One-component primer/bonding-resin systems

• US 5,658,963 A
• Filed: 02/02/1995
• Issued: 08/19/1997
• Est. Priority Date: 02/02/1995
• Status: Expired due to Term

• Current Assignee: Bisco, Inc.
• Original Assignee: Bisco, Inc.
• Inventors: Qian, Xuejun, Suh, Byoung I., Tobias, Russell H., Hamer, Martin
• Primary Examiner(s): CHAPMAN, MARK A
• Application Number:
  US08/382,617
• Time in Patent Office: 929 Days
• Field of Search: 522/14, 522/908, 106/35, 523/116, 433/228.1
• US Class Current: 522/14
• CPC Class Codes: A61K 6/30 Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
• CPC Class Codes: A61K 6/40 Primers for dental adhesives A61K6/30
• CPC Class Codes: A61K 6/60 comprising organic or organo-metallic additives
• CPC Class Codes: A61K 6/887 Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C08F 220/00 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 a salt, anhydride ester, amide, imide or nitrile thereof
• CPC Class Codes: C09J 4/00 Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
• CPC Class Codes: Y10S 522/908 Dental utility

Abstract

Primer/bonding-resin compositions include certain hydrophilic monomers, reactive diluent monomers, high viscosity adhesive resins and photo-initiator systems, all provided in a one-component solution containing ethanol or acetone or other suitable solvents. Methods of use of such compositions include a single step application for priming and imparting enhanced adhesion between dental substrates and dental restoratives or components.

Claims

1. A primer/bonding-resin composition comprising:

(A) a polymerizable resin component comprising a mixture of

(i) at least one of a hydrophilic primer monomer having at least one carboxylic acid group and at least one polymerizable vinyl group, said primer monomer comprising a reaction product of at least one of an anhydride and a dianhydride compound with a compound having at least one vinyl group and at least one hydroxyl group,

(ii) at least one high viscosity bonding resin compound having at least one reactive vinyl group, and

(iii) a reactive monomer for diluting the viscosity of at least one of said high viscosity bonding resin compound and said hydrophilic primer monomer, said reactive monomer having at least one vinyl group reactive with at least one of said high viscosity bonding resin and said hydrophilic monomer;

(B) a photo-initiator system for initiating polymerization of said resin component when said system is combined with said resin component and exposed to activating radiation; and

(C) a solvent for dissolving or suspending said resin component and said photo-initiator system in a flowable form,

wherein said resin component, said photo-initiator system and said solvent are selected so that a mixture thereof results in a shelf stable composition substantially polymerizable upon exposure of said mixture to at least one of an activating radiation and an external polymerization catalyst.

2. The composition of claim 1 wherein said polymerizable resin component is between about 2 wt. % and about 80 wt. % of said composition.

3. The composition of claim 1 wherein said hydrophilic primer monomer is between about 0.5 wt. % and about 50 wt. % of said composition.

4. The composition of claim 1 wherein said hydrophilic primer monomer is between about 2 wt. % and about 40 wt. % of said composition.

5. The composition of claim 1 wherein said hydrophilic primer monomer is between about 5 wt. % and about 30 wt. % of said composition.

6. The composition of claim 1 wherein said hydrophilic primer monomer is selected from the group consisting of BPDM, EDMT, DSDM, PMDM, PMGDM and mixtures thereof.

7. The composition of claim 6 wherein said hydrophilic primer monomer is selected from the group consisting of BPDM and EDMT and mixtures thereof.

8. The composition of claim 7 wherein said hydrophilic primer monomer is BPDM.

9. The composition of claim 1 wherein said hydrophilic primer monomer is a reaction product of at least one of an anhydride and a dianhydride with a compound having at least one reactive hydroxyl group and at least one vinyl group.

10. The composition of claim 1 wherein said high viscosity bonding resin compound is between about 0.5 wt. % and about 50 wt. % of said composition.

11. The composition of claim 1 wherein said high viscosity bonding resin compound is between about 1 wt. % and about 30 wt. % of said composition.

12. The composition of claim 1 wherein said high viscosity bonding resin compound is between about 5 wt. % and about 15 wt. % of said composition.

13. The composition of claim 1 wherein said high viscosity bonding resin compound is selected from the group consisting of Bis-GMA, DPEPA, PEDM, UDMA, and mixtures thereof.

14. The composition of claim 1 wherein said reactive monomer for diluting the viscosity of said high viscosity bonding resin compound is between about 0.5 wt. % and about 50 wt. % of said composition.

