Classifications

• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q15/00—Anti-perspirants or body deodorants
• • 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
  • A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
  • A61K8/22—Peroxides; Oxygen; Ozone
• • 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
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/38—Percompounds, e.g. peracids
• • 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
  • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
  • A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
• • 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
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/66—Non-ionic compounds
  • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/88—Ampholytes; Electroneutral compounds
  • C11D1/94—Mixtures with anionic, cationic or non-ionic 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
  • C11D3/39—Organic or inorganic per-compounds
  • C11D3/3947—Liquid compositions
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
  • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
  • A61K2800/51—Chelating agents

Definitions

• a stable liquid concentrate comprises about 01-50% of an active oxygen yielding compound, about 05-50% of a sulfobetaine or betaine surfactant. about l50% of a nonionic polyoxyethylene-polyoxypropylene block copolymer surfactant, and l0-80% water.
• the concentrate exhibits a loss of active oxygen of as little as 6.7% after 675 days and has utility as a bleaching and cleaning composition.
• the composition can be diluted with pure or ordinary tap water.
• This invention relates to new liquid concentrate compositions which have a unique stabilizing action on oxygen yielding compounds, and more particularly relates to stable aqueous solutions of per-oxygen compounds in a surface active vehicle.
• Hexachlorophene containing preparations for contact with the human skin has been discouraged becasue these preparations have been shown to cause brain damage in animals through absorption and elicit untoward systemic effects.
• Hexachlorophene containing preprations have been used for a wide variety of purposes such as a skin bathing composition in infant nurseries and cleansing compositions in preoperative preparation and scrubbing. A continuing search is going on for a suitable replacement for such hexachlorophene compositions.
• the present invention has found that an aqueous concentrate containing an active oxygen yielding compound can be given extended shelf-life with little loss of active oxygen through the use of a combination of certain surfactants in certain amounts.
• the present invention provides a stable liquid concentrate comprising about 0.1 50% of an active oxygen yielding compound; about 0.5 50% of a sulfobetaine or betaine surfactant; about 1 50% of a nonionic polyoxyethylene-polyoxypropylene surfactant and 80% water.
• the concentrate can be diluted or used full strength and exhibits a loss of active oxygen of as little as 6.7% after 675 days.
• the concentrates can also be used as substitutes for hexachlorophenes containing compositions.
• the liquid detergent concentrate of this invention is an aqueous solution.
• the water used in the preparation of the concentrates of this invention is highly purified water and is preferably purified by distillation using pyrex glass equipment. Properly deionized water essentially free of dissolved organic substances can also be used in preparing the concentrates.
• Preliminary stability studies indicate that the use of a high purity water is an important factor in obtaining concentrates having extended shelf-life. Significantly extended shelf-life is obtained for the concentrates of this invention when the highest purity water is used.
• the concentrates of the present invention are formulated to be diluted at the time of use as explained in greater detail hereafter. Dilution at the time of use of the concentrates can be achieved by ordinary tap water without significantly altering the stablity of the diluted product, but only the highest purity water can be used to prepare the initial concentrate to insure an extended shelf-life.
• an active oxygen yielding compound is provided in the concentrate.
• the active oxygen yielding compounds are detergent vehicle soluble per-oxygen compounds and are used in amounts ranging from 0.l 50% by weight, preferably 0.5 10%, based on the total weight of the concentrate.
• the per compounds are bleaching agents that impart a high level of cleaning and bleaching power to the compositions of the present invention.
• the per compounds derive their bleaching power from the release of active oxygen.
• the active oxygen yielding compound is hydrogen peroxide and is used in amounts of 0.5 10%.
• the hydrogen peroxide may also be present wholly or partially in the form of addition products with such well known materials as urea, alkali borates, polyphosphates and orthophosphates.
• Metal peroxides, peroxyacids, alkyl peroxides, acyl peroxides, peroxyesters and perborates such as alkali metal perborates can also be used.
• suitable active oxygen yielding compounds for use in this invention are lauryl peroxide urea peroxide, benzoyl peroxide, lauroyl peroxide, peroxyacetic acid, sodium peroxydisulfate, di-tertbutyl peroxide, methyl ethyl ketone peroxide, sodium peroxide, and sodium perborate.
• a particular advantage in the use of hydrogen peroxide as a disinfectant, cleaing or a bleaching agent in the concentrates of the present invention is that it decomposes to yield active oxygen and water. Both of these resulting agents can be readily removed and are essentially non-additive to the material or tissue being treated.
• the concentrate contains a polyoxypropylene-polyoxyethylene block copolymer.
