Abstract: In one embodiment, an orthodontic article is described comprising the reaction product of a polymerizable composition comprising: a) 30-70 parts by weight of monofunctional (meth)acrylate monomer, wherein a cured homopolymer of at least one monofunctional (meth)acrylate monomer has a Tg of at least 30, 35, 40, 45, 50, 55, or 60° C.; and b) urethane (meth)acrylate polymer comprising polymerized units of an aliphatic polyester diol. Also described are polymerizable compositions, as well as methods and systems for making an article utilizing 3D printing.

Abstract: Dental compositions and methods of formulating a dental composition are described. In one embodiment, the dental composition comprises a polymerizable resin comprising one or more ethylenically unsaturated monomers or oligomers and nano-particles. The nanoparticles have a refractive index of at least 1.600 and an average discrete or aggregate particle size of no greater than 100 nm. The dental composition further comprises inorganic metal oxide filler having a discrete or aggregate average particle size of at least 200 nm. The nanoparticles are present at a concentration to provide a refractive index differential between the cured polymerizable resin and inorganic metal oxide filler such that the contrast ratio of the dental composition is at least 40.

Abstract: Provided is an addition-fragmentation agent of the formula (I) where Ramine comprises a tertiary amine group; R2 linking group of valence a+2; Z is an ethylenically unsaturated polymerizable group; and subscript a is 0 or 1.

Abstract: An orthodontic article is described comprising a cured composition comprising the reaction product of free-radically polymerizable resin comprising at least one monomer, oligomer and/or polymer, comprising at least two (meth)acryl moieties; a monofunctional reactive diluent; and a polymer or macromolecule comprising a free-radical photoinitiator group. The polymer or macromolecule has a molecular weight of at least 500 g/mole. In one embodiment, the cured composition comprises a first and second photoinitiator wherein at least one is a polymer or macromolecule. Also described are photopolymerizable compositions and methods.

Abstract: Novel stress-reducing crosslinking oligomers that have application in dental restoratives, thin films, hardcoats, composites, adhesives, and other uses subject to stress reduction are described. The addition-fragmentation process of crosslinking results in a chain-transfer event that provides novel polymers that may be further functionalized. In addition, the addition-fragmentation oligomer comprises pendent functional groups that bond to a substrate by forming an ionic or covalent bond, or etch the substrate by chemically removing some material from the substrate.

Abstract: The present disclosure provides an inorganic dental filler including a surface treated with at least one silane. Exemplary silanes described in the present disclosure for the surface treatment of the inorganic filler include silanes of Formula I and/or Formula II: (RSi)—(CR1R2)n—(NH—C(O)—O—CH2—CH2)q—N(R5)—C(O)—NH—(CH2—CH2—O)t—CR3R4—CH2-(A) Formula I (RSi)—(CR1R2)n—NH—C(O)—O—CR3R4-(L)q-CH2-(A) Formula II, wherein: RSi is a silane-containing group of the formula —Si(Yp)(R6)3-p, wherein Y is a hydrolysable group, R6 is a monovalent alkyl or aryl group, and p is 1, 2, or 3. Methods of making and using the surface treated inorganic dental fillers are also disclosed.

Abstract: The present disclosure provides an aqueous dispersion. The aqueous dispersion includes a) water; b) a surfactant having at least one ethylenically unsaturated group; and c) polyester particles dispersed in the water. The polyester particles include a water-insoluble polyester having a weight average molecular weight of 20 kiloDaltons or greater, and the polyester particles have an average diameter that is submicron in size. Further, the present disclosure provides a method of making the aqueous dispersion. The method includes a) dissolving a water-insoluble polyester in a water-immiscible solvent to form a polyester solution; b) combining the polyester solution with an aqueous solution including water and a surfactant; and c) removing at least a portion of the water-immiscible solvent to form the aqueous dispersion including polyester particles dispersed in the water.

Abstract: Orthodontic articles and polymerizable resin compositions are described. The orthodontic article comprises a cured composition comprising the reaction product of free-radically polymerizable resin comprising 30 to 70 wt. %, inclusive, of at least one urethane component, and 25 to 70 wt. %, inclusive, of reactive diluent(s) comprising at least one monofunctional (meth)acrylate monomer. The polymerizable resin comprises no greater than 35 wt. % of reactive diluent(s) having a high affinity for water. Reactive diluent(s) such as monofunctional (meth)acrylate monomers having a high affinity for water have low log P values. In one embodiment, the polymerizable resin comprises at least one acidic monomer.

