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Publication numberUS2527075 A
Publication typeGrant
Publication dateOct 24, 1950
Filing dateFeb 24, 1947
Priority dateFeb 24, 1947
Publication numberUS 2527075 A, US 2527075A, US-A-2527075, US2527075 A, US2527075A
InventorsPreston Walter C
Original AssigneeProcter & Gamble
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Detergent composition
US 2527075 A
Images(6)
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Description  (OCR text may contain errors)

Patented Oct. 24, 1950 DETERGENT COMPOSITION Walter C. Preston, Cincinnati, Ohio, asaignor to The Procter & Gamble Company, Cincinnati, Ohio, a corporation of Ohio No Drawing. Application February 24, 1947, Serial No. 730,558

The present invention relates to detergent compositions, and more particularly to soap-comtaining compositions which are highly resistant to curd-forming ingredientsof hard water.

It is well known that the use of ordinary toilet or household soap in hard water results in the formation and precipitation of insoluble fatty acid salts, more commonly referred to as lime soaps. It is also known that such precipitated lime soaps have a tendency to coagulate and form a sticky curd. This curd is commonly observed in the washstand and bath tub and also in the laundry rinse tub where it rises to the surface of the water as a scum, adheres to the walls of the tub as a ring, and sticks to the clothes during the rinsing operation, thereby giving to the clothes an unsightly dingy appearance, producing spots upon subsequent ironing, and often causing the development of a rancid odor. When soap is used for shampooing the hair, rinsing with hard water results in deposition of the lime soaps on the hair. In applications as divergent as the dyeing of textile fabrics and the plating of metals, the formation of lime soaps has undesirable effects.

In face, whenever soap is used in hard water, insoluble lime soap curd forms during the rinsing process when the soap dilution becomes sufficiently great to destroy the foaming and dispersing power of the soap.

The coagulation of the lime soaps to form soap curd is dependent not only on the degree of dilution of the soap in the hard water, but also on the age of the solution and on the degree of violence of agitation to which it is subjected, increasing age and increasing agitation both being important factors in promoting coagulation.

The primary object of the present invention is to provide a soap composition which forms little or no lime soap curd when used with hard water.

Another object is to provide a detergent composition which will not form a sticky lime soap curd which 'will cling to clothes or form the unsightly, difficulty removable soap ring in the washstand or bathtub.

A further object is to increase the resistance of soap-containing detergent compositions to precipitation of lime soap and the coagulation thereof to form curd when such compositions are used in hard water under conditions involving prolonged standing or agitation.

It is known that synthetic detergents such as the various organic sulfonates, alkyl sulfates, and other organic sulfuric acid derivatives, when mixed or used with soap in hard water are capable of 5 reducing the formation of lime soap curd. Sev- 14 Claims. (01.252-121) I erai such mixtures have been proposed. Some have been commercially produced and designated as hard water soaps," allegedly free of curd forming characteristics when used in hard watera However, according to my investigations and experience, products prepared in accordance with prior art practices, even those which contain more synthetic detergent than soap, frequently form objectionable curd in hard water under normal conditions of use. As the proportion of synthetic detergent increases, the trouble with such hard water curd may decrease in seriousness, but at the same time the cost .of the product increases and some of the desirable physical properties found in soap are adversely affected.

As more fully hereinafter described, I have discovered that higher molecular alcohols (although possessing no power to inhibit curd formation. when used with soap alone) have a marked power to inhibit lime soap precipitation and curd formation in the case of curd-forming detergent compositions comprising essentially a mixture of soap and synthetic detergent in proportions more fully hereinafter described. This power exists even when the compositions are used under conditions wherein the solution is subjected to prolonged standing or to mild or vigorous agitation.