• This copolymer is a primary cleaning ingredient of the composition.
• the products sold under the trademark Pluronic by Wyandotte Chemical Corp. are a series of closely related block polymers that may be generically classifled as polyoxypropylene-polyoxyethylene condensates terminating in primary hydroxyl groups. They are formed by the condensation of propylene oxide onto a propylene glycol nucleus followed by the condensation of ethylene oxide onto both ends of the polyoxypropylene base.
• the polyoxyethylene hydrophilic groups on the ends of the molecule are controlled in length to constitute anywhere from 10% to by weight of the final molecule.
• This series of products may be represented empirically by the formula:
• polystyrene foams where a and care statistically equal.
• These polyol block copolymers are nonionic surface agents.
• block copolymers used in the concentrates of the present invention are selected on the basis such as methyl, ethyl or hydroxy ethyl groups; x is or 1; R is an alkylene or hydroxy alkylene of from 1 to about 4 carbon atoms; and Z is a radical selected from the group consisting of carboxylate and sulfonatc of their solubility, wetting effect, detergency, emulsifigroups. Exemplary of suitable betaine and sulfobetaine cation capability, foam properties and viscosity.
• Block copolymers having a solubility of at least one gram per 100 ml. of water and a molecular weight ranging between 1000 and 15,500 are useful in the present invencompounds for use in the present invention are the following compounds:
• cetyl sulfobetaine cetyl sulfobetaine
• polyoxypropylene-polyoxyethylene 4-[N,N-di(2-hydroxyethyl)-N-octadecylammonio]- block copolymers satisfying the above conditions are butane 1 -carboxylate; the following Pluronic copolymers: Pluronic F-127; 3-(N,N-dimethyl N hexadecylammonio) propane Pluronic F-68', Pluronic F108; and Pluronic L-62.
• the -1-sulfonate following Table 1 lists the properties ofa number of the 3(N,N-dimethyl N hexadecylammonia) 2 -hyblock copolymers that can be used in the present invent5 droxypropane 1 sulfonate tion. 4-[N,N-di( 2-hydroxyethyl )-N-( 2-hydroxydodecyl) TABLE 1 Average Cloud Point Solubility FOAMlNG PROPERTIES PLURONlC Molecular 1n 1% Aq. 1n Foam Heights (mm)' Weight Solution. C. Water at flow of 400ml/min.
• the Foam Height is the value obtained on a Dynamic Foam Tester Operated at a temperature of 120F using a 0.1! polyol conccntration at n flow rate of 400 ml.lmin. for ten minutes.
• the block copolymers should be present in an amount of from 1 to 50 weight percent of the concentrate, and preferably are present in an amount of 5 to percent of the concentrate.
• the concentrate contains a betaine or sulfobetaine surfactant.
• surfactants are zwitterionic synthetic detergents and can be broadly described as derivatives of aliphatic quaternary ammonium compounds in which the aliphatic radicals can be straight chain or branched, and wherein one of the aliphatic substituents contains from about 8 to 24 carbon atoms and one contains an anionic water solubilizing group such as a carboxy or sulfonate group.
• the anionic water solubilizing group is a sulfonate
• the compounds are called sulfobetaine or sultaines and are commercially available from Textilana Corp., Hawthorne, Calif.
• the anionic water solubilizing group is a carboxy group
• the compounds are called betaines and are available from E. 1. du Pont de Nemours, 1nc.; Onyx Chemical Co., Jersey City, N. 1.; and Textilana Corp. 1n the range from about pH 4 to pH 8, long chain betaines and sulfobetaines are equally ionized as acids and as bases and exist as zwitter ions or inner salts.
• betaine and sulfobetaine surfactants useful in the concentrates of this invention can be represented by the following formula:
• R is a long chain radical and contains an alkyl, alkenyl, or hydroxy alkyl radical of from about 8 to about 24 carbon atoms, from 0 to about 10 ethylene oxide moieties and from 0 to 1 glyceryl moiety;
• Y is nitrogen;
• R and R are short chain alkyl or monohydroxy alkyl groups containing 1 to about 3 carbon atoms,
• betaine or sulfobetaine detergents described above are utilized in this invention in amounts of from 0.5% to about 50% by weight of the concentrate.
• these detergents are utilized in amounts of from about 5 to about 30% by weight of the concentrate.
• Acetanilid can be used in the concentrates of the present invention to provide added stability during use of diluted compositions prepared from the concentrate, especially when the concentrates are diluted with water that has not been properly purified.
• the acetanilid can be incorporated in the concentrate in amounts of 0 0.5%.
• the concentrate of this invention can optionally contain about 0.01 1% of complex-forming compounds such as ethylene-diaminetetraacetic acid or its water soluble salts, or analogues, such as diethylenetriaminepentaacetic acid or its water soluble salts.
• complex-forming compounds such as ethylene-diaminetetraacetic acid or its water soluble salts, or analogues, such as diethylenetriaminepentaacetic acid or its water soluble salts.
• the alkali metal salts of the acids are presently preferred, such as, monosodium edetate (ethylenediaminetetraacetate), disodium edetate and sodium diethylene triamine pentaacetate. Combinations of several complex-forming compounds can be used as well.
• the complex-forming compounds impart additional cleaning power to the concentrates of this invention, and this is particularly so where insoluble chelatable metal ion salts of fatty acids, such as, for example, calcium stearate are to be removed from skin.
• the complex-forming compounds tie up divalent and trivalent cations often present in water, thereby preventing undesirable precipitates from forming.
