Mid-chain branched alkyl sulfate surfactants

• US 6,060,443 A
• Filed: 10/13/1998
• Issued: 05/09/2000
• Est. Priority Date: 04/16/1996
• Status: Expired due to Term

• Current Assignee: The Procter & Gamble Company
• Original Assignee: The Procter & Gamble Company
• Inventors: Vinson, Phillip Kyle, Burckett-St. Laurent, James Charles Theophile Roger, Dupont, Jeffrey Scott, Connor, Daniel Stedman, Cripe, Thomas Anthony, Willman, Kenneth William
• Primary Examiner(s): OGDEN JR, NECHOLUS
• Application Number:
  US09/170,511
• Time in Patent Office: 574 Days
• Field of Search: 510/424, 510/426, 510/428, 510/506, 568/458, 568/882, 560/76
• US Class Current: 510/426
• CPC Class Codes: A61K 2800/596 Mixtures of surface active compounds
• CPC Class Codes: A61K 8/463 containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
• CPC Class Codes: A61Q 11/00 Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
• 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 305/06 Hydrogenosulfates
• CPC Class Codes: C07C 305/10 being further substituted by singly-bound oxygen atoms
• CPC Class Codes: C11D 1/123 derived from carboxylic acids, e.g. sulfosuccinates
• CPC Class Codes: C11D 1/126 Acylisethionates
• CPC Class Codes: C11D 1/146 Sulfuric acid esters
• CPC Class Codes: C11D 1/29 Sulfates of polyoxyalkylene ethers
• CPC Class Codes: C11D 1/521 Carboxylic amides (R1-CO-NR2R3), where R1, R2 and R3 are alkyl or alkenyl groups
• CPC Class Codes: C11D 1/62 Quaternary ammonium compounds
• CPC Class Codes: C11D 1/65 Mixtures of anionic with cationic compounds
• CPC Class Codes: C11D 1/72 Ethers of polyoxyalkylene glycols
• CPC Class Codes: C11D 3/08 Silicates
• CPC Class Codes: C11D 3/128 Aluminium silicates, e.g. zeolites C11D3/1253 takes precedence
• CPC Class Codes: C11D 3/18 Hydrocarbons C11D3/164 takes precedence

Abstract

Mixtures of mid-chain branched primary alkyl sulfate surfactants useful in cleaning compositions, especially for lower water temperature applications, alone or formulated with other surfactants for the purpose of modifying the low temperature cleaning properties of the cleaning formulations. The present invention also relates to novel mid-chain branched primary alkyl sulfate surfactants suitable for use in surfactant mixtures.

Claims

1. A surfactant composition comprising from about 0.001% to about 100% of a mixture of two or more mid-chain branched primary alkyl sulfates having the formula:

##STR39## wherein the total number of carbon atoms in the branched primary alkyl moiety of this formula, including the R, R¹, and R² branching, is from 14 to 20, and wherein further for this surfactant mixture the average total number of carbon atoms in the branched primary alkyl moieties having the above formula is within the range of greater than 14.5 to about 17.5, R, R¹, and R² are each independently selected from hydrogen and C₁ -C₃ alkyl, provided R, R¹, and R² are not all hydrogen and, when z is 1, at least R or R¹ is not hydrogen;

M is one or more cations;

w is an integer from 0 to 13;

x is an integer from 0 to 13;

y is an integer from 0 to 13;

z is an integer of at least 1; and

w+x+y+z is from 8 to 14.

2. A composition according to claim 1 wherein at least 0.001%, of the mixture comprises one or more mid-chain branched primary alkyl sulfates having the formula ##STR40## wherein the total number of carbon atoms, including branching, is from 15 to 18, and wherein further for this surfactant mixture the average total number of carbon atoms in the branched primary alkyl moieties having the above formula is within the range of greater than 14.5 to about 17.5;

R¹ and R² are each independently hydrogen or C₁ -C₃ alkyl;

M is a water soluble cation;

x is from 0 to 11;

y is from 0 to 11;

z is at least 2; and

x+y+z is from 9 to 13;

provided R¹ and R² are not both hydrogen.

