University of Southern Mississippi

Covestro LLC

Jie Wu

Robson F Storey

Alan Ekin

R Hunter Cooke, Iii

Harrison A Livingston

An alternative polyurethane composition is provided which comprises a reaction product of an azidated polyol and a poly(alkynyl carbamate) prepolymer, wherein reaction occurs at a temperature of from 20° C. to 200° C., optionally in the presence of a catalyst, wherein the poly(alkynyl carbamate) prepolymer comprises a reaction product of stoichiometric equivalents of a polyisocyanate and a component comprising 1-100% of an alkynol-ether of the formula (I): HC≡C—R—OH (I), wherein R is a linear or branched ether chain having from 1 to 15 atoms, and wherein the remainder of the hydroxyl-functional component comprises a first alkynol. The inclusion of an alkynol-ether reduces the viscosity of the composition without compromising its performance. The inventive alternative polyurethane compositions may find use in providing coatings, adhesives, sealants, films, elastomers, castings, foams, and composites.

Low viscosity poly(alkynyl carbamate) prepolymers

A waterborne poly(alkynyl carbamate) prepolymer is provided which comprises a reaction product of a polyisocyanate comprising a first portion and a second portion of isocyanate groups; an isocyanate-reactive component comprising 0.1 mol % to 6 mol % of a C-Cglycol ether; and 99.9 mol % to 94 mol % of an alkynol, wherein the mol % is based on the moles of isocyanate in the polyisocyanate, wherein the first portion of isocyanate groups reacts with the C-Cglycol ether, wherein the second portion of isocyanate groups reacts with the alkynol, and wherein reaction occurs optionally in the presence of a catalyst. The reaction of long chain glycol ethers with the polyisocyanate at a level of from 0.1 mol % to 6 mol % imparts water dispersibility to the prepolymer, and when the prepolymer is dispersed in water, the performance of waterborne alternative polyurethane compositions made therefrom, such as coatings, adhesives, sealants, films, elastomers, castings, foams, and composites, are not compromised. The invention allows for the use of water as a carrier, thus eliminating the need for organic solvents.

Waterborne azido-alkyne click compositions

An alternative polyurethane composition is provided which comprises a reaction product of an azidated polyol and a poly(alkynyl carbamate) prepolymer reacted at a temperature of from 20&#xb0; C. to 120&#xb0; C., wherein the poly(alkynyl carbamate) prepolymer comprises a reaction product of a polyisocyanate and a stoichiometric equivalent of an alkynol of the formula (I),HC&#x2261;C&#x2014;RR&#x2014;OH&#x2003;&#x2003;(I),and wherein Ris an electron-withdrawing group selected from the group consisting of carbonyl, ester, amide, and urethane and Ris a linear or branched alkyl chain having from 1 to 15 carbon atoms. The inventive alternative polyurethane composition position may be used to provide adhesives, sealants, films, elastomers, castings, foams, and composites.

Polyurethane polymers cured via azido-alkyne cycloaddition at ambient or mild curing conditions

An alternative polyurethane composition is provided which comprises a reaction product of an azidated polyol and a poly(alkynyl carbamate) prepolymer, wherein reaction occurs at a temperature of from 20&#xb0; C. to 200&#xb0; C., optionally in the presence of a Cu-containing catalyst and wherein the poly(alkynyl carbamate) prepolymer comprises a reaction product of a polyisocyanate, an alkynol, and a glycol ether, wherein from 1 mol % to 33 mol % of isocyanate groups are reacted with glycol ether and the remaining isocyanate groups are reacted with the alkynol. The inclusion of glycol ethers into the polyisocyanate chain of the poly(alkynyl carbamate) prepolymer at a level of from 1 mol % to 33 mol %, is efficient in reducing the viscosity of the composition without compromising its performance in coatings, adhesives, sealants, films, elastomers, castings, foams, and composites made with the inventive alternative polyurethane compositions.

Low viscosity poly(alkynyl carbamate) polymers

A waterborne alternative polyurethane composition is provided which comprises a reaction product of: an azidated polyol; and a waterborne poly(alkynyl carbamate) prepolymer comprising a reaction product of a polyisocyanate and from 1 wt. % to 20 wt. % of an alkynol-polyether having a formula (I),R&#x2014;R&#x2014;O&#x2014;R&#x2014;OH&#x2003;&#x2003;(I),wherein,

An alternative polyurethane composition is provided comprising a reaction product of an azidated polyol and a poly(alkynyl carbamate) allophanate prepolymer, wherein the poly(alkynyl carbamate) allophanate prepolymer comprises a reaction product of a first alkynol and a poly(alkynyl carbamate) prepolymer, in the presence of a metallo-organic compound of the formula: M(acac), wherein, M=a metal, acac=an acetylacetonate residue, and n=2 or 3, wherein the poly(alkynyl carbamate) prepolymer comprises a reaction product of a polyisocyanate and a stoichiometric equivalent of a second alkynol, and wherein the polyisocyanate comprises isocyanate groups and uretdione groups. The inventive alternative polyurethane compositions may be used to provide solventborne or waterborne coatings, adhesives, sealants, films, elastomers, castings, foams, and composites.

Growing community of inventors

Hattiesburg, MS, United States of America

Jie Wu