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US4546131A Expired / Lapsed US ⏱️ 0.0 years remaining

Polymer modified cyanate mixture and epoxy resins thereof

Assignee: Dow Chemical Co
•
Filing: 1985-01-15
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Granted: 1985-10-08
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Expires: 2005-01-15
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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)

US4142034A Cited
US4477629A Cited
US4489202A Cited
US4487915A Cited
US4506063A Cited

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

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