US20080026974A1 - Antimicrobial hand wash - Google Patents

Antimicrobial hand wash Download PDF

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Publication number
US20080026974A1
US20080026974A1 US11/494,473 US49447306A US2008026974A1 US 20080026974 A1 US20080026974 A1 US 20080026974A1 US 49447306 A US49447306 A US 49447306A US 2008026974 A1 US2008026974 A1 US 2008026974A1
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Prior art keywords
acid
hand wash
primary
antimicrobial
base
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US11/494,473
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English (en)
Inventor
Ronald A. Barnhart
David P. Lerner
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Go-Jo Industries Inc
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Go-Jo Industries Inc
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Priority to US11/494,473 priority Critical patent/US20080026974A1/en
Application filed by Go-Jo Industries Inc filed Critical Go-Jo Industries Inc
Assigned to GOJO INDUSTRIES, INC. reassignment GOJO INDUSTRIES, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BARNHART, RONALD A., LERNER, DAVID P.
Priority to AT07252834T priority patent/ATE486568T1/de
Priority to DE602007010213T priority patent/DE602007010213D1/de
Priority to PT07252834T priority patent/PT1886660E/pt
Priority to DK07252834.2T priority patent/DK1886660T3/da
Priority to EP07252834A priority patent/EP1886660B1/en
Priority to AU2007203322A priority patent/AU2007203322B2/en
Priority to ES07252834T priority patent/ES2352158T3/es
Priority to CA2594270A priority patent/CA2594270C/en
Priority to BRPI0703313-3A priority patent/BRPI0703313A/pt
Priority to JP2007195824A priority patent/JP2008056912A/ja
Publication of US20080026974A1 publication Critical patent/US20080026974A1/en
Priority to US12/434,355 priority patent/US7851424B2/en
Assigned to PNC BANK, NATIONAL ASSOCIATION reassignment PNC BANK, NATIONAL ASSOCIATION SECURITY AGREEMENT Assignors: GOJO INDUSTRIES, INC.
Assigned to STEEL CITY CAPITAL FUNDING, A DIVISION OF PNC BANK, NATIONAL ASSOCIATION reassignment STEEL CITY CAPITAL FUNDING, A DIVISION OF PNC BANK, NATIONAL ASSOCIATION SECURITY AGREEMENT Assignors: GOJO INDUSTRIES, INC.
Priority to US13/095,284 priority patent/US8372790B2/en
Assigned to GOJO INDUSTRIES, INC. reassignment GOJO INDUSTRIES, INC. RELEASE BY SECURED PARTY (SEE DOCUMENT FOR DETAILS). Assignors: STEEL CITY CAPITAL FUNDING, A DIVISION OF PNC BANK, NATIONAL ASSOCIATION
Abandoned legal-status Critical Current

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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
    • 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/361—Carboxylic acids having more than seven carbon atoms in an unbroken chain; Salts or anhydrides 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
    • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
    • A61K8/36—Carboxylic acids; Salts or anhydrides thereof
    • A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
    • 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
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/02—Local antiseptics
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/10—Washing or bathing preparations
    • 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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents ; Methods for using cleaning compositions
    • C11D11/04—Special methods for preparing compositions containing mixtures of detergents ; Methods for using cleaning compositions by chemical means, e.g. by sulfonating in the presence of other compounding ingredients followed by neutralising
    • 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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/08—Liquid soap, e.g. for dispensers; capsuled
    • 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
    • C11D3/485—Halophors, e.g. iodophors
    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/002—Non alkali-metal soaps
    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22—Organic compounds, e.g. vitamins
    • C11D9/26—Organic compounds, e.g. vitamins containing oxygen
    • 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
    • C11D9/00—Compositions of detergents based essentially on soap
    • C11D9/04—Compositions of detergents based essentially on soap containing compounding ingredients other than soaps
    • C11D9/22—Organic compounds, e.g. vitamins
    • C11D9/30—Organic compounds, e.g. vitamins containing nitrogen

Definitions

  • the present invention generally relates to antimicrobial compositions, and, more articularly, relates to soaps that include an efficacy boosting chemical derived from the neutralization of a nitrogeneous base with a neutralizing acid.
  • True soaps are created through a saponification reaction in which fats, more appropriately, fatty acids, are neutralized with a base. To ensure that the reaction is driven to completion, it is common practice to employ an excess of base. Because soaps are generally compatible with antimicrobial agents, they are often used in liquid antimicrobial hand washes. Such soap-based antimicrobial hand washes are found in numerous markets including healthcare, food services, and consumer.
