Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/62—Oxygen or sulfur atoms
  • C07D213/70—Sulfur atoms
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/58—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing atoms other than carbon, hydrogen, halogen, oxygen, nitrogen, sulfur or phosphorus
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/10—Washing or bathing preparations
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q5/00—Preparations for care of the hair
  • A61Q5/02—Preparations for cleaning the hair
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
  • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic System
  • C07F9/94—Bismuth compounds
• • 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
• • 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
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
  • A61Q17/005—Antimicrobial preparations

Definitions

• the present invention relates to a new compound, phenylbismuth bis(2-pyridinethiol l-oxide), which can be formed by the reaction between sodium 2-pyridinethiol 1- oxide and diphenylbismuth acetate.
• This invention also relates to the use of this compound, which is highly efiective against a broad spectrum of bacteria as well as yeast and fungal species, especially when used on the skin, where the compound is fairly substantive, and to compositions, including detergent compositions, containing said compound.
• Phenylbismuth bis(2pyridinethiol l-oxide) has the formula:
• N l o Compositions containing phenylbismuth bis(2-pyridinethiol l-oxide) have excellent broad-spectrum antibacterial and antifungal action.
• Phenylbismuth bis(2-pyridinethiol l-oxide), hereinafter referred to as PBDP, is a yellow powder having a melting point at about 215-218". It is generally insoluble in most common solvents, but is soluble to the extent of about 1% in dimethylsulfoxide, dimethylformamide or dimethylacet- 3,753,990 Patented Aug. 21, 1973 ice amide. The dry solid PBDP is stable and the PBDP appears stable in the presence of soap solutions (pH 9-10) and hydrochloric acid (pH 1).
• Phenylbismuth bis(2-pyridinethiol l-oxide) has been shown to exhibit antibacterial and antifungal effectiveness against, e.g., Gram-positive organisms such as: Brevibacterium ammoniagenes, Erysipelothrix insidiosa, Lact0- bacillus leichmanni, Bacillus subtilus,, Clostridium perfringens, Staphylococcus aureus, Staphylococcus epidermiais, Sarcina lutea, Streptococcus faecalis, Cor ynebacterium acnes, Axilla diphtheriod #16, Oral Streptococcus #126, Mycobacterium phlei, Mycobactei'ium smegmatis, and Mycobacterium balnei; Gram-negative organisms such as: Alkaligenes faecalis, Salmonella typhosa, Shigella flexneri, Mima polymvr
• PBDP Because of the extremely broad antibacterial and antifungal eifectiveness of PBDP it is desirably used as a component of surgical scrub products, bar soaps, shampoos, oral products (e.g., toothpastes, mouthwashes, etc.), first aid sprays, foot powder, deodorants (especially underarm deodorants), first aid creams, toilet bowl cleaners, hard surface cleaners, detergents, paints, cosmetics, spermicides, burn dressings, animal feeds, wood preservatives, mildewcides, germicides, algacides, fungicides, medicines, packing preservatives, etc. In extremely small amounts, e.g., 10 ppm, the 'PBD'P will inhibit the growth of a broad variety of organisms.
• oral products e.g., toothpastes, mouthwashes, etc.
• first aid sprays foot powder, deodorants (especially underarm deodorants)
• first aid creams toilet bowl cleaners, hard surface cleaners, detergents,
• the compositions can be used to destroy organisms, as required.
• the PBDP can be used to treat a variety of diseases and/or organisms including acne, leprosy psoriasis, warts, intestinal parasites, dandruif, pseudomonas or coli bacteria, fungus (e.g., athletes foot), vaginal infections, etc.
• Compositions containing PBDP can be used to treat tissue either to prevent infections or to cure infections.
• PBDP is not inactivated by urine or hair oil, but its activity is somewhat diminished by human serum or human red blood cell lysate. Its activity is somewhat greater in acid to neutral media against S. aureus and E. coli.
• PBDP is substantive to tooth enamel and cellulose.
• PBDP can be used to prevent the growth of plaque in the mouth and can be used against gingivitis. Also, it can be used on bandages, diapers, and sanitary napkins to prevent infections, diaper rash, odor, etc.
• PBDP can also be used as a slimicide and preservative for paper and wood.
