US2695881A - Antiseptic soap composition - Google Patents

Antiseptic soap composition Download PDF

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US2695881A
US2695881A US207246A US20724651A US2695881A US 2695881 A US2695881 A US 2695881A US 207246 A US207246 A US 207246A US 20724651 A US20724651 A US 20724651A US 2695881 A US2695881 A US 2695881A
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hydroxy
detergent
tetra
antiseptic
soap
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US207246A
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Eugene W Elliott
Roland S Shumard
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Monsanto Chemicals Ltd
Monsanto Chemical Co
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Monsanto Chemicals Ltd
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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

Definitions

  • This invention relates to new and novel detergent compositions. More particularly it relates to antiseptic detergent compositions containing a synergistic mixture of a tetra-alkyl thiuram disulfide and a halogenated 2-hydrocarbon substituted-8-hydroxy quinoline or a metal salt thereof. Still more particularly it relates to antiseptic detergent compositions containing a synergistic mixture of tetra-methyl thiuram disulfide and a halogenated 2- methyl-S-hydroxy quinoline more commonly known as halogenated 8-hydroxy quinaldines.
  • Patented Nov. 30, 1954 tikons containing the new mixture are not irritating to the s 1n.
  • detergent containing compositions are prepared by intimately mixing the ingredients listed below to form a composite containing 2% by weight active ingredient:
  • Composition A B O D E Ivory brand neutral white high grade tallow toilet soap parts by weight 98 98 98 9B Tetra-methyl thiuram disulfide ,do 2 1 1 5,7-dlbromo-8-hydroxy quinaldine do 2 1 1 5,7-dibromo-8-hydroxy quinoline -ldo- Table I Composition Period of Incubation rs. Growth Legend:
  • the tetra-alkyl thiuram disulfide and the halogenated 2- hydrocarbon substituted-8-hydroxy quinoline or its alkali metal salt are readily incorporated either separately or admixed with one another in detergent compositions whether the latter be solid or liquid.
  • the components of the new mixture remain permanently in the detergent composition. They do not affect the lathering, cleansing or physical properties of the detergent nor do they impart an unpleasant odor nor discolor the finished detergent composition. Furthermore detergent composi- No growth.
  • a halogenated Z-hydrocarbon substituted-S-hydroxy quinoline is admixed with a tetra-alkyl thiuram disulfide and compounded in a detergent composition to form a 2% by weight active ingredient composite and compared to detergent compositions containing an equal weight of each of the respective components.
  • compositions are:
  • Composition F Ivory brand neutral white high grade tallow toilet soap Tetra-methyl thiuram disu1fide 2 5,7-dichloro-8-hydroxy quinaldine Aliquots of each of the above described compositions are added to a nutrient agar medium so as to give in each instance concentrations of 0.67 p. p. m. of active ingredient. The agar in each case is then poured into a petri dish, allowed to harden, and then is streaked with a 24 hour old culture of Staphylococcus aureus of standard resistance.
  • Staphylococcus aureus Salmonella typhosa Legend: Same as in Table I.
  • composition F fide detergent composition
  • composition A the corresponding results in the prior example
  • composition A the test organism (Staphylococcus aureus) 'in each instance was prepared Divergencies of this kind are common in antiseptic technology, however, the respective results for the 2% tetra-methyl thiuram disulfide detergent composition provide proper comparison in each example.
  • alkali metal salts of the aforementioned hydroxy substituted compounds of this invention when combined with a tetra-alkyl thiuram disulfide, such as tetra-methyl thiuram disulfide, in a detergent composition also exhibit a synergistic antiseptic effect, however, the alkali metal salts are not as effective as the
  • tetra-alkyl thiuram disulfides tetra-methyl thiuram disulfide is preferred, however, other tetra-alkyl thiuram disulfides such as the tetra-ethyl and the tetrabutyl thiuram disulfide when employed in conjunction with a halogenated 2-hydrocarbon substituted-S-hydroxy quinoline exhibit an antiseptic synergistic effect in a detergent composition.
  • the weight ratio of the tetra-alkyl thiuram disulfide to the halogenated 2-hydrocarbon substituted-S-hydroxy quinoline or its alkali metal salt will vary from 25-75 parts of the former to 75-25 parts of the latter.
  • antiseptic agents may be incorporated in the new antiseptic detergent composition as well as emollients, water softeners and the well known vehicles of the detergent trade.
  • Various colors, antioxidants, perfumes and the like may be incorporated where desirable.
  • detergent includes soap and synthetic detergents, particularly the anionic detergents such as the substituted amides and the alkyl aryl sulfonates.
  • detergent includes also mixtures of synthetic detergents and soap.
  • soap or detergent soap as used herein is employed in its popular or ordinary meaning, that is, those cleansing compositions prepared from an alkali metal compound such as sodium or potassium hydroxide and a fat or fatty acid.
  • halogenated Z-hydrocarbon substituted-8-hydroxy quinolines or their metal salts and the tetra-alkyl thiuram disulfides of this invention may be added to the detergent composition in any suitable manner during the crutching or milling or similar operation.
  • the halogenated 2-hydrocarbon substituted-S-hydroxy quinolines or their metal salts and the tetra-alkyl disulfide may be first dissolved either separately or jointly in a suitable solvent and then incorporated in the detergent if so desired.
  • An antiseptic detergent composition comprising a detergent soap and a minor weight proportion in respect to the detergent soap suflicient to impart antiseptic properties of a mixture of a halogenated 2-hydrocarbon substituted-S-hydroxy quinoline of the formula R I N where X is a halogen atom, where n is a whole number from 1 to 2, where R is selected from the group consisting of hydrogen, halogen atoms and short-chain alkyl groups, and where R is a hydrocarbon group containing not more than 7 carbon atoms selected from the group consisting of alkyl, aralkyl, aryl and alkaryl radicals, and a tetra-alkyl thiuram disulfide wherein each alkyl substituent is a short-chain alkyl group, said thiuram disulfide being a synergist for said halogenated compound.
  • An antiseptic detergent composition comprising a detergent soap and, aminor weight proportion in respect to the detergent soap sufficient to impart antiseptic properties of a mixture of tetra-methyl thiuram disulfide and a halogenated 8-hydroxy quinaldine of the formula -8-hydroxy quinaldine.
  • X1 and X2 are halogen atoms.
  • An antiseptic detergent composition comprising a detergent soap and 0.5 to by weight based-upon the detergent soap of a mixture of equal parts by weight of tetra-methyl thiuram disulfide and a dihalo-S-hydroxy quinaldine of the formula where X1 and X2 are halogen atoms.
  • An antiseptic detergent composition comprising a detergent soap and l to 3% by weight based upon the detergent soap of a mixture of equal parts by weight of 6 tetra-methyl thiuram disulfide and a di-halo-S-hydroxy quinaldine of the formula X; CHI
  • X1 and X2 are halogen atoms.
  • An antiseptic detergent composition comprising a detergent soap and 1 to 3% by weight based upon the detergent soap of a mixture of equal parts by weight of 5,7 dichloro 8- ydroxy quinaldine and tetra-methyl thiuram disulfide.
  • An antiseptic detergent composition comprising a detergent soap and 1 to 3% by weight based upon the detergent soap of a mixture of equal parts by weight of 5,7- dibromo-S-hydroxy quinaldine and tetra-methyl thiuram disulfide.
  • An antiseptic detergent composition comprising a detergent soap and 1 to 3% by weight based upon the detergent soap of a mixture of equal parts by weight of 5-chloro-7-bromo-8-hydroxy quinaldine and tetra-methyl thiuram disulfide.
  • An antiseptic detergent composition comprising a detergent soap and 1 to 3% by weight based upon the detergent soap of a mixture of equal parts by weight of S-chloro-7-iodo-8-hydroxy quinaldine and tetra-methyl thiuram disulfide.
  • An antiseptic detergent composition comprising a detergent soap and 1 to 3% by weight based upon the detergent soap of a mixture of equal parts by weight of 5-chlgro-8-hydroxy quinaldine and tetra-methyl thiuram disul de.

