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US2546383A - Method of making a rubberlike cleaning composition - Google Patents

Method of making a rubberlike cleaning composition Download PDF

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US2546383A
US2546383A US623435A US62343545A US2546383A US 2546383 A US2546383 A US 2546383A US 623435 A US623435 A US 623435A US 62343545 A US62343545 A US 62343545A US 2546383 A US2546383 A US 2546383A
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parts
oil
solid
diluted
cooling
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    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D13/00Making of soap or soap solutions in general; Apparatus therefor
    • C11D13/02Boiling soap; Refining
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D9/00Compositions of detergents based essentially on soap
    • C11D9/04Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/06Inorganic compounds
    • C11D9/18Water-insoluble compounds

Definitions

  • This invention relates to hand cleaner compo- -sitions which areof a type-characterized bytthe fact that they maybe employed .forythe complete cleaning of the hands, without the use .of either water or towels of ,any kind.
  • certainsubstanoes may be converted chemically to a form having aconsistency which constitutes a soft solid'base which may be dispersed in finely-divided form intostiff emulsions orpaste-likeplastic creams. And it is further found that these substances, in such'dis- ,persed condition, upon being subjected to rubbing friction, break the dispersion and coalesce into .aggregates, having moist soft surfaces which are highly adsorbent and of an increasingfrictional resistance as the exposed moist surfaces gradually become dry.
  • fatty oils generally may be employed including vegetable oils, , suchas corn ,oil, linseed oil, mustard seed oil, soya bean oil, castor oil, cottonseed oil, and peanut oil (but not coconut oil) fish oil (but not-sperm oil) and lard ,oil, as well as a number vofthe waxes.
  • One procedure for converting the fatty oil to the desired semi-solid form is to subject it .to sulphur chloride (monochloride), the reaction being controlled by a preliminary neutralization of the oil with an excess of an alkali, such ,as lime, hydrated lime, etc.
  • ,A-further-control of the conversion ofthe fatty oil may be effected by diluting the reactants, e. g. by diluting the sulphur mono-chloride with high boiling inert petroleum solvents, such as Stoddard solvent, which has aninitialflash point of 117 R, an initial boiling point of 311 F. and final boiling point of 411, F.
  • high boiling inert petroleum solvents such as Stoddard solvent
  • the reaction may also be retarded against a too rapid or uneven development throughout the charge or too drastic a degree of conversion of the fatty oil, or to a too solid consistency, by incorporating a voluminous material ,into the charge which is inert to the reaction, such aspotato-starch, in proportions up to -approximately .for example, On the tweightqof thetoil.
  • a still further control of the rate and degree .cf-the :conversionsof-thefatty oil for the purposes of this invention effected'by cooling the reagent materials preliminary to their addition and admixture and/.01 by ,making such admixturesgradually, with intimateagitation and suitable provisions for cooling the reaction mixture.
  • thesolidified products, obtained by the controlled-but completereaction of thefatty oils with the sulphur chloride may be effectively vstabilizedin the condition-developed-by the foregoing procedures by the addition of neutralizing agents such as lime, magnesium carbonate, urea, terpenes, and soaps, 'and' more-especially soaps ofpolyvalent metals suohas the -aluminum soaps of coconut oil, Japan wax,jand the like.
  • the fatty oils are reacted and developed "to 'a semi-solid condition, from which theymay bereduced to finely divided or colloidal condition and dispersed in suitablemedia to develop resulting compositions of various consistencies and properties.
  • Sulphurmono-chloride (.15 parts by weight) v,is then diluted with one third of its volume of Stoddards solvent (or other inert high-boiling petroleum solvent of suitable consistency).
  • the diluted sulphur mono-chloride is then added slowly to the alkaline reaction product of the soya beanoil and lime, with continued stirring of the'mixture. This mixture ,is then again allowed ,to cool to 50 F,, .Or below.
  • reaction mass solidifies into a firm rubber-like substance of light color. After aging several days (at room temperature) the mass is broken up and ground. Prolonged aging will greatly improve the product thus obtained and promote its disintegration to finely divided form, as a crumbly mass.
  • the product as thus obtained contains considerable free lime which may have a harsh action upon the hands, it is well to remove it. This may be done by Washing with water or by neutralizing. Lactic acid serves this purpose with good success. It is, however, desirable to leave and maintain a slight excess of alkali as it will act as a stabilizer.
  • the end product is a light crumbly solid which constitutes the basic ingredient of the hand cleaner composition.
  • a typical dry hand cleaner composition may accordingly be prepared as follows:
  • diethylene glycol mono-ethyl ether 0 parts di-glycol laurate 10 parts sorbitan mono laurate.
  • the finely divided base may be first mixed well with the sorbitan mono laurate, the water being then added and thoroughly mixed, followed by the remaining ingrefients.
