Polymerization of beta-substituted-beta-propiolactones initiated by alkylzinc alkoxides

• US 5,648,452 A
• Filed: 06/01/1995
• Issued: 07/15/1997
• Est. Priority Date: 01/28/1994
• Status: Expired due to Fees

• Current Assignee: The Procter & Gamble Company
• Original Assignee: The Procter & Gamble Company
• Inventors: Kemper, Joseph Jay, Schechtman, Lee Arnold
• Primary Examiner(s): Dodson, Shelley A.
• Application Number:
  US08/447,136
• Time in Patent Office: 775 Days
• Field of Search: 528/354, 528/357, 528/361
• US Class Current: 528/357
• CPC Class Codes: A61L 15/26 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof A61L15/225 takes precedence
• CPC Class Codes: A61L 15/62 Compostable, hydrosoluble or hydrodegradable materials
• CPC Class Codes: C08G 63/823 for the preparation of polylactones or polylactides
• CPC Class Codes: C08J 2367/04 Polyesters derived from hydroxy carboxylic acids, e.g. lactones C08J2367/06 takes precedence
• CPC Class Codes: C08J 5/18 Manufacture of films or sheets
• CPC Class Codes: C08L 67/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C08L67/06 takes precedence
• CPC Class Codes: C09J 167/04 Polyesters derived from hydroxycarboxylic acids, e.g. lactones C09J167/06 takes precedence

Abstract

The present invention relates to a method of preparing a polyester comprising polymerizing at least one β-substituted-β-propiolactone in the presence of an initiating amount of alkylzinc alkoxide in bulk or in solvent for a reaction time and temperature sufficient to produce said polyester.

Claims

1. A method of preparing a polyester comprising polymerizing at least one β

-substituted-β

-propiolactone in the presence of an initiating amount of alkylzinc alkoxide for a reaction time and temperature sufficient to produce the polyester, wherein the alkylzinc alkoxide has the structure R¹ ZnOR² wherein R¹ and R² are independently a C₁, C₂, C₃, C₄, C₅, C₆, C₇, C₈, C₉, or C₁₀ alkyl.

2. The method of claim 1, wherein the alkylzinc alkoxide is nonchiral.

3. The method of claim 2, wherein the polymerizing is conducted in bulk.

4. The method of claim 2, wherein the polymerizing is conducted in a solvent for the nonchiral alkylzinc alkoxide and for the β

-substituted-β

-propiolactone.

5. The method of claim 4, wherein the solvent is an aryl hydrocarbon comprising from about 6 to about 15 carbons or alkyl hydrocarbon comprising from about 5 to about 18 carbons.

6. The method of claim 5, wherein the solvent is toluene or xylene.

7. The method of claim 2, wherein the method comprises copolymerizing two different β

-substituted-β

-propiolactones to produce a copolyester.

8. The method of claim 7, wherein the dissimilar β

-substituted-β

-propiolactones comprise [S]-β

-butyrolactone and [S]-β

-alkyl-β

-propiolactone wherein the [S]-β

-alkyl-β

-propiolactone comprises an alkyl group having two or more carbons.

9. The method of claim 7, wherein the dissimilar β

-substituted-β

-propiolactones comprise [R]-β

-butyrolactone and [R]-β

-alkyl-β

-propiolactone wherein the [R]-β

-alkyl-β

-propiolactone comprises an alkyl group having two or more carbons.

10. The method of claim 7, wherein the dissimilar β

-substituted-β

-propiolactones comprise [S]-β

-butyrolactone and [R]-β

-alkyl-β

-propiolactone wherein the [R]-β

-alkyl-β

-propiolactone comprises an alkyl group having two or more carbons.

11. The method of claim 7, wherein the dissimilar β

-substituted-β

-propiolactones comprise [R]-β

-butyrolactone and [S]-β

-alkyl-β

-propiolactone wherein the [S]-β

-alkyl-β

-propiolactone comprises an alkyl group having two or more carbons.

12. The method of claim 2, wherein said β

-substituted-β

-propiolactone comprises racemic β

-butyrolactone.

13. The method of claim 2, wherein the nonchiral alkylzinc alkoxide is ethylzinc isopropoxide, methylzinc isopropoxide, ethylzinc ethoxide, or ethylzinc methoxide.

14. The method of claim 13, wherein the nonchiral alkylzinc alkoxide is ethylzinc isopropoxide.

15. The method of claim 1, wherein the reaction time is about 3 to 100 hours.

16. The method of claim 7 wherein the reaction time is about 3 to 100 hours.

17. The method of claim 1, wherein the temperature is from about 20°

C. to about 80°

C.

18. The method of claim 17, wherein the temperature is from about 45°

C. to about 60°

C.

19. The method of claim 7, wherein the temperature is from about 40°

C. to about 80°

C.

20. The method of claim 18, wherein the temperature is from about 45°

C. to about 60°

C.

21. The method of claim 1, wherein the temperature is from about 70°

C. to about 80°

C.

22. The method of claim 7, wherein the temperature is from about 70°

C. to about 80°

C.

23. The method of claim 1, wherein the alkylzinc alkoxide is present in an amount to give a mole percent range of Zn to β

-substituted-β

-propiolactone monomers from about 0.005 to about 1.

24. The method of claim 7, wherein the nonchiral alkylzinc alkoxide is present in an amount to give a mole percent range of Zn to β

-substituted-β

-propiolactone monomers from about 0.005 to about 1.

25. A polyester made by the method of claim 1, wherein the β

-substituted-β

-propiolactone is substituted with an alkyl comprising from about 1 to about 19 carbons, alkenyl comprising from about 2 to about 19 carbons, aryl comprising from about 6 to about 19 carbons, aralkyl comprising from about 7 to about 19 carbons, alkaryl comprising from about 7 to about 19 carbons, or cycloalkyl comprising from about 3 to about 19 carbons.

26. A copolyester made by the method of claim 7, wherein the two different β

-substituted-β

-propiolactones are independently substituted with an alkyl comprising from about 1 to about 19 carbons, alkenyl comprising from about 2 to about 19 carbons, aryl comprising from about 6 to about 19 carbons, aralkyl comprising from about 7 to about 19 carbons, alkaryl comprising from about 7 to about 19 carbons, or cycloalkyl comprising from about 3 to about 19 carbons.