US3637495A - Agent for the posttreatment of laundry - Google Patents

Agent for the posttreatment of laundry Download PDF

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US3637495A
US3637495A US656136A US3637495DA US3637495A US 3637495 A US3637495 A US 3637495A US 656136 A US656136 A US 656136A US 3637495D A US3637495D A US 3637495DA US 3637495 A US3637495 A US 3637495A
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carbon atoms
agents
water
acid
glycamide
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Hans-Werner Eckert
Arnold Heins
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Henkel AG and Co KGaA
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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
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/32—Amides; Substituted amides
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/525—Carboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain two or more hydroxy groups per alkyl group, e.g. R3 being a reducing sugar rest
    • 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
    • D06M13/372—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 containing etherified or esterified hydroxy groups ; Polyethers of low molecular weight

Definitions

  • a softening agent for the posttreatment of washed laundry is disclosed, the same being adapted for addition to the rinse water either as a solid or in liquid form.
  • the softening agent corresponds to the following formula:
  • R is alkyl containing 10 to 22 carbon atoms, and mayleinterrugtedby either p ty/gen atoms in the vicinity of the N atom group, R is alkyl containing seven to 21 carbon atoms and n is either 3 or 4.
  • n is either 3 or 4.
  • the total number of 3 Claims, 3 Drawing Figures AGENT FOR THE ROSTTREATMENT OF LAUNDRY This invention relates to softening agents for use in the posttreatment of laundry, to compositions containing such softening agents as active ingredient and to the methods of preparing and using such agents and compositions.
  • cationic substances are added to the final rinse, which substances contain at least two fatty radicals of high molecular weight in their molecules.
  • dialkyl dimethyl ammonium salts that are dispersable in water have become popular for this purpose, each of the two alkyl radicals in this latter compound contains l6 to 18 carbon atoms.
  • These cationic softening agents are usually marketed in the form of their aqueous dispersions.
  • .lt- is an object of this invention to eliminate disadvantages of the prior art methods of posttreating laundry by the provision of a new softening agent.
  • R represents an alkyl radical having to 22, preferably 12 to 20, and most preferably 16 to l8 carbon atoms
  • R represents an alkyl radical having 7 to 21, preferably ll to 19, and most preferably to 17 carbon atoms
  • n is either of the whole numbers 3 or 4, further wherein the alkyl radical R can be interrupted by an ether oxygen atom in the vicinity of the NH group, and the sum of the carbon atoms contained in R, and R; amounts to at least 23 and preferably to from 27 to 35, is characterized by improved feel, i.e., softness and absorbency.
  • n 4, i.e., N- alkyl-N-acylglycamines are employed as softening agents.
  • glycamides for the sake of simplicity.
  • These softening agents can be employed in the treatment of washed textiles, alone or together with other conventional laundry posttreatment agents, such as acidifiers or disincrusting agents, optical brighteners and/or heavy metal-free, oxidizing, watersoluble antimicrobial agents.
  • the textiles or other laundered items which have been rinsed with the products of the invention possess, after drying, not only a high degree of fullness and softness, but they also possess excellent absorbency.
  • the softening agents of the invention are quite compatible with anionic optical brightening agents. If any of the above-mentioned antimicrobial agents are used, not only are any microbes that might be present in the washed textiles or in the rinse water killed, but often antimicrobial properties are conferred upon the posttreated textiles.
  • the glycamides to be used in the method of the invention or contained in the preparations according to the invention can be prepared by amidation in the known manner from the ap limbate glycamines which can be produced by the hydrogenation of hexoses or their oligomers using therefor Raney nickel catalyst in the presence of higher alkyl amines.
  • hexoses The principal hexoses involved are monosaccharides such as glucose, mannose, galactose, fructose, sorbose or their mixtures such as invert sugar; however, their oligomers can also be used, such as maltose, for example. lnstead of hexoses, pentoses, mixtures of pentoses or mixtures of pentoses and hexoses can be used.
  • the amines suitable for use in the reaction are primary alkylmonoamines.
  • the alkyl radicals of these amines like the alkyl radicals of the fatty esters to be used in the amidation, can be saturated, straight-chained or branched, and of synthetic or natural origin.
  • the radicals R present in the glycamides can be derived from decyl, lauryl, myristyl, cetyl, stearyl, oleyl, arachyl, or behenyl amine.
  • Such amines, in which the N atom and the ether oxygen atom are separated from one another by three carbon atoms are obtained for example by addition of acrylonitrile to a suitable fatty alcohol followed by reduction of the nitrile group.
  • the fatty acid radicals R CO can be derived from capric, lauric, myristic, palniitic, stearic, oleic, arachic or behenic acid.
  • Glycamides can also be used in which the amine and/or the fatty acid radicals are present as isomer mixtures, such as those which can be obtained from fats of natural origin. Accordingly, these amines and fatty esters can be made from the fats derived from plants, land or marine animals, as, for example, from coconut oil, palm oil, linseed oil, cottonseed oil, peanut oil, rapeseed oil, etc., from hog lard, tallow or fish or whale oil or from fractions of the fatty acids contained in these fats.
  • the amines or fatty esters to be used are not to be excessively unsaturated, i.e., they are not to have an iodine number higher than 50, and preferably not higher than 30. In fact, even substantially completely hardened products having iodine numbers below 10 and preferably below 5 can be used.
  • the methyl esters which are employed are preferably fatty acid esters.
  • the esters of monoalcohols having two to four carbon atoms as, for example, the esters of ethyl, propyl, isopropyl, butyl and isobutyl alcohol etc.
  • Suitable for use herein are also the fatty acid glycerides.
  • the glycamide thus obtained can be used directly for the purposes of the invention. If desired, however, it can first be purified, as for example by recrystallization.
  • the glycamides are moderately soluble in water, but are readily soluble in water-soluble organic solvents, such as monohydric or polyhydric alcohols having one to four carbon atoms, or in ether alcohols, such as the monoethers formed by reaction of the above-mentioned univalent alcohols with ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, or by the monoethers or diethers of the said monohydric alcohols formed by reaction of the monohydric alcohols with glycerine.
  • the glycamides are also soluble in the lower watersoluble ketones.
  • the aforesaid solvents particularly those having boil' ing points below 100 C., are also suitable for the recrystallization of the glycamides.
  • the washed textiles or other laundered items are contacted with a rinse water containing the glycamides in concentrations of approximately 0.05 to about 2 grams per liter and preferably from 0.1 to about 0.5 g./l.
  • the glycamides can be used directly in the first rinse, even if the remains of the washing medium have not been completely washed out of the goods. Since, of course, it has become an established practice to add the softening agent to the final rinse, the same can, obviously be done when using the glycamides of the invention or the softening agents containing them.
  • the laundry is dried in the conventional manner.
  • the laundry is soft and full and has a pleasant feel, which becomes pleasantly observable especially in the case of articles which come in contact with the skin, such as underwear, bed linen, and handkerchiefs.
  • wash-and-drying cloths exhibit a remarkably good absorbency, which is greatly appreciated in the case of dish towels and bath towels.
  • the moist articles which have been soft-rinsed according to the invention yield their moisture more quickly than others on being subjected to drying.
  • the textiles thus treated are observed to iron more easily than the conventionally laundered articles.
  • the glycamides act on the textiles or other laundered items for only a relatively short period especially in the case of automatic washing machines, it is advantageous to use the moderately water-soluble glycamides in finely divided form. This is accomplished in accordance with the invention by using the posttreatment agents in solid or liquid form and in a form in which the glycamide is mixed together with the conventional solid or liquid diluents and/or fillers.
  • Water-soluble inorganic, preferably weakly alkaline, neutral or weakly acid substances are suitable for use as solid fillers.
  • inorganic or organic salts are of primary importance, as for example the alkali salts of sulfuric acid, orthophosphoric acid or pyrophosphoric acid.
  • salts of organic acids can also be used, such as the nonsurface-active salts of carboxylic acids or hydroxycarboxylic acids having one to l0, preferably one to six carbon atoms, as for example, salts of acetic acid, propionic acid, lactic acid, citric acid, tartaric acid, benzoic acid, phthalic acid, etc.
  • Water-soluble inorganic or organic acid amides or their salts may also be present as solid fillers, as for example, amidosulfuric acid salts, amidophosphoric acid salts and water-soluble amides or carboxylic acids, such as urea, acetamide, etc.
  • Solid polyethylene glycols are also usable as fillers.
  • the solid posttreating agents of the "invention canbe prepared for example by spraying a solution or dispersion of the glycamides in a suitable liquid onto the finely divided solid filler substances. It is also possible to spray aqueous solutions or suspensions of glycamides having a percentage of fillers dis solved or dispersed therein, in the known manner, and thus to obtain readily soluble powders or granules. Lastly, solutions or dispersions of the glycamides in fused urea or in fused polyethylene glycols can be sprayed or otherwise converted into easily soluble powders or granules.
  • the time which is required for the glycamides added as concentrates to the rinse water to reach the desired concentration for use can be still further reduced by using liquid products in which the glycamides are dissolved in a solvent or dispersed in water. In this manner no time is lost, i.e., taken up in the dissolution of a solid filler, and instead the desired concentration for use establishes itself immediately after the addition of the liquid concentrate to the rinse water.
  • the liquid aqueous concentrates are prepared by dispersing the moderately water-soluble glycamides in an aqueous phase. It has proved advantageous for the glycamides first to be dissolved in one of the above-named water-soluble organic solvents and thereafter for the resulting solutions to combine with water.
  • the solid glycamides thereupon separate in finely divided form, the organic solvents serving as solubilizers.
  • These aqueous solutions can of course contain any of abovenamed solid fillers if the stability of dispersion is not adversely affected thereby. in many cases the stability may be improved by such addition.
  • alkali salts of lower carboxylic acids or hydroxycarboxylic acids containing up to six carbon atoms, and urea or acetamide have proved particularly suitable and can be used instead of, or together with the above-mentioned water-soluble organic solvents also as solubilizers.
  • the known dispersing and emulsifying agents or emulsion stabilizers can be used for effecting the stabilization of the aqueous glycamide dispersions.
  • Suitable dispersing or emulsifying agents include the known anionic or nonionic wash-active substances whose action is based on the simultaneous presence of one hydrophobic and one hydrophilic radical in their molecules.
  • the hydrophobic radical consists usually of an alkyl radical having eight to 20, preferably 12 to 18 carbon atoms.
  • Anionic or nonionic groups are suitable as hydrophilic radicals.
  • the anionic groups include carboxyl, sulfonic acid or sulfuric acid semiester groups; the nonionic groups include aggregations of hydroxyl groups or polyethylene glycol ether chains.
  • alkylbenzenesulfonates fatty alcohol sulfates, fatty alcohol glycol ether sulfates having one to five ethylene glycol ether radicals in the molecule, fatty acid monoglycerides, polyethylene glycol ethers of fatty alcohols or alkylphenols having five to 20 ethylene glycol ether radicals in the molecule are suitable for use as dispersing and emulsifying agents.
  • the amount of these dispersing and emulsifying agents be greater than the amount of the glycamide present and preferably the dispersing or emulsifying agent should be present in substantially lesser quantities amounting to at the most to 50 percent, and preferably amounting to from 5 to 25 percent of the glycamides.
  • Suitable emulsion stabilizers include the water-soluble colloids, such as the salts of ether carboxylic acids or ether sulfonic acids of cellulose, cellulose sulfate, polyacrylic acid or polymethacrylic acid salts, water-soluble polyacrylamides and polyethylene glycols, preferably those having a molecular weight greater than 600, and particularly the solid polyethylene glycols.
  • Many of these emulsion stabilizers produce a great increase in the viscosity of the aqueous solutions, and therefore they are used in quantities preferably of less than 1 percent so that the posttreatment agents will still be readily fiuid in nature.
  • Others, particularly the polyethylene glycols can be used in substantially greater quantities, without raising the viscosity to undesirable levels.
  • glycamides according to the invention and the compositions containing such glycamides can advantageously be combined with other substances which have heretofore been used as posttreatment agents. These include, for example, op-
  • tical brighteners tical brighteners, acidifying and disincrusting agents, colorants, perfumes, etc. These substances can be incorporated into the solid or liquid posttreatment agents according to the invention.
  • the biighteners are intended mainly for cellulose fibers, but brighteners for cellulose and/or other fibers, especially synthetic fibers, can be used as well.
  • brighteners for cellulose and/or other fibers, especially synthetic fibers, can be used as well.
  • the following types of brighteners can be used:
  • Suitable additives for acidification and/or for the removal of ash or other fiber incrustations include the nonoxidizing acids which have been found to be not harmful to the fibers to be treated and particularly those additives which form soluble alkaline earth salts, and complex compound formers.
  • the acid reacting substances include for example amidosulfuric acid, urea compounds of orthophosphoric acid or solid organic acids like citric acid.
  • the complex compound formers include for example tripolyphosphates or the higher but still watersoluble polyphosphates of alkalies, salts of nitrilotriacetic acid, ethylenediamine tetracetic acid, N-oxyethylethylenediaminetriacetic acid and other conventional organic complex compound forming agents, such as the salts of certain di-,tri-, or tetraphosphonic acids.
  • antimicrobial agents as used herein is understood to mean both bactericidal and bacteriostatic, and fungicidal and/or fungistatic products.
  • the antimicrobial agents are required to be water-soluble either per se or in the form of their salts.
  • suitable antimicrobial agents for use herein are formaldehyde, halogenated phenols, nitrated monoor polyalcohols, and antimicrobial surfactants.
  • halogenated phenols which may be used as antimicrobials
  • chlorination and bromination products of phenol such as pentachlorophenol
  • halogenated cresols xylenols, such as 4-bromo-3,5-xylenol or halogenated cyclohexylphenols, methylcyclohexylphenols or benzylphenols.
  • water-soluble antimicrobial substances of the cationic or hybrid ionic surfactant type which serve in the final posttreatment agents also as dispersing agents.
  • Instances of cationic substances which are suitable as antimicrobials include quaternary ammonium compounds which contain on the nitrogen atom thereof an aliphatic hydrocarbon radical containing eight to 18, and preferably 10 to l4 carbon atoms, or alternatively contain on the nitrogen atom at least one aromatic radical or a radical having double bonds, the latter radical being linked to the nitrogen atom by an aliphatic carbon atom.
  • ca tionic compounds suitable for use in the invention include: diethylbenzyldodecyl ammonium chloride, diethylbenzyloctyl ammonium chloride, and dibutylallyl, methylethylbenzyl, ethylcyclohexylallyl and ethylcrotyldiethylaminoethyl dodecyl ammonium chloride.
  • tertiary amines suitable for use which can be prepared by condensing a primary or secondary amine containing up to four basic nitrogen atoms and one aliphatic or alkylaromatic radical having eight to 18 and preferably eight to 14 aliphatic carbon atoms with a phenol or lower aliphatic aldehyde, preferably formaldehyde or acetaldehyde.
  • the phenol employed in the condensation reaction may have in its molecule a plurality of sites capable of condensation, and these may be substituted with lower alkyl, alkoxyl or benzyl radicals containing up to four carbon atoms.
  • the phenol, alkyl, alkoxyl, and benzyl radicals may additionally be substituted with chlorine or bromine atoms and/or with nitro groups.
  • condensation products include, for instance, the following compounds: oxybenzyloctylamine, oxybenzyldodecyldiethylenetriamine, (2-oxy-5-chloro-6-methylbenzyl)-dodecyldiethylenetriamine, (2-oxy-5-methyl-benzyl)- octyldiethylenetriamine, (2-oxy-5-chloro-4,6-dimethylbenzyl)-octyldiethylenetriamine, (tris-oxybenzyl)-dodecyltriethylenetetramine, o,o-bis-(tetradecylaminomethyl )-pcresol, o,o-bis-(dodecyldiethylenetriaminomethyl)-p-chlorom-cresol, m,m-bis(do
  • the hybrid-ionic surfactants which have achieved particular importance as antimicrobials include compounds of the aminocarboxylic acid, polyamlnocarboxylic acid and betainc type.
