WO2005058364A2 - Preservative system - Google Patents
Preservative system Download PDFInfo
- Publication number
- WO2005058364A2 WO2005058364A2 PCT/GB2004/005139 GB2004005139W WO2005058364A2 WO 2005058364 A2 WO2005058364 A2 WO 2005058364A2 GB 2004005139 W GB2004005139 W GB 2004005139W WO 2005058364 A2 WO2005058364 A2 WO 2005058364A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- essential oil
- biocide
- essential
- composition
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/44—Oils, fats or waxes according to two or more groups of A61K47/02-A61K47/42; Natural or modified natural oils, fats or waxes, e.g. castor oil, polyethoxylated castor oil, montan wax, lignite, shellac, rosin, beeswax or lanolin
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
-
- 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
- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical at least one of the bonds to hetero atoms is to nitrogen
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
- A01N37/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system having at least one carboxylic group or a thio analogue, or a derivative thereof, and one oxygen or sulfur atom attached to the same aromatic ring system
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- 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
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
-
- 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
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/22—Lamiaceae or Labiatae [Mint family], e.g. thyme, rosemary, skullcap, selfheal, lavender, perilla, pennyroyal, peppermint or spearmint
-
- 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
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/28—Myrtaceae [Myrtle family], e.g. teatree or clove
-
- 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
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/36—Rutaceae [Rue family], e.g. lime, orange, lemon, corktree or pricklyash
-
- 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
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/40—Liliopsida [monocotyledons]
- A01N65/44—Poaceae or Gramineae [Grass family], e.g. bamboo, lemon grass or citronella grass
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/45—Ericaceae or Vacciniaceae (Heath or Blueberry family), e.g. blueberry, cranberry or bilberry
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/53—Lamiaceae or Labiatae (Mint family), e.g. thyme, rosemary or lavender
- A61K36/534—Mentha (mint)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/61—Myrtaceae (Myrtle family), e.g. teatree or eucalyptus
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0014—Skin, i.e. galenical aspects of topical compositions
Definitions
- the present invention relates to new preservative systems and their use in liquid composition, in particular pharmaceutical compositions.
- Preservatives are well known. Preservatives are intended to preserve a product, such as a food or a pharmaceutical, against microbial growth and product spoilage. Preservatives usually have good selective toxicity. Thus, they are typically safe for topical application and/or ingestion.
- preservatives include biocides, which inhibit the growth of microorganisms, such as bacteria.
- biocides include phenolic compounds, such as esters of p-hydroxy benzoic acid.
- esters are known as parabens, examples of which are methyl paraben (methyl ester of p-hydroxy benzoic acid) , ethyl paraben (ethyl ester of p-hydroxy benzoic acid) , propyl paraben (propyl ester of p-hydroxy benzoic acid) and butyl paraben (butyl ester of p-hydroxy benzoic acid) .
- methyl paraben methyl ester of p-hydroxy benzoic acid
- ethyl paraben ethyl ester of p-hydroxy benzoic acid
- propyl paraben propyl ester of p-hydroxy benzoic acid
- butyl paraben butyl ester of p-hydroxy benzoic acid
- Estragol, trans-anethole and fenchone were also found to synergistically enhance the antimicrobial activity of methyl paraben.
- the present inventors have discovered a relationship between the physical properties of essential oil and its ability to potentiate the antimicrobial activity of a biocide. Specifically, it is believed that essential oil having a. relatively high specific gravity and a relatively low dielectric constant can be used to potentiate the antimicrobial activity of a biocide, such as a paraben.
- an essential oil to potentiate the activity of a biocide, wherein the essential oil has a specific gravity of at least 0.89 and a dielectric constant of 1 to 20, and, preferably, wherein the essential oil does not consist of a single essential oil selected from fennel oil, anise oil, basil oil, fenchone, trans-anethole and estragol.
- an essential oil as a preservative in a liquid composition comprising a biocide, wherein the essential oil has a specific dielectric of at least 0.89 and a gravity constant of 1 to 20, and, preferably, wherein the essential oil does not consist of a single essential oil selected from fennel oil, anise oil, basil oil, fenchone, trans-anethole and estragol.
