CA1093398A - Process for the preparation of coatings - Google Patents
Process for the preparation of coatingsInfo
- Publication number
- CA1093398A CA1093398A CA261,526A CA261526A CA1093398A CA 1093398 A CA1093398 A CA 1093398A CA 261526 A CA261526 A CA 261526A CA 1093398 A CA1093398 A CA 1093398A
- Authority
- CA
- Canada
- Prior art keywords
- weight
- imidazoline
- mixture
- dicyandiamide
- powder
- 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
- 238000000576 coating method Methods 0.000 title claims abstract description 14
- 238000000034 method Methods 0.000 title claims abstract description 11
- 238000002360 preparation method Methods 0.000 title description 2
- 239000000203 mixture Substances 0.000 claims abstract description 51
- 239000000843 powder Substances 0.000 claims abstract description 40
- 239000004922 lacquer Substances 0.000 claims abstract description 31
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 claims abstract description 22
- 238000002844 melting Methods 0.000 claims abstract description 19
- 230000008018 melting Effects 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 18
- 239000004593 Epoxy Substances 0.000 claims abstract description 17
- 150000002462 imidazolines Chemical class 0.000 claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 239000011248 coating agent Substances 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
- 239000001257 hydrogen Substances 0.000 claims abstract description 7
- 239000000654 additive Substances 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 238000004519 manufacturing process Methods 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 5
- 239000004848 polyfunctional curative Substances 0.000 claims description 18
- 229940083254 peripheral vasodilators imidazoline derivative Drugs 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229920002554 vinyl polymer Chemical group 0.000 claims description 4
- 125000006585 (C6-C10) arylene group Chemical group 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000005551 pyridylene group Chemical group 0.000 claims 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims 1
- -1 arylene radical Chemical class 0.000 abstract description 9
- 125000000217 alkyl group Chemical group 0.000 abstract description 5
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 4
- 150000003254 radicals Chemical class 0.000 abstract description 3
- 150000005840 aryl radicals Chemical class 0.000 abstract description 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 2
- 229920000647 polyepoxide Polymers 0.000 description 27
- 239000003822 epoxy resin Substances 0.000 description 19
- 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 description 15
- 239000007787 solid Substances 0.000 description 13
- BKCCAYLNRIRKDJ-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1h-imidazole Chemical compound N1CCN=C1C1=CC=CC=C1 BKCCAYLNRIRKDJ-UHFFFAOYSA-N 0.000 description 11
- 239000003795 chemical substances by application Substances 0.000 description 11
- 230000009257 reactivity Effects 0.000 description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 230000001737 promoting effect Effects 0.000 description 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- 238000005452 bending Methods 0.000 description 6
- 150000002118 epoxides Chemical class 0.000 description 5
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
- 150000001241 acetals Chemical class 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000000049 pigment Substances 0.000 description 3
