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US4600760A Expired / Lapsed US ⏱️ 0.0 years remaining

Thermosettable resin composition containing alkenyl phenyl cyanate

Assignee: Dow Chemical Co
•
Filing: 1985-04-11
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Granted: 1986-07-15
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Expires: 2005-04-11
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Abstract

Abstract Thermosettable compositions comprising an alkenyl phenyl cyanate and at least one of an aromatic polycyanate, a polymaleimide or a polymerizable ethylenically unsaturated aromatic monomer are disclosed.

Inventors

  • 👤 Robert E. Hefner, Jr.

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 17:41
CPC Classifications
C; C08; C08F; C08F212/00; C08F212/02; C08F212/04; C08F212/14; C08F212/26; C08F267/00; C08F267/10

Claims Analysis

Total Claims: 17
Claim 1
Independent Claim 176 words
A thermosettable composition which comprises (A) at least one alkenyl phenyl cyanate containing at least 10 percent by weight of monomeric material represented by formula I ##STR25## wherein each R, R 1 and R 2 is independently hydrogen or a hydrocarbyl group having from 1 to about 3 carbon atoms; each X is independently hydrogen, a hydrocarbyl group or a hydrocarbyloxy having from 1 to about 10 carbon atoms, chlorine or bromine; each Y is independently hydrogen or a hydrocarbyl group having from 1 to about 10 carbon atoms; Y 1 is a ##STR26## group and x and y are positive integers and the sum of x plus y has a value of 4; and (B) at least one of (1) at least one aromatic polycyanate, (2) at least one polymaleimide, or (3) at least one polymerizable ethylenically unsaturated aromatic compound; wherein component A comprises from about 1 to about 99 percent by weight of the combined weight of components A and B; with the proviso that component (B-3) is not used alone with component (A).
Claim 2
Dependent Claim 176 words
A thermosettable composition which comprises (A) at least one alkenyl phenyl cyanate containing at least 10 percent by weight of monomeric material represented by formula I ##STR25## wherein each R, R 1 and R 2 is independently hydrogen or a hydrocarbyl group having from 1 to about 3 carbon atoms; each X is independently hydrogen, a hydrocarbyl group or a hydrocarbyloxy having from 1 to about 10 carbon atoms, chlorine or bromine; each Y is independently hydrogen or a hydrocarbyl group having from 1 to about 10 carbon atoms; Y 1 is a ##STR26## group and x and y are positive integers and the sum of x plus y has a value of 4; and (B) at least one of (1) at least one aromatic polycyanate, (2) at least one polymaleimide, or (3) at least one polymerizable ethylenically unsaturated aromatic compound; wherein component A comprises from about 1 to about 99 percent by weight of the combined weight of components A and B; with the proviso that component (B-3) is not used alone with component (A).
Claim 3
Dependent Claim 336 words
A thermosettable composition of claim 1 wherein (i) component (A) contains at least about 90 percent by weight of monomeric material represented by formula I; (ii) component (B-1) is represented by the following formulas IIIA, IIIB, IIIC, IIID or any combination thereof ##STR27## wherein each Z is independently hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms, chlorine, bromine, or a --O--C.tbd.N group; Z 1 is independently a direct bond, an alkylene group having from 1 to about 5 carbon atoms, --S--, --S--S--, ##STR28## Z 2 is independently a divalent hydrocarbon group having from 1 to about 6, carbon atoms or a ##STR29## group; Z 3 is a hydrogen, a hydrocarbyl or hydrocarbyloxy group having from 1 to about 10 carbon atoms, chlorine or bromine; m has a value of zero to about 100, m 1 has a value of from about 0.001 to about 6; n has a value of from zero to about 10; n 1 has a value of 4 and n 2 has a value of 3; (iii) component (B-2) is represented by formulas V, VI, VII or any combination thereof ##STR30## wherein R, R 1 and Z 1 are as above; Q is a divalent alkyl radical having 2 to about 12 carbon atoms and m 1 has a value of 0.01 to about 10; (iv) component (B-3) is represented by the following formula XII ##STR31## wherein R, R 1 , R 2 and Y 1 are as above defined, each Q 1 is independently hydrogen, a hydrocarbyl group or hydrocarbyloxy group having from 1 to about 10 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 and w and w 1 are each positive integers, the sum of which is 5; (v) 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 28 words
A thermosettable 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 140 words
