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

Advertisement

Isocyanate-Free Polyurethanes Using Azide-Alkyne Click Chemistry

Title: SYNTHESIS OF POLYURETHANE POLYMERS VIA COPPER AZIDE-ALKYNE CLICK CHEMISTRY FOR COATINGS, ADHESIVES, SEALANTS AND ELASTOMER APPLICATIONS

 Number/Link: WO2014/122153

Applicant/Assignee: Sika

Publication date: 14-08-2014

Gist”: Polyurethane prepolymers capped with azides and alkynes are reacted using copper catalysis.

Why it is interesting: Because of safety, health and envriromental issues, isocyanate-free systems have clearly been gaining in importance the last few years.  Especially for coatings, adhesives and OCF applications, alternative curings systems are being developed. In the current invention an isocyanate-free system is based on the reaction between a prepolymer having at least two azide groups and a prepolymer having at least two alkyne groups. The reaction is copper catalyzed such that it can be performed at ambient temperature. The first prepolymer is (pref.)  prepared by reacting an isocyanate ended prepolymer with glycidol (2,3-epoxy-1-propanol) and subsequently with sodium azide. The second prepolymer is similarly prepared by reacting an isocyanate ended prepolymer with propargyl alcohol (2-propyn-1-ol).  The systems are said to be especially useful for roof coatings.

Example of an azide-alkyne reaction resulting in 1,4-disubstituded triazoles.

Example of an azide-alkyne reaction resulting in 1,4-disubstituded triazoles.

 

More Non-Isocyanate Polyurethanes

Title:  METHOD FOR PREPARING POLY(CARBONATE-URETHANE) OR POLY(ESTER-URETHANE)

 Number/Link: US20130144027

Applicant/Assignee: CENTRE NAT RECH SCIENT; TOTAL RES & TECHNOLOGY

Publication date: 6-06-2013 (priority PCT/EP)

Gist”: Non-isocyanate polycarbonate- or polyester- polyurethane with very high softblock molecular weight produced by “immortal” ring opening polymerization.

Why it is interesting: Non-isocyanate PU systems appear to become a growing trend – at least in scientific and patent literature. In addition to not using phosgene or isocyanates, advantages quoted are improved biodegradability and recyclability.  The current invention teaches the use of “immortal” ringopening polymerization to polymerize 5,6 or 7 membered cyclic carbonates or cyclic esters. This type of ROP is highly efficient and is described in e.g. US2011092664.  The resulting polymer is subsequently modified with anhydrides to a polymer with carboxylic end-groups, which are then reacted with cyclic carbonates bearing hydroxyl groups.  The resulting polymer has a MW of (preferably) 50,000 to 100,000 and can be reacted with polyamines to produce the polyurethanes. See the reaction scheme below.

Reaction sequence according to the invention

Reaction sequence according to the invention

  • Pages

  • Categories

  • Enter your email address to follow this blog and receive notifications of new posts by email.

    Join 1,089 other subscribers
  • Follow Innovation in PU on Twitter

%d bloggers like this: