POLY(ARYLENE ETHER) COPOLYMER, METHOD TO PREPARE THE SAME, AND ARTICLE DERIVED THEREFROM

1 . 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.

2 . The capped poly(arylene ether) copolymer of claim 1 , wherein the capped poly(arylene ether) copolymer has an average of 1.1 to 2 reactive end groups per molecule; or 1.4 to 2 reactive end groups per molecule; or 1.8 to 2 reactive end groups per molecule.

3 . The capped poly(arylene ether) copolymer of claim 1 , wherein the capped poly(arylene ether) copolymer is derived from a reaction of a dihydric phenol and a monohydric phenol comprising a 2-(alkyl)-6-(aryl)phenol;

or wherein the monohydric phenol is a 2-(C 1-12 primary or secondary alkyl)-6-(unsubstituted C 6-12 aryl)phenol.

4 . The capped poly(arylene ether) copolymer of claim 1 , wherein the capped poly(arylene ether) copolymer is derived from oxidative polymerization of the dihydric phenol and the monohydric phenol comprising a 2-(alkyl)-6-(aryl)phenol in the presence of a catalyst composition.

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

wherein

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 Re 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 9 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; and

R x and R y are each independently R or a hydrogen atom, provided that at least one of R x and R y is not a hydrogen atom.

6 . The capped poly(arylene ether) copolymer of claim 5 , wherein

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

each occurrence of Q 1b 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.

7 . The capped poly(arylene ether) copolymer of claim 5 , wherein at least one repeating unit is derived from the monohydric phenol of the formula:

wherein Q 1a is C 1-6 primary alkyl, Q 1b is unsubstituted phenyl, and Q 2 is as defined in claim 5 .

8 . The capped poly(arylene ether) copolymer of claim 5 , 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 5 ;

or wherein R 1 and R 2 are each independently hydrogen or C 1-6 alkyl.

9 . The capped poly(arylene ether) copolymer of claim 5 , 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 5 .

10 . A process for forming the capped poly(arylene ether) copolymer of claim 1 , the process comprising oxidatively copolymerizing a 2-(alkyl)-6-(aryl)phenol and a dihydric phenol in a solvent in the presence of a catalyst composition.

11 . The process of claim 10 , further comprising reacting a capping agent and an uncapped poly(arylene ether) copolymer comprising a phenolic end group under conditions effective to provide a reaction mixture comprising the capped poly(arylene ether) copolymer.

12 . The process of claim 10 , further comprising oxidatively copolymerizing the 2-(alkyl)-6-(aryl)phenol and the dihydric phenol in the solvent in the presence of the catalyst composition to provide a reaction product comprising the uncapped poly(arylene ether) copolymer, wherein the solvent is not removed from the reaction product before the reacting with the capping agent.

13 . The process of claim 1 , wherein an additional monohydric phenol different from the 2-(alkyl)-6-(aryl)phenol is present during the oxidatively copolymerizing.

14 . A curable thermosetting composition comprising the capped poly(arylene ether) copolymer of claim 1 .

15 . An article derived from the curable thermosetting composition of claim 14 , 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.