• Phenylbismuth bis(2-pyridinethiol l-oxide) can be prepared by reacting diphenylbismuth acetate with sodium Z-pyridinethiol l-oxide in a 1:1 molar ratio in a solvent such as dimethyl formamide. The compound, a yellow precipitate, can then be filtered and purified as exemplified hereinafter in Example I.
• phenylbismuth bis(2-pyridinethiol l-oxide) include the reaction of sodium, potassium, ammonium, or lithium 2- pyridinethiol 1 oxide or any other salt containing a loosely held cation with a phenylbismuth dihalide (e.g., a chloride, bromide, or iodide).
• a phenylbismuth dihalide e.g., a chloride, bromide, or iodide
• compositions containing phenylbismuth bis(2-pyridinethiol l-oxide) can be used in aqueous and/ or non-aqueous solvents to provide antibacterial action.
• the compositions will contain from about 0.2% to about 3% phenylbismuth bis(2- pyridinethiol l-oxide), most preferably from about 1% to about 2%.
• Desirable compositions are those containing soap and non-soap synthetic detergent compounds.
• the synthetic detergent compounds are cationic, amphoteric, including zwitterionic or nonionic.
• soap as used herein is meant to designate alkali metal soaps such as the 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 neutralization 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 synthetic detergents which can be used with the antibacterial, antifungal, and antiyeast compound of the present invention can be broadly defined as the watersoluble salts, including the alkali metal, ammonium and substituted ammonium 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.
• alkali metal e.g., sodium and potassium
• ammonium and substituted ammonium e.g., lower alkyl ammonium
• alkyl sulfates especially those obtained by sulfating the higher alcohols produced by reducing the glycerides of tallow or coconut oil
• random paraflin sulfonates in which the alkyl group contains from about 8 to about 22 carbon atoms, prepared by treating random paraffin hydrocarbons in sulfur dioxide and chlorine in the presence of light followed by treating with a base
• branched or linear alkyl benzene sulfonates in which the alkyl group contains from about 8 to about 18 carbon atoms, preferably from about to about 14 carbon atoms, especially those of the types described in US.
• the length of the hydrophilic or polyoxyalkylene radical which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements.
• nonionic synthetic detergents are made available on the market under the trade name of Pluronic. These compounds are formed by condensing ethylene oxide with a hydrophobic base formed by the condensation of propylene oxide with propylene glycol.
• the hydrophobic portion of the molecule which, of course, exhibits water insolubility has a molecular weight of from about 1,500 to about 1,800.
• the addition of polyoxyethylene radicals to this hydrophobic portion tends to increase the water solubility of the molecule as a whole and the liquid character of the products is retained up to the point where polyoxyethylene content is about 50% of the total weight of the condensation product.
• nonionic synthetic detergents include:
• the polyethylene oxide condensates of alkyl phenols, e.g., the condensation products of alkyl phenols having an alkyl group containing from about 6 to 12 carbon atoms in either a straight chain or branched chain configuration, with ethylene oxide, the said ethylene oxide being present in amounts equal to 10 to 60 moles of ethylene oxide per mole of alkyl phenol.
• the alkyl substituent in such compounds may be derived from polymerized propylene, diisobutylene, octane, or nonane, for example.
• R R R N Long chain tertiary amine oxides corresponding to the following general formula, R R R N 0, wherein R contains an alkyl, alkenyl or monohydroxy alkyl radical of from about 8 to about 18 carbon atoms, from 0 to about 10 ethylene oxide moieties, and from 0 to 1 glyceryl moiety, and R and R contain from 1 to about 3 carbon atoms and from 0 to about 1 hydroxy group, e.g., methyl, ethyl, propyl, hydroxy ethyl, or hydroxy propyl radicals.
• the arrow in the formula is a conven tional representation of a semi-polar bond.
• amine oxides suitable for use in this invention include dimethyldodecylamine oxide, oleyldi(2 hydroxyethyl)- amine oxide, dimethyloctylamine oxide, dimethyldecylamine, oxide, dimethyltetradecylamine oxide, 3,6,9-trioxaheptadecyldiethylamine oxide, di(2 hydroxyethyl)tetradecylamine oxide, Z-dodecoxyethyldimethylamine oxide, 3 dodecoxy-Z-hydroxypropyldi(3-hydroxypropyl)amine oxide, dimethylhexadecylamine oxide.
