Process for treating hard tissues

• US 5,980,253 A
• Filed: 01/12/1998
• Issued: 11/09/1999
• Est. Priority Date: 01/12/1998
• Status: Expired due to Term

• Current Assignee: 3M Innovative Properties Company (3M Company)
• Original Assignee: 3M Innovative Properties Company (3M Company)
• Inventors: Oxman, Joel D., Jacobs, Dwight W., Bui, Hoa T.
• Primary Examiner(s): Berman, Susan W.
• Application Number:
  US09/005,885
• Time in Patent Office: 666 Days
• Field of Search: 522/170, 522/25, 522/29, 522/28, 522/182, 522/31, 522/81, 522/83, 522/908, 523/116, 433/228.1, 206/63.5, 106/35
• US Class Current: 433/228.1
• CPC Class Codes: A61K 6/30 Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
• CPC Class Codes: C08L 33/00 Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
• CPC Class Codes: C08L 63/00 Compositions of epoxy resins; Compositions of derivatives of epoxy resins
• CPC Class Codes: Y10S 522/908 Dental utility

Abstract

In a first aspect, a method for treating hard tissue that includes: (a) applying to hard tissue a composition that includes a cationically active functional group, a free radically active functional group, and a polymerization initiator capable of initiating free radical polymerization, where the number of moles of cationically active functional groups per gram of composition is no greater than about 0.0075; and (b) exposing the composition to polymerization conditions to form an adhesive bonded to the hard tissue.

In a second aspect, a method for treating hard tissue that includes: (a) applying to hard tissue a first polymerizable composition that includes a free radically active functional group and a polymerization initiator capable of initiating free radical polymerization, but is essentially free of polymerizable components having cationically active functional groups and is capable of forming an adhesive bonded to the hard tissue upon exposure to polymerization conditions; (b) applying a second polymerizable composition; and (c) exposing the second composition to polymerization conditions to form a hardened composition adhered to the hard tissue. The second composition includes (i) a cationically active functional group and (ii) an polymerization initiator capable of initiating cationic polymerization.

Claims

1. A method for treating hard tissue comprising:

(a) applying to hard tissue a composition comprising a cationically active functional group, a free radically active functional group, and a polymerization initiator capable of initiating free radical polymerization,

wherein the number of moles of said cationically active functional groups per gram of said composition is no greater than about 0.0075; and

(b) exposing said composition to polymerization conditions to form an adhesive bonded to said hard tissue.

2. A method according to claim 1 wherein the number of moles of said cationically active functional groups per gram of said composition is no greater than about 0.002.

3. A method according to claim 1 further comprising treating said hard tissue prior to application of said composition with an agent selected from the group consisting of etchants, primers, adhesion promoters, and combinations thereof.

4. A method according to claim 1 comprising exposing said composition to visible light to form said adhesive bonded to said hard tissue.

5. A method according to claim 1 wherein said composition comprises an epoxy resin.

6. A method according to claim 1 wherein said composition comprises an ethylenically unsaturated compound.

7. A method according to claim 1 wherein said composition comprises an acrylic acid ester, a methacrylic acid ester, or a combination thereof.

8. A method according to claim 1 wherein said composition comprises a hydroxy-functional acrylic acid ester, a hydroxy-functional methacrylic acid ester, or a combination thereof.

9. A method according to claim 1 wherein said composition comprises (a) an epoxy resin and (b) an acrylic acid ester, a methacrylic acid ester, or a combination thereof.

10. A method according to claim 1 wherein said composition comprises a polymerizable component comprising a cationically active functional group and a free radically active functional group.

11. A method according to claim 10 wherein said polymerizable component comprises an epoxy-functional acrylic acid ester, methacrylic acid ester, or a combination thereof.

12. A method according to claim 1 wherein said initiator is capable of initiating free radical polymerization and cationic polymerization.

13. A method according to claim 1 wherein said initiator comprises an iodonium salt.

14. A method according to claim 1 wherein said initiator comprises an iodonium salt and a visible light sensitizer.

15. A method according to claim 1 wherein said initiator comprises an iodonium salt, a visible light sensitizer, and an electron donor,

wherein said initiator has a photoinduced potential greater than or equal to that of 3-dimethylamnino benzoic acid in a standard solution of 2.9×

10^-5 moles/g diphenyl iodonium hexafluoroantimonate and 1.5×

10^-5 moles/g camphorquinone in 2-butanone.

16. A method according to claim 1 wherein said composition comprises a hydroxy-functional component.

17. A method according to claim 16 wherein said hydroxy-functional component comprises a polyol.

18. A method according to claim 1 wherein the strength of the bond formed between said adhesive and said hard tissue is at least about 3 MPa.

19. A method according to claim 1 wherein said hard tissues comprises tooth enamel.

20. A method according to claim 1 wherein said hard tissue comprises dentin.

21. A method according to claim 1 further comprising applying a dental material to said adhesive.

22. A method according to claim 21 wherein said dental material comprises a dental composite.

23. A method according to claim 1 farther comprising applying a dental material to said composition prior to polymerization.

24. A method according to claim 23 wherein said dental material comprises a dental composite.

25. A method according to claim 22 or 24 wherein said dental composite comprises a cationically active functional group, a polymerization initiator, and a filler.

26. A method according to claim 25 wherein said dental composite further comprises a free radically active functional group.

27. A method according to claim 25 wherein said polymerization initiator of said dental composite is capable of initiating cationic polymerization.

28. A kit comprising:

(a) a composition comprising a cationically active functional group, a free radically active functional group, and a polymerization initiator capable of initiating free radical polymerization,

wherein the number of moles of said cationically active functional groups per gram of said composition is no greater than about 0.0075,

wherein said composition forms an adhesive capable of bonding to a tooth upon exposure to polymerization conditions; and

(b) a dental material capable of bonding to said adhesive.

29. A kit according to claim 28 wherein said dental material comprises a dental composite.

30. A kit according to claim 29 wherein said dental composite comprises a cationically active functional group, a polymerization initiator, and a filler.

31. A kit according to claim 30 wherein said dental composite further comprises a free radically active functional group.

32. A method for treating hard tissue comprising:

(a) applying to hard tissue a first polymerizable composition comprising a free radically active functional group and a polymerization initiator capable of initiating free radical polymerization,

said first composition being essentially free of polymerizable components having cationically active functional groups and being capable of forming an adhesive bonded to said hard tissue upon exposure to polymerization conditions;

(b) applying a second polymerizable composition comprising (i) a cationically active functional group and (ii) a polymerization initiator capable of initiating cationic polymerization; and

(c) exposing said second composition to polymerization conditions form a hardened composition adhered to said hard tissue.

33. A method according to claim 32 comprising exposing said first composition to polymerization conditions to form said adhesive prior to application of said second polymerizable composition.

34. A method according to claim 32 comprising exposing said first composition to polymerization conditions to form said adhesive subsequent to application of said second polymerizable composition.

35. A method according to claim 32 further comprising treating said hard tissue prior to application of said first composition with an agent selected from the group consisting of etchants, primers, adhesion promoters, and combinations thereof.

36. A method according to claim 32 wherein said first composition comprises a functional group capable of covalently bonding to said second composition.

37. A method according to claim 36 wherein said functional group comprises a hydroxyl group.

38. A method according to claim 32 wherein said first composition comprises a polyol.

39. A method according to claim 32 wherein said first composition comprises a component having a free radically active functional group and a functional group capable of covalently bonding to said second composition.

40. A method according to claim 32 wherein said first composition comprises a hydroxy-fuictional acrylic acid ester, a hydroxy-functional methacrylic acid ester, or a combination thereof.

41. A method according to claim 32 wherein said second composition comprises an epoxy resin.

42. A method according to claim 32 wherein said second composition further comprises a free radically active functional group.

43. A method according to claim 42 wherein said second composition comprises an acrylic acid ester, a methacrylic acid ester, or a combination thereof.

44. A method according to claim 32 wherein said second composition comprises a component comprising a cationically active functional group and a free radically active functional group.

45. A method according to claim 32 wherein at least one of said initiators comprises an iodonium salt.

46. A method according to claim 32 wherein at least one of said initiators comprises an iodonium salt and a visible light sensitizer.

47. A method according to claim 32 wherein at least one of said initiators comprises an iodonium salt, a visible light sensitizer, and an electron donor,

wherein said initiator has a photoinduced potential greater than or equal to that of 3-dimethylamino benzoic acid in a standard solution of 2.9×

10^-5 moles/g diphenyl iodonium hexafluoroantimonate and 1.5×

10^-5 moles/g camphorquinone in 2-butanone.

48. A method according to claim 32 wherein said hard tissue comprises tooth enamel.

49. A method according to claim 32 wherein said hard tissue comprises dentin.

50. A method according to claim 32 wherein said second composition comprises a dental material.

51. A method according to claim 32 wherein said second composition comprises a dental composite.

52. A kit comprising:

(a) a first polymerizable composition comprising a free radically active functional group and a polymerization initiator capable of initiating free radical polymerization,

said first composition being essentially free of polymerizable components having cationically active functional groups,

wherein said first composition forms an adhesive capable of bonding to a tooth upon exposure to polymerization conditions; and

(b) a second polymerizable composition comprising a cationically active functional group and a polymerization initiator capable of initiating cationic polymerization,

wherein said second composition forms a hardened composition adhered to the tooth upon exposure to polymerization conditions.

53. A kit according to claim 52 wherein said first composition comprises a hydroxy-functional component capable of covalently bonding to said second composition.

54. A kit according to claim 52 wherein said second composition comprises a dental composition.