AU715706B2 - Antiseptic composition containing a quaternary ammonium compound a chelating agent and a polyol - Google Patents
Antiseptic composition containing a quaternary ammonium compound a chelating agent and a polyol Download PDFInfo
- Publication number
- AU715706B2 AU715706B2 AU11033/97A AU1103397A AU715706B2 AU 715706 B2 AU715706 B2 AU 715706B2 AU 11033/97 A AU11033/97 A AU 11033/97A AU 1103397 A AU1103397 A AU 1103397A AU 715706 B2 AU715706 B2 AU 715706B2
- Authority
- AU
- Australia
- Prior art keywords
- topical
- ready
- aqueous
- antiseptic composition
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- 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
Description
WO 97/24927 PCT/GB96/03037 -1- ANTISEPTIC COMPOSITION CONTAINING A QUATERNARY AMMONIUM COMPOUND A CHELATING AGENT AND A POLYOL The invention relates to antiseptic compositions, and in particular to ready to use antiseptic compositions.
Many compounds suitable for killing or inhibiting the growth of microorganisms are known. Compositions containing such compounds and suitable for application to the human, or animal, body are generally referred to as antiseptics.
Traditionally, antiseptic compositions have been produced, and provided to the public, in concentrated form to be diluted at the time of use. This has a number of drawbacks, including the unavailability of water when antisepsis is required, unclean or contaminated water used for dilution, or inaccurate dilution by the user.
To overcome the above problems the trend has been to produce dilute (or ready to use) antiseptics.
Many of the recent ready-to-use antiseptics are fairly complex, comprising mixtures of antimicrobial compounds, surfactants, solvents etc. However, many of these extra ingredients may be irritating to the skin (eg. alcohols or surfactants) or may interfere WO 97/24927 PCT/GB96/03037 -2with the antiseptic activity of the active agents (eg surfactants).
We have now found that an effective ready to use antiseptic composition may be produced by the combination of a relatively small number of ingredients.
According to the invention, there is therefore provided an aqueous, topical, ready to use, antiseptic composition comprising a) 0.05 to 1% w/v of a biocidal compound of formula I 15 (RI)3 R2 1 6- e (CH2)n-N-R4
X
R3 wherein each R 1 is independently selected from hydrogen, a Ci-, alkyl group, a C.
4 alkoxy group, a halogen or a hydroxy group; n is 0 to 3;
R
2 and R 3 are independently selected from C, 4 alkyl groups;
R
4 is a C6-22 alkyl chain (or a mixture thereof), and WO 97/24927 PCT/GB96/03037 -3- X is an anion; b) 0.005 to 0.2% w/v of a chelating agent, and c) 1 to 5% w/v of a polyhydric alcohol; the composition further comprising substantially no monohydric alcohols.
The monohydric alcohols to be excluded from the compositions of the invention include ethanol and methanol.
Preferably in the compounds of formula I R 1 is hydrogen, n is 1 or 2 (most preferably R 2 and R 3 are each methyl, R 4 is an alkyl chain of C-s, length (or a mixture thereof) and X is a halogen.
Most preferably, the compound of formula I is a mixture of alkyldimethylbenzyl ammonium chlorides (commercially available as "benzalkonium chloride").
Preferably in the compositions of the invention the concentration of the compound of formula I is from 0.1 to 0.5 w/v, more preferably 0.15 to 0.3% w/v.
Preferably the chelating agents are selected from ethylenediamine tetraacetic acid (EDTA) or a derivative or a salt thereof, or ethylene glycol bis WO 97/24927 PCT/GB96/03037 -4- [P-aminoethyl ether] N'-tetraacetic acid (EGTA) or a derivative or salt thereof.
More preferably the chelating agent is EDTA or a sodium or potassium salt thereof, or EGTA or a sodium or potassium salt thereof; most preferably it is a sodium salt of EDTA.
Preferably in the compositions of the invention the concentration of the chelating agent is from 0.005 to 0.1% w/v, more preferably 0.01 to 0.05% w/v (expressed as the free acid where appropriate) Preferably the polyhydric alcohol is selected from polyethylene glycols of average molecular weight 200 to 1000 (particularly 200 to 600), propylene glycol, ethylene glycol or mixtures thereof. Most preferably the polyhydric alcohol is propylene glycol.
Preferably the amount of polyhydric alcohol in a composition of the invention is from 2 to 4% w/v, more preferably 2 to 3% w/v.
By topical, ready to use, antiseptic compositions it is meant that the compositions of the invention are suitable (and are intended) to be used directly on the skin of humans or animals without further dilution.
WO 97/24927 PCT/GB96/03037 Therefore preferably the compositions of the invention are substantially free of any compound which may cause irritation to the skin.
Preferably the compositions of the invention contain substantially no biocidal phenolic compounds (other than compounds of formula I, where appropriate). More preferably the compositions of the invention are substantially free of any biocidal compounds other than compounds of formula I. For the avoidance of doubt, we do not consider EDTA or EGTA (or salts thereof) to be biocidal compounds.
The compositions of the invention may further contain conventional ingredients of antiseptic compositions, as appropriate. However, it is preferred that the compositions of the invention contain substantially no nonionic surfactants and most preferably they contain substantially no surfactants at all (other than quaternary ammonium biocides of Formula I) A preferred extra component in the compositions of the invention is a topical anaesthetic. Most preferably the topical anaesthetic is lignocaine or the hydrochloride salt thereof.
When present, the lignocaine will be present at an amount of from 1 to 5% w/v, more preferably from 2 to 3.5% w/v.
WO 97/24927 PCT/GB96/03037 -6- Further according to the invention there is provided an aqueous, topical, ready to use, antiseptic composition comprising a) 0.1 to 0.5 w/v benzalkonium chloride; b) 0.005 to 0.1% w/w EDTA, or a sodium salt thereof; c) 1 to 5% w/v propylene glycol; and d) 0 to 5% w/v (preferably 1 to 5% w/v, more preferably 2 to 3.5% w/v) lignocaine hydrochloride; the composition further containing substantially no biocidal phenolic compounds (and preferably no further biocides); and substantially no monohydric alcohols.
Further conventional components include buffering and pH control agents (for example sodium acid phosphate and sodium phosphate), perfumes and colouring agents.
The balance of the compositions of the invention will be water. Preferably the water is softened, distilled or deionised water, most preferably it is softened water.
The compositions of the invention may be produced by any conventional manufacturing process; for example by simply mixing all of the ingredients at room temperature, or whilst heating the mixture, until a solution is formed. The compositions may be produced directly in dilute form or as concentrates to be diluted before packaging.
The compositions of the invention may be packaged in any conventional form. Examples include in sprayable form such as aerosols (also comprising a propellant) or so called pump packs; dispersed onto cloths as antiseptic wipes; in ampoules as single use packs or in conventional (multiple dose) bottles.
The advantages of the compositions of the invention are that they are in a ready to use form, are simple S: to produce, none irritant and have effective antiseptic properties on the skin.
Throughout this specification the word "comprise", or variations such as "comprises" or "comprising", will be understood to imply the inclusion of a stated element, integer or step, or group of elements, integers or steps, but not the exclusion of any other element, integer or step, or group of elements, integers or steps.
0
A
WO 97/24927 PCT/GB96/03037 -8- The invention will now be illustrated by the following examples.
Example 1 A composition was made up at 25 0 C by mixing the following components together w/v Benzalkonium chloride 50% Disodium EDTA Propylene glycol Sodium acid phosphate Sodium phosphate Perfume Softened Water 0.395 0.015 2.080 0.718 0.143 0.050 (ml) to 100 ml A composition was made up at 25 0 C by mixing the following components together Benzalkonium chloride 50% Disodium EDTA Propylene glycol Lignocaine HC1 Sodium acid phosphate Sodium phosphate Perfume Softened water w/v 0.395 0.015 2.080 2.200 0.718 0.143 0.050 (ml) to 100 ml WO 97/24927 PCT/GB96/03037 -9- The compositions of Examples 1 and 2 can be applied to the skin "neat" and have good antiseptic properties.
Exam P1 3 A composition was made up at 25 0 C by mixing the following components together.
%w/v Cetrimide (available as Cetavlon from ICI) Tetrasodium EDTA Polyethylene glycol 400 Sodium acid phosphate Sodium phosphate Perfume Softened water 0.15 0.02 0.718 0.143 0.05 (ml) to 100 ml Example 4 The microbiological activity of the composition of Example 2 was tested using the Proposed Suspension Test for the Evaluation of Antimicrobial Efficacy of Antiseptic and Disinfectant products for Medical Usage (WG1 phase 2 step 1) of the Committee for European Normalisation TC 216 (1995).
Activity after a 5 minute contact time against Staphylococcus aureus ATCC 6538, Methicillin Resistant WO 97/24927 PCT/GB96/03037 S. aureus (MRSA), Enterococcus hirae ATCC 10541, Escherichia coli ATCC 10536, Citrobacter freundii ATCC 8090, Klebsiella pneumoniae ATCC 13883, Proteus mirabilis ATCC 14153 and Pseudomonas aeruginosa ATCC 15442 was assessed in the presence of 1% combined albumin/yeast extract (CAY). Under the test conditions the maximum concentration of product that can be tested is 80% v/v.
The composition of Example 2 achieved excellent activity, log reductions in excess of 5, against all the challenge organisms, see Table 1.
WO 97/24927 WO 9724927PCT/GB96/03037 -11- TABLE 1: Antibacterial Activity in the presence of 1organic soil ME value (after 5 minute contact time) on Organismthree consecutive days: Staphylococcus aureus ATCC 6538 5.7 Methicillin Resistant >3.3 Staphylococcus aureus >6.3 clinical isolate >6.3 Enterococcus hirae >6.4 ATCC 10541 >6.6 Escherichia coli ATCC 10536 >6.8 >6.3 Citrobacterfreundii ATCC 8090 >6.8 >6.1 Kiebsiella pneumoniae >6.8 ATCC 13883 >6.8 >6.3 Proteus mirabilis ATCC 14153 4.8 Pseudomonas aeruginosa >5.9 ATCC 15442 >6.2 >6.2 WO 97/24927 PCT/GB96/03037 -12- Example The lack of irritancy of the composition of Example 2 was tested by the following procedure.
Twenty-six human volunteers of either sex aged between 18 and 65 took part in the trial. The composition of Example 2 was applied to the skin undiluted. Deionised water and a blank untreated site were included as controls. Each sample was applied to the upper outer arm via an occlusive aluminium Finn chamber which provided a test area of 50 mm 2 and a volume of 25 1. Patches were applied for an initial period of 6 hours, then removed and assessed using a numerical scoring system.
After assessment an identical fresh patch was applied to the same site for a further 17 hours and test sites were examined for irritation 1 hour later.
A third identical fresh patch was applied to the same skin site for a further 23 hours and test sites were examined 1 hour later. Twenty-four out of 26 subjects completed the study. No adverse events were observed.
Claims (16)
1. An aqueous topical, ready to use, antiseptic composition suitable for application to the skin comprising a) 0.05 to 1% w/v of a biocidal compound of formula I (R )3 R1 2 (CH 2 )n-N-R X R 3 wherein each R 1 is independently selected from hydrogen, a CI 4 alkyl group, a C 1 4 alkoxy group, a halogen or a hydroxy group; n is 0 to 3; R 2 and R 3 are independently selected from C 1 4 alkyl groups; R 4 is a C 6 -C 22 alkyl chain or a mixture thereof; and X is an anion; b) 0.005 to 0.2% w/v of a chelating agent, and c) 1 to 5% w/v of a polyhydric alcohol, selected from polyethylene 20 glycols of average molecular weight 200 to 1000, propylene glycol, ethylene glycol or mixtures thereof, the composition further comprising substantially no monohydric alcohols.
2. An aqueous, topical, ready to use antiseptic composition as claimed in Claim 1 wherein the polyethylene glycols have an average molecular weight 25 of 200 to 600.
3. An aqueous, topical, ready to use, antiseptic composition as claimed in Claim 1 or 2 wherein in the compounds of formula I R 1 is hydrogen, n is 1 or 2, R 2 and R 3 are each methyl, R 4 is an alkyl chain of C 8 length or a mixture thereof and X is a halogen.
4. An aqueous, topical, ready to use, antiseptic composition as claimed in Claim 3 wherein n is 1. An aqueous, topical, ready to use, antiseptic composition as claimed in any one of Claims 2 to 4 wherein the compound of formula I is a mixture of alkyldimethylbenzyl ammonium chlorides.
6. An aqueous, topical, ready to use, antiseptic composition as claimed in any one of the preceding claims wherein the concentration of the compound of formula I is from 0.1 to 0.5% w/v.
7. An aqueous, topical, ready to use, antiseptic composition as claimed in any one of the preceding claims wherein the chelating agent is selected from ethylenediamine tetraacetic acid (EDTA) or a derivative or a salt thereof, or ethylene glycol bis [P-aminoethyl ether] N'-tetraacetic acid (EGTA) or a derivative or salt thereof.
8. An aqueous, topical, ready to use, antiseptic composition as claimed in Claim 7 wherein the chelating agent is EDTA or a sodium or potassium salt thereof, or EGTA or a sodium or potassium salt thereof.
9. An aqueous, topical, ready to use antiseptic composition as claimed in any one of the preceding claims wherein the concentration of chelating agent is from 0.005 to 0.1% w/v (expressed as the free acid where appropriate).
10. An aqueous, topical, ready to use, antiseptic composition as claimed in any one of the preceding claims wherein the concentration of polyhydric alcohol is from 2 to 4% w/v.
11. An aqueous, topical, ready to use, antiseptic composition as claimed in Claim 10 wherein the concentration of polyhydric alcohol is from 2 to 3% w/v.
12. An aqueous, topical, ready to use, antiseptic composition as claimed in any one of the preceding claims containing substantially no nonionic surfactants.
13. An aqueous, topical, ready to use, antiseptic composition as claimed in 25 Claim 12 containing substantially no surfactants other than quaternary ammonium biocides of Formula I.
14. An aqueous, topical, ready to use, antiseptic composition as claimed in any one of the preceding claims further comprising a topical anaesthetic. An aqueous, topical, ready to use antiseptic composition as claimed in Claim 14 wherein the topical anaesthetic is lignocaine or the hydrochloride salt thereof.
16. An aqueous, topical, ready to use, antiseptic composition as claimed in Claim 15 wherein the concentration of lignocaine is from 1 to 5% w/v.
17. An aqueous, topical, ready to use, antiseptic composition according to Claim 1 comprising a) 0.1 to 0.5% w/v benzalkonium chloride; \vp j/"j b) 0.005 to 0.1% w/w EDTA, or a sodium salt thereof; c) 1 to 5% w/v propylene glycol; and d) 1 to 5% w/v lignocaine hydrochloride the composition further containing substantially no biocidal phenolic compounds; and substantially no monohydric alcohols.
18. An aqueous, topical, ready to use, antiseptic composition as hereinbefore described with reference to any one of Examples 1-3. Dated this secod day of December 1999 RECKITT COLMAN PRODUCTS LTD Patent Attorneys for the Applicant: F B RICE CO 9 S* a a S a S. Sa a S 'Z ii L~l- 'i~Qij
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9600140 | 1996-01-05 | ||
GBGB9600140.9A GB9600140D0 (en) | 1996-01-05 | 1996-01-05 | Improvements in or relating to organic compositions |
PCT/GB1996/003037 WO1997024927A1 (en) | 1996-01-05 | 1996-12-11 | Antiseptic composition containing a quaternary ammonium compound a chelating agent and a polyol |
Publications (2)
Publication Number | Publication Date |
---|---|
AU1103397A AU1103397A (en) | 1997-08-01 |
AU715706B2 true AU715706B2 (en) | 2000-02-10 |
Family
ID=10786607
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU11033/97A Expired AU715706B2 (en) | 1996-01-05 | 1996-12-11 | Antiseptic composition containing a quaternary ammonium compound a chelating agent and a polyol |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP0877553A1 (en) |
CN (1) | CN1120662C (en) |
AU (1) | AU715706B2 (en) |
GB (2) | GB9600140D0 (en) |
NZ (1) | NZ323980A (en) |
WO (1) | WO1997024927A1 (en) |
ZA (1) | ZA9610838B (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IL126933A0 (en) * | 1997-12-08 | 1999-09-22 | Bernardo Birnbaum Kisilevich | A disinfectant composition |
ES2179763B1 (en) * | 2001-02-21 | 2004-05-01 | Luis Buil Torres | NEW DISINFECTANT AND CONSERVANT FORMULATION, PROCEDURE FOR PREPARATION AND APPLICATIONS. |
WO2004019682A1 (en) * | 2002-08-28 | 2004-03-11 | Luis Buil Torres | Pharmaceutical composition for the treatment of viral, fungal and bacterial infections and applications of same |
JP5225651B2 (en) | 2007-10-26 | 2013-07-03 | 花王株式会社 | Anti-fungal composition |
MX361642B (en) * | 2013-09-13 | 2018-12-13 | 3M Innovative Properties Co | Cationic antiseptic compositions. |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2031889A1 (en) * | 1969-12-22 | 1971-07-15 | Schenco Ltd., Luzern (Schweiz) | Antiseptic preparation |
CH604730A5 (en) * | 1974-04-11 | 1978-09-15 | Richard H Conn | Disinfectant concentrate contg alkyl benzalkonium halides |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1161528A (en) * | 1967-05-18 | 1969-08-13 | Prebbles Medical Ltd | Improvements in or relating to Surgical Dressings |
US3639576A (en) * | 1968-06-19 | 1972-02-01 | Barnes Hind Pharm Inc | Resterilizing contact lens solution |
GB1452374A (en) * | 1974-03-26 | 1976-10-13 | Conn R H | Disinfectant compositions |
HU192885B (en) * | 1984-06-01 | 1987-07-28 | Planorg Mernoeki Iroda Gm | Disinfecting compositions and process for the preparation thereof |
US4923899A (en) * | 1987-12-22 | 1990-05-08 | Cetylite Industries, Inc. | Sterilant composition |
IT1231939B (en) * | 1989-09-08 | 1992-01-15 | Avalon Finanziaria Srl | DISINFECTANT AND RELATED METHOD OF PREPARATION. |
JPH0646968A (en) * | 1992-07-31 | 1994-02-22 | Daio Paper Corp | Wet tissue |
US5414124A (en) * | 1993-01-19 | 1995-05-09 | Huntington Laboratories, Inc. | Method of preparing quarternary ammonium formulations with high flash points |
ES2166366T3 (en) * | 1993-08-19 | 2002-04-16 | Kao Corp | COMPOSITION OF DETERGENT GERMICIDA-DISINFECTANTE. |
FR2721801B1 (en) * | 1994-07-01 | 1998-01-16 | Francais Prod Ind Cfpi | NON-IRRITATING FAST ACTING DISINFECTANT COMPOSITION |
-
1996
- 1996-01-05 GB GBGB9600140.9A patent/GB9600140D0/en active Pending
- 1996-12-10 GB GB9625759A patent/GB2308812B/en not_active Expired - Lifetime
- 1996-12-11 CN CN96180186A patent/CN1120662C/en not_active Expired - Lifetime
- 1996-12-11 NZ NZ323980A patent/NZ323980A/en unknown
- 1996-12-11 WO PCT/GB1996/003037 patent/WO1997024927A1/en not_active Application Discontinuation
- 1996-12-11 EP EP96941752A patent/EP0877553A1/en not_active Withdrawn
- 1996-12-11 AU AU11033/97A patent/AU715706B2/en not_active Expired
- 1996-12-23 ZA ZA9610838A patent/ZA9610838B/en unknown
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2031889A1 (en) * | 1969-12-22 | 1971-07-15 | Schenco Ltd., Luzern (Schweiz) | Antiseptic preparation |
US3624224A (en) * | 1969-12-22 | 1971-11-30 | Schering Corp | Novel first aid products |
CH604730A5 (en) * | 1974-04-11 | 1978-09-15 | Richard H Conn | Disinfectant concentrate contg alkyl benzalkonium halides |
Also Published As
Publication number | Publication date |
---|---|
CN1120662C (en) | 2003-09-10 |
WO1997024927A1 (en) | 1997-07-17 |
GB2308812A (en) | 1997-07-09 |
GB9600140D0 (en) | 1996-03-06 |
EP0877553A1 (en) | 1998-11-18 |
GB9625759D0 (en) | 1997-01-29 |
GB2308812B (en) | 2000-01-19 |
NZ323980A (en) | 2000-01-28 |
CN1213948A (en) | 1999-04-14 |
ZA9610838B (en) | 1997-06-27 |
AU1103397A (en) | 1997-08-01 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FGA | Letters patent sealed or granted (standard patent) | ||
HB | Alteration of name in register |
Owner name: RECKITT BENCKISER HEALTHCARE (UK) LIMITED Free format text: FORMER NAME WAS: RECKITT AND COLMAN PRODUCTS LIMITED |