CA1054627A - Mono hydroxy unsaturated diesters - Google Patents
Mono hydroxy unsaturated diestersInfo
- Publication number
- CA1054627A CA1054627A CA214705A CA214705A CA1054627A CA 1054627 A CA1054627 A CA 1054627A CA 214705 A CA214705 A CA 214705A CA 214705 A CA214705 A CA 214705A CA 1054627 A CA1054627 A CA 1054627A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- anhydride
- acid
- group
- isobutanol
- 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.)
- Expired
Links
- 125000002887 hydroxy group Chemical group [H]O* 0.000 title claims abstract description 22
- 150000005690 diesters Chemical class 0.000 title claims abstract description 17
- 239000000178 monomer Substances 0.000 claims abstract description 28
- 239000002253 acid Substances 0.000 claims abstract description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 20
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 18
- -1 2,3-dihydroxypropyl group Chemical group 0.000 claims abstract description 14
- 150000008064 anhydrides Chemical class 0.000 claims abstract description 14
- 239000003054 catalyst Substances 0.000 claims abstract description 13
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims abstract description 13
- 238000005886 esterification reaction Methods 0.000 claims abstract description 12
- 229920005862 polyol Polymers 0.000 claims abstract description 11
- 150000003077 polyols Chemical class 0.000 claims abstract description 11
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000003138 primary alcohols Chemical class 0.000 claims abstract description 10
- 230000032050 esterification Effects 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 66
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 52
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 24
- 229920001577 copolymer Polymers 0.000 claims description 22
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 claims description 20
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 18
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 16
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 16
- 239000011976 maleic acid Substances 0.000 claims description 16
- 229920001187 thermosetting polymer Polymers 0.000 claims description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 12
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 10
- 239000000839 emulsion Substances 0.000 claims description 9
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 claims description 8
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 8
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 8
- 238000004132 cross linking Methods 0.000 claims description 7
- 125000005395 methacrylic acid group Chemical group 0.000 claims description 7
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 5
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 5
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 claims description 5
- 239000000376 reactant Substances 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 4
- 239000001530 fumaric acid Substances 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000010992 reflux Methods 0.000 claims description 2
- 239000004094 surface-active agent Substances 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
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 2
- 239000007795 chemical reaction product Substances 0.000 claims 2
- 239000011953 free-radical catalyst Substances 0.000 claims 2
- 239000004160 Ammonium persulphate Substances 0.000 claims 1
- 235000019395 ammonium persulphate Nutrition 0.000 claims 1
- 238000004821 distillation Methods 0.000 claims 1
- 229920000642 polymer Polymers 0.000 abstract description 22
- 239000000203 mixture Substances 0.000 abstract description 19
- 150000001875 compounds Chemical class 0.000 abstract description 9
- 229920003180 amino resin Polymers 0.000 abstract description 8
- 150000003254 radicals Chemical class 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 15
- 239000000463 material Substances 0.000 description 15
- 241000894007 species Species 0.000 description 9
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000004908 Emulsion polymer Substances 0.000 description 4
- 239000012190 activator Substances 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 150000002191 fatty alcohols Chemical class 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 229960005335 propanol Drugs 0.000 description 4
