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US2773834A - Shampoo compositions containing monomethylol dimethyl hydantoin - Google Patents

Shampoo compositions containing monomethylol dimethyl hydantoin Download PDF

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US2773834A
US2773834A US381509A US38150953A US2773834A US 2773834 A US2773834 A US 2773834A US 381509 A US381509 A US 381509A US 38150953 A US38150953 A US 38150953A US 2773834 A US2773834 A US 2773834A
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shampoo
dimethyl hydantoin
compositions
shampoo compositions
weight
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US381509A
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Henkin Hyman
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Colgate Palmolive Co
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Colgate Palmolive Co
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
    • A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
    • A61K8/4946—Imidazoles or their condensed derivatives, e.g. benzimidazoles

Definitions

  • the present invention relates to shampoo compositions and has particular reference to shampoo compositions comprising in combination a water-soluble organic anionic synthetic detergent and monomethylol dimethyl hydantoin in an aqueous medium.
  • shampoo compositions containing many different types of detergents are suggested in the prior art.
  • some shampoo compositions contain soap, i. e., watersoluble salts of fatty acids as the active detersive or cleansing ingredient.
  • soap i. e., watersoluble salts of fatty acids
  • non-soap synthetic detergents are used instead of soap, while in still others various synthetic detergents are used in combination with soap.
  • compositions which contain anionic sulfate and sulfonate salts as the principal cleaning ingredient have enjoyed a considerable amount of commercial success in recent years. Such compositions exhibit high water solubility and have excellent detergent and foaming properties.
  • Representative compounds which may be suitably employed include the sulfuric acid esters of polyhydric alcohols incompletely esterified with higher fatty acids, e. g., coconut oil monoglyceride monosulfate, tallow diglyceride monosulfate; the long chain pure or mixed alkyl sulfates, e. g., lauryl sulfate, cetyl sulfate, higher fatty alcohol sulfates derived from coconut oil; the hydroxy sulfonated higher fatty acid esters, e. g., higher fatty acid esters of 2,3-dihydroxy propane sulfonic acid; the higher fatty acid esters of low molecular weight alkylol sulfonic acids, e.
  • higher fatty acids e. g., coconut oil monoglyceride monosulfate, tallow diglyceride monosulfate
  • the long chain pure or mixed alkyl sulfates e. g., la
  • oleic acid esters of isethionic acid e.g., oleic acid esters of isethionic acid
  • the sulfated higher fatty acid alkylolamides e. g., ethanolamide sulfates
  • the higher fatty acid amides of amino alkyl sulfonic acids e. g., lauric amide of taurine, and the like.
  • anionic synthetic detergent materials which may be employed include those materials known generally as the alkylated aromatic hydrocarbon compounds having an alkyl substituent containing about 8 to 26 carbon atoms.
  • the aromatic portion of the 4 molecule may be monoor polynuclear in structure, e. g.,
  • the darkening in color and the development of an unpleasant odor is associated with the growth and multiplication of bacteria and mold. It is further believed that the synthetic detergent material furnishes the nutrient medium in which the bacteria and mold grow and multiply.
  • the shampoo compositions of this invention consist essentially of at least one water-soluble organic anionic synthetic detergent selected from the group consisting of sulfated and sulfonated detersive salts, and monomethylol dimethyl hydantoin in an aqueous medium.
  • the invention is applicable to shampoo compositions containing water-soluble anionic synthetic detergents which are well known in the art.
  • Representative exbenzene, toluene, xylene, naphthalene, phenanthrene, anthracene, etc. and may contain other substituents such as hydroxyl groups, e. g., phenols, cresols, phenol ethers, short chain alkyl groups, e. g., alkylated toluene, alkylated xylene, etc.
  • the long chain alkyl substituent of the alkylated aromatic molecule preferably is saturated and may be straight or branched.
  • Representative long chain alkyl groups include such radicals as dodecyl; hexyl; octyl; nonyl; decyl; mixed alkyls derived from fatty materials, cracked parafiin wax olefins, and polymers of lower mono olefins; etc. 7
  • the alltylated aromatic detergent materials employed will be a mixture of compounds having alkyl substituents of varying chain lengths, the range of lengths depending upon the sharpness of the fractionation of the aliphatic hydrocarbon used in the alkylation reaction.
  • the average chain length of the alkyl substituents should be from about 9 to about 15 carbon atoms and preferably between about 12 and about 14 carbon atoms.
  • the detergents may be used in the form of their alkali metal salts, e. g., sodium, potassium or lithium salts, as well as in the form of salts of nitrogen containing bases, e. g., ammonium and lower alkylolamine salts, such as the ethanolamhie salts including mono, di-, and tri-ethanolamine salts, and mixtures thereof.
  • alkali metal salts e. g., sodium, potassium or lithium salts
  • nitrogen containing bases e. g., ammonium and lower alkylolamine salts, such as the ethanolamhie salts including mono, di-, and tri-ethanolamine salts, and mixtures thereof.
