Non-Isocyanate Polyurethanes from Sucrose-Fatty Acid Esters


 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

Cooperative Catalyst System for NIPU

Title: Catalyst for Non-Isocyanate Based Polyurethane


Applicant/Assignee: Dow; Univ. Northwestern

Publication date: 3-09-2015

Gist”: The cyclocarbonate-amine reaction is catalysed by a lewis acid/lewis base combination

Why it is interesting: It is well known that polyhydroxyurethanes can be produced from cyclic carbonates and amines.  These “nonisocyanate polyurethanes” can have advantages over conventional polyurethanes, e.g. as coatings with improved chemical resistance. The reactivity of (especially 5-ring)  cyclocarbonates is however much lower than that of isocyanates making the reaction much less practical.  According to this invention that problem can be solved by using a ‘cooperative’ catalyst system consisting of a lewis acid and an organic lewis base. In an example a difunctional cyclocarbonate-capped prepolymer is reacted with 1,3-cyclohexane-bis(methylamine) catalysed by a mixture of  lithium trifluoromethanesulfonate and triazabicyclodecene.
It has been noted before in this blog that Dow, as one of the major isocyanate producers, also appears to be interested in non-iso PU.



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