US3244636A - Antimicrobial detergent compositions - Google Patents

Antimicrobial detergent compositions Download PDF

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US3244636A
US3244636A US298491A US29849163A US3244636A US 3244636 A US3244636 A US 3244636A US 298491 A US298491 A US 298491A US 29849163 A US29849163 A US 29849163A US 3244636 A US3244636 A US 3244636A
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antimicrobial
dibenziodolium
compounds
detergent
oxiodinium
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Herbert H Reller
Quinn Herbert
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Procter and Gamble Co
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Procter and Gamble Co
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Priority to US298491A priority Critical patent/US3244636A/en
Priority to SE9122/64A priority patent/SE324424B/xx
Priority to DEP34778A priority patent/DE1258006B/de
Priority to FI1627/64A priority patent/FI41184B/fi
Priority to DK376064AA priority patent/DK124618B/da
Priority to FR983372A priority patent/FR1448750A/fr
Priority to GB31045/64A priority patent/GB1046896A/en
Priority to CH515065A priority patent/CH455116A/de
Priority to NL6510151A priority patent/NL6510151A/xx
Priority to BE675135A priority patent/BE675135A/xx
Priority to AU784/66A priority patent/AU410302B1/en
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • C—CHEMISTRY; METALLURGY
    • C21—METALLURGY OF IRON
    • C21C—PROCESSING OF PIG-IRON, e.g. REFINING, MANUFACTURE OF WROUGHT-IRON OR STEEL; TREATMENT IN MOLTEN STATE OF FERROUS ALLOYS
    • C21C7/00—Treating molten ferrous alloys, e.g. steel, not covered by groups C21C1/00 - C21C5/00
    • C21C7/04—Removing impurities by adding a treating agent
    • C21C7/06—Deoxidising, e.g. killing