  • aminocarboxylic and polyaminocarboxylic acid antimicrobial agents are compounds having the following structural formula:
  • R represents an alkyl or alkylaryl radical of high molecular weight, preferably such a hydrocarbon radical having six to 18 and most preferably eight to 14 aliphatic carbon atoms
  • R represents an ethylene or propylene radical
  • x represents a whole number of from 1 to 6
  • R represents an aliphatic-aromatic or aromatic bridge having one to six carbon atoms.
  • the following compounds are illustrative of aminocarboxylic and polyaminocarboxylic compounds having the above-mentioned formula: dodecylaminopropylglycine, tetradecylaminoethyl-B-alanine, dodecyl-di-(aminoethyl)- glycine, dodecylaminoisopropylaminomethylsalicylic acid, hexadecyl-tri-(aminoethyl)-B-aminobutyric acid, dodecylbenzylaminopropyl-fl-alanine, octylphenoxyethyl-di- (aminoethyU-glycine, dodecylaminoethylphenylalanine, dodecylaminoethylaminobenzoic acid, etc.
  • the radical R can also be interrupted by an ether oxygen atom, as is the case, for example, in the following compounds: dodecyloxypropylaminopropionic acid, lauryl-l ,3-oxypropyl- B-aminobutyric acid, C -alkyloxyethylaminoacetic acid,
  • R has the same meaning as in the preceding formula R, represents an ethylene or propylene group, and R R and R represent aliphatic bridges of low molecular weight, X an ether oxygen atom or the CONH-group.
  • carboxybetaine compounds are lauroyl-l,3-midopropyldimethylaminoacetic acid, lauryloxyethyldi-(hydroxyethyl)- aminopropionic acid, octylphenoxyethyldi-(hydroxyethyl)- aminoacetic acid, etc.
  • the antimicrobial agents can be combined in any desired manner with solid or liquid diluents or fillers, with hydrotropic substances, with dispersing and emulsifying agents, with emulsion stabilizers, with brighteners and with acidification and disincrusting agents.
  • the amounts of the antimicrobial agents contained in the solid or liquid laundry posttreatment agents can vary within wide limits according to the subsequent intended use of the laundered articles, amounting to 0.5-30percent and preferably l-20percent by weight.
  • the antimicrobial agents are hybrid-ionic surface active substances, their quantity is always smaller than the quantity of the softening agent; preferably the quantity of the hybrid-ionic surface-active antimicrobial agents amounts to no more than 50 percent of the quantity of the softening agent.
  • laundry posttreatment agents according to the invention as noted above constitute solid products and as such have the following composition:
  • l-lS weight percent of a surface-active dispersing or emulsifying agent, the quantity thereof always being less than the amount of the glycamide and preferably no more than 50 percent and most preferably from 5 to 25 percent of the amount of glycamide.
  • an emulsion stabilizer or thickening agent 0-20 and preferably 0.ll0 weight percent of an emulsion stabilizer or thickening agent, the quantity thereof being regulated so that a percent aqueous solution or dispersion of the entire solid preparation will have a good fluidi- 0-30 and preferably 1-20 weight percent of a least one of the above-mentioned antimicrobial agents, with the proviso that if they are antimicrobial hybrid-ion surfactants, the quantity thereof is always to be smaller than the quantity of the glycamide, amounting preferably to no more than 50 percent and most preferably to from 5 to 25 percent of the quantity of the glycamide.
  • liquid, laundry posttreatment preparations in accordance with the invention have the following composition:
  • optical brightener 0-10 and preferably 1-8 weight percent of a optical brightener but preferably such a quantity of optical brightener as to amount to 5 to 25 percent of the amount of the glycamide.
  • a surface-active emulsifying or dispersing agent preferably 0-5 weight percent of a surface-active emulsifying or dispersing agent, the amount thereof always being less than the amount of glycamide and amounting preferably to no more than 50, and most preferably 5 to 25 weight percent of the amount of glycamide.
  • a water-soluble emulsion stabilizer or thickening agent 0-20 and preferably 0. 1-10 weight percent of a water-soluble emulsion stabilizer or thickening agent, the quantity thereof, however, being regulated so that the final preparation will have good fluidity.
  • antimicrobial agents 0-30 and preferably l-20 weight percent of at least one of the above-named antimicrobial agents; if they are antimicrobial hybrid-ion surfactants, the quantity thereof always being less than the quantity of the glycamide, amounting preferably to no more than 50 percent and most preferably from 5 to 25 percent of the quantity of the glycamide.
  • the water in the liquid preparations the water can be entirely replaced by water-soluble organic solvents, or at least to such an extent that all of the components and especially the glycamide, are dissolved.
  • N-alkyl-N-acyl glycamines thus prepared were in the form of pastes or solids, depending on the chain length and on the chain length distribution of the alkyl or acyl radicals. If desired, they could be purified by recrystallization from the water-soluble organic solvents mentioned previously, or from benzene or acetic acid ethyl ester.
  • the feel is very soft and full 2. The feel is soft 3. The feel is medium-stiff 4. The feel is stiff In many cases the evaluation scores given by all of the testers were identical; where there were differences, an average was taken of the individual scores.
  • the material to be tested rests on the baseplate l and is compressed by the feeler descending vertically.