I am aware that prior workers in the art have suggested the combination of soap with synthetic detergents (Patents 1,906A8, 2,026,816 and 2,088,308). I am also familiar with recently issued patents covering the use of certain higher alcohols with synthetic detergents to improve the sudsing and detergent power thereof (Patents 2,166,314 and 2,166,315). None of these patents, however, suggests the use of higher alcohols for inhibiting the curd formation when compositions comprising soap and synthetic detergent are employed in hard water.

Higher molecular alcohols which come within the scope of the invention are primary and secondary saturated or unsaturated aliphatic alcohols having from about 10 to about 20 carbons. Of especial interest are straight chain primary saturated aliphatic alcohols having 10 to 14 carbon atoms.

Some specific alcohols which may be used in the practice of the present invention are:

n-decyl alcohol, CH3 CH2 aCHaOI-I n-dodecyl alcohol, CHa(CH2) mCHaOE n-tetradecyl alcohol, CHa(CH2)12CH2OE n-hexadecyl alcohol, CHa(CH2)14CH2OH n-octadecyl alcohol, CHa(CHz)1aCHzOI-I octadecenyl alcohol,

CHflCI'I?) 1CH:CH(CH:)1CH2OH Corresponding secondary alcohols such as secondary lauryl alcohol, secondary tetradecyl alcohol and the like may be used.

Instead of employing individual alcohols as above indicated, mixtures of such alcohols, especially those mixtures obtainable by reduction of oils, fats, and waxes of animal and vegetable origin, may be employed without departing from the spirit of the invention. For example, the mixture or higher alcohols derived by reduction of oils of the coconut oil group (a group of tropical nut oils characterized by their high content of lauric and myristic acids) such as coconut oil, palm kernel oil, and babassu oil are of particular value, but higher alcohols derived by reduction of other oils and fats such as palm oil, tallow, cottonseed oil, sunflower seed oil, fish oils such as menhaden oil and the like, as well as hydrogenated and partially hydrogenated fats and oils in general, may also be employed. In addition, higher alcohols derived by the oxidation of aliphatic hydrocarbons, for example those secondary alcohols having from to carbon atoms derived by the oxidation of parailln hydrocarbons, have been found suitable in the practice of the invention.

The kind of soap which is used in preparing my improved detergent compositions is not a limitation of the invention. Any of the water-soluble soaps formulated for industrial, household, and toilet use may be employed. Thus the character of the soap constituent may vary widely in its composition depending on whether the final ternary composition is to be in powdered, spray dried, flake, bar, paste, thread, liquid or other form, and it is to be understood that the specific soaps referred to in the examples given below are not to be construed as limiting in nature. Water-soluble soaps such as the sodium, potassium and other suitable alkali metal or ammonium soaps or soaps prepared from nitrogen bases, such as triethanolamine, derived from other fats and oils such as cottonseed oil, soybean oil, corn oil, olive oil, palm oil, peanut oil, palm kernel, lard, greases, fish oils and the like as well as their hydrogenated derivatives, and mixtures thereof, properly blended to yield the desired soap quality, may be used in compounding the ternary mixtures herein contemplated.

The synthetic detergent constituent of the present detergent compositions may be broadly designated as a detergent of the class consisting of water-soluble salts of organic sulfonic acids and water-soluble salts of aliphatic sulfuric acid esters, that is, water-soluble salts of organic sulfuric reaction products having in the molecular structure a radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals. As indicated above in the designation of the soaps which may be used in compounding the compositions of my invention, the choice of synthetic detergent will depend inter alia on the physical characteristics of the final product, that is, whether the composition is to be in flake, bar, paste, or other form. Obviously if a detergent composition in bar form is desired, it will be impractical to combine ingredients which are too soft to retain their shaped form in use.