Definitions

  • This invention relates to cleansing and detergent compositions which in addition to effectively removing soil also possess antimicrobial activitiy. More especally, this invention relates to antimicrobial detergent compositions which contain as the primary antimicrobial agent, certain heterocyclic iodine-containing compounds termed broadly as dibenziodolium compounds, which are characterized in detail below.
  • compositions containing anionic detergent surface active agents including soaps and non-soap compounds, and previously known antimicrobial agents.
  • anionic detergent is less effective in its cleaning function than when used alone and the microbial control is substantially less than when the agent is used alone.
  • Similiar interference commonly occurs in compositions containing nonionic, cationic and amphoteric surface active agents also.
  • antimicrobial agents have become available recently which do impart some static or cidal action to soap and synthetic detergent systems against Gram positive bacteria such as Staphylococcus aureus', Bacterium ammoniagener, Lactolmcillus casei, etc.
  • Gram positive bacteria such as Staphylococcus aureus', Bacterium ammoniagener, Lactolmcillus casei, etc.
  • antimicrobial agents are known which are compatible with, and impart significant antibacterial activity to soap and detergent systems against the more resistant Gram negative bacteria such as Escherichia coli, Proteus mirabilis, Pseudomonas aeruginosa, Salmonella choleraeszn's, etc.
  • Compatible antimicrobial agents are especially sought for use in detergent compositions which are to be used in laundering applications. In such situations it is desirable to have a residual amount of the disinfecting agent retained on the cloth in order to provide longer lasting effectiveness.
  • the dibenziodolium compounds, described hereinafter, as a class have been discovered to possess such activity to a considerable degree.
  • antimicrobial agents are '4/ a United States Patent 0 3,244,636 Patented Apr. 5, 1966 ice needed which can be used in a washing solution, remain on the fabric, and prevent multiplication of bacteria and/ or fungi and the development on the fabric of body odors.
  • One advantage and application of such a treatment occurs in the washing of infants diapers, especially if the adherent antimicrobial agent is effective against Gram negative bacteria.
  • Such bacteria attack nitrogen-containing compounds present in the materials with which the diapers are soiled forming ammonia.
  • the Gram negative bacteria are effectively destroyed, the unpleasant odor problems encountered in storing soiled diapers until they can be washed can be alleviated.
  • Trichlorocarbanilides and salicylanilides are good examples of agents which are destroyed by chlorine-type bleaches such as the widely used 5%% sodium hypochlorite solutions and potassium dichlorocyanurate-based dry bleaches.
  • An unexpected advantage of the compositions of this invention is that they are stable in the presence of chlorinetype bleaches.
  • Antimicrobial agents which are compatible with soaps and synthetic detergents also find utility in the area of deodorant soap and cosmetic bars, i.e. toilet soaps.
  • the active compound it is desirable for the active compound to exhibit substantivity to human skin so that the agent can be present to control the bacterial flora of the skin, which decomposes perspiration with concomitant odor development after a washing treatment.
  • an object of this invention to provide highly improved antimicrobial detergent compositions comprising a cleansing agent and an effective amount of a compatible heterocyclic iodine-containing antimicrobial agent. Another object is to provide an antimicrobial detergent composition which cleans effectively and is simultaneously capable of controlling a broad spectrum of Gram positive and, more especially, Gram negative organisms. Another object is to provide an antimicrobial detergent composition which may be used conjointly with and is effective in the presence of chlorine-type bleaches. A yet further object is to provide a new method of imparting antimicrobial properties to fabrics washed by the detergent compositions of this invention.
  • Another object is to provide cotton and other fabrics having substantively distributed thereon an effective amount of an antimicrobial dibenziodolium compound deposited by a washing step employing an antimicrobial detergent composition of this invention ina manner described hereinafter.
  • a still further object is to provide a so-called germicidal deodorant toilet soap bar comprising a cleansing agent and a minor but effective amount of the antimicrobial dibenziodolium compound.
  • detergent compositions containing a cleansing agent and an effective amount of at least one dibenziodolium compound having the structure set forth below.
  • Dibenziodolium antimicrobial agents are compositions of matter having the following generic structural formula:
  • R is selected from the group consisting of oxygen, sulfur, and --(CH,),,,-, m being an integer from 0 to 3;
  • Y and Y represent radicals selected from the group consisting of halogen, nitro, alkyl radicals containing up to 3 carbon atoms, halogen substituted alkyl radicals containing up to 3 carbon atoms, amino and sulfamyl, and Y and Y can be dissimilar;
  • n and n represent integers selected from the group consisting of 0, 1 and 2, and when n is 2, the Y radicals can be dissimilar and when n is 2 the Y radicals can be dissimilar and,
  • X is selected from the group consisting of organic and inorganic anions.
  • dibenziodolium compounds i.e., where m and n are in the above formula and, what may be thought of as the parent compounds, contain a C 1 heterocyclic ring and no substituents on the phenylene rings.
  • Such compounds are structurally represented by the following formula in which X is an anion:
  • the anionic portion, X can be either an organic or inorganic anion.
  • Inorganic anions sulfate, bisulfate, sulfite, iodide, chloride, bromide, phosphate, biphosphite, pyrophosphate, nitrate, nitrite and the like.
  • Exemplary organic anions include acetate, propionate, decanoate, benzoate, substituted benzoate, phenylacetate, benzenesulfonate, substituted benzenesulfonate, fumarate, lactate, tartrate, citrate and the like.
  • the anion By selectively varying the anion, it is possible to adapt the dibenziodolium compounds to a variety of applications, due to the different physical and solubility characteristics of the different salt forms. Wide selection exists as to the anion, for the anion is not critical to the antimicrobial and compatibility characteristics of the compositions of this invention.
  • R can be an alkylenc group such as methylene, ethylene or propylene
  • R can be an alkylenc group such as methylene, ethylene or propylene
  • propylene-containing compounds, dihydrodibenziodocinium compounds These compounds have the following structural formula wherein m is 1, 2, or 3 respectively:
  • the heterocyclic ring can contain an oxygen atom or a sulfur atom in place of methylene, ethylene and propylene along with iodine and carbon.
  • Such compounds are referred to respectively as dibenzoxiodinium compounds having the following structural formula:
  • dibenziodolium is used in the description of this invention in its broadest sense to include each of the specific compound forms illustrated above. It has been discovered that the beneficial characteristics described in this invention are possessed according to varying degrees by all of the compounds falling within the above structural formulas.
  • Typical of the antimicrobial compounds contemplated by this invention include:
  • o-iodobiphenyl or o-iodobiphenyl alkane (V1) is oxidized with peracetic acid to yield the corresponding iodoso acetate compound (VH).
  • VH iodoso acetate compound
  • This compound is reacted with sulfuric acid and thus reduced to a heterocyclic dibenziodolium compound bial activity to a broad spectrum of detergent surfactant compositions. Due to the cationic nature of the dibenziodolium compounds, it was confidently expected that incompatibilties might exist with anionic and amphoteric detergent surface active agents. Contrary to expectations, it was found that the dibenziodolium compounds can be used with excellent results in combination with anionic and amphoteric detergent surfactants.
  • compositions of this invention are effective against a large number of yeast and fungus organisms which are known to cause infections of the skin and mucous membranes.
  • Relatively small amounts of the dibenziodolium antimicrobial agents are sufficient to render the detergent compositions germicidal. Amounts as low as 0.01% based on the weight of the detergent composition have proved satisfactory in some cases.
  • the preferred concentration range is from 0.05% to 4% by weight of the synthetic detergent or soap composition used. The upper limit will generally be determined by practical considerations such as economics and desired solubility characteristics. Usage levels as high as 10% by weight of the detergent composition can be used to advantage. As a general rule, increasing the concentration of the agent increases the antimicrobial effectiveness of the composition.
  • Anionic organic detergents which can be used in the composition of this invention, if desired, include both the soap and non-soap variety.
  • soaps as used herein is meant to designate alkali metal soaps such as sodium and potassium salts of the higher fatty acids of naturally occurring plant or animal esters, e.g., palm oil, coconut oil, babassu oil, soybean oil, castor oil, tallow, whale and fish oils, grease and lard, and mixtures thereof.
  • Sodium and potassium soaps can be made by direct saponification of the fats and oils or by the neutraliza tion of the fatty acids which are prepared in a separate manufacturing process.
  • Suitable soaps are the sodium, potassium, ammonium and alkylolammonium salts of higher fatty acids (C C Particularly useful are the sodium and potassium salts of the mixtures of fatty acids derived from coconut oil and tallow, i.e., sodium or potassium tallow and coconut soap.
  • anionic organic non-soap detergents include those broadly described as the water-soluble salts, particularly the alkali metal salts, of organic sulfuric reaction products having in their molecular structure an alkyl radical containing from about 8 to about 22 carbon atoms and a radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals. Included in the term alkyl is the alkyl portion of higher acyl radicals.
  • the synthetic non-soap detergents which form a part of the preferred compositions of the present invention are the sodium alkyl sulfates, especially those obtained by sulfating the higher alcohols (C -C carbon atoms) produced by reducing the glycerides of tallow or coconut oil; sodium or potassium alkylbenzenesulfonates, in which the alkyl group contains from about 9 to about 15 carbon atoms in a straight or branched chain, for example, those of the types described in United States Letters Patents Nos.
  • sodium alkyl glyceryl ether sulfonates especially those ethers of the higher alcohols derived from tallow and coconut oil; sodium coconut oil fatty acid monoglycerides sulfates and sulfonates; sodium or potassium salts of sulfuric acid esters of the reaction product of one mole of a higher fatty alcohol, e.g., tallow or coconut oil alcohols, and about 1 to 6 moles of ethylene oxide, sodium or potassium salts of alkylphenol ethylene oxide ether sulfate with about 1 to about 10 units of ethylene oxide ether per molecule and in which the alkyl radicals contain about 9 to 12 carbon atoms; the reaction product of fatty acids esten'fied with isethionic acid and neutralized with sodium hydroxide, where, for example, the fatty acids are derived from coconut oil; sodium or potassium salts of fatty acid amide of a methyltauride in which the fatty acids,
  • amphoteric synthetic detergents which can be used within by this invention can broadly be described as derivatives of aliphatic amines which contain a long chain of about 8 to about 18 carbon atoms, and an anionic water-solubilizing group, e.g., carboxyl, sulfo, sulfato. Examples of compounds falling within this definition are sodium-3dodecylaminopropanesulfonate and sodium-3- dodecylaminopropionate. I Zwitterionic surface active compounds which are structurally similar to the amphoterics as just described are intended to be covered by that term in this invention.
