DE4238210C1 - Fatty acid bis:sorbityl amide(s) and their prepn. - useful for the prepn. of washing, rinsing or cleaning agents and hair or body care prods. - Google Patents

Abstract

Fatty acid bissorbitylamides of formula (I) are claimed, where R1CO = aliphatic 6-22C acyl; and Z = sorbityl gp. Also claimed is the prepn. of (I) by reacting fatty acids (lower alkyl esters) of formula (II) with bissorbitylamine in the presence of a base catalyst. In (II) R2 = H or 1-4C alkyl. For (II) pref. R1CO is 12-18C acyl and R2 is methyl. (II) and bissorbitylamine are pref. reacted in the mol. ratio of 0.95-1:1-1.2. The base catalyst is pref. one of alkali(ne earth) oxide, hydroxide, carbonate or 1-4C alkoxide, and is pref. added in amts. of 0.1-5 wt.% w.r.t. starting materials. Pref. the raction is carried out at 60-150 deg.C in the presence of a solvent. USE/ADVANTAGE - The use of (I) for the prepn. of washing, rinsing or cleaning agents or hair and body care prods. is claimed. (I) have improved hydrophilicity and cold water solubility. In an example, 346 g bissorbitylamine was dissolved in 200 ml DMF, then N2 was bubbled through and the mixt. was then heated to 130 deg.C. 4g solid K2CO3 and 256g Edenor K1218 (RTM: 12/18C cocoa fatty acid methyl ester, degree of saponification 240) were added, after 2 hrs. the mixt. was then cooled and then neutralised with phosphoric acid. The unreacted methyl ester was distilled off to give 492g (90% yield) cocoa fatty acid bissorbitylamide white solid.

Description

Field of the Invention

The invention relates to fatty acid bis-sorbitylamide, a process for their production, in which fatty acids or Reacting fatty acid lower alkyl esters with bis-sorbitylamine, aqueous detergent mixtures and surfactants, the which contain fatty acid bis-sorbitylamide as well as the use the fatty acid bis-sorbitylamide for the production of surface-active Medium.

State of the art

Mono- and polysaccharides are inexpensive, recent raw materials the use of which to protect fossil, contributes to non-renewable raw materials such as oil or coal. So have in the field of sugar surfactants in addition to Sucrose and sorbitan esters, especially the alkyl polyglucosides can establish that alongside excellent Detergent properties over a particularly advantageous have ecotoxicological tolerance [Tens. Surf. Det. 28, 419 (1991)].  

Another group of sugar surfactants are the aminopentaols and their acylation products, such as, for example by H. Kelkenberg in Tens. Surf. Det. 25, 8 (1988) have been. Such fatty acid N-alkyl glucamides have been known for more than 30 years and are usually by reductive amination of glucose with amines and optionally subsequent acylation with fatty acid esters produced [US 29 65 576 (Procter & Gamble)]. Specific Variants of this process are the subject of international Patent applications WO 92/6984 and WO 92/8687 (Procter & Gamble).

Also the use of the fatty acid-N-alkylglucamides mentioned is the subject of a large number of publications. From the European patent application EP-A1 02 85 768 (Huls) is for example its use as a thickener is known. In the French patent application FR-A 15 80 491 (Henkel) aqueous detergent mixtures based on sulfates and / or sulfonates, nonionic surfactants and optionally soaps, the fatty acid N-alkylglucamides as foam regulators contain.

Subject of international patent applications WO 92/6153; 6156; 6157; 6158; 6159 and 6160 (Procter & Gamble) are mixtures of polyhydroxy fatty acid, especially fatty acid N-alkyl glucamides with anionic surfactants, surfactants with Sulfate and / or sulfonate structure, ether carboxylic acids, ether sulfates, Methyl ester sulfonates and nonionic surfactants. The use of these substances in a wide variety Detergents, dishwashing detergents and cleaning agents are used in the  international patent applications WO 92/6152; 6154; 6155; 6161; 6162; 6164; 6170; 6171 and 6172 (Procter & Gamble).

