US2742436A - Preparation of non-dusting organic - Google Patents

Preparation of non-dusting organic Download PDF

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US2742436A
US2742436A US2742436DA US2742436A US 2742436 A US2742436 A US 2742436A US 2742436D A US2742436D A US 2742436DA US 2742436 A US2742436 A US 2742436A
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detergent
phenol
ethylene oxide
dusting
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United States PREPARATION OF NON-DUSTING ORGANIC I DETERGENT COMPOSITIONS Russell L. Jenkins, Webster Groves, Mo., assignor to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware No Drawing. Application July 16, 1952, Serial No. 299,243
15 Claims. (Cl. 252-461) ate'nt' the tendency of these synthetic organic detergents to form dust when they are converted into flakes, grains, agglomerates, chips or other physical forms having at least one short dimension. This is a serious disadvantage since, in addition to the undesirability from a merchandising standpoint, the very fine dust 'sifts from the packages in which the detergents are sold, thus producing a shortage in weight to the consumer. Moreover, the dust from the detergent causes a very objectionable irritation of the eyes and nose of those engaged in its manufacture and also the consumer who, in the case of most packaged goods,
In addition, excessive dustis generally the housewife. ing results in a substantial reduction in the yield of these products to say nothing of the unsightly appearance created by the accumulation of dust in adjacent parts of the plant.
Because of the complaints made by manufacturers and members of the consuming public as a result of the tendency of these products to dust, considerable eifort has been made to solve this problem. Substantial progress in this direction has been made, but there is still an urgent demand in the art for an improved dedusting agent and also for a dedusting agent which will not have a deleterious efiect on the lathering and detergent properties of the detergent with which it is associated.
'It is, therefore, the primary object of the instant invention to provide a new synthetic organic detergent composition characterized by a substantially reduced tendency to dust as compared with the active material or the untreated detergent composition containing same.
Another object of the invention is to provide a novel non-dusting synthetic organic detergent composition which'retains the lathering and detergent properties of the active material and/or the untreated detergent composition containing same.
Another object of the invention is to provide a substantially non-dusting synthetic organic detergent which does not tend to cake excessively.
A further object of the invention is to provide dedusting agents which, when associated with normally-dusting synthetic organic detergents, minimizes the loss in yield of the product which accompanies excessive dusting of the active material or the untreated detergent compositions containing same.
Other objects and advantages will become apparent to those skilled in the art as the description of the invention p'roceeds.
I. have discovered that normally-dusting, solid, synthetic organic detergents of the type hereinafter described may be rendered substantially non-dusting by incorporating" therewith about 0.5% to about 5% by weight of a phenol-ethylene oxide condensation product containing from 1 to 25 moles of ethylene oxide per mole of phenol. These condensation products are oily liquids to waxy solids and are prepared by the method described in Patent 1,970,578 to I. G. Farbenindustrie.
The condensation products of the instant invention may be incorporated in the product in any suitable manner such as by mixing with the solid detergent; by spraying onto the solid detergent; and by adding same to the neutralized solution or slurry of the detergent and then drum drying or spray drying the resulting product.
For a more complete understanding of the present invention reference is made to the following specific examples.
EXAMPLE I Samples of a normally-dusting detergent containing approximately 40% dodecylbenzene sodium sulfonate and 60% sodium sulfate, in the form of particles passing a 20 mesh screen, were sprayed with the following amounts of a condensate of 12 moles of ethylene oxide with 1 mole of phenol, using spraying times of 3.3, 8.0, 6.5 and 8.0 minutes, respectively. The products thus obtained were tested by the method hereinafter described to determine the dedusting action of the above condensate. The following results were obtained.
Spraying Dust Percent: Additive Time, Value,
' Minutes M. A. S.
None 2, 513 1. 880 367 182 70 This example demonstrates that the phenol-ethylene oxide condensation product markedly reduces the tendency of theabove detergent composition to dust; it also shows the importance of not spraying too fast.
EXAMPLE II The salt mixture of Example I including dodecylbenzene sodium sulfonate and sodium sulfate was sprayed with 0.5% by weight of the condensate of one mole of phenol with 12 moles of ethylene oxide. This product was then evaluated from the standpoint of dusting with the following results:
Per cent additive: Dustvalue M. A. S. None 4300 0.5 1850 Table I Condensation Product 1 Dust (Ethylene Oxide/ Synthetic Detergent 1 Value Phenol Molar Ratio) v M. A.
None Composition Containing Approx- 4,165
imately 40% Dodecylbeuzene Sodium Sultonate and 60% Sodium Sulfate.
The tests involving this series of dedusting agents were :arried out in a 'gallon rotating drum using a charge of lbs. of the detergent mixture. The additives were all heated to 100 C. before application, but they were transferred to a graduated funnel for measuring and then introduced in through a tube so that the temperature of application of the dedusting agents to the detergent mix- 4 Z the dedusted products of the insatnt invention represent a substantial advance in the art over the listed commercial products.
The dedusting agents of the instant invention have the property of substantially reducing the tendency of normally-dusting solid synthetic organic detergents. .to dust without adversely afiecting their detergent properties. As
ture was considerably below 100 C. The additive was evidence of this fact, reference 18 made to the experiintroduced in a period of about 2.5 minutes and in an mental data set forth inTable III. Table III Detergency At 0.2% Concentration Basis, Standard Detergent Mixture Congmgg a Basis, Gerdinol, mining Ap 0.125%6011- WA mately odeccenmmmh,
ylbenzene Sodium Seconds Sultanate and 60% Rammed Sodium Suliate to we;
300 so 300 p. p. m p. p. m. p. p. m. p. p. m.
Detergent I:
Composition Containing Approximately 40% Dodecylbenzene Sodium Sulionate and Sodium Sulfate Plus 1% oi Condensete of 12 Moles oi Ethylene Oxide with 1 Mole oi Phenol 100 102 28.1 Detergent II:
Composition Containing Approximately 40% Dodecylbenzene Sodium Sulionate and 60% Sodium Sulfate Plus 1% oi Condensate of 6 Moles oi Ethylene Oxide with 1 Mole oi Phenol 102 90 100 38. 8 Detergent III: I
Composition Containing Approximately 40% Dodeeylbenzene Sodium Sulionate and 60% Sodium Sulfate Plus 2% oi Condensate of 12 Moles oi Ethylene Oxide with 1 Mole oi Phenol 100 90 102 100 25. 3 Detergent IV:
Composition Containing Approximately 40% Dodecylbenzene Sodium Sulionate and 60% Sodium Sulfate Plus 2% oi Condensate oi 6 Moles oi Ethylene Oxide with 1 Mole of Phenol; 101 90 104 100 27. 6' Detergent V: I i
Composition Containing Approximately 40% Dodecylbenzene Sodium Sulionate and 60% Sodium Sulfate r 99 112 109 31.!
1 Draves-Clarkson test for wetting out etficleney.
amount corresponding to 1.25% by weight. After the dedusting agent had been added, the rotation of the drum was continued for 2 minutes. The product thus'obtained was then evaluated from the standpoint of dusting with the results indicated above. 7
It will be noted from Table I that while all of the given ratios were efiective, the condensation product containing 10 moles of ethylene oxide per mole of phenol gave the optimum results.
Typical products of the instant invention were evaluated from the standpoint of dustiness and compared with commercially availabel products with the following results.
Table 11 Synthetic detergent: Dust values M. A. S.
' Composition containing approximately 40% dodecylbenzene sodium sulionate and 60% sodium sulfate 3200 Composition containing approximately 40% dodeeylbenzene sodium sulionate and 60% sodium sulfate plus 1.3% Phenolethylene oxide condensation product containing 12 moles of ethylene oxide per mole of phenol 250 Commercial detergent A based upon a soluble salt oi an alkyl 3200 "'fiiiKrifibiiifii'itbi'fiiiiyi 355 Commercial deterg C 5556565631ybifiu'itbi'iifiiiiii aryl sulionic aeld-. 1465 Commercial detergent D based upon a soluble salt of a suliated higher aleohol 1415 Composition containing approximately 40% dodecylbenzene sodium sulionate and 60% sodium suiiate plus 1.25% phenolethylene oxide condensation product containing 12 moles of ethylene oxide per mole of phenol 275 Commercial deter ent E based upon a soluble salt or a suliated higher nice 01 305 Commercial deter ent F based upon a soluble salt oi a suliated higher alco ol 090 The experimental data given in this table indicate that i products,
The standard Launderonieter procedure employed herein for evaluating detergency is that described by Jay C. Harris in Soap and Sanitary Chemicals for August and September 1943. The hard water employed had a hardness of 300 p. p. m., the soft water ahardne ss of 50 p. p. m. The detergent was employed in a concentra. tion of 0.2%. However, instead of reporting theresults, as per cent of soil removed, as described by Harris, the eflectiveness of the detergent compositions is" compared with that of .Gardinol WA (sodium lorol sulfate) and 'a standard detergent mixture containing approximately 40%.. dodecylbenzene sodium sulionate and 6.0% sodiumsul-I fate, the value of each being taken as 100%. i
The Draves-Clarkson test involves a determination of the time required to wet a standard skein sample, using the method described in the 1935-1936 Yearbook of the. American Association of Textile Colorists, at pages 1162- 165.
It will be noted from the data given in Table III thatthe phenol-ethylene oxide condensation product had no significant elfect on the detergency or wetting action of? the detergent mixture.
The phenol-ethylene oxide condensation productsof the" instant invention also have the highly advantageous prop 'erty' of substantially abating the tendency of normally;
dusting solid synthetic organic detergents to dust witho'u adversely affecting their lathering properties. In':c0ntrast to the actionof phenol-ethylene oxide condensation the alkylated derivatives thereof have the prop erty of abating dust when associated with these detergents but are subject to the disadvantage of substantially redu'C Q '5 ing their lathering action. As evidence of these facts, reference is made to the experimental data given in the following table.
Table IV Lather at 0.1%, 300 p. p. m.
At Once 5 Min.
Composition Containing Approximately 40% 14. B 12. S Dodeeylhenzene Sodium Sultonate and 60% V 12.7 10. 4 Sodium Sulfate 14.0 14. 5 Composition Containing Approximately 40% 'Dodecylbenzene Sodium Sultanate and 60% 6; 5 6. Sodium SuliatePlus 1.25% by Weight of an Alkyl G. 3 5.
Phenoxy Polyethoxy Ethanol (Triton X155) Composition I Containing Approximately 40% Dodecylbenzene Sodium Sultanate and 60% u 5 n 0 Sodium Sulfate Plus 1.25% by Weight of Conden- 5 0 satlagt 12 Moles 0t Ethylene Oxide With 1 M010 1 I 0 sun a.
It will be observed from the data given in Table"I V that the lathering property of the detergent mixturewas' substantially reduced in hard water by the presence of Triton X155 whereas the phenolethylene oxide condensate had substantially no effect onthis property of the detergent mixture.
The phenol-ethylene oxide condensates of the instant invention have a further highly advantageous'properjty' which is manifested when the products of the instant invention are employed in the manufacture-bf detergent compositions containing sodum dichromate to inhibit cor aqueous medium over that ofthe same detergent not containing the condensate.
In the practice of the instant invention, the phenolethylene oxide condensates are employed in an amount varying from about 0.5% to about 5% by weight or, more. specifically, within the range of about 1% to about 3% by, weight and within the above limits about 1.25% to about 2% by Weight is preferred. The above figures are based on the total solids content of the detergent.
When the phenol-ethylene oxide condensate is incorporated in a solution or slurry of the detergent and the product spray dried, larger amounts are required than when the condensate is mixed with the dry detergent. Roughly it requires the use of 1.25%, 2.5%, 5.0%,'7.5%, 10.0% and 12.5% of the condensate, basis total solids, content, in order to obtain a dedusting action equivalent to that obtainable by incorporating the additive to the dry detergent in the proportions of 0.5 1%, 2%, 3%, 4% and 5%, respectively.
The phenol-ethylene oxide condensates within the scope of the present invention are those having a molar ratio of ethylene oxide to phenol of from 1:1 to about 25:1 and within the foregoing limits those products having a molar ratio range of from 6:1 to 16:1 and particularly those having a molar ratio range of 6:1 to 10:1 are preferred. a
The normally-dusting, solid organic detergents within the scope of the present invention include long-chain primary alkyl hydrogen sulfates; long-chain primary alkyl sulfonates; long-chain secondary alkyl hydrogen sulfates; salts of monocarboxylic acid amides of taurine; salts of long-chain alkyl amides of sulfo-acetic acid; sulfosucdodecyl sulfate, sodium salt of sulfated fatty alcohols obtained by hydrogenation of 'coco'anut oil; sodium cetane s'ulfonate, sodium dodecyl sulfonate, and sodium tetradecyl sulfonate; sodium secondary dodecyl sulfate; sodium salt of the amide from oleic acid and methyl taurine, sodiurn dioctyl sulfo succinate; sodium dibutyl naphthalene sulfates and in many instances, the last two salts are as indicated earlier herein,
sulfonate, sodium dodecyl benzene sulfonate and sodium hexyl naphthalene sulfonate; salts of aryl naphthene sulfonates with short and long chain substituents, salts of sulfonated aromatic mineral oil extracts in sulfur dioxide and salts of sulfonated aliphatic mineral oils; and the sodium salt of the sulfate of diethylene glycol monolaurate. The above detergents have an increased tendency to dust when mixed with inorganic salts such as sodium carbon ate, borax, sodium'silicate, sodium phosphates or sodium formed in the product during the the sulfonated or sulfated product.
Although the above examples are directed to the treat-. ment of the sodium salts of the organicdetergents, the invention is applicable to the dedusting of other salts including those of calcium, barium, magnesium and stronprocess of neutralizing tium; alkaline metals; earth metals; ammonium and substituted ammonium such as ethanolamine, and mono-, diand triamylamine; and other organic nitrogen bases.- Moreover, although the above examples are directed to the processing of mixtures containing synthetic organic detergents, it is to be understood that the invention is applicable to the dedusting of the organic detergents per se.
Other materials may be added before, during or after producing the final detergent. Examples of these are soaps, coloring agents, inert fillers, builders such as sodium carbonate, ammonia and ammonium salts, perfume, fats, oils, waxes, gums, resins, germicides and deodorants, water softening agents such as pyroand hexametaphosphoric acid compounds, sodium triphosphate, trisodium phosphate, alkali metal salts of ethylene bis (iminodiacetic) acid and other conventional water soluble alkaline metal salts. The resulting products find use in the household and in the textile, cosmetic, paper, plastic and leather industries.
The products of the instant invention may be produced in the form of flakes, grains, hollow beads, ribbons or chips, which products will have a substantially reduced tendency to dust over the original untreated material.
The specific examples have been restricted to a meth 0d of producing non-dusting detergents in which the phenol-ethylene oxide condensate is incorporated with the normally dusting synthetic solid organic detergent by spraying the condensate onto the detergent. However, other methods of achieving the above objective may be employed.