  • Zwitterionic synthetic detergents can be broadly described as derivatives of aliphatic quaternary ammonium compounds, in which the aliphatic radical may be straight chain or branched and wherein one of the aliphatic substituents contains from about 8 to 18 carbon atoms and one contains an anionic watersolubilizing group, e.g., carboxy, sulfo, or sulfato.
  • anionic watersolubilizing group e.g., carboxy, sulfo, or sulfato.
  • Examples of compounds falling within the definition are 3- (N,N dimethyl N hexadecylammonio) propane-1- sulfonate (APS) and 3-(N,N-dimethyl-N-hexadecylammonio)-2-hydroxy-propane-l-sulfonate (HAPS).
  • 0.1 ml. of the organism (10" cells) is added to the tube containing the agent after which the tube is incubated for 24 hours at 37 C., and thereafter the bacteriostatic breakpoint is determined turbidometrically.
  • compositions of this invention in the form of a sulfate salt (I). the compositions of this invention.
  • the iodo starting material of Reaction A is chlorinated t form the iodo dichloride compound (VIII).
  • Treatment of the iodo dichloride with alkali yields the corresponding iodoso compound (VII) which can in turn be transformed to the desired heterocyclic dibenziodolium compound (I) by treatment with sulfuric acid or other strong Lewis acid.
  • Other salts can be prepared from the above salts by methods well known to the art, such as a metathetic reaction. For example, an aqueous solution of bis(dibenziodolium)sulfate can be treated with an aqueous solution of barium chloride or barium nitrate to form dibenziodolium nitrate or chloride and a readily separable insoluble precipitate of barium sulphate.
  • barium hydroxide can be reacted with bis(dibenziodoliurn)sulfate to yield an insoluble precipitate of barium sulphate plus a solution of dibenziodolium hydroxide.
  • Neutralization of the hydroxide with any suitable acid yields a dibenziodolium salt in which the anion of the acid becomes the anion 0f the dibenziodolium salt.
  • R is hydrogen, lower alkyl, or hydroxy lower alkyl; R" is lower alkyl, lower alkenyl, carboxy-substituted lower alkyl, or a-hydroxy carboxy-substituted lower alkyl.
  • This group of salts can be prepared in the same manner as outlined above except that lactic, tartaric, or citric acid is used to neutralize the dibenziodolium hydroxide, dibenziodinium hydroxide, dihydrodibenziodepinium hydroxide, or dihydrodibenziodocinium hydroxide.
  • the oxygen and sulfur derivatives as exemplified respectively by Formulas IV and V can be prepared by tetra-azotizing a suitably substituted 2,2'-diamino-diphenyl oxide or 2,2-diamino-diphenylsulfide and then decomposing the tetra-azoate in the presence of an iodide salt.
  • a preferable method, however, for the preparation of the oxygen and sulfur compounds involves the direct iodination of a suitably substituted diphenyl ether or diphenyl sulfide using iodosyl sulfate in sulfuric acid solution as the iodinating reagent.
  • the product of this reaction is usually a dibenz(be)( 1,4)oxiodinium or thiaiodinium bisulfate. Recrystallization of the bisulfate salt from water usually serves to convert it to the corresponding sulfate salt.
  • the various dibenzoxiodinium and dibenzthiaiodinium salts which are prodced by any of the above three reactions can be transformed to other salts by standard metathetic processes.
  • a sulfate salt can be dissolved in water and treated with a large excess of sodium chloride to yield the corresponding chloride, or with a large excess of sodium nitrate to yield the corresponding nitrate.
  • Other methods of preparing salts of the dibenzoxiodinium or dibenzthiaiodinium compounds of this invention will be readily apparent to those skilled in the art.
  • the representative amphoteric surface active compound was 3-(hexadecyldimethylammonio -2-hydroxypropane-l-sulfonate HAPS)
  • HAPS 3-(hexadecyldimethylammonio -2-hydroxypropane-l-sulfonate HAPS)
  • Iodolium compound Slaphylo- Eschericoccus chin coli aumts Bis (dibenziodolium) sulfate, alone 3. 75 3.13 with u ABS 6. 25 l 6. 25 Dlbenzlodolium bisulfate, alone 6.25 12. with ABS 6. 25 1 12. 5 Bis (3-nitrodibenziodolium) sulfate, alone 47 1 .12 with Cu ABS 2-3 5 with HAPS.. 1 5 3,7dinitrodibenz(be) (1,4)oxiod1nium bisultate.
  • the Cloth Protection Test consists of washing cloth swatches in an aqueous solution containing a detergent composition and the antimicrobial agents to be tested, drying the swatches in a microorganism free atmosphere, and then inoculating the dried swatch with 0.1 ml. of a suspension of test organism in 5% serum (0.1 ml. containing approximately 5000 organisms).
  • the swatches are again allowed to dry and then they are planted in an agar medium Petri plate with the inoculated surface facing up and an overlay of nutrient is carefully applied over the fabric.
  • the Petri plates are then incubated at 37 C. for 48 hours, after which bacterial counts are taken by means of a low power binocular microscope.
  • the relative ability of a treated fabric to inhibit growth or kill the organism is the measure of the effectiveness of a particular agent or mixtures of agents being tetsed.
  • Tables 11, 111 and IV where these experimental results are given, the lower number of colonies counted indicates the relative greater antimicrobial control of the organism as compared to a control figure obtained without one of the agents. Each figure represents an average of the colonies counted on six replicate cloth swatches.
  • the standardized detergent composition employed in these tests consisted of the following ingredients on a weight basis:
  • the composition was used at a concentration of .25% by weight of the washing solution.
  • the temperature of the washing solution was F. and contained 7 grains of hardness.
  • the antimicrobial agent was used at the percentage levels indicated in the tables. All percentages are on a weight basis and the percent of the dibenziodolium is based on weight of the total detergent composition.
  • dibenziodolium compounds and other anionic detergent surfactants were evaluated in a similar manner and these data are presented in Table V.
