CA2101234A1 - Anti-urease cosmetic or dermatological composition - Google Patents
Anti-urease cosmetic or dermatological compositionInfo
- Publication number
- CA2101234A1 CA2101234A1 CA 2101234 CA2101234A CA2101234A1 CA 2101234 A1 CA2101234 A1 CA 2101234A1 CA 2101234 CA2101234 CA 2101234 CA 2101234 A CA2101234 A CA 2101234A CA 2101234 A1 CA2101234 A1 CA 2101234A1
- Authority
- CA
- Canada
- Prior art keywords
- urease
- composition
- agent
- cosmetic
- oil
- 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.)
- Abandoned
Links
Abstract
Abstract An anti-urease cosmetic or dermatological com-position, more particularly an antiperspirant and anti-nappy rash composition containing a condensed tannin of carob or Hamamelis and a chlorogenic acid derivative in an effective quantity as anti-urease agent in combination with a suitable cosmetic support.
Description
This invention relates to an anti-urease cosmetic or dermatological composition.
The formation of ammonia through the degradation of urea by urease plays an important part in perspira-tion and nappy rash. In the particularcase of nappy rash, the formation of ammonia is not the direct cause, but initiates an increase in pH which pro-motes an increase in the activity of fecal lipases and proteases which in turn causes irritation of the skin.
Numerous avenues have been eXplored with a view to solving the problem of nappy rash.
Disposable nappies ensuring maximum absorption have been introduced. The function of the pharmaceutical or cosmetic products available on the market is to sooth dermatitis of the buttocks. These products contain protective agents (the use of some of these products may be dangerous), antiseptics, anti-inflammatories (avail-able only prescription) or buffer systems (simple neutralization of ammonia and the acids formed by bacterial degradation).
However, the known solutions mentioned above are confined to reducing the effects of the activity of the enzymes without attacking the cause of that activity.
In addition, some anti-urease agents are known to be active against erythema of the buttocks and as de-odorants, including for example hydroxamic acid (cf., for example, JP-A-57104276) and hydroximic acid tcf., for example, JP-A-57119997). More generally, poly-hydroxyphenols and quinones are known for their anti-urease activity (cf., for example, H.J. Michel, "DiePharmazie", No. 2, February 1980, page 66, paragraph 6", although there has been no reference to their use in the 210123~
treatment of nappy rash or as an antiper-spirant.
The problem addressed by the present invention was to provide an antiperspirant or anti-nappy rash composition of which the active princi-ple would be of natural or synthetic origin and, in the latter case, would be a compound found in nature and resynthesized. In the case of an anti-nappy rash composi-tion, the problem was also to provide it with a more pleasant appearance and feel than known anti-erythema compositions of the pharmaceutical ointment type.
Accordingly, the present invention relates to an anti-urease cosmetic or dermatological composition containing tannins, characterized in that it contains an effective quantity of an anti-urease agent selected from condensed carob tannins and chlorogenic acid deriva-tives.
In the context of the invention, the condensed carob tannins consist of gallic acid esters or more complex forms gallic acid involving depsidic bonds (bond between 2 galloyls) and glucose. The condensed tannins of Hamamelis consist of esters of gallic acid or the more complex forms of gallic acid mentioned above and hamamelose. These tannins may be in the form of more or less purified vegetable extracts.
Chlorogenic acid derivatives are understood to be caffeoyl, dicaffeoyl, feruloyl, coumaroyl and caffeoyl feruloyl quinic acids and the corresponding quinides (lactones of quinic acid). These derivatives may be in the form of natural plant extracts, for example coffee or artichoke extracts, or in synthetic form. A prefer-red source of these chlorogenic acids is the residue from the decaffeination of an aqueous extract of green coffee by adsorption, for example to active carbon.
This residue is obtained by desorption of the adsorbate 210123~
by elution from the adsorbent and elimination of the caffeine from the eluate by liquid/liquid extraction.
In the context of the invention, an effective quantity of the anti-urease agent is the quantity which produces 50% inhibition of the urease activity as measured by the method described hereinafter in Example 1. This inhibition is obtained with a quantity of 200 to 2000 microg anti-urease agent.
A cosmetic composition according to the invention may be in the form of an optionally aqueous solution or dispersion or, preferably, a water-in-oil or oil-in-water emulsion. It preferably contains 0.1 to 10% by weight anti-urease agent in combination with a cosmetic support, such as for example a lotion, a cream or a milk.