For example, one very practical method of producing non-dusting detergents is to incorporate the phenol-ethylene oxide condensate in a solution or slurry of the detergent and then spray dry the mixture to form a granular product. Thus, a granular non-dusting detergent may be produced by preparing a 30% 50% slurry of the following mixture:
Parts by weight Magnesium sulfate (anhydrous basis) Condensate'of 10 moles of ethylene oxide with 1 mole of phenol 10 ama and then spray drying the resulting composition under the following conditions:
Temperature of feed stock C 54 Inlet gas temperature C.. 232' Outlet gas temperature C 121 Spray wheel type Small labyrinth type Speed of spray wheel R. P. M.-- 3,000
Parts by weight Mixture of dodecyl benzene and tridecyl benzene sodium sulfonates 100 Sodium sulfate (anhydrous) 60 Sodium carbonate (anhydrous) 40 Hydrated magnesium sulfate 4 Condensate of 16 moles of ethylene oxide with 1 mole of phenol;
and then drum drying the above composition under the following conditions: Temperature of suspension fed to drier 70 C.
Drum spacing (aperture between rolls) 0.021 inch.
Roll temperature 121 C.
Speed of rolls 4 R. P. M. Steam pressure 30-32 lbs./in. Flake thickness of dried product 0018-0022 inch. Moisture in dried product 2.8%
Apparent specific gravity 0.3586.
The dust values given earlier herein as M. A. S.
(microampere seconds) were determined in the following manner.
A light source was adjusted so that the light. coming through the test chamber gave an output of 100 microamperes from a photoelectric cell. A sample of the detergent was dropped into the test chamber and the dust cloud reduced the light received by the cell with a corresponding amperage output decrease. The microampere reading from the cell during the test was plotted and the area between this plot and the plot that would be obtained if no dust were present (a straight lineat 100 microamperes) was a measure of the dustiness. Therefore, a high M. A. 5. value indicates a dusty product.
It is to be understood that the invention is not tobe limited by the specific examples hereinabove set forth as they are illustrative only. The invention is limited solely by the appended claims.
What I claim is:
l. The method of preparing a substantially non-dusting detergent, having a M. A. S. dust value of less than 1000, which comprises spray drying an aqueous composition containing a normally-dusting, solid synthetic anionic organic detergent of the class consisting of sulfates and sulfonates and about 1.25% to about 12.5% by weight, based, on total solids content, of a condensate of from 1 to moles of ethylene oxide with 1 mole of phenol.
2. The method of preparing a substantially non-dust ing detergent, having a M. A. S. dust value of less than 1000, which comprises spray drying an aqueous corn v position containing a normally-dusting, solid synthetic anionic organic detergent of the class consisting of sulfates and sulfonates and about 1.25% to about 12.5% by weight, based on the total solids content, of a condensate of from 6 to 16 moles of ethylene oxide with 1 mole of phenol.
3. Themethod of producing a substantially non-dusting detergent having a M. A. S. dust value ofless than 1000,
containing a water soluble salt of a higher alkyl aryl sulfonic acid and about 2.5% to about 7.0% by weight,
based on total solids content, of a condensate of from 6 to 16 moles of ethylene'oxide with 1 mole of phenol.
4; The method of producing a substantially non-dusting detergent having a M. A. S. dust value of less than 1000, which comprises drying on an evaporative surface an aqueous composition containing a water soluble salt of a higher alkyl aryl sulfonic acid and about 0.5% to about 5% by weight, based on total solids content, of a condensate of from 1 to 25 moles of ethylene oxid with 1 mole of phenol. Y
. 5. The method of preparing a substantially non-dusting detergent, having'a M; A. S. dust value of less than 1000, which comprises drum drying an aqueous composition containing a water soluble salt of a higher alkyl aryl sulfonic acid and about 0.5 to about 5% by Weight, based on total solids content, of a condensate of about 6 I to 16 moles of ethylene oxide with 1 mole of phenol.
6. The method of preparing a substantially non-dusting detergent, having a M. A. S. dust value of less than 1000, which comprises producing an aqueous composition containing a water soluble'salt of a higher alkyl aryl sulfonic acid and about 0.5% to about 12.5% by weight, based on total solids content, of a condensate of from 1 to 25 moles of ethylene oxide with 1 mole of phenol, and then conver'ting said mixture to particle form with substantial drying.