Synthetic detergents 01. special interest and particular value are the water-soluble salts of higher alkyl sulfuric acids containing from 8 to 18 carbon atoms in the alkyl radical. More specifically, the alkali metal salts of sulfuric acid esters of normal primary aliphatic alcohols having 10 to 18 carbon atoms, particularly those whose principal active ingredient is a watersoluble salt of lauryl sulfuric acid or oleyl sulfuric acid, have proved of value in compounding products of the present invention. Thus the sodium salt of alkyl sulfates obtained from the mixed higher alcohols derived by the reduction of coconut oil, palm kernel oil, babassu oil, or other oils of the coconut oil group or the sodium alkyl sulfate derived from sperm oil alcohols may be employed. In addition, water-soluble alkyl sulfates having pronounced detergent power and derived from high molecular branched chain primary alcohols or from high molecular secondary alcohols may be used.

Other aliphatic sulfuric acid esters which may be employed in the preparation of detergent compositions of the present invention include watersoluble salts of sulfuric acid esters of polyhydric alcohols incompletely esterifled with high molecular weight soap forming carboxylic acids. Such synthetic detergents include the watersoluble salts of sulfuric acid esters of higher molecular weight fatty acid monoglycerides such as sodium salt of the coconut oil fatty acid mono-ester of l,2-dihydroxypropane-3-sulfuric acid ester, triethanolamine salt of monooleoyl diethylene glycol sulfate, sodium mono-myristoyl ethylene glycol sulfate, and sodium monolauroyl diglycerol sulfate.

Similarly water-soluble salts of ethers of high molecular weight normal primary alcohols and lower molecular weight hydroxy alkyl sulfuric acid esters may be employed. Specific examples of such. synthetic detergents are sodium salt of mono fatty-alcohol-of-coconut-oil ether of glycerol monosulfuric acid and sodium salt of lauryl ether of ethylene glycol monosulfuric acid and sodium salt of lauryl ether of diethylene glycol monosulfuric acid.

In addition, sulfuric acid ester synthetic detergents such as water-soluble salts of sulfated higher fatty acid alkylolamides, for example the sodium salt of sulfated coconut oil fatty acid e'thanolamide and of sulfated babassu oilfatty acid glycerol amide, may be employed in the practice of the invention.

The higher alcohols hereinabove mentioned are active also in inhibiting curd formation in the case of those detergent compositions which contain in combination with soap an organic synthetic detergent having a true sulfonate group. These synthetic detergents include salts of higher molecular weight monofatty acid esters of lower molecular weight hydroxy alkyl sulfonic acids such as the sodium salt of the coconut oil fatty acid monoester of 1,2-dihyroxy-propane-3-sulfonic acid, and the oleic acid ester of the sodium salt of isethionic acid. Included also are the higher molecular weight fatty acid amides of lower molecular weight animo alkyl sulfonic acids (for example, potassium salt of oleic acid amide of N-methyl taurine), the water-soluble salts of the higher molecular weight alcohol esters of sulfocarboxylic acids (for example, sodium salt of the lauryl alcohol ester of sulfoacetic acid), lower molecular weight sulfocarboxylic acid amides of alkylolamine esters of higher molecular weight fatty acids (for example, sodium salt of the sulfoacetamide of amino ethyl laurate), higher alkylated aryl sulfonic acids (for example, potassium salt of the sulfonic acid derived from the condensation product of benzene and a chlorinated kerosene fraction containing predominantly 12 carbon atoms per molecule), and ethers of higher molecular weight alcohols and lower molecular weight hydroxy alkyl sul- Ionic acids(for example, monolauryl ether of the sodium salt of isethionic acid).

Although the cleansing agent of the compositions of the present invention comprises essentially a ternary mixture of higher alcohol, soap and synthetic detergent, it will be appreciated that the incorporation in the mixture of additional ingredients commonly used with cleansing compositions, such as perfumes, starch, urea, triethanolamine, inorganic salts (silicates, carbonates, ortho-, meta-, pyro-, and triphosphates and the like), albuminous substances, glycerin, insecticides and germicides and the like, is contemplated as part of the instant invention.

The following examples will illustrate the manner in which the invention may be practiced, but it is to be understood that such details are given merely for exempliflcation purposes and are not to be construed as limiting the scope of the appended claims. In all instances the proportions are expressed in parts by weight.

