Phase segregated block copolymers with tunable properties

Patent metadata

Field	Value
Publication number	US-9840593-B2
Application number	US-201615134739-A
Country	US
Kind code	B2
Filing date	Apr 21, 2016
Priority date	Feb 24, 2015
Publication date	Dec 12, 2017
Grant date	Dec 12, 2017

Abstract

Phase segregated block-copolymer based on repeating structural elements represented by formula I

wherein PHA represents at least one block based on one or more α-hydroxy acids, PDAS represents a central block based on a dialkylsiloxane,
the PDAS block has a weight average molecular weight in the range of from 4000 to 10000,
the blocks PHA have a weight average molecular weight in the range of from 2000 to 10 000,
the phase segregated block copolymer has a weight average molecular weight of from 40 000 to 120 000.

First claim

The invention claimed is:

1. A product comprising a stent, a suture, an orthodontic material, a bone screw, a nail, a catheter, a tube, an orthopedic brace, a splint, or a scaffold for tissue engineering, the product further comprising a phase segregated block-copolymer comprising repeating structural elements represented by formula I

wherein PHA represents at least one block comprising one or more α-hydroxy acids,
PDAS represents a central block comprising a dialkylsiloxane,
the PDAS block has a weight average molecular weight in the range of from 4,000 to 10,000,
the blocks PHA have a weight average molecular weight in the range of from 1,500 to 10,000,
the phase segregated block copolymer has a weight average molecular weight of from 40,000 to 120,000, and
R is a residue of a diisocyanate.

2. The product in accordance with claim 1 wherein the α-hydroxy acids are represented by the formula

wherein R is a linear, branched, or cyclic aliphatic group having 1 to 30 carbon atoms, an aryl group comprising 6 to 30 carbon atoms which may comprise a fused ring, or an alkylaryl group having 7 to 40 carbon atoms.

3. The product in accordance with claim 1 , wherein the α-hydroxy acid is selected from glycolic acid, lactic acid, malic acid, fumaric acid, citric acid, tartaric acid or from products obtained through diazotation of α-amino acids.

4. The product in accordance with claim 3 wherein the α-hydroxy acid is selected from malic acid, lactic acid or glycolic acid or mixtures thereof.

5. The product in accordance with claim 4 wherein the α-hydroxy acid is selected from lactic acid or glycolic acid or mixtures thereof.

6. The product in accordance with claim 1 , wherein the alkyl groups of the dialkylsiloxane may be the same or different at each occurrence, and represent linear, branched or cyclic alkyl groups.

7. The product in accordance with claim 6 wherein the alkyl groups of the dialkylsiloxane are linear or branched alkyl groups having 1 to 12 carbon atoms.

8. The product of claim 7 , wherein the phase segregated block-copolymer has a weight average molecular weight of from 50,000 to 90,000.

9. The product in accordance with claim 6 wherein the alkyl groups of the dialkylsiloxane are methyl groups.

10. The product of claim 9 , wherein the phase segregated block-copolymer has a weight average molecular weight of from 50,000 to 90,000.

11. The product of claim 9 , wherein the phase segregated block-copolymer has a weight average molecular weight of from 50,000 to 90,000, and wherein the copolymer is biodegradable.

12. The product of claim 9 , wherein the phase segregated block-copolymer has a weight average molecular weight of from 50,000 to 90,000, wherein the copolymer is a shape memory copolymer.

13. The product of claim 6 , wherein the phase segregated block-copolymer has a weight average molecular weight of from 50,000 to 90,000.

14. The product in accordance with claim 1 , wherein the phase segregated block-copolymer is biodegradable.

15. The product in accordance with claim 1 , wherein the phase segregated block-copolymer is a shape memory polymer.

16. The product in accordance with claim 1 , wherein the product is a suture, an orthodontic material, a bone screw, a nail, a catheter, a tube, an orthopedic brace, a splint, or a scaffold for tissue engineering.

17. The product in accordance with claim 1 , wherein the product is a shape recovery polymer stent.

18. The product of claim 1 , wherein the phase segregated block-copolymer has a weight average molecular weight of from 50,000 to 90,000.

Assignees

• Univ Freiburg Albert Ludwigs

Inventors

• Shastri V Prasad
• Matloubigharagozloo Maziar

Classifications

• A61L31/06 Primary

  obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds {(A61L31/041 takes precedence)} · CPC title

• A61L2400/16

  Materials with shape-memory or superelastic properties · CPC title

• C08G18/61

  Polysiloxanes · CPC title

• A61L27/18

  obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds · CPC title

• A61L31/14

  Materials characterised by their function or physical properties {, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials} · CPC title