  • the composition as thus obtained is advantageously milled in a paint mill to a smooth, uniform cream or paste. In this condition, the composition is ready for packaging, storage or immediate use.
  • the consistency of the product may be varied somewhat, according to the intended use, as already indicated. Thus abrasives may be added for especially active cleaning action. Other fillers may be added, with a milder action of the same sort. In addition, the consistency may be varied from a stiff, hard paste, useful in cases where this may seem the more effective, to a soft, wet paste, cream or even an emulsion stage, if desired.
  • the action of the composition upon rubbing on and between the hands, is first to spread it out, and then to break the emulsion and coagulate it into separate crumbs, which are coarse, slightly adherent, but soft solid particles. These are adsorbent, plastic, soft, and moist and characteristically roll up in the hand, carrying with them the dirt, grease and all foreign matter from the surfaces, pores and wrinkles of the skin.
  • the liquid components are absorbed by the skin, or evaporate into the air.
  • composition passes from a soft, creamy or even fluid condition to an increasingly firm, solid condition with continued rubbing, and finally forms into dry, pasty solid particles which soon dust off from the hands completely, leaving them suitably dry and thoroughly clean but soft and without any harsh action chemically or physically such as by chappin or scratching.
  • the action of the cleaner composition may be varied in several ways by the compounding ingredients employed.
  • an increased proportion of water or other liquid will render the mixture softer or more fluid and home 7 more of petroleum hydrocarbons of somewhat slower action on the hands while it is drying off or being absorbed by the hands.
  • polyvinyl acetate or vinyl butyrate up to about 20%, it effects the quicker breaking of the dispersion emulsion of the composition upon coming into contact with the skin.
  • Natural or synthetic rubber likewise may be added and act in the same manner. Upon rubbing, the particles then form and roll up faster into crumbs which are also larger and may be shaken off sooner and more easily.
  • the composition is a paste or smooth cream so that it spreads well.
  • the diethylene glycol monoethyl ether and glycol laurate and other such fatty substances tend to delay the crumb-forming action of the mixture and permit or require longer rubbing before the crumbly stage is reached and before the particles dry sufficiently to be dusted off the hands completely.
  • the diethylene glycol mono-ethyl ether and diglycol laurate may be replaced by lanolin, mineral oil, sulphonated oils, or oxidized oils for raw vegetable, animal or fish oils to a degree.
  • the diethylene glycol'mono-ethyl ether is active as a general solvent and has beneficial action on the skin.
  • the sorbitan mono laurate is a good wetting agent and is effective to promote uniformity of the composition and complete spreading action of the composition on the hands. Very good results are obtained, for example, with additions of soaps such as 40 to 50 parts of alcoholic potash soap to 100 parts of the base, preferably, along with 40 to 50 parts of water or alcohol.
  • a method of making a solid, dry, cleaner base comprising the steps of reacting approximately 100 parts of soya bean oil with 6-12 parts of hydrated lime, cooling to 50 F., adding ap-- proximately 15 parts of sulphur monochloride diluted with one-third of its volume of inert petroleum solvent, cooling to 50 F., adding approximately 16 parts of sulphur monochloride diluted with /2 its volume of inert petroleum solvent, with vigorous stirring until the mass solidifies as a whole.
  • a method of making a solid, dry, cleaner base comprising the steps of reacting approximately 100 parts of soya bean oil with 6-12 parts of hydrated lime, cooling to 50 F., adding approximately 15 parts of sulphur monochloride diluted with one-third of its volume of inert petroleum solvent, cooling to 50 F., and then adding up to 10% of starch, adding approximately 16 parts of sulphur monochloride diluted with its volume of inert petroleum solvent, with vigorous stirring until the mass solidifies as a whole.
  • a method of making a solid, dry, cleaner base comprising the steps of reacting approximately 100 parts ofsoya bean oil with 6-12 parts of hydrated lime, cooling to 50 F., adding approximately 15 parts of sulphur monochloride diluted with one-third of its volume of inert petroleum solvent, cooling to 50,EL, adding approximately 16 parts of sulphur monochloride diluted with A2 its volume of inert petroleum solvent, with vigorous stirring until the mass solidifies as a whole, grinding said product and dispersing the same in finely divided condition with a liquid vehicle which is non-solvent of and non-reactive upon and present in substantially equal proportions to the solid components.
  • a method of making a solid, dry, cleaner base comprising the steps of reacting approximately 100 parts of soya bean oil with 6-12 parts of hydrated lime, cooling to 50 F., adding approximately 15 parts of sulphur monochloride diluted with one-third of its volume of inert petroleum solvent, cooling to 50 F., and then adding up to 10% of starch, adding approximately 16 /2 parts of sulphur monochloride diluted with /g' its volume of inert petroleum solvent, with vigorous stirring until the mass solidifies as a, whole, grinding said product and dispersing the same in finely divided condition with a liquid vehicle which is non-solvent of and non-reactive upon and present in substantially equal proportions to the solid components.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)

