US2299604A - Fungicidal composition - Google Patents
Fungicidal composition Download PDFInfo
- Publication number
- US2299604A US2299604A US307185A US30718539A US2299604A US 2299604 A US2299604 A US 2299604A US 307185 A US307185 A US 307185A US 30718539 A US30718539 A US 30718539A US 2299604 A US2299604 A US 2299604A
- Authority
- US
- United States
- Prior art keywords
- salt
- phenoxyacetic acid
- composition
- water
- solution
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title description 38
- 230000000855 fungicidal effect Effects 0.000 title description 19
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 64
- 235000002639 sodium chloride Nutrition 0.000 description 38
- 150000003839 salts Chemical class 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 27
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 7
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000011780 sodium chloride Substances 0.000 description 6
- 230000009182 swimming Effects 0.000 description 6
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 5
- 201000004647 tinea pedis Diseases 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 4
- 241000233866 Fungi Species 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- 235000019574 salt enhancing Nutrition 0.000 description 3
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 3
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 208000002474 Tinea Diseases 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- 235000011148 calcium chloride Nutrition 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 229910017053 inorganic salt Inorganic materials 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 235000011147 magnesium chloride Nutrition 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000001103 potassium chloride Substances 0.000 description 2
- 235000011164 potassium chloride Nutrition 0.000 description 2
- OTYBMLCTZGSZBG-UHFFFAOYSA-L potassium sulfate Chemical compound [K+].[K+].[O-]S([O-])(=O)=O OTYBMLCTZGSZBG-UHFFFAOYSA-L 0.000 description 2
- 229910052939 potassium sulfate Inorganic materials 0.000 description 2
- 239000001120 potassium sulphate Substances 0.000 description 2
- 235000011151 potassium sulphates Nutrition 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000011592 zinc chloride Substances 0.000 description 2
- 235000005074 zinc chloride Nutrition 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 230000001066 destructive effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/24—Heavy metals; Compounds thereof
- A61K33/30—Zinc; Compounds thereof
Definitions
- the present invention relates to compositions for killing fungi which cause epidermophytosis, popularly referred to as athlete's foot," which latter name is commonly employed owing to the prevalence of the disease.among. persons making use of gymnasiums, locker rooms, swimming pools and bathrooms which are utilized by large numbers of persons.
- the infection known as athletes foot is contagious and communicable by means of contaminated clothing and contaminated equipment, structures and floors, particularly the floors of gymnasiums, swimming pool rooms or of areas around swimming pools, and of locker rooms used in connection with gymnasiums and swimming pools, on the floors of which the skin of the feet of persons come in direct contact.
- a further object of the invention is to provide a composition suitable for use in water as a foot bath, in which persons utilizing gymnasiums, swimming pools, public baths, and locker rooms used in connection therewith, may immerse or bathe their feet in order to kill the fungi of athlete's foot" which may have lodged upon, or adhered to, their feet by walking upon infected floors, equipment or structures.
- composition is prepared for use by dissolving the phenoxyacetic acid and the salt in water.
- mixtures of two or more of the salts may be employed, instead of a single salt.
- the composition so prepared may also include other fungicidal agents, such as paranitrophenol, or other components which are compatible with the phenoxyacetic acid and salt or mixtures of salts.
- a composition including phenoxyacetic acid, paranitrophenol, water and one or more of the salts described above is a particularly advantageous composition, owing to the fact that the solubility of the paranitrophenol or the phenoxyacetic acid in the salt solutions is not sigin the prepared solution may vary within wide salt,- a resulting fungicidal power high enough 'for the purposes herein described.
- the salt limits but in view of the foregoing disclosures it will be evident'to the person skilled in the art that itshould be employed in high enough concentration in solution to give, in combination with the enhancement of its fungicidal power by the concentration in the solution may also vary within wide limits in the composition prepared for use.
