USRE33512E - Novel anti-microbial systems containing the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide and a water soluble zinc salt - Google Patents
Novel anti-microbial systems containing the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide and a water soluble zinc salt Download PDFInfo
- Publication number
- USRE33512E USRE33512E US07/289,962 US28996288A USRE33512E US RE33512 E USRE33512 E US RE33512E US 28996288 A US28996288 A US 28996288A US RE33512 E USRE33512 E US RE33512E
- Authority
- US
- United States
- Prior art keywords
- magnesium sulfate
- zinc salt
- zinc
- adduct
- sulfate adduct
- 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 - Fee Related
Links
Classifications
-
- 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
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/16—Heavy metals; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- 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
-
- 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
- A61K8/27—Zinc; Compounds thereof
-
- 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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4933—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having sulfur as an exocyclic substituent, e.g. pyridinethione
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- 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
- 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
- This invention relates to novel antimicrobial systems containing a water-soluble, non-ionic pyrethione derivative known chemically as the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide (referred to hereinafter as "the magnesium sulfate adduct") and a water soluble zinc salt. More particularly, it has been found that the presence of a water soluble zinc salt appears to enhance to an unexpected extent the antimicrobial activity of the magnesium sulfate adduct against certain types of microorganisms such, for example, as .[.Staphylococcus epidermidis, Staphylococcus aureus and.]. Pseudomonas aeruginosa.
- the antimicrobial system of this invention may be incorporated in various useful therapeutic and cleansing compositions such, for example, as surgical scrub compositions, skin disinfectants, mouthwashes, deodorants, hospital cleaners, etc.
- the magnesium sulfate adduct used in accordance with this invention is a well known broad spectrum antimicrobial agent.
- a well known commercially available form is sold by Olin Chemicals of Stanford, Conn. under the trade name "OMADINE MDS" which is the trihydrate form.
- magnesium sulfate adduct used in this invention has broad spectrum antimicrobial activity, it lacks the desired activity against Pseudomonas aeruginosa, the microorganism associated with infection that often follows severe burning of the skin.
- An object of the invention is to provide novel antimicrobial systems wherein enhanced antimicrobial activity of the magnesium sulfate adduct is effectuated against certain types of microorganisms.
- Another object of this invention is to provide novel therapeutic and cleansing compositions having incorporated therein the antimicrobial system set forth in the foregoing object.
- the objects of this invention may be realized by forming an antimicrobial system containing the magnesium sulfate adduct and a water soluble salt.
- microbiological testing indicates that the activity of magnesium sulfate adduct against Ps. aeruginosa is enhanced in the presence of water soluble zinc salts.
- the preferred zinc salt used in accordance with this invention is zinc chloride (ZnCl 2 ).
- Other water soluble zinc salts which may be used are zinc acetate, zinc sulfate, zinc nitrate, zinc phenylsulfonate, etc.
- the zinc salt should be in an amount from about 1 to about 10, and preferably from about 1 to 1 parts by weight per part of the magnesium sulfate adduct.
- the magnesium sulfate adduct in general is in an amount from about 0.1 to 1.5% by weight and the zinc salt from about 0.1 to 1% by weight, of the total composition.
- a most useful antimicrobial composition that may be obtained utilizing the present invention is a surgical scrub compositions employing the antimicrobial system of this invention in an anhydrous foamable base composition.
- Such surgical scrub compositions have been found useful in killing .[.both Staphylococcus aureus and.]. .Iadd.the .Iaddend.Pseudomonas aeruginosa .[.types of bacteria.]..Iadd.bacterium.Iaddend..
- the anhydrous foamable base composition contains petroleum jelly, mineral oil and a mild detergent (Sodium cocoyl isethionate).
- compositions containing the magnesium sulfate adduct and zinc chloride in accordance with the invention were tested for antimicrobial activity and compared with control compositions containing either the magnesium sulfate adduct and/or zinc chloride. These compositions are disclosed in Table I and their antimicrobial activity determined using the "Zone of Inhibition Test" determined.
- Zone of inhibition test is the relationship between a standard application of a test formulation on a solid agar surface and the resulting zone of inhibited growth of a test organism applied to the agar surface. The larger the zone of growth inhibition, the greater the antimicrobial activity. This test method is used to determine antimicrobial activity in both liquids and solids.
- compositions of Table I which exemplify of the present invention are:
- M.I.C. minimal inhibitory concentration
- the minimal inhibitory concentration is a serial twofold dilution of the test formulation in a broth culture medium which is innoculated with a standardized culture of microorganisms.
