Classifications

• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/39—Organic or inorganic per-compounds
  • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
  • C11D3/3905—Bleach activators or bleach catalysts
  • C11D3/3907—Organic compounds
  • C11D3/3915—Sulfur-containing compounds
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/39—Organic or inorganic per-compounds
  • C11D3/3902—Organic or inorganic per-compounds combined with specific additives
  • C11D3/3905—Bleach activators or bleach catalysts
  • C11D3/3907—Organic compounds
  • C11D3/391—Oxygen-containing compounds

Definitions

• the present invention relates to the use of oxacarboxylic acid esters as Bleach activators for activating peroxygen compounds, especially for Bleaching of color stains when washing textiles, as well as detergents, cleaning agents and disinfectants, which contain such bleach activators.
• Inorganic peroxygen compounds especially hydrogen peroxide and solid peroxygen compounds, which dissolve in water to release hydrogen peroxide, such as sodium perborate and sodium carbonate perhydrate, have long been used as oxidizing agents for disinfection and bleaching purposes.
• the oxidizing effect of these substances in dilute solutions depends strongly on the temperature; For example, with H 2 O 2 or perborate in alkaline bleaching liquors, sufficiently quick bleaching of soiled textiles can only be achieved at temperatures above about 80 ° C.
• the oxidation effect of the inorganic peroxygen compounds can be improved by the addition of so-called bleach activators, which are able to deliver peroxocarboxylic acids under the perhydrolysis conditions mentioned and for which numerous suggestions, especially from the substance classes of the N- or O-acyl compounds, for example, multiple acylation Alkylenediamines, in particular N, N, N ' , N ' -tetraacetylethylenediamine (TAED), acylated glycolurils, in particular tetraacetylglycoluril, N-acylated hydantoins, hydrazides, triazoles, hydrotriazines, urazoles, diketopiperazines, sulfurylamides and cyanuric anhydrides, in particular carboxylic acid anhydrides, in addition carboxylic acid anhydrides, in addition, carboxylic acid anhydrides, in addition, carboxylic acid anhydrides, in addition, carbonic acid anhydrides,
• Carboxylic acid esters in particular sodium nonanoyloxy-benzenesulfonate (NOBS), sodium isononanoyloxy-benzenesulfonate, O-acylated sugar derivatives, such as pentaacetyl glucose, and N-acylated lactams, such as N-benzoylcaprolactam, have become known in the literature.
• NOBS sodium nonanoyloxy-benzenesulfonate
• O-acylated sugar derivatives such as pentaacetyl glucose
• N-acylated lactams such as N-benzoylcaprolactam
• bleach activators which are peroxocarboxylic acids release in which methylene groups are replaced by oxygen atoms are (hereinafter referred to as oxaperoxocarboxylic acids), an excellent bleach activating Effect against both hydrophobic and hydrophilic colored Soiling and especially at low temperatures Release the corresponding peroxocarboxylic acid faster than known ones Bleach activators.
• R 1 represents an alkyl or alkenyl radical having 1 to 5 carbon atoms, an aryl radical optionally substituted by alkyl or alkenyl radicals having 1 to 5 carbon atoms, an aryl radical optionally substituted by alkyl or alkenyl radicals having 1 to 5 carbon atoms C 3 - to C 10 cycloalkyl radical or the rest
• R 2 is an alkylene, alkenylene or arylene radical having 1 to 10 carbon atoms and their mixtures
• X drove an ionic or ionizable group, in particular -SO 3 M, -OSO 3 M, -COOM, -PO (OM ) 2 , -OPO (OM) 2 , - N + R 3 R 4 R 5 Y - , M for hydrogen, an alkali metal or optionally substituted ammonium ion, R 3 , R 4 and R 4 independently of one another for hydrogen, an alkyl
• the one ionic or ionizable group -X on the aromatic ring of the leaving group is preferably in the ortho or para position to the ester function.
• the preferred groups X include -SO 3 M.
• Preferred alkali metals M are sodium and potassium.
• the radicals R 1 and R 2 in the compounds of the general formula I can, if they are alkyl or alkenyl or alkylene or alkenylene radicals, be linear or branched.
