US3265625A - Liquid detergent - Google Patents
Liquid detergent Download PDFInfo
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- US3265625A US3265625A US234240A US23424062A US3265625A US 3265625 A US3265625 A US 3265625A US 234240 A US234240 A US 234240A US 23424062 A US23424062 A US 23424062A US 3265625 A US3265625 A US 3265625A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/26—Organic compounds containing nitrogen
- C11D3/33—Amino carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/02—Anionic compounds
- C11D1/34—Derivatives of acids of phosphorus
- C11D1/345—Phosphates or phosphites
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/38—Cationic compounds
- C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
- C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/72—Ethers of polyoxyalkylene glycols
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/34—Organic compounds containing sulfur
- C11D3/3418—Toluene -, xylene -, cumene -, benzene - or naphthalene sulfonates or sulfates
Definitions
- This invention relates to liquid detergents and more particularly to substantially clear, homogeneous aqueous compositions of high concentration for home laundering and general cleaning use.
- the essential active ingredients in these aqueous detergents are surfactants and salts of aminocar-boxylic acids.
- the liquid detergent composition of this invention otters several advantages over the granular detergent compositions, such as, to name a ⁇ few, freedom from dust, ease of measuring the proper amount for optimum performance, pre-trea-ting of heavily soiled items by spotting them with the undiluted product before placing these items in the washing machine and a soft feel imparted to laundered cotton goods.
- Prior art liquid detergents utilized large quantities of inorganic phosphate builders. The preparation of such products was relatively diificult; sometimes large quantities of hydrotropes were required to produce stable compositions and the amount and type of surfactant was often dictated by limited compatibility of surfactant and phosphate builder.
- the detergent compositions of this invention are stable products at room temperature, exhibiting high 'detergency with moderate to little sudsing in automatic Washing machines. Most of the components making up this invention are supplied in liquid tform facilitating the manufiacture of the end product by requiring only conventional equipment.
- the detergents of this invention generally comprise aqueous compositions containing by weight:
- composition Water which may include such optional constituents as optical brighteners, dyes, and perfumes and the like as is known in the art.
- compositions wherein the concentration of active ingredients exceeds about 20% by weight it is necessary to include as a solubilizing agent trom 1 to by weight of an alkali metal salt of a short chain alkyl aryl sulfonic acid to yield homogeneous, stable compositions.
- compositions as prepared have a pH of about 8 and it is desirable to add alkali to adjust the pH in range of 10 to 11.
- Suitable materials utilizable as component A include the alkali metal salts of ethylenediamine tetra acetic acid such as trisodium ethylenediamine tetraacetate, trisodium hydroxyethyl ethylene-diamine triacetate, penta sodium diethylenetriamine pentaacetate and the like. Suitable materials also are the alkali metal salts of nitrilotriacetic acid such as the mono, 'di or trisodium or potassium salts. Mixtures of two or more aminocarboxylates may be used. The materials may be utilized in the torm of powders or, more conveniently, as aqueous solutions.
- nonionic alkyl aryl polyether alcohols such as tertiary octyl phenoxy polyethoxy ethanol containing 6-20 ethylene oxide units per mole, or nonylphenoxy polyethoxy ethanol containing iirom 6-20 ethylene oxide units per molecule. These materials are supplied as essentially active liquids.
- Suitable materials useable as component C include pnonylphenol condensed with 5-20 moles ethylene oxide which is then esterified with orthophosphoric acid. Additional phosphate esters include those based on tridecyl alcohol condensed with 5-20 moles of ethylene'oiiide, as
- Component D is a so called Krit-chevs-ky condensate of a C to C fatty acid with ethanolamine, propanolamine, diethanolamine and the like. They are mixtures of alkanolamides with alkanolamine soaps of tatty acids and are substantially :100% active liquids.
- the sodium or potassium salts of xylene sulfonic acid, toluene sulfonic acid or benzene sulfonic acid may be used.