- JJUVAPMVTXLLFR-UHFFFAOYSA-N 5-methyl-2-phenyl-4,5-dihydro-1h-imidazole Chemical compound N1C(C)CN=C1C1=CC=CC=C1 JJUVAPMVTXLLFR-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 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 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N phosphine group Chemical group P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 238000005245 sintering Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- LOCJFVVULRDEEL-UHFFFAOYSA-N 1-[4-(4,5-dihydroimidazol-1-yl)phenyl]-4,5-dihydroimidazole Chemical compound C1=NCCN1C1=CC=C(N2C=NCC2)C=C1 LOCJFVVULRDEEL-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- VDSAXHBDVIUOGV-UHFFFAOYSA-N 1-ethenyl-2-methyl-4,5-dihydroimidazole Chemical compound CC1=NCCN1C=C VDSAXHBDVIUOGV-UHFFFAOYSA-N 0.000 description 1
- SDRZFSPCVYEJTP-UHFFFAOYSA-N 1-ethenylcyclohexene Chemical compound C=CC1=CCCCC1 SDRZFSPCVYEJTP-UHFFFAOYSA-N 0.000 description 1
- CNIIGCLFLJGOGP-UHFFFAOYSA-N 2-(1-naphthalenylmethyl)-4,5-dihydro-1H-imidazole Chemical compound C=1C=CC2=CC=CC=C2C=1CC1=NCCN1 CNIIGCLFLJGOGP-UHFFFAOYSA-N 0.000 description 1
- FAZYMPYKTJYGNR-UHFFFAOYSA-N 2-(3-methylphenyl)-4,5-dihydro-1h-imidazole Chemical compound CC1=CC=CC(C=2NCCN=2)=C1 FAZYMPYKTJYGNR-UHFFFAOYSA-N 0.000 description 1
- YFBPRBZDQSMTKG-UHFFFAOYSA-N 2-(chloromethyl)-4,5-dihydroimidazole Chemical compound ClCC1=NCCN1 YFBPRBZDQSMTKG-UHFFFAOYSA-N 0.000 description 1
- QUPKCFBHJFNUEW-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1h-imidazole Chemical compound CCC1=NCCN1 QUPKCFBHJFNUEW-UHFFFAOYSA-N 0.000 description 1
- CBECDWUDYQOTSW-UHFFFAOYSA-N 2-ethylbut-3-enal Chemical compound CCC(C=C)C=O CBECDWUDYQOTSW-UHFFFAOYSA-N 0.000 description 1
- VWSLLSXLURJCDF-UHFFFAOYSA-N 2-methyl-4,5-dihydro-1h-imidazole Chemical compound CC1=NCCN1 VWSLLSXLURJCDF-UHFFFAOYSA-N 0.000 description 1
- ZXTHWIZHGLNEPG-UHFFFAOYSA-N 2-phenyl-4,5-dihydro-1,3-oxazole Chemical compound O1CCN=C1C1=CC=CC=C1 ZXTHWIZHGLNEPG-UHFFFAOYSA-N 0.000 description 1
- OXQXGKNECHBVMO-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical compound C1C(C(=O)O)CCC2OC21 OXQXGKNECHBVMO-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- MLVSWIXRZNPEKF-UPHRSURJSA-N bis(oxiran-2-ylmethyl) (z)-but-2-enedioate Chemical compound C1OC1COC(=O)\C=C/C(=O)OCC1CO1 MLVSWIXRZNPEKF-UPHRSURJSA-N 0.000 description 1
- JRPRCOLKIYRSNH-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) benzene-1,2-dicarboxylate Chemical compound C=1C=CC=C(C(=O)OCC2OC2)C=1C(=O)OCC1CO1 JRPRCOLKIYRSNH-UHFFFAOYSA-N 0.000 description 1
- KBWLNCUTNDKMPN-UHFFFAOYSA-N bis(oxiran-2-ylmethyl) hexanedioate Chemical compound C1OC1COC(=O)CCCCC(=O)OCC1CO1 KBWLNCUTNDKMPN-UHFFFAOYSA-N 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 1
- 125000002636 imidazolinyl group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000004714 phosphonium salts Chemical group 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- JIVZKJJQOZQXQB-UHFFFAOYSA-N tolazoline Chemical compound C=1C=CC=CC=1CC1=NCCN1 JIVZKJJQOZQXQB-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- DIHAURBCYGTGCV-UHFFFAOYSA-N xi-4,5-Dihydro-2,4(5)-dimethyl-1H-imidazole Chemical compound CC1CN=C(C)N1 DIHAURBCYGTGCV-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- C08G59/40—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 curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
- C08G59/4021—Ureas; Thioureas; Guanidines; Dicyandiamides
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31511—Of epoxy ether
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Epoxy Resins (AREA)
