Modified soybean oil-extended SBR compounds and vulcanizates filled with carbon black

Patent metadata

Field	Value
Publication number	US-10035903-B2
Application number	US-201415037154-A
Country	US
Kind code	B2
Filing date	Nov 18, 2014
Priority date	Nov 18, 2013
Publication date	Jul 31, 2018
Grant date	Jul 31, 2018

Abstract

Rubber formulations include a rubber and a norbornylized seed oil. The norbornylized seed oil is a seed oil that is modified with norbornylene groups. The norbornylized seed oil can replace petroleum oils currently often used in rubber formulations. A process for creating a rubber formulation includes the steps of adding a norbornylized seed oil to a rubber, wherein the norbornylized seed oil is a seed oil modified with norbornylene groups.

First claim

What is claimed is:

1. A rubber formulation comprising:
a rubber including norbornylized seed oil, wherein said norbornylized seed oil is a seed oil modified with norbornylene groups.

2. The rubber formulation of claim 1 , wherein said rubber is selected from natural and synthetic rubbers.

3. The rubber formulation of claim 1 , wherein said seed oil is selected from soybean oil, linseed oil, sunflower oil, safflower oil, palm oil, and kernel oil.

4. The rubber formulation of claim 1 , wherein said seed oil, prior to modification with norbornylene groups, has fatty acid chains with carbon-carbon double bonds, and said seed oil is modified with norbornylene groups by having at least some of said carbon-carbon double bonds converted into norbornylene groups.

5. The rubber formulation of claim 4 , wherein from 3% or more to 50% or less of the carbon-carbon double bonds of said seed oil is converted into norbornylene groups.

6. The rubber formulation of claim 4 , wherein from 3% or more to 20% or less of the carbon-carbon double bonds of said seed oil is converted into norbornylene groups.

7. The rubber formulation of claim 1 , wherein said rubber formulation includes from 5 to 40 parts norbornylized seed oil per hundred parts rubber.

8. The rubber formulation of claim 1 , wherein said rubber formulation includes from 10 to 30 parts norbornylized seed oil per hundred parts rubber.

9. The rubber formulation of claim 1 , wherein said rubber formulation further comprises a filler selected from carbon black, silica filler, nanoclay, carbon nanotubes, carbon nanofibers, nanodiamonds, graphite, graphene and mixtures thereof.

10. The rubber formulation of claim 1 , wherein said rubber is a natural and synthetic rubber and said norbornylized seed oil is norbornylized soybean oil.

11. A process for creating a rubber formulation comprising:
adding a norbornylized seed oil to a rubber, wherein the norbornylized seed oil is a seed oil modified with norbornylene groups.

12. The process for creating a rubber formulation as in claim 11 , wherein said rubber is selected from natural and synthetic rubbers.

13. The process for creating a rubber formulation as in claim 11 , wherein said seed oil is selected from soybean oil, linseed oil, sunflower oil, safflower oil, palm oil, kernel oil, or the like.

14. The process for creating a rubber formulation as in claim 11 , further comprising the step of creating the norbornylized seed oil by reacting the seed oil with dicyclopentadiene.

15. The process for creating a rubber formulation as in claim 14 , wherein, in said step of creating the norbornylized seed oil, the stoichiometric ratio of dicyclopentadiene to carbon-carbon double bonds of the seed oil is from 1 to 10 to 5:1.

16. The process for creating a rubber formulation as in claim 11 , wherein, in said step of creating the norbornylized seed oil, at least 5% or more to 40% or less of the carbon-carbon double bonds of the seed oil are converted into norbornylene groups.

17. The process for creating a rubber formulation as in claim 11 , wherein, in said step of adding a norbornylized seed oil, from 3 to 40 parts norbornylized seed oil per hundred parts rubber is added to the rubber.

18. The process for creating a rubber formulation as in claim 11 , further comprising the step of adding a filler to the rubber, wherein said filler is selected from carbon black, silica filler, nanoclay, carbon nanotubes, carbon nanofibers, nanodiamonds, graphite, graphene and mixtures thereof.

19. The process for creating a rubber formulation as in claim 18 , wherein, in said step of adding a filler, from 10 to 80 parts carbon black per hundred parts rubber is added to the rubber.

20. The process for creating a rubber formulation as in claim 11 , further comprising the step of curing the rubber.

21. A process for creating a vulcanized composition, the process comprising vulcanizing a rubber formulation:
including norbornylized seed oil, wherein said norbornylized seed oil is a seed oil modified with norbornylene groups,
wherein the vulcanized composition has a greater elongation at break than an identical vulcanized composition prepared using a rubber formulation that includes an otherwise identical non-norbornylized seed oil.

Assignees

• Soucek Mark
• Isayev Avraam
• Univ Akron

Inventors

• Soucek Mark
• Isayev Avraam

Classifications

• C08L2207/322

  Liquid component is processing oil · CPC title

• C08L91/00

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

• C08K3/04

  Carbon · CPC title

• C08L9/06 Primary

  Copolymers with styrene · CPC title

• C08L2205/06

  having improved processability or containing aids for moulding methods · CPC title