In an emulsion, the fatty phase may contain animal, vegetable, mineral or synthetic oils and may also contain waxes, long-chain alcohols, thickeners or gelling agents. A composition in the form of an emul-sion preferably contains 1 to 20% by weight of an emulsifier.
A composition according to the invention may also contain various additives, particularly colorants, per-fumes, preservatives, humectants, buffers, pearlescers and mineral or organic fillers. It advantageously contains antioxidants, preferably in a quantity of 0.02 to 0.2% by weight.
The present invention also relates to the use of an extract of Hamamelis as an anti-urease agent.
In such a use, the Hamamelis extract may be incorporated in a cosmetic or dermatological composition as described above.
The invention is illustrated by the following Examples in which parts and percentages are by weight unless otherwise indicated.
210123~
~xample 1 The anti-urease activity of the inhibiting compounds useable in accordance with the invention is determined at various concentrations.
Method The method of analyzing the anti-urease activity of an inhibitor is based on the principle of determining ammonia. The urea present in a substrate sample con-taining a mixture of inhibitor, urea and urease isdegraded by urease at 37C over a fixed incubation period of lS minutes. The last two reagents are in the following proportions: 7 microg urea to 25 microg urease (vegetable origin, namely jack beans), or 0.25 unit, i.e. 0.25 ml of a solution of 25 mg urease dissolved in 25 ml buffer solution itself prepared by dissolving 6 g 4-(2-hydroxyethyl)-piperazine-1-ethane sulfonic acid and 0.2 g ethylene diamine tetraacetate in 1 1 water and pH
adjustment to 7.5 by addition of a dilute sodium hydrox-ide solution. The ammonia from the enzymatic reaction quantitatively forms an indophenol derivative with the reagents sodium hypochlorite, phenol and sodium nitro-prusside. 4 ml solution prepared by dissolving 10 g phenol and 50 mg sodium nitroprusside in 1 1 water are added to the sample which is then made up to 10 ml by addition of a sodium hypochlorite solution (prepared by dissolving 5 g sodium hydroxide and 10 ml sodium hypo-chlorite in 1 1 water). After incubation for 20 minutes at 37C, the adsorption is measured by spectrophotometry in comparison with the same, but sample-free mixture of reagents, the indophenol derivative obtained being characterized by a coloration of which the intensity is proportional to the quantity of ammonia released and measurable at 634 nm in 10 mm cells. The % ammonia released is expressed by the relation: optical density of the sample with inhibitor/optical density of the sample without inhibitor x 100.
Results The anti-urease activity is expressed as the quantity of inhibitor tin microg) required to obtain 50%
inhibition represented by the mean value of 4 to 5 determinations for each inhibitor tested.
The results are set out in Table 1 below.
T~ble 1 Inhibitor Activity (microg) Usnic acid 250 (glycolic extract of Usnea barbata containing 7.5% usnate) Chlorogenic acid 200 (artichoke extract containing 46.7%
chlorogenic acid) Hamamelis 200 (15% tannins) Residue from the 500 decaffeination of green coffee eluted from the fraction retained on active carbon Extract of green carob 500 (desugared with hot water) Extract of green tea1000 Table 1 (continued) Inhibitor Activity (microg) l-CQA 250 3,4-Di-CQA 250 3-CoQA 350 3,4-di-CoQA 1000 3,4-di-FQA 1000 3,4-di-CFQA 1000 Legend CQA = caffeoyl quinic acid FQA = feruloyl quinic acid CoQA = coumaroyl quinic acid CFQA = caffeoyl feruloyl quinic acid The quinic acid derivatives mentioned above were prepared in accordance with applicants' patent applica-tions filed on the same day as the present application under the following titles: "Quinic acid derivatives and a process for their production" and "3- and/or 4-Substi-tuted quinic acid derivatives and a process for their production".
Ex~mple 2 An in vitro test is carried on a protective cosmetic cream of which the anti-urease activity is evaluated as described in Example 1 by colorimetric determination of the ammonia released and of which the pH is directly measured in the reaction mixtures using a glass electrode. The initial hypothesis is that an infant with an average weight of 6 kg has its nappy changed every 4 h. During these 4 h, it produces on average 40 ml urine corresponding to 300 mg urea and 30 210123~
g feces containing a quantity of urease varying from 3 to 30 U. Thus, the quantity of cream to be applied to the sensitive areas is evaluated at 10 g containing 400 mg Hamamelis extract as inhibitor.