  • the shampoo compositions may contain various additional materials.
  • the compositions ordinarily will contain a perfume which should be selected so as to be compatible with the character of the finished shampoo. 1
  • compositions which are sometimes used in shampoos for imparting desirable qualities to the hair after washing may be incorporated in the present compositions.
  • superfatting materials such as fatty alcohols, fatty amides, lanolin, etc.
  • the higher fatty alcohols such as myristyl, cetyl, and stearyl alcohols are useful not only for their effect on the hair but also to increase the foaming properties of the composition;
  • suitable amides are p the higher fatty acid amides such as myris'tamide,
  • an alkylolamine such as palmityl ethanolamide, myristyl propano'lamide
  • Glycerine may be present in amount up to about 10%. Titanium dioxide may be added to impart opacity and/ or increased whiteness to the compositions and preferably it should not exceed about 0.5 of the final composition. If a color other than white is desired, a color or dye may be added.
  • compositions may be prepared and marketed in any form.
  • the various ingredients may be so proportioned as to form a clear or an opaque liquid, cream, paste, gel, or aerosol type shampoo composition.
  • the concentration of the detergent in the shampoo composition generally should amount to at least about 5% usually about 5 to about 45% and preferably from about 15 to about 35% by weight. It has been determined that the beneficial effects of the instant invention are achieved to an optimum degree when the shampoo composition contains an appreciable amount of detergent such as specified Within the preferred range.
  • the monomethylol dimethyl hydantoin incorporated in the shampoo compositions of this invention has the following structural formula:
  • l-methylol 5,5-dimethyl hydantoin This material serves as a preservative in the shampoo composition in that it inhibits bacterial and mold growth and prevents the compositions from developing an unpleasant odor or darkening in" color even on long standing.
  • the amount of monomethylol dimethyl hydantoin used in formulating the present shampoo compositions is variable and .will be in minor proportion such as'up to about 1% by weight of the composition. In general, it has been found that a't'least about 0.05% is required, but it is preferred to use at least about 0.1% by with excellent results being obtained with amounts of at least about 0.2% by weight.
  • Example I The following is. a satisfactory white, opaque cream shampoo composition of pasty consistency:
  • Example 11 The following is a satisfactory paste shampoo composition:
  • S0dium salt of sulfated monoglyceride of hydrogenated coconut oil fatty acids It contains about 10% by Weight of sodium sulfate.
  • Example III The following is a satisfactory liquid shampoo containing only the essential ingredients:
  • Monomethylol dimethyl hydantoin do 0.25 Water balance 1 Ammonium salt of sulfated monoglyceride of hydrogenated coconut oil fatty acids. It contained a few percent of ammonium sulfate.
  • Example IV The'following is a satisfactory liquid shampoo containing only the essential ingredients:
  • the solid ingredients preferably are melted and stirred into the aqueous medium at elevated temperatures to form a homogeneous mixture.
  • the composition then is cooled methylol dimethyl hydantoin and perfume added, and the shampoo bottled, filled into jars, or otherwise prepared for use.
  • Other methods of manufacture may be employed, if desired, including continuous proportioning of the ingredients into a mixing apparatus wherein the ingredients are blended thoroughly at elevated temperatures, cooled, and thereafter filled into suitable containers.
  • a shampoo composition comprising at least about 5% by weight of an organic detergent selected from the group consisting of sulfated and sulfonateddetersive salts in an aqueous medium which is normally subject to bacterial and mold growth and a minor proportion up to about 1% of l-methylol 5,5-dimethyl hydantoin sufficient to inhibit said growth.
  • a shampoo composition comprising at least about 5% by weight of a water-soluble higher fatty acid monoglyceride sulfate detergent salt in' an aqueous medium which is normally subject to bacterial and mold growth and a minor proportion up to about 1% of l-methylol 5,5-dimethyl hydantoin sufiicient to inhibit said growth.
  • a shampoo composition comprising at least about 5% by weight of a water-soluble higher alkyl sulfate detergent salt in an aqueous medium which is normally subject to bacterial and mold growth and a minor propor 4.
  • a shampoo composition comprising at least about 5% by weight of an organic detergent selected from the References Clted 111 the file of thls Patent group consisting of sjulfated gut; sulfonatec;1 iletersriye saltts UNITED STATES PATENTS m an aqueous me rum w 1c is norm y su ect o bacterial and mold growth and about 0.11% by weight 5 g a?
  • a shampoo composition comprising about 15-35% 2579436 Mac ey by weight of an organic detergent selected from the group OTHER REFERENCES consisting of sulfated and sulfonated detersive salts in an 10 aqueous medium which is normally subject to bacterial sfngerz Artlqle, Chelatmg agents for soaps Soap and and mold growth and abnt0 1 1% by weight f Lmeth.
  • ylol 5,5-dimethyl hydantoin sufficient to inhibit said schlmmel Brwfs 185, August 1950- growth.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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  • Epidemiology (AREA)
  • Cosmetics (AREA)