- the amount of test agent that will inhibit visible microbial growth is termed the minimal inhibitory concentration (M.I.C.) level. The lower the amount of test agent, the gretaer the antimicrobial activity.
- Example 7 formed in accordance with the present invention and controls containing only the magnesium sulfate adduct and/or zinc chloride..].
- compositions were prepared and evaluated both by the minimum inhibitory concentration method and the zone of inhibition. The results were similar for all salts tested at 1% concentration with Omadine MDS at 0.5%. .[.The activities for all the controls were from 125 to 550 ppm using the M.I.C. method and from 4 to 8 ppm for the combination of zinc salt with Omadine MDS..]. Again, the zone of inhibition was almost non-existent for controls 0-2 mm and 10-14 mm for the combination of the magnesium sulfate adduct and ZnCl 2 combination employed in the present invention.
- Table 3 there is disclosed a surgical scrub composition Composition I employing the anhydrous foaming base composition of pending application Ser. No. .Iadd.028,072 .Iaddend.containing petroleum jelly, mineral oil, glycerine, TiO 2 and sodium cocoyl isethionate and the magnesium sulfate adduct and ZnCl 2 combination of the present invention and the control base Composition II.
- the minimum inhibitory concentration activity was enhanced .[.from 125 ppm for the 2% Omadine MDS control Composition II to 2.0 ppm.]. for the Omadine MDS 2%, ZnCl 2 1% in Composition I.[.. This is over.]..Iadd., providing .Iaddend.a .[.sixtyfold.].
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Inorganic Chemistry (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Birds (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Organic Chemistry (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Dermatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
This invention relates to novel antimicrobial systems containing a water-soluble, non-ionic pyrethione derivative known chemically as the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide (referred to hereinafter as "the magnesium sulfate adduct") and a water soluble zinc salt.
The antimicrobial systems of this invention may be incorporated in various useful therapeutic and cleansing compositions such, for example, as surgical scrub compositions, skin disinfectants, mouthwashes, deodorants, hospital cleaners, etc.
Description
This invention relates to novel antimicrobial systems containing a water-soluble, non-ionic pyrethione derivative known chemically as the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide (referred to hereinafter as "the magnesium sulfate adduct") and a water soluble zinc salt. More particularly, it has been found that the presence of a water soluble zinc salt appears to enhance to an unexpected extent the antimicrobial activity of the magnesium sulfate adduct against certain types of microorganisms such, for example, as .[.Staphylococcus epidermidis, Staphylococcus aureus and.]. Pseudomonas aeruginosa.
The antimicrobial system of this invention may be incorporated in various useful therapeutic and cleansing compositions such, for example, as surgical scrub compositions, skin disinfectants, mouthwashes, deodorants, hospital cleaners, etc.
The magnesium sulfate adduct used in accordance with this invention is a well known broad spectrum antimicrobial agent. For example, a well known commercially available form is sold by Olin Chemicals of Stanford, Conn. under the trade name "OMADINE MDS" which is the trihydrate form.
While the magnesium sulfate adduct used in this invention has broad spectrum antimicrobial activity, it lacks the desired activity against Pseudomonas aeruginosa, the microorganism associated with infection that often follows severe burning of the skin.
.[.Examples of additional microorganisms against which it would be desirable to enhance the antimicrobial activity of the pyrithione derivative used in this invention are Staphylococcus aureus and Staphylococcus epidermidis..].
An object of the invention is to provide novel antimicrobial systems wherein enhanced antimicrobial activity of the magnesium sulfate adduct is effectuated against certain types of microorganisms.
Another object of this invention is to provide novel therapeutic and cleansing compositions having incorporated therein the antimicrobial system set forth in the foregoing object.
It has been found that the objects of this invention may be realized by forming an antimicrobial system containing the magnesium sulfate adduct and a water soluble salt.
For example, microbiological testing indicates that the activity of magnesium sulfate adduct against Ps. aeruginosa is enhanced in the presence of water soluble zinc salts.
The preferred zinc salt used in accordance with this invention is zinc chloride (ZnCl2). Other water soluble zinc salts which may be used are zinc acetate, zinc sulfate, zinc nitrate, zinc phenylsulfonate, etc.
In general, it has been found that in order to obtain the desired enhancement of antimicrobial activity in accordance with the present invention the zinc salt should be in an amount from about 1 to about 10, and preferably from about 1 to 1 parts by weight per part of the magnesium sulfate adduct.
In the therapeutic and/or cleansing composition of this invention the magnesium sulfate adduct in general is in an amount from about 0.1 to 1.5% by weight and the zinc salt from about 0.1 to 1% by weight, of the total composition.
It has been found that a most useful antimicrobial composition that may be obtained utilizing the present invention is a surgical scrub compositions employing the antimicrobial system of this invention in an anhydrous foamable base composition. Such surgical scrub compositions have been found useful in killing .[.both Staphylococcus aureus and.]. .Iadd.the .Iaddend.Pseudomonas aeruginosa .[.types of bacteria.]..Iadd.bacterium.Iaddend.. The anhydrous foamable base composition contains petroleum jelly, mineral oil and a mild detergent (Sodium cocoyl isethionate).
In order to illustrate the invention by specific examples a number of compositions containing the magnesium sulfate adduct and zinc chloride in accordance with the invention were tested for antimicrobial activity and compared with control compositions containing either the magnesium sulfate adduct and/or zinc chloride. These compositions are disclosed in Table I and their antimicrobial activity determined using the "Zone of Inhibition Test" determined.
Zone of inhibition test is the relationship between a standard application of a test formulation on a solid agar surface and the resulting zone of inhibited growth of a test organism applied to the agar surface. The larger the zone of growth inhibition, the greater the antimicrobial activity. This test method is used to determine antimicrobial activity in both liquids and solids.
The compositions of Table I which exemplify of the present invention are:
TABLE I ______________________________________ SYNERGISTIC EFFECTS OF ZnCl.sub.2 ON THE ACTIVITY OF THE MAGNESIUM SULFATE ADDUCT ® vs. PSEUDOMONAS PHYSI- ZONES (mm) ACTIVE ING.'S CAL vs. PSEUDO- AND PERCENTAGE FORM MONAS ______________________________________ Example Omadine MDS @ 0.135% Solution 0 Example Aluminum Chlorohydrate Solution 0 B (ACH) @ 17.5% Example Omadine MDS @ 0.135% Solution 0 C ACH @ 17.5% Example Omadine MDS @ 0.135% Solution 7.6 1 (ACH) @ 17.5% ZnCl.sub.2 @ 0.1% Example ZnCl.sub.2 @ 0.1% Lotion 0 D Example Omadine MDS @ 0.135% Solution 0 E ACH @ 17.5% Example Omadine MDS @ 0.135% Solution 8.6 2 ACH @ 17.5% ZnCl.sub.2 @ 0.1% Example Omadine MDS @ 0.135% Solution 0 F Example Omadine MDS @ 0.135% Solution 5.6 3 ZnCl.sub.2 @ 0.10% Example ZnCl.sub.2 @ 0.10% Solution 0 G Example Omadine MDS @ 0.135% Solution 0 H Example Omadine MDS @ 0.135% Solution 0 I ACH @ 17.5% Example Omadine MDS @ 0.135% Solution 8.3 4 ACH @ 17.5% ZnCl.sub.2 @ 0.10% Example Base Formula Only Lotion 0 J Example ZnCl.sub.2 1.0% Lotion 2.9 K Example Omadine MDS 0.225% Lotion 1.9 L Example Omadine MDS 0.225% Lotion 11.9 5 ZnCl.sub.2 1.0% Example ZnCl.sub.2 2.0% Solution 1 M Example Omadine MDS 0.225 Solution 0.5 N Example Omadine MD @ 0.5% Powder 11.3 6 ZnCl.sub.2 2.0% ______________________________________ *The magnesium sulfate adduct is sold by Olin Chemicals under the trade name OMADINE MDS.
Another useful determination for evaluating antimicrobial activity is to the minimal inhibitory concentration (M.I.C.) amount. The minimal inhibitory concentration is a serial twofold dilution of the test formulation in a broth culture medium which is innoculated with a standardized culture of microorganisms. The amount of test agent that will inhibit visible microbial growth is termed the minimal inhibitory concentration (M.I.C.) level. The lower the amount of test agent, the gretaer the antimicrobial activity.
.[.In Table 2 there is reported minimal inhibitory concentration values for Example 7 formed in accordance with the present invention and controls containing only the magnesium sulfate adduct and/or zinc chloride..].
TABLE 2 __________________________________________________________________________ FORMULA ACTIVE ING.'S PHYSICAL MIMINUM INHIBITORY CONCENTRATION NOS. AND PERCENTAGE FORM (PPM) vs. PSEUDOMONAS __________________________________________________________________________ Example O ZnCl.sub.2 0.1% Solution No Activity Example P Omadine MDS Solution 250 0.135% Example 7 Omadine MDS Solution 30 0.135% ZnCl.sub.2 0.1% __________________________________________________________________________
The results .[.reported in Table 2.]. .Iadd.of experimental analyses .Iaddend.indicated .[.no activity for ZnCl2, activity of 250 ppm for Omadine MDS alone and 30 ppm for the combination of ZnCl2 with Omadine MDS. This indicates.]. an eightfold increase in activity against Pseudomonas aeruginosa for the combination of ZnCl2 with omadine MDS compared to the activity of ZnCl2 alone or Omadine MDS alone.
In still further comparison study compositions were prepared and evaluated both by the minimum inhibitory concentration method and the zone of inhibition. The results were similar for all salts tested at 1% concentration with Omadine MDS at 0.5%. .[.The activities for all the controls were from 125 to 550 ppm using the M.I.C. method and from 4 to 8 ppm for the combination of zinc salt with Omadine MDS..]. Again, the zone of inhibition was almost non-existent for controls 0-2 mm and 10-14 mm for the combination of the magnesium sulfate adduct and ZnCl2 combination employed in the present invention.
In Table 3 there is disclosed a surgical scrub composition Composition I employing the anhydrous foaming base composition of pending application Ser. No. .Iadd.028,072 .Iaddend.containing petroleum jelly, mineral oil, glycerine, TiO2 and sodium cocoyl isethionate and the magnesium sulfate adduct and ZnCl2 combination of the present invention and the control base Composition II.
TABLE 3 ______________________________________ Formula Composition I Composition II ______________________________________ Petroleum Jelly 31.00 31.00 Mineral Oil 19.50 19.50 Glycerin 5.00 5.00 TiO.sub.2 0.50 0.50 Na Cocoyl Isethionate 40.00 42.00 Omadine MDS 2.00 2.00 ZnCl.sub.2 (50% Solution) 2.00 ______________________________________
When tested for antimicrobial activity, the minimum inhibitory concentration activity was enhanced .[.from 125 ppm for the 2% Omadine MDS control Composition II to 2.0 ppm.]. for the Omadine MDS 2%, ZnCl2 1% in Composition I.[.. This is over.]..Iadd., providing .Iaddend.a .[.sixtyfold.]. .Iadd.substantial .Iaddend.increase in activity .Iadd.against Pseudomonas aeruginosa compared to Composition II.Iaddend...[.Evidence for synergism was also observed against Staphylococcus aureus, for Composition I activity is 0.003 ppm, while the control Composition II with 2% Omadine is 0.1 ppm. This is a thirty-threefold increase in activity. For Staphylococcus epidermidis, once again the synergism was confirmed, with 0.0007 ppm activity for the 2% Omadine MDS 1% ZnCl2 combination, while the Composition II control is 0.006 ppm. This is an elevenfold increase in activity..].
Claims (5)
1. An antimicrobial composition comprising the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide and a water soluble zinc salt, the zinc salt being in an amount from about 1 to 10 parts by weight per part of the antimicrobial adduct.
2. An antimicrobial composition according to claim 1 wherein the zinc salt is selected from the group consisting of zinc chloride, zinc acetate, zinc sulfate, zinc nitrate and zinc phenylsulfonate.
3. An antimicrobial system according to claim 1 wherein the zinc salt is zinc chloride.
4. An antimicrobial composition according to claim 1, 2 or 3 wherein the zinc salt is in an amount of 1 part by weight per part of the microbial adduct.
5. An antimicrobial composition according to claims 1, 2 or 3 wherein the magnesium sulfate adduct is in an amount from about 0.1 to 1.5% by weight and the zinc salt is in an amount from about 0.1 to 1% by weight of the total composition.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/289,962 USRE33512E (en) | 1985-09-11 | 1988-12-23 | Novel anti-microbial systems containing the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide and a water soluble zinc salt |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/774,725 US4654213A (en) | 1985-09-11 | 1985-09-11 | Novel anti-microbial systems containing the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide and a water soluble zinc salt |
US07/289,962 USRE33512E (en) | 1985-09-11 | 1988-12-23 | Novel anti-microbial systems containing the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide and a water soluble zinc salt |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/774,725 Reissue US4654213A (en) | 1985-09-11 | 1985-09-11 | Novel anti-microbial systems containing the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide and a water soluble zinc salt |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE33512E true USRE33512E (en) | 1991-01-01 |
Family
ID=25102079
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/774,725 Ceased US4654213A (en) | 1985-09-11 | 1985-09-11 | Novel anti-microbial systems containing the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide and a water soluble zinc salt |
US07/289,962 Expired - Fee Related USRE33512E (en) | 1985-09-11 | 1988-12-23 | Novel anti-microbial systems containing the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide and a water soluble zinc salt |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06/774,725 Ceased US4654213A (en) | 1985-09-11 | 1985-09-11 | Novel anti-microbial systems containing the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide and a water soluble zinc salt |
Country Status (10)
Country | Link |
---|---|
US (2) | US4654213A (en) |
EP (1) | EP0216558B1 (en) |
JP (1) | JPS6296402A (en) |
AU (1) | AU584455B2 (en) |
CA (1) | CA1276876C (en) |
DE (1) | DE3685923T2 (en) |
ES (1) | ES2001673A6 (en) |
HK (1) | HK34393A (en) |
MX (1) | MX164791B (en) |
ZA (1) | ZA866461B (en) |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20070141172A1 (en) * | 2005-12-21 | 2007-06-21 | Robert Baltzell | Method of treating bacterial hoof infections of sheep and cattle |
US20070191620A1 (en) * | 2006-02-03 | 2007-08-16 | Ramirez Jose E | Chemical compositions and methods of making them |
US20070203354A1 (en) * | 2006-02-03 | 2007-08-30 | Ramirez Jose E | 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 |
US20110008271A1 (en) * | 2009-07-13 | 2011-01-13 | Jr Chem, Llc | Rosacea treatments using polymetal complexes |
US7927614B2 (en) | 2006-02-03 | 2011-04-19 | Jr Chem, Llc | Anti-aging treatment using copper and zinc compositions |
WO2011094670A1 (en) | 2010-02-01 | 2011-08-04 | Presstek, Inc. | Lithographic imaging and printing without defects of electrostatic origin |
EP2374614A1 (en) | 2010-04-09 | 2011-10-12 | Presstek, Inc. | Ablation-type lithographic Imaging with enhanced debris removal |
US8273791B2 (en) | 2008-01-04 | 2012-09-25 | Jr Chem, Llc | Compositions, kits and regimens for the treatment of skin, especially décolletage |
WO2012158318A1 (en) | 2011-05-17 | 2012-11-22 | Presstek, Inc. | Ablation-type lithographic printing members having improved exposure sensitivity and related methods |
WO2014031828A1 (en) | 2012-08-22 | 2014-02-27 | Presstek, Inc. | Ablation-type lithographic printing members having improved shelf life and related methods |
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 |
WO2018039595A1 (en) | 2016-08-25 | 2018-03-01 | Presstek, Llc. | Dry printing with simplified plate cleaning |
WO2018132365A1 (en) | 2017-01-11 | 2018-07-19 | Presstek Llc | Ablation-type lithographic printing members having improved exposure sensitivity and related methods |
US11559053B1 (en) | 2016-09-23 | 2023-01-24 | Specialty Sales, LLC | Livestock footbath solutions and methods of use |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5186857A (en) * | 1988-11-14 | 1993-02-16 | Imaginative Research Associates, Inc. | Self-foaming oil compositions and process for making and using same |
US4931204A (en) * | 1988-11-14 | 1990-06-05 | Imaginative Research Associates, Inc. | Self-foaming oil compositions and process for making and using same |
WO1990011343A1 (en) * | 1989-03-21 | 1990-10-04 | Imaginative Research Associates, Inc. | Self-foaming oil compositions and process for making and using same |
AU662161B2 (en) * | 1991-07-18 | 1995-08-24 | Procter & Gamble Company, The | Liquid deodorant compositions |
DE4200499A1 (en) * | 1992-01-10 | 1993-07-15 | Bode Chemie Gmbh & Co | DISINFECTANT |
US5227156A (en) * | 1992-04-14 | 1993-07-13 | Amway Corporation | Use of zinc compounds to stabilize a thiazolinone preservative in an anti-dandruff shampoo |
FR2739775B1 (en) * | 1995-10-16 | 1997-11-21 | Oreal | DEODORANT COMPOSITION COMPRISING A WATER-SOLUBLE SALT OF ZINC AS AN ODOR-ABSORBING AGENT |
US5863524A (en) * | 1997-03-26 | 1999-01-26 | Church & Dwight Co., Inc. | Transparent bicarbonate salt containing deodorant cosmetic stick product |
