NOPs from GMOs

Patent Title: Low Polyunsaturated Fatty Acid Oils and Uses Thereof

 Number/Link: US20160194584

Applicant/Assignee: Solazyme

Publication date: 7-07-2016

Gist”: Natural oil polyols from genetically modified organisms

Why it is interesting: Natural oils usually contain significant (and variable) amounts of polyunsaturated fatty acids, i.e. fatty acids with more than one double bond in the backbone. Soybean oil for example contains up to 60% PUFAs that can easily engage in side reactions like autooxidation and polymerization, resulting in side products that contaminate the oil – and therefore the polyols derived from them.  According to this (299 page) application, oils containing >85% oleic acid and very low PUFA concentration can be made from certain genetically modified microalgae. Polyols derived from these oils by hydroxylation can be used to prepare polyurethane foams with reduced discolorouration, reduced odour, improved reproducibility and improved physical properties as compared to foams based on conventional NOPs.

Triglicerid with PUFA

Trigliceride with PUFA

Polyols from Proteins

Patent Title: POLYOLS FROM PROTEIN BIOMASS

 Number/Link: WO2016/094859

Applicant/Assignee: Inventors

Publication date: 16-06-2016

Gist”: Transamidation of protein with diamines followed by carbonation

Why it is interesting: Currently most renewable polyols are based on natural oils (NOPs) like soy-oil, but it is also possible to make polyols from proteins. According to this invention this can be accomplished by first cleaving the protein amide bonds by transamidation with an excess of low molecular weight polyamines using a boric acid derivative as catalyst. Then stripping the excess amines and reacting with cyclocarbonates. In an example soy-meal is reacted with ethylenediamine and then with ethylene carbonate resulting in a urethane polyol. The polyols have a high primary OH content, are auto-catalytic and are said to be useful for the production of PU resins and rigid foams.

Diol acoording to the invention. R is an amino acid residue.

Polyol according to the invention. R is an amino acid residue.

 

Polyurethanes from Mevalonolactone

Patent Title: POLYMERS PREPARED FROM MEVALONOLACTONE AND DERIVATIVES

 Number/Link: US2016/0130389

Applicant/Assignee: Visolis

Publication date: 12-05-2016

Gist”: Use of mevalonolactone derivatives as monomers for PU and other polymers

Why it is interesting: 3,5-Dihydroxy-3-methylvaleric acid and its corresponding lactone “mevalonolactone”, is a common metabolic intermediate and can be produced industrially by fermentation of biomass. Mevalonolactone can be converted to diacids, (unsaturated) diols, triols etc., which could be useful as a renewable and inexpensive feedstock for polymers like polyester, polyamides and polyurethanes. In an example mevalonolactone is reacted with ethanolamine resulting in the triol  3,5-dihydroxy-N-(2-hydroxyethyl)-3-methylpentanamide which is in turn reacted with 4,4′ MDI to make a model polyurethane.

Dihydroxymethylvaleric acid and its corresponding lactone

Dihydroxymethylvaleric acid and its corresponding lactone

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