Biodegradable material and method of producing biodegradable material

Patent metadata

Field	Value
Publication number	US-9504768-B2
Application number	US-201314387718-A
Country	US
Kind code	B2
Filing date	Mar 28, 2013
Priority date	Mar 28, 2012
Publication date	Nov 29, 2016
Grant date	Nov 29, 2016

Abstract

A biodegradable material has an improved biodegradability, an enhanced shape recovery rate after deformation of the material and an improved flexibility. The biodegradable material is a chemically cross-linked product of: a multivalent compound A having 3 or more functional groups X such as hydroxyl group; a multivalent compound B having 3 or more functional groups Y such as carboxyl group; and a compound C having a structure originated from a hydroxycarboxylic acid whose homopolymer formed by homopolymerization has a glass transition point of −40° C. or lower.

First claim

The invention claimed is:

1. A biodegradable material which is a chemically cross-linked product of:
a multivalent compound A having 3 or more functional groups X selected from the group consisting of hydroxyl group, thiol group and amino group;
a multivalent compound B having 3 or more functional groups Y selected from the group consisting of carboxyl group, isocyanate group and thioisocyanate group; and
a compound C which is a copolymer of a hydroxycarboxylic acid(s) and a monomer(s) of a water-soluble polymer(s) selected from the group consisting of polyethylene glycol, polypropylene glycol, polyvinyl alcohol, polyhydroxyethyl acrylate, polyhydroxyethyl methacylate, carboxymethyl cellulose, hydroxymethyl cellulose and hydroxyethyl cellulose,
wherein the hydroxycarboxylic acid(s) is selected from a homopolymer formed by homopolymerization and has a glass transition point of −40° C. or lower, and
wherein the compound C has a degree of branching of 5 to 16.

2. The biodegradable material according to claim 1 , wherein the weight ratio of said structure originated from said compound C is 18 to 70% by weight.

3. The biodegradable material according to claim 1 , wherein said multivalent compound A is one of a) to e):
a) a homopolymer of a monomer(s) of a water-soluble polymer(s) selected from the group consisting of polyethylene glycol, polypropylene glycol, or, a homopolymer or a copolymer of a monomer(s) of a water-soluble polymer(s) selected from the group consisting of polyvinyl alcohol, polyhydroxyethyl acrylate, polyhydroxyethyl methacrylate, carboxymethyl cellulose, hydroxymethyl cellulose and hydroxyethyl cellulose;
b) a copolymer of the monomer of said water-soluble polymer and a monomer(s) of a hydrophobic polymer(s) selected from the group consisting of vinyl acetate and vinyl caprolactam;
c) a copolymer of the monomer of said water-soluble polymer and a hydroxycarboxylic acid(s) whose homopolymer(s) formed by homopolymerization has/have a glass transition point of −39° C. or higher;
d) a branched polymer formed by binding all of hydroxyl groups of a polyol with a homopolymer or a copolymer of a monomer(s) of a water-soluble polymer(s) selected from the group consisting of polyethylene glycol and polypropylene glycol;
e) a copolymer of said branched polymer and a hydroxycarboxylic acid(s) whose homopolymer(s) formed by homopolymerization has/have a glass transition point of −39° C. or higher.

4. The biodegradable material according to claim 1 , wherein said multivalent compound B is one of f) to i):
f) a compound formed by binding a hydroxyl group(s) of a homopolymer of a monomer(s) of a water-soluble polymer(s) selected from the group consisting of polyethylene glycol, polypropylene glycol, or, a homopolymer or a copolymer of a monomer(s) of a water-soluble polymer(s) selected from the group consisting of polyvinyl alcohol, polyhydroxyethyl acrylate, polyhydroxyethyl methacrylate, carboxymethyl cellulose, hydroxymethyl cellulose and hydroxyethyl cellulose, with a polycarboxylic acid(s);
g) a compound formed by binding a hydroxyl group(s) of a copolymer of the monomer of said water-soluble polymer and a hydroxycarboxylic acid(s) whose homopolymer(s) formed by homopolymerization has/have a glass transition point of −39° C. or higher, with a polycarboxylic acid(s);
h) a compound formed by binding a hydroxyl group(s) of a branched polymer formed by binding all of hydroxyl groups of a polyol with a homopolymer or a copolymer of a monomer(s) of a water-soluble polymer(s) selected from the group consisting of polyethylene glycol and polypropylene glycol, with a polycarboxylic acid(s);
i) a compound formed by binding a hydroxyl group(s) of a copolymer of said branched polymer and a hydroxycarboxylic acid(s) whose homopolymer(s) formed by homopolymerization has/have a glass transition point of −39° C. or higher, with a polycarboxylic acid(s).

5. The biodegradable material according to claim 1 , wherein the hydroxycarboxylic acid of compound C is 6-hydroxycaproic acid.

6. The biodegradable material according to claim 3 , wherein said polyol is selected from the group consisting of glycerin, polyglycerin and pentaerythritol.

7. The biodegradable material according to claim 3 , wherein said hydroxycarboxylic acid(s) whose homopolymer(s) formed by homopolymerization has/have a glass transition point of −39° C. or higher is/are selected from the group consisting of glycolic acid, lactic acid, glyceric acid, hydroxybutyric acid, malic acid, tartaric acid, hydroxyvaleric acid and 3-hydroxyhexanoic acid.

8. The biodegradable material according to claim 4 , wherein said polycarboxylic acid(s) is/are selected from the group consisting of oxalic acid, malonic acid, succinic acid, glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, malic acid, tartaric acid and fumaric acid.

9. A vascular embolization material comprising said biodegradable material according to claim 1 .

10. An anti-adhesive material comprising said biodegradable material according to claim 1 .

11. A wound dressing material comprising said biodegradable material according to claim 1 .

12. A hemostatic material comprising said biodegradable material according to claim 1 .

13. A urinary incontinence-preventing material comprising said biodegradable material according to claim 1 .

14. A process of producing a biodegradable material comprising a chemical cross-linking step wherein a multivalent compound A having 3 or more functional groups X selected from the group consisting of hydroxyl group, thiol group and amino group, a multivalent compound B having 3 or more functional groups Y selected from the group consisting of carboxyl group, isocyanate group and thioisocyanate group, and a compound C which is a copolymer of a monomer(s) of a water-soluble polymer(s) selected from the group consisting of polyethylene glycol, polypropylene glycol, polyvinyl alcohol, polyhydroxyethyl acrylate, polyhydroxyethyl methacrylate, carboxymethyl cellulose, hydroxymethyl cellulose and hydroxyethyl cellulose, and a hydroxycarboxylic acid(s) whose homopolymer formed by homopolymerization has a glass transition point of −40° C. or lower, the compound C having a degree of branching of 5 to 16, are dissolved in a solvent to allow chemical cross-linking reaction to proceed, to obtain said biodegradable material.

Assignees

• Toray Industries

Inventors

• Fujita Masaki
• Nakanishi Megumi
• Tanahashi Kazuhiro

Classifications

• A61L15/64

  specially adapted to be resorbable inside the body · CPC title

• C08L101/16

  the macromolecular compounds being biodegradable · CPC title

• A61L24/0042

  Materials resorbable by the body · CPC title

• A61L24/046 Primary

  obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds (A61L24/043 takes precedence) · CPC title

• A61L2400/04

  Materials for stopping bleeding · CPC title