CA2287395A1 - Hardenable mixtures made of glycidyl compounds, aminic hardeners and heterocyclic accelerators - Google Patents
Hardenable mixtures made of glycidyl compounds, aminic hardeners and heterocyclic accelerators Download PDFInfo
- Publication number
- CA2287395A1 CA2287395A1 CA002287395A CA2287395A CA2287395A1 CA 2287395 A1 CA2287395 A1 CA 2287395A1 CA 002287395 A CA002287395 A CA 002287395A CA 2287395 A CA2287395 A CA 2287395A CA 2287395 A1 CA2287395 A1 CA 2287395A1
- Authority
- CA
- Canada
- Prior art keywords
- epoxy resin
- hardeners
- accelerators
- weight
- approximately
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 25
- 239000004848 polyfunctional curative Substances 0.000 title claims abstract description 25
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 title description 9
- 125000000623 heterocyclic group Chemical group 0.000 title 1
- 239000003822 epoxy resin Substances 0.000 claims abstract description 30
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 30
- 239000000049 pigment Substances 0.000 claims abstract description 4
- 239000002904 solvent Substances 0.000 claims abstract description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 claims abstract description 3
- 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 description 14
- 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 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 7
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 7
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000975 dye Substances 0.000 claims description 3
- 239000004014 plasticizer Substances 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000003381 stabilizer Substances 0.000 claims description 2
- -1 softeners Substances 0.000 abstract description 11
- 239000000463 material Substances 0.000 abstract description 2
- 239000012963 UV stabilizer Substances 0.000 abstract 1
- 239000003086 colorant Substances 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 description 8
- 241001550224 Apha Species 0.000 description 8
- 229930040373 Paraformaldehyde Natural products 0.000 description 8
- 229920002866 paraformaldehyde Polymers 0.000 description 8
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 7
- 239000007795 chemical reaction product Substances 0.000 description 5
- KFYRJJBUHYILSO-YFKPBYRVSA-N (2s)-2-amino-3-dimethylarsanylsulfanyl-3-methylbutanoic acid Chemical compound C[As](C)SC(C)(C)[C@@H](N)C(O)=O KFYRJJBUHYILSO-YFKPBYRVSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- 230000002745 absorbent Effects 0.000 description 2
- 239000002250 absorbent Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 125000002636 imidazolinyl group Chemical group 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- UDGSVBYJWHOHNN-UHFFFAOYSA-N n',n'-diethylethane-1,2-diamine Chemical compound CCN(CC)CCN UDGSVBYJWHOHNN-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical class NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- SWVGZFQJXVPIKM-UHFFFAOYSA-N n,n-bis(methylamino)propan-1-amine Chemical compound CCCN(NC)NC SWVGZFQJXVPIKM-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000006259 organic additive Substances 0.000 description 1
- 150000008442 polyphenolic compounds Polymers 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000013008 thixotropic agent Substances 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/686—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing nitrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP97106231.0 | 1997-04-16 | ||
| EP97106231A EP0872505B1 (de) | 1997-04-16 | 1997-04-16 | Härtbare Mischungen aus Glycidylverbindungen, aminischen Härtern und heterocyclischen Beschleunigern |
| PCT/EP1998/000327 WO1998046660A1 (de) | 1997-04-16 | 1998-01-22 | Härtbare mischungen aus glycidylverbindungen, aminischen härtern und heterocyclischen beschleunigern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2287395A1 true CA2287395A1 (en) | 1998-10-22 |
Family
ID=8226700
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002287395A Abandoned CA2287395A1 (en) | 1997-04-16 | 1998-01-22 | Hardenable mixtures made of glycidyl compounds, aminic hardeners and heterocyclic accelerators |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US6355763B1 (https=) |
