WO1997024927A1 - 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
- WO1997024927A1 WO1997024927A1 PCT/GB1996/003037 GB9603037W WO9724927A1 WO 1997024927 A1 WO1997024927 A1 WO 1997024927A1 GB 9603037 W GB9603037 W GB 9603037W WO 9724927 A1 WO9724927 A1 WO 9724927A1
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- 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.)
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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
Definitions
- the invention relates to antiseptic compositions, and in particular to ready to use antiseptic compositions.
- compositions containing such compounds and suitable for application to the human, or animal, body are generally referred to as antiseptics.
- 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
- an aqueous, topical, ready to use, antiseptic composition comprising
- each R 1 is independently selected from hydrogen, a C 1-4 alkyl group, a C 1-4 alkoxy group, a halogen or a hydroxy group;
- n 0 to 3 ;
- R 2 and R 3 are independently selected from C 1-4 alkyl groups
- R 4 is a C 6-22 alkyl chain (or a mixture thereof) , and X is an anion;
- composition further comprising substantially no monohydric alcohols.
- the monohydric alcohols to be excluded from the compositions of the invention include ethanol and methanol.
- R 1 is hydrogen, n is 1 or 2 (most preferably 1) , R 2 and R 3 are each methyl, R 4 is an alkyl chain of C 8 . 1B length (or a mixture thereof) and X is a halogen.
- the compound of formula I is a mixture of alkyldimethylbenzyl ammonium chlorides (commercially available as "benzalkonium chloride”) .
- 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.
- the chelating agents are selected from ethylenediamine tetraacetic acid (EDTA) or a derivative or a salt thereof, or ethylene glycol bis [ ⁇ -aminoethyl ether] -N,N,N', N' -tetraacetic acid (EGTA) or a derivative or salt thereof.
- EDTA ethylenediamine tetraacetic acid
- EGTA ethylene glycol bis [ ⁇ -aminoethyl ether] -N,N,N', N' -tetraacetic acid
- 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.
- 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)
- 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.
- 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.
- compositions of the invention are suitable (and are intended) to be used directly on the skin of humans or animals without further dilution. Therefore preferably the compositions of the invention are substantially free of any compound which may cause irritation to the skin.
- 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.
- 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.
- the topical anaesthetic is lignocaine or the hydrochloride salt thereof.
- the lignocaine 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. Further according to the invention there is provided an aqueous, topical, ready to use, antiseptic composition comprising
- composition further containing substantially no biocidal phenolic compounds (and preferably no further biocides) ;
- buffering and pH control agents for example sodium acid phosphate and sodium phosphate
- perfumes and colouring agents for example sodium acid phosphate and sodium phosphate
- the balance of the compositions of the invention will be water.
- the water is softened, distilled or deionised water, most preferably it is softened water.
- 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.
- 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.
- compositions of the invention are in a ready to use form, are simple to produce, none irritant and have effective antiseptic properties on the skin.
- a composition was made up at 25°C by mixing the following components together
- a composition was made up at 25°C by mixing the following components together
- compositions of Examples 1 and 2 can be applied to the skin "neat” and have good antiseptic properties .
- a composition was made up at 25°C by mixing the following components together.
- Example 2 The microbiological activity of the composition of Example 2 was tested using the Proposed Suspension Test for the Evaluation of Antimicrobial Efficacy of
- Staphylococcus aureus ATCC 6538 Methicillin Resistant S . aureus (MRSA) , Enterococcus hirae ATCC 10541, Escherichia coli ATCC 10536, CitroJbacter 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.
- CAY albumin/yeast extract
- Example 2 achieved excellent activity, log reductions in excess of 5, against all the challenge organisms, see Table 1.
- Example 2 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 ⁇ l . Patches were applied for an initial period of 6 hours, then removed and assessed using a numerical scoring system.
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Cosmetics (AREA)
- Detergent Compositions (AREA)
Abstract
Aqueous, topical, ready to use, antiseptic compositions comprising: a) 0.05 to 1 % w/v of a biocidal compound of formula (I) wherein each R1 is independently selected from hydrogen, a C¿1-4? alkyl group, a C1-4 alkoxy group, a halogen or a hydroxy group; n is 0 to 3; R?2 and R3¿ are independently selected from C¿1-4? alkyl groups; R?4¿ is a C¿6-22? 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; the composition further comprising substantially no monohydric alcohols.
Description
ANTISEPTIC COMPOSITION CONTAINING A QUATERNARY AMMONIUM COMPOUND A CHELATING AGENT AND A POLYOL
5 The invention relates to antiseptic compositions, and in particular to ready to use antiseptic compositions.
Many compounds suitable for killing or inhibiting 10 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.
15 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
20 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. 25
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 30 skin (eg. alcohols or surfactants) or may interfere
with 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
wherein
each R1 is independently selected from hydrogen, a C1-4 alkyl group, a C1-4 alkoxy group, a halogen or a hydroxy group;
n is 0 to 3 ;
R2 and R3 are independently selected from C1-4 alkyl groups;
R4 is a C6-22 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;
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 R1 is hydrogen, n is 1 or 2 (most preferably 1) , R2 and R3 are each methyl, R4 is an alkyl chain of C8.1B 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
[β-aminoethyl ether] -N,N,N', 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.
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.
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 to produce, none irritant and have effective antiseptic properties on the skin.
The invention will now be illustrated by the following examples.
Example 1
A composition was made up at 25°C by mixing the following components together
% w/v
Benzalkonium chloride 50% 0.395
Disodium EDTA 0.015
Propylene glycol 2.080
Sodium acid phosphate 0.718
Sodium phosphate 0.143 Perfume 0.050 (ml)
Softened Water to 100 ml
Example 2
A composition was made up at 25°C by mixing the following components together
% w/v Benzalkonium chloride 50% 0.395 Disodium EDTA 0.015
Propylene glycol 2.080
Lignocaine HCl 2.200
Sodium acid phosphate 0.718
Sodium phosphate 0.143 Perfume 0.050 (ml]
Softened water to 100 ml
The compositions of Examples 1 and 2 can be applied to the skin "neat" and have good antiseptic properties .
Example 3
A composition was made up at 25°C by mixing the following components together.
%w/v Cetrimide (available as
Cetavlon from ICI) 0.15
Tetrasodium EDTA 0.02 Polyethylene glycol 400 2.5
Sodium acid phosphate 0.718
Sodium phosphate 0.143
Perfume 0.05 (ml)
Softened water 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
S . aureus (MRSA) , Enterococcus hirae ATCC 10541, Escherichia coli ATCC 10536, CitroJbacter 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.
TABLE 1 : Antibacterial Activity in the presence of 1% organic soil
ME value (after 5 minute contact time) on three consecutive days:
Organism
Staphylococcus aureus >6.5
ATCC 6538 >6.5
5.7
Methicillin Resistant >3.3
Staphylococcus aureus >6.3 clinical isolate >6.3
Enterococcus hirae >6.4
ATCC 10541 >6.5 >6.6
Escherichia coli >6.5
ATCC 10536 >6.8 >6.3
Citrobacter freundii 2.0
ATCC 8090 >6.8
>6.1
Klebsiella pneumoniae >6.8
ATCC 13883 >6.8 >6.3
Proteus mirabilis >6.0
ATCC 14153 4.8 >6.0
Pseudomonas aeruginosa >5.9
ATCC 15442 >6.2
>6.2
Example 5
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 mm2 and a volume of 25 μl . 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
1. An aqueous, topical, ready to use, antiseptic composition comprising
a) 0.05 to 1% w/v of a biocidal compound of formula I
wherein
each R1 is independently selected from hydrogen, a C1-4 alkyl group, a C1-4 alkoxy group, a halogen or a hydroxy group;
n is 0 to 3 ;
R2 and R3 are independently selected from C1-4 alkyl groups;
R4 is a C6-22 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;
the composition further comprising substantially no monohydric alcohols .
2. An aqueous, topical, ready to use, antiseptic composition as claimed in Claim 1 wherein in the compounds of formula I R1 is hydrogen, n is 1 or 2 (most preferably 1) , R2 and R3 are each methyl, R4 is an alkyl chain of C8_1B length (or a mixture thereof) and X is a halogen.
3. An aqueous, topical, ready to use, antiseptic composition as claimed in claim 2 wherein the compound of formula I is a mixture of alkyldimethylbenzyl ammonium chlorides .
4. An aqueous, topical, ready to use, antiseptic composition as claimed in any preceding claim wherein the concentration of the compound of formula I is from 0.1 to 0.5 % w/v.
5. An aqueous, topical, ready to use, antiseptic composition as claimed in any preceding claim wherein the chelating agent is selected from ethylenediamine tetraacetic acid (EDTA) or a derivative or a salt thereof, or ethylene glycol bis [β-aminoethyl ether] -N,N,N', N' -tetraacetic acid (EGTA) or a derivative or salt thereof.
6. An aqueous, topical, ready to use, antiseptic composition as claimed in claim 5 wherein the chelating agent is EDTA or a sodium or potassium salt thereof, or EGTA or a sodium or potassium salt thereof.
7. An aqueous, topical, ready to use, antiseptic composition as claimed in any preceding claim wherein the concentration of chelating agent is from 0.005 to 0.1% w/v (expressed as the free acid where appropriate) .
8. An aqueous, topical, ready to use, antiseptic composition as claimed in any preceding claim wherein 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.
9. An aqueous, topical, ready to use, antiseptic composition as claimed in any preceding claim wherein the concentration of polyhydric alcohol is from 2 to 4% w/v, more preferably 2 to 3% w/v.
10. An aqueous, topical, ready to use, antiseptic composition as claimed in any preceding claim containing substantially no nonionic surfactants.
11. An aqueous, topical, ready to use, antiseptic composition as claimed in claim 10 containing substantially no surfactants (other than quaternary ammonium biocides of Formula I) .
12. An aqueous, topical, ready to use, antiseptic composition as claimed in any preceding claim further comprising a topical anaesthetic.
13. An aqueous, topical, ready to use, antiseptic composition as claimed in claim 12 wherein the topical anaesthetic is lignocaine or the hydrochloride salt thereof.
14. An aqueous, topical, ready to use, antiseptic composition as claimed in claim 13 wherein the concentration of lignocaine is from 1 to 5% w/v.
15. 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) 1 to 5% w/v lignocaine hydrochloride;
the composition further containing substantially no biocidal phenolic compounds;
and substantially no monohydric alcohols.
16. An aqueous, topical, ready to use, antiseptic composition as claimed in any preceding claim substantially as described in any of Examples 1 to 3.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ323980A NZ323980A (en) | 1996-01-05 | 1996-12-11 | Antiseptic composition containing a quaternary ammonium compound, a chelating agent and a polyol |
| AU11033/97A AU715706B2 (en) | 1996-01-05 | 1996-12-11 | Antiseptic composition containing a quaternary ammonium compound a chelating agent and a polyol |
| EP96941752A EP0877553A1 (en) | 1996-01-05 | 1996-12-11 | Antiseptic composition containing a quaternary ammonium compound a chelating agent and a polyol |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB9600140.9 | 1996-01-05 | ||
| GBGB9600140.9A GB9600140D0 (en) | 1996-01-05 | 1996-01-05 | Improvements in or relating to organic compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO1997024927A1 true WO1997024927A1 (en) | 1997-07-17 |
Family
ID=10786607
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/GB1996/003037 Ceased WO1997024927A1 (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) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002065839A1 (en) * | 2001-02-21 | 2002-08-29 | Luis Buil Torres | Disinfectant and preservative formulation and applications thereof |
| 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 |
| WO2009054540A1 (en) | 2007-10-26 | 2009-04-30 | Kao Corporation | Antifungal composition |
| US11684069B2 (en) * | 2013-09-13 | 2023-06-27 | 3M Innovative Properties Company | Cationic antiseptic compositions |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL126933A0 (en) * | 1997-12-08 | 1999-09-22 | Bernardo Birnbaum Kisilevich | A disinfectant composition |