- the alkali for adjusting the pH may be potassium hydroxide, sodium hydroxide, ammonia or amines. 'Usually about 0.5% by weight is required.
- Suitable optical brighteners which may be optionally included are the well known stilbene derivatives, such as 4,4'-di'benzoyl ⁇ diamino stilbene 2,2 disul fonic acid. They are usually employed in the range of 0.1 to 0.5 by weight.
- the optical brightener if any, and dispersed with agitation.
- about one-fourth of component A is added with agitation following in succession by the solubilizing agent, if any, and components B, C, and D.
- the remaining threetourths of component A are added and the composition neutralized and the pH adjusted to pH 10-11 by the addition of alkali.
- the end product may be dyed and perfumed as desired.
- the resulting product is a clear liquid, stable at room temperature, only moderately viscous and highly concentrated.
- the product is economical to use; two to three liquid ounces are a sufiicient amount for a top loading automatic washing machine of 12-14 gallons water capacity.
- compositions were prepared consisting of the following:
- compositions I, II, and III are highly concentrated formulations with moderate sudsing.
- Compositions IV and V are highly concentrated, but little sudsing.
- Compositions VI, VII, and VIII are more diluted compositions, but excellent detergents.
- Example IX The following composition was prepared:
- a substantially clear, homogeneous liquid detergent consisting of about 1 to 5% by weight of trisodium hydroxyethyl ethylenediamine triacetate, about 1 to 10% by weight of sodium xylene sulfonate, about 5 to by Weight of oetyl phenol condensed with 12 to 13 moles of ethylene oxide, per mole of phenol about 1 to 10% by weight of the phosphate ester of tridecyl alcoholethylene oxide condensate, having 5 to ethoxy groups per mole of alcohol about 2 to 8% by weight of coconut fatty acid-diethanolamine condensate, about 4 to 10% by weight of trisodium nitrilotriacetate and the remainder water.
- a substantially clear, homogeneous liquid detergent consisting of about 2.05% by weight of trisodium hydroxyethyl ethylenediamine triacetate, about 5% by weight of sodium xylene sulfonate, about 12% by weight of oetyl phenol condensed with 12 to 13 moles of ethylene oxide, per mole of phenol about 5% by weight of the phosphate ester of tridecyl alcohol-ethylene oxide condensate, having 5 to 20 ethoxy groups per mole of alcohol about 7% by weight of coconut fatty acid-diethanolamine condensate, about 7.5% by weight of trisodium nitrilotriacetate, and the remainder water.
- a substantially clear, homogeneous liquid detergent consisting of about 5 to 15% by weight of an alkylphenolethylene oxide condensate having 6 to 20 ethoxy groups per mole of phenol and the alkyl group having 8 to 9 carbon atoms nonionic detergent, about 1 to 10% by weight of a long chain alcohol-ethylene oxide condensate having 5 to 20 ethoxy groups per mole of alcohol esterified with phosphoric acid, said long chain alcohol being selected from the group consisting of tridecyl alcohol and alkyl phenols having 8 to 20 carbon atoms in' the alkyl group, about 2 to 8% by weight of a fatty acid-alkanolamine condensate, the fatty acid having 12 to 16 carbon atoms and the alkanolamine being selected from the group consisting of ethanolamine, diethanolamine and propanolamine, about 4 to 15% of an alkali metal salt of an aminopolyacetic acid selected from the group consisting of nitrilotriacetic acid, ethylenedi
- a detergent composition set forth in claim 3 including about 1 to 10% by weight of a solubilizing agent selected from the group consisting alkali metal salts of toluene sulfonic acid and alkali metal salts of xylene sulfonic acid.
- a detergent composition set forth in claim 3 where the salt of the aminocarboxylic acid is sodium nitrilotriacetate.