The compilation shows that the class of Fatty acid N-alkylglucamides to intensively studied nonionic Sugar surfactants. It is therefore surprising in itself that it has so far not succeeded in many applications have insufficient hydrophilicity and cold water solubility of said fatty acid N-alkylglucamides in more desirable Way to improve.

The object of the invention was therefore to create new nitrogenous ones Develop sugar surfactants that are free from the disadvantages described.

Description of the invention

The invention relates to fatty acid bis-sorbitylamide Formula (I)

in the
R¹CO for an aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms and
Z for a sorbityl residue
stands.

Surprisingly, it was found that the inventive Fatty acid bis-sorbitylamide doesn't just have excellent Detergent properties and high ecotoxicological compatibility have, but also one against the fatty acid N-alkyl glucamides greatly improved cold water solubility have.

Another object of the invention relates to a method for the preparation of fatty acid bis-sorbitylamides of the formula (I)

in the
R¹CO for an aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms and
Z for a sorbityl residue
in which fatty acids or fatty acid lower alkyl esters of the formula (II)

R¹CO-OR² (II)

in which R¹CO has the meaning given above and R² for Hydrogen or an alkyl radical having 1 to 4 carbon atoms stands, in the presence of basic catalysts with bis-sorbitylamine implements.

Typical examples of fatty acids or fatty acid lower alkyl esters, those for acylation of bis-sorbitylamine come are caproic acid, caprylic acid, capric acid, Lauric acid, myristic acid, palmitic acid, palmoleic acid, Stearic acid, isostearic acid, stearic acid, oleic acid, elaidic acid, Petroselinic acid, linoleic acid, linolenic acid, ricinoleic acid, 12-hydroxystearic acid, arachidic acid, gadoleic acid, Behenic and erucic acids and their technical Mixtures such as those used in the pressure splitting of Greases and oils occur. In addition to the fatty acids mentioned their esters also come with methanol, ethanol, or propanol Butanol into consideration. Fatty acid lower alkyl esters are preferred of formula (II) used in the R¹CO for one Acyl radical with 12 to 18 carbon atoms and R² for a methyl group stands. Are particularly preferred Methyl laurate and technical coconut or tallow fatty acid methyl esters.

Bis-sorbitylamine is a well-known substance that follows the relevant methods of preparative organic chemistry can be obtained. A process for its manufacture consists, for example, in the reductive amination of glucose with ammonia.

The fatty acids or fatty acid lower alkyl esters can usually be used and the bis-sorbitylamine in a molar ratio of  0.95: 1 to 1: 1.2, preferably 1: 1 to 1: 1.1 will.

The basic catalysts can be selected from the Group consisting of alkali and alkaline earth oxides, hydroxides, -carbonates and C₁-C₄ alcoholates is formed. Typical Examples are sodium hydroxide, sodium carbonate, sodium methylate, Potassium carbonate and potassium tert-butoxide. It has proved to be optimal, the catalysts in amounts of 0.1 to 5, preferably 1 to 2 wt .-% - based on the starting materials - use.

The implementation of the fatty acids or fatty acid lower alkyl esters with the bis-sorbitylamine can be used at temperatures from 60 to 150, preferably 90 to 130 ° C. In a preferred embodiment of the invention is acylation in a solvent, for example methanol, dimethylformamide, Dimethyl sulfoxide, N-methylpyrrolidone or Tetrahydrofuran instead. After completion of the implementation, this can Solvent be distilled off again.

Another object of the invention relates to aqueous detergent mixtures containing the fatty acid bis-sorbitylamides of formula (I)

in the
R¹CO for an aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms and
Z for a sorbityl residue
stands as well as other anionic, nonionic, cationic and / or amphoteric or zwitterionic surfactants.

