US5401783A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Adhesion-promoting agents incorporating polyvalent cations
Assignee: American Dental Association
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Filing: 1993-11-24
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Granted: 1995-03-28
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Expires: 2013-11-24
Abstract
Abstract Materials and methods for preparing the surface of dentin, enamel, or other natural or industrial substrates containing or capable of binding metallic ions, for adhesion of composite materials or resins, are disclosed. Preferably, the substrate is treated with an aqueous solution comprising at least one acid, acidic salt, or chelating or sequestering agent. The resultant surface is then treated with a solution comprising a solvent and at least one adhesion-promoting agent selected from the group consisting of N-phenylglycine (NPG) and derivatives and analogues thereof, and other amino acids in the form of salts and complexes of these compounds with at least one species of divalent or polyvalent cation, or diamine or polyamine, wherein the divalent and polyvalent cations are preferably selected from the group consisting of alkaline earth elements, iron, aluminum, zinc, barium, chromium, manganese, cobalt, copper, and molybdenum, and wherein the divalent and polyvalent salts and complexes for each mixture comprise between 1 and 100% of the total mixture. Finally, a solution is applied which contains at least one monomer selected from the group consisting of (1) reaction products of dianhydrides with molecules containing at least one methacrylate, acrylate or other polymerizable group and also one reactive hydroxyl group, or primary or secondary amino group, (2) 4-methacryloxyethyltrimelliticanhydride and its dicarboxylic acid hydrolysis derivative, and (3) other compounds containing at least one group or moiety capable of free radical polymerization and at least one aromatic ring or moiety containing electron-withdrawing substituents that do not interfere with free radical polymerization, in the presence of a solvent, wherein the solvent comprises between 0 and 99.9% of the liquid. Alternative embodiments are also set forth.
Inventors
- 👤 Rafael L. Bowen
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 15:06
CPC Classifications
A; A61; A61K; A61K6/00; A61K6/60; A61K6/69; A61K6/30; A61K6/40
Claims Analysis
Total Claims: 44
Claim 1
Independent Claim
255 words
A method for preparing the surface of dentin, enamel, or other natural or industrial substrates containing or capable of binding divalent or polyvalent cations or amines, for adhesion of composite materials or resins, which method comprises: (a) contacting the surface with a solution comprising a composition having at least one acid, acidic salt, or chelating or sequestering agent, wherein the composition is soluble in water; (b) contacting the surface with a solution comprising a composition having at least one adhesion-promoting agent selected from the group consisting of N-phenylglycine (NPG), N-phenylalanine, 2-(N-phenyl) alkanoic acids and derivatives and analogues thereof, and other amino acids, in the form of salts or complexes of these compounds with at least one member of the group consisting of divalent cations, polyvalent cations, amines, diamines and polyamines, wherein the composition is soluble in an organic solvent; and (c) contacting the surface with a liquid comprising at least one adhesive resin monomer selected from the group consisting of (1) reaction products of dianhydrides with molecules containing at least one methacrylate, acrylate or other polymerizable group and also one reactive hydroxyl group, or primary or secondary amino group, (2) 4-methacryloxyethyltrimelliticanhydride and its dicarboxylic acid hydrolysis derivative, (3) other compounds containing at least one group or moiety capable of free radical polymerization and at least one aromatic ring or moiety containing electron-withdrawing substituents that do not interfere with free radical polymerization, and (4) other compounds containing at least one group or moiety capable of free-radical polymerization and at least one carboxyl group or salt thereof.
