CA2209338A1 - Hardeners for epoxy resins - Google Patents
Hardeners for epoxy resinsInfo
- Publication number
- CA2209338A1 CA2209338A1 CA002209338A CA2209338A CA2209338A1 CA 2209338 A1 CA2209338 A1 CA 2209338A1 CA 002209338 A CA002209338 A CA 002209338A CA 2209338 A CA2209338 A CA 2209338A CA 2209338 A1 CA2209338 A1 CA 2209338A1
- Authority
- CA
- Canada
- Prior art keywords
- acid
- reaction product
- ester
- product according
- carboxylic acid
- 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.)
- Abandoned
Links
- 239000003822 epoxy resin Substances 0.000 title claims abstract 5
- 229920000647 polyepoxide Polymers 0.000 title claims abstract 5
- 239000004848 polyfunctional curative Substances 0.000 title claims abstract 4
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 title 1
- 239000007795 chemical reaction product Substances 0.000 claims abstract 16
- 125000002843 carboxylic acid group Chemical group 0.000 claims abstract 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract 6
- -1 aromatic polyol Chemical class 0.000 claims 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 6
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 5
- 239000004971 Cross linker Substances 0.000 claims 5
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims 4
- 239000000178 monomer Substances 0.000 claims 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 4
- 229920002554 vinyl polymer Polymers 0.000 claims 4
- 229920001577 copolymer Polymers 0.000 claims 3
- 239000000047 product Substances 0.000 claims 3
- MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 claims 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical group C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims 2
- LCFVJGUPQDGYKZ-UHFFFAOYSA-N Bisphenol A diglycidyl ether Chemical compound C=1C=C(OCC2OC2)C=CC=1C(C)(C)C(C=C1)=CC=C1OCC1CO1 LCFVJGUPQDGYKZ-UHFFFAOYSA-N 0.000 claims 2
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims 2
- 239000002202 Polyethylene glycol Substances 0.000 claims 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims 2
- 150000001412 amines Chemical class 0.000 claims 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 claims 2
- XLYMOEINVGRTEX-UHFFFAOYSA-N fumaric acid monoethyl ester Natural products CCOC(=O)C=CC(O)=O XLYMOEINVGRTEX-UHFFFAOYSA-N 0.000 claims 2
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 229920001223 polyethylene glycol Polymers 0.000 claims 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims 2
- XLYMOEINVGRTEX-ONEGZZNKSA-N (e)-4-ethoxy-4-oxobut-2-enoic acid Chemical compound CCOC(=O)\C=C\C(O)=O XLYMOEINVGRTEX-ONEGZZNKSA-N 0.000 claims 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 claims 1
- ZWUBFMWIQJSEQS-UHFFFAOYSA-N 1,1-bis(ethenyl)cyclohexane Chemical compound C=CC1(C=C)CCCCC1 ZWUBFMWIQJSEQS-UHFFFAOYSA-N 0.000 claims 1
- JJBFVQSGPLGDNX-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(=O)C(C)=C JJBFVQSGPLGDNX-UHFFFAOYSA-N 0.000 claims 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims 1
- JSMLAJLJKICUJG-UHFFFAOYSA-N 2-(3-oxopent-4-enoxycarbonyl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C(=O)OCCC(=O)C=C JSMLAJLJKICUJG-UHFFFAOYSA-N 0.000 claims 1
- CYOAEBLVGSUAKP-UHFFFAOYSA-N 2-(4-ethenylphenyl)acetic acid Chemical compound OC(=O)CC1=CC=C(C=C)C=C1 CYOAEBLVGSUAKP-UHFFFAOYSA-N 0.000 claims 1
- FTUONIFJANQDSN-UHFFFAOYSA-N 2-(4-methyl-3-oxopent-4-enoxy)carbonylbenzoic acid Chemical compound CC(=C)C(=O)CCOC(=O)C1=CC=CC=C1C(O)=O FTUONIFJANQDSN-UHFFFAOYSA-N 0.000 claims 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims 1