  • the dibenziodolium compound selected being representative of the broad class of di'benziodoliums was dibenziodolium sulfate, corresponding to Formula II above.
  • the detergent composition used in Table V was exactly as described previously and was used at the same concentration in the washing solution. Where a one-toone detergent surfactant mixture was tested in place of a sole detergent surfactant, the mixture was present at 17.5% by weight in the compositions. By virtue of the one-to-one ratio, each surfactant was used at an 8.75% by weight level.
  • dichlorocyanuric acid and the sodium and potassium salts thereof are dichlorocyanuric acid and the sodium and potassium salts thereof; trichlorocyanuric acid; 1,3-dichloro-5,5-dimethyl hydantoin; N,N'-dichlorobenzoylene urea; paratoluene sulfondichloroamide; trichloromelamine; N-chloroammeline; N-chlorosuccinimide; N,N'-dichloroazodicarbonamidine; N-chloroacetyl urea; N,N'-dichlorobiuret; chlorinated dicyandiamide; sodium hypochlorite; calcium hypochlorite; lithium hypochlorite; chlorinated trisodium phosphate.
  • oxiodinium chloride 3 890 3, 110 3, 010 600 1-eh1or0dibenz( )(l,4) oxiodinium chloride. 3, 930 210 0 Control figure 3, 910 3, 580 3, 420 2, 300
  • the bactericidal assay test used in this series was carried out by determining the percent kill of typical organisms by exposing a suspension of bacteria to a desired test agent, removing aliquots of the treated suspension at a specified time interval and inoculating onto a 5% serum-agar plate, and thereafter incubating the agar plate 24-48 hours and noting the number of bacterial colonies which develop.
  • this series of tests was carried out by determining the percent kill of Staphylococcus aureus FDA 209 and Escherichia coli in a matrix with an exposure time of 10 minutes to a predetermined concentration of the antimicrobial agent.
  • the suspending medium was FDA nutrient broth, and the inoculum size was approximately 500,000 cells/ml.
  • One-tenth milliliter of the suspension was removed after the 10-minute exposure and placed in 9.9. ml. of 0.1% peptone water.
  • One-tenth ml. of the diluted suspension was plated into Trypticasesoy Agar and allowed to incubate for 24-48 hours at 37 C. Colonies were then counted and the percent reduction in viable count was determined in relation to a colony of dodecylbenzcnc sulionate, the dodecyl substituent derived from tetrapropylcnc,
  • Table VI and VII show that a broad range of activity is achieved between the dibenziodolium compounds and anionic and amphoteric detergent compounds.
  • the markedenhanced activity apparent from Tables VI and VII was completely unexpected. Apparently there is an unexplainable favorable interaction between detergent compounds, the antimicrobal agents and the microorganisms.
  • the preferred compounds according to this invention are the dibenzoxiodinium compounds corresponding to Formula IV above.
  • the chloro-derivatives such as bis(3,7-dichlorodibenz(be)(l,4)oxiodinium)sulfate, 3 chlorodibenz(be)(1,4)oxiodinium chloride, 2 chlorodibenz(be) (1,4)oxiodinium chloride, and l chlorodibenz(be)(1,4) oxiodinium chloride.
  • the unsubstituted species, dibenz- (be) (l,4)oxiodinium chloride also is preferred.
  • the dibenziodolium compounds have been found compatible with the above identified soaps and non-soap synthetic detergent compositions in bar, liquid, flake, granular, and other built or unbuilt forms and can be incorporated into the soap or detergent composition by any suitable method which preferably yields as a result a uniform distribution of agents throughout the whole mass.
  • the detergent compositions of this invention can contain any of the usual adjuvants, diluents, and additives, for example, builders, perfumes, anti-tarnishing agents, anti-redeposition agents, dyes, fluorescers, suds builders, suds depressors as well as cationic synthetic detergent surfactants, without detracting from the advantageous properties of the compositions.
  • adjuvants for example, builders, perfumes, anti-tarnishing agents, anti-redeposition agents, dyes, fluorescers, suds builders, suds depressors as well as cationic synthetic detergent surfactants, without detracting from the advantageous properties of the compositions.
  • toilet soap bar containing 1.0% of a suitable dibenziodolium compound of this invention such as 3,7-dinitrodibenz(be)(1,4)oxiodinium bisulfate, bis- (2-nitrodibenziodolium)sulfate, or bis(3-nitrodibenziodolium)sulfate, results in substantial reduction in bacterial population of the skin and thereby markedly reduces body odor attributable to the bacterial degradation of perspiration.
  • a suitable dibenziodolium compound of this invention such as 3,7-dinitrodibenz(be)(1,4)oxiodinium bisulfate, bis- (2-nitrodibenziodolium)sulfate, or bis(3-nitrodibenziodolium)sulfate
  • Example 1 A sample formula for a milled toilet detergent bar which can be prepared by means known and used in the art is as follows: (The term middle cut as used herein refers to that fraction of distilled coconut alcohol which consists of predominantly lauryl and myristyl alcohols.)
  • Example 2 A granular built synthetic detergent composition having 16 the following formulation can be prepared and the antimicrobial agents of this invention can be incorporated therein.
  • the composition in addition to performing well in its cleaning capacity, imparts considerable antimicrobial activity to fabrics cleansed in the solution.
  • Example 3 An excellent antimicrobial granular detergent composition has the following formula:
  • a water solution containing from 0.15 to 0.45% concentrations of the above formula provides very good cleaning results in both laundering and dishwashing situations, while controlling bacteria.
  • Example 4 The following composition containing an effective bleaching agent performs very well in cleaning and disinfecting capacities:
  • Example 5 An excellent built liquid laundering composition which cleans as it disinfects and which is suitable for any household cleaning situation can have the following composi- An excellent built liquid detergent com-position accordmg to this invention has the following composition:
  • Example 7 An excellent household scouring cleanser can contain the following ingredients:
  • Percent Silica flour (abrasive) 84.5 Detergent consisting of 85% trisodium phosphate and dimethyl coconut ammonio acetate 14.0 Lithium hypochlorite .5 Dibenziodolium bisulfate 1.0
  • This composition disinfects as it cleans and can be usefully employed in kitchen and bathroom situations.
  • Example 8 An effective antimicrobial granular detergent composition has the following formulation:
  • Example 10 An antimicrobial laundering composition especially effective at cool water temperatures has the following composition:
  • Example 11 Another effective antimicrobial cool water built granular composition according to this invention has the following composition:
  • An antimicrobial detergent composition consisting essentially of a water-soluble detergent selected from the group consisting of fatty acid soaps, anionic organic nonsoap detergents which are water-soluble salts of organic sulfuric reaction products having in their molecular structure an alkyl radical containing from about 8 to about 22 carbon atoms and a radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals, and amphoteric synthetic detergents which are derivatives of aliphatic amines which contain a long chain of about 8 to about 18 carbon atoms, and an anionic water-solubilizing group selected from carboxy, sulfo, or sulfato and mixtures thereof and an active antimicrobial dibenziodolium compound having the structural formula Y and Y represent radicals selected from the group consisting of halogen, nitro, alkyl radicals containing up to 3 carbon atoms, halogen substituted alkyl radicals containing up to 3 carbon atoms, amino and sulfa
  • n represent integers selected from the group consisting of 0, 1 and 2, and when n is 2, the Y radicals can be dissimilar and when n' is 2 the Y radicals can be dissimilar and,
  • X represents an inorganic anion selected from sulfate
  • said active dibenziodolium compound being present in said detergent composition in an antimicrobially effective amount.
  • dibenziodolium compound is bis(3,7-dichlorodibenz(be) (1,4) oxiodinium) sulfate.
  • the antimicrobial detergent composition of claim 1 wherein the dibenziodolium compound is 3-chlorodibenz (be) 1,4)oxiodinium chloride.
  • the antimicrobial detergent composition of claim 1 wherein the dibenziodolium compound is 2-chlorodibenz (be) 1,4) oxiodiniurn chloride.
  • amphoteric detergent is selected from the group consisting of 3-(N,N-dimethyl-N-alkylammonio)-propane-1- sulfonate and 3-(N,N-dimethyl-N-alkylammonio)-2-hydroxy-propane-1-sulfonate, wherein the alkyl radical con tains from 12 to 18 carbon atoms.
  • An antimicrobial detergent composition consisting essentially of (a) a water-soluble detergent selected from the group consisting of fatty acid soaps, anionic organic non-soap detergents which are water-soluble salts of organic sulfuric reaction products having in their molecular structure an alkyl radical containing from about 8 to about 22 carbon atoms and a radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals, and amphoteric synthetic detergents which are derivatives of aliphatic amines which contain a long chain of about 8 to about 18 carbon atoms, and an anionic water-solubilizing group selected from carboxy, sulfo, or sulfato and mixtures thereof; (b) an active antimicrobial dibenziodolium compound having the structural formula Yn 'n' wherein Y and Y represent radicals selected from the group consisting of halogen, nitro, alkyl radicals containing up to 3 carbon atoms, halogen substituted alkyl radicals
  • n and n represent integers selected from the group consisting of 0, 1 and 2, and when n is 2, the Y radicals can be dissimilar and when n' is 2 the Y radicals can be dissimilar and,
  • X represents an inorganic anion selected from sulfate
  • a chlorine bleaching agent selected from sodium hypochlon'te, dichlorocyanuric acid and the sodium and potassium salts thereof; trichlorocyanuric acid; 1,3-dichloro-5,5-dimethyl hydantoin', N,N-dichlorobenzoylene urea; paratoluene sulfondichloroamide; trichloromelamine; N-chloroammeline; N-chlorosuccinimide; N,N- dichloroazodicarbonamidine; N-chloracetyl urea; N,N'- dichlorobiuret; chlorinated dicyandiamide; calcium hypochlorite; lithium hypochlorite; chlorinated trisodium phosphate at a level which provides from about .5% to about 50% available chloride.
  • a method of imparting antimicrobial properties to a cotton fabric which consists essentially of washing said fabric in an aqueous solution of an organic detergent selected from the group consisting of fatty acid soaps, anionic organic non-soap detergents which are watersoluble salts of organic sulfuric reaction products having in their molecular structure an alkyl radical containing from about 8 to 22 carbon atoms and a radical selected from the group consisting of sulfonic acid and sulfuric acid ester radicals, and amphoteric synthetic detergents which are derivatives of aliphatic amines which contain a long chain of about 8 to 18 carbon atoms, and an anionic water-solubilizing group selected from carboxy, sulfo, or sulfato having incorporated therein from 0.01% to 4% by weight, based on the detergent surfactant of an active antimicrobial dibenziodolium compound having the structural formula wherein Y and Y represent radicals selected from the group consisting of halogen, nitro, alkyl radicals
  • n and n' represent integers selected from the group consisting of 0, 1 and 2, and when n is 2, the Y radicals can be dissimilar and when n is 2 the Y radicals can be dissimilar and,
  • X represents an inorganic anion selected from sulfate
  • a cosmetic detergent soap bar composition consisting essentially of a soap detergent and an antimicrobially effective amount of an active antimicrobial dibenziodolium compound having the structural formula n Y n X wherein Y and Y' represent radicals selected from the group consisting of halogen, nitro, alkyl radicals containing up to 3 carbon atoms, halogen substituted alkyl radicals containing up to 3 carbon atoms, amino and sulfamyl, and Y and Y can be dissimilar;
  • n and n represent integers selected from the group consisting of 0, 1 and 2, and when n is 2, the Y radicals can be dissimilar and when n is 2 the Y radicals can be dissimilar and,
  • X represents an inorganic anion selected from sulfate