• the radicals R 1 and R 2 can also be linked in a ring-closing manner and thus be part of a heterocyclic system.
• the bleach activators according to formula (I) to be used according to the invention can release oxaperoxocarboxylic acids with one or two percarboxy units.
• R 1 is a phenyl, methyl, ethyl, propyl or isopropyl radical or a mixture of these, in particular a methyl radical, the alkyl radicals being linear or (where possible) ) can be branched.
• the preferred compounds of the formula (I) also include those in which R 2 is methylene, 1,2-ethylene, 1,2-propylene, 1,3-propylene, 1,2-phenylene, 1 , 3-phenylene and / or 1,4-phenylene group.
• Preferred values for n are in the range from 1 to 5.
• the particularly preferred compounds of the general formula (I) include those of the formulas (II) or (III), in which m means 1 or 2.
• washing agents and disinfectants for use in particulate detergents, cleaning agents and disinfectants Substances according to formula I to be used according to the invention preferably at room temperature firmly.
• the compounds according to formula I are preferably used for bleaching of color stains when washing textiles, especially in aqueous, Fleet containing surfactant used.
• the phrase "bleaching paint stains" is to be understood in its broadest meaning and includes both the bleaching of dirt on the textile, the bleaching of in the wash liquor dirt detached from the textile as well as the oxidative destruction of itself textile dyes in the wash liquor, which are under the washing conditions of Peel off textiles before they can be drawn onto textiles of a different color.
• bleaching means both the bleaching of what is on the hard surface Dirt, especially tea, as well as bleaching in the dishwashing liquor dirt that is detached from the hard surface.
• detergents, cleaning agents and disinfectants which contain a compound of formula I as a bleach activator and a process for Activation of peroxygen compounds using such a compound according to formula I.
• the compounds of formula I can be used as activators anywhere there be where there is a special increase in the oxidation effect of inorganic Peroxygen compounds arrive at low temperatures, for example at Bleaching of textiles, hair or hard surfaces, with the oxidation of organic or inorganic intermediates and in disinfection.
• the use according to the invention consists essentially in conditions create, among which a peroxygen compound and a compound of formula I. can react with each other with the aim of having more oxidizing secondary products to obtain.
• Such conditions exist especially when the reactants meet in aqueous solution.
• This can be done by adding the Peroxygen compound and the bleach activator in a separate form if necessary detergent or detergent solution happen.
• an inventive Detergent, cleaning agent or disinfectant which the bleach activator according to formula I and optionally contains a peroxidic oxidizing agent.
• the peroxygen compound can also be separately, in bulk or as a preferably aqueous solution or suspension, for washing, cleaning or disinfecting solution be added if a peroxygen-free agent is used.
• the conditions can be varied widely depending on the intended use. So come in addition to purely aqueous solutions, also mixtures of water and suitable organic Solvents as a reaction medium in question.
• the quantities of peroxygen compounds used are generally chosen so that in the solutions between 10 ppm and 10% active oxygen, preferably between 50 and 5000 ppm active oxygen available.
• the amount of bleach activator according to formula I used also depends depending on the application. Depending on the desired degree of activation, so much of the Bleach activator according to formula I to be used according to the invention that 0.03 mol to 1 mol, preferably 0.1 mol to 0.5 mol bleach activator per mol Peroxygen compounds are used, but in special cases they can Limits can also be exceeded or fallen short of.
• a washing, cleaning or disinfecting agent according to the invention preferably contains 0.2% by weight to 30% by weight, in particular 1% by weight to 20% by weight Bleach activator according to formula I in addition to the usual ones compatible with the bleach activator Ingredients.
• the activating substances to be used according to the invention can adsorbed onto carrier substances and / or in coating substances in a manner known in principle be embedded.
• the detergents, cleaning agents and disinfectants according to the invention which in particular powdery solids, in compacted particle form, as homogeneous solutions or suspensions may also be present in addition to the invention using bleach activator according to formula I in principle all known and in such Contain common ingredients.
