Denture tooth and material

The present invention relates to a dental polymer composition, in particular to a polymerizable resin composition combining comonomers capable of intermolecular hydrogen bonding with one or more hydrophobic comonomers. Polymers employing the present resin system exhibit high mechanical strength properties that are retained in the presence of water.

Water compatible nanogel compositions

The present invention relates to preparation and use of water dispersible nanogels and solvent dispersible reactive nanogels as additives to enhance polymer properties or as precursors to polymeric networks.

Water Compatible Nanogel Compositions

The present invention relates to preparation and use of water dispersible nanogels and solvent dispersible reactive nanogels as additives to enhance polymer properties or as precursors to polymeric networks. 1. A water dispersible nanogel produced by a process comprising:(i) combining a monomer mixture comprising at least one monovinyl monomer, at least one divinyl monomer, a difunctional chain transfer agent, and an initiator; and(ii) polymerizing said mixture to form a water dispersible nanogel.2. The nanogel according to claim 1 , wherein the divinyl monomer is selected from one or more of the group consisting of ethylene glycoldi(meth)acrylate claim 1 , tetraethyleneglycoldi(meth)acrylate (TTEGDMA) claim 1 , urethane dimethacrylate (UDMA) claim 1 , the condensation product of bisphenol A and glycidyl (meth)acrylate claim 1 , 2 claim 1 ,2′-bis [4-(3-methacryloxy-2-hydroxy propoxy)-phenyl] propane (bis-GMA) claim 1 , ethoxylated bisphenol-A-di(meth)acrylate (BisEMA) claim 1 , hexanediol di(meth)acrylate claim 1 , polyethyleneglycol dimethacrylate claim 1 , tripropylene glycol di(meth)acrylate claim 1 , butanediol di(meth)acrylate claim 1 , neopentyl glycol di(meth)acrylate claim 1 , diethylene glycol di(meth)acrylate claim 1 , triethylene glycol di(meth)acrylate claim 1 , dipropylene glycol di(meth)acrylate claim 1 , allyl (meth)acrylate claim 1 , divinyl benzene claim 1 , bis(meth)acrylamide claim 1 , and 1 claim 1 ,3-diglycerolatediacrylate..3. The nanogel according to claim 2 , wherein said divinyl monomer is tetraethyleneglycoldi(meth)acrylate (TTEGDMA) claim 2 , ethoxylated bisphenol-A-di(meth)acrylate (BisEMA) claim 2 , or polyethyleneglycol dimethacrylate.4. The nanogel according to claim 1 , wherein the said monovinyl monomer is selected from one or more of the group consisting of (meth)acrylates and acrylates claim 1 , styrene and derivatives thereof (styrenics) claim 1 , vinyl acetate claim 1 , maleic anhydride claim 1 , itaconic acid claim 1 , N-alkyl ( ...

Water Compatible Nanogel Compositions

The present invention relates to preparation and use of water dispersible nanogels and solvent dispersible reactive nanogels as additives to enhance polymer properties or as precursors to polymeric networks. 17-. (canceled)8. A method to improve adhesive polymer wet flexural strength , the method comprising:(i) combining a first monomer mixture comprising at least one functional monomer, at least one divinyl monomer, a difunctional chain transfer agent, and an initiator;(ii) polymerizing said first monomer mixture to form a functionalized nanogel;(iii) reacting the functionalized nanogel with a reactive olefinic compound to form a reactive nanogel with pendant olefinic groups;(iv) adding the reactive nanogel to an adhesive resin to create a second mixture; and(v) polymerizing the second mixture to provide an adhesive polymer with increased polymer wet flexural strength compared to an adhesive polymer prepared from the adhesive resin without the added reactive nanogel.9. The method according to claim 8 , wherein the pendant olefinic groups are selected from styryl claim 8 , allyl claim 8 , vinyl ether claim 8 , and (meth)acrylate groups.10. The method according to claim 8 , wherein the reactive olefinic compound is selected from (meth)acryloyl chloride claim 8 , (meth)acrylic anhydride claim 8 , (meth)acrylic acid claim 8 , isocyanatoalkyl(meth)acrylate claim 8 , isocyanatoethyl(meth)acrylate vinylbenzene chloride claim 8 , chloroethyl vinyl ether claim 8 , allyl chloride and isocyanatomethyl(meth)acrylate.11. The method according to claim 8 , wherein the difunctional chain transfer agent is selected from mercaptoethanol claim 8 , mercaptopropanol claim 8 , 3-mercapto-2-butanol claim 8 , 2-mercapto-3-butanol claim 8 , 3-mercapto-2-methyl-butan-1-ol claim 8 , 3-mercapto-3-methyl-hexan-1-ol claim 8 , 3-mercaptohexanol claim 8 , 3-mercaptopropionic acid claim 8 , and cysteine.12. The method according to claim 8 , wherein the reactive nanogel is added in about 10 wt % to ...

