US3697423A - Wash cycle softener - Google Patents

Wash cycle softener Download PDF

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US3697423A
US3697423A US164827A US3697423DA US3697423A US 3697423 A US3697423 A US 3697423A US 164827 A US164827 A US 164827A US 3697423D A US3697423D A US 3697423DA US 3697423 A US3697423 A US 3697423A
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sodium
amine
water
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mixture
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Bjorn Sundby
Harold Eugene Wixon
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Colgate Palmolive Co
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Colgate Palmolive Co
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
    • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
    • C08G65/32—Polymers modified by chemical after-treatment
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/40—Monoamines or polyamines; Salts thereof
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • 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
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/368—Hydroxyalkylamines; Derivatives thereof, e.g. Kritchevsky bases

Definitions

  • an N-2-hydroxy higher alkyl amine is used as a fabric softener during the washing of the fabric.
  • the amine may be employed in the automatic machine washing of clothes, in which it may be added either during the wash cycle (that is, together with the detergent composition which, as is well known, may comprise an organic detergent, builder salt, etc.) or during the rinse cycle (that is, after the completion of the wash cycle).
  • N-Z-hydroxy higher alkyl amines used in this invention have the formula:
  • R is a monovalent aliphatic hydrocarbon radical of 8 to 24, preferably 10 to 20, carbon atoms
  • R is the radical of an amine of the formula
  • R has an alcoholic hydroxyl group, e.g. it is a hydroxyalkyl radical of the formula --R (OR ),,OH where n is, for example, zero to three, and R and R are alkylene radicals such as ethylene, propylene, isopropylene etc.
  • R and R are alkylene radicals such as ethylene, propylene, isopropylene etc.
  • radicals of this class are and related compounds in which the radicals contain more carbon atoms than in the formula shown above, e.g.
  • radicals of di(isopropanol)amine N-methyl-N-isopropanolamine, N-ethyl-N-ethanolamine, N-ethyl-N-isopropanolamine, N-propyl-N-ethanolamine, N-propyl-N-isopropanolamine, N-methyl-N-hydroxyethoxyethylamine, N-butyl-N-hydroxyethoxyethylamine, N-cyclohexyl-N-hydroxyethoxyethylamine, N-butyl-N-ethanolamine, di(hydroxyethoxyethyl)amine,
  • examples of radicals of this type are the radicals of morpholine, i.e.
  • R is hydrocarbon and R is hydrogen or hydrocarbon; examples of such radicals are
  • R (and R radical may carry a substituent other than the alcoholic hydroxyl previously mentioned; for instance it may be an amino group as in cyclohexyl
  • the ratio of the amount of organic detergent to the amount of hydroxy long chain alkyl amine softener of this invention is in the range of :1 to 1:1, preferably about 2:1 to 1.5 :1.
  • the amine may be preblended with the entire detergent composition or it may be added separarely to. the wash water or it may be preblended with a portion of the detergent composition.
  • One techniqueof incorporating the amine in a granular washing composition is to form an aqueous slurry containing the, organic detergent, the builder salt, the amine and other components (such as agents for preventing soil redeposition, brighteners, bluing agents, bleaching aids, germicidal materials, etc).
  • the slurry may then be converted to solid form by such methods as spray drying and/or hydration of the builder salt to convert the liquid water to water of crystallization.
  • This hydration operation may be effected while bubbles of gas are dispersed in a mass of the mixture so as to lower the density of the final product and to give a crumbly or granular product; the gas bubblesmay result, for example, from the inclusion of hydrogen peroxide to generate oxygen in .the mixture, or from the generation of steam in the mixture (as 'by the exothermic heat of the reaction of sodium trimetaphosphate with NaOH to form sodium tripolyphosphate), or from the dispersing of air in the mixture with violent agitation.
  • the amine when it is a solid, may be mechanically blended, as small particles, with particles of the granular washing composition. Or the amine (e.g.. in molten state or in aqueous dispersion) may be sprayed onto the particles of the granular washing composition, or agglomerated with those particles in other ways.
