IL95096A - Stabilized aqueous solutions of hydrogen peroxide - Google Patents
Stabilized aqueous solutions of hydrogen peroxideInfo
- Publication number
- IL95096A IL95096A IL9509690A IL9509690A IL95096A IL 95096 A IL95096 A IL 95096A IL 9509690 A IL9509690 A IL 9509690A IL 9509690 A IL9509690 A IL 9509690A IL 95096 A IL95096 A IL 95096A
- Authority
- IL
- Israel
- Prior art keywords
- hydrogen peroxide
- solution according
- solution
- acid
- integer equal
- Prior art date
Links
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 title claims abstract description 61
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 19
- 239000000243 solution Substances 0.000 claims abstract description 36
- 239000002253 acid Substances 0.000 claims abstract description 24
- 239000000203 mixture Substances 0.000 claims abstract description 21
- 239000003381 stabilizer Substances 0.000 claims abstract description 17
- 235000011180 diphosphates Nutrition 0.000 claims abstract description 15
- -1 alkaline-earth metal pyrophosphate Chemical class 0.000 claims abstract description 12
- 238000004061 bleaching Methods 0.000 claims abstract description 9
- 150000003839 salts Chemical class 0.000 claims abstract description 9
- 150000007513 acids Chemical class 0.000 claims abstract description 7
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims abstract description 7
- 239000004753 textile Substances 0.000 claims abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 230000000087 stabilizing effect Effects 0.000 claims description 5
- 229920001131 Pulp (paper) Polymers 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000010348 incorporation Methods 0.000 abstract description 2
- 229940048084 pyrophosphate Drugs 0.000 description 9
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 230000007774 longterm Effects 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- WYMDDFRYORANCC-UHFFFAOYSA-N 2-[[3-[bis(carboxymethyl)amino]-2-hydroxypropyl]-(carboxymethyl)amino]acetic acid Chemical compound OC(=O)CN(CC(O)=O)CC(O)CN(CC(O)=O)CC(O)=O WYMDDFRYORANCC-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
- 150000001768 cations Chemical class 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- 238000002161 passivation Methods 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FYUDERIVRYVSGE-UHFFFAOYSA-N 1,3-diaminoprop-1-en-2-ol Chemical compound NCC(O)=CN FYUDERIVRYVSGE-UHFFFAOYSA-N 0.000 description 1
- UYBWIEGTWASWSR-UHFFFAOYSA-N 1,3-diaminopropan-2-ol Chemical compound NCC(O)CN UYBWIEGTWASWSR-UHFFFAOYSA-N 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000007857 degradation product Substances 0.000 description 1
- 230000000249 desinfective effect Effects 0.000 description 1
- 238000001784 detoxification Methods 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- TVQLLNFANZSCGY-UHFFFAOYSA-N disodium;dioxido(oxo)tin Chemical compound [Na+].[Na+].[O-][Sn]([O-])=O TVQLLNFANZSCGY-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000009854 hydrometallurgy Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000002452 interceptive effect Effects 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000005304 optical glass Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
- FQENQNTWSFEDLI-UHFFFAOYSA-J sodium diphosphate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]P([O-])(=O)OP([O-])([O-])=O FQENQNTWSFEDLI-UHFFFAOYSA-J 0.000 description 1
- 229940048086 sodium pyrophosphate Drugs 0.000 description 1
- 229940079864 sodium stannate Drugs 0.000 description 1
- 238000013112 stability test Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 235000019818 tetrasodium diphosphate Nutrition 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B15/00—Peroxides; Peroxyhydrates; Peroxyacids or salts thereof; Superoxides; Ozonides
- C01B15/01—Hydrogen peroxide
- C01B15/037—Stabilisation by additives
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Detergent Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Paper (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- External Artificial Organs (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Dental Preparations (AREA)
Abstract
Aqueous solution of hydrogen peroxide stabilized by incorporation of a composition containing a mixture of alkaline or alkaline-earth metal pyrophosphate with a stabilizer pertaining to the class of aminopolycarboxylic acids having the general formula (I) wherein x is an integer equal to 0,1 or 2 and y is also an integer equal to 0,1 or 2; and salts of such acids. The solution finds application to the bleaching of textiles and pulp.
