CN1258560C - 一种可热固化单罐装环氧组合物 - Google Patents
一种可热固化单罐装环氧组合物 Download PDFInfo
- Publication number
- CN1258560C CN1258560C CNB011372583A CN01137258A CN1258560C CN 1258560 C CN1258560 C CN 1258560C CN B011372583 A CNB011372583 A CN B011372583A CN 01137258 A CN01137258 A CN 01137258A CN 1258560 C CN1258560 C CN 1258560C
- Authority
- CN
- China
- Prior art keywords
- epoxy
- imidazoles
- dihydrogen phosphate
- epoxy composite
- dyhard
- 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
- 239000004593 Epoxy Substances 0.000 title claims abstract description 67
- 239000000203 mixture Substances 0.000 title claims abstract description 33
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 title abstract description 5
- 229910019142 PO4 Inorganic materials 0.000 title 1
- 239000010452 phosphate Substances 0.000 title 1
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 20
- 150000002460 imidazoles Chemical class 0.000 claims description 52
- 239000002131 composite material Substances 0.000 claims description 21
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 claims description 17
- 238000005580 one pot reaction Methods 0.000 claims description 16
- 229920005989 resin Polymers 0.000 claims description 15
- 239000011347 resin Substances 0.000 claims description 15
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims description 14
- 239000007787 solid Substances 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- -1 4Be hydrogen Chemical class 0.000 claims description 9
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 claims description 8
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 claims description 7
- 229940015043 glyoxal Drugs 0.000 claims description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 238000007725 thermal activation Methods 0.000 claims 2
- 125000003700 epoxy group Chemical group 0.000 claims 1
- 150000003573 thiols Chemical group 0.000 claims 1
- LPXDNEQTGPFOPF-UHFFFAOYSA-N hydron;1h-imidazol-1-ium;phosphate Chemical compound C1=CNC=N1.OP(O)(O)=O LPXDNEQTGPFOPF-UHFFFAOYSA-N 0.000 abstract description 19
- 229920000647 polyepoxide Polymers 0.000 abstract description 16
- 239000003822 epoxy resin Substances 0.000 abstract description 12
- 239000011248 coating agent Substances 0.000 abstract description 7
- 238000000576 coating method Methods 0.000 abstract description 7
- 239000000853 adhesive Substances 0.000 abstract description 2
- 230000001070 adhesive effect Effects 0.000 abstract description 2
- 230000001681 protective effect Effects 0.000 abstract description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 32
- 235000011007 phosphoric acid Nutrition 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000001723 curing Methods 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 239000002585 base Substances 0.000 description 10
- 150000003839 salts Chemical class 0.000 description 9
- 239000000839 emulsion Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 238000013035 low temperature curing Methods 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 150000002118 epoxides Chemical class 0.000 description 4
- 238000007711 solidification Methods 0.000 description 4
- 230000008023 solidification Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 238000007605 air drying Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 150000003016 phosphoric acids Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- MNAHQWDCXOHBHK-UHFFFAOYSA-N 1-phenylpropane-1,1-diol Chemical compound CCC(O)(O)C1=CC=CC=C1 MNAHQWDCXOHBHK-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 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
- 238000007766 curtain coating Methods 0.000 description 2
- 229920006332 epoxy adhesive Polymers 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- 125000000524 functional group Chemical group 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
- 230000007774 longterm Effects 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000007704 transition Effects 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
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical class CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 1
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 description 1
- 241000963007 Anelosimus may Species 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920003341 Epi-rez 3510-W-60 Polymers 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000004411 aluminium Substances 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
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 239000004567 concrete Substances 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
- 239000013530 defoamer Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000009189 diving Effects 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
- 229920006334 epoxy coating Polymers 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000013007 heat curing Methods 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
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [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
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000006254 rheological additive Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/703,311 | 2000-11-01 | ||
| 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 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1351092A CN1351092A (zh) | 2002-05-29 |
| CN1258560C true CN1258560C (zh) | 2006-06-07 |
Family
ID=24824881
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB011372583A Expired - Fee Related CN1258560C (zh) | 2000-11-01 | 2001-11-01 | 一种可热固化单罐装环氧组合物 |
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 |
| KR102197405B1 (ko) * | 2019-12-05 | 2020-12-31 | 주식회사 제일화성 | 친환경 바이오매스 기반의 아이소소바이드 에폭시 원료를 이용한 고체상 에폭시 수지의 제조 방법 |
| CN116478344A (zh) * | 2022-01-17 | 2023-07-25 | 万华化学集团股份有限公司 | 一种水性单组份环氧乳液及其制备方法 |
| 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 |
| CN121379466B (zh) * | 2025-12-24 | 2026-04-17 | 厦门优佰电子材料有限公司 | 一种ar/vr眼镜用耐溶剂型防水密封胶及其制备方法 |
Family Cites Families (12)
| 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 |
| US5508328A (en) * | 1994-11-17 | 1996-04-16 | Alliedsignal Inc. | Curing epoxy resins using dicy, imidazole and acid |
-
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
-
2003
- 2003-09-24 JP JP2003331270A patent/JP2004010618A/ja active Pending
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 |
| JP3509799B2 (ja) | 2004-03-22 |
| ATE317867T1 (de) | 2006-03-15 |
| DE60117212D1 (de) | 2006-04-20 |
| US6441064B1 (en) | 2002-08-27 |
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