- the salt concentration should be at least two and one-half per cent based upon the weight of the prepared solution, since below this percentage there does not appear to be any practical or commercial enhancement of fungicidal power, so far as determinable by present known methods of determining fungicidal power. In general it is moreadvantageous to employ higher percentages of salt in the prepared solution, for
- compositions of the present invention may be prepared, by adding the phenoxyacetic acid and salt as separate reagents to the same body of water and dissolving them therein, or a mixture or the phenoxyacetic acid and salt may be preliminarily prepared and the mixture thereai'ter dissolved in water, the relative proportion of phenoxyacetic acid and the salt, without dissolving them in water, and sell these mixtures, in powdered, granular or crystalline form, with suitable instructions for utilizing them in water solution according to the present invention.
- the said mixtures therefore, constitute an essential part of my invention, and are to be understood as being included within the terms of the appended claims.
- a small amount of suitable acid material cheaper than the phenoxya'cetic acid may be included in the mixture as a butler to prevent partial neutralization of the .phenoxyacetic acid by such soap.
- suitable acid material cheaper than the phenoxya'cetic acid
- examples of such addition agents which in the concentrations used are without fungicidal power, are sodium bisulfate and citric acid.
- fungicidal powers or properties of a water solution containing both the phenoxyacetic acid and the salt in dissolved condition are greater than the sum of the fungicidal powers of separate solutions of the DhenoXyacetic acid and the salt of respectively the same concentrations in which the phencxyacetic ,acid and the salt are present in a minture of them in dissolved condition in the some body of solvent.
- Example If form, and 0.0% pound of powdered citric acid.
- Example H 0.050 pound of powdered phenoxyacetic acid are intimatelymixed with 0.945 pound of solid malnesium sulphate in fine crystal or pulverized form, and 0.005 pound of powdered sodium bisulfate.
- Example IV 0.030 pound of powdered phenoxyacetic acid and 0.030 pound of powdered paranitrophenol are intimately mixed with 0.935 pound of finely divided solid sodium chloride, and 0.005 pound of powdered sodium bisulfate.
- Example V 0.050 pound of powdered phenoxyacetic acid m intimately mixed with 0.445 pound of pow- I phenoxyacetic acid in the composition, the said salt enhancing the fungicidal properties of the phenoxyacetic acid when the composition is dissolved in water to form a solution containing at least 2 per cent concentration of the salt based upon the weight of the solution.
- a fungicidal composition comprising phenoxyacetic acid and sodium chloride, the proportion of sodium chloride therein greatly exceeding the proportion of phenoxyacetic acid.
- a fungicidal composition comprising phenoxyacetic acid, paranitrophenol and a water soiuisle inorganic salt compatible in water solution with said piricnoxyacetic acid and said paranitrophenol, the proportion of said salt in the composition greatly exceeding the proportions of phenoxyacetic acid and paranitrophenol in the composition, the salt enhancing the fungipropertics oi the pnenomacetic acid and the paranitrophcnol when the composition is dissolved in to force a solution containing at least 2%.; per cent concentration of the salt based upon the weight of the solution.
- E. fungicidal composition for killing organisms causing athlete's foot comprising a solntion containing phenoxyacetic acid, water and a water soluble inorganic salt compatible in water solution with phenoxyacetic acid, the proportion 'of said salt in the composition greatly exceeding the proportion of phenoxyacetic acid in the composition, the said salt and water being present in the solution in such proportions as to provide an aqueous solution of said salt of at least 2 /2 per cent, based upon the weight of the solution and said salt at said concentrationenhancing the fungicidal properties of said phenoxyacetic acid.
- a fungicidal-composition for killing organisms causing athlete's foot comprising a solution containing phenoxyacetic acid, water, and material selected from the group consisting of sodium chloride, sodium sulphate, potassium chloride, potassium sulphate, magnesium chloride, magnesium sulphate, calcium chloride, ammonium chloride and zinc chloride, the proportion of said material in the solution greatly exceeding the proportion of phenoxyacetic acid and being present in a concentration of at least 2 per cent
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Inorganic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Description
Patented Oct. 20, 1942 F'EICE.
