US4429112A
Expired / Lapsed
US
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Process of delaying cure of curable resin composition containing cyanate ester compound with benzene sulfonic acid compound
Assignee: Mitsubishi Gas Chemical Co Inc
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Filing: 1982-06-01
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Granted: 1984-01-31
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Expires: 2002-06-01
Abstract
Abstract A method for delaying curing rate of a curable resin composition comprising a polyfunctional cyanate ester compound or mixture of a polyfunctional cyanate ester compound and a polyfunctional maleimide compound, characterized in that a specific benzene sulfonic acid is added to said composition is disclosed.
Inventors
- 👤 Morio Gaku
- 👤 Syunichi Nagai
- 👤 Hidenori Kimpara
- 👤 Satoshi Ayano
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-03 17:36
CPC Classifications
C; C08; C08G; C08G85/00; C08G85/004; C08G59/00; C08G59/18; C08G59/40; C08G59/4007; C08G59/4014
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
144 words
A method for delaying curing rate of a curable resin composition comprising: (a) at least one cyanate ester compound selected from the group consisting of (1) a polyfunctional aromatic cyanate ester monomer having the formula R--OCN).sub.m wherein m is 2 to 5 and R is an aromatic organic group, the cyanate groups being bonded to an aromatic ring of said aromatic organic group, (2) a homoprepolymer of one or more cyanate esters of (1), (3) a coprepolymer of (1) and an amine, characterized in that at least one alkyl substituted or non-substituted benzene sulfonic acid represented by the formula ##STR6## wherein R is alkyl having 1-3 carbon atoms, l is 0 or integer of 1-3 and n is 0 or integer of 1-4 in an amount of 0.0001-5% by weight on the basis of total weight of the composition is added to said composition.
Claim 2
Independent Claim
144 words
A method for delaying curing rate of a curable resin composition comprising: (a) at least one cyanate ester compound selected from the group consisting of (1) a polyfunctional aromatic cyanate ester monomer having the formula R--OCN).sub.m wherein m is 2 to 5 and R is an aromatic organic group, the cyanate groups being bonded to an aromatic ring of said aromatic organic group, (2) a homoprepolymer of one or more cyanate esters of (1), (3) a coprepolymer of (1) and an amine, characterized in that at least one alkyl substituted or non-substituted benzene sulfonic acid represented by the formula ##STR6## wherein R is alkyl having 1-3 carbon atoms, l is 0 or integer of 1-3 and n is 0 or integer of 1-4 in an amount of 0.0001-5% by weight on the basis of total weight of the composition is added to said composition.
Claim 3
Dependent Claim
68 words
The method as defined in claim 1 wherein the cyanate ester is selected from the group consisting of 1,3- or 1,4-dicyanatobenzene; 1,3,5-tricyanatobenzene; 1,3-, 1,4-, 1,6-, 1,8-, 2,6- or 2,7-dicyanatonaphthalene; 1,3,6-tricyanatonaphthalene; 4,4'-dicyanatobiphenyl; bis(4-cyanatopheny)methane; 2,2-bis(4-cyanatophenyl)propane, 2,2-bis(3,5-dichloro-4-cyanatophenyl)propane, 2,2-bis(3-dibromo-4-dicyanatophenyl)propane; bis(4-cyanatophenyl)ether; bis(4-cyanatophenyl)thioether; bis(4-cyanatophenyl)sulfone; tris(4-cyanatophenyl)phosphite; tris(4-cyanatophenyl)phosphate; bis(3-chloro-4-cyanatophenyl)methane; cyanated novolak produced by reacting a novolak with cyanogen halide, cyanated bisphenol polycarbonate oligomer produced by reacting a bisphenol polycarbonate oligomer with cyanogen halide; and mixtures thereof.
Claim 4
Dependent Claim
30 words
The method as defined in claim 1 wherein said benzene sulfonic acid is selected from the group consisting of benzene sulfonic acid, toluene sulfonic acid and toluene sulfonic acid monohydrate.