  • the water-insoluble amine softener may also be incorporated in :aqueous liquid washing compositions.
  • aqueous liquid washing compositions For example it may be dispersed in a built aqueous liquid mixture containing dispersed builder salt, organic detergent and hydrotrope (commonly an alkali metal aromatic sulfonate, such as a benzene-, toluene-, or xylene-sulfonate), together with the other components of the types previously mentioned in the discussion of granular compositions.
  • the amine When the amine is not part of a single washing com-- position it may be added to thewash water as a liquid or solid. Thusit may be dispersed, emulsified or solubilized in alkalineor neutral aqueous medium; the aqueous medium may contain a hydrotrope (which may be the aromatic sulfonate type mentioned above or water miscible alcohol, such as methanol, ethanol, ethylene glycol, diethylene glycol; etc.). An organic detergent, preferably in minor amount, may also be present in the aqueous medium, the low-foaming nonionic detergents being suitable here.
  • a hydrotrope which may be the aromatic sulfonate type mentioned above or water miscible alcohol, such as methanol, ethanol, ethylene glycol, diethylene glycol; etc.
  • An organic detergent preferably in minor amount, may also be present in the aqueous medium, the low-foaming nonionic detergents being suitable here.
  • a particularly suitable mixture contains minor proportions of both a long chain alkyl sulfate detergent and a long chain sulfonate detergent, such as an alkylbenzenesulfonate (e.g. in a ratio of sulfate to sulfonate of about 1:10 to 2:1).
  • the amount of the amine present in the liquid may be, for example, in the range of about 2-25%, preferably about 5-20% (e.g. about 10-20%).
  • the liquid compositions are easily pourable; however, solid gel-like compositions, made with proportions of amine in the above ranges in the presence of aqueous gelling media, may also be used.
  • An-acidic aqueous dispersion of the amine which forms a water soluble salt with the acid present in the water (e.g. acetic, hydrochloric, lactic, glycollic or phosphoric acid), may be used in place of the neutral or alkaline dispersion; when such an acidic composition is mixed with the alkaline agitated wash water the amine is converted to its water-insoluble form, and is finely dispersed in the wash water.
  • Solid amine-containing compositions for inclusions in the wash water may have the amine distributed on a builder salt or other suitable water-soluble or water-diSpersible carrier, preferably one which exerts a beneficial effect on the washing process.
  • the amine in liquid state (e.g. molten) maybe sprayed on, or otherwise agglomerated with, particles of such salts as phosphates (e.g. anhydrous or hydrated pentasodium tripolyphosphate), borax or the so-called pulfed borax (which is an expanded partial hydrate of sodium tetraborate made, for example, by heating borax or sodium tetraborate pentahydrate in heated air), sodium carbonate, sodium bicarbonate, sodium sesquicarbonate, sodium sulfate, sodium chloride or other carrier materials, to form granular or powdered compositions.
  • the amount of amine present in the solid composition may be, for instance, in the range of about 2-25%, preferably about 5-20%.
  • the foregoing liquid or solid compositions may be added to the wash water in amounts such as to provide, for example, about 30 to 400 parts of the amine per million parts of wash water.
  • the organic detergent may be a surface-active agent of the anionic, non-ionic, amphoteric or cationic type, or a mixture of such types.
  • the anionic surface active agents include those surface active or detergent compounds which contain an organic hydrophobic group and an anionic solubilizing group.
  • anionic solubilizing groups are sulfonate, sulfate, carboxylate, phosphonate and phosphate.
  • 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 origin, eg, the sodium soaps of tallow, grease, coconut oil, tall oil and mixtures thereof; and the sulfated and sulfonated synthetic detergents, particularly those having about 8 to 26, and preferably about 12 to 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 origin, eg, the sodium soaps of tallow, grease, coconut oil, tall oil and mixtures thereof
  • sulfated and sulfonated synthetic detergents particularly those having about 8 to 26, and preferably about 12 to 22, carbon atoms to the molecule.
  • suitable synthetic anionic detergents there may be cited the higher alkyl mononuclear aromatic sulfonates such as the higher alkyl benzene sulfonates containing from 10 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 10 to 16 carbon atoms in the alkyl group in a straight or branched chain, e.g., the sodium salts of higher alky
  • 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%) 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 U.S. Pat. 3,320,174, May 16, 1967, of J. Rubinfeld.
  • anionic detergents are the olefin sulfonates, including long chain alkene sulfonates, long chain hydroxyalkane sulfonates or mixtures of alkenesulfonates and hydroxyalkanesulfonates.
  • parafiin 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 of higher alcohols; salts of a-sulfofatty esters (e.g. of about 10- to ZO-carbon atoms, such as methyl a-sulfomyristate or a-sulfotallowate).
  • alpha olefins and bisulfites e.g. sodium bisulfite
  • primary paraffin sulfonates of about 10-20, preferably about 15-20, carbon atoms
  • sulfates of higher alcohols e.g. salts of a-sulfofatty esters (e.g. of about 10- to ZO-carbon atoms, such as methyl a-sulfomyristate or a-sulf
  • sulfates of higher alcohols are sodium lauryl sulfate, sodium tallow alcohol sulfate. Turkey Red Oil or other sulfated oils, or sulfates of monoor diglycerides 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 1 to 5 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 1 to 6 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 of the higher alkyl benzene sulfonates, olefin sulfonates, the higher alkyl sulfates, and the higher fatty acid monoglyceride sulfates.
  • alkali metal such as sodium and potassium
  • alkaline earth metal such as calcium and magnesium
  • 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 a solubilizing group such as carboxylate, hydroxyl, amido 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 6 to 30 ethylene oxide units; condensation products of alkyl thiophenols with 10 to 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 mono-oleate and mannitan monopalmitate, and the condensation products of polypropylene glycol with ethylene oxide.
  • 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 H NH wherein R is an alkyl group of about 12 to 22 carbon atoms, such as N-Z-aminoethyl stearyl amine and N-2-aminoethyl myristyl amine; amide-linked amines such as those of the type R CONHC H NH wherein R is an alkyl group of about 9 to 20 carbon atoms, such as N-2-amino-ethyl stearyl amide and N-aminoethyl 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 1 to 3 carbon atoms, including such 1 to 3 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, benzyl-dimethyl-stearyl ammonium chloride, trimethyl stearyl ammonium chloride, trimethyl-cetyl ammonium bromide, dimethyl-ethyl dilauryl ammonium chloride, dimethyl-propyl-myristyl 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.
  • R2 e.g. of the formula Rl I--RO 00M
  • the N-long chain alkyl iminodicarboxylic acids e.g. of the formula RN(RC0 OM)2
  • the N-long chain alkyl betaines where R is a long chain alkyl group, e.g. 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 saltforming metal
  • R is a hydrogen or another monovalent substituent (e.g. methyl or other lower alkyl)
  • 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-alkylbeta-iminodipropionic acid, and N-alkyl, N,N-dimethyl glycine; the alkyl group may be, for example, that derived from coco fatty alcohol, lauryl alcohol, myristyl 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 2 to 6 carbon atoms, e.g. l-coco-S-hydroxethyl-S-carboxymethylimidazoline; betaines containing a sulfonic group instead of the carboxylic group; betaines in which the long chain substituent is joined to the carboxylic group without an intervening nitrogen atom, e.g. inner salts of Z-trimethylamino fatty acids such as Z-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 2 to 6 carbon atoms e.g. l-
  • water-soluble builder salts which may be used, particularly when heavy duty cleaning is desired, include phosphates and particularly condensed phosphates (e.g. pyrophosphates or tripolyphosphates), silicates, borates and carbonates (including bicarbonates), as well as organic builders such as salts of nitrilotriacetic acid or ethylene diamine tetracetic acid.
