Plant oil-based materials

Patent metadata

Field	Value
Publication number	US-9834626-B2
Application number	US-201414761082-A
Country	US
Kind code	B2
Filing date	Jan 13, 2014
Priority date	Jan 15, 2013
Publication date	Dec 5, 2017
Grant date	Dec 5, 2017

Abstract

Plant oil-based compounds are provided which possess both low viscosity and high reactive functionality. These compounds are useful in coating and composite applications, as well as related methods. Exemplary compounds can be produced by transesterification of a plant oil triglyceride with a nucleophile reactant, such as a vinyl-functional alcohol, to yield reactive fatty acid-containing monomers.

First claim

What is claimed is:

1. A functionalized polysiloxane comprising a compound having formula I:

wherein R 1 is an organic group comprising at least one double or triple carbon-carbon bond; X is O, NR 3 , N, or S; R 2 is a fatty acid residue; and R 3 is H or alkyl; provided that where R 1 comprises a double carbon-carbon bond, neither atom α to the double carbon-carbon bond is O.

2. The functionalized polysiloxane of claim 1 , wherein the fatty acid residue is from a plant oil triglyceride.

3. The functionalized polysiloxane of claim 1 , wherein R 1 is allyl.

4. The functionalized polysiloxane of claim 2 , wherein the plant oil is selected from the group consisting of soybean oil, linseed oil, sunflower oil, safflower oil, canola oil, corn oil, cashew nut oil, olive oil, peanut oil, palm oil, sesame oil, cottonseed oil, rapeseed oil, walnut oil, almond oil and coconut oil.

5. The functionalized polysiloxane of claim 4 , wherein the oil is soybean oil.

6. The functionalized polysiloxane of claim 1 , wherein at least one of R 1 and R 2 contains at least one functionality selected from the group consisting of epoxide, acrylate, methacrylate, hydroxyl, and cyclic carbonate.

7. A composition comprising a plurality of functionalized polysiloxanes of claim 1 .

8. The composition of claim 7 , wherein the plant oil is soybean oil, and wherein for each of the plurality of compounds, R 2 is a fatty acid residue independently selected from a linolenic acid, a linoleic acid, an oleic acid, a stearic acid, and a palmitic acid.

9. A curable composition comprising at least one functionalized polysiloxane of claim 1 .

10. The curable composition of claim 9 comprising a reactive diluent comprising the functionalized polysiloxane of claim 1 .

11. A urethane or polyurethane comprising the functionalized polysiloxane of claim 1 or a derivative thereof.

12. A method for making a functionalized polysiloxane comprising contacting a compound having formula I:

wherein R 1 is an organic group comprising at least one double or triple carbon-carbon bond; X is O, NR 3 , N, or S; R 2 is a fatty acid residue; and R 3 is H or alkyl; provided that where R 1 comprises a double carbon-carbon bond, neither atom α to the double carbon-carbon bond is O, with a polysiloxane to yield a functionalized polysiloxane.

13. A coating, film, fiber, foam, adhesive, ink, plastic, elastomer, paint, molding compound, thermoplastic, resin, sealant, lubricant or composite comprising the functionalized polysiloxane of claim 1 or a derivative thereof.

Assignees

• Chisholm Bret Ja
• Kalita Harjyoti
• Alam Samim
• Chernykh Andrey
• Ndsu Res Foundation

Inventors

• Chisholm Bret Ja
• Kalita Harjyoti
• Alam Samim
• Chernykh Andrey

Classifications

• C07C69/533

  Monocarboxylic acid esters having only one carbon-to-carbon double bond · CPC title

• C08G77/38

  Polysiloxanes modified by chemical after-treatment · CPC title

• C07C69/587

  Monocarboxylic acid esters having at least two carbon-to-carbon double bonds · CPC title

• C07D303/42

  Acyclic compounds having a chain of seven or more carbon atoms, e.g. epoxidised fats · CPC title

• C09D129/10

  Homopolymers or copolymers of unsaturated ethers (C09D135/08 takes precedence) · CPC title