Description

United States Patent SHAMPOO COB POSITIONS CGNTAINING MONO- lVIETHYLOL DIMIETHYL HYDANTOIN Hyman Henkin, Bayside, N. Y., assignor to Colgate- Palmolive Company, Jersey City, N. 5., a corporation of Delaware No Drawing. Application September 21, E53, Serial No. 381,509
Claims. (Cl. 252-152) The present invention relates to shampoo compositions and has particular reference to shampoo compositions comprising in combination a water-soluble organic anionic synthetic detergent and monomethylol dimethyl hydantoin in an aqueous medium.
Shampoo compositions containing many different types of detergents are suggested in the prior art. Thus, some shampoo compositions contain soap, i. e., watersoluble salts of fatty acids as the active detersive or cleansing ingredient. In others, the so-called non-soap synthetic detergents are used instead of soap, while in still others various synthetic detergents are used in combination with soap.
Those shampoo compositions which contain anionic sulfate and sulfonate salts as the principal cleaning ingredient have enjoyed a considerable amount of commercial success in recent years. Such compositions exhibit high water solubility and have excellent detergent and foaming properties.
It has been observed, however, that such shampoo compositions sometimes develop an unpleasant odor on standing and often darken in color thereby losing their desirable appearance. Bacteriological examination of those shampoo compositions which have darkened and which have developed an unpleasant odor reveal that those compositions also are contaminated with certain bacteria and mold. Since the freshly manufactured shampoo has a desirable color and odor, it is believed 2,773,834 Patented Dec. 11, 1956 amples of these detergents are the sulfated materials having an alkyl substituent containing about 8 to about 26 carbon atoms per molecule, those containing at least about 10 and preferably about 12 to about 22 carbon atoms per molecule having particularly useful detergent properties.
Representative compounds which may be suitably employed include the sulfuric acid esters of polyhydric alcohols incompletely esterified with higher fatty acids, e. g., coconut oil monoglyceride monosulfate, tallow diglyceride monosulfate; the long chain pure or mixed alkyl sulfates, e. g., lauryl sulfate, cetyl sulfate, higher fatty alcohol sulfates derived from coconut oil; the hydroxy sulfonated higher fatty acid esters, e. g., higher fatty acid esters of 2,3-dihydroxy propane sulfonic acid; the higher fatty acid esters of low molecular weight alkylol sulfonic acids, e. g., oleic acid esters of isethionic acid; the sulfated higher fatty acid alkylolamides, e. g., ethanolamide sulfates; the higher fatty acid amides of amino alkyl sulfonic acids, e. g., lauric amide of taurine, and the like.
Additional well known anionic synthetic detergent materials which may be employed include those materials known generally as the alkylated aromatic hydrocarbon compounds having an alkyl substituent containing about 8 to 26 carbon atoms. The aromatic portion of the 4 molecule may be monoor polynuclear in structure, e. g.,
that the darkening in color and the development of an unpleasant odor is associated with the growth and multiplication of bacteria and mold. It is further believed that the synthetic detergent material furnishes the nutrient medium in which the bacteria and mold grow and multiply.
It now has been discovered that the incorporation of relatively small amounts of monomethylol dimethyl hydantoin in shampoo compositions which contain Watersoluble anionic sulfate and sulfonate salts as the active cleansing ingredient provides a shampoo composition which has a desirable initial color and odor and further provides a shampoo composition which does not darken in color or develop an unpleasant odor, and which is not contaminated with bacteria or mold, even on long standing. The composition has further advantages in that it has excellent stability against phase separation, is non-irritating to the skin, and has high foaming power and excellent cleansing properties when applied to human hair in either soft or hard water. The composition is simple to manufacture and can be produced in conventional shampoo formulating equipment.
The shampoo compositions of this invention consist essentially of at least one water-soluble organic anionic synthetic detergent selected from the group consisting of sulfated and sulfonated detersive salts, and monomethylol dimethyl hydantoin in an aqueous medium.
