GB963058A - Improvements in the curing of epoxy resins - Google Patents
Improvements in the curing of epoxy resinsInfo
- Publication number
- GB963058A GB963058A GB2204659A GB2204659A GB963058A GB 963058 A GB963058 A GB 963058A GB 2204659 A GB2204659 A GB 2204659A GB 2204659 A GB2204659 A GB 2204659A GB 963058 A GB963058 A GB 963058A
- Authority
- GB
- United Kingdom
- Prior art keywords
- aniline
- added
- toluidine
- amine
- naphthylamine
- 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
- 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 title abstract 3
- 229920000647 polyepoxide Polymers 0.000 title abstract 3
- 239000003822 epoxy resin Substances 0.000 title abstract 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 4
- RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 abstract 4
- WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 abstract 2
- JJYPMNFTHPTTDI-UHFFFAOYSA-N 3-methylaniline Chemical compound CC1=CC=CC(N)=C1 JJYPMNFTHPTTDI-UHFFFAOYSA-N 0.000 abstract 2
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 abstract 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 abstract 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 abstract 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 abstract 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methyl-N-phenylamine Natural products CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 abstract 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 abstract 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 abstract 2
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 abstract 2
- AASABFUMCBTXRL-UHFFFAOYSA-N n-ethyl-4-methylaniline Chemical compound CCNC1=CC=C(C)C=C1 AASABFUMCBTXRL-UHFFFAOYSA-N 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- OWRCNXZUPFZXOS-UHFFFAOYSA-N 1,3-diphenylguanidine Chemical compound C=1C=CC=CC=1NC(=N)NC1=CC=CC=C1 OWRCNXZUPFZXOS-UHFFFAOYSA-N 0.000 abstract 1
- RBHIUNHSNSQJNG-UHFFFAOYSA-N 6-methyl-3-(2-methyloxiran-2-yl)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CC2(C)OC2CC1C1(C)CO1 RBHIUNHSNSQJNG-UHFFFAOYSA-N 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
- 229960001413 acetanilide Drugs 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000008430 aromatic amides Chemical class 0.000 abstract 1
- -1 b -naphthylamine Chemical compound 0.000 abstract 1
- 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 abstract 1
- BQQUFAMSJAKLNB-UHFFFAOYSA-N dicyclopentadiene diepoxide Chemical compound C12C(C3OC33)CC3C2CC2C1O2 BQQUFAMSJAKLNB-UHFFFAOYSA-N 0.000 abstract 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 150000003142 primary aromatic amines Chemical class 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 150000003336 secondary aromatic amines Chemical class 0.000 abstract 1
- 150000005846 sugar alcohols Polymers 0.000 abstract 1
- 238000007738 vacuum evaporation Methods 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
- C08G59/40—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
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
An acetone solution of metaphenylene diamine is added dropwise to aqueous hydrofluoboric acid. Orange red crystalline metaphenylene diamine monohydro fluoborate is obtained by vacuum evaporation of the solvent. Aniline hydrofluoborate was similarly prepared.ALSO:A curable composition comprises (i) a polyglycidyl ether of a polyhydric phenol or polyhydric alcohol and (ii) a salt of an amine and hydrofluoboric acid. Epoxy resins (i) used in the examples are glycidyl ethers of hydroquinone and bisphenol A. Amine salts (ii) specified are those of aniline, p-toluidine, m- or p-phenylene diamine and b -naphthylamine. There may also be added as an inhibitor up to 5% by weight of (iii) a free primary or secondary aromatic amine or an aromatic amide, e.g. aniline, m- or p-toluidine, p-amino phenol, p-phenylene diamine, o-amino benzoic acid, b -naphthylamine, benzylamine, N-ethyl aniline, N-ethyl p-toluidine, diphenylamine, diphenyl guanidine, carbazole, or acetanilide. Conventional fillers, resins and solvents may be added, of which lists are given; monoepoxides (lists) and polyepoxides (polyglycidyl ether of glycerol; dicyclopentadiene dioxide and limonene dioxide) may also be added as reactive diluents.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2204659A GB963058A (en) | 1959-06-26 | 1959-06-26 | Improvements in the curing of epoxy resins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2204659A GB963058A (en) | 1959-06-26 | 1959-06-26 | Improvements in the curing of epoxy resins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB963058A true GB963058A (en) | 1964-07-08 |
Family
ID=10172999
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2204659A Expired GB963058A (en) | 1959-06-26 | 1959-06-26 | Improvements in the curing of epoxy resins |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB963058A (en) |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4503211A (en) * | 1984-05-31 | 1985-03-05 | Minnesota Mining And Manufacturing Co. | Epoxy resin curing agent, process and composition |
| EP0257757A2 (en) | 1986-08-11 | 1988-03-02 | Minnesota Mining And Manufacturing Company | Coated abrasive having radiation curable binder |
