Block polyesters and like compounds useful as soil release agents in detergent compositions

• US 4,702,857 A
• Filed: 11/22/1985
• Issued: 10/27/1987
• Est. Priority Date: 12/21/1984
• Status: Expired due to Term

• Current Assignee: The Procter & Gamble Company
• Original Assignee: The Procter & Gamble Company
• Inventors: Gosselink, Eugene P.
• Primary Examiner(s): WILLIS JR, PRINCE E
• Application Number:
  US06/801,020
• Time in Patent Office: 704 Days
• Field of Search: 252/8.6, 252/8.7, 252/8.9, 252/89.1, 252/174.21, 252/174.23, 252/174.24, 252/DIG. 2, 252/DIG. 15, 252/525, 252/526, 252/544, 252/545, 560/11, 560/90, 560/91, 528/301
• US Class Current: 510/299
• CPC Class Codes: C08G 63/66 Polyesters containing oxygen in the form of ether groups C08G63/42, C08G63/58 take precedence
• CPC Class Codes: C08G 63/688 containing sulfur
• CPC Class Codes: C11D 3/3715 Polyesters or polycarbonates

Abstract

Block polyesters useful as soil release agents in detergent compositions are disclosed. Preferred polyesters have the formula: ##STR1## wherein each R¹ is a 1,4-phenylene moiety; the R² consist essentially of ethylene moieties, 1,2-propylene moieties or a mixture thereof; each X is ethyl or preferably methyl; each n is from about 12 to about 43; u is from about 3 to about 10.

Claims

1. Compounds of the formula:

space="preserve" listing-type="equation">X[(OCH.sub.2 CH.sub.2).sub.n (OR.sup.5).sub.m ][(A--R.sup.1 --A--R.sup.2).sub.u (A--R.sup.3 --A--R.sup.2).sub.v ]A--R.sup.4 --A[(R.sup.5 O).sub.m (CH.sub.2 CH.sub.2 O).sub.n ]X

wherein each of the A moieties is selected from the group consisting of ##STR29## and combinations thereof with either or both of the moieties ##STR30## each of the R¹ moieties is selected from the group consisting of 1,4-phenylene and combinations thereof with 1,3-phenylene, 1,2-phenylene, 1,8-naphthylene, 1,4-naphthylene, 2,2'"'"'-biphenylene, 4,4'"'"'-biphenylene, C₁ -C₈ alkenylene or C₁ -C₈ alkylene, or mixtures thereof;

the R² moieties are each selected from the group consisting of ethylene moieties, substituted ethylene moieties having C₁ -C₄ alkyl or alkoxy substituents, or mixtures thereof;

the R³ moieties are substituted C₂ -C₁₈ hydrocarbylene moieties having least one --COOM, --O[(R⁵ O)_m (CH₂ CH₂ O)_n ]X or --A[(R² --A--R⁴ --A)]_w [(R⁵ O)_m (CH₂ CH₂ O)_n ]X substituent;

the R⁴ moieties are R¹ or R³ moieties, or a mixture thereof;

each R⁵ is C₃ -C₄ alkylene, or the moiety --R² --A--R⁶ --, wherein R⁶ is a C₁ -C₁₂ alkylene, alkenylene, arylene or alkarylene moiety;

each M is H or a water-soluble cation;

each X is C₁ -C₄ alkyl;

m and n are numbers such that the moiety --(CH₂ CH₂ O)-- comprises at least about 50% by weight of the moiety [(R⁵ O)_m (CH₂ CH₂ O)_n ], provided that when R⁵ is the moiety --R² --A--R⁶ --, m is 1;

each n is at least about 10;

u and v are numbers such that the sum of u+v is from about 3 to about 25;

w is 0 or at least 1; and

when w is at least 1, u, v and w are numbers such that the sum of u+v+w is from about 3 to about 25.