  • the feeler consists of the feeler plate 2, the vertical shaft 3 and the bearing 4, and is guided by the vertical shaft 3, although during the measurement it rests fully on the specimen without any friction on the shaft.
  • the moment at which contact occurs between feeler 5 and bearing 4 is indicated in some instances electrically, e.g., by a neon lamp, and in other instances of the apparatus it is indicated interferometrically in that the bearing 4, for example, is a black glass plate on which even the slightest deformations of the surface by the pressure of the micrometer can be detected interferometrically.
  • the fabric specimen is placed on the baseplate l.
  • the specimen must completely cover the baseplate and extend beyond the margins thereof.
  • the feeler surface area 25 cm.*, weight 50 g.
  • the procedure is twice repeated on the same piece of fabric, the pressure being increased, by placing weights on the feeler plate 2, tenfold (500 grams) and twentyfivefold (1,250 grams).
  • the relative compressibility of the nonsoft-rinsed fabric, z,, was determined in the same manner, and the percentage compressibilities for the 20 and 50 p/cm. loads were calculated from the figures obtained. These values were averaged to form a figure which is taken as the percentage compressibility 2., for the purpose of evaluating the effect achieved with various softening agents. The percentage compressibility of the nonsoft-rinsed fabrics is taken as 100 percent.
  • the value 2 is computed according to the following formula:
  • a rail 7 which is vertically displaceable in relation to these gauges'and bears the holding means 9 for holding the textile strips 10.
  • a trough ll containing distilled water 12.
  • the gauges 8 are adjusted so that their zero mark is even with the surface of the water.
  • the fabric strips 10 are kept tense by a weight attached to the bottom thereof, for example, by a glass rod 13 passed through two holes in each strip.
  • the rail 7 bearing the strips is lowered until the strips 10 dip into the water, and the height to which water rises is read on gauges after 1, 2, 5, 10, 20, 30, and 60 minutes.
  • the values determined represent reciprocal velocities (sec./cm.); an increase in the absorption time q accordingly corresponds to a loss of absorbency.
  • Glucamide R C 'C mixture of coconut fatty acids avg. about C
  • Liquid rinsing agents of the type which have been used heretofor in conventional laundering procedures can easily be prepared by the incorporation of the claimed glycamides, i.e., by dissolving the glycamide and the optical brightencr, if any, in an organic solvent and then dispersing this solution in water or in an aqueous solution of the other components.
  • Theproducts described in the following examples' were obtained in this manner.
  • EXAMPLE 1 l 10% glucamide according to example 6 30% isopropanol 2% nonyl phenyl 9.5 ethoxy compound 58% water
  • EXAMPLE 12 10% glucamide according to example 6 30% ethyleneglycol monoethyl ether nonyl phenol 9.5 ethoxy compound 55% water
  • EXAMPLE 13 glucamide according to example 6 30% isopropanol 2% ethoxylated dimethylpolysiloxane 10% citric acid 48% water
  • EXAMPLE 14 10% glucamide according to example 6 30% isopropanol 2% ethoxylated dimethylpolysiloxane 10% tartaric acid 48% water
  • Example 15 10% glucamide according to example 6 30% ethylene glycol monoethyl ether 2% nonylphenol 9.5 ethoxy compound l% brightencr as in formula la, above 57% water
  • EXAMPLE [6 10% glucamide according to example 6 30% ethylene
  • examples 1 l-l 8 can have antimicrobial agents added to them.
  • brightening agents can be incorporated, if needed, into the afterrinsing agents of examples 11-14 and 19-20.
  • the brightening agents can be, for example, one of the compounds listed previously. In all these formulation changes, it may be advantageous, depending on the solubility of the glycamides or of the antimicrobial substance, to vary the nature and quantity of the organic solvent and/or of the emulsifying agent.
  • a liquid composition adapted for softening of laundered textile fabrics consisting essentially of a solvent selected from the group consisting of water, a water-soluble organic solvent and a mixture of water and a water-soluble organic solvent and 2-30 wt. percent of an effective textile-fabric softening glycamide of the formula:
  • R is l alkyl or alkenyl of to 22 carbon atoms or (2) alkyl or alkenyl of 10 to 22 carbon atoms with an ether oxygen linkage between either the 2 and 3 or 3 and 4 carbon atoms from the nitrogen atom, R is alkyl or alkenyl of seven to 21 carbon atoms, R,+R have 23 to 39 carbon atoms, and n is 3 or 4, said water-soluble organic solvent being selected from the group consisting of unsubstituted aliphatic monohydric alcohols of one to four carbon atoms, ether alcohols thereof formed by the reaction of said aliphatic alcohols with a glycol selected from the group consisting of ethylene glycol diethylene glycol, propylene glycol, and butylene glycol, lower ketones, and monoethers or diethers formed by reacting said aliphatic alcohols with glycerine.
  • liquid composition of claim 1 consisting essentially of 5-15 wt. percent of said glycamide, wherein R, has l2 to carbon atoms, wherein R, has H to 19 carbon atoms, and wherein R,+R have a total of 27 to 35 carbon atoms.
  • a method for treating a textile-fabric article comprising laundering said article, and thereafter rinsing said article with water containing dissolved therein in the range of 0.05 to 2 grams per liter of a glycamide of the formula:
  • R is l) alkyl of 10 to 22 carbon atoms or (2) alkyl of 10 to 22 carbon atoms with an ether oxygen linkage between either the 2 and 3 or 3 and 4 carbon atoms from the nitrogen atom, R is alkyl of seven to 21 carbon atoms, R +R have 23 to 39 carbon atoms, and n is 3 or 4.

