US3609090A - Built detergent compositions containing hydroxy ether sulfonates - Google Patents

Built detergent compositions containing hydroxy ether sulfonates Download PDF

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US3609090A
US3609090A US780172A US3609090DA US3609090A US 3609090 A US3609090 A US 3609090A US 780172 A US780172 A US 780172A US 3609090D A US3609090D A US 3609090DA US 3609090 A US3609090 A US 3609090A
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hydroxy
sulfonate
sodium
detergent
composition
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Bjorn Sundby
Harold Eugene Wixon
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Colgate Palmolive Co
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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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J8/00—Chemical or physical processes in general, conducted in the presence of fluids and solid particles; Apparatus for such processes
    • B01J8/0015—Feeding of the particles in the reactor; Evacuation of the particles out of the reactor
    • B01J8/003—Feeding of the particles in the reactor; Evacuation of the particles out of the reactor in a downward flow
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
    • C07C309/01—Sulfonic acids
    • C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
    • C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
    • C07C309/09—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton
    • C07C309/10—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing etherified hydroxy groups bound to the carbon skeleton with the oxygen atom of at least one of the etherified hydroxy groups further bound to an acyclic carbon atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/64—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton
    • C07C323/66—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and sulfur atoms, not being part of thio groups, bound to the same carbon skeleton containing sulfur atoms of sulfo, esterified sulfo or halosulfonyl groups, bound to the carbon skeleton
    • 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
    • C11D1/002—Surface-active compounds containing sulfur
    • 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

