Polyurethanes based on terminal diol- and diaminopolyphosphazenes and their hydrogels

Patent metadata

Field	Value
Publication number	US-2023220147-A1
Application number	US-202118000832-A
Country	US
Kind code	A1
Filing date	Jun 21, 2021
Priority date	Jun 26, 2020
Publication date	Jul 13, 2023
Grant date	—

Abstract

The present invention relates to polyphosphazenes, polyurethanes based on these polyphosphazenes, methods for their manufacture and hydrogels based on the polyurethanes. The invention further relates to the use of the hydrogels in medical, veterinary and agricultural applications. The terminal ends of the polyphosphazenes bear NCO-reactive hydrogen atoms for reaction with polyisocyanates.

First claim

1 . A polyphosphazene of the general formula (I):

where:
each radical R is, independent of other radicals R, an organic radical which does not contain a terminal group with an NCO-reactive hydrogen atom;
each radical R 1 is, independent of other radicals R 1 , an organic rest;
each radical X is, independent of other radicals X, an organic rest;
n is zero or a positive integer;
characterized in that
each radical ZH is, independent of other radicals ZH, a group comprising an NCO-reactive hydrogen atom.

2 . The polyphosphazene according to claim 1 , wherein at least one radical ZH is a hydroxyl group, a primary amino group or a secondary amino group.

3 . The polyphosphazene according to claim 1 or 2 , wherein at least one radical X comprises one of the following groups: —B—CH 2 —CH 2 —, —Si—CH 2 —CH 2 — or —S—CH 2 —CH 2 —, wherein the —CH 2 —CH 2 — groups are located between the B, Si or S atoms and a P atom to which radicals R 1 are bond.

4 . The polyphosphazene according to one of claims 1 to 3 , wherein at least one radical X comprises one of the following groups: —(CH 2 ) m —B—, —(CH 2 ) m —Si— or —(CH 2 ) m —S— with m being an integer from 1 to 16, wherein the —(CH 2 ) m groups are located between the B, Si or S atoms and a radical ZH.

5 . The polyphosphazene according to one of claims 1 to 4 , wherein at least one radical X—ZH comprises the group —Ar—CH 2 —CH 2 —S—(CH 2 ) m —OH or —Ar—CH 2 —CH 2 —S—(CH 2 ) m —NH 2 with m being an integer from 1 to 16 and Ar being a phenyl ring with or without additional substituents.

6 . The polyphosphazene according to one of claims 1 to 5 , wherein at least one radical R comprises an oxygen or nitrogen atom bound to a phosphorus atom of a phosphazene group and/or at least one radical R 1 is a substituted or unsubstituted phenyl group.

7 . A method of manufacturing a polyphosphazene according to the general formula (II), comprising reacting a C═C double bond-carrying compound of the general formula (III) with an element-hydrogen bond-carrying compound of the general formula H-E-L-ZH:

where:
each radical E is, independent of other radicals E, B, Si or S;
each radical L is, independent of other radicals L, an organic radical;
each radical ZH is, independent of other radicals ZH, a group comprising an NCO-reactive hydrogen atom;
each radical R is, independent of other radicals R, an organic radical which does not contain a terminal group with an NCO-reactive hydrogen atom;
each radical R 1 is, independent of other radicals R 1 , an organic rest;
each radical Y is, independent of other radicals Y, an organic rest and
n is zero or a positive integer.

8 . A polyurethane polymer obtained by reacting a polyphosphazene (I) according to one of claims 1 to 6 with a polyisocyanate.

9 . A method of manufacturing a polyurethane polymer comprising reacting a polyphosphazene (I) according to one of claims 1 to 6 with a polyisocyanate.

10 . The polymer of claim 8 or the method of claim 9 , wherein the polyisocyanate is an NCO-terminated prepolymer obtained by the reaction of a monomeric polyisocyanate and a polyether polyol.

11 . The polymer of claim 10 or the method of claim 10 , wherein the polyether polyol is a random copolymer of an alkylene oxide and a comonomer selected from: lactides, glycolides, cyclical dicarboxylic acid anhydrides and mixtures of at least two of the aforementioned compounds.

12 . A hydrogel obtained by contacting a polyphosphazene (I) according to one of claims 1 to 6 and/or a polyurethane according to claim 8 with water.

13 . The hydrogel of claim 12 , further comprising, distributed within the hydrogel, a pharmaceutical compound, a pesticide, a herbicide, a pheromone or a combination of at least two of the aforementioned compounds.

14 . A hydrogel according to claim 12 for use as a post-operative separator between internal organs of a human or an animal.

15 . A hydrogel according to claim 13 for use as a delayed-release formulation for the pharmaceutical compound, pesticide, herbicide, pheromone or combination of at least two of the aforementioned compounds distributed within the hydrogel.

Assignees

• Covestro Deutschland Ag

Inventors

• Suetterlin Jan
• Heckroth Heike
• Richter Frank
• Teasdale Ian
• Brueggemann Oliver
• Plavcan Oliver

Classifications

• C08G18/797 Primary

  containing carbodiimide and/or uretone-imine groups · CPC title

• C08G18/6461 Primary

  having phosphorus · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08G65/33348

  containing isocyanate group · CPC title

• A01N25/04

  Dispersions, {emulsions, suspoemulsions, suspension concentrates} or gels (foams A01N25/16) · CPC title