Claim 5
Independent Claim
203 words
A method for delaying curing rate of a curable resin composition comprising: (a) at least one cyanate ester compound selected from the group consisting of (1) a polyfunctional aromatic cyanate ester monomer having the formula R--OCN).sub.m wherein m is 2 to 5 and R is an aromatic organic group, the cyanate groups being bonded to an aromatic ring of said aromatic organic group, (2) a homoprepolymer of one or more cyanate esters of (1), (3) a coprepolymer of (1) and an amine; (b) at least one compound selected from the group consisting of: (1) a polyfunctional maleimide, (2) a homoprepolymer of (1), and (3) a coprepolymer of (1) and an amine, said composition including a mixture of components (a) and (b), a preliminary reaction product of components (a) and (b), or the combination of said mixture and said preliminary reaction product, characterized in that at least one alkyl substituted or non-substituted benzene sulfonic acid represented by the formula ##STR7## wherein R is alkyl having 1-3 carbon atoms, l is 0 or integer of 1-3 and n is 0 or integer of 1-4 in an amount of 0.0001-5% by weight on the basis of total weight of the composition is added to said composition.
Claim 6
Independent Claim
203 words
A method for delaying curing rate of a curable resin composition comprising: (a) at least one cyanate ester compound selected from the group consisting of (1) a polyfunctional aromatic cyanate ester monomer having the formula R--OCN).sub.m wherein m is 2 to 5 and R is an aromatic organic group, the cyanate groups being bonded to an aromatic ring of said aromatic organic group, (2) a homoprepolymer of one or more cyanate esters of (1), (3) a coprepolymer of (1) and an amine; (b) at least one compound selected from the group consisting of: (1) a polyfunctional maleimide, (2) a homoprepolymer of (1), and (3) a coprepolymer of (1) and an amine, said composition including a mixture of components (a) and (b), a preliminary reaction product of components (a) and (b), or the combination of said mixture and said preliminary reaction product, characterized in that at least one alkyl substituted or non-substituted benzene sulfonic acid represented by the formula ##STR7## wherein R is alkyl having 1-3 carbon atoms, l is 0 or integer of 1-3 and n is 0 or integer of 1-4 in an amount of 0.0001-5% by weight on the basis of total weight of the composition is added to said composition.
Claim 7
Dependent Claim
68 words
The method as defined in claim 4 wherein the cyanate ester is selected from the group consisting of 1,3- or 1,4-dicyanatobenzene; 1,3,5-tricyanatobenzene; 1,3-, 1,4-, 1,6-, 1,8-, 2,6- or 2,7-dicyanatonaphthalene; 1,3,6-tricyanatonaphthalene; 4,4'-dicyanatobiphenyl; bis(4-cyanatophenyl)methane; 2,2-bis(4-cyanatophenyl)propane, 2,2-bis(3,5-dichloro-4-cyanatophenyl)propane, 2,2-bis(3-dibromo-4-dicyanatophenyl)propane; bis(4-cyanatophenyl)ether; bis(4-cyanatophenyl)thioether; bis(4-cyanatophenyl)sulfone; tris(4-cyanatophenyl)phosphite; tris(4-cyanatophenyl)phosphate; bis(3-chloro-4-cyanatophenyl)methane; cyanated novolak produced by reacting a novolak with cyanogen halide, cyanated bisphenol polycarbonate oligomer produced by reacting a bisphenol polycarbonate oligomer with cyanogen halide; and mixtures thereof.
Claim 8
Dependent Claim
30 words
The method as defined in claim 4 wherein said benzene sulfonic acid is selected from the group consisting of benzene sulfonic acid, toluene sulfonic acid and toluene sulfonic acid monohydrate.
Claim 9
Dependent Claim
21 words
The method as defined in claim 4 wherein said composition further contains an epoxy compound having at least two 1,2-epoxy groups.
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) | 1987-01-30 | 1987-08-01 | 1988-01-31 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-01-30 | 1991-08-01 | 1992-01-31 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-01-30 | 1995-08-01 | 1996-01-31 | $7700.00 | Window Closed / Lapsed |