Patent US4002599A successfully refreshed from Google Patents.
US4002599A
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Epoxy resin compositions from glycidyl derivatives of aminophenols cured with tetracarboxylic dianhydrides
Assignee: Lord Corp
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Filing: 1975-11-06
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Granted: 1977-01-11
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Expires: 1995-11-06
Abstract
Abstract Disclosed are epoxy resin compositions comprising at least one polyglycidyl derivative of an aminophenol having the structure ##STR1## and at least one biphenyl anhydride having the structure ##STR2## wherein m is 1 or 2; wherein A is selected from the group consisting of ##STR3## WHEREIN EACH R o is individually a monovalent radical selected from the group consisting of hydrogen, halogen, hydroxy, alkyl radical having from 1 to 5 carbon atoms, alkoxy radical having from 1 to 5 carbon atoms and ##STR4## wherein R 1 is an alkyl radical having from 1 to 5 carbon atoms; and wherein each R 2 is individually a monovalent radical selected from the group consisting of hydrogen, halogen, alkyl radical having from 1 to 5 carbon atoms, --NO 2 , --COOH --SO 3 H, and --NH 2 . The compositions are useful in such applications as molding resins, laminates, adhesives, coatings, and the like. The disclosed epoxy resin-anhydride systems can be cured at ambient temperatures to afford products having useful properties at high temperature.
Inventors
- 👤 James A. Graham
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 11:43
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/50; C08G59/52; C08G59/20; C08G59/32; C08G59/3227; C08G59/42; C08G59/4223; Y; Y10; Y10S; Y10S525/00; Y10S525/939
Claims Analysis
Total Claims: 42
Claim 1
Independent Claim
146 words
A room temperature stable two-pack epoxy resin system consisting essentially of a. a first pack comprising at least one polyglycidyl aminophenol having the structure ##STR11## wherein m is 1 or 2; and b. a second pack comprising at least one biphenyl anhydride having the structure ##STR12## wherein A is selected from the group consisting of ##STR13## wherein each R 0 is individually a monovalent radical selected from the group consisting of hydrogen, halogen, hydroxy, alkyl radical having from 1 to 5 carbon atoms, alkoxy radical having from 1 to 5 carbon atoms and ##STR14## wherein R 1 is an alkyl radical having from 1 to 5 carbon atoms; and wherein each R 2 is individually a monovalent radical selected from the group consisting of hydrogen, halogen, alkyl radical having from 1 to 5 carbon atoms, --NO 2 , --COOH, --SO 3 H, and --NH 2 .
Claim 2
Dependent Claim
146 words
A room temperature stable two-pack epoxy resin system consisting essentially of a. a first pack comprising at least one polyglycidyl aminophenol having the structure ##STR11## wherein m is 1 or 2; and b. a second pack comprising at least one biphenyl anhydride having the structure ##STR12## wherein A is selected from the group consisting of ##STR13## wherein each R 0 is individually a monovalent radical selected from the group consisting of hydrogen, halogen, hydroxy, alkyl radical having from 1 to 5 carbon atoms, alkoxy radical having from 1 to 5 carbon atoms and ##STR14## wherein R 1 is an alkyl radical having from 1 to 5 carbon atoms; and wherein each R 2 is individually a monovalent radical selected from the group consisting of hydrogen, halogen, alkyl radical having from 1 to 5 carbon atoms, --NO 2 , --COOH, --SO 3 H, and --NH 2 .
Claim 3
Dependent Claim
26 words
An epoxy resin system according to claim 1 wherein the overall ratio of anhydride equivalents to epoxide equivalents is in the range of 0.2 - 1.3:1.
Claim 4
Dependent Claim
56 words
An epoxy resin system according to claim 2 wherein said second pack has incorporated therein at least one other carboxylic anhydride epoxy curing agent, said other anhydride is not a biphenyl anhydride; of the structure of claim 1 and wherein at least about 40 percent of the total anhydride equivalents is provided by said biphenyl anhydride.
Claim 5
Dependent Claim
12 words
An epoxy resin system according to claim 1 wherein A is ##STR15##
Claim 6
Dependent Claim
12 words
An epoxy resin system according to claim 2 wherein A is ##STR16##
Claim 7
Dependent Claim
23 words
An epoxy resin system according to claim 5 wherein said anhydride: epoxy ratio of equivalents is in the range of 0.55 - 1.1:1.
Claim 8
Dependent Claim
12 words
An epoxy resin system according to claim 6 wherein m is 1.