- a pharmaceutical composition comprising: a) an alginate, b) a bicarbonate and/or a carbonate, c) a biocide, and d) an essential oil, wherein the essential oil has a specific gravity of at least 0.89 and a dielectric constant of 1 to 20, and, preferably, wherein the essential oil does not consist of a single essential oil selected from fennel oil, anise oil, basil oil, fenchone, trans-anethole and estragol. It is believed that the antimicrobial activity of the biocide may be enhanced by the presence of an essential oil having a specific gravity of at least 0.89 and a dielectric constant of 1 to 20.
- a further aspect of the present invention provides the use of an essential oil to potentiate the activity of a biocide, wherein the essential oil has a specific gravity of at least 0.89 and a dielectric constant of 1 to 20, and wherein the essential oil does not consist of a single essential oil selected from fennel oil, anise oil, basil oil, fenchone, trans-anethole and estragol.
- the antimicrobial activity of the biocide is synergistically enhanced by the essential oil.
- the antimicrobial activity of the combination of the biocide and the oil is greater than the sum of the antimicrobial activity of the biocide in the absence of the oil and the antimicrobial activity of the oil in the absence of the biocide.
- the number of bacteria eliminated in the sample after a predetermined period of time is preferably greater than the sum of i) the number of bacteria eliminated after the same predetermined period in an identical culture treated with the biocide in the absence of the oil and ii) the number of bacteria eliminated after the same predetermined period in another identical culture treated with the oil in the absence of the biocide.
- the essential oil has a specific gravity of greater than 0.890, more preferably, at least 0.990.
- the essential oil may have a specific gravity of 0.990 to 2.000, for example, 1.000 to 1.700, preferably, 1.010 to 1.500.
- the specific gravity of the essential oil is 1.020 to 1.300, preferably, 1.030 to 1.250, most preferably, 1.170 to 1.200.
- Specific gravity may be measured using any suitable method. For example, conventional instruments, such as a pycnometer may be used. Gravimetric analysis may also be employed.
- the essential oil may have a dielectric constant of 2 to 18, preferably 3 to 12, more preferably 5 to 11, for example, 6 to 9. Dielectric constant is measured using any suitable method.
- a parallel plate capacitor may be employed.
- Any suitable essential oil may be employed in the composition of the claimed invention.
- essential plant oils may be employed.
- essential oil covers essential oils and the oily components of essential oils.
- a mixture of two or more oils may also be employed, particularly if the mixture has a specific gravity of at least 0.89 and a dielectric constant of 1 to 20.
- the oil has an aromatic component content of at least 30 %, more preferably at least 50%, even more preferably, at least 60 %, for example, at least 80%.
- the aromatic components are preferably water-insoluble.
- the essential oil is present in the liquid composition as an oil-in-water emulsion.
- the ratio of spearmint oil to clove oil or eugenol may be 10 - 90: 90 - 10, preferably, 30 - 70: 70 - 30, for example, 40 - 60: 60 - 40.
- the oil is a mixture of wintergreen oil and eugenol.
- the weight ratio of wintergreen oil to eugenol may be 10 - 90: 90 - 10, preferably, 30 - 70: 70 - 30, for example, 40 - 60: 60 - 40.
- oils consisting of one of fennel oil, basil oil and anise oil are excluded from the scope of the invention.
- the oil may be present in an amount of from 0.01 to 5 volume % of the composition, preferably, from 0.05 to 2 volume %, more preferably, from 0.07 to 1 volume %. In one embodiment, the oil is present in an amount of 0.01 to 0.5, for example, 0.01 to 0.1 volume %.
- the biocide employed in the composition may be an ester of p-hydroxy benzoic acid. Such esters are known as parabens. Examples of suitable parabens include methyl paraben, ethyl paraben, propyl paraben and butyl paraben (or their salts [e.g. soluble salts]). Mixtures of parabens may be employed.
- the biocide may be bronopol, chlorocresol or an isothiazole.