- LEHNQGSPRXHYRT-UHFFFAOYSA-N 2-dodecyl-1h-imidazole Chemical compound CCCCCCCCCCCCC1=NC=CN1 LEHNQGSPRXHYRT-UHFFFAOYSA-N 0.000 claims 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims 1
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 claims 1
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims 1
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical group C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims 1
- VFZKVQVQOMDJEG-UHFFFAOYSA-N 2-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(=O)C=C VFZKVQVQOMDJEG-UHFFFAOYSA-N 0.000 claims 1
- FUOZJYASZOSONT-UHFFFAOYSA-N 2-propan-2-yl-1h-imidazole Chemical compound CC(C)C1=NC=CN1 FUOZJYASZOSONT-UHFFFAOYSA-N 0.000 claims 1
- SBWOBTUYQXLKSS-UHFFFAOYSA-N 3-(2-methylprop-2-enoyloxy)propanoic acid Chemical compound CC(=C)C(=O)OCCC(O)=O SBWOBTUYQXLKSS-UHFFFAOYSA-N 0.000 claims 1
- CYUZOYPRAQASLN-UHFFFAOYSA-N 3-prop-2-enoyloxypropanoic acid Chemical compound OC(=O)CCOC(=O)C=C CYUZOYPRAQASLN-UHFFFAOYSA-N 0.000 claims 1
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 claims 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 claims 1
- IRQWEODKXLDORP-UHFFFAOYSA-N 4-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=C(C=C)C=C1 IRQWEODKXLDORP-UHFFFAOYSA-N 0.000 claims 1
- PONXUVXMHVOCEC-UHFFFAOYSA-N 4-ethenylcyclohexane-1-carboxylic acid Chemical compound OC(=O)C1CCC(C=C)CC1 PONXUVXMHVOCEC-UHFFFAOYSA-N 0.000 claims 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 claims 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims 1
- XLYMOEINVGRTEX-ARJAWSKDSA-N Ethyl hydrogen fumarate Chemical compound CCOC(=O)\C=C/C(O)=O XLYMOEINVGRTEX-ARJAWSKDSA-N 0.000 claims 1
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims 1
- YVTVFZKHLXIJEY-UHFFFAOYSA-N OC(=O)C=C.OC(=O)C=C.C1OC1COCC1CO1 Chemical compound OC(=O)C=C.OC(=O)C=C.C1OC1COCC1CO1 YVTVFZKHLXIJEY-UHFFFAOYSA-N 0.000 claims 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims 1
- 150000008065 acid anhydrides Chemical class 0.000 claims 1
- 125000005396 acrylic acid ester group Chemical group 0.000 claims 1
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000005907 alkyl ester group Chemical group 0.000 claims 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims 1
- 229930016911 cinnamic acid Natural products 0.000 claims 1
- 235000013985 cinnamic acid Nutrition 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000004386 diacrylate group Chemical group 0.000 claims 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims 1
- 239000001530 fumaric acid Substances 0.000 claims 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims 1
- 239000011976 maleic acid Substances 0.000 claims 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims 1
- 238000000034 method Methods 0.000 claims 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 claims 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 claims 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims 1
- NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
- 229920000768 polyamine Polymers 0.000 claims 1
- 229920005862 polyol Polymers 0.000 claims 1
- 229920005650 polypropylene glycol diacrylate Polymers 0.000 claims 1
- 229920005651 polypropylene glycol dimethacrylate Polymers 0.000 claims 1
- QTECDUFMBMSHKR-UHFFFAOYSA-N prop-2-enyl prop-2-enoate Chemical compound C=CCOC(=O)C=C QTECDUFMBMSHKR-UHFFFAOYSA-N 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 125000003011 styrenyl group Chemical group [H]\C(*)=C(/[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/44—Preparation of metal salts or ammonium salts
