US3929678A - Detergent composition having enhanced particulate soil removal performance - Google Patents

Detergent composition having enhanced particulate soil removal performance Download PDF

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US3929678A
US3929678A US493953A US49395374A US3929678A US 3929678 A US3929678 A US 3929678A US 493953 A US493953 A US 493953A US 49395374 A US49395374 A US 49395374A US 3929678 A US3929678 A US 3929678A
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alkyl
detergent composition
group
composition according
detergent
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Robert Gene Laughlin
Vincent Paul Heuring
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Procter and Gamble Co
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Procter and Gamble Co
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Priority to DE2437090A priority Critical patent/DE2437090A1/de
Priority to US493953A priority patent/US3929678A/en
Priority to CA231,524A priority patent/CA1059867A/en
Priority to NL7508895A priority patent/NL7508895A/xx
Priority to AU83477/75A priority patent/AU501799B2/en
Priority to DE2533758A priority patent/DE2533758C2/de
Priority to NL7509077A priority patent/NL7509077A/xx
Priority to LU73103A priority patent/LU73103A1/xx
Priority to GB32084/75A priority patent/GB1507083A/en
Priority to IT2598175A priority patent/IT1040279B/it
Priority to FR7523931A priority patent/FR2280706A1/fr
Priority to BE158838A priority patent/BE831995A/xx
Priority to FR7524026A priority patent/FR2280705A1/fr
Priority to BE158875A priority patent/BE832048A/xx
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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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium 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
    • C11D1/88—Ampholytes; Electroneutral 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
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/886—Ampholytes containing P
    • 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
    • C11D3/16—Organic compounds
    • C11D3/36—Organic compounds containing phosphorus
    • C11D3/361—Phosphonates, phosphinates or phosphonites

Definitions

  • This invention relates to detergent compositions having improved particulate soil removal capability. More particularly, this invention relates to detergent compositions incorporating certain ethoxylated compounds which provide unexpectedly good clay soil removal.
  • Zwitterionic surfactants i.e., those surface active compounds that contain both positive and negative charge centers in the same molecule while being electrically neutral.
  • U.S. Pat. Nos. 3,668,240 and 3,764,568 to Melvin A. Barbera issued respectively on June 6, 1972, and Oct. 9, 1973, disclose zwitterionic surfactants having a 2, 3-butene moiety between the charge centers.
  • U.S. Pat. No. 3,332,875 to Adriaan Kessler and Phillip Floyd Pflaumer also discloses mixtures of certain olefin sulphonates with zwitterionic detergents in which the charge centers are separated by a 2-hydroxy propane group.
  • the present invention concerns detergent compositions incorporating certain zwitterionic surfactants in a polyethenoxy group of a size that permits not only adsorption of the molecule from an aqueous system onto particulate and other soils, and the subsequent removal of the soil by emulsification or dispersion but also the continued maintenance of the removed soil in suspension in the aqueous solution.
  • the present invention is directed to the discovery that a wider range of zwitterionic compounds, of the type disclosed in the above identified Applications, in combination with certain other surfactant and detergent builder materials can provide unexpectedly good particulate soil removal and also good oily soil removal from hard surfaces and textile materials.
  • the ethoxylated zwitterionic compounds useful in the present invention possess an ability to remove particulate soil that is independent of water hardness over a very wide range or Ca and Mg levels. Furthermore, this performance is relatively insensitive to temperature changes in the range of 70140F, the normal range for domestic cleaning functions.
  • Another object of the present invention is the provision of detergent compositions having improved particulate and oily soil removal performance in both liquid and granular forms.
  • composition of a watersoluble compound having a formula selected from the group consisting of:
  • R is selected from the group consisting of straight and branched chain C C alkyl and alkenyl moieties and alkaryl moieties in which the alkyl group has 10-24 carbon atoms;
  • R is selected from the group consisting of straight and branched chain C -C alkyl and alkenyl moieties, alkaryl moieties in which the alkyl group has 6-16 carbonatoms, and C alkyl and hydroxyalkyl moieties;
  • R is selected from the group consisting of straight and branched chain C C alkyl and alkenyl moieties, alkaryl moieties in which the alkyl group has 6-16 carbon atoms, C alkyl and hydroxyalkyl moieties and -(C H O),I-I wherein x has a value of about 3 to about 50;
  • R is selected from the group consisting of C alkylene, C -C alkenylene, 2-hydroxy C alkylene and 2- and 3- hydroxy C alkylene moieties and C -C alkarylene moieties provided that where R is (C H O),l-I then R, is CH Cl-I X is an anion selected from the group consisting of sulfate and sulfonate radicals;
  • R is selected from the group consisting of linear and branched C -C alkyl and alkenyl radicals
  • R is selected from the group consisting of linear and branched C -C alkyl and alkenyl radicals and C -C alkyl and hydroxyalkyl radicals;
  • X is selected from the group consisting of sulfate and sulfonate;
  • y and x have values in the range of 2-100 provided that y x B 12;
  • M is a cation selected from the group consisting of alkali metal, ammonium and alkanolammonium B. 99 to 1% by weight of the composition of an organic detergent, preferably selected from the group consisting of anionic, nonionic, ampholytic, and zwitterionic detergents.
  • ethoxylated zwitterionic compounds having hydroxy substituents on the carbon atoms immediately adjacent the nitrogen atom and/or X moiety are not preferred as they are unstable in water, especially at pI-Is other than neutrality, and are extremely difficult to prepare compared to other hydroxy substituted compounds.
  • the ethoxylated zwitterionic compound is one of either:
  • the FIGURE illustrates the sudsing characteristics of a series of blends of an ethoxylated zwitterionic compound (C EZ) and an anionic cosurfactant (C LAS).
  • C EZ ethoxylated zwitterionic compound
  • C LAS anionic cosurfactant
  • the FIGURE constitutes a plot of the suds height (in cms.) developed by the Recirculating Suds Generator (R.S.G.) as a function of time (in minutes) for C EZ alone, for blends of C EZ:C LAS of 19:1, 7:1, 3:1 and 1:1 by weight and for C LAS alone.
  • PERFORMANCE TESTING In this specification the assessment of particulate and a. Particulate soil removal testing This is carried out in either an automatic mini washing machine (AMW) having a capacity of 4,700 ml. and a cloth/liquor ratio of 1:30 or a Tergotometer having a capacity of 1,000 ml. and a cloth/liquor ratio of 1:140. In both instances the machines are fitted with horizonally rotating paddle agitators, the AMW having a speed of 100 RPM, while the Tergotometer uses a speed of 80 RPM.
  • AMW automatic mini washing machine
  • the AMW washing procedure involves a l2-minute wash cycle at 105F in 7 grains per US. gallon hard water (calculated as CaCO using a 2:1 ratio of CazMg salts. The first two minutes of the cycle are used for product dissolution following which the fabric load is added and washed for the remaining 10 minutes. A 5-minute rinse cycle then follows, 2 minutes of which is with agitation, the remaining 3 minutes being a spin to remove excess moisture. The fabrics are then tumbledried prior to being graded.