- the amount of biocide present in the composition may be 0.001 to 50 weight % of the composition, preferably, from 0.01 to 30 weight %.
- the ratio of essential oil to biocide in the composition may be 1:20 to 20:1, preferably, from 1:10 to 10:1, and more preferably, from 1:5 to 5:1.
- the composition is an aqueous composition comprising up to 99.99% water.
- the aqueous composition may comprise from 60 to up to 99.99 weight % water, for example, from 70 to 98 weight % water.
- the composition may be substantially anhydrous or may contain water in an amount of 0.1 to 50 weight %, preferably, 10 to 30 weight %. Such a concentrate may be diluted with water or an aqueous composition before use .
- the composition may also comprise a chelating agent.
- the chelating agent may enhance the interactions between the biocide and the bacterial wall by exposing more lipophilic surfaces on the bacterium. Suitable chelating agents include ethylene diaminetetraacetic acid (EDTA) or its derivatives (e.g. salts).
- EDTA ethylene diaminetetraacetic acid
- the composition is in the form of a liquid.
- the biocide may be present in an amount from 0.001 to 5 weight % of the composition, preferably, from 0.01 to 2 weight %, more preferably, from 0.07 to 1 weight %, for example, from 0.1 to 0.2 weight %.
- the composition may be used to inhibit the growth of a number of different bacteria.
- the composition may be useful against Ps aeruginosa , Enterobacter cloacae f Klebsiella oxytoca , Klebsiella pneumonia and Ci tobacter freundii .
- compositions comprising methyl paraben, propyl paraben and a number of different oils were tested for their antimicrobial activity against the Ps aeruginosa .
- the following oils were tested: I) spearmint oil, ii) spearmint oil and eugenol ( 63.5 : 36.5) and iii) eugenol.
- a control sample Cl) of spearmint oil and eugenol was also prepared (63.5:36.5). However, no parabens were included in the control . To carry out the tests, the following procedure was adopted.
- This sample was added to 9ml of a neutralizer comprising HEPES, Tween [l.ll%w/v Tween ® 80 (polysorbate 80); laboratory grade, Product #560234H, Cas# 9005-65-6 (BDH, Poole, Dorset, UK)] and Lecithin [0.085% w/v Lechitin Soya Bean; Laboratory grade, Product # 298632A, Cas#8030-76-0] .
- the test tube was then returned to the 25°C stirred water bath for the next sample .
- Each neutralized sample (20 ⁇ l) was spread out onto a plate containing Tryptone Soy Agar (Oxoid) and incubated overnight at 30°C.
- Figure 1 shows how the number of bacteria decreased over time.
- the samples containing ii) spearmint oil and eugenol (63.5:36.5) and iii) eugenol were very effective at reducing the number of bacteria.
- the oils in these samples had specific gravities of 0.9895 (ii) and 1.0775 (iii) , respectively.
- the sample containing I) spearmint oil had some antimicrobial activity, this sample was less effective than samples containing oils ii) and iii) .
- the specific gravity of spearmint oil (I) was 0.9508.
- the results for the Control show that the oil combination has little or no antimicrobial activity on its own.
- Example 1 was repeated with the following oils: iv) spearmint oil and wintergreen oil (49:51) and v) wintergreen oil. A control C2) of wintergreen oil only was also prepared. However, no parabens were included in the control. The results are also shown in Figure 1. As can be seen from the Figure, samples containing iv) wintergreen oil and spearmint oil and v) wintergreen oil had excellent antimicrobial activity. The oils in these samples had specific gravities of iv) 1.067 and v) 1.186, respectively.
- Example 2 the procedure of Example 1 was repeated to test the activity of a composition comprising methyl paraben, propyl paraben and wintergreen oil against Enterobacter cloacae .
- a composition comprising methyl paraben, propyl paraben and fennel oil was also tested. In each case, 0.117%w/v methyl paraben and 0.018%w/v propyl paraben were employed. The amount of oil in each case was 0.078%v/v.
- Figure 2 As can be seen from the Figure, the wintergreen oil composition had better antimicrobial activity than the fennel oil composition. Wintergreen oil has a specific gravity of 1.1864, whereas fennel oil has a specific gravity of 1.001.
