US3764531A - Antimicrobial and laundry softening compositions - Google Patents

Antimicrobial and laundry softening compositions Download PDF

Info

Publication number
US3764531A
US3764531A US00088486A US3764531DA US3764531A US 3764531 A US3764531 A US 3764531A US 00088486 A US00088486 A US 00088486A US 3764531D A US3764531D A US 3764531DA US 3764531 A US3764531 A US 3764531A
Authority
US
United States
Prior art keywords
acid
water
glycamide
antimicrobial
agents
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US00088486A
Inventor
H Eckert
A Heins
H Bellinger
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henkel AG and Co KGaA
Original Assignee
Henkel AG and Co KGaA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henkel AG and Co KGaA filed Critical Henkel AG and Co KGaA
Application granted granted Critical
Publication of US3764531A publication Critical patent/US3764531A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • 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

  • An antimicrobial and softening composition for laundry use comprises a water-soluble heavy metal-free non-oxidizing antimicrobial agent, and a glycamide of the formula:
  • the glycamides have the formula given in the Abstract of the Disclosure.
  • R represents an alkyl radical having to 22, preferably 12 to 20, and most preferably 16 to 18 carbon atoms
  • R represents an alkyl radical having 7 to 21, preferably 1 l 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 N-atom, and the sum of the carbon atoms contained in R and R amounts to at least 23 and preferably to from 27 to 35.
  • n 4 i.e., N-alkyl-N-acylglycamines are employed as softening agents. The latter will hereinafter be called glycamides for the sake of simplicity.
  • the data given on the glycamide softening agents also apply accordingly to compounds wherein n 3.
  • 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.
  • the present composition can be use in the treatment of washed textiles, alone or together with other conventional laundry detergents and post-treatment agents, such as acidifiers or disincrusting agents, optical brighteners; and may be made and marketed in powdered or liquid form, as is customary.
  • the textiles fabrics or other laundered items which have been rinsed with the products fabrics of the invention possess, after drying, not only a high degree of fullness and softness, but they also possess excellent absorbency. Furthermore, the sotening 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 anti-microbial properties are conferred upon the post-treated 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 appropriate 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.
  • pentoses mixtures of pentoses or mixtures of pentoses and hexoses can be used.
  • the amines suitable for use in the reaction are primary alkylmonamines.
  • the alkyl radicals of these amines like the alkyl radicals of the fatty esters to be used in the amidation, can be saturated or unsaturated, 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 NH group 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, palmitic, 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, rapseed 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 amidation of the alkylglycamines is carried out by heating the fatty esters with the amines at temperatures of to C, preferably with agitation.
  • the course of the reaction can easily be observed by intercepting the alcohol released by the reaction. When the amount of liberated alcohol has reached approximately the theoretical, the reaction is stopped. In no case is the reaction mixture or the reaction product that has been formed to be heated so intensely or so long as to produce dehydration.
  • 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 univalent or polyvalent alcohols having one to four carbon atoms, or in ether alcohols, such as the monoethers formed by reaction of the abovementioned univalent alcohols with ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, or by the monoethers or diethers of the said univalent alcohols formed by reaction of the univalent alcohols with glycerine.
  • the glycamides are also soluble in the lower water-soluble ketones.
  • the aforesaid solvents particularly those having boiling points below 100C,
  • 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
  • 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 dishtowels 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 10, 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 post-treating agents of the invention can be 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 dissolved 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 abovenamed 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 the above-named 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 6 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 serving 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 non-ionic 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 non-ionic groups are suitable as hydrophilic radicals.
  • the anionic groups include carboxyl, sulfonic acid or sulfurnic acid semi-ester groups; the non-ionic 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 emulsifyingagents.
  • 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%, and preferably amounting to from 5 to 25% of the glycamides.
  • Suitable emulsion stabilizers include the watersoluble 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% so that the post-treatment agents will still be readily fluid in nature.
  • Others, particularly the polyethylene glycols can be used in substantially greater quantities, without raising the viscosity to undesirable levels.
  • the glycamides according to the invention and the compositions containing such glycamides can advantageously be combined with other substances which have heretofore been used as post-treatment agents. These include, for example, optical brighteners, acidifying and disincrusting agents, colorants, perfumes, etc. These substances can be incorporated into the solid or liquid post-treatment agents according to the invention.