Definitions

  • R. is a straight or branched higher alkyl group of Ct; to C and preferably Cw to C (2) R is a straight or branched alkyl of C to C and preferably C to C6;
  • R3 to R1 are, independently, hydrogen or straight or branched alkyl of C to C and preferably hydrogen or lower alkyl of C to C (4) Z is oxygen (O) or sulfur (S);
  • M is a cation such as hydrogen, alkali metal, ammonium, substituted ammonium or amine and preferably a water-solubilizing, salt-forming group.
  • the hydroxy oxa (or thia) s u lfonates of the detergent composition provide both detergency and fabric softening characteristics and are hereinafter referred to generally as hydroxy ether sulfonates.
  • the present invention is directed to novel detergent compositions, and more particularly, to novel detergent compositions based upon hydroxy ether sulfonates and water-soluble alkaline detergency builder salts.
  • anionic detergents based upon linear alkyl benzene sulfonates or alkyl aryl sulfonates in general possess the undesirable characteristics of phase incompatibility with various water-soluble alkaline detergent builders in aqueous systems.
  • the anionic detergents are incompatible with various phosphate builders generally employed in detergent compositions thereby eliminating the all purpose functionality of the detergents. Accordingly, a clear single-phase liquid detergent composition cannot be prepared from the conventional phosphate builders and the linear alkyl benzene sulfonate detergents since a separation of phases usually results.
  • detergent compositions comprising certain hydroxy ether sulfonates in conjunction with water-soluble alkaline detergency builder salts possess all of the characteristics desired.
  • the active hydroxy ether sulfonate possesses not only exceptional detergency characteristics, but also possesses fabricsoftening characteristics and is completely compatible with conventional water-soluble alkaline detergency builder salts.
  • the combination of the present invention comprising the hydroxy ether sulfonates and the conventional water-soluble alkaline detergency builder salts can be produced both as a homogeneous single-phase liquid detergent composition or can be conveniently prepared in the form of bars, flakes, granular r tableted granular compositions.
  • a further object of the present invention is to provide novel detergency compositions wherein the detergent component thereof possesses, in addition to detergency characteristics, fabric-softening characteristics, and is completely compatible with conventional water-soluble alkaline detergency builder salts.
  • a still further object of the present invention is to provide a novel detergent composition comprising certain detergents and fabric-softening hydroxy ether sulfonates in combination with water-soluble alkaline detergency builder salts. 5 Still further objects and advantages of the novel detergent composition of the present invention will become more apparent from the following more detailed description thereof.
  • hydroxy ether sulfonates possess the unusual characteristics of excellent detergency and fabric-softening ability in addition to complete compatibility with water-soluble alkaline detergency builder saltsconventionally employed in detergent compositions. Accordingly, the present invention is directed to such detergent compositions based upon hydroxy ether sulfonates and water-soluble alkaline detergency builder salts.
  • R is straight or branched higher alkyl group of C to C and preferably C, to C 2.
  • R is a straight or branched alkyl of C to C and preferably C to C 3.
  • R to R- are, independently, hydrogen or straight or branched alkyl of C, to C,,,, and preferably hydrogen or lower alkyl of C, to C 4.
  • Z is oxygen (O) or sulfur (S);
  • M is a cation such as hydrogen alkali metal, ammonium,
  • substituted ammonium or amine and preferably a watersolubilizing, salt-forming group.
  • sodium salts of the hydroxy ether sulfonates of the present invention are preferred, it is, of course, possible to advantageously employ any water-solubilizing cation e.g. other alkali metals such as potassium or lithium.
  • ammonium and amine salts e.g., trialkanolamine salts such as triethanolamine can be advantageously employed with exceptional results.
  • the novel hydroxy ether sulfonates of the present invention are prepared by reacting an epoxy alkane with an unsaturated aliphatic alcohol with subsequent sulfonation of the reaction product.
  • the epoxy alkane reactants that are useful in the preparation of the hydroxy ether sulfonates of the present invention can be any epoxy alkane having a terminal group i.e., an epoxy alkane having the structure:
  • n-octyl iso-octyl n-nonyl iso-nonyl n-decyl n-dodecyl tert-dodecyl 2-propylheptyl S-ethylnonyl 2-butyloctyl n-undecyl n-tridecyl n-tetradecyl n-pentadecyl tert-octadecyl 2,6,8 -trimethylnonyl 7 -ethyl-2 -methy]-4 -undecyl n-hexadecyl n-octadecyl eicosyl docosyl tricosyl pentacosyl triacontyl etc.
  • the alkyl radicals may also include unsaturated alkyl radicals such as hexaryl, oleoyl, dodecenyl, hexadecenyl, and the like.
