Bridged monomers

• US 7,135,589 B2
• Filed: 04/30/2004
• Issued: 11/14/2006
• Est. Priority Date: 03/07/2001
• Status: Expired due to Fees

• Current Assignee: Board of Regents of the University of Texas System (University of Texas System)
• Original Assignee: Board of Regents of the University of Texas System (University of Texas System)
• Inventors: Satsangi, Neera, Norling, Barry K.
• Primary Examiner(s): Wu, Shean C.
• Application Number:
  US10/836,532
• Publication Number:
  US 20040206934A1
• Time in Patent Office: 928 Days
• Field of Search: 252/299.01, 252/299.64, 252/299.67, 560/77, 560/76, 560/85, 524/534, 524/559
• US Class Current: 560/85
• CPC Class Codes: C08G 63/60 derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
• CPC Class Codes: C08G 63/605 the hydroxy and carboxylic groups being bound to aromatic rings
• CPC Class Codes: C09K 19/2007 the chain containing -COO- or -OCO- groups
• CPC Class Codes: C09K 2019/0448 the end chain group being a polymerizable end group, e.g. -Sp-P or acrylate

Abstract

Liquid crystal monomers and secondary monomers useful to blend with liquid crystal monomers to maintain a nematic state under processing conditions while maintaining low cure shrinkage, particularly suitable for use in dental resin composites.

Claims

1. Monomers having the following general structure:

2. The monomers of claim 1 wherein n and m are selected from the group consisting of from about 4 to about 11.

3. The monomer α

,ω

,-bis-4-[4-{4-(ω

-R-acryloxy-alkyloxy) -benzoyloxy}-2-R⁷-phenoxy carbonyl]-phenoxy-alkane wherein;

R is selected from the group consisting of H and CH₃;

said alkyloxy and said alkcane have from about 2 to about 12 carbon atoms; and

R⁷ independently is selected from the group consisting of t-butyl groups, phenyl groups, isopropyl groups, and secondary butyl groups.

4. The monomer of claim 3 wherein R⁷ independently is selected from the group consisting of t-butyl groups and phenyl groups.

5. The monomer of claim 3 wherein R⁷ is a t-butyl group.

6. The monomer of claim 3 wherein said alkyloxy and said alkane have from about 2 to about 10 carbon atoms.

7. The monomer of claim 3 wherein said alkyloxy and said alkane have from about 2 to about 6 carbon atoms.

8. The monomer of claim 4 wherein said alkyloxy and said alkane have 6 carbon atoms.

9. Monomers having the following general structure:

10. The monomers n-[4-({n-[(2-(R⁷)-4-{4-[n-(2-R-prop-2-noyloxy)alkyloxy]phenylcarbonyloxy}phenyl)oxycarbonyl]alkyl} oxycarbonyl)phenoxy]alkyl 2-R-prop-2-enoate wherein:

R is selected from the group consisting of H and CH₃;

said alkyls and said alkyloxys have from about 2 to about 12 carbon atoms; and

R⁷ is selected from the group consisting of t-butyl groups, phenyl groups, isopropyl groups, and secondary butyl groups.

11. The monomers of claim 10 wherein R⁷ is selected from the group consisting of t-butyl groups and phenyl groups.

12. The monomers of claim 10 wherein said alkyls and said alkyloxys have from about 2 to about 10 carbon atoms.

13. The monomers of claim 11 wherein said alkyls and said alkyloxys have from about 2 to about 6 carbon atoms.

14. The monomers of claims 11 wherein said alkyls and said alkyloxys have 6 carbon atoms.

15. Monomers having the following general structure:

16. The monomers of claim 15 wherein n and m independently are selected from the group consisting of from about 2 to about 10.

17. The monomers of claim 15 wherein n and m independently are selected from the group consisting of from about 2 to about 6.

18. The monomers of claim 15 wherein n and m are 6.

19. Monomers having the following general structure:

20. Monomers having the following general structure:

21. Monomers comprising nonanedjoic acid bis-(2-R⁷-4-[4-[6-(2-R-acryloyloxy)-alkyloxy]-benzoyloxy]-phenyl) ester wherein:

R is selected from the group consisting of H and CH₃;

said alkyloxy has from about 2 to about 12 carbon atoms; and

R⁷ is selected from the group consisting of t-butyl groups, phenyl groups, isopropyl groups, and secondary butyl groups.

