US2535972A - Alkylbenzenesulfonate detergents containing guanidine salts of inorganic acids - Google Patents

Alkylbenzenesulfonate detergents containing guanidine salts of inorganic acids Download PDF

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Publication number
US2535972A
US2535972A US89581A US8958149A US2535972A US 2535972 A US2535972 A US 2535972A US 89581 A US89581 A US 89581A US 8958149 A US8958149 A US 8958149A US 2535972 A US2535972 A US 2535972A
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United States
Prior art keywords
guanidine
sodium
weight
carbonate
alkyltoluenesulfonate
Prior art date
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Expired - Lifetime
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US89581A
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English (en)
Inventor
Emil A Vitalis
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Wyeth Holdings LLC
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American Cyanamid Co
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Filing date
Publication date
Priority to BE495205D priority Critical patent/BE495205A/xx
Application filed by American Cyanamid Co filed Critical American Cyanamid Co
Priority to US89581A priority patent/US2535972A/en
Priority to GB8556/50A priority patent/GB690821A/en
Priority to FR1018893D priority patent/FR1018893A/fr
Priority to ES0192667A priority patent/ES192667A1/es
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Publication of US2535972A publication Critical patent/US2535972A/en
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/046—Salts
    • 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
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic compounds
    • 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
    • C11D1/62—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/02—Inorganic compounds ; Elemental compounds
    • C11D3/04—Water-soluble compounds
    • C11D3/10—Carbonates ; Bicarbonates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions

Definitions

  • This invention relates to detergent compositions, and more particularly toalkylbenzenesul-L fonate detergents having greatly improved woolscouring properties.
  • Synthetic detergents of the alkybenzenesulfonate type are well known and are in wide commercial use. They are the sulfonation products of mononuclear aromatic hydrocarbons containing a ⁇ single long alkyl radical, usually of about -16 carbon atoms, with or without one or two additional short chain hydrocarbon substituents on thefbenzene nucleus)
  • the hydrocarbons oi this type are ordinarily prepared by one of two methods; either by condensing an oleiin oi' about 'l0-16 carbon atoms such as a propylene or butylene polymer with benzene, toluene or xylene, or by condensing any one or more of these aromatic hydrocarbons with a chlorinated kerosene fraction of lll-16 carbon atoms, usually with the aid of an aluminum chloride catalyst.
  • 'Ihe resulting alkylbenzene compound is sulfonated by well known sulfonation procedures, usually by
  • the sulfonation of the alkylbenzene compounds is usually carried out with an excess of acid, about 3-4 mois of acid per mol of alkylbenzene compound being used. After the sulfonation is complete the mixture is ordinarily neutralized with a water-soluble alkali such as sodium, potassium or ammonium hydroxide, which produces a mixture of the alkylbenzenesulfonate detergent with ⁇ approximately 50-200% of its weight of sodium sulfate, potassium sulfate or ammonium sulfate.
  • a water-soluble alkali such as sodium, potassium or ammonium hydroxide
  • the alkylbenzenesulfonate detergents of the above-described ⁇ class are effective for the washing of cotton cloth and other cotton textiles, but for some unknown reason they are not as good on wool. It is a principal object of the present invention to improve the detergency of this class of compounds for woven and knitted wool or wool-containing textiles by the addition s claims. (C1. cs2-isz) 2 i thereto of a water-soluble guanidine salt. I have found that a mixture of an alkylbenzenel sulfonate detergent of the above-described class with from about 2% to'about 50% of its weight of guanidine salt Vpossesses greatly improved scouring properties for wool and woolen textiles,
  • any of the alkylbenzenesulfonate detergents described above may be improved by admixture ⁇ with guanidine salts
  • the preferred compositions of my invention are those in which an alkyltoluenesulfonate is employed.
  • R is an alkyl radical of 10-16 carbon atoms, and preferably one of about 12-14 carbon atoms.
  • these alkyltoluenesulfonate detergents when admixed with 2-50% of their weight of guanidne carbonate orsulfate, possess excellent detergency 3 4 for wool, and also possess good stability on storage.
  • any water-soluble guanidine salt may be used to obtain an improved detergency of the alkylbenzenesulfonates on wool, although for most practical purposes the guanidinesalts of inorganic acids are preferred. Typical of these are guanidine nitrate, guanidine hydrochloride, guanidine sulphate, guanidine phosphate, and the guanidine carbonate referred to above. However, the corresponding water-soluble salts of organic acids may be used if desired, and particularly such compounds as guanidine acetate, guanidine benzoate, guanidine phthalate, guanidine carbamate and guanidine anthranilate.
  • Example 1 An alkyltoluenesulfonate prepared by condensing toluene with a propylene polymer fraction and having an average composition of CH3.C6H4.C12H:5 was sulfonated with 20% oleum. The sulfonation was carried out by adding the oleum to the hydrocarbon, using a 4: 1 molar ratio and maintaining the temperature of the mixture at 15-25" C. Under these conditions the formation of the monosulfonate was complete in about 0.5-3 hours.
  • One portion of the sulfonation mixture was purified by the process described in U. S. Patent No. 2,433,316. A small amount of water was added and the product was then extracted with toluene. The resulting toluene solution of the sulfonic acid was separated from the residue and agitated with 2-3 times its volume of water followed by neutralizing with 40% sodium hydroxide solution and evaporation on a steam bath. This produced a purified sodium alkyltoluenesulfonate containing only a small quantity (about of sodium sulfate.
  • the remainder of the sulfonaton mixture was neutralized by pouring it into a slight excess of sodium hydroxide solution of -20% concentration. This produced a slurry of approximately 35% solids, of which about 45-50% was sodium the fabric was then air dried at room temperature. The impregnation and drying was repeated for a total of four times after which the alkyltoluenesulfonate and about 50-55 was sodium sulfate: 'I'his slurry was dried to ake form on a steam-heated drum dryer.
  • Varying amounts of guanidine carbonate and oi' guanidine sulfate were mixed with the alkyltoluenesulfonate-sodium sulfate mixture prepared by the second of 'the two methods described to produce compositions containing from 0.1% to 100% of guanidine carbonate and from 0.1% to of guanidine sulfate, these percentages-being based on the weight of the alkyltoluenesulfonate in the detergent mixture.
  • Wool cloth was passed through this solution and held vertically, allowing the excess liquor to drain. During this period the fabric was inverted several times to insure uniform distribufabric was cut into four inch squares. Reflectance measurements were taken o! these squares at 600 millimicrons on a G. E. Recording Spectrophotometer.
  • Detergency tests were run at 0.1% concentration of sodium alkyltoluenesulfonate in the Launderometer according to A. A. T. C. C. procedure.
  • Into each pint jar were placed 20 onefourth inch glass beads, 200 m1. of the detergent solution under test, and one numbered soiled swatch. ⁇
  • the jars were rotated at 42 R. P. M. in the machine at F. for 20 minutes and this was repeated for a total of 3 times using fresh detergent solution for each wash.
  • the third wash was followed by three ve minute rinses.
  • the cloth pieces were then squeezed, ironed dry, and again measured for reilectance in the spectrophotometer. The percent ofreturn ofthe cloth to its original reflectance. prior to application of the soil, is the measure of detergency.
  • Example 2 Varying quantities of guanidine carbonate were mixed with an alkylbenzene sodium sulfonate prepared by condensing benzene with a propylene polymer fraction ranging from CioHzz to about Cul-Iso and having an average molecular weight of 168 and sulfonating the product as described in Example 1. The sulfonation mixture was neutralized by pouring it into a 20% aqueous sodium hydroxide solution and the guanidine carbonate was added to the resulting slurry which was then drum dried.
  • an alkylbenzene sodium sulfonate prepared by condensing benzene with a propylene polymer fraction ranging from CioHzz to about Cul-Iso and having an average molecular weight of 168 and sulfonating the product as described in Example 1.
  • the sulfonation mixture was neutralized by pouring it into a 20% aqueous sodium hydroxide solution and the guanidine carbonate was added
  • the detergency values were determined by the method described in Example 1 and were as follows, the percent of guanidine carbonate being based on the weight of the alkylbenzene sodium sulfonate.
  • a composition consisting essentially of a detergent mixture of 98% to 50% by weight of a member of the group consisting of sodium, potassium and ammonium salts of an alkyi fonate containing a single long alkyl radical of 10-16 carbon atoms and 2% to 50% of a watersoluble guanidine salt of an inorganic acid.
  • a composition consisting essentially of a detergent mixture of 98% to 50% by weight of an alkyltoluenesulfonate of the formula GHaCsHaSOxNn Appearance Aitor Storage Additive Per Cent ⁇ Room Com 65% R H 90 100% ditions 2 -25 C 2 R. H,30 Months Months C. 4 Days None Gaked--..---- Wet Lumps..-- Liquid. Guanidine Carbonate-- 5 Dry Powder-- Slightly Damp-- Do. Do 7 -do Dry Powder..-- Do. Dn 12 dn do Wet Solid.
  • Example 4 Test samples containing az number of diierent guanidine salts were prepared from an alkyltoluenesulfonate produced from a commercially available alkyltoluene fraction having an A. S. T. M. distillation boiling range (5 to 95%) of 289304 C. and an average molecular weight. (cryoscopic)A of 268. This alkyltoluene was sulfonated and neutralized with aqueous sodium hydroxide solution by the procedure described inExample l.
  • a composition consisting essentially oi' a de- ⁇ tergent mixture of 98% to 50% by weight oi' an alkylarylsulfonate of the formula in which X is a member of the group of hydrogen and the -CBJ radical, M is a mono- ⁇ valent salt-forming radical selected from the ⁇ group consisting of sodium. potassium and ammesma 7 monium and R is an alkyl radica! o! 10-16 carbon atoms and 2% to 50% ot a. water-soluble guanidine salt of an inorganic acid.

