Polymeric acetal carboxylates

• US 4,144,226 A
• Filed: 08/22/1977
• Issued: 03/13/1979
• Est. Priority Date: 08/22/1977
• Status: Expired due to Term

• Current Assignee: Solutia Incorporated (Eastman Chemical Company)
• Original Assignee: Monsanto Company (Bayer AG)
• Inventors: Warren, Craig B., Papanu, Victor D., Crutchfield, Marvin M.
• Primary Examiner(s): Anderson, Harold D.
• Assistant Examiner(s): Nielsen, E. A.
• Application Number:
  US05/826,425
• Time in Patent Office: 568 Days
• Field of Search: 260/67 R, 260/484 R, 260/535 P, 560/180
• US Class Current: 525/401
• CPC Class Codes: C08G 2/14 Polymerisation of single aldehydes not provided for in groups C08G2/08 - C08G2/12
• CPC Class Codes: C08G 2/18 Copolymerisation of aldehydes or ketones
• CPC Class Codes: C08G 2/30 Chemical modification by after-treatment
• CPC Class Codes: C11D 3/3711 Polyacetal carboxylates

Abstract

Ether and acetal carboxylates useful as detergent builders to replace sodium tripolyphosphate (STP) in detergent formulations are known to the art. According to the present invention, new and novel polymeric acetal carboxylates are provided which are stable under laundry use conditions, but depolymerize in acid media, making the polymer fragments more readily biodegradable in waste streams.

Claims

1. An acetal carboxylate polymer having the following general formula:

##STR17## wherein M is selected from the group consisting of alkali metal, ammonium, alkyl groups having 1 to 4 carbon atoms;

tetralkyl ammonium groups and alkanol amine groups having from 1 to 4 carbon atoms in the alkyl chain;

n averages at least 4; and

R₁ and R₂ are individually any chemically stable group which stabilize the polymer against rapid depolymerization in alkaline solution.

2. A polymer of claim 1 wherein n averages between about 10 and about 400.

3. A polymer of claim 1 wherein n averages between about 50 and about 200.

4. A polymer of claim 1 wherein R₁ and R₂ are individually selected from the groups consisting of alkyl, alkyl groups containing oxygen and cyclic alkyl groups containing oxygen.

5. A polymer of claim 1 wherein R₁ is HO(CH₂ CH₂ O--_1-3 and R₂ is --CH₂ CH₂ O_1-3 H and n averages between about 50 O)_and about 200.

6. A polymer of claim 1 wherein M is an alkali metal.

7. A polymer of claim 1 wherein M is sodium, R₁ is ##STR18## and mixtures thereof, R₂ is ##STR19## and n averages about 50.

16. A polymer of claim 1 wherein n averages between about 10 and about 100.

17. A polymer of claim 16 wherein R₁ and R₂ individually are selected from the groups consisting of alkyl, alkyl groups containing oxygen and cyclic alkyl groups containing oxygen.

18. A polymer of claim 16 wherein R₁ is selected from the group consisting of --OCH₃, --OC₂ H₅, --OCHCH₃ OC₂ H₅, ##STR23## and mixtures thereof.

19. A polymer of claim 16 wherein R₂ is selected from the group consisting of --CH₃, --C₂ H₅, --CHCH₃ OC₂ H₅, ##STR24## and mixtures thereof.

20. A polymer of claim 17 wherein R₁ is ##STR25## or mixtures thereof.

21. A polymer of claim 17 wherein R₂ is ##STR26##

22. A polymer of claim 17 wherein M is an alkali metal.

23. A polymer of claim 17 wherein M is sodium.

8. A method which comprises

(A) bringing together under polymerization conditions, an ester of glyoxylic acid and a polymerization initiator;

(B) adding to the termini of the resulting polymer a chemically stable end group to stabilize the polymer against rapid depolymerization in alkaline solution.

9. A method of claim 8 wherein the temperature at the beginning of the polymerization is below about 20°

C.

10. A method of claim 8 wherein the polymerization initiator is selected from the group consisting of 2-hydroxy pyridine --H₂ O complex, triethyl amine, hydroxy ion and cyanide ion.

11. A method of claim 8 wherein the polymer is stabilized by adding to the polymer termini a moiety selected from the group consisting of alkyl, alkyl groups containing oxygen and cyclic alkyl groups containing oxygen.

12. A method of claim 11 wherein the polymer is stabilized by adding to the polymer termini moieties to form a polymer of the general formula ##STR20## wherein R₁ is selected from the group consisting of --OCH₃, ##STR21## and mixtures thereof R₂ is selected from the group consisting of --CH₃, --C₂ H₅, --CHCH₃ OC₂ H₅, ##STR22## and mixtures thereof, M is alkali metal, ammonium, alkanol ammonium, tetralkyl ammonium group and alkyl group containing 1 to 4 carbon atoms in the alkyl chain;

and R is hydrogen or alkyl group of 1 to 8 carbon atoms, and n is at least 4.

13. A method of claim 8 wherein the stabilized polymer is converted to a polymer salt selected from the group consisting of alkali metal, ammonium, alkanol ammonium and tetralkyl ammonium salts.

14. A method of claim 13 wherein the stabilized polymer is converted to the alkali metal salt.

15. A method of claim 13 wherein the stabilized polymer is converted to the sodium salt.