EP0360331B1 - Composition pour traiter le linge - Google Patents

Composition pour traiter le linge Download PDF

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Publication number
EP0360331B1
EP0360331B1 EP89202298A EP89202298A EP0360331B1 EP 0360331 B1 EP0360331 B1 EP 0360331B1 EP 89202298 A EP89202298 A EP 89202298A EP 89202298 A EP89202298 A EP 89202298A EP 0360331 B1 EP0360331 B1 EP 0360331B1
Authority
EP
European Patent Office
Prior art keywords
fabric
alkyl
benzimidazolyl
carbamate
treatment composition
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP89202298A
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German (de)
English (en)
Other versions
EP0360331A2 (fr
EP0360331A3 (fr
Inventor
Christine Morris
Graham Andrew Turner
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Unilever PLC
Unilever NV
Original Assignee
Unilever PLC
Unilever NV
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Filing date
Publication date
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Publication of EP0360331A2 publication Critical patent/EP0360331A2/fr
Publication of EP0360331A3 publication Critical patent/EP0360331A3/fr
Application granted granted Critical
Publication of EP0360331B1 publication Critical patent/EP0360331B1/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/402—Amides imides, sulfamic acids
    • D06M13/425—Carbamic or thiocarbamic acids or derivatives thereof, e.g. urethanes
    • 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
    • C11D3/48—Medical, disinfecting agents, disinfecting, antibacterial, germicidal or antimicrobial compositions
    • 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
    • C11D3/0005—Other compounding ingredients characterised by their effect
    • C11D3/001—Softening compositions
    • C11D3/0015—Softening compositions liquid
    • 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
    • C11D3/16—Organic compounds
    • C11D3/26—Organic compounds containing nitrogen
    • C11D3/28—Heterocyclic compounds containing nitrogen in the ring

