UV-curing thiolenes for pressure sensitive and hotmelt adhesives

• US 20050119366A1
• Filed: 11/28/2003
• Published: 06/02/2005
• Est. Priority Date: 11/28/2003
• Status: Abandoned Application

• Current Assignee: Ashland Licensing and Intellectual Property Llc
• Original Assignee: Ashland Incorporated (Bank of Montreal)
• Inventors: Day, David, Warmkessel, Jeffrey, Moy, Thomas M.
• Application Number:
  US10/722,478
• Publication Number:
  US 20050119366A1
• Time in Patent Office: Days
• US Class Current: 522/173
• CPC Class Codes: C08G 18/3876 containing mercapto groups
• CPC Class Codes: C08G 18/42 Polycondensates having carboxylic or carbonic ester groups in the main chain
• CPC Class Codes: C08G 18/6715 Unsaturated monofunctional alcohols or amines
• CPC Class Codes: C08G 2170/20 Compositions for hot melt adhesives
• CPC Class Codes: C08G 2170/40 Compositions for pressure-sensitive adhesives
• CPC Class Codes: C08G 75/045 from mercapto compounds and unsaturated compounds
• CPC Class Codes: C08G 75/12 Polythioether-ethers C08G75/0245 takes precedence
• CPC Class Codes: C09J 175/16 having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: G03F 7/038 Macromolecular compounds which are rendered insoluble or differentially wettable G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021

Abstract

Thiolene-curing adhesive formulations, methods of preparation, and uses thereof are provided.

Claims

1. A UV-curable adhesive composition comprising:

a vinyl-ether terminated urethane; and

a poly-functional mercaptan.

2. The UV-curable adhesive composition, according to claim 1, wherein said urethane is synthesized from at least one polyester polyol and at least one aliphatic diisocyanate.

3. The UV-curable adhesive composition, according to claim 1, wherein said urethane has a molecular weight, <

Mn>

, in the range of 1000 to 50,000, more preferably 2000 to 12,000 and most preferably 3000 to 7000.

5. The UV-curable adhesive composition, according to claim 1, wherein said polyol has a molecular weight in the range of from about 1000 to about 3200 AMU.

6. The UV-curable adhesive composition, according to claim 1, wherein said diisocyanate is selected from the group consisting of Desmodur W, IPDI, and TMDI.

7. The UV-curable adhesive composition, according to claim 1, wherein said poly-functional mercaptan has at least 2 thiol groups.

8. The UV-curable adhesive composition, according to claim 1, wherein said poly-functional mercaptan is selected from the group consisting of

ethylene bis(3-mercaptopropionate),

trimethylolpropane tris(2-mercaptoacetate),

trimethylolpropane tris(3-mercaptopropionate),

triethyl-1,3,5,-triazine-2,4,6-trione tris(3-mercaptopropionate),

pentaerythritol tetrakis(2-mercaptoacetate),

pentaerythritol tetrakis(3-mercaptopropionate),

dimethyl bis(3-mercaptopropyl)silane,

1,6-hexanedithiol,

1,10-decanedithiol, and

3,6-Dioxaoctane-1,8-dithiol.

9. The UV-curable adhesive composition, according to claim 1, wherein said poly-functional mercaptan is a 3-mercaptopropionic acid ester of a polyhydroxy compound.

10. The UV-curable adhesive composition, according to claim 9, wherein said polyhydroxy compound is selected from the group consisting of glycols, propylene glycol, butanediol, hexanediol, cyclohexanedimethanol, glycerol, polyethylene glycol, polypropylene glycol, and polyester polyols.

11. The UV-curable adhesive composition, according to claim 1, wherein said poly-functional mercaptan is trimethylpropane tris(trimercaptopropionate).

12. The UV-curable adhesive composition, according to claim 1, further comprising at least one additive selected from the group consisting of polymerization inhibitors, antioxidants, tackifiers, flow and leveling agents, pigments, fillers, odor-masking agents, and UV-stabilizers.

14. The thiolene composition, according to claim 11, wherein said curing agent is ultraviolet light.

19. A hot-melt coater containing the curable thiol-ene formulation of claim 1.

13. A thiolene composition comprising the reaction product of:

a vinyl-ether terminated urethane; and

a poly-functional mercaptan, wherein

said composition is crosslinked with a curing agent.

15. A thiol-ene formulation curable to a crosslinked polymer comprising:

a polyfunctional mercaptan; and

a vinyl-terminated urethane.

16. An adhesive product comprising

a layer of a backing material;

and

a layer of a curable thiol-ene formulation comprising;

a polyfunctional mercaptan, and

a vinyl-terminated urethane, wherein said thiol-ene formulation is cured to a crosslinked polymer.

17. A method of using a curable thiol-ene formulation comprising:

providing a backing material;

providing on said backing material a layer of a curable thiol-ene formulation comprising;

a polyfunctional mercaptan, and

a vinyl-terminated urethane; and

curing said thiol-ene formulation.

18. The method of using a curable thiol-ene formulation, according to claim 17, further comprising applying said formulation with a hot-melt coater.