Copolymers of D,L-lactide and epsilon caprolactone

• US 4,045,418 A
• Filed: 01/28/1975
• Issued: 08/30/1977
• Est. Priority Date: 01/28/1975
• Status: Expired due to Term

• Current Assignee: Chevron Research Company (Chevron Corp.)
• Original Assignee: Gulf Oil Corporation Limited
• Inventors: Sinclair, Richard G.
• Primary Examiner(s): Anderson, Harold D.
• Assistant Examiner(s): Nielsen, E. A.
• Application Number:
  US05/544,789
• Time in Patent Office: 945 Days
• Field of Search: 260/78.3
• US Class Current: 528/357
• CPC Class Codes: C08G 63/08 Lactones or lactides

Abstract

Copolymers which can be fabricated into films, fibers and structural shapes are prepared by copolymerizing an optically inactive lactide, i.e., D,L-lactide, and epsilon caprolactone in the presence of a tin ester of a carboxylic acid. A copolymer prepared from 85 parts by weight of D,L-lactide and 15 parts by weight of epsilon caprolactone is a thermoplastic elastomer. A copolymer prepared from 90 parts by weight of D,L-lactide and 10 parts by weight of epsilon caprolactone is a rigid, clear, thermoplastic solid.

Claims

1. A thermally stable copolymer of an optically inactive lactide and epsilon caprolactone, said copolymer being obtained by heating a mixture of L,L-lactide having a melting point above 100°

C. and epsilon caprolactone at a temperature above the melting point of D,L-lactide and below 200°

C. in the presence of a catalyst, said mixture comprising about 60 to about 95 per cent by weight of D,L-lactide.

2. A thermally stable copolymer in accordance with claim 1 wherein said mixture comprises about 75 to about 90 percent by weight of D,L-lactide.

7. A thermally stable copolymer in accordance with claim 1 wherein said catalyst is a tin ester of a carboxylic acid containing up to 18 carbon atoms.

3. A thermoplastic elastomer of an optically inactive lactide and epsilon caprolactone, said elastomer being obtained by heating 85 parts by weight of D,L-lactide having a melting point above 100°

C. and 15 parts by weight of epsilon caprolactone at a temperature above the melting point of D,L-lactide and below 200°

C. in the presence of a tin ester of a carboxylic acid containing up to 18 carbon atoms.

4. A thermoplastic elastomer in accordance with claim 3 wherein the D,L-lactide and epsilon caprolactone are heated at about 125°

to about 130°

C.

5. A rigid, clear, thermoplastic solid of an optically inactive lactide and epsilon caprolactone, said solid being obtained by heating 90 parts by weight of D,L-lactide having a melting point above 100°

C. and 10 parts by weight of epsilon caprolactone at a temperature above the melting pont of D,L-lactide and below 200°

C. in the presence of a tin ester of a carboxylic acid containing up to 18 carbon atoms.

6. A rigid, clear, thermoplastic solid in accordance with claim 5 wherein the D,L-lactide and epsilon caprolactone are heated at about 105°

to about 110°

C.

8. A terpolymer of an optically inactive lactide, glycolide and epsilon caprolactone, said terpolymer being obtained by heating a mixture of D,L-lactide having a melting point above 100°

C., glycolide and epsilon caprolactone at a temperature above the melting point of D,L-lactide and below 200°

C. in the presence of about 0.001 to about 2 percent by weight, based on the total weight of the D,L-lactide, glycolide and epsilon caprolatone, of catalyst, said mixture comprising about 60 to about 95 percent by weight of D,L-lactide and about 5 to about 40 percent by weight of glycolide and epsilon caprolactone, the weight ratio of glycolide;

epsilon caprolactone being within the range of 1;

9 to 9;

1.

9. A terpolymer in accordance with claim 8 wherein the D,L-lactide, glycolide and epsilon caprolactone are heated at about 100°

to about 160°

C.

10. A terpolymer in accordance with claim 9 wherein said mixture of D,L-lactide, glycolide and epsilon caprolactone comprises about 75 percent by weight of D,L-lactide and about 25 percent by weight of glycolide and epsilon caprolactone.

11. A terpolymer in accordance with claim 10 wherein the D,L-lactide, glycolide and epsilon caprolactone are heated at about 118°

to 138°

C. and the weight ratio of glycolide;

epsilon caprolactone is 3;

2.

12. A terpolymer in accordance with claim 8 in which said catalyst is a tin ester of a carboxylic acid containing up to 18 carbon atoms.