Definitions

  • This invention relates to a fabric treatment composition for treating fabrics during the rinse step of a fabric laundry process, and to a method for using said composition.
  • the invention relates to a fabric treatment composition comprising a fabric-softening material, which is preferably a cationic fabric softening material and an antimicrobial agent.
  • benzimidazolyl-alkyl-carbamates when combined with fabric-softening materials into a fabric treatment composition, are particularly effective in inhibiting fungal growth on fabrics which have been rinsed with said fabric treatment composition.
  • a fabric treatment composition comprising a softening material and a benzimidazolyl-alkyl-carbamate.
  • the softening material comprises a cationic fabric softener.
  • Benzimidazolyl-alkyl-carbamates are well-known fungicides for use in agriculture. It has also been suggested in Japanese patent application 49 093 537 (Yoshitomi) to treat textiles with a composition containing Me-2-benzimidazole-carbamate in a solvent. This treatment, however, requires a separate processing step for applying the benzimidazolyl-alkyl-carbamate and a further separate processing step for removing the undesirable solvent compound.
  • benzimidazolyl-alkyl-carbamate as used in a textile treatment composition of the invention is preferably of the following formula: wherein:
  • benzimidazolyl-alkyl-carbamate substances are: benzimidazolyl-methyl-carbamate, benzimidazolyl-ethyl-carbamate, 5-ethyl-benzimidazolyl-ethyl-carbamate, benzimidazolyl-isopropyl-carbamate, 4-ethyl-benzimidazolyl-isopropyl-carbamate, 4-propyl-benzimidazolyl-isopropyl-carbamate, 4-butyl-benzimidazolyl-isopropyl-carbamate, 4-isobutyl-benzimidazolyl-isopropyl-carbamate, benzimidazolyl-ethylmethoxy-carbamate, 4-ethyl-benzimidazolyl-ethylmethoxy-carbamate, 5-ethyl-benzimidazolyl-ethylmethoxy-carbamate,
  • the preferred benzimidazolyl-alkyl-carbamate is benzimidazolyl-methyl-carbamate.
  • Intace® B 350 (75% carbendazim ex Intace
  • Intace® B 300 (100% carbendazim ex Intace).
  • antimicrobial substances may be incorporated in a fabric treatment composition according to the invention.
  • antimicrobial substances are meant both antibacterial and antifungal products. Examples of such material are formaldehyde, halogenated phenols, nitrated mono- or polyalcohols and antimicrobial surface-active tensides.
  • benzimidazolyl-alkyl-carbamates Particularly suitable for use in conjunction with benzimidazolyl-alkyl-carbamates are tetra-methylthiuramdisulphid, 1-methylol-2-thiono-2-dihydrobenzthiazol, N-dimethyl-N′-phenyl-(N′-fluordichloromethyl-thio) sulfphamid and 3-isothiazolone compounds such as for instance described in US-A-4,424,134.
  • the amount of additional antimicrobial substances in the textile treatment composition is less than two times the amount of benzimidazolyl-alkyl-carbamate.
  • the fabric softening materials may be selected from cationic, nonionic, amphoteric or anionic fabric softening materials.
  • Suitable amphoteric fabric conditioning material for use in a composition according to the invention are fabric substantive amphotheric materials forming a particulate dispersion at a concentration of less than 1 g/l at at least one temperature between 0 and 100°C. Preferably at at least one temperature between 10 and 90 °C, more preferred between 20 and 80 °C.
  • a fabric substantive amphoteric material is preferably an amphoteric or zwitterionic tertiary or quaternary ammonium compound having either one single long hydrocarbyl side chain or two long hydrocarbyl chains.
  • amphoteric or zwitterionic ammonium compounds having two long hydrocarbyl chains is particularly preferred for many reasons including costs, ease of processing and better stability and performance.
  • Suitable amphoteric materials are for example disclosed in EP-A-0332270.
  • hydrocarbyl chain refers to linear or branched alkyl or alkenyl chains optionally substituted or interrupted by functional groups such as -OH,-O-,-CONH-, and -COO-.
  • amphoteric fabric substantive materials are water insoluble and have a solubility in water at pH 2.5 at 20°C of less than 10 g/l.
  • the HLB of the amphoteric fabric substantive material is preferably less than 10.0.
  • Suitable cationic fabric softener materials for use in a composition according to the present invention are cationic materials which are water-insoluble in that the material has a solubility in water at pH 2.5 and 20°C of less than 10 g/l.
  • Highly preferred materials are cationic quaternary ammonium salts having two C12-24 hydrocarbyl chains.
  • R1 and R2 represent hydrocarbyl groups from 12 to 24 carbon atoms
  • R3 and R4 represent hydrocarbyl groups containing from 1 to 4 carbon atoms
  • X is an anion, preferably selected from halide, methyl sulfate and ethyl sulfate radicals.
  • quaternary softeners include ditallow dimethyl ammonium chloride; ditallow dimethyl ammonium methyl sulfate; dihexadecyl dimethyl ammonium chloride; di(hydrogenated tallow) dimethyl ammonium methyl sulfate; dihexadecyl diethyl ammonium chloride; di(coconut) dimethyl ammonium chloride.
  • Ditallow dimethyl ammonium chloride, di(hydrogenated tallow) dimethyl ammonium chloride, di(coconut) dimethyl ammonium chloride and di(coconut) dimethyl ammonium methosulfate are preferred.
  • Suitable materials also include dialkyl ethoxyl methyl ammonium methosulphate based on soft fatty acid, dialkyl ethoxyl methyl ammonium methosulphate based on hard fatty acid, and a material in which R3 and R4 represent methyl, R1 is C13 ⁇ 15, R2 is CH2CH2OCOR, Where R is stearyl, and X is methosulphate.
  • Ditallow dimethyl ammonium chloride, di(hydrogenated tallow alkyl) dimethyl ammonium chloride, di(coconut alkyl) dimethyl ammonium chloride and di(coconut alkyl) dimethyl ammonium methosulfate are preferred.
  • R5 being tallow, which is available from Stepan under the tradename Stepantex VRH 90 and where R8, R9 and R10 are each alkyl or hydroxyalkyl groups containing from 1 to 4 carbon atoms, or a benzyl group.
  • R6 and R7 are each an alkyl or alkenyl chain containing from 11 to 23 carbon atoms, and X ⁇ is a water soluble anion.
  • hydrocarbylimidazolinium salts believed to have the formula: wherein R13 is a hydrocarbyl group containing from 1 to 4, preferably 1 or 2 carbon atoms, R11 is a hydrocarbyl group containing from 8 to 25 carbon atoms, R14 is an hydrocarbyl group containing from 8 to 25 carbon atoms and R12 is hydrogen or an hydrocarbyl containing from 1 to 4 carbon atoms and A ⁇ is an anion, preferably a halide, methosulfate or ethosulfate.
  • Preferred imidazolinium salts include 1-methyl-1-(tallowylamido-) ethyl -2-tallowyl- 4,5-dihydro imidazolinium methosulfate and 1-methyl-1-(palmitoylamido)ethyl -2-octadecyl-4,5- dihydroimidazolinium chloride.
  • Other useful imidazolinium materials are 2-heptadecyl-1-methyl-1- (2-stearylamido)ethyl-imidazolinium chloride and 2-lauryl-1-hydroxyethyl-1-oleyl-imidazolinium chloride.
  • Also suitable herein are the imidazolinium fabric softening components of US patent No 4 127 489.
  • Representative commercially available materials of the above classes are the quaternary ammonium compounds Arquad® 2HT (ex AKZO); Noramium® M2SH (ex CEKA); Aliquat 2HT (Trade Mark of General Mills Inc), Stepantex Q185 (ex Stepan); Stepantex VP85 (ex Stepan); Stepantex VRH90 (ex Stepan); Synprolam® FS (ex ICI) and the imidazolinium compounds Varisoft 475 (Trade Mark of Sherex Company, Columbus Ohio) and Rewoquat W7500 (Trade Mark of REWO).
  • compositions according to the invention may also possibly in addition to the above mentioned softening agents, one or more amine softening materials.
  • R15 is a C6 to C24, hydrocarbyl group
  • R16 is a C1 to C24 hydrocarbyl group
  • R17 is a C1 to C10 hydrocarbyl group.
  • Suitable amines include those materials from which the quaternary ammonium compounds disclosed above are derived, in which R15 is R1, R16 is R2 and R17 is R3.
  • the amine is such that both R15 and R16 are C6-C20 alkyl with C16-C18 being most preferred and with R17 as C1 ⁇ 3 alkyl, or R15 is an alkyl or alkenyl group with at least 22 carbon atoms and R16 and R12 are C1 ⁇ 3 alkyl.
