JP3509799B2 - 一液性エポキシ組成物中のジシアンジアミドのための促進剤としてのイミダゾール−燐酸塩 - Google Patents
一液性エポキシ組成物中のジシアンジアミドのための促進剤としてのイミダゾール−燐酸塩Info
- Publication number
- JP3509799B2 JP3509799B2 JP2001333608A JP2001333608A JP3509799B2 JP 3509799 B2 JP3509799 B2 JP 3509799B2 JP 2001333608 A JP2001333608 A JP 2001333608A JP 2001333608 A JP2001333608 A JP 2001333608A JP 3509799 B2 JP3509799 B2 JP 3509799B2
- Authority
- JP
- Japan
- Prior art keywords
- imidazole
- epoxy
- dihydrogen phosphate
- phosphate salt
- epoxy composition
- 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 - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 62
- 239000004593 Epoxy Substances 0.000 title claims abstract description 56
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 title claims abstract description 34
- LPXDNEQTGPFOPF-UHFFFAOYSA-N hydron;1h-imidazol-1-ium;phosphate Chemical compound C1=CNC=N1.OP(O)(O)=O LPXDNEQTGPFOPF-UHFFFAOYSA-N 0.000 title claims abstract description 34
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 26
- 239000003822 epoxy resin Substances 0.000 claims abstract description 22
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 60
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 36
- 239000007787 solid Substances 0.000 claims description 13
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 6
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 6
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims description 5
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 150000002825 nitriles Chemical class 0.000 claims description 4
- 229920001187 thermosetting polymer Polymers 0.000 claims description 4
- CLNLPMJHCMQMPN-UHFFFAOYSA-N 2-methyl-1h-imidazole;phosphoric acid Chemical group OP(O)(O)=O.CC1=NC=CN1 CLNLPMJHCMQMPN-UHFFFAOYSA-N 0.000 claims 1
- GQLRFPJNVQIFPK-UHFFFAOYSA-N dihydrogen phosphate;3-methyl-1h-imidazol-3-ium Chemical group OP(O)(O)=O.CN1C=CN=C1 GQLRFPJNVQIFPK-UHFFFAOYSA-N 0.000 claims 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims 1
- 238000000576 coating method Methods 0.000 abstract description 6
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 239000011248 coating agent Substances 0.000 abstract description 2
- 230000001681 protective effect Effects 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 235000011007 phosphoric acid Nutrition 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000001723 curing Methods 0.000 description 14
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 11
- 150000003839 salts Chemical class 0.000 description 11
- 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 9
- 150000002460 imidazoles Chemical class 0.000 description 9
- 238000000113 differential scanning calorimetry Methods 0.000 description 8
- 239000004849 latent hardener Substances 0.000 description 7
- 239000000523 sample Substances 0.000 description 7
- 239000000839 emulsion Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 5
- 238000013035 low temperature curing Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000010408 film Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000002253 acid Substances 0.000 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 description 3
- 239000008199 coating composition Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- PQAMFDRRWURCFQ-UHFFFAOYSA-N 2-ethyl-1h-imidazole Chemical compound CCC1=NC=CN1 PQAMFDRRWURCFQ-UHFFFAOYSA-N 0.000 description 2
- -1 2-ethylhexyl Chemical group 0.000 description 2
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 2
- 150000002118 epoxides Chemical class 0.000 description 2
