Patent Title: POLYURETHANE MATERIALS FORMED FROM EPOXIDIZED PLANT OILS
Number/Link: US2017/0081460
Applicant/Assignee: IBM
Publication date: 23-mar-2017
“Gist”: Natural oils are converted into isocyanate-functional polyols and then polymerized
Why it is interesting: Epoxidized vegetable oils are hydrolized and saponified using NaOH, resulting in a mixture of acid-ended polyols. The acid groups are then converted into azides using diphenylphosphoryl azide, which then rearrange into isocyanate groups (Curtius rearrangement). The isocyanate-ended polyols can be polymerized and further crosslinked using di-isocyanates. The materials are said to be useful as components for acoustic foams, used e.g. in mainframe computers.
This is the second IBM PU patent discussed in this blog. However, I doubt if they have an actual chemistry lab since their examples are “prophetic” rather than real.
Reaction scheme according to the invention
Innovation in Polyurethanes 
Gerhard Bleys
/ April 14, 2017This is what you get for doing “desktop” chemistry and making only “prophetic examples”. I wonder why IBM does that. Maybe it is an AI generated idea or something?
Z. Petrovic
/ April 8, 2017Hydroxylated isocyanates are not stable. Fatty acids with dihydroxylated double bonds are solid. It is not clear how they are obtained from epoxidized oil since we get epoxy groups preserved after base methylation. Using azides is academic exercise but not very practical.