JPH0160164B2 - - Google Patents
Info
- Publication number
- JPH0160164B2 JPH0160164B2 JP16455782A JP16455782A JPH0160164B2 JP H0160164 B2 JPH0160164 B2 JP H0160164B2 JP 16455782 A JP16455782 A JP 16455782A JP 16455782 A JP16455782 A JP 16455782A JP H0160164 B2 JPH0160164 B2 JP H0160164B2
- Authority
- JP
- Japan
- Prior art keywords
- latent curing
- curing agent
- epoxy
- compound
- phenol
- 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
- 239000003795 chemical substances by application Substances 0.000 claims description 33
- 150000001875 compounds Chemical class 0.000 claims description 23
- 239000003822 epoxy resin Substances 0.000 claims description 16
- 229920000647 polyepoxide Polymers 0.000 claims description 16
- 239000004593 Epoxy Substances 0.000 claims description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 9
- 125000001302 tertiary amino group Chemical group 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- -1 phenol compound Chemical class 0.000 claims description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- 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 12
- 239000000047 product Substances 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 8
- 125000003700 epoxy group Chemical group 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
- 239000002253 acid Substances 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 4
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 4
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 4
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 description 3
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 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 3
- 238000010438 heat treatment Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 238000010298 pulverizing process Methods 0.000 description 3
- ASWPBPHMBJLXOE-UHFFFAOYSA-N 1-(2-ethyl-4-methylimidazol-1-yl)-3-phenoxypropan-2-ol Chemical compound CCC1=NC(C)=CN1CC(O)COC1=CC=CC=C1 ASWPBPHMBJLXOE-UHFFFAOYSA-N 0.000 description 2
- RHTXCFRIEYHAHM-UHFFFAOYSA-N 1-(2-methylimidazol-1-yl)-3-phenoxypropan-2-ol Chemical compound CC1=NC=CN1CC(O)COC1=CC=CC=C1 RHTXCFRIEYHAHM-UHFFFAOYSA-N 0.000 description 2
- NCXUNZWLEYGQAH-UHFFFAOYSA-N 1-(dimethylamino)propan-2-ol Chemical compound CC(O)CN(C)C NCXUNZWLEYGQAH-UHFFFAOYSA-N 0.000 description 2
- PZAHYZLSKYNENE-UHFFFAOYSA-N 1-butoxy-3-(2-methylimidazol-1-yl)propan-2-ol Chemical compound CCCCOCC(O)CN1C=CN=C1C PZAHYZLSKYNENE-UHFFFAOYSA-N 0.000 description 2
- LYUVLUOMAJAVPI-UHFFFAOYSA-N 1-phenoxy-3-(2-phenyl-4,5-dihydroimidazol-1-yl)propan-2-ol Chemical compound C1CN=C(C=2C=CC=CC=2)N1CC(O)COC1=CC=CC=C1 LYUVLUOMAJAVPI-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CWLKGDAVCFYWJK-UHFFFAOYSA-N 3-aminophenol Chemical compound NC1=CC=CC(O)=C1 CWLKGDAVCFYWJK-UHFFFAOYSA-N 0.000 description 2
- ALEBYBVYXQTORU-UHFFFAOYSA-N 6-hydrazinyl-6-oxohexanoic acid Chemical compound NNC(=O)CCCCC(O)=O ALEBYBVYXQTORU-UHFFFAOYSA-N 0.000 description 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920003986 novolac Polymers 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229940079877 pyrogallol Drugs 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 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 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IMJCKVKBXYZZGJ-UHFFFAOYSA-N 1-(dimethylamino)-3-phenoxypropan-2-ol Chemical compound CN(C)CC(O)COC1=CC=CC=C1 IMJCKVKBXYZZGJ-UHFFFAOYSA-N 0.000 description 1
- IFLCSHCQLDMGJB-UHFFFAOYSA-N 1-butoxy-3-(2-ethyl-4-methylimidazol-1-yl)propan-2-ol Chemical compound CCCCOCC(O)CN1C=C(C)N=C1CC IFLCSHCQLDMGJB-UHFFFAOYSA-N 0.000 description 1
- SDWZQKKODUFTEY-UHFFFAOYSA-N 1-butoxy-3-(dimethylamino)propan-2-ol Chemical compound CCCCOCC(O)CN(C)C SDWZQKKODUFTEY-UHFFFAOYSA-N 0.000 description 1
- ANFXTILBDGTSEG-UHFFFAOYSA-N 1-methyl-4,5-dihydroimidazole Chemical compound CN1CCN=C1 ANFXTILBDGTSEG-UHFFFAOYSA-N 0.000 description 1
- AUABZJZJXPSZCN-UHFFFAOYSA-N 2-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC=C1O AUABZJZJXPSZCN-UHFFFAOYSA-N 0.000 description 1
- 229940013085 2-diethylaminoethanol Drugs 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- 229940018563 3-aminophenol Drugs 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N Alumina Chemical compound [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000011810 insulating material Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical class NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 239000012925 reference material Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Priority Applications (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16455782A JPS5953526A (ja) | 1982-09-21 | 1982-09-21 | エポキシ樹脂用潜在性硬化剤 |
| DE3382819T DE3382819T2 (de) | 1982-09-21 | 1983-09-15 | Latente Härter für Epoxyharze |
| DE3382736T DE3382736T2 (de) | 1982-09-21 | 1983-09-15 | Latente Härter für Epoxyharze. |
| EP83305398A EP0104837B1 (en) | 1982-09-21 | 1983-09-15 | Latent curing agents for epoxy resins |
| EP93109367A EP0569044B1 (en) | 1982-09-21 | 1983-09-15 | Latent curing agents for epoxy resins |
| US06/532,901 US4542202A (en) | 1982-09-21 | 1983-09-16 | Latent curing agents for epoxy resins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP16455782A JPS5953526A (ja) | 1982-09-21 | 1982-09-21 | エポキシ樹脂用潜在性硬化剤 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5953526A JPS5953526A (ja) | 1984-03-28 |
| JPH0160164B2 true JPH0160164B2 (d) | 1989-12-21 |
Family
ID=15795422
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP16455782A Granted JPS5953526A (ja) | 1982-09-21 | 1982-09-21 | エポキシ樹脂用潜在性硬化剤 |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5953526A (d) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4689390A (en) | 1985-04-01 | 1987-08-25 | Asahi Denka Kogyo K.K. | Curable epoxy resin composition |
| JPS63183920A (ja) * | 1987-01-27 | 1988-07-29 | Somar Corp | 液状エポキシ樹脂組成物およびその製造方法 |
| JPS6436672A (en) * | 1987-07-31 | 1989-02-07 | Somar Corp | Epoxy polymer composition for bonding chip part |
| US6451931B1 (en) | 2000-12-29 | 2002-09-17 | Asahi Denki Kogyo Kabushiki Kaisha | Reaction product of primary and tertiary amine-containing compound, dihydrazide an polyisocyanate |
| JP4752131B2 (ja) | 2001-05-16 | 2011-08-17 | 味の素株式会社 | エポキシ樹脂用潜在性硬化剤及び硬化性エポキシ樹脂組成物 |
| JP4906071B2 (ja) * | 2006-04-28 | 2012-03-28 | 株式会社Ａｄｅｋａ | エポキシ樹脂用硬化剤組成物およびそれを含有してなる硬化性エポキシ樹脂組成物 |
| US8288447B2 (en) | 2006-06-07 | 2012-10-16 | Henkel Ag & Co. Kgaa | Foamable compositions based on epoxy resins and polyesters |
| JP7198644B2 (ja) | 2018-11-27 | 2023-01-04 | 住友化学株式会社 | エポキシ樹脂組成物及びその硬化物 |
| US12384874B2 (en) | 2020-03-31 | 2025-08-12 | Namics Corporation | Curing catalyst, resin composition, sealing material, adhesive and cured product |
| US20230203237A1 (en) | 2020-03-31 | 2023-06-29 | Namics Corporation | Epoxy amine adduct, curing catalyst, resin composition, sealing material, adhesive and cured article |
| US20230212385A1 (en) | 2020-05-27 | 2023-07-06 | Sumitomo Chemical Company, Limited | Epoxy resin composition and cured product thereof |
| JP2022175617A (ja) | 2021-05-14 | 2022-11-25 | 住友化学株式会社 | エポキシ樹脂組成物及びその硬化物 |
-
1982
- 1982-09-21 JP JP16455782A patent/JPS5953526A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5953526A (ja) | 1984-03-28 |
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