• RRR"P- O Long chain tertiary phosphine oxides corresponding to the following general formula RRR"P- O, wherein R contains an alkyl, alkenyl or monohydroxyalkyl radical ranging from 8 to 18 carbon atoms in chain length, from 0 to about 10 ethylene oxide moieties and from 0 to l glyceryl moiety and R and R" are each alkyl or monohydroxyalkyl groups containing from 1 to 3 carbon atoms.
• the arrow in the formula is a conventional representation of a semi-polar bond. Examples of suitable phosphine oxides are:
• dodecyldimethylphosphine oxide dodecyldimethylphosphine oxide, tetradecyldimethylphosphine oxide, tetradecylmethylethylphosphine oxide, 3,6,9-trioxaoctadecyldimethylphosphine oxide, cetyldimethylphosphine Oxide, 3-dodecoxy-2-hydroxypropyldi (Z-hydroxyethyl phosphine oxide, stearyldimethylphosphine oxide, cetylethylpropylphosphine oxide, oleyldiethylphosphine oxide, dodecyldiethylphosphine oxide, tetradecyldiethylphosphine oxide, dodecyldipropylphosphine oxide, dodecyldi(hydroxymethyl)phosphine oxide, dodecyldi(2-hydroxyethyl)phosphine
• Examples include:
• the zwitterionic synthetic detergents useful with the antibacterial agent of the present invention can be broadly described as derivatives of aliphatic quaternary ammonium, phosphonium, and sulfonium compounds, in which the aliphatic radicals can 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 water solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
• a general formula for these compounds is:
• R contains an alkyl, alkenyl, or hydroxy alkyl radical of from about 8 to about 18 carbon atoms, from 0 to about 10 ethylene oxide moieties and from 0 to l glyceryl moiety;
• Y is selected from the group consisting of nitrogen, phosphorus, and sulfur atoms;
• R is an alkyl or monohydroxyalkyl group containing 1 to about 3 carbon atoms;
• x is 1 when Y is a sulfur atom and 2 when Y is a nitrogen or phosphorus atom,
• R is an alkylene or hydroxyalkylene of from 1 to about 4 carbon atoms and Z is a radical selected from the group consisting of carboxylate, sulfonate, sulfate, phosphonate, and phosphate groups.
• Examples include:
• amphoteric synthetic detergents useful in the present invention can be broadly described as derivatives of aliphatic secondary and tertiary amines in which the aliphatic radical can be straight chain or branched and wherein one of the aliphatic substitutents contains from about 8 to about 18 carbon atoms and one contains an anionic water solubilizing group, e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
• an anionic water solubilizing group e.g., carboxy, sulfonate, sulfate, phosphate, or phosphonate.
• Examples of compounds falling within this definition are sodium 3-dodecylaminopropionate, sodium 3-dodecylaminopropane sulfonate, dodecyl-fi-alanine, N-alkyl-taurines such as the one prepared by reacting dodecylamine with sodium isethionate according to the teaching of US. Pat. No. 2,658,072, N-higher alkyl aspartic acids such as those produced according to the teaching of US. Pat. No. 2,438,091, and the products sold under the trade name Miranol and described in U.S. Pat. No. 2,528,378.
• Cationic synthetic detergents include those quaternary ammonium, quaternary phosphonium, and ternary sulfonium compounds containing a single straight chain or branched aliphatic radical containing from about six to about 20 carbon atoms such as dodecyltrimethylammonium chloride; nonylbenzylethyldimethylammonium nitrate; tetradecylpyridinium bromide; octadecylbutylpropylmethylphosphonium nitrite; decyldimethylsulfonium chloride; etc.
• Detergent formulations containing the antibacterial compositions of the present invention can also contain from about 0% to about 90%, preferably from about 10% to about 90% of water-soluble alkaline detergency builder salts, either of the organic or inorganic types. Examples of such builder salts can be found in US. Pat. No. 3,336,233, issued Aug. 15, 1967, column 9, lines 2966, which is incorporated herein by reference. However, at a very high pH, the compound may undergo alkaline hydrolysis and accordingly, for long-term stability, the detergent formulations should have a pH of less than about 10 and preferably the pH should be approximately neutral.
• the detergent formulations can also contain any of the usual adjuvants, diluents, and additives, for example, perfumes, anti-tarnishing agents, anti-redeposition agents, dyes, fluorescers, suds builders, suds depressors and the like without detracting from the advantageous properties of the antibacterial compositions of the present invention.