| EP (1) | EP0872505B1 (https=) |
| JP (1) | JP3932404B2 (https=) |
| KR (1) | KR20010006463A (https=) |
| AU (1) | AU732395B2 (https=) |
| CA (1) | CA2287395A1 (https=) |
| DE (1) | DE59704012D1 (https=) |
| ES (1) | ES2159067T3 (https=) |
| WO (1) | WO1998046660A1 (https=) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE50103081D1 (de) | 2000-07-03 | 2004-09-09 | Vantico Gmbh & Co Kg | Härtbare Zusammensetzungen aus Glycidylverbindungen, aminischen Härtern und niedrigviskosen Härtungsbeschleunigern |
| JP2011001451A (ja) * | 2009-06-18 | 2011-01-06 | Sekisui Chem Co Ltd | 低温硬化性組成物 |
| WO2012119968A1 (en) | 2011-03-07 | 2012-09-13 | Akzo Nobel Coatings International B.V. | Cargo tank coating |
| WO2014049602A1 (en) * | 2012-09-28 | 2014-04-03 | Director General, Defence Research & Development Organization (Drdo) | An epoxy resin formulation for large and thick composite structures |
| DE102014215382A1 (de) | 2014-08-05 | 2016-02-11 | Evonik Degussa Gmbh | Stickstoffhaltige Verbindungen, geeignet zur Verwendung bei der Herstellung von Polyurethanen |
| JP6845226B2 (ja) | 2015-09-09 | 2021-03-17 | カーボン，インコーポレイテッド | 積層造形用エポキシ二重硬化樹脂 |
| CN108139665B (zh) | 2015-12-22 | 2022-07-05 | 卡本有限公司 | 用于用双重固化树脂的增材制造的双重前体树脂系统 |
| US11097259B2 (en) | 2016-07-18 | 2021-08-24 | Sika Technology Ag | Catalyst for curable compositions containing hexahydrotriazine structural units |
| EP3569629B1 (de) | 2018-05-17 | 2022-07-06 | Evonik Operations GmbH | Schnell härtende epoxysysteme |
| US11359048B2 (en) * | 2018-05-17 | 2022-06-14 | Evonik Operations Gmbh | Fast-curing epoxy systems |
| EP3569630B1 (de) | 2018-05-17 | 2022-08-03 | Evonik Operations GmbH | Schnell härtende epoxysysteme |
| US11286335B2 (en) | 2018-05-17 | 2022-03-29 | Evonik Operations Gmbh | Fast-curing epoxy systems |
| WO2020055682A1 (en) | 2018-09-10 | 2020-03-19 | Carbon, Inc. | Dual cure additive manufacturing resins for production of flame retardant objects |
| WO2022066565A1 (en) | 2020-09-25 | 2022-03-31 | Carbon, Inc. | Epoxy dual cure resin for the production of moisture-resistant articles by additive manufacturing |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5483096A (en) * | 1977-12-14 | 1979-07-02 | Hitachi Ltd | Thermosetting resin composition |
| US4228310A (en) * | 1979-03-19 | 1980-10-14 | Texaco Development Corp. | Polyol preparation |
| DE2918827A1 (de) * | 1979-05-10 | 1980-11-20 | Basf Ag | Ueberzugs-, impraegnier- und bindemittel auf basis waessriger dispersionen von copolymerisaten, die epoxydgruppen aufweisen |
| JPS59232117A (ja) * | 1983-06-15 | 1984-12-26 | Toray Chiokoole Kk | エポキシ樹脂の硬化方法 |
| US4740539A (en) * | 1986-04-21 | 1988-04-26 | Ashland Oil, Inc. | Flexible two-component epoxy structural adhesives |
| US4728384A (en) * | 1986-06-23 | 1988-03-01 | Ashland Oil, Inc. | Two component epoxy structural adhesives with improved flexibility |
| GB8824391D0 (en) * | 1988-10-18 | 1988-11-23 | Ciba Geigy Ag | Compositions |
| JP3442191B2 (ja) * | 1995-05-12 | 2003-09-02 | 旭化成株式会社 | 低温硬化性１液塗料組成物 |
-
1997
- 1997-04-16 ES ES97106231T patent/ES2159067T3/es not_active Expired - Lifetime
- 1997-04-16 DE DE59704012T patent/DE59704012D1/de not_active Expired - Lifetime
- 1997-04-16 EP EP97106231A patent/EP0872505B1/de not_active Expired - Lifetime
-
1998
- 1998-01-22 KR KR1019997009553A patent/KR20010006463A/ko not_active Ceased
- 1998-01-22 WO PCT/EP1998/000327 patent/WO1998046660A1/de not_active Ceased
- 1998-01-22 AU AU62932/98A patent/AU732395B2/en not_active Ceased
- 1998-01-22 US US09/402,980 patent/US6355763B1/en not_active Expired - Lifetime
- 1998-01-22 CA CA002287395A patent/CA2287395A1/en not_active Abandoned
- 1998-01-22 JP JP54339298A patent/JP3932404B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0872505A1 (de) | 1998-10-21 |
| EP0872505B1 (de) | 2001-07-11 |
| AU732395B2 (en) | 2001-04-26 |
| WO1998046660A1 (de) | 1998-10-22 |
| JP3932404B2 (ja) | 2007-06-20 |
| ES2159067T3 (es) | 2001-09-16 |
| AU6293298A (en) | 1998-11-11 |
| US6355763B1 (en) | 2002-03-12 |
| DE59704012D1 (de) | 2001-08-16 |
| JP2001518966A (ja) | 2001-10-16 |
| KR20010006463A (ko) | 2001-01-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued |