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 PDF

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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
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Prior art keywords
magnesium sulfate
zinc salt
zinc
adduct
sulfate adduct
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Expired - Fee Related
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US07/289,962
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Jose E. Ramirez
Robert J. Tanko
Mohan Vishnupad
William H. Schmitt
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Chesebrough Ponds Inc
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Chesebrough Ponds Inc
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    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • 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.].

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

SUMMARY OF INVENTION
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.
BACKGROUND OF THE INVENTION
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..].
OBJECTS OF THE INVENTION
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.
GENERAL DESCRIPTION OF THE INVENTION
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).
SPECIFIC DESCRIPTION OF THE PRESENT INVENTION
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)

What is claimed is:
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.
US07/289,962 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 Expired - Fee Related USRE33512E (en)

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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

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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
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US8273791B2 (en) 2008-01-04 2012-09-25 Jr Chem, Llc Compositions, kits and regimens for the treatment of skin, especially décolletage
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US8952057B2 (en) 2011-01-11 2015-02-10 Jr Chem, Llc Compositions for anorectal use and methods for treating anorectal disorders
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US4654213A (en) 1987-03-31
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CA1276876C (en) 1990-11-27
DE3685923T2 (en) 1993-02-25

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