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Cyanate functional maleimide thermosetting composition

Assignee: Dow Chemical Co
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Filing: 1988-05-17
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Granted: 1989-04-11
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Expires: 2008-05-17
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Abstract

Abstract Thermoset products are prepared by polymerizing (A) at least one thermosettable compound which contains both a maleimide group and a cyanate group such as 3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl cyanate and optionally (B) at least one of (1) at least one aromatic polycyanate such as bisphenol A dicyanate; (2) at least one polymaleimide such as N,N'-(methylenedi-p-phenylene)bismaleimide; (3) at least one material having an average of more than one vicinal epoxide group per molecule such as a diglycidyl ether of bisphenol A; (4) at least one polymerizable ethylenically unsaturated material such as styrene; or (5) a mixture of any two or more of components 1-4 in any combination.

Inventors

  • 👤 Robert E. Hefner, Jr.

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-02 09:23
CPC Classifications
C; C08; C08F; C08F22/00; C08F22/36; C08F22/40; C08G; C08G73/00; C08G73/06; C08G73/10; C08G73/12

Claims Analysis

Total Claims: 13
Claim 1
Independent Claim 80 words
A composition which comprises (A) at least one thermosettable compound which simultaneously contains both a maleimide group and a cyanate group and (B) at least one of (1) at least one polymaleimide; (2) at least one material having an average of more than one vicinal epoxide group per molecule; or (3) at least one polymerizable ethylenically unsaturated material; wherein component (A) comprises from about 1 to about 99 percent by weight of the combined weight of components (A) and (B).
Claim 2
Dependent Claim 80 words
A composition which comprises (A) at least one thermosettable compound which simultaneously contains both a maleimide group and a cyanate group and (B) at least one of (1) at least one polymaleimide; (2) at least one material having an average of more than one vicinal epoxide group per molecule; or (3) at least one polymerizable ethylenically unsaturated material; wherein component (A) comprises from about 1 to about 99 percent by weight of the combined weight of components (A) and (B).
Claim 3
Dependent Claim 631 words
A composition of claim 1 wherein (i) component (A) is represented by the formulas ##STR22## wherein each R and R 1 is independently hydrogen or a hydrocarbyl group having from 1 to about 3 carbon atoms; each R' is independently hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms or a halogen atom; A is a divalent hydrocarbon group having from 1 to about 10 carbon atoms, ##STR23## n has a value of zero or 1 and x has a value of 4; (ii) component (B-1) is represented by the following formulas ##STR24## wherein each A is independently a divalent hydrocarbon group having from 1 to about 10 carbon atoms, ##STR25## n has a value of zero or 1 and x has a value of 4; each A' is independently a divalent hydrocarbon group having from 1 to about 6 carbon atoms or a ##STR26## group; R' is hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms or a halogen atom; each Z is independently hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 4 carbon atoms, chlorine, bromine or a --O--C.tbd.N group; m has a value of from zero to about 100; n has a value of zero or 12; n" has a value of from about 0.001 to about 6; and p has a value from zero to about 10; (iii) component (B-2) is represented by the following formulas ##STR27## wherein Q is a divalent hydrocarbyl group having from 2 to about 12 carbon atoms; each R and R 1 is independently hydrogen or a hydrocarbyl group having from 1 to about 3 carbon atoms; each R' is independently hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms or a halogen atom; Z 1 is a direct bond, or Z 1 is a direct bond, a divalent hydrocarbyl group having from 1 to about 5 carbon atoms, ##STR28## and m 1 has a value of from about 0.001 to about 10; (iv) component (B-3) is represented by the following formulas ##STR29## wherein each A is independently a divalent hydrocarbon group having from 1 to about 10 carbon atoms, ##STR30## each A' is independently a divalent hydrocarbon group having from 1 to about 6 carbon atoms or a ##STR31## group; each R' is independently hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms or a halogen atom; each R" is independently hydrogen or an alkyl group having from 1 to about 4 carbon atoms; n has a value of zero or 1; n' has a value of from about zero to about 30; n" has a value of from about 0.001 to about 6; p has a value from zero to about 10; x has a value of 4; and x' has a value of 3; (v) component (B-4) is represented by the following formulas ##STR32## wherein R 3 is a hydrocarbyl group having from 2 to about 25 carbon atoms and may be branched, cyclic or polycyclic; R 4 is hydrogen or a methyl group; each Q 1 is independently hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 4 carbon atoms, a vinyl group, an allyl group, chlorine or bromine; each Q 2 is independently hydrogen or a hydrocarbyl or hydrocarbyloxy group having from 1 to about 4 carbon atoms; Y 1 is ##STR33## wherein each R, R 1 and R 2 is independently hydrogen or a hydrocarbyl group having from 1 to about 3 carbon atoms; w and w 1 are each positive integers, the sum of which is 5; and (vi) component (A) comprises from about 1 to about 75 percent by weight of the combined weight of components (A) and (B).
Claim 4
Dependent Claim 27 words
A composition of claim 2 wherein component (A) comprises from about 5 to about 50 percent by weight of the combined weight of components (A) and (B).
Claim 5
Dependent Claim 86 words
A composition of claim 3 wherein when A is present and is a divalent hydrocarbyl group, it has from 1 to about 4 carbon atoms; A 1 is independently a divalent hydrocarbon group having from 1 to about 4 carbon atoms; when R' is a hydrocarbyl or hydrocarbyloxy group it has from 1 to about 4 carbon atoms; n' has a value from zero to about 5; n" has a value from 0.01 to about 3; and p has a value from zero to about 3.
Claim 6
Dependent Claim 46 words
A composition of claim 4 wherein (i) component (B-1) is bisphenol A dicyanate or the polycyanate of a dicyclopentadiene and phenol condensation product; (ii) component (B-2) is N,N'-(methylenedi-p-phenylene)bismaleimide; (iii) component (B-3) is a diglycidyl ether of bisphenol A; and (iv) component (B-4) is styrene or 2-ethylhexylacrylate.
Claim 7
Dependent Claim 14 words
A composition of claim 5 wherein component (A) is 3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl cyanate, or 4-(1-(4-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)phenyl)-1-methylethyl)phenyl cyanate.
Claim 8
Dependent Claim 10 words
The product resulting from copolymerizing a composition of claim 1.
Claim 9
Dependent Claim 10 words
The product resulting from copolymerizing a composition of claim 2.
Claim 10
Dependent Claim 10 words
The product resulting from copolymerizing a composition of claim 3.
Claim 11
Dependent Claim 10 words
The product resulting from copolymerizing a composition of claim 4.
Claim 12
Dependent Claim 10 words
The product resulting from copolymerizing a composition of claim 5.
Claim 13
Dependent Claim 10 words
The product resulting from copolymerizing a composition of claim 6.

References Cited (Backward Citations)

US3491060A Cited
US4110364A Cited
US4371689A Cited
US4396745A Cited
US4683276A Cited
US4769440A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1992-04-10 1992-10-10 1993-04-11 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1996-04-10 1996-10-10 1997-04-11 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2000-04-10 2000-10-10 2001-04-11 $7700.00 Window Closed / Lapsed

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