HIGHLY EFFICIENT FREE RADICAL PHOTOPOLYMERIZATIONS THROUGH ENABLED DARK CURE

A quaternary ammonium salt comprising a chromophore constituent, a tertiary amine cation constituent connected to the para-position of the chromophore constituent via a methylene linkage, and a borate anion constituent, wherein chromophore constituent is a 3-ketocoumarin constituent or a benzophenone constituent. Also, a photobase-redox initiating system comprising the quaternary ammonium salt and a peroxide. 20. The quaternary ammonium salt of claim , wherein each alkoxy group is independently selected from the group consisting of methoxy and butoxy.30. The quaternary ammonium salt of claim , wherein Ris —H or alkoxy.40. The quaternary ammonium salt of claim , wherein Ris —H.50. The quaternary ammonium salt of claim , wherein:{'sub': 1', '8', '1', '8', '1', '6, 'the substituted -phenyl group has one or more independently selected substituents selected from the group consisting of linear or branched C-Calkyl group, linear or branched C-C-alkoxy group, -halogen, and halogenated C-C-alkyl group;'}{'sub': 1', '8', '1', '8', '1', '6, 'the substituted -napthyl group has one or more independently selected substituents selected from the group consisting of linear or branched C-Calkyl group, linear or branched C-C-alkoxy group, -halogen, and halogenated C-C-alkyl group; and'}{'sub': 2', '10, 'the unsubstituted vinyl group is Cand the substituted vinyl group is an extended vinylene up to C.'}60. The quaternary ammonium salt of claim , wherein at least one of the Rgroups is the substituted aromatic ring.70. The quaternary ammonium salt of claim , wherein the amine cation constituent is selected from the group consisting of N-methyl morpholine , N-methyl pyrrolidine , N ,N-dimethyl aniline , N ,N ,4-trimethyl aniline , N-N-dimethyl-4-methoxyaniline , N ,N-pyrrolidine-4-methoxyaniline , and N ,N-ethoxy-4-methylaniline.80. The quaternary ammonium salt of claim , wherein the borate anion constituent is selected from the group consisting of tetraphenyl , tetra-4-methyl-phenyl , ...

MULTILAYER POLYMERIC MATRIX BASED MEDICAL DEVICES

The disclosure relates to multilayer polymeric matrix based medical devices. In one example, a device comprises an inner first polymeric matrix and an outer second polymeric matrix. The addition of second polymeric matrix modifies bulk properties of each matrix thus resulting in a device where specific bulk properties are incorporated. The disclosure also relates to methods of manufacturing various embodiments of medical devices and their uses. 1. A device comprising:an outer layer of a first polymeric matrix having a first bulk property, the first polymeric matrix comprising a cross-linked polymer or a linear polymer or a combination thereof selected from the group consisting of hydrophilic or hydrophobic nanogels, nanotubes, poly(propylene glycol), polyvinyl alcohol, polyurethanes, isocyanates, polyvinyl alcohol, acrylic acid, methacrylic acid, chitosan, alginates, acrylamides, and nanoparticles, acrylates and methacrylates.2. The device of claim 1 , further comprising:an inner core of a second polymeric matrix having a second bulk property, wherein the second polymeric matrix is covalently linked with the first polymeric matrix via an interfacial polymerization reaction forming a polymeric macroscopic cross-linked network, and further wherein the interfacial polymerization reaction modifies the first bulk property of the first polymeric matrix, and the second bulk property of the second polymeric matrix, and the second polymeric matrix comprises a cross-linked polymer or a linear polymer or a combination thereof selected from the group consisting of polyurethane, poly(ethylene, glycol), poly(propylene glycol), polyvinyl alcohol, acrylic acid, methacrylic acid, chitosan, alginates, acrylamides, epoxies, isocyanates vinyl ethers, allyl ethers, acrylates, methacrylates, acrylamides, nanogels, or nanoparticles, nanotubes.3. (canceled)4. The device of claim 2 , wherein the second first polymeric matrix comprises at least one pharmaceutically active compound claim 2 , ...