2. The compound of claim 1, wherein each A is ##STR31##

3. The compound of claim 2, wherein said R¹ moieties comprise from about 50 to 100% of said 1,4-phenylene moieties.

4. The compound of claim 3, wherein each R¹ moiety is a 1,4-phenylene moiety.

5. The compound of claim 2, wherein said R³ moieties are selected from the group consisting of substituted C₂ -C₁₂ alkylenes, alkenylenes, arylenes, alkarylenes and mixtures thereof.

6. The compound of claim 5, wherein each of said R³ moieties has only one --A[(R² --A--R⁴ --A)]_w [(R⁵ O)_m (CH₂ CH₂ O)_n ]X substituent and w is at least 1.

7. The compound of claim 2, wherein v is 0.

8. The compound of claim 7, wherein said R² moieties comprise from about 20 to 100% of said ethylene, or substituted ethylene moieties.

9. The compound of claim 8, wherein said R² moieties comprise from about 80 to 100% of said ethylene, or substituted ethylene moieties.

10. The compound of claim 7, wherein said R² moieties comprise from about 20 to 100% ethylene moieties, 1,2-propylene moieties or mixtures thereof.

11. The compound of claim 7, wherein m is 0 and each n is from about 12 to about 119.

12. The compound of claim 8, wherein each n is from about 12 to about 43.

13. Compounds of formula:

##STR32## wherein each R¹ moiety is a 1,4-phenylene moiety;

the R² moieties are each selected from the group consisting of ethylene moieties, 1,2-propylene moieties, 1,2 butylene moieties, 1,2 hexylene moieties, 3-methoxy-1,2-propylene moieties or mixtures thereof, provided that said R² moieties are not exclusively 1,2 butylene moieties, 1,2 hexylene moieties, 3-methoxy-1,2-propylene moieties or mixtures thereof;

the R³ moieties are each selected from the group consisting of substituted 1,3-phenylene moieties having the substituent ##STR33## at the 5-position;

the R⁴ moieties are R¹ or R³ moieties, or a mixture thereof;

each X is C₁ -C₄ alkyl;

each n is from about 12 to about 43;

when w is 0, u+v is from about 3 to about 10;

when w is at least 1, u+v+w is from about 3 to about 10.

14. The compounds of claim 13, wherein v is 0.

15. The compounds of claim 14, wherein said R² moieties comprise from about 80 to 100% of ethylene moieties, 1,2-propylene moieties, or mixtures thereof.

16. A detergent composition which comprises:

(a) from about 1 to about 75% by weight of a nonionic, anionic, ampholytic, zwitterionic, or cationic detergent surfactant, or mixture thereof; and

(b) a soil release component which comprises an effective amount of a soil release compound of the formula;

space="preserve" listing-type="equation">X[(OCH.sub.2 CH.sub.2).sub.n (OR.sup.5).sub.m ][(A--R.sup.1 --A--R.sup.2).sub.u (A--R.sup.3 --A--R.sup.2).sub.v ]A--R.sup.4 --A[(R.sup.5 O).sub.m (CH.sub.2 CH.sub.2 O).sub.n ]X

wherein each of the A moieties is selected from the group consisting of ##STR34## and combinations thereof with either or both of the moieties ##STR35## each of the R¹ moieties is selected from the group consisting of 1,4-phenylene and combinations thereof with 1,3-phenylene, 1,2-phenylene, 1,8-naphthylene, 1,4-naphthylene, 2,2'"'"'-biphenylene, 4,4'"'"'-biphenylene, C₁ -C₈ alkenylene or C₁ -C₈ alkylene, or mixtures thereof;

the R² moieties are each selected from the group consisting of ethylene moieties, substituted ethylene moieties having C₁ -C₄ alkyl or alkoxy substituents or mixtures thereof;

the R³ moieties are substituted C₂ -C₁₈ hydrocarbylene moieties having least one --COOM, --O[(R⁵ O)_m (CH₂ CH₂ O)_n ]X or --A[(R² --A--R⁴ --A)--]_w [--(R⁵ O)_m (CH₂ CH₂ O)_n ]X substituent;

