US3909480A
Expired / Lapsed
US
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Epoxy resin compositions containing tetraphenylborates of imidazoles
Assignee: Hitachi Ltd
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Filing: 1974-03-27
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Granted: 1975-09-30
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Expires: 1994-03-27
Abstract
Abstract This invention provides an epoxy resin composition excellent in curability and storage stability (shelf life or potting life) and capable of yielding a cured product excellent in various characteristics, comprising an epoxy resin and a tetrasubstituted borate of imidazoles incorporated therein, and also provides a method for manufacturing said composition.
Inventors
- 👤 Masatzugu Ogata
- 👤 Ritsuro Tada
- 👤 Motoyo Wajima
- 👤 Masahiro Kitamura
- 👤 Hiroshi Suzuki
- 👤 Mikio Sato
- 👤 Etuzi Kubo
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 18:20
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/55
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
92 words
AN EPOXY RESIN COMPOSITION CONSISTING ESSENTIALLY OF (A) 100 PARTS BY WEIGHT OF AN EPOXY RESIN HAVING AT LEAST TWO VICINAL EPOXY GROUPS AND (B) 0.01 TO 30 PARTS BY WEIGHT OF AT LEAST ONE ORGANOBORON COMPOUND SELECTED FROM THE GROUP CONSISTING OF TETRAPHENYL BORATES OF IMIDAZOLE AND TETRAPHENYLBORATES OF IMIDAZOLE DERIVATIVES OBTAINED BY REACTING ALKALI METAL SALTS OF TETRAPHENYLBORON WITH AT LEAST ONE MEMBER SELECTED FROM THE GROUP CONSISTING OF SALTS OF IMIDAZOLE AND SALTS OF IMIDAZOLE DERIVATIVES OBTAINED BY REACTING IMIDAZOLE OR AN IMIDAZOLE DERIVATIVE REPRESENTED BY THE GENERAL FORMULA:
Claim 2
Dependent Claim
92 words
AN EPOXY RESIN COMPOSITION CONSISTING ESSENTIALLY OF (A) 100 PARTS BY WEIGHT OF AN EPOXY RESIN HAVING AT LEAST TWO VICINAL EPOXY GROUPS AND (B) 0.01 TO 30 PARTS BY WEIGHT OF AT LEAST ONE ORGANOBORON COMPOUND SELECTED FROM THE GROUP CONSISTING OF TETRAPHENYL BORATES OF IMIDAZOLE AND TETRAPHENYLBORATES OF IMIDAZOLE DERIVATIVES OBTAINED BY REACTING ALKALI METAL SALTS OF TETRAPHENYLBORON WITH AT LEAST ONE MEMBER SELECTED FROM THE GROUP CONSISTING OF SALTS OF IMIDAZOLE AND SALTS OF IMIDAZOLE DERIVATIVES OBTAINED BY REACTING IMIDAZOLE OR AN IMIDAZOLE DERIVATIVE REPRESENTED BY THE GENERAL FORMULA:
Claim 3
Dependent Claim
26 words
An epoxy resin composition according to claim 1, wherein the amount of the at least one organoboron compound (b) is 0.5 to 20 parts by weight.
Claim 4
Dependent Claim
89 words
An epoxy resin composition consisting essentially of (a) 100 parts by weight of an epoxy resin having at least two vicinal epoxy groups, (b) 0.01 to 30 parts by weight of at least one organoboron compound selected from the group consisting Of tetraphenylborates of imidazole and tetraphenylborates of imidazole derivatives obtained by reacting alkali metal salts of tetraphenylboron with at least one member selected from the group consisting of salts of imidazole and salts of imidazole derivatives formed by reacting imidazole or imidazole derivatives represented by the general formula:
Claim 5
Dependent Claim
89 words
An epoxy resin composition consisting essentially of (a) 100 parts by weight of an epoxy resin having at least two vicinal epoxy groups, (b) 0.01 to 30 parts by weight of at least one organoboron compound selected from the group consisting Of tetraphenylborates of imidazole and tetraphenylborates of imidazole derivatives obtained by reacting alkali metal salts of tetraphenylboron with at least one member selected from the group consisting of salts of imidazole and salts of imidazole derivatives formed by reacting imidazole or imidazole derivatives represented by the general formula:
Claim 6
Dependent Claim
48 words
An epoxy resin composition according to claim 3, wherein the amount of the at least one organoboron compound (b) is 0.01 to 20 parts by weight; the curing agent (c) is an acid anhydride and the amount of said acid anhydride is 0.1 to 200 parts by weight.