DENTURE TOOTH AND MATERIAL

The present invention relates to a dental polymer composition, in particular to a polymerizable resin composition combining comonomers capable of intermolecular hydrogen bonding with one or more hydrophobic comonomers. Polymers employing the present resin system exhibit high mechanical strength properties that are retained in the presence of water. 1. A polymerizable resin composition comprising a urethane monomer , an acidic monomer and one or more hydrophobic monomers.2. The resin composition of claim 1 , wherein the weight ratio of urethane monomers plus acidic monomers compared to hydrophobic monomers is selected from about 99:1 to 50:50; 90:10 to 60:40; 85:15 to 75:25 claim 1 , or about 80:20.3. The resin composition of further comprising a surfactant.4. The resin composition of further comprising an initiator.5. The resin composition of further comprising a prepolymer.6. The resin composition of claim 1 , wherein the urethane monomer is selected from 1 claim 1 ,6-bis(methacryloxy-2-ethoxycarbonylamino)-2 claim 1 ,2 claim 1 ,4(2 claim 1 ,4 claim 1 ,4)-trimethylhexane (UDMA) or bis(2-(methacryloyloxy)ethyl) 5 claim 1 ,7 claim 1 ,7 claim 1 ,24 claim 1 ,24 claim 1 ,26-hexamethyl-10 claim 1 ,21-dioxo-11 claim 1 ,14 claim 1 ,17 claim 1 ,20-tetraoxa-2 claim 1 ,9 claim 1 ,22 claim 1 ,29-tetraazatriacontanedioate.7. The resin composition of claim 1 , wherein the acidic monomer is selected from the group consisting of methacrylic acid (MAA) claim 1 , bis (2-methacryloxyethyl)phthalate claim 1 , pyromellitic glycerol dimethacrylate claim 1 , methacroyloxyethyl maleate claim 1 , hydroxyethyl methacrylate/succinate adduct claim 1 , 1 claim 1 ,3-glycerol dimethacrylate/maleate adduct and 1 claim 1 ,3-glycerol dimethacrylate/succinate adduct.8. The resin composition of claim 1 , wherein the hydrophobic monomer is selected from the group consisting of isostearyl methacrylate (ISMA) claim 1 , ethoxylated bisphenol A dimethacrylate (EBDMA) claim 1 , stearyl methacrylate claim 1 ...

CONTROL OF POLYMER NETWORK STRUCTURES VIA NANOGELS

A method of increasing a polymerization reaction rate of a base monomer composition that has slow free-radical polymerization kinetics. The method comprises combining an effective amount of a nanogel to the base monomer composition to form a monomer-nanogel mixture having a polymerization reaction rate that is greater than the polymerization reaction rate of the base monomer composition when subjected to an identical free-radical polymerization reaction conducted under identical conditions. The base monomer composition comprises one or more slow-kinetic monomers with slow free radical polymerization kinetics in which <25% of the double bonds are converted within the first 10 mintes of said reaction. The nanogel is soluble in the base monomer composition. The nanogel is derived from a nanogel-forming monomer mixture that comprises: at least one monovinyl monomer; at least one divinyl monomer; a chain transfer agent; and an initiator. 1. A method of increasing a polymerization reaction rate of a base monomer composition that has slow free-radical polymerization kinetics , the method comprising combining an effective amount of a nanogel to the base monomer composition to form a monomer-nanogel mixture having a polymerization reaction rate that is greater than the polymerization reaction rate of the base monomer composition when subjected to an identical free-radical polymerization reaction conducted under identical conditions;wherein the base monomer composition comprises one or more slow-kinetic monomers with slow free radical polymerization kinetics in which <25% of the double bonds are converted within the first 10 mintes of said reaction; andwherein the nanogel is soluble in the base monomer composition and wherein the nanogel is derived from a nanogel-forming monomer mixture that comprises:at least one monovinyl monomer;at least one divinyl monomer;a chain transfer agent; andan initiator.2. The method of claim 1 , wherein the nanogel has an effective diameter in a ...