  • phosphates and particularly condensed phosphates e.g. pyrophosphates or tripolyphosphates
  • silicates e.g. pyrophosphates or tripolyphosphates
  • borates and carbonates including bicarbonates
  • organic builders such as salts of nitrilotriacetic acid or ethylene diamine tetracetic acid.
  • Sodium and potassium salts are preferred. Specific examples are sodium tripolyphosphate, potassium pyrophosphate, sodium hexametaphosphate, sodium carbonate, sodium bicarbonate, sodium sesquicarbonate, sodium
  • Na salt of methylene diphosphonic acid, trisodium nitrilotriacetate, or mixtures of such builders, including mixtures of pentasodium tripolyphosphate and trisodium nitrilotriacetate in a ratio, of these two builders, of 1:10 to :1, e.g. 1:1".
  • the proportions of builders salt may be, forexample, 50 parts or, more (e.g. 50 to 1000 parts) per 100 parts of detergent.
  • This invention makes it possible to obtain a high degree of softening in the wash cycle and without the yellowing effects of prior cationic softeners.
  • the invention has found its greatest utility thus far in the washing of cotton fabrics, but it may be used with fabrics made of other cellulosic fibers, e.g. rayon, or other textile fibers, e.g. nylon, silk, wool, polyethylene terephthalate, cellulose acetate, acrylonitrile polymers or copolymers, or blends of any two or more of these fibers (e.g. cotton-polyester blends).
  • cellulosic fibers e.g. rayon, or other textile fibers, e.g. nylon, silk, wool, polyethylene terephthalate, cellulose acetate, acrylonitrile polymers or copolymers, or blends of any two or more of these fibers (e.g. cotton-polyester blends).
  • a wash cycle softener composition is prepared as follows: A blend is formed from 46.3 parts of water; 12.6 parts of a mixture of N-2 hydroxy higher alkyl diethanolamines in which the higher alkyl radicals have to 18 carbon atoms; 37 parts of an aqueous 43% solution of sodium cumene sulfonate; and 1.5 parts of an aqueous 1% solution of blue dyestutr' (Acid Blue 80, Polar Brilliant Blue). This blend is heated moderately (e.g. to 60 C.) until the amine is fully solubilized.
  • aqueous 8% dispersion of polystyrene (which opacifies the mixture) is added to the heated blend, which is then allowed to cool to about 35-40 C. whereupon a small amount (e.g. 0.1 part) of a perfume is added.
  • the resulting mixture is an opaque, homogeneous liquid atroom temperature, having a viscosity of about 10-20 cps., a specific gravity of 1.05 and a pH of 10.7.
  • this composition In use, 60 grams of this composition is mixed, together with 110 grams of a built detergent mixture, with the white cotton fabrics and hot wash water (at 50 C.) in the wash cycle of an automatic washing machine.
  • the built detergent mixture contains 3.3% sodium linear dodecylbenzenesulfonate, 3.8% sodium tallow alcohol sulfate, 1.7% sodium soap of fatty acids (mixed tallow coconut oil fatty acids), 2.1% of nonionic detergent (e.g.
  • hydrophilic ether of a polyalkylene glycol which may be of moderately high molecular weight, for example molecular weight about 3,000), 56.5% pentasodium tripolyphosphate, 4.7% tetrasodium pyrophosphate, 0.5% trisodium phosphate, 4.4% sodium silicate (1:2.35 Na,o:sio, mol ratio), 1.6% sodium carbonate, about /2% sodium carboxymethylcellulose, about /2% fluorescent brighteners, 6% Water (including water of hydration) and the balance Na SO
  • the wash water is New Brunswick, NJ. tap water (whose hardness is 100 p.p.m.), in amount of 17 gallons (35 liters).
  • the fabrics so washed have a very soft and pleasant feel. They are just as white (and much softer than) similar fabrics washed in an identical manner except that only the built detergent mixture is used.