22. The monomers of claim 21 wherein R⁷ is selected from the group consisting of t-butyl groups and phenyl groups.

23. The monomers of claim 22 wherein R⁷ a t-butyl group.

24. The monomers of claims 21 wherein said alkyloxy has from about 2 to about 10 carbon atoms.

25. The monomers of claims 22 wherein said alkyloxy has from about 2 to about 6 carbon atoms.

26. The monomers of claim 23 wherein said alkyloxy has 6 carbon atoms.

27. Monomers having the following general structure:

28. The monomers of claim 27 wherein at least one of said polymerizable groups of R⁵ and R⁹ comprises a nucleophile selected from the group consisting of ester groups, organic acid groups, amine groups, hydroxyl groups, and sulfhydryl groups.

29. The monomers of claim 27 wherein at least one of said polymerizable groups of R⁵ and R⁹ comprise electron deficient alkenes.

30. The monomers of claim 29 wherein said electron deficient alkene independently is selected from the group consisting of substituted and unsubstituted alkenyl ester groups comprising a polymerizable unsaturated carbon-carbon bond, wherein said alkenyl group has from about 2 to about 12 carbon atoms.

31. The monomers of claim 29 wherein said electron deficient alkene is selected from the group consisting of acryloyl groups and methacryloyl groups.

32. The monomers of claim 27 wherein R⁷ is selected from the group consisting of t-butyl groups and phenyl groups.

33. The monomers of claim 27 wherein R⁷ is selected from the group consisting of t-butyl groups and phenyl groups.

34. The monomers of claim 28 wherein R⁷ is selected from the group consisting of t-butyl groups and phenyl groups.

35. The monomers of claim 29 wherein R⁷ is selected from the group consisting of t-butyl groups and phenyl groups.

36. The monomers of claim 30 wherein R⁷ is selected from the group consisting of t-butyl groups and phenyl groups.

37. The monomers of claim 31 wherein R⁷ is selected from the group consisting of t-butyl groups and phenyl groups.

38. The monomers of claim 27 wherein X, Y and Z independently comprise from about 2 to about 10 carbon atoms.

39. The monomers of claim 37 wherein X, Y and Z independently comprise from about 2 to about 10 carbon atoms.

40. The monomers of claim 27 wherein X, Y, and Z independently comprise from about 2 to about 6 carbon atoms.

41. The monomers of claim 37 wherein X, Y, and Z independently comprise from about 2 to about 6 carbon atoms.

42. The monomers of claim 37 wherein X, Y, and Z have 6 carbon atoms.

43. Monomers having the following structure:

44. The monomer of claim 43 wherein R⁷ independently is selected from the group consisting of t-butyl groups and phenyl groups.

45. The monomer of claim 43 wherein R⁷ is a t-butyl group.

46. The monomer of claim 43 wherein X, Y, and Z have from about 2 to about 10 carbon atoms.

47. The monomer of claim 44 wherein X, Y, and Z have from about 2 to about 6 carbon atoms.

48. The monomer of claim 44 wherein X, Y, and Z have 6 carbon atoms.

49. Monomers having the following structure:

50. The monomer of claim 49 wherein R⁷ independently is selected from the group consisting of t-butyl groups and phenyl groups.

51. The monomer of claim 49 wherein R⁷ is a t-butyl group.

52. The monomer of claim 49 wherein X, Y, and Z have from about 2 to about 10 carbon atoms.

53. The monomer of claim 49 wherein X, Y, and Z have from about 2 to about 6 carbon atoms.

54. The monomer of claim 50 wherein X, Y, and Z have from about 2 to about 6 carbon atoms.

55. The monomer of claim 50 wherein X, Y, and Z have 6 carbon atoms.

60. The monomer of claim 55 wherein X, Y, and Z have from about 2 to about 6 carbon atoms.

56. Monomers having the following general structure:

57. The monomer of claim 56 wherein R⁷ independently is selected from the group consisting of t-butyl groups and phenyl groups.

58. The monomer of claim 56 wherein R⁷ is a t-butyl group.

59. The monomer of claim 56 wherein X, Y, and Z have from about 2 to about 10 carbon atoms.

61. The monomer of claim 57 wherein X, Y, and Z have from about 2 to about 6 carbon atoms.

62. The monomer of claim 57 wherein X, Y, and Z have 6 carbon atoms.