US2577503A - Detergent composition - Google Patents

Detergent composition Download PDF

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Publication number
US2577503A
US2577503A US746320A US74632047A US2577503A US 2577503 A US2577503 A US 2577503A US 746320 A US746320 A US 746320A US 74632047 A US74632047 A US 74632047A US 2577503 A US2577503 A US 2577503A
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United States
Prior art keywords
ethylene oxide
carbon atoms
fatty
condensation product
group
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Expired - Lifetime
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US746320A
Inventor
Baird William
Parry Edryd Gwylfa
Thompson Thomas Edward
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Imperial Chemical Industries Ltd
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Imperial Chemical Industries Ltd
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    • C—CHEMISTRY; METALLURGY
    • C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
    • C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
    • C25B1/00—Electrolytic production of inorganic compounds or non-metals
    • C25B1/01—Products
    • C25B1/24—Halogens or compounds thereof
    • C25B1/26—Chlorine; Compounds thereof
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/74—Carboxylates or sulfonates esters of polyoxyalkylene glycols

Definitions

  • This invention relates to detergent compositions and detergent baths and to processes for making them.
  • detergent compositions which comprise a p-monohydroxyethylamide of a fatty acid of from 8 to 20 carbon atoms and at leastl0% by weight of an ethylene oxide condensation product'of afatty alcohol or a fatty-acid of the formula wherein R' is an aliphatic 'ra' dical of from 8- to 22 carbon atoms, x is 000 or o Yis "hydrogen or an alkyl radical of not more than 5 carbon atoms and n is a whole number greater than 3.
  • the said ethylene oxide condensation products have surface active properties and with a suitable number of ethylene oxide residues they possess good detergent properties.
  • Our invention is based on the discovery that the detergent properties of the ethylene oxide condensation product can be improved when already present, or conferred when virtually absent by the said admixture with the p-monohydroxyethylamides.
  • s-monohydroxyethylamides there may be used in the detergent compositions of the invention for example, stearo-p-hydroxyethylamide, lauro-;8-hydroxyethylamide, oleo-fi-hydroxyethylamide and ricinoleo e hydroxyethylamide.
  • p-monohydroxyethylamides of mixtures of fatty acids particularly those occurring naturally for example coconut oil acids, tallow acids and castor oil acids.
  • fatty alcohols and fatty acids of which the ethylene oxide condensation products and derivatives thereof may be used in the detergent compositions of the invention there may be used for example cetyl alcohol, sperm oil alcohol, dodecyl alcohol or mixtures of such alcohols as are obtained for example by reduction of natural oils and fats, stearic acid, oleic acid, lauric acid and natural mixtures of such acids, for example, coconut oil acids.
  • the detergent compositions of the invention are made by mechanically mixing together as by stirring the constituents.
  • the mixing process may with advantage be accelerated by application of heat.
  • This application of heat may or may not be such as to melt the ingredients when they are solid at atmospheric temperature.
  • alkali phosphates Other components commonly added to detergent compositions, for example alkali phosphates,
  • compositionsof this invention may also be added. to the compositionsof this invention.
  • the invention is illustra'ted but not limited by the followingexamples'in which parts are by -E'mample 1 1 316 'ipar'ts of a -'c'onden's'ation product of 'cetyl alcohol with 17 molecular proportionsof ethylene oxideand 6T4 part'sof thep 'monohydroxyethylamide of coconut "oil fatty acids are meltedand stirred together "until a homogeneous mixture is obtained. For'the scouring-of artificially soiled botany wool serge the mixture is considerably superior t'othe ethylene oxide" condensate alone.
  • Example 2 13.6 parts of a condensation product of cetyl alcohol with 30 molecular proportions of ethylene oxide and 6.4 parts of the fl-monohydroxyethylamide of coconut oil fatty acids are melted and stirred together until a homogeneous mixture is obtained. The mixture is considerably superior to the ethylene oxide condensate alone for the scouring of artificially soiled botany wool serge.
  • Example 4 16 parts of a condensation product of stearic acid with 13 molecular proportions of ethylene oxide and 4 parts of the p-monohydroxyethylamide of coconut oil fatty acids are melted and stirred together until a homogeneous mixture is obtained. The mixture is considerably superior to the ethylene oxide condensate alone for the scouring of artificially soiled botany wool serge.
  • Example 5 The monomethyl ether of ethylene glycol is condensed with 6 molecular proportions of ethylene oxide and the product is esterified with coconut oil fatty acids. 94 parts of the ester and 6 parts of the p-monohydroxyethylamide of stearic acid are melted and stirred together until a homogeneous mixture is obtained. The mixture is a better wool detergent, especially in alka- 3 line soft water, than the coconut oil fatty acid and ester alone.
  • Example 6 97 parts of a condensation product of dodecyl alcohol with 5 molecular proportions of ethylene oxide and 3 parts of stearoethanolamide are melted and stirred together until a homogeneous mixture is obtained.
  • the mixture is a better wool detergent than the ethylene oxide condensate alone.
  • a detergent composition which consists essentially of a fl-monohydroxy-ethylamide of a fatty acid of from 12 to 20 carbon atoms mixed with at least 10% by weight of an ethylene oxide condensation product of a fatty compound selected from the group consisting of fatty alcohols and fatty acids, said ethylene oxide condensation product having the formula RX(CH2CH2O)1Y wherein R is an aliphatic radical of from 12 to 22 carbon atoms, X is a divalent radical selected from the group consisting of -C-- and O, Y is selected from the group consisting of hydrogen and alkyl of up to carbon atoms and n is a whole number from 4 to 30.
  • a detergent composition consisting essentially of a p-monohydroxyethylamide of a fatty acid of from 12 to 20 carbon atoms mixed with tially of a 13-monohydroxyethylamide of a fatty u acid of from 12 to 20 carbon atoms mixed with at least 10% by weight of a condensation product of a fatty acid of from 12 to 22 carbon atoms with from 4 to 30 molecular proportions of ethylene oxide.
  • a detergent composition which consists essentially of the fi-monohydroxyethylamides of cocoanut oil acids mixed with at least 10% by weight of a condensation product of a fatty compound selected from the group consisting of fatty alcohols and fatty acids of from 12 to 22 carbon atoms, with from 4 to 30 molecular proportions of ethylene oxide.
  • a detergent composition which consists essentially of the fl-monohydroxyethylamides of castor oil acids mixed with at least 10% by weight of a condensation product of a fatty compound selected from the group consisting of fatty alcohols and fatty acids of from 12 to 22 carbon atoms, with from 4 to 30 molecular proportions of ethylene oxide.