  • a similar washing procedure is used for the Tergotometer with the exception that 5.5 grains/gallon water is employed having a 3:1 ratio of CazMg salts (calculated as CaCO).
  • the wash is followed by one rinse cycle of 3 minutes in F water of the same hardness, level, and type as for the wash, after which the swatches are machine-dried before being graded.
  • the fabric load for particulate soil removal testing comprises a mixture of white cotton, polycotton (65% DACRON/35% cotton), and polyester (KODEL) swatches which are stained with a standardized illite clay soil.
  • AMW three 5 X 5 inch swatches of each fabric are used in each load, while in the Tergotometer, three 2% X 2% inch swatches of each fabric type are employed.
  • Performance is determined by finding the difference in whiteness (AW) before and after washing as:
  • Grease and oil removal testing Identical equipment and washing conditions are used to evaluate grease and oil removal performance.
  • the fabric load comprises a mixture of green polycotton (65% DACRON/35% cotton) and polyester (KODEL) swatches, four 2% X 2% inch swatches of each type being used in the tergotometer.
  • Two triglyceride stains, namely bacon grease and vegetable oil, and two hydrocarbon-based stains, namely dirty motor oil and simulated lipid soil are employed.
  • a circulating pump which is connected to the base of the cylinder and which discharges to an exit jet located in the cylinder above the level of the test solution.
  • the desired solution temperature is maintained by heating tapes secured around tubing connecting the pump to the exit jet.
  • test solution approximately 200 ml. is placed in the cylinder and continuously circulated at a selected temperature within the range of 70-125F.
  • the force of the downward-directed solution from the exit jet onto the bulk of the test solution in the graduated cylinder generates a level of suds in the cylinder which is measured at one-minute intervals.
  • compositions of the present invention contain two essential components, namely the ethoxylated zwitterionic compound and a surfactant compound.
  • the zwitterionic and surfactant may be present in a ratio of from 99:1 to 1:99 by weight, preferably :1 to 1:10 by weight, and most preferably 4:1 to 1:10 by weight depending on the nature of the zwitterionic compound and the type of product to be formulated.
  • a product intended for prewash treatment of laundry to remove specific stains by direct application to the fabric will be formulated to contain a lower level of zwitterionic compound and different optional ingredients than a product designed as a main wash detergent.
  • the level of ethoxylated zwitterionic compound in the product will lie in the range 535% by weight, preferably 1025%, and most preferably -20%, the level of the surfactant compound being 05-15%, preferably l10%, and most preferably l-5% by weight.
  • a main wash detergent can be formulated as a conventional granule or as a liquid, paste, flake, ribbon, noodle, pellet, or tablet. As will be shown hereinafter, this formulation flexibility is due, at least in part, to the ability of the zwitterionic surfactants of the present invention to achieve satisfactory particulate soil removal performance equivalent to that of commercial heavy duty laundry detergents when used in blends with other surfactants.
  • Ethoxylated zwitterionic compounds useful in the present invention may have one or other of the following formulae:
  • R is a hydrocarbon moiety that can be a straight or branched chain C -C alkyl or alkenyl group or an alkaryl group in which the alkyl portion has 10-24 carbon atoms;
  • R and R are C C alkyl or hydroxyalkyl groups;
  • R is a C -C alkylene, C -C alkenylene or 2-hydroxy propylene or 2- or 3- hydroxy butylene group or a C -C alkarylene group;
  • X is a sulfonate or sulfate radical; and y has a value in the range 2-100.
  • preferred groups for R are C C, alkyl, particularly C -C alkyl, while preferred groups for R and R are C alkyl and C hydroxyalkyl, the most preferred groups being methyland hydroxyethylradicals.
  • the preferred range of values for y is 6-50, more preferably 6-25, and most preferably 912.
  • the synthesis of the above compounds can be achieved using readily available commercial starting materials.
  • One such synthetic route is as follows. Sodium hydride is slowly and stoichiometrically reacted (2:1 molar ratio) with polyethylene glycol in a solution of tetrahydrofuran under an atmosphere of an inert gas, e.g., argon. The reaction is carried out over a period of 4-10 hours in an ice bath to cool the reaction, which is exothermic.
  • the polyethylene glycol used is the commercially available material comprising a mixture of compounds having chain lengths from about 4 to about 100.
  • the resultant product is the sodium salt represented by (I) N21*0(CH CH O) CH CI-I ONa wherein y can be, for example, 3, 21, 32, 67, or 99.
  • reaction product (I) A stoichometric amount of tosyl chloride dissolved in tetrahydrofuran is then added slowly to reaction product (I), cooled in an ice bath, and the resultant mixture is stirred for 12 to 20 hours to form i.e., the polyethylene glycol ditosylate.
  • Pyridine or other suitable base is added to the mixture, and the solution is then poured into ice water and acidified with l-ICl to a pH of about 2-3.
  • the aqueous solution is then extracted with chloroform, rinsed with water and the chloroform extract is dried over sodium sulfate to give purified polyethylene glycol ditosylate (II).
  • the ditosylate (II) is then reacted with a tertiary amine of the structure (III) wherein R R and R are as defined above.
  • the reaction of (III) with (II) is conveniently carried out neat, or with a suitable solvent as N,N-dimethyl formamide 7 or CH CN at temperatures of 80 to about 100C to produce a mixture of R. .H. cH..
  • Compound (V1) can optionally be further purified using the mixed bed resin and tested for purity by thin layer chromatography.
  • zwitterionic compounds of the general formula (VI) can be prepared using any of a variety of tertiary amines (III).
  • zwitterionic compounds having any desired, specific degree of ethoxylation (y) can be prepared by fractionating the polyethylene glycol used in the reaction and using the desired fraction in the synthesis scheme.
  • relatively narrowly defined distillation cuts of polyoxyethylene glycol having any desired average degree of ethoxylation, and containing individual compounds having differing degrees of ethoxylation within the desired range can be used in the reaction.
  • sodium salt (I) can be reacted with a variety of epoxy compounds (e.g., butylene epoxide) or halohydrins (e.g., -chlorohexanol or 8- bromooctanol) to provide zwitterionics having various R groups within the scope of this invention.
  • epoxy compounds e.g., butylene epoxide
  • halohydrins e.g., -chlorohexanol or 8- bromooctanol
  • the mixture was heated overnight at 100C (still under nitrogen) and then filtered hot to remove most of the sodium chloride. Excess triethyleneglycol was stripped under vacuum and the mixture was again filtered while hot. The material was purified by molecular distillation and has a b.p. of 170175C at 0.001 mm.
  • Nonaethyleneglycol ditosylate B
  • the nonaethyleneglycol (A) 300 grams, (0.72 moles) was dissolved in 800 ml (10.3 moles) of dry pyridine and cooled to 0C.
  • Tosyl chloride i.e., p-toluene-sulfonyl chloride, 420 grams, 2.2 moles
  • the temperature increased to 10C and the clear reaction mixture became cloudy.
  • the mixture was stirred at 0-l0C for an additional 3 hrs., then poured into an equal volume of ice water and acidified to pH 2-3 with 6N HCl.
  • the dimethyloctadecylamine can be replaced by dimethylhexadecylamine, dimethylnonadecylamine, dimethyleicosylamine, and dimethyldocosylamine, respectively, and the corresponding compounds wherein R is C C C and C are secured, respectively.
