Farnesene-based polymers and liquid optically clear adhesive compositions incorporating the same

Patent metadata

Field	Value
Publication number	US-9850329-B2
Application number	US-201514753449-A
Country	US
Kind code	B2
Filing date	Jun 29, 2015
Priority date	Jun 29, 2015
Publication date	Dec 26, 2017
Grant date	Dec 26, 2017

Abstract

A low viscosity polymer having a linear or branched backbone derived from farnesene monomers and at least one terminal-end functionalized with a hydroxyl group. This polymer may be further hydrogenated to reduce unsaturation and acrylated, such that it may be incorporated into a LOCA composition. The LOCA composition may be used in a laminated screen assembly, such as a touch screen, for electronic devices by adhering the LOCA composition between an optically transparent layer, such as a cover glass, and a display. The cured LOCA composition has a refractive index similar to the optically transparent layer. A method of making the low viscosity polymer for the LOCA composition includes anionically polymerizing farnesene monomers, quenching a living end of the polymer to provide the hydroxyl-terminated polymer; hydrogenating the hydroxyl-terminated polymer; and reacting the at least partially saturated hydroxyl-terminated polymer with at least one reagent to provide an acrylate terminated hydrogenated polymer.

First claim

We claim:

1. A liquid optically clear adhesive composition comprising a polymer derived from monomers comprising farnesene, the polymer being obtained from a diol wherein hydroxyl groups of the diol have been further reacted to provide terminal ends functionalized with (meth)acrylate groups and wherein the polymer has a degree of unsaturation of less than or equal to 50%, wherein the adhesive composition has a refractive index greater than 1.45 after curing.

2. The liquid optically clear adhesive of claim 1 , wherein the polymer is derived from monomers further comprising one or more dienes.

3. The liquid optically clear adhesive of claim 2 , wherein the dienes are selected from the group consisting of butadiene, isoprene, and myrcene.

4. The liquid optically clear adhesive of claim 1 , wherein the polymer further comprises urethane groups.

5. The liquid optically clear adhesive composition of claim 1 , wherein the polymer further comprises ester groups.

6. The liquid optically clear adhesive composition of claim 1 , wherein the polymer has a degree of unsaturation less than or equal to 10%.

7. The liquid optically clear adhesive composition of claim 1 , wherein the polymer is curable by UV light, electron beam, or heat.

8. The liquid optically clear adhesive composition of claim 1 , wherein when cured, the adhesive has a refractive index greater than 1.5.

9. The liquid optically clear adhesive composition of claim 1 , wherein the polymer has a number average molecular weight less than or equal to 100,000 g/mol.

10. The liquid optically clear adhesive composition of claim 1 , wherein the polymer has a number average molecular weight less than or equal to 25,000 g/mol.

11. The liquid optically clear adhesive composition of claim 1 having a viscosity at 25° C. less than 10,000 cP.

12. A laminated screen assembly comprising the liquid optically clear adhesive of claim 1 disposed between optically transparent substrate layers.

13. A laminated screen assembly comprising a transparent layer adhered to a display and a cured adhesive between the transparent layer and the display, wherein the adhesive is the liquid optically clear adhesive composition of claim 1 .

14. The laminated screen assembly of claim 13 further comprising a touch panel sensor layer between the transparent layer and the display, wherein the cured adhesive is adhered to the touch panel sensor layer and at least one of the transparent layer and the display.

15. The laminated screen assembly of claim 13 , wherein the cured adhesive has a refractive index within 10% of the refractive index of the transparent layer.

16. The laminated screen assembly of claim 13 , wherein the cured adhesive has a refractive index within 5% of the refractive index of the transparent layer.

17. A method of preparing a liquid optically clear adhesive composition comprising:
anionically polymerizing monomers to provide a polymer having at least one living end, the monomers comprising farnesene;
quenching the at least one living end to provide a hydroxyl-terminated polymer;
hydrogenating the hydroxyl-terminated polymer to provide an at least partially saturated hydroxyl-terminated polymer; and
reacting the at least partially saturated hydroxyl-terminated polymer with one or more reagents to provide an acrylate terminated hydrogenated polymer.

18. The method of claim 17 , wherein the monomers further comprise one or more dienes.

19. The method of claim 18 , wherein the dienes are selected from the group consisting of butadiene, isoprene, and myrcene.

20. The method of claim 17 , wherein the polymer has two living ends that are quenched to provide a diol.

21. The method of claim 17 , wherein the at least partially saturated hydroxyl-terminated polymer has a degree of unsaturation less than or equal to 50%.

22. The method of claim 17 , wherein the at least partially saturated hydroxyl-terminated polymer has a degree of unsaturation less than or equal to 10%.

23. The method of claim 17 , wherein reacting the at least partially saturated hydroxyl-terminated polymer with the one or more reagents forms an ester group.

24. The method of claim 17 , wherein reacting the at least partially saturated hydroxyl-terminated polymer with the one or more reagents forms a urethane group.

25. The method of claim 24 , wherein the one or more reagents comprise isophorone diisocyanate and 2 hydroxyethyl acrylate.

26. A polymer comprising a linear or branched backbone derived from a monomer feed comprising farnesene and a comonomer, the farnesene content of the monomer feed being greater than or equal to 25%, by mole, the polymer having terminal ends functionalized with (meth)acrylate groups and a viscosity at 60° C. of equal to or less than 25,000 cP before curing.

27. The polymer of claim 26 having a degree of unsaturation less than or equal to 50%.

28. The polymer of claim 26 , wherein the comonomer consists of a diene.

29. The polymer of claim 26 , wherein the farnesene content of the monomer feed is greater than or equal to 50%, by mole.

Assignees

• Fina Technology

Inventors

• Yoo Taejun
• Chao Herbert
• Henning Steven K

Classifications

• G09G3/36

  using liquid crystals · CPC title

• C08F236/22

  the radical having three or more carbon-to-carbon double bonds · CPC title

• C08F136/22 Primary

  the radical having three or more carbon-to-carbon double bonds · CPC title

• B32B2307/418

  Refractive · CPC title

• C08F8/46

  Reaction with unsaturated dicarboxylic acids or anhydrides thereof, e.g. maleinisation · CPC title