Process for preparing synthetic absorbable poly(esteramides)

• US 4,529,792 A
• Filed: 05/06/1982
• Issued: 07/16/1985
• Est. Priority Date: 12/17/1979
• Status: Expired due to Term

• Current Assignee: 3M Company
• Original Assignee: 3M Company
• Inventors: Barrows, Thomas H.
• Primary Examiner(s): Anderson, Harold D.
• Application Number:
  US06/375,744
• Time in Patent Office: 1,167 Days
• Field of Search: 528/291, 528/274, 528/361, 528/367, 528/370, 528/288, 528/289, 528/372
• US Class Current: 528/291
• CPC Class Codes: A61L 17/105 Polyesters not covered by A61L17/12
• CPC Class Codes: C08G 69/44 Polyester-amides

Abstract

A body absorbable polymeric material for implantation which is a condensation product of reacting a diamine with lactic or glycolic acid to form a diamidediol which is then reacted with a bischloroformate or a compound selected from the group consisting of dicarboxylic acids, methyl and ethyl esters of dicarboxylic acids, diacidchlorides, and anhydrides of a dicarboxylic acid.

Claims

1. A process for making a body absorbable polymeric material having a plurality of units of the general formula:

##STR3## in which R¹ is hydrogen or methyl;

R³ and R⁵ are identical or different and are groups selected from the class consisting of linear and branched alkylene, alkylene having 1 or 2 nonadjacent catenary oxygen or sulfur atoms, alkenylene, cycloalkylene and arylene;

said groups having up to 25 carbon atoms in the cyclic compounds and from 2 to 25 carbon atoms in the non-cyclic compounds;

R² and R⁴ are hydrogen or alkyl having 1 to 4 carbon atoms or R² and R⁴ together are linear or branched alkylene having one to four carbons forming with N--R³ --N a heterocyclic group having 5 or 6 ring atoms; and

a and b are independently zero or one

said process comprising the steps of;

reacting at least one diamine with lactic or glycolic acid to form at least one diamidediol; and

reacting said at least one diamidediol with a bischloroformate or a compound selected from the group consisting of dicarboxylic acids, methyl and ethyl esters of dicarboxylic acids, diacidchlorides, and anhydrides of a dicarboxylic acid to provide said body adsorbable polymeric material.

2. The process of claim 1 wherein said diamidediol is placed in a solvent prior to reacting with said compound or said bischloroformate.

3. The process of claim 1 wherein said compound is succinyl chloride.

4. The process of claim 2 wherein said solvent is selected from the group consisting of chlorobenzene, 1,1,2-trichloroethane and 1,4-dioxane.

5. The process of claim 2 which includes the additional step of removing said solvent after reacting with said compound or said bischloroformate.

6. The process of claim 1 wherein said diamidediol is a mixture comprised of 1,12-di(hydroxyacetamido)-4,9-dioxadodecane and 1,12-di(hydroxyacetamide)dodecane.