- Example 3 The procedure of Example 3 was repeated with a culture of Klebsiella oxytoca . As can be seen from Figure 3, the wintergreen oil composition had better antimicrobial activity than the fennel oil composition.
- Example 4 The procedure of Example 4 was repeated with a culture of Ps . Aeruginosa . As can be seen from Figure 4, the wintergreen oil composition had better antimicrobial activity than the fennel oil composition.
- Deionised water to 1 litre is made up as follows 1. 917ml of deionised water are dispensed into a mixing vessel and cooled to approximately 20°C.
- biocides, carbonates, essential oil and sweetener are added to the mixture and stirred for 5 minutes.
- the alginate is added with stirring over a period of 3 minutes .
- the temperature is controlled during manufacture to 22°C (plus or minus 5°C) .
Abstract
Description
Claims
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP04805959A EP1742666A2 (en) | 2003-12-12 | 2004-12-10 | Preservative system |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB0328845A GB2408933A (en) | 2003-12-12 | 2003-12-12 | Antimicrobial composition |
GB0328845.3 | 2003-12-12 |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2005058364A2 true WO2005058364A2 (en) | 2005-06-30 |
WO2005058364A3 WO2005058364A3 (en) | 2006-02-23 |
Family
ID=30130120
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/GB2004/005139 WO2005058364A2 (en) | 2003-12-12 | 2004-12-10 | Preservative system |
Country Status (3)
Country | Link |
---|---|
EP (1) | EP1742666A2 (en) |
GB (1) | GB2408933A (en) |
WO (1) | WO2005058364A2 (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7816410B2 (en) | 2003-12-02 | 2010-10-19 | Biofutures PI Ltd. | Pesticidal compositions |
CN103429088A (en) * | 2011-03-18 | 2013-12-04 | 拜欧方吉特克有限责任公司 | Phytosanitary compositions comprising essential oils that potentiate antifungal activity |
CN104814047A (en) * | 2015-05-14 | 2015-08-05 | 荆丙艳 | Traditional Chinese medicine composition disinfectant for disinfecting B ultrasonic rooms |
US9364419B2 (en) * | 2014-05-15 | 2016-06-14 | The Procter & Gamble Company | Oral care compositions containing polyethylene glycol for physical stability |
WO2018009532A1 (en) * | 2016-07-06 | 2018-01-11 | Mccormick & Company, Incorporated | Natural encapsulation flavor products |
US9913783B2 (en) | 2014-05-15 | 2018-03-13 | The Procter & Gamble Company | Dentifrice compositions having optimized preservatives |
US10039697B2 (en) | 2014-05-15 | 2018-08-07 | The Procter & Gamble Company | Dentifrice compositions having improved fluoride ion stability or fluoride uptake |
US10820597B2 (en) | 2011-03-18 | 2020-11-03 | Biofungitek, S.L. | Phytosanitary composition comprising essential oils that potentiate antifungal activity |
US10835477B2 (en) | 2014-05-15 | 2020-11-17 | The Procter & Gamble Company | Oral care compositions containing polyethylene glycol for physical stability |
Citations (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US321839A (en) * | 1885-07-07 | Stanley w | ||
US737529A (en) * | 1902-12-27 | 1903-08-25 | Alfred H Thieme | Paper-hanger's size. |
US1149777A (en) * | 1913-06-26 | 1915-08-10 | Evan L Moore | Composition for use as a protective coating for the hands. |
GB191503343A (en) * | 1915-03-02 | 1915-12-30 | Walter Millne Scott | An Appliance for Destroying Vermin. |
GB143312A (en) * | 1919-02-19 | 1920-05-19 | Meter Louis Rhein | Dentrifice |