3D PRINTING WITH POLYMERIC NANOGEL PARTICLES

A photoinitiated polymerizable composition for 3D printing, the polymerizable composition comprising a nanogel component that comprises nanogel particles, wherein the nanogel particles comprise a copolymer with polymerizable reactive groups suitable for reacting with each other or a reactive diluent monomer, a reactive oligomer, a resin, or a combination thereof that is present in the polymerizable composition upon photoinitiation, wherein the nanogel component has a glass transition temperature that is in a range of about −50 C and about 20 C and an average molecular weight that is in a range of about 10 kg/mol and about 100 kg/mol, and wherein the nanoparticles have an average hydrodynamic radius that is in a range of 1 nm to about 5 nm. 1. A photoinitiated polymerizable composition for 3D printing , the polymerizable composition comprising: (i) the copolymer is the polymerized product of a mixture that comprises a monovinyl monomer, a divinyl monomer, and a chain transfer agent, wherein the divinyl monomer is at a concentration in a range of about 20 mol % to about 80 mol % of the monomer content of the mixture;', '(ii) the polymerizable reactive groups of the copolymer are at a concentration that is in a range of about 5% to about 20% of the reactive group density of the divinyl monomer;', '(iii) at least one of the monovinyl monomer and the divinyl monomer is a glassy polymer when homopolymerized and at least one of the monovinyl monomer and the divinyl monomer is a rubbery polymer when homopolymerized;', {'sub': 'g', '(iv) the nanogel component has a glass transition temperature (T), corresponding to the peak of a tan delta plot created via Dynamic Mechanical Analysis (DMA), is in a range of about −50° C. and about 20° C.;'}, {'sub': 'n', '(v) the nanogel component has an average molecular weight (M), determined with triple-detector gel permeation chromatography (TD-GPC) analysis, that is in a range of about 10 kg/mol and about 100 kg/mol; and'}, {'sub': 'h', ...

Water compatible nanogel compositions

The present invention relates to preparation and use of water dispersible nanogels and solvent dispersible reactive nanogels as additives to enhance polymer properties or as precursors to polymeric networks.

Reactive oligomeric thiol and ene materials as dental restorative mixtures

The present invention provides a dental composition comprising a curable blend of one or more polythiol compounds and one or more polyvinyl compounds; where one or both compounds are oligomers. In one aspect, the polythiol compounds are polythiol oligomers formed by prepolymerization of polyvinyl monomers in the presence of an excess of polythiol monomers. In another aspect, the polyvinyl compounds are polyvinyl oligomers formed by prepolymerization of polythiol monomers in the presence of an excess of polyvinyl monomers. The dental composition may further comprise one or more fillers or photoinitiators known in the art. The invention also comprises methods of making a dental prosthesis comprising the composition described above. Use of the thiol-ene oligomeric system results in cured (polymerized) dental compositions having improved physical properties, including low-shrinkage properties and reduced shrinkage induced-stress, enhanced double bond conversion percentage, and reduced odor.