Claim 2
Independent Claim
255 words
A method for preparing the surface of dentin, enamel, or other natural or industrial substrates containing or capable of binding divalent or polyvalent cations or amines, for adhesion of composite materials or resins, which method comprises: (a) contacting the surface with a solution comprising a composition having at least one acid, acidic salt, or chelating or sequestering agent, wherein the composition is soluble in water; (b) contacting the surface with a solution comprising a composition having at least one adhesion-promoting agent selected from the group consisting of N-phenylglycine (NPG), N-phenylalanine, 2-(N-phenyl) alkanoic acids and derivatives and analogues thereof, and other amino acids, in the form of salts or complexes of these compounds with at least one member of the group consisting of divalent cations, polyvalent cations, amines, diamines and polyamines, wherein the composition is soluble in an organic solvent; and (c) contacting the surface with a liquid comprising at least one adhesive resin monomer selected from the group consisting of (1) reaction products of dianhydrides with molecules containing at least one methacrylate, acrylate or other polymerizable group and also one reactive hydroxyl group, or primary or secondary amino group, (2) 4-methacryloxyethyltrimelliticanhydride and its dicarboxylic acid hydrolysis derivative, (3) other compounds containing at least one group or moiety capable of free radical polymerization and at least one aromatic ring or moiety containing electron-withdrawing substituents that do not interfere with free radical polymerization, and (4) other compounds containing at least one group or moiety capable of free-radical polymerization and at least one carboxyl group or salt thereof.
Claim 3
Dependent Claim
16 words
The method of claim 1 wherein steps (a), (b) and (c) are performed in that order.
Claim 4
Dependent Claim
45 words
The method according to claim 1 wherein the divalent and polyvalent salts and complexes of subpart (b) are N-arylglycine and N-arylalanine derivatives and ring-substituted N-arylglycine and N-arylalanine derivatives, and wherein the derivatives contain at least one free carboxyl group and at least one polymerizable group.
Claim 5
Dependent Claim
22 words
The method according to claim 3 wherein the polymerizable group is a methacrylate, acrylate, vinyl or other group capable of free-radical polymerization.
Claim 6
Dependent Claim
47 words
The method of claim 1 wherein the monomer of subpart (c) is selected from the group consisting of (1) the addition reaction product of pyromellitic acid dianhydride and glyceroldimethacrylate, (2) the addition reaction product of 3,3',4,4'-benzophenonetetracarboxylic dianhydride and glyceroldimethacrylate, (3) 4-methacryloxyethyltrimellitic anhydride, and (4) trimellitic anhydride dimethacrylate.
Claim 7
Dependent Claim
24 words
The method of claim 1 wherein the concentration of acid, acidic salt, or chelating or sequestering agent is from about 0.1% to about 50%.
Claim 8
Dependent Claim
28 words
The method of claim 1 wherein the acid, acidic salt, or chelating or sequestering agent is in an aqueous solution which is substantially isotonic with physiological saline solution.
Claim 9
Dependent Claim
44 words
The method of claim 1 wherein the acid, acidic salt, or chelating or sequestering agent is selected from the group consisting of nitric acid, citric acid, phosphoric acid, hydrochloric acid, a sulfinic acid, formic acid, maleic acid, pyruvic acid and salts of ethylenediamine-tetraacetic acid.
Claim 10
Dependent Claim
25 words
The method of claim 1 wherein the concentration of the monomer in the solution of subpart (c) is from about 0.1% to a saturated solution.
Claim 11
Dependent Claim
24 words
The method of claim 1 wherein the di- and polyvalent cations are cations of alkaline earth elements or transition metal elements or mixtures thereof.
Claim 12
Dependent Claim
13 words
The method of claim 1 wherein the solvent of subpart (c) is acetone.
Claim 13
Dependent Claim
17 words
The method of claim 1 wherein the substrate surface is a dentin surface or an enamel surface.
Claim 14
Dependent Claim
11 words
The method of claim 1 wherein the adhesion-promoting agent is N-phenylglycine.
Claim 15
Dependent Claim
11 words
The method of claim 1 wherein the adhesion-promoting agent is N-methyl-N-phenylglycine.
Claim 16
Dependent Claim
11 words
The method of claim 1 wherein the adhesion-promoting agent is N(p-tolyl)glycine.
Claim 17
Dependent Claim
17 words
The method of claim 1 wherein the adhesion-promoting agent is the adduct of N-phenylglycine and glycidyl methacrylate.
Claim 18
Dependent Claim
19 words
The method of claim 1 wherein the adhesion-promoting agent is the addition reaction product of N(p-tolyl)glycine and glycidyl methacrylate.
Claim 19
Dependent Claim
23 words
The method of claim 1 wherein the composition of subpart (b) also includes a composition comprised of a solvent and a polymerization initiator.
