US4546131A
Expired / Lapsed
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Polymer modified cyanate mixture and epoxy resins thereof
Assignee: Dow Chemical Co
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Filing: 1985-01-15
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Granted: 1985-10-08
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Expires: 2005-01-15
Abstract
Abstract Novel thermosettable compositions comprising a mixed cyanate of a polyphenol containing a copolymer of an ethylenically unsaturated compound and an alkenylphenyl cyanate are disclosed. These compositions are also useful in the preparation of novel epoxy resin compositions.
Inventors
- 👤 Robert E. Hefner, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 11:38
CPC Classifications
C; C08; C08L; C08L25/00; C08L25/18; C08G; C08G59/00; C08G59/02; C08G59/04; C08G59/06; C08G59/066; C08G59/18; C08G59/20; C08G59/32; C08G59/3236; C08G59/3245; C08L57/00
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
318 words
A composition which comprises a mixture of (A) from about 0.5 to about 95 percent by weight (%bw) of total composition of a product resulting from copolymerizing (1) from about 0.1 to about 50, %bw of the combined weight of components (A-1) and (A-2) of at least one alkenylphenyl cyanate represented by the formula ##STR11## wherein Z is a ##STR12## group; 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 or hydrocarbyloxy group having from 1 to about 4 carbon atoms, chlorine, bromine or a phenyl group; and x has a value of 4; and (2) from 50 to about 99.9 %bw of the combined weight of components (A-1) and (A-2) of at least one ethylenically unsaturated monomer; and (B) from about 5 to about 99.5 %bw of total composition of a mixed cyanate of a polyphenol prepared by the reaction of at least 0.01 but not more than 0.95, mole of a cyanogen halide or mixture of cyanogen halides per mole of aromatic hydroxyl groups in the presence of a suitable base in a quantity of from about 0.01 to about 1.0, mole per mole of aromatic hydroxyl groups with an aromatic polyphenol represented by the formulas ##STR13## wherein each A is independently a divalent hydrocarbon group having from 1 to about 12, carbon atoms, ##STR14## and the like; each A' is a divalent hydrocarbyl group having from 1 to about 3, carbon atoms or a ##STR15## group; each R' is independently hydrogen or a hydrocarbyl group having from 1 to about 6 carbon atoms or a halogen; n has a value of zero or 1; n' has a value from about 0.001 to about 6; n" has a value from about 1 to about 100; and p has a value of from zero to about 10.
Claim 2
Dependent Claim
318 words
A composition which comprises a mixture of (A) from about 0.5 to about 95 percent by weight (%bw) of total composition of a product resulting from copolymerizing (1) from about 0.1 to about 50, %bw of the combined weight of components (A-1) and (A-2) of at least one alkenylphenyl cyanate represented by the formula ##STR11## wherein Z is a ##STR12## group; 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 or hydrocarbyloxy group having from 1 to about 4 carbon atoms, chlorine, bromine or a phenyl group; and x has a value of 4; and (2) from 50 to about 99.9 %bw of the combined weight of components (A-1) and (A-2) of at least one ethylenically unsaturated monomer; and (B) from about 5 to about 99.5 %bw of total composition of a mixed cyanate of a polyphenol prepared by the reaction of at least 0.01 but not more than 0.95, mole of a cyanogen halide or mixture of cyanogen halides per mole of aromatic hydroxyl groups in the presence of a suitable base in a quantity of from about 0.01 to about 1.0, mole per mole of aromatic hydroxyl groups with an aromatic polyphenol represented by the formulas ##STR13## wherein each A is independently a divalent hydrocarbon group having from 1 to about 12, carbon atoms, ##STR14## and the like; each A' is a divalent hydrocarbyl group having from 1 to about 3, carbon atoms or a ##STR15## group; each R' is independently hydrogen or a hydrocarbyl group having from 1 to about 6 carbon atoms or a halogen; n has a value of zero or 1; n' has a value from about 0.001 to about 6; n" has a value from about 1 to about 100; and p has a value of from zero to about 10.
Claim 3
Dependent Claim
67 words
A composition of claim 1 wherein (i) component (A) is present in quantities of from about 5 to about 50 %bw; (ii) component (A-1) is present in quantities of from about 0.5 to about 15 %bw; (iii) component (A-2) is present in quantities of from about 85 to about 99.5 %bw; and (iv) component (B) is present in quantities of from about 50 to about 95 %bw.
Claim 4
Dependent Claim
67 words
A composition of claim 2 wherein (i) component (A) is present in quantities of from about 10 to about 25 %bw; (ii) component (A-1) is present in quantities of from about 1 to about 5 %bw; (iii) component (A-2) is present in quantities of from about 95 to about 99 %bw; and (iv) component (B) is present in quantities of from about 75 to about 90 %bw.