Description

Patented Mar. 27, 1951 OFFICE METHOD OFMAKING, ARUBBERLIKE CLEANING CONEPOSITION Hans-.Blumberg, Peabody, Mass.
No Drawing. Application October" 19, 1945, "Serial No. 623,435
.4 Claims. 1
This invention relates to hand cleaner compo- -sitions which areof a type-characterized bytthe fact that they maybe employed .forythe complete cleaning of the hands, without the use .of either water or towels of ,any kind.
It is found, inaccordance with the discovery of this invention, that certainsubstanoes may be converted chemically to a form having aconsistency which constitutes a soft solid'base which may be dispersed in finely-divided form intostiff emulsions orpaste-likeplastic creams. And it is further found that these substances, in such'dis- ,persed condition, upon being subjected to rubbing friction, break the dispersion and coalesce into .aggregates, having moist soft surfaces which are highly adsorbent and of an increasingfrictional resistance as the exposed moist surfaces gradually become dry.
.For the preparation of the solid base constituent of these properties it is found that fatty oils generally may be employed including vegetable oils, ,suchas corn ,oil, linseed oil, mustard seed oil, soya bean oil, castor oil, cottonseed oil, and peanut oil (but not coconut oil) fish oil (but not-sperm oil) and lard ,oil, as well as a number vofthe waxes.
In general I have found that the fatty.-oils as exemplified by those mentioned above-may be uniformly and completely converted :to :the soft solid form, and that when this isdone, the resulting product is characterizedby the properties above described, which make it applicable to be used as the base or principal ingredient of a dry hand cleaner composition.
One procedure for converting the fatty oil to the desired semi-solid form is to subject it .to sulphur chloride (monochloride), the reaction being controlled by a preliminary neutralization of the oil with an excess of an alkali, such ,as lime, hydrated lime, etc.
,A-further-control of the conversion ofthe fatty oil, may be effected by diluting the reactants, e. g. by diluting the sulphur mono-chloride with high boiling inert petroleum solvents, such as Stoddard solvent, which has aninitialflash point of 117 R, an initial boiling point of 311 F. and final boiling point of 411, F.
The reaction may also be retarded against a too rapid or uneven development throughout the charge or too drastic a degree of conversion of the fatty oil, or to a too solid consistency, by incorporating a voluminous material ,into the charge which is inert to the reaction, such aspotato-starch, in proportions up to -approximately .for example, On the tweightqof thetoil.
A still further control of the rate and degree .cf-the :conversionsof-thefatty oil for the purposes of this invention effected'by cooling the reagent materials preliminary to their addition and admixture and/.01 by ,making such admixturesgradually, with intimateagitation and suitable provisions for cooling the reaction mixture.
And finally, thesolidified products, obtained by the controlled-but completereaction of thefatty oils with the sulphur chloride may be effectively vstabilizedin the condition-developed-by the foregoing procedures by the addition of neutralizing agents such as lime, magnesium carbonate, urea, terpenes, and soaps, 'and' more-especially soaps ofpolyvalent metals suohas the -aluminum soaps of coconut oil, Japan wax,jand the like.
Bysuch procedureand controls, the fatty oils are reacted and developed "to 'a semi-solid condition, from which theymay bereduced to finely divided or colloidal condition and dispersed in suitablemedia to develop resulting compositions of various consistencies and properties. Ordinarily liquid vehicles .will be 'usedfor this purpose forming emulsions, or soft or stiff pastes, according to the proportions, but often solids may be added and gasesmayact as a dispersing medium, in the'form ofbubblesor the like,.within jthe invention.
.A representative example of thepractical carrying out of the invention, which results in a composition of preferred properties as a dry lhand cleaner, is as follows:
Mix ,lOOparts by weight of refined soya bean oil with 6-12 partsby weight of hydrated lime, and then cool the reaction mixture at least to 50F or preferably vtolower temperatures.
