US2383739A - Detergent composition - Google Patents

Description

Patented Aug. 28, 1945 DETERGENT COMPOSITION Nathaniel Beverley Tucker, Louisville, Km, assignor to The Procter & Gamble Company, Cincinnati, Ohio, a corporation of Ohio No Drawing. Application July 2, 1942,

a Serial No. 449,496

22 Claims.

The present invention relates to cleansing, washing and laundering compositions of improved efficiency and to the process of producing the semen.

It is an object of my invention to improve the cleansing power of detergent compositions comprising as the essential detergent material watersoluble organic sulfuric acid derivatives containing a sulfate or sulfonate group.

Another object is to prepare detergent compositions of superior cleansing and detergent properties.

Other objects will be apparent from the following description of my invention.

I have found that certain new compounds closely related to each other are outstandingly effective for increasing the cleansing action of sulfate and sulfonate detergents, especially in the washing of woolen fabrics. These compounds are amides having the formula wherein RrCO is the acyl radical of a fatty acid having ten to fourteen carbon atoms, R is selected from the group consisting of hydrogen, methyl, ethyl, and methylol, and each R is selected from the group consisting of hydrogen and methyl. By themselves these amides, which may be referred to as amides of -amino 1,3-dioxanes, are not laundering agents, but when added to a detergent of the class above above named they markedly enhance the cleansing efl'ect thereof. For this purpose the amides described above are in a different class from those preparations such as stearamide and palmitamide which have heretofore been proposed for use with water-soluble compounds in the softening of textile.

Examples of amides which come within the scope of the above general formula and which may be employed in the practice of the present invention are the lauramide of 5-amino 5-methyl 1.3-dioxane, the capramide of 5-amino 5-ethyl 1,3-dioxane, the lauramide of 5-amino 5-ethyl 1,3- dioxane, the myristamide of 5-amino 5-met-hylol 1,3-dioxane, the lauramide of 5-amino 2.5-dimethyl 1,3-dioxane, the lauramide of 5-amino 5- methylol 2,2-dimethyl 1,3-dioxane, the capramide of 5-amino 4,5-dimethyl 1,3-dioxane, the capra mide of 5-amino 5-methylo1 2,6-dimethyi 1,3-dioxane, and corresponding amide mixtures prepared from fatty acid mixtures consisting predominantly of fatty acids having ten to fourteen carbon atoms, such as .those mixtures obtainable from oils of the coconut oil type. of which coconut oil and palm kernel oil are well known examples. The above amides may be prepared from the corresponding amines, which may be synthesized in accordance with U. S. Patent 2,247,256, issued June 24, 1941, to Senkus, and fatty acid chlorides having ten to fourteen carbon atoms in the acyl radical, as follows:

A mixture of 100 parts water, 6 parts sodium carbonate and 12.9 parts 5-amino 5-ethyl 1,3- dioxane is prepared and cooled to 0 C. To this mixture are added dropwise 21.8 parts iauroyl chloride, the temperature of the reaction mixture being maintained at about 0 C. After all lauroyl chloride has been added the mixture is dissolved in ether and washed with 4% sodium carbonate solution and then with water. The washed material is then dried and the amide recovered by evaporation of the ether solvent.

The invention is applicable to the improvement of all detergents coming within the class above mentioned, the advantage of the invention being the improvement in the cleansing power of those sulfates and sulfonates already characterized by substantial power to cleanse rather than the conferring of cleansing power on those materials such as wetting and softening agents which are inactive as detergents.

outstandingly interesting detergent compounds with which the above amides may be used with advantage are the water-soluble salts of the higher molecular weight alkyl sulfuric acids which have distinct and pronounced detergent power making the product suitable for use in cleansing and laundering operations. Thus the invention is particularlyapplicable to the improvement of the already known detergents in which the principal active constituent is a water-soluble salt of other alkyl sulfuric acids having decided detergent value and having eight to eighteen carbon atoms in the alkyl radical are improved by the addition of the amides of the 5-amino 1,3-dioxanes herein covered, and especially are these amides useful in -acid amide of N-methyl taurine).

improving the detergent power 'of the salts of those alkyl sulfuric acids derived from a mixture of higher alcohols obtained from oils of the coconut oil type such asecgconut oil, palm kernel oil,

etc.