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Epoxy Resins (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH165896 | 1996-07-02 | ||
| CH1658/96 | 1996-07-10 | ||
| CH174596 | 1996-07-10 | ||
| CH1745/96 | 1996-07-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2209338A1 true CA2209338A1 (en) | 1998-01-02 |
Family
ID=25688298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002209338A Abandoned CA2209338A1 (en) | 1996-07-02 | 1997-06-30 | Hardeners for epoxy resins |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US5994475A (enExample) |
| EP (1) | EP0816393B1 (enExample) |
| JP (1) | JP4126623B2 (enExample) |
| CA (1) | CA2209338A1 (enExample) |
| DE (1) | DE59711017D1 (enExample) |
| ES (1) | ES2210484T3 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6562884B1 (en) * | 1999-03-17 | 2003-05-13 | Vantico, Inc. | Epoxy resin compositions having a long shelf life |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2000049991A2 (en) * | 1999-02-23 | 2000-08-31 | Phairson Medical Inc. | Treatment of trauma |
| US6878776B1 (en) * | 1999-03-31 | 2005-04-12 | Cray Valley, S.A. | Thermosetting resin compositions comprising cross-linked reactive microparticles with improved mechanical strength |
| US7041769B2 (en) * | 1999-12-17 | 2006-05-09 | Acushnet Company | Polyurethane compositions for golf balls |
| TWI298412B (enExample) * | 2000-06-21 | 2008-07-01 | Mitsui Chemicals Inc | |
| EP1387860B1 (en) * | 2001-05-14 | 2005-07-20 | Huntsman Advanced Materials (Switzerland) GmbH | Moulding composition for producing bipolar plates |
| US8109402B2 (en) | 2001-10-04 | 2012-02-07 | Schoeller Arca Systems Ab | Collapsible container for transport and storage |
| MXPA03002222A (es) * | 2002-03-28 | 2004-10-29 | Rohm & Haas | Polvos de recubrimiento, metodos para su elaboracion y articulos formados a partir de los mismos. |
| US20060194896A1 (en) * | 2004-05-26 | 2006-08-31 | Sun Benjamin J | Low shrinkage dental material and method |
| US20060270778A1 (en) * | 2005-05-26 | 2006-11-30 | Dow Global Technologies Inc. | Sealer compositions |
| US20070054978A1 (en) * | 2005-09-07 | 2007-03-08 | Kabushiki Kaisha Shofu | One-liquid medical and dental curable composition |
| EP2435490A1 (en) * | 2009-05-28 | 2012-04-04 | Corning Incorporated | Swellable synthetic microcarriers for culturing cells |
| JP5700238B2 (ja) * | 2009-09-02 | 2015-04-15 | 三菱レイヨン株式会社 | エポキシ樹脂用硬化剤、エポキシ樹脂組成物及びエポキシ樹脂硬化物 |
| ES2664268T3 (es) | 2009-10-09 | 2018-04-18 | Henkel Ag & Co. Kgaa | Un agente de curado latente y composiciones epoxi que contienen el mismo |
| EP2325229A1 (en) | 2009-11-13 | 2011-05-25 | Cytec Surface Specialties, S.A. | Polyesters for coatings |
| JP5275295B2 (ja) * | 2010-07-21 | 2013-08-28 | 信越化学工業株式会社 | 半導体封止用エポキシ樹脂組成物及び半導体装置 |
| JP5620323B2 (ja) * | 2011-04-06 | 2014-11-05 | 積水化学工業株式会社 | 硬化剤及び／又は硬化促進剤複合粒子の製造方法、硬化剤及び／又は硬化促進剤複合粒子、並びに、熱硬化性樹脂組成物 |
| JP2014532800A (ja) * | 2011-11-10 | 2014-12-08 | ダウ グローバル テクノロジーズ エルエルシー | エポキシ硬化用途の潜在性触媒としてのカルボン酸アンモニウム基を有するポリマー |
| CA2896653C (en) * | 2012-12-28 | 2021-02-23 | Cytec Industries Inc. | Corrosion-inhibiting microgels and non-chromated primer compositions incorporating the same |
| US9080007B2 (en) * | 2013-02-28 | 2015-07-14 | Air Products And Chemicals, Inc. | Anhydride accelerators for epoxy resin systems |
| WO2014157464A1 (ja) * | 2013-03-28 | 2014-10-02 | 株式会社日本触媒 | 架橋微粒子の分散体およびその製造方法 |