  • the combined use of the above-described softening agents with optical brighteners is to be considered as an important and novel feature of the invention.
  • the brighteners are intended mainly for cellulose fibers, but brighteners for cellulose and/or other fibers, especially synthetic fibers, can be used as well.
  • Suitable additives for acidification and/or for the removal of ash or other fiber incrustations include the non-oxidizing acids which have been found to be not harmful to the fibers to be treated and particularly those additives which form soluble alkaline earth metal salts, and complex compound formers.
  • the acid reacting substances include for example amidosulfuric acid, urea compounds or orthophosphoric acid or solid organic acids like citric acid.
  • the complex compound formers include for example tripolyphosphates or the higher but still water soluble 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-, trior tetraphosphonic acids.
  • 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 post-treatment agents also as dispersing agents.
  • the following are instances of the cationic compounds suitable for use in the invention include: diethylbenzyldodecyl ammonium chloride, diethylbenzyloctyl ammonium chloride, and dibutylallyl, me-
  • 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 phenyl, 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-methylbenzyl)octyldiethylenetriamine, (2-oxy-5-chloro-4,6-
  • 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: dodecylaminopropylglycinc, tetra- I decylaminoethyl-B-alanine, dodecyl-di-(aminoethyl)- glycine, dodecylaminoisopropylaminomethylsalicylic acid, hexadecyl-tri-(aminoethyl)-B-aminobutyric acid, dodecylbenzylaminopropyl-B-alanine, octylphenoxyethyl-di-(aminoethyl)-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- 1 ,3-oxypropyl-B-aminobutyric acid, C alkyloxyethylaminoacetic acid, dodecyl-l ,2-
  • the compounds that can be used according to the invention furthermore include carboxybetaines of the formula:
  • R which can be used both in the betaine form, i.e., in the form of inner salts, and in the form of acidic or basic salts.
  • R has the same meaning as in the preceding formula, R represents an ethylene or propylene group,
  • 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-amidopropyldimethylaminoacetic 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 post-treatment agents can vary within wide limits according to the subsequent intended use of the laundered articles, amounting to 0.5 30% and preferably 1 20% by weight. If 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% of the quantity of the softening agent.
  • the laundry post-treatment agents according to the invention as noted above constitute solid products and as such have the following composition 30 95 and preferably 70 90 wt-% of solid vehicle substance 70 5 and preferably 30 10 wt-% glycamide 20 and preferably 1 15 wt-% of an optical brightener,-the same being present in a quantity amounting to to 25% of the amount of glycamide present;
  • a surface active dispersing or emulsifying agent 0 30 and preferably 1 15 wt-% 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% and most preferably from 5 to 25% of the amount of glycamide;
  • emulsion stabilizer or thickening agent 0 20 and preferably 0.1 wt-% of an emulsion stabilizer or thickening agent, the quantity thereof being regulated so that a 10% aqueous solution or dispersion of the entire solid preparation will have a good fluidity;
  • the quantity thereof is always to be smaller than the quantity of the glycamide, amounting preferably to no more than 50% and most preferably to from 5 to 25% of the quantity of the glycamide.
  • the liquid, laundry post-treatment preparations in accordance with the invention have the following composition 2 30 and preferably 5 wt-% glycamide.
  • optical brightener 0 l0 and preferably 1 8 wt-% of an optical brightener but preferably such a quantity of optical brightener as to amount to 5 to 25% of the amount of the glycamide.
  • a surface active emulsifying or dispersing agent 0 l0 and preferably 0 5 wt-% 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 wt-% of the amount of glycamide.
  • 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.
  • glycamides incorporated into the softening agents of the invention and tested in the manner to be described below were prepared on the basis of the fol lowing procedure:
  • 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.
  • Fructamide R C C mixture of coconut fatty acids avg. approx. C
  • a laundry textile antimicrobial and softening composition consisting substantially of 0.5 to 30 weight percent of a water-soluble, heavy metal-free, nonoxidizing antimicrobial agent selected from the group consisting of nitrated polyalcohols and a quaternary ammonium compound and about 2 to weight percent of a textile fabric softening glycamide of the formula:
  • R 1) alkyl of to 22 carbon atoms or, (2) alkyl of 10 to 22 carbon atoms with an ether oxygen linkage between either the two and three or 3 and 4 carbon atoms from the nitrogen atom,
  • R R have 23 to 39 carbon atoms.
  • composition of claim 1 in solid form wherein said glycamide comprises 10 to 30 weight percent thereof.
  • composition of claim 2 in the form of a solution wherein said glycamide comprises 2 to 30 weight percent thereof, and, other than said antimicrobial agent, the balance being water or a water-soluble or- UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,764,531 Dated October 9, 1973 lnvent fl Hans-Werner Eckert et a1.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Detergent Compositions (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)

Abstract

An antimicrobial and softening composition for laundry use comprises a water-soluble heavy metal-free non-oxidizing antimicrobial agent, and a glycamide of the formula:

WHEREIN R1 and R2 are alkyl groups having a total of 23 to 39 carbon atoms, and n is 3 or 4, preferably 4.

Description

United States Patent [191 Eckert et a1.
[451 Oct. 9, 1973 ANTIMICROBIAL AND LAUNDRY SOFTENING COMPOSITIONS Inventors: Hans-Werner Eckert, Dusseldorf;
Arnold Heins, I-Iilden/Rhld.; Horst Bellinger, Dusseldorf, all of Germany Assignee: I'Ienkel & Cie G.m.b.H., Dusseldorf,
Germany Filed: Nov. 10, 1970 App]. No.: 88,486
Related U.S. Application Data Continuation-impart of Ser. No. 656,136, July 26, 1967, Pat. No. 3,637,495.
Foreign Application Priority Data Aug. 1, 1969 Germany H 60 12 48 May 23, 1967 Germany H 62 81 68 U.S. Cl... 252/8-8, 117/1395 CO, ll7/l39.5 F, 252/86, 252/8.9
Int. Cl. D06m 13/40, D06m 13/46 Field of Search 252/88, 8.9, 8.6; 117/1395 F, 143, 139.5 CQ; 260/404, 211
References Cited UNITED STATES PATENTS l/l972 Eckert et a1. 25218.8
Primary ExaminerHerbert B. Guynn Attorney-Burgess, Dinklage & Sprung [57] ABSTRACT An antimicrobial and softening composition for laundry use comprises a water-soluble heavy metal-free non-oxidizing antimicrobial agent, and a glycamide of the formula:
l (CIHOHL. cnron wherein R and R are alkyl groups having a total of 23 to 39 carbon atoms, and n is 3 or 4, preferably 4.
4 Claims, No Drawings ANTIMICROBIAL AND LAUNDRY SOFTENING COMPOSITIONS RELATED APPLICATION This application is a continuation -inpart of Agent for the Post-Treatment of Laundry, filed July 26, 1967, the applicable priority document being on file in the parent application, Ser. No. 656,136, now US. Pat. No. 3,637,495.
THIS INVENTION It has now been found that the glycamides disclosed in the parent application can be used effectively with certain water-soluble antimicrobial agents to both disinfect and soften textile fabrics.
The glycamides have the formula given in the Abstract of the Disclosure. Preferably R, represents an alkyl radical having to 22, preferably 12 to 20, and most preferably 16 to 18 carbon atoms, R represents an alkyl radical having 7 to 21, preferably 1 l to 19, and most preferably to 17 carbon atoms, and 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 N-atom, and the sum of the carbon atoms contained in R and R amounts to at least 23 and preferably to from 27 to 35. Preferably n 4, i.e., N-alkyl-N-acylglycamines are employed as softening agents. The latter will hereinafter be called glycamides for the sake of simplicity. The data given on the glycamide softening agents also apply accordingly to compounds wherein n 3.
The term 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. Examples of suitable antimicrobial agents for use herein are formaldehyde, halogenated phenols, nitrated monoor polyalcohols, and antimicrobial surfactants.
The present composition can be use in the treatment of washed textiles, alone or together with other conventional laundry detergents and post-treatment agents, such as acidifiers or disincrusting agents, optical brighteners; and may be made and marketed in powdered or liquid form, as is customary.
The textiles fabrics or other laundered items which have been rinsed with the products fabrics of the invention, possess, after drying, not only a high degree of fullness and softness, but they also possess excellent absorbency. Furthermore, the sotening 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 anti-microbial properties are conferred upon the post-treated 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 appropriate 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.
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. Instead 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 alkylmonamines. The alkyl radicals of these amines, like the alkyl radicals of the fatty esters to be used in the amidation, can be saturated or unsaturated, 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. There are also suitable those amines whose carbon chain is interrupted by an ether oxygen atom in the vicinity of the N-atoms, preferably between carbon atoms 2 and 3 or 3 and 4 (counting from the N-atom). Such amines, in which the NH group 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, palmitic, 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, rapseed 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. There can, however, be used to equal advantage 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 amidation of the alkylglycamines is carried out by heating the fatty esters with the amines at temperatures of to C, preferably with agitation. The course of the reaction can easily be observed by intercepting the alcohol released by the reaction. When the amount of liberated alcohol has reached approximately the theoretical, the reaction is stopped. In no case is the reaction mixture or the reaction product that has been formed to be heated so intensely or so long as to produce dehydration.
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 univalent or polyvalent alcohols having one to four carbon atoms, or in ether alcohols, such as the monoethers formed by reaction of the abovementioned univalent alcohols with ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, or by the monoethers or diethers of the said univalent alcohols formed by reaction of the univalent alcohols with glycerine. The glycamides are also soluble in the lower water-soluble ketones. The aforesaid solvents, particularly those having boiling points below 100C,
are also suitable for the recrystallization of the glycamides.
In accordance with the invention, 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 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.
After the rinse, as effected in accordance with the invention, 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. In particular, wash and drying cloths exhibit a remarkably good absorbency, which is greatly appreciated in the case of dishtowels and bath towels. Further the moist articles which have been soft-rinsed according to the invention yield their moisture more quickly than others on being subjected to drying. Finally, the textiles thus treated are observed to iron more easily than the conventionally laundered articles.
