US4593056A
Expired / Lapsed
US
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Epoxy/aromatic amine resin systems containing aromatic trihydroxy compounds as cure accelerators
Assignee: BP Corp North America Inc
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Filing: 1985-06-21
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Granted: 1986-06-03
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Expires: 2005-06-21
Abstract
Abstract Curable thermosetting resin compositions comprising an epoxy resin having at least two 1,2-epoxy groups per molecule, an aromatic diamine hardener, and as a cure accelerator an aromatic trihydroxy compound are disclosed. The aromatic trihydroxy compound, such as for example, phloroglucinol, n-propyl gallate, or pyrogallol, improves the cure speed of the epoxy/aromatic diamine resin system, while at the same time producing cured compositions having excellent mechanical and thermal properties. The disclosed compositions find particular application in the preparation of composites by, e.g., filament winding procedures.
Inventors
- 👤 Shahid P. Qureshi
- 👤 Hugh C. Gardner
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-04 09:14
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/50; C08G59/5033; C08G59/56; C08G59/68
Claims Analysis
Total Claims: 29
Claim 1
Independent Claim
110 words
A curable, thermosetting epoxy composition comprising: (a) an epoxy resin containing at least two 1,2-epoxy groups per molecule; (b) an aromatic diamine hardener in an amount sufficient to provide from about 0.4 to about 2.0 equivalents of amine N--H per equivalent of 1,2-epoxy group in the epoxy resin; and (c) an aromatic trihydroxy cure accelerator of the formula: ##STR10## wherein R is hydrogen, aryl, alkyl, ##STR11## SO 2 R', or SO 2 NHR', and R' is alkyl or aryl of from 1 to 12 carbon atoms, in an amount sufficient to provide from about 0.01 to about 0.35 equivalents of hydroxy per equivalent of 1,2-epoxy groups in the epoxy resin.
Claim 2
Dependent Claim
110 words
A curable, thermosetting epoxy composition comprising: (a) an epoxy resin containing at least two 1,2-epoxy groups per molecule; (b) an aromatic diamine hardener in an amount sufficient to provide from about 0.4 to about 2.0 equivalents of amine N--H per equivalent of 1,2-epoxy group in the epoxy resin; and (c) an aromatic trihydroxy cure accelerator of the formula: ##STR10## wherein R is hydrogen, aryl, alkyl, ##STR11## SO 2 R', or SO 2 NHR', and R' is alkyl or aryl of from 1 to 12 carbon atoms, in an amount sufficient to provide from about 0.01 to about 0.35 equivalents of hydroxy per equivalent of 1,2-epoxy groups in the epoxy resin.
Claim 3
Dependent Claim
17 words
The composition of claim 1, wherein the cure accelerator is phloroglucinol, n-propyl gallate, pyrogallol or mixtures thereof.
Claim 4
Dependent Claim
10 words
The composition claim 2, wherein the cure accelerator is phloroglucinol.
Claim 5
Dependent Claim
12 words
The composition of claim 2, wherein the cure accelerator is n-propyl gallate.
Claim 6
Dependent Claim
11 words
The composition of claim 2, wherein the cure accelerator is pyrogallol.
Claim 7
Dependent Claim
13 words
The composition of claim 2, wherein the epoxy resin is a cycloaliphatic epoxide.
Claim 8
Dependent Claim
52 words
The composition of claim 6, wherein the aromatic diamine hardener is m-phenylenediamine, a eutectic mixture of m-phenylenediamine and 4,4'-diaminodiphenyl methane, 4,4'-diaminediphenyl methane, 4,4'-bis(3-aminophenoxy)-diphenyl sulfone, 2,2-bis[4-(4-aminophenoxy)phenyl]propane, trimethylene glycol di-para-aminobenzoate, 4,4-diaminodiphenyl sulfone, 4,4'-bis(4-aminophenoxy)diphenyl sulfone, adducts of epoxy resins with m-phenylenediamine, 4,4'-bis(4-aminophenoxy)-3,3',5,5'-tetramethyl diphenyl sulfone, 4,4'-bis(4-amino-3-methylphenoxy)diphenyl sulfone, the ring alkylated derivatives of m-phenylenediamine or mixtures thereof.
Claim 9
Dependent Claim
33 words
The composition of claim 6, wherein the aromatic diamine hardener is m-phenylenediamine, the ring alkylated derivatives thereof, adducts of epoxy resins and m-phenylenediamine, eutectic mixtures of m-phenylenediamine and 4,4'-diaminodiphenyl methane, or mixtures thereof.
Claim 10
Dependent Claim
11 words
The composition of claim 6, wherein the cycloaliphatic epoxide is bis(2,3-epoxycyclopentyl)ether.
Claim 11
Dependent Claim
29 words
The composition of claim 6, wherein the cycloaliphatic epoxide is vinylcyclohexene diepoxide, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane meta-dioxane, 3,4-epoxycyclohexyl-methyl 3,4-epoxycyclohexane carboxylate, 3,4-epoxy-6-methylcyclohexylmethyl 3,4-epoxy-6-methylcyclohexane carboxylate, dipentene dioxide, epoxidized polybutadiene, bis(3,4-epoxy cyclohexylmethyl)adipate or mixtures thereof.
Claim 12
Dependent Claim
39 words
The composition of claim 6 wherein the cycloaliphatic epoxide is selected from one or more of: ##STR12## where b is 1 to 4, m is (5-b), and R 2 is H, halogen, or C 1 to C 4 alkyl.
