DE4225921A1 - Aminoacrylate, ein Verfahren zu ihrer Herstellung und ihre Verwendung - Google Patents
Aminoacrylate, ein Verfahren zu ihrer Herstellung und ihre VerwendungInfo
- Publication number
- DE4225921A1 DE4225921A1 DE4225921A DE4225921A DE4225921A1 DE 4225921 A1 DE4225921 A1 DE 4225921A1 DE 4225921 A DE4225921 A DE 4225921A DE 4225921 A DE4225921 A DE 4225921A DE 4225921 A1 DE4225921 A1 DE 4225921A1
- Authority
- DE
- Germany
- Prior art keywords
- molecular weight
- groups
- acrylic acid
- component
- ether
- 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.)
- Withdrawn
Links
- UQBOJOOOTLPNST-UHFFFAOYSA-N Dehydroalanine Chemical class NC(=C)C(O)=O UQBOJOOOTLPNST-UHFFFAOYSA-N 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims abstract description 5
- 238000002360 preparation method Methods 0.000 title claims abstract description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 10
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims abstract description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 150000004985 diamines Chemical class 0.000 claims abstract description 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
- 125000001033 ether group Chemical group 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 5
- 150000005846 sugar alcohols Polymers 0.000 claims abstract description 4
- QDHUQRBYCVAWEN-UHFFFAOYSA-N amino prop-2-enoate Chemical class NOC(=O)C=C QDHUQRBYCVAWEN-UHFFFAOYSA-N 0.000 claims description 10
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 8
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000004185 ester group Chemical group 0.000 claims description 7
- 201000006747 infectious mononucleosis Diseases 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- -1 ether alcohols Chemical class 0.000 claims description 6
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 239000011230 binding agent Substances 0.000 claims description 4
- 238000000576 coating method Methods 0.000 claims description 3
- 239000011248 coating agent Substances 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 abstract description 3
- 238000007259 addition reaction Methods 0.000 abstract description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract description 2
- 239000007787 solid Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 150000001298 alcohols Chemical class 0.000 description 5
- 238000007046 ethoxylation reaction Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229940113165 trimethylolpropane Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- LTHNHFOGQMKPOV-UHFFFAOYSA-N 2-ethylhexan-1-amine Chemical compound CCCCC(CC)CN LTHNHFOGQMKPOV-UHFFFAOYSA-N 0.000 description 1
- NLGDWWCZQDIASO-UHFFFAOYSA-N 2-hydroxy-1-(7-oxabicyclo[4.1.0]hepta-1,3,5-trien-2-yl)-2-phenylethanone Chemical compound OC(C(=O)c1cccc2Oc12)c1ccccc1 NLGDWWCZQDIASO-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- ASCJPSZPEUOKAW-UHFFFAOYSA-N C(C)(C)(C)C1C=C(O)C=CC1(O)C(C)(C)C Chemical compound C(C)(C)(C)C1C=C(O)C=CC1(O)C(C)(C)C ASCJPSZPEUOKAW-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 238000006845 Michael addition reaction Methods 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 235000000126 Styrax benzoin Nutrition 0.000 description 1
- 244000028419 Styrax benzoin Species 0.000 description 1
- 235000008411 Sumatra benzointree Nutrition 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
- GHWVXCQZPNWFRO-UHFFFAOYSA-N butane-2,3-diamine Chemical class CC(N)C(C)N GHWVXCQZPNWFRO-UHFFFAOYSA-N 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013065 commercial product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- VKIRRGRTJUUZHS-UHFFFAOYSA-N cyclohexane-1,4-diamine Chemical compound NC1CCC(N)CC1 VKIRRGRTJUUZHS-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000010894 electron beam technology Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- SYECJBOWSGTPLU-UHFFFAOYSA-N hexane-1,1-diamine Chemical class CCCCCC(N)N SYECJBOWSGTPLU-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- UKASIOIEWZDBIT-UHFFFAOYSA-N phenyl-(2,3,4-trimethylphenyl)methanone Chemical compound CC1=C(C)C(C)=CC=C1C(=O)C1=CC=CC=C1 UKASIOIEWZDBIT-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical class CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/331—Polymers modified by chemical after-treatment with organic compounds containing oxygen
- C08G65/332—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof
- C08G65/3322—Polymers modified by chemical after-treatment with organic compounds containing oxygen containing carboxyl groups, or halides, or esters thereof acyclic
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/14—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of carbon skeletons containing rings
-
- 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
- C07C69/533—Monocarboxylic acid esters having only one carbon-to-carbon double bond
- C07C69/54—Acrylic acid esters; Methacrylic 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/022—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations
- C08F299/024—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polycondensates with side or terminal unsaturations the unsaturation being in acrylic or methacrylic groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Adhesives Or Adhesive Processes (AREA)
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4225921A DE4225921A1 (de) | 1992-08-05 | 1992-08-05 | Aminoacrylate, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
| US08/095,886 US5482649A (en) | 1992-08-05 | 1993-07-22 | Aminoacrylates and a process for their preparation |
| AT93111848T ATE129515T1 (de) | 1992-08-05 | 1993-07-23 | Aminoacrylate, ein verfahren zu ihrer herstellung und ihre verwendung. |
| EP93111848A EP0586849B1 (de) | 1992-08-05 | 1993-07-23 | Aminoacrylate, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
| ES93111848T ES2080566T3 (es) | 1992-08-05 | 1993-07-23 | Aminoacrilatos, un procedimiento para su fabricacion y su uso. |
| DK93111848.3T DK0586849T3 (da) | 1992-08-05 | 1993-07-23 | Aminoacrylater, en fremgangsmåde til deres fremstilling og deres anvendelse |
| DE59300819T DE59300819D1 (de) | 1992-08-05 | 1993-07-23 | Aminoacrylate, ein Verfahren zu ihrer Herstellung und ihre Verwendung. |
| CA002101769A CA2101769A1 (en) | 1992-08-05 | 1993-08-02 | Aminoacrylates and a process for their preparation |
| JP5209993A JPH0687804A (ja) | 1992-08-05 | 1993-08-03 | アミノアクリレートおよびその製造方法 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4225921A DE4225921A1 (de) | 1992-08-05 | 1992-08-05 | Aminoacrylate, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4225921A1 true DE4225921A1 (de) | 1994-02-10 |
Family
ID=6464917
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4225921A Withdrawn DE4225921A1 (de) | 1992-08-05 | 1992-08-05 | Aminoacrylate, ein Verfahren zu ihrer Herstellung und ihre Verwendung |
| DE59300819T Revoked DE59300819D1 (de) | 1992-08-05 | 1993-07-23 | Aminoacrylate, ein Verfahren zu ihrer Herstellung und ihre Verwendung. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE59300819T Revoked DE59300819D1 (de) | 1992-08-05 | 1993-07-23 | Aminoacrylate, ein Verfahren zu ihrer Herstellung und ihre Verwendung. |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US5482649A (enExample) |
| EP (1) | EP0586849B1 (enExample) |
| JP (1) | JPH0687804A (enExample) |
| AT (1) | ATE129515T1 (enExample) |
| CA (1) | CA2101769A1 (enExample) |
| DE (2) | DE4225921A1 (enExample) |
| DK (1) | DK0586849T3 (enExample) |
| ES (1) | ES2080566T3 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4343246A1 (de) * | 1993-12-17 | 1995-06-22 | Thera Ges Fuer Patente | Prepolymere, daraus hergestellte radikalisch polymerisierbare Massen und deren Verwendung |