Description

United States Patent '0 AN TISEPTIC SOAP COMPOSITION Eugene W. Elliott, Pine Lawn, and Roland S.
Brentwood, Mo., assignors to Monsanto Chemical Company, St. Louis, Mo., a corporation of Delaware No Drawing. Application January 22, 1951,
I Serial No. 207,246
11 Claims. (Cl. 252-107) This invention relates to new and novel detergent compositions. More particularly it relates to antiseptic detergent compositions containing a synergistic mixture of a tetra-alkyl thiuram disulfide and a halogenated 2-hydrocarbon substituted-8-hydroxy quinoline or a metal salt thereof. Still more particularly it relates to antiseptic detergent compositions containing a synergistic mixture of tetra-methyl thiuram disulfide and a halogenated 2- methyl-S-hydroxy quinoline more commonly known as halogenated 8-hydroxy quinaldines.
Shumard,
Patented Nov. 30, 1954 tikons containing the new mixture are not irritating to the s 1n.
As e emplary of this invention detergent containing compositions are prepared by intimately mixing the ingredients listed below to form a composite containing 2% by weight active ingredient:
"ice
Composition A B O D E Ivory brand neutral white high grade tallow toilet soap parts by weight 98 98 98 98 9B Tetra-methyl thiuram disulfide ,do 2 1 1 5,7-dlbromo-8-hydroxy quinaldine do 2 1 1 5,7-dibromo-8-hydroxy quinoline -ldo- Table I Composition Period of Incubation rs. Growth Legend:
In co-pending application Serial Number 206,123, filed January 15, 1951, in the name of R. S. Shumard there is described a class of hydroxy substituted aromatic compounds and their alkali metal salts which when incorporated in alkaline media such as soap form highly etiective antiseptic detergent compositions. This class of compounds is represented by the formula RI N where X is a halogen atom, where n is a whole number from 1 to 2, where R is selected from the group consisting of hydrogen, halogen atoms and alkyl groups, where Z is hydrogen or an alkali metal such as sodium, potassium or lithium, and where R is a hydrocarbon group such as an alkyl, aralkyl, aryl, or an alkaryl group.
In accordance with this invention it has been found that a synergistic antiseptic effect is obtained by employing a halogenated Z-hydrocarbon substituted-8-hydroxy quinoline or an alkali metal salt thereof of co-pending application Serial Numer 206,123, filed January 15, 1951, in the name of R. S. Shumard in conjunction with a tetraalkyl thiuram disulfide in a detergent composition. In other words the resultant antiseptic detergent composition is more active than a detergent composition containing either component and beyond the mere additive effect of the proportions of the individual components. The tetra-alkyl thiuram disulfide and the halogenated 2- hydrocarbon substituted-8-hydroxy quinoline or its alkali metal salt are readily incorporated either separately or admixed with one another in detergent compositions whether the latter be solid or liquid. The components of the new mixture remain permanently in the detergent composition. They do not affect the lathering, cleansing or physical properties of the detergent nor do they impart an unpleasant odor nor discolor the finished detergent composition. Furthermore detergent composi- No growth.
Extremely light growth. Very light growth.
Light to moderate growth. Normal heavy growth.
As further exemplary of this invention a halogenated Z-hydrocarbon substituted-S-hydroxy quinoline is admixed with a tetra-alkyl thiuram disulfide and compounded in a detergent composition to form a 2% by weight active ingredient composite and compared to detergent compositions containing an equal weight of each of the respective components.
The compositions are:
Composition F Ivory brand neutral white high grade tallow toilet soap Tetra-methyl thiuram disu1fide 2 5,7-dichloro-8-hydroxy quinaldine Aliquots of each of the above described compositions are added to a nutrient agar medium so as to give in each instance concentrations of 0.67 p. p. m. of active ingredient. The agar in each case is then poured into a petri dish, allowed to harden, and then is streaked with a 24 hour old culture of Staphylococcus aureus of standard resistance. In a similar manner aliquots of the aforedescribed F, G and H compositions containing 2% by weight active ingredient are added to a nutrient agar medium so as to give in each instance a concentration of 2.5 p. p. m. of active ingredient. The agar in each case is then poured into a petri dish, allowed to harden, and then is streaked with a 24 hour old culture of Salmonella typhosa of standard resistance. The degree of growth of both Staphylococcus aureus and Salmonella typhosa is noted below after an incubation period of 72 hours at 37 C. in the respective instances:
