Asphalt, copolymer and elastomer composition

• US 4,818,367 A
• Filed: 04/14/1986
• Issued: 04/04/1989
• Est. Priority Date: 04/14/1986
• Status: Expired due to Fees

• Current Assignee: J H Diamond Company
• Original Assignee: J H Diamond Company
• Inventors: Winkler, David S.
• Primary Examiner(s): Sneed, H. M. S.
• Assistant Examiner(s): MYERS, HELANE ELEANORA
• Application Number:
  US06/851,835
• Time in Patent Office: 1,086 Days
• Field of Search: 208/22, 208/23, 106/273 R, 106/273 N, 106/281 R, 524/69, 524/62, 525/54.5, 527/500
• US Class Current: 208/23
• CPC Class Codes: C08L 15/00 Compositions of rubber derivatives C08L11/00, C08L13/00 take precedence
• CPC Class Codes: C08L 23/025 Copolymer of an unspecified olefin with a monomer other than an olefin
• CPC Class Codes: C08L 2666/04 Macromolecular compounds according to groups C08L7/00 - C08L49/00, or C08L55/00 - C08L57/00; Derivatives thereof
• CPC Class Codes: C08L 95/00 Compositions of bituminous materials, e.g. asphalt, tar, pitch

Abstract

An asphalt composition containing an asphalt, a copolymer of an olefin with an anhydride or a nitrile, and an unsaturated elastomer having at least two terminal groups each with an active hydrogen, a halogen, an epoxy oxygen or a cyanocarbon. The composition may be prepared by copolymerizing an olefin with an anhydride or a nitrile in the presence of a free radical initiator, and thereafter mixing the copolymer with the asphalt and elastomer. The copolymer may be mixed first with a petroleum oil, then with the elastomer and lastly with the asphalt. The copolymer may be a polyanhydride from maleic anhydride and 1-octadecene and the elastomer may be a hydroxy-terminated polybutadiene.

Claims

1. An asphalt composition comprising a reaction product from reaction of a copolymer and an unsaturated elastomer in the presence of an asphalt;

said coploymer having substantial anhydride functionality and comprising a reaction product from reaction of an anhydride and an olefin; and

said unsaturated elastomer having at least two terminal allylic groups.

2. An asphalt composition according to claim 1 which further includes a petroleum oil.

3. An asphalt composition according to claim 2 in which said oil is paraffinic or cycloparaffinic.

4. An asphalt composition according to claim 1 in which said alpha-olefin is an aliphatic olefin.

5. An asphalt composition according to claim 4 in which the number of carbon atoms in said aliphatic olefin is greater than 5.

6. An asphalt composition according to claim 4 in which the number of carbon atoms in said aliphatic olefin is greater than 15.

7. An asphalt composition according to claim 4 in which the number of carbon atoms in said aliphatic olefin is in the range of 16 to 18.

8. An asphalt composition according to claim 1 in which said olefin is 1-hexadecene;

2-hexadecene;

1-heptadecene;

1-octadecene;

2-octadecene;

or 2-methyl-1-heptadecene.

9. An asphalt composition according to claim 1 in which said olefin is 1-octadecene and said elastomer is a hydroxy-terminated polybutadiene.

10. An asphalt composition according to claim 1 in which said olefin is 1-octadecene and said anhydride is maleic anhydride.

11. An asphalt composition according to claim 10 in which said elastomer is a polychloroprene polymer, a nitrile-butadiene polymer, a styrene-butadiene polymer or a polybutadiene polymer.

12. An asphalt composition according to claim 1 in which said elastomer is capable of undergoing a Diels-Alder reaction with at least one constituent of said asphalt.

13. An asphalt composition according to claim 1 in which said copolymer has a molecular weight of at least about 10,000.

14. An asphalt composition according to claim 1 in which said copolymer has a molecular weight of at least about 40,000.

15. An asphalt composition according to claim 1 in which said copolymer is a polyanhydride.

16. An asphalt composition according to claim 1 in which said olefin is 1-hexadecene, 2-hexadecene;

1-heptadecene;

1-octadecene, 2-octadecene, or 2-methyl-1-heptadecene;

in which said anhydride is maleic anhydride, citraconic anhydride, itaconic anhydride, glutaconic anhydride or methyl itaconic anhydride; and

in which said elastomer is a polychloroprene polymer, a nitrile-butadiene polymer, a styrene-butadiene polymer or a polybutadiene polymer.

17. An asphalt composition according to claim 10 in which said elastomer is a hydroxy-terminated polybutadiene.

18. An asphalt composition according to claim 1 which further includes solid particles of a natural or synthetic filler material.

19. An asphalt composition according to claim 1 in which said copolymer and said elastomer are present in relative amounts sufficient to lower the viscosity of said asphalt.

20. An article of manufacture comprising a substrate coated with an asphalt composition according to claim 1.

36. An asphalt composition according to claim 1 which is a paving composition further comprising solid particles of a natural or synthetic aggregate.

21. An asphalt composition comprising a reaction product from reaction of:

an asphalt;

a copolymer having substantial anhydride functionality and comprising a reaction product from reaction of an olefin and an anhydride; and

,

an unsaturated elastomer having at least two terminal groups at least one of which is an allylic hydroxyl group and the other of which has an active hydrogen, a halogen, an epoxy oxygen or a cyanocarbon.

41. An asphalt composition according to claim 21 in which both of said terminal groups are allylic hydroxyl groups, and said anhydride comprises maleic anhydride.

