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

Definitions

• halogenated bisphenols are photosensitive and tend to cause discoloration in the finished product on exposure to ligh Also, they are somewhat toxic and present a potential hazard to domestic animals .which are prone to eat things,.even soap. Therefore, it
• the germicidal activity of unalkylated halogenated bisphenol is enhanced, synergized or potentiated by the incorporation therewith bisphenol in which the alkyl groupscont ain from 1 to 4 carbon atoms.
• the products of this invention therefore, are antiseptic compositions containing as their essential active ingredient a synergistic combination of an unalkylated halogenated bisphenol and an alkylated halogenated bisphenol in which the alkyl groups contain from 1 to 4 carbon atoms.
• the unalkylated halogenated bisphenol used in accordance with the present invention can be represented by the following structural formula: i
• unalkylated halogenated bisphenols include 2,2'-dihydroxy halogenated diphenyl methanes such as 2,2-dihydroxy-3,5, 6,35','6'-hexachlorodiphenyl methane '(hexachlorophene), 2,2'-dihydroxy- 3,5,3',5 tetrachlorodiphenyl methane, 2,2 dihydroxy- 4,5,4','5' tetrachlorodiphenyl methane, 2,2 dihydro-Xy- 3,4,3,4-tetrachlorodiphenyl methane, and 2,2'-dihydroxy- 5;5-dibromodiphenyl methane.
• 2,2'-dihydroxy halogenated diphenyl methanes such as 2,2-dihydroxy-3,5, 6,35','6'-hexachlorodiphenyl methane '(hexachlorophene), 2,2'-dihydroxy-
• alkylated halogenated bisphenols used in conjunction with the unalkylated halogenated bisphenols in the present invention can be any suitable bisphenol composi tion characterized by the presence of short-chain alkyl groups in the aromatic rings. These substances can be ⁇ epresented according to their chemical structure as folows:
• HO OH wherein X represents a halogen such as chlorine or bromine, n is an integer of from 1 to 3, R is an alkyl group containing from 1 to 4 carbon atoms and Y is a divalent radical including alkylene radicals having from 1 to 4' carbon atoms such as illustrated above, are used together in an antiseptic composition, a germicidal effect is achieved which is greater than the mere total of the individual effects of the individual ingredients.
• the invention relates to the synergistic cooperation of these two types of compounds when used in minor proportions in an antiseptic composition, and especially an antiseptic detergent composition, and the discovery that this synergistic phenomenon occurs even at pH conditions existing in soap and detergent formulations provides one of the important phases of the present invention.
• Relatively small amounts of the unalkylatcd halogenated bisphenol and the alkylated halogenated bisphenol are sufficient for the increased germicidal effect of the present invention. Satisfactory results are obtained when the combined weight of the two types of bisphenols are from 1 to 3% of the total weight of the composition.
• the objects of the invention are achieved when the weight ofthe unalkylated halogenated bisphenol is about 0.1% to 3% and the 'alkylated halogenated bisphenol is about 3% to 0.1% by Weight based upon the detergent or soap.
• the preferred weight is a concentration of about 0.25% to 1.75% of the unalkylated halogenated *bisphenol and about 1.75% to about 0.25% of the alkylated halogenated bisphenol, and an excellent product is one containing a detergent soap and about 1% of each of the unalkylated halogenated bisphenol and the alkylated halogenated bisphenol. It will be understood that even concentrations below the ranges just set out will provide some degree of germicidal eflYect and that substantially higher concentrations than those given will provide satisfactory results, although there are certain practical considerations, such as the cost of the bisphenol and a certain impairment in detergent properties, which limit the desirability of including greater amounts of the germicide in the soap.
• soap refers to the water-soluble ammonium, metallic, organic base salts of various fatty acids, which are chiefly lauric, oleic, stearic, and palrnitic acids. As used in this specification and claims, the term is intended to cover all products in which soap is a major constituent, for example, bar, flake, powdered, soft and liquid soaps; shaving creams, toothpastes, cleansing creams, etc.
• the invention also contemplates the use of anionictype synthetic detergents in place of the soap.
• anionic-type synthetics suitable for use in the invention can be described as those detergents having pronounced cleansing power and including in their molecular structure an alkyl radical containing from 6 to 18 carbon atoms and a sulfonic acid or sulfuric acid ester radical. Either organic base, ammonium, sodium or potassium salts of the anionic-type detergents can be used.