Table II Composition F G H Organism:
Staphylococcus aureus Salmonella typhosa Legend: Same as in Table I.
It will be appreciated that the difference between the resultsobtainedwith the 2% tetra-methyl thiuram disulon different occasions.
fide detergent composition (composition F) in this example and the corresponding results in the prior example (composition A) is due to the fact that the test organism (Staphylococcus aureus) 'in each instance was prepared Divergencies of this kind are common in antiseptic technology, however, the respective results for the 2% tetra-methyl thiuram disulfide detergent composition provide proper comparison in each example.
Substantially the same synergistic antiseptic results are obtained with tetra-methyl thiuram disulfide as in the aforedescribed examples by replacing the respective 5,7- dihalo-8-hydroxy quinaldines of compositions C and H with other dihalogenated-8-hydroxy quinaldines such as 5,7-diiodo-8-hydroxy quinaldine, 5-chloro7-iodo-8-hydroxy quinaldine, and 5 chloro 7-bromo-8-hydroxy quinaldine. A synergistic antiseptic effect is also obtained with a detergent composition containing a minor proportion of equal parts by weight of tetra-methyl thiuram disulfide and 5-chloro-8-hydroxy quinaldine.
While combinations of tetra-methyl thiuram disulfide and a monoor di-halogenated-8-hydroxy quinaldine,
particularly the 5,7-dihalo-8-hydroxy quinaldines of the formula N as where Xi and X2 are like or unlike halogen atoms, are the most effective and exhibit the most pronounced synergistic antiseptic effect when admixed in a detergent composition, other halogenated 2-hydrocarbon substituted-8-hydroxy quinolines and their alkali metal salts when admixed with tetra-methyl thiuram disulfide in a detergent composition also exhibit synergism. As exemplary of such are:
5-bromo-8-hydroxy quinaldine 5-iodo-8-hydroxy quinaldine 6-chloro-8-hydroxy quinaldine 7-chloro-8-hydroxy quinaldine 7-bromo-8-hydroxy quinaldine 7-iodo-8-hydroxy quinaldine 5-bromo-7-methyl-8-hydroxy quinaldine 5-bromo-7-tert. butyl-8-hydroxy quinaldine 5,6,7-tri chloro-S-hydroxy quinaldine 5,6,7-tri bromo-8-hydroxy quinaldine 2-ethyl-5-chloro-8-hydroxy quinoline 2-ethyl-5,6-dichloro-8-hydroxyquinoline 2-propyl-5,7-dichloro-8-hydroxy quinoline 2-butyl-5,7-dichloro-8-hydroxy quinoline 2-phenyl-5-bromo-8-hydroxy quinoline 2-phenyl-5,7-dibromo-8-hydroxy quinoline 2-benzyl-5,7-dibromo-8-hydroxy quinoline The alkali metal salts of the aforementioned hydroxy substituted compounds of this invention when combined with a tetra-alkyl thiuram disulfide, such as tetra-methyl thiuram disulfide, in a detergent composition also exhibit a synergistic antiseptic effect, however, the alkali metal salts are not as effective as the parent compound.
Of the tetra-alkyl thiuram disulfides tetra-methyl thiuram disulfide is preferred, however, other tetra-alkyl thiuram disulfides such as the tetra-ethyl and the tetrabutyl thiuram disulfide when employed in conjunction with a halogenated 2-hydrocarbon substituted-S-hydroxy quinoline exhibit an antiseptic synergistic effect in a detergent composition.
Relatively small amounts of the synergistic mixture of a tetra-alkyl thiuram disulfide and a halogenated 2-hydrocarbon substituted-8-hydroxy quinoline in a detergent composition yield effective antiseptic detergent compositions. Amounts as low as 0.51% by weight of the mixture based upon the weight of the detergent have proved satisfactory in some instances, However, it is preferred to employ amounts in the order of 1-3% by weight. Larger amounts may be employed, as for example up to 10% by weight of the synergistic mixture, however, the-upper limit-used is determined by practical considerations.
The proportions of the component parts of the synergistic mixture will vary between wide limits depending upon the particular tetra-alkyl thiuram disulfide and. halo-. .genated 2-hydrocanbon. substituted-8.-hydroxy= quinoline employed, the availability and cost of the component parts, the detergent base, and the purpose of the antiseptic detergent composition. However, in general the weight ratio of the tetra-alkyl thiuram disulfide to the halogenated 2-hydrocarbon substituted-S-hydroxy quinoline or its alkali metal salt will vary from 25-75 parts of the former to 75-25 parts of the latter. While particularly good synergistic antiseptic results are obtained employing a weight ratio of 40-60 parts of a tetra-alkyl thiuram disulfide to 60-40 parts of a halogenated 2-hydrocarbon substituted-S-hydroxy quinaldine or its alkali metal salt the preferred mixture is that containing equal weights of each component.
Other antiseptic agents may be incorporated in the new antiseptic detergent composition as well as emollients, water softeners and the well known vehicles of the detergent trade. Various colors, antioxidants, perfumes and the like may be incorporated where desirable.