US5958462A (en) * | 1997-05-23 | 1999-09-28 | Mclean; Linsey | Therapeutic bath salts and method of use |
AU2005200050B2 (en) * | 1999-06-25 | 2008-04-03 | Arch Chemicals, Inc. | Pyrithione biocides enchanced by silver, copper, or zinc ions |
US7455851B1 (en) * | 1999-06-25 | 2008-11-25 | Arch Chemicals, Inc. | Pyrithione biocides enhanced by silver, copper, or zinc ions |
JP2003522734A (en) * | 1999-06-25 | 2003-07-29 | アーチ ケミカルズ,インコーポレイテッド | Pyrithione biocides enhanced by silver, copper, or zinc ions |
US7026308B1 (en) | 1999-06-25 | 2006-04-11 | The Procter & Gamble Company | Topical anti-microbial compositions |
AU2008202828B8 (en) * | 1999-06-25 | 2011-08-11 | Arch Chemicals, Inc. | Pyrithione biocides enhanced by silver, copper, or zinc ions |
US7674785B2 (en) * | 2000-06-22 | 2010-03-09 | The Procter & Gamble Company | Topical anti-microbial compositions |
DE10196338D2 (en) * | 2001-04-12 | 2004-04-29 | Meissner Dieter | Foam, process for making foam and using foam |
CN100496480C (en) * | 2002-04-22 | 2009-06-10 | 宝洁公司 | Personal care compositions comprising a zinc containing material in an aqueous surfactant composition |
WO2003088965A1 (en) * | 2002-04-22 | 2003-10-30 | The Procter & Gamble Company | Use of materials having zinc ionophoric behavior |
US9381148B2 (en) * | 2003-03-18 | 2016-07-05 | The Procter & Gamble Company | Composition comprising particulate zinc material with a high relative zinc lability |
US20050202984A1 (en) * | 2003-03-18 | 2005-09-15 | Schwartz James R. | Composition comprising zinc-containing layered material with a high relative zinc lability |
US8491877B2 (en) * | 2003-03-18 | 2013-07-23 | The Procter & Gamble Company | Composition comprising zinc-containing layered material with a high relative zinc lability |
US9381382B2 (en) * | 2002-06-04 | 2016-07-05 | The Procter & Gamble Company | Composition comprising a particulate zinc material, a pyrithione or a polyvalent metal salt of a pyrithione and a gel network |
US20040213751A1 (en) * | 2003-03-18 | 2004-10-28 | Schwartz James Robert | Augmentation of pyrithione activity or a polyvalent metal salt of pyrithione activity by zinc-containing layered material |
US20040191331A1 (en) * | 2003-03-18 | 2004-09-30 | The Procter & Gamble Company | Composition comprising particulate zinc materials having a defined crystallite size |
US7910118B2 (en) | 2004-07-16 | 2011-03-22 | Bannister Dennis R | Skin treatment |
US20120195944A9 (en) * | 2009-08-12 | 2012-08-02 | Amy Michelle Capretta | Rinse-Off Care Products and Consumer Product Line-ups Comprising Same |
CN103889394A (en) | 2011-08-15 | 2014-06-25 | 宝洁公司 | Methods of enhancing skin hydration and improving non-diseased skin |
GB201211701D0 (en) | 2012-07-02 | 2012-08-15 | Reckitt Benckiser Llc | Aqueous alcoholic microbicidal compositions comprising zinc ions |
GB201211702D0 (en) | 2012-07-02 | 2012-08-15 | Reckitt Benckiser Llc | Sprayable aqueous alcoholic microbicidal compostions comprising zinc ions |
US9707162B2 (en) | 2012-11-30 | 2017-07-18 | Reckitt & Colman (Overseas) Limited | Microbicidal personal care compositions comprising metal ions |
Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3890434A (en) * | 1971-10-18 | 1975-06-17 | Olin Corp | Hair and antiseptic formulations containing adducts of bis-(2-pyridyl-1-oxide) disulfide |
JPS5415939A (en) * | 1978-07-01 | 1979-02-06 | Hokko Chem Ind Co Ltd | Underwater antifouling coating compound |
US4152431A (en) * | 1977-09-22 | 1979-05-01 | William H. Rorer, Inc. | Compositions and method of use |
US4161526A (en) * | 1978-07-20 | 1979-07-17 | Sterling Drug Inc. | Zinc salt prevention or removal of discoloration in pyrithione, pyrithione salt and dipyrithione compositions |
US4163783A (en) * | 1977-09-22 | 1979-08-07 | Klein Robert W | Synergistic compositions and method of use to treat inflammation |
US4235873A (en) * | 1979-03-30 | 1980-11-25 | Dermik Laboratories | Antiperspirant-deodorant compositions |
US4410446A (en) * | 1979-06-07 | 1983-10-18 | Petrolite Corporation | Zinc oxide dispersions by decomposition of zinc acetate |