Sulphurmono-chloride (.15 parts by weight) v,is then diluted with one third of its volume of Stoddards solvent (or other inert high-boiling petroleum solvent of suitable consistency).
The diluted sulphur mono-chloride is then added slowly to the alkaline reaction product of the soya beanoil and lime, with continued stirring of the'mixture. This mixture ,is then again allowed ,to cool to 50 F,, .Or below.
half its volume of Stoddard ysolvent, or;similar .inert .;high-iboilin ip troleum solvent. This :is
then also added slowly to the cooled reaction mixture, while vigorously stirring.
In about or minutes thereafter the whole reaction mass solidifies into a firm rubber-like substance of light color. After aging several days (at room temperature) the mass is broken up and ground. Prolonged aging will greatly improve the product thus obtained and promote its disintegration to finely divided form, as a crumbly mass.
Since the product as thus obtained contains considerable free lime which may have a harsh action upon the hands, it is well to remove it. This may be done by Washing with water or by neutralizing. Lactic acid serves this purpose with good success. It is, however, desirable to leave and maintain a slight excess of alkali as it will act as a stabilizer.
The end product is a light crumbly solid which constitutes the basic ingredient of the hand cleaner composition.
A typical dry hand cleaner composition may accordingly be prepared as follows:
100 parts of the product, obtained as above described and reduced at least to granular form.
parts diethylene glycol mono-ethyl ether 0 parts di-glycol laurate 10 parts sorbitan mono laurate.
-60 parts water (with or without the addition of methyl cellulose) Fillers, abrasives and perfumes, as and if desired.
The finely divided base may be first mixed well with the sorbitan mono laurate, the water being then added and thoroughly mixed, followed by the remaining ingrefients. The composition as thus obtained is advantageously milled in a paint mill to a smooth, uniform cream or paste. In this condition, the composition is ready for packaging, storage or immediate use.
The consistency of the product may be varied somewhat, according to the intended use, as already indicated. Thus abrasives may be added for especially active cleaning action. Other fillers may be added, with a milder action of the same sort. In addition, the consistency may be varied from a stiff, hard paste, useful in cases where this may seem the more effective, to a soft, wet paste, cream or even an emulsion stage, if desired.
In general, the action of the composition, upon rubbing on and between the hands, is first to spread it out, and then to break the emulsion and coagulate it into separate crumbs, which are coarse, slightly adherent, but soft solid particles. These are adsorbent, plastic, soft, and moist and characteristically roll up in the hand, carrying with them the dirt, grease and all foreign matter from the surfaces, pores and wrinkles of the skin. The liquid components are absorbed by the skin, or evaporate into the air. Consequently, the composition passes from a soft, creamy or even fluid condition to an increasingly firm, solid condition with continued rubbing, and finally forms into dry, pasty solid particles which soon dust off from the hands completely, leaving them suitably dry and thoroughly clean but soft and without any harsh action chemically or physically such as by chappin or scratching.
The action of the cleaner composition, as above described, may be varied in several ways by the compounding ingredients employed. Thus an increased proportion of water or other liquid will render the mixture softer or more fluid and home 7 more of petroleum hydrocarbons of somewhat slower action on the hands while it is drying off or being absorbed by the hands. It is found, on the other hand, for example, that by adding polyvinyl acetate or vinyl butyrate up to about 20%, it effects the quicker breaking of the dispersion emulsion of the composition upon coming into contact with the skin. Natural or synthetic rubber likewise may be added and act in the same manner. Upon rubbing, the particles then form and roll up faster into crumbs which are also larger and may be shaken off sooner and more easily. The composition is a paste or smooth cream so that it spreads well. On the other hand,'the diethylene glycol monoethyl ether and glycol laurate and other such fatty substances tend to delay the crumb-forming action of the mixture and permit or require longer rubbing before the crumbly stage is reached and before the particles dry sufficiently to be dusted off the hands completely.
