US2861956A - Liquid detergent compositions - Google Patents

Liquid detergent compositions Download PDF

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US2861956A
US2861956A US338885A US33888553A US2861956A US 2861956 A US2861956 A US 2861956A US 338885 A US338885 A US 338885A US 33888553 A US33888553 A US 33888553A US 2861956 A US2861956 A US 2861956A
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liquid detergent
condensation product
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US338885A
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Fernandez Louis
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Monsanto Chemicals Ltd
Monsanto Chemical Co
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Monsanto Chemicals Ltd
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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
    • C11D1/00Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/02Anionic compounds
    • C11D1/12Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29Sulfates of polyoxyalkylene ethers

Definitions

  • An object of the invention is to provide a liquid detergent capable of producing a voluminous stable foam.
  • Another object of the invention is to provide a liquid detergent having a proper balance of foaming and detergent properties which render it eminently useful for washing dishes and glassware.
  • a further object of the invention is to provide a liquid detergent combining the property of resistance to the formation of curd in hard water with mildness towards the skin.
  • a further object of the invention is to provide a liquid detergent which is stable against deterioration during storage and use.
  • a still further object of the invention is to provide an eflicient and economical liquid detergent having in combination all of the highly advantageous properties mentioned above.
  • liquid detergents having the above highly advantageous properties are prepared by mixing together in the proportions hereinafter indicated a low molecular weight aliphatic alcohol, water and a water-soluble salt of a sulfated condensation product of about 1 to about 5 mols of ethylene oxide with 1 mol of a C to C aliphatic alcohol. More specifically, these liquid detergents are prepared by mixing together the above three components, with or without a higher aliphatic alcohol and/or a water soluble or water dispersible fatty acid alkanolamide, in the following proportions to make 100% by weight:
  • these liquid detergents are prepared by mixing togetherthe following components in the indicated proportions to make 100% by weight:
  • EXAMPLE I Methanol, water and the triethanolamine salt of the sulfated condensation product of 1 mol of ethylene oxide with 1 mol of dodecyl alcohol were mixed together in the proportionsof 20%, 20% and 60% by weight, respectively. This resulted in the production of a clear liquid detergent which on agitation formed a voluminous stable lather.
  • Lorol is a technical grade of lauryl alcohol, i. e. it is predominately lauryl alcohol containing a mixture of other straight-chain, even-numbered-carbon alcohols having from 10 to 18 carbon atoms.
  • EXAMPLE VI A liquid detergent was prepared by .blending together itheffollow'ing materials in the indicated proportions by Weight.
  • the resulting .products were subjected to the hereinafter described modified dishpan test with the following results:
  • Liquid detergents were prepared by blending the following components in the indicated proportions by The above products were subjected to the modified dishpan test hereinafter described and the following results were obtained:
  • the salts of the sulfated condensation products of ethylene oxide with the C to C -aliphatic alcohols serve as detergents, lathering, emulsifying, and surface active materials; the lower aliphatic alcohols as viscosity controlling agents; the higher aliphatic alcohols as lather stabilizers; the fatty acid alkanolamides as lather producers and lather stabilizers, and the water as a solvent or carrier for the other components.
  • liquid detergents of the instant invention are use ful as windshield cleaning compositions and as household detergents, particularly for washing dishes, glassware, windows, and ceramic articles.
  • a proper balance of lathering and detergent properties I is important since a material may have excellent lathering properties without having satisfactory detergent properties and vice versa.
  • the housewife is accustomed to judge the detergency of a product by its lathering properties and, therefore, she uses this as a criterion to determine whether sufficient detergent has been added to the water to efiect the desired cleansing action.
  • it is quite important, as far as the housewife is concerned, that optimum cleaning coincides or substantially coincides with optimum lathering.
  • a liquid detergent composition comprising the following components in substantially the indicated proportions to make 100% by weight:
  • a liquid detergent composition comprising the following materials in substantially the indicated proportions to make 100% by weight:
  • a liquid detergent composition consisting of 60% by weight of the triethanolamine salt of the sulfated condensation product of 1 mol of lauryl alcohol with 1 mol of ethylene oxide, 6% by weight of lauric acid ethanolamide, 14% by weight of ethanol and by weight of water.
  • a liquid detergent composition consisting of by weight of the triethanolamine salt of the sulfated condensation product of lauryl alcohol with 5 mols of ethylene oxide, 9% by weight of lauryl alcohol, 23% by weight of methanol and 13% by weight of water.
  • a liquid detergent composition consisting of 54% by weight of the triethanolamine salt of the sulfated condensation product of 3 mols of ethylene oxide with 1 mol of tridecyl alcohol, 30% by weight of isopropanol, 6% by weight of lauric acid ethanolamide and 10% by weight of water.
  • a liquid detergent composition comprising (1) from about 20 to about percent by weight of a water-soluble salt of a sulfated condensation product of about 1 to about 5 mols of ethylene oxide with 1 mol of a C to C -aliphatic alcohol, said salt being selected from the group consisting of the sodium, potassium and triethanolamine salts of said sulfated condensation product; (2) from about 5 to about 30 percent by weight of an aliphatic alcohol containing from 1 to 5 carbon atoms; (3) up to 20 percent by weight of an aliphatic alcohol containing from 12 to 14 carbon atoms; (4) up to 20 percent by weight of lauric acid ethanolamide; and (5) the balance to make percent by weight of water; and at least one of components (3) and (4) is present in an amount of at least about 5 percent by weight.
  • liquid detergent composition of claim 8 wherein the water-soluble salt of the sulfated condensation product is the sodium salt.

