MXPA98001150A

MXPA98001150A - Oxides of polyhydroxyalyl-amidoam

Info

Publication number: MXPA98001150A
Application number: MXPA/A/1998/001150A
Authority: MX
Inventors: Papenfuhs Bernd
Original assignee: Hoechst Ag 65929 Frankfurt De
Priority date: 1995-08-11
Filing date: 1998-02-10
Publication date: 1999-01-11

Abstract

The described amine oxides correspond to the following formula (1) (See Formula) in which RCO is an aliphatic acyl radical having from 6 to 22 carbon atoms, Z is a linear polyhydroxyhydrocarbon radical having at least three optionally oxyalkylated hydroxyl groups, m is an integer from 1 to 4, R1 is C1 to C4 alkyl or C2 to C4 hydroxyalkyl and R2 is C21 to C4 alkyl or C2 to C4 hydroxyalkyl, amine oxides are prepared and aqueous solutions are alcoholic or aqueous -alcoholic, by oxidation of the corresponding compounds of tertiary amine with hydrogen peroxide, novel amine oxides and their solutions are particularly suitable for the preparation of surfactant compositions for hair and body care

Description

POLYHYDROXYALYKYLAMID OXIDES-AMIDOAMINE DESCRIPTIVE MEMORY The invention relates to polyhydroxyalkyl amidoamine oxides, to aqueous, alcoholic or aqueous-alcoholic solutions thereof, to a process for the preparation of these amine oxides and their solutions, and to the use of novel amine oxide compounds and solutions of them. Amine oxides are valuable compounds of zwitterionic surfactant groups. Because of their considerable cleaning power and their other advantageous properties, in particular with respect to foaming properties and skin tolerance, they are used in the form of liquid formulations especially for cleaning the hair and the body. Solvents are generally water, lower alkanols, such as methanol, ethanol, isopropanol, ethylene glycol and / or propylene glycol, or mixtures thereof. Concentrated to highly concentrated formulations (containing as little solvent as possible) and at the same time reduced viscosity are convenient with respect to storage and transport costs, prior processing and use at the application site. Commercially available amine oxide solutions generally have an amine oxide content (active compound content) of less than 30% by weight. Reference is made to concentrated amine oxide solutions in the case of a content in the active compound from 30 to about 35% by weight and in highly concentrated amine oxide solutions in a higher active compound content. The amine oxides are generally prepared by oxidation of tertiary amine compounds with hydrogen peroxide in an aqueous or aqueous-alcoholic medium. In the case of amidoamine oxides in particular, whose fields of application are mostly in the cosmetics and cleaning compositions sector (compare US-A-4). 077 990, JP-A-61 283695 and EP-A-367 926), the solubility is severely limited. A novel class of amidoamine oxides has now been discovered which is distinguished by a considerable water solubility and also reduced viscosity formulations having a high concentration of amine oxide. The amine oxides according to the invention of the group consisting of oxidized polyhydroxyalkylamidoamines correspond to the following formula (1) Ri RC0-N- (CH2) m-N > 0 (1) 2 R2 in which RC0 is an aliphatic acyl radical having from 6 to 22 carbon atoms. Z is a linear polyhydroxyhydrocarbon radical having at least 3 optionally oxyalkylated hydroxyl groups, m is an integer from 1 to 4, Ri is Ci to G alkyl; or C2 to C2 hydroxyalkyl and R2 is Ci to C alkyl < or hydroxyalkyl of C2 a. The preferred compounds of the formula (1) according to the invention are those in which. RCO is a fatty acid radical having 8 to 18 carbon atoms, Z is a sugar alcohol radical which is derived from a mono- or dialkyl reducing, in particular glucose, m is number 3 and R1 and R2 ( identical or different) are methyl, ethyl, propyl or hydroxyethyl. The following can also be expressed with respect to RCO and Z: the aliphatic acyl radical RCO, which is preferably the aforementioned fatty acyl radical, can be saturated or unsaturated (preferably mono- to tri-unsaturated). Some examples that may be mentioned are the acrylic radicals of caprylic, capric, lauric, palmitic, stearic and oleic acids, as well as coco-acyl, tallow-acyl, preferably hydrogenated tallow-acyl, and the like. The fatty acid radical is often a mixture of two or more acyl groups, for example C12 and C14 acyl (C12 / 1, acyl of Cie and ee (C? &? /?) Or acyl of C12 to Cie. already mentioned above, in the linear polyhydroxyhydrocarbon radical it is preferably originated from sugar alcohols derived from the group consisting of reducing sugars or reducing sugar derivatives.The preferred reducing sugars are the onoscarides, preferably pentoses and hexoses, and the oligosaccharides, preferably discarnates and, when appropriate, also the triacharides. Some examples of monosaccharides are glucose, galactose, mannose and talose such as hexoses, and arabigosa, ribose and xylose as pentoses. Of the monosaccharides, hexoses are preferred. Some examples of oligosaccharides (polysaccharides) are lactose, maltose, maltotriose and the like. Particularly preferred polyhydroxyalkyl radicals originate from reducing hexoses, and in particular glucose (sorbityl radical). The amine oxides of the formula (1) according to the invention are prepared by oxidation of a tertiary amine compound having the formula (2). Ri RC0-N- (CH2) m - (2) in