Non-Isocyanate Polyurethanes from Sucrose-Fatty Acid Esters

Patent Title: BIOBASED CYCLIC CARBONATE FUNCTIONAL RESINS AND POLYURETHANE THERMOSETS THEREFROM

 Number/Link: US2016/0312060

Applicant/Assignee: NDSU

Publication date: 27-10-2016

Gist”: Epoxidized sucrose-fatty acid esters are reacted with CO2, then with polyamines

Why it is interesting:  Esters of unsaturated fatty acids and sucrose have been known since the 1960s and are useful in e.g. coatings.  Highly subsituted sucrose esters with an average of 7.7 fatty acid chains per molecule, a molecular weight of about 2400 and a relatively low viscosity of 300-400 mPa.s are commercially available. According to this invention, epoxidized sucrose-fatty acid esters can be further reacted with carbon dioxide resulting in a resin with a ‘pluraility’ of cyclocarbonate groups. Curing with polyamines results in highly crosslinked poly(hydroxyurethanes) useful for coatings, composites and adhesives.

Epoxidized sucrose-fatty acid ester

Epoxidized sucrose-fatty acid ester

 

 

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

Non-Isocyanate Polyurethane Using Thiol-Ene “Click Chemistry”

Title: POLY(HYDROXYL URETHANE) COMPOSITIONS AND METHODS OF MAKING AND USING THE SAME

 Number/Link: US20140182784

Applicant/Assignee:  Inventors but with US goverment interest

Publication date: 3-07-2014

Gist”: Crosslinked poly(hydroxyurethanes) are prepared by reacting a cyclic carbonate comprising a carbon-carbon double bond, a di-thiol and a polyamine.

Why it is interesting: According to this invention hydroxyurethanes are produced by first reacting a cyclic carbonate which has a double bond (e.g. 4-vinyl-1,3-dioxolan-2-one) with a dithiol (e.g. 1,6-hexanedithiol) using UV radiation and a UV initiator. The resulting di-carbonate is then reacted with a polyamine (e.g. diethylene triamine) resulting in a crosslinked poly(hydroxyurethane). Alternatively the carbonate-amine reaction can happen before the thiol-ene ‘click’ reaction. The materials can be used for binders and adhesives a.o.  The reactions have the advantage of being solvent-, catalyst- and isocyanate-free and having a high yield.

Thiol-ene reaction followed by carbonate-amine reaction

Thiol-ene reaction followed by carbonate-amine reaction

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