The invention is applicable to shampoo compositions containing water-soluble anionic synthetic detergents which are well known in the art. Representative exbenzene, toluene, xylene, naphthalene, phenanthrene, anthracene, etc., and may contain other substituents such as hydroxyl groups, e. g., phenols, cresols, phenol ethers, short chain alkyl groups, e. g., alkylated toluene, alkylated xylene, etc. The long chain alkyl substituent of the alkylated aromatic molecule preferably is saturated and may be straight or branched. Representative long chain alkyl groups include such radicals as dodecyl; hexyl; octyl; nonyl; decyl; mixed alkyls derived from fatty materials, cracked parafiin wax olefins, and polymers of lower mono olefins; etc. 7
In general, the alltylated aromatic detergent materials employed will be a mixture of compounds having alkyl substituents of varying chain lengths, the range of lengths depending upon the sharpness of the fractionation of the aliphatic hydrocarbon used in the alkylation reaction. For most purposes the average chain length of the alkyl substituents should be from about 9 to about 15 carbon atoms and preferably between about 12 and about 14 carbon atoms.
These various anionic detergents are employed in the compositions of this invention in the form of their watersoluble salts. Thus, the detergents may be used in the form of their alkali metal salts, e. g., sodium, potassium or lithium salts, as well as in the form of salts of nitrogen containing bases, e. g., ammonium and lower alkylolamine salts, such as the ethanolamhie salts including mono, di-, and tri-ethanolamine salts, and mixtures thereof.
Although the essential ingredients are the three mentioned above, the shampoo compositions may contain various additional materials. Thus, the compositions ordinarily will contain a perfume which should be selected so as to be compatible with the character of the finished shampoo. 1
Other ingredients which are sometimes used in shampoos for imparting desirable qualities to the hair after washing may be incorporated in the present compositions. Thus, superfatting materials such as fatty alcohols, fatty amides, lanolin, etc., may be used in amounts up, to about 5%. The higher fatty alcohols such as myristyl, cetyl, and stearyl alcohols are useful not only for their effect on the hair but also to increase the foaming properties of the composition; Among suitable amides are p the higher fatty acid amides such as myris'tamide,
' weight,
palmitylamide, stearylamide, or the amides produced by condensing a higher fatty acid or mixtures of such acids with an alkylolamine such as palmityl ethanolamide, myristyl propano'lamide, and they may be 'used either alone or in combination with the fatty alcohols arid/or lanolin.
Glycerine may be present in amount up to about 10%. Titanium dioxide may be added to impart opacity and/ or increased whiteness to the compositions and preferably it should not exceed about 0.5 of the final composition. If a color other than white is desired, a color or dye may be added.
Furthermore, the compositions may be prepared and marketed in any form. Thus, the various ingredients may be so proportioned as to form a clear or an opaque liquid, cream, paste, gel, or aerosol type shampoo composition.
The concentration of the detergent in the shampoo composition generally should amount to at least about 5% usually about 5 to about 45% and preferably from about 15 to about 35% by weight. It has been determined that the beneficial effects of the instant invention are achieved to an optimum degree when the shampoo composition contains an appreciable amount of detergent such as specified Within the preferred range.
The monomethylol dimethyl hydantoin incorporated in the shampoo compositions of this invention has the following structural formula:
and further may be defined as l-methylol 5,5-dimethyl hydantoin. This material serves as a preservative in the shampoo composition in that it inhibits bacterial and mold growth and prevents the compositions from developing an unpleasant odor or darkening in" color even on long standing. The amount of monomethylol dimethyl hydantoin used in formulating the present shampoo compositions is variable and .will be in minor proportion such as'up to about 1% by weight of the composition. In general, it has been found that a't'least about 0.05% is required, but it is preferred to use at least about 0.1% by with excellent results being obtained with amounts of at least about 0.2% by weight.