[WO9101268A1]
Description
>j.ran-b3> ΐη>η *σ ηι^ΐ'ο nv»a»n n o'nii Stabilized aqueous solutions of hydrogen peroxide INTEROX C. 81109 The present invention relates to aqueous solutions of hydrogen peroxide stabilized against decomposition into oxygen and water by means of compositions containing organic stabilizers belonging to the family of aminopolycarboxylic acids.
The process for stabilizing aqueous solutions of hydrogen peroxide by means of such stabilizers also falls within the scope of the invention.
It is known to use 1, 3-diamino-2-hydroxypropane-N Ν,Ν' ,Ν'-tetraacetic acid to stabilize per-compounds (GB-1383741 (CIBA-GEIGY, AG) * page 1, lines 44 to 61 *) . However, this compound is not stable in the presence of per-compounds and is rapidly converted during storage, giving rise to degradation products which no longer have a stabilizing effect on the solutions of per-compounds.
The object of the invention is solutions of hydrogen peroxide effectively stabilized in the long term by the incorporation of a composition containing an aminopolycarboxylic acid.
To this end, the invention relates to an aqueous solution of hydrogen peroxide stabilized by means of a composition containing a mixture of an alkali metal pyrophosphate or alkaline earth metal pyrophosphate with a stabilizer belonging to the category of aminopoly-carboxylic acids, in which composition the stabilizer is an aminopolycarboxylic acid corresponding to the following general formula: HOOC-CH2 CH2-COOH \ / where x is an integer equal to 0, 1 or 2 and y is also an integer equal to 0, 1 or 2; or a salt of this acid.
An aqueous solution of hydrogen peroxide is understood to be any aqueous solution of hydrogen peroxide in which the concentration by weight is between 0.1 and 99 g H202/100 g of solution and preferably 0.5 and 95%. Advantageously, this solution can be a commercial solution of hydrogen peroxide having a concentration by weight of between 25 and 70 g H2O2/100 g of solution.
Most frequently it is advantageous that the numbers x and y in the general formula of the aminopoly-carboxylie acid are such that their sum is not greater than 3 and preferably not greater than 2.
According to another variant of the process according to the invention, which is preferred, the aminopolycarboxylie acid which is used is such that the numbers x and y which occur in its formula are equal.
An aminopolycarboxylie acid which has given particularly worthwhile results is 1, 3-diamino-2-hydroxy-propane-Ν,Ν,Ν' ,Ν'-tetraacetic acid.
According to a supplementary variant of the process according to the invention, the numbers x and y in the general formula of the aminopolycarboxylie acid are such that one of them is zero. In such a case it is desirable that the other number differs from zero and, for example, is 1.
According to the invention, the salts of the aminopolycarboxylic acid comprise the salts resulting from the replacement of the hydrogen atom or one or more of the four carboxy1 groups of the aminopolycarboxylic acid by a metal cation or by ammonium. The metal cation is preferably a alkali metal or alkaline earth metal cation. The alkali metals and ammonium are particularly recommended.
Hereinafter the term aminopolycarboxylate will denote the aminopolycarboxylic acids and their salts according to the invention.
In the stabilizing compositions according to the invention, the proportion by weight of pyrophosphate and of aminopolycarboxylate can vary between 0.2 and 4.0 and preferably between 0.7 and 1.3. Excellent results have been obtained with a ratio by weight of pyrophosphate: aminopolycarboxylate of 1.0.
The optimum content of pyrophosphate/aminopolycarboxylate composition in the aqueous solutions of hydrogen peroxide depends on various parameters , in particular on the hydrogen peroxide concentration of the solution, its pH and the aminocarboxylate selected. In practice, it is generally desirable that the aqueous solution of hydrogen peroxide contains at least 0.5 mg of pyrophosphate/aminopolycarboxylate composition per kg of solution, and preferably not more than 1500 mg. The preferred contents are between 1 and 300 g.