FUNGICIDALV com'osnron Clarence L. Weirich, Westport, Conn, assignor to The C. B. Dolge Company, Westport, Conn., a corporation of Connecticut No Drawing. Application December 1, 1939, Serial No. 307,185
6 Claims. (01. 1s7- -3o The present invention relates to compositions for killing fungi which cause epidermophytosis, popularly referred to as athlete's foot," which latter name is commonly employed owing to the prevalence of the disease.among. persons making use of gymnasiums, locker rooms, swimming pools and bathrooms which are utilized by large numbers of persons.
The infection known as athletes foot is contagious and communicable by means of contaminated clothing and contaminated equipment, structures and floors, particularly the floors of gymnasiums, swimming pool rooms or of areas around swimming pools, and of locker rooms used in connection with gymnasiums and swimming pools, on the floors of which the skin of the feet of persons come in direct contact.
It is an object of the present invention to provide a composition which, when applied to the floors of gymnasiums, to the floor around swimmlng pools, to the floors of bathrooms, and on the floors of locker rooms used in connection with gymnasiums and swimming pools, will kill, or render harmless to humans, the fungi which cause'epidermophytosis or athlete's. foot," and thereby prevent, or lessen, the communication of the disease to persons not infected with it.
A further object of the invention is to provide a composition suitable for use in water as a foot bath, in which persons utilizing gymnasiums, swimming pools, public baths, and locker rooms used in connection therewith, may immerse or bathe their feet in order to kill the fungi of athlete's foot" which may have lodged upon, or adhered to, their feet by walking upon infected floors, equipment or structures.
I have discovered that many water soluble- Examples of compatible salts of inorganic acids which increase the fungicidal powers of phenoxyacetic acid are: sodium chloride, sodium sulphate, potassium chloride, potassium sulphate, magnesium chloride, magnesium sulphate, calcium chloride, ammonium chloride, and zinc chloride.
The composition is prepared for use by dissolving the phenoxyacetic acid and the salt in water. In preparing this solution mixtures of two or more of the salts may be employed, instead of a single salt. The composition so prepared may also include other fungicidal agents, such as paranitrophenol, or other components which are compatible with the phenoxyacetic acid and salt or mixtures of salts.
A composition including phenoxyacetic acid, paranitrophenol, water and one or more of the salts described above is a particularly advantageous composition, owing to the fact that the solubility of the paranitrophenol or the phenoxyacetic acid in the salt solutions is not sigin the prepared solution may vary within wide salt,- a resulting fungicidal power high enough 'for the purposes herein described. The salt limits, but in view of the foregoing disclosures it will be evident'to the person skilled in the art that itshould be employed in high enough concentration in solution to give, in combination with the enhancement of its fungicidal power by the concentration in the solution may also vary within wide limits in the composition prepared for use. In the composition as prepared for use in the form of a solution, I have found that the salt concentration should be at least two and one-half per cent based upon the weight of the prepared solution, since below this percentage there does not appear to be any practical or commercial enhancement of fungicidal power, so far as determinable by present known methods of determining fungicidal power. In general it is moreadvantageous to employ higher percentages of salt in the prepared solution, for
example from 6 per cent to saturation of the salt in the prepared solution. In general, the
- enhancement of the fungicidal power increases as the percentage of salt in the solution increases.
The compositions of the present invention may be prepared, by adding the phenoxyacetic acid and salt as separate reagents to the same body of water and dissolving them therein, or a mixture or the phenoxyacetic acid and salt may be preliminarily prepared and the mixture thereai'ter dissolved in water, the relative proportion of phenoxyacetic acid and the salt, without dissolving them in water, and sell these mixtures, in powdered, granular or crystalline form, with suitable instructions for utilizing them in water solution according to the present invention. The said mixtures, therefore, constitute an essential part of my invention, and are to be understood as being included within the terms of the appended claims. Since the feet of persons, coming from showers may be slightly alkaline from soap, a small amount of suitable acid material cheaper than the phenoxya'cetic acid may be included in the mixture as a butler to prevent partial neutralization of the .phenoxyacetic acid by such soap. Examples of such addition agents, which in the concentrations used are without fungicidal power, are sodium bisulfate and citric acid.