GB169189A (en) * | 1920-03-17 | 1921-09-19 | Alec Edward Sherman | Improvements in and relating to preserving meat |
GB961659A (en) * | 1960-01-15 | 1964-06-24 | Unilever Ltd | Dentifrice compositions |
US4022881A (en) * | 1974-06-18 | 1977-05-10 | Beecham Group Limited | Dentifrice |
GB1578541A (en) * | 1976-07-15 | 1980-11-05 | Bayer Ag | Preserving liquid antacid medicinal formulations |
GB2068730A (en) * | 1980-02-06 | 1981-08-19 | Lion Corp | Oral composition |
EP0202359A2 (en) * | 1985-05-23 | 1986-11-26 | Block Drug Company Inc. | Dental preparation, article and method for storage and delivery thereof |
US4645662A (en) * | 1984-07-26 | 1987-02-24 | Lion Corporation | Oral composition |
EP0241804A2 (en) * | 1986-04-10 | 1987-10-21 | Bayer Ag | Preserved antacid preparations |
EP0244363A1 (en) * | 1986-05-02 | 1987-11-04 | Warner-Lambert Company | Composition and method to inhibit the growth of organisms by the use of bis-biguanido hexanes and essential oil mixture combinations |
US4844883A (en) * | 1987-01-20 | 1989-07-04 | Florasynth, Inc. | Stabilization of wintergreen flavor in chalk-based dentifrice and method |
WO1993009770A1 (en) * | 1991-11-13 | 1993-05-27 | Pierre Fabre Medicament | Bactericidal pharmaceutical composition containing chlorhexidine and eugenol |
FR2697133A1 (en) * | 1992-10-28 | 1994-04-29 | Transbiotech | Synergistic biocidal and biostatic compsns, active against eg bacteria, fungi and viruses - contg a sesquiterpene, eg pinene, and an aromatic cpd, eg carvacrol |
WO1997040812A1 (en) * | 1996-04-26 | 1997-11-06 | Warner-Lambert Company | Enhanced zinc containing oral composition |
WO1999009836A1 (en) * | 1997-08-23 | 1999-03-04 | Queen Margaret College | Inhibitor and preservative formulation |
EP0937394A1 (en) * | 1998-01-20 | 1999-08-25 | Ethicon, Inc. | Antimicrobial composition |
WO2000078276A1 (en) * | 1999-06-23 | 2000-12-28 | Warner-Lambert Company | Multi-benefit oral hygiene product |
US6248343B1 (en) * | 1998-01-20 | 2001-06-19 | Ethicon, Inc. | Therapeutic antimicrobial compositions |
WO2001087095A1 (en) * | 2000-05-15 | 2001-11-22 | Unilever Plc | Ambient stable beverage |
WO2002055056A2 (en) * | 2001-01-10 | 2002-07-18 | Walther Schoenenberger Pflanzensaftwerk Gmbh & Co. Kg | Local use of essential oils for treating herpes labialis |
US20030194454A1 (en) * | 1998-07-28 | 2003-10-16 | Bessette Steven M. | Pesticidal compositions containing rosemary oil and wintergreen oil |
Family Cites Families (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4428929A (en) * | 1983-03-04 | 1984-01-31 | Wicheta William E | New oral cleansing medium for wearers of partial and full dentures |
JPH0629176B2 (en) * | 1983-06-17 | 1994-04-20 | ライオン株式会社 | Oral composition |
DE3702983A1 (en) * | 1986-06-09 | 1987-12-10 | Henkel Kgaa | DISINFECTANT AND THEIR USE FOR SKIN AND MUCUS SKIN DISINFECTION |
JP2682020B2 (en) * | 1988-06-29 | 1997-11-26 | ライオン株式会社 | Oral composition |
US5296241A (en) * | 1991-04-03 | 1994-03-22 | Brimberg Barnett J | Therapeutic composition and method of using same for treatment of hangover |
JPH05320032A (en) * | 1992-05-20 | 1993-12-03 | Kao Corp | Composition for oral cavity application |
JPH06217747A (en) * | 1993-01-25 | 1994-08-09 | Nippon Oil & Fats Co Ltd | Antibacterial agent |
BR9707610A (en) * | 1996-02-23 | 1999-07-27 | Procter & Gamble | Disinfectant compositions and processes for disinfecting surfaces |