- a substantially clear, homogeneous liquid detergent consisting essentially of about 12% by weight p-nonyl phenoxy polyethoxy ethanol having 14 ethoxy units per mole of phenol, about 5% by weight of lauric aciddiethanolamine condensate, about 5% by weight of the phosphate ester of p-nonyl phenol condensed with 10 moles of ethylene oxide per mole of phenol, about 5 by Weight of sodium toluene sulfonate, about 2% by weight of tetrasodium ethylene diamine tetraacetate, about 8% by weight of trisodium nitrilotriacetate, and remainder water.
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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)
- Detergent Compositions (AREA)
Description
United States Patent 3,265,625 LIQUID DETERGENT Erwin Grob, Philadelphia, Pa., assignor to C. P. Baker & Company, Philadelphia, Pa., a corporation of Pennsylvania No Drawing. Filed Oct. 30, 1962, Ser. No. 234,240 9 Claims. (Cl. 252-152) This invention relates to liquid detergents and more particularly to substantially clear, homogeneous aqueous compositions of high concentration for home laundering and general cleaning use.
The essential active ingredients in these aqueous detergents are surfactants and salts of aminocar-boxylic acids.
The liquid detergent composition of this invention otters several advantages over the granular detergent compositions, such as, to name a \few, freedom from dust, ease of measuring the proper amount for optimum performance, pre-trea-ting of heavily soiled items by spotting them with the undiluted product before placing these items in the washing machine and a soft feel imparted to laundered cotton goods.
Prior art liquid detergents utilized large quantities of inorganic phosphate builders. The preparation of such products Was relatively diificult; sometimes large quantities of hydrotropes were required to produce stable compositions and the amount and type of surfactant was often dictated by limited compatibility of surfactant and phosphate builder.
it is an object of this invention to provide an effective liquid detergent utilizing organic builders or sequestrants in relatively smaller amounts. The detergent compositions of this invention are stable products at room temperature, exhibiting high 'detergency with moderate to little sudsing in automatic Washing machines. Most of the components making up this invention are supplied in liquid tform facilitating the manufiacture of the end product by requiring only conventional equipment.
The detergents of this invention generally comprise aqueous compositions containing by weight:
A. 4-15 of an alkali metal salt of an aminocarboxylic acid or a mixture of two salts of such acids.
B. 5-15 of a nonionic surfactant of the type of an al-kyl aryl polyether alcohol.
C. 1-1-0% of a phosphate ester modified by the addition of alkylene oxides.
:D. 2-8% of a fatty acid alkanolamine condensate.
The remainder of the composition is Water which may include such optional constituents as optical brighteners, dyes, and perfumes and the like as is known in the art.
(In compositions wherein the concentration of active ingredients exceeds about 20% by weight, it is necessary to include as a solubilizing agent trom 1 to by weight of an alkali metal salt of a short chain alkyl aryl sulfonic acid to yield homogeneous, stable compositions.
The compositions as prepared have a pH of about 8 and it is desirable to add alkali to adjust the pH in range of 10 to 11.
Suitable materials utilizable as component A include the alkali metal salts of ethylenediamine tetra acetic acid such as trisodium ethylenediamine tetraacetate, trisodium hydroxyethyl ethylene-diamine triacetate, penta sodium diethylenetriamine pentaacetate and the like. Suitable materials also are the alkali metal salts of nitrilotriacetic acid such as the mono, 'di or trisodium or potassium salts. Mixtures of two or more aminocarboxylates may be used. The materials may be utilized in the torm of powders or, more conveniently, as aqueous solutions.
As component B one may use the nonionic alkyl aryl polyether alcohols such as tertiary octyl phenoxy polyethoxy ethanol containing 6-20 ethylene oxide units per mole, or nonylphenoxy polyethoxy ethanol containing iirom 6-20 ethylene oxide units per molecule. These materials are supplied as essentially active liquids.
