US2941950A - Concentrated liquid detergent - Google Patents

Concentrated liquid detergent Download PDF

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Publication number
US2941950A
US2941950A US459240A US45924054A US2941950A US 2941950 A US2941950 A US 2941950A US 459240 A US459240 A US 459240A US 45924054 A US45924054 A US 45924054A US 2941950 A US2941950 A US 2941950A
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US
United States
Prior art keywords
alcohol
ammonia
alkyl
moles
carbon atoms
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US459240A
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English (en)
Inventor
Edwin O Korpi
Robert P Davis
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Procter and Gamble Co
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Procter and Gamble Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to NL200262D priority Critical patent/NL200262A/xx
Priority to BE541262D priority patent/BE541262A/xx
Application filed by Procter and Gamble Co filed Critical Procter and Gamble Co
Priority to US459240A priority patent/US2941950A/en
Priority to FR1136823D priority patent/FR1136823A/fr
Priority to CH354195D priority patent/CH354195A/de
Priority to GB27926/55A priority patent/GB791704A/en
Application granted granted Critical
Publication of US2941950A publication Critical patent/US2941950A/en
Anticipated expiration legal-status Critical
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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
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/29—Sulfates of polyoxyalkylene ethers
    • 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
    • C11D1/65—Mixtures of anionic with cationic compounds
    • C11D1/655—Mixtures of sulfonated products with alkylolamides of carboxylic acids
    • 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

Definitions

  • This invention relates to liquid synthetic detergent compositions, and particularly to those that are intended primarily for washing dishes, glassware, etc. in a dishpan or in a kitchen sink.
  • Such detergents to be accepted by the user, should have certain characteristics-pourability, chill point well below normal room temperature, short reliquefaction time at room temperature after having been congealed by storage at low temperatures, good sudsing and detergent qualities; and above all, mildness to the hands of the user. While possessing all of these characteristics, the liquid detergent should be concentrated enough so that a moderate sized bottle or can of the liquid will provide detergent mileage for about as many dishwashings as a package of soap flakes or of synthetic detergent.
  • the high molecular weight alcohol used can be the middle cut produced in distilling the fatty alcohols derived from reducing coconut oil, coconut fatty acids, or their alkyl esters. Such middle cut fatty alcohols are the normal primary alcohols having 10 to 1 6 carbons in the molecule and obviously may be produced from other oils of the coconut group such as palm kernel and babassu.
  • alkylol substituted ammonias we prefer are mono-, di-, and triethanol, mono-, di-, and tripropanol, mono-, di-, and triisopropanol and mono-, di-, and triglyceryl amines, those in which the alkylol group is of 2 to 3 carbon chain length.
  • the compound that makes the compositions of the present invention differ from those previously known is the sulfated and neutralized reaction product of about three I Patented June 21, 1960 middle cut fatty alcohol from coconut oil was carried out in an autoclave, equipped with an agitator, an internal cooling coil, and an external electric heater. 23.45 parts of fatty alcohol were placed in the autoclave and sodium hydroxide pellets (0.25% based on the alcohol) were added. The cover was bolted onto the autoclave. The agitator was started and the external heater turned on. The autoclave was scavenged with nitrogen during the heating period which continued until a temperature of 270 F.
  • reaction product of the above example was sulfated with 105% of the theoretical amount of chlorosulfonic acid at a temperature of to F.
  • alkyl (Et O) sulfate the sulfated mixture of reaction products produced by reacting 1 mole of fatty alcohol with 1 mole of ethylene oxide.
  • Example 2 using the equipment and operating conditions described in Example 1, 18.35 parts of middle cut fatty-alcohol,”to which caustic soda pellets were added to the amount of 0.25% on the Weight of the alcohol, were reacted with 12.35 parts of ethylene oxide. This is 3 moles of ethylene oxide to 1 mole of fatty alcohol. In this reaction the; temperature went to 315 F. After scavenging with nitrogen and cooling, 2. portion of this product was analyzed. Its composition was approxiwhere n is more than 3 and R is a mixture of alkyls from middle-cut CNO alcohol. e e a The reaction product was sulfated with 'of the theoretical amount of chlorosulfonic" acid. Analysis indicated a completeness of approximately 98%. .'The product was neutralized with ammonia. For'convenience the product is '"eaned'an i (Hi0); sulfate althoiigh ap- V plex, for convenience.
  • iii-bxinnatelyhalf of it is alkyl sulfate plus alkyl ethylene 1 to 305 F. After scavenging with nitrogen and cooling, 1 the product was removed from the autoclave.
  • n may be as high as 12 in this preparation since the data and calculations as presented in Figure 1 show that n is 11 or less in only 90% of the composition.
  • reaction product was sulfated with 105% of the theoretical chlorosulfonic acid, and was determined to beabout 98% sulfated.
  • the product was neutralized with ammonia.
  • this reaction product is called alkyl (EtO) -s'ulfate although the actual molar percent of the condensation product of fatty alcohol with 5 moles of ethylene oxide is only about 10%.
  • the product may be used'in liquid. detergent preparations meeting the objects set forth above.
  • alkyl ethylene oxide ammonium sulfate products made according to themethods set forth in Examples 1, 2, and 3 were tested for dishpan sudsing against a commercial liquid dishwashing detergent in which the anionic sulfuric reaction product was ammonium alkyl sulfate, the alkyl being middle cut coconut alcohol.
  • the coconut amide was made by reacting monoethanol amine with coconut fatty acids.
  • the active builder por- 'tion of these amides is comprised essentially of the with one of high molecular alcohol.
  • alkylol amines may be used in place of monoethanol amine, for example, diethanol amine, and monoand dipropanol and isopropanol amines and monoand diglyceryl amine may be considered substantial equivalents for the present purpose, thus producing alkylolamides with not more than three carbon atoms in each alkylol radical.
  • the dishpan sudsing test used in this composition determines the amount of detergent required to wash a standard number of soiled plates and have a definite suds level after theplates are washed.
  • the plates are soiled with a mixture of tallow, salad oil, flour and powdered gelatin. Successive trials with varying amounts of detergent are made until the amount required to wash the plates and have a definite levelof suds at the finish is determined.
  • the tests on the preparations of Examples 1, 2, and 3 were made in water of 7 grains per gallon hardness.
  • alkyl sulfate liquid detergent the alkyl radical being derived from a similar middle cut alcohol as used in the alkyl (EtO) sulfate.
  • freeze recovery time of a comammonium alkyl sulfate is 24 hours.
  • test tubes Portions of this wererplaced in test tubes and held for five days at 50 F. No clouding occurred.
  • Four test tubes were filled with portions and held for 4 days at 0 F., F., ⁇ 30 F., and 40 -F. respectively. They were then brought into a space maintained at 75 F. and
