CA1056252A

CA1056252A - Aqueous germicidal soap

Info

Publication number: CA1056252A
Application number: CA232,754A
Authority: CA
Inventors: Charles B. Talley
Original assignee: Pennwalt Corp
Current assignee: Arkema Inc
Priority date: 1974-08-02
Filing date: 1975-08-01
Publication date: 1979-06-12
Also published as: BR7504928A; DE2534481A1; SE7508563L; LU73129A1; IE41400B1; IE41400L; NL7509121A; FR2280394A1; GB1458166A; FI752200A; IL47655A0; AU8292975A; IL47655A; ES439885A1; IT1041040B; FR2280394B1; JPS5137904A

Abstract

Abstract of the Disclosure An aqueous, antiseptic composition, the active ingredients of which are (a) p-halo-m-xylenol (PHMX) as an antimicrobial agent and (b) a water-soluble soap formed by at least partial saponification of a diacid from the class consisting of (i) a dicarboxylic acid of the formula

Description

D;i United States 1,953,413 discloses an antiseptic preparation containing p-chloro-sym.-m-xylenol incorporated in an aqueous vehicle, employing a soap as a dispersing agent, such as the soluble alkali metal soaps of fatty acids of corn oil, linseed oil, olive oil, castor oil, or other vegetable or animal fatty oils. It is further taught in the sales brochure of the Ottawa Chemical Co., Toledo, Ohio, that alcoholic solutions of p-chloro-m-xylenol (sold under the trademark "Ottasept" as an antimicrobial additive) are soluble in liquid soaps such as the potassium and triethanolamine salts of oleic, ricinoleic, myristic, and coconut fatty acids. United States 3,326,808 concerns a liquid antiseptic detergent composition containing at least one disinfectant ; agent selected from the group consisting of hexachlorophene, fluorophene, p-chloro-m-xylenol, bithionol, biphenamine hydrochloride, and a synergistic mixture consisting essentially of 20% of 5,4~-dibromosalicylanilide and 80% of 3,5,4'-tribromosalicylanilide, a water-soluble, non-irritating and non-sensitizing surface-active, organic synthetic anionic detergent; a super fatting emollient selected from the group consisting of animal, vegetable and mineral oils and synthetic fatty acid ester oils, and a polyethylene glycol ether of a higher fatty alcohol. (It is noted that the most widely used germicidal liquid hand soaps heretofore have contained hexachlorophene or iodine; however, hexachloro-phene is now out of favor because of recent disclosures relating to possible toxicity, and iodine is undesirable because of its staining properties.) Other ~: aqueous soap-containing detergent compositions containing chloro-xylenols are taught in United States 2,191,405, 2,906,664 and 3,370,014. United States 3,538,009 concerns an aqueous detergent composition, which may contain a bacteriostatic agent, and which contains a mildness additive comprising the polymerized p~oduct of 2 to 4 molecules of a monomeric C12 to C26 fatty acid, preferably the dimer acid derived from linoleic acid, said dimer acid derived from linoleic acid, said dimer acid having the structure

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(CH2) 4-CH3 . It has been discovered that soaps of such acids, as well as soaps of many : other common fatty acids derived from naturally occurring vegetable and animal ` fats, such as ricinoleic and coconut fatty acids, do not operate to give suitable bactericidal and germicidal compositions in combination with P~X, compared to the soaps of the dicarboxylic acids embodied in this invention.
Summary of the Invention The present invention provides a novel and useful aqueous . antiseptic composition comprising (a) at least about 2~ by weight of p-halo-m-~: xylenol as an antimicrobial agent and (b) at least about 5% by weight of a .~ water soluble mono- or di-soap formed by at least partial saponification of a diacid from the class consisting of ti) a dicarboxylic acid of the formula C~ = C O

CH - CH
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wherein x and y are integers from 3 to 9 and x and y together equal 12 and wherein X and X~ are different members of the class consisting of hydrogen and a carboxylic acid group and (ii) the mono or di, 3-chloro-2-hydroxy propane sulfonate ester of the dicarboxylic acid of (i). The soaps may be of the

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`: ~ ' .' ' partially or completely saponified diacid and may be of the sodium, potassium, lithium, ammonium or organic amine variety. In the preferred structure x is 5, - y is 7, X is carboxylic acid and X' is hydrogen. The diacid from which the preferred soap is made is sold by Westvaco Corp. under the mark "Westvaco DiAcid 1550", with the suggestion that the potassium and sodium soaps show remarkable water solubility and that liquid soaps up to 80% solids (K soap) or 65% solids (Na soap) can be prepared. It is the reaction product of the linoleic acid portion of a fatty acid mixture with acrylic acid as taught in United States 3,753,968. Preparation of the mono- and bis-hydroxy propane sulfonates is taught in United States 3,842,119. Soap compositions made from the acid and certain salts are disclosed in United States 3,734,859.
Detailed Descrlption of the Invention The aqueous antiseptic soap of this invention comprises, as essential ingredients, from about 5 to about 50% by weight based on the weight of the total composition (preferably from 8 to 18%) of the sodium, potassium, lithium, ammonium or organic amine soap of the above-described dicarboxylic acid or the halo-substituted propane sulfonate ester thereof, from about 2 to 10% by weight (preferably from 2 to 5%) of P~MX as an antimicrobial agent and from about 30 to about 90% by weight (preferably from 60 to 80%) of water.
The potassium and amine soaps wherein the diacid is saponified to from about 50% to 75% are preferred since such compositions are less basic and more soluble than soaps containing other cations; the trithanolamine soaps are of particular value because they are less irritating to the skin.
i The composition of the present invention is prepared by dissolving in water appropriate amounts of (i) PHMX as an antimicrobial and ~ii) the soap described above to provide ingredient concentrations within the expressed ranges. At the lower concentrations of antiseptic (i.e. below about 2% by . -, ` , ' ':

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weight) the composition is less bactericidal (i.e. at times only partial kills are experienced) while compositions containing more than 2% (preferably at least 3.75%) by weight of the antimicrobial are completely bactericidal (i.e.
100% kill). Although the defined antimicrobial is only sparsely soluble in water its water solubility is enhanced by the presence of the partially or fullysaponified soap. In addition it has been found that the presence of minor amounts (i.e. 1-5%) of an alcohol or glycol supplementary solubilizer will aid the solubility of the PHMX and improve the stability of the final composition during storage.
During the mixing operation it has been found essential to add . the ingredients to the water. Reversal of the recommended order of addition, i.e. adding the water last, has been observed to result in compositions ineffective as bactericides presumably due to micellization that masks the antimicrobial. The preferable order of addition of ingredients is to first combine the antimicrobial and solubilizer (where used) and add this mixture ~ to the required water containing (i) part of the alkali (intended to saponify - the diacid) and (ii) the chelating agent where appropriate. Thereafter the remainder of the alkali to form the soap is added, followed by optional ingredients such as surface active agents, emollients, perfumes and the like.
A final pH adjustment is made by addition of more alkali or diacid to provide a pH of about 6 to about 10.
Solubilization of the PHMX
. _ _ _ . . _ As noted, the presence of the diacid soap identified above enhances the solubility of PHMX in water. Thus the amount of PHMX that may be solubilized in any given formulation of the present invention will depend upon the concentration of the diacid soap; it will also depend upon the nature and concentration of any supplementary solubilizer that may be present. Finally it has been observed that the effectiveness of the final composition as a bactericide is generally directly proportional to the solubility of the PHMX in water.