JP2002068923A (en) * | 2000-08-28 | 2002-03-08 | Sakamoto Yakuhin Kogyo Co Ltd | Low-irritant cosmetic composition |
WO2003077885A2 (en) * | 2002-03-12 | 2003-09-25 | Neurogesx, Inc. | Free-base formulations of local anesthetics |
-
2003
- 2003-12-12 GB GB0328845A patent/GB2408933A/en not_active Withdrawn
-
2004
- 2004-12-10 WO PCT/GB2004/005139 patent/WO2005058364A2/en active Application Filing
- 2004-12-10 EP EP04805959A patent/EP1742666A2/en not_active Withdrawn
Patent Citations (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US321839A (en) * | 1885-07-07 | Stanley w | ||
US737529A (en) * | 1902-12-27 | 1903-08-25 | Alfred H Thieme | Paper-hanger's size. |
US1149777A (en) * | 1913-06-26 | 1915-08-10 | Evan L Moore | Composition for use as a protective coating for the hands. |
GB191503343A (en) * | 1915-03-02 | 1915-12-30 | Walter Millne Scott | An Appliance for Destroying Vermin. |
GB143312A (en) * | 1919-02-19 | 1920-05-19 | Meter Louis Rhein | Dentrifice |
GB169189A (en) * | 1920-03-17 | 1921-09-19 | Alec Edward Sherman | Improvements in and relating to preserving meat |
GB961659A (en) * | 1960-01-15 | 1964-06-24 | Unilever Ltd | Dentifrice compositions |
US4022881A (en) * | 1974-06-18 | 1977-05-10 | Beecham Group Limited | Dentifrice |
GB1578541A (en) * | 1976-07-15 | 1980-11-05 | Bayer Ag | Preserving liquid antacid medicinal formulations |
GB2068730A (en) * | 1980-02-06 | 1981-08-19 | Lion Corp | Oral composition |
US4645662A (en) * | 1984-07-26 | 1987-02-24 | Lion Corporation | Oral composition |
EP0202359A2 (en) * | 1985-05-23 | 1986-11-26 | Block Drug Company Inc. | Dental preparation, article and method for storage and delivery thereof |
EP0241804A2 (en) * | 1986-04-10 | 1987-10-21 | Bayer Ag | Preserved antacid preparations |
EP0244363A1 (en) * | 1986-05-02 | 1987-11-04 | Warner-Lambert Company | Composition and method to inhibit the growth of organisms by the use of bis-biguanido hexanes and essential oil mixture combinations |
US4844883A (en) * | 1987-01-20 | 1989-07-04 | Florasynth, Inc. | Stabilization of wintergreen flavor in chalk-based dentifrice and method |
WO1993009770A1 (en) * | 1991-11-13 | 1993-05-27 | Pierre Fabre Medicament | Bactericidal pharmaceutical composition containing chlorhexidine and eugenol |
FR2697133A1 (en) * | 1992-10-28 | 1994-04-29 | Transbiotech | Synergistic biocidal and biostatic compsns, active against eg bacteria, fungi and viruses - contg a sesquiterpene, eg pinene, and an aromatic cpd, eg carvacrol |
WO1997040812A1 (en) * | 1996-04-26 | 1997-11-06 | Warner-Lambert Company | Enhanced zinc containing oral composition |
WO1999009836A1 (en) * | 1997-08-23 | 1999-03-04 | Queen Margaret College | Inhibitor and preservative formulation |
EP0937394A1 (en) * | 1998-01-20 | 1999-08-25 | Ethicon, Inc. | Antimicrobial composition |
US6248343B1 (en) * | 1998-01-20 | 2001-06-19 | Ethicon, Inc. | Therapeutic antimicrobial compositions |
US20030194454A1 (en) * | 1998-07-28 | 2003-10-16 | Bessette Steven M. | Pesticidal compositions containing rosemary oil and wintergreen oil |
WO2000078276A1 (en) * | 1999-06-23 | 2000-12-28 | Warner-Lambert Company | Multi-benefit oral hygiene product |
WO2001087095A1 (en) * | 2000-05-15 | 2001-11-22 | Unilever Plc | Ambient stable beverage |
WO2002055056A2 (en) * | 2001-01-10 | 2002-07-18 | Walther Schoenenberger Pflanzensaftwerk Gmbh & Co. Kg | Local use of essential oils for treating herpes labialis |
Non-Patent Citations (6)
Title |
---|
DATABASE CA [Online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; "Dentifrices containing bactericides" XP002357076 retrieved from STN Database accession no. 102:172444 & JP 60 001118 A2 (CANON K. K., JAPAN) 7 January 1985 (1985-01-07) & DATABASE WPI Week 1985 Derwent Publications Ltd., London, GB; AN 1985-041559 & JP 60 001118 A (LION CORP) * |
DATABASE WPI Section Ch, Week 199436 Derwent Publications Ltd., London, GB; Class D13, AN 1994-289996 XP002357828 & JP 06 217747 A (NIPPON OILS & FATS CO LTD) 9 August 1994 (1994-08-09) * |
DATABASE WPI Section Ch, Week 200238 Derwent Publications Ltd., London, GB; Class D21, AN 2002-346928 XP002357827 & JP 2002 068923 A (SAKAMOTO YAKUHIN KOGYO KK) 8 March 2002 (2002-03-08) * |
DE M ET AL: "ANTIMICROBIAL SCREENING OF SOME INDIAN SPICES" PHYTOTHERAPY RESEARCH, JOHN WILEY & SONS LTD. CHICHESTER, GB, vol. 13, no. 7, November 1999 (1999-11), pages 616-618, XP008047201 ISSN: 0951-418X * |
FRIEDMAN M ET AL: "BACTERICIDAL ACTIVITIES OF PLANT ESSENTIAL OILS AND SOME OF THEIR ISOLATED CONSTITUENTS AGAINST CAMPYLOBACTER JEJUNI, ESCHERICHIA COLI, LISTERIA MONOCYTOGENES, AND SALMONELLA ENTERICA" JOURNAL OF FOOD PROTECTION, DES MOINES, IO, US, vol. 65, no. 10, October 2002 (2002-10), pages 1545-1560, XP009020265 ISSN: 0362-028X * |
HAMMER K A ET AL: "ANTIMICROBIAL ACTIVITY OF ESSENTIAL OILS AND OTHER PLANT EXTRACTS" JOURNAL OF APPLIED MICROBIOLOGY, OXFORD, GB, vol. 86, no. 6, 1999, pages 985-990, XP001108841 ISSN: 1364-5072 * |
Cited By (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7816410B2 (en) | 2003-12-02 | 2010-10-19 | Biofutures PI Ltd. | Pesticidal compositions |
CN103429088A (en) * | 2011-03-18 | 2013-12-04 | 拜欧方吉特克有限责任公司 | Phytosanitary compositions comprising essential oils that potentiate antifungal activity |
EP2687095A1 (en) * | 2011-03-18 | 2014-01-22 | Biofungitek, Sociedad Limitada | Phytosanitary composition comprising essential oils that potentiate antifungal activity |
EP2687095A4 (en) * | 2011-03-18 | 2014-09-03 | Biofungitek Sl | Phytosanitary composition comprising essential oils that potentiate antifungal activity |
US10863749B2 (en) | 2011-03-18 | 2020-12-15 | Biofungitek, S.L. | Phytosanitary composition comprising essential oils that potentiate antifungal activity |
US10820597B2 (en) | 2011-03-18 | 2020-11-03 | Biofungitek, S.L. | Phytosanitary composition comprising essential oils that potentiate antifungal activity |
CN107079926A (en) * | 2011-03-18 | 2017-08-22 | 拜欧方吉特克有限责任公司 | The composition of control plant disease comprising the essential oil for strengthening antifungal activity |
US10813360B2 (en) | 2011-03-18 | 2020-10-27 | Biofungitek, S.L. | Phytosanitary composition comprising essential oils that potentiate antifungal activity |
US9913783B2 (en) | 2014-05-15 | 2018-03-13 | The Procter & Gamble Company | Dentifrice compositions having optimized preservatives |
US10039697B2 (en) | 2014-05-15 | 2018-08-07 | The Procter & Gamble Company | Dentifrice compositions having improved fluoride ion stability or fluoride uptake |
US10149806B2 (en) | 2014-05-15 | 2018-12-11 | The Procter & Gamble Company | Oral care compositions containing polyethylene glycol for physical stability |
US9364419B2 (en) * | 2014-05-15 | 2016-06-14 | The Procter & Gamble Company | Oral care compositions containing polyethylene glycol for physical stability |