which R, Ri, R2 Z and m have the given meanings, with hydrogen peroxide in water, a lower alcohol or a mixture of water and a lower alcohol as a solvent. The reaction of the tertiary amine compound, for example N, N-dimethylaminopropyl- (fatty acyl) -gluca ida, is carried out with hydrogen peroxide, specifically in such a way that it is used in the tertiary amine and the oxidizing agent in a molar ratio of 1: 1 to 1.2, preferably 1: 1 to 15; if appropriate, a sequestering agent is added. The solvent may be water, and a lower alcohol, preferably methanol, ethanol, isopropanol, ethylene glycol and / or propylene glycol, or a mixture of water and the alcohols mentioned. The amount of solvent (which is introduced into the reaction mixture as such or in the form of solutions of the starting compounds) is chosen in general such that the amine oxide solution obtained after the reaction has an oxide content. of amine (content of active compound from 30 to about 65% by weight and preferably from 30 to 60% by weight, based on the percentages by weight in the solution) Hydrogen peroxide is used and in the form of commercially available aqueous solutions in the range of 20 to 90% by weight The reaction temperature is generally 60 to 110 ° C, preferably 70 to 100 ° C. The oxidation reaction, which takes place at atmospheric pressure, is maintained until it is achieved The resulting amine oxide solutions contain the amine oxide according to the invention in a high concentration, it can be obtained in pure form by removing the solvent, this is generally unnecessary, because the amine oxides according to the invention are used, in any case especially in solutions. Advantageously, the amine compounds having the formula (2) are obtained since they are required for the preparation of the amine oxides according to the invention and their solutions, by means of a) The reaction of a polyhydroxyhydrocarbon compound from which it is derived the radical Z in the formula (1) or the formula (2) with an amine having the formula (3). wherein m, R * and R2 have the given meanings, in an aqueous or aqueous-alcoholic medium and in the presence of a hydrogenation catalyst to give the polyhydroxyalkylamine having the formula (4). Rl I Z-NH- (CH2) m-N (4) wherein Z, m, R1 and R2 have the given meanings, and b) The reaction of the product obtained in step a), which contains essentially polyhydroxyalkylamine having the formula (4), with an alkyl ester of fatty acid having the formula (5). OR RC-OR3 (5) wherein R has the given meaning and R3 is an alkyl group of Ci to C3, to give the polyhydroxylamidoamine of the given formula (2). Steps a) and b) are described in more detail below: Step a) is a reductive amination of a polyhydroxy compound of the aforementioned type, such as mono- or disaccharide compounds, preferably hexoses, such as glucose, with an amine which has the formula (3). The sugar compound and the amine compound are used in a molar ratio of about 1: 1 to 1.2. The solvent, which is preferably water or a mixture of water and a lower alcohol, such as methanol, ethanol and / or isopropanol, is employed in an amount of about 30 to 50% by weight, based on the polyhydroxyalkylamine formed. The catalysts that can be used are the usual hydrogenation catalysts, such as palladium active carbon, copper brocade and, in particular, Raney nickel, an amount in general from 0.01 to 3% by weight, preferably from 0.1 to 1%. in weight, based on the sugar compound by amine. The reductive amination reaction is carried out at a temperature of 40 to 150 ° C, preferably 50 to 120 ° C, and under a hydrogen pressure of 10 to 200 bar, preferably 20 to 100 bar. The indo-sugar compound according to formula (4) is obtained in practically quantitative yields. In step b), acylate the reaction product obtained in step a) (if appropriate, after removing catalyst by filtration) with about 1 mole of fatty acid ester having the formula (5) forming the amino-sugar compound in the presence of a basic catalyst. This is preferably carried out at a temperature of about 60 to 130 ° C, for example by cooling the reaction mixture under reflux, which leads to the acylated sugar amine having the formula (2). The amine oxides according to the invention have unexpectedly convenient properties. They are soluble in water, lower alcohols or mixtures thereof at room temperature (20 to 25 ° C) up to high concentrations. Concentrated to highly concentrated solutions are surprisingly of reduced viscosity, ie they are easily flowable, pourable, pumpable and the like, at room temperature. In addition, the aqueous, alcoholic or aqueous-alcoholic amine oxide solutions according to the invention are distinguished by their high transparency) transparent to the naked eye like water) and their storage stability. The amine oxides according to the invention are based on regenerating starting materials and are biologically degradable, which is a further advantage of these surfactant compounds with remarkable surfactant properties. Based on this property profile, the amine oxides and the amine oxide solutions according to the invention are advantageously used for the preparation of surfactant compositions for hair and body care.

The invention will now be explained in more detail by way of examples, in which the abbreviation "DMAP" is dimethylaminopropyl and the abbreviation "GA" is glucamide.