In order to indicate even more fully the nature of the present invention the following specific examples of shampoo compositions are set forth. Each of these compositions has a desirable odor and color when initially produced and they do not develop an unpleasant odor or darken or discolor and are not contaminated with bacteria or mold even on long standing. The examples are presented for illustrative purposes only and are not intended to limit the scope of the invention in any manner.
Example I The following is. a satisfactory white, opaque cream shampoo composition of pasty consistency:
Siidium lauryl' sulfate.
Example 11 The following is a satisfactory paste shampoo composition:
S0dium salt of sulfated monoglyceride of hydrogenated coconut oil fatty acids. It contains about 10% by Weight of sodium sulfate.
Example III The following is a satisfactory liquid shampoo containing only the essential ingredients:
Detergent 1 percent 30.00
Monomethylol dimethyl hydantoin do 0.25 Water balance 1 Ammonium salt of sulfated monoglyceride of hydrogenated coconut oil fatty acids. It contained a few percent of ammonium sulfate.
Example IV The'following is a satisfactory liquid shampoo containing only the essential ingredients:
Detergent percent 25.00 Monomethylol dimethyl hydantoin do 0.05 Water balance 1 Sodium dodecyl benzene sulfonate. It contains about 1 0% by weight sodium sulfate.
In formulating the shampoo compositions of this invention the solid ingredients preferably are melted and stirred into the aqueous medium at elevated temperatures to form a homogeneous mixture. The composition then is cooled methylol dimethyl hydantoin and perfume added, and the shampoo bottled, filled into jars, or otherwise prepared for use. Other methods of manufacture may be employed, if desired, including continuous proportioning of the ingredients into a mixing apparatus wherein the ingredients are blended thoroughly at elevated temperatures, cooled, and thereafter filled into suitable containers.
While there has been disclosed and described what is at present considered to be the preferred embodiment of the invention, it will be understood, of course, that many modifications and changes and substitutions may be made therein without departing from the true scope of the invention as defined in the appended claims.
Having thus described the invention, what is claimed 1. A shampoo composition comprising at least about 5% by weight of an organic detergent selected from the group consisting of sulfated and sulfonateddetersive salts in an aqueous medium which is normally subject to bacterial and mold growth and a minor proportion up to about 1% of l-methylol 5,5-dimethyl hydantoin sufficient to inhibit said growth.
2. A shampoo composition comprising at least about 5% by weight of a water-soluble higher fatty acid monoglyceride sulfate detergent salt in' an aqueous medium which is normally subject to bacterial and mold growth and a minor proportion up to about 1% of l-methylol 5,5-dimethyl hydantoin sufiicient to inhibit said growth.
3. A shampoo composition comprising at least about 5% by weight of a water-soluble higher alkyl sulfate detergent salt in an aqueous medium which is normally subject to bacterial and mold growth and a minor propor 4. A shampoo composition comprising at least about 5% by weight of an organic detergent selected from the References Clted 111 the file of thls Patent group consisting of sjulfated gut; sulfonatec;1 iletersriye saltts UNITED STATES PATENTS m an aqueous me rum w 1c is norm y su ect o bacterial and mold growth and about 0.11% by weight 5 g a? of l-methylol 5,5-dimethyl hydantoin sufiicient to inhibit 2542385 F 1951 said growth. 1951 5. A shampoo composition comprising about 15-35% 2579436 Mac ey by weight of an organic detergent selected from the group OTHER REFERENCES consisting of sulfated and sulfonated detersive salts in an 10 aqueous medium which is normally subject to bacterial sfngerz Artlqle, Chelatmg agents for soaps Soap and and mold growth and abnt0 1 1% by weight f Lmeth. Sanitary Chemtcals, March 1950, pp. 45, 46, 47 and 73. ylol 5,5-dimethyl hydantoin suficient to inhibit said schlmmel Brwfs 185, August 1950- growth.

