EP0332270B2 - Composition de conditionnement pour le linge - Google Patents

Composition de conditionnement pour le linge Download PDF

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Publication number
EP0332270B2
EP0332270B2 EP89200545A EP89200545A EP0332270B2 EP 0332270 B2 EP0332270 B2 EP 0332270B2 EP 89200545 A EP89200545 A EP 89200545A EP 89200545 A EP89200545 A EP 89200545A EP 0332270 B2 EP0332270 B2 EP 0332270B2
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Prior art keywords
weight
amine
fabric
fabric conditioning
cationic
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German (de)
English (en)
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EP0332270A3 (en
EP0332270A2 (fr
EP0332270B1 (fr
Inventor
John Robert Martin
William Frederick Soutar Neillie
Graham Andrew Turner
Douglas Wraige
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Unilever PLC
Unilever NV
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Unilever PLC
Unilever NV
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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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/88—Ampholytes; Electroneutral compounds
    • C11D1/94—Mixtures with anionic, cationic or non-ionic 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/66—Non-ionic compounds
    • C11D1/75—Amino oxides
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/40—Monoamines or polyamines; Salts thereof
    • 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
    • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
    • C11D1/38—Cationic compounds
    • C11D1/62—Quaternary ammonium compounds

Definitions

  • This invention relates to a fabric conditioning composition suitable for conditioning fabrics during the rinse step of a fabric laundry process.
  • anionic surface active materials carried over from the wash cycle of the fabric laundry process can have a detrimental effect on the effectiveness of fabric conditioning compositions containing fabric softening agents which are used in the rinse step of the fabric laundry process.
  • This problem can be alleviated if the fabrics are thoroughly rinsed before they are treated with a fabric conditioner, alternatively this problem can possibly be overcome by using fabric conditioning compositions which are not as sensitive to the presence of anionic surface active agents.
  • European patent 63 899 (UNILEVER) to overcome the problem of anionic carry-over by the use of anionic scavengers, such as aluminium chlorohydrate.
  • EP-A-0,210,704 discloses a water-insoluble, water-dispersible fabric softening composition comprising an amine, a phosphate ester and an amine oxide.
  • the softening composition is intended for use with detergents, to provide a softening-through-the-wash effect.
  • GB-A-2,160,886 discloses a solid detergent bar which is also capable of softening fabrics during washing.
  • the bar comprises an anionic, nonanionic, amphoteric, cationic or zwitterionic surfactant; a builder; a long chain aliphatic amide or amine oxide; a cellulosic derivative; a softening agent and talc, aluminium formate or calcined sodium carbonate.
  • the softening agent may be a quaternary ammonium salt having at least one C 16 -C 22 aliphatic radical, an imidazolinium salt, a tertiary amine or a smectic clay. The combination of an amine and a quaternary ammonium softening agent is not, however, specifically disclosed.
  • FR-A-2,593,517 describes a detergent composition which is also capable of softening fabrics.
  • the composition includes, inter alia, an anionic surfactant; a cationic softener, which may be a di-lower-di-higher alkyl quaternary ammonium compound; and an ethoxylated tertiary amine.
  • an aqueous liquid fabric conditioning composition comprising from 1 to 60% by weight of a combination of:
  • Fabric conditioning compositions according to the present invention comprise at least the following three active ingredients:
  • the cationic fabric softening agent The cationic fabric softening agent
  • the cationic fabric softener material is a cationic material which is water-insoluble in that these materials have a solubility in water at pH 2.5 and 20°C of less than 10 g/l.
  • the materials are cationic quaternary ammonium salts having two C12-24 hydrocarbyl chains.
  • R 1 and R 2 represent hydrocarbyl groups trom about 12 to about 24 carbon atoms
  • R 3 and R 4 represent hydrocarbyl groups containing from 1 to about 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 R 3 and R 4 represent methyl, R 1 is C 13-15 , R 2 is CH 2 CH 2 OCOR, where R is stearyl, and X is methosulphate.
  • R 2 , R 3 and R 4 each represent methyl, R 1 is the group where R is hardened tallow and X is methosulphate are also suitable.
  • 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.
  • hydrocarbyl group refers to alkyl or alkenyl groups optionally substituted or interrupted by functional groups such as -OH, -O-, -CONH-, -COO-, etc.
  • R 5 being partially hardened tallow, which is available from Stepan under the tradename Stepantex VRH 90 and where R 8 , R 9 and R 10 are each alkyl or hydroxyalkyl groups containing from 1 to 4 carbon atoms, or a benzyl group.
  • R 6 and R 7 are each an alkyl or alkenyl chain containing from 11 to 23 carbon atoms, and X - is a water soluble anion, substantially free of the corresponding monoester.