Claim 7
Dependent Claim
48 words
An epoxy resin composition according to claim 3, wherein the amount of the at least one organoboron compound (b) is 0.01 to 20 parts by weight; the curing agent (c) is an amine compound and the amount of said amine compound is 0.1 to 150 parts by weight.
Claim 8
Dependent Claim
37 words
An epoxy resin composition according to claim 1, wherein the organoboron compound (b) is at least one member selected from the group consisting of imidazolium tetraphenylborate, 2-ethyl-4-methylimidazolium tetraphenylborate, 1-cyanoethyl-2-phenylimidazolium tetraphenylborate, 1-cyanoethyl-2-undecylimidazolium tetraphenylborate, 1-cyanoethyl-2-ethyl-4-methylimidazolium tetraphenylborate, and 2-ethyl-1,4-dimethylimidazolium tetraphenylborate.
Claim 9
Dependent Claim
37 words
An epoxy resin composition according to claim 3, wherein the organoboron compound (b) is at least one tetraphenylborate selected from the group consisting of imidazolium tetraphenylborate, 2-ethyl-4-methylimidazolium tetraphenylborate, 1-cyanoethyl-2-phenylimidazolium tetraphenylborate, 1-cyanoethyl-2-undecylimidazolium tetraphenylborate, 1-cyanoethyl-2-ethyl-4-methylimidazolium tetraphenylborate, and 2-ethyl-1,4-dimethylimidazolium tetraphenylborate.
Claim 10
Dependent Claim
66 words
An epoxy resin composition according to claim 3, wherein the curing agent (c) is at least one member selected from the group consisting of maleic anhydride, dichloromaleic anhydride, dodecenylsuccinic anhydride, pyromellitic dianhydride, trimellitic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride, methylendomethylenetetrahydrophthalic anhydride, hexachloroendomethylenetetrahydrophthalic anhydride, m-phenylenediamine, diaminodiphenyl ether, diaminodiphenylmethane, 4,4''-diaminodiphenylmethane-3,3''-dicarbonic acid, diaminodiphenyl sulfone, benzidine, 4,4''-bis(o-toluidine), 4,4''-thiodianiline, dianisidine, methylenebis(o-chloroaniline), bis(3,4-diaminophenyl) sulfone, and diaminoditolyl sulfone.
Claim 11
Dependent Claim
50 words
An epoxy resin composition according to claim 4, wherein the curing agent (c) is at least one acid anhydride selected from the group consisting of maleic anhydride, dichloromaleic anhydride, dodecenylsuccinic anhydride, pyromellitic dianhydride, trimellitic anhydride, phthalic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydrIde, hexahydrophthalic anhydride, endomethylenetetrahydrophthalic anhydride, methylendomethylenetetrahydrophthalic anhydride, and hexachloroendomethylenetetrahydrophthalic anhydride.
Claim 12
Dependent Claim
44 words
An epoxy resin composition according to claim 5, wherein the curing agent (c) is at least one aromatic amine compound selected from the group consisting of m-phenylenediamine, diaminodiphenyl ether, diaminodiphenylmethane, 4,4''-diaminodiphenylmethane-3,3''-dicarbonic acid, diaminodiphenyl sulfone, benzidine, 4,4''-bis(o-toluidine), 4,4''-thiodianiline, dianisidine, methylene-bis(o-chloroaniline), bis(3,4-diaminophenyl) sulfone, and diaminoditolyl sulfone.