The cream is an oil-in-water emulsion of which the composition is shown in Table 2 below (the nomencla-ture used for the ingredients is that of the "Cosmetic, Toiletry and Fragrance Association, Inc., Washington DC"
in its French translation).
Table 2 Ingredient %
Phase A
Glycerol stearate 10 Cetoaryl octanoate 3 Palm olein (containing 3 Cl214 fatty acids) Sunflower oil 4 Wheat germ oil 0.3 Ph~se B
Glycerol 5 Water qsf 100 Phase C
Cyclomethicone 3 DL-alpha-tocopherol acetate 0.2 Preservative 0.2 Hamamelis extract 4 To prepare the cream, phases A and B are sepa-rately heated to 80C, after which phase B is poured into phase A with vigorous stirring. The mixture is then left to cool to 40C with continuous stirring, phase C is incorporated with vigorous stirring and the 210123~
whole is left to cool to ambient temperature with continuous stirring. The activity of the cream contain-ing the inhibitor is determined by comparison with an inhibitor-free cream in concentrations of 0.75 U and 7.5 U enzyme. The results relating to the quantity of ammonia released are set out in Table 3 below while those relating to the pH are set out in Table 4.
T~ble 3 O Composition Quantity Ammonia released ~mg) after of enzyme an incubation period X
(U) (h) Cream contain- 0.75 0.47 0.89 0.97 0.97 0.92 ing 4~ Hamam- 7.5 1.13 1.04 1.27 -- 0.87 elis extract Cream with no 0.75 1.38 2.18 1.74 2.26 2.61 inhibitor 7.5 5.92 9.66 9.66 -- 9.38 0 T~ble 4 Composition Quantity pH after a period X (h) of enzyme (U) 0 24 Cream contain- 0.75 5.79 5.84 ing 4% Hamam- 7.5 5.78 5.83 elis extract Cream with no 0.75 5.94 6.53 inhibitor 7.5 5.94 7.73 The results obtained show that the cream contain-ing the Hamamelis extract is capable of completely inhibiting urease in the two concentrations of 3 and 30 U.
~xample 3 A protective cream is prepared in the form of a 21012'3~
water-in-oil emulsion of which the composition is shown in Table 5 below.
Table 5 Ingredients %
Ph~se A
Microcrystalline wax, 9 pentaerythritol cocoate, stearyl citrate, glycerol oleate, aluminium stearate and propylene glycol Decyl oleate 3 Palm olein (containing 10 Cl214 fatty acids) Sunflower oil 12 Ozocerite 0.5 Wheat germ oil 0.3 Ph~se B
Glycerol 5 Water qsf 100 Ph~se C
DL-alpha-tocopherol acetate 0.2 Cyclomethicone 3 Preservative 0.2 Hamamelis extract 4 The oil-in-water cream is prepared as described above for the cream of Example 2.
The formation of ammonia through the degradation of urea by urease plays an important part in perspira-tion and nappy rash. In the particularcase of nappy rash, the formation of ammonia is not the direct cause, but initiates an increase in pH which pro-motes an increase in the activity of fecal lipases and proteases which in turn causes irritation of the skin.
Numerous avenues have been eXplored with a view to solving the problem of nappy rash.
Disposable nappies ensuring maximum absorption have been introduced. The function of the pharmaceutical or cosmetic products available on the market is to sooth dermatitis of the buttocks. These products contain protective agents (the use of some of these products may be dangerous), antiseptics, anti-inflammatories (avail-able only prescription) or buffer systems (simple neutralization of ammonia and the acids formed by bacterial degradation).
However, the known solutions mentioned above are confined to reducing the effects of the activity of the enzymes without attacking the cause of that activity.
In addition, some anti-urease agents are known to be active against erythema of the buttocks and as de-odorants, including for example hydroxamic acid (cf., for example, JP-A-57104276) and hydroximic acid tcf., for example, JP-A-57119997). More generally, poly-hydroxyphenols and quinones are known for their anti-urease activity (cf., for example, H.J. Michel, "DiePharmazie", No. 2, February 1980, page 66, paragraph 6", although there has been no reference to their use in the 210123~
treatment of nappy rash or as an antiper-spirant.