  • R and R are hydrocarbon moieties that can be straight or branched chain C -C alkyl or alkenyl groups;
  • R R and X are as in (i) (a.) above and y has an average value in the range 6-100.
  • R and R are identical and comprise alkyl groups each having 10 to 16 carbon atoms, most preferably alkyl groups each having 10 to 24 carbon atoms.
  • Preferred values for y lie in the range 9 to 50, most preferably in the range 12 to 25.
  • Methylation of di-n-octylamine was accomplished by slowly mixing 50 grams of the secondary amine with, first, formic acid (30.03 grams), and then formaldehyde, at C. The reaction mixture was kept at 80C for 24 hours, then adjusted to pH 8-9 with NaOH solution. The resulting tertiary amine was extracted with CHCl and dried over Na SO The tertiary amine (25.6 grams, 0.10 mole) was then refluxed with 72 grams (0.10 mole) of nonaethylene glycol ditosylate (compound B, prepared as in the previous procedure) in acetonitrile for 6 hours.
  • compound B nonaethylene glycol ditosylate
  • R R R are all hydrocarbon moieties that can be straight or branched chain C -C alkyl or alkenyl groups; R and x are as in (i) (a.) and (b.) above and y has a value in the range 6-100.
  • R R and R are each identical and each comprise an alkyl group having 8-16 carbon atoms in the chain. Most preferably each chain contains 8-12 carbon atoms.
  • y has a preferred value in the range 9-50, most preferably in the range 12-50.
  • Tri-n-octylamine was distilled to insure purity and 42 grams of the purified product (0.12 mole) was reacted with 87 grams (0.12 mole) of the ditosylate of nonaethylene glycol (compound B in the mono-long chain preparation) in dry N,N-dimethylformamide at C for 2 hours.
  • the dimethylformamide was removed and the mixture of monoand diquaternary material was dissolved in methanol. This mixture was refluxed for 16 hours with 100 grams of NA SO predissolved in water.
  • the insoluble salts were filtered and the filtrate was stirred with 500 grams mixed bed resin (Rexyn 300 HOH) for 24 hours. An additional treatment with 500 grams fresh resin was used to further purify the product.
  • R can be a linear or branched C;,C alkyl or alkenyl group, preferably a C1848 alkyl or alkenyl group; R can also be a C -C alkyl or alkenyl group or can be a C -C alkyl or hydroxyalkyl group, preferably a methyl group; and X can be a sulfonate or sulfate radical.
  • the number of ethylene oxide groups in each chain can be from 1 to 100 but their sum should be greater than 10. Normally there will be approximately the same number in each chain, the sum of the groups in both chains preferably having a value in the range 12-50 and most preferably in the range 12-25.
  • Ethoquad is a mixture of quaternary ammonium compounds whose predominant component is a di-ethoxylate of the structure wherein y and x are each non-zero integers whose average sum is, for example, 5, 10, 15, 50, depending on the cut selected, and R and R are C C alkyl and C -C alkyl, respectively.
  • the compounds herein are prepared by dissolving Ethoquad in pyridine or other suitable base and cooling the mixture to a temperature of about C. Tosyl chloride is slowly added to the Ethoquad mixture at a 1:1 stoichiometric ratio while the reaction mixture is kept at about 0C5C in an ice bath. The mixture is then stirred for about 24 hours at OC-5C. At the end of that time the reaction mixture is poured into water and acidified to a pH of 2-3 with HCl.
  • tosylate ester is then dissolved in methanol and refluxed for about 24 hours with about a molar excess of sodium sulfite predissolved in H O.
  • the reaction mixture is cooled and excess sodium sulfite and sodium tosylate are removed by filtration.
  • the filtrate is stirred with a mixed bed (anion-cation) resin to purify the product.
  • a second resin treatment can optionally be used to remove substantially all traces of all cationic and anionic impurities.
  • the purified monosulfonate corresponding to (I) above is recovered by evaporating the solvent.
  • the product can optionally be recrystallized from acetone.
  • the cation M can be alkali metal, ammonium, and alkanolammonium, e.g. ethanolammonium or methanolammonium but is most preferably sodium.
  • the disulfonate (II) is prepared in the same manner as the mono-sulfonate (l), but using excess tosyl chloride (about 3:1 mole ratio, or greater) in the first step and a larger excess of sodium sulfite (20:1 mole ratio) in the second step. If a cation, M, other than sodium is desired in the final product, the corresponding sulfite can be used in the second step. Alternatively, the sodium form of compound (II) can be ion-exchanged in standard fashion to any desired cation, M. The resin purification treatment is unnecessary when preparing the disulfonate. v
  • the sulfates of the type (I) and (II) are easily prepared by reacting one of two moles of chlorosulfonic acid with the Ethoquads, respectively.
  • the same consideration with regard to selection of cation M holds true for the sulfates as for the sulfonates.
  • diethoxylated amino starting materials can be employed in the fore-- going reaction scheme.
  • Ethoquad derivatives having variations in groups R and R are commercially available, e.g., compounds wherein R is an average C cut.
  • precursor compounds having varying sums of y and x can be selected according to the desires of the user. Compounds wherein y and x are of approximately equal length, the sum of y and x being from about 12 to about 25, most preferably fom 15 to about 25, are especially useful herein.
  • Ethomeens (a tradename of a clas of compounds marketed by the Armak Company, a division of the Armour Company) can be quaternized to produce variations of the commercial Ethoquads.
  • Ethomeens of the general formula reacted with excess alkyl iodide or hydroxy-substituted alkyl iodide (Cl-I 1, C l-1 L etc.) to produce a quaternary ammonium compound which can be sulfated or sulfonated on one or both ethylene oxide groups in the manner disclosed above.
  • mixtures of any of these zwitterionic compounds in any proportions may be used in the compositions of the present invention.
  • Such 2 mixtures may be produced intentionally by blending individual species or may arise as a result of the choice of feedstocks or as a result of the processing steps involved.
  • the ethoxylated zwitterionic compounds useful in the present invention desirably display appreciable solubility in aqueous media.
  • the second essential component of a composition in accordance with the present invention is an organic detergent. This can be present at a level of from l-99% by weight of the composition, the actual level being dependent on the end use of the composition and its desired physical form.
  • a wide range of organic detergents can be mixed i.e. can be considered compatible with the ethoxylated zwitterionic compounds to form compositions useful in the present invention.
  • compatible is defined as causing no appeciable decrease in the ability of the ethoxylated zwitterionic compound to remove and suspend particulate soil.
  • Classes of compatible detergents that can serve as cosurfactants include the nonionic, zwitterionic, and
  • ampholytic surfactants which can be used in a broad range of proportions to the ethoxylated zwitterionic compound.
  • anionic detergents do not enhance the particulate soil removal performance of the ethoxylated zwitterionic compounds to the same extent, especially on synthetic fibers, although delayed solubility of the anionic surfactant improves the performance of the combination.
  • cationic surfactants only those having a polyoxyalkylene function are compatible with the ethoxylated zwitterionic compounds useful in the present invention.
  • nonionic surfactants are compounds produced by the condensation of an alkylene oxide (hydrophilic in nature) with an organic hydrophobic compound which is usually aliphatic or alkyl aromatic in nature.
  • the length of the hydrophilic or polyoxyalkylene moiety which is condensed with any particular hydrophobic compound can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements.
  • Another variety of nonionic surfactant is the semi-polar nonionic typified by the amine oxides, phosphine oxides, and sulfoxides.
  • Suitable nonionic surfactants include:
  • the polyethylene oxide condensates of alkyl phenols. These compounds include the condensation products of alkyl phenols having an alkyl group containing from about 6 to 12 carbon atoms in either a straight chain or branched chain configuration, with ethylene oxide, the said ethylene oxide being present in amounts equal to to 25 moles of ethylene oxide per mole of alkyl phenol.
  • the alkyl substituent in such compounds may be derived, for example, from polymerized propylene, diisobutylene, octene, or nonene.
  • Examples of compounds of this type include nonyl phenol condensed with about 9.5 moles of ethylene oxide per mole of nonyl phenol, dodecyl phenol condensed with about 12 moles of ethylene oxide per mole of phenol, dinonyl phenol condensed with about moles of ethylene oxide per mole of phenol, di-isooctylphenol condensed with about 15 moles of ethylene oxide per mole of phenol.
  • Commercially available nonionic surfactants of this type include lgepal CO-6l0 marketed by the GAP Corporation; and Triton X-45, X-l l4, X-100 and X- 102, all marketed by the Rohm and Haas Company.
  • the condensation products of aliphatic alcohols with ethylene oxide may either be straight or branched and generally contains from about 8 to about 22 carbon atoms.
  • ethoxylated alcohols include the condensation product of about 6 moles of ethylene oxide with 1 mole of tridecanol, myristyl alcohol condensed with about 10 moles of ethylene oxide per mole of myristyl alcohol, the condensation product of ethylene oxide with coconut fatty alcohol wherein the coconut alcohol is a mixture of fatty alcohols with alkyl chains varying from 10 to 14 carbon atoms and wherein the condensate contains about 6 moles of ethylene oxide per mole of alcohol, and the condensation product of about 9 moles of ethylene oxide with the abovedescribed coconut alcohol.
  • nonionic surfactants of this type include Tergitol l5-S-9 marketed by the Union Carbide Corporation, Neodol 23-6.5 marketed by the Shell Chemical Company and Kyro EOB marketed by The Procter & Gamble Company.
  • Preferred nonionic surfactants R being selected from the group consisting of hydrogen and mixtures thereof with not more than 40% by weight of lower alkyl, wherein R and R together form an alkyl residue having a mean chain length in the range of 8-15 carbon atoms, at least 65% by weight of said residue having a chain length within 1': 1 carbon atoms of the mean, wherein 3.5 n,,,, 6.5 provided that the total amount by weight of components in which n 0 shall be not greater than 5% and the total amount by weight of components in which n 2-7 inclusive shall be not less than 63% based on the total weight of the, or each, said ethoxylate material and the I-ILB of the or each said ethoxylate material shall lie in the range 9.5-11.5, said composition being otherwise free of nonionic surfactants having an l-ILB outside of this range.
  • Preferred embodiments of this invention utilize blends of primary alcohols in which at least and most preferably by weight of the alcohol has a chain length within i 1 carbon atom of the mean, wherein the amount of unethoxylated alcohol is less than 1% by weight and wherein the amount of ethoxylated alcohols having 2-7 ethylene oxide groups is at least 70% by weight.
  • ethoxylates having a mean chain length of C and below contain at least 55% by weight of material having 2-6 ethoxylate groups while for ethoxylates having a chain length of C C at least 5 5 by weight of the material has 3-7 ethoxylate groups.
  • Ethoxylates having a chain length in the C range preferably have at least 55% by weight of E -E material.
  • the I-ILB of the ethoxylates are in the range 10.0-1 L1.
  • the condensation products of ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol.
  • the hydrophobic portion of these compounds has a molecular weight of from about 1500 to 1800 and of course exhibits water insolubility.
  • the addition of polyoxyethylene moieties to this hydrophobic portion tends to increase the water-solubility of the molecule as a whole, and the liquid character of the product is retained up to the point where the polyoxyethylene content is about 50% of the total weight of the condensation product.
  • Examples of compounds of this type include certain of the commercially available Pluronic surfactants marketed by the Wyandotte Chemicals Corporation.
  • the condensation products of ethylene oxide with the product resulting from the reaction of propylene oxide and ethylene diamine consist of the reaction product of ethylene diamine and excess propylene oxide, said base having a molecular weight of from about 2500 to about 3000.
  • This base is condensed with ethylene oxide to the extent that the condensation product contains from about 40 to about 80% by weight of polyoxyethylene and has a molecular weight of from about 5,000 to about 1 1,000.
  • this type of nonionic surfactant include certain of the commercially available Tetronic compounds marketed by the Wyandotte Chemicals Corporation.
  • Surfactants having the formula RR R N O (amine oxide surfactants) wherein R is an alkyl group containing from about 10 to about 18 carbon atoms, from to about 2 hydroxy groups and from 0 to about ether linkages, there being at least one moiety of R which is an alkyl group containing from about to about 18 carbon atoms and no ether linkages, and each R and R is selected from the group consisting of alkyl groups and hydroxyalkyl groups containing from 1 to about 3 carbon atoms;
  • amine oxide surfactants include: dimethyldodecylamine oxide, dimethyltetradecylamine oxide, ethylmethyltetradecylamine oxide, cetyldimethylamine oxide, dimethylstearylamine oxide, cetylethylpropylamine oxide, diethyldodecylamine oxide, diethyltetradecylamine oxide, dipropyldodecylamine oxide, bis-(2-hydroxyethyl)dodecylamine oxide, bis- (2-hydroxyethyl)-3-dodecoxy-2-hydroxypropylamine oxide, (2-hydroxypropyl )methyltetradecylamine oxide, dimethyloleylamine oxide, dimethyl-(2-hydroxydodecyl)amine oxide, and the corresponding decyl,
  • R R R P O phosphine oxide surfactants
  • R is an alkyl group containing from about 10 to about 28 carbon atoms, from 0 to about 2 hydroxy groups and from O to about 5 ether linkages, there being at least one moiety of R which is an alkyl group containing from about 10 to about l8 carbon atoms and no ether linkages, and
  • R is an alkyl group containing from about 10 to about 18 carbon atoms, from 0 to about 5 ether linkages and from 0 to about 2 hydroxyl substituents, at least one moiety of R being an alkyl group containing no ether linkages and containing from about 10 to about 18 carbon atoms, and wherein R is an alkyl group containing from 1 to 3 carbon atoms and from zero to two hydroxyl groups.
  • sulfoxide surfactants include octadecyl methyl sulfoxide, dodecyl methyl sulfoxide, tetradecyl methyl sulfoxide, 3-hydroxytridecyl methyl sulfoxide, 3-methoxytridecyl methyl sulfoxide, 3-hydroxy- 4-dodecoxybutyl methyl sulfoxide, octadecyl 2-hydroxyethyl sulfoxide, and dodecylethyl sulfoxide.