Suitable materials useable as component C include pnonylphenol condensed with 5-20 moles ethylene oxide which is then esterified with orthophosphoric acid. Additional phosphate esters include those based on tridecyl alcohol condensed with 5-20 moles of ethylene'oiiide, as
well as those based on C to C al-kylphenols condensed with ethylene oxide. They may be used in the iorm of the free acid or as the alkali metal salt. These materials are supplied as essentially 100% active liquids.
Component D is a so called Krit-chevs-ky condensate of a C to C fatty acid with ethanolamine, propanolamine, diethanolamine and the like. They are mixtures of alkanolamides with alkanolamine soaps of tatty acids and are substantially :100% active liquids.
For more concentrated compositions requiring the use of a solubilizing agent or hydrotrope, the sodium or potassium salts of xylene sulfonic acid, toluene sulfonic acid or benzene sulfonic acid may be used.
The alkali [for adjusting the pH may be potassium hydroxide, sodium hydroxide, ammonia or amines. 'Usually about 0.5% by weight is required.
Suitable optical brighteners which may be optionally included are the well known stilbene derivatives, such as 4,4'-di'benzoyl \diamino stilbene 2,2 disul fonic acid. They are usually employed in the range of 0.1 to 0.5 by weight.
A preferred procedure for mixing the ingredients is as follows:
To the required amount of water is added the optical brightener, if any, and dispersed with agitation. Then about one-fourth of component A is added with agitation following in succession by the solubilizing agent, if any, and components B, C, and D. Then the remaining threetourths of component A are added and the composition neutralized and the pH adjusted to pH 10-11 by the addition of alkali. The end product may be dyed and perfumed as desired. The resulting product is a clear liquid, stable at room temperature, only moderately viscous and highly concentrated. The product is economical to use; two to three liquid ounces are a sufiicient amount for a top loading automatic washing machine of 12-14 gallons water capacity.
The iollowing examples illustrate the practice of the invention, in which all parts are by weight. Compositions were prepared consisting of the following:
Components on percent active basis by weight Examples I II III IV V VI VII VIII In the above examples, the pH was adjusted to about pH 10.5 with potassium hydroxide. The optical brightener in the examples was 4,4'-dibenzoyl diamino stilbene- 2,2'-disul-fonic acid.
Compositions I, II, and III are highly concentrated formulations with moderate sudsing. Compositions IV and V are highly concentrated, but little sudsing. Compositions VI, VII, and VIII are more diluted compositions, but excellent detergents.
Example IX The following composition was prepared:
Parts p-Nonyl phenoxy polyethoxy ethanol (14 ethoxy units) 12 Laurie acid-diethanolamine condensate p-Nonyl phenol phosphate-ethylene oxide condensate mols ethylene oxide) 5 Sodium toluene sulfonate 5 Tetrasodium ethylenediamine tetraacetate 2 Trisodium nitrilotriacetate 8 Water to 100.
The above was a clear, heavy duty, moderately sudsing laundry detergent.
While the invention has been described in terms of certain examples, they are to be considered illustrative rather than limiting, and it is intended to cover all further embodiments and modifications apparent to those skilled in the art that fall within the spirit of the claims.
I claim:
1. A substantially clear, homogeneous liquid detergent consisting of about 1 to 5% by weight of trisodium hydroxyethyl ethylenediamine triacetate, about 1 to 10% by weight of sodium xylene sulfonate, about 5 to by Weight of oetyl phenol condensed with 12 to 13 moles of ethylene oxide, per mole of phenol about 1 to 10% by weight of the phosphate ester of tridecyl alcoholethylene oxide condensate, having 5 to ethoxy groups per mole of alcohol about 2 to 8% by weight of coconut fatty acid-diethanolamine condensate, about 4 to 10% by weight of trisodium nitrilotriacetate and the remainder water.