| KR102094218B1 (ko) * | 2013-04-05 | 2020-03-27 | 에보니크 오퍼레이션즈 게엠베하 | 하이드록시알킬아미노 사이클로알칸을 포함하는 1 성분 에폭시 경화제 |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1104287A (en) * | 1975-07-14 | 1981-06-30 | Goodrich (B.F.) Company (The) | Reaction products of non-cycloaliphatic epoxy resins and amine-terminated liquid polymers and process for preparation thereof |
| US4415697A (en) * | 1980-10-23 | 1983-11-15 | Ford Motor Company | Paint composition comprising hydroxy functional film former and crosslinked dispersion flow control additive |
| AU563372B2 (en) * | 1982-12-16 | 1987-07-09 | Celanese Corporation | Crosslinked microgel particles |
| US4539348A (en) * | 1982-12-16 | 1985-09-03 | Celanese Corporation | Water-swellable crosslinked polymeric microgel particles and aqueous dispersions of organic film-forming resins containing the same |
| JPS59142220A (ja) * | 1983-02-04 | 1984-08-15 | Dainippon Ink & Chem Inc | 常温硬化性樹脂組成物 |
| US4503174A (en) * | 1983-09-06 | 1985-03-05 | E. I. Du Pont De Nemours And Company | Low temperature curing coating composition |
| JPS614761A (ja) * | 1984-06-18 | 1986-01-10 | Nippon Paint Co Ltd | 架橋反応プロモ−タ−微小樹脂粒子およびその使用方法 |
| JPS61133221A (ja) * | 1984-11-30 | 1986-06-20 | Du Pont Mitsui Polychem Co Ltd | 剛性および耐熱性にすぐれた熱可塑性重合体の製造法 |
| US4833226A (en) * | 1987-08-26 | 1989-05-23 | Asahi Kasei Kogyo Kabushiki Kaisha | Hardener for curable one-package epoxy resin system |
| EP0362787A3 (en) * | 1988-10-06 | 1992-04-01 | Henkel Research Corporation | Modified amino curing agents for epoxy resins |
| JPH03174432A (ja) * | 1989-09-27 | 1991-07-29 | Dainippon Ink & Chem Inc | 水性樹脂組成物 |
| EP0440583A3 (en) * | 1990-02-02 | 1993-03-03 | Ciba-Geigy Ag | Latent epoxy resin hardeners |
| DE4007559C2 (de) * | 1990-03-09 | 1994-08-25 | Franz Peter Dr Schmitz | Polymeres mit Hydrogel-Eigenschaften und Verfahren zu seiner Herstellung |
| KR100193147B1 (ko) * | 1990-03-30 | 1999-06-15 | 월터클라웨인, 한느-피터 위트린 | 개질된 에폭시 수지 |
| JP3042546B2 (ja) * | 1991-04-23 | 2000-05-15 | 昭和電工株式会社 | 微粒子状の架橋型ｎ−ビニルアミド樹脂及びミクロゲル、その製造法及び用途 |
| DE4141693A1 (de) * | 1991-12-18 | 1993-07-01 | Roehm Gmbh | Verfahren zur herstellung einer wasserloeslichen polymersuspension |
| DE59310074D1 (de) * | 1992-07-09 | 2000-08-17 | Ciba Sc Holding Ag | Härtbare Suspensionen auf Basis von Epoxidharzen |
| JP3468583B2 (ja) * | 1994-06-20 | 2003-11-17 | 神東塗料株式会社 | アニオン性水分散型樹脂組成物及びその製造方法 |
-
1997
- 1997-06-23 EP EP97810395A patent/EP0816393B1/de not_active Expired - Lifetime
- 1997-06-23 DE DE59711017T patent/DE59711017D1/de not_active Expired - Lifetime
- 1997-06-23 ES ES97810395T patent/ES2210484T3/es not_active Expired - Lifetime
- 1997-06-30 CA CA002209338A patent/CA2209338A1/en not_active Abandoned
- 1997-07-01 US US08/886,308 patent/US5994475A/en not_active Expired - Lifetime
- 1997-07-02 JP JP19189797A patent/JP4126623B2/ja not_active Expired - Fee Related
-
1999
- 1999-08-18 US US09/376,797 patent/US6274673B1/en not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6562884B1 (en) * | 1999-03-17 | 2003-05-13 | Vantico, Inc. | Epoxy resin compositions having a long shelf life |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0816393A3 (de) | 1999-01-07 |
| EP0816393A2 (de) | 1998-01-07 |
| US6274673B1 (en) | 2001-08-14 |
| DE59711017D1 (de) | 2003-12-24 |
| EP0816393B1 (de) | 2003-11-19 |
| US5994475A (en) | 1999-11-30 |
| ES2210484T3 (es) | 2004-07-01 |
| JPH1067819A (ja) | 1998-03-10 |
| JP4126623B2 (ja) | 2008-07-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Dead |