Preparation of alkylpolyglycosides and cleaning compositions comprising same

• US 5,962,399 A
• Filed: 11/13/1997
• Issued: 10/05/1999
• Est. Priority Date: 10/10/1991
• Status: Expired due to Term

• Current Assignee: Cognis IP Management GmbH (BASF SE)
• Original Assignee: Henkel Corporation (Henkel AG & Co KGaA)
• Inventors: Salka, Barry A., Kozak, William G., Siracusa, Paul A., McCurry, Patrick M. Jr., Urfer, Allen D., Bator, Patricia E., Aleksejczyk, Robert A., Wulff, Harald P., Howell, Gail, Counts, Michael W., McDaniel, Robert S.
• Primary Examiner(s): HERTZOG, ARDITH E
• Application Number:
  US08/969,254
• Time in Patent Office: 691 Days
• Field of Search: 510/470, 510/535, 252/FOR 239, 536/4.1, 536/18.6, 536/120, 536/124, 536/127
• US Class Current: 510/470
• CPC Class Codes: A61K 2800/596 Mixtures of surface active compounds
• CPC Class Codes: A61K 8/604 Alkylpolyglycosides; Derivatives thereof, e.g. esters
• 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: A61Q 5/12 Preparations containing hair conditioners
• CPC Class Codes: C07H 15/04 attached to an oxygen atom of the saccharide radical
• CPC Class Codes: C11D 1/662 Carbohydrates or derivatives

Abstract

A process for preparing high detergency or surfactant alkyl polyglycoside compositions and a purified alkyl monoglycoside and to compositions employing the polyglycosides for various end use applications. The process involves removal of a substantial portion of the monoglycoside present in a reaction product mixture containing alkyl polyglycosides resulting from the reaction of an alcohol and saccharide at elevated temperatures in the presence of an acid catalyst. Separation of the monoglycoside from the reaction product mixture may be carried out by molecular distillation.

Claims

1. A hard surface cleaner containing

(i) an alkylpolyglycoside surfactant composition having an HLB in the range of about 10 to about 16, in which the alkyl group contains from about 6 to about 20 carbon atoms, said alkyl polyglycoside surfactant composition comprising a mixture of:

(a) an alkylpolyglycoside component having a non-Flory distribution of glycosides containing a degree of polymerization of 2 and higher in progressively decreasing amounts, in which the amount by weight of polyglycoside having a degree of polymerization of 2, or mixtures thereof with a polyglycoside having a degree of polymerization of 3, predominate and having an average degree of polymerization of about 1.8 to about 3; and

(b) at least one other glycoside component having an average alkyl chain length less than the average alkyl chain length of component (a); and

wherein the alkylpolyglycoside component (a) is an at least binary component and the glycoside component (b) is an alkylpolyglycoside at least binary component and each of the binary components (a) and (b) is present in the mixture in relation to the average carbon chain length in an amount to provide the alkylpolyglycoside surfactant composition with an average carbon chain length of about 9 to about 14 and an HLB in the range of about 10 to about 16; and

(ii) at least one hard surface cleaner adjuvant selected from the group consisting of a co-surfactant;

a conditioning agent;

a hydrotrope;

a solvent;

a filler;

a coloring agent;

a dye;

a brightening agent;

a fragrance;

a preservative;

a consistency regulator;

a polishing agent; and

a humectant.

2. A hard surface cleaner as defined in claim 1 in which the average chain length of the alkylpolyglycoside surfactant composition is above 9 and below about 12 and component (a) is a mixture of a C₁₂ alkylpolyglycoside, a C₁₄ alkylpolyglycoside, and a C₁₆ alkylpolyglycoside;

and component (b) is a binary mixture of a C₈ alkylpolyglycoside and a C₁₀ alkylpolyglycoside in which the ratio by weight of the C₈ and C₁₀ alkylpolyglycoside component (b) to the mixture of the C₁₂, C₁₄, and C₁₆ alkylpolyglycoside component (a) is about 1;

1 to about 10;

1.

3. A hard surface cleaner as defined in claim 2 in which the ratio by weight of the mixture of C₈ and C₁₀ alkylpolyglycosides to the mixture of C₁₂, C₁₄ and C₁₆ alkylpolyglycosides is above 1.25:

1 to about 4;

1.

4. A hard surface cleaner as defined in claim 3 in which said ratio is about 2:

1.