The invention applies without differentiation to hydrogen peroxide solutions which are acid, neutral or basic. In particular, it finds an advantageous application for acid solutions which have a pH of between 2 and 5.
Examples of such solutions are . the hydrogen peroxide solutions used for cleaning optical glasses, in particular contact lenses , the H202 solutions for hydro- metallurgy, in particular in extraction of metals by leaching the ores, the H202 solutions for engraving, cleaning and polishing metals (for example the baths for chemical polishing of copper, such as those described in Patent application FR-A-87.13407 (SOLVAY & Cie) publication No. FR-A-2621052 ) , the H202 solutions used for protection of the environment, such as those used for detoxification of liquid or gaseous effluents and those used for the purification of water, the H202 solutions used in the foodstuffs industry and, in particular, those used for disinfecting packaging and containers .
According to an advantageous embodiment of the invention, the aqueous solution of hydrogen peroxide can be an aqueous bleaching bath containing hydrogen peroxide in a concentration of between 0.5 and 50 g H2O2/100 g of solution. Examples of such bleaching baths are the washing or bleaching liquors containing hydrogen peroxide for textile materials and the bleaching liquors containing hydrogen peroxide for paper pulps.
In the techniques for bleaching paper pulps using aqueous solutions of hydrogen peroxide it can sometimes prove advantageous to pretreat the paper pulp to be bleached with a pyrophosphate/aminopolycarboxylate composition of the same type as those used in accordance with the invention as defined hereinabove before carrying out the bleaching treatment with hydrogen peroxide. This latter technique is particularly interesting when the pulp to be bleached belongs to the category of high-yield pulps .
The invention also relates to a process for stabilizing an aqueous solution of hydrogen peroxide, according to which a composition containing a mixture of an alkali metal pyrophosphate or alkaline earth metal pyrophosphate with a stabilizer belonging to the category of the aminopolycarboxylie acids corresponding to the following general formula: H00C-CH2 CH2-C00H \ / where x is an integer equal to 0, 1 or 2 and y is also an integer equal to 0, 1 or 2; or salts of these acids is incorporated in the aqueous solution.
The invention has the advantage of providing aqueous solutions of hydrogen peroxide which have a long-term stability which is improved in respect of the decomposition induced by heavy metal and transition metal cations compared with known organic and inorganic stabilizers. The non-limiting examples which follow are given with the aim of illustrating the invention.
Examples 1R to 14 Passivation of the equipment; The equipment used in all of the examples which will be given below was subjected beforehand to a passivation treatment with the aim of eliminating the interfering effect of impurities adsorbed on the surface in contact with the stabilized hydrogen peroxide solutions used.
To carry out this treatment, all of the glassware which may be brought into contact with H202 was immersed in a 65% by weight aqueous solution of HN03 and the whole was kept at 75°C for 24 hours.
Long-term stability tests An 85% by weight aqueous solution of hydrogen peroxide, twice-distilled water, the stabilizer and a solution of metal ions containing FeCl3 and CuCl2 in a ratio of 5 moles of FeCl3 to 1 mole of CuCl2 were mixed in a l l conical flask passivated as described above. The amounts of the various components used were calculated to make up two types of final mixture containing, respectively, 35 g H2O2/100 g of solution and 70 g H2O2/100 g of solution as well as 5 mg of metals (expressed as Fe + Cu) per kg of solution and 250 mg of stabilizer (containing 100% of active material) per kg of solution.
The results obtained are given in Tables I (35% by weight H202) and II (70% by weight H202) , which follow.
In Experiments 5R, 7, 12R and 14, where a mixture of two stabilizers was used, 125 mg of each of the two stabilizers was introduced per kg of solution.