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: ' The Drawing The drawing is a plot defining solubility limits and bactericidal effectiveness of related concentrations of p-chloro-m-xylenol (PCMX) and Westvaco : .
Diacid 1550. In the drawing, percentage of Diacid is plotted as abscissa against the percentage of p-chloro-m-xylenol (PCMX) as ordinate using compo-sitions that otherwise contain the ingredients of the soap of Example 1. The Example uses isopropyl alcohol at a 5% by weight level as a supplementary solubilizer. Curve "A" represents the solubility limit of the PCMX in the system; above curve A, the PCMX component crystallizes out. Curve C represents 10 the dividing line between complete bactericidal versus partial bactericidal activity, i.e. concentrations within the area between curves A and C represent concentrations that are 100% bactericidal in nature whereas those below C are generally less than 100% bactericidal. Concentrations of diacid soap and PCMX
between curves C and B represent preferred concentrations not only because of high bactericidal activity but also because of the high shelf-life of the resulting compositions.
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It will be obvious to those skilled in the art that the curves will depend upon the identity of the critical components and the supplementary solubilizer. However from this teaching those skilled in the art can readily ~ 20 determine the most effective proportion of ingredients for any combination.
; Supplementary Solubilizers The use of small amounts of alcohols and glycols as supplementary solubilizers for PHMX has been discussed above. While up to 20% by weight of supplementary solubilizer will be found effective in making compositions of the present invention, usually the minimum amount will be employed not only because of safety (flash-point) and cost considerations but because such substances tend to defat the skin, causing dryness. Thus the use of from 1 to 5% by weight of supplementary solubilizer is preferred. Among suitable supplementary solubilizers are alcohols, glycols and sulfonated fatty acids such as ,~ ~
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~i hexylene glycol, ethylene glycol, sulfonated oleic acid and the like.
In addition to increasing the solubility of the PHMX in water, the presence of the solubilizer appears to enhance the antimicrobial properties of the PHMX so that a concentration of PCMX as low as about 2% by weight has t been found effective to provide bactericidal protection (equivalent to the action ; of 50 ppm available chlorine) whereas in the absence of the solubilizer about 3.75% by weight of antimicrobial is required to reach such a level of effective-ness.
Optional~In~_edients o There are a number of ingredients which may be optionally in-cluded in the germicidal soap of this invention, some of which enhance per-formance and others of which are cosmetic in nature. Suitable ingredients for use as skin conditioning agents, surface-active agents, organic chelating agents, perfumes and thickening agents are well known to those skilled in the art. Thus from about 1 to about 5% by weight of a polyhydric alcohol such as glycerol or sorbitol is useful as an additive to provide skin conditioning or emollient properties. As a surface-active agent the composition of present invention will usually have incorporated therein from about 0.5 to about 15% by weight (pre-ferably from 1 to 3% by weight) of an amphoteric or anionic surface-active agent, for example, alkyl imiazolinium decarboxylate sodium salt, alkyl benzene sulfonate, alkyl sulfate, alkyl benzene sulfate, alkyl sulfonate, alkyl ether sulfonate or like anionic sulfonated detergent; higher concentrations, e.g. 10% by weight, are often useful when high foam generation is desired. A particularly preferred detergent is a sodium salt of a lauryl sulfate of an alkylphenoxypoly (ethyleneoxy) ethanol made from naturally occurring lauric acid.
For some applications, the use of from about 0.05 to about 5% by weight of an organic chelating agent to enhance the biological activity by "-,. ' : . ' ' ' ' , :
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sequestering water hardness or other metal ions from the system is beneficial.
Representative chelating agents are the alkali metal salts of ethylene diamine-tetraacetic acid, the sodium salt of hydroxyethylene diamine triacetic acid, l-hydroxy-ethylidene-1, l-diphosphonic acid, nitrile triacetic acid, sodium salts of gluconates, hepta gluconates and citrates. Conventional water soluble perfumes may also be desirably added to enhance the attractiveness of the germicidal hand soap, for example, in amounts ranging from about 0 to 2% by weight.
Thickeners may be used to adjust the viscosity of the final product. Carboxymethylcellulose, carboxyethylene ether cellulose and the like are suitable and may be added in sufficient quantity to provide a wide range of products from a liquid to a thick paste.
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Supplementary antimicrobial agents can also be added to the composition. While such additions have been found useful in reducing the amount of PHMX necessary to provide antimicrobial activity, none has been observed to make the PHMX bactericidal below a concentration of PHMX of about 2% by weight.
Suitable supplementary animicrobials are "Irgasan DP-300" (manufactured by the Chemical Division of the Ciba~Geigy Corporation), "Troysan 142" (made by the Troy Chemicals Co.) and "Santophen 1" (made by the Monsanto Corp.) pH Adjustment Since the composition is intended for topical application to the skin, a pH adjustment close to neutral or slightly alkaline is recommended.
Generally this is done by addition of aqueous alkali (such as potassium hydroxide) to the final composition to provide a pH from about 6 to about 10.5. While a higher pH can be used, the increased alkalinity tends to reduce the antimicrobial activity and to increase irritability of the composition upon application to theskin.

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., Test Procedures In the Examples that follow the bactericidal efficacies of the various compositions are determined using the standard A.O.A.C. tests as set forth in Methods of Analysis, 11th Edition (1970) pg. 65, that is, the Available Chlorine Germicidal Equivalent Concentration Tests against the test organisms Staphylococcus aureus (ATCC 6538) and Salmonella Typhosa (ATCC 6539).
Examples ~ The following Examples are intended to illustrate the invention.
They are not intended to limit it in any manner.

Example 1 The following ingredients are mixed together in a mixing vessel with agitation:
Ingredients % by Weight Water 63.95 EDTA (1) * 0 10 Natrosol 250 HR (2) 0 20 Potassium Hydroxide (45% solution) 5.00 Ottasept Technical (3) 3.75 Isopropyl Alcohol 5.00 Westvaco Diacid 1550 (4) 10.00 Sodium Lauryl Sulfate (30%) (5) 10.00 - Glycerol 2.00 (1) Sodium salt of ethylenediaminetetraacetic acid (2) Hydroxyethylene ether of cellulose (3) Para-chloro-meta-xylenol

(4) 5-Carboxy-4-hexyl-2-cyclohexene-1-octanoic acid

(5) Alipal CO 433*(Ciba-Geigy) from naturally occurring lauric acid.
In mixing the above ingredients, the chelating agent (EDTA) is first added to the water followed by the alkali. Sufficient alkali is used to form slightly in excess of that required to form the half soap. Thereafter the bactericide (p-chloro-m-xylenol) is stirred in followed by the solubilizer (isopropyl alcohol) and the diacid (Westvaco Diacid) to form a stable complex.

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The composition is tested on Salmonella typhosa (ATCC No. 6539) using Letheen Broth. Sodium hypochlorite is used as a control. The results :'t where "+" indicates growth and "-" indicates absence of growth~ are given below:
. ., ~ Example 1 ~.
- Subculture Series Germicide 1 2 3 4 5 6 7 8 9 10 . ,:
; Sample A - - +
Sample B
Control Conc. ppm Subculture Series (NaOCl) Avail. C1 ~, --- -- -- 1 2 3 4 5 6 7 8 9 10 .; ~ _ _ _ _ _ _ _ _ _ _ 200 - - ~ ~ ~ + + + + +
t- 100 _ _ + + + + + + + +
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; Comparative Control Culture Resistance to Phenol Dilution Intervals in Minutes 5 min. 10 15 min.
1:80 +
~, 1:90 + +
1 :100 + + +
From the above it will be noted that the composition of Example 1 is more effective as a bactericide against Salmonella typhosa than chlorine at a concentration of 200 ppm where the culture resistance to phenol is 1:80.
: The composition of this Example 1 is further tested on Staphylo-coccus aureus (ATCC No. 6538) with the following results Example 1 Subculture Series ;
Germicide 1 2 3 4 5 6 7 8 9 10 . Sample C - - - - - - +
: Sample D - - - +
Sample E - - - - + - - +
Sample F

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Control Concn. ppm Subculture Series NaCCl ~vail. C1 l 2 3 4 5 6 7 8 9 10 . 200 ~ ~ ~ ~ ~ + + + + +
, 100 -- -- -- + + + + + + +
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. -_ Comparative Control ; Culture Resistance to Phenol Intervals in ~inutes Dilution 5 min. 10 min. 15 min.

1:60 1:70 +
1:80 +
From the above it will be noted that the composition of Example 1 is more effective as a bactericide against Staphylococcus aureus than chlorine at a concentration of 200 ppm where the culture resistance to phenol is 1:70.
` While a technical grade of the PCMX was used in this Example, a more pure, recrystallized form is available and may be used. The recrystallized form is preferred in applications where a low odor level is important.
Utility ; The composition of the present invention is useful as a surgical hand scrub, an anti-microbial soap, as a skin antiseptic or as a health care personnel hand wash. Among other locations the present composition has been recommended for use in official establishments operating under the Federal meat and poultry products inspection program. In such use, the composition is dis-pensed from adequate dispensers located a sufficient distance from the processing line to preclude accidental product contamination. The hands need not be washed prior to the use of the composition, but afterwards must be thoroughly rinsed with potable water. The composition as it is proposed for use in official establishments is free rinsing and, will not deleteriously affect . - 1 1 -: . . - . , , ;. : ..

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the meat and/or poultry being p~oce5sed.

.. In Examples 2 to 14 presented below in Table 1, various com-positions within the sCope of the invention are illustrated. Each iS effective ; as a bactericide. In each of the Examples of Table 1 except Example 11, the dicarboxylic acid is Diacid 1550; in Example 11, the dicarboxylic acid is the . bis-hydroxypropane sulfonate of Diacid 1550. The letters "N.M.I' in the Table indicates that the value was not measured. In Example 14 there are additional ingredients not listed in the Table as follows: 2.0% by weight of 2,4,4-tri-chloro-2-hydroxy-diphenyl ether (supplementary antimicrobial) and 5.0~ by .. 10 weight of propylene glycol (as supplementary solubilizer).

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~xample 15 While PCMX is the preferred microbial for use in compositions of the present invention, other para halogenated meta-xylenols have been found effective. Thus in tests using parabromo-m-xylenol as the microbial against Salmonella typhus, three out of ten bottles displayed an effective kill, equi-valent to available chlorine at a 100 ppm concentration.
In Table 2, a series of Comparative Control compositions are listed which are presented to illustrate the critical nature of the antimicrobial and dicarboxylic acid combination of the present invention. None of the compositions of Table 2 is an effective bactericide despite the close similarity of the formulations to those of Table 1. In Table 2 the various superscripts ("a" through "n") are used to identify the carboxylic acid and antimicrobial employed. These are identified as follows:
(a): ricinoleic acid (12-hydroxyoleic acid) (b): para-chloro-m-xylenol ,.,~
(c): a mixture of 75% dimer acid (C36 dibasic acid) and 22% trimer acid (C54 tribasic acid) with 3~ monobasic acid (C18 fatty acids), sold as "Empol 1022" by Emery Industries, described in United States 3,538,009.