  • Example 1 is repeated (with the wash cycle softener compositions changed to omit the blue dyestuff, polystyrene dispersion and perfume and to use less, or none, of the hydrotrope) using 60 grams of a wash cycle softener composition as follows:
  • the composition contains 12.6% of the amine softener, 11% of sodium cumene sulfonate and the balance water. It is a clear single-phase low viscosity liquid at room temperature.
  • composition of (a) above is blended with 15 g. of a composition containing 12.6% of a long chain alkyl amine oxide having at least 18 carbon atoms in the long chain alkyl, specifically, stearyl dimethyl amine oxide, 16% sodium cumenesulfonate, 1.5% of emulsified polystyrene (emulsifier) and the balance water (containing small amounts of perfume and color).
  • a composition containing 12.6% of a long chain alkyl amine oxide having at least 18 carbon atoms in the long chain alkyl specifically, stearyl dimethyl amine oxide, 16% sodium cumenesulfonate, 1.5% of emulsified polystyrene (emulsifier) and the balance water (containing small amounts of perfume and color).
  • the 60 g. of the composition of (a) above is blended with 2 g. of a nonionic detergent, namely a polyethoxylated long chain alkanol, specifically the condensation product'of 10% of ethylene oxide and of an alkanol of 16-20 carbon atoms.
  • a nonionic detergent namely a polyethoxylated long chain alkanol, specifically the condensation product'of 10% of ethylene oxide and of an alkanol of 16-20 carbon atoms.
  • the 60 grams is a dispersion, in hot water, of 7.6 grams of the amine softener and 2 grams-of a sodium olefin sulfonate made in well-known manner by sulfonation (with an SO -diluent gas mixture) of an alpha monoolefin of 15-18 carbon atoms followed by alkalinization (as with aqueous NaOH) of the sulfonated product and hydrolysis by heating (giving a mixture containing sodium alkenyl sulfonate and sodium hydroxyalkane sulfonate).
  • the 60 grams is a dispersion, in hot water, of 7.6 of the amine softener and sufiicient cumene sulfonate to produce a clear single-phase liquid.
  • Example (h) is repeated, using .3 g. of phosphoric acid in place of the acetic acid.
  • Example (i) is repeated using 3 g. of aqueous concentrated (37.2%) hydrochloric acid in place of the acetic acid.
  • compositions yield very good results in washing process in terms of fabric softness and detergent power, for example.
  • Example 5(a) above is repeated, substituting 23 parts of an aqueous 44% slurry of the sodium olefin sulfonate (of Example 3(d)) for the alkylbenzenesulfonate slurry (giving, in each case, a composition containing detergent). A similar clear liquid is obtained.
  • EXAMPLE 6 The following mixtures are used (in the amounts given below) in the same manner as the wash cycle softener composition of Example 1, with 110 grams of the same detergent composition as in Example 1.
  • EXAMPLE 7 The following mixtures are used in amounts of 60 grams each, as wash cycle softener compositions, with 110 grams of commercial heavy duty built detergent mixture (such as that of Example 1 or Example (e) for washing fabrics as in Example 1.
  • N-2-hydroxy higher alkyl diethanolamine used in Example 1 may be prepared by epoxidizing (e.g. with hydrogen peroxide) in conventional manner a mixture of alpha olefins having 15 to 18 carbon atoms and then reacting the resulting 1,2-epoxide mixture with diethanolamine in stoichiometric proportions.
  • the mixture of olefins and the 1,2-epoxide mixture made therefrom each has the following approximate distribution of components: 1.5% of 14 carbon atoms, 28% of 15 carbon atoms, 28% of 16 carbon atoms, 22.9% of 17 carbon atoms and 19.6% of 18 carbon atoms.
  • EXAMPLE 9 The other N-2-hydroxy higher alkyl amines mentioned in the preceding examples, are made in essentially the same manner as described in Example 8 using, of course, the appropriate epoxide and amine.
  • 1,2-epoxydodecane and morpholine as the reactants. It is preferred to use about equimolar proportions, at a reaction temperature in the range of 90-150 C. under substantially anhydrous conditions. No added catalyst is needed.