15. The composition of claim 1 wherein said reactive monomer for diluting the viscosity of said high viscosity bonding resin compound is between about 1 wt. % and about 30 wt. % of said composition.

16. The composition of claim 1 wherein said reactive monomer for diluting the viscosity of said high viscosity bonding resin compound is between about 5 wt. % and about 25 wt. % of said composition.

17. The composition of claim 1 wherein said reactive monomer for diluting the viscosity of said high viscosity bonding resin compound is selected from the group consisting of 2-HEMA, GM, HPMA, and mixtures thereof.

18. The composition of claim 1 wherein said photo-initiator system comprises a mixture of

(A) a light-sensitive initiator compound;

and

(B ) a polymerization accelerator compound activatable by said light-sensitive initiator compound to a state causing accelerated polymerization of said resin component, said accelerator compound selected from the group consisting of

(i) a tertiary aromatic amine compound having the formula ##STR4## wherein R is at least one of C₁ -C₃ alkyl, C₁ -C₃ alkyl alcohol, and CN(CH₂)_n wherein n is 1-3;

R'"'"' is at least one of C₁ -C₃ alkyl, C₁ -C₃ alkyl alcohol, and CN(CH₂)_n wherein n is 1-3; and

X is an electron-withdrawing substituent; and

(ii) a cyclic amine compound having the formula ##STR5## wherein Y is selected from the group consisting of CH₂ CH₂ Z, CH₂ CH₂ CH₂ Z, and CH₂ CH(CH₃)Z wherein Z is selected from the group consisting of acrylates, methacrylates, alcohols, carboxylic acids, derivatives of carboxylic acids, halogens, and other substituents which do not prevent polymerization of said resin component.

19. The composition of claim 18 wherein R is selected from the group consisting of CH₃, CH₂ CH₃, and CH₂ CH₂ CH₃ and R'"'"' is selected from the group consisting of CH₃, CH₂ CH₃, and CH₂ CH₂ CH₃.

20. The composition of claim 18 wherein Y selected from the group consisting of ethyl methacrylate and isopropyl methacrylate.

21. The composition of claim 18 wherein X is selected from the group consisting of COOH, alkali metal salts of COOH, COOR" wherein R" is an alkyl group, SO₃ H, salts of SO₃ H, CHO, halogen atoms, CH₂ COOH, salts of CH₂ COOH, and CN.

22. The composition of claim 18 wherein said fight-sensitive initiator compound is an alpha-diketone.

23. The composition of claim 18 wherein said light-sensitive initiator compound is selected from the group consisting of camphorquinone and derivatives thereof.

24. The composition of claim 18 wherein said light-sensitive initiator compound is between about 0.01 wt. % and about 5 wt. % of said composition.

25. The composition of claim 18 wherein said light-sensitive initiator compound is between about 0.05 wt. % and about 2 wt. % of said composition.

26. The composition of claim 18 wherein said light-sensitive initiator compound is between about 0.1 wt. % and about 1.0 wt. % of said composition.

27. The composition of claim 18 wherein said photo-initiator system comprises camphorquinone and said tertiary aromatic amine compound.

28. The composition of claim 18 wherein said polymerization accelerator compound comprises said tertiary aromatic amine compound being selected from the group consisting of DMABA, EDMAB and DMABAL.

29. The composition of claim 27 wherein said tertiary aromatic amine compound is selected from the group consisting of DMABA and DMABAL.

30. The composition of claim 29 wherein said tertiary aromatic amine compound is DMABAL.

31. The composition of claim 18 wherein said polymerization accelerator compound is between about 0.01 wt. % and about 10 wt. % of said composition.

32. The composition of claim 18 wherein said polymerization accelerator compound is between about 0.05 wt. % and about 5 wt. % of said composition.

33. The composition of claim 1 wherein said solvent is between about 5 wt. % and about 98 wt. % of said composition.

34. The composition of claim 1 wherein said solvent is between about 10 wt. % and about 90 wt. % of said composition.

35. The composition of claim 1 wherein said solvent is between about 20 wt. % and about 80 wt. % of said composition.

36. The composition of claim 1 wherein said solvent is selected from the group consisting of water, ethanol, acetone, and mixtures thereof.

37. The composition of claim 1 wherein said solvent comprises a mixture of ethanol, acetone and optionally water.

38. The composition of claim 37 wherein said solvent is a mixture of ethanol and acetone.

39. The composition of claim 36 wherein said solvent is ethanol.

40. The composition of claim 36 wherein said solvent is acetone.