Example 1.Five parts of an unfractionated mixture of higher molecular alcohols derived by the reduction of coconut oil, 70 parts of sodium soap derived from a mixture of 80% tallow and coconut oil and containing about 15% moisture, and parts of a commercial alkyl sulfate containing about 88% synthetic detergent (the sodium salt of alkyl sulfuric acids derived from coconut oil alcohols) were mixed and milled by passing over soap milling rolls in accordance with accepted procedure to produce a homogeneous product. The product resulting from the milling was then plodded and cut and stamped in the form of a bar. The ratio of soapzsynthetic was about 27:1, and the ratio of syntheticzalcohol was about 4.421. The detergent bar may be employed with 21 grain hard water in the washstand or bathtub for toilet use without the formation of objectionable soap ring.

In an ancillary example, lauryl alcohol or myristyl alcohol instead of the mixture of alcohols derived from coconut oil may be used.

. Example 2.-In accordance with the procedure of Example 1 a detergent bar was prepared from the same three ingredients with amounts as follows: l6 parts-coconut oil higher alcohol, 24 parts alkylsulfate synthetic detergent, parts soap. The ratio of soapzsynthetic was about 24:1, and the ratio of syntheticzalcohol was about 1.3:1.

Instead of employing coconut oil alcohol as set forth in Example 2, a mixture of C10 to C20 secondary alcohols derived by the oxidation of paraffin wax may be used.

Another example along the same lines involves substitution of 26.4 parts of Nacconol NRSF (a synthetic detergent product containing 80% of the sodium salt of the sulfonic acid of the condensation product of benzene and the chloride of a kerosene fraction containing predominantly 12 carbon atoms, in the hydrocarbon chain, and 20% inorganic salts) for the 24 parts alkyl sulfate used in Example 2.

Example 3.In accordance with the procedure of Example 1, a detergent bar was prepared from the same three ingredients with amounts as folsubstitution of about 255 parts of the sodium salt of the sulfuric acid mono-ester of coconut oil monoglyceride or of about 55.5 parts of "Igepon A" (containing 46% ot the oleic acid ester of sodium isethionate as the active synthetic de- 1 tergent and about 54% of inorganic salts) for the alkyl sulfate synthetic detergent used in Example 3.

Example, 4.The following mixture was suitably milled and converted into bar form. 15 parts octadecyl alcohol, 60 parts of the same soap used in Example 1, and 25 parts of Nacconol LA" (containing about 73% of the sodium salt of coconut 011 higher alcohol ester of sulfoacetic acid as the active synthetic detergent and about 27% inorganic salts). The ratio of soap:synthetic was about 2.8:1, and the ratio of syntheticzalcohol was-about 12:1. The product was used in 21 grain hard water without the formation of objectionablesticky curd.

An efllcient bar may also be produced by substituting about 18.2 parts of sodium oleyl sulfate or of coconut oil monoglyceride sodium sulfonate for the 25 parts of "Nacconol LA" used in Example 4.

Example 5.-5l.6 parts of dry sodium soap prepared from fish oil hydrogenated to an iodine value of about 65, 16.1 parts of dry sodium soap prepared from coconut oil, 24.3 parts of alkyl sulfate detergent used in Example 1, and 8 parts of an unfractionated mixture of higher molecular alcohols derived by the reduction of coconut oil were combined and mixed with about 4% water. The mixture was then run over a soap milling roll until a homogeneous mixture of ingredients was obtained. The soap was removed from the rolls in the form of thin ribbons which were dried and then broken up into suitable flake form. In the composition thus prepared, the ratio of soaprsynthetic was about 3.221, and the ratio of syntheticzalcohol was about 2.7 :1. No sticky curd is formed when the flakes are used to wash dishes in water of 21 grain hardness.

In an ancillary example, 21.4 parts of the oleic acid amide of the sodium salt of methyl taurine may be substituted for the alkyl sulfate synthetic detergent used in Example 5.