Claim 20
Dependent Claim
19 words
The method of claim 18 wherein the polymerization initiator is comprised of a salt or derivative of sulfinic acid.
Claim 21
Dependent Claim
20 words
The method of claim 18 wherein the polymerization initiator is applied to the substrate immediately before polymerization initiation is desired.
Claim 22
Dependent Claim
24 words
The method of claim 1 wherein one or more of the solutions of subparts (a)-(c) are mixed together immediately before application to the surface.
Claim 23
Dependent Claim
22 words
The method of claim 1 wherein at least one of the solutions of subparts (a)-(c) also contains at least one polymerization inhibitor.
Claim 24
Dependent Claim
33 words
The method of claim 22 wherein the polymerization inhibitor is selected from the group consisting of 4-hydroxymethyl-2,6-di-tert-butylphenol; BHT; 2,5-di-tert-butylhydroquinone; tert-butylhydroquinone; 4-hydroxy-3,5-di-tert-butylphenyl propionic acid; 3,3'-thiodipropionic acid; 3,5-di-tert-butyl-4-hydroxyanisole; the monomethyl ether of hydroquinone; and hydroquinone.
Claim 25
Dependent Claim
22 words
The method of claim 1 wherein at least one of the compositions of subparts (a)-(c) contains camphorquinone or a derivative of camphorquinone.
Claim 26
Dependent Claim
33 words
The method of claim 1 wherein at least one of the compositions of subparts (a)-(c) contains a tertiary amine having a hydrogen atom attached to a carbon atom adjacent to a nitrogen atom.
Claim 27
Dependent Claim
20 words
The method of claim 1 wherein at least one of the compositions of subparts (a)-(c) contains benzoyl or other peroxide.
Claim 28
Dependent Claim
19 words
The method of claim 1 wherein at least one of the compositions of subparts (a)-(c) contains an antimicrobial agent.
Claim 29
Dependent Claim
27 words
The method of claim 27 wherein the antimicrobial agent is a quaternary ammonium salt, a benzalkonium salt, a cetylpyridinium salt, a chlorhexidine salt or an alexidine salt.
Claim 30
Dependent Claim
26 words
A structure comprising a composite material or resin bonded to a dentin or enamel surface which has been prepared according to the method of claim 1.
Claim 31
Dependent Claim
26 words
A structure comprising a composite material or resin bonded to a natural or industrial substrate which has been prepared according to the method of claim 1.
Claim 32
Dependent Claim
54 words
A method for bonding a composite material or resin to the surface of dentin, enamel, or other natural or industrial substrates containing or capable of binding divalent or polyvalent cations or amines which comprises practicing the method of claim 1, and then contacting the surface with an unfilled light-cure resin and light-curing the resin.
Claim 33
Dependent Claim
142 words
A method for preparing the divalent and polyvalent salts and complexes of adhesion-promoting agents of subpart (b) of claim 1 comprising: (a) providing a first solution comprised of monovalent cationic salts or ammonium or amine salts of at least one adhesion-promoting agent selected from the group consisting of N-phenylglycine (NPG), and derivatives and analogues thereof, and other amino acids; (b) providing a second concentrated solution of at least one salt of magnesium, calcium, aluminum, strontium, zinc, barium, iron, chromium, manganese, cobalt, copper, molybdenum, other di- or polyvalent cations, amine salts, or quaternary ammonium compounds, or mixtures thereof, wherein these salts do not form totally insoluble reaction products with the compounds of subpart (a); (c) mixing the first and second solutions by stirring to form a precipitate of divalent or polyvalent salts and complexes thereof; and (d) separating the precipitate from the solution.
