Biodegradable elastomers prepared by the condensation of an organic di-, tri- or tetra-carboxylic acid and an organic diol

Patent metadata

Field	Value
Publication number	US-9422396-B2
Application number	US-201313864759-A
Country	US
Kind code	B2
Filing date	Apr 17, 2013
Priority date	May 28, 2007
Publication date	Aug 23, 2016
Grant date	Aug 23, 2016

Abstract

The present disclosure relates to biodegradable and biocompatible elastomeric polymers that are amorphous and have a glass transition temperature below both room temperature and body temperature, and which will homogenously degrade to water soluble by-products with no reported toxicity.

First claim

I claim:

1. A thermoset copolymer comprising: polymerizing units of:
a) about 1 to about 99% by weight of, based on the total mass of the copolymer, a monomer of the formula III:

in which R 2 is C 3 -C 20 cycloalkylene, C 1 -C 30 alkylene, C 2 -C 30 alkenylene, or C 2 -C 30 alkynylene, said latter 3 groups being straight-chained or branched and/or interrupted by one, two or three C 3 -C 10 cyclic moieties therein, and said 4 groups being optionally substituted by one or more groups selected from OH, halo, OR 4 and R 4 , in which R 4 is selected from C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl;
b) about 1 to about 99%, by weight, based on the total mass of the copolymer, of a monomer of the formula V
HO—R 5 —OH  (V)

in which the radical R 5 is C 3 -C 20 cycloalkylene, C 1 -C 30 alkylene, C 2 -C 30 alkenylene, C 2 -C 30 alkynylene, said latter 3 groups being straight-chained or branched and/or interrupted by one, two or three C 3 -C 10 cyclic moieties therein, wherein one or more of the carbon atoms may be replaced by oxygen, and said 4 groups being optionally substituted by one or more groups selected from OH, halo, OR 4 and R 4 , in which R 4 is selected from C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl; or R 5 is a polyalkylene glycol or a poly-ε-caprolactone; wherein the co-polymer is crosslinked with a photosensitive compound, wherein said copolymer is a thermoset elastomer and an alternating copolymer having the monomer of Formula III alternating with the monomer of Formula V and wherein said copolymer is uniformly biodegradable.

2. The polymer according to claim 1 , wherein R 2 is C 3 -C 10 cycloalkylene, C 1 -C 14 alkylene, C 2 -C 10 alkenylene, or C 2 -C 10 alkynylene, said latter 3 groups being straight-chained or branched and/or interrupted by one, two or three C 3 -C 6 cyclic moieties therein, and said 4 groups being optionally substituted by one to six groups selected from OH, halo, OR 4 and R 4 , in which R 4 is selected from C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl.

3. The polymer according to claim 1 , wherein the monomer of formula III is selected from

4. The polymer according to claim 3 , wherein the monomer of formula III is.

5. The polymer according to claim 1 , wherein R 5 is C 3 -C 10 cycloalkylene, C 1 -C 10 -alkylene, C 2 -C 10 alkenylene, C 2 -C 10 alkynylene, said latter 3 groups being straight-chained or branched and/or interrupted by one, two or three C 3 -C 6 cyclic moieties therein, wherein one or more of the carbon atoms may be replaced by oxygen, and said 4 groups being optionally substituted by one to six groups selected from OH, halo, OR 4 and R 4 , in which R 4 is selected from C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl or C 3 -C 6 cycloalkyl.

6. The polymer according to claim 5 , wherein the monomer of formula V is selected from,

7. The polymer according to claim 5 , wherein the monomer of formula V is polyethylene glycol, polypropylene glycol or a poly-ε-caprolactone.

8. The polymer according to claim 7 , wherein the monomer of formula V is polyethylene glycol or a poly-ε-caprolactone.

9. The polymer according to claim 7 , wherein the polyethylene glycol or poly-ε-caprolactone is PEG 200, PEG 400, PEG 600, PEG 1000, PEG 2000, PEG 6000 or poly-ε-caprolactone diol of molecular weight range 500-2000D.

10. The polymer of claim 1 , wherein the copolymer comprises free hydroxyl groups or carboxyl groups which are derivatized with the photosensitive compound.

11. The polymer of claim 10 , wherein the photosensitive compound is a UV or visible light photosensitive compound.

12. The polymer of claim 11 , wherein the photosensitive compound is selected from

and derivatives thereof.

13. The polymer according to claim 1 , wherein the polymer is crosslinked with UV, laser or visible light.

14. The polymer according to claim 1 , wherein the polymer is a thermoset elastomer having a glass transition temperature (T g ) below 0° C.

15. A process for preparing the thermoset elastomer polymer of claim 1 , comprising a reacting monomers of the formula (III) with monomers of the formula (V) to form a condensation co-polymer, wherein the condensation co-polymer is reacted with a photosensitive compound to form a photosensitive condensation polymer which is photocrosslinked to provide the thermoset elastomer polymer.

16. The process according to claim 15 , wherein the photosensitive compound is acrolyl chloride or an acrylate derivative, coumarin or a coumarin-derivative, or a cinnamate or a cinnamate derivative.

17. The process according to claim 16 , wherein the photosensitive compound is acryloyl chloride.

18. The process according to claim 17 , wherein the condensation co-polymer forms an acrylated condensation polymer when reacted with acryloyl chloride.

19. The process according to claim 18 , wherein the photosensitive condensation polymer is photocrosslinked upon exposure to UV or visible light having a wavelength of between about 200 to 750 nm.

20. The process according to claim 19 , wherein the photosensitive condensation polymer is photocrosslinked upon exposure to visible light having a wavelength of between about 380 to 750 nm.

21. The copolymer according to claim 1 , wherein the photosensitive crosslinking compound is capable of reacting to light in the visible region of the electromagnetic spectrum.

Assignees

• Younes Husam
• Univ Qatar

Inventors

• Younes Husam

Classifications

• A61L15/26 Primary

  Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof {(A61L15/225 takes precedence)} · CPC title

• C08J3/243

  Two or more independent types of crosslinking for one or more polymers · CPC title

• A61L15/44

  Medicaments · CPC title

• C08G64/42 Primary

  Chemical after-treatment · CPC title

• C08K5/151

  having one oxygen atom in the ring · CPC title