44. An asphalt composition according to claim 21 in which both of said terminal groups are allylic hydroxyl groups, and said copolymer is a polyanhydride having an anhydride equivalent in the range of 3.10 to 3.25 meg/g.

45. An asphalt composition according to claim 21 in which both of said terminal groups are allylic hydroxyl groups, and said copolymer is a polyanhydride having an anhydride content by weight of about 15% to about 23%.

22. A method of preparing an asphalt composition comprising:

mixing a petroleum oil with a copolymer having substantial anhydride functionality and comprising a reaction product from reaction of an anhydride and an olefin; and

,

mixing and reacting said copolymer and oil mixture with an unsaturated elastomer in the presence of an asphalt, said unsaturated elastomer having at least two terminal groups at least one of which is an allylic hydroxyl group and the other of which has an active hydrogen, a halogen, an epoxy oxygen or a cyanocarbon.

23. The method according to claim 22 in which said oil is paraffinic or cycloparaffinic.

24. The method according to claim 22 in which said olefin is 1-octadecene, said anhydride is maleic anhydride, and said unsaturated elastomer is a hydroxy-terminated polybutadiene.

25. A method according to claim 24 in which said oil is paraffinic.

26. A method according to claim 22 in which said copolymer and oil mixture is first mixed with said unsaturated elastomer and thereafter mixed with said asphalt.

42. An asphalt composition according to claim 22 in which both of said terminal groups are allylic hydroxyl groups, and said anhydride comprises maleic anhydride.

48. A method according to claim 22 which further comprises heating said copolymer and oil mixture before said mixture is mixed and reacted with said unsaturated elastomer in the presence of the asphalt.

49. A method according to claim 48 which further comprises cooling said heated copolymer and oil mixture before said mixture is mixed and reacted with said unsaturated elastomer in the presence of the asphalt.

50. A method according to claim 49 which further comprises mixing said cooled copolymer and oil mixture with said unsaturated elastomer, and thereafter heating said copolymer, oil and elastomer mixture in the presence of said asphalt.

27. An asphalt composition prepared by copolymerizing maleic anhydride and an aliphatic olefin in the presence of a free radical initiator to provide a copolymer product having substantial anhydride functionality, and thereafter mixing and reacting said copolymer product with an unsaturated elastomer in the presence of an asphalt, said unsaturated elastomer having at least two terminal allylic hydroxyl groups.

28. The composition of claim 27 in which said aliphatic olefin is 1-octadecene, and said unsaturated elastomer is a hydroxy-terminated polybutadiene.

29. The composition of claim 27 in which said copolymer product is uniformly mixed with a petroleum oil before being mixed with said asphalt and said unsaturated elastomer.

30. An asphalt composition according to claim 29 in which said copolymer product and oil mixture is first mixed with said unsaturated elastomer and thereafter mixed with said asphalt.

37. An asphalt composition according to claim 27 in which said unsaturated elastomer is a butadiene homopolymer, a butadiene-styrene copolymer, a butadiene-acrylonitrile copolymer, or a mixture thereof.

31. An asphalt composition comprising a reaction product from reaction of a copolymer and an unsaturated elastomer in the presence of an asphalt;

said copolymer having substantial anhydride functionality and comprising a reaction product from reacting an olefin with an anhydride; and

said unsaturated elastomer having at least two terminal groups at least one of which is an allylic hydroxyl group and the other of which has an active hydrogen, a halogen, an epoxy oxygen, or a cyanocarbon.

32. An asphalt composition according to claim 31 in which said olefin is an aliphatic alpha-olefin.

33. An asphalt composition according to claim 32 in which said anhydride is maleic anhydride, citraconic anhydride, itaconic anhydride, glutaconic anhydride or methyl itaconic anhydride.

34. An asphalt composition according to claim 33 in which said olefin is 1-hexadecene;

2hexadecene;

1-heptadecene;

1-octadecene;

2-octadecene;

or 2-methyl-1-heptadecene;

in which both of said hydroxyl groups are of the allylic type; and

in which said elastomer is a polychloroprene polymer, a nitrile-butadiene polymer, a styrene-butadiene polymer or a polybutadiene polymer.

35. An asphalt composition according to claim 31 in which said copolymer product is first mixed with a petroleum oil and thereafter the resulting copolymer and oil product is mixed and reacted with said asphalt and said elastomer.

43. An asphalt composition according to claim 31 in which both of said terminal groups are allylic hydroxyl groups, and said anhydride comprises maleic anhydride.

46. An asphalt composition according to claim 31 in which both of said terminal groups are allylic hydroxyl groups, and said copolymer is a polyanhydride having an anhydride equivalent in the range of 3.10 to 3.25 meg/g.

47. An asphalt composition according to claim 31 in which both of said terminal groups are allylic hydroxyl groups, and said coploymer is a polyanhydride having an anhydride content by weight of about 15% to about 23%.

38. An asphalt composition comprising a reaction product from reaction of:

an asphalt;

an additive comprising a copolymer mixed with a petroleum oil, said copolymer having substantial anhydride functionality and comprising a reaction product from reaction of an anhydride and an alpha-olefin; and

,

an unsaturated elastomer having at least two terminal groups at least one of which is an allylic hydroxyl group and the other of which has an active hydrogen, a halogen, an epoxy oxygen or a cyanocarbon.

39. An asphalt composition according to claim 38 in which said copolymer is first mixed and heated with said petroleum oil and the resulting mixture is thereafter reacted with said unsaturated elastomer.

40. An asphalt composition according to claim 39 in which both of said terminal groups are allylic hydroxyl groups, and said anhydride comprises maleic anhydride.