Claim 9
Dependent Claim
37 words
An epoxy resin system according to claim 7 wherein said polyglycidyl aminophenol is triglycidyl p-aminophenol, said biphenyl anhydride is 3,3',4,4'-benzophenone tetacarboxylic dianhydride, and the ratio of anhydride equivalents to epoxide equivalents is in the range of 0.6-0.95:1.
Claim 10
Dependent Claim
15 words
An epoxy resin system according to claim 3 wherein said other anhydride is maleic anhydride.
Claim 11
Dependent Claim
12 words
An epoxy resin system according to claim 9 wherein A is ##STR17##
Claim 12
Dependent Claim
38 words
An epoxy resin system according to claim 9 wherein said polyglycidyl aminophenol is triglycidyl p-aminophenol, said biphenyl anhydride is 3,3',4,4'-benzophenone tetracarboxylic dianhydride, and the overall ratio of anhydride equivalents to epoxide equivanents is in the range of 0.6-0.95:1.
Claim 13
Dependent Claim
47 words
An epoxy resin system according to claim 2 wherein said first pack has incorporated therein at least one other epoxy resin, said other epoxy resin is not a polyglycidyl aminophenol; and wherein at least about 50 percent of said epoxide equivalents is provided by said polyglydicyl aminophenol.
Claim 14
Dependent Claim
12 words
An epoxy resin system according to claim 12 wherein A is ##STR18##
Claim 15
Dependent Claim
56 words
An epoxy resin system according to claim 13 wherein said polyglycidyl aminophenol is triglycidyl p-aminophenol; said biphenyl anhydride is 3,3',4,4'-benzophenone tetracarboxylic dianhydride; said other epoxy resin is selected from the group consisting of epoxypolyethers, polyepoxypolyhydroxypolyethers and epoxy novolaks; and the overall ratio of anhydride equivalents to epoxide equivalents is in the range of 0.6 - 0.95:1.
Claim 16
Dependent Claim
48 words
An epoxy resin system according to claim 3 wherein said first pack has incorporated therein at least one other epoxy resin, said other epoxy resin is not a polyglycidyl aminophenol; and wherein at least about 50 percent of said epoxide equivalents is provided by said polyglycidyl amino phenol.
Claim 17
Dependent Claim
12 words
An epoxy resin system according to claim 15 wherein A is ##STR19##
Claim 18
Dependent Claim
62 words
An epoxy resin system according to claim 16 wherein said polyglycidyl aminophenol is triglycidyl p-aminophenol; said biphenyl anhydride is 3,3',4,4'-benzophenone tetracarboxylic dianhydride; said other epoxy resin is selected from the group consisting of epoxypolyethers, polyepoxypolyhydroxypolyethers, and epoxy novolaks; said other anhydride is maleic anhydride; and the overall ratio of anhydride equivalents to epoxide equivalents is in the range of 0.6 - 0.95:1.
Claim 19
Dependent Claim
158 words
An epoxy resin composition comprising the admixture of i. at least one polyglycidyl aminophenol epoxy resin having the structure ##STR20## wherein m is 1 or 2; and ii. at least one biphenyl anhydride having the structure ##STR21## wherein A is selected from the group consisting of ##STR22## wherein each R is individually a monovalent radical selected from the group consisting of hydrogen, halogen, hydroxy, alkyl radical having from 1 to 5 carbon atoms, alkoxy radical having from p to 5 carbon atoms, and ##STR23## wherein R is an alkyl radical having from 1 to 5 carbon atoms; and wherein each R is individually a monovalent radical selected from the group consisting of hydrogen, halogen, alkyl radical having 1 to 5 carbon atoms, --NO 2 --COOH, --SO 3 H, and --NH 2; said composition having a ratio of anhydride equivalents to epoxide equivalents in the range of 0.2 - 1.3:1; said composition being adapted to cure at room temperature.
Claim 20
Dependent Claim
158 words
An epoxy resin composition comprising the admixture of i. at least one polyglycidyl aminophenol epoxy resin having the structure ##STR20## wherein m is 1 or 2; and ii. at least one biphenyl anhydride having the structure ##STR21## wherein A is selected from the group consisting of ##STR22## wherein each R is individually a monovalent radical selected from the group consisting of hydrogen, halogen, hydroxy, alkyl radical having from 1 to 5 carbon atoms, alkoxy radical having from p to 5 carbon atoms, and ##STR23## wherein R is an alkyl radical having from 1 to 5 carbon atoms; and wherein each R is individually a monovalent radical selected from the group consisting of hydrogen, halogen, alkyl radical having 1 to 5 carbon atoms, --NO 2 --COOH, --SO 3 H, and --NH 2; said composition having a ratio of anhydride equivalents to epoxide equivalents in the range of 0.2 - 1.3:1; said composition being adapted to cure at room temperature.
