US4618526A
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US
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Curable compositions containing multiglycidyl ethers and a sulfonic acid amide
Assignee: Dow Chemical Co
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Filing: 1985-07-22
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Granted: 1986-10-21
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Expires: 2005-07-22
Abstract
Abstract Curable compositions are disclosed which comprise a multiglycidyl ether such as the triglycidylether of tris(hydroxyphenyl)methane and an amine substituted sulfonic acid amide such as sulfanilamide. These compositions can be cured by heating in the presence or absence of an accelerator such as 2-methyl imidazole. These compositions are particularly useful in the preparation of electrical laminates.
Inventors
- 👤 Jody R. Berman
- 👤 Dennis L. Steele
- 👤 Michael P. Kubisiak
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 01:04
CPC Classifications
C; C08; C08G; C08G59/00; C08G59/18; C08G59/40; C08G59/44; C08G59/444; C08G59/20; C08G59/32; C08G59/3218; H; H05; H05K; H05K1/00; H05K1/02; H05K1/03; H05K1/0313; H05K1/032; H05K1/0326; Y; Y10; Y10S; Y10S428/00; Y10S428/901; Y10T; Y10T428/00; Y10T428/24; Y10T428/24802; Y10T428/24917; Y10T428/31504; Y10T428/31511; Y10T428/31529
Claims Analysis
Total Claims: 27
Claim 1
Independent Claim
345 words
A curable composition comprising a mixture of (A) at least one of (1) at least one epoxy resin represented by the following formulas (I) or (II) ##STR10## wherein each B is represented by the formula ##STR11## each B' is represented by the formula ##STR12## each B" is represented by the formula ##STR13## each R is independently hydrogen or an alkyl group having from 1 to about 4 carbon atoms; each Q is independently hydrogen or a hydrocarbyl group having from 1 to about 10 carbon atoms; each R' is independently hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms or a halogen; m has a value of n-1; m' has a value of n'-1; m" has a value of n"-1; each n, n' and n" independently has a value from zero to about 3; q has a value from zero to about 4; and each z and z' independently has a value from zero to about 3; (2) the reaction product of (a) at least one epoxy resin as defined in component (A-1) and (b) at least one dihydric phenol represented by the following formulas (III) or (IV) ##STR14## wherein A is a divalent hydrocarbon group having from 1 to about 12 carbon atoms, --S--, --S--S--, ##STR15## or --O--; each Y is independently hydrogen, a halogen or a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms; and n has a value of zero or 1; and wherein components (a) and (b) are present in quantities such that the ratio of phenolic hydroxyl groups to epoxide groups is from about 0.01:1 to about 0.5:1; (3) mixtures thereof; (B) at least one amine substituted aromatic sulfonic acid amide represented by the following formula (V) ##STR16## wherein each X is independently hydrogen, a monovalent hydrocarbyl group having from 1 to about 10 carbon atoms or a halogen; and wherein components (A) and (B) are present in quantities such that the ratio of epoxy groups to hydrogen atoms attached to a nitrogen atom is from about 0.8:1 to about 2:1.
Claim 2
Dependent Claim
345 words
A curable composition comprising a mixture of (A) at least one of (1) at least one epoxy resin represented by the following formulas (I) or (II) ##STR10## wherein each B is represented by the formula ##STR11## each B' is represented by the formula ##STR12## each B" is represented by the formula ##STR13## each R is independently hydrogen or an alkyl group having from 1 to about 4 carbon atoms; each Q is independently hydrogen or a hydrocarbyl group having from 1 to about 10 carbon atoms; each R' is independently hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms or a halogen; m has a value of n-1; m' has a value of n'-1; m" has a value of n"-1; each n, n' and n" independently has a value from zero to about 3; q has a value from zero to about 4; and each z and z' independently has a value from zero to about 3; (2) the reaction product of (a) at least one epoxy resin as defined in component (A-1) and (b) at least one dihydric phenol represented by the following formulas (III) or (IV) ##STR14## wherein A is a divalent hydrocarbon group having from 1 to about 12 carbon atoms, --S--, --S--S--, ##STR15## or --O--; each Y is independently hydrogen, a halogen or a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms; and n has a value of zero or 1; and wherein components (a) and (b) are present in quantities such that the ratio of phenolic hydroxyl groups to epoxide groups is from about 0.01:1 to about 0.5:1; (3) mixtures thereof; (B) at least one amine substituted aromatic sulfonic acid amide represented by the following formula (V) ##STR16## wherein each X is independently hydrogen, a monovalent hydrocarbyl group having from 1 to about 10 carbon atoms or a halogen; and wherein components (A) and (B) are present in quantities such that the ratio of epoxy groups to hydrogen atoms attached to a nitrogen atom is from about 0.8:1 to about 2:1.
Claim 3
Dependent Claim
32 words
A composition of claim 1 wherein components (A) and (B) are present in quantities such that the ratio of epoxy groups to hydrogen atoms attached is from about 0.9:1 to about 1.25:1.