Besides the alkyl sulfate detergents referred to above other compounds having a sulfuric acid ester group and value as washing and detergent agents in aqueous solution are improved sulfonate group, these compounds possessing a substantial power to wash and cleanse in aqueous solution in the absence of an enhancing agent. For example, beneficial results will be noted when the amides are employed with water-soluble salts of higher fatty acid esters of 1,2-dihydroxy propane il-sulfonic acid, the sodium salt of the coconut oil fatty acid ester being an excellent example of this type of detergent. Beneiicial results will be noted also when the amides of the S-amino 1,3-dioxanes and their derivatives a,ses,vse

Example 1.To 95 parts of a commercial detergent containing as. active ingredient 40% of the sodium salt of the sulfuric acid ester prepared from the higher alcohols obtained by the reduction of coconut oil, are added parts of the lauramide of 5-amino 5-ethyl 1,3-dioxane. The

- detergent thus preparedis much superior to the commercial detergent alone in cleansing operations.

Example 2.A superior detergent coming within the scope of the present invention is prepared by mixing 90 parts of the commercial alkyl sulfate detergent employed in Example 1 with 10 38% sodium salt of oleic acid amide of N-methyl as above defined are employed with such deter- 1 gents as the water-soluble salts of the higher fatty acid monoesters of lower molecular weight hydroxyalkyl sulfonic acid (oleic acid ester of the sodium salt of isethionic acid) and of the higher fatty acid amides of lower molecular amino alkyl sulfonic acids (ammonium salt of oleic Likewise the amide may be employed with water-soluble salts of the higher alcohol esters of suli'ocarboxylic acids (sodium salt of the lauryl alcohol ester of suifoacetic acid), higher alkylated benzene sulfonic acids (potassium salt of the sulfonic acid derived from the condensation product of benacne and a chlorinated kerosene fraction containing predominantly twelve carbon atoms per molecule), and ethers of high molecular alcohols and lower hydroxy sulfonic acid (monolauryl ether of 1,2-dihydroxy propane 3-sodium sulfonate).

' do not Wish to be limited thereto.

In the practice of my invention, the amide usage will vary depending on the specific combination of ingredients, but in general the quantity of amide will be less than the quantity of active detergent ingredient. I prefer to employ from about eight to about twenty per cent of amide based on the active detergent, but marked improvement can be obtained with smaller proportions and larger proportions, for example proportions within the range from about five per cent to about fifty per cent.

The invention will be more clearly understood from the following examples, but these examples are merely illustrative of the manner in which my invention may be practiced and are not to beconstruedaslimiting. Allpartsareby weight.

taurine as active ingredient with 10 parts of the lauramide of 5-amino 5-ethyl 1,3-dioxane.

Example 5.-To parts of a commercial detergent containing 38% of the sodium salt of the ester of sulfoacetic acid and the mixture of higher alcohols obtained from coconut oil by reduction are added 10 parts of the lauramide of 5- amino 5-ethyl 1,3-dioxane. The resulting mixture has detergent power superior to the suiteacetic acid ester without amide.

Example 6.An improved detergent is prepared by mixing 90 parts of a detergent containing as active constituent 38% of the coconut oil fatty acid monoester of 1,2-dihydroxy propane 3-sodium sulfonate with 10 parts of the lauramide of 5-amino 5-ethyi 1,3-dioxane.

Example -7.A detergent of superior washing power, especially on wool, is prepared by mixing 90 parts of a commercial detergent containing as active constituent the coconut oil fatty acid monoester of 1,2-dihydroxy propane 3-sodium sulfate with 10 parts of the lauramide of 5-amino 5-" ethyl 1,3-dioxane.