Claim 21
Dependent Claim
12 words
An epoxy resin composition according to claim 18 wherein A is ##STR24##
Claim 22
Dependent Claim
15 words
An epoxy resin composition according to claim 18 wherein said polyglycidyl aminophenol is triglycidyl p-aminophenol.
Claim 23
Dependent Claim
16 words
An epoxy resin composition according to claim 20 wherein said biphenyl anhydride is 3,3',4,4'-benzophenone tetracarboxylic dianhydride.
Claim 24
Dependent Claim
35 words
An epoxy resin composition according to claim 18 having incorporated therein at least one other and different epoxy resin, wherein at least 50 percent of the total epoxide equivalents is provided by said polyglycidyl aminophenol.
Claim 25
Dependent Claim
12 words
An epoxy resin composition according to claim 22 wherein A is ##STR25##
Claim 26
Dependent Claim
27 words
An epoxy resin composition according to claim 23 wherein said other and different epoxy resin is selected from the group consisting of epoxypolyethers, polyepoxypolyhdroxypolyethers and epoxy novolaks.
Claim 27
Dependent Claim
15 words
An epoxy resin composition according to claim 24 wherein said polyglycidyl aminophenol is triglycidyl p-aminophenol.
Claim 28
Dependent Claim
31 words
An epoxy resin composition according to claim 25 wherein said biphenyl anhydride is 3,3',4,4'-benzophenone tetracarboxylic dianhydride and said ratio of anhydride equivalents to epoxide equivalents is in the range of 0.6-0.95:1.
Claim 29
Dependent Claim
36 words
An epoxy resin composition according to claim 18 having incorporated therein at least one other and different carboxylic anhydride, and wherein at least 40 percent of the total anhydride equivalents is provided by said biphenyl anhydride.
Claim 30
Dependent Claim
12 words
An epoxy resin composition according to claim 27 wherein A is ##STR26##
Claim 31
Dependent Claim
17 words
An epoxy resin composition according to claim 28 wherein said other and different anhydride is maleic anhydride.
Claim 32
Dependent Claim
15 words
An epoxy resin composition according to claim 29 wherein said polyglycidyl aminophenol is triglycidyl p-aminophenol.
Claim 33
Dependent Claim
33 words
An epoxy resin composition according to claim 30 wherein said biphenyl anhydride is 3,3',4,4'-benzophenone tetracarboxylic dianhydride and said ratio of anhydride equivalents to epoxide equivalents is in the range of 0.6 - 0.95:1.
Claim 34
Dependent Claim
36 words
An epoxy resin composition according to claim 22 having incorporated therein at least one other and different carboxylic anhydride, and wherein at least 40 percent of the total anhydride equivalents is provided by said biphenyl anhydride.
Claim 35
Dependent Claim
12 words
An epoxy resin composition according to claim 32 wherein A is ##STR27##
Claim 36
Dependent Claim
17 words
An epoxy resin composition according to claim 33 wherein said other and different anhydride is maleic anhydride.
Claim 37
Dependent Claim
26 words
An epoxy composition according to claim 33 wherein said other and different epoxy resin is selected from the group consisting of epoxypolyethers, polyepoxypolyhydroxypolyethers and epoxy novolaks.
Claim 38
Dependent Claim
17 words
An epoxy resin composition according to claim 35 wherein said other and different anhydride is maleic anhydride.
Claim 39
Dependent Claim
15 words
An epoxy resin composition according to claim 35 wherein said polyglycidyl aminophenol is triglycidyl p-aminophenol.
Claim 40
Dependent Claim
17 words
An epoxy resin composition according to claim 37 wherein said other and different anhydride is maleic anhydride.
Claim 41
Dependent Claim
32 words
An epoxy composition according to claim 37 wherein said biphenyl anhydride is 3,3',4,4'-benzophenone tetracarboxylic dianhydride and said ratio of anhydride equivalents to epoxide equivalents is in the range of 0.6 - 0.95:1.
Claim 42
Dependent Claim
17 words
An epoxy resin composition according to claim 39 wherein said other and different anhydride is maleic anhydride.
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) | 1980-01-11 | 1980-07-12 | 1981-01-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-01-11 | 1984-07-12 | 1985-01-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-01-11 | 1988-07-12 | 1989-01-11 | $7700.00 | Window Closed / Lapsed |