  • Illustrative examples of the epoxy alkanes which can be employed as reactants in the process of the present invention to produce the novel hydroxy ether sulfonates of the present invention include:
  • Exemplary hydroxy ether sulfonates in accordance with the present invention include:
  • ll-methyl-6-oxahexadecyl sodium sulfonate 8-hydroxy-7-isopropyl l l-methyl-9,9-dimethyl-6-oxahexadecyl sodium sulfonate 8-hydroxy-7-isopropyl, ll-methyl-fi-oxadocosyl potassium sulfonate 8-hydroxy-7-isopropyl, l l-methyl-6-oxahexadecyl ammonium sulfonate l-hydroxy-9-t-butyl-8-oxahexadecyl sodium sulfonate l0-hydroxy-9-t-butyl-7,7-dimethyl-8-oxahexadecyl sodium sulfonate lO-hydroxy-9-t-butyl 8-oxahe
  • water-soluble inorganic detergency builder salts are alkali metal carbonates, phosphates, polyphosphates, sulfates, and silicates, etc.
  • Specific examples of such salts are sodium, potassium and lithium tripolyphosphates, carbonates, pyrophosphates, orthophosphates and hexamethaphosphates, sodium, potassium and lithium sulfates and sodium, potassium O and lithium silicates.
  • organic alkaline detergency builder salts are (l) alkali metal aminopolycarboxylates ⁇ e.g., sodium and potassium ethylenediaminetetraacetates, N-(Z- hydroxyethyl)-ethyl-enediarninetriacetates, nitrilo triacetates, and N-(2-hydroxyethyl)-nitriol diacetates]; (2) alkali metal salts of phytic acid (e.g., sodium and potassium phytates-see US Pat. No.
  • alkali metal aminopolycarboxylates ⁇ e.g., sodium and potassium ethylenediaminetetraacetates, N-(Z- hydroxyethyl)-ethyl-enediarninetriacetates, nitrilo triacetates, and N-(2-hydroxyethyl)-nitriol diacetates
  • alkali metal salts of phytic acid e.g.
  • water-soluble salts of ethane-lhydroxyl l-diphosphonate e.g., the trisodium and tripotassium salts-see U.S. Pat. No. 3,159,581
  • water-soluble salts of methylene diphosphonic acid e.g., trisodium and tripotassium methylene diphosphonate and the other salts described in U.S. Pat. No.
  • water-soluble salts of substituted methylene diphosphonic acids e.g., trisodium and tripotassium ethylidene, isopropylidene, benxylmethylidene, and halomethylidene diphosphonates
  • water-soluble salts of polycarboxylate polymers and copolymers e.g., homopolymers of itaconic acid, aconitic acid; maleic acid; mesaconic acid; fumaric acid; methylene malonic acid; and citronic acid and copolymers thereof with other compatible copolymerizable monomers such as ethylene; and mixtures thereof.
  • the active hydroxy ether sulfonate is generally employed in an amount of from about 1 to about percent by weight of the total composition, while the water-soluble detergency builder salts comprise from about ID to about 99 percent by weight of the total composition.
  • the hydroxy ether sulfonate Comprises about 5 -50 percent by weight while the detergent builders comprise from 15-90 percent of the total composition.
  • the ratio of the water-soluble detergency builder salts to the total detergent is in the range of 1:3 to 20:1.
  • compositions of this invention may be formulated as liquids, solids, pastes, gels, etc.
  • the compositions are unexpectedly, characterized by unique clarity and homogeneity i.e. the compositions are single-phase systems.
  • the detergent compositions of this invention can contain any of the usual compatible adjuvants, diluents and additives including other detergents, for example, anionic nonionic, ampholytic, cationic or zwitterionic detergents; perfumes, antitarnishing agents, antiredeposition agents, bacteriostatic agents, dyes, fluorescers, suds builders, suds depressors, and
  • Suitable anionic surface active agents include those surfaceactive or detergent compounds which contain an organic hydrophobic group and an anionic solubilizing group. Typical examples of anionic solubilizing groups are sulfonate, sulfate, carboxyiate, phosphonate and phosphate. Examples of suitable anionic detergents which fall within the scope of the invention include the soaps, such as the water-soluble salts of higher fatty acids or rosin acids, such as may be derived from fats, oils and waxes of animal, vegetable or marine origin, e.g. the sodium soaps of tallow, grease, coconut oil, tall oil and mixtures thereof; and the sulfated and sulfonated synthetic detergents, particularly those having about eight to 26, and preferably about 12-22, carbon atoms to the molecule.
  • soaps such as the water-soluble salts of higher fatty acids or rosin acids, such as may be derived from fats, oils and waxes of animal, vegetable or marine origin, e.g. the sodium soap
  • suitable synthetic anionic detergents there may be cited the higher alkyl mononuclear aromatic sulfonates such as the higher alkyl benzene sulfonates containing from to 16 carbon atoms in the alkyl group in a straight or branched chain, e.g., the sodium salts of higher alkyl benzene sulfonates or of the higher alkyl toluene, xylene and phenol sulfonates; alkyl naphthalene sulfonate, ammonium diamyl naphthalene sulfonate, and sodium dinonyl naphthalene sulfonate.
  • the higher alkyl mononuclear aromatic sulfonates such as the higher alkyl benzene sulfonates containing from to 16 carbon atoms in the alkyl group in a straight or branched chain, e.g., the sodium salts of higher alkyl
  • one preferred type of composition there is used a linear alkyl benzene sulfonate having a high content of 3- (or higher) phenyl isomers and a correspondingly low content (well below 50 percent of 2- (or lower) phenyl isomers; in other terminology, the benzene ring is preferably attached in large part at the 3 or higher (e.g. 4, 5, 6 or 7) position of the alkyl group and the content of isomers in which the benzene ring is attached at the 2 or 1 position is correspondingly low.
  • Particularly preferred materials are set forth in US. Pat. No. 3,320,174, May 16, 1967, OH. Rubinfeld.
  • mixtures containing linear alkylbenzene sulfonates and the detergent compounds of this invention have unexpectedly good properties, particularly with respect to softening power. These mixtures are the invention of Harold Wixon.
  • anionic detergents are the olefin sulfonates, including long-chain alkene sulfonates, long-chain hydroxy-alkane sulfonates or mixtures of alkenesulfonates and hydroxyalkanesulfonates.
  • paraffin sulfonates such as the reaction products of alpha olefins and bisulfites (e.g. sodium bisulfite), e.g., primary paraffin sulfonates of about 10-20, preferably about 15-20, carbon atoms; sulfates or higher alcohols; salts of a-sulfofatty esters (e.g. of about 10-20 carbon atoms, such as methyl orsulfomyristate or a-sulfotallowate).
  • alpha olefins and bisulfites e.g. sodium bisulfite
  • a-sulfofatty esters e.g. of about 10-20 carbon atoms, such as methyl orsulfomyristate or a-sulfotallowate.
  • sulfates of higher alcohols are sodium lauryl sulfate, sodium tallow alcohol sulfate, Turkey Red Oil or other sulfated oils, or sulfates of monoor di-glycerides of fatty acids (e.g.
  • alkyl poly (ethenoxy) ether sulfates such as the sulfates of the condensation products of ethylene oxide and lauryl alcohol (usually having one to five ethenoxy groups per molecule); lauryl or other higher alkyl glyceryl ether sulfonates; aromatic poly (ethenoxy) ether sulfates such as the sulfates of the condensation products of ethylene oxide and nonyl phenol (usually having one to six oxyethylene groups per molecule).
  • the suitable anionic detergents include also the acyl sarcosinates (e.g. sodium lauroylsarcosinate) the acyl esters (e.g. oleic acid ester) of isethionates, and the acyl N-methyl taurides (e.g. potassium N-methyl lauroylor oleyl tauride).
  • acyl sarcosinates e.g. sodium lauroylsarcosinate
  • the acyl esters e.g. oleic acid ester
  • acyl N-methyl taurides e.g. potassium N-methyl lauroylor oleyl tauride
  • the most highly preferred water soluble anionic detergent compounds are the ammonium and substituted ammonium (such as mono-, diand triethanolamine), alkali metal (such as sodium and potassium) and alkaline earth metal (such as calcium and magnesium) salts or the higher alkyl benzene sulfonates, olefin sulfonates, the higher alkyl sulfates, and the higher fatty acid monoglyceride sulfates.
  • the particular salt will be suitably selected depending upon the particular formulation and the proportions therein.
  • Nonionic surface active agents include those surface active or detergent compounds which contain an organic hydrophobic group and a hydrophilic group which is a reaction product of solubilizing group such as carboxylate, hydroxyl, amide or amino with ethylene oxide or with the polyhydration product thereof, polyethylene glycol.
  • nonionic surface active agents which may be used there may be noted the condensation products of alkyl phenols with ethylene oxide, e.g., the reaction product of isooctyl phenol with about six to 30 ethylene oxide units; condensation products of alkyl thiophenols with Wm 15 ethylene oxide units; condensation products of higher fatty alcohols such as tridecyl alcohol with ethylene oxide; ethylene oxide addends of monoesters of hexahydric alcohols and inner ethers thereof such as sorbitan monolaurate, sorbitol monooleate and mannital monopalmitate, and the condensation products of polypropylene glycol with ethylene oxide.
  • Other nonionics include amine oxides, e.g. lauryl dimethyl amine oxide; sulfoxides and the like.
  • Cationic surface-active agents may also be employed. Such agents are those surface active detergent compounds which contain an organic hydrophobic group and a cationic solubilizing group. Typical cationic solubilizing groups are amine and quaternary groups.
  • suitable synthetic cationic detergents there may be noted the diamines such as those of the type RNHC PLHN wherein R is an alkyl group of about 12 to 22 carbon atoms, such as N-2-aminoethyl stearyl amine and N-2- aminoethyl myristyl amine; amide-linked amines such as those of the type RCONl-IC I-LNH wherein R is an alkyl group of about nine to 20 carbon atoms, such as N-Z-amino ethylstearyl amide and N-amino ethyl myristyl amide; quaternary ammonium compounds wherein typically one of the groups linked to the nitrogen atom is an alkyl group of about 12 to 18 carbon atoms and three of the groups linked to the nitrogen atom are alkyl groups which contain one to three carbon atoms, including such one to three carbon alkyl groups bearing inert substituents, such as phenyl groups, and there is