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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 2,861,956 LIQUID DETERGENT COMPOSITIONS Louis Fernandez, St. Louis, Mo., assignor to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware No Drawing. Application February 25, 1953 Serial No. 338,885
11 Claims. (Cl. 252-453) The present invention relates to liquid detergents, particularly liquid household detergents, and to a method of producing same.
An object of the invention is to provide a liquid detergent capable of producing a voluminous stable foam.
Another object of the invention is to provide a liquid detergent having a proper balance of foaming and detergent properties which render it eminently useful for washing dishes and glassware.
A further object of the invention is to provide a liquid detergent combining the property of resistance to the formation of curd in hard water with mildness towards the skin.
A further object of the invention is to provide a liquid detergent which is stable against deterioration during storage and use.
A still further object of the invention is to provide an eflicient and economical liquid detergent having in combination all of the highly advantageous properties mentioned above.
Other objects and advantages of the present invention will appear from the detailed description hereinafter set forth.
To the accomplishment of the foregoing and related objects, the invention comprises the features hereinafter disclosed, and particularly pointed out in the claims, the following description setting forth in detail some of the various forms in which the principle may be applied.
In accordance with the present invention, liquid detergents having the above highly advantageous properties are prepared by mixing together in the proportions hereinafter indicated a low molecular weight aliphatic alcohol, water and a water-soluble salt of a sulfated condensation product of about 1 to about 5 mols of ethylene oxide with 1 mol of a C to C aliphatic alcohol. More specifically, these liquid detergents are prepared by mixing together the above three components, with or without a higher aliphatic alcohol and/or a water soluble or water dispersible fatty acid alkanolamide, in the following proportions to make 100% by weight:
Percent A water soluble salt selected from the group consisting of sodium, potassium and alkanolamine salts of the sulfated condensation product of about 1 to about 5 mols of ethylene oxide with 1 mol of a C to C -aliphatic alcohol 20-80 An aliphatic alcohol containing from 1 to 5 carbon atoms 0-30 An aliphatic alcohol containing from 12 to 14 carbon atoms 0-20 A water soluble or water dispersible fatty acid alkanolamide such as disclosed in Patent 1,981,-
792 to Orelup and 2,353,081 to Robinson 0-20 Water -Balance Still more specifically, these liquid detergents are prepared by mixing togetherthe following components in the indicated proportions to make 100% by weight:
2,861,956 Patented Nov. 25, 1958 bon atoms 5-20 An aliphatic alcohol containing from 12 to 14 carbon atoms 5-10 A water soluble or water dispersible fatty acid alkanolamide such as disclosed in Patent 1,981; 792 to Orelup and 2,353,081 to Robinson 5-15 Water Balance For a more complete understanding of the present invention reference is made to the following specific examples.
EXAMPLE I Methanol, water and the triethanolamine salt of the sulfated condensation product of 1 mol of ethylene oxide with 1 mol of dodecyl alcohol were mixed together in the proportionsof 20%, 20% and 60% by weight, respectively. This resulted in the production of a clear liquid detergent which on agitation formed a voluminous stable lather.
EXAMPLE H oxide 60 Laurie acid ethanolamide 6 Ethanol 14 Water 20 On agitation, this detergent produced a voluminous lather which was somewhat more stable than that produced by the detergent of Example I.
Lorol is a technical grade of lauryl alcohol, i. e. it is predominately lauryl alcohol containing a mixture of other straight-chain, even-numbered-carbon alcohols having from 10 to 18 carbon atoms.
EXAMPLE III A liquid detergent was prepared by mixing together the following materials in the indicated proportions by weight:
Percent Triethanolamine salt of the sulfated condensation product of 1 mol of Lorol with 1 mol of ethylene oxide 60 Methanol 30 Laurie acid monoethanolamide 6 Water 4 The clear amber liquid thus obtained was evaluated from the standpoint of lathering in the following manner.
One teaspoonful of the detergent was added to two liters of tap water (approximately p. p. m. hardness) at 40 C. in an 8% quart oval dishpan. After adding 100 cc. of Wesson oil to the resulting solution, it was agitated by placing the hand with the fingersspread into the dishpan and moving the hand back and forth just as the housewife does. This was done until 50 cycles had been completed. As a result of this agitation, a very voluminous and stable lather was produced which was reduced to a thin layer of bubbles after a. period of 1 hour and 20 minutes. A commercial liquid detergent having the same content of active material was subjected G 1 to the same test and it produced a foam which subsided 'tothe same level in a period of 1 hour.
The liquid detergent prepared in accordance with this example and the above-mentioned commercial detergent "vi/ere subjected to. the Ross-Miles lather test and the following results were ob't'ainedi 50p. p. m. 300 p. p. m.
Sample 7 "At '5'Mln. At -5'- Min. M Once 4 Once Sommercial liquid detergent cn 1., 1 7. 3 17. 3 17. 8 17. 7 Liquid detergent prepared-in accordance with this example cm.. "20. 7 20.7 19. 9 19:9
These data demonstrate that the liquid detergent prepared in accordancewith this example is superior to the "commercial detergent from the standpoint of lather volume and stability.
The Ross-Miles lather test was applied to a sample of the product produced in accordance with this example after. storage for 5 /2 months. The'following'results were =btained:
60 p. p. m. 300 pop. in.
Sample 7 At Min. At 'oMin. Once Once Stored sample prepared in accord- 'ance with this example .cm 20.2 20.0 20.1 19. 8