- 229920006332 epoxy adhesive Polymers 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 235000021317 phosphate Nutrition 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- KUBDPQJOLOUJRM-UHFFFAOYSA-N 2-(chloromethyl)oxirane;4-[2-(4-hydroxyphenyl)propan-2-yl]phenol Chemical compound ClCC1CO1.C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 KUBDPQJOLOUJRM-UHFFFAOYSA-N 0.000 description 1
- NCVGSSQICKMAIA-UHFFFAOYSA-N 2-heptadecyl-4,5-dihydro-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NCCN1 NCVGSSQICKMAIA-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- 229920001453 Arcel Polymers 0.000 description 1
- 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 description 1
- MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 235000009137 Quercus alba Nutrition 0.000 description 1
- 241001531312 Quercus pubescens Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000008186 active pharmaceutical agent Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229940106691 bisphenol a Drugs 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229920006334 epoxy coating Polymers 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009730 filament winding Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 238000007761 roller coating Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- C08G59/40—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
- C08G59/50—Amines
- C08G59/5093—Complexes of amines
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K1/00—Printed circuits
- H05K1/02—Details
- H05K1/03—Use of materials for the substrate
- H05K1/0313—Organic insulating material
- H05K1/032—Organic insulating material consisting of one material
- H05K1/0326—Organic insulating material consisting of one material containing O
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/703311 | 2000-11-01 | ||
| US09/703,311 US6441064B1 (en) | 2000-11-01 | 2000-11-01 | Imidazole-phosphoric acid salts as accelerators for dicyandiamide in one-component epoxy compositions |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003331270A Division JP2004010618A (ja) | 2000-11-01 | 2003-09-24 | ジシアンジアミドのための促進剤としてのイミダゾール燐酸塩を含む組成物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2002161127A JP2002161127A (ja) | 2002-06-04 |
| JP3509799B2 true JP3509799B2 (ja) | 2004-03-22 |
Family
ID=24824881
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2001333608A Expired - Fee Related JP3509799B2 (ja) | 2000-11-01 | 2001-10-31 | 一液性エポキシ組成物中のジシアンジアミドのための促進剤としてのイミダゾール−燐酸塩 |
| JP2003331270A Pending JP2004010618A (ja) | 2000-11-01 | 2003-09-24 | ジシアンジアミドのための促進剤としてのイミダゾール燐酸塩を含む組成物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003331270A Pending JP2004010618A (ja) | 2000-11-01 | 2003-09-24 | ジシアンジアミドのための促進剤としてのイミダゾール燐酸塩を含む組成物 |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US6441064B1 (https=) |
| EP (1) | EP1203782B1 (https=) |
| JP (2) | JP3509799B2 (https=) |
| CN (1) | CN1258560C (https=) |
| AT (1) | ATE317867T1 (https=) |
| DE (1) | DE60117212T2 (https=) |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20060194064A1 (en) * | 2002-03-01 | 2006-08-31 | Xiao Allison Y | Underfill encapsulant for wafer packaging and method for its application |
| JP4481011B2 (ja) | 2002-03-05 | 2010-06-16 | トランス テック ファーマ，インコーポレイテッド | リガンドのｒａｇｅとの相互作用を阻害する単環式および二環式アゾール誘導体 |
| EP1635823A1 (en) * | 2003-05-20 | 2006-03-22 | TransTech Pharma Inc. | Rage antagonists as agents to reverse amyloidosis and diseases associated therewith |
| EP1646054A4 (en) * | 2003-07-11 | 2010-05-19 | Ube Industries | ACIDS-BASE MIXTURE AND ION CONDUCTOR COMPOSED FROM SUCH A MIXTURE |
| WO2011025040A1 (ja) * | 2009-08-31 | 2011-03-03 | 日本合成化学工業株式会社 | エポキシ樹脂用硬化剤 |
| ES2467923T3 (es) | 2009-09-30 | 2014-06-13 | Transtech Pharma, Llc | Derivados de imidazol substituidos para el tratamiento de la enfermedad de Alzheimer |