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

Description

Patented Dec. 4, 1951 2,577,503 DET'ERTGENT COMPOSITION WilliainBairH,-Edryd Gwylfa Parry, and Thomas Edward Thompson, Blackfey, Manchsth Eifgland, =assig'nors to Imperial "Chemical Industries Limited, a corporation :"of Great Britain No Draw ng. 'Am'plijcationi May ,6, 19417,; SrialNo.
746,320. In Great BritainMay 6, 1946 Claims. (01; 252"152') This invention relates to detergent compositions and detergent baths and to processes for making them.
According to the intention we provide detergent compositions which comprise a p-monohydroxyethylamide of a fatty acid of from 8 to 20 carbon atoms and at leastl0% by weight of an ethylene oxide condensation product'of afatty alcohol or a fatty-acid of the formula wherein R' is an aliphatic 'ra' dical of from 8- to 22 carbon atoms, x is 000 or o Yis "hydrogen or an alkyl radical of not more than 5 carbon atoms and n is a whole number greater than 3.
It has hitherto been known that the said ethylene oxide condensation products have surface active properties and with a suitable number of ethylene oxide residues they possess good detergent properties. Our invention is based on the discovery that the detergent properties of the ethylene oxide condensation product can be improved when already present, or conferred when virtually absent by the said admixture with the p-monohydroxyethylamides.
As s-monohydroxyethylamides there may be used in the detergent compositions of the invention for example, stearo-p-hydroxyethylamide, lauro-;8-hydroxyethylamide, oleo-fi-hydroxyethylamide and ricinoleo e hydroxyethylamide. There may also be used the p-monohydroxyethylamides of mixtures of fatty acids particularly those occurring naturally for example coconut oil acids, tallow acids and castor oil acids.
As fatty alcohols and fatty acids, of which the ethylene oxide condensation products and derivatives thereof may be used in the detergent compositions of the invention there may be used for example cetyl alcohol, sperm oil alcohol, dodecyl alcohol or mixtures of such alcohols as are obtained for example by reduction of natural oils and fats, stearic acid, oleic acid, lauric acid and natural mixtures of such acids, for example, coconut oil acids.
The detergent compositions of the invention are made by mechanically mixing together as by stirring the constituents. The mixing process may with advantage be accelerated by application of heat. This application of heat may or may not be such as to melt the ingredients when they are solid at atmospheric temperature.
Other components commonly added to detergent compositions, for example alkali phosphates,
weight.
'silicaites'andborates, may also be added. to the compositionsof this invention.
The invention -is illustra'ted but not limited by the followingexamples'in which parts are by -E'mample 1 1 316 'ipar'ts of a -'c'onden's'ation product of 'cetyl alcohol with 17 molecular proportionsof ethylene oxideand 6T4 part'sof thep 'monohydroxyethylamide of coconut "oil fatty acids are meltedand stirred together "until a homogeneous mixture is obtained. For'the scouring-of artificially soiled botany wool serge the mixture is considerably superior t'othe ethylene oxide" condensate alone.
Example 2 Example 3 13.6 parts of a condensation product of cetyl alcohol with 30 molecular proportions of ethylene oxide and 6.4 parts of the fl-monohydroxyethylamide of coconut oil fatty acids are melted and stirred together until a homogeneous mixture is obtained. The mixture is considerably superior to the ethylene oxide condensate alone for the scouring of artificially soiled botany wool serge.
Example 4 16 parts of a condensation product of stearic acid with 13 molecular proportions of ethylene oxide and 4 parts of the p-monohydroxyethylamide of coconut oil fatty acids are melted and stirred together until a homogeneous mixture is obtained. The mixture is considerably superior to the ethylene oxide condensate alone for the scouring of artificially soiled botany wool serge.
Example 5 The monomethyl ether of ethylene glycol is condensed with 6 molecular proportions of ethylene oxide and the product is esterified with coconut oil fatty acids. 94 parts of the ester and 6 parts of the p-monohydroxyethylamide of stearic acid are melted and stirred together until a homogeneous mixture is obtained. The mixture is a better wool detergent, especially in alka- 3 line soft water, than the coconut oil fatty acid and ester alone.
Example 6 97 parts of a condensation product of dodecyl alcohol with 5 molecular proportions of ethylene oxide and 3 parts of stearoethanolamide are melted and stirred together until a homogeneous mixture is obtained. The mixture is a better wool detergent than the ethylene oxide condensate alone.
We claim:
1. A detergent composition which consists essentially of a fl-monohydroxy-ethylamide of a fatty acid of from 12 to 20 carbon atoms mixed with at least 10% by weight of an ethylene oxide condensation product of a fatty compound selected from the group consisting of fatty alcohols and fatty acids, said ethylene oxide condensation product having the formula RX(CH2CH2O)1Y wherein R is an aliphatic radical of from 12 to 22 carbon atoms, X is a divalent radical selected from the group consisting of -C-- and O, Y is selected from the group consisting of hydrogen and alkyl of up to carbon atoms and n is a whole number from 4 to 30.
2. A detergent composition consisting essentially of a p-monohydroxyethylamide of a fatty acid of from 12 to 20 carbon atoms mixed with tially of a 13-monohydroxyethylamide of a fatty u acid of from 12 to 20 carbon atoms mixed with at least 10% by weight of a condensation product of a fatty acid of from 12 to 22 carbon atoms with from 4 to 30 molecular proportions of ethylene oxide.
.4. A detergent composition which consists essentially of the fi-monohydroxyethylamides of cocoanut oil acids mixed with at least 10% by weight of a condensation product of a fatty compound selected from the group consisting of fatty alcohols and fatty acids of from 12 to 22 carbon atoms, with from 4 to 30 molecular proportions of ethylene oxide.
5. A detergent composition which consists essentially of the fl-monohydroxyethylamides of castor oil acids mixed with at least 10% by weight of a condensation product of a fatty compound selected from the group consisting of fatty alcohols and fatty acids of from 12 to 22 carbon atoms, with from 4 to 30 molecular proportions of ethylene oxide.
WILLIAM BAIRD. EDRYD GWYLFA PARRY. THOMAS EDWARD THOMPSON.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 1,970,578 :Schoeller et a1. Aug. 21, 1934 2,317,112 Pings Apr. 20, 1943 2,353,081 Robinson et a1. July 4, 1944

