Amine-substituted pyrrolidine-2,5-dionyl copolymers, polyimides, articles, and methods

1. A copolymer comprising monomers according to formula (I), formula (II), formula (III), or formula (IV):

wherein—

R 1 and R 6 , independently, are a C 1 -C 30 hydrocarbyl;

R a , R b , R c , R 2 , R 3 , R 4 , and R 5 , independently, are selected from the group consisting of hydrogen and a C 1 -C 30 hydrocarbyl;

m and n, independently, are integers from 1 to 10,000; and

p is 0 or 1.

2. The copolymer of claim 1 , wherein (i) R 3 , R 4 , and R 5 are hydrogen, and R 2 is a C 1 -C 30 hydrocarbyl, or (ii) R 4 is a C 1 -C 30 hydrocarbyl and R 2 , R 3 , and R 5 are hydrogen.

3. The copolymer of claim 1 , wherein, in formula (I), (i) R a and R b are hydrogen, (ii) R a is a C 1 -C 30 hydrocarbyl and R b is hydrogen, or (iii) R a is hydrogen and R b is a C 1 -C 30 hydrocarbyl.

4. The copolymer of claim 1 , wherein R 1 is an unsubstituted or substituted oxy-diphenyl.

5. The copolymer of claim 1 , wherein R 1 is an unsubstituted oxy-diphenyl, and the copolymer comprises monomers of formula (Ia), formula (IIa), formula (IIIa), or formula (IVa):

6. The copolymer of claim 5 , wherein (i) R 3 , R 4 , and R 5 are hydrogen, and R 2 is a C 1 -C 30 hydrocarbyl, or (ii) R 4 is a C 1 -C 30 hydrocarbyl and R 2 , R 3 , and R 5 are hydrogen.

7. The copolymer of claim 5 , wherein (i) R 3 , R 4 , and R 5 are hydrogen, and R 2 is an unsubstituted or substituted phenyl, (ii) R 4 is an unsubstituted or substituted phenyl, and R 2 , R 3 , and R 5 are hydrogen, (iii) R 3 , R 4 , and R 5 are hydrogen, and R 2 is a methoxy, or (iv) R 4 is a methoxy, and R 2 , R 3 , and R 5 are hydrogen.

8. The copolymer of claim 1 , wherein R 1 is an unsubstituted oxy-diphenyl, and the copolymer comprises monomers of formula (Ib), formula (IIb), formula (IIIc), or formula (IVd):

9. The copolymer of claim 8 , wherein (i) R 3 , R 4 , and R 5 are hydrogen, and R 2 is an unsubstituted phenyl, (ii) R 4 is an unsubstituted phenyl, and R 2 , R 3 , and R 5 are hydrogen, (iii) R 3 , R 4 , and R 5 are hydrogen, and R 2 is a methoxy, or (iv) R 4 is a methoxy, and R 2 , R 3 , and R 5 are hydrogen.

10. The copolymer of claim 9 , wherein p is 1, and R 6 is a C 1 -C 5 hydrocarbyl.

11. A polyimide of formula (V), formula (VI), formula (VII), or formula (VIII):

wherein—

R 1 , R 6 , and R 8 , independently, are a C 1 -C 30 hydrocarbyl;

R a , R b , R c , R 2 , R 3 , R 4 , and R 5 , independently, are selected from the group consisting of hydrogen and a C 1 -C 30 hydrocarbyl;

R 7 is a monocyclic or polycyclic C 1 -C 30 hydrocarbyl;

m and n, independently, are integers from 1 to 10,000;

p is 0 or 1; and

q is selected from the group consisting of 0 and an integer from 1 to 10,000.

12. The polyimide of claim 11 , wherein q is 0.

13. The polyimide of claim 11 , wherein R 7 is selected from the group consisting of—

(i) an unsubstituted benzene moiety, wherein a monomer comprising R 7 has the following structure—

(ii) an unsubstituted biphenyl moiety, wherein a monomer comprising R 7 has the following structure—

(iii) an unsubstituted benzophenonyl moiety, wherein a monomer comprising R 7 has the following structure—

(iv) an unsubstituted oxy-diphenyl moiety, wherein a monomer comprising R 7 has the following structure—

and

(v) an unsubstituted naphthalenyl moiety, wherein a monomer comprising R 7 has the following structure—

14. The polyimide of claim 11 , wherein (i) R 1 , (ii) R 8 , or (iii) R 1 and R 8 is/are an unsubstituted or substituted oxy-diphenyl.

15. The polyimide of claim 11 , wherein (i) R 3 , R 4 , and R 5 are hydrogen, and R 2 is an unsubstituted or substituted phenyl, (ii) R 4 is an unsubstituted or substituted phenyl, and R 2 , R 3 , and R 5 are hydrogen, (iii) R 3 , R 4 , and R 5 are hydrogen, and R 2 is a methoxy, or (iv) R 4 is a methoxy, and R 2 , R 3 , and R 5 are hydrogen.

16. A wire comprising:

a conductor; and

at least one layer of a polymeric enamel insulation adjacent the conductor, the polymeric enamel insulation comprising the polyimide of claim 11 .

17. A method of forming a polyimide, the method comprising:

providing a polymer comprising a first monomer, the first monomer comprising a 1-(amino-C 1 -C 30 hydrocarbyl)pyrrolidinyl-2,5-dione moiety;

contacting the polymer and (i) a dianhydride, or (ii) a dianhydride and a diamine to form a polyamic acid; and

heating the polyamic acid at a temperature effective to form the polyimide.

18. The method of claim 17 , wherein the polymer is a copolymer, and the providing of the polymer comprises:

contacting (i) an olefinic anhydride and (ii) an olefin or olefinic monomer to form a precursor polymer; and

contacting the precursor polymer and a diamine to form the polymer.

19. The method of claim 18 , wherein the olefinic anhydride is selected from the group consisting of maleic anhydride, citraconic anhydride, itaconic anhydride, and a compound of formula (IX):

formula (IX),

wherein—

R 9 is a C 1 -C 30 hydrocarbyl;

R 10 , R 11 , and R 12 , independently, are selected from the group consisting of hydrogen and a C 1 -C 30 hydrocarbyl; and

r is 0 or 1.

20. The method of claim 17 , wherein the dianhydride is selected from the group consisting of

(i) 1H,3H-benzo[1,2-c:4,5-c′]difuran-1,3,5,7-tetraone—

(ii) [5,5′-biisobenzofuran]-1,1′,3,3′-tetraone—

(iii) 5,5′-carbonylbis(isobenzofuran-1,3-dione)—

(iv) 5,5′-oxybis(isobenzofuran-1,3-dione)—

 and

(v) isochromeno[6,5,4-def]isochromene-1,3,6,8-tetraone—