The term detergent includes soap and synthetic detergents, particularly the anionic detergents such as the substituted amides and the alkyl aryl sulfonates. The term detergent includes also mixtures of synthetic detergents and soap. The term soap or detergent soap as used herein is employed in its popular or ordinary meaning, that is, those cleansing compositions prepared from an alkali metal compound such as sodium or potassium hydroxide and a fat or fatty acid.
The halogenated Z-hydrocarbon substituted-8-hydroxy quinolines or their metal salts and the tetra-alkyl thiuram disulfides of this invention may be added to the detergent composition in any suitable manner during the crutching or milling or similar operation. The halogenated 2-hydrocarbon substituted-S-hydroxy quinolines or their metal salts and the tetra-alkyl disulfide may be first dissolved either separately or jointly in a suitable solvent and then incorporated in the detergent if so desired. In general any method which results in the halogenated 2-hydrocarbon substituted-8-hydroxy quinolines or their alkali metal salts and the tetra-alkyl thiuram disulfides of this invention being uniformly incorporated in the final detergent composition is satisfactory.
While the invention has been described relative to several particular embodiments it is to be understood it is not so limited but that many variations and modifications which are obvious to those skilledin the art to which the invention appertains may be made without departing from the spirit or scope of the invention.
What is claimed is:
1. An antiseptic detergent composition comprising a detergent soap and a minor weight proportion in respect to the detergent soap suflicient to impart antiseptic properties of a mixture of a halogenated 2-hydrocarbon substituted-S-hydroxy quinoline of the formula R I N where X is a halogen atom, where n is a whole number from 1 to 2, where R is selected from the group consisting of hydrogen, halogen atoms and short-chain alkyl groups, and where R is a hydrocarbon group containing not more than 7 carbon atoms selected from the group consisting of alkyl, aralkyl, aryl and alkaryl radicals, and a tetra-alkyl thiuram disulfide wherein each alkyl substituent is a short-chain alkyl group, said thiuram disulfide being a synergist for said halogenated compound. 2. An antiseptic detergent composition comprising a detergent soap and, aminor weight proportion in respect to the detergent soap sufficient to impart antiseptic properties of a mixture of tetra-methyl thiuram disulfide and a halogenated 8-hydroxy quinaldine of the formula -8-hydroxy quinaldine.
where X1 and X2 are halogen atoms.
5. An antiseptic detergent composition comprising a detergent soap and 0.5 to by weight based-upon the detergent soap of a mixture of equal parts by weight of tetra-methyl thiuram disulfide and a dihalo-S-hydroxy quinaldine of the formula where X1 and X2 are halogen atoms.
6. An antiseptic detergent composition comprising a detergent soap and l to 3% by weight based upon the detergent soap of a mixture of equal parts by weight of 6 tetra-methyl thiuram disulfide and a di-halo-S-hydroxy quinaldine of the formula X; CHI
where X1 and X2 are halogen atoms.
7. An antiseptic detergent composition comprising a detergent soap and 1 to 3% by weight based upon the detergent soap of a mixture of equal parts by weight of 5,7 dichloro 8- ydroxy quinaldine and tetra-methyl thiuram disulfide.
8. An antiseptic detergent composition comprising a detergent soap and 1 to 3% by weight based upon the detergent soap of a mixture of equal parts by weight of 5,7- dibromo-S-hydroxy quinaldine and tetra-methyl thiuram disulfide.
9. An antiseptic detergent composition comprising a detergent soap and 1 to 3% by weight based upon the detergent soap of a mixture of equal parts by weight of 5-chloro-7-bromo-8-hydroxy quinaldine and tetra-methyl thiuram disulfide.
10. An antiseptic detergent composition comprising a detergent soap and 1 to 3% by weight based upon the detergent soap of a mixture of equal parts by weight of S-chloro-7-iodo-8-hydroxy quinaldine and tetra-methyl thiuram disulfide.
11. An antiseptic detergent composition comprising a detergent soap and 1 to 3% by weight based upon the detergent soap of a mixture of equal parts by weight of 5-chlgro-8-hydroxy quinaldine and tetra-methyl thiuram disul de.
References Cited in the file of this patent Condensed Chemical Dictionary-4th Ed. (1950), p. 654
Dictionary De Specialties Pharmaceutiques-Vidal, Office of Vulgarisation Pharmaceutique (Paris), 1950, p. 1950.
Repertorium Pharmazeutischer Spezialpraparate-Supplernent I (August 1947), p. 211.