- 102200073741 rs121909602 Human genes 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229920013701 VORANOL™ Polymers 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 150000002009 diols Chemical class 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 229920000728 polyester Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- LCQPFOZNYVLABG-UHFFFAOYSA-N 1-Isobutanol Chemical compound C1=CC(CNC(=O)OC)=CC=C1OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(C)O1 LCQPFOZNYVLABG-UHFFFAOYSA-N 0.000 description 1
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 description 1
- YFWIACABGHWPLP-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;propane-1,2,3-triol Chemical compound OCC(O)CO.OCCOCCO YFWIACABGHWPLP-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- HQPMKSGTIOYHJT-UHFFFAOYSA-N ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CC(O)CO HQPMKSGTIOYHJT-UHFFFAOYSA-N 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 229910002804 graphite Inorganic materials 0.000 description 1
- 239000010439 graphite Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- 229920006305 unsaturated polyester Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/12—Esters of phenols or saturated alcohols
- C08F222/20—Esters containing oxygen in addition to the carboxy oxygen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/593—Dicarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/60—Maleic acid esters; Fumaric acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F22/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides or nitriles thereof
- C08F22/10—Esters
- C08F22/12—Esters of phenols or saturated alcohols
- C08F22/14—Esters having no free carboxylic acid groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA214705A CA1054627A (en) | 1974-11-26 | 1974-11-26 | Mono hydroxy unsaturated diesters |
| GB47989/75A GB1526825A (en) | 1974-11-26 | 1975-11-21 | Hydroxy unsaturated diesters |
| DE2559857A DE2559857C2 (de) | 1974-11-26 | 1975-11-24 | Quervernetzbares, wärmehärtbares Copolymer und Verfahren zu dessen Herstellung |
| AT890575A AT347417B (de) | 1974-11-26 | 1975-11-24 | Verfahren zur herstellung von hydroxy-einfach ungesaettigte diester enthaltenden ester- gemischen |
| DE2552634A DE2552634C3 (de) | 1974-11-26 | 1975-11-24 | Verfahren zur Herstellung von Malein- oder Fumarsäureestern |
| FR7535910A FR2292695B1 (fr) | 1974-11-26 | 1975-11-25 | Diesters insatures hydroxyles et procede pour leur obtention |
| IT09627/75A IT1053089B (it) | 1974-11-26 | 1975-11-25 | Diestere monoidrossi non saturo e suo processo di preparazione |
| US05/838,863 US4166893A (en) | 1974-11-26 | 1977-10-03 | Hydroxy unsaturated diesters and copolymers thereof |
| AT712477A AT354730B (de) | 1974-11-26 | 1977-10-06 | Verfahren zur herstellung von quervernetzbaren copolymeren fuer waermehaertende mischungen |
| FR8022397A FR2463117A1 (fr) | 1974-11-26 | 1980-10-20 | Procede de preparation de diesters insatures hydroxyles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA214705A CA1054627A (en) | 1974-11-26 | 1974-11-26 | Mono hydroxy unsaturated diesters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1054627A true CA1054627A (en) | 1979-05-15 |
Family
ID=4101721
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA214705A Expired CA1054627A (en) | 1974-11-26 | 1974-11-26 | Mono hydroxy unsaturated diesters |
Country Status (6)
| Country | Link |
|---|---|
| AT (1) | AT347417B (enExample) |
| CA (1) | CA1054627A (enExample) |
| DE (2) | DE2552634C3 (enExample) |
| FR (2) | FR2292695B1 (enExample) |
| GB (1) | GB1526825A (enExample) |
| IT (1) | IT1053089B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2907997C2 (de) * | 1979-03-01 | 1982-04-15 | Hoechst Ag, 6000 Frankfurt | Verfahren zur Herstellung von härtbaren Copolymeren |
| DE3819738A1 (de) * | 1988-06-10 | 1989-12-14 | Stockhausen Chem Fab Gmbh | Drei funktionelle estergruppen enthaltende verbindungen, zwischenprodukte zu ihrer herstellung, ihre herstellung und verwendung |
| NL8901490A (nl) * | 1989-06-13 | 1991-01-02 | Stamicarbon | Harssamenstelling geschikt voor nagenoeg oplosmiddelvrije verfsamenstellingen. |
| US5942475A (en) * | 1996-09-06 | 1999-08-24 | Exxon Chemical Patents Inc. | Engine oil lubricants formed from complex alcohol esters |
| US5750750C1 (en) * | 1997-02-07 | 2001-03-27 | Exxon Chemical Patents Inc | High viscosity complex alcohol esters |
| US5922658A (en) * | 1996-09-06 | 1999-07-13 | Exxon Chemical Patents Inc. | Two-cycle engine oil formed from a blend of a complex alcohol ester and other basestocks |