Claim 34
Independent Claim
232 words
A method for preparing the surface of dentin, enamel, or other natural or industrial substrates containing or capable of binding divalent or polyvalent cations or amines, for adhesion of composite materials or resins, which method comprises: (a) contacting the surface with a solution comprising a composition having at least one acid, acidic salt, or chelating or sequestering agent, wherein the composition is soluble in water; (b) contacting the surface with a solution comprising a composition having at least one adhesion-promoting agent selected from the group consisting of N-phenylglycine (NPG), N-phenylalanine, 2-(N-phenyl) alkanoic acids and derivatives and analogues thereof, and other amino acids, in the form of salts or complexes of these compounds with at least one member of the group consisting of divalent cations, polyvalent cations, amines, diamines and polyamines, wherein the composition is soluble in an organic solvent; and (c) contacting the surface with a liquid comprising at least one adhesive resin monomer selected from the group consisting of (1) reaction products of dianhydrides with molecules containing at least one methacrylate, acrylate or other polymerizable group and also one reactive hydroxyl group, or primary or secondary amino group, (2) 4-methacryloxyethyltrimelliticanhydfide and its dicarboxylic acid hydrolysis derivative, and (3) other compounds containing at least one group or moiety capable of free radical polymerization and at least one aromatic ring or moiety containing electron-withdrawing substituents that do not interfere with free radical polymerization.
Claim 35
Independent Claim
232 words
A method for preparing the surface of dentin, enamel, or other natural or industrial substrates containing or capable of binding divalent or polyvalent cations or amines, for adhesion of composite materials or resins, which method comprises: (a) contacting the surface with a solution comprising a composition having at least one acid, acidic salt, or chelating or sequestering agent, wherein the composition is soluble in water; (b) contacting the surface with a solution comprising a composition having at least one adhesion-promoting agent selected from the group consisting of N-phenylglycine (NPG), N-phenylalanine, 2-(N-phenyl) alkanoic acids and derivatives and analogues thereof, and other amino acids, in the form of salts or complexes of these compounds with at least one member of the group consisting of divalent cations, polyvalent cations, amines, diamines and polyamines, wherein the composition is soluble in an organic solvent; and (c) contacting the surface with a liquid comprising at least one adhesive resin monomer selected from the group consisting of (1) reaction products of dianhydrides with molecules containing at least one methacrylate, acrylate or other polymerizable group and also one reactive hydroxyl group, or primary or secondary amino group, (2) 4-methacryloxyethyltrimelliticanhydfide and its dicarboxylic acid hydrolysis derivative, and (3) other compounds containing at least one group or moiety capable of free radical polymerization and at least one aromatic ring or moiety containing electron-withdrawing substituents that do not interfere with free radical polymerization.
Claim 36
Independent Claim
241 words
A method for preparing the surface of dentin, enamel, or other natural or industrial substrates containing or capable of binding divalent or polyvalent cations or amines, for adhesion of composite materials or resins, which method comprises: (a) contacting the surface with a solution comprising a composition having at least one acid, acidic salt, or chelating or sequestering agent, wherein the composition is soluble in water; (b) contacting the surface with a solution comprising a composition having at least one adhesion-promoting agent selected from the group consisting of N-phenylglycine (NPG), N-phenylalanine, 2-(N-phenyl) alkanoic acids and derivatives and analogues thereof, and other amino acids, in the form of salts or complexes of these compounds with at least one member of the group consisting of divalent cations, polyvalent cations, amines, diamines and polyamines, wherein the composition is soluble in an organic solvent; and p1 (c) contacting the surface with a liquid comprising at least one adhesive resin monomer selected from the group consisting of reaction products of dianhydrides with molecules containing at least one methacrylate, acrylate or other polymerizable group and also one reactive hydroxyl group, or primary or secondary amino group, wherein the dianhydrides are selected from one or more of the group consisting of 5-(2,5-dioxotetrahydro-3-furanyl)-3-cyclohexene- 1,2-dicarboxylic anhydride, symmetrical biphenyl tetracarboxylic dianhydride, glycerol acetate bistrimellitate dianhydride, polyol trimellitate dianhydride, 3,3',4,4'-diphenylsulfone tetracarboxylic dianhydride, 4,4'-oxydiphthalic anhydride, 4,4'-hexafluoroisopropylidene-bisphthalic anhydride, pyromellitic dianhydride, 3,3',4,4'-benzophenone tetracarboxylic dianhydride, ethylene glycol bistrimellitate dianhydride, mellophanic dianhydride, bicyclo(2.2.2)octane-2,3,5,6-tetracarboxylic dianhydride, bicyclo(2.2.2)-7-octene-2,3,5,6-tetracarboxylicdianhydride, and 1,2,3,4-cyclopentanetetracarboxylic dianhydride.
