Radiation-curable binder compositions having high elongation and toughness after cure

• US 6,265,476 B1
• Filed: 10/04/1999
• Issued: 07/24/2001
• Est. Priority Date: 04/08/1997
• Status: Expired due to Fees

• Current Assignee: DSM IP Assets BV (DSM-Firmenich AG)
• Original Assignee: DSM B.V.
• Inventors: Sullivan, Michael G., Krongauz, Vadim V., Murphy, Edward J., Lapin, Stephen C.
• Primary Examiner(s): Dawson, Robert
• Assistant Examiner(s): Peng, Kuo-Liang
• Application Number:
  US09/411,326
• Time in Patent Office: 659 Days
• Field of Search: 524/81, 524/262, 526/301, 522/90, 522/96, 522/97, 528/30, 427/515, 427/516, 385/123, 654/25, 428/378, 428/441, 556/427, 556/458, 568/61, 568/21
• US Class Current: 524/262
• CPC Class Codes: C08F 290/067 Polyurethanes; Polyureas
• CPC Class Codes: C08G 18/10 Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
• CPC Class Codes: C08G 18/672 Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
• CPC Class Codes: C09D 175/16 having terminal carbon-to-carbon unsaturated bonds
• CPC Class Codes: C09D 4/06 Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
• CPC Class Codes: Y10T 428/2938 Coating on discrete and individual rods, strands or filaments
• CPC Class Codes: Y10T 428/31645 Next to addition polymer from unsaturated monomers

Abstract

Radiation-curable compositions, having high elongation at break and toughness after cure can include the following pre-mixture components:

a) a polymer, oligomer or monomer having at least one (meth)acrylate functional group;

b) an oligomer or monomer, exclusive of (meth)acrylate functional groups, having an ethylenically unsaturated functional group; and

c) an elongation promoter;

wherein the composition, after radiation-cure, has an elongation at break of at least about 200%. Glass substrates and optical fibers are coated with the radiation-curable composition. Monofilament fiber or a plurality of fiber filaments, such as sewing thread, are coated with the radiation-curable binder composition, which after cure, demonstrates high elongation at break.

Claims

1. A radiation-curable composition comprising the folowing pre-mixture components:

a) a polymer, oligomer, or monomer having at lease one (meth)acrylate functional group;

b) an oligomer or monomer, exclusive of (meth)acrylate functional groups, having an ethylenically unsaturated functional group;

c) an elongation promoter comprising a mercapto or sulfide group; and

d) a photoinitiator;

wherein

the composition, after ratiation cure, has an elongation at break of at least about 400%; and

said elongation promoter is present in an amount sufficient to result in an elongation that is at least 1.5 times the elongation of a corresponding composition that does not comprise the elongation promoter.

2. The radiation-curable composition according to claim 1, wherein the component (b) is present in an amount of from 3-20 wt. %, relative to the total composition.

3. The radiation-curable composition according to claim 1, wherein the ethylenically-unsaturated functional group includes a N-vinyl group.

4. The radiation-curable composition according to claim 1, wherein the ethylenically-unsaturated functional oligomer or monomer is N-vinyl formamide, N-vinyl pyrrolidone or N-vinyl caprolactam.

5. The radiation-curable composition according to claim 1, wherein the oligomer or monomer component (b) is monofunctional.

6. The radiation-curable composition according to claim 1, wherein the component (a) includes a (meth)acrylurethane polymer, oligomer or monomer.

7. The radiation-curable composition according to claim 1, wherein the component (a) has two (meth)acrylate functional groups.

8. The radiation-curable composition according to claim 1, wherein the component (a) is a (meth)acrylurethane polymer or oligomer having a polyether, polycarbonate or hydrocarbon backbone.

9. The radiation-curable composition according to claim 1, wherein the components (a) and (b) do not contain a silicone group.

10. The radiation-curable composition according to claim 1, wherein the composition is free of difunctional monomers.

11. The radiation-curable composition according to claim 1, wherein the sulfur-containing compound has a sulfur atom attached to an aliphatic group.

12. The radiation-curable composition according to claim 1, wherein the elongation promoter includes a silane group.

13. The radiation-curable composition according to claim 1, wherein the composition comprises, relative to the total composition, about 0.5 to about 8 wt. % of the elongation promoter.

14. The radiation-curable composition according to claim 1, wherein said photoinitiator is present in an amount sufficient to accelerate curing of the composition upon exposure to ultra-violet and/or visible light.

15. An article comprising a coating, binder, or adhesive formed from a composition according to claim 1.

16. The article of claim 15, wherein the article is a coated optical fiber.

17. The article of claim 15, wherein the article is a sewing thread.

18. The article of claim 15, wherein the article is a multi-layered glass.

19. A process for making an article comprising a cured coating, binder or adhesive comprising, the steps of:

applying to a substrate a composition according to claim 1, and curing the composition.

20. The process of claim 19, further comprising the step of curing the composition by exposure to 0.2 to 2.0 J/cm² of ultraviolet and/or visible light.

21. The composition of claim 1, wherein said composition, after radiation cure, has an elongation at break of at least about 600%.

22. The composition of claim 1, wherein said composition, after radiation cure, has an elongation at break of at least about 800%.

23. The composition of claim 1, wherein said composition, after radiation cure, has a secant modulus of at least about 3 MPa.

24. The composition of claim 1, wherein said composition, after radiation cure, has a secant modulus of at least about 10 MPa.

25. The composition of claim 1, wherein said composition, after radiation cure, has a secant modulus of at least about 3 MPa and less than about 70 MPa.

26. The composition of claim 1, wherein said composition, after radiation cure, has a dry adhesion of above 300 g/inch.

27. The composition of claim 1, wherein said composition, after radiation cure, has a wet adhesion of above 150 g/inch.

28. The composition of claim 1, wherein said composition, after cure, has an alcohol extraction value that does not exceed 8 wt %.

29. The composition of claim 1, wherein said composition comprises, relative to the total weight of the composition, 5 to 8 wt % of elongation promoter.

30. The composition of claim 1, comprising, relative to the total weight of the composition, less than 14 wt % of said component (b).