A thermosettable composition of claim 3 wherein (i) component A is selected from p-isopropenylphenyl cyanate, p-vinyl phenyl cyanate, m-vinyl phenyl cyanate, methyl-p-isopropenylphenyl cyanate, 3-chloro-4-isopropenylphenyl cyanate, p-allylphenyl cyanate, p-methallylphenyl cyanate, m-allylphenyl cyanate, 2,6-dimethyl-4-allylphenyl cyanate, or mixtures thereof; (ii) component (B-1) is selected from bisphenol A dicyanate, the dicyanates of 4,4'-dihydroxydiphenyl oxide, resorcinol, 4,4'-thiodiphenol, 4,4'-sulfonyldiphenol, 3,3',5,5'-tetrabromobisphenol A, 2,2',6,6'-tetrabromobisphenol A, 3-phenylbisphenol A, 4,4'-dihydroxybiphenyl, 2,2'-dihydroxybiphenyl, 2,2',4,4'-tetrahydroxydiphenyl methane, 2,2',6,6'-tetramethyl-3,3',5,5'-tetrabromobisphenol A, 3,3'-dimethoxybisphenol A, ##STR32## the tricyanate of tris (hydroxyphenyl) methane, the polycyanate of a phenolformaldehyde condensation product (novolac), the polycyanate of a dicyclopentadiene and phenol condensation product, or mixtures thereof; (iii) component (B-2) is selected from N,N'-ethylenebismaleimide, N,N'-ethylenebis(2-methylmaleimide), N,N'-hexamethylenemaleimide, N,N'-(oxydi-p-phenylene)bismaleimide, N,N'-(methylenedi-p-phenylene)bismaleimide, N,N'-(methylenedi-p-phenylene)bis(2-methylmaleimide), N,N'-(thiodi-p-phenylene)bismaleimide, N,N'-(sulfonyldi-m-phenylene)bismaleimide, N,N'-(isopropylidenedi-p-phenylene)bismaleimide, polymethylene polyphenylene polymaleimides, or mixtures thereof; (iv) component (B-3) is selected from styrene, alpha-methylstyrene, chlorostyrene, bromostyrene, t-butylstyrene, p-methylstyrene, p-methoxystyrene, divinylbenzene, propylstyrene, chloro-alpha-methylstyrene, m-methylstyrene, o-methylstyrene, allylbenzene, methallylbenzene, p-allylstyrene, divinylbenzene, or mixtures thereof.
Claim 6
Dependent Claim 49 words
A thermosettable composition of claim 1 wherein (i) component (A) is p-isopropenyl phenyl cyanate; (ii) component (B) consists of a mixture of components (B-1), (B-2) and (B-3); (iii) component (B-1) is bisphenol A dicyanate; (iv) component (B-2) is the bismaleimide of methylene dianiline; and (v) component (B-3) is styrene.
Claim 7
Dependent Claim 49 words
A thermosettable composition of claim 2 wherein (i) component (A) is p-isopropenyl phenyl cyanate; (ii) component (B) consists of a mixture of components (B-1), (B-2) and (B-3); (iii) component (B-1) is bisphenol A dicyanate; (iv) component (B-2) is the bismaleimide of methylene dianiline; and (v) component (B-3) is styrene.
Claim 8
Dependent Claim 49 words
A thermosettable composition of claim 3 wherein (i) component (A) is p-isopropenyl phenyl cyanate; (ii) component (B) consists of a mixture of components (B-1), (B-2) and (B-3); (iii) component (B-1) is bisphenol A dicyanate; (iv) component (B-2) is the bismaleimide of methylene dianiline; and (v) component (B-3) is styrene.
Claim 9
Dependent Claim 27 words
A thermosettable composition of claim 1 wherein (i) component (A) is p-isopropenyl cyanate; (ii) component (B) consists of component (B-1); (iii) component (B-1) is bisphenol A cyanate.
Claim 10
Dependent Claim 27 words
A thermosettable composition of claim 2 wherein (i) component (A) is p-isopropenyl cyanate; (ii) component (B) consists of component (B-1); (iii) component (B-1) is bisphenol A cyanate.
Claim 11
Dependent Claim 27 words
A thermosettable composition of claim 3 wherein (i) component (A) is p-isopropenyl cyanate; (ii) component (B) consists of component (B-1); (iii) component (B-1) is bisphenol A cyanate.
Claim 12
Dependent Claim 39 words
A thermosettable composition of claim 1 wherein (i) component (A) is p-isopropenyl phenyl cyanate; (ii) component (B) consists of a mixture of components (B-1) and (B-3); (iii) component (B-1) is bisphenol A dicyanate; and (iv) component (B-3) is styrene.
Claim 13
Dependent Claim 39 words
A thermosettable composition of claim 2 wherein (i) component (A) is p-isopropenyl phenyl cyanate; (ii) component (B) consists of a mixture of components (B-1) and (B-3); (iii) component (B-1) is bisphenol A dicyanate; and (iv) component (B-3) is styrene.
Claim 14
Dependent Claim 39 words
A thermosettable composition of claim 3 wherein (i) component (A) is p-isopropenyl phenyl cyanate; (ii) component (B) consists of a mixture of components (B-1) and (B-3); (iii) component (B-1) is bisphenol A dicyanate; and (iv) component (B-3) is styrene.
Claim 15
Dependent Claim 43 words
A thermosettable composition of claim 1 wherein (i) component (A) is p-isopropenyl phenyl isocyanate; (ii) component (B) consists of a mixture of components (B-1) and (B-2); (iii) component (B-1) is bisphenol A dicyanate; and (iv) component (B-2) is the bismaleimide of methylene dianiline.
Claim 16
Dependent Claim 43 words
A thermosettable composition of claim 2 wherein (i) component (A) is p-isopropenyl phenyl isocyanate; (ii) component (B) consists of a mixture of components (B-1) and (B-2); (iii) component (B-1) is bisphenol A dicyanate; and (iv) component (B-2) is the bismaleimide of methylene dianiline.
Claim 17
Dependent Claim 43 words
A thermosettable composition of claim 3 wherein (i) component (A) is p-isopropenyl phenyl isocyanate; (ii) component (B) consists of a mixture of components (B-1) and (B-2); (iii) component (B-1) is bisphenol A dicyanate; and (iv) component (B-2) is the bismaleimide of methylene dianiline.

References Cited (Backward Citations)

US4298720A Cited
US4477629A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1989-07-14 1990-01-13 1990-07-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1993-07-14 1994-01-13 1994-07-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1997-07-14 1998-01-13 1998-07-15 $7700.00 Window Closed / Lapsed

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