American Dental Association Health Foundation

Ada Foundation

American Dental Association Health

Rafael L Bowen

Jirun Sun

A composition of matter includes one or more functionalized vinylbenzyl components of the formula covalently connected to one or more R functional components; the one or more R functional groups selected from a group including one or more hydroxyl methyl (&#x2014;CHOH&#x2014;) moieties and/or derivatives thereof, one or more ethoxy (&#x2014;CH&#x2014;CH&#x2014;O&#x2014;) moieties and/or derivatives thereof, end one or more benzene (CH) and/or derivatives thereof; and ether links that connect the functionalized vinylbenzyl components and the R functional components.

Resin composites for use in dental preventive and restorative applications

A composition of matter includes one or more functionalized vinylbenzyl components of the formula wherein n is an integer equal to or greater than 1 covalently connected to one or more R functional components; the one or more R functional groups selected from a group including one or more hydroxyl methyl (&#x2014;CHOH&#x2014;) moieties and/or derivatives thereof, one or more ethoxy (&#x2014;CH&#x2014;CH&#x2014;O&#x2014;) moieties and/or derivatives thereof, and one or more benzene derivatives; and ether links that connect the functionalized vinylbenzyl components and the R functional components.

Enzymatically and hydrolytically stable dental preventive and restorative systems

A composition of matter includes one or more functionalized vinylbenzyl components of the formula covalently connected to one or more R functional components; the one or more R functional groups selected from a group including one or more hydroxyl methyl (&#x2014;CHOH&#x2014;) moieties and/or derivatives thereof, one or more ethoxy (&#x2014;CH&#x2014;CH&#x2014;O&#x2014;) moieties and/or derivatives thereof, and one or more benzene (CH) and/or derivatives thereof; and ether links that connect the functionalized vinylbenzyl components and the R functional components.

Enzymatically and hydrolytically stable resins, resin monomers, and resin composites for use in dental preventive and restorative applications

Disclosed are compositions that comprise vinylarylalkylene ethers of cyclodextrins optionally containing ether-linked adhesion-promoting groups, in combination with copolymerizable monomer or monomers. The copolymerizable monomer or monomers may include vinylarylalkylene ethers of oligohydroxy compounds (for example, sorbitol divinylbenzyl ether and others). The composition further may include stabilizers (for example, 1,3,5-trimethyl-2,4,6-tris(3,5-di-(tert)-butyl-4-hydroxybenzyl)benzene and others), and polymerization initiators (for example, phenylbis[2,4,6-trimethylbenzoyl]phosphine oxide and others) and reinforcing materials (for example, imogolite). Methods of preparing the compositions as well as the components of compositions and methods for their use in dental and other applications are also disclosed.

Hydrolytically stable, hydrophilic adhesion-promoting monomers and polymers made therefrom

The polymerizable cyclodextrin derivatives (&ldquo;PCDs&rdquo;) of this invention relate to cyclodextrin derivatives wherein substantially each molecule of which contains one or more covalently attached polymerizable group or groups, may also contain one or more other types of functional groups covalently attached, may also have other types of molecules that are complexed or more particularly within the otherwise empty spaces within the cyclodextrin derivatives, and combinations and permutations of these characteristics.

Polymerizable cyclodextrin derivatives

The polymerizable cyclodextrin derivatives (&ldquo;PCDs&rdquo;) of this invention relate to cyclodextrin derivatives wherein substantially each molecule of which contains one or more covalently attached polymerizable group or groups, may also contain one or more other types of functional groups covalently attached, may also have other types of molecules that are complexed or more particularly within the otherwise empty spaces within the cyclodextrin derivatives, and combinations and permutations of these characteristics. The PCDs are referred to herein as &ldquo;MCDs&rdquo; when only methacrylate groups comprise the polymerizable groups of the PCDs. These PCDs are organofunctional monomers that are derivatives of one or more forms of cyclodextrin, hydroxyalkyl cyclodextrins, or both (&ldquo;CDS&rdquo;), the molecules of which to a very high probability contain no fewer than one polymerizable group per molecule and also to a very high probability contain no fewer than one ligand group per molecule and optionally may contain molecularly encapsulated molecules within the PCDs.