7.The method of preparing. a substantially non-dusting detergent, having a M. A. S. dust value of less than 1000, which comprises spraying onto the particles of a normallydusti'ng', solid synthetic anionic organic detergent of the class'consi'sting of'sulfates and sulfonates about 0.5% to about 5% by weight of a condensate of from 1 to 25 moles'of ethylene oxide with 1 mole of phenol.
18. The method of preparing a substantially non-dusting detergent, having a M. A. S. dust value of less than 1000, which comprises spraying onto the particles of a water soluble salt of r a higher alkyl aryl sulfonic acid about 1.25% to about 2.0% by weight of a condensate of from 6 to 16'moles of ethylene oxide with 1 mole of phenol.
'9. A detergent. composition in particle form comprising a normally-dusting, solid synthetic anionic organic detergent of the class consisting of sulfates and sulfonates and'a sufficient amount of a phenol-ethylene oxide condens'ate toreduce theM. A. S. dust value of said detergent to lessthan 1000', said phenol-ethylene oxide condensate containing from I to 25 moles of ethylene oxide per mole ofphenol.
10. A' substantially non-dusting detergent composition in particle form having at least one short dimension comprising a normally-dusting, solid synthetic anionic organic detergent of the class consisting of sulfates and sulfonates and about 0.5% to about 5% by weight of a condensate of from 1 to 25 moles of ethylene oxide with 1 mole of phenol as a dedusting agent therein and suffici'ent-to reduce the M. A. S. dust value of said detergent to'lessthan I000.
'11. A substantially non-dusting detergent composition inparticl'e form having at least. one short dimension comprising a water soluble salt of a higher alkyl aryl sulfonic acid and about. 0.5 to about 5% by weight of a condensate of from 6 to16 moles of ethylene oxide with 1 mole of phenol as a'dedusting agent therein and sufficient to reduce the M. A. S. dust value of said detergent to -less than 1 000. g
12. A substantially non-dusting detergent composition in the form of spray dried particles comprising a water soluble salt of a higher alkyl aryl sul'fonic acid and about 0.5% to about 5% by weight of a condensate of from 6 to 16 moles of ethyleneoxid'e with 1 mole of phenol as a dedusting agent therein and sulficient to reduce the A- S. dust value of said detergent to less than 1000.
tion containing a normallydusting, solid synthetic anionic 7 organic detergent of the class consisting of sulfates and sulfonates and a sufiicient amount of a condensate of from 1 to 25 moles of ethylene oxide with 1 mole of 10 phenol to render said detergent substantially non-dustiug, and then converting said mixture to particle form with substantial drying.
15. The detergent composition of claim 11 wherein the water-soluble salt of a higher alkyl aryl sulfonic acid is sodium dodecylbenzene sulfonate.
References Cited in the file of this patent UNITED STATES PATENTS 1,970,578 Schoeller Aug. 21, 1934 2,423,450 Heald July 8, 1947 2,489,955
Colgate Nov. 29, 1949

Claims (2)

1. THE METHOD OF PREPARING A SUBSTANTIALLY NON-DUSTING DETERGENT, HAVING A M. A. S. DUST VALUE OF LESS THAN 1000, WHICH COMPRISES SPRAY DRYING AN AQUEOUS COMPOSITION CONTAINING A NORMALLY-DUSTING, SOLID SYNTHETIC ANIONIC ORGANIC DETERGENT OF THE CLASS CONSISTING OF SULFATES AND SULFONATES AND ABOUT 1.25% TO ABOUT 12.5% BY WEIGHT, BASED ON TOTAL SOLIDS CONTENT, OF A CONDENSATE OF FROM 1 TO 25 MOLES OF ETHYLENE OXIDE WITH 1 MOLE OF PHENOL.