2. A substantially clear, homogeneous liquid detergent consisting of about 2.05% by weight of trisodium hydroxyethyl ethylenediamine triacetate, about 5% by weight of sodium xylene sulfonate, about 12% by weight of oetyl phenol condensed with 12 to 13 moles of ethylene oxide, per mole of phenol about 5% by weight of the phosphate ester of tridecyl alcohol-ethylene oxide condensate, having 5 to 20 ethoxy groups per mole of alcohol about 7% by weight of coconut fatty acid-diethanolamine condensate, about 7.5% by weight of trisodium nitrilotriacetate, and the remainder water.
3. A substantially clear, homogeneous liquid detergent consisting of about 5 to 15% by weight of an alkylphenolethylene oxide condensate having 6 to 20 ethoxy groups per mole of phenol and the alkyl group having 8 to 9 carbon atoms nonionic detergent, about 1 to 10% by weight of a long chain alcohol-ethylene oxide condensate having 5 to 20 ethoxy groups per mole of alcohol esterified with phosphoric acid, said long chain alcohol being selected from the group consisting of tridecyl alcohol and alkyl phenols having 8 to 20 carbon atoms in' the alkyl group, about 2 to 8% by weight of a fatty acid-alkanolamine condensate, the fatty acid having 12 to 16 carbon atoms and the alkanolamine being selected from the group consisting of ethanolamine, diethanolamine and propanolamine, about 4 to 15% of an alkali metal salt of an aminopolyacetic acid selected from the group consisting of nitrilotriacetic acid, ethylenediamine tetraaeetic acid, hydroxyethyl ethyl-diamine triacetic acid, and diethy-lenetriamine pentaacetic acid and the remainder Water.
4. A detergent composition set forth in claim 3 including about 1 to 10% by weight of a solubilizing agent selected from the group consisting alkali metal salts of toluene sulfonic acid and alkali metal salts of xylene sulfonic acid.
5. A deter-gent composition set forth in claim 3 where the nonionie detergent is tert.-octylphenoxy polyethoxy ethanol with from 6 to 20 moles of ethylene oxide per mole of phenol.
6. A detergent composition set forth in claim 3 where the nonionic detergent is nonylphenoxy polyethoxy ethanol with from 6 to 20 moles of ethylene oxide per mole of phenol.
'7. A detergent composition set forth in claim 3 where the salt of the aminocarboxylic acid is sodium ethylenediamine tetraacetate.
8. A detergent composition set forth in claim 3 where the salt of the aminocarboxylic acid is sodium nitrilotriacetate.
9. A substantially clear, homogeneous liquid detergent consisting essentially of about 12% by weight p-nonyl phenoxy polyethoxy ethanol having 14 ethoxy units per mole of phenol, about 5% by weight of lauric aciddiethanolamine condensate, about 5% by weight of the phosphate ester of p-nonyl phenol condensed with 10 moles of ethylene oxide per mole of phenol, about 5 by Weight of sodium toluene sulfonate, about 2% by weight of tetrasodium ethylene diamine tetraacetate, about 8% by weight of trisodium nitrilotriacetate, and remainder water.
References Cited by the Examiner UNITED STATES PATENTS 2,089,212 8/ 1937 Kritchevsky. 2,859,182 11/1958 Carroll. 2,877,178 3/1959 Bergman et al. 252152 XR 2,943,058 6/1960 Cook 252152 XR 3,001,945 9/1961 Drew et al. 252152 3,033,889 5/1962 Chiddix et al 252-89 XR LEON D. ROSDOL, Primary Examiner.
JULIUS GREENWALD, Examiner.
w. E. SCHULZ, J. GREENWALD, Assistant Examiners.