  • Table 1 illustrates the clay soil removal performance of mixtures of ethoxylated zwitterionic compounds and various nonionic surfactants.
  • Experimental Run 1 shows that the C ethoxylated zwitterionic material alone at a level of 250 ppm in water closely approaches the cleaning performance of the fully formulated control product A on polyester and polycotton fabrics and achieves a major proportion of the control product performance on cotton.
  • Experimental Run 2 shows that an appreciable proportion of this performance is retained at half the level of the ethoxylated zwitterionic compound.
  • Table V is a presentation of the grease and oil removal performance achieved by detergent compositions of the present invention.
  • Runs 4 and 5 show respectively combinations of 125 p.p.m. C ethoxylated zwitterionic compound of Table l with 125 ppm of Neodol 45 E7 and with 125 ppm of G secondary alcohol ethoxylate (Tergitol 15-S-9 marketed by Union Carbide Corporation).
  • Runs 11 and 12 give the same data for the C ethoxylated zwitterionic of Table 1.
  • advantages can be seen on polyester fabric for the combinations relative to the performance of the ethoxylated zwitterionic compound alone at 250 ppm.
  • nonionic surfactants can be used to reduce the level of ethoxylated zwitterionic necessary to achieve a 17 18 given level of performance.
  • level of performance can be raised by ics not having such good particulate soil removal perthe addition of nonionic surfactants and builders.
  • “Stripped C E” is a linear primary C alcohol condensed with approximately 3 moles of ethylene oxide per mole of alcohol and then stripped to remove at least 95% of the unethoxylated alcohol and a proportion of the monoethoxylate, so as to leave a condensate having a mean of 4 moles ethylene oxide per mole of alcohol.
  • ""Ethomeen 18/60 is a tertiary C amine having 2 ethoxy side chains directly attached to the nitrogen atom and containing a total of ethylene oxide groups.
  • Examples of compounds falling within this definition are sodium 3- (dodecylamino )propionate, sodium 3-(dodecylamino propane-l-sulfonate, sodium 2-(dodecylamino)ethyl sulfate, sodium Z-(dimethylamino)octadecanoate, disodium 3-(N-carboxymethyldodecylamino )propanel sulfonate, disodium octadecyl-iminodiacetate, sodium l-carboxymethyl-2-undecylimidazole, and sodium N,N-bis(Z-hydroxyethyl)-2-sulfato-3-dodecoxypropylamine.
  • Sodium 3-(dodecylamino)propane-l-su1- fonate is preferred.
  • ZWITTERIONIC SYNTHETIC DETERGENTS can be broadly described as derivatives of secondary and tertiary amines, derivatives of heterocyclic secondary and tertiary amines, or derivatives of quaternary ammonium, quaternary phosphonium or tertiary sulfonium compounds.
  • the cationic atom in the quaternary compound can be part of a heterocyclic ring.
  • aliphatic group straight chain or branched, containing from about 3 to 18 carbon atoms and at least one aliphatic substituent containing an anionic water-solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • anionic water-solubilizing group e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
  • R is alkyl, alkenyl or a hydroxyalkyl containing from about 8 to about 18 carbon atoms and containing if desired up to about ethylene oxide moieties and/or a glyceryl moiety;
  • Y is nitrogen, phosphorus or sulfur,
  • R is C -C alkyl or a C -C B- or ymonohydroxy alkyl containing I to 3 carbon atoms;
  • x is I when Y is S, 2 when Y is N or P;
  • R is C -C alkylene or 2-hydroxy-, 3-propylene or 2- or 3-hydroxy butylene containing from 1 to about 5 carbon atoms; and
  • Z is a carboxy, sulfonate, sulfate, phosphate or phosphonate group.
  • Examples of this class of zwitterionic surfactants include 3-(N,N-dimethyl-N-hexadecylammonio )-propanel -sulfonate; 3-( N,N-dimethyl-N-hexadecylammonio )-2-hydroxypropanel -sulfonate; N,N-dimethyl-N-dodecylammonio acetate; 3- (N,N-dimethyl-N-dodecylammonio)propionate; 2- (N,N-dimethyl-N-octadecylammonio)ethyl sulfate; 3 P,P-dimethyl-P-dodec ylphosphonio )propanel -sulfonate; 2-(S-methyl-S-tert-hexadecylsulfonio)ethanel-sulfonate; 3-(S-methyl-S-dodecyls
  • Preferred compounds of this class from a commercial standpoint are 3-(N,N-dimethyl-N-hexadecylammonio)-2-hydroxypropane-l-sulfonate; 3-(N,N-dimethyl-N- alkylammonio )-2-hydroxypropane-l -sulfonate, alkyl group being derived from tallow fatty alcohol; 3-( N,N-dimethyI-N-hexadecylammonio )propane-l suffonate; 3-(N,N-dimethyl-N-tetradecylammonio)- propane- I -sulfonate; 3-(N,N-dimethyl-N-alkylammonio )-2-hydroxypropane-l-sulfonate, the alkyl group being derived from the middle cut of coconut fatty alcohol; 3-(N,N-dimethyldodecylammonio)-2-hydroxypropane-l -
  • R is an alkyl, cycloalkyl, aryl, aralkyl or alkaryl group containing from I0 to 20 carbon atoms
  • M is a bivalent radical selected from the group consisting of aminocarbonyl, carbonylamino, carbonyloxy, oxycarbonyloxy, aminocarbonylamino, the corresponding thio groupings and substituted amino derivatives
  • R and R are alkylene groups containing from I to 12 carbon atoms
  • R is alkyl or hydroxyalkyl containing from I to 10 carbon atoms
  • R is selected from the the group consisting of R groups R MR and R COOMe wherein R R R R and R are as defined above and Me is a monovalent salt-forming cation.
  • Compounds of the type include N,N-bis(oleylamidopropyl)- N-methyl-N-carboxymethylammonium betaine; N,N- bis(stearamidopropyl)-N-rnethyl-N-carboxymethylammonium betaine; N-(stearamidopropyl)-N-dimethy1-N- carboxymethylammonium betaine; N,N-bis- (oleylamidopropyl)-N-(2-hydroxyethyl)-N-carboxymethylammonium betaine; and N-N-bis-(stearamidopropyl)-N-( 2-hydroxyethyl)-N-carboxymethylammonium betaine.
  • Zwitterionic surfactants of this type are prepared in accordance with methods described in US. Pat. No. 3,265,719 and DAS 1,018,421.
  • R is an alkyl group
  • R is a hydrogen atom or an alkyl group, the total number of carbon atoms in R and R being from 8 to 16 and represents a quaternary ammonio group in which each group R R and R is an alkyl or hydroxyalkyl group or the groups R R and R are conjoined in a heterocyclic ring and n is 1 or 2.
  • zwitterionic surfactants of this type include the y and 8 hexadecyl pyridino sulphobetaines, the 'y and 8 hexadecyl 'ypicolino sulphobetaines, the 7 and 8 tetradecyl pyridino sulphobetaines and the hexadecyl trimethylammonio sulphobetaines.