Since 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. For the manufacture of solid preparations, inorganic or organic salts are of primary importance, as for example the alkali salts of sulfuric acid, orthophosphoric acid or pyrophosphoric acid. However, salts of organic acids can also be used, such as the nonsurface-active salts of carboxylic acids or hydroxycarboxylic acids having one to 10, 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 post-treating agents of the invention can be 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 dissolved 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 abovenamed 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 the above-named solid fillers if the stability of dispersion is not adversely affected thereby. In many cases the stability may be improved by such addition. For this purpose, the alkali salts of lower carboxylic acids or hydroxycarboxylic acids containing up to 6 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 serving 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 non-ionic 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 non-ionic groups are suitable as hydrophilic radicals. The anionic groups include carboxyl, sulfonic acid or sulfurnic acid semi-ester groups; the non-ionic groups include aggregations of hydroxyl groups or polyethylene glycol ether chains. Accordingly, 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 emulsifyingagents. In no case, however, must 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%, and preferably amounting to from 5 to 25% of the glycamides.
Suitable emulsion stabilizers include the watersoluble 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% so that the post-treatment agents will still be readily fluid in nature. Others, particularly the polyethylene glycols, can be used in substantially greater quantities, without raising the viscosity to undesirable levels.
The glycamides according to the invention and the compositions containing such glycamides can advantageously be combined with other substances which have heretofore been used as post-treatment agents. These include, for example, optical brighteners, acidifying and disincrusting agents, colorants, perfumes, etc. These substances can be incorporated into the solid or liquid post-treatment agents according to the invention.
The combined use of the above-described softening agents with optical brighteners is to be considered as an important and novel feature of the invention. The brighteners are intended mainly for cellulose fibers, but brighteners for cellulose and/or other fibers, especially synthetic fibers, can be used as well.
Suitable additives for acidification and/or for the removal of ash or other fiber incrustations include the non-oxidizing acids which have been found to be not harmful to the fibers to be treated and particularly those additives which form soluble alkaline earth metal salts, and complex compound formers. The acid reacting substances include for example amidosulfuric acid, urea compounds or orthophosphoric acid or solid organic acids like citric acid. The complex compound formers include for example tripolyphosphates or the higher but still water soluble 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-, trior tetraphosphonic acids.
As instances of halogenated phenols which may be used as antimicrobials, there may be mentioned, for example, chlorination and bromination products of phenol, such as pentachlorophenol, and also halogenated cresols, xylenols, such as 4-bromo-3,5-xylenol or halogenated cyclohexylphenols, methylcyclohexylphenols or benzylphenols.
There may also be used the water-soluble antimicrobial substances of the cationic or hybrid ionic surfactant type, which serve in the final post-treatment 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 to 14 carbon atoms, or alternatively contain 0n 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 car bon atom. The following are instances of the cationic compounds suitable for use in the invention include: diethylbenzyldodecyl ammonium chloride, diethylbenzyloctyl ammonium chloride, and dibutylallyl, me-
thylethylbenzyl, ethylcyclohexylallyl and ethylcrotyldiethylaminoethyl dodecyl ammonium chloride.
There are also 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 phenyl, alkyl, alkoxyl and benzyl radicals may additionally be substituted with chlorine or bromine atoms and/or with nitro groups. Examples of such condensation products include, for instance, the following compounds: oxybenzyloctylamine, oxybenzyldodecyldiethylenetriamine, (2-oxy-5-chloro-6-methylbenzyl)- dodecyldiethylenetriamine, (2-oxy-5-methylbenzyl)octyldiethylenetriamine, (2-oxy-5-chloro-4,6-
diemethylbenzyl)octyldiethylenetriamine, (trisoxybenzyl)-dodecyltriethylenetetramine, o,o-bis-( tetradecylaminomethyl )-p-cresol, o ,0-
wherein 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 and 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: dodecylaminopropylglycinc, tetra- I decylaminoethyl-B-alanine, dodecyl-di-(aminoethyl)- glycine, dodecylaminoisopropylaminomethylsalicylic acid, hexadecyl-tri-(aminoethyl)-B-aminobutyric acid, dodecylbenzylaminopropyl-B-alanine, octylphenoxyethyl-di-(aminoethyl)-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- 1 ,3-oxypropyl-B-aminobutyric acid, C alkyloxyethylaminoacetic acid, dodecyl-l ,2-
oxypropylaminomethylsalicylic acid, octylphenoxyethylaminobenzoic acid.
The compounds that can be used according to the invention furthermore include carboxybetaines of the formula:
which can be used both in the betaine form, i.e., in the form of inner salts, and in the form of acidic or basic salts. 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. Examples of such carboxybetaine compounds are lauroyl-l,3-amidopropyldimethylaminoacetic 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 post-treatment agents can vary within wide limits according to the subsequent intended use of the laundered articles, amounting to 0.5 30% and preferably 1 20% by weight. If 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% of the quantity of the softening agent.
The laundry post-treatment agents according to the invention as noted above constitute solid products and as such have the following composition 30 95 and preferably 70 90 wt-% of solid vehicle substance 70 5 and preferably 30 10 wt-% glycamide 20 and preferably 1 15 wt-% of an optical brightener,-the same being present in a quantity amounting to to 25% of the amount of glycamide present;
0 30 and preferably 1 15 wt-% 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% and most preferably from 5 to 25% of the amount of glycamide;
0 20 and preferably 0.1 wt-% of an emulsion stabilizer or thickening agent, the quantity thereof being regulated so that a 10% aqueous solution or dispersion of the entire solid preparation will have a good fluidity;
0 30 and preferably 1 20 wt-% of at 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% and most preferably to from 5 to 25% of the quantity of the glycamide.
The liquid, laundry post-treatment preparations in accordance with the invention have the following composition 2 30 and preferably 5 wt-% glycamide.
