Fatty acid derivatives and their use as surfactants in detergents and cleaners

• US 6,057,283 A
• Filed: 07/06/1999
• Issued: 05/02/2000
• Est. Priority Date: 10/27/1995
• Status: Expired due to Fees

• Current Assignee: BASF AG (BASF SE)
• Original Assignee: BASF AG (BASF SE)
• Inventors: Oetter, Gunter, Oftring, Alfred, Baur, Richard, Ott, Christian, aus dem Kahmen, Martin
• Primary Examiner(s): Kopec, Mark
• Assistant Examiner(s): Hardee, John R.
• Application Number:
  US09/348,673
• Time in Patent Office: 301 Days
• Field of Search: 554/36, 510/502, 510/494
• US Class Current: 510/502
• CPC Class Codes: C07C 229/16 to carbon atoms of hydrocarbon radicals substituted by amino or carboxyl groups, e.g. ethylenediamine-tetra-acetic acid, iminodiacetic acids
• CPC Class Codes: C07C 229/22 the carbon skeleton being further substituted by oxygen atoms
• CPC Class Codes: C07C 229/26 having more than one amino group bound to the carbon skeleton, e.g. lysine
• CPC Class Codes: C07C 237/06 having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
• CPC Class Codes: C07C 237/08 having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
• CPC Class Codes: C07C 237/10 having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms not being part of nitro or nitroso groups
• CPC Class Codes: C07C 237/22 having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated peptides C07K
• CPC Class Codes: C11D 1/10 Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof
• CPC Class Codes: C11D 1/46 Esters of carboxylic acids with amino alcohols; Esters of amino carboxylic acids with alcohols
• CPC Class Codes: C11D 1/523 Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
• 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 1/528 Carboxylic amides (R1-CO-NR2R3), where at least one of the chains R1, R2 or R3 is interrupted by a functional group, e.g. a -NH-, -NR-, -CO-, or -CON- group ethers C11D1/526

Abstract

Fatty acid derivatives based on epoxidized unsaturated fatty acid esters or triglycerides and reacted with amines such as hydroxy- and/or amino-substituted hydrophilic amines or amino acids and/or with alkanols or with water on the epoxy group and/or the carboxylic ester groups are described. These fatty amides are suitable as surfactants in detergents and cleaners.

Claims

1. A fatty amide derivative of the formula XV:

##STR29## wherein A⁴ is an aliphatic C₈ -C₂₄ radical having an unbranched carbon chain which contains one or more groups of the formula XVI;

##STR30## R¹² is a hydroxyl- and/or amino-substituted hydrophilic radical having 2 to 40 carbon atoms;

R¹³ is hydrogen, an unsubstituted C₁ -C₆ -alkyl radical or a radical R¹²,

R¹⁴ is a C₁ -C₁₄ -alkyl radical which has carboxyl and/or sulfo groups in the form of the free acids and/or their alkali metal or ammonium salts and which may be interrupted by nonadjacent oxygen atoms, --NH groups and/or N-C₁ -C₄ -alkyl groups,

R¹⁵ is a hydrogen, an unsubstituted C₁ -C₆ -alkyl radical or a radical R¹⁴, wherein the meaning of the two pairs of substituents R¹² /R¹³ and R¹⁴ /R¹⁵ may also be interchanged.

2. The fatty amide derivative of claim 1, wherein

^A is derived from an unsaturated C₁₈ -fatty acid.

3. The fatty amide derivative of claim 1, wherein R¹² is an unbranched ω

-aminoalkyl group having, in each case, 2 to 6 carbon atoms, it being possible for the alkyl group to be interrupted by nonadjacent oxygen atoms, NH groups, N-C₁ -C₄ -alkyl groups, N-C₁ -C₄ -hydroxyalkyl groups or N-C₁ -C₄ -aminoalkyl groups.

4. The fatty amide derivative of claim 1, wherein the group ##STR31## is the radical of an amino acid.

5. A process for preparing the fatty amide derivative of claim 1, comprising reacting an epoxidized fatty amide having formula XVII:

##STR32## wherein B³ is an aliphatic C₈ -C₂₄ radical having an unbranched carbon chain which contains one or more epoxy groups, and R¹² and R¹³ are as defined as in claim 1,

with at least one equivalent of an amine having the formula HN(R¹⁴)R¹⁵ per epoxy unit, wherein R¹⁴ and R¹⁵ are as defined in claim 1.

6. A method of cleaning an article, comprising contacting the article with the fatty amide derivative of claim 1.

7. A detergent or cleaner composition comprising the fatty amide derivative of claim 1, and other additives conventional in a detergent or cleaner composition.