| US5994278A (en) * | 1996-09-06 | 1999-11-30 | Exxon Chemical Patents Inc. | Blends of lubricant basestocks with high viscosity complex alcohol esters |
| EP1712599A1 (en) * | 2005-04-14 | 2006-10-18 | Hexion Specialty Chemicals Research Belgium S.A. | Coating composition comprising an unsaturated hydroxydiester with superior outdoor durability |
| EP3360532B1 (en) * | 2017-02-13 | 2022-04-27 | Dentsply DeTrey GmbH | Dental composition |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL127295C (enExample) * | 1961-06-08 | |||
| BE655602A (enExample) * | 1963-11-15 | 1965-03-01 | ||
| US3391183A (en) * | 1964-08-28 | 1968-07-02 | Pittsburgh Plate Glass Co | Method of preparing beta-hydroxyalkyl esters including the isomerization of maleic acid half-esters |
| US3418363A (en) * | 1965-07-21 | 1968-12-24 | Monsanto Co | Process of preparing alkyl hydroxyalkyl fumarates |
| US3414635A (en) * | 1965-10-18 | 1968-12-03 | Jefferson Chem Co Inc | Hydroxyalkyl esters in surface coatings |
-
1974
- 1974-11-26 CA CA214705A patent/CA1054627A/en not_active Expired
-
1975
- 1975-11-21 GB GB47989/75A patent/GB1526825A/en not_active Expired
- 1975-11-24 DE DE2552634A patent/DE2552634C3/de not_active Expired
- 1975-11-24 DE DE2559857A patent/DE2559857C2/de not_active Expired
- 1975-11-24 AT AT890575A patent/AT347417B/de not_active IP Right Cessation
- 1975-11-25 IT IT09627/75A patent/IT1053089B/it active
- 1975-11-25 FR FR7535910A patent/FR2292695B1/fr not_active Expired
-
1980
- 1980-10-20 FR FR8022397A patent/FR2463117A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2292695B1 (fr) | 1983-04-01 |
| GB1526825A (en) | 1978-10-04 |
| AT347417B (de) | 1978-12-27 |
| FR2463117B1 (enExample) | 1984-12-07 |
| ATA890575A (de) | 1978-05-15 |
| IT1053089B (it) | 1981-08-31 |
| DE2552634C3 (de) | 1982-04-22 |
| FR2292695A1 (fr) | 1976-06-25 |
| DE2552634B2 (de) | 1981-06-19 |
| DE2552634A1 (de) | 1976-08-12 |
| FR2463117A1 (fr) | 1981-02-20 |
| DE2559857C2 (de) | 1982-11-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CA1054627A (en) | Mono hydroxy unsaturated diesters | |
| US4504635A (en) | Process for the preparation of polymeric compositions | |
| EP2325214B1 (en) | Synthesis of acrylic or methacrylic acid/acrylate or methacrylate ester polymers using pervaporation | |
| CA1302636C (en) | Polymers and crosslinked compositions made therefrom | |
| US4075242A (en) | Low molecular weight acrylates or methacrylates | |
| KR101810311B1 (ko) | 다관능성 아크릴레이트 에테르-에스테르 생성물, 이의 제조 방법 및 관련 가교 조성물 | |
| US3163615A (en) | Amide interpolymer containing unsaturated polyester | |
| US4276432A (en) | Low molecular weight acrylates or methacrylates and methods for their preparation | |
| US3230275A (en) | Interpolymers comprising acrylamide and a hydroxy-substituted monomer and heat curable resin compositions therewith | |
| US3320336A (en) | Unsaturated polyesters having branched structures | |
| US4166893A (en) | Hydroxy unsaturated diesters and copolymers thereof | |
| JPH07300510A (ja) | 水希釈可能なバインダーの製造方法並びに塗装組成物におけるそれらの使用 | |
| US3474076A (en) | Method of preparing soluble binders | |
| US4085082A (en) | Polymers of vinyl acetate plasticized with low molecular weight polyesters | |
| US3845023A (en) | Heat-curable copolymers based on hydroxyalkylesters and n-alkoxymethacrylamides,showing excellent adhesive properties especially on metallic substrates | |
| US3335102A (en) | Resinous compositions obtained by copolymerizing a partial ester of a polyhydric alcohol, a monocarboxylic acid and an unsaturated dicarboxylic acid with a vinyl monomer | |
| US4972036A (en) | Thermosetting acrylic copolymers modified with citric esters | |
| US3663599A (en) | Method of producing vinylic polymerizable monomers | |
| AT354730B (de) | Verfahren zur herstellung von quervernetzbaren copolymeren fuer waermehaertende mischungen | |
| US2677671A (en) | Interpolymer from lower alkyl ester of methacrylic acid, fatty acid ester of epoxy resin and ester of alpha, beta unsaturated dicarboxylic acid with diels-alder adduct of cyclopentadiene and allyl alcohol | |
| US4985506A (en) | Oxidatively cross-linkable, water dilutable binders, a process for their preparation and their use | |
| US2557667A (en) | Reaction products of a cyanuric triester and a polyhydric alcohol and methods of preparing the same | |
| US5798434A (en) | Monomer mixture and method for the preparation thereof | |
| JP2002517528A (ja) | アリル／エチレン系共重合体の製造方法 | |
| US5763644A (en) | Method for transesterification |