Rare earth metal coordination compounds as lactone polymerization catalysts

• US 5,292,859 A
• Filed: 12/22/1992
• Issued: 03/08/1994
• Est. Priority Date: 12/22/1992
• Status: Expired due to Fees

• Current Assignee: Ecological Chemical Products Company
• Original Assignee: E. I. du Pont de Nemours and Company (Corteva, Inc.)
• Inventors: McLain, Stephan J., Ford, Thomas M.
• Primary Examiner(s): Kight, III, John
• Assistant Examiner(s): Dodson, Shelley A.
• Application Number:
  US07/995,457
• Time in Patent Office: 441 Days
• Field of Search: 525/415, 528/354, 528/357
• US Class Current: 528/354
• CPC Class Codes: C08G 63/823 for the preparation of polylactones or polylactides

Abstract

A process for polymerizing lactide and up to 20 mole percent of another lactone is disclosed. The cayalysts used have the formula MZ₃ wherein M is scandium, yttrium, bismuth, a lanthanide series rare earth metal or a mixture thereof and the Zs are independently the same or different highly coordinating ligands. The preferred metals M are lanthanum, cerium, praseodymium and neodymium with lanthanum being especially preferred. The preferred ligands are betadiketones, betaketoesters and malonate anions with the betadiketones such as 2,2,6,6-tetramethyl-3,5-heptanedionates being especially preferred.

Claims

1. A process for polymerizing lactide comprising:

contacting at 100°

C. to 220°

C. a lactide and up to 20 mole percent of another lactone selected from the group consisting of ##STR6## and mixtures thereof, where n is 4 or 5, h, i, k and m are independently 1 or 2, each R is independently selected from H, a hydrocarbyl containing up to 12 carbon atoms or substituted hydrocarbyl containing up to 12 carbon atoms with a catalytic amount of a catalyst of the formula MZ₃, or MZ₃ coordinated with one or more neutral ligands, wherein M is metal selected from the group consisting of scandium, yttrium, bismuth and lanthanide series rare earth metals and the Zs are independently the same or different highly coordinating ligands and cooling the resulting polymer.

2. The process of claim 1 wherein the R in the lactone comonomer is H or CH₃.

3. The process of claim 2 wherein at least one Z is a betadiketone, betaketoester or malonate anion.

4. The process of claim 2 wherein all three Zs are a betaketone, betaketoester or malonate anion.

5. The process of claim 4 wherein the polymerization is carried out in the melt and a lactide homopolymer is being prepared.

6. The process of claim 5 wherein the metal M is lanthanum, cerium, praseodymium, neodymium, or mixtures thereof.

7. The process of claim 4 wherein all three Zs are a betaketone anion.

8. The process of claim 7 wherein the polymerization is carried out in the melt and a lactide homopolymer is being prepared.

9. The process of claim 8 wherein the metal M is lanthanum, cerium, praseodymium, neodymium, or mixtures thereof.

10. The process of claim 7 wherein all three Zs are 2,2,6,6-tetramethyl-3,5-heptanedionate.

11. The process of claim 10 wherein the polymerization is carried out in the melt and a lactide homopolymer is being prepared.

12. The process of claim 11 wherein the metal M is lanthanum, cerium, praseodymium, neodymium, or mixtures thereof.

13. The process of claim 12 wherein the metal M is lanthanum.

14. The process of claim 4 wherein MZ₃ is lanthanum tris (t-butylacetoacetate).

15. The process of claim 4 wherein MZ₃ is lanthanum tris (acetylacetone).

16. The process of claim 1 wherein MZ₃ is coordinated with one or more neutral ligands.

17. The process of claim 5 wherein MZ₃ is coordinated with one or more neutral ligands.

18. The process of claim 16 wherein the neutral ligand is selected from the group consisting of water, amines, alcohols, ethers, esters, phosphates, phosphine oxides, and amine oxides.

19. The process of claim 17 wherein the neutral ligand is selected from the group consisting of water, amines, alcohols, ethers, esters, phosphates, phosphine oxides, and amine oxides.