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

 

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