The results of this test indicate that after storage for anexten'de'd period oftime there is no deterioration of the'lathe'ring characteristics of the liquid detergent.
EXAMPLE IV A liquid detergent was "prepared byinix'irig together 'thefollowing components in the indicated proportions by weight.
. No. 1, percent Triethanolamine salt of "the sulfated condensation product of 5 mols of ethylene "oxide with 1 mol When subjected to theabove described dishpan test, th is liquid detergent produced a relatively stable volluminousdoam. 7 I U EXAMPLE V 'Liquid detergents were prepared by mixing thewfollow- I The resulting liquid detergents were very c lear light amber "solutions of low viscosity. Both of these solutrons gave excellent results in the dishpan test.
EXAMPLE VI A liquid detergent was prepared by .blending together itheffollow'ing materials in the indicated proportions by Weight.
Percent Triethariolamine salt of the 'sultatea condensation product of Lorol with 5 mols of ethylene oxide- 55 Lauryl alcohol 9 Methanol 23 Water 13 This product was subjected to the dishpan 'test described in Example III and was found to yield a voluminous stable "lather.
EXAMPLE VII Lorol, water, methanol and the triethanolamine salt of the sulfated condensation product of 5 mols of ethylene oxide with 1 mol of'Lorol were mixed together in the proportions of about 5%, 15%, 20% and 60% by weight, respectively. The resulting liquid detergent .mixture "was subjected in a concentration of 0.2% to the 'Ro's's Miles "lather test 'withtlie following results:
DistilledWater 50 p.p. in. 30013.1). m. r
7 At 'sivnns. At 5 Mins. At sMins;
Once Once Once cm. Cm. cm. Om. cm. 1 Cm. 11.9 11.8 11.1 11.0 15.3 15.3
The data listed in theabove table show that there is littledifierence in the lather values of .the-liquiddetergent when employed in distilled or hard water. Moreover, they demonstrate that the action of this product is not adversely affected by .hard water.
EXAMPLE Vin A series of liquid detergents was prepared from :the following materials in the indicated proportions by weight.
Trlethanolamine salt ofthesul- I fated condensa- Laurie I I tionproduct of acid Methanol Ethanol 'Isopro- Water -3-mols.offethyl-' ethanolpanel I one oxldewithl amide liuol 0! tridecyl alcohol fercent -.Percent' Percent. Percent Percent; Percent -54 6 30 10 154 6 10 5;; 6 '30 10 The resulting .products were subjected to the hereinafter described modified dishpan test with the following results:
No Oil 50 C(L'Gl'lSGO 50 cc. Lard Y SaIhple 1 Inst. 5'Mins. Inst. 5'Mins. Inst. 5Mins.
' Inches Inches Inches Inches Inches Inches MethanoL- 1:1 4 2% 1 EthanoL.-- II 4 2% 1% 1% 1% Isopro- I panola- III 4 2% It will be observed .from these data that a volumi 'inous lather was obtained; "thatethanol and :isopropanol :were superior to methanol; and that ethanol was'the best of the three alcohols used.
EXAMPLE IX A liquid detergent was prepared by mixing together the following components in the indicated proportions by weight:
Percent The sodium salt of the sulfated condensation product of 3 mols of ethylene oxide with 1 mol of a G -aliphatic alcohol 60 Methanol 30 Fatty acid ethanolamiden 6 Distilled Water 4 The resulting product was a light yellow liquid which, on being subjected to the dishpan test described in EX- ample III using water Containing 109. parts per million hardness, produced a voluminous stable lather, even in the presence of 50 cc. of lard or Wesson oil,
The preceding example was repeated substituting the triethanolamine salt for the sodium salt and a more voluminous and more stable foam was produced, thus demonstrating the superiority of the triethanolamin salt over the sodium salt.
EXAMPLE X Liquid detergents were prepared by blending the following components in the indicated proportions by The above products were subjected to the modified dishpan test hereinafter described and the following results were obtained:
Crisco (44 g.) Lard (44 g.) Sample Inst., 5 Mins., Inst., 5 Mins, Inches Inches Inches Inches The foregoing results clearly demonstrate the superiority of the detergents prepared by the above method over that of the commercial detergent from the standpoint of foam volume.
EXAMPLE XI A series of liquid detergents were prepared by mixing the following components in the indicated proportions by weight.
Triethanolamiue salt of the sulfated condensation product of 5 mols of ethylene oxide with 1 mol of a tridecyl alcohol pereent 60 55. 5 54 A f :tty acid ethanolamide. do 6 2. 8 6 Methan 0 .d0. 30 27. 8 30 Water, distilled ,.do 4 13.9 10
All of these detergents were clear amber liquids which,
6 on being subjected to. a temperature of about 0 C. for 5 hours, showed no signs of turbidity.-
The salts of the sulfated condensation products of ethylene oxide with the C to C -aliphatic alcohols serve as detergents, lathering, emulsifying, and surface active materials; the lower aliphatic alcohols as viscosity controlling agents; the higher aliphatic alcohols as lather stabilizers; the fatty acid alkanolamides as lather producers and lather stabilizers, and the water as a solvent or carrier for the other components.
The liquid detergents of the instant invention are use ful as windshield cleaning compositions and as household detergents, particularly for washing dishes, glassware, windows, and ceramic articles.
The liquid detergents of the instant invention are characterized by possessing the following combination of properties:
(1) The ability to produce a voluminous stable foam (2) A proper balance of lathering and detergent properties (3) Resistance to the formation of precipitates in hard water (4) The ability to efficiently cut grease from dishes containing same without having a deleterious action on the human skin (5) Stability against deterioration during storage and use The production of a voluminous stable lather is quite essential since lather plays a very important role in the removal of oils and fats from smooth surfaces such as are encountered in dishwashing (J. Soc. Dyers Colorists 68, pages 57-9, 1952). In addition, a voluminous. lather is highly desirable since a poorly lathering detergent has very little consumer appeal for household use.
