalization and reversibility of the aza-Michael addition of pendants | |
| DE3789464T2 (de) | Lactonacrylat mit Carboxyl als Endgruppe. | |
| JP2012521471A (ja) | 不飽和ポリエステルを製造するための方法 | |
| CA2193529C (en) | Polyester and vinyl ether radiation curable compositions with reactive diluent | |
| US4632975A (en) | Polyfunctional acrylate derivatives of caprolactone-polyols | |
| US2967173A (en) | Polymerizable esters of acrylic and methacrylic acid and polymers thereof | |
| JPS5921333B2 (ja) | ウレタンアクリレ−トエステルジオ−ルアルコキシレ−トの製造方法 | |
| CN115677997A (zh) | 一种低粘度uv光固化超支化聚酯丙烯酸酯树脂及其制备方法与应用 | |
| TW420699B (en) | Radiation-curable compound | |
| US5731406A (en) | Macromonomer preparation | |
| US5714568A (en) | Methods of preparing polyesters from cycle organic carbonates in the presence alkali metal-containing catalysts | |
| TW513444B (en) | Polyester oligomer acrylates | |
| US4859792A (en) | Accelerated preparation of esters | |
| JP3198833B2 (ja) | 不飽和ポリエステル樹脂の製造方法 | |
| US4923958A (en) | Novel unsaturated polyesters | |
| EP0751158A1 (en) | Monomer mixture and process for producing the same | |
| JP2000016967A (ja) | シクロヘキサンジメタノールモノ（メタ）アクリラート・ラクトン変性物、その組成物及びそれらの製造方法 | |
| US3819760A (en) | Process for preparation of unsaturated polyester | |
| US5488138A (en) | Process for producing highly pure carboxylic acid phenyl esters | |
| US3008928A (en) | Use of sulfonamides to accelerate esterification and polycondensation reactions in the manufacture of polyester and alkyd resins | |
| TWI302909B (en) | Method for producing a methacryloyl product | |
| Johansson et al. | Synthesis, characterization, and curing of well‐defined allyl ether‐maleate functional ester oligomers: Linear versus nonlinear structures | |
| FR2790761A1 (fr) | Copolyester aliphatique biodegradable et son procede d'obtention |