  • Preparation of such zwitterionic surfactants is described in British patent specification No. 1,277,200.
  • R is an alkarylmethylene group containing from about 8 to 24 carbon atoms in the alkyl chain; R is selected from the group consisting of R groups and alkyl and hydroxyalkyl groups containg from 1 to 7 carbon atoms; R is alkyl or hydroxyalkyl containing from 1 to 7 carbon atoms; R is alkylene or hydroxyalkylene containing from 1 to 7 carbon atoms and Z is selected from the group consisting of sulfonate, carboxy and sulfate.
  • Examples of zwitterionic surfactants of this type include 3-(N-4-n-dodecylbenzyl-N,N-dimethylammonio)propane-l-sulfonate; 4-(N-4-n-dodecylbenzyl-N,N-dimethylammonio)butane-1-sulfonate; 3- (N-4-n-hexadecylbenzyl-N,N-dimethylammmonio)- propane- 1 -sulfonate; 3-( N-4-n-dodecylbenzyl-N,N- dimethylammonio)propionate; 4-(N-4-n-hexadecylbenzyl-N,N-dimethylammonio)butyrate; 3-(N-4-n-tetradecylbenzyl-N,N-dimethylammonio)propane-1-sulfate; 3-(N-4-n-dodecylbenzyl-
  • Examples of zwitterionic surfactants of this type include 3-(N-dodecylphenyl- N,N-dimethylammonio)- propane-1 -su1fonate; 4-(N-hexadecylphenyl-N ,N- dimethylammonio)butane-l-sulfonate; and 3-(N- dodecylphenyl-N,N-dimethylammonio)-2-hydroxypropane-l-sulfonate.
  • Compounds of this type are described more fully in British Pat. Nos. 970,883 and 1,046,252, incorporated herein by reference.
  • preferred compounds include 3(N,N-dimethyl-N-alkylammonio )-propane- 1 -sulfonate and 3 (N ,N- dimethyl-N-alkylammonio)-2-hydroxypropane-1-sulfonate wherein in both compounds the alkyl group averages 14.8 carbon atoms in length; 3(N,N-dimethyl- N-hexadecylammonio)-propanel -sulfonate; 3(N ,N- dimethyl-N-hexadecylammonio)-2-hydroxypropane-1- sulfonate; 3-(N-dodecylbenzyl-N,N-dimethylammonio)-propane-1-sulfonate; 3-(N-dodecylbenzyl- N ,N ,dimethylammonio)-2-hydr0xypropane-1-
  • the C ethoxylated zwitterionic material on its own at 250 ppm is as good as the C APS material at 125 ppm with 1000 ppm of builder and better than C APS at 250 ppm with 400 ppm of 24 process).
  • Resin acids are suitable such as rosin and those resin acids in tall oil.
  • Napthenic acids are also suitable.
  • Sodium and potassium soaps can be made by direct saponification of the fats and oils or by the neubuilder, on both cotton and polyester fabrics. tralization of the free fatty acids which are prepared in Grease and oil removal data for combinations of the a separate manufacturing process.
  • Particularly useful C and C ethoxylated zwitterionic compounds with are the sodium and potassium salts of the mixtures of zwitterionic cosurfactants are shown in Table V, Runs fatty acids derived from coconut oil and tallow, i.e., 6 and 7 (C and 13 and 14 (C Advantages are sodium or potassium tallow and coconut soap. again apparent for the combinations in removing both Anionic synthetic detergents include water-soluble triglyceride and hydrocarbon stains from polyester salts, particularly the alkali metal salts, of organic sulfufabrics although the results for polycotton are more ric reaction products having in their molecular strucvariable.
  • Cosurfactants were 3-(N-alkyl N,N-dimethyl ammonio)propane-l-sulphonate(APS) and 3-(N-alkyl N,N-dimethyl ammonio)-2-hydroxy propane- I -sulphonate( HAPS) RELATIVE ETHOXYLATED LEVEL LEVEL LEVEL CLAY REMOVAL INDEX ZWI'ITERIONIC PPM IN PPM IN BUILDER PPM IN POLY- POLY- NO.
  • This class of detergents includes ordinary alkali metal soaps such as the sodium, potassium, ammonium and alkylolamminium salts of higher fatty acids containing from about eight to about 24 carbon atoms and preferably from about 10 to about 20 carbon atoms.
  • Suitable fatty acids can be obtained from natural sources such as, for instance, from plant or animal esters (e.g., palm oil, coconut oil, babassu oil, soybean oil, caster oil, tallow, whale and fish oils, grease, lard, and mixtures thereof).
  • the fatty acids also can be synthetically prepared (e.g., by the oxidation of petroleum, or by hydrogenation of carbon monoxide by the Fischer-Tropsch carbon atoms and a moiety selected from the group consisting of sulfonic acid and sulfuric acid ester moieties.
  • alkyl is the alkyl portion of higher acyl moieties.
  • examples of this group of synthetic detergents are the sodium and potassium alkyl sulfates, especially those obtained by sulfating the higher alcohols (C -C carbon atoms) produced by reducing the glycerides of tallow or coconut oil; sodium and potassium alkyl benzene sulfonates, in which the alkyl group contains from about 9 to about 20 carbon atoms in straight-chain or branched-chain configuration, e.g. those of the type described in US. Pat. Nos.
  • 2,220,099 and 2,477,383 (especially valuable are linear straight chain alkyl benzene sulfonates in which the 25 average of the alkyl groups is about 11.8 carbon atoms and commonly abbreviated as C LAS); sodium alkyl glyceryl ether sulfonates, especially those ethers of higher alcohols derived from tallow and coconut oil; sodium coconut oil fatty acid monoglyceride sulfonates and sulfates.
  • Anionic phosphate surfactants are also useful in the present invention. These are surface active materials having substantial detergent capability in which the anionic solubilizing group connecting hydrophobic moieties is an oxy acid of phosphorus.
  • the more common solubilizing groups are SO H and SO H.
  • Alkyl phosphate esters such as (R-O PO H and ROPO H in which R represents an alkyl chain containing from about 8 to about 20 carbon atoms are useful herein.
  • phosphate esters can be modified by including in the molecule from one to about 40 alkylene oxide units, e.g., ethylene oxide units.
  • Formulae for these niodified phosphate anionic detergents are in which R represents an alkyl group containing from about 8 to 20 carbon atoms, or an alkylphenyl group in which the alkyl group contains from about 8 to 20 carbon atoms, and M represents a soluble cation such as hydrogen, sodium, potassium, ammonium or substituted ammonium; and in which n is an integer from 1 to about 40.
  • Suitable anionic organic detergents particularly useful in this invention includes salts of 2-acyloxyalkane-l-sulfonic acids exemplified by the reaction product of fatty acids esterified with isethionic acid and neutralized with sodium hydroxide where, for example, the fatty acids are derived from coconut oil.
  • These salts have the formula where R is alkyl of about 9 to about 23 carbon atoms (forming with the two carbon atoms an alkane group); R is alkyl of 1 to about 8 carbon atoms; and M is a water-soluble cation.
  • the water-soluble cation, M, in the hereinbefore described structural formula can be, for example, an alkali metal cation (e.g., sodium, potassium, lithium), ammonium or substituted-ammonium cation.