. 20 (d): Westvaco Diacid, 1550 CH = CH

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(f): 1-(3-chloroalkyl)-3,5,7-triaza-1-azoniaadamantane ; chloride, sold as "Dowicide 100*", germicide by Dow Chemical Co.
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(g): an isomer of 1-(3-chloroalkyl)-3,5,7-triaza-1-azonia-adamantane chloride, sold as "Dowicide 200*"
germicide by Dow Chemical Co.
: (h): aqueous solution of an amine and 1,2-benziso-thiazolin-3-one, sold as "Proxel CRL*" germicide by ICI America, Ltd.
(i): sodium salt of 2-mercaptopyridine-N-oxide, sold as sodium omidine germicide by Olin Corp.
(j): tris(hydroxymethyl)nitromethane, sold as Tris Nitro* germicide by Commercial Solvents Corp.
(k): 3,5-dimethyltetrahydro-1,3,5-2H-thiadiazine-2-thione, sold as "Troysan 142*", by Troy Chemicals .,~ Co.
(m): ortho-benzyl-para-chlorophenol, sold as 75% sol-; ution~in isopropanol under the mark "Santophen l*"
' by Monsanto Corp.
(n): distilled coconut acid, a blend of 8% caprylic, 7% capric, 48% lauric, 18% myristic; 9% palmitic, 2% stearic, 8% oleic and 1% linoleic; sold as "Emery 621*" by Emery Industries.

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Claims

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. A novel and useful aqueous antiseptic composition comprising (a) from about 2 to about 10% by weight of p-halo-m-xylenol from the class consisting of p-chloro-m-xylenol and p-bromo-m-xylenol as an antimicrobial agent, (b) from about 5 to about 50% by weight of a water soluble mono- or di-soap formed by at least partial saponification of a diacid from the class consisting of (i) a dicarboxylic acid of the formula wherein x and y are integers from 3 to 9 and x and y together equal 12 and wherein X and X' are different members of the class consisting of hydrogen and a carboxylic acid group and (ii) the mono or di, 3-chloro-2-hydroxy propane sulfonate ester of the dicarboxylic acid of (i) and (c) from about 30 to about 90%
by weight water, the concentration of (a) in said composition being at least sufficient to provide a ratio of (a) to (b) char-acterized by germicidal activity and the concentration of (a) being within the solubility limit for (a) in said composition.

2. The composition of Claim 1 wherein the antimi-crobial agent is p-chloro-m-xylenol.

3. The composition of Claim 2 wherein X is carboxyl and X' is hydrogen.

4. The composition of Claim 3 wherein the cation of said soap is sodium.

5. The composition of Claim 4 wherein said soap is the partially saponified acid.

6. The composition of Claim 3 wherein the cation of said soap os alkanolamine.

7. The composition of Claim 6 wherein said soap is the partially saponified acid.

8. The composition of Claim 3 wherein the cation of said soap is potassium.

9. The composition of Claim 8 wherein said soap is the partially saponified acid.

10. The composition of Claim 1 wherein from about 1 to about 20% of an alcohol is present as a supplementary solubilizer for said p-halo-m-xylenol.

11. The composition of Claim 1 wherein the dicarboxylic acid is in the form of the 3-chloro-2-hydroxypropane sulfonate ester.

12. The composition of Claim 1 wherein the diacid is

13. A method of preparing an aqueous antiseptic com-position comprising (a) from about 2 to about 10% by weight of p-halo-m-xylenol from the class consisting of p-chloro-m-xylenol and p-bromo-m-xylenol as an antimicrobial agent, (b) from about 5 to about 50% by weight of a water soluble mono- or di-soap formed by at least partial saponification of a diacid from the class consisting of (i) a dicarboxylic acid of the formula wherein x and y are integers from 3 to 9 and x and y together equal 12 and wherein X and X' are different members of the class consisting of hydrogen and a carboxylic acid group and (ii) the mono or di, 3-chloro-2-hydroxy propane sulfonate ester of the dicarboxylic acid of (i) and (c) from about 30 to about 90%
by weight water, which method comprises the steps of admixing ingredients (a), (b) and (c) in the order of adding a mixture of ingredients (a) and (b) to ingredient (c) in such amounts that the concentration of (a) in said composition is at least sufficient to provide a ratio of (a) to (b) characterized by germicidal activity and the concentration of (a) is within the solubility limit for (a) in said composition.