Bio-Based Acoustic Polyurethane Foam

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.

IBM

Reaction scheme according to the invbention

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2 Comments

  1. Z. Petrovic

     /  April 8, 2017

    Hydroxylated 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.

    Reply
  2. This 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?

    Reply

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