Highly eflicient washing agents will result if instead of the specific amides used in the above examples, any of those amides referred to in the general description of the invention is employed.

I have repeatedly referred to the superior washing power of detergents prepared in accordance with my invention and wish to emphasize here that this superiority is apparent to the user and represents a source of substantial saving in detergent usage. For example, detergents such as those of the above specific examples, that is, commercial detergent in admixture with the amides of 5-amino 1,3-dioxanes, when employed in 0.2 per cent concentration in hard water, a. normal concentration used in laundering, will wash much whiter than any concentration of the commercial detergent without added amide. In general, a solution containing any given concentration of a cleansing compound prepared in accordance with the present invention will wash as white as, or whiter than, a solution containing a much larger concentration of detergent without added amide.

My invention is not limited to any particular method of mixing the amide compounds with the essence 3 pounds to water prior to the adding of the detergent, or vice versa, or to add both amide and detergent simultaneously but water. I

Having thus described my invention, :what I claim and desire to secure by Letters Patent'is:

l. A cleansing and laundering comprising essenuauy a mixture of swam-solufole' salt of an organic sulfuric having in its molecularstructurea" radical aelected from the group consisting ofsu li'onic acid and sulfuric acid ester radicals. the said salt having pronounced .deterge'nt power. and. an

amide having the following general formula m-co-Nn came-o a wherein RrCO is the acyl of a fatty separately to claimed in claim 1, in which the acyl radical of the amide i derived from lauric acid.

.8. A cleansing and laundering composition claimed in claim 1, in which the acyl radical of the 5 amide is derived from myristic acid.

;'l. A cleansing and laundering composition claimed in claim 1, in which the amide is the lauramlde of li-amino 5-ethy1 Lit-diorama.-

.8. A cleansing and laundering composition claimed in claim 1, in which the amide is the myristamide of B-amino ii-ethyl 1.3-dioxane. v 9. A cleansing and laundering composition inclaim 1, in which the amide is the on fatty acid amide of Ii-amino fi-methyl l5 LS dioxane.

1 A cleansing and laundering composition in claim 1, in which the detergent. material. is 'ja water-soluble salt of an aliphatic sulfin'icja'cidester containing eight to eighteen carurainide of ii -amino li-ethyl 1,3-dioirane.

, cleansing and laundering composition in; claim 1, in which the detergent materialjis the water soluble salt of an alkyl sulfuric g5- acid derived-from higher alcohols obtained from coconut on and the amide is the lauramide of 5- amino li-ethyl l,3'-dioxane.

- i2, Ajcleansin'g and laundering composition claimed in claim 1, in which the detergent mathe' alkyl radical, and the amide isfhaving 10 to 14 arbon atoms, R i selected 3o "terial ita'w'ater-soluble salt of an alkyl sulfuric the group consisting of hydrogen, methyl, mech- ,facid {derived from the higher alcohols obtained y lol, and ethyl. and each R is selected from the from coconut oil and the amide is the lauramide of group consisting of hydrogenandinethyl. the amount by weight of the amide being less .thanthe amount by weight of. the said detergent nia terial but sui'ilcient to enhance thedetergcnt power thereof.

2. A cleansing and laundering composition comprising essentially a mixture of a detergent selected from the group consisting of water-soluble salts of: higher alkyl sulfuric acids, higher fatty acid esters of lower molecular weight hydroxy alkyl sulfonic acids, higher .fatty acid amides of low molecular amino alkyl sulfonic acids, higher fatty acid monoglyceride sulfuric acids, higher alcohol esters of sulfocarboxylic acids, higher alkylated benzene sulfonic acids, higher alcohol ether; of low, molecular hydroxy alkyl sulfonic acids, and higher fatty acid alkylolamide sulfuric acidaand an amide of the formula R1.C0-NH CH(R')- 0 a l n on n' -o n' wherein Rl'CO is the acyl radical of a fatty acid having 10 to 14 carbon atoms, R. is selected from the group consisting of hydrogen, methyl, methylol, and ethyl, and each R is selected from the group consisting of hydrogen and methyl, the amount by weight of the amide being less than the amount by weight of the said detergent material but sufficient to enhance the detergent power thereof.

