Synthesis of cross-linked plant-oil based polymers using bismaleimides as crosslinkers

Patent metadata

Field	Value
Publication number	US-10059790-B2
Application number	US-201414916625-A
Country	US
Kind code	B2
Filing date	Sep 5, 2014
Priority date	Sep 5, 2013
Publication date	Aug 28, 2018
Grant date	Aug 28, 2018

Abstract

A method of preparing a plant oil based polymer comprising heating a plant oil in the presence of a bismaleimide crosslinker in the substantial absence of a solvent at a temperature at or above the melting temperature of the bismaleimide crosslinker, where the bismaleimide crosslinker is defined by the formula

where R 1 is a divalent organic group.

First claim

What is claimed is:

1. A method of preparing a plant oil based polymer comprising heating a plant oil in the presence of a bismaleimide crosslinker in the substantial absence of a solvent at a temperature of 130° C. to 200° C. to thereby form a plant oil based polymer in one step, where the bismaleimide crosslinker is defined by the formula

where R l is a divalent organic group.

2. The method of claim 1 , where the method is performed in less than 5% solvent.

3. The method of claim 1 , where the method is performed in the absence of a solvent.

4. The method of claim 1 , where at least 22% maleimine groups of the bismaleimide crosslinker react with the plant oil through an ene reaction.

5. The method of claim 1 , where the plant oil is a fatty acid, fatty ester, glycerolipid or combination thereof.

6. The method of claim 1 , where the plant oil is a glycerolipid and the glycerolipid is a triglyceride.

7. The method of claim 1 , where the plant oil is selected from soybean oil, linseed oil, corn oil, cotton seed oil, palm oil, and peanut oil.

8. The method of claim 1 , where the bismaleimide crosslinker is defined by the formula

where R 2 is a divalent organic group and each p is individually 0 to about 36 units, and n is about 1 to about 10 units.

9. The method of claim 1 , where the bismaleimide crosslink is defined by the formula

where each R 3 is individually a divalent organic group and each n is individually about 1 to about 10 units.

10. The method of claim 1 , where the bismaleimide crosslinker is selected from the group consisting of

where each p is individually 0 to about 36 units, and

where n is about 1 to about 10.

11. A method of preparing a plant oil based polymer comprising heating a reaction mixture consisting essentially of a plant oil and a bismaleimide crosslinker at a temperature of 130° C. to 200° C. to thereby form a plant oil based polymer in one step, where the bismaleimide crosslinker is defined by the formula

where R l is a divalent organic group.

12. A method of preparing a plant oil based polymer comprising:
(i)preparing a reaction mixture that is essentially solvent free by combining a plant oil and a bismaleimide crosslinker;
(ii) heating said reaction mixture at a temperature of 130° C. to 200° C. until a crosslinked polymer is formed, where the bismaleimide crosslinker is defined by the formula

where R 1 is a divalent organic group.

13. A method of preparing a plant oil based polymer comprising
heating a plant oil in the presence of a bismaleimide crosslinker in the substantial absence of a solvent to a temperature at or above the melting temperature of the bismaleimide crosslinker, where the bismaleimide crosslinker is defined by the formula

where R 2 is a divalent organic group and each p is individually 0 to about 36 units, and n is about 1 to about 10 units.

14. A method of preparing a plant oil based polymer comprising heating a plant oil in the presence of a bismaleimide crosslinker in the substantial absence of a solvent to a temperature at or above the melting temperature of the bismaleimide crosslinker, where the bismaleimide crosslink is defined by the formula

where each R 3 is individually a divalent organic group and each n is individually about 1 to about 10 units.

Assignees

• Pugh Coleen
• Watt Paula
• Mehta Brinda
• Univ Akron

Inventors

• Pugh Coleen
• Watt Paula
• Mehta Brinda

Classifications

• C07D487/04

  Ortho-condensed systems · CPC title

• B01J31/06

  containing polymers {(organometallic polymers B01J31/123; polymer-bound organometallic complexes B01J31/165; coordination polymers B01J31/1691)} · CPC title

• C07D403/10

  linked by a carbon chain containing aromatic rings · CPC title

• C07D207/452

  with hydrocarbon radicals, substituted by hetero atoms, directly attached to the ring nitrogen atom · CPC title

• C08F222/40 Primary

  Imides, e.g. cyclic imides · CPC title