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  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US656136A 1966-08-01 1967-07-26 Agent for the posttreatment of laundry Expired - Lifetime US3637495A (en)

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DEH0060124 1966-08-01
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AT (1) AT280938B (no)
BE (1) BE702083A (no)
CH (1) CH517208A (no)
DK (1) DK118182B (no)
ES (1) ES343644A1 (no)
FR (1) FR1550144A (no)
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US3764531A (en) * 1966-08-01 1973-10-09 Henkel & Cie Gmbh Antimicrobial and laundry softening compositions
US3844952A (en) * 1972-05-03 1974-10-29 Procter & Gamble Detergent compositions
US3904359A (en) * 1972-09-07 1975-09-09 Colgate Palmolive Co Post-wash fabric treating method
US3984335A (en) * 1975-01-16 1976-10-05 Basf Wyandotte Corporation Compositions for souring and softening laundered textile materials and stock solutions prepared therefrom
US4134838A (en) * 1977-02-15 1979-01-16 Lever Brothers Company Fabric conditioning product
US4151097A (en) * 1976-07-26 1979-04-24 Lever Brothers Company Liquid systems
US4778823A (en) * 1985-12-20 1988-10-18 Kao Corporation Amide derivative and external medicament comprising same
US5174927A (en) * 1990-09-28 1992-12-29 The Procter & Gamble Company Process for preparing brightener-containing liquid detergent compositions with polyhydroxy fatty acid amines
WO1993001267A1 (en) * 1991-07-08 1993-01-21 The Procter & Gamble Company Detergent compositions containing polyhydroxy fatty acid amide surfactants and a clay softening system
US5194639A (en) * 1990-09-28 1993-03-16 The Procter & Gamble Company Preparation of polyhydroxy fatty acid amides in the presence of solvents
US5234618A (en) * 1989-10-09 1993-08-10 Kao Corporation Liquid detergent composition
US5254281A (en) * 1991-01-29 1993-10-19 The Procter & Gamble Company Soap bars with polyhydroxy fatty acid amides
US5332528A (en) * 1990-09-28 1994-07-26 The Procter & Gamble Company Polyhydroxy fatty acid amides in soil release agent-containing detergent compositions
US5338487A (en) * 1990-09-28 1994-08-16 The Procter & Gamble Company Catalyzed process for glucamide detergents
US5338486A (en) * 1990-09-28 1994-08-16 The Procter & Gamble Company High catalyst process for glucamide detergents
US5354425A (en) * 1993-12-13 1994-10-11 The Procter & Gamble Company Tissue paper treated with polyhydroxy fatty acid amide softener systems that are biodegradable
US5380891A (en) * 1990-09-28 1995-01-10 The Procter & Gamble Company Phase transfer assisted process for glucamide detergents
US5449770A (en) * 1992-01-14 1995-09-12 The Procter & Gamble Company Process for making N-alkylamino polyols
US5454982A (en) * 1990-09-28 1995-10-03 The Procter & Gamble Company Detergent composition containing polyhydroxy fatty acid amide and alkyl ester sulfonate surfactants
USH1513H (en) * 1994-06-01 1996-01-02 The Procter & Gamble Company Oleoyl sarcosinate with polyhydroxy fatty acid amides in cleaning products
US5512699A (en) * 1994-01-25 1996-04-30 The Procter & Gamble Company Poly polyhydroxy fatty acid amides
US5534197A (en) * 1994-01-25 1996-07-09 The Procter & Gamble Company Gemini polyhydroxy fatty acid amides
US5625098A (en) * 1991-07-26 1997-04-29 The Procter & Gamble Company Process for preparing N-alkyl polyhydroxyalkyl amines in aqueous/hydroxy solvents
US5669984A (en) * 1994-01-25 1997-09-23 The Procter & Gamble Company Method for hand washing dishes containing polyhydroxy amines
US5700771A (en) * 1990-09-28 1997-12-23 The Procter & Gamble Company Polyhydroxy fatty acid amide surfactants in percarbonate bleach-containing compositions
US5723673A (en) * 1995-06-07 1998-03-03 The Procter & Gamble Company Process for preparing amides of N-alkyl polyhydroxyalkyls
US5777165A (en) * 1995-06-07 1998-07-07 The Procter & Gamble Company Process for preparing amides of N-alkyl polyhydroxyalkyl amines
EP0919608A1 (en) * 1997-11-25 1999-06-02 The Procter & Gamble Company Use of a polyhydroxyfatty acid amide compound as a softening compound
WO1999060198A1 (fr) * 1998-05-20 1999-11-25 Kao Corporation Composition d'appret adoucissante
US6405809B2 (en) 1998-01-08 2002-06-18 M-I Llc Conductive medium for openhold logging and logging while drilling
WO2002088287A1 (en) * 2001-03-15 2002-11-07 Unilever Plc Fabric softening compositions
US20030060390A1 (en) * 2001-03-07 2003-03-27 The Procter & Gamble Company Rinse-added fabric conditioning composition for use where residual detergent is present
US6541444B1 (en) 1998-05-20 2003-04-01 Kao Corporation Softener composition
US20030075360A1 (en) * 1998-01-08 2003-04-24 Patel Arvind D. Double emulsion based drilling fluids
US6787505B1 (en) 1997-09-15 2004-09-07 M-I Llc Electrically conductive non-aqueous wellbore fluids
US7026278B2 (en) 2000-06-22 2006-04-11 The Procter & Gamble Company Rinse-added fabric treatment composition, kit containing such, and method of use therefor

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US3899616A (en) * 1973-11-09 1975-08-12 Frank A Simonelli Fungistatic fabric treatment
GB2124618A (en) * 1982-06-11 1984-02-22 Nat Res Dev Aliphatic hydroxy amides
ES2053762T3 (es) * 1987-11-19 1994-08-01 British Petroleum Co Plc Acondicionadores de generos.