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US298491A 1963-07-29 1963-07-29 Antimicrobial detergent compositions Expired - Lifetime US3244636A (en)

Priority Applications (11)

Application Number Priority Date Filing Date Title
US298491A US3244636A (en) 1963-07-29 1963-07-29 Antimicrobial detergent compositions
SE9122/64A SE324424B (enrdf_load_stackoverflow) 1963-07-29 1964-07-27
DEP34778A DE1258006B (de) 1963-07-29 1964-07-28 Wasch- und Reinigungsmittel mit antibakterieller Wirkung
DK376064AA DK124618B (da) 1963-07-29 1964-07-29 Antimikrobiel rensemiddelblanding.
FR983372A FR1448750A (fr) 1963-07-29 1964-07-29 Compositions détergentes antimicrobiennes
FI1627/64A FI41184B (enrdf_load_stackoverflow) 1963-07-29 1964-07-29
GB31045/64A GB1046896A (en) 1963-07-29 1964-08-04 Antimicrobial detergent compositions
CH515065A CH455116A (de) 1963-07-29 1965-04-13 Antibakteriell wirkendes Wasch- und Reinigungsmittel
NL6510151A NL6510151A (enrdf_load_stackoverflow) 1963-07-29 1965-08-04
BE675135A BE675135A (enrdf_load_stackoverflow) 1963-07-29 1966-01-14
AU784/66A AU410302B1 (en) 1963-07-29 1966-01-25 Antimicrobal detergent composition

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US298491A US3244636A (en) 1963-07-29 1963-07-29 Antimicrobial detergent compositions

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US3244636A true US3244636A (en) 1966-04-05

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US298491A Expired - Lifetime US3244636A (en) 1963-07-29 1963-07-29 Antimicrobial detergent compositions

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US (1) US3244636A (enrdf_load_stackoverflow)
AU (1) AU410302B1 (enrdf_load_stackoverflow)
BE (1) BE675135A (enrdf_load_stackoverflow)
CH (1) CH455116A (enrdf_load_stackoverflow)
DE (1) DE1258006B (enrdf_load_stackoverflow)
DK (1) DK124618B (enrdf_load_stackoverflow)
FI (1) FI41184B (enrdf_load_stackoverflow)
FR (1) FR1448750A (enrdf_load_stackoverflow)
GB (1) GB1046896A (enrdf_load_stackoverflow)
NL (1) NL6510151A (enrdf_load_stackoverflow)
SE (1) SE324424B (enrdf_load_stackoverflow)

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3428736A (en) * 1967-07-26 1969-02-18 Lilly Co Eli Synergistic combination containing an oxiodinium compound and bis-(3,5,6-trichloro-2-hydroxyphenyl)methane
US3435119A (en) * 1967-07-27 1969-03-25 Lilly Co Eli Synergistic combination containing an oxiodinium compound and 3,4,4'-trichlorocarbanilide
US3506719A (en) * 1966-08-17 1970-04-14 Lilly Co Eli Novel oxiodinium and thiaiodinium compounds
US3507796A (en) * 1967-05-11 1970-04-21 Procter & Gamble Antibacterial compositions
US3525696A (en) * 1966-04-25 1970-08-25 West Laboratories Inc Low-foaming germicidal surfactantiodine compositions for cleaned-inplace equipment
US3545014A (en) * 1968-02-05 1970-12-08 Elbert Davis Sanitizers
US4193935A (en) * 1970-03-04 1980-03-18 Eli Lilly And Company Novel oxiodinium and thiaiodinium compounds
US4283349A (en) * 1973-03-02 1981-08-11 Eli Lilly And Company Novel oxiodinium and thiaiodinium compounds
US4440943A (en) * 1982-03-15 1984-04-03 The Dow Chemical Company Phenoxiodinin-5-ium antimicrobial compounds
US4613620A (en) * 1966-08-17 1986-09-23 Eli Lilly And Company Novel oxiodinium and thiaiodinium compounds
US4975217A (en) * 1981-07-20 1990-12-04 Kimberly-Clark Corporation Virucidal composition, the method of use and the product therefor
US20150360987A1 (en) * 2013-01-24 2015-12-17 Sonitec-Vortisand Technologies Inc. Reactor with antimicrobial medium for liquid disinfection

