Vegetable oil-based pressure-sensitive adhesives

Patent metadata

Field	Value
Publication number	US-9556368-B2
Application number	US-201214363781-A
Country	US
Kind code	B2
Filing date	Dec 5, 2012
Priority date	Dec 7, 2011
Publication date	Jan 31, 2017
Grant date	Jan 31, 2017

Abstract

One embodiment is a pressure sensitive adhesive construct comprising:
(a) a backing substrate; and (b) a pressure sensitive adhesive composition disposed on the backing substrate, wherein the pressure sensitive adhesive composition includes a product made from
(i) at least one epoxidized vegetable oil and; (ii) a dimer acid or anhydride thereof, a trimer acid or anhydride thereof, a polymerized fatty acid or anhydride thereof, or a mixture thereof.

A further embodiment is a pressure sensitive adhesive construct comprising:
(A) a backing substrate; and (B) a pressure sensitive adhesive composition disposed on the backing substrate, wherein the pressure sensitive adhesive composition includes a product made from
(i) at least one epoxidized vegetable oil and; (ii) a prepolymer or oligomer capped with a carboxylic acid group at both prepolymer or oligomer chain ends, or a branched prepolymer or oligomer with at least two of the prepolymer or oligomer branches and chain ends capped with a carboxylic acid group, wherein the carboxylic acid-capped prepolymer or oligomer is made from (a) a dibasic acid reacted with (b) a glycidyl or an epoxidized compound having at least two epoxy groups, a diol or polyol, a diamine, or a combination thereof.

First claim

What is claimed is:

1. A pressure sensitive adhesive construct comprising:
(A) a backing substrate; and
(B) a pressure sensitive adhesive composition disposed on the backing substrate, wherein the pressure sensitive adhesive composition includes a product made from
(i) at least one epoxidized vegetable oil and;
(ii) a prepolymer or oligomer capped with a carboxylic acid group at both prepolymer or oligomer chain ends, or a branched prepolymer or oligomer with at least two of the prepolymer or oligomer branches and chain ends capped with a carboxylic acid group, wherein the carboxylic acid-capped prepolymer or carboxylic acid-capped oligomer is made from (a) an excess of dibasic acid reacted with (b) a glycidyl or an epoxidized compound having at least two epoxy groups, or a combination thereof.

2. The construct of claim 1 , wherein the epoxidized vegetable oil is epoxidized soybean oil.

3. The construct of claim 1 , wherein the pressure sensitive adhesive composition includes at least about 50 weight percent of the product, based on the total weight of the pressure sensitive adhesive composition.

4. The construct of claim 1 , wherein the pressure sensitive adhesive is disposed on the backing substrate at a coating level of 2 to 10 mg/cm 2 .

5. The construct of claim 1 , wherein the dibasic acid comprises a dimer acid.

6. The construct of claim 5 , wherein the dimer acid is a dimer of linoleic acid, oleic acid, or a mixture thereof.

7. The construct of claim 5 , wherein the dimer acid is a dimer of an unsaturated fatty acid.

8. The construct of claim 1 , wherein the dibasic acid comprises sebacic acid.

9. The construct of claim 1 , wherein the dibasic acid is reacted with a diglycidyl ether.

10. The construct of claim 1 , wherein the pressure sensitive adhesive composition comprises a polymer that is a reaction product of (i) and (ii).

11. The construct of claim 1 , wherein the glycidyl or the epoxidized compound having at least two epoxy groups is selected from bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol A propoxylate diglycidyl ether, bisphenol A ethoxylate diglycidyl ether, diethylene glycol diglycidyl ether, 1,3-butanediol diglycidyl ether, 1,4-butanediol diglycidyl ether, poly(ethylene glycol) diglycidyl ether, poly(propylene glycol) diglycidyl ether, neopentyl glycol diglycidyl ether, glycerol diglycidyl ether, diglycidyl 1,2,3,6-tetrahydrophthalate, 1,2-cyclohexanedicarboxylate diglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether, resorcinol diglycidyl ether, poly(dimethylsiloxane) terminated with diglycidyl ether, epoxidized linoleic acid ester, epoxidized vegetable oils with two epoxy functional groups, trimethylolpropane triglycidyl ether, trimethylolethane triglycidyl ether, N,N-Diglycidyl-4-glycidyloxyaniline, tris(4-hydroxyphenyl)methane triglycidyl ether, or tris(2,3-epoxypropyl) isocyanurate.

12. The construct of claim 1 , wherein the prepolymer or oligomer includes repeating units having a structure of:

wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 independently represents hydrogen or a substituted or unsubstituted alkyl or heteroalkyl group.

