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)

 

Vinyl-Functional UV-Curable Polyurethanes

Patent Title: ALKENYL ETHER POLYOLS

 Number/Link: WO2016038112 (German)

Applicant/Assignee: Henkel

Publication date: 17-03-2016

Gist”: Alkenylether-functional polyols are used in oligomeric PU adhesives.

Why it is interesting: Alkenylether-functional groups are highly reactive and can be cured by UV-initiated cationic polymerization. This has the advantage of being unsensitive to oxigen which allows for so-called “dark cure”, i.e. the continuing polymerization after a first pulse of UV light. According to this invention, vinyl functional polyols are prepared by polymerizing a hydroxyl- or amine functional vinyl ether, e.g. 4-hydroxybutylvinylether (HBVE) or 3-aminopropylvinylether with epoxides or cyclocarbonates. The polyols can then be reacted with isocyanates resulting in UV curable polyurethanes.  In an example HBVE is reacted with 1,4-butanedioldiglycidylether to make the vinyl-functional polyol which is then further reacted with isophorondiisocyanate to make the PU adhesive.

1,4-butandioldiglycidylether

1,4-butandioldiglycidylether

Polyurethane with Thermally Reversible Crosslinks

Patent Title: THERMALLY REVERSIBLE CROSSLINKED POLYURETHANE

 Number/Link: WO2016/018956

Applicant/Assignee: Lubrizol

Publication date: 4-02-2016

Gist”: Diels-Alder adducts of furan and maleimide are used as reversible crosslinks

Why it is interesting: Polyurethanes with thermally reversible crosslinks can be useful: these materials can be processed and recycled as thermoplastics while showing increased mechanical properties and the reduced compression set of thermosets. They can also show self-healing properties in certain circumstances.
According to this invention PU with thermally reversible crosslinks can be prepared by reacting a diisocyanate with a diol containing a furan functional group and then incorporating a polymaleimide. For example: the diol can be prepared by reacting furfurylmethacrylate with thioglycerol and the polymaleimide can be 1,1′-(methylenedi-4,1-phenylene)bismaleimide.
Interesting idea but very similar to WO2015119688 discussed before.

1,1'-(methylenedi-4,1-methylene)bismaleimide

1,1′-(methylenedi-4,1-phenylene)bismaleimide

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