Polymerizable cyclodextrin derivatives (PCDs) for use in dental applications are disclosed. Each PCD molecule contains covalently attached polymerizable groups, and may also contain other covalently attached functional ligand groups, and molecularly encapsulated comonomers, polymerization inhibitors (stabilizers), polymerization initiators, and other desirable molecules. The covalently attached groups are ether or ester substituents, or their derivatives, in statistically predetermined proportions. The molecular members of PCD libraries may have quasi-random molecular configurations in the numbers and locations of their various substituents. Appropriate formulations containing PCD libraries can yield unique structural adhesives and resins for use in health-care procedures.

Polymerizable cyclodextrin derivatives for use in dental applications

A library of diverse molecular configurations containing many combinations and permutations of polymerizable cyclodextrin derivatives (PCDs) is disclosed for use in dental bonding formulations and other applications. Each PCD molecule in the library contains numerous (at least one or more) covalently attached polymerizable groups, and may also contain covalently attached ligand groups, such as free carboxyl groups, tertiary amino groups, or both, which substituents are attached in statistically predetermined proportions by ether or ester linkages. The PCDs may also contain molecularly encapsulated comonomers, polymerization inhibitors (stabilizers), polymerization initiators, and other desirable molecules. The molecular members of the PCD libraries may have quasi-random molecular configurations in the numbers and locations of their various substituents. Appropriate formulations containing PCD libraries can yield unique structural adhesives and resins for use in health-care procedures and in other applications.

A method for preparing polymerized libraries of polymerizable cyclodextrin derivatives (PCDs) for use in dental and other applications is disclosed. This is done by first preparing PCDs that are mixtures of reaction products resulting from reacting a cyclodextrin with a sufficient number of moles of reagents that will, with high probability, covalently attach one or more polymerizable groups on substantially every cyclodextrin molecule. These reactions are carried out in the presence of solvents and catalysts, and the reaction products are formulated with compatible comonomers to the desired viscosity. The resulting formulations(s) is (are) combined with one or more polyemerization initiators, and the polymerization initiators are activated to form one or more polymerized cyclodextrin libraries.

Polymerizable cyclodextrin derivatives (PCDs) are disclosed, wherein each molecule contains at least one covalently attached polymerizable group, may also contain one or more other covalently attached functional ligand group(s), such as free carboxyl group(s), may also contain molecularly encapsulated comonomers, polymerization inhibitors (stabilizers), and polymerization initiators. The groups are attached covalently as ether or ester derivatives in statistically predetermined proportions, in a homogeneous solution, to form a 'combinatorial' library having quasi-random molecular configurations of free carboxyl or other ligand groups. In the resulting PCD library, appropriate comonomers and polymerization initiators can be added that will enable timely polymerization to form unique structural adhesives and resins. The adhesive resins can be utilized in preventative and restorative dentistry.

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-methacryloxy-ethyltrimelliticanhydride 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.

Adhesion-promoting agents incorporating polyvalent cations

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.

This invention relates primarily to organofunctional monomers, predominantly dimethacrylates and/or diacrylates containing one or more (predominantly two carboxyl groups, with moieties that provide sufficient affinity with water to allow any desired amount of water and/or miscible fugitive solvents to be mixed homogeneously with these monomers and formulations containing them. The activity of water in the monomer formulations can be adjusted so that it is equal to the water activity in biological tissues. This promotes biocompatibility and enhances the adhesive characteristics of polymers prepared from these formulations. Probability statistics are disclosed that optimize the compositions of polymer reaction products. Also disclosed are novel, dual-purpose synthesis reaction monomers, catalysts, stabilizers, polymerization initiators and/or cophotoinitiators that have solubility and surface-activity characteristics such that they will not become separated by partitioning during penetration of hydrated layers on or in the substrate adherends. These formulations may be used for light-cured or chemical-cured bonding to soft or hard tissues, metal, porcelain, ceramic or other surfaces. A potential application for the composition is the holding together, by an overlying layer of resulting polymer, tissues adjacent to incisions and wounds. The polymerized composition might replace suturing, and allow for the healing of soft tissues.

Growing community of inventors

Gaithersburg, MD, United States of America

Rafael L Bowen