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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)
  • Inorganic Chemistry (AREA)
  • Detergent Compositions (AREA)
US89581A 1949-04-26 1949-04-26 Alkylbenzenesulfonate detergents containing guanidine salts of inorganic acids Expired - Lifetime US2535972A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
BE495205D BE495205A (en, 2012) 1949-04-26
US89581A US2535972A (en) 1949-04-26 1949-04-26 Alkylbenzenesulfonate detergents containing guanidine salts of inorganic acids
GB8556/50A GB690821A (en) 1949-04-26 1950-04-05 Improvements in or relating to detergent compositions
FR1018893D FR1018893A (fr) 1949-04-26 1950-04-13 Perfectionnements aux compositions détergentes
ES0192667A ES192667A1 (es) 1949-04-26 1950-04-24 MEJORAS INTRODUCIDAS EN LA PREPARACIoN DE COMPOSICIONES DETERGENTES

Applications Claiming Priority (1)

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US89581A US2535972A (en) 1949-04-26 1949-04-26 Alkylbenzenesulfonate detergents containing guanidine salts of inorganic acids

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US (1) US2535972A (en, 2012)
BE (1) BE495205A (en, 2012)
ES (1) ES192667A1 (en, 2012)
FR (1) FR1018893A (en, 2012)
GB (1) GB690821A (en, 2012)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2832743A (en) * 1949-09-29 1958-04-29 Lever Brothers Ltd Free flowing alkyl aryl sulfonate detergent compositions
US2921881A (en) * 1957-11-13 1960-01-19 American Cyanamid Co Fungitoxic-bacteriotoxic guanidine compositions
US2967832A (en) * 1954-11-15 1961-01-10 American Cyanamid Co Polyphosphate detergent compositions containing dicyandiamide tarnish inhibitor
US3960782A (en) * 1974-09-27 1976-06-01 The Procter & Gamble Company Shampoo compositions which impart high luster and manageability to hair
JPWO2006025373A1 (ja) * 2004-08-31 2008-05-08 三洋化成工業株式会社 界面活性剤
US10066193B2 (en) * 2012-02-17 2018-09-04 The Clorox Company Targeted performance of hypohalite methods thereof

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2374187A (en) * 1945-04-24 Detergent composition
US2445975A (en) * 1946-05-08 1948-07-27 American Cyanamid Co Solubilized alkaryl sulfonate composition
US2459818A (en) * 1944-08-04 1949-01-25 Lever Brothers Ltd Soap product containing guanidine stearate
US2464247A (en) * 1947-01-03 1949-03-15 American Cyanamid Co Preparation of guanidine sulfates
US2469338A (en) * 1946-12-24 1949-05-03 American Cyanamid Co Preparation of guanidine phosphates

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2374187A (en) * 1945-04-24 Detergent composition
US2459818A (en) * 1944-08-04 1949-01-25 Lever Brothers Ltd Soap product containing guanidine stearate
US2445975A (en) * 1946-05-08 1948-07-27 American Cyanamid Co Solubilized alkaryl sulfonate composition
US2469338A (en) * 1946-12-24 1949-05-03 American Cyanamid Co Preparation of guanidine phosphates
US2464247A (en) * 1947-01-03 1949-03-15 American Cyanamid Co Preparation of guanidine sulfates

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2832743A (en) * 1949-09-29 1958-04-29 Lever Brothers Ltd Free flowing alkyl aryl sulfonate detergent compositions
US2967832A (en) * 1954-11-15 1961-01-10 American Cyanamid Co Polyphosphate detergent compositions containing dicyandiamide tarnish inhibitor
US2921881A (en) * 1957-11-13 1960-01-19 American Cyanamid Co Fungitoxic-bacteriotoxic guanidine compositions
US3960782A (en) * 1974-09-27 1976-06-01 The Procter & Gamble Company Shampoo compositions which impart high luster and manageability to hair
JPWO2006025373A1 (ja) * 2004-08-31 2008-05-08 三洋化成工業株式会社 界面活性剤
JP4792396B2 (ja) * 2004-08-31 2011-10-12 三洋化成工業株式会社 界面活性剤
US10066193B2 (en) * 2012-02-17 2018-09-04 The Clorox Company Targeted performance of hypohalite methods thereof

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Publication number Publication date
ES192667A1 (es) 1951-04-16
GB690821A (en) 1953-04-29
FR1018893A (fr) 1953-01-14
BE495205A (en, 2012)

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