0 50 and preferably 5 30 wt-% solid water-soluble hydrotropic substance and/or water-soluble organic solvent.
0 l0 and preferably 1 8 wt-% of an optical brightener but preferably such a quantity of optical brightener as to amount to 5 to 25% of the amount of the glycamide.
0 l0 and preferably 0 5 wt-% 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 wt-% of the amount of glycamide.
O 20 and preferably 0.1 10 wt-% of a watersoluble emulsion stabilizer or thickening agent, the quantity thereof, however, being regulated so that the final preparation will have good fluidity.
0 30 and preferably 1 20 wt-% 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% and most preferably from 5 to 25% of the quantity of the glycamide. Balance 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.
The Examples given hereinafter serve to illustrate the invention without being in any way or form considered as limitative of the scope of the same.
The glycamides incorporated into the softening agents of the invention and tested in the manner to be described below were prepared on the basis of the fol lowing procedure:
In a three-necked flask equipped with a gas feed tube, agitator, condenser, and a receiver for the distillate, a mixture of 0.22 mole of N-alkylglycamine and 0.20 mole of fatty acid' methyl ester was heated slowly under a current of nitrogen, with intense agitation, to 150 to 170C. The methanol released in the reaction was distilled off and held in a graduated receiver. The reaction mixture was maintained at 150 to 170C until about to of the theoretical amount of methanol had passed over. This required from 2 to 5 hours depending on the starting material. Thereafter the rest of the methanol was removed by two hours of heating in vacuo; the methanol was frozen out in a cooling trap. As soon as 94 to 98% of the theoretical amount of methanol had been recovered, the reaction was ended.
The 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 advantageous effects that are achieved with the aforesaid glycamides i.e. high degree of softness, fullness and absorbency were demonstrated in tests carried out on ordinary cotton fabrics and on cotton terrycloth fabrics, which tests are described fully in the parent application.
EXAMPLE 1 Glucamide R C 2H25; R2 C 7H35; Total C atoms Feel: 2.0
compressibility: Vertical Absorbency: Absorption value:
2 127 St,= 68% S,= 75% A 2% 27 66 St,,= 200% A S, 1700% EXAMPLE 2 Glucamide R C I-I R C I-I Total 29 C atoms Feel: 2.0
Compressibility: Vertical Absorbency: Absorption Value: 2% 122 St,=52% S,=36% A 2 22 A st, 140% A s, 800% EXAMPLE 3 Glucamide R1 C3H OC H33; R2 C15H3 Total C atoms Feel: 1.5
compressibility: Vertical Absorbency: Absorption Value: Z 132 St ,=47% S,=23% AZ =32 ASt,,= 120% AS,, 470% EXAMPLE 4 Glucamide R cm as; R C I-1 Total 27 C atoms F eel: 1.0
Compressibility: Vertical Absorbency: Absorption Value 2% 143 St 30% Not determined because of A Z 43 A St, 35% lack of substance EXAMPLE 5 Glucamide R C I-I R C H Total 25 C atoms Feel: l.5 Compressibility: Vertical Absorbency: Absorption Value 2 134 St, 36% Not determined because of A 2 34 A St, 6l% lack of substance EXAMPLE 6 Glucamide R C C mixture of coconut fatty acids, avg. about C R C f' C mixture of tallow fatty acids, avg.
about C;
Total about 29 carbon atoms Feel: 1.0
compressibility: Vertical Absorbency: Absorption Value EXAMPLE 7 Glucamide R C C fmixture of tallow fatty acids, avg. about C R C c fmixture of coconut fatty acids, avg.
Fructamide R, C C mixture of coconut fatty acids avg. approx. C
R C C 'mixture of tallow fatty acids avg.
approx. C Feel:
Vertical Absorbency: Absorption Compressibility:
Value 2.. 147 St, 40% s, 23% A 2 47 A St 79% s,, 470% EXAMPLE 9 Glycamide mixture from invert sugar R C C fmixture 18coconut fatty acids, avg.
approx. C R C C fmixture of tallow fatty acids, avg.
approx. C Total approx. 29 C atoms Feel: 1.0
Compressibility: Vertical Absorbency: Absorption Value 2% 155 St, 46% S, 23% A z... 55 A st, 100% s,, 490% EXAMPLE 10 Glycamide mixture from invert sugar R C C mixture of tallow fatty acids avg.
approx. C R c fC -fmixture of coconut fatty acids avg.
approx. C Total approx. 29 C atoms Feel: 1.0 Compressibility: Vertical Absorbency: Absorption Value 2 St 34% Not determined because of in- A 2 A St, 62% sufficient substance EXAMPLE A A post-treatment agent according to the invention for use with textiles having the following composition was prepared:
10 wt-% glucamide according to Example 6 30 wt-% isopropanol 2 wt-% ethoxylated dimethylpolysiloxane 1 wt-% 2-bromo-Z-nitro-propanediol-l ,3
10 wt-% tartaric acid 47 wt-% water EXAMPLE B A post-treatment agent for use with conventional laundry .having the following composition was prepared:
10 wt-% glucamide according to Example 1 60 wt-% isopropanol 2 wt-% ethoxylated dimethylpolysiloxane 2 wt-% N-dodecyl-N-benzyl-N,N-dimethyl ammonium chloride 10 wt-% tartaric acid 16 wt-% water The glycamide incorporated into the preparations of Examples A and B are replaced by any of the compounds of Examples 2-5 or 7-10, to secure afterrinsing agents having a similar action We claim:
1. A laundry textile antimicrobial and softening composition consisting esentially of 0.5 to 30 weight percent of a water-soluble, heavy metal-free, nonoxidizing antimicrobial agent selected from the group consisting of nitrated polyalcohols and a quaternary ammonium compound and about 2 to weight percent of a textile fabric softening glycamide of the formula:
wherein:
R, 1) alkyl of to 22 carbon atoms or, (2) alkyl of 10 to 22 carbon atoms with an ether oxygen linkage between either the two and three or 3 and 4 carbon atoms from the nitrogen atom,
R alkyl of seven to 21 carbon atoms,
R R; have 23 to 39 carbon atoms.
2. The composition of claim 1 in solid form wherein said glycamide comprises 10 to 30 weight percent thereof.
3. The composition of claim 2 in the form of a solution wherein said glycamide comprises 2 to 30 weight percent thereof, and, other than said antimicrobial agent, the balance being water or a water-soluble or- UNITED STATES PATENT OFFICE CERTIFICATE OF CORRECTION Patent No. 3,764,531 Dated October 9, 1973 lnvent fl Hans-Werner Eckert et a1.
It is certified that error appears inthe above-identified patent and that said Letters Patent: are hereby corrected as shown below:
' Col,- 3, line, 7 afte rf'about insert- 0.5g/l
Col. 8, line 67, upder 'A bs dr pti o n Value" change 75% f 'to i37. V I I I Col 8,? line 68; Under VIe-rtiozial 'Ab'sorbency'" charxge "66" t :o
u A If. I 1001. 10,line 5 cancel 18" and substitute of Col. 11, linev9 (Claim 2 line 1) caneel "in solid form";
Signed and sealed this ZBfd day of July 197 (SEAL) Attest: MCCOY M. GIBSON JR. c. MARS ALL DANN Atte'stingoffieer Commissioner of Patents