Example 6.32 parts dry sodium soap derived from tallow, 8 parts of dry potassium soap from coconut oil, 48.4 parts of the sodium salt of lauryl ether of ethylene glycol monosulfuric acid, and 5 parts; of decyl alcohol are mixed with about 4 parts water and milled and converted into flake form as in Example 5. In'the instant example the ratio of soap :synthetic is about 0.83:1 and the ratio of syntheticzalcohol is about 9.7:1.

Other examples along the same line involve the substitution of the sodium salt of sulfated coconut oil fatty acid ethanolamide, or the sodium salt of the sulfo acid amide of amino ethyl laurate, or the monolauryl ether of 1,2-dihydroxy-propane-S-sodium sulfonate, for the synthetic detergent used in Example 6.

Example 7 .3 .parts of mixed alcohols derive by the reduction of coconut oil are mixed with 81 parts of essentially dry sodium soap derived from a mixture of 75% tallow and 25% coconut oil; and with 16 parts of the dry sodium salt of the sulfuric acid esters of coconut oil monoglyceride. Enough water is added to produce a homogeneous coherent flake when the mixture is subsequently passed over soap milling rolls to convert it into flake form. In the mixture thus formed the ratio of soapzsynthetic is 51:1, and the ratio of syntheticzalcohol is 5.3:1. The resulting product may be used for detergent purposes in hard water with decreased formation of hard water curd.

Example 8.23 parts of mixed alcohols used in Example 7 are mixed with 54 parts of sodium soap used in Example 7, and with 23 parts .of the dry sodium salt of the sulfonic acid of the condensation product of benzene and the chloride of a kerosene fraction containing predominantly 12 carbon atoms. Enough water is added to give a homogeneous paste upon stirring at elevated temperature. The ratio of soap:synthetic is about 2.4:1, and the ratio of syntheticzalcohol is about 1:1. detergent purposes with decreased formation hard water curd.

E's-ample 9.24 parts of the mixed alcohols used in Example 'I are mixed with 36 parts of sodium soap used in Example 7, and with 40 parts of the dry sodium salt of the sulfuric acid ester of mixed alcohols derived by the reduction of coconut oil. Enough water is added to give a homogeneous paste upon stirring at elevated temperature. The ratio of soapzsynthetic is about 0.9:1. and the ratio of synthetic:alcohol is about 1.7:1.

Example 10.4 parts of the mixed alcohols used in Example 7 are mixed with 36 parts of the dry soap used in Example 7, and with 60 parts of the synthetic detergent used in Example 8. Enough water is added to produce a homogeneous coherent flake when the mixture is passed over The resulting product may be used for soap milling rolls. The ratio of soapzsynthetic is about 0.621, and the ratio of soapzalcohol is about 15:1.

Example 11.- 10 parts of the mixed alcohols used in Example 7 are mixed with parts of the soap used in Example 7, and with 40 parts of the synthetic detergent used in Example 9. Enough water is added to produce a homogeneous coherent flake when the mixture is passed over soap milling rolls. The ratio of soap:synthetic is about 1.221, and the ratio of synthetic:alcohol is about 4: 1.

Reference has been made above to the use of the detergent compositions of the present invention in water of 21 grains of hardness per gallon. It is to be understood, however, that 21 grain water is referred to only as being representative of hard waters in general. According to my experience and investigations my ternary detergent composition is eifective in hard water of any municipal water system or any domestically used water source of which I am aware.

Besides possessing resistance to curd formation in hard water, products of the present invention dissolve at a desirable rate in water, suds profusely and cleanse emciently. I

The amount of alcohol that can advantageously be used decreases with increasing molecular weight of the alcohol and is also to a degree dependent upon the nature and amount of synthetic detergent present in the composition, but it has been found that the most useful products result when the amount of alcohol exceeds 5 per cent of, but is not greater than. the amount of synthetic detergent present and constitutes at least 2 per cent of the combined weights of the soap, synthetic and alcohol.

