US2808404A - Sulfated fatty urea nu-glycosides - Google Patents

Description

Patented Oct. 1, 1957 ice 2,808,404 SULEATED FATTY UREA N-errcosrons John G. Erickson, Minneapolis, Minn., assignor to General Mills, Inc., a corporation of Delaware No Drawing. Application May 11, 1953, Serial N0. 354,417

5 Claims. (Cl. 260-2115) The present invention relates to sulfation products of fatty urea N-glycosides. These products are obtained by the sulfation of the reaction products of fatty ureas with aldose sugars. Typical products obtainable with aldohexoses include the following:

O O RNHiiNHOHOHOHCHOHCHCHCHaOSOaM OSOQM 0803M OS OaM OSOaM OSOaM in which R is a long chain aliphatic hydrocarbon group containing from 8-22 carbon atoms and M is alkali metal or ammonium. These compounds are useful as emulsifiers and wetting agents, detergents and the like.

It is, therefore, an object of the present invention to provide novel compounds derived by the sulfation of reaction products of fatty ureas and aldose sugars.

These compounds may be prepared by first reacting fatty amines with urea to obtain a fatty urea which'is then reacted with an aldose sugar to form the fatty urea N-glycosides. These glycosides are then sulfated to form the products of the present invention. The fatty amines which may be used are the primary fatty amines containing from 8-22 carbon atoms. They may be the mixed amines prepared from the mixed acids of a fat or oil or from any isolated single fatty acid or any particular group of fatty acids. Thus the fatty group in the ultimate product may :be either saturated or unsaturated. Typical fatty groups include octyl decyl, dodecyl, tetradecyl, hexadecyl, octadecyl, etc.

Any aldose may be used for reaction with the fatty urea. Since the 'aldohexoses and aldopentoses are the most readily available, they are preferred. Typical aldoses include glucose, galactose, mannose, arabinose, lyxose, xylose, ribose and the like. The reaction between the aldose and the fatty urea is preferably carried out in the presence of a small quantity of mineral acid and in the presence of ethanol as a solvent. Reaction temperatures of around 50 C. for 50-60 hours are suitable.

The fatty urea N-glycoside thus formed is then reacted with any suitable sulfating agent such as sulfur trioxide, chlorosulfonic acid or sulfuric acid. The reaction is carried out in a solvent which is inert to the reactants such as carbon tetrachloride, chloroform, tetrachloroethane and so forth. The reaction may be carried out at temperatures from 10 C. to 100 C. Preferred temperatures are from 15-50 C. It is known that strong acids tend to cause discoloration, darkening and decomposition of sugar compounds. Notwithstanding this fact, it has been observed that there appears to be no decomposition of the sugar residue during this reaction. The products obtained are white or very faintly tinged with yellow. After thesulfation reaction, it is desirable to neutralize the acid sulfate ester. This is done by adding a suitable alkaline material such as sodium or potassium hydroxides, carbonates or acetates, ammonium hydroxide and the like.

The number of sulfate groups introduced into the molecule is determined by regulating the amount of sulfating agent employed. In general, the molar ratio of sulfating agent to glycoside is approximately equal to the "number of sulfate groups to be introduced.

All of these compounds possess wetting, cleansing and detergent properties. With the shorter chain fatty groups, for example, those containing from 8-12 carbon atoms,best results are obtained with a single sulfate group. Where the fatty group contains 18-22 carbon atoms, it is preferred to introduce 3 or 4 sulfate groups. At intermediate carbon chain lengths, two sulfate groups are desirable.

EXAMPLE 1 A solution of 0.69 part of chlorosulfonic acid in 22 parts of chloroform was added to a suspension of 1.95 parts of dodecylurea N-galactoside in parts of chloroform at 25 C. The mixture became homogeneous. After ten minutes, it was made alkaline with a solution of sodium hydroxide in aqueous alcohol. It was then made slightly acidic with acetic acid and allowed to evaporate. This left a very light yellow solid as residue. This was the sodium salt of the monosulfate of dodecylurea N- galactoside. It dissolved readily in water, giving a solution which foamed very well.

The compound was tested for foaming and for detergency as a 0.1% aqueous solution, pH 9.0.

Ross-Miles foam test (25 C.)

Initial height Height after 5 min. (min) Detergency (increase in reflectance, expressed as percent: MgO

Compound Percent Sodium dodecylurea N-galaetoside monosulfate 5. 1 Commercial sample of sodium dodecylbenzenesulfonate. 24. 9

3 EXAMPLE 2 A mixture of 6.2 parts of octadecylurea, 4.0 parts of glucose, 0.5 part of concentrated hydrochloric acid and 80 partsof 95% ethanol was stirred and heated to 50 Cfifor 147.5 ,hours. It .was then cooled and filtered, yielding a white solid. This was washed with hot benzene to give octadecylurea N-glucoside, M. P. 175188 C. with decomposition. V

A solution of 0.35 part of chlorosulfonic acid in 15 parts of chloroform was added to a suspension of 0.47 part of octadecylurea N-glucoside in 37 parts of chloroform. The solid dissolved rapidly. After '20 minutes,

the mixture was made slightly basic with an aqueousalcoholic solution of potassium hydroxide, then made acidic with a drop of acetic acid. The mixture was allowed to evaporate, leaving a White solid as residue. It was the tripotassium salt of the trisulfate of octadecylurea iN-glucoside. Aqueous solutions of this product showed surface-"active properties.

Numerous-other products coming within the scope of the present invention may be made according to the above examples by substituting fatty urea N-glycosides derived from other aldoses and other fatty amines. The reaction conditions are essentially the same and the products obtained vary in their properties as described above.

I claim as my invention:

1. A sulfated fatty urea N- glycoside in which the fatty group contains from 8-22 carbon atoms.

2. A sulfated fatty urea N-galactoside in which the fatty group contains from 8-22 carbon atoms.

3. A sulfated fatty urea N-glucoside in which the fatty group contains from 8-22 carbon atoms.

4. The sodium salt of the monosulfate of dodecylurea N-galactoside.

5. The tripotassium salt of the trisulfate of octadecylurea N-glueoside.

References Cited in the file of this patent UNITED STATES PATENTS 2,002,613 Orthner et a1 May 28, 1935 2,596,268 Meijer May 13, 1952 2,599,172 Hadidian June 3, 1952 2,612,497 Meijer Sept. 30, 1952 2,612,499 Pulver "Sept. 30, 1952 OTHER REFERENCES Hudson et al.: Advances in Carbohydrate Chemistry, vol. 8, published by Academic Press (New York), 1953 (pages 116 and 117).

Claims (1)

1. A SULFATED FATTY UREA N-GLYCOSIDE IN WHICH THE FATTY GROUP CONTAINS FROM 8-22 CARBON ATOMS.