Claim 4
Dependent Claim
32 words
A composition of claim 1 wherein component (A) is component (A-1) wherein Q is hydrogen, each R' is hydrogen and m has an average value of from about 0.1 to about 2.
Claim 5
Dependent Claim
26 words
A composition of claim 3 wherein in component (A-1) m has an average value of from about 0.5 to about 1.5 and component (B) is sulfanilamide.
Claim 6
Dependent Claim
32 words
A composition of claim 2 wherein component (A) is component (A-1) wherein Q is hydrogen, each R' is hydrogen and m has an average value of from about 0.1 to about 2.
Claim 7
Dependent Claim
26 words
A composition of claim 5 wherein in component (A-1) m has an average value of from about 0.5 to about 1.5 and component (B) is sulfanilamide.
Claim 8
Dependent Claim
91 words
A composition of claim 1 wherein component (A) is component (A-2) wherein in component (A-2-a) Q is hydrogen, each R' is hydrogen and m has an average value of from about 0.1 to about 2; component (A-2-b) is represented by formula (IV) wherein A is a divalent hydrocarbyl group having from about 1 to about 6 carbon atoms, n has a value of 1, and components (A-2-a) and (A-2-b) are employed in quantities such that the ratio of phenolic hydroxyl groups to epoxide groups is from about 0.05:1 to about 0.25:1.
Claim 9
Dependent Claim
52 words
A composition of claim 7 wherein in component (A-2-a) n has an average value of from about 0.5 to about 1.5; components (A-2-a) and (A-2-b) are employed in quantities which provides a ratio of phenolic hydroxyl groups to epoxide groups of from about 0.1:1 to about 0.2:1; and component (B) is sulfanilamide.
Claim 10
Dependent Claim
91 words
A composition of claim 2 wherein component (A) is component (A-2) wherein in component (A-2-a) Q is hydrogen, each R' is hydrogen and m has an average value of from about 0.1 to about 2; component (A-2-b) is represented by formula (IV) wherein A is a divalent hydrocarbyl group having from about 1 to about 6 carbon atoms, n has a value of 1, and components (A-2-a) and (A-2-b) are employed in quantities which provides a ratio of phenolic hydroxyl groups to epoxide groups of from about 0.05:1 to about 0.25:1.
Claim 11
Dependent Claim
52 words
A composition of claim 9 wherein in component (A-2-a) n has an average value of from about 0.5 to about 1.5; components (A-2-a) and (A-2-b) are employed in quantities which provides a ratio of phenolic hydroxyl groups to epoxide groups of from about 0.1:1 to about 0.2:1; and component (B) is sulfanilamide.
Claim 12
Dependent Claim
377 words
A curable composition comprising a mixture of (A) at least one of (1) at least one epoxy resin represented by the following formulas (I) or (II) ##STR17## wherein each B is represented by the formula ##STR18## each B' is represented by the formula ##STR19## each B" is represented by the formula ##STR20## each R is independently hydrogen or an alkyl group having from 1 to about 4 carbon atoms; each Q is independently hydrogen or a hydrocarbyl group having from 1 to about 10 carbon atoms; each R' is independently hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms or a halogen; m has a value of n-1; m' has a value of n'-1; m" has a value of n"-1; each n, n' and n" independently has a value from zero to about 3; q has a value from zero to about 4; and each z and z' independently has a value from zero to about 3; (2) the reaction product of (a) at least one epoxy resin as defined in component (A-1) and (b) at least one dihydric phenol represented by the following formulas (III) or (IV) ##STR21## wherein A is a divalent hydrocarbon group having from 1 to about 12 carbon atoms, --S--, --S--S--, ##STR22## or --O--; each Y is independently hydrogen, a halogen or a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms; and n has a value of zero or 1; and wherein components (a) and (b) are present in quantities such that the ratio of phenolic hydroxyl groups to epoxide groups is from about 0.01:1 to about 0.5:1; (3) mixtures thereof; (B) at least one amine substituted aromatic sulfonic acid amide represented by the following formula (V) ##STR23## wherein each X is independently hydrogen, a monovalent hydrocarbyl group having from 1 to about 10 carbon atoms or a halogen; and x has a value of zero; and (C) from zero to about 50 percent by weight of the combined weight of components (A), (B) and (C) of at least one solvent; and wherein components (A) and (B) are present in quantities such that the ratio of epoxy groups to hydrogen atoms attached to a nitrogen atom is from about 0.8:1 to about 2:1.
