Pressure sensitive adhesives based on fatty acids

Patent metadata

Field	Value
Publication number	US-10030182-B2
Application number	US-201214363785-A
Country	US
Kind code	B2
Filing date	Dec 5, 2012
Priority date	Dec 7, 2011
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

A method for making a pressure sensitive adhesive comprising:
(a) making at least one epoxidized fatty acid from at least one plant oil, marine oil, other ester of unsaturated fatty acid, or a mixture thereof; and (b) polymerizing the at least one epoxidized fatty acid to produce a pressure sensitive adhesive.

A method for making a pressure sensitive adhesive comprising:
(a) making epoxidized oleic acid, an epoxidized linoleic acid (including fully and partially epoxidized linoleic acid), or an epoxidized linolenic acid (including fully and partially epoxidized linolenic acid) from at least one plant oil, marine oil, other ester of unsaturated fatty acid, or making mixture thereof; and (b) polymerizing the epoxidized oleic acid, the epoxidized linoleic acid, the epoxidized linolenic acid, or the mixture thereof to produce a pressure sensitive adhesive.

First claim

What is claimed is:

1. A method for making a pressure sensitive adhesive comprising:
(a) making at least one epoxidized fatty acid from at least one plant oil, marine oil, animal fat, or a mixture thereof; and
(b) polymerizing the at least one epoxidized fatty acid to produce a pressure sensitive adhesive, wherein the pressure sensitive adhesive product is a polyester.

2. The method of claim 1 , wherein polymerizing the at least one epoxidized fatty acid to produce a pressure sensitive adhesive comprises pre-polymerizing the at least one epoxidized fatty acid at a temperature of 20 to 300° C. for 1 to 180 minutes, and then polymerizing the resulting prepolymer at a temperature of 100 to 300° C. for 10 seconds to 100 minutes.

3. The method of claim 1 , wherein polymerizing the at least one epoxidized fatty acid to produce a pressure sensitive adhesive comprises pre-polymerizing the at least one epoxidized fatty acid by reacting the at least one epoxidized fatty acid with (i) at least one carboxylic acid compound having at least two carboxylic acid groups or (ii) at least one epoxide having at least two epoxy groups.

4. The method of claim 3 , further comprising polymerizing the resulting prepolymer at a temperature of 100 to 300° C. for 10 seconds to 100 minutes.

5. The method of claim 3 , wherein the carboxylic acid compound comprises a dibasic acid or an anhydride thereof.

6. The method of claim 3 , wherein the epoxide compound is selected from an aliphatic triglycidyl or polyglycidyl ether, an aromatic triglycidyl or polyglycidyl ether, epoxy functionalized polybutadiene, alkyl diglycidyl ether, an alkyl diglycidyl ester, epoxidized fatty acid ester, epoxidized plant oil, epoxidized marine oil, or a bisphenol diglycidyl ether.

7. The method of claim 3 , further comprising applying the prepolymer onto a backing substrate or a release liner and heating the reaction product on the backing substrate or release liner at a temperature of 100-300° C. for 10 seconds to 100 minutes.

8. The method of claim 1 , wherein polymerizing the at least one epoxidized fatty acid to produce a pressure sensitive adhesive comprises pre-polymerizing the at least one epoxidized fatty acid, and co-polymerizing and/or curing the prepolymer with (i) at least one carboxylic acid compound having at least two carboxylic acid groups or (ii) at least one epoxide having at least two epoxy groups.

9. The method of claim 1 , wherein the at least one epoxidized fatty acid is made from a plant oil.

10. The method of claim 1 , comprising epoxidizing the plant oil, marine oil, or ester of unsaturated fatty acid to produce a first intermediate product, saponifying the first intermediate product to produce a second intermediate product, and acidifying the second intermediate product to produce the at least one epoxidized fatty acid.

11. The method of claim 1 , wherein the epoxidized fatty acid has a structure of R—X 1 —R—X 2 —R—X 3 —R—C(═O)—OH,
wherein X 1 , X 2 , and X 3 each independently represent

or a substituted or unsubstituted alkyl or heteroalkyl group, provided at least one of X 1 , X 2 , or X 3 is

and each R independently represents hydrogen or a substituted or unsubstituted alkyl or heteroalkyl group.

