Polyols from Natural Oils using the Alkyne Zipper Reaction

Title: POLYURETHANE MATERIALS FORMED FROM UNSATURATED PLANT OILS VIA AN ALKYNE ZIPPER REACTION

Number/Link: US2017/0166679 US2017/0166680

Applicant/Assignee: IBM

Publication Date: 15-june-2017

“Gist”: Oils are turned into alkyne alcohols, ‘zippered’ and oxidized to polyols

Why it is interesting: This is yet  another IBM patent application about interesting, albeit somewhat exotic, chemistry and featuring only “prophetic” examples. In this case unsaturated natural oils are first converted into unsaturated alcohols and then into alkynes by bromination and elimination.  The internal alkynes are then converted to terminal alkynes by an “alkyne zipper reaction” and then into hydroxyl groups by hydroboration and epoxidation/ring-opening. This series of reactions should result in polyols having two primary- and one or more secondary OH groups, useful, for example, for the preparation of sound absorbing foams.

Reaction sequence according to the invention

Polycarbonate PU Foams with Reduced VOC Emissions

Title: POLYURETHANE FOAMS BASED ON POLYETHER CARBONATE POLYOLS

Number/Link: WO2017/085201 (German)

Applicant/Assignee: Covestro

Publication Date: 26-may-2017

“Gist”: Use of urea reduces the formation of propylenecarbonate from polycarbonate polyols

Why it is interesting: Covestry is betting heavily on polyethercarbonate polyols for use in polyurethane foams, using the carbon-negative footprint as a selling point. The use of polyethercarbonate polyols in PU foams can, however, result in the formation of propylenecarbonate resulting from a retro reaction promoted by conventional amine catalysts. Propylenecarbonate will contribute to the total VOC emissions of foams and other materials. According to this invention, the retro reaction can -surprisingly- be prevented or reduced by using urea or urea-derivatives in the foam formulation. In the examples urea and dimethylaminopropylurea are used together with a tin catalyst,  polyethercarbonate polyols and TDI to produce flexible foams with reduced propylenecarbonate content.

Propylenecarbonate

 

 

TPU from Oleic Acid

Title: RENEWABLY DERIVED THERMOPLASTIC POLYESTER-BASED URETHANES AND METHODS OF MAKING AND USING THE SAME

Number/Link: US2017/0145145

Applicant/Assignee: Trent University

Publication Date: 25-may-2017

“Gist”: Thermoplastic polyurethane made entirely from C9 monomers derived from oleic acid.

Why it is interesting: Azaleic acid can be prepared by oxidative cleavage of the oleic acid double bond.  Azaleic acid in turn can be converted to 1,9-nonanediol and to 1,7-heptamethyldiisocyanate via azides and Curtius rearrangment (see previous blog post). In this invention a polyester diol is prepared from azaleic acid and nonanediol and is then reacted with 1,7-heptamethylenediisocyanate together with nonanediol as chain extender, resulting in a phase-separated TPU. Best properties are obtained when the nonanediol is first prepolymerized with the diisocyanate. The TPU is said to degrade without cytotoxic degradation products, and is therefore useful for medical applications such as resorbable implants and scaffolds.
Related case: US2017/0145146.

Oleic Acid

 

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