• diluents which may be incorporated into a synthetic detergent bar in amounts of up to about of the bar include soaps, especially alkaline earth metal insoluble soaps (alkaline earth salts of higher fatty acids); starches such as cornstarch; and clays such as china clay or fullers earth.
• Other diluents include inorganic salts such as sodium and potassium chlorides and sulfates. Such diluents add bulk to the bar and improve its cosmetic properties without impairing its detergent or cohesive properties.
• this phenylbisrnuth bis(2- pyridinethiol I-oxide) was purified as follows: 30 g. of the crude material was dissolved in 2,000 ml. dimethylacetamide at about 60 C. The solution was stirred for approximately 5 minutes, during which time the phenylbismuth bis(2-pyridinethiol l-oxide) was dissolved, leaving the impurities which were separated by filtering. The filtrate was then diluted with an equal volume of water to precipitate out the phenylbismuth bis(2-pyridinethiol l-oxide). The mixture was cooled in an ice bath to precipitate as much material as possible, and this. material was then separated by filtering.
• MIC Minimal inhibitory concentration in agar 10,000 ppm. stock solutions of phenylbismuth bis(2- pyridinethiol l-oxide) were prepared in dirnethylformamide (DMF). The active was diluted to the desired test concentration and added to 19-20 ml. of molten trypticase soy agar (TSA) to give a series of graded concentrations (p.p.m.). Thorough rotation of plates assured adequate mixing of the sanitizer before agar solidification. Appropriate control plates containing plain TSA were ineluded. All plates remained at room temperature overnight.
• Staphylococcus aureus (S. a.) Staphylococcus epidermidis (S. ep.) Streptococcus faecalis (St. 1'.) Streptococcus sp. (St. 126) Sarcina lutea (Sar. l.) Diphtheroid sp. (Dip.
• Pseudomonas aerugz'nosa Ps. a.) Escherichia coil (E. c.) Serratia marcescens (S. m.) Klebsiella pneumoniae (K. p.) Enterobacter aerogenes (E.
• Fungistatic tests were performed using a modified gradient plate technique reported by Hunt and Sandham (Applied Microbiology 17 #2:329-30, 1969). Results were as follows: Aspergillus niger5.8 p.p.m.; Microsporum gypseum-1 p.p.m.
• the product was then distributed over the hands and the lather was worked for 90 seconds.
• the hands were then rinsed under running tap water for 30 seconds.
• the four exposures were spread over two days, and on the afternoon of the second day, the subjects washed their hands four times using a blank bar soap containing no antibacterial agents.
• a fifth standardized washing was then done in a basin containing one liter of sterile distilled water with careful rinsing in this basin. Aliquots were taken from the thoroughly mixed basin contents, added to 30 ml. of sterile distilled water in a membrane funnel, and passed through sterile membrane filters with vacuum suction.
• the filters were then incubated on pads saturated with 2x concentrated trypticase soy broth plus horse serum and 1% Tween 80 in plastic dishes for 48 hours at 37 C. Colonies appearing on the filters were counted and these numbers multiplied by the appropriate dilution factor to determine the number of bacteria/ liter in the fifth basin contents. The numbers per basin for each panelist were converted to logarithms to minimize unusually high or low counts. These values were averaged to determine the mean log of the fifth basin bacterial count. Calculation of the log percent reduction for each subject was made using the log of 1.3 10 or 6.1184, an average fifth basin bacterial count obtained from more than 500 handwashings by non-antibacterial soap users. These values were averaged to obtain the mean log percent reduction. The results were as follows:
• Composition #4 Percent Dimethyl coconut 1 amine oxide 8.0 Disodium lauryl beta-iminodipropionate 5.0 Sodium coconut 1 sulfate 4.0 Coconut 2 diethanolamide 1.0 Phenylbismuth bis(2-pyridinethiol l-oxide) 1.0 Perfume 0.5 Color 0.01
• Citric acid to adjust pH to 7.5 Water, balance.
• the alkyl radical is derived from middle cut coconut alcohol and has approximately the following chain length compo sivtplllg C10, 66% C12, 23% C14, and 9% Cm.
• Composition #5 A shampoo composition is obtained by uniformly mixing together the following ingredients:
• Shampoo formulations containing phenylbismuth bis(2- pyridinethiol l-oxide) are desirable since they will control dandruff.
