Rafael L Bowen

US Patent:

6583248, Jun 24, 2003

Filed:

Oct 10, 2000

Appl. No.:

09/684513

Inventors:

Rafael L. Bowen - Gaithersburg MD

Assignee:

American Dental Association Health Foundation - Gaithersburg MD

International Classification:

C08F 812

US Classification:

5262382, 5253282, 5253284, 5253288, 525367, 525379

Abstract:

The polymerizable cyclodextrin derivatives (âPCDsâ) 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.

US Patent:

20090188622, Jul 30, 2009

Filed:

Jan 27, 2009

Appl. No.:

12/360421

Inventors:

Rafael L. Bowen - Gaithersburg MD, US

Assignee:

ADA Foundation - Chicago IL

International Classification:

B32B 37/00
A61K 6/00

US Classification:

156305, 523118

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.

US Patent:

47447591, May 17, 1988

Filed:

May 13, 1986

Appl. No.:

6/862706

Inventors:

Rafael L. Bowen - Gaithersburg MD

Assignee:

American Dental Association Health Foundation - Washington DC

International Classification:

A61C 504
A61K 602

US Classification:

4332281

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. The glass insert, together with the surrounding hardened composite, is contoured with high-speed rotary diamond instruments.

US Patent:

54017831, Mar 28, 1995

Filed:

Nov 24, 1993

Appl. No.:

8/158115

Inventors:

Rafael L. Bowen - Gaithersburg MD

Assignee:

American Dental Association Health Foundation - Gaithersburg MD

International Classification:

A61K 608
A61C 500

US Classification:

523116

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.

US Patent:

61807397, Jan 30, 2001

Filed:

Apr 9, 1998

Appl. No.:

9/057766

Inventors:

Rafael L. Bowen - Gaithersburg MD

Assignee:

American Dental Association Health Foundation

International Classification:

C08F 2400

US Classification:

5262382

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. These PCDs are organofunctional monomers that are derivatives of one or more forms of cyclodextrin, hydroxyalkyl cyclodextrins, or both ("CDS"), 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.

US Patent:

59105518, Jun 8, 1999

Filed:

Nov 24, 1997

Appl. No.:

8/979441

Inventors:

Rafael L. Bowen - Gaithersburg MD

Assignee:

American Dental Association Health Foundation - Chicago IL

International Classification:

C08F22400

US Classification:

5262382

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.

US Patent:

45887560, May 13, 1986

Filed:

Feb 7, 1985

Appl. No.:

6/699079

Inventors:

Rafael L. Bowen - Gaithersburg MD

Assignee:

American Dental Association Health Foundation - Washington DC

International Classification:

A61K 600

US Classification:

523116

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. Finally, a solution is applied which contains at least one compound selected from the group consisting of (1) the addition reaction product of pyromellitic acid dianhydride and 2-hydroxyethyl methacrylate ("PMDM"), (2) the addition reaction product of 3,3',4,4'-benzophenonetetracarboxylic dianhydride and 2-hydroxyethyl methacrylate ("BTDA-HEMA"), and (3) 4-methacryloxyethyltrimellitic anhydride ("4-META"). Alternative embodiments are also set forth.

US Patent:

57896100, Aug 4, 1998

Filed:

Jan 9, 1995

Appl. No.:

8/370538

Inventors:

Rafael L. Bowen - Gaithersburg MD

Assignee:

American Dental Association Health Foundation - Chicago IL

International Classification:

C07F 1100
C07F 300
C07F 506

US Classification:

556 50

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-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.