• the concentrates of this invention can optionally contain from 0.01 to of a quaternary ammonium surface active agent.
• the quaternary ammonium surface active agents useful in this invention are exemplitied by benzalkonium chloride, cetalkonium chloride, cetylpyridinium chloride, benzethonium chloride, and cethexonium bromide. These agents may be added for the purpose of increasing detergency and foam stability as well as for imparting residual germicidal activity. Active oxygen releasing compounds such as hydrogen peroxide react relatively quickly upon contact with oxidizable organic materials and their germicidal effectiveness is dissipated soon thereafter.
• the foam stabilizing effect of quaternary ammonium surface active agents in the concentrates of this invention contributes to the overall combination of desirable properties achieved by the concentrates of this invention.
• concentrates having at least three different types of surfactants enables the stability arid physical properties of the concentrates to be varied as required by different end uses of the concentrates. For example, if more foaming is desired, the concentration of the betaine and/or sulfobetaine and/or quaternary ammonium surfactant can be increased. If less foam and less detergency is desired, the concentration of the polyoxypropylene-polyoxyethylene copolymer can be increased and/or the amount of the quaternary ammonium surfactant and/or the betaine or sulfobetaine surfactant can be decreased.
• the liquid detergent concentrates of this invention have a wide pH range between 2 and 10 and preferably have a pH between 3 and 7.
• a desired acid pH can be imparted to the concentrates of this invention by addition of hydrochloric acid, phosphoric acid, acetic acid, sulfuric acid, nitric acid or any other acid which does not react with active oxygen.
• adjustment of the pH in the alkaline region can be accomplished with any non-reactive water-soluble non-volatile basic substance such as for example, sodium hydroxide, potassium hydroxide, borax, trisodium phosphate, and the like.
• the concentrates of this invention are useable for many different purposes in industry and/or in the household.
• the concentrates have broad medical and non-medical applications as nonselective germicides and bleaching agents. Examples include the bleaching of hair, textiles, wood and/or plastic composition, use in the bleaching steps of paper manufacture; the cleaning, degerming and/or bleaching of floors, work surfaces, animal areas, laboratories, sterile work areas and the like; the cleaning and degerming of skin areas prior to surgery; use as a presurgical hand scrubbing agent; and the cleaning and degerming of infants in nurseries to prevent cross infection.
• the concentrates can be diluted for a particular application or used full strength.
• Water of a high degree of purity is preferably used to bring about dilution and prolong the stability of the resulting compostion, but ordinary tap water can be used if pure water is not available. Dilutions of from 2 to 200 fold can be made with the concentrates of this invention.
• a liquid concentrate is prepared in accordance with the present invention having the following composition:
• This concentrate is tested as a cleanser by acne patients and is subjectively found to be effective in promoting healing of acne lesions.
• the hands and face of the patient are wetted with water, followed by application with the finger tips of the concentrate to the lesions on the face and other affected parts.
• the cleanser is allowed to remain on the patients skin for l to 2 minutes, and is then rinsed off with hot water. This treatment is performed for 10 to 21 days.
• the concentrate of this example along the hair line causes the hair to be bleached.
• the concentrate can thus be used as a cosmetic hair bleach, but it must be kept out of the eyes.
• the germicidal and bactericidal activity of the concentrate is tested against the following organisms:
• Twenty-four hour broth cultures of the above microorganisms are centrifuged and resuspended in normal saline. Each bacterial suspension in the amount of 0.2 ml is added to 3.8 ml samples of each concentrate and to 3.8 ml samples of a control solution of normal saline. The resulting suspensions are then held at room temperature and tested for bacterial viability at 15 minutes, 30 minutes and 1 hour post-inoculation. Tests for bacterial viability are performed by inoculating 0.1 ml of sample into 0.9 m1 Tryptic Soy Broth and incubating at 37 C for 1 week.
• Control cultures are all in the range of 10 to 10 colony forming units (CFU) per ml.
• the stability of the concentrate of this example is evaluated in 2 oz. natural polyethylene containers at room temperature (68-72 F) using a standard potassiurn permanganate titration procedure for the assay.
• a liquid concentrate in accordance with the present invention is prepared having the following composition:
• cetyl betaine (du Pont) 25.0% polyoxypropylenc-polyoxyethylene condensate (Pluronic F68, Wyandotte) 15.07: hydrogen peroxide 30.0% phosphoric acid to pH 4.0 purified water 0.8. 100.0%
• This concentrate can be diluted with water as required to form a dilute solution containing about 0.1% to 20.0% of concentrate.
• the diluted concentrate can be used to bleach, degerm and/or clean dirtied, aged, or discolored surfaces such as plastic floor coverings, wood, desk or laboratory bench surfaces and the like.
• the concentrate is particularly effective in removing aged or yellowed wax.
• Urea peroxide 10.0% Polyoxypropylene-polyoxyethylene concentrate (Pluronic F-108) 10.0% Disodium edetate 0.1% Dodecyl sulfobetaine 10.0% Cetalkonium chloride 0.25% Purified Water Q.S.. ad 100
• This concentrate is useful as a skin cleanser and debriding agent.