3. A composition according to claim 1 wherein M is selected from the group consisting of sodium, potassium, calcium, magnesium, quaternary alkyl amines having the formula ##STR41## wherein R³, R⁴, R⁵ and R⁶ are independently selected from hydrogen, C₁ -C₂₂ alkylene, C₄ -C₂₂ branched alkylene, C₁ -C₆ alkanol, C₁ -C₂₂ alkenylene, C₄ -C₂₂ branched alkenylene, and mixtures thereof.

4. A composition according to claim 1 wherein M is sodium, potassium, and mixtures thereof.

5. A composition according to claim 1 wherein at least 5%, preferably at least about 20%, of the mixture comprises one or more mid-chain branched primary alkyl sulfates wherein x+y is equal to 9 and z is equal to 2.

6. A composition according to claim 1 wherein at least 5%, preferably at least about 20%, of the mixture comprises mid-chain branched primary alkyl sulfates wherein x+y is equal to 9 and z is equal to 2.

7. A composition according to claim 1 wherein at least 5%, preferably at least about 20%, of the mixture comprises mid-chain branched primary alkyl sulfates wherein x+y is equal to 10 and z is equal to 2.

8. A surfactant composition comprising a mixture of branched primary alkyl sulfates having the formula ##STR42## wherein the total number of carbon atoms per molecule, including branching, is from 14 to 20, and wherein further for this surfactant mixture the average total number of carbon atoms in the branched primary alkyl moieties having the above formula is within the range of greater than 14.5 to about 17.5;

R, R¹, and R² are each independently selected from hydrogen and C₁ -C₃ alkyl, provided R, R¹, and R² are not all hydrogen;

M is a water soluble cation;

w is an integer from 0 to 13;

x is an integer from 0 to 13;

y is an integer from 0 to 13;

z is an integer of at least 1; and

w+x+y+z is from 8 to 14;

provided that when R² is a C₁ -C₃ alkyl the ratio of surfactants having z equal to 1 to surfactants having z of 2 or greater is at least about 1;

1.

9. A surfactant composition according to claim 8 wherein the amount of branched surfactants, when R² is a C₁ -C₃ alkyl, comprises less than about 20%, of branched primary alkyl sulfates having the above formula wherein z equals 1.

10. A detergent composition comprising:

(a) from about 0.001% to about 99% of a mixture of mid-chain branched primary alkyl sulfate surfactants, said mixture comprising at least about 5% by weight of two or more mid-chain branched alkyl sulfates having the formula;

##STR43## or mixtures thereof;

wherein M represents one or more cations;

a, b, d, and e are integers, a+b is from 10 to 16, d+e is from 8 to 14 and wherein further

when a+b=10, a is an integer from 2 to 9 and b is an integer from 1 to 8;

when a+b=11, a is an integer from 2 to 10 and b is an integer from 1 to 9;

when a+b=12, a is an integer from 2 to 11 and b is an integer from 1 to 10;

when a+b=13, a is an integer from 2 to 12 and b is an integer from 1 to 11;

when a+b=14, a is an integer from 2 to 13 and b is an integer from 1 to 12;

when a+b=15, a is an integer from 2 to 14 and b is an integer from 1 to 13;

when a+b=16, a is an integer from 2 to 15 and b is an integer from 1 to 14;

when d+e=8, d is an integer from 2 to 7 and e is an integer from 1 to 6;

when d+e=9, d is an integer from 2 to 8 and e is an integer from 1 to 7;

when d+e=10, d is an integer from 2 to 9 and e is an integer from 1 to 8;

when d+e=11, d is an integer from 2 to 10 and e is an integer from 1 to 9;

when d+e=12, d is an integer from 2 to 11 and e is an integer from 1 to 10;

when d+e=13, d is an integer from 2 to 12 and e is an integer from 1 to 11;

when d+e=14, d is an integer from 2 to 13 and e is an integer from 1 to 12;

wherein for this surfactant mixture the average total number of carbon atoms in the branched primary alkyl moieties having the above formulas is within the range of greater than 14.5 to about 17.5; and

(b) from about 1% to about 99.999% of detergent composition adjuct ingredients.