  • Monoethanolamine, diethanolamine and triethanolamine or the corresponding isopropanolamines may be used in place of ammonia, to neutralize the sulfate with *no significant change in the characteristics of these comcleared in less than 4 hours.
  • Example 5 --Another preparation was made from the materials of Example 4, but the proportions were as follows:
  • the ethyl or propyl-alcohol used as a solvent will be about 15% to I 25% by weight ofthe liquid detergent as it is ready for ammonia.
  • ammonium and substituted ammonium salts of sulfuric and hydrochloric acid are important to control the ammonium and substituted ammonium salts of sulfuric and hydrochloric acid, called for convenience electrolyte salts.
  • the hydrochloric acid not driven off during the process is there as free acid. This is driven off by aeration to, preferably, the amount that will produce not over 0.5% NH CI (finished product basis) when neutralized with Up to 1% NH Cl may be tolerated but a limit of 0.5 NH Cl is preferable. If substituted ammonias are used, the amine chlorides should be held down to the s'toichiornetric equivalents of the above values for NI-LiCl.
  • Electrolyte salts are therefore present preferably in the amount of (.6+.5)/37 .5% or just under 3% of the alkyl (EtO), sulfate and the maximum tolerated would be about (1+1)/37.5 or 5.4% of a the alkyl (EtO) sulfate.
  • Example Example Example 6 7 8 Alkyl (Et)a sulfate 36 39 40%, Ethyl alcohol 19% 21% 23 Coconut ethanol amide 8.7 9. 35 V 9. 75 Clcuding days at -50 F none none none Freeze recovery after 4 days at 0 F... .K. 0K. 0K.
  • product including unreacted alcohol and otherwise consisting essentially of'a mixture of fatty alcohol-ethylene oxide ethers of the general formula of moc zcanoa
  • R represents an alkyl chain of 10 to 16 carbon atoms in the alkyl radical
  • x is a plurality of Whole numbers within the range from 1 to 12 inclusive, said unreacted alcohol and mixed alkyl ethers being sulfated,.and then neutralized with a neutralizing agent selected from the group consisting of ammonia and alhylol-substituted ammonia having from 2 to 3 carbon atoms in the alkylol group;
  • a (b) 'An organic builder substance consisting essentially of alkylolamide of saturated fatty acids having 10, 12 and 14 carbon atoms and an alkylol amine, said alkylol amide having not more than'3 carbon atoms in each alkylol radical and the amount thereof being from 6 to 12% of the composition;
  • a single phase concentrated liquid detergent composition consisting essentially of a solution of (a) 25 to 40% of a sulfated and neutralizedreaction product obtained from condensing 2 to 4 moles of ethylene oxide and one mole of. monohydric alcohol of-from -10 to 16 carbon atoms in the molecule, said, reaction product including unreacted alcbhol and otherwise consisting essentially of a mixture'of fatty alcohol-ethylene oxide ethers of the general formula of V mocn cnp on v where R represents an alkyl chain of 10 to 16 carbon atoms in the alkyl radical, x is a plurality of Whole numbers within the range from 1 to 12 inclusive, said unreacted alcohol and mixed alkyl ethers being sulfated,
  • a single phase concentrated liquid detergent composition consistingessentially of a solution of (a) 25 to 40% of a sulfated and neutralized reaction product obtained from condensing 1 to 5 moles of ethylene oxide and 1 mole of fatty alcohol, said fatty alcohol being a Straight chain primary alcohol of 10 to 16 carbons and having a terminal hydroxyl group, said reaction product including unreacted alcohol and otherwise consisting essentially of a mixture of fatty.alcohol-ethylene oxide ethers of the general formula of mocri cnp on where R represents an alkyl chain of 10 to 16 carbon atoms in the alkyl radical, x is a plurality of whole numbers within the range from 1 to 12 inclusive, said unreacted alcohol and mixed alkyl ethers being sulfated, and then neutralized with a neutralizing agent selected from the group consisting of ammonia and an alkylol substituted ammonia having from 2 to 3 carbon atoms in the alkylol group;
  • An organic builder substance consisting essentially of alkylol amide of unsaturated fatty acids having 10, 12 and 14 carbon atoms and an alkylol amine, said alkylol amide having not more than 3 carbon atoms in each alkylol radical and the amount thereof being from 6 to 12% of the composition;
  • a single phase concentrated liquid detergent composition consisting essentially of a solution of (a) 25 to 40% of a sulfated and neutralized reaction product obtained from condensing 2 to 4 moles of ethylene oxide and 1 mole of fatty alcohol, said fatty alcohol being a straight chain primary alcohol of to 16 carbons and having a terminal hydroxyl group, said reaction product including unreacted alcohol and otherwise consisting essentially of a mixture of fatty alcoholethylene oxide ethers of the general formula of where R represents an alkyl chain of 10 to 16 carbon atoms in the alkyl radical, x is a plurality of whole numbers Within the range from 1 to 12 inclusive, said unreacted alcohol and mixed alkyl ethers being sulfated, and then neutralized with a neutralizing agent selected from the group consisting of ammonia and an alkylol substituted ammonia having from 2 to 3 carbon atoms in the alkyl group;
  • An organic builder substance consisting essentially of alkylol amide of saturated fatty acids having 10, 12 and 14 carbon atoms and an alkylol amine, said alkylol amide having not more than 3 carbon atoms in each alkylol radical and the amount thereof being from 6 to 12% of the composition.
  • liquid detergent composition of claim 4 in which the straight chain primary alcohol constituent is a middle cut coconut alcohol mixture and in which the number of moles of ethylene oxide per mole of fatty alcohol is approximately 3.

