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

PUDs for Superhydrophobic Coatings

Patent Title: Vegetable Oil-Modified, Hydrophobic Polyurethane Dispersions

 Number/Link: US20160009852

Applicant/Assignee: Rust-Oleum

Publication date: 14-01-2016

Gist”: PUDs containing saturated monoglycerids

Why it is interesting: Aqueous polyurethane dispersions are popular for use in environmentally friendly coating compositions. Because of the inherent presence of hydrophilic (often acid-) groups to stabilise these dispersions, the resulting coatings often lack hydrolytic stability. According to this invention, this can be improved by incorporating monoglycerids, prepared by reacting vegetable oils with glycerol followed by distillation, into the PU backbone.  A prepolymer is prepared by reacting the monoglicerids, together with a non-isocyanate urethane polyol (prepared from polyamines and monocyclic carbonates), a conventional long-chain polyol and dimethylolpropionic acid, with an excess of isocyanate. The prepolymer is then neutralized with an amine and subsequently reacted with a chain extender in water to make the PUD. Coatings made with these dispersions are said to be superhydrophobic and have a low friction coeficient.

Dimethylolpropionic acid

Dimethylolpropionic acid

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