Typical examples of anionic surfactants are alkylbenzenesulfonates, Alkane sulfonates, olefin sulfonates, alkyl ether sulfonates, Glycerol ether sulfonates, α-methyl ester sulfonates, sulfofatty acids, Alkyl sulfates, fatty alcohol ether sulfates, glycerol ether sulfates, Hydroxy mixed ether sulfates, monoglyceride (ether) sulfates, Fatty acid amide (ether) sulfates, sulfosuccinates, Sulfosuccinamates, sulfotriglycerides, ether carboxylic acids, isethionates, Taurides, sarcosinates, alkyl oligoglucoside sulfates and Alkyl (ether) phosphates. If the anionic surfactants polyglycol ether chains contain a conventional, but preferably have a narrow homolog distribution.

Typical examples of nonionic surfactants are fatty alcohol polyglycol ethers, Alkylphenol polyglycol ether, fatty acid polyglycol ester, Fatty acid amide polyglycol ether, fatty amine polyglycol ether, alkoxylated triglycerides, alk (en) yl oligoglycosides, Fatty acid glucamides, polyol fatty acid esters, sugar esters, sorbitan esters and polysorbates. Unless the nonionic surfactants Containing polyglycol ether chains, they can be a conventional, but preferably a narrow homolog distribution exhibit.  

Typical examples of cationic surfactants are quaternary ammonium compounds and quaternized difatty acid trialkanolamine esters.

Typical examples of amphoteric or zwitterionic surfactants are aminobetaines, alkylamidobetaines, aminopropionates, aminoglycinates, Imidazolinium betaines and sulfobetaines.

The surfactants mentioned are exclusively known connections. In terms of structure and manufacture these substances are on relevant reviews, for example J. Falbe (ed.), "Surfactants in Consumer Products", Springer Verlag, Berlin, 1987, pp. 54-124 or J. Falbe (ed.), "Catalysts, surfactants and mineral oil additives", Thieme Verlag, Stuttgart, 1978, pp. 123-217.

The aqueous detergent mixtures can be those according to the invention Fatty acid bis-sorbitylamide in amounts of 1 to 99, preferably 2 to 50 and in particular 5 to 25 wt .-% - based on the solids content of the mixtures - included.

Industrial applicability

The fatty acid bis-sorbitylamides according to the invention have excellent detergent properties. For example, they promote wetting hard surfaces and emulsification otherwise immiscible phases. A a particular advantage is their surprisingly good solubility in cold water. Further configurations of the invention relate to therefore surfactants that the invention  Contain substances and characterized in more detail below will:

• Universal powder detergent containing 10 to 30 % By weight - based on the average - of the invention Fatty acid bis-sorbitylamide of formula (I) and optionally further anionic, nonionic, cationic, amphoteric or zwitterionic surfactants as well as usual Auxiliaries and additives.
• Liquid universal detergent containing 10 to 70 % By weight - based on the average - of the invention Fatty acid bis-sorbitylamide of formula (I) and optionally further anionic, nonionic, cationic, amphoteric or zwitterionic surfactants as well as usual Auxiliaries and additives.
• Liquid mild detergent containing 10 to 50% by weight - based on the agent - the fatty acid according to the invention - bis-sorbitylamides of the formula (I) and, if appropriate further anionic, nonionic, cationic, amphoteric or zwitterionic surfactants and usual auxiliaries and Additives.
• Hand dishwashing detergent, containing 10 to 50% by weight - based on the agent - the fatty acid according to the invention - bis-sorbitylamides of the formula (I) and, if appropriate further anionic, nonionic, cationic, amphoteric or zwitterionic surfactants and usual auxiliaries and Additives.  
• Rinse aid, containing 10 to 50 wt .-% - based on the Agent - the fatty acid bis-sorbitylamide according to the invention of formula (I) and optionally further anionic, non-ionic, cationic, amphoteric or zwitterionic surfactants as well as usual auxiliaries and additives.
• Containing liquid detergents and disinfectants 10 to 30 wt .-% - based on the agent - of the invention Fatty acid bis-sorbitylamide of formula (I) and optionally further anionic, nonionic, cationic, amphoteric or zwitterionic surfactants and usual auxiliaries and additives.
• Hair shampoos containing 10 to 30 wt .-% - based on the agent - the fatty acid bis-sorbitylamide according to the invention of formula (I) and optionally further anionic, non-ionic, cationic, amphoteric or zwitterionic surfactants as well as usual auxiliaries and additives.
• Hair rinses containing 10 to 30 wt .-% - based on the agent - the fatty acid bis-sorbitylamide according to the invention of formula (I) and optionally further anionic, non-ionic, cationic, amphoteric or zwitterionic surfactants as well as usual auxiliaries and additives.
• Bubble baths containing 10 to 30% by weight the agent - the fatty acid bis-sorbitylamide according to the invention of the formula (I) and optionally further  anionic, nonionic, cationic, amphoteric or zwitterionic surfactants as well as usual auxiliaries and additives.