It is also possible to combine up to or (upon the weight of the fluid components of the composition) with the dry base material. When this is done, upon allowing the mixture to stand for three or four days, the composition will be found to require but little milling or none at all.
In place of the water and other liquid vehicles used, other appropriate liquids may be substituted, so long as they are compatible with the base ingredient and its characteristic properties and action in the cleaner composition as a whole. Thus, the diethylene glycol mono-ethyl ether and diglycol laurate may be replaced by lanolin, mineral oil, sulphonated oils, or oxidized oils for raw vegetable, animal or fish oils to a degree. However, the diethylene glycol'mono-ethyl ether is active as a general solvent and has beneficial action on the skin. The sorbitan mono laurate is a good wetting agent and is effective to promote uniformity of the composition and complete spreading action of the composition on the hands. Very good results are obtained, for example, with additions of soaps such as 40 to 50 parts of alcoholic potash soap to 100 parts of the base, preferably, along with 40 to 50 parts of water or alcohol.
I claim: 1. A method of making a solid, dry, cleaner base, comprising the steps of reacting approximately 100 parts of soya bean oil with 6-12 parts of hydrated lime, cooling to 50 F., adding ap-- proximately 15 parts of sulphur monochloride diluted with one-third of its volume of inert petroleum solvent, cooling to 50 F., adding approximately 16 parts of sulphur monochloride diluted with /2 its volume of inert petroleum solvent, with vigorous stirring until the mass solidifies as a whole.
2. A method of making a solid, dry, cleaner base, comprising the steps of reacting approximately 100 parts of soya bean oil with 6-12 parts of hydrated lime, cooling to 50 F., adding approximately 15 parts of sulphur monochloride diluted with one-third of its volume of inert petroleum solvent, cooling to 50 F., and then adding up to 10% of starch, adding approximately 16 parts of sulphur monochloride diluted with its volume of inert petroleum solvent, with vigorous stirring until the mass solidifies as a whole.
3. A method of making a solid, dry, cleaner base, comprising the steps of reacting approximately 100 parts ofsoya bean oil with 6-12 parts of hydrated lime, cooling to 50 F., adding approximately 15 parts of sulphur monochloride diluted with one-third of its volume of inert petroleum solvent, cooling to 50,EL, adding approximately 16 parts of sulphur monochloride diluted with A2 its volume of inert petroleum solvent, with vigorous stirring until the mass solidifies as a whole, grinding said product and dispersing the same in finely divided condition with a liquid vehicle which is non-solvent of and non-reactive upon and present in substantially equal proportions to the solid components.
4. A method of making a solid, dry, cleaner base, comprising the steps of reacting approximately 100 parts of soya bean oil with 6-12 parts of hydrated lime, cooling to 50 F., adding approximately 15 parts of sulphur monochloride diluted with one-third of its volume of inert petroleum solvent, cooling to 50 F., and then adding up to 10% of starch, adding approximately 16 /2 parts of sulphur monochloride diluted with /g' its volume of inert petroleum solvent, with vigorous stirring until the mass solidifies as a, whole, grinding said product and dispersing the same in finely divided condition with a liquid vehicle which is non-solvent of and non-reactive upon and present in substantially equal proportions to the solid components. j
HANS BLUMBERG.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,904,580 Mayer Apr. 28, 1914 1,629,802 Faber May 24, 1927 1,869,557 Gillespie Aug. 2, 1932 1,976,807 Schaeffer Oct. 16, 1934 2,054,283 Ellis Sept. 15, 1936 2,090,708 Stahl 'Aug. 24, 1937 2,234,545 Auer Mar. 11, 1941 2,393,222 Pischel Jan. 15, 1946 2,433,831 Auer Jan. 6, 1948 FOREIGN PATENTS Number Country Date 585,533 Germany Sept. 21, 1933

