US3626034A - Dialkyl phosphoryl n-alkyltaurinates - Google Patents

Abstract

WHEREIN R is an alkyl group containing from six to 16 carbon atoms; R1 is an alkyl group containing from six to 16 carbon atoms; R2 can be hydrogen, an alkyl group containing from one to eight carbon atoms or an aryl group containing from one to eight carbon atoms; Y is selected from the group consisting of sodium, potassium, ammonium and mixtures thereof, and n is an integer from one to four.

A composition of matter useful in the process of dry cleaning clothing consisting essentially of the formula:

Description

United States Patent [72] inventor Ralph B. Fearing Bardonia, N.Y. [2]] Appl. No. 686,747 [22] Filed Nov. 29, 1967 {45] Patented Dec. 7, 1971 [73] Assignee Stauifer Chemical Company New York, N.Y.

[54] DIALKYL PHOSPl-IORYL N-ALKYLTAURINATES 1 Claim, No Drawings [52] U.S. Cl 260/947, 8/142, 260/984 [51] Int. Cl C07f 9/24, D061 H04 [50] Field of Search 260/947, 920

[56] References Cited UNITED STATES PATENTS 3,298,937 ll/l967 Strauss et a] 260/947 X Primary ExaminerCharles B. Parker Assistant E.raminerAnton H. Sutto Attorneys-Daniel C. Block, Robert C. Sullivan, Donald M.

MacKay and Paul J. Juettner ABSTRACT: A composition of matter useful in the process of dry cleaning clothing consisting essentially of the formula:

ROORz wherein R is an alkyl group containing from six to 16 carbon atoms; R is an alkyl group containing from six to 16 carbon atoms; R can be hydrogen, an alkyl group containing from one to eight carbon atoms or an aryl group containing from one to eight carbon atoms; Y is selected from the group consisting of sodium, potassium, ammonium and mixtures thereof, and n is an integer from one to four.

1 DIALKYL PHOSPIIORYL N-ALKYLTAURINATES BACKGROUND OF THE INVENTION In the art of dry cleaning clothing, it is the practice to place the clothing in a solvent system and saturate or otherwise agitate the clothing therein. The solvents commonly used are 70-80 percent can be maintained at a maximum water content without fabric shrinkage or wrinkling;

e. remove insoluble soils and minimize their redeposition on clothes,

remove water soluble soils such as sodium chloride and sugars, thereby preventing visual or cumulative redeposition on the clothes;

g. allow dissipation of static charge, particularly in tumbler dryers; to avoid shock to personnel; to avoid lint problems; and allow easy garment handling and pressing;

h. be nontoxic in formulation and in use;

i. be harmless to textile dyes.

It is common practice to add up to about percent by weight of detergents such as amine alkyl aryl sulfonate, an anionic phosphate ester such as the well known alkyl aryl polyoxyethylene phosphates, or sodium dioctyl sulfosuccinate to the solvent system. However, these detergentshave failed to fill all the above noted requirements of a detergent in sol- BRIEF DESCRIPTION OF THE INVENTION It has been discovered that dialkyl phosphoryl N-alkyl taurinates provide superior cleaning properties when employed as a detergent within the commonly employed solvent systems. Compounds of the present invention are represented by the following formula:

P-N-(GHzh-SOgY wherein R can be an alkyl group containing from six to 16 carbon atoms; R can be an alkyl group containing from six to 16 carbon atoms; R can be hydrogen, an alkyl group containing from one to eight carbon atoms or an aryl group containing from one to eight carbon atoms and Y can be sodium, potassi um or ammonium and n can be an integer from one to four. It has been found that the above compound is provided with all the properties that are required of detergents employed in the common solvent systems as above noted. The amount of materials of the present invention that can be employed with the solvent system may range between 0. l0 to 10.0 percent by weight.

DETAILED DESCRIPTION OF THE INVENTION In the practice of the present invention, the dialkyl phosphoryl N-alkyl taurinates are formulated by first reacting phosphorus trichloride with an alkyl alcohol to form a dialkyl phosphite. The alcohols that may be used may be methanol, ethanol, propanol, isopropanol, butanol, and isobutanol. Thereafter, the dialkyl phosphite may be reacted with another alcohol containingfrom six to 16 carbon atoms to produce transesteritication to the higher molecular weight phosphite. ester. The reaction product is then chlorinated to produce the corresponding dialkyl phosphorochloridate. Thelatter intermediate is then reacted with sodium or potassium N-alkyl taurinate or a homolo gthereof, in a manner well known in the art, producing the final product in high yield.

It has been found in practice that from 0.10 to 10.0 percent by weight can be added to the commonly used perc hloroethylene, naphtha, carbon tetrachloride, trichloroethylene or trichloroethane systems to provide superior cleaning properties to the solvent systems.

In order to illustrate the merits of the present invention, the following examples are provided:

EXAMPLE 1 A 500 g. solution of 65 percent N-me'thyl sodium taurinate (46 percent excess over 2 mole proportions) was treated at 20 C., with octyl decylphosphorochloridate and toluene by adding the same over a period of L5 hours and then stirring the same at 25 C., for 2 additional hours. The solids and aqueous byproducts were separated by centrifuging. Thereafter, the solution phase was subjected to evaporation which yielded approximately 100 percent of pure product. The product was determined to be octyl-decyl phosphoryl N-methyl sodium taurinate.