In connection with the use of synthetic detergents made from higher alcohols, such as the alhrl sulfates for example, the desired proportion of alcohol in the final mixture may be arrived at by employing a synthetic which has been prepared .under controlled conditions of reaction adapted to leave unreacted higher alcohol in the product in uitable proportion.

Most of the above examples cover compositions in which theratios of essential ingredients come within the preferred ranges, that is, a ratio of soapzsynthetic from about 0.6:1 to about 4:1 and a ratio of syn thetic:higher alcohol from about 1:1 to about 10:1. The advantages of my discovery, however, are to be realized in compositions falling outside the preferred ranges of proportions, and accordingly compositions coming within the ratios of soap:synthetic of about 0.5:1 to about 6:1 and of syntheticzhigher alcohol 0! about 1:1 to about 20:1 are contemplated as part of the broad invention, the higher alcohol constituting at least 2 per cent of the combined weights of soap, synthetic, and higher alcohol. Optimum results in the case of each composition may be realized by adjustment of the ratios used depending on the types of soap, synthetic detergent, and higher alcohol employed.

As indicated above, the physical form of the compositions is not a limitation of the invention and may be varied in well known manner. In some instances, however, it may be necessary to adjust temperature conditions or moisture content of the mixture to give a product of the desired consistency for handling in the various processing operations required in the development of the desired physical form. Such adjustments of course are well within the scope of those skilled in the art.

. The manner of mixing the ingredients is not a limitation of the invention. Any suitable mixing device such as a series of milling rolls ordinarily used in mixing plastic soap with added incredients 0r crutching mechanism of high mixing efficiency as employed in mixing more fluid constituents may be employed to effect homogeneity in the mixture of higher alcohol, soap, and synthetic detergent.

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

-1. A detergent composition characterized by reduced tendency to form sticky lime curd when used in hard water at rinsing dilutions, comprising essentially a ternary mixture of a watersoluble soap, a water-soluble salt 01' an organic sulfuric reaction product having pronounced detergent properties and having in it molecular I soap:sulfuric reaction product salt being from about 0.5:1 to about 6:1, the ratio of sulfuric reaction product saltzhigher alcohol being from about 1 :1 to about 20:1, and the amount of higher alcohol constituting at least 2 per cent of the combined weights of the soap. sulfuric reaction product salt and higher alcohol.

2. A detergent composition characterized by reduced tendency to form sticky lime curd when used in hard water at'rinsing dilutions, comprising essentially a ternary mixture of a water-soluble soap, a water-soluble salt of an organic sulfuric reaction product having pronounced detergent properties and having in its molecular structure a radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals, and a higher aliphatic alcohol selected from the group consisting of primary and secondary saturated and unsaturated higher alcohols having from to carbon atoms, the ratio of soap:suliuric reaction product salt being from about 0.6: 1 to about 4:1, the ratio of sulfuric reaction product saltzhigher alcohol being from about 1:1 to about 10:1, and the amount of higher alcohol constituting at least 2 per cent of the combined weights of the soap, sulfuric reaction product salt and higher alcohol.

3. The composition of claim 1 in which the higher alcohol is a mixture of higher molecular primary alcohols obtainable by reduction of a naturally occurring fat.

4. The composition of claim 1 in which the higher alcohol is a mixture of higher molecular primary alcohols derived from an oil of the group consisting of coconut, palm kernel and babassu oils and consisting predominantly of saturated alcohols having 10 to 14 carbon atoms.

5. The composition of claim 1 in which the higher alcohol is a mixture of higher molecular primar alcohols derived from coconut oil and consisting predominantly of saturated alcohols having 10 to 14 carbon atoms.