Dimer acid-derived dimethacrylates and use in dental restorative compositions

The present invention provides polymerizable dental compositions comprising a dimer acid-derived monomer such as a dimer acid-derived di(meth)acrylate monomer. In one embodiment, the dimer acid-derived monomer is of the formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from H and optionally substituted C 1 -C 25 straight-chained or branched aliphatic, optionally containing 1 or more double or triple bonds, wherein one or more carbons are optionally replaced by R* wherein R* is —C(O)—, —C(O)C(O)—, —C(O)NR 7 —, —C(O)NR 7 NR 8 —, —C(O)O—, —OC(O)—, —NR 7 CO 2 —, —O—, —NR 7 C(O)NR 8 —, —OC(O)NR 7 —, —NR 7 NR 8 —, —NR 7 C(O)—, —NR 7 C(O)O—, —S—, —SO—, —SO 2 —, —NR 7 —, —SO 2 NR 7 — or —NR 7 SO 2 —, where R 7 and R 8 are independently selected from H and optionally substituted aliphatic, cycloalkyl, heterocycloalkyl, aryl or heteroaryl; provided that at least two of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are substituted C 1-25 straight-chained or branched aliphatic wherein at least one carbon is replaced by R* and at least one of the substituents is an alkenyl group.

Dimer acid-derived dimethacrylates and use in dental restorative compositions

The present invention provides polymerizable dental compositions comprising a dimer acid-derived monomer such as a dimer acid-derived di(meth)acrylate monomer. In one embodiment, the dimer acid-derived monomer is of the formula (I): wherein R1, R2, R3, R4, R5 and R6 are independently selected from H and optionally substituted C1-C25 straight-chained or branched aliphatic, optionally containing 1 or more double or triple bonds, wherein one or more carbons are optionally replaced by R* wherein R* is -C(O)-, -C(O)C(O)-, -C(O)NR7-, -C(O)NR7NR8-, -C(O)O-, -OC(O)-, -NR7CO2-, -O-, -NR7C(O)NR8-, -OC(O)NR7-, -NR7NR8-, -NR7C(O)-, -NR7C(O)O-, -S-, -SO-, -SO2-, -NR7-, -SO2NR7- or -NR7SO2-, where R7 and R8 are independently selected from H and optionally substituted aliphatic, cycloalkyl, heterocycloalkyl, aryl or heteroaryl; provided that at least two of R1, R2, R3, R4, R5 and R6 are substituted C1-25 straight-chained or branched aliphatic wherein at least one carbon is replaced by R* and at least one of the substituents is an alkenyl group.

Dimer acid-derived dimethacrylates and use in dental restorative compositions

Reactive oligomeric thiol and ene materials as dental restorative mixtures

The present invention provides a dental composition comprising a curable blend of one or more polythiol compounds and one or more polyvinyl compounds; where one or both compounds are oligomers. In one aspect, the polythiol compounds are polythiol oligomers formed by prepolymerization of polyvinyl monomers in the presence of an excess of polythiol monomers. In another aspect, the polyvinyl compounds are polyvinyl oligomers formed by prepolymerization of polythiol monomers in the presence of an excess of polyvinyl monomers. The dental composition may further comprise one or more fillers or photoinitiators known in the art. The invention also comprises methods of making a dental prosthesis comprising the composition described above. Use of the thiol-ene oligomeric system results in cured (polymerized) dental compositions having improved physical properties, including low-shrinkage properties and reduced shrinkage induced-stress, enhanced double bond conversion percentage, and reduced odor.

Water compatible nanogel compositions

The present invention relates to preparation and use of water dispersible nanogels and solvent dispersible reactive nanogels as additives to enhance polymer properties or as precursors to polymeric networks.

3D printing with polymeric nanogel particles

A photoinitiated polymerizable composition for 3D printing, the polymerizable composition comprising a nanogel component that comprises nanogel particles, wherein the nanogel particles comprise a copolymer with polymerizable reactive groups suitable for reacting with each other or a reactive diluent monomer, a reactive oligomer, a resin, or a combination thereof that is present in the polymerizable composition upon photoinitiation, wherein the nanogel component has a glass transition temperature that is in a range of about −50 C and about 20 C and an average molecular weight that is in a range of about 10 kg/mol and about 100 kg/mol, and wherein the nanoparticles have an average hydrodynamic radius that is in a range of 1 nm to about 5 nm.