• the main types of detergents falling within this category are the alkyl-aryl sulfonates, such as sodium or potassium dodecyl benzene sulfonate, sodium or potassium octadecyl benzene sul-fonate and sodium; or potassium octyl naphthalene sulfonate; the alkyl sulfates such as sodium or potassium salts of dodecyl, hexadecyl, and octadecyl sulfate; the sulfonated fatty acid amides such as the sodium or potassium salts of the oleic acids of methyl taurine; and the sulfonated monoglycerides such as the mono-coconut oil fatty acid ester of 1,2-hydroxy propane-3-sodium sulfonate.
• alkyl-aryl sulfonates such as sodium or potassium dodecyl benzene sulfonate,
• the unalkylated halogenated bisphenol and the alkylated halogenated :bisphenol can be added to the soap or the detergent by any suitable method which results in a uniform'distr'ibution of the additives throughout the entire mass.
• a high satisfactory dispersion method of carrying out the addition step is described more fully in the copending application Serial No. 263,302, filed December 26, 1'95 1, now abandoned.
• EXAMPLE I The procedure employed for determining the minimum effective dose (M.E.D.) represents a variation of a method published in the Journal of General Microbiology, volume 10, No. 2, April 1954, on Observations on the Mode of Action of Antibiotic Synergism and Antagonism, Department of Microbiology, University of California School of Medicine. In place of the plate counts used in the published method, the end point of chemical activity in the present method was taken as that point at which no growth was apparent in the broth tubes.
• the minimum effective dose of 2,2-dihydroxy-3,5,6,3', 5',6' -hexachlorodiphenyl methane (hexachlorophene), 2,2-dihydroxy-3,3'-dimethyl 5,5 dichlorodiphenyl sulfide, and 2,2-hydroxy 3,3 dimethyl 5,5 di-chlorodiphenyl trichloroethane were first determined by diluting the prepared stock solutions of the test chemicals in a series of tubes containing 10 ml. of nutrient broth culture medium. Each successive tube in the series contained the test chemicals at /2 the concentration of the previous tube. 0.1 ml. of a 1-10 dilution of a 24 hour broth culture of the test organisms M.
• each of the other two test chemicals were combined with hexachlorophene in a series of broth tubes at a concentration in broth at sub-inhibitory and near sub-inhibitory levels of all chemicals.
• Inoculation with the test organism M. pyogenes var. aurells was made in each tube in the series by adding to each tube 0.1 ml. of a 1-10 dilution of a 24 hour broth culture of the organism. The incubation period was 48 hours at a temperature of 37 C.
• the determination of synergistic activity was made in the tube or tubes having the lowest sub-inhibitory concentration of both hexachlorophene and the individual test chemical showing no apparent growth of the test organism.
• dichlorodiphenyl trichloroethane (C). 0.5 0 (A)+(B) 0 synergism. (AH-(C) 0 synergism.
• Composition I A B I C I D J E Fine Art neutral white toilet soap 2,2 dlhydroxy 3,5,6,3,5,6' hexachlorodiphenyl methane" 2,2 dihydroxy 3,3 methyl-5,5 diehlorodiphenyl sulfide 2 1 2,2 dihydroxy 3,3 dimethyl 5,5 dichlorodiphenyl triehloroethane 2 1 Aliquots of each of the above described compositions containing 2% by weight active ingredient were added Table III Composition A i B 0 D E Period of Incubation 48 48 48 48 48 Amount 0! growth 3+ 3+ 3+ 1+ Legend:
• An antiseptic detergent composition comprising a water-soluble soap and an antiseptic combination having a synergistic effect consisting of from about 0.1% to about 3.0% by weight-based upon the soap of 2,2-di- 6 hydroxy-3,S,6,3,5',6'-hexachlorodiphenyl methane and from about 3.0% to about 0.1% by weight based upon the soap of 2,2-dihydroxy-3,3-dimethyl-5,5'-dichlorodiphenyl sulfide.

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• Chemical & Material Sciences (AREA)
• Life Sciences & Earth Sciences (AREA)
• Engineering & Computer Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Organic Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Cosmetics (AREA)
• Detergent Compositions (AREA)

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Citations (5)

• 0
  • NL NL210944D patent/NL210944A/xx unknown
  • NL NL210943D patent/NL210943A/xx unknown
• 1955
  • 1955-09-27 US US537057A patent/US3081266A/en not_active Expired - Lifetime
• 1956
  • 1956-09-25 DE DEA25737A patent/DE1017335B/de active Pending
  • 1956-09-25 DE DEA25738A patent/DE1017312B/de active Pending
  • 1956-09-26 GB GB29448/56A patent/GB814483A/en not_active Expired
  • 1956-09-26 FR FR1187638D patent/FR1187638A/fr not_active Expired
  • 1956-09-27 NL NL210944A patent/NL104630C/nl active
  • 1956-09-27 NL NL210943A patent/NL102603C/nl active

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