Dual functional poly(arylene ether) compounds

1. A capped poly(arylene ether) copolymer having the formula:

wherein

Q 1a is a C 1 -C 12 primary or secondary alkyl;

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

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

z is 0 or 1;

x and y represent the relative mole ratios of the arylene ether units wherein x and y are independently 0 to 50, or e is the number of moles of the arylene ether unit;

Y is a divalent linking group of the formula

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

each occurrence of D is independently a group of the formula

wherein

each occurrence of G is independently C 1 -C 12 hydrocarbylene;

each occurrence of Q is independently C 1 -C 6 alkylene or C 6 -C 12 arylene, wherein a is 0 or 1;

each occurrence of A is independently a single bond or —O—;

each occurrence of J is independently a single bond, C 1 -C 6 alkylene, or —(CH 2 ) n NH(CH 2 ) n (C═O)O— wherein n is 1 to 6; and

each occurrence of Z is independently of the formula

wherein

W a is O or S;

each of R and R′ is independently hydrogen, C 1 -C 12 hydrocarbyl, or C 1 -C 6 hydrocarbylene, optionally wherein both R and R′ together are a C 2 -C 8 alkylene group; and

m is 0 or 1.

2. The capped poly(arylene ether) copolymer of claim 1 , wherein

Q 1a is C 1 -C 12 primary alkyl;

Q 1b is C 1 -C 12 alkyl;

Q 2 is hydrogen; and

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

3. The capped poly(arylene ether) copolymer of claim 1 , wherein

Q 1a is C 1 -C 6 primary alkyl;

Q 1b is C 1 -C 6 alkyl;

Q 2 is hydrogen; and

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

4. The capped poly(arylene ether) copolymer of claim 1 , wherein

Q 1a and Q 1b are methyl;

Q 2 is hydrogen; and

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

5. The capped poly(arylene ether) copolymer of claim 1 , wherein R 5 is a (C 1 -C 6 -hydrocarbyl)(C 1 -C 6 -hydrocarbyl)aminomethylene group.

6. The capped poly(arylene ether) copolymer of claim 1 , wherein

Q 1a is C 1 -C 6 primary alkyl;

Q 1b is C 1 -C 6 alkyl;

Q 2 is hydrogen;

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

R 5 is a (C 1 -C 6 -alkyl)(C 1 -C 6 -alkyl)aminomethylene group.

7. The capped poly(arylene ether) copolymer of claim 1 , wherein the capped poly(arylene ether) copolymer is of the formula

8. The capped poly(arylene ether) copolymer of claim 1 , wherein

each occurrence of Q is independently C 1 -C 3 alkylene or C 6 phenylene;

each occurrence of J is independently a single bond or —(CH 2 ) n NH(CH 2 ) n (C═O)O—; and

n is 1 to 3.

9. The capped poly(arylene ether) copolymer of claim 1 , wherein D is a group of the formulas

10. The capped poly(arylene ether) copolymer of claim 1 , wherein

W a is O; and

R and R′ are independently hydrogen or C 1 -C 6 alkyl.

11. A process for forming the capped poly(arylene ether) copolymer of claim 1 , the process 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 11 , wherein the capping agent comprises a compound of the formula

wherein

each occurrence of G is independently C 1 -C 12 hydrocarbylene;

each occurrence of Q is independently C 1 -C 6 alkylene or C 6 -C 12 arylene, wherein a is 0 or 1;

A is a single bond or —O—;

J is a single bond, C 1 -C 6 alkylene, or —(CH 2 ) n NH(CH 2 ) n (C═O)O— wherein n is 1 to 6;

X is halogen, tosylate, mesylate, or triflate;

R″ is C 1 -C 6 alkyl; and

each occurrence of Z is independently

wherein

W a is O or S;

each of R and R′ is independently hydrogen, C 1 -C 12 hydrocarbyl, or C 1 -C 6 hydrocarbylene, optionally wherein both R and R′ together are a C 2 -C 8 alkylene group; and

m is 0 or 1.

13. The process of claim 12 , wherein

X is a halogen;

each occurrence of G is independently C 1-3 hydrocarbylene;

each occurrence of Q is independently C 1 -C 3 alkylene or phenylene;

J is a single bond, C 1 -C 3 alkylene, or —(CH 2 ) n NH(CH 2 ) n (C═O)O— wherein n is 1 to 3;

W a is O;

each of R and R′ is independently hydrogen or C 1 -C 6 hydrocarbyl; and

m is 0 or 1.

14. The process of claim 13 , wherein

X is Cl;

J is C 1 -C 3 alkylene or —(CH 2 ) n NH(CH 2 ) n (C═O)O— wherein n is 1 or 2;

R and R′ are hydrogen; and

m is 1.

15. The process of claim 11 , wherein the uncapped poly(arylene ether) copolymer has the formula

wherein

Q 1a is a C 1 -C 12 primary or secondary alkyl;

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

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

z is 0 or 1;

x and y represent the relative mole ratios of the arylene ether units or e is the number of moles of the arylene ether unit; and

Y is divalent linking group of the formula

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

16. The process of claim 15 , wherein

Q 1a is C 1 -C 12 primary alkyl;

Q 1b is C 1 -C 12 alkyl;

Q 2 is hydrogen; and

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

17. The process of claim 11 , wherein the reacting is in the presence of a capping catalyst.

18. The process of claim 11 , further comprising reacting a monohydric phenol and a dihydric phenol under conditions effective to provide the uncapped poly(arylene ether) copolymer.

19. A curable composition comprising a thermosetting resin and the capped poly(arylene ether) copolymer of claim 1 .

20. A cured composition obtained by heating the curable composition of claim 19 for a time and temperature sufficient to effect curing.