11. A mid-chain branched primary alkyl sulfate having the formula ##STR44## wherein R¹ and R² are each independently hydrogen or C₁ -C₃ alkyl;

M is a water soluble cation;

x is an integer from 0 to 12;

y is an integer from 0 to 12;

z is an integer of at least 2; and

x+y+z is from 11 to 14;

provided;

a) R¹ and R² are not both hydrogen;

b) when one R¹ or R² is hydrogen and the other R¹ or R² is methyl, then x+y+z is not 12 or 13; and

c) when R¹ is hydrogen and R² is methyl, x+y is not 11 when z is 3, and x+y is not 9 when z is 5.

12. A compound according to claim 11 wherein M is selected from the group consisting of sodium, potassium, calcium, magnesium, quaternary alkyl amines having the formula ##STR45## wherein R³, R⁴, R⁵ and R⁶ are independently selected from hydrogen, C₁ -C₂₂ alkylene, C₄ -C₂₂ branched alkylene, C₁ -C₆ alkanol, C₁ -C₂₂ alkenylene, C₄ -C₂₂ branched alkenylene, and mixtures thereof.

13. A compound according to claim 11 wherein M is sodium, potassium, and mixtures thereof.

14. A compound according to claim 11 wherein R is methyl, R¹ is hydrogen, x is from 0 to 10, y is from 0 to 10, z is 2, x+y+z is equal to 11.

15. Alkyl sulfate compounds of formula:

##STR46## wherein;

a and b are integers and a+b is 12 or 13, a is an integer from 2 to 11, b is an integer from 1 to 10 and M is selected from sodium, potassium, ammonium and substituted ammonium.

16. Alkyl sulfate compounds of formula:

##STR47## wherein;

d and e are integers and d+e is from 10 or 11; and

wherein further

when d+e=10, d is an integer from 2 to 9 and e is an integer from 1 to 8;

when d+e=11, d is an integer from 2 to 10 and e is an integer from 1 to 9;

and M is selected from sodium, potassium, ammonium and substituted ammonium.

17. Mono-methyl branched primary alkyl sulfates selected from the group consisting of:

3-methyl pentadecanol sulfate, 4-methyl pentadecanol sulfate, 5-methyl pentadecanol sulfate, 6-methyl pentadecanol sulfate, 7-methyl pentadecanol sulfate, 8-methyl pentadecanol sulfate, 9-methyl pentadecanol sulfate, 10-methyl pentadecanol sulfate, 11-methyl pentadecanol sulfate, 12-methyl pentadecanol sulfate, 13-methyl pentadecanol sulfate, 3-methyl hexadecanol sulfate, 4-methyl hexadecanol sulfate, 5-methyl hexadecanol sulfate, 6-methyl hexadecanol sulfate, 7-methyl hexadecanol sulfate, 8-methyl hexadecanol sulfate, 9-methyl hexadecanol sulfate, 10-methyl hexadecanol sulfate, 11-methyl hexadecanol sulfate, 12-methyl hexadecanol sulfate, 13-methyl hexadecanol sulfate, 14-methyl hexadecanol sulfate, and mixtures thereof.

18. Di-methyl branched primary alkyl sulfates selected from the group consisting of:

2,3-methyl tetradecanol sulfate, 2,4-methyl tetradecanol sulfate, 2,5-methyl tetradecanol sulfate, 2,6-methyl tetradecanol sulfate, 2,7-methyl tetradecanol sulfate, 2,8-methyl tetradecanol sulfate, 2,9-methyl tetradecanol sulfate, 2,10-methyl tetradecanol sulfate, 2,11-methyl tetradecanol sulfate, 2,12-methyl tetradecanol sulfate, 2,3-methyl pentadecanol sulfate, 2,4-methyl pentadecanol sulfate, 2,5-methyl pentadecanol sulfate, 2,6-methyl pentadecanol sulfate, 2,7-methyl pentadecanol sulfate, 2,8-methyl pentadecanol sulfate, 2,9-methyl pentadecanol sulfate, 2,10-methyl pentadecanol sulfate, 2,11-methyl pentadecanol sulfate, 2,12-methyl pentadecanol sulfate, 2,13-methyl pentadecanol sulfate, and mixtures thereof.