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| 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 |
| DE2031889A1 (en) * | 1969-12-22 | 1971-07-15 | Schenco Ltd., Luzern (Schweiz) | Antiseptic preparation |
| GB1292412A (en) * | 1968-06-19 | 1972-10-11 | Barnes Hind Pharm Inc | Resterilising contact lens solution |
| CH604730A5 (en) * | 1974-04-11 | 1978-09-15 | Richard H Conn | Disinfectant concentrate contg alkyl benzalkonium halides |
| DE3519557A1 (en) * | 1984-06-01 | 1985-12-05 | Interkémia Vegyipari Gazdasági Társaság, Budapest | Disinfecting preparation and the process for preparing it |
| EP0422349A1 (en) * | 1989-09-08 | 1991-04-17 | AVALON FINANZIARIA S.r.l. | Disinfectant and method of preparation thereof |
| JPH0646968A (en) * | 1992-07-31 | 1994-02-22 | Daio Paper Corp | Wet tissue |
| EP0639636A2 (en) * | 1993-08-19 | 1995-02-22 | Kao Corporation | Germicidal-disinfectant detergent composition |
| US5414124A (en) * | 1993-01-19 | 1995-05-09 | Huntington Laboratories, Inc. | Method of preparing quarternary ammonium formulations with high flash points |
| EP0689768A1 (en) * | 1994-07-01 | 1996-01-03 | C F P I | Composition and process for the rapid prophylactic and not irritating treatment of udder inflammation of milkers |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1452374A (en) * | 1974-03-26 | 1976-10-13 | Conn R H | Disinfectant compositions |
| US4923899A (en) * | 1987-12-22 | 1990-05-08 | Cetylite Industries, Inc. | Sterilant 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 WO PCT/GB1996/003037 patent/WO1997024927A1/en not_active Ceased
- 1996-12-11 AU AU11033/97A patent/AU715706B2/en not_active Expired
- 1996-12-11 NZ NZ323980A patent/NZ323980A/en unknown
- 1996-12-11 EP EP96941752A patent/EP0877553A1/en not_active Withdrawn
- 1996-12-11 CN CN96180186A patent/CN1120662C/en not_active Expired - Lifetime
- 1996-12-23 ZA ZA9610838A patent/ZA9610838B/en unknown
Patent Citations (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 |
| GB1292412A (en) * | 1968-06-19 | 1972-10-11 | Barnes Hind Pharm Inc | Resterilising contact lens solution |
| 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 |
| DE3519557A1 (en) * | 1984-06-01 | 1985-12-05 | Interkémia Vegyipari Gazdasági Társaság, Budapest | Disinfecting preparation and the process for preparing it |
| EP0422349A1 (en) * | 1989-09-08 | 1991-04-17 | AVALON FINANZIARIA S.r.l. | Disinfectant and method of preparation thereof |
| 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 |
| EP0639636A2 (en) * | 1993-08-19 | 1995-02-22 | Kao Corporation | Germicidal-disinfectant detergent composition |
| EP0689768A1 (en) * | 1994-07-01 | 1996-01-03 | C F P I | Composition and process for the rapid prophylactic and not irritating treatment of udder inflammation of milkers |
Non-Patent Citations (1)
| Title |
|---|
| DATABASE WPI Section Ch Week 9413, Derwent World Patents Index; Class D22, AN 94-103894, XP002028385 * |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2002065839A1 (en) * | 2001-02-21 | 2002-08-29 | Luis Buil Torres | Disinfectant and preservative formulation and applications thereof |
| ES2179763A1 (en) * | 2001-02-21 | 2003-01-16 | Torres Luis Buil | Disinfectant and preservative formulation and applications thereof |
| 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 |
| WO2009054540A1 (en) | 2007-10-26 | 2009-04-30 | Kao Corporation | Antifungal composition |
| EP2206430A4 (en) * | 2007-10-26 | 2012-08-22 | Kao Corp | Antifungal composition |
| US11684069B2 (en) * | 2013-09-13 | 2023-06-27 | 3M Innovative Properties Company | Cationic antiseptic compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0877553A1 (en) | 1998-11-18 |
| AU1103397A (en) | 1997-08-01 |
| ZA9610838B (en) | 1997-06-27 |
| NZ323980A (en) | 2000-01-28 |
| AU715706B2 (en) | 2000-02-10 |
| GB2308812A (en) | 1997-07-09 |
| GB2308812B (en) | 2000-01-19 |
| GB9600140D0 (en) | 1996-03-06 |
| GB9625759D0 (en) | 1997-01-29 |
| CN1120662C (en) | 2003-09-10 |
| CN1213948A (en) | 1999-04-14 |
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