• the urea has a desirable keratolylic effect particularly in those instances where a hyperkeratotic skin condition exists.
• the concentrate when diluted about 1:20 with water is an efiective vaginal douche.
• EXAMPLE 1V Another concentrate is prepared having the following composition:
• Benzoyl peroxide 5.07: Polyoxypropylcne-polyoxyethy1ene concentrate (Pluronic L452) 15.0? Lauryl sulfobetninc DCH (Textiluna) 5.0; Cctylpyridinium chloride 0.05% Acetunilid 0.0l'7r Sodium diethylcne triamine pentaacctate 0.2% Purified Water, Q.S. 100.0%
• the concentrate of this example can be used for the same purposes and in the same manner as the concentrate of Example I but is less harsh in removing natural skin oils, e.g., in presurgical scrub.
• Hydrogen peroxide 1.01 Polyoxyethylene-Polyoxypropylcne condensate (Pluronic F-l27) 20.0% Cetyl sulfobctainc DLH (Tcxliltmu) 15.0% Monosodium edetate 0.17r Benzalkonium chloride 0.1% Purified water, 0.5. 100.0%
• This concentrate is particularly useful in infant nurseries as a skin bathing composition. Although the concentrate is also effective in preoperative preparation and scrubbing, it has the desired mildness as well as adequate antimicrobial effects. This concentrate is thus a valuable substitute for hexachlorophene containing detergent compositions that have been used for these pur poses.
• a stable liquid concentrate composition consisting essentially of:
• a water soluble zwitterionic detergent selected from the group consisting of sulfobetaine and betaine surfactants of the formula:
• R is a long chain radical and contains an alkyl, alkenyl, or hydroxy alkyl radical of from about 8 to about 24 carbon atoms, from 0 to about 10 ethylene oxide moieties and from 0 to l glyceryl moiety;
• Y is nitrogen;
• R and R are short chain alkyl or monohydroxy alkyl groups containing 1 to about 3 carbon atoms; 1: is 0 to l;
• R is an alkylene or hydroxy alkylene of from 1 to about 4 carbon atoms; and
• Z is a radical selected from the group consisting of carboxylate and sulfonate groups;
• a nonionic polyoxyethylenepolyoxypropylene block copolymer surfactant having a water solubility of at least one gram per 100 m1. of water and a molecular weight within the range of about 1,000 to about 15,000;
• composition of claim 1 wherein the active oxygen yielding compound is hydrogen peroxide.
• composition of claim 2 wherein the concentration of hydrogen peroxide is from about 0.5% to about 10%.
• composition according to claim 1 wherein the active oxygen-containing compound is selected from the group consisting of urea peroxide, benzoyl peroxide and hydrogen peroxide.
• composition according to claim 1 including 0.01 10% of a water soluble quaternary ammonium surface active agent.
• composition according to claim 1 including a complex-forming compound selected from the group consisting of ethylene-diaminetetraacetic acid, diethylcnetriaminepentaacetic acid, and their water-soluble salts.
• composition according to claim 1 including acetanilid.
• composition of claim 1 including 0.01 10% of a water soluble quaternary ammonium surfaceactive and a complex-forming compound selected from the group consisting of ethylene-diaminetetraacetic acid, diethylenetriaminepentaacetic acid, and their water-soluble salts.
• composition according to claim 1 wherein the concentration of the active oxygen yielding compound is from about 0.5% to about 10%.
• a stable liquid concentrate consisting essentially of:
• a water soluble zwitterionic detergent selected from the group consisting of sulfobetaine and betaine surfactants of the formula:
• R is a long chain radical and contains an alkyl, alkenyl, or hydroxy alkyl radical of from about 8 to about 24 carbon atoms, from to about 10 ethylene oxide moieties and from 0 to l glyceryl moiety;
• Y is nitrogen;
• R and R are short chain alkyl or monohydroxy alkyl groups containing 1 to about 3 carbon atoms;
• x is 0 or 1;
• R is an alkylene 5 or hydroxy alkylene of from 1 to about 4 carbon atoms; and
• Z is a radical selected from the group consisting of carboxylate and sulfonate groups; c.
• a nonionic polyoxyethylenepolyoxypropylene block copolymer surfactant having a water solubility of at least one gram per 100 ml. of water and a molecular weight within the range of about 1,000 to about 15,500; d. about 0.01 to about 1% of a complex-forming compound selected from the group consisting of ethylene-diaminetatraacetic acid, diethylenetriaminepentaacetic acid, and their water-soluble salts;
• composition of claim 2 wherein the zwitterionic detergent is dodecyl sulfobetaine.
• composition according to claim 5 wherein the quaternary ammonium surface active agent is selected from the group consisting of benzalkonium chloride, cetalkonium chloride, cetylpyridinium chloride, benzethonium chloride and cethexonium bromide.
• composition according to claim 6 wherein the complex-forming compound is present in an amount of about 0.01 1%.
• composition according to claim 9 wherein the active oxygen yielding compound is selected from the group consisting of urea peroxide, benzoyl peroxide, lauryl peroxide, peroxyacetic acid, sodium peroxydisulfate, di-tert-butyl peroxide, methyl ethyl ketone peroxide, sodium peroxide, and sodium perborate.
• composition of claim 10 wherein the quaternary ammonium surface active agent is selected from the group consisting of benzalkonium chloride, cetalkonium chloride, cetylpyridinium chloride, benzethonium chloride, and cethexonium bromide.
• composition of claim 10 wherein the concentration of hydrogen peroxide is from about 0.5% to about 10%, the concentration of the zwitterionic detergent is from about 5% to about 30%, and the concentration of the block copolymer is from about 5% to about 25%.
• Claim 1 Col. 8, line 64, change '0 to 1"
• Claim 1 Col. 9, line 5, change "15,000"