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115485358A (zh) * 2020-04-30 2022-12-16 诺力昂化学品国际有限公司 烷基醚胺聚甘油表面活性剂

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2129264A (en) * 1935-03-29 1938-09-06 Du Pont Nitrogen-containing organic compounds
GB578210A (en) * 1944-06-03 1946-06-19 Kurt Israel Jacobson Antiseptic preparations
US2487799A (en) * 1941-01-24 1949-11-15 Givaudan Corp Germicidal soap
GB654139A (en) * 1948-12-31 1951-06-06 Unilever Ltd Improvements in or relating to germicidal detergents
US2878293A (en) * 1953-09-03 1959-03-17 Chilean Nitrate Sales Corp Iodonium compounds
US3084097A (en) * 1961-01-10 1963-04-02 Procter & Gamble Antibacterial compositions
US3118842A (en) * 1959-07-13 1964-01-21 Marveli Ind Multi-purpose cleaner-germicide-deodorizer composition

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2129264A (en) * 1935-03-29 1938-09-06 Du Pont Nitrogen-containing organic compounds
US2487799A (en) * 1941-01-24 1949-11-15 Givaudan Corp Germicidal soap
GB578210A (en) * 1944-06-03 1946-06-19 Kurt Israel Jacobson Antiseptic preparations
GB654139A (en) * 1948-12-31 1951-06-06 Unilever Ltd Improvements in or relating to germicidal detergents
US2878293A (en) * 1953-09-03 1959-03-17 Chilean Nitrate Sales Corp Iodonium compounds
US3118842A (en) * 1959-07-13 1964-01-21 Marveli Ind Multi-purpose cleaner-germicide-deodorizer composition
US3084097A (en) * 1961-01-10 1963-04-02 Procter & Gamble Antibacterial compositions

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3525696A (en) * 1966-04-25 1970-08-25 West Laboratories Inc Low-foaming germicidal surfactantiodine compositions for cleaned-inplace equipment
US3506719A (en) * 1966-08-17 1970-04-14 Lilly Co Eli Novel oxiodinium and thiaiodinium compounds
US4613620A (en) * 1966-08-17 1986-09-23 Eli Lilly And Company Novel oxiodinium and thiaiodinium compounds
US3507796A (en) * 1967-05-11 1970-04-21 Procter & Gamble Antibacterial compositions
US3428736A (en) * 1967-07-26 1969-02-18 Lilly Co Eli Synergistic combination containing an oxiodinium compound and bis-(3,5,6-trichloro-2-hydroxyphenyl)methane
US3435119A (en) * 1967-07-27 1969-03-25 Lilly Co Eli Synergistic combination containing an oxiodinium compound and 3,4,4'-trichlorocarbanilide
US3545014A (en) * 1968-02-05 1970-12-08 Elbert Davis Sanitizers
US4193935A (en) * 1970-03-04 1980-03-18 Eli Lilly And Company Novel oxiodinium and thiaiodinium compounds
US4283349A (en) * 1973-03-02 1981-08-11 Eli Lilly And Company Novel oxiodinium and thiaiodinium compounds
US4975217A (en) * 1981-07-20 1990-12-04 Kimberly-Clark Corporation Virucidal composition, the method of use and the product therefor
US4440943A (en) * 1982-03-15 1984-04-03 The Dow Chemical Company Phenoxiodinin-5-ium antimicrobial compounds
US20150360987A1 (en) * 2013-01-24 2015-12-17 Sonitec-Vortisand Technologies Inc. Reactor with antimicrobial medium for liquid disinfection

Also Published As

Publication number Publication date
GB1046896A (en) 1966-10-26
DE1258006B (de) 1968-01-04
SE324424B (enrdf_load_stackoverflow) 1970-06-01
BE675135A (enrdf_load_stackoverflow) 1966-05-03
DK124618B (da) 1972-11-06
CH455116A (de) 1968-04-30
FI41184B (enrdf_load_stackoverflow) 1969-06-02
AU410302B1 (en) 1971-02-08
FR1448750A (fr) 1966-03-18
NL6510151A (enrdf_load_stackoverflow) 1967-02-06

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