A proper balance of lathering and detergent properties I is important since a material may have excellent lathering properties without having satisfactory detergent properties and vice versa. Moreover, the housewife is accustomed to judge the detergency of a product by its lathering properties and, therefore, she uses this as a criterion to determine whether sufficient detergent has been added to the water to efiect the desired cleansing action. Thus, in order to ensure the best a given detergent, it is quite important, as far as the housewife is concerned, that optimum cleaning coincides or substantially coincides with optimum lathering.
The resistance to the formation of precipitates in hard water is highly desirable since such precipitates consume the detergent and remove it from the scene of the action. Thus, if the detergent does not possess this desirable property, an excessive amount of detergent will be required to carry out a given cleaning operation unless the hardness is counteracted by the addition of water softening or calcium sequestering agents.
The provision of a liquid detergent having the property of removing grease from smooth articles such as dishes without having a deleterious efiect on the human skin is extremely important to the housewife for obvious reasons.
The importance of providing a liquid detergent which is stable to change in detergency and ability to produce a stable voluminous lather is also self-evident,
The Ross-Miles lather test used in evaluating the liquid detergents described herein is described in an article by John Ross and G. D. Miles, entitled An Apparatus for Comparison of Foaming Properties of Soaps and Detergents, which is reported in Oil and Soap, vol. 18, pages 99-102 (1941).
Description of modified dishpan test One teaspoonful of the detergent was added to two liters of water (approximately 100 parts per million hardness) at 40 C. in a 4-gallon rectangular vessel which was 13 inches long, 9 inches wide and 8 /2 inches tall,
results with .7 When desired, 44 grams of Crisco or lard was added. The product was then agitated by placing the hand with. the fingers spread apart into the vessel and moving'the hand back and forth until fifty cycles had been completed. At the end of this operation, the height of the foam was measuredin inches to the nearest one-eighth inch up to two inches of suds and to the nearest one-fourth inch above two inches of suds.
.What I claim is:
1. A liquid detergent composition comprising the following components in substantially the indicated proportions to make 100% by weight:
' Percent A triethanolamine salt of a sulfated condensation product of about 1 mol ethylene oxide with 1 mol of a C to C -aliphatic alcohol 40-60 An aliphatic alcohol containing from 1 to 5 carbon atoms 5-20 An aliphatic alcohol containing from 12 to 14 carbon atoms 5-10 Lauric acid ethanolamide 5-15 Water Balance 2. A liquid detergent composition comprising the following materials in substantially the indicated proportions to make 100% by weight:
Percent A triethanolamine salt of a sulfated condensation product of about 5 mols of ethylene oxide with 1 mol of C to c -aliphatic alcohol 40-60 An aliphatic alcohol containing from 1 to 5 carbon atoms 5-20 An aliphatic alcohol containing from 12 to 14 carbon atoms 5-10 Lauric acid ethanolamide 5-15 Water Balance 3. A liquid detergent composition consisting of 60% by weight of the triethanolamine salt of the sulfated condensation product of 1 mol of lauryl alcohol with 1 mol of ethylene oxide, 6% by weight of lauric acid ethanolamide, 14% by weight of ethanol and by weight of water.
4. A' liquid detergent composition consisting of 60% by weight of the triethanolamine salt of the sulfated condensation product of 1 mol of lauryl alcohol with 1 mol of ethylene oxide, by weight of methanol, 6% by weight of lauric acid monoethanolamide and 4% by weight of water.
5. A liquid detergent composition consisting of by weight of the triethanolamine salt of the sulfated condensation product of lauryl alcohol with 5 mols of ethylene oxide, 9% by weight of lauryl alcohol, 23% by weight of methanol and 13% by weight of water.
6. A liquid detergent composition consisting of 54% by weight of the triethanolamine salt of the sulfated condensation product of 3 mols of ethylene oxide with 1 mol of tridecyl alcohol, 6% by weight of lauric acid ethanolamide, 30% by weight of ethanol and 10% by weight of water.
7. A liquid detergent composition consisting of 54% by weight of the triethanolamine salt of the sulfated condensation product of 3 mols of ethylene oxide with 1 mol of tridecyl alcohol, 30% by weight of isopropanol, 6% by weight of lauric acid ethanolamide and 10% by weight of water.
8. A liquid detergent composition comprising (1) from about 20 to about percent by weight of a water-soluble salt of a sulfated condensation product of about 1 to about 5 mols of ethylene oxide with 1 mol of a C to C -aliphatic alcohol, said salt being selected from the group consisting of the sodium, potassium and triethanolamine salts of said sulfated condensation product; (2) from about 5 to about 30 percent by weight of an aliphatic alcohol containing from 1 to 5 carbon atoms; (3) up to 20 percent by weight of an aliphatic alcohol containing from 12 to 14 carbon atoms; (4) up to 20 percent by weight of lauric acid ethanolamide; and (5) the balance to make percent by weight of water; and at least one of components (3) and (4) is present in an amount of at least about 5 percent by weight.
9. The liquid detergent composition of claim 8, wherein the water-soluble salt of the sulfated condensation product is the triethanolamine salt.
10. The liquid detergent composition of claim 8, wherein the water-soluble salt of the sulfated condensation product is the potassium salt.
11. The liquid detergent composition of claim 8, wherein the water-soluble salt of the sulfated condensation product is the sodium salt.
References Cited in the file of this patent UNITED STATES PATENTS 1,970,578 Schoeller et al Aug. 21, 1934 2,089,305 Stickdorn Aug. 10, 1937 FOREIGN PATENTS 674,896 Great Britain July 2, 1952