Claims (1)
- 3. A SUBSTANTIALLY CLEAR, HOMOGENOUS LIQUID DETERGENT CONSISTING OF ABOUT 5 TO 15% BY WEIGHT OF AN ALKYLPHENOLETHYLENE OXIDE CONDENSATE HAVING 6 TO 20 ETHOXY GROUPS PER MOLE OF PHENOL AND THE ALKYL GROUP HAVING 8 TO 9 CARBON ATOMS NONIONIC DETERGENT, ABOUT 1 TO 10% BY WEIGHT OF A LONG CHAIN ALCOHOL-ETHYLENE OXIDE CONDENSATE HAVING 5 TO 20 ETHOXY GROUPS PER MOLE OF ALCOHOL ESTERIFIED WITH PHOSPHORIC ACID, SAID LONG CHAIN ALCOHOL BEING SELECTED FROM THE GROUP CONSISTING OF TRIDECYL ALCOHOL AND ALKYL PHENOLS HAVING 8 TO 20 CARBON ATOMS IN THE ALKYL GROUPS, ABOUT 2 TO 8% BY WEIGHT OF A FATTY ACID-ALKANNOLAMINE CONDENSATE, THE FATTY ACID HAVING 12 TO 16 CARBON ATOMS AND THE ALKANOLAMINE BEING SELECTED FROM THE GROUP CONSISTING OF ETHANOLAMINE, DIETHANOLAMINE AND PROPANOLAMINE, ABOUT 4 TO 15% OF AN ALKALI METAL SALT OF AN AMINOPOLYACETIC ACID SELECTED FROM THE GROUP CONSISTING OF NITRILOTRIACETIC ACID, ETHYLENEDIAMINE TETRAACETIC ACID, HYDROXYETHYL ETHLDIAMINE TRIACETIC ACID, AND DIETHYLENETRIAMINE PENTAACETIC ACID AND THE REMAINDER WATER.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US234240A US3265625A (en) | 1962-10-30 | 1962-10-30 | Liquid detergent |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US234240A US3265625A (en) | 1962-10-30 | 1962-10-30 | Liquid detergent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3265625A true US3265625A (en) | 1966-08-09 |
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ID=22880534
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US234240A Expired - Lifetime US3265625A (en) | 1962-10-30 | 1962-10-30 | Liquid detergent |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US3265625A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3763631A (en) * | 1971-06-01 | 1973-10-09 | Chemical Detergents Coinc | Method and apparatus for removing entrained matter from centrifugal filter media |
| US3953380A (en) * | 1970-10-28 | 1976-04-27 | Colgate-Palmolive Company | Liquid detergent |
| US3956198A (en) * | 1972-12-15 | 1976-05-11 | Days-Ease Home Products Corporation | Liquid laundry washing-aid |
| US3966649A (en) * | 1972-09-28 | 1976-06-29 | Colgate-Palmolive Company | Liquid detergents containing chelidamic acids and salts thereof |
| DE2715351A1 (en) * | 1976-08-23 | 1978-03-02 | Henkel Kgaa | Stable liq. low foaming dishwashing concentrates - contg. phosphorus free complexing agent, low foam nonionic surfactant, a hydrotrope and an alkanolamine |
| US4097305A (en) * | 1975-03-14 | 1978-06-27 | Bickmore, Inc. | Method for removing bot eggs from animal hair |
| US4560492A (en) * | 1984-11-02 | 1985-12-24 | The Procter & Gamble Company | Laundry detergent composition with enhanced stain removal |
| US4692276A (en) * | 1984-06-22 | 1987-09-08 | Schramm Charles H | Non-alkaline, foamable bathroom cleaner |
| WO2004104147A1 (en) * | 2003-05-22 | 2004-12-02 | Reckitt Benckiser N.V. | Aqueous cleaning compositions |
| EP2134734A1 (en) * | 2007-03-08 | 2009-12-23 | American Sterilizer Company | Biodegradable alkaline disinfectant cleaner with analyzable surfactant |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2089212A (en) * | 1936-06-08 | 1937-08-10 | Kritchevsky Wolf | Hydrotropic fatty material and method of making same |
| US2859182A (en) * | 1956-11-02 | 1958-11-04 | Lever Brothers Ltd | Heavy duty liquid detergent composition |
