FARNESENE-BASED POLYMERS AND LIQUID OPTICALLY CLEAR ADHESIVE COMPOSITIONS INCORPORATING THE SAME

• US 20160376386A1
• Filed: 06/29/2015
• Published: 12/29/2016
• Est. Priority Date: 06/29/2015
• Status: Active Grant

• Current Assignee: Fina Technology, Inc. (Totalenergies Se)
• Original Assignee: Fina Technology, Inc. (Totalenergies Se)
• Inventors: YOO, Taejun, Chao, Herbert, Henning, Steven K.
• Granted Patent: US 9,850,329 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: B32B 2307/412 Transparent
• CPC Class Codes: B32B 2457/202 LCD, i.e. liquid crystal displays
• CPC Class Codes: B32B 2457/208 Touch screens
• CPC Class Codes: B32B 7/12 using interposed adhesives or interposed materials with bonding properties
• CPC Class Codes: C08C 19/02 Hydrogenation
• CPC Class Codes: C08C 19/04 Oxidation
• CPC Class Codes: C08C 19/28 Reaction with compounds containing carbon-to-carbon unsaturated bonds graft polymers C08F279/00
• CPC Class Codes: C08C 19/38 with hydroxy radicals
• CPC Class Codes: C08F 136/22 the radical having three or more carbon-to-carbon double bonds
• CPC Class Codes: C08F 36/22 the radical having three or more carbon-to-carbon double bonds
• CPC Class Codes: C08G 18/246 containing also tin-carbon bonds
• CPC Class Codes: C08G 18/62 Polymers of compounds having carbon-to-carbon double bonds
• CPC Class Codes: C08G 18/6208 Hydrogenated polymers of conjugated dienes
• CPC Class Codes: C08G 18/755 and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
• CPC Class Codes: C08G 18/8175 with esters of acrylic or alkylacrylic acid having only one group containing active hydrogen
• CPC Class Codes: C09J 147/00 Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds; Adhesives based on derivatives of such polymers C09J145/00 takes precedence; based on conjugated diene rubbers C09J109/00 - C09J121/00
• CPC Class Codes: C09J 175/16 having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: C09J 2203/318 for the production of liquid crystal displays
• CPC Class Codes: C09J 2423/00 Presence of polyolefin
• CPC Class Codes: G06F 2203/04103 Manufacturing, i.e. details related to manufacturing processes specially suited for touch sensitive devices
• CPC Class Codes: G06F 3/0412 : Digitisers structurally integrated in a display
• CPC Class Codes: G09G 3/36 : using liquid crystals

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.

Claims

1. A liquid optically clear adhesive composition comprising a polymer derived from monomers comprising farnesene and having at least one terminal end functionalized with an acrylate group and a degree of unsaturation less than or equal to 50%.

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 terminal ends of the polymer are functionalized with an acrylate group.

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

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

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

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

9. The liquid optically clear adhesive composition of claim 1, wherein when cured, the adhesive has a refractive index greater than 1.45.

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

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

12. The liquid optically clear adhesive composition of claim 1 having a viscosity at 25°

C. less than 10,000 cP.

23. 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.

24. The laminated screen assembly of claim 23 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.

25. The laminated screen assembly of claim 23, wherein the cured adhesive has a refractive index within 10% of the refractive index of the transparent layer.

26. The laminated screen assembly of claim 23, wherein the cured adhesive has a refractive index within 5% of the refractive index of the transparent layer.

13. A liquid optically clear adhesive composition comprising a polymer having a structure according to Formula (I),

14. 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.

15. The method of claim 14, wherein the monomers further comprise one or more dienes.

16. The method of claim 15, wherein the dienes are selected from the group consisting of butadiene, isoprene, and myrcene.

17. The method of claim 14, wherein the polymer has two living ends that are quenched to provide a diol.

18. The method of claim 14, wherein the at least partially saturated hydroxyl-terminated polymer has a degree of unsaturation less than or equal to 50%.

19. The method of claim 14, wherein the at least partially saturated hydroxyl-terminated polymer has a degree of unsaturation less than or equal to 10%.

20. The method of claim 14, wherein reacting the at least partially saturated hydroxyl-terminated polymer with the one or more reagents forms an ester group.

21. The method of claim 14, wherein reacting the at least partially saturated hydroxyl-terminated polymer with the one or more reagents forms a urethane group.

22. The method of claim 21, wherein the one or more reagents comprise isophorone diisocyanate and 2 hydroxyethyl acrylate.

27. A polymer comprising a linear or branched backbone derived from monomers comprising farnesene and at least one terminal end functionalized with a hydroxyl group.

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