The problem addressed by the present invention was to provide an antiperspirant or anti-nappy rash composition of which the active princi-ple would be of natural or synthetic origin and, in the latter case, would be a compound found in nature and resynthesized. In the case of an anti-nappy rash composi-tion, the problem was also to provide it with a more pleasant appearance and feel than known anti-erythema compositions of the pharmaceutical ointment type.
Accordingly, the present invention relates to an anti-urease cosmetic or dermatological composition containing tannins, characterized in that it contains an effective quantity of an anti-urease agent selected from condensed carob tannins and chlorogenic acid deriva-tives.
In the context of the invention, the condensed carob tannins consist of gallic acid esters or more complex forms gallic acid involving depsidic bonds (bond between 2 galloyls) and glucose. The condensed tannins of Hamamelis consist of esters of gallic acid or the more complex forms of gallic acid mentioned above and hamamelose. These tannins may be in the form of more or less purified vegetable extracts.
Chlorogenic acid derivatives are understood to be caffeoyl, dicaffeoyl, feruloyl, coumaroyl and caffeoyl feruloyl quinic acids and the corresponding quinides (lactones of quinic acid). These derivatives may be in the form of natural plant extracts, for example coffee or artichoke extracts, or in synthetic form. A prefer-red source of these chlorogenic acids is the residue from the decaffeination of an aqueous extract of green coffee by adsorption, for example to active carbon.
This residue is obtained by desorption of the adsorbate 210123~
by elution from the adsorbent and elimination of the caffeine from the eluate by liquid/liquid extraction.
In the context of the invention, an effective quantity of the anti-urease agent is the quantity which produces 50% inhibition of the urease activity as measured by the method described hereinafter in Example 1. This inhibition is obtained with a quantity of 200 to 2000 microg anti-urease agent.
A cosmetic composition according to the invention may be in the form of an optionally aqueous solution or dispersion or, preferably, a water-in-oil or oil-in-water emulsion. It preferably contains 0.1 to 10% by weight anti-urease agent in combination with a cosmetic support, such as for example a lotion, a cream or a milk.
In an emulsion, the fatty phase may contain animal, vegetable, mineral or synthetic oils and may also contain waxes, long-chain alcohols, thickeners or gelling agents. A composition in the form of an emul-sion preferably contains 1 to 20% by weight of an emulsifier.
A composition according to the invention may also contain various additives, particularly colorants, per-fumes, preservatives, humectants, buffers, pearlescers and mineral or organic fillers. It advantageously contains antioxidants, preferably in a quantity of 0.02 to 0.2% by weight.
The present invention also relates to the use of an extract of Hamamelis as an anti-urease agent.
In such a use, the Hamamelis extract may be incorporated in a cosmetic or dermatological composition as described above.
The invention is illustrated by the following Examples in which parts and percentages are by weight unless otherwise indicated.
210123~
~xample 1 The anti-urease activity of the inhibiting compounds useable in accordance with the invention is determined at various concentrations.
Method The method of analyzing the anti-urease activity of an inhibitor is based on the principle of determining ammonia. The urea present in a substrate sample con-taining a mixture of inhibitor, urea and urease isdegraded by urease at 37C over a fixed incubation period of lS minutes. The last two reagents are in the following proportions: 7 microg urea to 25 microg urease (vegetable origin, namely jack beans), or 0.25 unit, i.e. 0.25 ml of a solution of 25 mg urease dissolved in 25 ml buffer solution itself prepared by dissolving 6 g 4-(2-hydroxyethyl)-piperazine-1-ethane sulfonic acid and 0.2 g ethylene diamine tetraacetate in 1 1 water and pH
adjustment to 7.5 by addition of a dilute sodium hydrox-ide solution. The ammonia from the enzymatic reaction quantitatively forms an indophenol derivative with the reagents sodium hypochlorite, phenol and sodium nitro-prusside. 4 ml solution prepared by dissolving 10 g phenol and 50 mg sodium nitroprusside in 1 1 water are added to the sample which is then made up to 10 ml by addition of a sodium hypochlorite solution (prepared by dissolving 5 g sodium hydroxide and 10 ml sodium hypo-chlorite in 1 1 water). After incubation for 20 minutes at 37C, the adsorption is measured by spectrophotometry in comparison with the same, but sample-free mixture of reagents, the indophenol derivative obtained being characterized by a coloration of which the intensity is proportional to the quantity of ammonia released and measurable at 634 nm in 10 mm cells. The % ammonia released is expressed by the relation: optical density of the sample with inhibitor/optical density of the sample without inhibitor x 100.
