Hybrid PU-Peptide PUDs

Patent Title: AQUEOUS PEPTIDE-FUNCTIONALIZED POLYURETHANE DISPERSIONS

 Number/Link: WO2016/135162

Applicant/Assignee: Henkel; Max-Panck Ges.

Publication date: 1-09-2016

Gist”: A maleimide-capped prepolymer is reacted with the -SH groups in a peptide

Why it is interesting: Polyurethane-protein hybrids are interesting novel materials which potentially have a number of unique properties unattainable with conventional synthetic polymers. In a previous case discussed in this blog an NCO-ended polyurethane prepolymer was reacted with a peptide in water to make a PU-peptide dispersion.  This type of grafting, however, is not very specific because the isocyanate will react mostly with the free amino groups of lysine, which is usually  ‘abundant’ in a typical peptide. According to this invention the grafting can be made very specific by first end-capping the NCO prepolymer with maleimide groups and dispersing in water. The dispersion is then reacted with a peptide solution at pH7. In these circumstances the maleimide will react selectively with the free thiol group of cysteine, of which usually very few are present in a typical peptide because most thiol groups are engaged in S-S disulfide bridges.  Preferably a peptide consisting of 10-200 amino acids is used, with preferably only one free thiol group. By selective grafting the properties of the peptide can be conserved.  The PU-peptide dispersions are claimed to be especially useful for metal adhesives.

L-cysteine

L-cysteine

 

 

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Highly Tuneable Shape Memory Polyurethanes

Patent Title: PROCESSABLE, TUNABLE THIOL-ENE CROSSLINKED POLYURETHANE SHAPE MEMORY POLYMERS

 Number/Link: WO2016/126703

Applicant/Assignee: Texas A&M University

Publication date: 11-08-2016

Gist”: SMPUs are made from combinations of different diisocyanates and chain extenders and different levels of crosslinking using thiol-ene click chemistry

Why it is interesting: This invention is about shape memory polyurethanes with tuneable glass transition temperature and stiffness. In a first step a low mole weight TPU is prepared from a diisocyanate and a short chain diol including some trimethylolpropane allyether (TMPAE) and allylalcohol as chain stopper. The TPU is then blended with a polythiol and a photoinitiator to allow for UV curing. The Tg can be tuned from 30 and 105°C by combining different types of chain extenders and di-iso’s ranging from DEG-HDI to CHDM-H12MDI.  The modulus (in the rubber state) can be  varied between 0.4 to 20 MPa by controlling the level of crosslinking through the amount of TMPAE and amount and type of polythiol.  The SMPUs are said to be especially useful for biomedical applications.

Reaction scheme of the invention

Reaction scheme of the invention

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