Polymerized oils and methods of manufacturing the same

Patent metadata

Field	Value
Publication number	US-11905415-B2
Application number	US-201816227836-A
Country	US
Kind code	B2
Filing date	Dec 20, 2018
Priority date	Feb 27, 2015
Publication date	Feb 20, 2024
Grant date	Feb 20, 2024

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 method of polymerizing a biorenewable, previously modified, or functionalized oil, comprising:
heating a biorenewable, previously modified, or functionalized oil to at least 100° C., wherein the oil comprises soybean oil, canola oil, rapeseed oil, castor oil, tall oil, sunflower oil, palm oil, peanut oil, safflower oil, corn oil, corn stillage oil, lecithin, an animal-based oil, or a combination thereof;
adding a sulfur-containing compound to the heated oil; and
allowing the sulfur-containing compound to react with the oil to produce a polymerized oil crosslinked with the sulfur-containing compound, the oil comprising
a polymeric distribution having about 2 to about 80 wt % oligomer content, and
a. sulfur content ranging from 0.001 wt % to 8 wt %.

2. The method of claim 1 , further comprising passing a gas-containing stream through the reaction mixture during the reaction of the sulfur-containing compound with the oil.

3. The method of claim 2 , wherein the gas-containing stream is selected from the group consisting of nitrogen and inert gas.

4. The method of claim 1 , wherein during the heating of the oil, the oil is heated to about 130° C. to about 250° C.

5. The method of claim 1 , wherein the sulfur-containing compound is added in a solid form.

6. The method of claim 1 , wherein the sulfur--containing compound is added in a molten form.

7. The method of claim 1 , wherein the sulfur-containing compound is a reduced form of sulfur.

8. The method of claim 1 , wherein the sulfur-containing compound is elemental sulfur.

9. The method of claim 1 , further comprising adding an accelerator after adding the sulfur-containing compound to the heated oil.

10. The method of claim 1 , wherein the oligomer content ranges from about 15 to about 60 wt %.

11. The method of claim 1 , wherein the sulfur content is less than about 6 wt %.

12. The method of claim 1 , wherein the sulfurcontent is less than about 2 wt %.

13. The method of claim 1 , wherein the polymerized oil has a flash point ranging from about 245° C. to about 275° C.

14. A modified asphalt comprising the polymerized oil made in accordance to claim 1 .

15. A modified asphalt for use in compositions for paving roads comprising the polymerized oil made in accordance to claim 1 .

16. A modified asphalt for use in compositions for roofing materials comprising the polymerized oil made in accordance to claim 1 .

17. A rejuvenator for use in asphalt comprising polymerized oil made according to claim 1 .

18. A performance grade modifier for use in asphalt comprising polymerized oil made according to claim 1 .

19. A compatibilizer and swelling agent for use in asphalt comprising polymerized oil made according to claim 1 .

20. A warm mix additive for use in asphalt comprising polymerized oil made according to claim 1 .

21. The method of claim 1 , wherein the polymerized oil crosslinked with the sulfur-containing compound is a liquid at 40° C.

22. The method of claim 1 , wherein a weight ratio of the polymerized oil to a combination of the biorenewable, previously modified, or functionalized oil and the sulfur content of the polymerized oil is 1:1.

23. The method of claim 1 , wherein all sulfur-containing crosslinks present in the polymerized oil are between molecules of the biorenewable, previously modified, or functionalized oil.

24. A method of polymerizing a biorenewable, previously modified, or functionalized oil, comprising:
heating a biorenewable, previously modified, or functionalized oil to at least 100° C.;
adding a sulfur-containing compound to the heated oil; and
allowing the sulfur-containing compound to react with the oil to produce a polymerized oil crosslinked with the sulfur-containing compound, the oil comprising
a polymeric distribution having about 2 to about 80 wt % oligomer content, and
a sulfur content ranging from 0.001 wt % to 8 wt %;

wherein
a weight ratio of the polymerized oil to a combination of the biorenewable, previously modified, or functionalized oil and the sulfur content of the polymerized oil is 1:1, or
all sulfur-containing crosslinks present in the polymerized oil are between molecules of the biorenewable, previously modified, or functionalized oil, or
a combination thereof.

25. A method of polymerizing a biorenewable, previously modified, or functionalized oil, comprising:
heating a biorenewable, previously modified, or functionalized oil to at least 100° C.;
adding a sulfur-containing compound to the heated oil;
allowing the sulfur-containing compound to react with the oil to produce a polymerized oil crosslinked with the sulfur-containing compound, the oil comprising
a polymeric distribution having about 2 to about 80 wt % oligomer content, and
a sulfur content ranging from 0.001 wt % to 8 wt %; and
further comprising passing a gas-containing stream through the reaction mixture during the reaction of the sulfur-containing compound with the oil, wherein the gas-containing stream is selected from the group consisting of nitrogen and inert gas.

Assignees

• Cargill Inc

Inventors

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

Classifications

• C08L91/00 Primary

  Compositions of oils, fats or waxes; Compositions of derivatives thereof · CPC title

• C08H3/00 Primary

  Vulcanised oils, e.g. factice · CPC title

• C08L91/02

  Vulcanised oils, e.g. factice · CPC title

• C08L95/00

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

• C08L95/005

  Aqueous compositions, e.g. emulsions · CPC title