5. A hard surface cleaner as defined in claim 1 and further comprising an anionic surfactant.

6. A soil cleaning composition containing

(i) an alkylpolyglycoside surfactant composition having an HLB in the range of about 10 to about 16, in which the alkyl group contains from about 6 to about 20 carbon atoms, said alkyl polyglycoside surfactant composition comprising a mixture of:

(a) an alkylpolyglycoside component having a non-Flory distribution of glycosides containing a degree of polymerization of 2 and higher in progressively decreasing amounts, in which the amount by weight of polyglycoside having a degree of polymerization of 2, or mixtures thereof with a polyglycoside having a degree of polymerization of 3, predominate and having an average degree of polymerization of about 1.8 to about 3, and

(b) at least one other glycoside component having an average alkyl chain length less than the average alkyl chain length of component (a); and

wherein the alkylpolyglycoside component (a) is an at least binary component and the glycoside component (b) is an alkylpolyglycoside at least binary component and each of the binary components (a) and (b) is present in the mixture in relation to the average carbon chain length in an amount to provide the alkylpolyglycoside surfactant composition with an average carbon chain length of about 9 to about 14 and an HLB in the range of about 10 to about 16; and

(ii) at least one soil cleaning adjuvant selected from the group consisting of a co-surfactant;

a conditioning agent;

a hydrotrope;

a solvent;

a filler;

a coloring agent;

a dye;

a brightening agent;

a fragrance;

a preservative;

a consistency regulator;

a polishing agent; and

a humectant.

7. A soil cleaning composition as defined in claim 6 in which the average chain length of the alkylpolyglycoside surfactant composition is above 9 and below about 12 and component (a) is a mixture of a C₁₂ alkylpolyglycoside, a C₁₄ alkylpolyglycoside, and a C₁₆ alkylpolyglycoside;

and component (b) is a binary mixture of a C₈ alkylpolyglycoside and a C₁₀ alkylpolyglycoside in which the ratio by weight of the C₈ and C₁₀ alkylpolyglycoside component (b) to the C₁₂, C₁₄, and C₁₆ alkylpolyglycoside component (a) is about 1;

1 to about 10;

1.

8. A soil cleaning composition as defined in claim 7 in which the ratio by weight of the mixture of C₈ and C₁₀ alkylpolyglycosides to the mixture of C₁₂, C₁₄ and C₁₆ alkylpolyglycosides is about 2:

1 to about 3;

1.

9. A laundry detergent containing an alkylpolyglycoside surfactant composition having an HLB in the range of about 10 to about 16, in which the alkyl group contains from about 6 to about 20 carbon atoms, said alkyl polyglycoside surfactant composition comprising a mixture of:

(a) an alkylpolyglycoside component having a non-Flory distribution of glycosides containing a degree of polymerization of 2 and higher in progressively decreasing amounts, in which the amount by weight of polyglycoside having a degree of polymerization of 2, or mixtures thereof with a polyglycoside having a degree of polymerization of 3, predominate and having an average degree of polymerization of about 1.8 to about 3; and

(b) at least one other glycoside component having an average alkyl chain length less than the average alkyl chain length of component (a); and

wherein the alkylpolyglycoside component (a) is an at least binary component and the glycoside component (b) is an alkylpolyglycoside at least binary component and each of the binary components (a) and (b) is present in the mixture in relation to the average carbon chain length in an amount to provide the alkylpolyglycoside surfactant composition with an average carbon chain length of about 9 to about 14 and an HLB in the range of about 10 to about 16; and

(ii) at least one laundry detergent adjuvant selected from the group consisting of a co-surfactant;

a conditioning agent;

a hydrotrope;

a solvent;

a filler;

a coloring agent;

a dye;

a brightening agent;

a fragrance;

a preservative;

a consistency regulator;

a polishing agent; and

a humectant.

10. A laundry detergent composition as defined in claim 9 in which the average chain length of the alkylpolyglycoside surfactant composition is above 9 and below about 12 and component (a) is a mixture of a C₁₂ alkylpolyglycoside, a C₁₄ alkylpolyglycoside, and a C₁₆ alkylpolyglycoside;

and component (b) is a binary mixture of a C₈ alkylpolyglycoside and a C₁₀ alkylpolyglycoside in which the ratio by weight of the C₈ and C₁₀ alkylpolyglycoside component (b) to the mixture of the C₁₂, C₁₄, and C₁₆ alkylpolyglycoside component (a) is about 1;

1 to about 10;

1.

11. A laundry detergent composition as defined in claim 10 in which the ratio of component (b) to component (a) is above 1.25:

1 to about 4;

1.

12. A laundry detergent composition as defined in claim 11 in which the ratio of component (b) to (a) is about 2:

1 to about 3;

1.

13. A method of preparing a cleaning composition comprising adding to said cleaning composition a surfactant effective amount of an alkylpolyglycoside surfactant having an HLB in the range of about 10 to about 16, in which the alkyl group contains from about 6 to about 20 carbon atoms, said alkyl polyglycoside surfactant composition comprising a mixture of:

(a) an alkylpolyglycoside component having a non-Flory distribution of glycosides containing a degree of polymerization of 2 and higher in progressively decreasing amounts, in which the amount by weight of polyglycoside having a degree of polymerization of 2, or mixtures thereof with a polyglycoside having a degree of polymerization of 3, predominate and having an average degree of polymerization of about 1.8 to about 3; and

(b) at least one other glycoside component having an average alkyl chain length less than the average alkyl chain length of component (a); and

wherein the alkylpolyglycoside component (a) is an at least binary component and the glycoside component (b) is an alkylpolyglycoside at least binary component and each of the binary components (a) and (b) is present in the mixture in relation to the average carbon chain length in an amount to provide the alkylpolyglycoside surfactant composition with an average carbon chain length of about 9 to about 14 and an HLB in the range of about 10 to about 16.