| WO2009037345A1 (en) * | 2007-09-21 | 2009-03-26 | Dsm Ip Assets B.V. | Branched polyesteramine acrylate |
Families Citing this family (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19535936A1 (de) * | 1995-09-27 | 1997-04-03 | Basf Lacke & Farben | Acryliertes Polyetherpolyol und dessen Verwendung für strahlenhärtbare Formulierungen |
| DE19543464A1 (de) | 1995-11-22 | 1997-05-28 | Basf Ag | Verfahren zur Herstellung von (Meth)acrylsäureestern |
| DE19625753C2 (de) * | 1996-06-27 | 2000-05-18 | Basf Coatings Ag | Holzbeschichtungsfolie |
| US6517343B2 (en) | 1997-09-26 | 2003-02-11 | Arizona Chemical Company | Coated candles and coating compositions |
| EP1328505A1 (en) * | 2000-10-20 | 2003-07-23 | Ucb, S.A. | Dimethylamine/ester adducts and their use in polymerizable compositions |
| EP1314777A1 (en) * | 2001-11-27 | 2003-05-28 | The Procter & Gamble Company | Pro-perfume compositions used in cleaning or fabric treatment products |
| JP2005532432A (ja) * | 2002-06-11 | 2005-10-27 | ビーエーエスエフ アクチェンゲゼルシャフト | ポリアルコキシル化されたトリメチロールプロパンの（メタ）アクリルエステル |
| RU2320677C2 (ru) * | 2002-06-11 | 2008-03-27 | Басф Акциенгезелльшафт | Сложный (мет)акриловый эфир полиалкоксилированного триметилолпропана (варианты) и его применение для получения абсорбирующих водосодержащие жидкости полимеров |
| ATE325150T1 (de) * | 2002-06-11 | 2006-06-15 | Basf Ag | (meth)acrylester von polyalkoxyliertem glycerin |
| US20050124722A1 (en) * | 2003-12-03 | 2005-06-09 | Arthur Samuel D. | Branched highly-functional monomers exhibiting low polymerization shrinkage |
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|---|---|---|---|---|
| US3844916A (en) * | 1972-09-18 | 1974-10-29 | Desoto Inc | Radiation curable non-gelled michael addition reaction products |
| US3925349A (en) * | 1972-09-18 | 1975-12-09 | Desoto Inc | Radiation curable non-gelled michael addition reaction products |
| US3914165A (en) * | 1972-09-18 | 1975-10-21 | Desoto Inc | Radiation curable non-gelled michael addition reaction products |
| DE3540464A1 (de) * | 1985-11-14 | 1987-05-21 | Polychemie Gmbh | Reaktive bindemittel |
| DE3706355A1 (de) * | 1987-02-27 | 1988-09-08 | Basf Ag | Additionsprodukte aus acrylaten und aminen sowie deren verwendung in strahlungshaertbaren massen |
| DE3836370A1 (de) * | 1988-10-26 | 1990-05-17 | Basf Lacke & Farben | Verfahren zum beschichten von holz, holzwerkstoffen und papier |
-
1992
- 1992-08-05 DE DE4225921A patent/DE4225921A1/de not_active Withdrawn
-
1993
- 1993-07-22 US US08/095,886 patent/US5482649A/en not_active Expired - Fee Related
- 1993-07-23 DK DK93111848.3T patent/DK0586849T3/da active
- 1993-07-23 EP EP93111848A patent/EP0586849B1/de not_active Revoked
- 1993-07-23 DE DE59300819T patent/DE59300819D1/de not_active Revoked
- 1993-07-23 AT AT93111848T patent/ATE129515T1/de not_active IP Right Cessation
- 1993-07-23 ES ES93111848T patent/ES2080566T3/es not_active Expired - Lifetime
- 1993-08-02 CA CA002101769A patent/CA2101769A1/en not_active Abandoned
- 1993-08-03 JP JP5209993A patent/JPH0687804A/ja active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE4343246A1 (de) * | 1993-12-17 | 1995-06-22 | Thera Ges Fuer Patente | Prepolymere, daraus hergestellte radikalisch polymerisierbare Massen und deren Verwendung |
| WO2009037345A1 (en) * | 2007-09-21 | 2009-03-26 | Dsm Ip Assets B.V. | Branched polyesteramine acrylate |
| US8334352B2 (en) | 2007-09-21 | 2012-12-18 | Dsm Ip Assets B.V. | Branched polyesteramine acrylate |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0586849B1 (de) | 1995-10-25 |
| ATE129515T1 (de) | 1995-11-15 |
| EP0586849A2 (de) | 1994-03-16 |
| CA2101769A1 (en) | 1994-02-06 |
| US5482649A (en) | 1996-01-09 |
| JPH0687804A (ja) | 1994-03-29 |
| DE59300819D1 (de) | 1995-11-30 |
| ES2080566T3 (es) | 1996-02-01 |
| DK0586849T3 (da) | 1996-01-22 |
| EP0586849A3 (enExample) | 1994-04-27 |
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