Two-component adhesive for bonding artificial teeth to a denture base

Abstract

Dental adhesives and their uses, for instance an adhesive containing at least one first component A and at least one second component B, characterized in that said at least one first component A comprises a methyl methacrylate, a copolymer of methyl methacrylate dissolved in excess methyl methacrylate, at least one polyfunctional (meth)acrylate and a peroxide-based free-radical initiator, wherein said copolymer of methyl methacrylate is present in an amount of 30-50 parts by weight dissolved in a solution of 65-85 parts by weight of monomeric methyl methacrylate and 3-15 parts by weight of the polyfunctional (meth)acrylate, especially the triethylene glycol dimethacrylate (TEGDMA), mixed with a solution of 0.5 to 3 parts by weight of said peroxide-based free-radical initiator, especially dibenzoyl peroxide, in 70-90 parts by weight of monomeric methyl methacrylate, and said at least one second component B comprises methyl methacrylate and a tertiary amine.

Claims

1. A dental adhesive system mixture comprising: at least one first component A and at least one second component B, wherein said at least one first component A comprises a methyl methacrylate, a copolymer of methyl methacrylate dissolved in excess methyl methacrylate, and a peroxide-based free-radical initiator, wherein said copolymer of methyl methacrylate is present in an amount of 30-50 parts by weight dissolved in a solution of 65-85 parts by weight of monomeric methyl methacrylate and 3-15 parts by weight of the polyfunctional (meth) acrylate, mixed with a solution of 0.5to 3 parts by weight of said peroxide-based free-radical initiator in 70-90 parts by weight of monomeric methyl methacrylate, and said at least one second component B comprises methyl methacrylate and a tertiary amine.

2. The adhesive system according to claim 1, wherein said at least one component A is obtainable by dissolving the copolymer of methyl methacrylate in monomeric methyl methacrylate in the presence of at least one polyfunctional (meth) acrylate, and mixing with a solution of dibenzoyl peroxide in monomeric methyl methacrylate.

3. The adhesive system of claim 1 wherein said tertiary amine in said at least one component B is N, N-dimethyl-p-toluidine.

4. The adhesive system of claim 3 wherein 1-5 parts by weight of N, N-dimethyl-p-toluidine is dissolved in 65-85 parts by weight of monomeric methyl methacrylate.

5. The adhesive system of claim 2 wherein the at least one polyfunctional (meth) acrylate comprises triethylene glycol dimethacrylate.

6. The adhesive system of claim 1 further comprising pigments for coloring in the mixture.

7. A dental prosthesis with a denture base and artificial teeth erected therein, comprising artificial teeth permanently bonded to the denture base with the adhesive system of claim 1.

8. The adhesive system of claim 1, wherein the adhesive system is a two component adhesive.

9. A process for preparing a dental prosthesis with a denture base and artificial teeth erected therein comprising: applying the adhesive system of claim 1 to an area of the artificial teeth coming into contact with the denture base, and/or applying the adhesive system to the surfaces of the area in the denture base in which the artificial teeth are arranged, and after inserting the artificial teeth into the denture base and after curing the adhesive system, a permanent bond of the artificial teeth with the denture base is formed.

10. The adhesive system of claim 1 further comprising, additionally dissolved in component A, a polyfunctional (meth)acrylate, ethylene glycol dimethacrylate, butanediol dimethacrylate, hexanediol dimethacrylate, triethylene glycol dimethacrylate (TEGDMA), tetraethylene glycol dimethacrylate, diurethane dimethacrylate, bis(hydroxymethacryloyloxypropoxy)phenylpropane (bis-GMA), polyethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, ditrimethylolpropane tetraacrylate , or triethylene glycol dimethacrylate (TEGDMA).

11. The adhesive system of claim 1 wherein said peroxide-based free-radical initiator comprises dibenzoyl peroxide.

12. A method of treating a patient comprising bonding artificial teeth to a denture base with the adhesive system of claim 1.

13. The method of claim 12 wherein the artificial base and/or the artificial teeth comprise polymethylmethacrylate and/or copolymers of methyl methacrylate.

14. A method of treating a dental restoration comprising using the adhesive system of claim 1 as a clear coat for sealing dental restorations or as a lacquer for painting dental restorations.

Description

BRIEF DESCRIPTION OF THE DRAWINGS

(1) FIG. 1 shows a test specimen with a prosthetic tooth.

(2) FIG. 2 shows a section along the line II-II of FIG. 1.

(3) FIG. 3 shows a test specimen after a fracture test with a prosthetic tooth bonded with the adhesive according to the invention.

(4) FIG. 4 shows a double section along the lines IV-IV and IV-IV through the test specimen of FIG. 3, taking into account the situation where even parts of the test specimen may be torn off during excavation.

(5) FIG. 5 shows a test specimen after a fracture test with a prosthetic tooth bonded with a conventional adhesive.

(6) FIG. 6 shows a double section along the lines VI-VI and VI-VI through the test specimen of FIG. 5.

