US4608404A
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Epoxy compositions containing oligomeric diamine hardeners and high strength composites therefrom
Assignee: BP Corp North America Inc
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Filing: 1985-05-02
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Granted: 1986-08-26
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Expires: 2005-05-02
Abstract
Abstract Described herein are compositions which contain a specific group of oligomeric diamine hardeners and epoxy compounds which when combined with structural fibers produce composites which have improved tensile properties, high compressive strengths, and improved impact resistance. These compositions also exhibit low moisture absorption.
Inventors
- 👤 Hugh C. Gardner
- 👤 George L. Brode
- 👤 Robert J. Cotter
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 08:49
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/50; C08G59/504; C08L; C08L63/00
Claims Analysis
Total Claims: 44
Claim 1
Independent Claim
67 words
A composition comprising: (a) a diamine hardener represented by the following general formulas: ##STR18## or mixtures thereof, wherein X is O, S, SO or SO 2 , Y is O or S, A is the residuum of a dihalobenzenoid compound, R is the residuum of a dihydric phenol and a is 0.05 to 20, and (b) an epoxy resin containing two or more 1,2-epoxide groups per molecule.
Claim 2
Dependent Claim
67 words
A composition comprising: (a) a diamine hardener represented by the following general formulas: ##STR18## or mixtures thereof, wherein X is O, S, SO or SO 2 , Y is O or S, A is the residuum of a dihalobenzenoid compound, R is the residuum of a dihydric phenol and a is 0.05 to 20, and (b) an epoxy resin containing two or more 1,2-epoxide groups per molecule.
Claim 3
Dependent Claim
26 words
A composition as defined in claim 1 wherein R is selected from bisphenol A, hydroquinone, resorcinol, 4,4'-biphenol, 4,4'-dihydroxydiphenyl sulfone, 4,4'-dihydroxydiphenyl sulfide, 4,4'-dihydroxy-3,3',5,5'-tetramethyldiphenyl sulfide, and 4,4-dihydroxy-3,3',5,5'-tetramethyldiphenyl sufone.
Claim 4
Dependent Claim
45 words
A composition as defined in claim 1 wherein A is selected from: ##STR19## wherein B is SO 2 , ##STR20## --C(CH 3 ) 2 , --C(CF 3 ) 2 or a direct bond, Z is halogen and b is an integer of 1 to 4.
Claim 5
Dependent Claim
21 words
A composition as defined in claim 1 wherein the diamine is of the formula: ##STR21## wherein c is 0.2 to 0.8.
Claim 6
Dependent Claim
21 words
A composition as defined in claim 1 wherein the diamine is of the formula: ##STR22## wherein c is 0.2 to 0.8.
Claim 7
Dependent Claim
21 words
A composition as defined in claim 1 wherein the diamine is of the formula: ##STR23## wherein c is 0.2 to 0.8.
Claim 8
Dependent Claim
21 words
A composition as defined in claim 1 wherein the diamine is of the formula: ##STR24## wherein c is 0.2 to 0.8.
Claim 9
Dependent Claim
13 words
A composition as defined in claim 1 wherein the epoxy resin is bis(2,3-epoxycyclopentyl)ether.
Claim 10
Dependent Claim
28 words
A composition as defined in claim 1 wherein the epoxy resin is of the following structure: ##STR25## where n has a value from about 0 to about 15.
Claim 11
Dependent Claim
26 words
A composition as defined in claim 1 wherein the epoxy resin is a phenol-formaldehyde novolak of the following formula: ##STR26## wherein n=0.1 to 8 and R=hydrogen.
Claim 12
Dependent Claim
30 words
A composition as defined in claim 1 wherein the epoxy resin is a cresol-formaldehyde novolak of the following formula: ##STR27## wherein n=0.1 to 8 and R is CH 3 .
Claim 13
Dependent Claim
14 words
A composition as defined in claim 1 wherein the epoxy resin is N,N,N'N'-tetraglycidyl-4,4'-diaminodiphenyl methane.
Claim 14
Dependent Claim
14 words
A composition as defined in claim 1 wherein the epoxy resin is N,N,N',N'-tetraglycidylxylylene diamine.
Claim 15
Dependent Claim
14 words
A composition as defined in claim 1 wherein the epoxy resin is N,N-diglycidyl toluidene.
Claim 16
Dependent Claim
14 words
A composition as defined in claim 1 wherein the epoxy resin is N,N-diglycidyl aniline.
Claim 17
Dependent Claim
13 words
A composition as defined in claim 1 wherein the epoxy resin is N,N,N',N'-tetraglycidylbis(methylamino)cyclohexane.
Claim 18
Dependent Claim
14 words
A composition as defined in claim 1 wherein the epoxy resin is diglycidyl isophthalate.
Claim 19
Dependent Claim
14 words
A composition as defined in claim 1 wherein the epoxy resin is diglycidyl terephthalate.
Claim 20
Dependent Claim
16 words
A composition as defined in claim 1 wherein the epoxy resin is O,N,N-triglycidyl-4-amino phenol or O,N,N-triglycidyl-3-aminophenol.
Claim 21
Dependent Claim
15 words
A composition as defined in claim 1 wherein the epoxy resin is 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexane carboxylate.
Claim 22
Dependent Claim
17 words
A composition as defined in claim 1 wherein the epoxy resin is a N,N'-diglycidyl derivative of dimethylhydantoin.
Claim 23
Dependent Claim
28 words
A composition as defined in claim 1 which contains a structural fiber selected from carbon, graphite, glass, silicon carbide, poly(benzothiazole), poly(benzimidazole), poly(benzoxazole), alumina, titania, boron, and aromatic polyamides.