The stabilizers used were, on the one hand, 1, 3-diamino-2-hydroxypropane-N,N,N' ,Ν'-tetraacetic acid (designated DPTA below) according to the invention and, on the other hand, some known stabilizers which are not in accordance with the invention and belong to 2 distinct groups, that is to say a polyphosphonate manufactured by Monsanto and sold under the brand name DEQUEST, and two stabilizers of the inorganic type. These various stabilizers were used on their own or as a mixture and have been designated by the following abbreviations: PYRO : Na2H2P207 : sodium pyrophosphate, STAN : NazSn03 : sodium stannate.
D2066 : diethylenetriaminepenta ( a methylenephosphonate ) , where the abbreviation D2066 symbolizes the product DEQUEST® from Monsanto.
Table I (*) after 1 day Table II (*) after 1 day The results clearly show the synergistic effect produced by DPTA and PYRO in accordance with the solution according to the invention.
Claims (10)
1. Aqueous solution of hydrogen peroxide stabilized by means of a composition containing a stabilizer belonging to the category of the aminopolycarboxylie acids, characterized in that the composition contains a mixture of an alkali metal pyrophosphate or alkaline earth metal pyrophosphate with an aminopolycarboxylic acid corresponding to the following general formula t where x is an integer equal to 0, 1 or 2 and y is also an integer equal to 0, 1 or 2; or with a salt of this acid.
2. Solution according to Claim 1, characterized in that x and y are such that their sum is not greater than 3.
3. Solution according to Claim 1 or 2, characterized in that x and y have the same value.
4. Solution according to Claim 1 or 2, characterized in that one of the numbers x or y is zero.
5. Solution according to any one of Claims 1 to 4, characterized in that the proportion by weight of alkali metal or alkaline earth metal pyrophosphate to aminopolycarboxylic acid or one of its salts is between 0.2 and 4.0.
6. Solution according to Claim 3, characterized in that the aminopolycarboxylic acid is lf 3-diamino-2-hydroxypropane-Ν,Ν,Ν' ,Ν'-tetraacetic acid.
7. Solution according to any one of Claims 1 to 6, characterized in that it is a commercially available concentrated solution having a concentration by weight of between 0.5 and 95% of hydrogen peroxide.
8. Solution according to any one of Claims 1 to 6, characterized in that it is a washing or bleaching bath for textiles.
9. Solution according to any one of Claims 1 to 6, characterized in that it is a bleaching liquor for paper pulp.
10. Process for stabilizing an aqueous solution of hydrogen peroxide by means of a composition containing a stabilizer belonging to the category of the aminopoly-carboxylic acids, characterized in that a mixture of an alkali metal pyrophosphate or alkaline earth metal pyrophosphate with an aminopolycarboxylic acid corresponding to the following general formula: where x is an integer equal to 0, 1 or 2 and y is also an integer equal to 0, 1 or 2; or with a salt of this acid, is incorporated in the solution. For fhe Applicants DR. REINHOtD COHN AND PARTNERS By: "
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE8900796A BE1004292A3 (en) | 1989-07-20 | 1989-07-20 | Stabilized aqueous solution of hydrogen peroxide and method for stabilizing aqueous solution of hydrogen peroxide. |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL95096A0 IL95096A0 (en) | 1991-06-10 |
| IL95096A true IL95096A (en) | 1995-03-30 |
Family
ID=3884260