Claim 13
Dependent Claim
88 words
An epoxy resin composition comprising (a) 100 parts by weight of an epoxy resin having at least two vicinal epoxy groups, (b) 0.01 to 30 parts by weight of at least one organoboron compound selected from the group consisting of tetraphenyl borates of imidazole and tetraphenylborates of imidazole derivatives obtained by reacting alkali metal salts of tetraphenylboron with at least one member selected from the group consisting of salts of imidazole and salts of imidazole derivatives formed by reacting imidazole or imidazole derivatives represented by the general formula:
Claim 14
Dependent Claim
88 words
An epoxy resin composition comprising (a) 100 parts by weight of an epoxy resin having at least two vicinal epoxy groups, (b) 0.01 to 30 parts by weight of at least one organoboron compound selected from the group consisting of tetraphenyl borates of imidazole and tetraphenylborates of imidazole derivatives obtained by reacting alkali metal salts of tetraphenylboron with at least one member selected from the group consisting of salts of imidazole and salts of imidazole derivatives formed by reacting imidazole or imidazole derivatives represented by the general formula:
Claim 15
Dependent Claim
49 words
An epoxy resin composition according to claim 1, comprising at least one inorganic filler selected from the group consisting of glass, quartz glass, mica, calcium carbonate, calcium sulfate, barium sulfate, alumina, talc, clay, zirconium silicate (zircon), zirconium oxide, lithium aluminum silicate, beryl, aluminum silicate, beryllia, calcium silicate, and silica.
Claim 16
Dependent Claim
51 words
An epoxy resin composition according to claim 3, which further contains at least one inorganic filler selected from the group consisting of glass, quartz glass, mica, calcium carbonate, calcium sulfate, barium sulfate, alumina, talc, clay, zirconium silicate (zircon), zirconium oxide, lithium aluminum silicate, beryl, aluminum silicate, beryllia, calcium silicate, and silica.
Claim 17
Independent Claim
133 words
A method for manufacturing an epoxy resin composition, which comprises bringing a mixture of starting materials into a softened or molten state by heating at 40* to 85*C. and subjecting the softened or molten mixture to a mixing treatment while applying a shearing force, said mixture of the starting materials comprising (a) 100 parts by weight of an epoxy resin having at least two vicinal epoxy groups, (b) 0.01 to 30 parts by weight of at least one organoboron compound selected from the group consisting of tetraphenylborates of imidazole and tetraphenylborates of imidazole derivatives obtained by reacting alkali metal salts of tetraphenylboron with at least one member selected from the group consisting of salts of imidazole and salts of imidazole derivatives formed by reacting imidazole or imidazole derivatives represented by the general formula:
Claim 18
Independent Claim
133 words
A method for manufacturing an epoxy resin composition, which comprises bringing a mixture of starting materials into a softened or molten state by heating at 40* to 85*C. and subjecting the softened or molten mixture to a mixing treatment while applying a shearing force, said mixture of the starting materials comprising (a) 100 parts by weight of an epoxy resin having at least two vicinal epoxy groups, (b) 0.01 to 30 parts by weight of at least one organoboron compound selected from the group consisting of tetraphenylborates of imidazole and tetraphenylborates of imidazole derivatives obtained by reacting alkali metal salts of tetraphenylboron with at least one member selected from the group consisting of salts of imidazole and salts of imidazole derivatives formed by reacting imidazole or imidazole derivatives represented by the general formula:
Claim 19
Dependent Claim
44 words
A method for manufacturing an epoxy resin composition according to claim 14, wherein the epoxy resin (a) is a solid epoxy resin, the curing agent (c) is an amine compound, and the amount of said amine compound is 0.1 to 150 parts by weight.
Claim 20
Dependent Claim
34 words
A method for manufacturing an epoxy resin composition according to claim 14, wherein the mixing treatment is carried out by means of a mixing roll, a Ko-kneader-type extruder, a ribbon mixer, or an extruder.
Claim 21
Dependent Claim
31 words
A method for manufacturing an epoxy resin composition according to claim 14, wherein the epoxy resin (a), the organoboron compound (b), and the curing agent are compounded with an inorganic filler.
References Cited (Backward Citations)
US3793247A
Cited
US3678007A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-09-29 | 1979-03-31 | 1979-09-30 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-09-29 | 1983-03-31 | 1983-09-30 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-09-29 | 1987-03-31 | 1987-09-30 | $7700.00 | Window Closed / Lapsed |