Results The anti-urease activity is expressed as the quantity of inhibitor tin microg) required to obtain 50%
inhibition represented by the mean value of 4 to 5 determinations for each inhibitor tested.
The results are set out in Table 1 below.
T~ble 1 Inhibitor Activity (microg) Usnic acid 250 (glycolic extract of Usnea barbata containing 7.5% usnate) Chlorogenic acid 200 (artichoke extract containing 46.7%
chlorogenic acid) Hamamelis 200 (15% tannins) Residue from the 500 decaffeination of green coffee eluted from the fraction retained on active carbon Extract of green carob 500 (desugared with hot water) Extract of green tea1000 Table 1 (continued) Inhibitor Activity (microg) l-CQA 250 3,4-Di-CQA 250 3-CoQA 350 3,4-di-CoQA 1000 3,4-di-FQA 1000 3,4-di-CFQA 1000 Legend CQA = caffeoyl quinic acid FQA = feruloyl quinic acid CoQA = coumaroyl quinic acid CFQA = caffeoyl feruloyl quinic acid The quinic acid derivatives mentioned above were prepared in accordance with applicants' patent applica-tions filed on the same day as the present application under the following titles: "Quinic acid derivatives and a process for their production" and "3- and/or 4-Substi-tuted quinic acid derivatives and a process for their production".
Ex~mple 2 An in vitro test is carried on a protective cosmetic cream of which the anti-urease activity is evaluated as described in Example 1 by colorimetric determination of the ammonia released and of which the pH is directly measured in the reaction mixtures using a glass electrode. The initial hypothesis is that an infant with an average weight of 6 kg has its nappy changed every 4 h. During these 4 h, it produces on average 40 ml urine corresponding to 300 mg urea and 30 210123~
g feces containing a quantity of urease varying from 3 to 30 U. Thus, the quantity of cream to be applied to the sensitive areas is evaluated at 10 g containing 400 mg Hamamelis extract as inhibitor.
The cream is an oil-in-water emulsion of which the composition is shown in Table 2 below (the nomencla-ture used for the ingredients is that of the "Cosmetic, Toiletry and Fragrance Association, Inc., Washington DC"
in its French translation).
Table 2 Ingredient %
Phase A
Glycerol stearate 10 Cetoaryl octanoate 3 Palm olein (containing 3 Cl214 fatty acids) Sunflower oil 4 Wheat germ oil 0.3 Ph~se B
Glycerol 5 Water qsf 100 Phase C
Cyclomethicone 3 DL-alpha-tocopherol acetate 0.2 Preservative 0.2 Hamamelis extract 4 To prepare the cream, phases A and B are sepa-rately heated to 80C, after which phase B is poured into phase A with vigorous stirring. The mixture is then left to cool to 40C with continuous stirring, phase C is incorporated with vigorous stirring and the 210123~
whole is left to cool to ambient temperature with continuous stirring. The activity of the cream contain-ing the inhibitor is determined by comparison with an inhibitor-free cream in concentrations of 0.75 U and 7.5 U enzyme. The results relating to the quantity of ammonia released are set out in Table 3 below while those relating to the pH are set out in Table 4.
T~ble 3 O Composition Quantity Ammonia released ~mg) after of enzyme an incubation period X
(U) (h) Cream contain- 0.75 0.47 0.89 0.97 0.97 0.92 ing 4~ Hamam- 7.5 1.13 1.04 1.27 -- 0.87 elis extract Cream with no 0.75 1.38 2.18 1.74 2.26 2.61 inhibitor 7.5 5.92 9.66 9.66 -- 9.38 0 T~ble 4 Composition Quantity pH after a period X (h) of enzyme (U) 0 24 Cream contain- 0.75 5.79 5.84 ing 4% Hamam- 7.5 5.78 5.83 elis extract Cream with no 0.75 5.94 6.53 inhibitor 7.5 5.94 7.73 The results obtained show that the cream contain-ing the Hamamelis extract is capable of completely inhibiting urease in the two concentrations of 3 and 30 U.