• the washing and Cleaning agents can in particular builder substances, surface-active surfactants organic and / or in particular inorganic peroxygen compounds, water-miscible organic solvents, enzymes, sequestrants, electrolytes, pH regulators and other auxiliaries, such as optical brighteners, graying inhibitors, Color transfer inhibitors, foam regulators, additional peroxygen activators, Dyes and fragrances included.
• a disinfectant according to the invention can be used to enhance the disinfectant effect compared to special germs in addition to the previously mentioned Contain ingredients common antimicrobial agents.
• Such antimicrobial Additives are preferably in the disinfectants according to the invention in Amounts up to 10 wt .-%, in particular from 0.1 wt .-% to 5 wt .-%, contain.
• bleach activators according to formula I to be used according to the invention can be the usual substances mentioned at the beginning under perhydrolysis conditions Form peroxocarboxylic acids and / or conventional transition metal complexes activating the bleach be used.
• Organic peracids in particular come as suitable peroxygen compounds peracidic salts of organic acids, such as phthalimidopercaproic acid, perbenzoic acid or salts of diperdodecanedioic acid, hydrogen peroxide and among Washing or cleaning conditions Hydrogen peroxide-releasing inorganic Salts such as perborate, percarbonate and / or persilicate. Hydrogen peroxide can also use an enzymatic system, that is an oxidase and its substrate. Provided solid peroxygen compounds to be used, they can be used in the form of powders or granules that can also be encased in a manner known in principle.
• the peroxygen compounds can, as such or in the form of compositions containing them, the in principle contain all the usual detergent, disinfectant ingredients can be added to the washing or cleaning liquor.
• Alkali percarbonate, alkali perborate monohydrate, alkali perborate tetrahydrate is particularly preferred or hydrogen peroxide in the form of aqueous solutions containing 3% by weight Contain 10 wt .-% hydrogen peroxide used.
• an inventive Detergents or cleaning agents contain peroxygen compounds, these are in quantities of preferably up to 50% by weight, in particular from 5% by weight to 30% by weight, present, while in the disinfectants according to the invention preferably from 0.5% by weight to 40% by weight, in particular from 5% by weight to 20% by weight, of peroxygen compounds are included.
• the agents according to the invention can contain one or more surfactants, in particular anionic surfactants, nonionic surfactants and their mixtures come into question.
• Suitable nonionic surfactants are especially alkyl glycosides and ethoxylation and / or propoxylation products of alkyl glycosides or linear or branched Alcohols each with 12 to 18 carbon atoms in the alkyl part and 3 to 20, preferably 4 to 10 alkyl ether groups.
• Corresponding ethoxylation and / or Propoxylation products of N-alkyl amines, vicinal diols, Fatty acid esters and fatty acid amides, the long-chain mentioned with respect to the alkyl part Alcohol derivatives correspond, as well as of alkylphenols with 5 to 12 carbon atoms usable in the alkyl radical.
• Suitable anionic surfactants are in particular soaps and those containing sulfate or Contain sulfonate groups with preferably alkali ions as cations.
• Usable soaps are preferably the alkali salts of saturated or unsaturated fatty acids with 12 to 18 carbon atoms. Such fatty acids can also be in a form which is not completely neutralized be used.
• the surfactants of the sulfate type include the salts of Sulfuric acid half-esters of fatty alcohols with 12 to 18 carbon atoms and the sulfation products of the nonionic surfactants mentioned with a low degree of ethoxylation.
• Usable sulfonate-type surfactants include linear alkyl benzene sulfonates with 9 to 14 carbon atoms in the alkyl part, alkane sulfonates with 12 to 18 carbon atoms, and olefin sulfonates with 12 to 18 carbon atoms, which are involved in the implementation corresponding monoolefins with sulfur trioxide are formed, as well as alpha-sulfofatty acid esters, which result from the sulfonation of fatty acid methyl or ethyl esters.
• Such surfactants are in the cleaning or washing agents according to the invention in Quantities of preferably 5% by weight to 50% by weight, in particular 8% by weight up to 30 wt .-%, while the disinfectants according to the invention such agents according to the invention for cleaning dishes, preferably 0.1% by weight to Contain 20 wt .-%, in particular 0.2 wt .-% to 5 wt .-% surfactants.