Claims (1)

  1. 8. A LIQUID DETERGENT COMPOSITION COMPRISING (1) FROM ABOUT 20 TO 80 PERCENT BY WEIGHT OF A WATER-SOLUBLE SALT OF A SULFATED CONDENSATION PRODUCT OF ABOUT 1 TO ABOUT 5 MOLS OF ETHYLENE OXIDE WITH 1 MOL OF C10 TO C18-ALIPHATIC ALCOHOL, SAID SALT BEING SELECTED FROM THE GROUP CONSISTING OF THE SODIUM, POTASSIUM AND TRIETHANOLAMINE SALTS OF SAID SULFATED CONDENSATION PRODUCT; (2) FROM ABOUT 5 TO ABOUT 30 PERCENT BY WEIGHT OF AN ALIPHATIC ALCOHOL CONTAINING FROM 1 TO 5 CARBON ATOMS; (3) UP TO 20 PERCENT BY WEIGHT OF AN ALIPHATIC ALCOHOL CONTAINING FROM 12 TO 14 CARBON ATOMS; (4) UP TO 20 PERCENT BY WEIGHT OF LAURIC ACID ETHANOLAMIDE; AND (5) THE BALANCE TO MAKE 100 PERCENT BY WEIGHT OF WATER; AND AT LEAST ONE OF COMPONENTS (3) AND (4) IS PRESENT IN AN AMOUNT OF AT LEAST ABOUT 5 PERCENT BY WEIGHT.
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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3179599A (en) * 1961-07-03 1965-04-20 Procter & Gamble Detergent composition
US3179598A (en) * 1961-07-03 1965-04-20 Procter & Gamble Detergent composition
US3186943A (en) * 1961-12-11 1965-06-01 Safety Dev Corp Foam method for atmosphere control
US3422011A (en) * 1966-05-03 1969-01-14 Kidde & Co Walter Foam producing material
US3479285A (en) * 1966-10-31 1969-11-18 Safety Dev Corp Foam producing materials and method for atmosphere control with high expansion foam
US4024078A (en) * 1975-03-31 1977-05-17 The Procter & Gamble Company Liquid detergent composition
US4717507A (en) * 1985-05-04 1988-01-05 Henkel Kommanditgesellschaft Auf Aktien Liquid detergent with fabric softening properties
US6765024B1 (en) * 1999-04-14 2004-07-20 Mcintyre Group, Ltd. Alkanolamide surfactant emulsions and process therefor