JPS6016973A (en) * | 1983-07-06 | 1985-01-28 | Kao Corp | Preparation of finely-ground particles of polyvalent metal salt of 2-mercaptopyridin-n-oxide |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3785985A (en) * | 1971-04-21 | 1974-01-15 | Colgate Palmolive Co | Cosmetic and textile-treating compositions |
WO1985003867A1 (en) * | 1984-03-01 | 1985-09-12 | Vernon Erk | Method of changing the rate of oxidation of amines in vertebrates and other organisms |
JPH0625121B2 (en) * | 1985-03-28 | 1994-04-06 | 花王株式会社 | Method for producing fine particles of 2-mercaptopyridine-N-oxide polyvalent metal salt |
AU6175586A (en) * | 1985-09-11 | 1987-03-12 | Chesebrough-Pond's Inc. | Petroleum jelly, mild detergent anhydrous base compositions |
-
1985
- 1985-09-11 US US06/774,725 patent/US4654213A/en not_active Ceased
-
1986
- 1986-08-26 ZA ZA866461A patent/ZA866461B/en unknown
- 1986-08-26 AU AU61851/86A patent/AU584455B2/en not_active Ceased
- 1986-09-03 MX MX3641A patent/MX164791B/en unknown
- 1986-09-08 JP JP61212533A patent/JPS6296402A/en active Granted
- 1986-09-09 EP EP86306932A patent/EP0216558B1/en not_active Expired - Lifetime
- 1986-09-09 DE DE8686306932T patent/DE3685923T2/en not_active Expired - Fee Related
- 1986-09-10 CA CA000517901A patent/CA1276876C/en not_active Expired - Lifetime
- 1986-09-10 ES ES8601748A patent/ES2001673A6/en not_active Expired
-
1988
- 1988-12-23 US US07/289,962 patent/USRE33512E/en not_active Expired - Fee Related
-
1993
- 1993-04-08 HK HK343/93A patent/HK34393A/en unknown
Patent Citations (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3890434A (en) * | 1971-10-18 | 1975-06-17 | Olin Corp | Hair and antiseptic formulations containing adducts of bis-(2-pyridyl-1-oxide) disulfide |
US4152431A (en) * | 1977-09-22 | 1979-05-01 | William H. Rorer, Inc. | Compositions and method of use |
US4163783A (en) * | 1977-09-22 | 1979-08-07 | Klein Robert W | Synergistic compositions and method of use to treat inflammation |
JPS5415939A (en) * | 1978-07-01 | 1979-02-06 | Hokko Chem Ind Co Ltd | Underwater antifouling coating compound |
US4161526A (en) * | 1978-07-20 | 1979-07-17 | Sterling Drug Inc. | Zinc salt prevention or removal of discoloration in pyrithione, pyrithione salt and dipyrithione compositions |
US4235873A (en) * | 1979-03-30 | 1980-11-25 | Dermik Laboratories | Antiperspirant-deodorant compositions |
US4410446A (en) * | 1979-06-07 | 1983-10-18 | Petrolite Corporation | Zinc oxide dispersions by decomposition of zinc acetate |
JPS6016973A (en) * | 1983-07-06 | 1985-01-28 | Kao Corp | Preparation of finely-ground particles of polyvalent metal salt of 2-mercaptopyridin-n-oxide |
Non-Patent Citations (7)
Title |
---|
Chemical Abstract 69:343387w (1968); Okomoto, et al. * |
Chemical Abstract 80:91617x (1974); Elkhouly, et al. * |
Chemical Abstract 87:161376p (1977); Wedig et al. * |
Chemical Abstract 88:177003w (1978); Wedig, et al. * |
Chemical Abstract 91:32995y (1979); Giloor, et al. * |
The Merck Index 9th Ed. (1976) pp. 1307 1309; Merck & Co. * |
The Merck Index 9th Ed. (1976)-pp. 1307-1309; Merck & Co. |
Cited By (22)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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 |
US8148563B2 (en) | 2006-02-03 | 2012-04-03 | Jr Chem, Llc | Chemical compositions and methods of making them |
US20070191620A1 (en) * | 2006-02-03 | 2007-08-16 | Ramirez Jose E | Chemical compositions and methods of making them |
US20070203354A1 (en) * | 2006-02-03 | 2007-08-30 | Ramirez Jose E | Chemical Compositions and Methods of Making Them |
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 |
US7927614B2 (en) | 2006-02-03 | 2011-04-19 | Jr Chem, Llc | Anti-aging treatment using copper and zinc compositions |
US20110178318A1 (en) * | 2006-02-03 | 2011-07-21 | Ramirez Jose E | Methods of making bimetal complexes |
US7867522B2 (en) | 2006-09-28 | 2011-01-11 | Jr Chem, Llc | Method of wound/burn healing using copper-zinc compositions |
US8505730B2 (en) | 2008-01-04 | 2013-08-13 | Jr Chem, Llc | Compositions, kits and regimens for the treatment of skin, especially décolletage |
US8273791B2 (en) | 2008-01-04 | 2012-09-25 | 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 |
