Preparation of anhydride copolymers

• US 4,789,724 A
• Filed: 10/17/1986
• Issued: 12/06/1988
• Est. Priority Date: 10/17/1986
• Status: Expired due to Term

• Current Assignee: Artery, LLC
• Original Assignee: Massachusetts Institute of Technology
• Inventors: Langer, Robert S., Domb, Abraham J.
• Primary Examiner(s): Anderson, Harold D.
• Assistant Examiner(s): KRASS, FREDERICK F
• Application Number:
  US06/920,724
• Time in Patent Office: 781 Days
• Field of Search: 528/176, 528/193, 528/194, 528/206, 528/271
• US Class Current: 528/176
• CPC Class Codes: A61K 9/2031 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyethylene glycol, polyethylene oxide, poloxamers
• CPC Class Codes: C08G 67/04 Polyanhydrides

Abstract

A method for preparation of very pure anhydride copolymers with high yield. The anhydride copolymers, consisting of aromatic and aliphatic diacids are formed by melt condensation of individually prepared, pure, isolated prepolymers. The method of preparation is characterized by high yield, reproducibility, polymer purity and controlled composition, and is a short and convenient procedure. The polyanhydrides produced by the disclosed method are particularly well suited to biomedical applications requiring low levels of toxic or inflammatory contaminants and physical and mechanical properties which closely conform to manufacturing specifications.

Claims

1. A method for preparing highly pure anhydride copolymers comprising:

providing at least two individually synthetized and purified diacids,

reacting the individual diacids and acetic anhydride separately to form mixed anhydrides of the invididual diacids,

separately removing the unreacted acetic anhydride and diacids from the individual mixed anhydrides formed by the reaction of the acetic anhydride with said diacids,

combining said individual mixed anhydrides, and

polymerizing said mixture of the purified mixed anhydrides of the individual diacids to form copolymers.

2. The method of claim 1 wherein the diacids are selected form the group consisting of sebacic acid, bis(p-carboxyphenoxy-propane, bis(p-carboxyphenoxy)hexane, isophthalic acid, 1,4 phenylene diporpionic acid, adipic acid and dodecanedioic acid.

3. A highly pure anhydride copolymer consisting essentially of individually synthetisized and purified monomers selected from the group consisting of mixed anhydrides of aliphatic and aromatic diacids, wherein said diacids were individually reacted with acetic anhydride and the unreacted diacid and acetic anhydride removed after the reaction.

4. The anhydride copolymer of claim 3 wherein said mixed anhydrides are formed by

separately refluxing individual diacids with acetic anhydride to form individual mixed anhydrides,

removing the excess acetic anhydride, and

recrystallizing the individual mixed anhydrides.

5. The anhydride copolymer of claim 3 wherein the copolymers are further purified by recrystallization.