Abstract: 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.

Abstract: 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.

Abstract: The polymerizable cyclodextrin derivatives (“PCDs”) 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.

Abstract: The polymerizable cyclodextrin derivatives (“PCDs”) 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 “MCDs” when only methacrylate groups comprise the polymerizable groups of the PCDs.

Abstract: 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.

Abstract: 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.

Abstract: 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.

Abstract: 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.

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.

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.

Abstract: 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.

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.

Abstract: Means to decrease the effects of polymerization shrinkage, increase stiffness, decrease the coefficient of thermal expansion to a greater extent than previously possible, and improve the durability of composite restorations by use of improved microcrystalline glass inserts. Shaped pieces of assorted sizes within the range of one-half to 10 millimeters are heat treated to produce microcrystallinity in which the crystalline phases, such as for example stuffed beta quartz, beta-eucryptite, beta-spodumene solid solutions, and keatite and/or other phases, give the microcrystalline glass pieces exceptionally low coefficients of thermal expansion and other desirable properties. Compositions and heat treatment conditions are given to provide the insert pieces with the desired translucencies/opacities, colors, and shades, to match a range of those properties found in teeth.

Abstract: Means to decrease the effects of polymerization shrinkage, increase stiffness, decrease the coefficient of thermal expansion and improve the durability of composite restorations by use of inserts are disclosed. Pieces of an aluminoborosilicate glass are phase-separated by heating to 870.degree. C. for 2 hours producing opaque inserts with silica-rich surfaces. Boiling for 1 hour in aqueous 0.5 N NaOH solution removes the surface layer, and produces a rough-textured surface with increased area. The surface texture plus treatment with an organofunctional silane provides for both micromechanical and chemical bonding with composite resins. Cavities in teeth are partially filled with unhardened composite material, and inserts of appropriate size and shape are pressed into the cavity so that the insert constitutes as much as possible of the finished restoration and its surface. The excess extruded composite material is removed with a hand instrument, and the composite containing the insert is light cured.

Abstract: Materials and methods for improving the adhesion of composite materials and resins to dentin, enamel and other substrates are disclosed. Preferably, the substrate surface is treated with an aqueous solution of (1) at least one acidic salt containing a polyvalent cation which preferably is capable of changing valence by unit steps (univalent changes) and which can bind to dentin or enamel surface sites, and at least one anion which preferably forms a relatively water-insoluble precipitate or precipitates with calcium, and which contains at least one carboxyl group and preferably two or more carboxyl groups; and (2) acid, preferably nitric acid. The resultant surface is then treated with a solvent containing at least one compound selected from the group consisting of (1) N-phenylglycine, (2) the adduct of N (p-tolyl) glycine and glycidyl methacrylate, and (3) the addition reaction product of N-phenylglycine and glycidyl methacrylate.

Abstract: Materials and methods for improving the adhesion of composite materials and resins to dentin, enamel and other substrates are disclosed. Preferably, the substrate surface is treated with an aqueous solution of at least one acidic salt containing a polyvalent cation which preferably is capable of changing valence by unit steps (univalent changes) and which can bind to dentin or enamel surface sites, and at least one anion which preferably forms a relatively water-insoluble precipitate or precipitates with calcium, and which contains at least one carboxyl group and preferably two or more carboxyl groups. The resultant surface is then treated with a solvent containing a composition preferably comprising N-phenylglycine.

Abstract: Materials and methods for improving the adhesion of composite materials and resins to dentin, enamel and other substrates are disclosed. Preferably, the substrate is treated with an aqueous solution of at least one acidic salt containing a polyvalent cation which preferably is capable of changing valence by unit steps (univalent changes) and which can bind to dentin or enamel surface sites, and at least one anion which preferably forms a relatively water-insoluble precipitate or precipitates with calcium, and which contains at least one carboxyl group and preferably two or more carboxyl groups. The resultant surface is then treated with a solvent containing at least one compound selected from the group consisting of (1) the adduct of N(p-tolyl)glycine and glycidyl methacrylate ("NTG-GMA"), and (2) the addition reaction product of N-phenylglycine and glycidyl methacrylate ("NPG-GMA").

Abstract: Application of a composition of matter comprising a solution of water in relatively nontoxic water-stable ethylenically unsaturated monomers, preferably methacrylate and/or acrylate and most preferably methacrylate monomers, which solution is substantially isotonic with normal physiological saline solution. As a further aspect of the invention, the compositions may be prepared by selecting ethylenically unsaturated monomers of varying hydrophilicity or water solubility, equilibrating each such monomer with water to form a two phase system and measuring the concentration of the monomer in the water-rich phase, preparing a mixture of monomers in equilibrium with water such that their cumulative concentration in the water phase is about 0.31 molar, and collecting the monomer-rich phase, which will be saturated with water and will also be isotonic with normal physiological saline.

Abstract: A family of polyfunctional surface-active comonomers which act to improve the adhesion between a resin or composite material and solid surfaces capable of binding polyvalent cations is described. These polyfunctional surface-active comonomers, or "PolySACs", are preferably the reaction product of an epoxy acrylate or methacrylate and an aminobenzoate. The adhesion of the resin or composite material to certain solid surfaces is also improved by the preparatory treatment of these surfaces with a monobasic acid of intermediate strength followed by treatment with a mordant.In its most preferred form the invention is employed in reconstructive dental work to improve the adhesion between a resin or composite material and dentin. The dentin is cleansed with isotonic formic acid, treated with an isotonic ferric chloride mordant and then treated with a PolySAC which is the reaction product of an oligomeric diglycidyl ether, acrylic acid and lithium ortho-aminobenzoate. The resin or composite material is then applied.