  • Typical quaternary ammonium detergents are ethyl-dimethyl-stearyl ammonium chloride, benzyl-dimethyl-stearyl ammonium chloride, benxyl-dirnethyl-stearyl ammonium chloride, trimethyl stearyl ammonium chloride, trimethyl-cetyl ammonium bromide, dimethyl-ethyl dilauryl ammonium chloride, dimethyl-propylmyristyl ammonium chloride, and the corresponding methosulfates and acetates.
  • amphoteric detergents are those containing both an anionic and a cationic group and a hydrophobic organic group, which is advantageously a higher aliphatic radical, e.g. of 10-20 carbon atoms.
  • suitable amphoteric detergents are those containing both an anionic and a cationic group and a hydrophobic organic group, which is advantageously a higher aliphatic radical, e.g. of 10-20 carbon atoms.
  • N- long chain alkyl aminocarboxylic acids e.g. of the formula the N-long chain alkyl iminodicarboxylic acids (e.g. of the formula RN(RCOOM)
  • the N-long chain alkyl betaines e.g. ofthe formula where R is a long chain alkyl group, eg of about 10-20 carbons, R is a divalent radical joining the amino and carboxyl portions of an amino acid (e.g.
  • M is hydrogen or a salt-forming metal
  • R is a hydrogen or another monovalent substituent (e.g. methyl or other lower allryl)
  • R and R are monovalent substituents joined to the nitrogen by carbon-to-nitrogen bonds (e.g. methyl or other lower alkyl substituents).
  • amphoteric detergents are N-alkyl-beta-aminopropionic acid; N-alkyl-beta-iminodipropionic acid, and N-alkyl, N,N- dimethyi glycine; the alkyl group may be, for example, that derived from coco fatty alcohol, lauryl alcohol, rnyristyl alcohol (or a lauryl-myristyl mixture), hydrogenated tallow alcohol, cetyl, stearyl, or blends of such alcohols.
  • the substituted aminopropionic and iminodipropionic acids are often supplied in the sodium or other salt forms, which may likewise be used in the practice of this invention.
  • amphoteric detergents examples include the fatty imidazolines such as those made by reacting a long-chain fatty acid (e.g. of 10 to 20 carbon atoms) with diethylene triamine and monohalocarboxylic acids having two to six carbon atoms, e.g. l-coco-5-hydroxethyl-5-carboxylmethylimidazoline; betaines containing a sulfonic groups instead of the carboxylic group; betaines in which the longchain substituent is joined to the carboxylic group without an intervening nitrogen atom, e.g. inner salts of 2- trimethylamino fatty acids such as 2-trimethylaminolauric acid, and compounds of any of the previously mentioned types but in which the nitrogen atom is replaced by phosphorus.
  • a long-chain fatty acid e.g. of 10 to 20 carbon atoms
  • diethylene triamine and monohalocarboxylic acids having two to six carbon atoms, e.g. l-
  • the detergent compositions of the present invention are excellent compositions for all types of cleaning operations, they are extremely effective for the cleaning of textiles in a conventional laundry or washing machine.
  • the detergent compositions of the present invention can be effectively used for laundering fabrics in water having a temperature from about 60 F. to about 212 F., the detergent composition of the present invention exhibiting unusually effective detergency and fabric softening characteristics in both cold and hot water.
  • the step of the present invention is followed by rinsing and drying of the fabric.
  • the detergent composition concentration in the wash solution should range from about 0.05 percent to about 0.5 percent by total weight, and the detergent composition should be added so as to provide an effective detergent and softening amount of the hydroxy ether sulfonate component of at least 0.002 percent.
  • the addition of the fabrics and the detergent composition can be conducted in any suitable conventional manner.
  • the fabrics can be added to the container or washer either before or after the washing solution is added.
  • the fabrics are then agitated in the detergent solution for varied periods of time, a wash cycle of from 8 to 15 minutes being generally used in the washing cycle of an automatic agitator type washer.
  • the detergent composition is drained off and the fabrics are rinsed in substantially pure water.
  • the fabrics can be rinsed as many times as desired. After rinsing of the fabrics, they are dried, first by spinning, and then by contact with the air as in a conventional hanging of the fabrics on a clothesline or in an automatic dryer type system.
  • the organic detergent and fabric-softening component as well as the builders and any minor ingredients are incorporated into the composition prior to its conversion into the final product form e.g. detergent granuied, flakes, bar etc.
  • the individual components of the novel detergent composition of the present invention can be added in the form of particles or directly as a liquid to produce a liquid detergent composition.
  • a particularly preferred detergent composition of the present invention comprises the hydroxy ether sulfonate detergent and softener component in combination with sodium xylene sulfonate and potassium pyrophosphate in a clear, aqueous single-phase liquid form.