Control of polymer network structures via nanogels

A method of increasing a polymerization reaction rate of a base monomer composition that has slow free-radical polymerization kinetics. The method comprises combining an effective amount of a nanogel to the base monomer composition to form a monomer-nanogel mixture having a polymerization reaction rate that is greater than the polymerization reaction rate of the base monomer composition when subjected to an identical free-radical polymerization reaction conducted under identical conditions. The base monomer composition comprises one or more slow-kinetic monomers with slow free radical polymerization kinetics in which <25% of the double bonds are converted within the first 10 mintes of said reaction. The nanogel is soluble in the base monomer composition. The nanogel is derived from a nanogel-forming monomer mixture that comprises: at least one monovinyl monomer; at least one divinyl monomer; a chain transfer agent; and an initiator.

Dimer Acid-Derived Dimethacrylates and Use in Dental Restorative Compositions

The present invention provides polymerizable dental compositions comprising a dimer acid-derived monomer such as a dimer acid-derived di(meth)acrylate monomer. In one embodiment, the dimer acid-derived monomer is of the formula (I): wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are independently selected from H and optionally substituted C 1 -C 25 straight-chained or branched aliphatic, optionally containing 1 or more double or triple bonds, wherein one or more carbons are optionally replaced by R* wherein R* is —C(O)—, —C(O)C(O)—, —C(O)NR 7 —, —C(O)NR 7 NR 8 —, —C(O)O—, —OC(O)—, —NR 7 CO 2 —, —O—, —NR 7 C(O)NR 8 —, —OC(O)NR 7 —, —NR 7 NR 8 —, —NR 7 C(O)—, —NR 7 C(O)O—, —S—, —SO—, —SO 2 —, —NR 7 —, —SO 2 NR 7 — or —NR 7 SO 2 —, where R 7 and R 8 are independently selected from H and optionally substituted aliphatic, cycloalkyl, heterocycloalkyl, aryl or heteroaryl; provided that at least two of R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are substituted C 1-25 straight-chained or branched aliphatic wherein at least one carbon is replaced by R* and at least one of the substituents is an alkenyl group.

Novel photopolymers and use in dental restorative materials

Photopolymerizable polymer composites based on dimethacrylate systems have been increasingly utilized as dental restorative materials. One of the biggest drawbacks of current dental resin systems is the volume shrinkage and shrinkage induced stresses that arise during the polymerization. Other major problems include incomplete double bond conversion and insufficient wear resistance. This invention involves the development of an entirely novel approach to the photopolymerization process that utilizes thiol-ene systems as low shrinkage and ultra-low shrinkage stress dental restorative materials. Compared with the traditional dimethacrylate dental resins, these novel photopolymerizations have demonstrated a dramatically decreased volume shrinkage, extremely rapid polymerization, abilities to photopolymerize ultrathick materials and achieve much higher conversion, lack of oxygen inhibition and ultra-low shrinkage stress due to low volume shrinkage and drastically delayed gel point conversion. These polymers have thus shown outstanding suitability as dental restorative materials.

Nanogels for ophthalmic applications

Nanogels particularly suited for medical applications including lenses such as intraocular lenses, contact lenses and other corneal prosthetics. Two monomers that are very different in nature can be combined to form the nanogels without deleterious phase separation. The nanogels allow crosslinked nanoscale structures to be formed from vastly different monomers. The nanogels are particularly suited as a filler, e.g., within another polymer or a solvent, or as coating. The nanogels can be homogeneously dispersed in any matrix (e.g., solvent, polymer) and can be reacted within the matrix. If the matrix is optically clear, addition of the nanogels does not destroy the clarity of the matrix. The nanogels are also particularly suited as a therapeutic agent delivery conduit. In some implementations, the nanogels are siloxane nanogels, having been formed from a composition including a siloxane acrylate.

Polymerizable composition for dental tooth and material 3d printing

Polymerizable resin compositions and methods are provided for preparing shaped parts such as dental prosthetic devices and non-prosthetic dental appliances. The compositions are amenable to 3D printing and the polymerized compositions are capable of exhibiting improved strength properties, increased toughness, and good flexibility.

Low viscosity urethane (meth)acrylate monomers and their use in production of tough polymers with well-controlled modulus and strength

Low viscosity urethane (meth)acrylate monomers and polymerizable resin compositions are provided to facilitate production of tough polymers with well- controlled modulus and strength.