DETAILED DESCRIPTION

(7) In another embodiment of the invention, said at least one first component A of the mixture according to the invention may comprise one or more polyfunctional (meth)acrylates, for example, ethylene glycol dimethacrylate, butanediol dimethacrylate, hexanediol dimethacrylate, triethylene glycol dimethacrylate (TEGDMA), tetraethylene glycol dimethacrylate, diurethane dimethacrylate, bis(hydroxymethacryloyloxypropoxy)phenylpropane (bis-GMA), polyethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, ditrimethylolpropane tetraacrylate, etc.

(8) According to the invention, the copolymer of methyl methacrylate is dissolved in an excess of methyl methacrylate in said at least one component A of the mixture according to the invention. In another embodiment of the invention, at least one of the mentioned polyfunctional (meth)acrylates, for example, ethylene glycol dimethacrylate, butanediol dimethacrylate, hexanediol dimethacrylate, triethylene glycol dimethacrylate (TEGDMA), tetraethylene glycol dimethacrylate, diurethane dimethacrylate, bis(hydroxymethacryloyloxypropoxy)phenylpropane (bis-GMA), polyethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, ditrimethylolpropane tetraacrylate, etc., may be present dissolved in component A.

(9) In another embodiment of the present invention, said at least one component A may be obtainable by dissolving the copolymer of methyl methacrylate in monomeric methyl methacrylate in the presence of at least one of the mentioned polyfunctional (meth)acrylates, for example, ethylene glycol dimethacrylate, butanediol dimethacrylate, hexanediol dimethacrylate, triethylene glycol dimethacrylate (TEGDMA), tetraethylene glycol dimethacrylate, diurethane dimethacrylate, bis(hydroxymethacryloyloxypropoxy)phenylpropane (bis-GMA), polyethylene glycol dimethacrylate, trimethylolpropane trimethacrylate, ditrimethylolpropane tetraacrylate, etc., and mixing with a solution of dibenzoyl peroxide in monomeric methyl methacrylate.

(10) Typically, said tertiary amine present in the mixture according to the invention in said at least one component B is N,N-dimethyl-p-toluidine. In particular, said tertiary amine may be dissolved in amounts of 1-5 parts by weight in the form of N,N-dimethyl-p-toluidine in 65-85 parts by weight of monomeric methyl methacrylate.

(11) The present invention also relates to a dental prosthesis with a denture base and artificial teeth erected therein, characterized in that said artificial teeth are permanently bonded to the denture base by means of the mixture according to the invention.

(12) The present invention also relates to the use of the mixture according to the invention as a two-component adhesive, especially for preparing the dental prosthesis according to the invention. Typically, according to the invention, the mixture according to the invention may be used for bonding artificial teeth, especially made of PMMA and/or its copolymers, to a denture base, especially made of PMMA and/or its copolymers.

(13) The present invention also relates to the use of the mixture according to the invention as a clear coat for sealing dental restorations, or of mixtures according to the invention colored by means of corresponding pigments for painting dental restorations.

(14) The present invention also relates to a process for preparing the dental prosthesis according to the invention, characterized in that the artificial teeth are permanently bonded to the denture base by applying the mixture according to the invention to the areas of the artificial teeth coming into contact with the denture base, and/or applying the mixture according to the invention to the surfaces of the areas in the denture base in which the artificial teeth are arranged, and by curing the mixture.

(15) The prostheses obtained with the mixture according to the invention were subjected to fracture tests according to the standard DIN 13998. Experience has shown that adhesive failure of the adhesive is to be expected without previous pretreatment of the adherend sites with a primer. This was also confirmed experimentally for prosthetic teeth bonded with conventional adhesives (FIGS. 5 and 6). Surprisingly, the prostheses prepared with the mixture according to the invention exclusively showed cohesive fracture surfaces in the teeth and/or denture base (FIG. 3, 4).

(16) The invention is further described hereinafter by means of the Examples.

Example 1

(17) 50 g of the copolymer of methyl methacrylate (Degacryl MW 332, Evonik, Germany) is dissolved in a mixture of 100 g of methyl methacrylate and 10 g of triethylene glycol dimethacrylate (TEGDMA) supplied by Lehmann & Voss & Co., Germany (Luvomaxx TEDMA). Thereafter, 2 g of dibenzoyl peroxide is dissolved in 80 g of methyl methacrylate, and to this solution is added 120 g of the first solution to obtain component A.

(18) Component B is prepared as follows: 3 g of N,N-dimethyl-p-toluidine is dissolved in 75 g of methyl methacrylate.

Example 2

(19) Component A as prepared in Example 1 was mixed with the mentioned component B at a ratio of 2:1 at room temperature. The mixture was applied either to the areas of the denture base coming into contact with the basal surface of the teeth, and/or to the basal surface of the artificial teeth, for example, with a paintbrush. The thus prepared prosthetic teeth were placed into the respective alveoli of the base. The thus prepared prosthesis was stored over night in an annealing furnace at 37 C. for the adhesive to cure.

(20) With test specimens prepared in the same way (FIGS. 1 and 2), fracture tests according to the standard DIN 13998 were performed. The prostheses exclusively showed cohesive fracture areas in the teeth and/or base (FIGS. 3 and 4).

LIST OF REFERENCE SYMBOLS

(21) 1. Test specimens for fracture tests according to DIN 13998 2. Prosthetic tooth bonded into the test specimen 3. Remnant of the prosthetic tooth after cohesive failure 4. Adhesive residues