Claim 37
Independent Claim
241 words
A method for preparing the surface of dentin, enamel, or other natural or industrial substrates containing or capable of binding divalent or polyvalent cations or amines, for adhesion of composite materials or resins, which method comprises: (a) contacting the surface with a solution comprising a composition having at least one acid, acidic salt, or chelating or sequestering agent, wherein the composition is soluble in water; (b) contacting the surface with a solution comprising a composition having at least one adhesion-promoting agent selected from the group consisting of N-phenylglycine (NPG), N-phenylalanine, 2-(N-phenyl) alkanoic acids and derivatives and analogues thereof, and other amino acids, in the form of salts or complexes of these compounds with at least one member of the group consisting of divalent cations, polyvalent cations, amines, diamines and polyamines, wherein the composition is soluble in an organic solvent; and p1 (c) contacting the surface with a liquid comprising at least one adhesive resin monomer selected from the group consisting of reaction products of dianhydrides with molecules containing at least one methacrylate, acrylate or other polymerizable group and also one reactive hydroxyl group, or primary or secondary amino group, wherein the dianhydrides are selected from one or more of the group consisting of 5-(2,5-dioxotetrahydro-3-furanyl)-3-cyclohexene- 1,2-dicarboxylic anhydride, symmetrical biphenyl tetracarboxylic dianhydride, glycerol acetate bistrimellitate dianhydride, polyol trimellitate dianhydride, 3,3',4,4'-diphenylsulfone tetracarboxylic dianhydride, 4,4'-oxydiphthalic anhydride, 4,4'-hexafluoroisopropylidene-bisphthalic anhydride, pyromellitic dianhydride, 3,3',4,4'-benzophenone tetracarboxylic dianhydride, ethylene glycol bistrimellitate dianhydride, mellophanic dianhydride, bicyclo(2.2.2)octane-2,3,5,6-tetracarboxylic dianhydride, bicyclo(2.2.2)-7-octene-2,3,5,6-tetracarboxylicdianhydride, and 1,2,3,4-cyclopentanetetracarboxylic dianhydride.
Claim 38
Independent Claim
345 words
A method for preparing the surface of dentin, enamel, or other natural or industrial substrates containing or capable of binding divalent or polyvalent cations or amines, for adhesion of composite materials or resins, which method comprises: (a) contacting the surface with a solution comprising a composition having at least one acid, acidic salt, or chelating or sequestering agent, wherein the composition is soluble in water; (b) contacting the surface with a solution comprising a composition having at least one adhesion-promoting agent selected from the group consisting of N-phenylglycine (NPG), N-phenylalanine, 2-(N-phenyl) alkanoic acids, N-phenylalanine, 2-(N-phenyl) alkanoic acids other amino acids, and derivatives and analogues thereof selected from the group consisting of the addition reaction product of N(p-tolyl)glycine and glycidyl methacrylate (NTG-GMA); the adduct of N-phenylglycine and glycidyl methacrylate (NPG-GMA); the adduct of N(4-chlorophenyl)glycine and glycidyl methacrylate (NCPG-GMA); the adduct of N-phenylglycine and 1,2-epoxy-3-phenoxypropane (NPG-PGE); the adduct of N-phenylglycine and p-chlorophenyl-2,3-epoxypropyl ether (NPG-CGE); the adduct of N-p-chlorophenylglycine and p-chlorophenyl-2,3-epoxypropyl ether (NCG-CGE); the reaction product of N-p-chlorophenylglycine and phenyl-2,3-epoxypropyl ether (NCG-PGE); the adduct of N-phenylalanine and glycidyl methacrylate (NPA-GMA); and the adduct of N-tolyl-2(or alpha)-alanine, N-phenylalanine or 2-(N-phenyl) alkanoic acids and glycidyl methacrylate (NTA-GMA), in the form of salts or complexes of these compounds with at least one member of the group consisting of divalent cations, polyvalent cations, amines, diamines and polyamines, wherein the composition is soluble in an organic solvent; and (c) contacting the surface with a liquid comprising at least one adhesive resin monomer selected from the group consisting of (1) reaction products of dianhydrides with molecules containing at least one methacrylate, acrylate or other polymerizable group and also one reactive hydroxyl group, or primary or secondary amino group, (2) 4-methacryloxyethyltrimelliticanhydride and its dicarboxylic acid hydrolysis derivative, (3) other compounds containing at least one group or moiety capable of free radical polymerization and at least one aromatic ring or moiety containing electron-withdrawing substituents that do not interfere with free radical polymerization, and (4) other compounds containing at least one group or moiety capable of free-radical polymerization and at least one carboxyl group or salt thereof.
