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Publication numberUS3764531 A
Publication typeGrant
Publication dateOct 9, 1973
Filing dateNov 10, 1970
Priority dateAug 1, 1966
Also published asUS3637495
Publication numberUS 3764531 A, US 3764531A, US-A-3764531, US3764531 A, US3764531A
InventorsBellinger H, Eckert H, Heins A
Original AssigneeHenkel & Cie Gmbh
Export CitationBiBTeX, EndNote, RefMan
External Links: USPTO, USPTO Assignment, Espacenet
Antimicrobial and laundry softening compositions
US 3764531 A
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:
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Description  (OCR text may contain errors)

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:


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

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Referenced by
Citing PatentFiling datePublication dateApplicantTitle
US3899616 *Nov 9, 1973Aug 12, 1975Simonelli Frank AFungistatic fabric treatment
US5234618 *Oct 1, 1991Aug 10, 1993Kao CorporationLiquid detergent composition
US5283009 *Mar 10, 1992Feb 1, 1994The Procter & Gamble Co.Process for preparing polyhydroxy fatty acid amide compositions
US5489393 *Jul 26, 1994Feb 6, 1996The Procter & Gamble CompanyHigh sudsing detergent with n-alkoxy polyhydroxy fatty acid amide and secondary carboxylate surfactants
US5698046 *Jun 7, 1996Dec 16, 1997The Procter & Gamble ComapnyReduces spotting and filming on tableware
US6405809Jan 10, 2001Jun 18, 2002M-I LlcConductive medium for openhold logging and logging while drilling
US6787505Feb 9, 1998Sep 7, 2004M-I LlcThe wellbore fluid can be used for providing enhanced information from electrical logging tools, measurement while drilling, logging while drilling, geosteering and the like.
US6793025Jun 17, 2002Sep 21, 2004M-I L. L. C.Double emulsion based drilling fluids
EP0422508A2 *Oct 4, 1990Apr 17, 1991Kao CorporationLiquid detergent composition
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U.S. Classification510/518
International ClassificationC11D3/32, C11D1/38, C11D1/52, C11D3/26, C11D3/00, D06M13/00, D06M13/372
Cooperative ClassificationD06M13/372, C11D1/525, C11D3/32, C11D3/001
European ClassificationC11D3/00B3, C11D1/52H, D06M13/372, C11D3/32