  • the water generally comprises from about 30 to about 70 percent of the total composition while the hydroxy ether sulfonate comprises from about 5 to 15 percent by weight; the sodium xylene sulfonate from 5 to 15 percent by weight and the potassium pyrophosphate or similar alkaline detergency builder salt from about 10 to 30 percent by weight.
  • a composition adapted for the washing of fine fabrics can comprise the hydroxy ether sulfonates with or without sodium xylene sulfonate in an aqueous, single phase system.
  • a composition comprising 15 percent by weight of 6- hydroxy-4-oxaeicosyl sodium sulfonate, 35 percent sodium tripolyphosphate, and 50 percent sodium sulfate is prepared by mixing respectively 3.75 grams, 8.75 grams, and 12.50 grams of the individual components. 25 grams of a powdered composition is prepared.
  • This powdered composition comprising the hydroxy ether sulfonate, sodium tripolyphosphate and sodium sulfate is added to grams of water thereby preparing a total of 200 grams of solution.
  • This solution is a clear single phase liquid at room temperature.
  • a further detergent composition in accordance with the present invention is prepared from the following components.
  • EXAMPLE ll The detergency of the compositions of the present invention compared with a conventional detergent composition is tested in a Spangler Soil (Sebum) detergency test in a tergotometer having normal reciprocating agitation.
  • the test conditions employ three soiled swatches of fabric with 1000 milliliters of detergent solution, the detergent concentration being 0.15 perequivalent amount of linear dodecyl benzene sulfonate, a conventional anionic detergent, in lieu of the 6-hydroxy-4-oxaeicosyl sulfonate, sodium salt of the present invention.
  • the anionic detergent cent in all cases. 5 with the water-soluble alkaline detergency builder salts, the
  • tion are prepared as in example i above by the mere addition EXAMPLE W of the three active components to an aqueous system, the compatibility of the components providing a clear single phase
  • the follqwins are typical detergent compositions in liquid detergent composition.
  • a dual-phase system is prepared cordance the P inventionin order to provide a liquid detergent composition comprising SOLID a linear tridecyl benzene sulfonate as the active detergent a component since, such anionic detergent is found to be incompatible with the alkaline detergency builder salts and thus a clear single phase solution can not be prepared.
  • control system is prepared by providing ggggzg 'ti z iz'f separate aqueous solutions of l) the linear tridecyl benzene Sodium fi z 08p a e 318 Fluumsccm sulfonate, xylene and water, and (2) sodium tripolyphosphate, dye 0.18 sodium xylene sulfonate, and water.
  • Table 1 The results of the detergent tests are shown in table 1 below:
  • the hydroxy ether sul- SOLID fonates of the present invention exhibit unusually good detergency in both hard and soft water under both hot and cold conditions. Accordingly, the compatible hydroxy ether sulmp n Percent fonate detergents and fabric softeners employed in the detergent compositions of the present invention not only possess v mxy -4- ducosyl sodium sulfonate 1 the desirable detergency and fabric-softening characteristics ll gg 3g 8 as well as the compatibility with water soluble alkaline detersodium silica, (Namsim: [.235] gency builder salts, but, in addition, possess detergency Brightener M characteristics substantially equal to or better than a conven- 2:12; tional anionic detergent. 1O
  • EXAMPLE Ill SOLID A novel detergent composition of the present invention is tested for softening ability against a conventional anionic build detergent system.
  • the composition of the present inven- .60 Perm" tion employed in the softening test is as follows:
  • the composition is prepared as in example 1 by blending the individual components and heating until a clear single SOLID phase liquid composition is formed. The clarity and homogeneity of the systems are maintained upon cooling to room temperature.
  • the single-phase liquid composition has a Component Percent specific gravity of 1.19, a'pH of 9.9, and a viscosity of 20 cps.
  • R is a straight or branched higher alltyl group of C to 2.
  • R is a straight or branded alkylene of C to C 3R to R are, independently, hydrogen.
  • Z is oxygen or sulfur;
  • M is a water-solubilizing salt-forming cation
  • B a water soluble detergency builder salt the ratio of (A) to (B) ranging from 3:l to I120.
  • composition of claim 1 wherein the hydroxy ether sulfonate is 6-hydroxy-4-oxaeicosyl sodium sulfonate.
  • composition of claim I wherein the builder is potassium pyrophosphate.
  • the detergent composition of claim 1 including a hydrotrope.
  • composition of claim 8 wherein the hydrotrope is xylene sulfonate.
  • T ifle composition of dais /E the builder salt is potassium pyrophosphate.
  • composition of claim 10 wherein the hydroxy ether sulfonate is -hydroxy-roxaeicosyl sodium sulfonate.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
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US780172A 1968-11-29 1968-11-29 Built detergent compositions containing hydroxy ether sulfonates Expired - Lifetime US3609090A (en)