| US4925901A (en) * | 1988-02-12 | 1990-05-15 | The Dow Chemical Company | Latent, curable, catalyzed mixtures of epoxy-containing and phenolic hydroxyl-containing compounds |
| US4946817A (en) * | 1984-07-17 | 1990-08-07 | The Dow Chemical Company | Latent catalysts for epoxy-containing compounds |
| US5140079A (en) * | 1990-02-06 | 1992-08-18 | The Dow Chemical Company | Latent, curable, catalyzed mixtures of epoxy-containing and phenolic-hydroxyl-containing compounds containing compounds or complexes formed from contacting organic phosphines or arsines with weak nucleophilic acids |
| US5169473A (en) * | 1990-05-21 | 1992-12-08 | The Dow Chemical Company | Latent catalysts, epoxy compositions incorporating same, and coating, impregnating and bonding methods employing the compositions |
| WO1994000527A1 (en) * | 1992-06-18 | 1994-01-06 | Minnesota Mining And Manufacturing Company | Epoxy adhesive composition |
| US5294582A (en) * | 1991-04-25 | 1994-03-15 | Nippon Paint Co., Ltd. | Urea-superacid salts and their use as a curing catalyst of epoxy resins |
| US5308895A (en) * | 1990-05-21 | 1994-05-03 | The Dow Chemical Company | Cure inhibited epoxy resin compositions and laminates prepared from the compositions |
| US5504161A (en) * | 1989-04-03 | 1996-04-02 | Reilly Industries, Inc. | Vinylpyridine polymer support complexed with boron trifluoride |
| US5503937A (en) * | 1984-07-17 | 1996-04-02 | The Dow Chemical Company | Curable composition which comprises adducts of heterocyclic compounds |
| US5514728A (en) * | 1993-07-23 | 1996-05-07 | Minnesota Mining And Manufacturing Company | Catalysts and initiators for polymerization |
| US5721323A (en) * | 1990-05-21 | 1998-02-24 | The Dow Chemical Company | Cure inhibited epoxy resin compositions and laminates prepared from the compositions |
| US6613839B1 (en) | 1997-01-21 | 2003-09-02 | The Dow Chemical Company | Polyepoxide, catalyst/cure inhibitor complex and anhydride |
| CN113294613A (en) * | 2021-04-30 | 2021-08-24 | 江苏龙山管件有限公司 | High-temperature-resistant alloy elbow and processing technology thereof |
-
1959
- 1959-06-26 GB GB2204659A patent/GB963058A/en not_active Expired
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4503211A (en) * | 1984-05-31 | 1985-03-05 | Minnesota Mining And Manufacturing Co. | Epoxy resin curing agent, process and composition |
| US4946817A (en) * | 1984-07-17 | 1990-08-07 | The Dow Chemical Company | Latent catalysts for epoxy-containing compounds |
| US5503937A (en) * | 1984-07-17 | 1996-04-02 | The Dow Chemical Company | Curable composition which comprises adducts of heterocyclic compounds |
| EP0257757A2 (en) | 1986-08-11 | 1988-03-02 | Minnesota Mining And Manufacturing Company | Coated abrasive having radiation curable binder |
| US4925901A (en) * | 1988-02-12 | 1990-05-15 | The Dow Chemical Company | Latent, curable, catalyzed mixtures of epoxy-containing and phenolic hydroxyl-containing compounds |
| US5504161A (en) * | 1989-04-03 | 1996-04-02 | Reilly Industries, Inc. | Vinylpyridine polymer support complexed with boron trifluoride |
| US5140079A (en) * | 1990-02-06 | 1992-08-18 | The Dow Chemical Company | Latent, curable, catalyzed mixtures of epoxy-containing and phenolic-hydroxyl-containing compounds containing compounds or complexes formed from contacting organic phosphines or arsines with weak nucleophilic acids |
| US5308895A (en) * | 1990-05-21 | 1994-05-03 | The Dow Chemical Company | Cure inhibited epoxy resin compositions and laminates prepared from the compositions |
| US5314720A (en) * | 1990-05-21 | 1994-05-24 | The Dow Chemical Company | Cure inhibited epoxy resin compositions and laminates prepared from the compositions |
| US5169473A (en) * | 1990-05-21 | 1992-12-08 | The Dow Chemical Company | Latent catalysts, epoxy compositions incorporating same, and coating, impregnating and bonding methods employing the compositions |
| US5620789A (en) * | 1990-05-21 | 1997-04-15 | The Dow Chemical Company | Cure inhibited epoxy resin compositions and laminates prepared from the compositions |
| US5721323A (en) * | 1990-05-21 | 1998-02-24 | The Dow Chemical Company | Cure inhibited epoxy resin compositions and laminates prepared from the compositions |
| US5294582A (en) * | 1991-04-25 | 1994-03-15 | Nippon Paint Co., Ltd. | Urea-superacid salts and their use as a curing catalyst of epoxy resins |
| US5280067A (en) * | 1992-06-18 | 1994-01-18 | Minnesota Mining And Manufacturing Company | Substituted pentafluoroantmonic acid-substituted aniline epoxy curing catalysts |
| WO1994000527A1 (en) * | 1992-06-18 | 1994-01-06 | Minnesota Mining And Manufacturing Company | Epoxy adhesive composition |
| US5514728A (en) * | 1993-07-23 | 1996-05-07 | Minnesota Mining And Manufacturing Company | Catalysts and initiators for polymerization |
| US6613839B1 (en) | 1997-01-21 | 2003-09-02 | The Dow Chemical Company | Polyepoxide, catalyst/cure inhibitor complex and anhydride |
| CN113294613A (en) * | 2021-04-30 | 2021-08-24 | 江苏龙山管件有限公司 | High-temperature-resistant alloy elbow and processing technology thereof |
| CN113294613B (en) * | 2021-04-30 | 2024-05-31 | 江苏龙山管件有限公司 | High-temperature-resistant alloy elbow and processing technology thereof |
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