Biodegradable alkylene oxide-lactone copolymers

• US 5,525,702 A
• Filed: 05/18/1995
• Issued: 06/11/1996
• Est. Priority Date: 05/18/1995
• Status: Expired due to Term

• Current Assignee: The Dow Chemical Company (Dow, Inc.)
• Original Assignee: The Dow Chemical Company (Dow, Inc.)
• Inventors: Nace, Vaughn M.
• Primary Examiner(s): Dodson, Shelley A.
• Application Number:
  US08/444,117
• Time in Patent Office: 390 Days
• Field of Search: 528/354, 528/361, 528/358, 528/357
• US Class Current: 528/354
• CPC Class Codes: C08G 63/664 derived from hydroxy carboxylic acids

Abstract

The biodegradability of polyglycol-based block copolymers is improved by including in the copolymer a lactone. Representative of these biodegradable enhanced copolymers are those made of 1,2-butylene oxide and ε-caprolactone capped with a homopolymer block of ethylene oxide. The copolymers of this invention have many uses, such as nonionic surfactants, foam control agents, lubricants, and the like.

Claims

1. A biodegradable, capped alkylene oxide-lactone copolymer, the copolymer comprising polymerized:

A. Alkylene oxide units derived from an alkylene oxide of the formula ##STR4## in which each R, individually, is hydrogen, a C₁ -C₆ alkyl or alkoxy radical, or in which the two R substituents together with both vicinal epoxy carbons form a saturated or monoethylenically unsaturated cycloaliphatic hydrocarbon ring; and

B. Lactone units derived from a lactone of the formula ##STR5## in which n is at least two and each R'"'"' is independently hydrogen, C₁ -C₄ alkyl, cyclohexyl, C₁ -C₄ alkoxy or a single ring aromatic hydrocarbon radical;

with the proviso that at least four R'"'"' are hydrogen; and

the cap comprising a polymer block of polymerized alkylene oxide units derived from an alkylene oxide of Formula I in (A) above.

2. The copolymer of claim 1 in which the alkylene oxide of Formula I is selected from the group consisting of ethylene oxide, propylene oxide and the butylene oxides.

3. The copolymer of claim 2 in which the lactone of Formula II is an ε

-caprolactone.

4. The copolymer of claim 3 in which the ε

-caprolactone is of the formula ##STR6## in which each are R", independently, is hydrogen or a C₁ -C₄ alkyl or alkoxy radical, with the proviso that no more than three R" substituents are groups other than hydrogen.

5. The copolymer of claim 4 in which the ε

-caprolactone is an unsubstituted ε

-caprolactone.

6. The copolymer of claim 5 in which the polymer block of polymerized alkylene oxide units in (C) is derived from ethylene oxide.

15. A surfactant comprising the copolymerof claim 1.

17. A foam control agent comprising the copolymer of claim 1.

19. A lubricant comprising the copolymer of claim 1.

7. A biodegradable alkylene oxide-lactone copolymer prepared by contacting under copolymerization conditions:

A. At least one alkylene oxide of the formula ##STR7## in which each R, individually, is hydrogen, a C₁ -C₆ alkyl or alkoxy radical, or in which the two R substituents together with both vicinal epoxy carbons form a saturated or monoethylenically unsaturated cycloaliphatic hydrocarbon ring; and

B. At least one lactone of the formula in which n is at least two and each R'"'"' is independently hydrogen, C₁ -C₄ alkyl, cyclohexyl, C₁ -C₄ alkoxy or a single ring aromatic hydrocarbon ##STR8## radical;

with the proviso that at least four R'"'"' are hydrogen;

C. A polyfunctional initiator of the formula

space="preserve" listing-type="equation">R.sup.v (YH).sub.z (V)

in which R^v is an aliphatic, cycloaliphatic, aromatic or heterocyclic radical;

z is at least two; and

each Y is independently --O--, --S--, --NH-- or --NR^vi --, R^vi being an alkyl, aryl, aralkyl or cycloalkyl radical; and

D. A catalyst selected from the group consisting of alkali metal hydroxide, alkaline earth hydroxides and Lewis acids, in an amount that will promote the copolymerization of the alkylene oxide and the lactone.

8. The copolymer of claim 7 in which the alkylene oxide of Formula I is selected from the group consisting of ethylene oxide, propylene oxide, and the butylene oxides.

9. The copolymer of claim 8 in which the lactone of Formula II is an ε

-caprolactone.

10. The copolymer of claim 9 in which the lactone is of the formula ##STR9## in which each are R", independently, is hydrogen or a C₁ -C₄ alkyl or alkoxy radical, with the proviso that no more than three R" substituents are groups other than hydrogen.

11. The copolymer of claim 10 in which the lactone is an unsubstituted ε

-caprolactone.

12. The copolymer of claim 11 in which the polyfunctional initiator is selected from the group consisting of ethylene glycol, propylene glycol, diethylene glycol, dipropylene glycol, 1,2-dibutylene glycol, glycerine, trimethylol propane, pentaerythritol, ethylendiamine, and ethanolamine.

13. The colpolymer of claim 12 in which the catalyst is selected from the group consisting of alkali metal and alkaline metal earth methal hydroxides.

14. The colpolymer of claim 13 in which the catalyst is potassium hydroxide.

16. A surfactant comprising a copolymer of claim 7.

18. A foam control agent comprising the copolymer of claim 7.

20. A lubricant comprising the copolymer of claim 7.