• An agent according to the invention preferably contains at least one water-soluble and / or water-insoluble, organic and / or inorganic builder.
• the water-soluble organic builder substances include polycarboxylic acids, in particular citric acid and sugar acids, monomeric and polymeric aminopolycarboxylic acids, in particular methylglycinediacetic acid, nitrilotriacetic acid and ethylenediaminetetraacetic acid, and also polyaspartic acid, polyphosphonic acids, in particular aminotris (methylenephosphonic acid), ethylenediaminephosphonic acid, ethylenediaminephosphonic acid, ethylenediaminephosphonic acid, ethylenediaminephosphonic acid, ethylenediaminephosphonic acid, ethylenediaminephosphonic acid, ethylenediaminephosphonic acid and ethylenediaminephosphonic acid, ethylenediaminephosphonic acid, ethylenediaminephosphonic acid, ethylenediaminephosphonic acid, ethylenediaminephosphonic acid, and ethylenediaminephosphonic
• the relative molecular weight of the homopolymers of unsaturated carboxylic acids is generally between 5,000 and 200,000, that of the copolymers between 2,000 and 200,000, preferably 50,000 to 120,000, in each case based on free acid.
• a particularly preferred acrylic acid-maleic acid copolymer has a relative molecular weight of 50,000 to 100,000.
• Suitable, albeit less preferred, compounds of this class are copolymers of acrylic acid or methacrylic acid with vinyl ethers, such as vinyl methyl ethers, vinyl esters, ethylene, propylene and styrene, in which the proportion of acid is at least 50% by weight.
• Terpolymers can also be used as water-soluble organic builder substances which contain two unsaturated acids and / or their salts as monomers and vinyl alcohol and / or an esterified vinyl alcohol or a carbohydrate as the third monomer.
• the first acidic monomer or its salt is derived from a monoethylenically unsaturated C 3 -C 8 carboxylic acid and preferably from a C 3 -C 4 monocarboxylic acid, in particular from (meth) acrylic acid.
• the second acidic monomer or its salt can be a derivative of a C 4 -C 8 dicarboxylic acid, maleic acid being particularly preferred, and / or a derivative of an allylsulfonic acid which is substituted in the 2-position by an alkyl or aryl radical.
• Polymers of this type can be produced in particular by processes which are described in German patent specification DE 42 21 381 and German patent application DE 43 00 772 and generally have a relative molecular weight of between 1,000 and 200,000. Further preferred copolymers are those which are described in German patent applications DE 43 03 320 and DE 44 17 734 and which preferably contain acrolein and acrylic acid / acrylic acid salts or vinyl acetate as monomers.
• the organic builder substances in particular for the production of liquid agents, can be used in the form of aqueous solutions, preferably in the form of 30 to 50 percent by weight aqueous solutions. All of the acids mentioned are generally used in the form of their water-soluble salts, in particular their alkali metal salts.
• Such organic builder substances can, if desired, in amounts up to 40% by weight, in particular up to 25% by weight and preferably from 1% by weight to 8% by weight be included. Amounts close to the above upper limit are preferably in paste-like or liquid, in particular water-containing agents according to the invention used.
• polymers come as water-soluble inorganic builder materials
• Alkali phosphates in the form of their alkaline neutral or acidic sodium or Potassium salts can be considered.
• Examples include tetrasodium diphosphate, Disodium dihydrogen diphosphate, pentasodium triphosphate, so-called Sodium hexametaphosphate and the corresponding potassium salts respectively Mixtures of sodium and potassium salts.
• water-insoluble, water-dispersible inorganic builder materials are in particular crystalline or amorphous alkali alumosilicates, in amounts of up to 50% by weight, preferably not more than 40% by weight and in liquid agents used in particular from 1 wt .-% to 5 wt .-%.
• crystalline sodium aluminosilicates in detergent quality in particular zeolite A, P and optionally X, preferred. Quantities will be close to the upper limit preferably used in solid, particulate compositions. Suitable aluminosilicates in particular have no particles with a grain size above 30 ⁇ m and exist preferably at least 80% by weight of particles with a size below 10 ⁇ m. your Calcium binding capacity, which according to the information in German patent DE 24 12 837 can usually be determined is in the range of 100 to 200 mg CaO per Grams.