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL9509690A IL95096A (en) | 1989-07-20 | 1990-07-16 | Stabilized aqueous solutions of hydrogen peroxide |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0483170B1 (en) |
| JP (1) | JPH04506951A (en) |
| KR (1) | KR920703440A (en) |
| AT (1) | ATE97390T1 (en) |
| AU (1) | AU630982B2 (en) |
| BE (1) | BE1004292A3 (en) |
| BG (1) | BG60097B2 (en) |
| BR (1) | BR9007544A (en) |
| CA (1) | CA2064048C (en) |
| DD (1) | DD296675A5 (en) |
| DE (1) | DE69004694T2 (en) |
| ES (1) | ES2062535T3 (en) |
| FI (1) | FI94617C (en) |
| HU (1) | HU211436B (en) |
| IE (1) | IE65415B1 (en) |
| IL (1) | IL95096A (en) |
| NO (1) | NO305894B1 (en) |
| NZ (1) | NZ234569A (en) |
| RO (1) | RO110224B1 (en) |
| RU (1) | RU2069638C1 (en) |
| SG (1) | SG61094G (en) |
| WO (1) | WO1991001268A1 (en) |
| YU (1) | YU47152B (en) |
| ZA (1) | ZA905408B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU689956B2 (en) * | 1994-10-04 | 1998-04-09 | Tetra Laval Holdings & Finance Sa | Method of disinfecting the food contact surfaces of food packaging machines and disinfecting solution therefor |
| CN105671933B (en) * | 2016-01-25 | 2018-01-19 | 苏州印丝特纺织数码科技有限公司 | A kind of polysiloxane-based stabilizer of hydrogen peroxide for being used to weave |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1383741A (en) * | 1971-04-13 | 1974-02-12 | Ciba Geigy Ag | Stabilisation of per-compounds |
| US3903244A (en) * | 1973-02-02 | 1975-09-02 | Fmc Corp | Stabilized hydrogen peroxide |
| US4320102A (en) * | 1980-10-10 | 1982-03-16 | Air Products And Chemicals, Inc. | Method of stabilizing hydrogen peroxide solutions |
| US4454224A (en) * | 1982-12-22 | 1984-06-12 | Eastman Kodak Company | Photographic bleaching compositions |
-
1989
- 1989-07-20 BE BE8900796A patent/BE1004292A3/en not_active IP Right Cessation
-
1990
- 1990-07-10 ZA ZA905408A patent/ZA905408B/en unknown
- 1990-07-12 AT AT90909593T patent/ATE97390T1/en not_active IP Right Cessation
- 1990-07-12 RU SU905011208A patent/RU2069638C1/en active
- 1990-07-12 EP EP90909593A patent/EP0483170B1/en not_active Expired - Lifetime
- 1990-07-12 KR KR1019920700130A patent/KR920703440A/en not_active Application Discontinuation
- 1990-07-12 AU AU58492/90A patent/AU630982B2/en not_active Ceased
- 1990-07-12 JP JP2509136A patent/JPH04506951A/en active Pending
- 1990-07-12 CA CA002064048A patent/CA2064048C/en not_active Expired - Fee Related
- 1990-07-12 DE DE69004694T patent/DE69004694T2/en not_active Expired - Fee Related
- 1990-07-12 ES ES90909593T patent/ES2062535T3/en not_active Expired - Lifetime
- 1990-07-12 BR BR909007544A patent/BR9007544A/en not_active IP Right Cessation
- 1990-07-12 WO PCT/BE1990/000041 patent/WO1991001268A1/en active IP Right Grant
- 1990-07-12 HU HU9200180A patent/HU211436B/en not_active IP Right Cessation
- 1990-07-12 RO RO149283A patent/RO110224B1/en unknown
- 1990-07-16 IL IL9509690A patent/IL95096A/en not_active IP Right Cessation
- 1990-07-18 DD DD90342880A patent/DD296675A5/en not_active IP Right Cessation
- 1990-07-18 YU YU140590A patent/YU47152B/en unknown
- 1990-07-19 NZ NZ234569A patent/NZ234569A/en unknown
- 1990-07-19 IE IE263690A patent/IE65415B1/en not_active IP Right Cessation
-
1992
- 1992-01-17 FI FI920211A patent/FI94617C/en active
- 1992-01-17 NO NO920243A patent/NO305894B1/en not_active IP Right Cessation
- 1992-01-20 BG BG95785A patent/BG60097B2/en unknown
-
1994
- 1994-04-29 SG SG61094A patent/SG61094G/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| KB | Patent renewed | ||
| RH | Patent void |