Radiation curable microstructure-bearing articles

• US 6,833,176 B2
• Filed: 01/06/2003
• Issued: 12/21/2004
• Est. Priority Date: 01/06/2003
• Status: Expired due to Fees

• Current Assignee: Sabic Innovative Plastics IP BV (Government of Saudi Arabia)
• Original Assignee: General Electric Company
• Inventors: Hay, Grant, Siclovan, Tiberiu Mircea, Molaison, Chris Anthony, Resue, James Alan, Coyle, Dennis Joseph, Chisholm, Bret Ja, Olson, Daniel Robert
• Primary Examiner(s): BERMAN, SUSAN W
• Application Number:
  US10/336,493
• Publication Number:
  US 20040131826A1
• Time in Patent Office: 715 Days
• Field of Search: 428/1--, 428/156, 428/141, 428/167, 359/457, 359/456, 359/459, 359/599, 359/837, 359/584, 522/175, 522/182, 522/173
• US Class Current: 428/156
• CPC Class Codes: C08F 222/102 of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
• CPC Class Codes: C08L 33/08 Homopolymers or copolymers of acrylic acid esters
• CPC Class Codes: C08L 33/10 Homopolymers or copolymers of methacrylic acid esters
• CPC Class Codes: G02B 1/041 Lenses
• CPC Class Codes: Y10T 428/24355 Continuous and nonuniform or irregular surface on layer or component [e.g., roofing, etc.]
• CPC Class Codes: Y10T 428/24479 including variation in thickness
• CPC Class Codes: Y10T 428/2457 Parallel ribs and/or grooves

Abstract

Blends of monofunctional and multifunctional (meth)acrylate monomers, optionally in addition to oligomeric multifunctional (meth)acrylates), can be cured by ultraviolet radiation in contact with a photoinitiator to produce optical resinous articles having a glass transition temperature of at least 35° C. and having physical properties making them suitable for use as microstructure-bearing articles.

Claims

1. An optical article having a surface with a replicated microstructure comprising a plurality of utilitarian discontinuities having an optical purpose, said optical article comprising an organic resin having a glass transition temperature of at least 35°

C.;

said resin being free from carbocyclic and heterocyclic polymerizable moieties and said resin being prepared by curing a radiation curable composition comprising

(A) at least one monofunctional acrylic monomer comprising

(1) at least one monomeric t-alkyl (meth)acrylate,

(2) optionally one or more monomeric N-substituted or N,N-disubstituted (meth)acrylamide and

(3) optionally one or more C_1-8 primary or secondary alkyl (meth)acrylate;

(B) at least one multifunctional (meth)acrylate or (meth)acrylamide monomer;

(C) optionally, at least one oligomeric multifunctional (meth)acrylate; and

(D) at least one photoinitiator.

2. An article according to claim 1 which is radiation curable to an optical resinous article having a glass transition temperature of at least 40°

C.

3. An article according to claim 1 having a dynamic tensile modulus that falls within the boundary of the area A-B-C-D in FIG. 2.

4. An article according to claim 1 wherein component A-1 is a t-butyl (meth)acrylate.

5. An article according to claim 1 comprising component A-2.

6. An article according to claim 5 wherein component A-2 is N-isopropylacrylamide, N-t-butylacrylamide, N,N-dimethylacrylamide or N,N-diethylacrylamide.

7. An optical article according to claim 5 wherein said curing is carried out using ultraviolet radiation.

8. An article according to claim 1 comprising component A-3.

9. An article according to claim 8 wherein component A-3 is methyl acrylate, methyl methacrylate, ethyl acrylate, 1-propyl acrylate or a 2-(N-butylcarbamyl)ethyl (meth)acrylate.

10. An optical article according to claim 8 wherein said curing is carried out using ultraviolet radiation.

11. An article according to claim 1 wherein component B is at least one polyol poly(meth)acrylate.

12. An article according to claim 11 wherein component B is ethylene glycol di(meth)acrylate, 1,6-hexanediol di(meth)acrylate. 2-ethyl-2-hydroxymethyl- 1,3-propanediol tri(meth)acrylate, di(trimethylolpropane) tetra(meth)acrylate or pentaerythritol tetra(meth)acrylate.

13. An optical article according to claim 11 wherein said curing is carried out using ultraviolet radiation.

14. An article according to claim 1 wherein component B is at least one N,N′

-alkylenebisacrylamide.

15. An article according to claim 14 wherein component B is N,N′

-methylenebisacrylamide.

16. An optical article according to claim 14 wherein said curing is carried out using ultraviolet radiation.

17. An article according to claim 1 comprising component C.

18. An article according to claim 17 wherein component C is an oligomeric polyether di(meth)acrylate having a glass transition temperature of at most 23°

C.

19. An article according to claim 17 wherein component C is a di(meth)acrylate of a polyester polyol or an oligomer thereof.

20. An optical article according to claim 17 wherein said curing is carried out using ultraviolet radiation.

21. An article according to claim 19 wherein component C is poly(ethylene glycol) di(meth)acrylate or poly(propylene glycol) di(meth)acrylate.

22. An article according to claim 17 wherein component C is an oligomeric urethane di(meth)acrylate.

23. An article according to claim 22 wherein component C is a reaction product of 2,2,4-trimethylhexane 1,6-diisocyanate, polycaprolactone diol and 2-hydroxyethyl methacrylate.

24. An article according to claim 1 wherein component A constitutes about 10-98% by weight based on total polymerizable components.

27. An optical article according to claim 1 wherein said curing is carried out using ultraviolet radiation.

25. An optical article having a surface with a replicated microstructure comprising a plurality of utilitarian discontinuities having an optical purpose, said optical resinous article comprising an organic resin having a glass transition temperature of at least 40°

C.;

said resin being free from carbocyclic and heterocyclic polymerizable moieties and said resin being prepared by curing a radiation curable composition comprising;

(A)

(1) t-butyl (meth)acrylate,

(2) optionally N-isopropylacrylamide, N-t-butylacrylamide, N,N-dimethylacrylamide or N,N-diethylacrylamide, and

(3) optionally methyl acrylate, methyl methacrylate, ethyl acrylate, 1-propyl acrylate or a 2-(N-butylcarbamyl)ethyl (meth)acrylate,

(B) at least one multifunctional (meth)acrylate or (meth)acrylamide monomer selected from the group consisting of ethylene glycol di(meth)acrylate, 1.6-hexanediol di(meth)acrylate, 2-ethyl-2-hydroxymethyl- 1,3-propanediol tri(meth)acrylate, di(trimethylolpropane) tetra(meth)acrylate, pentaerythritol tetra(meth)acrylate and N,N′

-methylenebisacrylamide, and

(C) optionally, at least one oligomeric multifunctional (meth)acrylate selected from the group consisting of oligomeric polyether di(meth)acrylates having a glass transition temperature of at most 23°

C., di(meth)acrylates of polyester polyols and oligomers thereof, and oligomeric urethane di(meth)acrylates; and

(D) at least one photoinitiator.

26. An article according to claim 25 wherein component C is a reaction product of 2,2,4-trimethylhexane 1,6-diisocyanate, polycaprolactone diol and 2-hydroxyethyl methacrylate.

28. An optical article according to claim 25 wherein said curing is carried out using ultraviolet radiation.