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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)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US459240A 1954-09-30 1954-09-30 Concentrated liquid detergent Expired - Lifetime US2941950A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
NL200262D NL200262A (ja) 1954-09-30
BE541262D BE541262A (ja) 1954-09-30
US459240A US2941950A (en) 1954-09-30 1954-09-30 Concentrated liquid detergent
FR1136823D FR1136823A (fr) 1954-09-30 1955-09-12 Détergent liquide
CH354195D CH354195A (de) 1954-09-30 1955-09-30 Verfahren zur Herstellung eines flüssigen Waschmittels
GB27926/55A GB791704A (en) 1954-09-30 1955-09-30 Detergent compositions

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US459240A US2941950A (en) 1954-09-30 1954-09-30 Concentrated liquid detergent

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US2941950A true US2941950A (en) 1960-06-21

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US459240A Expired - Lifetime US2941950A (en) 1954-09-30 1954-09-30 Concentrated liquid detergent

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US (1) US2941950A (ja)
BE (1) BE541262A (ja)
CH (1) CH354195A (ja)
FR (1) FR1136823A (ja)
GB (1) GB791704A (ja)
NL (1) NL200262A (ja)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3186943A (en) * 1961-12-11 1965-06-01 Safety Dev Corp Foam method for atmosphere control
US3211661A (en) * 1961-12-15 1965-10-12 Procter & Gamble Liquid detergent composition
US3330346A (en) * 1965-01-27 1967-07-11 Union Oil Co Method of treating a subterranean formation with a foam bank
US3422011A (en) * 1966-05-03 1969-01-14 Kidde & Co Walter Foam producing material
US3755206A (en) * 1970-03-09 1973-08-28 Colgate Palmolive Co Detergent compositions
US3893955A (en) * 1971-10-20 1975-07-08 Albright & Wilson Aqueous concentrate detergent component
US3959186A (en) * 1973-06-19 1976-05-25 Ici Australia Limited Process for manufacturing detergent builders
JPS51109002A (en) * 1975-03-20 1976-09-27 Kao Corp Senjozaisoseibutsu
US4013577A (en) * 1972-04-14 1977-03-22 Colgate-Palmolive Company Heavy duty dry biodegradable detergent composition
US4060490A (en) * 1976-08-23 1977-11-29 Union Oil Company Of California Composition and method for enhanced oil recovery utilizing aqueous polyacrylamide solutions
US4071475A (en) * 1975-09-16 1978-01-31 Kao Soap Co., Ltd. Transparent highly viscous liquid shampoo composition
US4092272A (en) * 1975-09-16 1978-05-30 Kao Soap Co., Ltd. Liquid detergent composition
US4132678A (en) * 1975-09-16 1979-01-02 Kao Soap Co., Ltd. Transparent liquid shampoo
US4316824A (en) * 1980-06-26 1982-02-23 The Procter & Gamble Company Liquid detergent composition containing alkyl sulfate and alkyl ethoxylated sulfate
US4464292A (en) * 1981-01-02 1984-08-07 Lengyel Stephen P Mixed ethoxylated alcohol/ethoxy sulfate surfactants and synthetic detergents incorporating the same
US4732704A (en) * 1985-09-25 1988-03-22 Henkel Kommanditgesellschaft Auf Aktien Manual dishwashing liquid detergent containing fatty alkylmonogluside
US5691299A (en) * 1994-12-08 1997-11-25 Henkel Corporation Anionic detergent mixtures
US20040092422A1 (en) * 2002-09-03 2004-05-13 Carr Charles D. Alkylaryl-o-ethoxylate blends with their respective sulfates

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5143483B2 (ja) * 1972-09-25 1976-11-22
ES475852A1 (es) * 1977-12-09 1980-03-01 Albright & Wilson Un metodo para la manufactura de una composicion acuosa ten-soactiva concentrada
EP0698658A1 (en) * 1994-08-23 1996-02-28 The Procter & Gamble Company Detergent compositions