• Suitable substitutes or partial substitutes for the aluminosilicate mentioned are crystalline alkali silicates, which can be present alone or in a mixture with amorphous silicates.
• the alkali silicates which can be used as builders in the agents according to the invention preferably have a molar ratio of alkali oxide to SiO 2 below 0.95, in particular from 1: 1.1 to 1:12, and can be amorphous or crystalline.
• Preferred alkali silicates are the sodium silicates, in particular the amorphous sodium silicates, with a Na 2 O: SiO 2 molar ratio of 1: 2 to 1: 2.8.
• Crystalline phyllosilicates of the general formula Na 2 Si x O 2x + 1 .yH 2 O are preferably used as crystalline silicates, which may be present alone or in a mixture with amorphous silicates, in which x, the so-called module, is a number 9 to 4 and y is a number from 0 to 20 and preferred values for x are 2, 3 or 4.
• Crystalline layered silicates which fall under this general formula are described, for example, in European patent application EP 0 164 514.
• Preferred crystalline layered silicates are those in which x assumes the values 2 or 3 in the general formula mentioned.
• ⁇ - and ⁇ -sodium disilicate Na 2 Si 2 O 5 .yH 2 O
• ⁇ -sodium disilicate can be obtained, for example, by the method described in international patent application WO 91/08171.
• ⁇ -sodium silicates with a modulus between 1.9 and 3.2 can be produced according to Japanese patent applications JP 04/238 809 or JP 04/260 610.
• Crystalline sodium silicates with a modulus in the range from 1.9 to 3.5 are used in a further preferred embodiment of agents according to the invention.
• a granular compound of alkali silicate and alkali carbonate is used, as is described, for example, in international patent application WO 95/22592 or as is commercially available, for example, under the name Nabion® 15.
• the weight ratio of aluminosilicate to silicate is preferably 1:10 to 10: 1.
• the weight ratio of amorphous alkali silicate to crystalline alkali silicate is preferably 1: 2 to 2: 1 and in particular 1: 1 to 2: 1.
• Builder substances are preferred in the washing or cleaning agents according to the invention in amounts up to 60% by weight, in particular from 5% by weight to 40% by weight, included, while the disinfectants according to the invention are preferably free of only the components of the water hardness complexing builder substances are and preferably not more than 20% by weight, in particular from 0.1% by weight to 5% by weight heavy metal complexing substances, preferably from the group comprising aminopolycarboxylic acids, Aminopolyphosphonic acids and hydroxypolyphosphonic acids and their water-soluble salts and mixtures thereof.
• the enzymes which can be used in the compositions are, besides the oxidase mentioned above those from the class of proteases, lipases, cutinases, amylases, pullulanases, Cellulases, hemicellulases, xylanases and peroxidases and mixtures thereof, for example proteases such as BLAP®.
• Fungi or bacteria such as Bacillus are particularly suitable subtilis, Bacillus licheniformis, Streptomyces griseus, Humicola lanuginosa, Humicola insolens, Pseudomonas pseudoalcaligenes or Pseudomonas cepacia obtained enzymatic Active ingredients.
• the optionally used enzymes can, for example in European patent EP 0 564 476 or in international patent applications WO 94/23005 described, adsorbed on carriers and / or in coating substances embedded to protect them against premature inactivation.
• usable organic solvents include alcohols with 1 to 4 carbon atoms, especially methanol, ethanol, isopropanol and tert-butanol, Diols with 2 to 4 carbon atoms, in particular ethylene glycol and propylene glycol, and their mixtures and the ethers derived from the compound classes mentioned.
• Such water-miscible solvents are in the washing, Detergents and disinfectants preferably not more than 30 wt .-%, in particular from 6% to 20% by weight.
• the agents according to the invention cannot system and pH environmentally compatible acids, especially citric acid, acetic acid, tartaric acid, malic acid, Lactic acid, glycolic acid, succinic acid, glutaric acid and / or adipic acid, however also mineral acids, especially sulfuric acid, or bases, especially ammonium or Alkali hydroxides included.
