Epoxidized polyfarnesene and methods for producing the same

Patent metadata

Field	Value
Publication number	US-10745503-B2
Application number	US-201816104384-A
Country	US
Kind code	B2
Filing date	Aug 17, 2018
Priority date	Aug 18, 2017
Publication date	Aug 18, 2020
Grant date	Aug 18, 2020

Abstract

Aspects of the present invention relate to polymers, and particularly to farnesene polymers functionalized with one or more oxirane groups and, optionally, one or more hydroxyl groups. According to one aspect of the invention, provided is an epoxidized and optionally hydroxyl-functionalized polyfarnesene. The epoxidized farnesene polymer has at least one of a side chain or a main backbone functionalized with at least one oxirane group and, optionally, at least one terminal end functionalized with a hydroxyl group. In accordance with another aspect of the invention, a method is provided for preparing an epoxidized and optionally hydroxyl-functionalized polyfarnesene. The method includes epoxidizing a farnesene polymer, which may optionally contain one or more terminal hydroxyl groups, to functionalize at least one of a side chain or a main backbone of the farnesene polymer with an oxirane group.

First claim

What is claimed is:

1. An epoxidized polyfarnesene comprising:
a farnesene polymer having at least a side chain or a main backbone functionalized with at least one oxirane group and wherein the farnesene polymer has at least one terminal end functionalized with a hydroxyl group.

2. The epoxidized polyfarnesene of claim 1 , wherein the farnesene polymer comprises at least one tri-substituted oxirane group.

3. The epoxidized polyfarnesene of claim 2 , wherein the tri-substituted oxirane group is bonded to the main backbone or the side chain of the farnesene polymer.

4. The epoxidized polyfarnesene of claim 1 , wherein the farnesene polymer comprises a farnesene monomer and at least one comonomer in polymerized form.

5. The epoxidized polyfarnesene of claim 4 , wherein the at least one comonomer comprises at least one comonomer selected from the group consisting of butadiene, isoprene, and vinyl aromatics.

6. The epoxidized polyfarnesene of claim 1 , wherein the farnesene polymer has a number average molecular weight of 100,000 g/mol or less.

7. The epoxidized polyfarnesene of claim 6 , wherein the farnesene polymer has a number average molecular weight of 25,000 g/mol or less.

8. The epoxidized polyfarnesene of claim 1 , wherein the farnesene polymer has a viscosity at 25° C. of 10,000 cP or less.

9. The epoxidized polyfarnesene of claim 1 , wherein the farnesene polymer has a viscosity at 25° C. of not more than 50% of that of a hydroxyl-terminated butadiene polymer of the same number average molecular weight and oxirane content.

10. The epoxidized polyfarnesene of claim 1 , wherein the farnesene polymer has an amount of oxirane oxygen of from 0.5% to 10%, by weight.

11. A method for preparing a crosslinked composition, comprising curing a composition comprised of an epoxidized farnesene polymer in accordance with claim 1 to produce cross linking between individual epoxidized farnesene polymer molecules, wherein the epoxidized farnesene polymer molecules are at least one of a homopolymer or a copolymer.

12. A method for preparing an epoxide functionalized polyfarnesene comprising:
epoxidizing a farnesene polymer to functionalize at least one of a side chain or a main backbone of the farnesene polymer with at least one oxirane group and further comprising functionalizing at least one terminal end of the farnesene polymer with a hydroxyl group.

13. The method of claim 12 , further comprising a step of hydrogenating the farnesene polymer.

14. The method of claim 13 , wherein the step of hydrogenating the farnesene polymer is performed such that the oxirane group is not opened.

15. The method of claim 13 , wherein the step of hydrogenating the farnesene polymer is performed before the epoxidation step.

16. A composition comprising:
at least one epoxide functionalized farnesene polymer having at least one side chain or main chain functionalized with an oxirane group and at least one terminal end functionalized with a hydroxyl group; and
at least one epoxide other than the epoxide functionalized farnesene polymer.

17. The composition of claim 16 , wherein the at least one epoxide other than the epoxide functionalized farnesene polymer comprises at least one epoxidized diene-based copolymer, the epoxidized diene-based copolymer comprising, in polymerized form, at least one diene monomer and, optionally, at least one vinyl aromatic monomer.

Assignees

• Fina Technology

Inventors

• Chao Herbert
• Yoo Taejun
• Nehache Sabrina

Classifications

• C08L63/08

  Epoxidised polymerised polyenes · CPC title

• C08G59/027

  obtained by epoxidation of unsaturated precursor, e.g. polymer or monomer · CPC title

• C08F236/22 Primary

  the radical having three or more carbon-to-carbon double bonds · CPC title

• C08F136/22

  the radical having three or more carbon-to-carbon double bonds · CPC title

• C08F36/22 Primary

  the radical having three or more carbon-to-carbon double bonds · CPC title