Claim 5
Dependent Claim
59 words
A composition of claim 3 wherein (i) component (A-1) is an alkenylphenyl cyanate represented by formula I wherein ##STR16## or a mixture thereof; (ii) component (A-2) is an acrylate ester represented by formula VII or a mixture thereof; and (iii) component (B) is a mixture of a diphenol, a monocyanate of a diphenol and a dicyanate of a diphenol.
Claim 6
Dependent Claim
21 words
A composition of claim 4 wherein component (A-2) is a vinyl aromatic monomer represented by formula VIII or a mixture thereof.
Claim 7
Dependent Claim
28 words
A composition of claim 4 wherein component (A-2) is a mixture of an acrylate monomer represented by formula VII and a vinyl aromatic monomer represented by formula VIII.
Claim 8
Dependent Claim
18 words
A polymer modified hydroxyaromatic triazine-containing oligomer resulting from trimerization of the polymer modified cyanate mixture of claim 1.
Claim 9
Dependent Claim
35 words
A polymer modified hydroxyaromatic triazine-containing and oxazoline-containing oligomer or polymer resulting from copolymerization of the polymer modified cyanate mixture of claim 1 and one or more epoxy resins represented by formulas IX, X, XI, XII.
Claim 10
Dependent Claim
58 words
A polymer modified hydroxyaromatic triazine-containing and oxazoline-containing oligomer of claim 8 resulting from cooligomerization of the polymer modified cyanate mixture of claim 1 and one or more epoxy resins represented by formulas IX, X, XI, XII wherein a mole ratio of about 1 to 10 to about 1 to 100 of epoxy groups to cyanate groups is used.
Claim 11
Dependent Claim
31 words
A polymer modified hydroxyaromatic triazine-containing and oxazoline-containing oligomer of claim 9 resulting from cooligomerization of the polymer modified cyanate mixture of claim 1 and an epoxy resin represented by formula X.
Claim 12
Dependent Claim
23 words
An epoxy resin composition resulting from dehydrohalogenating the reaction product of a polymer modified hydroxyaromatic triazine-containing oligomer of claim 7 and an epihalohydrin.
Claim 13
Dependent Claim
25 words
An epoxy resin composition resulting from dehydrohalogenating the reaction product of a polymer modified hydroxyaromatic triazine and oxazoline-containing oligomer of claim 9 and an epihalohydrin.
Claim 14
Dependent Claim
60 words
An advanced epoxy resin composition resulting from reacting (A) a polymer modified hydroxyaromatic triazine-containing oligomer of claim 7 and (B) one or more epoxy resins represented by formulas IX, X, XI, XII wherein components (A) and (B) are employed in quantities which provide a hydroxyl to epoxy mole ratio of from about 0.01 to 1 to about 0.99 to 1.
Claim 15
Dependent Claim
33 words
The composition of claim 13 wherein components (A) and (B) are employed in quantities which provide a hydroxyl to epoxy mole ratio of from about 0.05 to 1 to about 0.70 to 1.
Claim 16
Dependent Claim
33 words
The composition of claim 14 wherein components (A) and (B) are employed in quantities which provide a hydroxyl to epoxy mole ratio of from about 0.10 to 1 to about 0.50 to 1.
Claim 17
Dependent Claim
62 words
An advanced epoxy resin composition resulting from reacting (A) a polymer modified hydroxyaromatic triazine-containing and oxazoline-containing oligomer of claim 9 and (B) one or more epoxy resins represented by formulas IX, X, XI, XII wherein components (A) and (B) are employed in quantities which provide a hydroxyl to epoxy mole ratio of from about 0.01 to 1 to about 0.99 to 1.
Claim 18
Dependent Claim
33 words
The composition of claim 16 wherein components (A) and (B) are employed in quantities which provide a hydroxyl to epoxy mole ratio of from about 0.05 to 1 to about 0.70 to 1.
Claim 19
Dependent Claim
33 words
The composition of claim 17 wherein components (A) and (B) are employed in quantities which provide a hydroxyl to epoxy mole ratio of from about 0.10 to 1 to about 0.50 to 1.
Claim 20
Dependent Claim
43 words
A product resulting from curing a composition comprising (A) a composition or mixture of the compositions of claims 11, 12, 13, 14, 15, 16, 17 or 18 and (B) a curing quantity of at least one suitable curing agent and/or curing catalyst therefor.
Claim 21
Dependent Claim
15 words
A product of claim 19 which is reinforced with a natural or synthetic reinforcing material.
Claim 22
Dependent Claim
28 words
A product of claim 20 wherein said reinforcing material is a fibrous material which is in woven, mat, random fiber or continuous roving form or a combination thereof.
Claim 23
Dependent Claim
17 words
A product of claim 21 wherein said fibrous material is glass, carbon, graphite, aramid or combination thereof.
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) | 1988-10-07 | 1989-04-08 | 1989-10-08 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1992-10-07 | 1993-04-08 | 1993-10-08 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1996-10-07 | 1997-04-08 | 1997-10-08 | $7700.00 | Window Closed / Lapsed |