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US4680341A
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Epoxy resins based on tetraglycidyl diamines
Assignee: BP Corp North America Inc
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Filing: 1986-04-17
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Granted: 1987-07-14
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Expires: 2006-04-17
Abstract
Abstract Novel 3-ring tetraglycidates having the formula ##STR1## wherein X=O, S, ##STR2## --CH 2 --, C═O; Y=halogen, C 1 -C 4 alkyl; and p0 n=0 to 4, are disclosed Epoxy resin systems exhibiting good tensile properties and moisture sensitivity can be made by copolymerizing the tetraglycidates with a polyamine curing agent. Prepregs can be made by combining the epoxy resin systems with a fiber reinforcement. The epoxy resin system may include a co-epoxide.
Inventors
- 👤 Richard H. Newman-Evans
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 00:03
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/50; C07; C07D; C07D303/00; C07D303/02; C07D303/36; C08G59/20; C08G59/32; C08G59/3227; C08G59/38; C08L; C08L63/00
Claims Analysis
Total Claims: 35
Claim 1
Independent Claim
24 words
A tetraglycidate of the formula ##STR23## wherein X=O, S, ##STR24## --CH 2 --, C═O; Y=halogen, C 1 -C 4 alkyl; and n=0 to 4.
Claim 2
Dependent Claim
24 words
A tetraglycidate of the formula ##STR23## wherein X=O, S, ##STR24## --CH 2 --, C═O; Y=halogen, C 1 -C 4 alkyl; and n=0 to 4.
Claim 3
Dependent Claim
35 words
Epoxy resin systems comprising (a) a tetraglycidate of the formula ##STR25## wherein X=O, S, ##STR26## --CH 2 --, C═O; Y=halogen, C 1 -C 4 alkyl; and n=0 to 4; and (b) a polyamine curing agent.
Claim 4
Dependent Claim
35 words
Epoxy resin systems comprising (a) a tetraglycidate of the formula ##STR25## wherein X=O, S, ##STR26## --CH 2 --, C═O; Y=halogen, C 1 -C 4 alkyl; and n=0 to 4; and (b) a polyamine curing agent.
Claim 5
Dependent Claim
26 words
An epoxy resin system as defined in claim 2, wherein said polyamine is selected from the group consisting of aliphatic polyamines and polyamines containing benzenoid unsaturation.
Claim 6
Dependent Claim
27 words
An epoxy resin system as defined in claim 3, wherein said aliphatic polyamine is selected from the group consisting of diethylene triamine, triethylene tetraamine, and tetraethylene pentaamine.
Claim 7
Dependent Claim
39 words
An epoxy resin system as defined in claim 3, wherein said polyamine containing benzenoid unsaturation is selected from the group consisting of m-phenylenediamine, p-phenylenediamine, 1,6-diaminonaphthalene, 4,4'-diaminodiphenyl methane, 4,4'-diaminodiphenyl ether, sulfanilamide, 3-methyl-4-aminobenzamide, 4,4'-diaminodiphenyl sulfone, 4,4'-diaminodiphenyl, and alkylated derivatives of m-phenylenediamine.
Claim 8
Dependent Claim
57 words
An epoxy resin system as defined in claim 2, wherein said polyamine has the formula ##STR27## wherein: a is 2 or 3; R 3 is hydrogen, alkyl of 1 to 8 carbon atoms or aryl of 6 to 18 carbon atoms; and X is a divalent or trivalent organic hydrocarbon, hetero-interrupted hydrocarbon, substituted hydrocarbon radical, or --N--.
Claim 9
Dependent Claim
86 words
An epoxy resin system as defined in claim 6, wherein R 3 is hydrogen, alkyl of 1 to 3 carbon atoms, or phenyl; and X is a divalent or trivalent radical selected from (1) divalent groups consisting of --(CH 2 ) 4 -- wherein y is an integer of from 2 to 12, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 -- ##STR28## (2) trivalent groups of the formula ##STR29## and --(CH.sub.2).sub.n --CH--(CH.sub.2).sub.m -- wherein n and m are the same or different integers from 1 to 4.
Claim 10
Dependent Claim
84 words
An epoxy resin system as defined in claim 2, wherein said polyamine is selected from the group consisting of (i) 4,4'-diaminodiphenyl sulfone, (ii) diamines having the formula ##STR30## wherein each of the two amino groups is meta or para to the carbonyl group bonded to the same ring and wherein Y is --(CH.sub.2).sub.q -- wherein q is an integer from 2 to 12, --CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 --, ##STR31## wherein t is an integer of from 0 to about 5, and ##STR32##
Claim 11
Dependent Claim
18 words
An epoxy resin system as defined in claim 8, wherein q is from about 2 to about 6.
Claim 12
Dependent Claim
13 words
An epoxy resin system as defined in claim 9 wherein q is 3.
Claim 13
Dependent Claim
39 words
An epoxy resin system as defined in claim 2, wherein said polyamine curing agent is mixed with said tetraglycidate in an amount which provides about 0.3 to about 2.0 moles of amine hydrogen for each mole of epoxy groups.
Claim 14
Dependent Claim
28 words
An epoxy resin system as defined in claim 11, wherein said amount provides about 0.4 to about 1.7 moles of amine hydrogen for each mole of epoxy groups.