  • these amines are protonated with hydrochloric acid, orthophosphoric acid (OPA), C1 ⁇ 5 carboxylic acids or any other similar acids, for use in the fabric conditioning compositions of the invention.
  • R18 is a C6 to C24 hydrocarbyl group
  • R19 is an alkoxylated group of formula -(CH2CH2O) y H, where y is within the range from 0 to 6
  • R20 is an alkoxylated group of formula -(CH2CH2O) z H where z is within the range from 0 to 6 and m is an integer within the range from 0 to 6, and is preferably 3.
  • m it is preferred that R18 is a C16 to C22 alkyl and that the sum total of z and y is within the range from 1 to 6, more preferably 1 to 3.
  • m is 1, it is preferred that R18 is a C16 to C22 alkyl and that the sum total of x and y and z is within the range from 3 to 10.
  • Ethomeen® Ex Armour
  • Ethoduomeen® Ex Armour
  • the amines of type (ii) or (iii) are also protonated for use in the fabric conditioning compositions of the invention.
  • R22 and R23 are divalent alkenyl chains having from 1 to 3 carbons atoms
  • R24 is an acyclic aliphatic hydrocarbon chain having from 15 to 21 carbon atoms.
  • a commercially available material of this class is Ceranine® HC39 (ex Sandoz).
  • compositions according to the invention may also contain nonionic fabric-softening agents.
  • Suitable nonionic fabric-softening agents include glycerol esters, such as glycerol monostearate, fatty alcohols, such as stearyl alcohol, alkoxylated fatty alcohols, fatty acids, lanolin and derivatives thereof.
  • Suitable materials are disclosed in European Patent Applications 88 520 (Unilever), 122 141 (Unilever) and 79 746 (Procter & Gamble). Prefererably, such materials are included at a level within the range of from 0.5% to 10% by weight of the composition.
  • compositions can also contain one or more optional ingredients selected from non-aqueous solvents such as C1-C4 alkanols and polyhydric alcohols, pH-buffering agents such as weak acids, e.g. phosphoric, benzoic or citric acids (the compositions preferably have a pH of less than 6.0 more preferred between 2.0 and 5.0), rewetting agents, viscosity modifiers such as electrolytes, included at levels from about 20 to 6000 ppm, aluminium chlorohydrate, antigelling agents, perfumes especially body odour reducing perfumes, perfume carriers, hydrocarbons, fluorescers, colourants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, stabilisers such as guar gum and polyethylene glycol, anti-shrinking agents, anti-wrinkle agents, soil-release agents, antioxidants, anti-corrosion agents, preservatives such as Bronopol (Trade Mark), a commercially available
  • Silicones can be included in the compositions as the ironing aid, re-wetting agent or the antifoaming agent.
  • Suitable silicones for use in the compositions according to the invention include predominantly linear polydialkyl or alkylaryl siloxanes in which the alkyl groups contain one to five carbon atoms.
  • the siloxanes can be amido- or amino-substituted. When the siloxane is amine-substituted the amine group may be quaternised.
  • compositions according to the invention may take a variety of forms. They may for example be liquids containing an aqueous base.
  • compositions according to the invention may be in the form of a powder, creams, pastes, a block or a tablet. Suitable types of blocks and tablets are disclosed in European Patent Specification EP-A-255 779 (Unilever).
  • the total level of the fabric softening material and the benzimidazolyl-alkyl-carbamate is preferably from 1 to 30% by weight.
  • the weight of the fabric-softening agent is preferably from 1 to 20% and the weight of the benzimidazolyl-alkyl-carbamate is preferably from 0.05 to 10%, more preferably from 0.1 to 5%, most preferably from 0.5 to 1.5%.
  • the weight ratio of softening agent to benzimidazolyl-alkyl-carbamate is preferably between 10:1 and 100:1, more preferably around 20:1.
  • Preferably more than 50 wt % of the softening materials are cationic softening materials.
  • compositions When the compositions are in the form of powders, blocks or tablets, they may contain means for restraining the release of the cationic fabric-softening agent and benzimidazolyl-alkyl-carbamate in water, such as paraffin and tallow alcohol.
  • suitable materials are disclosed in the European Patent Specification EP-A-255 779 (Unilever).
  • the compositions may also contain an electrolyte to aid dispersion of the cationic fabric-softening agent and the benzimidazolyl-alkyl-carbamate, after the release inhibitor has ceased to have effect, and an antifoam material.
  • a suitable antifoam granule may be of the type described in our European Patent Specification EP-A-94 250.
  • the compositions are preferably added to a large volume of water to form a liquor with which the fabrics to be treated are contacted.
  • the liquor can be formed by adding the fabric treatment composition to water during the rinse stage of a hand-washing process.
  • the composition can be added by hand or by way of an automatic dispensing device to rinse water in the tub of a washing machine of the type which is common in Europe, that is a machine in which the fabrics are rinsed in a tub which is filled with rinse water, agitated to achieve efficient rinsing and then drained.
  • a washing machine of the type which is common in Europe, that is a machine in which the fabrics are rinsed in a tub which is filled with rinse water, agitated to achieve efficient rinsing and then drained.
  • the total concentration of the fabric-softening agent and the benzimidazolyl-alkyl-carbamate in the rinse liquor will be between 30 and 500 ppm.
  • the compositions can be used in a washing machine which is designed in such a manner that the fabrics are rinsed in running water.
  • a washing machine which is designed in such a manner that the fabrics are rinsed in running water.
  • the fabrics will normally have been previously washed in the same tub of the machine, or they may be placed in the tub specifically for rinsing.
  • the running water When previously washed, they will have at least some of the wash liquor containing a detergent active still adsorbed on or otherwise associated with them, the running water then serving to flush this wash liquor out of the fabrics.
  • the rinse water running into the tub will be substantially free of any detergent actives.
  • the composition can be added to the fabrics in the tub before the rinse water flows into the tub, simultaneously with the rinse water or part-way through the rinse cycle.
  • Aqueous compositions were prepared according to the formulations in the following tables.
  • the compositions were prepared by co-melting the cationic fabric-softening agent and benzimidazolyl-alkyl-carbamate at 80°C.
  • the co-melt thus formed was added to water at 80°C to form a dispersion.
  • the benzimidazolyl-alkyl-carbamate was post-dosed to a dispersion containing the cationic fabric-softening agent.
  • compositions were tested by the following method.
  • Tablets comprising 8 g sodium bicarbonate, 2 g Adogen and 0.4 g carbendazim (Intace B 300) were prepared and compared with tablets comprising 8 g sodium bicarbonate and 2 g Adogen®.
  • Pieces of 50/50 resinated polyester cotton fabrics and pieces of a 100% cotton poplin fabric were washed in a Japanese washing machine at room temperature with 31 g of a commercially available wash powder. After a 1 minute spin to separate the wash liquor, the fabrics were rinsed for ten minutes in running water. One tablet was added and the rinse continued for a further 5 minutes. After line drying, the treated fabrics were assessed for microbial activity as in Example 1.
  • aqueous compositions were prepared as in examples 1-6 and tested on cotton as in these examples.
  • the carbendazim used was Intace B300. These examples again show a reduction in fungal growth when carbendazim is added to fabric softening compositions of the invention.
  • Product Fungal Growth A Niger Penicillium 17.
  • Water 50 18. 7.56% Stepantex VRH 90 50 50 19. 7.56% Stepantex VRH 90 + 1.0% Carbendazim 0-10 5 20.
  • DTTMAPC (1,2 ditallow oxytrimethylammonium propane chloride) 50 50 21.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Claims (6)

  1. Composition pour traiter le linge comprenant un matériau adoucissant le linge et un benzimidazolylalkylcarbamate.
  2. Composition pour traiter le linge selon la Revendication 1, caractérisée en ce que le benzimidazolylalkylcarbamate présente la formule suivante :
    Figure imgb0012
        où R¹ est un alkyle en C₁₋₄, un alkoxy ou un phénoxyalkyle; et
       R² est un alkyle en C₁₋₄, un hydrogène, un azote ou un halogène.
  3. Composition pour traiter le linge selon la Revendication 1, caractérisée en ce qu'elle contient :
       1 à 30 % en masse du matériau adoucissant le linge ; et
       0,1 à 5 % en masse de benzimidazolylalkylcarbamate.
  4. Composition pour traiter le linge selon la Revendication 1, comprenant un matériau cationique adoucissant le linge.
  5. Composition pour traiter le linge selon la Revendication 1, caractérisée en ce qu'elle contient en outre au moins une autre substance antimicrobienne.
  6. Procédé de traitement du linge consistant à rincer les tissus dans un bain aqueux qui comprend une composition pour traiter les textiles contenant un matériau adoucissant le linge et un benzimidazolylalkylcarbamate, dans laquelle la concentration totale du matériau adoucissant le linge et de la composition de benzimidazolylalkylcarbamate dans le bain est comprise entre 30 et 500 ppm.
EP89202298A 1988-09-21 1989-09-13 Composition pour traiter le linge Expired - Lifetime EP0360331B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB8822206 1988-09-21
GB888822206A GB8822206D0 (en) 1988-09-21 1988-09-21 Fabric treatment composition

