Epoxybenzyl-terminated poly(arylene ether)s, method for preparation thereof, and curable compositions comprising same

1. A poly(arylene ether) having the structure

R—W—R,

wherein

W is a divalent poly(arylene ether) residue terminated with phenolic oxygen atoms, and

R is an epoxybenzyl group having the structure

wherein each occurrence of R is the same or different, and each occurrence of m is independently 1 or 2.

2. The poly(arylene ether) of claim 1 , having the structure

wherein each occurrence of m is independently 1 or 2; Q 1 and Q 2 are each independently selected from the group consisting of halogen, unsubstituted or substituted C 1 -C 12 primary or secondary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; each occurrence of Q 3 and Q 4 is independently selected from the group consisting of hydrogen, halogen, unsubstituted or substituted C 1 -C 12 primary or secondary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; x and y are independently 0 to about 30, provided that the sum of x and y is at least 2; and L has the structure

wherein each occurrence of R 1 and R 2 and R 3 and R 4 is independently selected from the group consisting of hydrogen, halogen, unsubstituted or substituted C 1 -C 12 primary or secondary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; z is 0 or 1; and Y has a structure selected from the group consisting of

wherein each occurrence of R 5 is independently selected from the group consisting of hydrogen and C 1 -C 12 hydrocarbyl, and each occurrence of R 6 and R 7 is independently selected from the group consisting of hydrogen, C 1 -C 12 hydrocarbyl, and C 1 -C 6 hydrocarbylene wherein R 6 and R 7 collectively form a C 4 -C 12 alkylene group.

3. The poly(arylene ether) of claim 1 , wherein the epoxybenzyl group is selected from the group consisting of

and a combination thereof.

4. A poly(arylene ether) having the structure

wherein each occurrence of a and b is independently 0 to about 20, provided that the sum of a and b is at least 2.

5. A process of making the poly(arylene ether) of claim 1 , comprising reacting a peroxide-containing reagent with a vinylbenzyl-terminated poly(arylene ether).

6. The process of claim 5 , wherein the vinylbenzyl-terminated poly(arylene ether) has the structure

wherein each occurrence of m is independently 1 or 2; Q 1 and Q 2 are each independently selected from the group consisting of halogen, unsubstituted or substituted C 1 -C 12 primary or secondary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; each occurrence of Q 3 and Q 4 is independently selected from the group consisting of hydrogen, halogen, unsubstituted or substituted C 1 -C 12 primary or secondary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; x and y are independently 0 to about 30, provided that the sum of x and y is at least 2; and L has the structure

wherein each occurrence of R 1 and R 2 and R 3 and R 4 is independently selected from the group consisting of hydrogen, halogen, unsubstituted or substituted C 1 -C 12 primary or secondary hydrocarbyl, C 1 -C 12 hydrocarbylthio, C 1 -C 12 hydrocarbyloxy, and C 2 -C 12 halohydrocarbyloxy wherein at least two carbon atoms separate the halogen and oxygen atoms; z is 0 or 1; and Y has a structure selected from the group consisting of

wherein each occurrence of R 5 is independently selected from the group consisting of hydrogen and C 1 -C 12 hydrocarbyl, and each occurrence of R 6 and R 7 is independently selected from the group consisting of hydrogen, C 1 -C 12 hydrocarbyl, and C 1 -C 6 hydrocarbylene wherein R 6 and R 7 collectively form a C 4 -C 12 alkylene group.

7. The process of claim 5 , wherein the peroxide-containing reagent is an aliphatic or aromatic peracid selected from the group consisting of perbenzoic acid, 3-chloroperbenzoic acid, monoperphthalic acid, p-methoxyperbenzoic acid, p-nitroperbenzoic acid, m-nitroperbenzoic acid, α-pernaphthoic acid, β-pernaphthoic acid, phenylperacetic acid, performic acid, peracetic acid, perpropionic acid, perbutyric acid perisovaleric acid, perheptanoic acid, and combinations thereof.

8. The process of claim 5 , further comprising reacting a hydroxyl terminated poly(arylene ether) with a vinylbenzyl halide in the presence of an alkali metal alkoxide to form the vinylbenzyl-terminated poly(arylene ether),

wherein the vinylbenzyl halide has the structure

wherein X is fluoride, chloride, bromide, or iodide, and m is 1 or 2; and

wherein the hydroxyl-terminated poly(arylene ether) has the structure

wherein each occurrence of a and b is independently 0 to about 20, provided that the sum of a and b is at least 2.

9. The process of claim 8 , wherein the vinylbenzyl halide is 3-vinylbenzyl chloride, 4-vinylbenzyl chloride, or a combination thereof.

10. A process of making a poly(arylene ether), comprising:

reacting a hydroxyl-terminated poly(arylene ether) having the structure

with 4-vinylbenzyl chloride to form a vinylbenzyl-terminated poly(arylene ether) having the structure

and

reacting the vinylbenzyl-terminated poly(arylene ether) with a peracid to form an epoxybenzyl-terminated poly(arylene ether) having the structure

wherein each occurrence of a and b is independently 0 to about 20, provided that the sum of a and b is at least 2.