Finally, a final object of the invention relates to Use of the fatty acid bis-sorbitylamide according to the invention for the production of detergents, dishwashing detergents and cleaning agents and Products for hair and body care in which they are in quantities from 1 to 70, preferably 5 to 35 wt .-% - based on the Means - may be included.

The following examples are intended to be the subject of the invention explain in more detail without restricting it.  

Examples Example 1 Coconut fatty acid bis-sorbity amide

In a 1 liter three-necked flask equipped with a stirrer, reflux condenser and dropping funnel, 346 g (1 mol) of bis-sorbitylamine were dissolved in 200 ml of dimethylformamide. The reaction mixture was pressurized with nitrogen and heated to 130 ° C. with stirring. 4 g of solid potassium carbonate were then added, 256 g (1.1 mol) of _methyl C _12/18 coconut _fatty acid (Edenor® K1218, saponification number 240, Henkel KGaA) were added in portions via the dropping funnel _{and the} mixture was stirred for a further 2 h. The mixture was then cooled, neutralized with phosphoric acid and the solvent and unreacted methyl ester were distilled off.

There were 492 g of coconut fatty acid bis-sorbitylamid - accordingly 90% of theory - in the form of a white solid receive.

Example 2 Lauric acid bis-sorbitylamide

Example 1 was used with 346 bis Sorbitylamine, 214 g (1 mol) of methyl laurate and 6 g solid sodium methylate repeated.

There were 480 g of lauric acid bis-sorbitylamid - accordingly 91% of theory - obtained in the form of a white solid.

Claims (9)

1. Fatty acid bis-sorbitylamides of the formula (I) in the
R¹CO for an aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms and
Z for a sorbityl residue
stands. 2. Process for the preparation of fatty acid bis-sorbitylamides of the formula (I) in the
R¹CO for an aliphatic, linear or branched acyl radical having 6 to 22 carbon atoms and
Z for a sorbityl residue
is in which fatty acids or fatty acid lower alkyl esters of the formula (II) R¹CO-OR² (II) in which R¹CO has the meaning given above and R² is hydrogen or an alkyl radical having 1 to 4 carbon atoms, in the presence of basic catalysts with bis-sorbitylamine implements. 3. The method according to claim 2, characterized in that fatty acid lower alkyl esters of the formula (II) are used, in the R¹CO for an acyl radical having 12 to 18 carbon atoms and R² represents a methyl group. 4. The method according to claim 2, characterized in that the fatty acids or fatty acid lower alkyl esters and the bis-sorbitylamine in a molar ratio of 0.95: 1 up to 1: 1.2. 5. The method according to claim 2, characterized in that basic catalysts selected are used from the group consisting of alkali and alkaline earth oxides, hydroxides, -carbonates and C₁-C₄ alcoholates formed becomes. 6. The method according to claim 2, characterized in that the catalysts in amounts of 0.1 to 5 wt .-% - based on the starting materials - used. 7. The method according to claim 2, characterized in that the reaction at temperatures from 60 to 150 ° C. carries out.   8. The method according to claim 2, characterized in that the reaction in the presence of a solvent carries out.   9. Use of the fatty acid bis-sorbitylamide according to the invention for the production of washing, rinsing and cleaning agents and products for hair and body care.