POLY(ARYLENE ETHER) COPOLYMER

1 . A poly(arylene ether) copolymer,

wherein the poly(arylene ether) copolymer is the product of oxidative copolymerization of monomers comprising a monohydric phenol and a dihydric phenol, wherein the dihydric phenol is of the formula

wherein R 3 and R 4 and R 5 and R 6 are independently at each occurrence hydrogen, halogen, unsubstituted or substituted C 1-12 primary or secondary 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; and Y has a structure

wherein each occurrence of R 7 is independently hydrogen or C 1-12 hydrocarbyl, and each occurrence of R 8 and R 9 is hydrogen, C 1-12 hydrocarbyl, or C 1-6 hydrocarbylene wherein R 8 and R 9 collectively form a C 4-12 cycloalkylene group;

wherein the poly(arylene ether) copolymer comprises less than or equal to 0.1 weight percent of incorporated amine groups.

2 . The poly(arylene ether) copolymer of claim 1 , wherein the monohydric phenol comprises 2,6-dimethyl phenol, 2,3,6-trimethyl phenol, or a combination thereof, and the dihydric phenol comprises 2,2-bis(3,5-dimethyl-4-hydroxyphenyl)propane.

3 . The poly(arylene ether) copolymer of claim 1 , wherein the poly(arylene ether) copolymer has a number average molecular weight of 500 to 2,500 grams per mole and a weight average molecular weight of 1,000 to 6,000 grams per mole, wherein number average molecular weight and weight average molecular weight are as determined by gel permeation chromatography.

4 . The poly(arylene ether) copolymer of claim 1 , wherein the poly(arylene ether) copolymer comprises 0.001 to 0.1 weight percent of incorporated amine groups.

5 . The poly(arylene ether) copolymer of claim 1 , wherein the poly(arylene ether) copolymer comprises 0.01 to 0.1 weight percent of incorporated groups.

6 . The polyarene ether) copolymer of claim 1 , wherein the oxidative copolymerization is in the presence of a catalyst composition excluding a secondary monoamine; and wherein the poly(arylene ether) copolymer is devoid of incorporated amine groups and the poly(arylene ether) copolymer has an average of 1.8 to 2 hydroxyl groups per molecule.

7 . The poly(arylene ether) copolymer of claim 1 , wherein the oxidative copolymerization is in the presence of a catalyst composition excluding a secondary monoamine; and wherein the poly(arylene ether) copolymer is devoid of incorporated amine groups and has a ratio of weight average molecular weight to number average molecular weight of 1.9 to 3.

8 . The poly(arylene ether) copolymer of claim 1 , wherein the oxidative copolymerization is in the presence of a catalyst composition excluding a secondary monoamine; and wherein the poly(arylene ether) copolymer is devoid of incorporated amine groups and has an intrinsic viscosity if 0.04 to 0.15 deciliter per gram measured at 25° C. in chloroform.

9 . The poly(arylene ether) copolymer of claim 1 , wherein the poly(arylene ether) copolymer has an intrinsic viscosity if 0.04 to 0.15 deciliter per gram measured at 25° C. in chloroform.

10 . The poly(arylene ether) copolymer of claim 5 , wherein the poly(arylene ether) copolymer has an average of 1.8 to 2 hydroxyl groups per molecule.

11 . A method of making a poly(arylene ether) copolymer, the method comprising:

oxidatively copolymerizing a monohydric phenol and a dihydric phenol in a solvent in the presence of a catalyst composition comprising

a metal source;

0.18 to 0.40 weight percent of a secondary alkylene diamine ligand;

0 to 0.2 weight percent of a secondary monoamine; and

a tertiary monoamine;

wherein weight percent of each component of the catalyst composition is based on the total weight of the monohydric phenol and the dihydric phenol;

to form the poly(arylene ether) copolymer.

12 . The method of claim 11 , wherein the catalyst composition comprises 0.05 to 0.15 weight percent secondary monoamine; and wherein the poly(arylene ether) copolymer comprises 0.01 to 0.1 weight percent of incorporated amine groups.

13 . The method of claim 11 , wherein the catalyst composition excludes a secondary monoamine and the poly(arylene ether) copolymer is devoid of incorporated amine groups.

14 . A poly(arylene ether) copolymer made by the method of claim 11 , wherein the poly(arylene ether) copolymer has

a number average molecular weight of 500 to 2,500 grams per mole and a weight average molecular weight of 1,000 to 6,000 grams per mole, wherein number average molecular weight and weight average molecular weight are as determined by gel permeation chromatography;

an intrinsic viscosity if 0.04 to 0.15 deciliter per gram measured at 25° C. in chloroform;

less than or equal to 0.1 weight percent of incorporated dibutylamine groups; and

0.5 to 1.5 weight percent of units derived from 3,3′,5,5′-tetramethyl-4,4′-biphenol.

15 . A curable composition comprising

the poly(arylene ether) copolymer of claim 1 ;

an auxiliary curable resin, a curable unsaturated monomer composition, or both; and

optionally, a curing promoter.

16 . The curable composition of claim 15 , wherein the auxiliary curable resin comprises an epoxy resin, a cyanate ester resin, a maleimide resin, a benzoxazine resin, a vinylbenzyl ether resin, an arylcyclobutene resin, a perfluorovinyl ether resin, oligomers or polymers with curable vinyl functionality, or a combination thereof, and the curable unsaturated monomer composition comprises a monofunctional styrenic compound, a monofunctional (meth)acrylic compound, a polyfunctional allylic compound, a polyfunctional (meth)acrylate, a polyfunctional (meth)acrylamide, a polyfunctional styrenic compound, or a combination thereof

17 . The curable composition of claim 15 , comprising

the poly(arylene ether) copolymer of claim 1 ,

an epoxy resin, a cyanate ester resin, or a combination thereof; and

optionally a curing promoter.

18 . A thermoset composition comprising a cured product of the composition of claim 15 .

19 . An article comprising the thermoset composition of claim 18 .

20 . The article of claim 19 , wherein the article is in the form of a composite, a foam, a fiber, a layer, a coating, an encapsulant, an adhesive, a sealant, a molded component, a prepreg, a casing, or a combination comprising at least one of the foregoing.