Polymerized oils and methods of manufacturing the same

Patent metadata

Field	Value
Publication number	US-10316189-B2
Application number	US-201715715665-A
Country	US
Kind code	B2
Filing date	Sep 26, 2017
Priority date	Feb 27, 2015
Publication date	Jun 11, 2019
Grant date	Jun 11, 2019

Abstract

Described herein is a polymerized biorenewable, previously modified, or functionalized oil, comprising a polymeric distribution having about 2 to about 80 wt % oligomer content, a polydispersity index ranging from about 1.30 to about 2.20, and sulfur content ranging from 0.001 wt % to about 8 wt %. Methods of manufacturing the polymerized oil as well as its incorporation into asphalt paving, roofing, and coating applications are also described.

First claim

The invention claimed is:

1. A polymerized oil comprising:
a biorenewable, previously modified, or functionalized oil crosslinked with a sulfur-containing compound and having
(a) a polymeric distribution having about 2 to about 80 wt % oligomer content;
(b) a polydispersity index ranging from about 1.30 to about 2.20; and
(c) sulfur content ranging from 0.001 wt % to about 8 wt %.

2. The polymerized oil of claim 1 , wherein the polymeric distribution has about 15 to about 60 wt % oligomer content.

3. The polymerized oil of claim 1 , wherein the polydispersity index ranges from about 1.50 to about 2.05.

4. The polymerized oil of claim 1 , wherein the sulfur content is less than about 6 wt %.

5. The polymerized oil of claim 1 , wherein the sulfur content is less than about 4 wt %.

6. The polymerized oil of claim 1 , wherein the sulfur content is less than about 2 wt %.

7. The polymerized oil of claim 1 , having a flash point ranging from about 100° C. to about 400° C.

8. The polymerized oil of claim 1 , having a flash point ranging from about 200° C. to about 350° C.

9. The polymerized oil of claim 1 , having a flash point ranging from about 245° C. to about 275° C.

10. The polymerized oil of claim 1 , wherein the biorenewable, previously modified, or functionalized oil is selected from the group consisting of palm oil, sunflower oil, corn oil, soybean oil, canola oil, rapeseed oil, linseed oil, tung oil, castor oil, tall oil, cottonseed oil, peanut oil, safflower oil, corn stillage oil, and combinations and crude streams thereof.

11. The polymerized oil of claim 1 , wherein the biorenewable, previously modified, or functionalized oil comprises an alkyl ester.

12. The polymerized oil of claim 11 , wherein the biorenewable, previously modified, or functionalized oil is selected from the group consisting of methyl, ethyl, propyl, and butyl esters, and combinations thereof.

13. The polymerized oil of claim 1 , wherein the biorenewable, previously modified, or functionalized oil has been previously modified.

14. The polymerized oil of claim 1 , wherein the biorenewable, previously modified, or functionalized oil is selected from the group consisting of triacylglycerides, diacylglycerides, monoacylglycerides, and combinations thereof.

15. The polymerized oil of claim 1 , wherein the sulfur-containing compound is elemental sulfur.

16. The polymerized oil of claim 15 , wherein the crosslinking comprises heating to about 130° C. to about 250° C.

17. The polymerized oil of claim 15 , wherein the crosslinking comprises heating to about 130° C. to about 220° C.

18. The polymerized oil of claim 15 , wherein the crosslinking comprises heating to about 160° C. to about 200° C.

19. The polymerized oil of claim 1 , wherein the sulfur content is 0.01 wt % to 8 wt %.

20. A modified asphalt comprising the polymerized oil of claim 1 .

21. A rejuvenator for use in asphalt comprising the polymerized oil of claim 1 .

22. A modified asphalt, comprising:
(a) about 60 to about 99.9 wt % asphalt binder; and
(b) about 0.1 to about 40 wt % polymerized oil crosslinked with a sulfur-containing compound and comprising
i. a polymeric distribution having about 2 to about 80 wt % oligomer content;
ii. a polydispersity index ranging from about 1.30 to about 2.20; and
iii. sulfur content less than about 8 wt %.

23. The modified asphalt of claim 22 , wherein the asphalt binder is for paving applications.

24. A method of incorporating a polymerized oil in asphalt applications, comprising:
(a) obtaining a polymerized oil crosslinked with a sulfur-containing compound, the polymerized oil comprising:
i. a polymeric distribution having about 2 to about 80 wt % oligomer content;
ii. a polydispersity index ranging from about 1.30 to about 2.20; and
iii. sulfur content less than about 8 wt %; and

(b) adding the polymerized oil to treat reclaimed asphalt pavement millings (RAP) to be reused in asphalt pavements, thereby obtaining a modified asphalt; wherein the amount of the polymerized oil ranges from 0.1 to 40 wt % of the modified and rejuvenated asphalt.

25. The method of claim 24 , further comprising blending the treated reclaimed asphalt pavement millings with bitumen.

Assignees

• Cargill Inc

Inventors

• Kurth Todd L
• Nivens Scott
• Stevermer Christopher Patrick
• Tabatabaee Hassan Ali

Classifications

• C08L95/00

  Compositions of bituminous materials, e.g. asphalt, tar, pitch · CPC title

• C09F7/06

  by polymerisation · CPC title

• C09D195/00

  Coating compositions based on bituminous materials, e.g. asphalt, tar, pitch · CPC title

• C08L91/02

  Vulcanised oils, e.g. factice · CPC title

• C08L99/00

  Compositions of natural macromolecular compounds or of derivatives thereof not provided for in groups C08L89/00 - C08L97/00 · CPC title