JPH0623087B2 (ja) * 1989-10-09 1994-03-30 花王株式会社 洗浄剤組成物
WO1992006153A1 (en) * 1990-09-28 1992-04-16 The Procter & Gamble Company Detergent compositions with polyhydroxy fatty acid amide surfactant and polymeric dispersing agent
US5283009A (en) * 1992-03-10 1994-02-01 The Procter & Gamble Co. Process for preparing polyhydroxy fatty acid amide compositions
WO1993025647A1 (en) * 1992-06-15 1993-12-23 The Procter & Gamble Company Liquid laundry detergent compositions with silicone antifoam agent
US5489393A (en) * 1993-09-09 1996-02-06 The Procter & Gamble Company High sudsing detergent with n-alkoxy polyhydroxy fatty acid amide and secondary carboxylate surfactants
EP0717766B1 (en) * 1993-09-09 1998-04-01 The Procter & Gamble Company Automatic dishwashing detergent with alkoxy or aryloxy amide surfactant
WO1995007334A1 (en) * 1993-09-09 1995-03-16 The Procter & Gamble Company Detergent compositions with mixture of n-alkoxy or n-aryloxy polyhydroxy fatty acid amide plus alkoxylated carboxylate surfactant
US20180171521A1 (en) * 2016-12-19 2018-06-21 John Mahdessian Green rejuvenation system and kit
EP4356733A1 (de) * 2022-10-19 2024-04-24 Bode Chemie GmbH Niedrigalkoholisches desinfektionsmittel

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US2993887A (en) * 1953-01-06 1961-07-25 Atlas Powder Co Anhydro amides
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US3349033A (en) * 1964-08-26 1967-10-24 Millmaster Onyx Corp Stable microbiologically active laundry softener
US3356526A (en) * 1964-05-13 1967-12-05 Armour & Co Method of preparing water-dispersible softener compositions and products produced thereby
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US3329609A (en) * 1965-03-22 1967-07-04 Wyandotte Chemicals Corp Compositions containing quaternary ammonium salts
SE319156B (no) * 1966-08-01 1970-01-12 Henkel & Cie Gmbh
DE1619086A1 (de) * 1967-08-14 1969-08-21 Henkel & Cie Gmbh Mittel zum Nachbehandeln gewaschener Waesche

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US2703798A (en) * 1950-05-25 1955-03-08 Commercial Solvents Corp Detergents from nu-monoalkyl-glucamines
US2993887A (en) * 1953-01-06 1961-07-25 Atlas Powder Co Anhydro amides
US3002923A (en) * 1957-03-29 1961-10-03 Atlas Chem Ind Water-in-oil emulsion drilling fluid
US3122502A (en) * 1960-10-10 1964-02-25 Milton M Waldman Stabilized germicidal textile softeners
US3356526A (en) * 1964-05-13 1967-12-05 Armour & Co Method of preparing water-dispersible softener compositions and products produced thereby
US3349033A (en) * 1964-08-26 1967-10-24 Millmaster Onyx Corp Stable microbiologically active laundry softener
US3364142A (en) * 1965-12-06 1968-01-16 Northern Petro Chem Co Composition for reconstituting frozen aqueous systems and method for making

Cited By (46)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3764531A (en) * 1966-08-01 1973-10-09 Henkel & Cie Gmbh Antimicrobial and laundry softening compositions
US3844952A (en) * 1972-05-03 1974-10-29 Procter & Gamble Detergent compositions
US3904359A (en) * 1972-09-07 1975-09-09 Colgate Palmolive Co Post-wash fabric treating method
US3954630A (en) * 1972-09-07 1976-05-04 Colgate-Palmolive Company Post-wash fabric treating composition and method
US3984335A (en) * 1975-01-16 1976-10-05 Basf Wyandotte Corporation Compositions for souring and softening laundered textile materials and stock solutions prepared therefrom
US4151097A (en) * 1976-07-26 1979-04-24 Lever Brothers Company Liquid systems
US4134838A (en) * 1977-02-15 1979-01-16 Lever Brothers Company Fabric conditioning product
US4778823A (en) * 1985-12-20 1988-10-18 Kao Corporation Amide derivative and external medicament comprising same
US5234618A (en) * 1989-10-09 1993-08-10 Kao Corporation Liquid detergent composition
US5194639A (en) * 1990-09-28 1993-03-16 The Procter & Gamble Company Preparation of polyhydroxy fatty acid amides in the presence of solvents
US5454982A (en) * 1990-09-28 1995-10-03 The Procter & Gamble Company Detergent composition containing polyhydroxy fatty acid amide and alkyl ester sulfonate surfactants
US5174927A (en) * 1990-09-28 1992-12-29 The Procter & Gamble Company Process for preparing brightener-containing liquid detergent compositions with polyhydroxy fatty acid amines
US5700771A (en) * 1990-09-28 1997-12-23 The Procter & Gamble Company Polyhydroxy fatty acid amide surfactants in percarbonate bleach-containing compositions