9. A DETERGENT COMPOSITION IN PARTICLE FORM COMPRISING A NORMALLY-DUSTING, SOLID SYNTHETIC ANIONIC ORGANIC DETERGENT OF THE CLASS CONSISTING OF SULFATES AND SULFONATES AND A SUFFICIENT AMOUNT OF A PHENOL-ETHYLENE OXIDE CONDENSATE TO REDUCE THE M. A. S. DUST VALUE OF SAID DETERGENT TO LESS THAN 1000, SAID PHENOL-ETHYLENE OXIDE CONDENSATE CONTAINING FROM 1 TO 25 MOLES OF ETHYLENE OXIDE PER MOLE OF PHENOL.
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Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2855367A (en) * 1954-09-07 1958-10-07 Colgate Palmolive Co Detergent composition
US2904468A (en) * 1954-04-13 1959-09-15 Carlen Corp Skin disinfectant containing polyoxyethylene alkyl phenol, calcium chelating agent and either an organic sulfate or sulfonate salt
US2952638A (en) * 1956-08-03 1960-09-13 Procter & Gamble Deaeration and purification of anionic detergent compositions
US2952571A (en) * 1957-02-18 1960-09-13 Standard Oil Co Cleaning oily hard surfaces
US2988510A (en) * 1956-06-01 1961-06-13 Monsanto Chemicals Non-dusting detergent and bleaching composition
US3010907A (en) * 1957-04-09 1961-11-28 Pennsalt Chemicals Corp Alkaline cleaning compositions
US3215630A (en) * 1964-11-12 1965-11-02 Cincinnati Milling Machine Co Cutting composition
US3351559A (en) * 1963-11-13 1967-11-07 Henkel & Cie Gmbh Pourable and free-flowing detergent, wetting, and emulsifying compositions
US3406208A (en) * 1962-05-17 1968-10-15 Henkel & Compagnie G M B H Polyglycol ethers suitable for detergent preparations, and process for preparing the same
US3714051A (en) * 1969-09-24 1973-01-30 Colgate Palmolive Co Process for making enzyme-containing granules

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
US2423450A (en) * 1941-04-17 1947-07-08 Colgate Palmolive Peet Co Preparation of synthetic organic detergent particles having only slight dust-forming tendencies
US2489955A (en) * 1943-08-25 1949-11-29 Colgate Palmolive Peet Co Preparation of nondusting organic 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
US2423450A (en) * 1941-04-17 1947-07-08 Colgate Palmolive Peet Co Preparation of synthetic organic detergent particles having only slight dust-forming tendencies
US2489955A (en) * 1943-08-25 1949-11-29 Colgate Palmolive Peet Co Preparation of nondusting organic detergent compositions

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2904468A (en) * 1954-04-13 1959-09-15 Carlen Corp Skin disinfectant containing polyoxyethylene alkyl phenol, calcium chelating agent and either an organic sulfate or sulfonate salt
US2855367A (en) * 1954-09-07 1958-10-07 Colgate Palmolive Co Detergent composition
US2988510A (en) * 1956-06-01 1961-06-13 Monsanto Chemicals Non-dusting detergent and bleaching composition
US2952638A (en) * 1956-08-03 1960-09-13 Procter & Gamble Deaeration and purification of anionic detergent compositions
US2952571A (en) * 1957-02-18 1960-09-13 Standard Oil Co Cleaning oily hard surfaces
US3010907A (en) * 1957-04-09 1961-11-28 Pennsalt Chemicals Corp Alkaline cleaning compositions
US3406208A (en) * 1962-05-17 1968-10-15 Henkel & Compagnie G M B H Polyglycol ethers suitable for detergent preparations, and process for preparing the same
US3351559A (en) * 1963-11-13 1967-11-07 Henkel & Cie Gmbh Pourable and free-flowing detergent, wetting, and emulsifying compositions
US3215630A (en) * 1964-11-12 1965-11-02 Cincinnati Milling Machine Co Cutting composition
US3714051A (en) * 1969-09-24 1973-01-30 Colgate Palmolive Co Process for making enzyme-containing granules

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