• Acrylamide polymer (contains 5-10 mole percent acrylic acid radicals; monomer is less than 0.05%; viscosity of a 0.5% soln. is about -15 centipoises at 25 C.)
• Salts sodium and potassium chloride and sulfate from detergents
• 1-2 Water Balance Coconut indicates alkyl radicals corresponding to those of middle cut coconut fatty alcohol containing approximately 2% C10, 66% C12, 23% C11, and 9% C15.
• Cream shampoo Composition Percent Sodium coconut glyccryl ether sulfonate (about 29% diglyceryl and the balance substantially monoglyceryl) 14.8 Sodium tallow glyceryl ether sulfonate (about 28% diglyceryl and the balance substantially monoglyceryl) 2.0 Sodium chloride 6.7 Sodium sulfate 3.5 Sodium N-lauroyl sarcosinate 3.0 Phenylbismuth bis(2-pyridinethiol l-oxide) 2.0 Middle-cut coconut 1 diethanolamine 0.5 Acetylated lanolin 1.0 Perfume 0.4 Water Balance 1 2% C10, 66% C12, 23% C14, and 9% C10.
• This bar cleans well and exhibits good odor reducing properties evidencing antibacterial eifectiveness. It reduces the number of bacteria on the skin significantly.
• EXAMPLE VII A granular built synthetic detergent composition having the following formulation can be prepared and the antibacterial compositions of the present invention can be incorporated therein.
• This composition in addition to performing well in its cleaning capacity, imparts considerable antibatcerial activity to fabrics cleansed in its solution.
• dodecyltrimethylammonium chloride nonylbenzylethyldimethylammonium nitrate; tetradecylpyridinium bromide; octadecylbutylpropylmethylphosphonium nitrite; decyldimethylsulfom'um chloride; (hexylphenyl)dimethylbenzylammonium fluoride; eicosyldimethylbenzylphosphonium chloride; coconutalkylmethylmorpholininm nitrate; octadecylmethylbenzylsulfonium sulfate; laurylpyridinium chloride;
• laurylpyridinium bisulfate laurylpyridinium-S-chloro-2-mercaptobenzothiazole; laurylpicolinium-p-toluenesulfonate; tetradecylpyridinium bromide;
• laurylisoquinolinium bromide laurylisoquinolinium saccharinate; alkylisoquinolinium bromide;
• N-cetyl- -ethyl-morpholinium ethosulfate benzalkonium chloride
• R N+X* one R group is fatty
• R.,N+X three R groups are fatty
• tri(hydrogenated tallow) methylammoniurn chloride distilled tallow amine acetate; diamine acetates; N-oleyl propylene diamine monoacetate; sodium tallow alkyl sulfate; potassium coconut alkyl glyceryl ether sulfonate; sodium salt of randomly sulfonated paraffin containing an average of 15.2 carbon atoms; ammonium tridecyl sulfate; condensation product of octyl phenol with 15 moles of ethylene oxide per mole of octyl phenol;
• a fabric softening composition having the following formulation can be prepared.
• the antibacterial and antifungal effectiveness of the phenylbismuth bis(2-pyridinethiol l-oxide) is especially desirable since the antibacterial and antifungal compound is extremely substantive to cloth.
• Phenylbismuth bis(2-pyridinethiol l-oxide) 1.0 Water Balance Twenty p.p.m. of PBDP were added to a 0.1% aqueous concentration of Downy, a commercial cationic softener containing a ditallowalkyl dimethylammonium chloride active. This composition, when used at 27 C.

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• 1972
  • 1972-01-17 US US00218584A patent/US3753990A/en not_active Expired - Lifetime
  • 1972-04-04 NL NL7204437A patent/NL7204437A/xx not_active Application Discontinuation
  • 1972-04-07 FR FR7212388A patent/FR2178819B1/fr not_active Expired
  • 1972-04-07 DE DE2216725A patent/DE2216725A1/de active Pending
  • 1972-04-13 GB GB1708872A patent/GB1341331A/en not_active Expired
  • 1972-04-14 BE BE782105A patent/BE782105A/xx unknown
  • 1972-05-26 JP JP47052417A patent/JPS4910908A/ja active Pending
• 1973
  • 1973-03-30 US US346396A patent/US3890242A/en not_active Expired - Lifetime
  • 1973-03-30 US US00346395A patent/US3824307A/en not_active Expired - Lifetime

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