Claims (3)

  1. 2. The composition of claim 1 in solid form wherein said glycamide comprises 10 to 30 weight percent thereof.
  2. 3. The composition of claim 2 in the form of a solution wherein said glycamide comprises 2 to 30 weight percent thereof, and, other than said antimicrobial agent, the balance being water or a water-soluble organic solvent 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.
  3. 4. The composition of claim 3 wherein said nitrated polyalcohols is 2-bromo-2-nitro-propanediol - 1, 3, and wherein said quaternary ammonium compound is N-dodecyl-N-benzyl-N, N-dimethyl ammonium chloride.
US00088486A 1966-08-01 1970-11-10 Antimicrobial and laundry softening compositions Expired - Lifetime US3764531A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEH0060124 1966-08-01
DEH0062816 1967-05-23

Publications (1)

Publication Number Publication Date
US3764531A true US3764531A (en) 1973-10-09

Family

ID=25980481

Family Applications (2)

Application Number Title Priority Date Filing Date
US656136A Expired - Lifetime US3637495A (en) 1966-08-01 1967-07-26 Agent for the posttreatment of laundry
US00088486A Expired - Lifetime US3764531A (en) 1966-08-01 1970-11-10 Antimicrobial and laundry softening compositions

Family Applications Before (1)

Application Number Title Priority Date Filing Date
US656136A Expired - Lifetime US3637495A (en) 1966-08-01 1967-07-26 Agent for the posttreatment of laundry

Country Status (10)

