GB832189A - Curing agents for epoxide resins - Google Patents
Curing agents for epoxide resinsInfo
- Publication number
- GB832189A GB832189A GB1347955A GB1347955A GB832189A GB 832189 A GB832189 A GB 832189A GB 1347955 A GB1347955 A GB 1347955A GB 1347955 A GB1347955 A GB 1347955A GB 832189 A GB832189 A GB 832189A
- Authority
- GB
- United Kingdom
- Prior art keywords
- parts
- glycidyl ether
- reacted
- amine
- mols
- 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
- 229920000647 polyepoxide Polymers 0.000 title abstract 5
- 150000001412 amines Chemical class 0.000 abstract 8
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 6
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 4
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 3
- 239000003795 chemical substances by application Substances 0.000 abstract 3
- 125000003700 epoxy group Chemical group 0.000 abstract 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 abstract 2
- JPYHHZQJCSQRJY-UHFFFAOYSA-N Phloroglucinol Natural products CCC=CCC=CCC=CCC=CCCCCC(=O)C1=C(O)C=C(O)C=C1O JPYHHZQJCSQRJY-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 abstract 2
- 229920005989 resin Polymers 0.000 abstract 2
- 239000011347 resin Substances 0.000 abstract 2
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract 1
- 229910052796 boron Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000002118 epoxides Chemical group 0.000 abstract 1
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 239000012074 organic phase Substances 0.000 abstract 1
- 229920001568 phenolic resin Polymers 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 238000005406 washing Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C08G59/182—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 using pre-adducts of epoxy compounds with curing agents
- C08G59/184—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 using pre-adducts of epoxy compounds with curing agents with amines
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)
Abstract
Secondary curing agents for epoxide resins are obtained by reacting a secondary monoamine having its N atom linked to two different carbon atoms with a glycidyl ether of a polyhydric phenol having at least 3 OH groups. At least 1.5 mols. of amine are used per epoxy group in the glycidyl ether and unreacted amine is removed. In the example diethylamine (3 mols.) was added to a solution in dioxane of a glycidyl ether of a low molecular weight phenol-formaldehyde condensate (equivalent to 1 epoxy group). Dioxane and excess amine were removed after reaction leaving a viscous liquid, 35 parts of which were equivalent for curing epoxide resins to 10 parts of diethylamine. Dimethylamine and piperidine are suitable amines and the glycidyl ether of 1,3,5-trihydroxy benzene is also suitable as a starting material. Specifications 691,543 and 705,786 are referred to.ALSO:Secondary curing agents for epoxide resins of the kind described in Specifications 691,543 and 705,786 are obtained by reacting a secondary monoamine having its N atom linked to two different C atoms with a glycidyl ether of a polyhydric phenol having at least three OH groups. At least 1.5 mols. of amine are used for each epoxy group in the glycidyl ether. Examples of suitable glycidyl ethers are (A) a mixture of 12.6 parts 1,3,5-trihydroxy benzene and 55.5 parts epichlorhydrin were reacted by dropwise addition of 120 parts NaOH in an equal weight of water, the temperature being maintained at 60 DEG C. A viscous resin was obtained by separating the organic phase from the inorganic and washing it free from NaCl. (B) 376 parts phenol were reacted with 83 parts formaldehyde using 154 parts boron p trifluoride-ethyl etherate complex as catalyst. 263 parts of the condensate were reacted with 365 parts epichlorhydrin in presence of 252 parts 50% NaOH. In preparing the secondary curing agent 220 parts diethylamine were reacted with 200 parts Resin B in 200 parts dioxan, there being 3 mols. amine present per epoxide group. The mixture was reacted at 60-70 DEG C. for 3 hours after which excess amine was removed under vacuum. A viscous resin was obtained. For the curing of epoxide resins, 35 parts of this product were equivalent to 10 parts free diethylamine. Other suitable amines mentioned are dimethylamine and piperidine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1347955A GB832189A (en) | 1955-05-10 | 1955-05-10 | Curing agents for epoxide resins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1347955A GB832189A (en) | 1955-05-10 | 1955-05-10 | Curing agents for epoxide resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB832189A true GB832189A (en) | 1960-04-06 |
Family
ID=10023718
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1347955A Expired GB832189A (en) | 1955-05-10 | 1955-05-10 | Curing agents for epoxide resins |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB832189A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4348505A (en) | 1980-07-23 | 1982-09-07 | Ciba-Geigy Corporation | Adducts from amines and di- and polyepoxides |
| EP0783010A3 (en) * | 1996-01-04 | 1998-01-07 | Air Products And Chemicals, Inc. | Methylamine adduct for cure of epony resins |
| EP0786481A3 (en) * | 1996-01-26 | 1998-01-07 | Air Products And Chemicals, Inc. | Reactive accelerators for amine cured epoxy resins |
| CN110891998A (en) * | 2017-07-14 | 2020-03-17 | Dic株式会社 | Epoxy resin, epoxy resin composition containing the same, and cured product using the epoxy resin composition |
-
1955
- 1955-05-10 GB GB1347955A patent/GB832189A/en not_active Expired
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4348505A (en) | 1980-07-23 | 1982-09-07 | Ciba-Geigy Corporation | Adducts from amines and di- and polyepoxides |
| EP0783010A3 (en) * | 1996-01-04 | 1998-01-07 | Air Products And Chemicals, Inc. | Methylamine adduct for cure of epony resins |
| EP0786481A3 (en) * | 1996-01-26 | 1998-01-07 | Air Products And Chemicals, Inc. | Reactive accelerators for amine cured epoxy resins |
| CN110891998A (en) * | 2017-07-14 | 2020-03-17 | Dic株式会社 | Epoxy resin, epoxy resin composition containing the same, and cured product using the epoxy resin composition |
| KR20200030050A (en) * | 2017-07-14 | 2020-03-19 | 디아이씨 가부시끼가이샤 | Epoxy resin, and an epoxy resin composition containing the same, and a cured product using the epoxy resin composition |
| EP3653659A4 (en) * | 2017-07-14 | 2021-04-07 | DIC Corporation | EPOXY RESIN, EPOXY RESIN COMPOSITION CONTAINING IT, AND CURED PRODUCT OBTAINED FROM THE SAID EPOXY RESIN COMPOSITION |
| CN110891998B (en) * | 2017-07-14 | 2022-06-10 | Dic株式会社 | Epoxy resin, epoxy resin composition containing same, and cured product using same |
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