  • alkali metal cation e.g., sodium, potassium, lithium
  • substituted ammonium cations include methyl-, dimethyl-, and trim'ethylammonium cations and quaternary ammonium cations such as tetramethyl-ammonium and dimethyl piperidinium cations and those derived from alkylamines such as ethylamine, diethylamine, triethylamine, mixtures thereof, and the like.
  • beta-acyloxy-alkane-l-sulfonates or alternatively 2-acyloxy-alkane-l-sulfonates, useful herein include the sodium salt of 2-acetoxy-tridecane-l-sulfonic acid; the potassium salt of 2-propionyloxy-tetradecane-l-sulfonic acid; the lithium salt of 2-butanoyloxy-tetradecane-l-sulfonic acid; the sodium salt of 2-pentanoyloxy-pentadecane-l-sulfonic acid; the sodium salt of Z-acetoxy-hexadecane-l-sulfonic acid; the potassium salt of 2-octanoyloxy-tetradecane-l-sulfonic acid; the sodium salt of 2-acetoxyheptadecane-l-sulfonic acid; the lithium salt of 2- acetoxy-octadecane-l-sulfonic acid; the potassium salt of 2-acetoxy-o
  • beta-acyloxy-alkane-l-sulfonate salts herein are the alkali metal salts of beta-acetoxy-alkanel-sulfonic acids corresponding to the above formula wherein R is an alkyl of about 12 to about 16 carbon atoms, these salts being preferred from the standpoints of their excellent cleaning properties and ready availability.
  • anionic detergent compounds herein both by virtue of superior cleaning properties and low sensitivity to water hardness (Ca-H- and Mg-H- ions) are the alkylated a-sulfocarboxylates, containing about 10 to about 23 carbon atoms, and having the formula:
  • R is C to C alkyl
  • M is a water-soluble cation as hereinbefore disclosed, preferably sodium ion
  • R' is either short chain length alkyl, e.g., methyl, ethyl, propyl, and butyl or medium chain length alkyl, e.g., hexyl, heptyl, octyl, and nonyl.
  • the total number of carbon atoms should ideally be in the range 18-20 for optimum performance.
  • These compounds are prepared by the esterification of a-sulfonated carboxylic acids, which are commercially available, using standard techniques. Specific examples of the alkylated a-sulfocarboxylates preferred for use herein include:
  • lithium methyl-a-sulfolaurate as well as mixtures thereof.
  • a preferred class of anionic organic detergents are the ,B-alkyloxy alkane sulfonates. These compounds have the following formula:
  • R is a straight chain alkyl group having from 6 to 20 carbon atoms
  • R is a lower alkyl group having from 1 (preferred) to 3 carbon atoms
  • M is a watersoluble cation as hereinbefore described.
  • anionic surfactants are the water-soluble salts of the organic, sulfuric acid reaction products of the general formula wherein R is chosen from the group consisting of a straight or branched chain, saturated aliphatic hydrocarbon radical having from 8 to 24, preferably 12 to 18, carbon atoms; and M is a cation.
  • R is chosen from the group consisting of a straight or branched chain, saturated aliphatic hydrocarbon radical having from 8 to 24, preferably 12 to 18, carbon atoms; and M is a cation.
  • the salts of an organic sulfuric acid reaction prodnot of a hydrocarbon of the methane series including iso-, neo-, meso-, and n-paraffins, having 8 to 24 carbon atoms, preferably 12 to 18 carbon atoms and a sulfonating agent e.g. S H 80 oleum, obtained according to known sulfonation methods, including bleaching and hydrolysis.
  • Preferred are alkali metal and ammonium s
  • alkyl ether sulfates Other synthetic anionic detergents useful herein are alkyl ether sulfates. These materials have the formula RO(C H O) SO M wherein R is alkyl or alkenyl of about to about 20 carbon atoms, x is 1 to 30, and M is a water-soluble cation as defined hereinbefore.
  • the alkyl ether sulfates useful in the present invention are condensation products of ethylene oxide and monohydric alcohols having about 10 to about 20 carbon atoms. Preferably, R has 14 to 18 carbon atoms.
  • the alcohols can be derived from fats, e.g., coconut oil or tallow, or can be synthetic. Lauryl alcohol and straight chain alcohols derived from tallow are preferred herein.
  • Such alcohols are reacted with 1 to 30, and especially 6, molar proportions of ethylene oxide and the resulting mixture of molecular species, having, for example, an average of 6 moles of ethylene oxide per mole of alcohol, is sulfated and neutralized.
  • alkyl ether sulfates of the present invention are sodium coconut alkyl triethylene glycol ether sulfate; lithium tallow alkyl triethylene glycol ether sulfate; and sodium tallow alky hexaoxyethylene sulfate.
  • Highly preferred alkyl ether sulphates are those comprising a mixture of individual compounds, said mixture having an average alkyl chain length of from about 12 to 16 carbon atoms and an average degree of ethoxylation of from about 1 to 4 moles of ethylene oxide.
  • Such a mixture also comprises from about 0 to 20% by weight C1243 compounds; from 60 to 100% by weight of CIMHG compounds; from about 0 to 20% by weight of C compounds; from about 3 to 30% by weight of compounds having a degree of ethoxylation of 0; from about 45 to by weight of compounds having a degree of ethoxylation of from 1 to 4; from about 10 to 25% by weight of compounds having a degree of ethoxylation of from 4 to 8; and from about 0.1 to 15% by weight of compounds having a degree of ethoxylation greater than 8.
  • anionic synthetic detergents which come within the terms of the present invention are the reaction product of fatty acids esterified with isethionic acid and neutralized with sodium hydroxide where, for example, the fatty acids are derived from coconut oil; sodium or potassium salts of fatty acid amides of methyl tauride in which the fatty acids, for example, are derived from coconut oil.
  • Other anionic synthetic detergents of this variety are set forth in U.S. Pat. Nos. 2,486,921; 2,486,922; and 2,396,278.
  • anionic synthetic detergents which come within the terms of the present invention, are the compounds which contain two anionic functional groups. These are referred to as di-anionic detergents.
  • Suitable dianionic detergents are the disulfonates, disulfates, or mixtures thereof which may be represented by the following formulae:
  • R is an acyclic aliphatic hydrocarbyl group having 15 to 20 carbon atoms and M is a water-solubilizing cation, for example, the C to C disodium 1,2-alkyldisulfates, C to C dipotassium-l ,2-alkyldisulfonates or disulfates, disodium 1,9-hexadecyl disulfates, C to C disodium-1,2-alkyldisulfonates, disodium 1,9- stearyldisulfates and 6,10-octadecyldisulfates.
  • the aliphatic portion of the disulfates or disulfonates is generally substantially linear, thereby imparting desirable biodegradable properties to the detergent compound.
  • the water-solubilizing cations include the customary cations known in the detergent art, i.e., the alkali metals, and the ammonium cations, as well as other metals in group 11A, 11B, IIIA, IVA and IVB of the Periodic Table except for boron.
  • the preferred water-solubilizing cations are sodium or potassium. These dianionic detergents are more fully described in British Pat. No. 1,151,392 which is hereby incorporated by reference.