Country Link
US (2) US3637495A (en)
AT (1) AT280938B (en)
BE (1) BE702083A (en)
CH (1) CH517208A (en)
DK (1) DK118182B (en)
ES (1) ES343644A1 (en)
FR (1) FR1550144A (en)
GB (1) GB1175234A (en)
NL (1) NL6709356A (en)
SE (1) SE319156B (en)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3899616A (en) * 1973-11-09 1975-08-12 Frank A Simonelli Fungistatic fabric treatment
EP0422508A2 (en) * 1989-10-09 1991-04-17 Kao Corporation Liquid detergent composition
WO1992006153A1 (en) * 1990-09-28 1992-04-16 The Procter & Gamble Company Detergent compositions with polyhydroxy fatty acid amide surfactant and polymeric dispersing agent
US5234618A (en) * 1989-10-09 1993-08-10 Kao Corporation Liquid detergent composition
US5283009A (en) * 1992-03-10 1994-02-01 The Procter & Gamble Co. Process for preparing polyhydroxy fatty acid amide compositions
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
US5698046A (en) * 1993-09-09 1997-12-16 The Procter & Gamble Comapny Automatic dishwashing detergent with alkoxy or aryloxy amide surfactant
US6405809B2 (en) 1998-01-08 2002-06-18 M-I Llc Conductive medium for openhold logging and logging while drilling
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
US20220372399A1 (en) * 2019-09-19 2022-11-24 Conopco, Inc., D/B/A Unilever Detergent compositions
EP4356733A1 (en) * 2022-10-19 2024-04-24 Bode Chemie GmbH Low alcohol disinfectant

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE319156B (en) * 1966-08-01 1970-01-12 Henkel & Cie Gmbh
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
US4151097A (en) * 1976-07-26 1979-04-24 Lever Brothers Company Liquid systems
GB1596791A (en) * 1977-02-15 1981-08-26 Unilever Ltd Deodorant detergent composition
GB2124618A (en) * 1982-06-11 1984-02-22 Nat Res Dev Aliphatic hydroxy amides
MY100343A (en) * 1985-12-20 1990-08-28 Kao Corp Amide derivative and external medicament comprising same
DE3877910T2 (en) * 1987-11-19 1993-05-19 British Petroleum Co CONDITIONING AGENTS FOR TEXTILE MATERIALS.
DE69105520T2 (en) * 1990-09-28 1995-06-08 Procter & Gamble PHASE TRANSFER METHOD FOR GLUCAMIDE DETERGENTS.
SK25193A3 (en) * 1990-09-28 1993-07-07 Procter & Gamble Detergent composition containing polyhydroxy fatty acid amides and alkyl ester sulfonate surfactants
US5194639A (en) * 1990-09-28 1993-03-16 The Procter & Gamble Company Preparation of polyhydroxy fatty acid amides in the presence of solvents
DE69114716T2 (en) * 1990-09-28 1996-06-13 Procter & Gamble POLYHYDROXY FATTY ACID AMIDES IN DETERGENT-RESISTANT COMPOSITIONS.
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
ES2069311T3 (en) * 1990-09-28 1995-05-01 Procter & Gamble IMPROVED CATALYST PROCEDURE FOR GLUCAMIDE DETERGENTS.
WO1992006070A1 (en) * 1990-09-28 1992-04-16 The Procter & Gamble Company High catalyst process for glucamide detergents
JPH06501043A (en) * 1990-09-28 1994-01-27 ザ、プロクター、エンド、ギャンブル、カンパニー Polyhydroxy fatty acid amide surfactants in bleach-containing detergent compositions
US5254281A (en) * 1991-01-29 1993-10-19 The Procter & Gamble Company Soap bars with polyhydroxy fatty acid amides
DE69113259T2 (en) * 1991-07-08 1996-05-15 Procter & Gamble Polyhydroxy fatty acid amide surfactants and a softening system based on clay-containing detergent compositions.
US5449770A (en) * 1992-01-14 1995-09-12 The Procter & Gamble Company Process for making N-alkylamino polyols
CA2339311C (en) * 1991-07-26 2002-09-17 Robert Edward Shumate Process for preparing improved nickel catalysts for use in hydrogenation reactions
AU4398793A (en) * 1992-06-15 1994-01-04 Procter & Gamble Company, The Liquid laundry detergent compositions with silicone antifoam agent
CN1134720A (en) * 1993-09-09 1996-10-30 普罗格特-甘布尔公司 Detergent compositions with mixture of n-alkoxy or n-aryloxy polyhydroxy fatty acid amide plus alkoxylated carboxylate surfactant
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
CA2181797A1 (en) * 1994-01-25 1995-07-27 Jeffrey John Scheibel Polyhydroxy diamines and their use in detergent compositions
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
EP0919608A1 (en) * 1997-11-25 1999-06-02 The Procter & Gamble Company Use of a polyhydroxyfatty acid amide compound as a softening compound
ES2217749T3 (en) 1998-05-20 2004-11-01 Kao Corporation SOFTENING FINISH COMPOSITION.
US6541444B1 (en) 1998-05-20 2003-04-01 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
MXPA03008101A (en) * 2001-03-07 2003-12-12 Procter & Gamble Rinse-added fabric conditioning composition for use where residual detergent is present.
GB0106466D0 (en) * 2001-03-15 2001-05-02 Unilever Plc Fabric softening compositions
US20180171521A1 (en) * 2016-12-19 2018-06-21 John Mahdessian Green rejuvenation system and kit