US20110008271A1 (en) * | 2009-07-13 | 2011-01-13 | Jr Chem, Llc | Rosacea treatments using polymetal complexes |
WO2011094670A1 (en) | 2010-02-01 | 2011-08-04 | Presstek, Inc. | Lithographic imaging and printing without defects of electrostatic origin |
EP2374614A1 (en) | 2010-04-09 | 2011-10-12 | Presstek, Inc. | Ablation-type lithographic Imaging with enhanced debris removal |
US8952057B2 (en) | 2011-01-11 | 2015-02-10 | Jr Chem, Llc | Compositions for anorectal use and methods for treating anorectal disorders |
WO2012158318A1 (en) | 2011-05-17 | 2012-11-22 | Presstek, Inc. | Ablation-type lithographic printing members having improved exposure sensitivity and related methods |
WO2014031828A1 (en) | 2012-08-22 | 2014-02-27 | Presstek, Inc. | Ablation-type lithographic printing members having improved shelf life and related methods |
WO2018039595A1 (en) | 2016-08-25 | 2018-03-01 | Presstek, Llc. | Dry printing with simplified plate cleaning |
US11559053B1 (en) | 2016-09-23 | 2023-01-24 | Specialty Sales, LLC | Livestock footbath solutions and methods of use |
WO2018132365A1 (en) | 2017-01-11 | 2018-07-19 | Presstek Llc | Ablation-type lithographic printing members having improved exposure sensitivity and related methods |
Also Published As
Publication number | Publication date |
---|---|
AU584455B2 (en) | 1989-05-25 |
JPH0442361B2 (en) | 1992-07-13 |
DE3685923T2 (en) | 1993-02-25 |
US4654213A (en) | 1987-03-31 |
CA1276876C (en) | 1990-11-27 |
AU6185186A (en) | 1987-03-12 |
EP0216558B1 (en) | 1992-07-08 |
JPS6296402A (en) | 1987-05-02 |
EP0216558A2 (en) | 1987-04-01 |
ES2001673A6 (en) | 1988-06-01 |
MX164791B (en) | 1992-09-24 |
HK34393A (en) | 1993-04-16 |
ZA866461B (en) | 1987-04-29 |
DE3685923D1 (en) | 1992-08-13 |
EP0216558A3 (en) | 1988-08-17 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
USRE33512E (en) | Novel anti-microbial systems containing the magnesium sulfate adduct of 2,2'-dithiobis-pyridine-1,1'-dioxide and a water soluble zinc salt | |
US5707993A (en) | Glycine anhydride dimethylol as a biocide and preservative | |
US7247295B2 (en) | Use of 1,2-decandiol for combating germs causing body odor | |
US5428050A (en) | Synergistic water soluble preservative compositions of biocidal mixtures | |
AU683719B2 (en) | Synergistic antimicrobial compositions containing a halogenated acetophenone and an organic acid | |
US4098877A (en) | Antimicrobial composition (enhanced activity from combination of phenol and a quaternary compound) | |
WO2009094198A1 (en) | Liquid preservative compositions | |
JP3637281B2 (en) | Disinfectant composition and disinfecting method using the same | |
EP0230698B1 (en) | Use of an ester compound as a temporary microbicide | |
CN107427006A (en) | Isobide ether derivant with antiseptic activity | |
CA2135427A1 (en) | Method and composition for controlling the growth of microorganisms | |
US5292776A (en) | Microbial inhibiting compositions and their use | |
CA2284543C (en) | Biocidal composition and use | |
JPH0643285B2 (en) | Microbial growth inhibitory composition | |
EP0651608B1 (en) | Synergistic antimicrobial compositions containing 2-(2-bromo-2-nitroethenyl)furan | |
US5352706A (en) | Method and composition for controlling the growth of microorganisms | |
JP2903582B2 (en) | Industrial antibacterial and antialgal compositions | |
JPH02169501A (en) | Control of formaldehyde | |
JPH1129408A (en) | Microbicidal disinfectant for pathogenic legionella bacteria | |
FI72254B (en) | ENPRODUKT FOER UTBREDNING PAO HUDEN FOER HYGIENI OCH / ELLER EFOHINDRANDE AV INFLAMMATIONER | |
JP2001181113A (en) | Industrial disinfectant/antiseptic and disinfecting/ antisepticizing method using the same | |
JPH11199408A (en) | Bactericidal composition and method for promoting manifestation of bactericidal activity, and disinfection | |
CA2121622A1 (en) | Process and composition for inhibiting microbial growth | |
TH2446A (en) | A microbial antiseptic ingredient |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
REMI | Maintenance fee reminder mailed | ||
LAPS | Lapse for failure to pay maintenance fees |