Polyurethane Tissue Adhesives

Patent Title: URETHANE DECOMPOSING METHOD AND URETHANE DECOMPOSING AGENT

 Number/Link:  US2016/0257800

Applicant/Assignee: Obihiro University

Publication date: 8-09-2016 (priority PCT/JP)

Gist”: Prepolymer from ether-ester polyol and aliphatic isocyanate

Why it is interesting: There is a growing trend in current surgerical practice to replace sutures and staples with adhesives. These tissue adhesives need to have a particular set of properties, like the correct viscosity, hardening speed, biodegradability and toxic and allergenic properties. Current surgical adhesives are often cyanoacrylates, which react very fast, are brittle and show poor biodegradability, or protein-based adhesives which are costly and form weak bonds. According to this invention an improved polyurethane tissue adhesive can be prepared from an isocyanate-ended prepolymer based on an aliphatic isocyanate and a polyol.  The polyol is prepared from a starter polyol or amine which is reacted with a mixture of an alkoxide and about 10-20% of a  lactide (or glycolide or cyclic acid anhydride).  The lactide is randomly copolymerized with the alkoxide using DMC catalysis. The polyol is then reacted with an aliphatic isocyanate, pref. HDI or IPDI in a NCO/OH ratio of about 8:1. After that monomeric isocyanate is removed by thin film distillation down to less than 1% free monomer.
The adhesives are said to be fast, non-toxic, non-allergenic and biodegradable.

L-Lactide

L-Lactide

Thermoplastic Polyurethane with a Percisely Controlled Biodegradation Rate

Title: PROCESS FOR MAKING BIODEGRADABLE AND/OR BIOABSORBABLE POLYMERS

 Number/Link: WO2014/004334

Applicant/Assignee: Lubrizol

Publication date: 03-01-2014

Gist”: Two sets of parameters are given (and claimed) which, when iteratively adjusted, allow to independently modify the mechanical properties and biodegradation rate of a TPU.

Why it is interesting: Many biomedical materials for implants such as screws, bone plates, tissue scaffolds, pins etc need high mechanical properties but also a controlled biodegradation rate which can vary from weeks to years.  According to this case the precise control of the degradation rate is not possible with currently available bio-polymers.  The invention claims two sets of parameters one which controls the physical properties of a TPU like the molecular weight, harblock content, crystallinity etc, and another set which controls the biodegradation rate like the amount of ‘hydrolyzable units’ in the backbone, hydrophilicity ect. It is claimed that both mechanical properties and degradation rate can be independently controlled by adjusting one or more parameters of each set. In the examples TPUs are prepared from HMDI, 1,4-butane diol and poly(lactide-co-caprolactone) diols where the lactide is the hydrolyzable unit.

A poly(lactide-co-caprolactone)

A poly(lactide-co-caprolactone)

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