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US3329609A (en) * 1965-03-22 1967-07-04 Wyandotte Chemicals Corp Compositions containing quaternary ammonium salts
US3349033A (en) * 1964-08-26 1967-10-24 Millmaster Onyx Corp Stable microbiologically active laundry softener
US3637495A (en) * 1966-08-01 1972-01-25 Henkel & Cie Gmbh Agent for the posttreatment of laundry
US3644204A (en) * 1967-08-14 1972-02-22 Henkel & Cie Gmbh Agent for the post-treatment of washed laundry

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US3364142A (en) * 1965-12-06 1968-01-16 Northern Petro Chem Co Composition for reconstituting frozen aqueous systems and method for making

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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
US3349033A (en) * 1964-08-26 1967-10-24 Millmaster Onyx Corp Stable microbiologically active laundry softener
US3329609A (en) * 1965-03-22 1967-07-04 Wyandotte Chemicals Corp Compositions containing quaternary ammonium salts
US3637495A (en) * 1966-08-01 1972-01-25 Henkel & Cie Gmbh Agent for the posttreatment of laundry
US3644204A (en) * 1967-08-14 1972-02-22 Henkel & Cie Gmbh Agent for the post-treatment of washed laundry

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3899616A (en) * 1973-11-09 1975-08-12 Frank A Simonelli Fungistatic fabric treatment
EP0422508A2 (en) * 1989-10-09 1991-04-17 Kao Corporation Liquid detergent composition
EP0422508A3 (en) * 1989-10-09 1992-08-26 Kao Corporation Liquid detergent composition
US5234618A (en) * 1989-10-09 1993-08-10 Kao Corporation Liquid detergent composition
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
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
US5698046A (en) * 1993-09-09 1997-12-16 The Procter & Gamble Comapny Automatic dishwashing detergent with alkoxy or aryloxy amide surfactant
US6787505B1 (en) 1997-09-15 2004-09-07 M-I Llc Electrically conductive non-aqueous wellbore fluids
US6405809B2 (en) 1998-01-08 2002-06-18 M-I Llc Conductive medium for openhold logging and logging while drilling
US20030075360A1 (en) * 1998-01-08 2003-04-24 Patel Arvind D. Double emulsion based drilling fluids
US6793025B2 (en) 1998-01-08 2004-09-21 M-I L. L. C. Double emulsion based drilling fluids
US20220372399A1 (en) * 2019-09-19 2022-11-24 Conopco, Inc., D/B/A Unilever Detergent compositions
EP4356733A1 (en) * 2022-10-19 2024-04-24 Bode Chemie GmbH Low alcohol disinfectant
WO2024083742A1 (en) * 2022-10-19 2024-04-25 Bode Chemie Gmbh Low-alcohol disinfectant

Also Published As

Publication number Publication date
SE319156B (en) 1970-01-12
US3637495A (en) 1972-01-25
FR1550144A (en) 1968-12-20
DK118182B (en) 1970-07-20
AT280938B (en) 1970-04-27
BE702083A (en) 1968-01-31
CH517208A (en) 1971-12-31
ES343644A1 (en) 1968-09-01
GB1175234A (en) 1969-12-23
NL6709356A (en) 1968-02-02

Similar Documents

Publication Publication Date Title
US3764531A (en) Antimicrobial and laundry softening compositions
US3644204A (en) Agent for the post-treatment of washed laundry
EP0158260B1 (en) Detergent for coloured textiles
GB1565808A (en) Fabric softeners and detergent compositions containing imidazolines derivatives
DE2327857B2 (en) Liquid foam-controlled detergent
EP0035263A2 (en) Polyester compounds, a process for their preparation, and their use as textile softeners
US4659487A (en) Concentrated fabric softeners
US3897347A (en) Washing agents containing a textile softener and process of washing and softening textiles
US4281196A (en) Quaternary ammonium compounds, their preparation, and their use as softening agents
JPS6338470B2 (en)
DE3205317A1 (en) AGENT AND METHOD FOR TREATING WASHED LAUNDRY
US3417023A (en) Detergent spotting stick
US3729416A (en) Liquid softening rinsing agent compositions
DE3444068A1 (en) AGENT AND METHOD FOR TREATING WASHED LAUNDRY
DE2925859A1 (en) Textile rinsing compsn. improving softness and absorption capacity - contg. quat. ammonium salt and water soluble quat. ammonium gp.-contg. poly:galactomannan ether
JPH027994B2 (en)
EP0056151B1 (en) Process for the microbicidal finishing of textiles
GB2095277A (en) Disinfecting cleaning intensifier for dry cleaning
US4873002A (en) Liquid detergent fabric conditioning compositions
CA1235860A (en) Liquid detergent fabric conditioning composition
US3625891A (en) Wash cycle fabric softeners and method of preparing and using same
US4129506A (en) Fabric softeners
GB2095254A (en) Tri-(tert-ammonium) salts of citric and tricarballylic acids and their use in reducing the discolouration of textiles during washing or dry cleaning
US3862905A (en) Washing agents containing an aminocarbonamide textile softener and process of washing and softening textiles
DE2360020A1 (en) LOW-FOAMING DETERGENT, DISHWASHER AND CLEANING AGENT