- Glass Compositions (AREA)
- Silicon Polymers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2542105A DE2542105B2 (de) | 1975-09-20 | 1975-09-20 | Verfahren zur Herstellung von Überzügen |
| DEP2542105.0 | 1975-09-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1093398A true CA1093398A (en) | 1981-01-13 |
Family
ID=5957044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA261,526A Expired CA1093398A (en) | 1975-09-20 | 1976-09-20 | Process for the preparation of coatings |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4246394A (OSRAM) |
| JP (1) | JPS5241643A (OSRAM) |
| AT (1) | ATA691376A (OSRAM) |
| AU (1) | AU510988B2 (OSRAM) |
| BE (1) | BE846373A (OSRAM) |
| CA (1) | CA1093398A (OSRAM) |
| DE (1) | DE2542105B2 (OSRAM) |
| ES (1) | ES451630A1 (OSRAM) |
| FR (1) | FR2324698A1 (OSRAM) |
| GB (1) | GB1554588A (OSRAM) |
| NL (1) | NL7610360A (OSRAM) |
| NO (1) | NO763102L (OSRAM) |
| SE (1) | SE7610423L (OSRAM) |
| ZA (1) | ZA765599B (OSRAM) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2304690A1 (fr) * | 1975-03-18 | 1976-10-15 | Sev Marchal | Procede de traitement d'une surface metallique destinee a etre aluminee, notamment pour l'obtention de reflecteurs de projecteurs |
| US4176142A (en) * | 1978-05-22 | 1979-11-27 | Western Electric Company, Inc. | Powder coating composition |
| US4537834A (en) * | 1982-11-10 | 1985-08-27 | The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration | Metal (II) 4,4',4",4'"-phthalocyanine tetraamines as curing agents for epoxy resins |
| JPH0699542B2 (ja) * | 1985-06-03 | 1994-12-07 | チバ−ガイギ− アクチエンゲゼルシヤフト | エポキシ樹脂のための硬化剤混合物及びその使用方法 |
| DE3700287A1 (de) * | 1986-01-10 | 1987-07-16 | Hitachi Chemical Co Ltd | Epoxyharz-zusammensetzung fuer kupfer-plattierte laminate |
| DE3714997A1 (de) * | 1987-05-06 | 1988-11-17 | Aeg Isolier Kunststoff | Epoxidharzformulierung mit extrem kurzer haertungszeit |
| US4946507A (en) * | 1989-07-12 | 1990-08-07 | E. I. Du Pont De Nemours And Company | Pigment dispersant resin: reaction product of imidazoline amine and alkylene carbonate |
| US5116903A (en) * | 1991-04-05 | 1992-05-26 | E. I. Du Pont De Nemours & Co. | Pigment dispersant resin: reaction product of imidazoline and alkylene carbonate adduct and a half blocked diisocyanate |
| TW274553B (OSRAM) * | 1992-06-05 | 1996-04-21 | Ciba Geigy Ag | |
| US5939557A (en) * | 1996-04-03 | 1999-08-17 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| EP2113525A1 (de) | 2008-04-30 | 2009-11-04 | Sika Technology AG | Aktivator für Epoxidharzzusammensetzungen |
| JP5687187B2 (ja) * | 2008-04-30 | 2015-03-18 | シーカ・テクノロジー・アーゲー | エポキシ樹脂組成物のための活性剤 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3549592A (en) * | 1968-08-05 | 1970-12-22 | Jefferson Chem Co Inc | Curing epoxy resins with amidines |
| DE1908752A1 (de) * | 1969-02-18 | 1970-08-20 | Schering Ag | Haertung von Epoxidverbindungen mit Dicyandiamid und Beschleunigern |
| US3631150A (en) * | 1970-05-20 | 1971-12-28 | Dexter Corp | Synergistic composition for curing polyepoxides comprising an imidazole compound and dicyandiamide |
| BE789216A (fr) * | 1971-10-01 | 1973-03-26 | Shell Int Research | Omposities werkwijze ter bereiding van poedervormige deklaagc |
| DE2248776C3 (de) * | 1972-10-05 | 1978-04-13 | Veba-Chemie Ag, 4660 Gelsenkirchen- Buer | Verfahren zur Herstellung von Überzügen auf der Basis von Pulverlacken |
| US3903048A (en) * | 1973-04-02 | 1975-09-02 | United States Steel Corp | Catalyst systems for lowering epoxy resin cure temperatures |