  • Antimicrobial agents are selected from a variety of classes, including bisguanidine (e.g., chlorhexidine digluconate), diphenyl compounds, benzyl alcohols, trihalocarbanilides, quaternary ammonium compounds, ethoxylated phenols, and phenolic compounds, such as halo-substituted phenolic compounds, like p-chloro-m-xylenol (known as “pcmx”) and 2,4,4′-trichloro-2′hydroxy-diphenylether (known as “triclosan”). Although these antimicrobial agents are used in numerous hand wash formulations, they are not without some detrimental properties. Antimicrobial agents are typically irritating to the skin.
  • wash formulation Another important concern for a wash formulation is the aesthetics of the product. For example, the public has come to associated foaming ability with cleaning ability, and, as a result, consumers are less likely to purchase a wash formulation that does not foam while washing. This consumer perception drives those in the market to formulate washing products which produce copious amounts of foam. As mentioned above, irritancy is a concern. The color and odor of a wash formulation is also important. When soaps are used in conjunction with antimicrobial agents, they do not present the best of each of these desired properties. Although the presence of the soap allows for a reduction in the amount of antimicrobial agent while maintaining a relatively high log kill, antimicrobial soap products tend to irritate the skin. Thusly, skin conditioning agents need added to produce an aesthetically pleasing hand wash.
  • This invention involves the creation of a soap through a saponification reaction and the creation of an amine salt for inclusion in the soap.
  • “primary” relates to those acids and bases employed in the saponification reaction
  • “secondary” relates to those acids and bases employed to create the amine salt, although, when a nitrogenous base is employed, it can serve as both the primary and the secondary base.
  • “Nitrogenous base” refers to bases that include at least one nitrogen bound to no more than three substituents.
  • this invention provides an antimicrobial hand wash comprising a soap and the reaction product of a nitrogenous base neutralized with a neutralizing acid selected from anhydrides, organic acids, and inorganic acids.
  • this invention provides an antimicrobial hand wash comprising a soap; an antimicrobial agent; and the reaction product of monoethanolamine neutralized with lactic acid.
  • an antimicrobial hand wash is produced.
  • Soap is produced through the saponification of a primary fatty acid with a primary nitrogenous base, wherein the mole to mole ratio for alkalinity of the primary nitrogenous base to free primary fatty acid is from about 1.5:1 to 3:1 such that there exists an excess of primary nitrogenous base after the saponification.
  • the excess primary nitrogenous base is reacted with a secondary acid added to the soap produced as above, the secondary acid being selected from the group consisting of carboxylic acids, organic acid anhydrides and mixed acid anhydrides to create an amine salt.
  • FIG. 1 is a hypothesized reaction between lactic acid and monoethanolamine, in accordance with an embodiment of this invention reduced to practice;
  • FIG. 2 is a titration curve for monoethanolamine-lactic acid neutralization that experimentally verifies the correctness of the equation derived herein below respecting such neutralization.
  • the hand wash herein includes a soap; an antimicrobial agent; and an amine salt.
  • the soap is made through a saponification reaction between a primary fatty acid and a primary base.
  • the amine salt is created through the neutralization of a nitrogenous base with a secondary acid.
  • the primary base may be a hydroxide; a nitrogenous base; an oxide of a group I element, calcium, strontium, or barium; or the conjugate base of a weak acid.
  • the selection of the primary base can affect the process methods that can be practiced to produce the hand wash.
  • the amine salt may be created either by neutralizing excess primary nitrogenous base left over after completion of the saponification reaction, in which case it is present in the soap, at creation, or by neutralizing the same primary nitrogenous base or a different secondary nitrogenous base in a separate process, in which case it is subsequently added to the soap created in the saponification reaction.
  • the primary base is chosen to be a hydroxide; an oxide of Group I, calcium, strontium, or barium; or the conjugate base of a weak acid
  • the amine salt cannot be created by neutralizing an excess of that base, and a secondary nitrogenous base is neutralized to create the amine salt.
  • a secondary acid is employed to neutralize the excess nitrogenous base or secondary nitrogenous base as the case may be.
  • “primary” relates to those acids and bases employed in the saponification reaction
  • “secondary” relates to those acids and bases employed to create the amine salt, although, when a nitrogenous base is employed, it can serve as both the primary and the secondary base.