Abstract: An orthodontic article is described comprising the reaction product of a free-radically polymerizable resin; a first free-radical photoinitiator having sufficient absorbance at a first wavelength range; and a second free-radical initiator selected from a second photoinitiator having sufficient absorbance at a second wavelength range, wherein the second wavelength range is different than the first wavelength range, or a thermal free-radical initiator. In some embodiments, a 1 g/liter acetonitrile solution, at a pathlength of 1 cm, has an absorbance of greater than 0.01, 0.02, 0.03, 0.04, 0.05, 0.06, 0.07, 0.08, 0.09, or 0.10 at a wavelength of the first wavelength range when measured with a spectrophotometer. In some embodiments, the first free-radical photoinitiator exhibits a maximum absorbance at a wavelength of the range of 370-380 nm or 320-330 nm and/or comprises photoinitiator groups selected from acyl phosphine oxide or alkyl amine acetophenone.

Abstract: The present disclosure provides an orthodontic article including the reaction product of the polymerizable composition. Further, the present disclosure provides polymerizable compositions and methods of making an orthodontic article. The method includes obtaining a polymerizable composition and selectively curing the polymerizable composition to form an orthodontic article. Further, methods are provided, including receiving, by a manufacturing device having one or more processors, a digital object comprising data specifying an orthodontic article; and generating, with the manufacturing device by an additive manufacturing process, the orthodontic article based on the digital object. A system is also provided, including a display that displays a 3D model of an orthodontic article; and one or more processors that, in response to the 3D model selected by a user, cause a 3D printer to create a physical object of an orthodontic article.

Abstract: The present disclosure provides an aqueous dispersion. The aqueous dispersion includes a) water; b) a surfactant having at least one ethylenically unsaturated group; and c) polyester particles dispersed in the water. The polyester particles include a water-insoluble polyester having a weight average molecular weight of 20 kiloDaltons or greater, and the polyester particles have an average diameter that is submicron in size. Further, the present disclosure provides a method of making the aqueous dispersion. The method includes a) dissolving a water-insoluble polyester in a water-immiscible solvent to form a polyester solution; b) combining the polyester solution with an aqueous solution including water and a surfactant; and c) removing at least a portion of the water-immiscible solvent to form the aqueous dispersion including polyester particles dispersed in the water.

Abstract: Disclosed are of the protected photoinitiators of the formula: wherein Aryl1 is an aromatic or heteroaromatic ring; Aryl2 is an aromatic ring; each R1 is an alkyl, an aryl, an electron donating group or an electron withdrawing group, and subscript a is 0 to 3; each R2 is an alkyl, an aryl, an electron donating group or an electron withdrawing group, and subscript b is 0 to 3; Prot is a protected carbonyl group.

Abstract: Disclosed herein are non-aqueous compositions including: a flowable Part A including at least one resin and Reactant A; and a flowable Part B including at least one resin and Reactant B; wherein at least one of flowable Part A and flowable Part B further includes a free radically polymerizable resin; wherein at least one of flowable Part A and flowable Part B further includes a free radical initiator system; wherein flowable Part A and flowable Part B are capable of being mixed to provide a flowable mixed composition; wherein when flowable Part A and flowable Part B are mixed, Reactant A and Reactant B are capable of interacting to cause a non-free radical reaction within a first staging time to provide a first staged stable consistency for the mixed composition; wherein Reactant A comprises an acid and Reactant B comprises a base, and upon mixing flowable Part A and flowable Part B, the Reactant A acid is capable of reacting with the Reactant B base in an ionic acid-base reaction; and wherein the mixed compo

Abstract: The present disclosure provides a photopolymerizable composition. The photopolymerizable composition includes at least one urethane component, at least one monofunctional reactive diluent, an initiator, and optionally an inhibitor. The present disclosure also provides an article including the reaction product of the photopolymerizable composition. Further, the present disclosure provides a method of making an article. The method includes (i) providing a photopolymerizable composition and (ii) selectively curing the photopolymerizable composition to form an article. The method optionally also includes (iii) curing unpolymerized urethane component and/or reactive diluent remaining after step (ii). Further, methods are provided, including receiving, by a manufacturing device having one or more processors, a digital object comprising data specifying an article; and generating, with the manufacturing device by an additive manufacturing process, the article based on the digital object.

