A two-component polyurethane composition comprising a polyisocyanate and an emulsion polymer having greater than 2.2% of hydroxy groups in the emulsion polymer and comprising structural units of a polymerizable surfactant, a first hydroxy-functional monomer, an acid monomer and/or a salt thereof, an additional monoethylenically unsaturated nonionic monomer, and optionally a second hydroxy-functional alkyl (meth)acrylate; the two-component polyurethane composition providing improved alcohol resistance without compromising both acid and alkali resistance.

A two-component polyurethane composition comprising a polyisocyanate and an emulsion polymer having greater than 2.2% of hydroxy groups in the emulsion polymer and comprising structural units of a polymerizable surfactant, a first hydroxy-functional monomer, an acid monomer and/or a salt thereof, an additional monoethylenically unsaturated nonionic monomer, and optionally a second hydroxy-functional alkyl (meth)acrylate; the two-component polyurethane composition providing improved alcohol resistance without compromising both acid and alkali resistance.

The present disclosure is drawn to polyurethane dispersions. In one example, a polyurethane dispersion can include a polyurethane with a polymeric ionic side chain and a polymeric non-ionic side chain. The polyurethane can be formed of polymerized monomers including a diisocyanate, a first polymeric diol, and a second polymeric diol. The first polymeric diol can include a first polymer chain replacing a hydrogen atom of a thiol group of a 1-thioglycerol molecule. The first polymer chain can include a block of a polymerized ionic group-containing vinyl monomer. The second polymeric diol can include a second polymer chain replacing a hydrogen atom of a thiol group of a 1-thioglycerol molecule. The second polymer chain can include a block of a polymerized non-ionic vinyl monomer, and the second polymer chain can be devoid of ionic groups.

The present disclosure is drawn to polyurethane dispersions. In one example, a polyurethane dispersion can include a polyurethane with a polymeric ionic side chain and a polymeric non-ionic side chain. The polyurethane can be formed of polymerized monomers including a diisocyanate, a first polymeric diol, and a second polymeric diol. The first polymeric diol can include a first polymer chain replacing a hydrogen atom of a thiol group of a 1-thioglycerol molecule. The first polymer chain can include a block of a polymerized ionic group-containing vinyl monomer. The second polymeric diol can include a second polymer chain replacing a hydrogen atom of a thiol group of a 1-thioglycerol molecule. The second polymer chain can include a block of a polymerized non-ionic vinyl monomer, and the second polymer chain can be devoid of ionic groups.

The present disclosure provides novel oligomer compounds (e.g., non-polar oligomers) that can produce desirable polymeric materials (e.g., with polar reactive diluents), polymer compositions, and/or photo-curable resins that have excellent stain resistance. Further provided herein are methods of producing polymerizable compositions, resins, devices, and polymeric materials. Also provided herein are methods of using polymerizable compositions, resins, and polymeric materials for the fabrication (e.g., via 3D printing) of medical devices, such as orthodontic appliances with increased stain resistance.