Biodegradable cationic surface-active agents containing ester or amide and polyalkoxy group

• US 4,228,042 A
• Filed: 06/26/1978
• Issued: 10/14/1980
• Est. Priority Date: 06/26/1978
• Status: Expired due to Term

• Current Assignee: The Procter & Gamble Company
• Original Assignee: The Procter & Gamble Company
• Inventors: Letton, James C.
• Primary Examiner(s): Pitlick, Harris A.
• Application Number:
  US05/919,343
• Time in Patent Office: 841 Days
• Field of Search: 252/547, 252/528, 252/8.8, 560/196, 560/60, 560/155, 560/179, 560/186, 260/404, 260/567.6 M, 260/567.6 R, 260/561 A, 260/561 B, 260/561 R, 260/463
• US Class Current: 510/331
• CPC Class Codes: C11D 1/62 Quaternary ammonium compounds
• CPC Class Codes: C11D 3/0021 Dye-stain or dye-transfer inhibiting compositions

Abstract

Novel, biodegradable cationic surface-active agents are disclosed. These compounds, when used in laundry detergent compositions together with selected nonionic surfactants, provide excellent removal of particulate and greasy/oily soils, as well as providing fabric softening, static control, and dye transfer inhibition benefits to the laundered fabrics.

Claims

1. A compound having the formula ##STR40## wherein each R¹ is C₁ to C₄ alkyl or hydroxyalkyl;

each R² is either hydrogen or C₁ to C₃ alkyl;

R³ is C₄ to C₃₀ straight or branched chain alkyl or alkenyl;

R⁴ is C₁ to C₁₀ alkylene or alkenylene;

n is from 2 to 4;

y is from 1 to 20;

a is 0 or 1, and t is 0 to 1, but t must be 1 when a is 1;

m is from 1 to 5;

Z² is selected from the group consisting of ##STR41## Z¹ is selected from the group consisting of ##STR42## said selections being made so that ##STR43## is an alkyl or alkenyl group which can be interrupted by only structures selected from the group consisting of;

##STR44## and wherein at least one of said Z¹ or Z² groups is selected from the group consisting of ester, reverse ester, amide, and reverse amide; and

X is an anion which makes the surfactant at least water-dispersible.

2. The compound of claim 1 wherein Z² is selected from the group consisting of ester, reverse ester, amide and reverse amide.

3. The compound of claim 2 wherein Z² is selected from the group consisting of ester and reverse ester.

4. The compound of claim 2 wherein Z² is selected from the group consisting of amide and reverse amide.

5. The compound of claim 2 wherein n is 4 and R² is hydrogen.

6. The compound of claim 2 wherein n is 2 and the R² groups are CH₃ and hydrogen respectively.

7. The compound of claim 2 wherein n is 2 and R² is hydrogen.

8. The compound of claim 7 wherein y is from 1 to 10.

9. The compound of claim 8 wherein R³ is C₈ to C₁₈ alkyl.

10. The compound of claim 7 wherein a is 1 and Z¹ is ##STR45##

11. The compound of claim 10 wherein t is 1 and R⁴ is C₂ alkylene.

12. The compound of claim 7 wherein a is 0.

13. The compound of claim 12 wherein m is 2.

14. The compound of claim 13 wherein t is 1 and R⁴ is methylene.

15. The compound of claim 14 wherein Z² is ##STR46##

16. The compound of claim 15 wherein y is from 1 to 10.

17. The compound of claim 16 wherein R³ is C₈ to C₁₈ alkyl.

18. The compound of claim 17 wherein R¹ is CH₃.

19. The compound of claim 18 wherein X is selected from the group consisting of halides, methyl sulfate, sulfate, and nitrate.

20. The compound of claim 19 wherein X is selected from the group consisting of chloride, bromide, iodide, sulfate and methyl sulfate.

21. The compound of claim 20 wherein y is 7.

22. The compound of claim 21 wherein R³ is C₁₂ alkyl.

23. The compound of claim 7 wherein Z² is ##STR47##

24. The compound of claim 23 wherein y is from 1 to 10.

25. The compound of claim 24 wherein R³ is C₈ to C₁₈ alkyl.

26. A detergent composition containing from 0 to about 20% of phosphate materials, and having a pH in the laundry solution of not greater than about 11, comprising from about 5 to about 100% of a surfactant mixture consisting essentially of

(a) a biodegradable nonionic surfactant having the formula R(OC₂ H₄)_n OH wherein R is a primary or secondary alkyl chain of from about 8 to about 22 carbon atoms and n is an average of from about 2 to about 12, having an HLB of from about 5 to about 17;

and

(b) the cationic surfactant of claim 1;

said composition having a pH of at least about 6.5 in the aqueous laundry solution, and wherein the ratio of said nonionic to said cationic component is in the range of from about 1;

1 to about 100;

1.