• pH regulators are in the invention Average preferably not more than 20 wt .-%, in particular from 1.2 wt .-% to 17% by weight.
• suitable color transfer inhibitors in particular polyvinylpyrrolidones, polyvinylimidazoles, polymeric N-oxides such as poly (vinylpyridine-N-oxide) and copolymers of vinyl pyrrolidone with vinyl imidazole.
• Graying inhibitors have the task of being of the hard surface and especially to keep dirt detached from the textile fibers suspended in the liquor.
• Water-soluble colloids of mostly organic nature are suitable for this, for example Starch, glue, gelatin, salts of ether carboxylic acids or ether sulfonic acids of starch or the cellulose or salts of acidic sulfuric acid esters of cellulose or Strength.
• Polyamides containing water-soluble acidic groups are also for this Suitable purpose.
• starch derivatives other than those mentioned above can be used use, for example aldehyde starches.
• Cellulose ethers such as Carboxymethyl cellulose (sodium salt), methyl cellulose, hydroxyalkyl cellulose and mixed ether, such as methylhydroxyethyl cellulose, methyl hydroxypropyl cellulose, methyl carboxymethyl cellulose and their mixtures, for example in amounts of 0.1 to 5% by weight, based on the funds used.
• the agents can be derivatives of diaminostilbenedisulfonic acid or whose alkali metal salts contain.
• diaminostilbenedisulfonic acid or whose alkali metal salts contain.
• Brighteners of the type of substituted diphenylstyryls may be present, for example the alkali salts of 4,4'-bis (2-sulfostyryl) diphenyl, 4,4'-bis (4-chloro-3-sulfostyryl) diphenyl, or 4- (4-chlorostyryl) -4 '- (2-sulfostyryl) diphenyl. Mixtures of the aforementioned optical Brighteners can be used.
• Suitable foam inhibitors are, for example, soaps of natural or synthetic origin, which have a high proportion of C 18 -C 24 fatty acids.
• Suitable non-surfactant-like foam inhibitors are, for example, organopolysiloxanes and their mixtures with microfine, optionally silanized silica, and also paraffins, waxes, microcrystalline waxes and their mixtures with silanized silica or bisfatty acid alkyl diamides. Mixtures of different foam inhibitors are also used with advantages, for example those made of silicone, paraffins or waxes.
• the foam inhibitors, in particular silicone and / or paraffin-containing foam inhibitors are preferably bound to a granular, water-soluble or dispersible carrier substance. Mixtures of paraffins and bistearylethylenediamide are particularly preferred.
• active ingredients can also be used Avoiding tarnishing of objects made of silver, so-called silver corrosion inhibitors, be used.
• Preferred silver corrosion inhibitors are organic Disulfides, dihydric phenols, trihydric phenols, optionally alkyl or aminoalkyl substituted Triazoles such as benzotriazole and cobalt, manganese, titanium, zirconium, Hafnium, vanadium or cerium salts and / or complexes in which the metals mentioned are in one of the oxidation states II, III, IV, V or VI.
• compositions according to the invention are not difficult and can be done in in a known manner, for example by spray drying or granulation, take place, the peroxygen compound and bleach activator optionally later be added.
• agents according to the invention with increased Bulk weight in particular in the range from 650 g / l to 950 g / l, is one of those European patent EP 486 592 known, having an extrusion step Process preferred.
• Detergents, cleaning agents or disinfectants according to the invention in the form of aqueous or other conventional solvent-containing solutions particularly advantageous by simply mixing the ingredients in bulk or as Solution can be placed in an automatic mixer.
• agents for the particular mechanical cleaning of Dishes are tablet-shaped and can be modeled on those in European Patent specifications EP 0 579 659 and EP 0 591 282 disclosed methods can be produced.

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• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

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Citations (7)

• 1997
  • 1997-05-23 DE DE1997121588 patent/DE19721588A1/de not_active Withdrawn
• 1998
  • 1998-05-14 EP EP98108785A patent/EP0879875A3/fr not_active Withdrawn

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