In the foregoing description and in the appended claims, it is to be noted that when refer ence is made to enhancement or increase of fungicidal powers or properties of the phenoxyacetic acid by means of the salts of inorganic acids which are compatible with the said phenoxyacetic acid, it is intended to indicate that the fungicidal powers or properties of the phenoxyacetic acid are greater in the presence of said salts than. in their absence, and that the resulting fungicidal powers or properties of a water solution containing both the phenoxyacetic acid and the salt in dissolved condition are greater than the sum of the fungicidal powers of separate solutions of the DhenoXyacetic acid and the salt of respectively the same concentrations in which the phencxyacetic ,acid and the salt are present in a minture of them in dissolved condition in the some body of solvent.
When I state herein that the salts of the inorganic acids or other substances are compatible with the phenoxyacetic acid, I intend to indicate that the said salts and other substances do not act upon the phenoxyacetic acid in water solution in such a manner as to be destructive of the iungicidai powers of the phenoxyacctic acid in water solution.
The following specific examples are given as 0.050 pound of powdered phenosyacetic acid are intimately mixed with 0.8 5 pound of fee divided solid sodium chloride.
The whole of this mixture is dissolved in gallon of water for use.
Example If form, and 0.0% pound of powdered citric acid.
' The whole of this mixture is dissolved in on gallon of water for use.
Example H! 0.050 pound of powdered phenoxyacetic acid are intimatelymixed with 0.945 pound of solid malnesium sulphate in fine crystal or pulverized form, and 0.005 pound of powdered sodium bisulfate.
The whole of this mixture is dissolved in one gallon of water for use.
Example IV 0.030 pound of powdered phenoxyacetic acid and 0.030 pound of powdered paranitrophenol are intimately mixed with 0.935 pound of finely divided solid sodium chloride, and 0.005 pound of powdered sodium bisulfate.
The whole of this mixture is dissolved in one gallon of water for use.
Example V 0.050 pound of powdered phenoxyacetic acid m intimately mixed with 0.445 pound of pow- I phenoxyacetic acid in the composition, the said salt enhancing the fungicidal properties of the phenoxyacetic acid when the composition is dissolved in water to form a solution containing at least 2 per cent concentration of the salt based upon the weight of the solution.
2. A fungicidal composition comprising phenoxyacetic acid and sodium chloride, the proportion of sodium chloride therein greatly exceeding the proportion of phenoxyacetic acid.
3. A fungicidal composition comprising phenoxyacetic acid, a water soluble inorganic sait compatible in water solution with phenoxyacetic acid, and another water soluble compatible acidic material for increasing the acidity of a water soiution or the composition over and above the acidity provided by the phenoxyacctic acid, the proportion of said salt in the composition greatly exceeding the proportion of phenorry= acetic acid in the composition, the said salt enhancing the fungicidal properties of the phcnoxyacetic acid when the composition m dissolved in water to form a solution containing at least 2%; per cent concentration of the salt based upon the weight of the solution.
a fungicidal composition comprising phenoxyacetic acid, paranitrophenol and a water soiuisle inorganic salt compatible in water solution with said piricnoxyacetic acid and said paranitrophenol, the proportion of said salt in the composition greatly exceeding the proportions of phenoxyacetic acid and paranitrophenol in the composition, the salt enhancing the fungipropertics oi the pnenomacetic acid and the paranitrophcnol when the composition is dissolved in to force a solution containing at least 2%.; per cent concentration of the salt based upon the weight of the solution.