27. The composition of claim 26 wherein, in the cationic surfactant, Z² is selected from the group consisting of ester, reverse ester, amide, and reverse amide.

28. The composition of claim 27 wherein the nonionic surfactant is selected from the group consisting of the condensation product of C₁₀ alcohol with 3 moles of ethylene oxide, the condensation product of coconut alcohol with 5 moles of ethylene oxide, the condensation product of C₁₂ alcohol with 5 moles of ethylene oxide, the condensation product of C_12-13 alcohol with 3 moles of ethylene oxide, and the same product which is stripped to remove substantially all lower ethoxylate and nonethoxylate fractins, the condensation product of C_12-13 alcohol with 6.5 moles of ethylene oxide, the condensation product of C_12-13 alcohol with 9 moles of ethylene oxide, the condensation product of C_14-15 alcohol with 3 moles of ethylene oxide, the condensation product of C_14-15 alcohol with 4 moles of ethylene oxide, the condensation product of C_14-15 alcohol with 7 moles of ethylene oxide, the condensation product of C_14-15 alcohol with 9 moles of ethylene oxide, and mixtures thereof.

29. The composition of claim 27 wherein, in the cationic surfactant, Z² is ##STR48##

30. The composition of claim 29 wherein, in the cationic surfactant, n is equal to 2 and R² is hydrogen.

31. The composition of claim 30, wherein, in the cationic surfactant, a is 0 and m is equal to 2.

32. The composition of claim 31 wherein, in the cationic sufactant, R⁴ is methylene and t is equal to 1.

33. The composition of claim 32 wherein, in the cationic surfactant, y is from 1 to 10.

34. The composition of claim 33 wherein, in the cationic surfactant, y is from 1 to 10.

35. The composition of claim 34 wherein, in the cationic surfactant, R¹ is CH₃.

36. The composition of claim 35 wherein, in the cationic surfactant, X is selected from the group consisting of chloride, bromide, iodide, methyl sulfate and sulfate.

37. The composition of claim 36 wherein, in the nonionic surfactant, R is an alkyl chain of from about 10 to about 18 carbon atoms.

38. The composition of claim 37 wherein, in the cationic surfactant, y is equal to 7.

39. The composition of claim 38 wherein, in the cationic surfactant, R³ is C₁₂ alkyl.

40. The composition of claim 27 wherein the ratio of nonionic surfactant to cationic surfactant is from about 1:

1 to 5;

1, and the reduced cationic monomer concentration of the nonionic/cationic surfactant mixture is from about 0.005 to about 0.2.

41. The composition of claim 36 wherein the ratio of nonionic surfactant to cationic surfactant is from about 1:

1 to 5;

1, and the reduced cationic monomer concentration of the nonionic/cationic surfactant mixture is from about 0.005 to about 0.2.

42. The composition of claim 40 wherein the ratio of nonionic surfactant to cationic surfactant is from about 5:

3 to 5;

1.

43. The composition of claim 42 which is substantially free of phosphate, polyphosphate, silicate, and polycarboxylate builder anions, carboxymethylcellulose, and anionic surfactants.

44. The composition of claim 40 which is substantially free of oily hydrocarbon materials.

45. The composition of claim 27 wherein the ratio of nonionic surfactant to cationic surfactant is from 5.1:

1 to about 100;

1, the nonionic/cationic surfactant mixture has a cloud point of from about 0°

to about 95°

C., and the reduced cationic monomer concentration of the nonionic/cationic surfactant mixture is from about 0.002 to about 0.2.

46. The composition of claim 36 wherein the ratio of nonionic surfactant to cationic surfactant is from 5.1:

1 to about 100;

1, the nonionic/cationic surfactant mixture has a cloud point of from about 0°

to about 95°

C., and the reduced cationic monomer concentration of the nonionic/cationic surfactant mixture is from about 0.002 to about 0.2.

47. The composition of claim 45 which additionally contains from about 1 to about 60% of a detergency builder salt.

48. The composition of claim 45 wherein said composition forms separated phases when added to water having a temperature of about 45°

C., at a concentration of from about 0.01 to about 0.3%.

49. The composition of claim 45 wherein the ratio of nonionic surfactant to cationic surfactant is from 5.1:

1 to about 50;

1.

50. The composition of claim 26 which has a pH of greater than about 7 in the aqueous laundry solution.