Cationic sugar surfactants

• US 5,773,595 A
• Filed: 10/18/1996
• Issued: 06/30/1998
• Est. Priority Date: 04/20/1994
• Status: Expired due to Term

• Current Assignee: Cognis International GmbH (BASF SE)
• Original Assignee: Henkel KGaA (Henkel AG & Co KGaA)
• Inventors: Hensen, Hermann, Weuthen, Manfred, Kahre, Joerg, Tesmann, Holger
• Primary Examiner(s): Kight, John
• Assistant Examiner(s): White, Everett
• Application Number:
  US08/722,086
• Time in Patent Office: 620 Days
• Field of Search: 536/4.1, 536/123.1, 536/124, 536/17.9, 252/174.17
• US Class Current: 536/17.9
• CPC Class Codes: A61K 8/604 Alkylpolyglycosides; Derivatives thereof, e.g. esters
• CPC Class Codes: A61Q 19/10 Washing or bathing preparations
• CPC Class Codes: A61Q 5/02 Preparations for cleaning the hair
• CPC Class Codes: C07H 15/04 attached to an oxygen atom of the saccharide radical
• CPC Class Codes: C09K 23/56 Glucosides; Mucilage; Saponins
• CPC Class Codes: C11D 1/06 Ether- or thioether carboxylic acids
• CPC Class Codes: C11D 1/10 Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
• CPC Class Codes: C11D 1/123 derived from carboxylic acids, e.g. sulfosuccinates
• CPC Class Codes: C11D 1/126 Acylisethionates
• CPC Class Codes: C11D 1/143 Sulfonic acid esters
• CPC Class Codes: C11D 1/146 Sulfuric acid esters
• CPC Class Codes: C11D 1/16 derived from divalent or polyvalent alcohols
• CPC Class Codes: C11D 1/22 derived from aromatic compounds
• CPC Class Codes: C11D 1/28 Sulfonation products derived from fatty acids or their derivatives, e.g. esters, amides
• CPC Class Codes: C11D 1/345 Phosphates or phosphites
• CPC Class Codes: C11D 1/44 Ethers of polyoxyalkylenes with amino alcohols; Condensation products of epoxyalkanes with amines
• 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 1/525 Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
• CPC Class Codes: C11D 1/526 Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 are polyalkoxylated
• CPC Class Codes: C11D 1/62 Quaternary ammonium compounds
• CPC Class Codes: C11D 1/645 : Mixtures of compounds all of which are cationic
• CPC Class Codes: C11D 1/65 : Mixtures of anionic with cationic compounds
• CPC Class Codes: C11D 1/662 : Carbohydrates or derivatives
• CPC Class Codes: C11D 1/667 : Neutral esters, e.g. sorbitan esters
• CPC Class Codes: C11D 1/72 : Ethers of polyoxyalkylene glycols
• CPC Class Codes: C11D 1/835 : Mixtures of non-ionic with cationic compounds
• CPC Class Codes: C11D 1/90 : Betaines
• CPC Class Codes: C11D 1/92 : Sulfobetaines ; Sulfitobetaines
• CPC Class Codes: C11D 1/94 : Mixtures with anionic, cationic or non-ionic compounds

Abstract

A cationic sugar surfactant made by a process involving: (a) reacting an alkyl or alkenyl oligoglycoside of the formula (I):

R.sup.1 O-- G!.sub.p                                       (I)

wherein R¹ is an alkyl or an alkenyl radical having from 4 to 22 carbon atoms, G is sugar unit having 5 or 6 carbon atoms and p is a number from 1 to 10, with either a chloroacetic acid, chloroacetic anhydride or chloroacetic acid methyl ester; and (b) reacting the product from step (a) with a tertiary amine of the formula (II): ##STR1## wherein each of R² and R³ is an alkyl or alkenyl radical having from 1 to 22 carbon atoms.

Claims

1. A cationic sugar surfactant made by the process which comprises the steps of

(a) reacting an alkyl or alkenyl oligoglycoside of the formula (I):

space="preserve" listing-type="equation">R.sup.1 O-- G!.sub.p (I)

wherein R¹ is an alkyl or an alkenyl radical having from 4 to 22 carbon atoms, G is sugar unit having 5 or 6 carbon atoms and p is a number from 1 to 10 with chloroacetic acid, chloroacetic anhydride or chloroacetic acid methyl ester;

(b) reacting the product from step (a) with a tertiary amine of the formula (II);

##STR14## wherein each of R² and R³ is an alkyl or alkenyl radical having from 1 to 22 carbon atoms.

2. A surface-active composition containing the cationic sugar surfactant of claim 1.

3. A surface active formulation selected from the group consisting of a laundry detergent, a dishwashing detergent, a fabric softener, a sanitary cleaner, a fabric softener, a flotation aid, a shampoo, a hair rinse aid, a hair conditioner, a personal cleanser comprised of from about 1% to about 50% by weight of a cationic sugar surfactant of claim 1.

4. A process for making a cationic sugar reactant made by the process which comprises the steps of:

(a) reacting an alkyl or alkenyl oligoglycoside of the formula (I);

space="preserve" listing-type="equation">R.sup.1 O-- G!.sub.p (I)

wherein R¹ is an alkyl or an alkenyl radical having from 4 to 22 carbon atoms, G is sugar unit having 5 or 6 carbon atoms and p is a number from 1 to 10 with chloroacetic acid, chloroacetic anhydride or chloroacetic acid methyl ester;

(b) reacting the product from step (a) with a tertiary amine of the formula (II);

##STR15##