Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C233/00—Carboxylic acid amides
  • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
  • C07C233/34—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups
  • C07C233/35—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
  • C07C233/38—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a carbon atom of an acyclic unsaturated carbon skeleton
• • 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
  • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
  • A01N33/02—Amines; Quaternary ammonium compounds
  • A01N33/12—Quaternary ammonium compounds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
  • C07C211/62—Quaternary ammonium compounds
  • C07C211/63—Quaternary ammonium compounds having quaternised nitrogen atoms bound to acyclic carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
  • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
  • C07C217/04—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
  • C07C217/06—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted
  • C07C217/08—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one etherified hydroxy group and one amino group bound to the carbon skeleton, which is not further substituted the oxygen atom of the etherified hydroxy group being further bound to an acyclic carbon atom
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/16—Nitrogen-containing compounds
  • C08K5/17—Amines; Quaternary ammonium compounds
  • C08K5/19—Quaternary ammonium compounds

Definitions

• antimicrobial compositions comprising:
• R ⁇ and R 2 are independently C 12 or C 14 -alky1;
• X is a halogen such as Cl, Br or I;
• compositions exhibit excellent antibacterial activity, low toxicity, water solubility and a low irritation effect on the skin of the user.
• the several bis-quaternary ammonium compounds which comprise the blend composition (a) are made by reacting one mole of a selected dihalo compound selected from:
• X is a halide such as Cl, Br and I, with 2 moles of dodecyldimethyl a ine, tetradecyldimethylamine or predetermined mixtures thereof.
• a typical reaction is the following:
• a reaction mixture of one mole of dodecyldimethyla ine, one mole of the tetradecyldimethylamine and one mole of the selected dichloro compound will provide the following blend compositions:
• Another way of introducing the quaternary nitrogen into the polymer structure is by using monomers with functionality, either tertiary amine or reactive alkylating groups which are quaternizable.
• the following vinyl ammonium monomers can be copolymerized with vinyl pyrrolidone by solution polymerization in isopropyl alcohol or by precipitation polymerization in cyclohexane or heptane and under conditions to provide low molecular weight copolymers, i.e. about 10,000 to about 20,000, suitable for coprecipitation or admixture with the blend of bis-quaternary ammonium compounds.
• a preferred copolymer is the copolymer of vinylpyrrolidone and MAPTAC, which is known as GAFQUAT ® HS-100 resin (ISP) , and is supplied as a 20% aqueous solution.
• the coprecipitate product comprising the blend composition and copolymer usually is prepared by reacting predetermined amounts of a dilute aqueous solution of the blend composition and copolymer, usually from 90:10 to 10:90 wt. ratio of each, respectfully, and removing the solvent.
• the desired coprecipitate is formed as a solid product.
• the antimicrobial compositions of the invention may be used as such; however, preferably they are admixed with inert materials as pharmaceutical and cosmetic formulations, e.g. in the form of powders, solutions, lotions, suspensions and the like. Typical inert additives include water, alcohols, starch, and the like. Active ingredients also may be included in the product, if desired.
• coprecipitate form of the antibacterial product of the invention is favored, admixtures of the blend and copolymer also may be used to prepare commercial compositions.
• the antimicrobial activity of the products herein are represented by their Minimum Inhibitory Concentration (MIC) against E.Coli, a Gram negative microorganism. Their effect on skin is indicated by an Irritation Index.
• MIC Minimum Inhibitory Concentration
• Irritation Index an Irritation Index
• the antibacterial activity of the compositions of the invention are up to 12.5 times more favorable than the individual compounds of the blend; the product containing the D blend shows only 1/3 to 1/4 as much irritation to the skin as the H and L blend products, respectively; and the blends are 5-20 less toxic than the individual compounds in the blends.
• the antimicrobial blend composition of bis-quaternary ammonium compounds is selected from those represented by the formula
• R j L and R are independently C 12 or
• X ⁇ is a halogen such as Cl, Br or I; and in the weight ratio of about 25% of the compound where both R. ⁇ and R 2 are C 12 -alkyl;
• the blend composition with polyvinylpyrrolidone usually is prepared by reacting a dilute solution of the blend composition in alcohol or water, preferably methanol, with a dilute solution of the bisquat blend composition in the same solvent, and removing the solvent to form the desired coprecipitate solid product.
• the blend coprecipitate compositions of the invention are prepared by refluxing the selected dichloro compound, the amines, and an alkali metal halide, in alcoholic solution, removing the solvent, precipitating the blend of bisquats in an organic solvent in substantially quantitative yield, and reacting a solution of the thus-prepared bisquat in methanol or water with a solution of soluble polyvinylpyrrolidone in the same solvent, and removing the solvent under reduced pressure to form the solid coprecipitate product.
• blend compositions with polyvinylpyrrolidone exhibit an enhanced antimicrobial activity and reduced toxicity as compared to the individual compounds therein. Furthermore, they show excellent solubility in water, and less irritation to the user, as compared to the blend composition itself, that is, without polyvinylpyrrolidone.
• the antimicrobial compositions of the invention may be used as such, or, preferably, admixed with an inactive or inert component to prepare pharmaceutical formulations such as powders, solutions, lotions, suspensions and the like. Typical additives include water, alcohols, starch, etc. Other active ingredients may be included if desired.
• coprecipitate form is favored, mixtures of the blend composition and polyvinylpyrrolidone may be used as well.
• Typical antimicrobial activities represented by their Minimum Inhibitory Concentration (MIC) , against E.Coli, a gram negative microorganism, is presented in the Table below for both the individual compounds in blend composition D and the D, H and L blend compositions with polyvinylpyrrolidone at different relative amounts of the compounds therein (as measured in a 10% active solution) .
• MIC Minimum Inhibitory Concentration
• the MIC values of the blend-PVP coprecipitate compositions in the TABLE are up to 25 times more favorable than the individual compounds in the blend.
• compositions of the invention also have increased water solubility than blends without PVP.
• the LD 50 toxicity of the D blend-PVP compositions above also is reduced by a factor of 5-6 as compared to the individual compounds in the blend, furthermore they exhibit a substantially reduced irritation to the skin as compared to the individual compounds or the blend without PVP.
• the blend composition comprised 25% by weight of A, 50% by weight of B and 25% by weight of C compounds.
• Typical antimicrobial activities represented by their Minimum Inhibitory Concentration (MIC) against E.Coli, a gram negative microorganism, is presented in the Table below for both the individual compounds in blend composition D and the blend composition itself, with PVP, with different relative amounts of the A, B and C compounds therein (as measured in a 10% active solution) .
• MIC Minimum Inhibitory Concentration
• the MIC values of the D blend compositions in the TABLE are up to 25 times more favorable than the individual compounds in the blend.
• the LDt jQ toxicity of the blend composition D (without PVP) above also is observed to be reduced by a factor of 5-6 as compared to the individual compounds.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Health & Medical Sciences (AREA)
• Dentistry (AREA)
• Zoology (AREA)
• Pest Control & Pesticides (AREA)
• Engineering & Computer Science (AREA)
• Agronomy & Crop Science (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Plant Pathology (AREA)
• Environmental Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Medicinal Preparation (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Applications Claiming Priority (7)

Publications (2)

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Citations (4)

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• 1992
  • 1992-08-12 WO PCT/US1992/006695 patent/WO1993007251A1/en not_active Ceased
  • 1992-08-12 AU AU24618/92A patent/AU2461892A/en not_active Abandoned
  • 1992-08-12 EP EP19920917984 patent/EP0607162A4/de not_active Withdrawn
  • 1992-08-12 CA CA 2120335 patent/CA2120335A1/en not_active Abandoned

Patent Citations (4)

Non-Patent Citations (2)

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