Publications (3)

Publication Number Publication Date
EP0360331A2 EP0360331A2 (fr) 1990-03-28
EP0360331A3 EP0360331A3 (fr) 1991-06-26
EP0360331B1 true EP0360331B1 (fr) 1995-03-22

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EP89202298A Expired - Lifetime EP0360331B1 (fr) 1988-09-21 1989-09-13 Composition pour traiter le linge

Country Status (13)

Country Link
EP (1) EP0360331B1 (fr)
JP (1) JPH02112473A (fr)
KR (1) KR950009497B1 (fr)
AU (1) AU613792B2 (fr)
BR (1) BR8904720A (fr)
CA (1) CA1340358C (fr)
DE (1) DE68921822T2 (fr)
ES (1) ES2070168T3 (fr)
GB (1) GB8822206D0 (fr)
MY (1) MY105854A (fr)
PH (1) PH27189A (fr)
TR (1) TR24561A (fr)
ZA (1) ZA897208B (fr)

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS4993537A (fr) * 1973-01-06 1974-09-05
DE2459354C2 (de) * 1974-12-16 1986-03-27 Hoechst Ag, 6230 Frankfurt Waescheweichspuelmittelkonzentrat mit desinfizierenden eigenschaften
JPS57210068A (en) * 1981-06-17 1982-12-23 Asahi Chemical Ind Production of polyurethane fiber having anti-fungal property
DE3444068A1 (de) * 1984-12-03 1986-06-05 Henkel KGaA, 4000 Düsseldorf Mittel und verfahren zum nachbehandeln gewaschener waesche

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Publication number Publication date
KR950009497B1 (ko) 1995-08-23
AU4153689A (en) 1990-03-29
ZA897208B (en) 1991-05-29
GB8822206D0 (en) 1988-10-26
TR24561A (tr) 1991-11-22
DE68921822D1 (de) 1995-04-27
ES2070168T3 (es) 1995-06-01
EP0360331A2 (fr) 1990-03-28
AU613792B2 (en) 1991-08-08
PH27189A (en) 1993-04-16
EP0360331A3 (fr) 1991-06-26
CA1340358C (fr) 1999-01-26
KR900005010A (ko) 1990-04-13
DE68921822T2 (de) 1995-07-13
MY105854A (en) 1995-02-28
JPH02112473A (ja) 1990-04-25
BR8904720A (pt) 1990-05-01

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