  • Still other anionic synthetic detergents include the class designated as succinamates.
  • This class includes such surface active agents as disodium N-octadecylsulfosuccinamate; tetrasodium N-(1,2-dicarboxyethyl)-N- octadecylsulfo-succinamate; diamyl ester of sodium sulfosuccinic acid; dihexyl ester of sodium sulfosuccinic acid; dioctyl esters of sodium sulfosuccinic acid.
  • olefin sulfonates having about 12 to about 24 carbon atoms.
  • olefin sulfonates is used herein to mean compounds which can be produced by the sulfonation of a-olefins by means of uncomplexed sulfur trioxide, followed by neutralization of the acid reaction mixture in conditions such that any sultones which have been formed in the reaction are hydrolyzed to give the corresponding hydroxy-alkanesulfonates.
  • the sulfur trioxide can be liquid or gaseous, and is usually,
  • inert diluents for example by liquid S chlorinated hydrocarbons, etc., when used in the liquid form, or by air, nitrogen, gaseous S0 etc., when used in the gaseous form.
  • the a-olefins from which the olefin sulfonates are derived are mono-olefins having 12 to 24 carbon atoms, preferably 14 to 16 carbon atoms. Preferably, they are straight chain olefins.
  • suitable l-olefins include l-dodecene; l-tetradecene; l-hexadecene; l-octadecene; l-eicosene and l-tetracosene.
  • the olefin sulfonates can contain minor amounts of other materials, such as alkene disulfonates depending upon the reaction conditions, proportion of reactants, the nature of the starting olefins and impurities in the olefin stock and side reactions during the sulfonation process.
  • Runs 35-40 inclusive demonstrate the effect of various anionic cosurfactants on the performance of the C ethoxylated zwitterionic compound, both with and without builder at a level of 125 ppm each (i.e. a 1:1 ratio) of the C compound and cosurfactant. It can be seen that for ethoxylated zwitterionic compounds having mediocre particulate soil removal performance addition of anionic cosurfactants provides a benefit but that incorporation of builder gives little further improvement.
  • Runs 15-32 and 41-88 demonstrate the effect of various anionic cosurfactants on the performance of the C ethoxylated zwitterionic compound in the presence and absence of builder. Runs 15-32 show that, at 125 ppm each of C compound and anionic cosurfactant in the absence of builder, particulate soil removal performance of the ethoxylated zwitterionic compound is depressed.
  • Runs 59-88 provide further evidence of the extent to which anionic surfactants inhibit the particulate soil removal performance of the ethoxylated zwitterionic compounds of the present invention.
  • a reduction in performance is still apparent at a ratio of ethoxylated zwitterionic to anionic cosurfactant of 4:1, the exception again being sodium stearate, but is much less noticeable at a ratio of 9:1, the addition of builder providing a benefit in each instance.
  • At an ethoxylated zwitterionic compound level of 300 ppm in solution and with 25 ppm cosurfactant (12:1 ratio) substantially no diminution in particulate soil removal performance is seen.
  • the results show the sequential dissolution of first the ethoxylated zwitterionic and then the anionic cosurfactant serves to minimize the adverse effect of the latter on the clay removal performance of the former.
  • Such sequential dissolution can be achieved by any one of a number of known methods, e.g., by coating, granulation, or agglomeration of the anionic with other conventional detergent components such as C fatty acids, c1248 fatty acid amides and alkanol amides, high molecular weight (i.e. MWt 1000) polyethylene glycols, hydratable inorganic builder salts such as alkali metal polyphosphates, and porous siliceous materials such as those sold under the Trade Name Zeosyl by J. M.
  • the diluent component is incorporated at a level of 5 to 50%, preferably 10 to 25%, by weight of the mixture of anionic surfactant plus diluent so as to effect a delay of at least 60 seconds in the complete dissolution or dispersion of the mixture in an aqueous medium at F.
  • microencapsulation using, e.g., hydrolysed gelatin, agar, or polyvinyl alcohol wall materials can be employed where low levels of anionic material are desired.
  • Techniques for microen'capsulating materials, including detergent components, are well known in the art. A typical disclosure of such techniques is given in Kirk-Othmer Encyclopedia of Chemical Technology, 2nd edition, 13, pp. 436-456, published in 1967 by John Wiley & Sons, Inc. This disclosure is incorporated adding builder to the system, which shows a benefit for 55 herein by reference.
  • the detergent compositions a 60 may also contain other ingredients conventionally employed in such products.
  • Suitable inorganic builders include the alkali metal Similarly, compounds having the structure polyphosphates (including the pyrophosphates and

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US493953A 1974-08-01 1974-08-01 Detergent composition having enhanced particulate soil removal performance Expired - Lifetime US3929678A (en)

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DE2437090A DE2437090A1 (de) 1974-08-01 1974-08-01 Reinigungsmittel
US493953A US3929678A (en) 1974-08-01 1974-08-01 Detergent composition having enhanced particulate soil removal performance
CA231,524A CA1059867A (en) 1974-08-01 1975-07-15 Detergent composition having enhanced particulate soil removal performance
NL7508895A NL7508895A (nl) 1974-08-01 1975-07-25 Reinigingsmiddelen.
DE2533758A DE2533758C2 (de) 1974-08-01 1975-07-29 Waschmittel
AU83477/75A AU501799B2 (en) 1974-08-01 1975-07-29 Detergent composition
NL7509077A NL7509077A (nl) 1974-08-01 1975-07-30 Werkwijze voor het bereiden van een wasmiddel met sterke, fijnverdeeld vuilverwijderende werking.
LU73103A LU73103A1 (xx) 1974-08-01 1975-07-30
GB32084/75A GB1507083A (en) 1974-08-01 1975-07-31 Detergent composition having enhanced particulate soil removal performance
IT2598175A IT1040279B (it) 1974-08-01 1975-07-31 Composizione detergente dotata di maggiore capacita di rimozione di sporco a carattere parti cellare
FR7523931A FR2280706A1 (fr) 1974-08-01 1975-07-31 Concentres d'agents de nettoyage
BE158838A BE831995A (fr) 1974-08-01 1975-07-31 Composition detergente ayant des performances ameliorees d'enlevement de salissures particulaires
FR7524026A FR2280705A1 (fr) 1974-08-01 1975-07-31 Composition detergente ayant des performances ameliorees d'enlevement de salissures particulaires
BE158875A BE832048A (fr) 1974-08-01 1975-08-01 Concentres d'agents de nettoyage

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DE2437090A1 (de) 1976-02-19
FR2280705B1 (xx) 1978-10-13
GB1507083A (en) 1978-04-12
DE2533758A1 (de) 1976-02-12
DE2533758C2 (de) 1984-03-01
LU73103A1 (xx) 1977-03-24
BE832048A (fr) 1976-02-02
FR2280706A1 (fr) 1976-02-27
NL7508895A (nl) 1976-02-03
BE831995A (fr) 1976-02-02
NL7509077A (nl) 1976-02-03
FR2280705A1 (fr) 1976-02-27
FR2280706B1 (xx) 1978-12-08

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