US10835477B2 (en) | 2014-05-15 | 2020-11-17 | The Procter & Gamble Company | Oral care compositions containing polyethylene glycol for physical stability |
CN104814047A (en) * | 2015-05-14 | 2015-08-05 | 荆丙艳 | Traditional Chinese medicine composition disinfectant for disinfecting B ultrasonic rooms |
CN109475161A (en) * | 2016-07-06 | 2019-03-15 | 麦克考米克有限公司 | Natural encapsulation flavoring products |
WO2018009532A1 (en) * | 2016-07-06 | 2018-01-11 | Mccormick & Company, Incorporated | Natural encapsulation flavor products |
Also Published As
Publication number | Publication date |
---|---|
EP1742666A2 (en) | 2007-01-17 |
WO2005058364A3 (en) | 2006-02-23 |
GB0328845D0 (en) | 2004-01-14 |
GB2408933A (en) | 2005-06-15 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1543830A1 (en) | Antiseptic bactericides and cosmetics, drugs and foods containing the antiseptic bactericides | |
AU598382B2 (en) | Taste and odour masked edible oil compositions | |
US7384646B2 (en) | Antiseptic disinfectant, and cosmetics and toiletries, medicine or food containing the same | |
DE3910170B4 (en) | Bacterial desorption composition | |
KR20190068565A (en) | Compositions comprising glycolipids and preservatives | |
CN102811702B (en) | Liquid oral composition and method for producing same | |
EP1742666A2 (en) | Preservative system | |
US7074439B2 (en) | Preparation of essential oil compositions for potable liquid disinfection | |
BR112020010125B1 (en) | EDIBLE PLANT-BASED OIL-IN-WATER EMULSION COMPOSITION AND USE THEREOF IN AN ORAL TISSUE | |
JP2009138028A (en) | Catechin-containing antioxidation and preservability improvement formulation excellent in storage stability and method for producing the same | |
Shahidi et al. | Green tea catechins as inhibitors of oxidation of meat lipids | |
JP2000128801A (en) | Antibacterial composition | |
CN106456485B (en) | Liquid oral composition and the method for improving its freezing restoration | |
BR112020003023A2 (en) | compositions and methods for inhibiting plant pathogens | |
JP2004307484A (en) | Antiseptic bactericide, and cosmetic, pharmaceutical and foodstuff blended with the same | |
RU2002130196A (en) | PHARMACEUTICAL COMPOSITION CONTAINING CALCIUM OR CALCIUM AND VITAMIN MIXTURE OR CALCIUM AND MAGNESIUM MIXTURE | |
KR102614880B1 (en) | Oral composition and growth promoter for oral bacteria | |
AU2018392886A1 (en) | Oral compositions and methods of use | |
US20090123395A1 (en) | Flavour Compositions | |
Yen et al. | Antioxidative properties of extracts from Aspergillus candidus broth filtrate | |
CA2987034C (en) | Use of an organic citrus extract with high antimicrobial capacity and xylitol as a preservative system in liquids, emulsions, suspensions, creams and antacids | |
EP0983339A1 (en) | Novel clear beverage optionally alcoholic containing anethol and cloudy diluted beverage obtained by dilution | |
O Bakr et al. | Antioxidant and anti-listerial activities of selected Egyptian medicinal plants | |
EP4329714A1 (en) | Composition comprising a zinc salt and an additional effective ingredient | |
EP3902510A1 (en) | Oral articles and methods of use |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A2 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A2 Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2004805959 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 2004805959 Country of ref document: EP |