Claims (1)

1. A DETERGENT COMPOSITION WHICH CONSISTS ESSENTIALLY OF A B-MONOHYDROXY-ETHYLAMIDE OF A FATTY ACID OF FROM 12 TO 20 CARBON ATOMS MIXED WITH AT LEAST 10% BY WEIGHT OF AN ETHYLENE OXIDE CONDENSATION PRODUCT OF A FATTY COMPOUND SELECTED FROM THE GROUP CONSISTING OF FATTY ALCOHOLS AND FATTY ACIDS, SAID ETHYLENE OXIDE CONDENSATION PRODUCT HAVING THE FORMULA RX(CH2CH2O)NY WHEREIN R IS AN ALIPHATIC RADICAL OF FROM 12 TO 22 CARBON ATOMS, X IS A DIVALENT RADICAL SELECTED FROM THE GROUP CONSISTING OF -COO-AND-O-, Y IS SELECTED FROM THE GROUP CONSISTING OF HYDROGEN AND ALKYL OF UP TO 5 CARBON ATOMS AND N IS A WHOLE NUMBER FROM 4 TO 30.
US746320A 1946-05-06 1947-05-06 Detergent composition Expired - Lifetime US2577503A (en)

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Cited By (6)

* 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
US2992994A (en) * 1954-07-20 1961-07-18 Ciba Ltd Detergent composition for the hair
US3312624A (en) * 1962-05-18 1967-04-04 Rohm & Haas Stable alkali soluble surfactants
US3953382A (en) * 1973-05-30 1976-04-27 Lever Brothers Company Detergent compositions
US4840942A (en) * 1983-10-14 1989-06-20 Kao Corporation Emulsifying dispersant and biocidal composition containing same
US5554315A (en) * 1993-12-28 1996-09-10 Kao Corporation Foaming surfactant composition comprising fatty acid polyoxyalkylene lower alkyl ether and fatty acid monoglyceride

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
US2317112A (en) * 1940-10-16 1943-04-20 Du Pont Cleaning composition
US2353081A (en) * 1939-06-14 1944-07-04 Nat Oil Prod Co Sulphated monoethanolamides and process for the preparation thereof

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
US2353081A (en) * 1939-06-14 1944-07-04 Nat Oil Prod Co Sulphated monoethanolamides and process for the preparation thereof
US2317112A (en) * 1940-10-16 1943-04-20 Du Pont Cleaning composition

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2992994A (en) * 1954-07-20 1961-07-18 Ciba Ltd Detergent composition for the hair
US2855367A (en) * 1954-09-07 1958-10-07 Colgate Palmolive Co Detergent composition
US3312624A (en) * 1962-05-18 1967-04-04 Rohm & Haas Stable alkali soluble surfactants
US3953382A (en) * 1973-05-30 1976-04-27 Lever Brothers Company Detergent compositions
US4840942A (en) * 1983-10-14 1989-06-20 Kao Corporation Emulsifying dispersant and biocidal composition containing same
US5554315A (en) * 1993-12-28 1996-09-10 Kao Corporation Foaming surfactant composition comprising fatty acid polyoxyalkylene lower alkyl ether and fatty acid monoglyceride

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Publication number Publication date
FR946955A (en) 1949-06-20
GB611683A (en) 1948-11-02
BE473077A (en)

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