  • the amine salt created via the acid-base neutralization between the secondary acid and either an excess primary nitrogenous base or a secondary nitrogenous base is found to have surprising antimicrobial properties when combined with an antibacterial agent.
  • the soap is made from a primary fatty acid and a primary base.
  • the primary fatty acid may be derived from crude fats or selected carboxylic acids, although it is typically less desirable to employ the crude fats.
  • the crude fats include known animal fats, vegetable oils and the like, and generally have a glycerol linked with at least 1, but no greater than three fatty acids.
  • the carboxylic acids which are more preferred, may be selected from carboxylic acids having from 6 to 40 carbon atoms in the main fatty chain. In other embodiments, the carboxylic acids are chosen to have from 6 to 20 carbon atoms in the main fatty chain.
  • Suitable carboxylic acids include, and are not limited to, arachidic acid, arachidonic acid, beeswax acid, behenic acid, coconut acid, corn acid, cottonseed acid, erucic acid, hydrogenated coconut acid, hydrogenated menhaden acid, hydrogenated palm acid, hydrogenated tallow acid, hydroxystearic acid, isomerized linoleic acid, isomerized safflower acid, isostearic acid, lauric acid, linoleic acid, myristic acid, oleic acid, olive acid, palm acid, palmitic acid, palm kernel acid, peanut acid, pelargonic acid, rapeseed acid, rice bran acid, ricinoleic acid, safflower acid, soy acid, stearic acid, sunflower seed acid, tall oil acid, tallow acid, undecanoic acid, undecylenic acid, and wheat germ acid. Mixtures of the forgoing might also be employed. In particular embodiments, lauric acid is preferred
  • Various primary bases can be selected for the saponification reaction, including hydroxides, nitrogenous bases, oxides of Group I, Ca, Sr, or Ba, and conjugate bases of weak acids.
  • a nitrogenous base is ultimately employed to create the desired amine salt component of the hand wash, and thus if a nitrogenous base is not employed as the primary base for the saponfication reaction, one must be employed as a secondary base to create the amine salt. If a nitrogenous base is used as the primary base, the amine salt can be formed directly in the soap solution. More particularly, an excess of nitrogenous base can be used in the saponification reaction, and, once that reaction is complete, the excess can be neutralized by a secondary acid to create the amine salt in situ.
  • the processes for creating the hand wash are disclosed more fully below.
  • the nitrogenous base can be selected from ammonia and virtually any hydroxylated nitrogenous base.
  • Suitable nitrogenous bases include, but are not limited to, 2-aminobutanol, aminoethyl propanediol, aminomethyl propanol, aminopropanediol, bis-hydroxyethyl tromethamine, butyl diethanolamine, butylethanolamine, dibutyl dthanolamine, diethanolamine, diisopropanolamine, diisopropylamine, dimethyl isopropanolamine, monoethanolamine, dimethyl monoethanolamine, ethyl ethanolamine, isopropanolamine, isopropylamine, methylethanolamine, methylglucamine, morpholine, triethanolamine, triispropanolamine, tromethamine. Mixtures of the forgoing might also be employed. In particular embodiments, monoethanolamine is preferred.
  • the other primary bases suitable for use include hydroxides such as calcium hydroxide, lithium hydroxide, potassium hydroxide, and sodium hydroxide; metal oxides such as calcium oxide, and sodium oxide; and conjugate bases of weak acids such as dipotassium phosphate, disodium phosphate, magnesium carbonate, pentapotassium triphosphate, petnasodium trisphosphate, potassium carbonate, sodium carbonate, tetrapotassium pyrophosphate, tetrasodium pyrophosphate, and trisodium phosphate. If one or more of these other primary bases is employed as the primary base, and there is not sufficient excess nitrogenous base (if any) employed, the nitrogenous base is to be employed as a secondary base.
  • hydroxides such as calcium hydroxide, lithium hydroxide, potassium hydroxide, and sodium hydroxide
  • metal oxides such as calcium oxide, and sodium oxide
  • conjugate bases of weak acids such as dipotassium phosphate, disodium phosphate, magnesium carbonate, pent
  • the secondary acid used to neutralize either an excess of nitrogenous base or a secondary nitrogenous base may generally be selected from the acid classes of anhydrides and organic and inorganic acids.
  • Appropriate organic compounds include, but are not limited to, carboxylic acids, organic acid anhydrides and mixed acid anhydrides.
  • a non-exhaustive list of useful secondary acids as neutralizing agents includes linear carboxylic acids such as acetic acid, lactic acid, and glycolic acid; homocyclic carboxylic acids such as acetylsalicylic acid; hetrocyclic carboxylic acids such as nicotinic acid; aromatic carboxylic acids such as benzoic acid; branched aliphatic carboxylic acids such as isopropanoic acid; polyprotic carboxylic acids such as oxalic acid and succinic acid; and organic and mixed anhydrides such as benzoic acid anhydride and mixed phosphoanhydride.
  • linear carboxylic acids such as acetic acid, lactic acid, and glycolic acid
  • homocyclic carboxylic acids such as acetylsalicylic acid
  • hetrocyclic carboxylic acids such as nicotinic acid
  • aromatic carboxylic acids such as benzoic acid
  • branched aliphatic carboxylic acids such as isopropanoic acid
  • Suitable inorganic acids may include, but are not limited to, strong and weak polyprotic acids such as sulfuric acid and phosphoric acid; monoprotic weak acids such as sodium bisulfate; monoprotic strong acids such as hydrogen halides and perchloric acid; and inorganic acid anhydrides such as carbon dioxide.
  • strong and weak polyprotic acids such as sulfuric acid and phosphoric acid
  • monoprotic weak acids such as sodium bisulfate
  • monoprotic strong acids such as hydrogen halides and perchloric acid
  • inorganic acid anhydrides such as carbon dioxide.
  • lactic acid is most preferred.
  • the antimicrobial hand wash contains at least one antimicrobial agent, which is generally appreciated as a term of art for those compounds that produce acceptable time-kill antimicrobial activity to be suitable for sanitizing. More specifically, the hand wash herein has efficacious properties against both Gram-positive and Gram-negative microorganisms.
  • the terms “antimicrobial agent” is to cover compositions that have greater than 2 log kill reduction on both Gram-negative bacteria, specifically Klebsiella pheumoniae, and Gram-positive bacteria, specifically Staphylococcus aureus.
  • the antimicrobial agent of the hand wash is selected from the group consisting of bisguanidines, quaternary ammonium compounds, benzyl alcohols, trihalocarbanilides, iodine containing compounds, and phenolic compounds. Mixtures of the forgoing might also be employed. In particular embodiments, phenolic compounds are employed.
  • phenol-based antimicrobial agents useful in this invention are exemplified by the following compounds, and may be used alone or in combination:
  • Y chlorine or bromine
  • Z is SO 2 H, NO 2 , or C 1 -C 4 alkyl
  • r is 0 to 3
  • o is 0 to 3
  • p m is 0, n is 0 or 1, o is 1 or 2, r is 1 or 2, and p is 0.
  • Y is chlorine
  • m is 0, n is 0, o is 1, r is 2, and p is 0.
  • a particularly useful 2-hydroxydiphenyl compound has the structure:
  • R 1 is hydro, hydroxy, C 1 -C 4 alkyl, chloro, nitro, phenyl, or benzyl
  • R 2 is hydro, hydroxy, C 1 -C 6 alkyl, or halo
  • R 3 is hydro, C 1 -C 6 alkyl, hydroxy, chloro, nitro, or a sulfur in the form of an alkali metal salt or ammonium salt
  • R.sub.4 is hydro or methyl
  • R 5 is hydro or nitro.
  • Halo is bromo or, preferably, chloro.
  • phenol derivatives include, but are not limited to, chlorophenols (o-, m-, p-), 2,4-dichlorophenol, p-nitrophenol, picric acid, xylenol, p-chloro-m-xylenol, cresols (o-, m-, p-), p-chloro-m-cresol, pyrocatechol, resorcinol, 4-n-hexylresorcinol, pyrogallol, phloroglucin, carvacrol, thymol, p-chlorothymol, o-phenylphenol, o-benzylphenol, p-chloro-o-benzylphenol, phenol, 4-ethylphenol, and 4-phenolsulfonic acid.
  • Other phenol derivatives are listed in WO 98/55096 and U.S. Pat. No. 6,113,933, incorporated herein by reference.
  • R 1 and R′ 1 are hydroxy, and R 2 , R′ 2 , R 3 , R′ 3 , R 4 , R′ 4 , R 5 , and R′ 5 , independent of one another, are hydro or halo.
  • diphenyl compounds are hexachlorophene, tetrachlorophene, dichlorophene, 2,3-dihydroxy-5,5′-dichlorodiphenyl sulfide, 2,2′-dihydroxy-3,3′,5,5′-tetrachlorodiphenyl sulfide, 2,2′-dihydroxy-3,5′,5,5′,6,6′-hexachlorodiphenyl sulfide, and 3,3′-dibromo-5,5′-dichloro-2,2′-dihydroxydiphenylamine.
  • Other diphenyl compounds are listed in WO 98/55096, incorporated herein by reference.
  • the phenol-based antimicrobial agent is selected from triclosan, 2,2′-dihydroxy-5,5′-dibromodiphenyl ether, pcmx, ortho-phenylphenol, and mixtures thereof.
  • additional compounds are typically used to produce an acceptable hand wash for consumer use.
  • These compounds include, but are not limited to, foam modifying agents, pH adjusting agents, emollients, humectants, skin conditioning agents, dyes and fragrances.
  • foam modifying agents include, but are not limited to, foam modifying agents, pH adjusting agents, emollients, humectants, skin conditioning agents, dyes and fragrances.
  • they may be employed in amounts and for reasons known in the prior art.
  • excess base is backtitrated with the secondary acid to create the amine salt directly within the soap solution.
  • the saponification reaction is carried out with near equivalence of primary nitrogenous base and primary fatty acid, such that there is not a significant excess of the primary base present after saponification.
  • the amine salt is added to the soap solution rather than being created therein, as in the super dosing process.
  • the mole to mole ratio for alkalinity to free fatty acid is preferably from about 1.5:1 to 3:1, as opposed to the 0.8:1 to 1.25:1 ratios generally practiced in saponification reactions.
  • the excess nitrogenous base is backtitrated with a second acid to an alkalinity to total acid ratio from about 0.8:1 to 1.25:1, wherein “total acid ratio” takes into account the number of moles of both the primary fatty acid employed in the saponification reaction and the secondary acid employed to create the amine salt.
  • total acid ratio takes into account the number of moles of both the primary fatty acid employed in the saponification reaction and the secondary acid employed to create the amine salt.
  • the mole to mole ratio for alkalinity to free fatty acid is substantially 1:1, such that there is an insubstantial amount of excess base at the completion of the saponification reaction.
  • This process is most likely used when the primary base employed is not a nitrogenous base, and thus cannot contribute to provide the amine salt in situ as in the super dosing process.
  • the amine salt can either be created in a separate process, or even purchased, and added to the soap solution, or it can be created by adding a secondary nitrogenous base to the soap solution and thereafter neutralizing it with a secondary acid.
  • the amine salt could be added to be present in virtually any amount, it is preferable added to comprise up to about 20% of the final hand wash formula, by weight.
  • the pH of the solution should be similar.
  • the preferred pH is between 7 and 10.5.
  • the invention goes against common day teachings by using a large amount of excess base, and then the excess base is titrated with a second acid to an alkalinity to total acid ratio from about 0.8:1 to 1.25:1. Normal saponification processes occur at alkalinity to fatty acid ratio from about 0.8:1 to 1.25:1.
  • the antimicrobial agent has a limited solubility in water, as is the case, for example, with phenol derivative antimicrobial agents
  • the antimicrobial agent is added to the soap solution as part of an “active premix,” which is a solution of the antimicrobial agent dissolved in a hydric solvent.
  • the hydric solvent should be chosen from either monohydric solvents, such as alcohols, or polyhydric solvents, such as glycols. The most preferred compounds are short carbon chain polyhydric compounds, on the order of eight or less carbons, but longer chains can be used.
  • the sole use of the solvent is to dissolve the antimicrobial agent; it is therefore pertinent that the solvent have the ability to readily dissolve the desired antimicrobial agent or agents.
  • the antimicrobial agent may be added anytime after the completion of the saponification reaction.
  • the antimicrobial agent comprises from about 0.01 to 10 wt % of the final formula; in other embodiments, from 0.05 to 7.5 wt %; and in yet other embodiments, from 0.1 to 1 wt %.
  • the hand wash formulations of this invention are typically comprised of from about 0.01 to 17.5 weight percent (wt %) of the primary fatty acid; from about 0.005 to 25 wt % of the primary base; and from about 0.01 to 10 wt % of the antimicrobial agent.
  • the primary fatty acid comprises from about 0.05 to 17.5 wt % of the final formula, and in yet other embodiments, from about 0.1 to 15 wt %.
  • the primary nitrogenous base comprises from about 0.025 to 25 wt % of the final formula; in other embodiments, from about 0.05 to 22 wt %.
  • the secondary base can be identified as any amount of base that exceeds that needed for equivalent saponfication.
  • the secondary base is from about 0.005 to 22.5 wt %, in yet other embodiments, from about 0.025 to 22.5 wt %, and more particular from about 0.05 to 20 wt %.
  • the secondary acid comprises from about 0.008 to 25 wt %, in yet other embodiments from about 0.04 to 25 wt %, and more particular from about 0.09 to 22.5 wt % of the hand wash formula.
  • monoethanolamine is both the primary and secondary base, and it is reacted with lactic acid as the secondary acid to produce an amine salt, believed to be monoethanolammonium lactate.
  • FIG. 1 shows the chemical reaction. As pictured the acid and base react in a one mole to one mole ratio. Lactic acid is a monoprotic acid, and this proton is the one transferred during this reaction, creating a carboxylate anion. The amine group found in monoethanolamine accepts the proton from the lactic acid via the lone pair of electrons on the nitrogen. This proton then creates an ammonium cation.
  • the reaction occurs spontaneously, and there is one distinct characteristic of the reactants that determine the quality of this reaction that need to be examined.
  • the reaction generates heat and the temperature needs to be monitored because of detrimental effects at high temperatures. With higher temperature, the oxidation of monoethanolamine via the loss of the amine group is expedited.
  • the reaction should be carried out slowly so the heat generated can dissipate and not degrade the monoethanolamine. This can be a concern with other nitrogenous bases, and should be taken into account to avoid negatively impacting the reaction.
  • the pH is determined by a complex equilibrium between both the weak conjugate base and weak conjugate acid of the product. Monoethanolammonium will donate the proton picked up from the lactic acid to water. Also, the absorption of a proton via the negative portion of lactic acid occurs.
  • the derivation of the equation to calculate the pH based on the acid and base used to create the salt is shown below:
  • [A ⁇ ] is equal to [BH+] at the equivalence point and assert that [HA] is equal to [B]
  • lactic acid, pK a of 3.86, and monoethanolamine, pK b of 4.56 the pH at the equivalence point should be 6.65. This is experimentally verified in FIG. 2 . Because of the spontaneity of the reaction the ratio of acid to base can be in any proportion, although near equivalence is most desired.
  • the resulting solution varies slightly in appearance depending on the reaction conditions. If the reaction is carried out slowly and the heat is allowed to dissipate the solution can be colorless, but if the reaction is done quickly and heat builds up, then the solution will turn to an amber color because of the oxidation of monoethanolamine.
  • the solution also has a slightly honey-like odor.
  • One inherent observation is an increase in the viscosity of the solution. Starting from two water thin liquids, the final solution has a viscosity of about 1500 to 3000 centipoise.
  • the most preferred embodiment contains halogenated diphenylether.
  • pcmx and/or triclosan is most desired. These two compounds, and most specifically triclosan, interact with the amine salt to produce a more efficacious hand wash.
  • Triclosan has a pK a value of 7.4, so, at the desired pH of the hand wash, the triclosan will be disassociated and have a negative charge. The positive charge on the amine is attracted to the negative charge on the triclosan and, thus, the triclosan is chelated and prevented from precipitating.
  • the antimicrobial properties of the hand wash containing an amine salt are improved compared to hand washes without. This improvement is seen both in the broad spectrum inhibition and the quick inhibition.
  • the triclosan was dissolved in dipropylene glycol, to make an “active premix.”
  • the monoethanolamine was added to the water and then the lauric acid was added. After allowing the saponification process to complete, lactic acid was added to neutralize the excess base, and was added until the solution was brought to a pH of 9.25.
  • the active premix was then added to the solution to create the antimicrobial hand wash.
  • the ingredient amounts were as follows:
  • Control 1 Control 2: Water q.s. to 100 g q.s. to 100 g q.s. to 100 g Lauric Acid 5 g 5 g 5 g Monoethanolamine 3.833 g 1.7 g 3.833 g Lactic Acid q.s. to pH 9.25 N/A N/A Dipropylene Glycol 3 g 3 g 3 g Triclosan 0.3 g 0.3 g 0.3 g pH: 9.22 pH: 9.21 pH: 10.30 A log reduction test was performed for each formulation. The samples were tested by placing a loopful (approx 10 microliters) of the formulation into a microbial broth ( Staph. Aureus ATCC#6538) for 15 seconds. A sample was then taken from the broth and plated. The bacteria was grown and then counted resulting in a quantitative reduction value, as shown below.
