Copolymers of polyaminopolyolefins and polyanhydrides and methods of their preparation

1. A copolymer of a polyamine that has two or more amino groups, and a polyanhydride that has two or more anhydride groups; wherein the polyamine comprises a polyaminopolyolefin; wherein the copolymer has the structure of Formula A:

R 5 X—Y n X—R 6   (A)

wherein:

each X is independently alkylene, cycloalkylene, arylene, heteroarylene, heterocyclylene, or a divalent polymer group, provided that at least one of the X groups is a divalent polyolefin group;

each Y is independently a moiety containing two groups, each of which is independently amido or imido;

R 5 and R 6 are each independently amino, amido, or imido; and

n is an integer ranging from about 1 to about 100.

2. The copolymer of claim 1 , wherein the polyamine is a polyaminopolymer or polyaminopolyisobutylene.

3. The copolymer of claim 1 , wherein the polyaminopolyolefin is a quasi-living polyaminopolyolefin or quasi-living polyaminopolyisobutylene.

4. The copolymer of claim 1 , wherein the polyaminopolyolefin has the structure of Formula I:

R x R b -L-Z—(CR 1 R 2 ) m NH 2 ] r   (I)

wherein:

each L is independently a bond, alkylene, alkenylene, cycloalkylene, arylene, heteroarylene, or heterocyclylene;

each Z is independently a bond, —O—, —S—, —NR z —, —C(O)—, —C(O)NR z —, —OC(O)NR z —, —NR z C(O)NR z —, or —NR z C(NR z )NR z —; where each R Z is independently hydrogen or alkyl;

each R b is independently a divalent oligoolefin group;

R x is an initiator residue of functionality r;

each R 1 and R 2 is independently hydrogen, hydroxy, or alkyl;

each m is independently an integer ranging from about 0 to about 20; and

r is an integer ranging from about 2 to about 8;

wherein the alkyl, alkylene, alkenylene, cycloalkylene, arylene, heteroarylene, and heterocyclylene are each independently and optionally substituted.

5. The copolymer of claim 4 , wherein each L is independently a bond, C 6-14 arylene, or 5-membered heteroarylene, wherein the arylene and heteroarylene are each independently and optionally substituted.

6. The copolymer of claim 4 , wherein each L is independently a bond, phenylene, or pyrrolene, wherein the phenylene and pyrrolene are each independently and optionally substituted.

7. The copolymer of claim 4 , wherein each L is 1,4-phenylene, optionally substituted.

8. The copolymer of claim 4 , wherein Z is a bond, —O—, or —S—.

9. The copolymer of claim 4 , wherein each R 1 is hydrogen or each R 2 is hydrogen.

10. The copolymer of claim 4 , wherein m is an integer of 0, 1, 2, 3, 4, 6, or 11.

11. The copolymer of claim 4 , wherein R b is a divalent oligoisobutylene group.

12. The copolymer of claim 4 , wherein R b is a divalent oligoisobutylene group of —[CH 2 —C(CH 3 ) 2 ] p —, wherein p is an integer ranging from about 2 to about 10,000.

13. The copolymer of claim 12 , wherein p is an integer from about 5 to about 100.

14. The copolymer of claim 4 , wherein R x is an initiator residue of:

wherein R c is hydrogen or alkyl, wherein the alkyl is optionally substituted.

15. The copolymer of claim 14 , wherein R c is hydrogen or t-butyl.

16. The copolymer of claim 4 , wherein r is an integer of 2, 3, or 4.

17. The copolymer of claim 4 , wherein r is 2.

18. The copolymer of claim 4 , wherein the moiety -L-Z—(CR 1 R 2 ) m NH 2 is each independently:

19. The copolymer of claim 4 , wherein:

each L-Z is independently phenyleneoxy, pyrrolene, or —S—;

each R b is independently a divalent oligoisobutylene group of —[CH 2 —C(CH 3 ) 2 ] p —, wherein p is an integer ranging from about 5 to about 100;

R x is an initiator residue of:

wherein R c is hydrogen or t-butyl;

each R 1 and R 2 is hydrogen;

each m is independently an integer ranging from about 2 to about 12; and

r is an integer of 2;

wherein the phenylene and pyrrolene are each independently and optionally substituted.

20. The copolymer of claim 1 , wherein the polyanhydride is a dianhydride.

21. The copolymer of claim 20 , wherein the dianhydride is an aryl dianhydride, optionally substituted.

22. The copolymer of claim 20 , wherein the dianhydride is pyromellitic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride, 4,4′-(4,4′-isopropylidenediphenoxy)bis(phthalic anhydride), benzophenone-3,3′,4,4′-tetracarboxylic dianhydride, or a mixture thereof.

23. The copolymer of claim 2 , wherein the polyaminopolymer is a polyaminopolyolefin.

24. The copolymer of claim 1 , wherein the polyamine further comprises a polyetheramine.

25. The copolymer of claim 24 , wherein the polyetheramine is a polyaminopoly(propylene oxide) or polyetherdiamine.

26. The copolymer of claim 24 , wherein the polyetheramine is a polyetherdiamine of Formula XI-1:

wherein x is an integer ranging from about 2 to about 100.

27. The copolymer of claim 26 , wherein x is an integer of about 6, about 33, or about 68.

28. The copolymer of claim 1 , wherein the copolymer is a copolymer of a quasi-living diaminopolyisobutylene, and pyromellitic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride, 4,4′-(4,4′-isopropylidenediphenoxy)bis(phthalic anhydride), benzophenone-3,3′,4,4′-tetracarboxylic dianhydride, or a mixture thereof.

29. The copolymer of claim 1 , wherein the copolymer is a copolymer selected from:

a copolymer of a quasi-living diaminopolyisobutylene and pyromellitic dianhydride;

a copolymer of a quasi-living diaminopolyisobutylene and 1,4,5,8-naphthalenetetracarboxylic dianhydride;

a copolymer of a quasi-living diaminopolyisobutylene and 4,4′-(4,4′-isopropylidenediphenoxy)bis(phthalic anhydride); and

a copolymer of a quasi-living diaminopolyisobutylene and benzophenone-3,3′,4,4′-tetracarboxylic dianhydride.

30. The copolymer of claim 1 , wherein the copolymer is a copolymer of a quasi-living diaminopolyisobutylene, polyetherdiamine, and pyromellitic dianhydride, 1,4,5,8-naphthalenetetracarboxylic dianhydride, 4,4′-(4,4′-isopropylidenediphenoxy)bis(phthalic anhydride), benzophenone-3,3′,4,4′-tetracarboxylic dianhydride, or a mixture thereof.

31. The copolymer of claim 1 , wherein the copolymer is a copolymer of a quasi-living diaminopolyisobutylene, polyetherdiamine, 1,4,5,8-naphthalenetetracarboxylic dianhydride, and benzophenone-3,3′,4,4′-tetracarboxylic dianhydride.

32. The copolymer of claim 1 , wherein the copolymer has a weight average molecular weight ranging from about 1,000 to about 50,000.

33. The copolymer of claim 1 , wherein the copolymer has a polydispersity index of no greater than about 5.

34. The copolymer of claim 1 , wherein each X is independently a divalent polyolefin group.

35. The copolymer of claim 1 , wherein each X is independently

wherein each R b is independently a divalent oligoolefin group and R c is hydrogen or alkyl, optionally substituted.

36. The copolymer of claim 35 , wherein R b is a divalent oligoisobutylene group.

37. The copolymer of claim 35 , wherein R b is a divalent oligoisobutylene group of —[CH 2 —C(CH 3 ) 2 ] p —, wherein p is an integer from about 5 to about 100.

38. The copolymer of claim 35 , wherein R c is hydrogen or t-butyl.

39. The copolymer of claim 1 , wherein each Y is independently a divalent aryl group containing two imido groups.

40. The copolymer of claim 39 , wherein each Y is independently

41. The copolymer of claim 1 , wherein R 5 is amino, imido, or phthalimido.

42. The copolymer of claim 1 , wherein R 6 is amino, imido, or phthalimido.

43. The copolymer of claim 1 , wherein n is an integer ranging from about 1 to about 10.

44. The copolymer of claim 34 , wherein each X is independently:

wherein a divalent oligoisobutylene group of —[CH 2 —C(CH 3 ) 2 ] p —, wherein p is an integer from about 5 to about 100; and R c is hydrogen or t-butyl;

each Y is independently

R 5 and R 6 are each independently —NH 2 or phthalimido; and

n is an integer ranging from about 1 to about 10.

45. The copolymer of claim 1 , wherein the copolymer has a number average molecular weight ranging from about 1,000 to about 50,000.

46. The copolymer of claim 1 , wherein the copolymer has a polydispersity index of no greater than about 5.

47. The copolymer of claim 1 , wherein the copolymer is formed by reacting the polyamine with the polyanhydride.

48. A lubricating oil composition comprising an oil of lubricating viscosity and the copolymer of claim 1 .

49. A concentrate comprising from about 20 to 60 wt. % of the copolymer of claim 1 and from about 80 to about 40 wt. % of an organic diluent.