Abstract: The present disclosure provides a photopolymerizable composition. The photopolymerizable composition includes at least one polypropylene oxide component and an initiator, plus optionally a urethane component, a multifunctional reactive diluent, and/or an inhibitor. The present disclosure also provides an article including the reaction product of the photopolymerizable composition. Typically, the article exhibits an elongation at break of 30% or greater. Further, the present disclosure provides a method of making an article. The method includes (i) providing a photopolymerizable composition and (ii) selectively curing the photopolymerizable composition to form an article. The method optionally also includes (iii) curing unpolymerized polypropylene oxide component, urethane component and/or multifunctional reactive diluent remaining after step (ii).

Abstract: The present disclosure provides an inorganic dental filler including a surface treated with at least one silane. Exemplary silanes described in the present disclosure for the surface treatment of the inorganic filler include silanes of Formula I and/or Formula II: (RSi)—(CR1R2)n—(NH—C(O)—O—CH2—CH2)q—N(R5)—C(O)—NH—(CH2—CH2—O)t—CR3R4—CH2-(A) Formula I (RSi)—(CR1R2)n—NH—C(O)—O—CR3R4-(L)q-CH2-(A) Formula II, wherein: RSi is a silane-containing group of the formula —Si(Yp)(R6)3-p, wherein Y is a hydrolysable group, R6 is a monovalent alkyl or aryl group, and p is 1, 2, or 3. Methods of making and using the surface treated inorganic dental fillers are also disclosed.

Abstract: A radiation curable composition including at least one radiation hardenable component, a photo-initiator, and a filler material having a population of particulates in an amount greater than or equal to 50% by weight of the printable composition. The population of particulates exhibits a median diameter (D50) of greater than or equal to 0.3 micrometer on a volume-average basis as determined using the Particle Size Test Method, and the radiation curable composition exhibits a viscosity of less than or equal to 150 Pa s when measured using the Viscosity Test Method. A method, apparatus, and systems for producing composite articles by selectively exposing a portion of the radiation curable composition to a source of actinic radiation to at least partially cure the exposed portion of the radiation curable composition, thereby forming a hardened layer, preferably by an additive manufacturing process such as stereophotolithography, are also described. The composite articles may include composite dental restorations.

Abstract: The present disclosure provides a photopolymerizable composition comprising 50-90 wt % of at least one urethane component, 5-50 wt % of at least one reactive diluent, 0.1-5 wt % of a photoinitiator, and optionally an inhibitor, wherein said composition has a viscosity at a temperature of 40 degrees Celsius of 10 Pa·s or less, as determined using a magnetic bearing rheometer using a 40 mm cone and plate measuring system at a shear rate of 0.1 l/s. The present disclosure also provides an article including the reaction product of the photopolymerizable composition, in which the article exhibits an elongation at break of 25% or greater. Further, the present disclosure provides a method of making an article including (i) providing a photopolymerizable composition and (ii) selectively curing the photopolymerizable composition to form an article. The method optionally also includes (iii) curing unpolymerized urethane component and/or reactive diluent remaining after step (ii).

Abstract: Novel stress-reducing crosslinking oligomers that have application in dental restoratives, thin films, hardcoats, composites, adhesives, and other uses subject to stress reduction are described. The addition-fragmentation process of crosslinking results in a chain-transfer event that provides novel polymers that may be further functionalized. In addition, the addition-fragmentation oligomer comprises pendent functional groups that bond to a substrate by forming an ionic or covalent bond, or etch the substrate by chemically removing some material from the substrate.

Abstract: Novel stress-reducing crosslinking oligomers that have application in dental restoratives, thin films, hardcoats, composites, adhesives, and other uses subject to stress reduction are described. The addition-fragmentation process of crosslinking results in a chain-transfer event that provides novel polymers that may be further functionalized. In addition, the addition-fragmentation oligomer comprises pendent functional groups that bond to a substrate by forming an ionic or covalent bond, or etch the substrate by chemically removing some material from the substrate.