Government of the United States of America, As Represented by the Secretary of Commerce

The United States of America As Represented by the Secretary of

Other

USA As Represented by Secretary of the Navy

United States of America As Represented by the Secretary of the Air Force

The United States of America As Represented by the Department of Health

Joseph M Antonucci

Jeffrey W Stansbury

Patricia A Bennett

Frederick C Eichmiller

Toru Takahashi

George T Davis

John Robert Kelly

Robert E Muller

Gary E Schumacher

Guo-Wei Cheng

Kyung M Choi

Drago Skrtic

Bruce O Fowler

Edward D Eanes

Chawan-Kang Chiang

A polymerizable biomedical composition includes a quaternary ammonium group bonded at its quaternary sites to respective groups R, R, R, and R. Rand Reach include a vinyl moiety such that the composition is at least bi-functional with respect to polymerization.

Polymerizable biomedical composition

Etchant/primer composition, etchant/primer/adhesive monomer composition, kits and methods using the same for improved bonding to dental structures

Disclosed are fluorinated materials for use in dental uses and non-dental uses, e.g., adhesives or coatings. Multifunctional monomers and prepolymers with pendant (meth)acrylate groups were prepared from epoxide ring-opening reactions. Resins based on the fluorinated monomers and prepolymers with diluent comonomers, were photocured as composites with particulate fillers. Fluorine contents of the prepolymers ranged from 15 to 65%. Composites with high transverse strength (up to 120 MPa), low water sorption (as low as 0.11 mass %) and extremely low polymerization shrinkage (as low as 3.4% by volume) were obtained. The fluorinated resins may be employed to produce hydrophobic dental composite materials with high strength and low polymerization shrinkage.

High strength polymeric networks derived from (meth) acrylate resins with organofluorine content and process for preparing same

A silylated resin suitable for use as an adhesive binder for composites and in sealant and adhesive dental applications is represented by the general formula (I):

Silylated resins and the synthesis thereof

An etchant/primer composition is provided which includes (a) a compound having the formula

Method and composition for promoting improved adhesion to substrates

An etchant primer composition is provided which includes (a) a compound hng the formula

Composites in the form of a three-dimensional framework or skeleton of ceic particles are formed by a low cost, low temperature sintering process which decomposes a pre-ceramic inorganic or organic precursor. Upon heating, preferably in air, the precursor decomposes to form a ceramic phase in the form of necks between the individual ceramic particles. The properties of the resulting porous ceramic bodies can be modified, such as toughened by impregnation with monomers, oligomers or polymers which are polymerized or cured in situ. Such composites find use as cosmetic products or protheses for humans and animals, such as dental restoratives and bone implants. Methods of fabrication are disclosed which include the use of a pre-ceramic polymer as a binder for the ceramic particles which forms the necks of material between the individual ceramic particles upon firing.

Pre-ceramic polymers in fabrication of ceramic composites

A mineralizing composition for skeletal tissue comprising a mixture of an saturated monomer system, and a particulate mineralizing agent.

Polymeric amorphous calcium phosphate compositions

The present invention provides a process for converting a hydrophobic siloxane diacrylate, an aromatic fluorinated diacrylate and a hydrophilic polyethylene glycol diacrylate to their respective multifunctional oligomers. Bis(4-acryloxybutyl)tetramethyldisiloxane, prepared from the corresponding diol, is converted to relatively low viscosity, multifunctional oligomers with the use of DMSO. The hydrophilic monomer, polyethylene glycol 400 diacrylate, formed more viscous, water soluble oligomeric products without the need for a solvent. Characterization of these oligomers by infrared spectroscopy and .sup.1 H NMR supports the assigned structures. Because of the predominant 1,6-arrangement of double bonds in these oligomers, they have a propensity to undergo cyclopolymerization as well as the usual crosslinking associated with the free radical polymerization of multifunctional monomers and oligomers. These novel oligomeric monomers have potential use in dental composites, sealants, adhesives, dentures, contact lenses, biomedical prostheses, cements, drug delivery systems, coatings and caulks.

Multifunctional acrylates and the synthesis thereof

A denture liner composition is provided comprising a methacrylate polymer and/or copolymer in powder form to be wetted by a liquid composition containing dimethacrylate, butyl methacrylate, and long chain methacrylate monomers, the mixture setting upon wetting and being polymerized by visible light and chemical action. A method for using the composition in denture liner formation is also provided.

Denture liners

Non-aqueous polycarboxylic acids such as dimer and trimer acids are reacted with a variety of polyvalent metal bases to yield a new, versatile class of cements. Many of these cements have unique energy-absorbing properties and excellent dimensional stability yielding mechanically tough and ductile materials. They also do not inhibit the polymerization of resin-based dental materials and thus can be formulated to yield hybrid resin-composite-cement materials. The bulky, hydrophobic nature of these acids with their relatively low carboxylic content results in cements that are low shrinking, hydrolytically resistant and biocompatible.

Non-aqueous dental cements based on dimer and trimer acids

Dental resin systems prepared from polyfunctional or monofunctional highly-fluorinated methacrylate prepolymers are described. Preferred systems comprise (a) a major amount of a polyfluorinated aligomeric polyfunctional methacrylate such as (PFMA), preferably in combination with a diluent monomer such as 1,10-decamethylene dimethacrylate (DMDMA), methyl methacrylate (MMA), neopentyl dimethacrylate (NPDMA), 1,6-hexamethylene dimethacrylate (HMDMA), etc., or mixtures thereof; and (b) a minor amount of a polyfluorinated monofunctional methacrylate (PFMMA), such as 1,1-dihydropentadecafluorooctyl methacrylate (PDFOMA) as a minor or secondary diluent monomer in a non-hydroxylated bis-GMA resin system. The products are generally useful as hydrophobic dental materials, esepcially as composited (with fillers), sealants and cements.

Hydrophobic dental composites based on a polyfluorinated dental resin

Polyethylene imine-metal salt solid electrolyte

A two paste dental composite formulation is disclosed, wherein one paste comprises a polymerizable monomer and a stable organic hydroperoxide initiator, and the other paste comprises a polymerizable monomer and a polythiol accelerator, the hydroperoxide having a ten-hour half-life temperature in excess of about 100.degree. C., and the polythiol being capable of accelerating the decomposition of the hydroperoxide into polymerization initiating free radicals at ambient temperatures.

Growing community of inventors

Kensington, MD, United States of America

Joseph M Antonucci