5. E. fungicidal composition for killing organisms causing athlete's foot comprising a solntion containing phenoxyacetic acid, water and a water soluble inorganic salt compatible in water solution with phenoxyacetic acid, the proportion 'of said salt in the composition greatly exceeding the proportion of phenoxyacetic acid in the composition, the said salt and water being present in the solution in such proportions as to provide an aqueous solution of said salt of at least 2 /2 per cent, based upon the weight of the solution and said salt at said concentrationenhancing the fungicidal properties of said phenoxyacetic acid.
6. A fungicidal-composition for killing organisms causing athlete's foot comprising a solution containing phenoxyacetic acid, water, and material selected from the group consisting of sodium chloride, sodium sulphate, potassium chloride, potassium sulphate, magnesium chloride, magnesium sulphate, calcium chloride, ammonium chloride and zinc chloride, the proportion of said material in the solution greatly exceeding the proportion of phenoxyacetic acid and being present in a concentration of at least 2 per cent
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US307185A US2299604A (en) | 1939-12-01 | 1939-12-01 | Fungicidal composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US307185A US2299604A (en) | 1939-12-01 | 1939-12-01 | Fungicidal composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2299604A true US2299604A (en) | 1942-10-20 |
Family
ID=23188620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US307185A Expired - Lifetime US2299604A (en) | 1939-12-01 | 1939-12-01 | Fungicidal composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2299604A (en) |
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2437527A (en) * | 1945-06-14 | 1948-03-09 | Rohm & Haas | Insecticidal compositions from halocaprylphenoxyacetic acid |
| US2437427A (en) * | 1945-06-14 | 1948-03-09 | Rohm & Haas | Insecticidal compositions comprising a phenyl ester of caprylphenoxyacetic acid |
| US2449787A (en) * | 1944-10-09 | 1948-09-21 | Dow Chemical Co | Preservation of cellulosic materials |
| US2451085A (en) * | 1945-06-14 | 1948-10-12 | Rohm & Haas | Insecticidal haloido-alkylene esters of caprylphenoxyacetic acid |
| US2559546A (en) * | 1948-04-13 | 1951-07-03 | Dow Chemical Co | 3-pyridoxy-alkanoic acid compounds |
| US2577969A (en) * | 1944-08-17 | 1951-12-11 | American Chem Paint Co | Compositions for killing weeds |
| US2580048A (en) * | 1948-04-12 | 1951-12-25 | Standard Oil Dev Co | Fungicidal emulsion comprising a copper salt of an alkylated phenoxy acetic acid |
| US2614963A (en) * | 1951-01-10 | 1952-10-21 | Kendall & Co | Keratin exfoliative compositions |
| US4172888A (en) * | 1978-09-12 | 1979-10-30 | Robert E. Delzell, Sr. | Athlete's foot treatment |
| US20070141172A1 (en) * | 2005-12-21 | 2007-06-21 | Robert Baltzell | Method of treating bacterial hoof infections of sheep and cattle |
| US20090176876A1 (en) * | 2008-01-04 | 2009-07-09 | Jr Chem, Llc | Compositions, kits and regimens for the treatment of skin, especially decolletage |
| US7687650B2 (en) | 2006-02-03 | 2010-03-30 | Jr Chem, Llc | Chemical compositions and methods of making them |
| US7867522B2 (en) | 2006-09-28 | 2011-01-11 | Jr Chem, Llc | Method of wound/burn healing using copper-zinc compositions |
| US7897800B2 (en) | 2006-02-03 | 2011-03-01 | Jr Chem, Llc | Chemical compositions and methods of making them |