Claims (1)

1. AN ANTISEPTIC DETERGENT COMPOSITION COMPRISING A DETERGENT SOAP AND A MINOR WEIGHT PROPORTION IN RESPECT TO THE DETERGENT SOAP SUFFICIENT TO IMPART ANTISEPTIC PROPERTIES OF A MIXTURE OF A HALOGENATED 2-HYDROCARBON SUBSTITUTED 8-HYDROXY QUINOLINE OF THE FORMULA
US207246A 1951-01-22 1951-01-22 Antiseptic soap composition Expired - Lifetime US2695881A (en)

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Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2927899A (en) * 1955-09-28 1960-03-08 Lever Brothers Ltd Detergent germicidal compositions and process of making the same
US2937147A (en) * 1955-09-28 1960-05-17 Lever Brothers Ltd Stabilized germicidal soaps and process of making the same
US2948684A (en) * 1957-05-10 1960-08-09 Lever Brothers Ltd Disinfectant and deodorant soap composition
US3088916A (en) * 1958-08-11 1963-05-07 Monsanto Chemicals Bacteriostatic and fungistatic cleansing compositions
US3152181A (en) * 1961-01-18 1964-10-06 Us Vitamin Pharm Corp Alkoxypropylene biguanides
US3330768A (en) * 1964-06-29 1967-07-11 Monsanto Chemicals Mycobacteriostatic compositions
US3886277A (en) * 1967-02-14 1975-05-27 Schwarzkopf Gmbh Hans Methods of controlling dandruff using 5,7-dichloro-8-hydroxy quinoline
US5120711A (en) * 1988-04-01 1992-06-09 Egis Gyogyszergyar Synergistically active veterinary compositions and process for preparing same

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2251935A (en) * 1936-09-21 1941-08-12 Sharp & Dohme Inc Germicidal soap
US2353735A (en) * 1941-02-21 1944-07-18 Burton T Bush Inc Germicidal soap

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2251935A (en) * 1936-09-21 1941-08-12 Sharp & Dohme Inc Germicidal soap
US2353735A (en) * 1941-02-21 1944-07-18 Burton T Bush Inc Germicidal soap

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2927899A (en) * 1955-09-28 1960-03-08 Lever Brothers Ltd Detergent germicidal compositions and process of making the same
US2937147A (en) * 1955-09-28 1960-05-17 Lever Brothers Ltd Stabilized germicidal soaps and process of making the same
US2948684A (en) * 1957-05-10 1960-08-09 Lever Brothers Ltd Disinfectant and deodorant soap composition
US3088916A (en) * 1958-08-11 1963-05-07 Monsanto Chemicals Bacteriostatic and fungistatic cleansing compositions
US3152181A (en) * 1961-01-18 1964-10-06 Us Vitamin Pharm Corp Alkoxypropylene biguanides
US3330768A (en) * 1964-06-29 1967-07-11 Monsanto Chemicals Mycobacteriostatic compositions
US3886277A (en) * 1967-02-14 1975-05-27 Schwarzkopf Gmbh Hans Methods of controlling dandruff using 5,7-dichloro-8-hydroxy quinoline
US5120711A (en) * 1988-04-01 1992-06-09 Egis Gyogyszergyar Synergistically active veterinary compositions and process for preparing same

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