  • Example 1 is repeated except that the wash cycle softener composition of the first paragraph of that example is replaced by one of the following compositions:
  • the wash cycle softener composition is a freely flowing liquid homogeneous dispersion, having a pH of 10.8, which remains pourable, without phase separation or precipitation on aging at 1 C. and which gives a highly uniform fabric-softening eflt'ect when included in alkaline wash water containing built detergent compositions. It has an opaque appearance without the need for addition of opacifiers.
  • the 2-hydroxy higher alkyl amines described in the foregoing specific examples are insoluble in water, both hot (e.g. at 70 C.) and at room temperature, even at low concentrations (e.g. 0.5% or 1%). They are either solids or, in some cases, oily liquids at room temperature.
  • a washing and fabric softening composition consisting essentially of a water-soluble organic detergent and an N-Z-hydroxy higher alkyl amine of the formula OH R; R-(lH-CHr-N wherein R is a monovalent alkyl radical of from 8 to 24 carbon atoms and is a radical of an amine of the formula wherein said N-Z-hydroxy higher alkylamine is present in the range of from about 10:1 to 1:1 with regard to said detergent.
  • composition of claim 1 which contains additionally a builder salt.
  • composition of claim 1 wherein R and R are hydroxyalkyl radicals selected from the group consisting of hydroxyethyl and hydroxypropyl radicals.
  • composition as in claim 1 in which said amine of the formula is selected from the group consisting of diethanolamine, methyl ethanolamine and diisopropanolamine.

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US (1) US3697423A (enrdf_load_stackoverflow)
CH (1) CH528590A (enrdf_load_stackoverflow)
DE (1) DE1929193C3 (enrdf_load_stackoverflow)
DK (1) DK133307A (enrdf_load_stackoverflow)
FR (1) FR2010764A1 (enrdf_load_stackoverflow)
GB (1) GB1261087A (enrdf_load_stackoverflow)
NL (1) NL6909011A (enrdf_load_stackoverflow)
SE (1) SE375320B (enrdf_load_stackoverflow)

Cited By (18)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3844952A (en) * 1972-05-03 1974-10-29 Procter & Gamble Detergent compositions
US3853770A (en) * 1969-07-31 1974-12-10 Du Pont Fabric softener compositions
US3882051A (en) * 1970-11-16 1975-05-06 Colgate Palmolive Co Liquid detergent composition
US3891709A (en) * 1972-06-27 1975-06-24 Daicel Ltd Polyoxyalkylene amines
US3893930A (en) * 1971-12-06 1975-07-08 Colgate Palmolive Co Detergent-softener compositions containing esters of dicarboxylic acids and polyhydroxy tertiary amines
US3897347A (en) * 1971-11-22 1975-07-29 Henkel & Cie Gmbh Washing agents containing a textile softener and process of washing and softening textiles
US3915867A (en) * 1973-04-24 1975-10-28 Stepan Chemical Co Domestic laundry fabric softener
US3997453A (en) * 1974-02-11 1976-12-14 Colgate-Palmolive Company Softener dispersion
US4083872A (en) * 1975-01-31 1978-04-11 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler N-2,3-Dihydroxypropyl-N-2-hydroxyalkyl-amine and its salts
US4179393A (en) * 1976-02-06 1979-12-18 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Stable aqueous suspension of water-insoluble, calcium-binding aluminosilicates and organic suspending agents
US4224250A (en) * 1977-06-02 1980-09-23 Colgate-Palmolive Company Novel fabric conditioning compounds
US4281201A (en) * 1979-12-10 1981-07-28 Quad Chemical Corporation Tertiary amines for use in water base hair care compositions
US4311692A (en) * 1979-12-10 1982-01-19 Quad Chemical Corporation Tertiary amine personal care composition