6. The composition of claim 1 in which the higher alcohol consists predominantly of lauryl alcohol.

7. The composition of claim 1 in which the higher alcohol consists predominantly of decyl alcohol.

8. The composition of claim 1 in which the higher alcohol consists predominantly of tetradecyl alcohol.

9. The composition of claim 1 in which the organic sulfuric reaction product salt is a watersoluble salt of an alkyl sulfuric acid having from 10 to 18 carbon atoms in the alkyl radical.

10. The composition of claim 1 in which the sulfuric reaction product salt is a water-soluble salt of alkyl sulfuric acids of higher alcohols de-' rived from an oil of the group consisting of coconut, palm kernel and babassu oils.

11. The composition of claim 1 in which the sulfuric reaction product salt consists of a watersoluble salt of dodecyl sulfuric acid and in which the higher alcohol consists of lauryl alcohol.

12. The composition of claim 1 in which the sulfuric reaction product salt consists of a watersoluble salt of a higher alkylated aryl sulfonic acid.

13. The composition of claim 1 in which the sulfuric reaction product salt is a water-soluble salt of the coconut oil-fatty acid-monoester of l,2-dihydroxy-propane-3-sulfuric acid ester.

14. A detergent composition characterized by reduced tendency to form sticky lime soap curd when used in hard water at rinsing dilutions, comprising essentially a mixture of a water-soluble soap, a water-soluble salt of an alkyl sulfuric acid having from 10 to 18 carbon atoms in the alkyl radical, and high molecular primary allphatic alcohols derived from an oil of the group consisting of coconut, palm kernel and babassu oils and consisting predominantly of saturated al- REFERENCES CITED The following references are of record in the file of this patent:

UNITED STATES PATENTS Number Name Date 2,004,874 La zier June 11, 1935 2,026,816 Bertsch Jan. 7, 1936 2,166,314 Martin July 18, 1939 Certificate of Correction Patent No. 2,527,075 October 24, 1950 WALTER C. PRESTON It is hereby certified that error appears in the printed specification of the above ni mbered patent requiring correction as follows:

Column 1, line 44, for difficulty read diyfimdtly; column 7 line 42, for 1.2 :1 read 1.3 :1;

. and that the said Letters Patent should be read as corrected above, so that the same may conform to the record of the case in the Patent Oflice. Signed and sealed this 2nd day of January, A. D. 1951.

THOMAS F. MURPHY,

Assistant Oommiaaioner of Patents.

Patent Citations
Cited PatentFiling datePublication dateApplicantTitle
US2004874 *Aug 18, 1932Jun 11, 1935Du PontProduct and process for preparing same
US2026816 *Oct 3, 1931Jan 7, 1936American Hyalsol CorpSoap preparation
US2166314 *Aug 13, 1935Jul 18, 1939Procter & GamblePreparation of detergents
Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US2731422 *Oct 18, 1949Jan 17, 1956Colgate Palmolive CoNon-soap detergent compositions
US3072580 *Aug 7, 1957Jan 8, 1963Gillette CoShampoo composition
US3625906 *Oct 29, 1968Dec 7, 1971Lever Brothers LtdSoap-detergent tablets
US4260507 *Sep 19, 1979Apr 7, 1981Lever Brothers CompanySoap-synthetic detergent tablets
US4304680 *Oct 13, 1977Dec 8, 1981Colgate-Palmolive CompanyLaundry soap
US5565420 *Jun 6, 1995Oct 15, 1996The Procter & Gamble CompanyGranular detergent composition containing admixed fatty alcohols for improved cold water solubility
WO1995031525A1 *Apr 17, 1995Nov 23, 1995Procter & GambleGranular detergent composition containing admixed fatty alcohols for improved cold water solubility
Classifications
U.S. Classification510/482, 510/448, 510/404, 510/445
International ClassificationC11D1/16, C11D9/26, C11D10/00, C11D1/22, C11D1/02, C11D10/04, C11D1/14, C11D9/04
Cooperative ClassificationC11D9/26, C11D1/16, C11D10/042, C11D1/22, C11D1/14
European ClassificationC11D10/04B, C11D9/26