| US7927614B2 (en) | 2006-02-03 | 2011-04-19 | Jr Chem, Llc | Anti-aging treatment using copper and zinc compositions |
| US8952057B2 (en) | 2011-01-11 | 2015-02-10 | Jr Chem, Llc | Compositions for anorectal use and methods for treating anorectal disorders |
| US9427397B2 (en) | 2009-01-23 | 2016-08-30 | Obagi Medical Products, Inc. | Rosacea treatments and kits for performing them |
| US11559053B1 (en) | 2016-09-23 | 2023-01-24 | Specialty Sales, LLC | Livestock footbath solutions and methods of use |
-
1939
- 1939-12-01 US US307185A patent/US2299604A/en not_active Expired - Lifetime
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2577969A (en) * | 1944-08-17 | 1951-12-11 | American Chem Paint Co | Compositions for killing weeds |
| US2449787A (en) * | 1944-10-09 | 1948-09-21 | Dow Chemical Co | Preservation of cellulosic materials |
| US2437427A (en) * | 1945-06-14 | 1948-03-09 | Rohm & Haas | Insecticidal compositions comprising a phenyl ester of caprylphenoxyacetic acid |
| US2451085A (en) * | 1945-06-14 | 1948-10-12 | Rohm & Haas | Insecticidal haloido-alkylene esters of caprylphenoxyacetic acid |
| US2437527A (en) * | 1945-06-14 | 1948-03-09 | Rohm & Haas | Insecticidal compositions from halocaprylphenoxyacetic acid |
| US2580048A (en) * | 1948-04-12 | 1951-12-25 | Standard Oil Dev Co | Fungicidal emulsion comprising a copper salt of an alkylated phenoxy acetic acid |
| US2559546A (en) * | 1948-04-13 | 1951-07-03 | Dow Chemical Co | 3-pyridoxy-alkanoic acid compounds |
| US2614963A (en) * | 1951-01-10 | 1952-10-21 | Kendall & Co | Keratin exfoliative compositions |
| US4172888A (en) * | 1978-09-12 | 1979-10-30 | Robert E. Delzell, Sr. | Athlete's foot treatment |
| US7670629B2 (en) | 2005-12-21 | 2010-03-02 | Robert Baltzell | Method of treating bacterial hoof infections of sheep and cattle |
| US20070141172A1 (en) * | 2005-12-21 | 2007-06-21 | Robert Baltzell | Method of treating bacterial hoof infections of sheep and cattle |
| US7927614B2 (en) | 2006-02-03 | 2011-04-19 | Jr Chem, Llc | Anti-aging treatment using copper and zinc compositions |
| US7687650B2 (en) | 2006-02-03 | 2010-03-30 | Jr Chem, Llc | Chemical compositions and methods of making them |
| US7897800B2 (en) | 2006-02-03 | 2011-03-01 | Jr Chem, Llc | Chemical compositions and methods of making them |
| US8148563B2 (en) | 2006-02-03 | 2012-04-03 | Jr Chem, Llc | Chemical compositions and methods of making them |
| US7867522B2 (en) | 2006-09-28 | 2011-01-11 | Jr Chem, Llc | Method of wound/burn healing using copper-zinc compositions |
| US20090176876A1 (en) * | 2008-01-04 | 2009-07-09 | Jr Chem, Llc | Compositions, kits and regimens for the treatment of skin, especially decolletage |
| US8273791B2 (en) | 2008-01-04 | 2012-09-25 | Jr Chem, Llc | Compositions, kits and regimens for the treatment of skin, especially décolletage |
| US8505730B2 (en) | 2008-01-04 | 2013-08-13 | Jr Chem, Llc | Compositions, kits and regimens for the treatment of skin, especially décolletage |
| US9427397B2 (en) | 2009-01-23 | 2016-08-30 | Obagi Medical Products, Inc. | Rosacea treatments and kits for performing them |
| US8952057B2 (en) | 2011-01-11 | 2015-02-10 | Jr Chem, Llc | Compositions for anorectal use and methods for treating anorectal disorders |
| US11559053B1 (en) | 2016-09-23 | 2023-01-24 | Specialty Sales, LLC | Livestock footbath solutions and methods of use |
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