  • microbial broth Staph. Aureus ATCC#6538
  • Control 1 log reduction 0.6
  • Excess Base log reduction 4.0
  • Control 2 log reduction 1.3
  • the neutralized excess base improves the antimicrobial properties of the hand wash.
  • alternate acids were considered for use in neutralizing excess base present after the saponification reaction, i.e, to replace the lactic acid specifically used in Example 1.
  • the samples were made in accordance with Example 1, except that the lactic acid was replaced with alternate acids.
  • a sample was also created having excess base and no second acid addition.
  • the samples were adjusted to pH: 9.2 ⁇ 0.10 with each acid, and then tested for log reduction properties.
  • the acids tested were as follows:
  • the monoethanolamine was dissolved in the water, and the lactic acid was slowly added to the solution, because, if added too quickly, the heat not dissipated from the neutralization reaction would degrade the monoethanolamine. The degradation can be seen by a color change from a clear colorless mixture to a dark amber hue.
  • a hand wash was made per Example 1 procedures, but without excess base (monoethanolamine). The solution was then split into four separate solutions so that the neutralization solution could be added in differing amounts.
  • the amount of monoethanolammonium lactate is directly proportional to the log reduction.
  • the hand wash here is a preferred hand wash containing optional ingredients that are generally appreciated for their beneficial properties in hand wash formulations.
  • the production process involves dissolving pcmx in dipropylene glycol, saponifying the lauric acid with monoethanolamine, and adding the remaining ingredients to the water.
  • the sample was then inoculated into samples containing a microorganism in duplicate. One of the two samples was neutralized at 15 seconds and the second at 30 seconds. The samples were then plated and incubated for later counting. The data are represented below.
  • the sample has broad spectrum, quick acting activity against these 17 tested organism.
US11/494,473 2006-07-26 2006-07-27 Antimicrobial hand wash Abandoned US20080026974A1 (en)

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US11/494,473 US20080026974A1 (en) 2006-07-27 2006-07-27 Antimicrobial hand wash
AT07252834T ATE486568T1 (de) 2006-07-27 2007-07-17 Antimikrobielle handwaschpaste
DE602007010213T DE602007010213D1 (de) 2006-07-27 2007-07-17 Antimikrobielle Handwaschpaste
PT07252834T PT1886660E (pt) 2006-07-27 2007-07-17 Lavagem de mãos antimicrobiana
DK07252834.2T DK1886660T3 (da) 2006-07-27 2007-07-17 Antimicrobielt håndvaskemiddel
EP07252834A EP1886660B1 (en) 2006-07-27 2007-07-17 Antimicrobial hand wash
AU2007203322A AU2007203322B2 (en) 2006-07-26 2007-07-17 Antimicrobial hand wash
ES07252834T ES2352158T3 (es) 2006-07-27 2007-07-17 Limpiador de manos antimicrobiano.
CA2594270A CA2594270C (en) 2006-07-27 2007-07-23 Antimicrobial hand wash
BRPI0703313-3A BRPI0703313A (pt) 2006-07-27 2007-07-26 produto antimicrobiano para lavar as mãos, e, processo para a produção do mesmo
JP2007195824A JP2008056912A (ja) 2006-07-27 2007-07-27 抗菌性ハンドウォッシュ
US12/434,355 US7851424B2 (en) 2006-07-27 2009-05-01 Antimicrobial hand wash
US13/095,284 US8372790B2 (en) 2006-07-27 2011-04-27 Antimicrobial hand wash

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US20110081431A1 (en) * 2009-10-02 2011-04-07 Simarna Kaur COMPOSITIONS COMPRISING AN NFkB-INHIBITOR AND A NON-RETINOID COLLAGEN PROMOTER
US20110081430A1 (en) * 2009-10-02 2011-04-07 Simarna Kaur COMPOSITIONS COMPRISING AN NFkB-INHIBITOR AND A TROPOELASTIN PROMOTER
US20110223114A1 (en) * 2008-10-20 2011-09-15 Amit Chakrabortty Antimicrobial composition
US20120128605A1 (en) * 2009-10-02 2012-05-24 Steven Cochran Compositions comprising a skin-lightening resorcinol and a skin darkening agent
US9132103B2 (en) 2009-09-24 2015-09-15 Conopco, Inc. Disinfecting agent comprising eugenol, terpineol and thymol
US9370474B2 (en) 2009-10-02 2016-06-21 Johnson & Johnson Consumer Inc. High-clarity aqueous concentrates of 4-hexylresorcinol
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CN109825386A (zh) * 2019-01-29 2019-05-31 丰益油脂科技（东莞）有限公司 一种含有有机葡萄糖酸钠的皂粒及环保皂
US10307352B2 (en) 2012-09-24 2019-06-04 Johnson & Johnson Consumer Inc. Low oil compositions comprising a 4-substituted resorcinol and a high carbon chain ester
US10716305B2 (en) 2015-01-23 2020-07-21 Biocidium Biopharmaceuticals Inc. Anti-bacterial compositions
US11065220B2 (en) 2017-02-13 2021-07-20 Wintermute Biomedical, Inc. Anti-pathogenic therapeutic compositions
US11103475B2 (en) 2018-10-01 2021-08-31 Wintermute Biomedical, Inc. Therapeutic compositions of undecylenic acid and arginine
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US10499636B2 (en) 2008-07-24 2019-12-10 Ecolab Usa Inc. Foaming alcohol compositions with selected dimethicone surfactants
US9414586B2 (en) 2008-07-24 2016-08-16 Ecolab Usa Inc. Foaming alcohol compositions with selected dimethicone surfactants
US9980483B2 (en) 2008-07-24 2018-05-29 Ecolab Usa Inc. Foaming alcohol compositions with selected dimethicone surfactants
US8945596B2 (en) 2008-10-20 2015-02-03 Conopco, Inc. Antimicrobial composition
US20110223114A1 (en) * 2008-10-20 2011-09-15 Amit Chakrabortty Antimicrobial composition
US9132103B2 (en) 2009-09-24 2015-09-15 Conopco, Inc. Disinfecting agent comprising eugenol, terpineol and thymol
US20120128605A1 (en) * 2009-10-02 2012-05-24 Steven Cochran Compositions comprising a skin-lightening resorcinol and a skin darkening agent
US9370474B2 (en) 2009-10-02 2016-06-21 Johnson & Johnson Consumer Inc. High-clarity aqueous concentrates of 4-hexylresorcinol
US8318217B2 (en) 2009-10-02 2012-11-27 Johnson & Johnson Consumer Companies, Inc. Compositions comprising an anti-inflammatory blend
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US9693941B2 (en) 2011-11-03 2017-07-04 Conopco, Inc. Liquid personal wash composition
US10307352B2 (en) 2012-09-24 2019-06-04 Johnson & Johnson Consumer Inc. Low oil compositions comprising a 4-substituted resorcinol and a high carbon chain ester
US10716305B2 (en) 2015-01-23 2020-07-21 Biocidium Biopharmaceuticals Inc. Anti-bacterial compositions
US11363814B2 (en) 2015-01-23 2022-06-21 Biocidium Ip Holdco, Co. Anti-bacterial compositions
US11065220B2 (en) 2017-02-13 2021-07-20 Wintermute Biomedical, Inc. Anti-pathogenic therapeutic compositions
US11406849B2 (en) 2017-04-10 2022-08-09 Kao Corporation Amino alcohol-containing skin cleansing composition for removing keratotic plugs from skin
US11633335B2 (en) 2017-04-10 2023-04-25 Kao Corporation Skin cleansing composition
CN108048242A (zh) * 2017-11-30 2018-05-18 广东嘉丹婷日用品有限公司 一种高效抗菌洗衣液及其制备方法
US11103475B2 (en) 2018-10-01 2021-08-31 Wintermute Biomedical, Inc. Therapeutic compositions of undecylenic acid and arginine
US11154524B2 (en) * 2018-10-01 2021-10-26 Wintermute Biomedical, Inc. Therapeutic compositions of decanoic acid and arginine
CN109825386A (zh) * 2019-01-29 2019-05-31 丰益油脂科技（东莞）有限公司 一种含有有机葡萄糖酸钠的皂粒及环保皂

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US7851424B2 (en) 2010-12-14
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CA2594270A1 (en) 2008-01-27
AU2007203322A1 (en) 2008-02-14
PT1886660E (pt) 2011-02-10
EP1886660B1 (en) 2010-11-03
ATE486568T1 (de) 2010-11-15
DE602007010213D1 (de) 2010-12-16
AU2007203322B2 (en) 2011-10-13
US8372790B2 (en) 2013-02-12
CA2594270C (en) 2015-03-10
US20110263471A1 (en) 2011-10-27
ES2352158T3 (es) 2011-02-16
JP2008056912A (ja) 2008-03-13
BRPI0703313A (pt) 2008-03-11
DK1886660T3 (da) 2011-01-31

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