Claims (1)

1. A SHAMPOO COMPOSITION COMPRISING AT LEAST ABOUT 5% BY WEIGHT OF AN ORGANIC DETERGENT SELECTED FROM THE GROUP CONSISTING OF SULFATED AND SULFONATED DETERSIVE SALTS IN AN AQUEOUS MEDIUM WHICH IS NORMALLY SUBJECT TO BACTERIAL AND MOLD GROWTH AND A MINOR PROPORTION UP TO ABOUT 1% OF 1-METHYLOL 5,5-DIMETHYL HYDANTOIN SUFFICIENT TO INHIBIT SAID GROWTH.
US381509A 1953-09-21 1953-09-21 Shampoo compositions containing monomethylol dimethyl hydantoin Expired - Lifetime US2773834A (en)

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3001949A (en) * 1957-01-24 1961-09-26 Colgate Palmolive Co Shampoo composition
US3210285A (en) * 1960-06-27 1965-10-05 Colgate Palmolive Co Liquid abrasive cleanser containing sodium chloride
US3240713A (en) * 1962-08-02 1966-03-15 Benjamin M Hulsh Wood flour rug cleaning composition
US3470102A (en) * 1965-01-22 1969-09-30 Lever Brothers Ltd Detergent composition
US3476489A (en) * 1964-11-27 1969-11-04 Colgate Palmolive Co Method of making a shampoo
EP0409302A3 (en) * 1989-07-19 1992-01-15 Blendax Gmbh Cosmetics

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2327323A (en) * 1940-07-13 1943-08-17 Du Pont Water-treating agent
US2469378A (en) * 1941-07-28 1949-05-10 Allied Chem & Dye Corp Mixtures of alkyl aryl sulfonates
US2542385A (en) * 1946-10-12 1951-02-20 Gen Aniline & Film Corp Detergent composition
US2579436A (en) * 1950-04-12 1951-12-18 Gen Aniline & Film Corp Process of inhibiting the degradation of photographic color images

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2327323A (en) * 1940-07-13 1943-08-17 Du Pont Water-treating agent
US2469378A (en) * 1941-07-28 1949-05-10 Allied Chem & Dye Corp Mixtures of alkyl aryl sulfonates
US2542385A (en) * 1946-10-12 1951-02-20 Gen Aniline & Film Corp Detergent composition
US2579436A (en) * 1950-04-12 1951-12-18 Gen Aniline & Film Corp Process of inhibiting the degradation of photographic color images

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3001949A (en) * 1957-01-24 1961-09-26 Colgate Palmolive Co Shampoo composition
US3210285A (en) * 1960-06-27 1965-10-05 Colgate Palmolive Co Liquid abrasive cleanser containing sodium chloride
US3240713A (en) * 1962-08-02 1966-03-15 Benjamin M Hulsh Wood flour rug cleaning composition
US3476489A (en) * 1964-11-27 1969-11-04 Colgate Palmolive Co Method of making a shampoo
US3470102A (en) * 1965-01-22 1969-09-30 Lever Brothers Ltd Detergent composition
EP0409302A3 (en) * 1989-07-19 1992-01-15 Blendax Gmbh Cosmetics

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