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US780172A Expired - Lifetime US3609090A (en) 1968-11-29 1968-11-29 Built detergent compositions containing hydroxy ether sulfonates
US780276A Expired - Lifetime US3627822A (en) 1968-11-29 1968-11-29 Novel compounds with detergency and fabric-softening ability and method of making the same

Family Applications After (1)

Application Number Title Priority Date Filing Date
US780276A Expired - Lifetime US3627822A (en) 1968-11-29 1968-11-29 Novel compounds with detergency and fabric-softening ability and method of making the same

Country Status (10)

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US (2) US3609090A (enrdf_load_stackoverflow)
BE (1) BE742104A (enrdf_load_stackoverflow)
CH (2) CH539009A (enrdf_load_stackoverflow)
DE (1) DE1959103A1 (enrdf_load_stackoverflow)
ES (1) ES373687A1 (enrdf_load_stackoverflow)
FR (1) FR2024489A1 (enrdf_load_stackoverflow)
GB (1) GB1286860A (enrdf_load_stackoverflow)
NL (2) NL6917975A (enrdf_load_stackoverflow)
NO (1) NO132430C (enrdf_load_stackoverflow)
SE (2) SE370070B (enrdf_load_stackoverflow)

Cited By (2)

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US3950276A (en) * 1971-09-01 1976-04-13 Colgate-Palmolive Company Sulfonate detergent compositions
CN112679687A (zh) * 2020-12-24 2021-04-20 华南理工大学 一种羟基磺酸亲水单体及其制备方法应用

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DE2410860A1 (de) * 1974-03-07 1975-09-11 Bayer Ag Dihydroxycarbamate mit sulfonsaeuregruppen
DE2412217A1 (de) * 1974-03-14 1975-10-09 Bayer Ag Polyalkylenoxidhaltige urethanpolyole mit sulfonsaeuregruppe(n)
DE2748722A1 (de) * 1977-03-03 1978-09-07 Texaco Development Corp Verfahren zur herstellung eines aethersulfonats
US4680358A (en) * 1985-11-08 1987-07-14 The B F Goodrich Company Styryl terminated macromolecular monomers of polyethers
US5368755A (en) * 1991-12-18 1994-11-29 Colgate-Palmolive Co. Free-flowing powder fabric softening composition and process for the manufacture of a free-flowing fabric softening composition
US5259964A (en) * 1991-12-18 1993-11-09 Colgate-Palmolive Co. Free-flowing powder fabric softening composition and process for its manufacture
US5529710A (en) * 1992-07-15 1996-06-25 The Procter & Gamble Company Production of detergent granules with excellent white appearance
NZ524610A (en) * 1999-03-12 2004-09-24 Pfizer Prod Inc Composition containing a soluble potassium salt, a sodium alkylsulphonate, a polar surfactant and a carrier, use as a toothpaste, oral rinse, skin detergent, shampoo, hard surface cleaner and a fabric detergent