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• Health & Medical Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Veterinary Medicine (AREA)
• Public Health (AREA)
• General Health & Medical Sciences (AREA)
• Animal Behavior & Ethology (AREA)
• Epidemiology (AREA)
• Engineering & Computer Science (AREA)
• Birds (AREA)
• Organic Chemistry (AREA)
• Wood Science & Technology (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Emergency Medicine (AREA)
• Inorganic Chemistry (AREA)
• Dermatology (AREA)
• Detergent Compositions (AREA)
• Medicinal Preparation (AREA)
• Anti-Oxidant Or Stabilizer Compositions (AREA)
• Cosmetics (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)

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Cited By (51)

Families Citing this family (25)

Citations (1)

• 1972
  • 1972-08-11 US US00279801A patent/US3852210A/en not_active Expired - Lifetime
• 1973
  • 1973-08-03 AU AU58879/73A patent/AU470214B2/en not_active Expired
  • 1973-08-07 NL NLAANVRAGE7310909,A patent/NL168878C/xx not_active IP Right Cessation
  • 1973-08-08 BE BE134362A patent/BE803362A/xx not_active IP Right Cessation
  • 1973-08-09 IT IT27706/73A patent/IT998336B/it active
  • 1973-08-09 FR FR7329233A patent/FR2328039A1/fr active Granted
  • 1973-08-09 GB GB3788973A patent/GB1398253A/en not_active Expired
  • 1973-08-10 CA CA178,501A patent/CA997647A/en not_active Expired
  • 1973-08-10 DE DE19732340568 patent/DE2340568B2/de not_active Ceased
  • 1973-08-11 JP JP48090477A patent/JPS5141105B2/ja not_active Expired
  • 1973-08-13 LU LU68215A patent/LU68215A1/xx unknown

Patent Citations (1)

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