3. A cleansing and laundering. composition claimed in claim 1, in which the acyl radical of the amide is derived from a mixture of fatty acids consisting predominantly of lauric and myristic m-co-Nn sj-ommo. B-methyl 1,3-dioxane.

d3. A cleansing and laundering composition 135.: comprising essentially a mixture of. a water-solu- ,ble salt of the coconut oil fatty acid monoester of 4' 1,2-dihydroxy propane 3-sulfonic acid, and an amide of the formula m-co-Nn omao-o B 5 from' the group consisting of hydrogen, methyl, methylol. and ethyl, and each R is selected from the group consisting of hydrogen and methyl, theweight of the amide being less than the weight of the said water soluble salt but sufllcient to enhanoc the detergent power thereof.

14. A cleansing and laundering composition comprising essentially a mixture of a water-soluble salt of coconut oil monoglyceride sulfuric acid ester and an amide of the formula cums-0 a v n cnum-o R wherein Rr-CO is the acyl radical of a fatty acid 0 having ten to fourteen carbon atoms, R is selected from the group consisting of hydrogemmethyl, methylol, and ethyl, and each R. is selected from the group consisting of hydrogen and methyl, the weight of the amide being less than the weight of the said. water soluble salt but suillcient to enhance the detergent powerthereof.

15. As a detergent improving agent possessing the power to enhance the cleansing efficiency of organic sulfate and sulfonate laundering agents,

especially on woolens, an amide of the formula to wherein ai-co is the acyl radical of a fatty so.

especially on woolens, an amide of the formula R/ cmn'i-o wherein R1-CO represents the acyl radicals of a mixture of fatty acids derived from coconut oil and consisting predominantly of lauric and myristic acids, R is selected from the group consisting of hydrogen, methyl, methylol, and ethyl, and each R is selected from the group consisting of hydrogen and methyl.

17. As a detergent improving agent possessing the power to enhance the cleansing efllciency of organic sulfate and sulfonate laundering agents, especially on woolens, the lauramide of S-amino 5-methyl 1,3-dioxane. ,7

18. As a detergent improving agent possessing the power to enhance the cleansing efllciency of organic sulfate and sulfonate laundering agents, especially on woolens, the myristamide of 5-amino 5-ethyl 1,3-dioxane.

19. As a detergent improving agent possessing the power to enhance the cleansing eiliciency of organic sulfate and sulfonate laundering agents, especially on woolens, an amide derived from a mixture of higher fatty acids contained in coconut oil and consisting predominantly of lauric and myristic acid, and 5--amino S-methyl 1,3- dioxane.

20 A cleansing and laundering composition comprising essentially a mixture of a water soluble salt of an alkyl sulfuric acid having eight to eighteen carbon atoms in the alkyl radical and having pronounced detergent power, and an amide of the formula c R CH(B')-0 \R wherein R1 00 is the acyl radical of a fatty acid having ten to fourteen carbon atoms, R is selected from the group consisting of hydrogen, methyl, methylol, and ethyl, and each R is selected from the group consisting of hydrogen and methyl, the amount by weight of the amide being less than the amount by weight of the said water soluble salt but suflicient to enhance the detergent power thereof.

21. A cleansing and laundering composition claimed in claim 1 in which the amount of the amide is from about 5 per cent to about per cent by weight of the detergent material having pronounced detergent power.

22. A cleansing and laundering composition claimed in claim 1 in which the amount of the amide is from about 8 per cent to about 20 per cent by weight of the detergent material having pronounced detergent power.

NATHANIEL BEVERLEY TUCKER.