US5332528A (en) * 1990-09-28 1994-07-26 The Procter & Gamble Company Polyhydroxy fatty acid amides in soil release agent-containing detergent compositions
US5338487A (en) * 1990-09-28 1994-08-16 The Procter & Gamble Company Catalyzed process for glucamide detergents
US5338486A (en) * 1990-09-28 1994-08-16 The Procter & Gamble Company High catalyst process for glucamide detergents
US5380891A (en) * 1990-09-28 1995-01-10 The Procter & Gamble Company Phase transfer assisted process for glucamide detergents
US5254281A (en) * 1991-01-29 1993-10-19 The Procter & Gamble Company Soap bars with polyhydroxy fatty acid amides
CN1037452C (zh) * 1991-07-08 1998-02-18 普罗格特-甘布尔公司 含有多羟基脂肪酸酰胺表面活性剂和粘土软化系的洗涤混合物
WO1993001267A1 (en) * 1991-07-08 1993-01-21 The Procter & Gamble Company Detergent compositions containing polyhydroxy fatty acid amide surfactants and a clay softening system
US5625098A (en) * 1991-07-26 1997-04-29 The Procter & Gamble Company Process for preparing N-alkyl polyhydroxyalkyl amines in aqueous/hydroxy solvents
US5449770A (en) * 1992-01-14 1995-09-12 The Procter & Gamble Company Process for making N-alkylamino polyols
US5354425A (en) * 1993-12-13 1994-10-11 The Procter & Gamble Company Tissue paper treated with polyhydroxy fatty acid amide softener systems that are biodegradable
US5534197A (en) * 1994-01-25 1996-07-09 The Procter & Gamble Company Gemini polyhydroxy fatty acid amides
US5512699A (en) * 1994-01-25 1996-04-30 The Procter & Gamble Company Poly polyhydroxy fatty acid amides
US5669984A (en) * 1994-01-25 1997-09-23 The Procter & Gamble Company Method for hand washing dishes containing polyhydroxy amines
USH1513H (en) * 1994-06-01 1996-01-02 The Procter & Gamble Company Oleoyl sarcosinate with polyhydroxy fatty acid amides in cleaning products
US5723673A (en) * 1995-06-07 1998-03-03 The Procter & Gamble Company Process for preparing amides of N-alkyl polyhydroxyalkyls
US5777165A (en) * 1995-06-07 1998-07-07 The Procter & Gamble Company Process for preparing amides of N-alkyl polyhydroxyalkyl amines
US6787505B1 (en) 1997-09-15 2004-09-07 M-I Llc Electrically conductive non-aqueous wellbore fluids
EP0919608A1 (en) * 1997-11-25 1999-06-02 The Procter & Gamble Company Use of a polyhydroxyfatty acid amide compound as a softening compound
WO1999027045A1 (en) * 1997-11-25 1999-06-03 The Procter & Gamble Company Use of a polyhydroxy fatty acid amide compound as a softening compound
US6793025B2 (en) 1998-01-08 2004-09-21 M-I L. L. C. Double emulsion based drilling fluids
US20030075360A1 (en) * 1998-01-08 2003-04-24 Patel Arvind D. Double emulsion based drilling fluids
US6405809B2 (en) 1998-01-08 2002-06-18 M-I Llc Conductive medium for openhold logging and logging while drilling
WO1999060198A1 (fr) * 1998-05-20 1999-11-25 Kao Corporation Composition d'appret adoucissante
US6541444B1 (en) 1998-05-20 2003-04-01 Kao Corporation Softener composition
US7351685B2 (en) 1998-05-20 2008-04-01 Kao Corporation Softener composition
US7026278B2 (en) 2000-06-22 2006-04-11 The Procter & Gamble Company Rinse-added fabric treatment composition, kit containing such, and method of use therefor
US20060075576A1 (en) * 2000-06-22 2006-04-13 Price Kenneth N Rinse-added fabric treatment composition, kit containing such, and method of use therefor
US20030060390A1 (en) * 2001-03-07 2003-03-27 The Procter & Gamble Company Rinse-added fabric conditioning composition for use where residual detergent is present
US20060019867A1 (en) * 2001-03-07 2006-01-26 Demeyere Hugo J M Rinse-added fabric conditioning composition for use where residual detergent is present
US20060030516A1 (en) * 2001-03-07 2006-02-09 Demeyere Hugo J M Rinse-added fabric conditioning composition for use where residual detergent is present
US20030181346A1 (en) * 2001-03-15 2003-09-25 Bijan Harichian Fabric softening compositions
WO2002088287A1 (en) * 2001-03-15 2002-11-07 Unilever Plc Fabric softening compositions
US6930082B2 (en) 2001-03-15 2005-08-16 Unilever Home & Personal Care Usa Division Of Conopco, Inc. Fabric softening compositions

Also Published As

Publication number Publication date
FR1550144A (no) 1968-12-20
AT280938B (de) 1970-04-27
GB1175234A (en) 1969-12-23
ES343644A1 (es) 1968-09-01
DK118182B (da) 1970-07-20
BE702083A (no) 1968-01-31
NL6709356A (no) 1968-02-02
US3764531A (en) 1973-10-09
CH517208A (de) 1971-12-31
SE319156B (no) 1970-01-12

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