Clickable waterborne polymers and click-crosslinked waterborne polymers, clickable functional compounds, click functionalized waterborne polymers, and uses thereof

A method of making a crosslinked polyurethane polymer comprising a 1,2,3-triazole crosslinking group comprising:

• a) reacting a diisocyanate with a macromolecular polyol;
• b) adding dimethylol propionic acid to the product from a) to introduce carboxylic acid groups;
• c) adding a clickable diol bearing alkyne or azide group(s) to the product from b) to modify polyurethane with clickable reactive groups;
• d) adding a base to neutralize carboxylic acid to render the resulting polyurethane dispersible in water;
• e) adding a chain extender the product from d),
• wherein the aqueous dispersion of a clickable waterborne polyurethane comprising alkyne groups or clickable waterborne polyurethanes comprising azide groups is formed;
• and
• f) contacting a clickable waterborne polyurethane comprising alkyne groups and a clickable polyurethane comprising azide groups with a copper(I) catalyst under conditions such that a crosslinked polyurethane polymer comprising a 1,2,3-triazole crosslinking group is formed from an alkyne group of the clickable waterborne polyurethane comprising alkyne groups and an azide group of the clickable polyurethane comprising azide groups, and
• optionally, contacting the crosslinked polyurethane polymer with alkyne modified nanoparticles or azide modified nanoparticles with a copper(I) catalyst under conditions such that a polyurethane polymer having at least one nanoparticle linked to the polymer backbone via a linking group comprising a 1,2,3-triazole group is formed from an alkyne group of the crosslinked polyurethane polymer or an azide group of the crosslinked polyurethane polymer and an azide group of an azide modified nanoparticle or an alkyne group of an alkyne modified nanoparticle, respectively,
• wherein a nanoparticle functionalized crosslinked polyurethane polymer is formed, or
• contacting a clickable waterborne polyurethane comprising alkyne groups or a clickable waterborne polyurethane comprising azide groups with azide modified nanoparticles or alkyne modified nanoparticles, respectively, with a copper(I) catalyst under conditions such that a polyurethane polymer having at least one nanoparticle linked to the polymer backbone via a linking group comprising a 1,2,3-triazole group is formed from an alkyne group of the crosslinked polyurethane polymer or an azide group of the crosslinked polyurethane polymer and an azide group of an azide modified nanoparticle or an alkyne group of an alkyne modified nanoparticle, respectively,
• wherein a nanoparticle functionalized clickable waterborne polyurethane polymer comprising alkyne groups or a nanoparticle functionalized clickable waterborne polyurethane polymer comprising azide groups is formed, and
• contacting the nanoparticle functionalized clickable waterborne polyurethane polymer comprising alkyne groups and a nanoparticle functionalized clickable waterborne polyurethane polymer comprising azide groups with a copper(I) catalyst under conditions such that a crosslinked polyurethane polymer comprising a 1,2,3-triazole crosslinking group is formed from an alkyne group of the clickable waterborne polyurethane comprising alkyne groups and an azide group of the clickable polyurethane comprising azide groups.