| US2877178A (en) * | 1955-12-20 | 1959-03-10 | Gen Aniline & Film Corp | Ampholytic compositions in wet treatments |
| US2943058A (en) * | 1956-10-15 | 1960-06-28 | Diamond Alkali Co | Liquid detergent compositions |
| US3001945A (en) * | 1959-04-29 | 1961-09-26 | Procter & Gamble | Liquid detergent composition |
| US3033889A (en) * | 1958-10-21 | 1962-05-08 | Gen Aniline & Film Corp | Phosphate esters of branched chain alcohols |
-
1962
- 1962-10-30 US US234240A patent/US3265625A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2089212A (en) * | 1936-06-08 | 1937-08-10 | Kritchevsky Wolf | Hydrotropic fatty material and method of making same |
| US2877178A (en) * | 1955-12-20 | 1959-03-10 | Gen Aniline & Film Corp | Ampholytic compositions in wet treatments |
| US2943058A (en) * | 1956-10-15 | 1960-06-28 | Diamond Alkali Co | Liquid detergent compositions |
| US2859182A (en) * | 1956-11-02 | 1958-11-04 | Lever Brothers Ltd | Heavy duty liquid detergent composition |
| US3033889A (en) * | 1958-10-21 | 1962-05-08 | Gen Aniline & Film Corp | Phosphate esters of branched chain alcohols |
| US3001945A (en) * | 1959-04-29 | 1961-09-26 | Procter & Gamble | Liquid detergent composition |
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3953380A (en) * | 1970-10-28 | 1976-04-27 | Colgate-Palmolive Company | Liquid detergent |
| US3763631A (en) * | 1971-06-01 | 1973-10-09 | Chemical Detergents Coinc | Method and apparatus for removing entrained matter from centrifugal filter media |
| US3966649A (en) * | 1972-09-28 | 1976-06-29 | Colgate-Palmolive Company | Liquid detergents containing chelidamic acids and salts thereof |
| US3956198A (en) * | 1972-12-15 | 1976-05-11 | Days-Ease Home Products Corporation | Liquid laundry washing-aid |
| US4097305A (en) * | 1975-03-14 | 1978-06-27 | Bickmore, Inc. | Method for removing bot eggs from animal hair |
| DE2715351A1 (en) * | 1976-08-23 | 1978-03-02 | Henkel Kgaa | Stable liq. low foaming dishwashing concentrates - contg. phosphorus free complexing agent, low foam nonionic surfactant, a hydrotrope and an alkanolamine |
| US4692276A (en) * | 1984-06-22 | 1987-09-08 | Schramm Charles H | Non-alkaline, foamable bathroom cleaner |
| EP0181025A2 (en) * | 1984-11-02 | 1986-05-14 | The Procter & Gamble Company | Laundry detergent composition with enhanced stain removal |
| JPS61166896A (en) * | 1984-11-02 | 1986-07-28 | ザ、プロクタ−、エンド、ギヤンブル、カンパニ− | Washing detergent composition having enhanced stain removal property |
| US4560492A (en) * | 1984-11-02 | 1985-12-24 | The Procter & Gamble Company | Laundry detergent composition with enhanced stain removal |
| EP0181025A3 (en) * | 1984-11-02 | 1989-12-13 | The Procter & Gamble Company | Laundry detergent composition with enhanced stain removal |
| JPH08918B2 (en) | 1984-11-02 | 1996-01-10 | ザ、プロクター、エンド、ギャンブル、カンパニー | Laundry detergent composition having enhanced stain removal |
| WO2004104147A1 (en) * | 2003-05-22 | 2004-12-02 | Reckitt Benckiser N.V. | Aqueous cleaning compositions |
| EP2134734A1 (en) * | 2007-03-08 | 2009-12-23 | American Sterilizer Company | Biodegradable alkaline disinfectant cleaner with analyzable surfactant |
| EP2134734A4 (en) * | 2007-03-08 | 2012-07-11 | American Sterilizer Co | Biodegradable alkaline disinfectant cleaner with analyzable surfactant |
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