| LU69177A1 (OSRAM) * | 1974-01-16 | 1974-04-08 |
-
1975
- 1975-09-20 DE DE2542105A patent/DE2542105B2/de not_active Ceased
-
1976
- 1976-09-09 NO NO763102A patent/NO763102L/no unknown
- 1976-09-16 AU AU17814/76A patent/AU510988B2/en not_active Expired
- 1976-09-17 ES ES451630A patent/ES451630A1/es not_active Expired
- 1976-09-17 AT AT691376A patent/ATA691376A/de not_active Application Discontinuation
- 1976-09-17 ZA ZA765599A patent/ZA765599B/xx unknown
- 1976-09-17 GB GB3868076A patent/GB1554588A/en not_active Expired
- 1976-09-17 JP JP11090276A patent/JPS5241643A/ja active Pending
- 1976-09-17 NL NL7610360A patent/NL7610360A/xx not_active Application Discontinuation
- 1976-09-20 CA CA261,526A patent/CA1093398A/en not_active Expired
- 1976-09-20 BE BE170766A patent/BE846373A/xx unknown
- 1976-09-20 FR FR7628211A patent/FR2324698A1/fr active Granted
- 1976-09-20 SE SE7610423A patent/SE7610423L/xx unknown
-
1978
- 1978-05-03 US US05/902,466 patent/US4246394A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| US4246394A (en) | 1981-01-20 |
| ES451630A1 (es) | 1977-08-01 |
| ATA691376A (de) | 1981-10-15 |
| ZA765599B (en) | 1977-10-26 |
| NL7610360A (nl) | 1977-03-22 |
| JPS5241643A (en) | 1977-03-31 |
| DE2542105B2 (de) | 1980-06-04 |
| DE2542105A1 (de) | 1977-03-31 |
| AU1781476A (en) | 1978-03-23 |
| FR2324698A1 (fr) | 1977-04-15 |
| FR2324698B1 (OSRAM) | 1980-05-09 |
| BE846373A (fr) | 1977-01-17 |
| AU510988B2 (en) | 1980-07-24 |
| GB1554588A (en) | 1979-10-24 |
| NO763102L (no) | 1977-03-22 |
| SE7610423L (sv) | 1977-03-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3756984A (en) | Epoxy imidazole adducts as curing agents for epoxy resins | |
| US3404018A (en) | Esters of polyepoxides and hydroxycarboxylic acids | |
| US3896082A (en) | Epoxy powder coatings and method therefor | |
| US4348505A (en) | Adducts from amines and di- and polyepoxides | |
| JP5325791B2 (ja) | 脂環式ジアミン硬化剤を含むエポキシ樹脂 | |
| CA1182949A (en) | Adducts from amines and di- and polyepoxides | |
| CA1093398A (en) | Process for the preparation of coatings | |
| US4296005A (en) | Adducts containing hydroxyl groups from mononuclear hydantoin glycidyl compounds and non-aromatic dicarboxylic acids | |
| EP0454271B1 (en) | Polyacetoacetate-containing epoxy resin compositions | |
| CA1281484C (en) | Advanced resins from diglycidyl ethers of di-secondary alcohols and dihydric phenols | |
| JP2019524967A (ja) | エポキシ樹脂系用のイミダゾール塩添加剤を含有する酸無水物エポキシ硬化剤 | |
| US3839281A (en) | N-hydroxyalkylpiperidyl,n-hydroxyalkylpiperazyl compounds as accelerating agents in epoxy resin compositions | |
| FI86645C (fi) | Epoxihartspulverbelaeggningskomposition. | |
| US4526940A (en) | Hydroxyl terminated polyfunctional epoxy curing agents | |
| AU594004B2 (en) | Coating compositions based on polyepoxides and polyacid curing agents | |
| CA1257045A (en) | Curable epoxy resin composition | |
| US4414250A (en) | Amine containing resin with oxalate esters for casting | |
| JPS6178826A (ja) | 溶剤系用ノボラツク型エポキシ樹脂硬化剤 | |
| KR20150023525A (ko) | 에폭시 코팅 적용을 위한 저점도 페놀 디글리시딜 에테르 | |
| US4007299A (en) | Method for making matt finish coatings | |
| US4146701A (en) | Polyether diureide epoxy additives | |
| US5017676A (en) | Acetoacetoxyethyl methacrylate in the cure of epoxy resins | |
| JPS6330570A (ja) | エポキシ樹脂／硬化剤−混合物を中間層高接着性の被覆物の製造に用いる方法 | |
| US5232990A (en) | Melamine derivative cross-linking agent | |
| CA1175194A (en) | Adducts, containing epoxide groups, from hydantoin polyepoxide and binuclear hydantoin compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |