Non-Isocyanate Polyurethane Using Thiol-Ene “Click Chemistry”

Title: POLY(HYDROXYL URETHANE) COMPOSITIONS AND METHODS OF MAKING AND USING THE SAME

 Number/Link: US20140182784

Applicant/Assignee:  Inventors but with US goverment interest

Publication date: 3-07-2014

Gist”: Crosslinked poly(hydroxyurethanes) are prepared by reacting a cyclic carbonate comprising a carbon-carbon double bond, a di-thiol and a polyamine.

Why it is interesting: According to this invention hydroxyurethanes are produced by first reacting a cyclic carbonate which has a double bond (e.g. 4-vinyl-1,3-dioxolan-2-one) with a dithiol (e.g. 1,6-hexanedithiol) using UV radiation and a UV initiator. The resulting di-carbonate is then reacted with a polyamine (e.g. diethylene triamine) resulting in a crosslinked poly(hydroxyurethane). Alternatively the carbonate-amine reaction can happen before the thiol-ene ‘click’ reaction. The materials can be used for binders and adhesives a.o.  The reactions have the advantage of being solvent-, catalyst- and isocyanate-free and having a high yield.

Thiol-ene reaction followed by carbonate-amine reaction

Thiol-ene reaction followed by carbonate-amine reaction

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