13. The construct of claim 1 , wherein (B)(ii)(b) is a glycidyl.

14. A pressure sensitive adhesive construct comprising:
(I) a backing substrate; and
(II) a pressure sensitive adhesive composition disposed on the backing substrate, wherein the pressure sensitive adhesive composition comprises a a reaction product made by reacting
(A) an epoxidized vegetable oil with;
(B) a component selected from:
(i) a dimer acid or anhydride thereof, a trimer acid or anhydride thereof, or a mixture thereof;
(ii) a prepolymer or oligomer capped with a carboxylic acid group at both prepolymer or oligomer chain ends, or a branched prepolymer or oligomer with at least two of the prepolymer or oligomer branches and chain ends capped with a carboxylic acid group, wherein the carboxylic acid-capped prepolymer or oligomer is made from a (a) an excess of a dibasic acid reacted with (b) a glycidyl or an epoxidized compound having at least two epoxy groups, or a combination thereof; or
(iii) a combination of (i) and (ii).

15. The construct of claim 14 , wherein component (B)(i) comprises a dimer acid.

16. The construct of claim 15 , wherein the dimer acid is a dimer of linoleic acid, oleic acid, or a mixture thereof.

17. The construct of claim 15 , wherein the dimer acid is a dimer of an unsaturated fatty acid.

18. The construct of claim 14 , wherein the epoxidized vegetable oil is epoxidized soybean oil.

19. The construct of claim 14 wherein component (B) is a dimer acid.

20. The construct of claim 19 , wherein the dimer acid is a dimer of an unsaturated fatty acid.

21. The construct of claim 14 , wherein the glycidyl or the epoxidized compound having at least two epoxy groups is selected from bisphenol A diglycidyl ether, bisphenol F diglycidyl ether, bisphenol A propoxylate diglycidyl ether, bisphenol A ethoxylate diglycidyl ether, diethylene glycol diglycidyl ether, 1,3-butanediol diglycidyl ether, 1,4-butanediol diglycidyl ether, poly(ethylene glycol) diglycidyl ether, poly(propylene glycol) diglycidyl ether, neopentyl glycol diglycidyl ether, glycerol diglycidyl ether, diglycidyl 1,2,3,6-tetrahydrophthalate, 1,2-cyclohexanedicarboxylate diglycidyl ether, 1,4-cyclohexanedimethanol diglycidyl ether, resorcinol diglycidyl ether, poly(dimethylsiloxane) terminated with diglycidyl ether, epoxidized linoleic acid ester, epoxidized vegetable oils with two epoxy functional groups, trimethylolpropane triglycidyl ether, trimethylolethane triglycidyl ether, N,N-Diglycidyl-4-glycidyloxyaniline, tris(4-hydroxyphenyl)methane triglycidyl ether, or tris(2,3-epoxypropyl) isocyanurate.

22. The construct of claim 14 , wherein the prepolymer or oligomer includes repeating units having a structure of:

wherein each of R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 independently represents hydrogen or a substituted or unsubstituted alkyl or heteroalkyl group.

23. The construct of claim 14 , wherein (B)(ii)(b) is a glycidyl.

24. A method for making a pressure sensitive adhesive construct comprising:
reacting (i) at least one epoxidized vegetable oil with (ii) a prepolymer or oligomer capped with a carboxylic acid group at both prepolymer or oligomer chain ends, or a branched prepolymer or oligomer with at least two of the prepolymer or oligomer branches and chain ends capped with a carboxylic acid group, wherein the carboxylic acid-capped prepolymer or carboxylic acid-capped oligomer is made from (a) an excess of dibasic acid reacted with (b) a glycidyl or an epoxidized compound having at least two epoxy groups, or a combination thereof; and
forming on a backing substrate a pressure sensitive adhesive from the resulting reaction product.

25. The method of claim 24 , wherein the method comprises:
initially reacting the epoxidized vegetable oil with component (ii) to produce a second prepolymer product;
applying the second prepolymer product onto a backing substrate or a release liner; and
further reacting the second prepolymer product to produce the pressure sensitive adhesive composition.

26.

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

• B32B2037/268

  Release layers · CPC title

• B32B37/26

  with at least one layer which influences the bonding during the lamination process, e.g. release layers or pressure equalising layers · CPC title

• C09J191/00

  Adhesives based on oils, fats or waxes; Adhesives based on derivatives thereof · CPC title

• C09J163/00 Primary

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

• C09J2467/00

  Presence of polyester · CPC title