the R⁴ moieties are R¹ or R³ moieties, or a mixture thereof;

each R⁵ is C₃ -C₄ alkylene, or the moiety --R² --A--R⁶ --, wherein R⁶ is a C₁ -C₁₂ alkylene, alkenylene, arylene or alkarylene moiety;

each M is H or a water-soluble cation;

each X is C₁ -C₄ alkyl;

m and n are numbers such that the moiety --(CH₂ CH₂ O)-- comprises at least about 50% by weight of the moiety [(R⁵ O)_m (CH₂ CH₂ O)_n ], provided that when R⁵ is the moiety --R² --A--R⁶ --, m is 1;

each n is at least about 6;

u and v are numbers such that the sum of u+v is from about 3 to about 25;

w is 0 or at least 1; and

when w is at least 1, u, v and w are numbers such that the sum of u+v+w is from about 3 to about 25.

17. The composition of claim 16, wherein each A is ##STR36## and wherein each said soil release compound comprises from about 0.1 to about 10% by weight of the composition.

18. The composition of claim 17, wherein said R¹ moieties comprise from about 50 to 100% of said 1,4-phenylene moieties.

19. The composition of claim 18, wherein each R¹ moiety is a 1,4-phenylene moiety.

20. The composition of claim 19, wherein v is 0.

21. The composition of claim 20, wherein said R² moieties are essentially ethylene moieties, 1,2-propylene moieties or mixtures thereof.

22. The composition of claim 21 wherein said R² moieties comprise from about 20 to 100% of said ethylene moieties, 1,2-propylene moieties or mixtures thereof.

23. The composition of claim 22, wherein said R² moieties comprise from about 80 to 100% of said ethylene moieties, 1,2-propylene moieties or mixtures thereof.

24. The compositions of claim 22, wherein u is from about 3 to about 10.

25. The compositions of claim 24, wherein m is 0 and each n is from about 12 to about 43.

26. The composition of claim 25, which is an isotropic liquid.

27. The composition of claim 26, wherein said soil release component further comprises an organic solvent or hydrotrope for said soil release compound.

28. The composition of claim 25, wherein said soil release compound comprises from about 0.1 to about 5% by weight of the composition.

29. The composition of claim 25, wherein said detergent surfactant comprises from about 10 to about 50% by weight of the composition.

30. The composition of claim 29, wherein said detergent surfactant comprises a nonionic surfactant, an anionic surfactant or a mixture thereof.

31. The composition of claim 29, which further comprises from about 3 to about 20% by weight of the composition of a detergent builder.

32. The composition of claim 29, which further comprises from about 20 to about 30% by weight of the composition of a detergent builder.

33. The composition of claim 29, which further comprises an optical brightener.

34. Compounds of the formula:

##STR37## wherein R² is selected from the group consisting of 1,2-propylene, ethylene, or mixtures thereof;

each X is C₁ -C₄ alkyl;

each n is from about 12 to about 43;

u is from about 3 to about 10.

35. The compounds of claim 34, wherein R² is selected from the group consisting of 1,2-propylene or mixtures of ethylene and 1,2-propylene.

36. A detergent composition which comprises (a) from about 1 to about 75% by weight of a nonionic, anionic, ampholytic, zwitterionic, or cationic detergent surfactant, or mixture thereof;

and (b) a soil release component which comprises an effective amount of a soil release compound according to claim 34.

37. A detergent composition which comprises (a) from about 1 to about 75% by weight of a nonionic, anionic, ampholytic, zwitterionic, or cationic detergent surfactant, or mixtures thereof;

and (b) a soil release component which comprises an effective amount of a soil release compound according to claim 35.

38. The composition of claim 37, which is an isotropic liquid.

39. The composition of claim 37, which further comprises from about 3 to about 30% by weight of the composition of a detergent builder.

40. The composition of claim 39, which further comprises an optical brightener.