Pressure-sensitive adhesives having high bio-based content and macromonomers for preparing same

Patent metadata

Field	Value
Publication number	US-9469797-B2
Application number	US-201113816389-A
Country	US
Kind code	B2
Filing date	Aug 11, 2011
Priority date	Aug 11, 2010
Publication date	Oct 18, 2016
Grant date	Oct 18, 2016

Abstract

A pressure sensitive adhesive composition comprising the polymerization product of: (A) a monomer selected from the group consisting of alkyl acrylates, alkyl methacrylates, and combinations thereof; and (B) a macromonomer comprising the reaction product of (a) a hydroxy-functional, ethylenically unsaturated monomer (e.g., an alkyl acrylate or methacrylate where the alkyl group is a C 1 -C 6 alkyl group), (b) a bio-based monomer, and (c) a modifying monomer that lowers the Tg of the macromonomer relative to the Tg of the same macromonomer prepared in the absence of the modifying monomer.

First claim

What is claimed is:

1. A macromonomer comprising the ring-opening reaction product of (a) a hydroxy-functional, ethylenically unsaturated monomer, (b) a bio-based monomer, and (c) a modifying monomer that lowers the Tg of the macromonomer relative to the Tg of the same macromonomer prepared in the absence of the modifying monomer, wherein monomers (a), (b), and (c) are different from each other.

2. The macromonomer according to claim 1 wherein the hydroxy-functional, ethylenically unsaturated monomer comprises a hydroxy alkyl acrylate or methacrylate where the alkyl group is a C 1 -C 6 alkyl group.

3. The macromonomer according to claim 2 wherein the hydroxy alkyl acrylate or methacrylate is selected from the group consisting of 2-hydroxy ethyl acrylate, 2-hydroxy ethyl methacrylate, and combinations thereof.

4. The macromonomer according to claim 1 wherein the bio-based monomer comprises a lactide.

5. The macromonomer according to claim 4 wherein the lactide is selected from the group consisting of L-lactide, D-lactide, and D,L-lactide.

6. The macromonomer according to claim 1 wherein the modifying monomer comprises a bio-based monomer.

7. The macromonomer according to claim 6 wherein the modifying monomer comprises a lactone.

8. The macromonomer according to claim 7 wherein the lactone comprises ε-caprolactone.

9. A pressure sensitive adhesive composition comprising the polymerization product of: (A) a monomer selected from the group consisting of alkyl acrylates, alkyl methacrylates, and combinations thereof; and (B) a macromonomer comprising the reaction product of (a) a hydroxy-functional, ethylenically unsaturated monomer, (b) a bio-based monomer, and (c) a modifying monomer that lowers the Tg of the macromonomer relative to the Tg of the same macromonomer prepared in the absence of the modifying monomer, wherein monomers (a), (b), and (c) of the macromonomer are different from each other.

10. The pressure sensitive adhesive composition according to claim 9 wherein the hydroxy-functional, ethylenically unsaturated monomer comprises a hydroxy alkyl acrylate or methacrylate where the alkyl group is a C 1 -C 6 group.

11. The pressure sensitive adhesive composition according to claim 10 wherein the hydroxy alkyl acrylate or methacrylate is selected from the group consisting of 2-hydroxy ethyl acrylate, 2-hydroxy ethyl methacrylate, and combinations thereof.

12. The pressure sensitive adhesive composition according to claim 9 wherein the bio-based monomer comprises a lactide.

13. The pressure sensitive adhesive composition according to claim 12 wherein the lactide is selected from the group consisting of L-lactide, D-lactide, and D,L-lactide.

14. The pressure sensitive adhesive composition according to claim 9 wherein the modifying monomer comprises a bio-based monomer.

15. The pressure sensitive adhesive composition according to claim 14 wherein the modifying monomer comprises a lactone.

16. The pressure sensitive adhesive composition according to claim 15 wherein the lactone comprises ε-caprolactone.

17. The pressure sensitive adhesive composition according to claim 9 , wherein the polymerization product contains at least 35% by weight of the macromonomer minus the hydroxy-functional, ethylenically unsaturated monomer, based upon the total weight of the polymerization product.

18. The pressure sensitive adhesive composition according to claim 9 wherein the polymerization product contains at least 40% by weight of the macromonomer minus the hydroxy-functional, ethylenically unsaturated monomer, based upon the total weight of the polymerization product.

19. The pressure sensitive adhesive composition according to claim 9 wherein the polymerization product contains at least 50% by weight of the macromonomer minus the hydroxy-functional, ethylenically unsaturated monomer, based upon the total weight of the polymerization product.

20. The pressure sensitive adhesive composition according to claim 9 wherein the polymerization product contains at least 55% by weight of the macromonomer minus the hydroxy-functional, ethylenically unsaturated monomer, based upon the total weight of the polymerization product.

21. The pressure sensitive adhesive composition according to claim 9 wherein the (A) monomer is selected from the group consisting of C 1 -C 12 alkyl acrylates, alkyl methacrylates, and combinations thereof.

22. The pressure sensitive adhesive composition according to claim 21 wherein the (A) monomer comprises n-butyl acrylate.

23. The pressure sensitive adhesive composition according to claim 21 wherein the (A) monomer comprises 2-ethylhexyl acrylate.

24. The pressure sensitive adhesive composition according to claim 9 wherein the composition further comprises a tackifier.

25. The pressure sensitive adhesive composition according to claim 9 wherein the composition comprises the polymerization product of the (A) monomer, the (B) macromonomer, and styrene.

Assignees

• Lander Monique Roerdink
• Zhang Jiguang
• Severtson Steven J
• Univ Minnesota

Inventors

• Lander Monique Roerdink
• Zhang Jiguang
• Severtson Steven J

Classifications

• C09J133/08

  Homopolymers or copolymers of acrylic acid esters · CPC title

• C09J167/04 Primary

  Polyesters derived from hydroxycarboxylic acids, e.g. lactones (C09J167/06 takes precedence) · CPC title

• C08G63/08

  Lactones or lactides · CPC title