Claim 39
Independent Claim
345 words
A method for preparing the surface of dentin, enamel, or other natural or industrial substrates containing or capable of binding divalent or polyvalent cations or amines, for adhesion of composite materials or resins, which method comprises: (a) contacting the surface with a solution comprising a composition having at least one acid, acidic salt, or chelating or sequestering agent, wherein the composition is soluble in water; (b) contacting the surface with a solution comprising a composition having at least one adhesion-promoting agent selected from the group consisting of N-phenylglycine (NPG), N-phenylalanine, 2-(N-phenyl) alkanoic acids, N-phenylalanine, 2-(N-phenyl) alkanoic acids other amino acids, and derivatives and analogues thereof selected from the group consisting of the addition reaction product of N(p-tolyl)glycine and glycidyl methacrylate (NTG-GMA); the adduct of N-phenylglycine and glycidyl methacrylate (NPG-GMA); the adduct of N(4-chlorophenyl)glycine and glycidyl methacrylate (NCPG-GMA); the adduct of N-phenylglycine and 1,2-epoxy-3-phenoxypropane (NPG-PGE); the adduct of N-phenylglycine and p-chlorophenyl-2,3-epoxypropyl ether (NPG-CGE); the adduct of N-p-chlorophenylglycine and p-chlorophenyl-2,3-epoxypropyl ether (NCG-CGE); the reaction product of N-p-chlorophenylglycine and phenyl-2,3-epoxypropyl ether (NCG-PGE); the adduct of N-phenylalanine and glycidyl methacrylate (NPA-GMA); and the adduct of N-tolyl-2(or alpha)-alanine, N-phenylalanine or 2-(N-phenyl) alkanoic acids and glycidyl methacrylate (NTA-GMA), in the form of salts or complexes of these compounds with at least one member of the group consisting of divalent cations, polyvalent cations, amines, diamines and polyamines, wherein the composition is soluble in an organic solvent; and (c) contacting the surface with a liquid comprising at least one adhesive resin monomer selected from the group consisting of (1) reaction products of dianhydrides with molecules containing at least one methacrylate, acrylate or other polymerizable group and also one reactive hydroxyl group, or primary or secondary amino group, (2) 4-methacryloxyethyltrimelliticanhydride and its dicarboxylic acid hydrolysis derivative, (3) other compounds containing at least one group or moiety capable of free radical polymerization and at least one aromatic ring or moiety containing electron-withdrawing substituents that do not interfere with free radical polymerization, and (4) other compounds containing at least one group or moiety capable of free-radical polymerization and at least one carboxyl group or salt thereof.
