Sulfated hydroxy mixed ethers, a process for their production, and their use

• US 4,931,218 A
• Filed: 07/13/1988
• Issued: 06/05/1990
• Est. Priority Date: 07/15/1987
• Status: Expired due to Fees

• Current Assignee: Henkel KGaA (Henkel AG & Co KGaA)
• Original Assignee: Henkel KGaA (Henkel AG & Co KGaA)
• Inventors: Piorr, Robert, Luettge, Sabine, Schenker, Gilbert
• Primary Examiner(s): Lieberman, Paul
• Assistant Examiner(s): NOT, DEFINED
• Application Number:
  US07/218,719
• Time in Patent Office: 692 Days
• Field of Search: 252/531, 252/532, 252/550, 252/551, 558/34
• US Class Current: 510/498
• CPC Class Codes: A61K 8/463 containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
• CPC Class Codes: A61Q 19/10 Washing or bathing preparations
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: C07C 303/24 of esters of sulfuric acids
• CPC Class Codes: C07C 305/10 being further substituted by singly-bound oxygen atoms
• CPC Class Codes: C11D 1/14 derived from aliphatic hydrocarbons or mono-alcohols
• CPC Class Codes: C11D 1/29 Sulfates of polyoxyalkylene ethers
• CPC Class Codes: C11D 1/37 Mixtures of compounds all of which are anionic

Abstract

Sulfated hydroxyalkyl polyethylene glycol and hydroxyalkyl polypropylene glycol ethers corresponding to general formula (II) ##STR1## in which R¹ is hydrogen or a linear C₁ -C₁₆ alkyl radical,

R² is a linear or branched, saturated C₁ -C₂₂ alkyl radical,

R₃ is hydrogen or a linear C₁ -C₁₆ alkyl radical,

R⁴ is hydrogen or a methyl group,

M represents hydrogen, ammonium, alkylammonium, alkanolammonium, in which the alkyl and alkanol radicals each contain from 1 to 4 carbon atoms, or a monovalent metal atom, and

n is a number of 1 to 30,

with the proviso that the total number of carbon atoms in R¹ and R₃ is between 6 and 16,

and mixtures of such compounds; a process for the preparation of the compounds of formula (II) from the corresponding hydroxyalkyl polyethylene glycol and hydroxyalkyl polypropylene glycol ethers by reaction with gaseous sulfur trioxide or chlorosulfonic acid at an elevated temperature; and the use of the sulfated compounds or mixture thereof as wetting agents and raw materials for detergents and cleaning preparations, especially cosmetic compositions.

Claims

1. A sulfated hydroxyalkyl polyethylene glycol or hydroxyalkyl polypropylene glycol ether of the formula ##STR9## in which R¹ is hydrogen or a linear C₁ -C₁₆ alkyl radical,

R² is a linear or branched, saturated C₁ -C₂₂ alkyl radical,

R³ is hydrogen or a linear C₁ -C₁₆ alkyl radical,

R₄ is hydrogen or a methyl group,

M represents hydrogen, ammonium, alkylammonium, alkanolammonium, in which the alkyl and alkanol radicals each contain from 1 to 4 carbon atoms, or a monovalent metal atom, and

n is a number of from 1 to 30.

with the proviso that the total number of carbon atoms in R¹ and R³ is between 6 and 16,

and mixtures of such compounds.

2. The compound of claim 1 in which R¹ is a linear C₈ -C₁₂ alkyl radical and R³ is hydrogen.

3. The compound of claim 1 in which R² is a linear, saturated C₁ -C₁₂ alkyl radical.

4. The compound of claim 2 in which R² is a linear, saturated C₁ -C₁₂ alkyl radical.

5. The compound of claim 3 in which R² is a C₁ -C₁₂ alkyl radical.

6. The compound of claim 4 in which R² is a C₁ -C₁₂ alkyl radical.

7. The compound of claim 1 in which R³ and R⁴ are hydrogen.

8. The compound of claim 4 in which R³ and R⁴ are hydrogen.

9. The compound of claim 6 in which R³ and R⁴ are hydrogen.

10. The compound of claim 1 in which M is an alkali metal ion, an ammonium group, a C₁ -C₂ mono-, di-, or tri-alkylammonium group, or a C₂ -C₃ mono-, di-, or tri-alkanolammonium group.

11. The compound of claim 4 in which M is an alkali metal ion, an ammonium group, a C₁ -C₂ mono-, di-, or tri-alkylammonium group, or a C₂ -C₃ mono-, di-, or tri-alkanolammonium group.

12. The compound of claim 8 in which M is an alkali metal ion, an ammonium group, a C₁ -C₂ mono-, di-, or tri-alkylammonium group, or a C₂ -C₃ mono-, di-, or tri-alkanolammonium group.