Claim 13
Dependent Claim
377 words
A curable composition comprising a mixture of (A) at least one of (1) at least one epoxy resin represented by the following formulas (I) or (II) ##STR17## wherein each B is represented by the formula ##STR18## each B' is represented by the formula ##STR19## each B" is represented by the formula ##STR20## each R is independently hydrogen or an alkyl group having from 1 to about 4 carbon atoms; each Q is independently hydrogen or a hydrocarbyl group having from 1 to about 10 carbon atoms; each R' is independently hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms or a halogen; m has a value of n-1; m' has a value of n'-1; m" has a value of n"-1; each n, n' and n" independently has a value from zero to about 3; q has a value from zero to about 4; and each z and z' independently has a value from zero to about 3; (2) the reaction product of (a) at least one epoxy resin as defined in component (A-1) and (b) at least one dihydric phenol represented by the following formulas (III) or (IV) ##STR21## wherein A is a divalent hydrocarbon group having from 1 to about 12 carbon atoms, --S--, --S--S--, ##STR22## or --O--; each Y is independently hydrogen, a halogen or a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms; and n has a value of zero or 1; and wherein components (a) and (b) are present in quantities such that the ratio of phenolic hydroxyl groups to epoxide groups is from about 0.01:1 to about 0.5:1; (3) mixtures thereof; (B) at least one amine substituted aromatic sulfonic acid amide represented by the following formula (V) ##STR23## wherein each X is independently hydrogen, a monovalent hydrocarbyl group having from 1 to about 10 carbon atoms or a halogen; and x has a value of zero; and (C) from zero to about 50 percent by weight of the combined weight of components (A), (B) and (C) of at least one solvent; and wherein components (A) and (B) are present in quantities such that the ratio of epoxy groups to hydrogen atoms attached to a nitrogen atom is from about 0.8:1 to about 2:1.
Claim 14
Dependent Claim
63 words
A composition of claim 11 wherein components (A) and (B) are present in quantities such that the ratio of epoxy groups to hydrogen atoms attached to a nitrogen atom is from about 0.9:1 to about 1.25:1 and component (C) is present in quantities of from about 10 to about 45 percent by weight of the combined weight of components (A), (B) and (C).
Claim 15
Dependent Claim
32 words
A composition of claim 11 wherein component (A) is component (A-1) wherein Q is hydrogen, each R' is hydrogen and m has an average value of from about 0.1 to about 2.
Claim 16
Dependent Claim
26 words
A composition of claim 13 wherein in component (A-1) m has an average value of from about 0.5 to about 1.5 and component (B) is sulfanilamide.
Claim 17
Dependent Claim
32 words
A composition of claim 12 wherein component (A) is component (A-1) wherein Q is hydrogen, each R' is hydrogen and m has an average value of from about 0.1 to about 2.
Claim 18
Dependent Claim
26 words
A composition of claim 15 wherein in component (A-1) m has an average value of from about 0.5 to about 1.5 and component (B) is sulfanilamide.
Claim 19
Dependent Claim
91 words
A composition of claim 11 wherein component (A) is component (A-2) wherein in component (A-2-a) Q is hydrogen, each R' is hydrogen and m has an average value of from about 0.1 to about 2; component (A-2-b) is represented by formula (IV) wherein A is a divalent hydrocarbyl group having from about 1 to about 6 carbon atoms, n has a value of 1, and components (A-2-a) and (A-2-b) are employed in quantities such that the ratio of phenolic hydroxyl groups to epoxide groups is from about 0.05:1 to about 0.25:1.
Claim 20
Dependent Claim
52 words
A composition of claim 17 wherein in component (A-2-a) n has an average value of from about 0.5 to about 1.5; components (A-2-a) and (A-2-b) are employed in quantities which provides a ratio of phenolic hydroxyl groups to epoxide groups of from about 0.1:1 to about 0.2:1; and component (B) is sulfanilamide.
Claim 21
Dependent Claim
91 words
A composition of claim 12 wherein component (A) is component (A-2) wherein in component (A-2-a) Q is hydrogen, each R' is hydrogen and m has an average value of from about 0.1 to about 2; component (A-2-b) is represented by formula (IV) wherein A is a divalent hydrocarbyl group having from about 1 to about 6 carbon atoms, n has a value of 1, and components (A-2-a) and (A-2-b) are employed in quantities such that the ratio of phenolic hydroxyl groups to epoxide groups is from about 0.05:1 to about 0.25:1.
Claim 22
Dependent Claim
52 words
A composition of claim 19 wherein in component (A-2-a) n has an average value of from about 0.5 to about 1.5; components (A-2-a) and (A-2-b) are employed in quantities which provides a ratio of phenolic hydroxyl groups to epoxide groups of from about 0.05:1 to about 0.25:1; and component (B) is sulfanilamide.
Claim 23
Dependent Claim
32 words
A composition of claim 20 wherein components (A-2-a) and (A-2-b) are employed in quantities such that the ratio of phenolic hydroxyl groups to epoxide groups is from about 0.1:1 to about 0.2:1.
Claim 24
Dependent Claim
20 words
A substrate impregnated with a composition of claims 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 or 21.
Claim 25
Dependent Claim
24 words
An electrical or structural laminate or composite containing one or more layers of a cured impregnated substrate or combination of substrates of claim 22.
Claim 26
Dependent Claim
17 words
An electrical laminate of claim 23 having at least one external layer of an electrically conductive material.
Claim 27
Dependent Claim
13 words
An electrical laminate of claim 24 wherein said electrically conductive material is copper.
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| 7.5 Years (Year 8) | 1993-10-20 | 1994-04-21 | 1994-10-21 | $3760.00 | Window Closed / Lapsed |
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