14. A method as defined in claim 13 wherein said cleaning composition is a hard surface cleaner or a laundry detergent composition.

15. An alkyl polyglycoside composition having an HLB in the range of about 10 to about 16, in which the alkyl group contains from about 6 to about 20 carbon atoms, said alkyl polyglycoside surfactant composition comprising a mixture of:

(a) an alkylpolyglycoside component having a non-Flory distribution of glycosides containing a degree of polymerization of 2 and higher in progressively decreasing amounts, in which the amount by weight of polyglycoside having a degree of polymerization of 2, or mixtures thereof with a polyglycoside having a degree of polymerization of 3, predominate and having an average degree of polymerization of about 1.8 to about 3; and

(b) at least one other glycoside component having an average alkyl chain length less than the average alkyl chain length of component (a); and

wherein the alkylpolyglycoside component (a) is an at least binary component and the glycoside component (b) is an at least binary monoglycoside component.

16. An alkylpolyglycoside composition as defined in claim 15 wherein the alkylpolyglycoside component (a) is a mixture of a C₁₂ alkylpolyglycoside, a C₁₄ alkylpolyglycoside and a C₁₆ alkylpolyglycoside.

17. An alkylpolyglycoside composition as defined in claim 16 in which component (b) is a binary mixture of a C₈ and C₁₀ monoglycoside.

18. An alkylpolyglycoside composition as defined in claim 17 in which the ratio by weight of (b) to (a) is about 1:

1 to about 4;

1.

19. A method of preparing an improved alkylpolyglycoside surfactant composition in which the alkyl groups contain from about 6 to about 20 carbon atoms comprising selecting a predetermined average carbon chain length of the alkyl moiety for the composition and mixing two or more of at least binary components of alkylpolyglycosides, each binary component having an average alkyl chain length such that when mixed, the amounts of the binary components mixed are effective to provide the predetermined selected average alkyl moiety and the surfactant properties and wherein at least one, or both binary components, comprise a non-Flory distribution of polyglycosides derived from an acid-catalyzed reaction of an alcohol containing 6-20 carbon atoms and a suitable saccharide from which excess alcohol has been separated.

20. A method as defined in claim 19, in which the predetermined average alkyl moiety chain length is above about 9 and one of the binary components has an average alkyl chain length less than the predetermined selected average alkyl moiety and another binary component has an average alkyl having alkyl chain length higher than the predetermined selected alkyl moiety.

21. A method as defined in claim 20 in which said binary component of alkylpolyglycosides having an average alkyl chain length higher than the predetermined selected alkyl moiety is a mixture of a C₁₂ alkylpolyglycoside, a C₁₄ alkylpolyglycoside and a C₁₆ alkylpolyglycoside.

22. A method as defined in claim 21 in which said binary component of alkylpolyglycosides having an average alkyl chain length less than the predetermined selected alkyl moiety is a mixture of a C₈ alkylpolyglycoside and a C₁₀ alkylpolyglycoside.

23. A method as defined in claim 22 in which the ratio by weight of the binary component of the C₈ and C₁₀ alkylpolyglycosides mixture to the binary component of the C₁₂, C₁₄ and C₁₆ alkylpolyglycosides mixture is about 1:

1 to about 10;

1.

24. A method as defined in claim 23 in which said ratio is above about 1:

1 to about 4;

1.

25. A method as defined in claim 23 in which said ratio is from about 1.5:

1 to about 4;

1.

26. A method as defined in claim 23 in which said ratio is about 1.7:

1 to about 2;

1.

27. A method as defined in claim 23 in which the average alkyl chain length is about 10.3 and the HLB of the composition is about 13.

28. A method as defined in claim 20, wherein said predetermined average alkyl moiety chain length is about 10.

29. A method as defined in claim 20, in which said binary component of alkylpolyglycoside having an average alkyl chain length less than the predetermined selected average alkyl moiety is a mixture of a C₈ alkylpolyglycoside and a C₁₀ alkylpolyglycoside.

30. A method as defined in claim 19, wherein the average chain length of the alkyl chain in the product resulting from the mixture of the binary components is in the range of about 9 to about 14.

31. A method as defined in claim 30, in which said average chain length is about 9 to about 12.

32. A method as defined in claim 31 in which said improved alkylpolyglycoside surfactant composition has an HLB in the range of about 10 to about 16.

33. A method as defined in claim 32, in which said improved alkylpolyglycoside surfactant composition has an HLB of about 11 to about 14.