Claim 13
Dependent Claim
17 words
The composition of claim 6, further comprising up to 40 percent by weight of a coepoxy resin.
Claim 14
Dependent Claim
55 words
The composition of claim 12, wherein the coepoxy is selected from one or more of the following: ##STR13## wherein n is from 0 to about 15; ##STR14## wherein n is from 0.1 to about 8 and R is hydrogen; and ##STR15## wherein n is from 0.1 to about 8 and R is CH 3 .
Claim 15
Dependent Claim
17 words
The composition of claim 6, further comprising up to about 20% by weight of a thermoplastic polymer.
Claim 16
Dependent Claim
23 words
The composition of claim 14, wherein said thermoplastic polymer is a polyhdroxyether, a polyetherimide, a polyarylether, a polysulfone, a polycarbonate or mixtures thereof.
Claim 17
Dependent Claim
23 words
The composition of claim 6, further comprising up to 35% by weight of a modifier which increases the modulus of the epoxy resin.
Claim 18
Dependent Claim
45 words
The composition of claims 1, 2, 6, 14 or 16, further comprising a structural fiber having a tensile strength of greater than about 100,000 psi, a tensile modulus of greater than about two million psi, and a decomposition temperature of greater than about 200° C.
Claim 19
Dependent Claim
33 words
The composition of claim 17, wherein said structural fiber is selected from the group consisting of from carbon, graphite, glass, silicon carbide, poly(benzothiazole), poly(benzimidazole), poly(benzoxazole), alumina, titania, boron, aromatic polyamides, and mixtures thereof.
Claim 20
Dependent Claim
11 words
The composition of claim 17 in the form of a composite.
Claim 21
Dependent Claim
138 words
A composite material comprising: (a) a cycloaliphatic epoxide resin containing at least two 1,2-epoxy groups per molecule; (b) an aromatic diamine hardener in an amount sufficient to provide from about 0.4 to 2.0 equivalents of amine N--H per equivalent of 1,2-epoxy groups in the epoxide resin; (c) an aromatic trihydroxy cure accelerator selected from the group consisting of phloroglucinol, n-propyl gallate, pyrogallol and mixtures thereof in an amount sufficient to provide from about 0.01 to about 0.35 equivalents of hydroxy per equivalent of 1,2-epoxy in the epoxide resin; and (d) up to about 85% by weight, based on the total weight of the composition, of a structural fiber having a tensile strength of greater than about 100,000 psi, a tensile modulus of greater than about two million psi, and a decomposition temperature of greater than about 200° C.
Claim 22
Dependent Claim
138 words
A composite material comprising: (a) a cycloaliphatic epoxide resin containing at least two 1,2-epoxy groups per molecule; (b) an aromatic diamine hardener in an amount sufficient to provide from about 0.4 to 2.0 equivalents of amine N--H per equivalent of 1,2-epoxy groups in the epoxide resin; (c) an aromatic trihydroxy cure accelerator selected from the group consisting of phloroglucinol, n-propyl gallate, pyrogallol and mixtures thereof in an amount sufficient to provide from about 0.01 to about 0.35 equivalents of hydroxy per equivalent of 1,2-epoxy in the epoxide resin; and (d) up to about 85% by weight, based on the total weight of the composition, of a structural fiber having a tensile strength of greater than about 100,000 psi, a tensile modulus of greater than about two million psi, and a decomposition temperature of greater than about 200° C.
Claim 23
Dependent Claim
11 words
The composite of claim 20, wherein the cycloaliphatic epoxide is bis(2,3-epoxycyclopentyl)ether.
Claim 24
Dependent Claim
29 words
The composite of claim 20, wherein the cycloaliphatic epoxide is vinylcyclohexene diepoxide, 2-(3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy)cyclohexane meta-dioxane, 3,4-epoxycyclohexylmethyl 3,4-epoxycyclohexane carboxylate, 3,4-epoxy-6-methylcyclohexylmethyl 3,4-epoxy-6-methylcyclohexane carboxylate, dipentene dioxide, epoxidized polybutadiene, bis(3,4-epoxy cyclohexylmethyl)adipate or mixtures thereof.
Claim 25
Dependent Claim
39 words
The composite of claim 20, wherein the cycloaliphatic epoxide is selected from one or more of: ##STR16## where b is 1 to 4, m is (5-b), and R 2 is H, halogen, or C 1 to C 4 alkyl.
Claim 26
Dependent Claim
36 words
The composite of claims 21, 22 or 23, wherein the aromatic diamine hardener is m-phenylenediamine, the ring alkylated derivatives thereof, adducts of epoxy resins and m-phenylenediamine, eutectic mixtures of m-phenylenediamine and 4,4'-diaminodiphenyl methane, or mixtures thereof.
Claim 27
Dependent Claim
32 words
The composite of claim 24, further comprising up to about 40 percent by weight of a coepoxy resin, based on the combined weight of the cycloaliphatic epoxide resin and the coepoxy resin.
Claim 28
Dependent Claim
36 words
The composite of claim 24, further comprising up to about 35% by weight, based upon the total weight of the resinous portion of the composite, of a modifier which increases the modulus of the epoxy resin.
Claim 29
Dependent Claim
29 words
The composite of claim 24, further comprising up to about 20% by weight, based upon the total weight of the resinous portion of the composite, of a thermoplastic polymer.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-06-02 | 1989-12-02 | 1990-06-03 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-06-02 | 1993-12-02 | 1994-06-03 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-06-02 | 1997-12-02 | 1998-06-03 | $7700.00 | Window Closed / Lapsed |