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

Hybrid Polyurethane-Peptide Dispersion

Patent Title: AQUEOUS PEPTIDE-STABILIZED POLYURETHANE DISPERSIONS

 Number/Link: W02016058909

Applicant/Assignee: Henkel; Max Planck Ges.

Publication date: 21-04-2016

Gist”: An NCO-ended prepolymer is reacted with a peptide mixture in water at correct pH

Why it is interesting: According to this invention a low-VOC, surfactant- free, stable dispersion can be prepared by reacting an isocyanate-ended preopolymer with an aqueous solution of peptides. The prepolymer is prepared from a polyether-, polyester- or PDMS diol and a surplus of (preferably) aliphatic isocyanate. The peptide mixture is obtained by hydrolysis or enzymatic cleaving of naturally occuring proteins and is dispersed in water at a pH well above the highest isoelectric point present in the mixture. This will ensure reaction of the isocyanate with the peptides instead of water.
Polymer-protein hybrids are interesting because they allow for unique properties not attainable with synthetic polymers alone, such as a selective and specific interaction with other biomolecules and a controlled response to external stimuli like pH and temperature.

Example of a tetrapeptide: Val-Gly-Ser-Ala. (Wikipedia)

Example of a tetrapeptide: Val-Gly-Ser-Ala. (Wikipedia)

 

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