Claim 24
Dependent Claim
14 words
A composition as defined in claim 1 or 22 which contains a thermoplastic polymer.
Claim 25
Dependent Claim
69 words
A composition as defined in claim 23 wherein the thermoplastic polymer is selected from one or more of a poly(aryl ether), a polyhydroxyether, a polycarbonate, a poly(ε-caprolactone), a polybutadiene/acrylonitrile copolymer, a polyester, an acrylonitrile/butadiene/styrene copolymer, a polyamide, a poly(amide imide), a polyolefin, a polyethylene oxide, a polybutyl methacrylate, an impact-modified polystyrene, a sulfonated polyethylene, a polyacrylate, poly(2,6-dimethyl phenylene oxide), polyvinyl chloride and its copolymers, polyphenylene sulfide and a polyacetal.
Claim 26
Dependent Claim
14 words
A composition as defined in claim 24 wherein the thermoplastic polymer is a polysulfone.
Claim 27
Dependent Claim
14 words
A composition as defined in claim 24 wherein the thermoplastic polymer is a polyhydroxyether.
Claim 28
Dependent Claim
14 words
A composition as defined in claim 24 wherein the thermoplastic polymer is a polycarbonate).
Claim 29
Dependent Claim
14 words
A composition as defined in claim 24 wherein the thermoplastic polymer is a polyetherimide.
Claim 30
Dependent Claim
14 words
A composition as defined in claim 24 wherein the thermoplastic polymer is a polyarylate.
Claim 31
Dependent Claim
21 words
A composition as defined in claims 1 or 22 or 24 which contains an accelerator which increases the rate of cure.
Claim 32
Dependent Claim
17 words
A composition as defined in claim 1 which contains 5 to 70 weight percent of component (a).
Claim 33
Dependent Claim
17 words
A composition as defined in claim 1 which contains 5 to 75 weight percent of component (b).
Claim 34
Dependent Claim
57 words
A composition comprising: (a) a diamine hardener represented by the following general formulas: ##STR28## or mixtures thereof, wherein X is O, S, SO or SO 2 , Y is O or S, A is the residuum of a dihalobenzenoid compound, R is the residuum of a dihydric phenol, and a is 0.05 to 20 and (b) bis(2,3-epoxycyclopentyl)ether.
Claim 35
Dependent Claim
57 words
A composition comprising: (a) a diamine hardener represented by the following general formulas: ##STR28## or mixtures thereof, wherein X is O, S, SO or SO 2 , Y is O or S, A is the residuum of a dihalobenzenoid compound, R is the residuum of a dihydric phenol, and a is 0.05 to 20 and (b) bis(2,3-epoxycyclopentyl)ether.
Claim 36
Dependent Claim
15 words
A composition as defined in claim 33 which contains a structural fiber and/or thermoplastic polymer.
Claim 37
Dependent Claim
72 words
A prepreg comprising: (a) a diamine hardener represented by the following general formulas: ##STR29## or mixtures thereof, wherein X is O, S, SO or SO 2 , Y is O or S, A is the residuum of a dihalobenzenoid compound, R is the residuum of a dihydric phenol, and a is 0.05 to 20 and (b) an epoxy resin containing two or more 1,2-epoxide groups per molecule and (c) a structural fiber.
Claim 38
Dependent Claim
72 words
A prepreg comprising: (a) a diamine hardener represented by the following general formulas: ##STR29## or mixtures thereof, wherein X is O, S, SO or SO 2 , Y is O or S, A is the residuum of a dihalobenzenoid compound, R is the residuum of a dihydric phenol, and a is 0.05 to 20 and (b) an epoxy resin containing two or more 1,2-epoxide groups per molecule and (c) a structural fiber.
Claim 39
Dependent Claim
17 words
A prepreg as defined in claim 35 which contains an accelerator which increases the rate of cure.
Claim 40
Dependent Claim
14 words
A prepreg as defined in claims 35 or 36 which contains a thermoplastic polymer.
Claim 41
Dependent Claim
76 words
A composite comprising: (i) a matrix resin comprising (a) a diamine hardener represented by the following formulas: ##STR30## or mixtures thereof, wherein X is O, S, SO or SO 2 , Y is O or S, A is the residuum of a dihalobenzenoid compound, R is the residuum of a dihydric phenol, and a is 0.05 to 20 and (b) an epoxy resin containing two or more 1,2-epoxide groups per molecule, and (c) a structural fiber.
Claim 42
Dependent Claim
76 words
A composite comprising: (i) a matrix resin comprising (a) a diamine hardener represented by the following formulas: ##STR30## or mixtures thereof, wherein X is O, S, SO or SO 2 , Y is O or S, A is the residuum of a dihalobenzenoid compound, R is the residuum of a dihydric phenol, and a is 0.05 to 20 and (b) an epoxy resin containing two or more 1,2-epoxide groups per molecule, and (c) a structural fiber.
Claim 43
Dependent Claim
25 words
A composite as defined in claim 38 wherein the epoxy resin was cured in the presence of an accelerator which increased the rate of cure.
Claim 44
Dependent Claim
14 words
A composite as defined in claims 38 or 39 which contains a thermoplastic polymer.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-08-25 | 1990-02-24 | 1990-08-26 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-08-25 | 1994-02-24 | 1994-08-26 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-08-25 | 1998-02-24 | 1998-08-26 | $7700.00 | Window Closed / Lapsed |