US4326966A (en) * 1979-06-20 1982-04-27 Ceskoslovenska Akademie Ved Agent for textile livening with an antistatic effect and favorable dermatologic properties
US4326967A (en) * 1980-06-24 1982-04-27 Lever Brothers Company Liquid formulations for depositing perfumes on fabrics
US4328371A (en) * 1980-12-15 1982-05-04 Henkel Corporation Alkylene oxide adducts of amino alcohols
US4384968A (en) * 1980-11-17 1983-05-24 Betz Laboratories, Inc. Electrostatic precipitator efficiency enhancement
US4666615A (en) * 1984-08-23 1987-05-19 Henkel Kommanditgesellschaft Auf Aktien Aqueous liquid cleaner containing an anionic surfactant and an ethoxylated aliphatic vicinal hydroxyamine

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3853770A (en) * 1969-07-31 1974-12-10 Du Pont Fabric softener compositions
US3882051A (en) * 1970-11-16 1975-05-06 Colgate Palmolive Co Liquid detergent composition
US3897347A (en) * 1971-11-22 1975-07-29 Henkel & Cie Gmbh Washing agents containing a textile softener and process of washing and softening textiles
US3893930A (en) * 1971-12-06 1975-07-08 Colgate Palmolive Co Detergent-softener compositions containing esters of dicarboxylic acids and polyhydroxy tertiary amines
US3844952A (en) * 1972-05-03 1974-10-29 Procter & Gamble Detergent compositions
US3891709A (en) * 1972-06-27 1975-06-24 Daicel Ltd Polyoxyalkylene amines
US3915867A (en) * 1973-04-24 1975-10-28 Stepan Chemical Co Domestic laundry fabric softener
US3997453A (en) * 1974-02-11 1976-12-14 Colgate-Palmolive Company Softener dispersion
US4083872A (en) * 1975-01-31 1978-04-11 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler N-2,3-Dihydroxypropyl-N-2-hydroxyalkyl-amine and its salts
US4179393A (en) * 1976-02-06 1979-12-18 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Stable aqueous suspension of water-insoluble, calcium-binding aluminosilicates and organic suspending agents
US4264480A (en) * 1976-02-06 1981-04-28 Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) Stable aqueous suspension of water-insoluble, calcium-binding aluminosilicates and organic suspending agents
US4224250A (en) * 1977-06-02 1980-09-23 Colgate-Palmolive Company Novel fabric conditioning compounds
US4326966A (en) * 1979-06-20 1982-04-27 Ceskoslovenska Akademie Ved Agent for textile livening with an antistatic effect and favorable dermatologic properties
US4281201A (en) * 1979-12-10 1981-07-28 Quad Chemical Corporation Tertiary amines for use in water base hair care compositions
US4311692A (en) * 1979-12-10 1982-01-19 Quad Chemical Corporation Tertiary amine personal care composition
US4326967A (en) * 1980-06-24 1982-04-27 Lever Brothers Company Liquid formulations for depositing perfumes on fabrics
US4384968A (en) * 1980-11-17 1983-05-24 Betz Laboratories, Inc. Electrostatic precipitator efficiency enhancement
US4328371A (en) * 1980-12-15 1982-05-04 Henkel Corporation Alkylene oxide adducts of amino alcohols
US4666615A (en) * 1984-08-23 1987-05-19 Henkel Kommanditgesellschaft Auf Aktien Aqueous liquid cleaner containing an anionic surfactant and an ethoxylated aliphatic vicinal hydroxyamine

Also Published As

Publication number Publication date
DK133307A (enrdf_load_stackoverflow)
NL6909011A (enrdf_load_stackoverflow) 1969-12-16
SE375320B (enrdf_load_stackoverflow) 1975-04-14
DE1929193B2 (de) 1979-03-22
CH528590A (de) 1972-09-30
FR2010764A1 (enrdf_load_stackoverflow) 1970-02-20
DE1929193A1 (de) 1970-01-02
DE1929193C3 (de) 1979-11-08
GB1261087A (en) 1972-01-19

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