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1970578A (en) * 1930-11-29 1934-08-21 Ig Farbenindustrie Ag Assistants for the textile and related industries
US2089305A (en) * 1932-11-11 1937-08-10 Stickdorn Kurt Liquid soap
GB674896A (en) * 1949-05-18 1952-07-02 Marchon Products Ltd Improvements in the manufacture of detergent compositions

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1970578A (en) * 1930-11-29 1934-08-21 Ig Farbenindustrie Ag Assistants for the textile and related industries
US2089305A (en) * 1932-11-11 1937-08-10 Stickdorn Kurt Liquid soap
GB674896A (en) * 1949-05-18 1952-07-02 Marchon Products Ltd Improvements in the manufacture of detergent compositions

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3179599A (en) * 1961-07-03 1965-04-20 Procter & Gamble Detergent composition
US3179598A (en) * 1961-07-03 1965-04-20 Procter & Gamble Detergent composition
US3186943A (en) * 1961-12-11 1965-06-01 Safety Dev Corp Foam method for atmosphere control
US3422011A (en) * 1966-05-03 1969-01-14 Kidde & Co Walter Foam producing material
US3479285A (en) * 1966-10-31 1969-11-18 Safety Dev Corp Foam producing materials and method for atmosphere control with high expansion foam
US4024078A (en) * 1975-03-31 1977-05-17 The Procter & Gamble Company Liquid detergent composition
US4717507A (en) * 1985-05-04 1988-01-05 Henkel Kommanditgesellschaft Auf Aktien Liquid detergent with fabric softening properties
US6765024B1 (en) * 1999-04-14 2004-07-20 Mcintyre Group, Ltd. Alkanolamide surfactant emulsions and process therefor

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