13. The compound of claim 10 in which M is the sodium or potassium ion.

14. The compound of claim 11 in which M is the sodium or potassium ion.

15. The compound of claim 12 in which M is the sodium or potassium ion.

16. The compound of claim 1 in which n is a number of from 1 to 12.

17. The compound of claim 14 in which n is a number of from 1 to 12.

37. In a detergent or cleaning composition, the improvement comprising the presence therein of a wetting-effective quantity of the compound of claim 1.

38. In a cosmetic washing or cleaning composition, the improvement comprising the presence therein of a wetting-effective quantity of the compound of claim 1.

39. In a cosmetic washing or cleaning composition, the improvement comprising the presence therein of a wetting-effective quantity of a mixture of

(a) a compound of claim 1, and

(b) a fatty alcohol (polyglycol ether) sulfate of formula (V)

18. A process for the preparation of a sulfated hydroxyalkyl polyethylene glycol or hydroxyalkyl polypropylene glycol ether of the formula ##STR10## in which R¹ is hydrogen or a linear C₁ -C₁₆ alkyl radical,

R² is a linear or branched, saturated C₁ -C₂₂ alkyl radical,

R³ is a hydrogen or a linear C₁ -C₁₆ alkyl radical,

R⁴ is hydrogen or a methyl group,

M represents hydrogen, ammonium, alkylammonium, alkanolammonium, in which the alkyl and alkanol radicals each contain from 1 to 4 carbon atoms, or a monovalent metal atom, and

n is a number of from 0 to 12,

with the proviso that the total number of carbon atoms in R¹ and R³ is between 6 and 16,

and mixtures of such compounds, comprising the steps of

A. reacting an epoxide or mixture of epoxides of the formula ##STR11## in which R¹ and R³ are as defined above,

with an alcohol or alcohol alkoxylate, or mixtures thereof, of the formula ##STR12## in which R², R⁴, and n are as defined above,

at an elevated temperature in the presence of a catalyst to form a hydroxyalkyl polyethylene glycol or a hydroxyalkyl polypropylene glycol ether, or mixtures thereof, of the formula ##STR13## in which R¹, R²,R³, R⁴, and n are as defined above,

B. reacting the compound (I) or mixtures thereof with a sulfating agent to form a crude sulfonation product.

C. contacting the crude sulfonation product with an aqueous, basic solution, and maintaining the resulting mixture at an elevated temperature,

D. adjusting the mixture to a pH value in the nuetral or mildly alkaline range, and

E. isolating the compound or mixture of compounds of formula (II) from the reaction mixture.

19. The process of claim 18 wherein in step A in the epoxide of formula III R¹ is a linear C₈ -C₁₂ alkyl radical and R³ is hydrogen.

20. The process of claim 18 wherein in step A in the alcohol or alcohol alkoxylate of formula IV R² is a linear, saturated C₁ -C₂₂ alkyl radical.

21. The process of claim 19 wherein in step A in the alcohol or alcohol alkoxylate of formula IV R² is a linear, saturated C₁ -C₂₂ alkyl radical.

22. The process of claim 18 wherein the step A in the compounds of formula IV R² is a linear C₁ -C₁₂ alkyl radical, R⁴ is hydrogen, and n is a number of from 1 to 12.

23. The process of claim 18 wherein in step A the molar ratio of the compounds of formula III to the compounds of formula IV is about 1:

1.

24. The process of claim 18 wherein in step A the elevated temperature is in the range of from about 100°

to about 180°

C.

25. The process of claim 24 wherein the elevated temperature is in the range of from about 120°

to about 160°

C.

26. The process of claim 18 wherein in step A the catalyst is an alkali metal alcoholate, sulfuric acid, or boron trifluoride etherate, and is used in an amount of from about 0.01 to about 2.0% by weight, based on the total weight of the reaction mixture.

27. The process of claim 26 wherein the catalyst is sodium methylate.

28. The process of claim 18 wherein in step B the sulfating agent is gaseous sulfur trioxide or chlorosulfonic acid.

29. The process of claim 28 wherein the sulfating agent is gaseous sulfur trioxide diluted with air or nitrogen.

30. The process of claim 29 wherein from about 1 to about 10% by volume sulfur trioxide is present in the air or nitrogen.

31. The process of claim 18 wherein in step B the sulfating reaction is carried out at a temperature in the range of from about 10°

to about 40°

C.

32. The process of claim 19 wherein in step C the aqueous basic solution is a solution of an alkali metal hydroxide, ammonia, a C₁ -C₂ mono-, di-, or tri-alkylamine, or a C₂ -C₃ mono-, di-, or tri-alkanolamine.

33. The process of claim 32 wherein the basic solution is a solution of sodium hydroxide.

34. The process of claim 33 wherein from about 1.0 to about 1.3 mol sodium hydroxide is present per mol of added sulfur trioxide.

35. The process of claim 32 wherein in step C the elevated temperature is in the range of from about 60°

to about 100°

C.

36. The process of claim 18 wherein in step D the pH adjustment is made with a dilute mineral acid.