EXAMPLE 2 A solution of 60 g. of taurine (0.48 moles) in 75 milliliters of water with 22.5 g. of potassium hydroxide, was treated with 68 g. of dioctyl phosphorochloridate (0.2 moles) with cooling and strong agitation. This mixture was allowed to react over night and was then diluted with xylene. Then the mixture was azeotropically distilled to remove water. The precipitated byproduct salt wasfiltered and washed with benzene. Since thetaurine' was used in excess, this precipitate consisted of a mixture of 47.4 g. of potassium chloride and taurine. The product, potassium-bis-(Z-ethyl hexyl) phosphoryl taurinate, as isolated from the hydrocarbon, was 89.5 g. The yield of the product was determined to be 95 percent.

EXAMPLE 3 The potassium chloride-taurine mixture of example 2 was mixed with additional potassium hydroxide and potassium taurinate in water and was treated with dihexyl phosphoryl chloridate with bigh-speed stirring, similarly as in example 2. The product was determined to be potassium dihexyl phosphoryl taurinate.

Since a certain amount of water is desirable in dry cleaning systems for optimum cleaning, the solvent relative humidity control of the detergent of example 1 was tested and compared to a commercial detergent. It is reported that the best solvent relative humidity control is between 70 and percent for best soluble, and'insoluble soil removal. The best detergent holds more water while maintaining the solvent relative humidity at these optimum values. Thus, the detergent of example l was added to a perchloroethylene solvent system and also to a naphtha solvent system and tested in a three neck round bottom flask equipped with a suitable stirrer, a thermometer and an Aminco hydrometer sensing element. The temperature of the entire assemblies was controlled by a water bath. The tests were conducted at 75 F. Then, incremental amounts of distilled water were added to each system and after the vapor phase stabilized above the solvent system, the amount of water added was recorded when the relative humidity was between 70 percent and 80 percent. The results of these tests are tabulated below:

alkyl aryl lull'onate 'An isopropyl amine salt of dodccylbenzenesulfonic acid sold under the Trade mark ATLAS G-7ll.

By comparing the results of the above tests with commercial detergents, the amount of water that may be added to the solvent system, using the detergent of this invention to achieve the optimum relative humidity, is higher than the commercial detergents. Thus, the detergents of the present invention have superior solvent relative humidity control properties.

EXAMPLE The detergent of example 1 was tested for insoluble soil removal and redeposition properties. This test measures the ability of the dry cleaning detergent test solutions to remove insoluble soils which are bound to cotton fibers by grease and oil. The test also measures the ability of these test solutions to keep the soil suspended, i.e., prevent its being redeposited upon the clean cloth during the washing cycle. Thus, standard test swatches from F. D. Snell, both soiled and unsoiled, were conditioned in a desiccator at 75 percent relative humidity for several days. The relative humidity of the test fabric was 75 percent when the clothes were placed into the washer. The test solution had a solvent relative humidity of 75 percent at the start of the washing cycle. The ratio of fabric to solvent used was 1 g. of fabric to 25 milliliters of solvent. The swatches were cleaned for 45 minutes in a closed glass container, equipped with a stirrer. After washing, the swatches were rinsed in solvents which contained no detergent, then they were air dried for 12 hours. The reflectances of the swatches were then measured. A drop in reflectance of unsoiled test swatches is a measure of soil redeposition and a gain in reflectance of the soiled swatches is a measure of soil removal. A plus change in reflectance indicates soil removal, a minus change indicates redeposition. High plus values and low minus values are the most desirable. The results of this test are tabulated below:

+33 -l5 A commercial amine l.0 Naphtha +25 -25 alkylaryl sulfonate None Naphtha 'An isopropyl amine salt of dodecylbenzenelulfonic acid sold under Trademark ATLAS G-7l lv EXAMPLE 6 The detergents of example I were tested for water soluble soil removal properties. This test measures the ability of dry cleaning detergent solvent systems to remove water soluble soil from clothing. The National Institute of Dry Cleaning, and most commercial dry cleaners have indicated that sugar removal is the most important of the water soluble soil removal properties. Good soluble soil removal is important to the cleaner because it reduces the need to spot clean certain soiled areas on garments with soap and water sprays. Thus, standard sugar impregnated rayon test swatches were obtained for this test. The test technique used is substantially the same as that outlined in example 5 The differences were that the test swatches contain a standard amount of sugar. The dry cleaning cycle was for 15 minutes rather than 45 minutes. After the swatches were air dried for 12 hours, the remaining sugar in the swatches was dissolved in water and titrated directly. The results are reported as percent sugar removed.

'An isopropyl amine salt of dodecyl enzenesulfonic acid sold under trademark ATLAS 0-7] I EXAMPLE 7 The detergents as set forth in examples 2 and 3 were tested similarly as in examples 4, 5 and 6, with the results being substantially the same.

What is claimed is:

1. (Amended Twice) A composition of the formula:

wherein R is an alkyl group containing from six to 16 carbon atoms; R is an alkyl group containing from six to 16 carbon atoms; R, is hydrogen or methyl an alkyl group containing from one to eight carbon atoms; Y is selected from the group consisting of sodium and potassium and mixtures thereof; and n is an integer from one to four.