12. The method of claim 1 , wherein the plant oil is soybean oil.

13. The method of claim 1 , wherein the polyester is a cross-linked hydroxy-functional polyester.

14. A method for making a pressure sensitive adhesive comprising:
(a) making epoxidized oleic acid, an epoxidized linoleic acid (including fully and partially epoxidized linoleic acid), or an epoxidized linolenic acid (including fully and partially epoxidized linolenic acid) from at least one plant oil, marine oil, animal fat, or making a mixture thereof; and
(b) polymerizing the epoxidized oleic acid, the epoxidized linoleic acid, the epoxidized linolenic acid, or the mixture thereof to produce a pressure sensitive adhesive, wherein the pressure sensitive adhesive product is a polyester.

15. The method of claim 14 , comprising saponifying the vegetable, marine oil, or ester of unsaturated fatty acid to produce a first intermediate product, acidifying the first intermediate product to produce a second intermediate product, and epoxidizing the second intermediate product to produce the at least one epoxidized fatty acid.

16. The method of claim 14 , wherein making an epoxidized oleic acid, an epoxidized linoleic acid, or epoxidized linolenic acid from a plant oil, marine oil, other ester of unsaturated fatty acid, or making the mixture thereof, comprises alkanolysis of the plant, marine oil, or other ester of unsaturated fatty acid to produce a first intermediate product, epoxidization of the first intermediate product to produce a second intermediate product, and saponification and acidification of the second intermediate product to produce the epoxidized oleic acid, the epoxidized linoleic acid, the epoxidized linolenic acid, or the mixture thereof.

17. The method of claim 14 , wherein polymerizing the epoxidized oleic acid, the epoxidized linoleic acid, the epoxidized linolenic acid, or the mixture thereof to produce a pressure sensitive adhesive comprises pre-polymerizing the epoxidized oleic acid, the epoxidized linoleic acid, the epoxidized linolenic acid, or the mixture thereof with (i) at least one carboxylic acid compound having at least two carboxylic acid groups or (ii) at least one epoxide having at least two epoxy groups.

18. The method of claim 14 , wherein polymerizing the epoxidized oleic acid, the epoxidized linoleic acid, the epoxidized linolenic acid, or the mixture thereof to produce a pressure sensitive adhesive comprises pre-polymerizing the epoxidized oleic acid, the epoxidized linoleic acid, the epoxidized linolenic acid, or the mixture thereof, and co-polymerizing and/or curing the prepolymer with (i) at least one carboxylic acid compound having at least two carboxylic acid groups or (ii) at least one epoxide having at least two epoxy groups.

19. The method of claim 14 , wherein the polyester is a cross-linked hydroxy-functional polyester.

20. A method for making a pressure sensitive adhesive construct comprising:
making at least one epoxidized fatty acid from at least one plant oil, marine oil, animal fat, or a mixture thereof; and
forming on a backing substrate a pressure sensitive adhesive from the resulting at least one epoxidized fatty acid, wherein the pressure sensitive adhesive is a polyester.

21. The method of claim 20 , wherein the forming of the pressure sensitive adhesive on the backing substrate comprises pre-polymerizing the at least one epoxidized fatty acid, applying the prepolymer to the backing substrate, and further polymerizing and/or thermally curing the prepolymer on the substrate.

22. The method of claim 21 , wherein
the prepolymer is applied onto a release liner or a backing substrate;
a backing substrate is placed onto a surface of the prepolymer coating opposing the release liner, or a release liner is placed on a surface of the prepolymer coating opposing the backing substrate, to form a release liner/prepolymer/backing substrate assembly;
pressure is applied to the resulting assembly; and
at least the prepolymer on the backing substrate or release liner is heated to produce the

Assignees

• State Of Oregon Acting By And Through The State Board Of Higher Education On Behalf Of Oregon State
• Univ Oregon State

Inventors

• Li Kaichang
• Li Anlong

Classifications

• C08G59/36

  together with mono-epoxy compounds · CPC title

• B32B37/02

  characterised by a sequence of laminating steps, e.g. by adding new layers at consecutive laminating stations · CPC title

• C09J2463/00

  Presence of epoxy resin · CPC title

• C09J163/00 Primary

  Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins · CPC title

• C09J2463/008

  in the pretreated surface to be joined · CPC title