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)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1658/96 | 1996-07-02 | ||
| CH165896 | 1996-07-02 | ||
| CH1745/96 | 1996-07-10 | ||
| CH174596 | 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 (https=) |
| EP (1) | EP0816393B1 (https=) |
| JP (1) | JP4126623B2 (https=) |
| CA (1) | CA2209338A1 (https=) |
| DE (1) | DE59711017D1 (https=) |
| ES (1) | ES2210484T3 (https=) |
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 |
|---|---|---|---|---|
| CA2363048A1 (en) * | 1999-02-23 | 2000-08-31 | Phairson Medical, Inc. | Treatment of trauma |
| BR0009489A (pt) * | 1999-03-31 | 2002-02-19 | Cray Valley Sa | Composições termocurável compreendendo micropartìculas com aperfeiçoada resistência mecânica |
| US7041769B2 (en) * | 1999-12-17 | 2006-05-09 | Acushnet Company | Polyurethane compositions for golf balls |
| TWI298412B (https=) * | 2000-06-21 | 2008-07-01 | Mitsui Chemicals Inc | |
| US20040147643A1 (en) * | 2001-05-14 | 2004-07-29 | Martin Spitzer | 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 |
| TW201042038A (en) * | 2009-05-28 | 2010-12-01 | Corning Inc | 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 |
| JP5490907B2 (ja) | 2009-10-09 | 2014-05-14 | ヘンケル・アクチェンゲゼルシャフト・ウント・コムパニー・コマンディットゲゼルシャフト・アウフ・アクチェン | 潜在性硬化剤および該潜在性硬化剤を含有するエポキシ組成物 |
| 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 |
| US20140343228A1 (en) * | 2011-11-10 | 2014-11-20 | Yanfei Liu | Polymers with Carboxylic Ammonium Groups as Latent Catalysts for Epoxy Curing Applications |
| ES2635551T3 (es) * | 2012-12-28 | 2017-10-04 | Cytec Industries Inc. | Microgeles inhibidores de la corrosión y composiciones de imprimación, no cromadas, que incorporan los mismos |
| US9080007B2 (en) * | 2013-02-28 | 2015-07-14 | Air Products And Chemicals, Inc. | Anhydride accelerators for epoxy resin systems |
| JP6014244B2 (ja) * | 2013-03-28 | 2016-10-25 | 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 |
| JP6159014B2 (ja) * | 2013-04-05 | 2017-07-05 | エア プロダクツ アンド ケミカルズ インコーポレイテッドＡｉｒ Ｐｒｏｄｕｃｔｓ Ａｎｄ Ｃｈｅｍｉｃａｌｓ Ｉｎｃｏｒｐｏｒａｔｅｄ | ヒドロキシアルキルアミノシクロアルカンを含む１成分形エポキシ硬化剤 |
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 |
| 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 |
| AU563372B2 (en) * | 1982-12-16 | 1987-07-09 | Celanese Corporation | Crosslinked microgel particles |
| 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 |
| EP0304503B1 (en) * | 1987-08-26 | 1994-06-29 | 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 |
| ES2148213T3 (es) * | 1992-07-09 | 2000-10-16 | Vantico Ag | Suspensiones endurecibles a base de resinas epoxi. |
| 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 |
|---|---|
| US5994475A (en) | 1999-11-30 |
| EP0816393A3 (de) | 1999-01-07 |
| EP0816393A2 (de) | 1998-01-07 |
| DE59711017D1 (de) | 2003-12-24 |
| JPH1067819A (ja) | 1998-03-10 |
| JP4126623B2 (ja) | 2008-07-30 |
| EP0816393B1 (de) | 2003-11-19 |
| US6274673B1 (en) | 2001-08-14 |
| ES2210484T3 (es) | 2004-07-01 |
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| Date | Code | Title | Description |
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| EEER | Examination request | ||
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