| JP6030028B2 (ja) * | 2013-07-11 | 2016-11-24 | 株式会社Adeka | 新規化合物、熱硬化剤及びエポキシ樹脂組成物 |
| US9546243B2 (en) * | 2013-07-17 | 2017-01-17 | Air Products And Chemicals, Inc. | Amines and polymeric phenols and usage thereof as curing agents in one component epoxy resin compositions |
| JP6161464B2 (ja) * | 2013-08-08 | 2017-07-12 | 株式会社Adeka | 一液型硬化性樹脂組成物 |
| CN109563240A (zh) | 2016-08-15 | 2019-04-02 | 赢创德固赛有限公司 | 用于环氧树脂体系的具有咪唑盐添加剂的酸酐环氧固化剂 |
| KR102439519B1 (ko) | 2016-12-12 | 2022-09-05 | 에보니크 오퍼레이션즈 게엠베하 | 신규한 저온 무수물 에폭시 경화된 시스템 |
| CN111032724B (zh) | 2017-08-22 | 2022-04-29 | 盛势达技研株式会社 | 固化性组合物 |
| DE102018121012A1 (de) * | 2018-08-28 | 2020-03-05 | Alzchem Trostberg Gmbh | Verfahren zur Herstellung eines Druckgasbehälters |
| KR102197406B1 (ko) * | 2019-12-05 | 2020-12-31 | 주식회사 제일화성 | 친환경 바이오매스 기반의 아이소소바이드 에폭시를 활용한 고체상 에폭시 수지의 제조 방법 |
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| CN120988566B (zh) * | 2025-10-27 | 2025-12-30 | 广东百慕新材料技术工程有限公司 | 一种薄涂水性石墨烯改性苯氧浸涂涂料及其制备方法与应用 |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5508328A (en) | 1994-11-17 | 1996-04-16 | Alliedsignal Inc. | Curing epoxy resins using dicy, imidazole and acid |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3356645A (en) * | 1964-04-20 | 1967-12-05 | Shell Oil Co | Process for curing epoxy resins with a salt of an imidazole and compositions thereof |
| NL130329C (https=) | 1964-04-20 | |||
| US3329652A (en) | 1965-02-15 | 1967-07-04 | Shell Oil Co | Process for curing polyepoxides with anhydrides and activators therefor |
| US3632427A (en) | 1970-05-15 | 1972-01-04 | Air Prod & Chem | Epoxy resin and imidazole alkyl acid phosphate fiber treatment |
| US3631150A (en) | 1970-05-20 | 1971-12-28 | Dexter Corp | Synergistic composition for curing polyepoxides comprising an imidazole compound and dicyandiamide |
| US3755253A (en) | 1971-09-24 | 1973-08-28 | Shell Oil Co | Catalization of diaminodiphenylsulfone cure of polyepoxides with an imidazole compound or a salt thereof |
| JPS5883023A (ja) | 1981-11-11 | 1983-05-18 | Taoka Chem Co Ltd | 硬化性組成物 |
| JPS5920371A (ja) | 1982-07-27 | 1984-02-02 | Toyo Ink Mfg Co Ltd | 導電性接着剤 |
| DE3624177A1 (de) | 1986-07-17 | 1988-01-21 | Huels Chemische Werke Ag | Pulverlacke, deren herstellung und verwendung |
| JPH0253777A (ja) | 1988-08-18 | 1990-02-22 | Shikoku Chem Corp | １−ベンジルイミダゾール化合物の合成方法 |
| WO1994014866A1 (en) | 1992-12-21 | 1994-07-07 | Alliedsignal, Inc. | Solvent free epoxy resin compositions |
-
2000
- 2000-11-01 US US09/703,311 patent/US6441064B1/en not_active Expired - Lifetime
-
2001
- 2001-10-30 DE DE60117212T patent/DE60117212T2/de not_active Expired - Lifetime
- 2001-10-30 EP EP01125886A patent/EP1203782B1/en not_active Expired - Lifetime
- 2001-10-30 AT AT01125886T patent/ATE317867T1/de not_active IP Right Cessation
- 2001-10-31 JP JP2001333608A patent/JP3509799B2/ja not_active Expired - Fee Related
- 2001-11-01 CN CNB011372583A patent/CN1258560C/zh not_active Expired - Fee Related
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2003
- 2003-09-24 JP JP2003331270A patent/JP2004010618A/ja active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5508328A (en) | 1994-11-17 | 1996-04-16 | Alliedsignal Inc. | Curing epoxy resins using dicy, imidazole and acid |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1351092A (zh) | 2002-05-29 |
| JP2002161127A (ja) | 2002-06-04 |
| EP1203782A1 (en) | 2002-05-08 |
| JP2004010618A (ja) | 2004-01-15 |
| DE60117212T2 (de) | 2006-07-27 |
| EP1203782B1 (en) | 2006-02-15 |
| ATE317867T1 (de) | 2006-03-15 |
| CN1258560C (zh) | 2006-06-07 |
| DE60117212D1 (de) | 2006-04-20 |
| US6441064B1 (en) | 2002-08-27 |
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