Claims (1)

1. A METHOD OF MAKING A SOLID, DRY, CLEANER BASE, COMPRISING THE STEPS OF REACTING APPROXIMATELY 100 PARTS OF SOYA BEAN OIL WITH 6-12 PARTS OF HYDRATED LIME, COOLING TO 50* D., ADDING APPROMIMATELY 15 PARTS OF SULPHUR MONOCHLORIDE DILUTED WITH ON-THIRD OF ITS VOLUME OF INERT PETROLEUM SOLVENT, COOLING TO 50* F., ADDING APPROXIMATELY 161/2 PARTS OF SULPHUR MONOCHLORIDE DILUTED WITH 1/2 ITS VOLUME OF INERT PETROLEUM SOLVENT, WITH VIGOROUS STIRRING UNTIL THE MASS SOLIDIFIES AS A WHOLE.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5259984A (en) * 1992-05-11 1993-11-09 Jim Hull Associates, Inc. Rinse-free cleansing composition

Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1629802A (en) * 1924-12-08 1927-05-24 Alfred A Norton Brush mounting for vacuum cleaners, etc.
US1869557A (en) * 1929-03-07 1932-08-02 Stamford Rubber Supply Company Rubber substitute
US1904580A (en) * 1931-07-24 1933-04-18 Gen Electric Protective circuit for enameling furnaces
DE585533C (en) * 1930-07-12 1933-10-04 Dunlop Rubber Co Dry cleaning agent
US1976807A (en) * 1930-08-07 1934-10-16 Carey Philip Mfg Co Protecting composition for materials and process of making and applying the same
US2054283A (en) * 1935-06-13 1936-09-15 Ellis Carleton Factis and process of making same
US2090708A (en) * 1932-10-08 1937-08-24 Standard Oil Dev Co Plastic cleaning composition
US2234545A (en) * 1926-05-19 1941-03-11 Randolph Newman J Manufacture of vulcanized, modified fatty oils
US2393222A (en) * 1942-04-30 1946-01-15 Eagle Pencil Co Rubberless flexible compositions and processes
US2433831A (en) * 1942-12-04 1948-01-06 Auer Laszlo Aqueous dispersions of vulcanized fatty oils

Patent Citations (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1629802A (en) * 1924-12-08 1927-05-24 Alfred A Norton Brush mounting for vacuum cleaners, etc.
US2234545A (en) * 1926-05-19 1941-03-11 Randolph Newman J Manufacture of vulcanized, modified fatty oils
US1869557A (en) * 1929-03-07 1932-08-02 Stamford Rubber Supply Company Rubber substitute
DE585533C (en) * 1930-07-12 1933-10-04 Dunlop Rubber Co Dry cleaning agent
US1976807A (en) * 1930-08-07 1934-10-16 Carey Philip Mfg Co Protecting composition for materials and process of making and applying the same
US1904580A (en) * 1931-07-24 1933-04-18 Gen Electric Protective circuit for enameling furnaces
US2090708A (en) * 1932-10-08 1937-08-24 Standard Oil Dev Co Plastic cleaning composition
US2054283A (en) * 1935-06-13 1936-09-15 Ellis Carleton Factis and process of making same
US2393222A (en) * 1942-04-30 1946-01-15 Eagle Pencil Co Rubberless flexible compositions and processes
US2433831A (en) * 1942-12-04 1948-01-06 Auer Laszlo Aqueous dispersions of vulcanized fatty oils

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5259984A (en) * 1992-05-11 1993-11-09 Jim Hull Associates, Inc. Rinse-free cleansing composition

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