~xample 3 A protective cream is prepared in the form of a 21012'3~
water-in-oil emulsion of which the composition is shown in Table 5 below.
Table 5 Ingredients %
Ph~se A
Microcrystalline wax, 9 pentaerythritol cocoate, stearyl citrate, glycerol oleate, aluminium stearate and propylene glycol Decyl oleate 3 Palm olein (containing 10 Cl214 fatty acids) Sunflower oil 12 Ozocerite 0.5 Wheat germ oil 0.3 Ph~se B
Glycerol 5 Water qsf 100 Ph~se C
DL-alpha-tocopherol acetate 0.2 Cyclomethicone 3 Preservative 0.2 Hamamelis extract 4 The oil-in-water cream is prepared as described above for the cream of Example 2.
Claims (8)
1. An anti-urease cosmetic or dermatological compo-sition containing tannins, characterized in that it contains an effective quantity of anti-urease agent selected from condensed carob tannins and chlorogenic acid derivatives.
2. An antiperspirant and anti-nappy rash composition as claimed in claim 1.
3. A composition as claimed in claim 1, charac-terized in that it contains a residue from the decaf-feination of an aqueous green coffee extract rich in chlorogenic acid as anti-urease agent.
4. A composition as claimed in any of claims 1 to 3, characterized in that it contains 0.1 to 10% by weight anti-urease agent.
5. A composition as claimed in claim 4, charac-terized in that it is formulated as a cream based on a water-in-oil or oil-in-water emulsion.
6. A process for the preparation of the composition claimed in claim 5, characterized in that a fatty phase containing an emulsifier and an aqueous phase are separately heated, the two phases thus heated are mixed with vigorous stirring, the mixture is left to cool with stirring to an intermediate temperature, additives and the anti-urease agent are incorporated and the mixture is then cooled to ambient temperature with continuous stirring.
7. The use of a Hamamelis extract as an anti-urease agent.
8. The use claimed in claim 7 as an anti-nappy rash agent.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP92113188 | 1992-08-03 | ||
| EP92113188.4 | 1992-08-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2101234A1 true CA2101234A1 (en) | 1994-02-04 |
Family
ID=8209869
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2101234 Abandoned CA2101234A1 (en) | 1992-08-03 | 1993-07-23 | Anti-urease cosmetic or dermatological composition |
Country Status (6)
| Country | Link |
|---|---|
| JP (1) | JPH06183989A (en) |
| AU (1) | AU4208293A (en) |
| CA (1) | CA2101234A1 (en) |
| FI (1) | FI933431A (en) |
| NO (1) | NO932741L (en) |
| ZA (1) | ZA935171B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR19980034292A (en) * | 1996-11-06 | 1998-08-05 | 성재갑 | Skin whitening composition containing galloylquinic acid |
| JP3661975B2 (en) * | 1998-11-24 | 2005-06-22 | 福寿水産株式会社 | Ammonia generation inhibitor, ammonia generation-suppressed food, production method thereof, and ammonia generation suppression method |
| MXPA05010890A (en) | 2003-04-16 | 2006-03-21 | Vdf Futureceuticals | Low-mycotoxin coffee cherry products. |
| AU2003225038A1 (en) | 2003-04-16 | 2004-11-26 | Vdf Futureceuticals | Methods for coffee cherry products |
| MXPA06011530A (en) | 2004-04-08 | 2007-03-21 | Vdf Futureceuticals Inc | Coffee cherry cosmetic compositions and methods. |
-
1993
- 1993-07-16 ZA ZA935171A patent/ZA935171B/en unknown
- 1993-07-20 AU AU42082/93A patent/AU4208293A/en not_active Abandoned
- 1993-07-23 CA CA 2101234 patent/CA2101234A1/en not_active Abandoned
- 1993-07-30 NO NO932741A patent/NO932741L/en unknown
- 1993-08-02 FI FI933431A patent/FI933431A/en not_active Application Discontinuation
- 1993-08-02 JP JP5191258A patent/JPH06183989A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FI933431A (en) | 1994-02-04 |
| NO932741D0 (en) | 1993-07-30 |
| FI933431A0 (en) | 1993-08-02 |
| JPH06183989A (en) | 1994-07-05 |
| ZA935171B (en) | 1994-03-02 |
| NO932741L (en) | 1994-02-04 |
| AU4208293A (en) | 1994-02-10 |
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