Claim 40
Independent Claim
304 words
A method for preparing the surface of dentin, enamel, or other natural or industrial substrates containing or capable of binding divalent or polyvalent cations or amines, for adhesion of composite materials or resins, which method comprises: (a) contacting the surface with a solution comprising a composition having at least one acid, acidic salt, or chelating or sequestering agent, wherein the composition is soluble in water; (b) contacting the surface with a solution comprising a composition having at least one adhesion-promoting agent selected from the group consisting of N-phenylglycine (NPG), N-phenylalanine, 2-(N-phenyl) alkanoic acids and derivatives and analogues thereof, and other amino acids, in the form of salts or complexes of these compounds with at least one member of the group consisting of divalent cations, polyvalent cations, amines, diamines and polyamines, wherein the composition is soluble in an organic solvent, and wherein the divalent and polyvalent salts or complexes of N-phenylglycine (NPG), and derivatives and analogues thereof are substantially in the form of salts and complexes selected from the group consisting of amine, diamine, polyamine, calcium, aluminum, magnesium, strontium, zinc, barium, iron, chromium, manganese, cobalt, copper and molybdenum salts, and (c) contacting the surface with a liquid comprising at least one adhesive resin monomer selected from the group consisting of (1) reaction products of dianhydrides with molecules containing at least one methacrylate, acrylate or other polymerizable group and also one reactive hydroxyl group, or primary or secondary amino group, (2) 4-methacryloxyethyltrimelliticanhydride and its dicarboxylic acid hydrolysis derivative, (3) other compounds containing at least one group or moiety capable of free radical polymerization and at least one aromatic ring or moiety containing electron-withdrawing substituents that do not interfere with free radical polymerization, and (4) other compounds containing at least one group or moiety capable of free-radical polymerization and at least one carboxyl group or salt thereof.
Claim 41
Independent Claim
304 words
A method for preparing the surface of dentin, enamel, or other natural or industrial substrates containing or capable of binding divalent or polyvalent cations or amines, for adhesion of composite materials or resins, which method comprises: (a) contacting the surface with a solution comprising a composition having at least one acid, acidic salt, or chelating or sequestering agent, wherein the composition is soluble in water; (b) contacting the surface with a solution comprising a composition having at least one adhesion-promoting agent selected from the group consisting of N-phenylglycine (NPG), N-phenylalanine, 2-(N-phenyl) alkanoic acids and derivatives and analogues thereof, and other amino acids, in the form of salts or complexes of these compounds with at least one member of the group consisting of divalent cations, polyvalent cations, amines, diamines and polyamines, wherein the composition is soluble in an organic solvent, and wherein the divalent and polyvalent salts or complexes of N-phenylglycine (NPG), and derivatives and analogues thereof are substantially in the form of salts and complexes selected from the group consisting of amine, diamine, polyamine, calcium, aluminum, magnesium, strontium, zinc, barium, iron, chromium, manganese, cobalt, copper and molybdenum salts, and (c) contacting the surface with a liquid comprising at least one adhesive resin monomer selected from the group consisting of (1) reaction products of dianhydrides with molecules containing at least one methacrylate, acrylate or other polymerizable group and also one reactive hydroxyl group, or primary or secondary amino group, (2) 4-methacryloxyethyltrimelliticanhydride and its dicarboxylic acid hydrolysis derivative, (3) other compounds containing at least one group or moiety capable of free radical polymerization and at least one aromatic ring or moiety containing electron-withdrawing substituents that do not interfere with free radical polymerization, and (4) other compounds containing at least one group or moiety capable of free-radical polymerization and at least one carboxyl group or salt thereof.
Claim 42
Dependent Claim
15 words
The method of claim 36 wherein the amines are ammonia, primary, secondary or tertiary amines.
Claim 43
Dependent Claim
26 words
The method of claim 37 wherein the amines are hexamethylenetetramine; 1,4-diazabicyclo[2.2.2]octane; quinuclidine; N,N-diethylethanolamine; N-ethyldiethanolamine; triethanolamine; N,N-dihydroxy-p-toluidine; 3-quinuclidinol; N,N-dihydroxyethylglycine; N,N-dimethylglycine; 2-quinuclidine carboxylic acid; N,N-dimethylaminoethylmethacrylate; or N, N-diethylaminoethylmethacrylate.
Claim 44
Dependent Claim
93 words
A method for preparing the di- and polyvalent salts and complexes of adhesion-promoting agents of subpart (b) of claim 1 comprising: (a) condensing divalent or polyvalent cation salts of 2-haloalkanoic acids with amines selected from the group consisting of aniline, ring-substituted derivatives and analogues of aniline, and amino acids, which salts do not undergo adverse interactions or form totally insoluble reaction products; (b) optionally reacting said reaction products with compounds containing alkylating moieties and polymerizable groups, and (c) separating the precipitated divalent and polyvalent salts and complexes of adhesion-promoting agents from the solution.
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