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE501145A (ja) * 1950-03-02
US1970578A (en) * 1930-11-29 1934-08-21 Ig Farbenindustrie Ag Assistants for the textile and related industries
US2508035A (en) * 1950-05-16 Compounds having surface activity
GB674896A (en) * 1949-05-18 1952-07-02 Marchon Products Ltd Improvements in the manufacture of detergent compositions
USRE23840E (en) * 1950-05-03 1954-06-15 Liquid anionic-dialkylolamide
US2758977A (en) * 1951-05-25 1956-08-14 Gen Aniline & Film Corp Detergent composition and method of producing same

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2508035A (en) * 1950-05-16 Compounds having surface activity
US1970578A (en) * 1930-11-29 1934-08-21 Ig Farbenindustrie Ag Assistants for the textile and related industries
GB674896A (en) * 1949-05-18 1952-07-02 Marchon Products Ltd Improvements in the manufacture of detergent compositions
BE501145A (ja) * 1950-03-02
USRE23840E (en) * 1950-05-03 1954-06-15 Liquid anionic-dialkylolamide
US2758977A (en) * 1951-05-25 1956-08-14 Gen Aniline & Film Corp Detergent composition and method of producing same

Cited By (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3186943A (en) * 1961-12-11 1965-06-01 Safety Dev Corp Foam method for atmosphere control
US3211661A (en) * 1961-12-15 1965-10-12 Procter & Gamble Liquid detergent composition
US3330346A (en) * 1965-01-27 1967-07-11 Union Oil Co Method of treating a subterranean formation with a foam bank
US3422011A (en) * 1966-05-03 1969-01-14 Kidde & Co Walter Foam producing material
US3755206A (en) * 1970-03-09 1973-08-28 Colgate Palmolive Co Detergent compositions
US3893955A (en) * 1971-10-20 1975-07-08 Albright & Wilson Aqueous concentrate detergent component
US4013577A (en) * 1972-04-14 1977-03-22 Colgate-Palmolive Company Heavy duty dry biodegradable detergent composition
US3959186A (en) * 1973-06-19 1976-05-25 Ici Australia Limited Process for manufacturing detergent builders
JPS51109002A (en) * 1975-03-20 1976-09-27 Kao Corp Senjozaisoseibutsu
JPS5413242B2 (ja) * 1975-03-20 1979-05-29
US4071475A (en) * 1975-09-16 1978-01-31 Kao Soap Co., Ltd. Transparent highly viscous liquid shampoo composition
US4092272A (en) * 1975-09-16 1978-05-30 Kao Soap Co., Ltd. Liquid detergent composition
US4132678A (en) * 1975-09-16 1979-01-02 Kao Soap Co., Ltd. Transparent liquid shampoo
US4060490A (en) * 1976-08-23 1977-11-29 Union Oil Company Of California Composition and method for enhanced oil recovery utilizing aqueous polyacrylamide solutions
US4316824A (en) * 1980-06-26 1982-02-23 The Procter & Gamble Company Liquid detergent composition containing alkyl sulfate and alkyl ethoxylated sulfate
US4464292A (en) * 1981-01-02 1984-08-07 Lengyel Stephen P Mixed ethoxylated alcohol/ethoxy sulfate surfactants and synthetic detergents incorporating the same
US4732704A (en) * 1985-09-25 1988-03-22 Henkel Kommanditgesellschaft Auf Aktien Manual dishwashing liquid detergent containing fatty alkylmonogluside
US5691299A (en) * 1994-12-08 1997-11-25 Henkel Corporation Anionic detergent mixtures
US20040092422A1 (en) * 2002-09-03 2004-05-13 Carr Charles D. Alkylaryl-o-ethoxylate blends with their respective sulfates
US6746997B2 (en) 2002-09-03 2004-06-08 Church & Dwight Co., Inc. Alkylaryl-o-ethoxylate blends with their respective sulfates

Also Published As

Publication number Publication date
FR1136823A (fr) 1957-05-20
GB791704A (en) 1958-03-12
BE541262A (ja)
CH354195A (de) 1961-05-15
NL200262A (ja)

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