Claim 15
Dependent Claim
28 words
An epoxy resin system as defined in claim 12, wherein said amount provides about 0.45 to about 1.3 moles of amine hydrogen for each mole of epoxy groups.
Claim 16
Dependent Claim
13 words
An epoxy resin system as defined in claim 2, further comprising a co-epoxide.
Claim 17
Dependent Claim
30 words
An epoxy resin system as defined in claim 14, wherein said co-epoxide is present in an amount up to about 40 wt. percent based on the total amount of tetraglycidate.
Claim 18
Dependent Claim
29 words
An epoxy resin system as defined in claim 15, wherein said co-epoxide is present in an amount up to about 30 wt. percent of the total amount of tetraglycidate.
Claim 19
Dependent Claim
27 words
An epoxy resin system as defined in claim 14, wherein said co-epoxide has the structure ##STR33## where n has a value from about 0 to about 15.
Claim 20
Dependent Claim
20 words
An epoxy resin system as defined in claim 17, wherein n has a value from about 0 to about 10.
Claim 21
Dependent Claim
20 words
An epoxy resin system as defined in claim 14, wherein said co-epoxide is a polyepoxide which is a polyglycidyl ether.
Claim 22
Dependent Claim
36 words
An epoxy resin system as defined in claim 19, wherein said co-epoxide is a polyepoxide selected from the group consisting of polyglycidyl ethers of 4,4'-dihydroxydiphenyl methane, 4,4'-dihydroxydiphenyl sulfone, 4,4'-biphenol, 4,4'-dihydroxydiphenyl sulfide, phenolphthalein, resorcinol, 4,2'-biphenol, and tris(4-hydroxyphenyl)methane.
Claim 23
Dependent Claim
24 words
An epoxy resin system as defined in claim 14, wherein said co-epoxide is a polyglycidyl derivative of a phenol-formaldehyde novolak or a cresol-formaldehyde novolak.
Claim 24
Dependent Claim
30 words
An epoxy resins system as defined in claim 21, wherein said phenol-formaldehyde novolak has the structure XI and said cresol-formaldehyde novolak has the structure XII ##STR34## where n=0.1 to 8.
Claim 25
Dependent Claim
25 words
An epoxy resin system as defined in claim 14, wherein said co-epoxide is a polyglycidyl adduct of an amine, an aminoalcohol, or a polycarboxylic acid.
Claim 26
Dependent Claim
38 words
An epoxy resin system as defined in claim 23, wherein said polyglycidyl adduct of an amine is selected from the group consisting of N,N-diglycidyl aniline, N,N-diglycidyl toluidine, N,N,N',N'-tetraglycidylxylylene diamine, N,N,N',N'-tetraglycidyl-bis(methylamino) cyclohexane, N,N,N',N'-tetraglycidyl-4,4'-methylene dianiline, N,N,N',N'-tetraglycidyl-3,3'-diaminodiphenyl sulfone, and N,N'-dimethyl-N,N'-diglycidyl-4,4'-diaminodiphenyl methane.
Claim 27
Dependent Claim
20 words
An epoxy resin system as defined in claim 23, wherein said polyglycidyl adduct of an aminoalcohol is O,N,N-triglycidyl-3-aminophenol or O,N,N-triglycidyl-4-aminophenol.
Claim 28
Dependent Claim
21 words
An epoxy resin system as defined in claim 23, wherein said polyglycidyl adduct of a polycarboxylic acid is a glycidyl ester.
Claim 29
Dependent Claim
29 words
An epoxy resin system as defined in claim 26, wherein said glycidyl ester is selected from the group consisting of diglycidyl phthalate, diglycidyl terephthalate, diglycidyl isophthalate, and diglycidyl adipate.
Claim 30
Dependent Claim
40 words
An epoxy resin system as defined in claim 14, wherein said co-epoxide is selected from the group consisting of triglycidyl cyanurates and isocyanurates, N,N-diglycidyl oxamides, N,N'-diglycidyl derivatives of hydantoins, diglycidyl esters of cycloaliphatic dicarboxylic acids, and polyglycidyl thioethers of polythiols.
Claim 31
Dependent Claim
29 words
An epoxy resin system as defined in claim 14, wherein said co-epoxide is a copolymer of an acrylic acid ester of glycidol with one or more copolymerizable vinyl compounds.
Claim 32
Dependent Claim
19 words
An epoxy resin system as defined in claim 14, wherein said co-epoxide is a silicone resin containing epoxy functionality.
Claim 33
Dependent Claim
23 words
An epoxy resin system as defined in claim 14, wherein said co-epoxide is an epoxy resin prepared by epoxidation of dienes or polyenes.
Claim 34
Dependent Claim
14 words
An epoxy resin system as defined in claim 14, wherein said co-epoxide is cycloaliphatic.
Claim 35
Dependent Claim
18 words
An epoxy resin system as defined in claim 2, further comprising a thermoplastic polymer, polymer blend, or elastomer.
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) | 1990-07-13 | 1991-01-12 | 1991-07-14 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1994-07-13 | 1995-01-12 | 1995-07-14 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1998-07-13 | 1999-01-12 | 1999-07-14 | $7700.00 | Window Closed / Lapsed |