DE2552634C3 - Verfahren zur Herstellung von Malein- oder Fumarsäureestern - Google Patents
Verfahren zur Herstellung von Malein- oder FumarsäureesternInfo
- Publication number
- DE2552634C3 DE2552634C3 DE2552634A DE2552634A DE2552634C3 DE 2552634 C3 DE2552634 C3 DE 2552634C3 DE 2552634 A DE2552634 A DE 2552634A DE 2552634 A DE2552634 A DE 2552634A DE 2552634 C3 DE2552634 C3 DE 2552634C3
- Authority
- DE
- Germany
- Prior art keywords
- acid
- moles
- water
- content
- maleic
- 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
- 238000000034 method Methods 0.000 title claims description 22
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 title claims description 14
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 title claims description 14
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 title claims description 9
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 title claims description 8
- 239000011976 maleic acid Substances 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- -1 2,3-dihydroxypropyl group Chemical group 0.000 claims description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 39
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 239000000178 monomer Substances 0.000 description 21
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 16
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 14
- 229920000642 polymer Polymers 0.000 description 14
- 150000005690 diesters Chemical class 0.000 description 13
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 12
- 238000005886 esterification reaction Methods 0.000 description 12
- 230000032050 esterification Effects 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 11
- 238000004458 analytical method Methods 0.000 description 10
- 229920001187 thermosetting polymer Polymers 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 239000004908 Emulsion polymer Substances 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 6
- 150000002688 maleic acid derivatives Chemical class 0.000 description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000007795 chemical reaction product Substances 0.000 description 5
- 239000001530 fumaric acid Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- ROOXNKNUYICQNP-UHFFFAOYSA-N ammonium persulfate Chemical compound [NH4+].[NH4+].[O-]S(=O)(=O)OOS([O-])(=O)=O ROOXNKNUYICQNP-UHFFFAOYSA-N 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 238000007334 copolymerization reaction Methods 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
- 239000004743 Polypropylene Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 239000012190 activator Substances 0.000 description 3
- 229920003180 amino resin Polymers 0.000 description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 125000005395 methacrylic acid group Chemical group 0.000 description 3
- 229920001155 polypropylene Polymers 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- UKXDHEBARGMWMO-ARJAWSKDSA-N (z)-4-(2-methylpropoxy)-4-oxobut-2-enoic acid Chemical compound CC(C)COC(=O)\C=C/C(O)=O UKXDHEBARGMWMO-ARJAWSKDSA-N 0.000 description 2
- SEKSGOSKIRTOJU-WAYWQWQTSA-N 1-O-ethyl 4-O-(2-methylpropyl) (Z)-but-2-enedioate Chemical compound C(\C=C/C(=O)OCC(C)C)(=O)OCC SEKSGOSKIRTOJU-WAYWQWQTSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- BJSGMMXNYQMKIV-ARJAWSKDSA-N CC(C)COC(/C=C\C(OCCO)=O)=O Chemical compound CC(C)COC(/C=C\C(OCCO)=O)=O BJSGMMXNYQMKIV-ARJAWSKDSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 229910001870 ammonium persulfate Inorganic materials 0.000 description 2
- 239000003945 anionic surfactant Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 239000002736 nonionic surfactant Substances 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 229920000647 polyepoxide Polymers 0.000 description 2
- 229920002689 polyvinyl acetate Polymers 0.000 description 2
- 239000011118 polyvinyl acetate Substances 0.000 description 2
- 239000000376 reactant 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
- VITRQSKRKNBVFL-PLNGDYQASA-N (Z)-4-(1-hydroxyhexan-3-yloxy)-4-oxobut-2-enoic acid Chemical compound CCCC(CCO)OC(=O)\C=C/C(O)=O VITRQSKRKNBVFL-PLNGDYQASA-N 0.000 description 1
- QGWRNISZKOSRCH-FPLPWBNLSA-N (Z)-4-(4-ethyl-2-hydroxyoctoxy)-4-oxobut-2-enoic acid Chemical compound CCCCC(CC)CC(O)COC(=O)\C=C/C(O)=O QGWRNISZKOSRCH-FPLPWBNLSA-N 0.000 description 1
- UKXDHEBARGMWMO-ONEGZZNKSA-N (e)-4-(2-methylpropoxy)-4-oxobut-2-enoic acid Chemical compound CC(C)COC(=O)\C=C\C(O)=O UKXDHEBARGMWMO-ONEGZZNKSA-N 0.000 description 1
- IQBLWPLYPNOTJC-FPLPWBNLSA-N (z)-4-(2-ethylhexoxy)-4-oxobut-2-enoic acid Chemical compound CCCCC(CC)COC(=O)\C=C/C(O)=O IQBLWPLYPNOTJC-FPLPWBNLSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- DILXLMRYFWFBGR-UHFFFAOYSA-N 2-formylbenzene-1,4-disulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(S(O)(=O)=O)C(C=O)=C1 DILXLMRYFWFBGR-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 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
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000005396 acrylic acid ester group Chemical group 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 125000005189 alkyl hydroxy group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 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
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- 229940023913 cation exchange resins Drugs 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 229960002887 deanol Drugs 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- HPCBDEIJFFYVRW-UHFFFAOYSA-N ethane-1,2-diol 2-(2-hydroxyethoxy)ethanol propane-1,2-diol propane-1,2,3-triol Chemical compound C(C(C)O)O.C(COCCO)O.OCC(O)CO.C(CO)O HPCBDEIJFFYVRW-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 239000002685 polymerization catalyst Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer 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)
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 (3)
| Publication Number | Publication Date |
|---|---|
| DE2552634A1 DE2552634A1 (de) | 1976-08-12 |
| DE2552634B2 DE2552634B2 (de) | 1981-06-19 |
| DE2552634C3 true DE2552634C3 (de) | 1982-04-22 |
Family
ID=4101721
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2552634A Expired DE2552634C3 (de) | 1974-11-26 | 1975-11-24 | Verfahren zur Herstellung von Malein- oder Fumarsäureestern |
| DE2559857A Expired DE2559857C2 (de) | 1974-11-26 | 1975-11-24 | Quervernetzbares, wärmehärtbares Copolymer und Verfahren zu dessen Herstellung |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2559857A Expired DE2559857C2 (de) | 1974-11-26 | 1975-11-24 | Quervernetzbares, wärmehärtbares Copolymer und Verfahren zu dessen Herstellung |
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 |
| FR2292695A1 (fr) | 1976-06-25 |
| DE2552634B2 (de) | 1981-06-19 |
| DE2552634A1 (de) | 1976-08-12 |
| CA1054627A (en) | 1979-05-15 |
| FR2463117A1 (fr) | 1981-02-20 |
| DE2559857C2 (de) | 1982-11-18 |
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