Solvent-free, radiation-curable, optical glass fiber coating composition and solvent-free method for making a solvent-free, radiation-curable, optical glass fiber coating composition

• US 6,107,361 A
• Filed: 10/08/1998
• Issued: 08/22/2000
• Est. Priority Date: 11/03/1995
• Status: Expired due to Fees

• Current Assignee: DSM IP Assets BV (DSM-Firmenich AG)
• Original Assignee: DSM B.V.
• Inventors: Murphy, Edward J., Tortorello, Anthony J.
• Primary Examiner(s): Berman, Susan W.
• Application Number:
  US09/168,290
• Time in Patent Office: 684 Days
• Field of Search: 522/96, 522/95, 522/116, 522/90, 522/136, 522/137, 528/65, 528/66, 528/69, 528/75
• US Class Current: 522/96
• CPC Class Codes: C03C 25/106 Single coatings
• CPC Class Codes: C03C 25/1065 Multiple coatings
• CPC Class Codes: C08G 18/40 High-molecular-weight compounds C08G18/2805 takes precedence
• CPC Class Codes: C08G 18/48 Polyethers
• CPC Class Codes: C08G 18/62 Polymers of compounds having carbon-to-carbon double bonds
• CPC Class Codes: C08G 18/6229 Polymers of hydroxy groups containing esters of acrylic or methacrylic acid with aliphatic polyalcohols
• CPC Class Codes: C08G 18/63 Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
• CPC Class Codes: C08G 18/8158 with unsaturated compounds having only one group containing active hydrogen
• CPC Class Codes: G03F 7/027 Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds G03F7/075 takes precedence
• CPC Class Codes: G03F 7/0388 with ethylenic or acetylenic bands in the side chains of the photopolymer
• CPC Class Codes: Y10T 428/2938 Coating on discrete and individual rods, strands or filaments

Abstract

The invention relates to a solvent-free radiation curable, optical glass fiber coating composition containing:

a) a urethane oligomer having a functional group capable of polymerization in the presence of actinic radiation, with an average functionality of at least about 1.2, having a vinyl addition polymer as backbone.

b) a urethane compound having a functional group capable of polymerization in the presence of actinic radiation, with an average functionality of at least about 1, containing an organic moiety having about 5 or more carbon atoms as backbone.

c) a reactive diluent.

Furthermore, the invention relates to a solvent-free method for producing a solvent-free, radiation curable urethane oligomer composition.

Claims

1. A process for making a radiation-curable, optical glass fiber coating composition comprising:

reacting

i) a hydroxy functional vinyl addition copolymer, and

ii) an isocyanate having a functional group capable of polymerization in the presence of actinic radiation,

wherein said reaction is solvent-free and conducted in a hydroxy-functional diluent to form a composition comprising a radiation-curable urethane-containing polymer having a vinyl addition copolymer backbone.

2. The process of claim 1, wherein said polymer and said compound in said composition have an average functionality of at least about 1.2 and at least about 1, respectively.

3. The process of claim 1, wherein said hydroxy-functional diluent includes monohydroxy functional diluents and/or dihydroxy functional diluents.

4. The process of claim 1, wherein said hydroxy-functional diluent includes ethoxylated derivatives of nonylphenol.

5. The process of claim 1, wherein said hydroxy-functional diluent includes C₈ -C₂₀ alcohols.

6. The process of claim 1, wherein said hydroxy-functional diluent includes a polytetramethylene diol.

7. The process of claim 1, further comprising reacting a hydroxy-functional ethylenically-unsaturated monomer with at least one ethylenically-unsaturated co-polymerizable monomer to form said vinyl addition copolymer.

8. The process of claim 7, wherein said vinyl addition copolymer forming reaction is conducted in the absence of a solvent.

9. The process of claim 7, wherein said vinyl addition copolymer forming reaction is conducted in the presence of said reactive hydroxy-functional diluent.

10. The process of claim 7, wherein said at least one ethylenically-unsaturated co-polymerizable monomer comprises a mixture of at least two monomers.

11. The process of claim 7, wherein said hydroxy-functional ethylenically-unsaturated monomer and said at least one ethylenically-unsaturated co-polymerizable each monomer have an ethylenic unsaturated group selected from the functional groups consisting of acrylate, methacrylate, styrene, vinylether, vinylester, acrylamide, maleate, and fumarate.

12. The process of claim 7, wherein said hydroxy-functional ethylenically-unsaturated monomer contains an acrylate functional group.

13. The process of claim 7, further comprising the step of adding a thermal initiator to said vinyl addition copolymer forming reaction.

14. The process of claim 13, further comprising the step of heating said hydroxy-functional ethylenically-unsaturated diluent to a polymerization temperature, and adding said hydroxy-functional monomer and said at least one ethylenically-unsaturated co-polymerizable monomer to said heated hydroxy-functional diluent.

15. A process for making a radiation-curable, optical glass fiber coating composition comprising:

conducting a solvent-free urethane reaction to form

(I) a urethane-containing polymer from

(a) a hydroxy-functional copolymer having a vinyl addition backbone, and

(b) a compound having at least one functional group capable of polymerization in the presence of actinic radiation; and

(ii) a urethane-containing compound from

(c) a hydroxy-functional compound having a hydrocarbon, polyether, polyester, polycarbonate, silicone, or fluorocarbon backbone, and

(d) said compound having at least one functional group capable of polymerization in the presence of actinic radiation.

16. The process of claim 15, wherein said urethane-containing polymer and said urethane-containing compound have an average functionality of at least about 1.2 and at least about 1, respectively.

17. The process of claim 15, wherein said urethane reaction includes as reactant:

a mono-functional isocyanate compound having said at least one functional group capable of polymerization in the presence of actinic radiation.

18. The process of claim 15, wherein said hydroxy-functional compound is a diluent.

19. The process of claim 18, wherein said hydroxy-functional diluent includes monohydroxy functional diluents and/or dihydroxy functional diluents.

20. The process of claim 18, wherein said hydroxy-functional diluent includes ethoxylated derivatives of nonylphenol.

21. The process of claim 18, wherein said hydroxy-functional diluent includes C₈ -C₂₀ alcohols.

22. The process of claim 18, wherein said hydroxy-functional diluent includes a polytetramethylene diol.

23. The process of claim 15, further comprising reacting a hydroxy-functional ethylenically-unsaturated monomer with at least one ethylenically-unsaturated co-polymerizable monomer to form said vinyl addition copolymer.

24. The process of claim 23, wherein said vinyl addition copolymer forming reaction is conducted in the absence of a solvent.

25. The process of claim 23, wherein said vinyl addition copolymer forming reaction is conducted in the presence of a reactive hydroxy-functional diluent.

26. The process of claim 25, wherein said hydroxy-functional diluent includes monohydroxy functional diluents and/or dihydroxy functional diluents.

27. The process of claim 25, wherein said hydroxy-functional diluent includes ethoxylated derivatives of nonylphenol.

28. The process of claim 25, wherein said hydroxy-functional diluent includes C₈ -C₂₀ alcohols.

29. The process of claim 25, wherein said hydroxy-functional diluent includes a polytetramethylene diol.

30. The process of claim 23, wherein said at least one ethylenically-unsaturated co-polymerizable monomer comprises a mixture of at least two monomers.

31. The process of claim 23, wherein said hydroxy-functional ethylenically-unsaturated monomer and said at least one ethylenically-unsaturated co-polymerizable monomer each have an ethylenic unsaturated group selected from the functional groups consisting of acrylate, methacrylate, styrene, vinylether, vinylester, acrylamide, maleate, and fumarate.

32. The process of claim 23, wherein said hydroxy-functional ethylenically-unsaturated monomer contains an acrylate functional group.