Granted Patent B2

US 12,503,593 · App. 17/924,384 · Granted Dec 23, 2025

Inventors: Eylem Tarkin-Tas (Delmar, NY); Yasser Dhahir (Selkirk, NY)

Assignee: SHPP GLOBAL TECHNOLOGIES B.V.

C08L71/10C08J3/28C09D171/10

Abstract

Claims (51)

1 . A curable thermosetting composition comprising a capped poly(arylene ether) copolymer comprising a reactive end group, wherein the capped poly(arylene ether) copolymer is derived from an alkyl, aryl-phenol;

wherein the capped poly(arylene ether) copolymer is of formula (1) or formula (2):

wherein

each of R x and R y is independently a reactive end group comprising a (meth)acrylate, a (meth)acrylonitrile, a vinyl benzene, an allyl, an epoxide comprising a glycidyl ether, a cyanate ester, an amine, maleimide, a carboxylic acid, a carboxylic acid alkyl ester, or a combination thereof,

each occurrence of Q 1a and Q 1b independently is halogen, C 1-12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C 1-12 hydrocarbylthio, C 1-12 hydrocarbyloxy, or C 2-12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms;

each occurrence of Q 2 is independently hydrogen, halogen, unsubstituted or substituted C 1-12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C 1-12 hydrocarbylthio, C 1-12 hydrocarbyloxy, or C 2-12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms;

each occurrence of R 1 , R 2 , R 3 , and R 4 is independently hydrogen, halogen, C 1-12 hydrocarbyl provided that the hydrocarbyl group is not tertiary hydrocarbyl, C 1-12 hydrocarbylthio, C 1-12 hydrocarbyloxy, or C 2-12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms;

x and y represent the relative mole ratios of the arylene ether units wherein x and y are each independently 0 to 50, or 0 to 30, provided that the sum of x and y is at least 2; or e is the number of moles of the arylene ether unit;

each occurrence of R 5a is independently Q 1a or a (C 1-6 -hydrocarbyl)(C 1-6 -hydrocarbyl)aminomethylene group;

each occurrence of R 5b is independently Q 1b or a (C 1-6 -hydrocarbyl)(C 1-6 -hydrocarbyl)aminomethylene group;

provided that the capped poly(arylene ether) copolymer comprises:

at least one repeating unit wherein Q 1a is a C 1-12 primary or secondary alkyl, and Q 1b is unsubstituted C 6-12 aryl,

at least one terminal unit where R 5a is a C 1-12 primary or secondary alkyl, and R 5b is unsubstituted C 6-12 aryl, or

a combination thereof;

Y 1 is a divalent linking group of any one or more of formulas

wherein

each occurrence of R a , R b , and R e is independently hydrogen, C 1-12 hydrocarbyl, or C 1-6 hydrocarbylene, optionally wherein R a and R b together are a C 4-8 cycloalkylene group,

each occurrence of R f is independently a C 1-6 hydrocarbylene group,

each occurrence of R g is independently hydrogen, C 1-12 hydrocarbyl, or C 1-12 halohydrocarbyl, and

n′ is 5 to 50;

z is 0 or 1; and

each occurrence of R is independently

wherein

Y 2 is a divalent linking group having one of formulas

wherein

each occurrence of R c and R d independently is hydrogen or C 1-12 alkyl,

R 5 is an epoxide-containing group, a cyanate-containing group, or a C 1-12 hydrocarbyl optionally substituted with one or two carboxylic acid groups,

each occurrence of R 6 , R 7 , and R 8 independently is hydrogen, C 1-18 hydrocarbyl, C 2-18 hydrocarbyloxycarbonyl, nitrile, formyl, carboxylic acid, imidate, or thiocarboxylic acid, and

each occurrence of R 9 , R 10 , R 11 , R 12 , and R 13 independently is hydrogen, halogen, C 1-12 alkyl, C 2-12 alkenyl, hydroxy, amino, maleimide, carboxylic acid, or a C 2-20 alkyl ester, provided that the capped poly(arylene ether) copolymer comprises: at least one repeating unit,

wherein Q1a is a C1-12 primary or secondary alkyl, and Q1b is unsubstituted C6-12 aryl.

2 . The curable thermosetting composition of claim 1 , wherein the capped poly (arylene ether) copolymer is derived from a reaction of the copolymerization of bisphenol A and 2-methyl-6-phenylphenol to form an uncapped poly (arylene ether) copolymer, and capping of the uncapped poly (arylene ether) copolymer with methacrylica nhydride to form the capped poly (arylene ether) copolymer.

3 . The curable thermosetting composition of claim 1 , wherein

each occurrence of Q 1a independently is C 1-12 primary alkyl, or C 1-6 primary alkyl;

each occurrence of Q 10 independently is C 1-12 alkyl or C 6-12 aryl; or C 1-6 alkyl or phenyl;

Q 2 is hydrogen; and

R 1 , R 2 , R 3 , and R 4 are each independently hydrogen, halogen, or C 1-12 alkyl; or hydrogen or C 1-6 alkyl,

optionally wherein the capped poly (arylene ether) copolymer comprises at least one repeating unit wherein Q 1a is the C 1-12 primary alkyl, and Q 1b is the unsubstituted C 6-12 aryl; or wherein the capped poly (arylene ether) copolymer comprises at least one repeating unit wherein Q 1a is C 1-6 primary alkyl, and Q 1b is unsubstituted phenyl.

4 . The curable thermosetting composition of claim 1 wherein the capped poly (arylene ether) copolymer is of formula (2a):

wherein Q 1a , Q 1b , Q 2 , R 1 , R 2 , R 5a , R 5b , R x , R y , x, and y are as defined in claim 1 .

5 . The curable thermosetting composition of claim 1 , wherein the capped poly (arylene ether) copolymer is of formula (2b):

wherein R 1 , R 2 , R 6 to R 8 , R 5a , R 5b , Q 1a , Q 1b , Q 2 , x, and y are as defined in claim 1 .

6 . The curable thermosetting composition of claim 1 , further comprising one or more of a crosslinking agent, a curing agent, a curing catalyst, a curing initiator, or a combination thereof.

7 . The curable thermosetting composition of claim 1 , further comprising one or more of a flame retardant, a filler, a coupling agent, or a combination thereof.

8 . A cured thermoset composition, comprising a cured product of the curable thermosetting composition of claim 1 .

9 . A method for the manufacture of the cured thermoset composition of claim 8 , comprising curing the curable thermosetting composition, or at a temperature of 50 to 250° C.

10 . An article comprising the cured thermoset composition of claim 8 ,

wherein the article is a composite, a foam, a fiber, a layer, a coating, an encapsulant, an adhesive, a sealant, a molded component, a prepreg, a casing, a cast article, a laminate, or a combination thereof;

or wherein the article is a metal clad laminate, an electronic composite, a structural composite, or a combination thereof.

11 . A varnish composition, comprising the curable thermosetting composition of claim 1 ; and a solvent.

12 . An article manufactured from the varnish composition of claim 11 , or wherein the article is a fiber, a layer, a coating, a cast article, a prepreg, a composite, or a laminate; or wherein the article is a metal clad laminate.

13 . A method for the manufacture of the article of claim 12 , comprising impregnating the varnish composition into a substrate to form a prepreg; and curing the varnish composition.

Assignments (2)

Priority Claims (1)

Continuity (2)

References Cited (40)