Citations (4)

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US2427577A (en) * 1945-03-01 1947-09-16 Colgate Palmolive Peet Co Production of ether sulphonates
US3082249A (en) * 1958-05-13 1963-03-19 Monsanto Chemicals Sodium 3-tridecyloxy-2-propanol-1-sulfonate
US3267040A (en) * 1960-08-02 1966-08-16 Lever Brothers Ltd Synergistic combinations of alkane sulfonates and alkoxy hydroxy propane sulfonates
DE1223831B (de) * 1965-05-18 1966-09-01 Basf Ag Verfahren zur Herstellung der Alkali- und Erdalkalisalze von in beta-Stellung durch eine AEthergruppe substituierten Alkansulfonsaeuren

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DE960196C (de) * 1953-07-04 1957-03-21 Boehme Fettchemie G M B H Verfahren zur Herstellung der Salze von Oxyalkansulfonsaeuren
US2913324A (en) * 1955-05-16 1959-11-17 Monsanto Chemicals Sulfoethyl carboxylic acid ester plant growth regulants
US3086043A (en) * 1959-12-21 1963-04-16 Monsanto Chemicals Alkenylsuccinic anhydride monoesters of sulfoalkyl derivatives
US3287420A (en) * 1963-04-26 1966-11-22 Eastman Kodak Co Glycol monovinyl ether
DE1218434B (de) * 1963-08-01 1966-06-08 Henkel & Cie Gmbh Verfahren zur Herstellung von Gemischen oberflaechenaktiver Verbindungen
US3419621A (en) * 1966-06-27 1968-12-31 Wyandotte Chemicals Corp Halogen containing ether compositions

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
US2427577A (en) * 1945-03-01 1947-09-16 Colgate Palmolive Peet Co Production of ether sulphonates
US3082249A (en) * 1958-05-13 1963-03-19 Monsanto Chemicals Sodium 3-tridecyloxy-2-propanol-1-sulfonate
US3267040A (en) * 1960-08-02 1966-08-16 Lever Brothers Ltd Synergistic combinations of alkane sulfonates and alkoxy hydroxy propane sulfonates
DE1223831B (de) * 1965-05-18 1966-09-01 Basf Ag Verfahren zur Herstellung der Alkali- und Erdalkalisalze von in beta-Stellung durch eine AEthergruppe substituierten Alkansulfonsaeuren

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3950276A (en) * 1971-09-01 1976-04-13 Colgate-Palmolive Company Sulfonate detergent compositions
CN112679687A (zh) * 2020-12-24 2021-04-20 华南理工大学 一种羟基磺酸亲水单体及其制备方法应用
CN112679687B (zh) * 2020-12-24 2022-06-21 华南理工大学 一种羟基磺酸亲水单体及其制备方法应用

Also Published As

Publication number Publication date
DE1959103A1 (de) 1970-06-11
CH539009A (de) 1973-07-15
NL6917975A (enrdf_load_stackoverflow) 1970-06-02
US3627822A (en) 1971-12-14
SE371837B (enrdf_load_stackoverflow) 1974-12-02
GB1286860A (en) 1972-08-23
SE370070B (enrdf_load_stackoverflow) 1974-09-30
NL132430C (enrdf_load_stackoverflow)
CH567096A5 (enrdf_load_stackoverflow) 1975-09-30
NO132430C (enrdf_load_stackoverflow) 1975-11-12
BE742104A (enrdf_load_stackoverflow) 1970-05-04
FR2024489A1 (enrdf_load_stackoverflow) 1970-08-28
NO132430B (enrdf_load_stackoverflow) 1975-08-04
ES373687A1 (es) 1972-06-01

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