EXAMPLE 1 CMA2 DMAP-CGA Oxide -amine Initially 209.4 g (0.45 mol) of DMAP- (GA of C12) is introduced at 96% concentration by weight that does not have or is low in alkaline metal or alkaline earth metal levels, 207.5 grams of distilled water and 0.1 g of disodium salt of ethylenediaminetetraacetic acid (EDTA), to a four-necked flask, equipped with reflux condenser, stirrer, thermometer and dropping funnel, and heated to 70 ° C, while stirring. Then, 45.9 g (0.473 mol) of an aqueous solution of hydrogen peroxide at 35% concentration by weight are continuously added dropwise over the course of 30 minutes; as a result of the exothermic reaction, the temperature rises to about 80 ° C. The reaction mixture is now stirred at 75-80 ° C for another 5-8 hours, during which a highly liquid solution comprising 44% by weight of the corresponding amine oxide having the formula (1) (97) is obtained. % yield); the residual content of hydrogen peroxide is not more than 0.1% by weight.

EXAMPLE 2 Oxides of DMAP- (GA of Ci2 / iA) -amine Lot Size: 263.0 g (0.55 mol) of a DMAP- (GA of C12 / 1O at 95% concentration by weight that does not have or is low in alkali metal or alkaline earth metal ions) 255.2 g of distilled water 0.1 g of EDTA 56.1 g (0.578 mol) of aqueous solution of hydrogen peroxide at 35% concentration by weight.

The reaction is carried out analogously to that of Example 1. A highly liquid solution comprising 44% by weight of the corresponding amine oxide having the formula (1) is obtained in a yield of 97%.

EXAMPLE 3 DMAS-CGA Oxides of Ciß / is) -amine Batch Dimension: 138.0 g (0.55 mol) of a DMAP- (GA of Ciß / iß) at 93% concentration by weight that does not have or is low in alkali metal or alkaline-earth metal ions. 259.9 g of distilled water 0.1 g of EDTA 25.5 g (0.263 mol) of aqueous solution of hydrogen peroxide at 35% concentration by weight.

The reaction is carried out analogously to that of Example 1. A highly liquid solution comprising 30% by weight of the corresponding amine oxide having the formula (1) is obtained in a yield of 96%.

Claims

NOVELTY OF THE INVENTION CLAIMS

1. - A polyhydroxyalkyl amidoamine oxide having the following formula (1). Ri RC0-N- (CH2) mN- or (1) iA »in which RCO is an aliphatic acyl radical having from 6 to 22 carbon atoms, Z is a linear polyhydroxyhydrocarbon radical having at least 3 hydroxyl groups optionally oxyalkylated, m is an integer from 1 to 4, R * is Ci to C alkyl or C2 to C "hydroxyalkyl and R2 is C2 to C alkyl << or C2 to C4 hydroxyalkyl.

2. An amine oxide according to claim 1, further characterized in that, in the formula (1), RCO is a fatty acid radical having from 8 to 18 carbon atoms, Z is a sugar alcohol radical which is derived from a mono- or disaccharide reducing, is number 3 and Rl and R2 are methyl, ethyl, propyl or hydroxyethyl.

3. An amine oxide according to claim 1, further characterized in that, in formula (1), RCO is a fatty acid radical having 8 to 18 carbon atoms, Z is a sorbityl radical, m is 3 , and Ri and R2 are methyl, ethyl, propyl or hydroxyethyl.

4. - A process for the preparation of a polyhydroxyalkyl amidoamine oxide according to claim 1, further characterized in that it comprises the oxidation of a tertiary amine compound having the formula (2). Ri RC0-N- (CH2) -N (2) Z R2 in which R, R1, R2, Z and m have the meanings given, with hydrogen peroxide in water, a lower alcohol or a mixture of water and a lower alcohol as solvent.

5. The process according to claim 4, further characterized in that 1 to 1.2 mol of hydrogen peroxide is used per gram molecule of the tertiary amine compound and the solvent is used in an amount such that the amine oxide solution obtained after the reaction has an amine oxide content of 30 to 65% by weight, based on the weight of the solution, and the oxidation reaction is carried out at a temperature of 60 to 110 ° C.

6. The process according to claim 4, further characterized in that a) the mixture of solvent and the tertiary amine compound is prepared, and this mixture is heated to 70-100 ° C, b) is introduced from 1 to 1.2 mole of hydrogen peroxide in the form of an aqueous solution at 90% concentration by weight per gram amine molecule, to the heated mixture, said temperature being maintained at 70-100"C, and c) the reaction mixture obtained in step b) at a temperature of 70-100 ° C until the desired content of amine oxide is achieved

7. An aqueous, alcoholic or aqueous-alcoholic solution of polyhydroxyalkyl amidoamine oxide, comprising A) from 30 to 65 % by weight of at least one compound having the formula (1) in claim 1 and B) water, a lower alcohol or a mixture of water and a lower alcohol as the remainder to constitute 100% by weight. - A solution according to claim 7, further characterized by component A) is present in an amount of 30 to 60% by weight. 9. The use of a polyhydroxyalkyl amidoamine oxide according to claim 1 for the preparation of surfactant compositions for hair and body care. 10. The use of an aqueous, alcoholic or aqueous-alcoholic solution according to claim 7 for the preparation of surfactant compositions for hair and body care.