  • Another class of preferred water-insoluble cationic materials are selected from the hydrocarbylimidazolinium salts believed to have the formula: wherein R 13 is a hydrocarbyl group containing from 1 to 4, preferably 1 or 2 carbon atoms, R 11 is a hydrocarbyl group containing from 12 to 24 carbon atoms, R 14 is an hydrocarbyl group containing from 12 to 24 carbon atoms and R 12 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, incorporated by reference.
  • 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 also contain in addition to cationic fabric softening agents, one or more amines.
  • R 15 is a C 6 to C 24 , hydrocarbyl group
  • R 16 is a C 1 to C 24 hydrocarbyl group
  • R 17 is a C 1 to C 10 hydrocarbyl group.
  • Suitable amines include those materials from which the quaternary ammonium compounds disclosed above are derived, in which R 15 is R 1 , R 16 6 is R 2 and R 17 is R 3 .
  • the amine is such that both R 15 and R 16 are C 6 -C 20 alkyl with C 16 -C 18 being most preferred and with R 17 as C 1-3 alkyl, or R 15 is an alkyl or alkenyl group with at least 22 carbon atoms and R 16 and R 12 are C 1-3 alkyl.
  • thee amines are protonated with hydrochloric acid, orthophosphoric acid (OPA), C 1-5 carboxylic acids or any other similar acids, for use in the fabric conditioning compositions of the invention.
  • R 18 is a C 6 to C 24 hydrocarbyl group
  • R 19 is an alkoxylated group of formula -(CH 2 CH 2 O) y H, where y is within the range from 0 to 6
  • R 20 is an alkoxylated group of formula -(CH 2 CH 2 O) 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 R 18 is a C 16 to C 22 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 R 18 is a C 16 to C 22 alkyl and that the sum total of x and y and z is within the range from 3 to 10.
  • Representative commercially available materials of this class include Ethomeen (ex Armour) and Ethoduomeen (ex Armour).
  • the amines of type (ii) or (iii) are also protonated for use in the fabric conditioning compositions of the invention.
  • R 22 and R 23 are divalent alkenyl chains having from 1 to 3 carbons atoms
  • R 24 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).
  • the tertiary amine oxide fabric conditioning material for use in a composition according to the invention should be a fabric substantive amphotheric material.
  • Suitable amphoteric materials form a particulate dispersion at a concentration of less than 1 g/l at at least one temperature between 0 and 100°C.
  • the tertiary amine oxide compounds have two long hydrocarbyl chains, each chain having 8-24 C-atoms, preferably 10-20 C-atoms, most preferred around 16 C-atoms.
  • 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.
  • amphoteric materials of the above groups and their method of preparation are given in our co-pending European patent application EP-A-0 326 213.
  • Amine oxides containing two hydrocarbyl groups with at least 14 C-atoms are particularly preferred. Amine oxides have been found to provide particularly advantageous softening effects, furthermore compositions comprising amine oxides are generally easy to prepare, are stable and have an interesting creamy appearance.
  • compositions of the present invention contain substantially no anionic material, in particular no anionic surface active material. If such materials are present, the weight ratio of the cationic fabric softening agent to the anionic material should preferably be more than 5:1.
  • the composition can also contain one or more optional ingredients selected from non-aqueous solvents such as C 1 -C 4 alkanols and polyhydric alcohols, pH buffering agents such as strong or weak acids eg. HCl, H 2 SO 4 , phosphoric, benzoic or citric acids (the pH of the liquid compositions ie preferably less than 5.0), rewetting agents, viscosity modifiers such as electrolytes, for example calcium chloride, antigelling agents, perfumes, perfume carriers, fluorescers, colourants, hydrotropes, antifoaming agents, antiredeposition agents, enzymes, optical brightening agents, opacifiers, stabilisers such as guar gum and polyethylene glycol, emulsifiers, anti-shrinking agents, anti-wrinkle agents, fabric crisping agents, anti-spotting agents, soil-release agents, germicides, linear or branched silicones, fungicides, anti-oxidants, anti-corrosion agents, preservatives such as
  • compositions are each present at levels up to 5% by weight of the composition.
  • the pH of the composition is preferably 5 or below, or adjusted thereto.
  • Anti-redeposition agents particularly preferred in the compositions according to the invention are polymers.
  • Suitable polymers include alkyl and hydroxoyalkyl cellulose ethers, such as methyl cellulose, and polyvinylpyrrolidone.
  • Silicones can be included in the compositions as the ironing aid, rewetting 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 may also contain, in addition to the cationic fabric softening agent, other non-cationic fabric softening agents, such as 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 C 9 -C 24 fatty acids and lanolin and derivatives thereof.
  • Suitable materials are disclosed in European Patent Application 88 520 (Unilever PLC/NV case C 1325), 122 141 (Unilever PLC/NV case C 1363) and 79 746 (Procter and Gamble). Typically such materials are included at a level within the range of from 0.5% to 10% by weight of the composition.
  • the total level of the three ingredients in a liquid composition is from 1 to 60% more preferred from 3 to 30% by weight of the composition.
  • the weight of the cationic softening agent is not more than 90%, preferably between 25 and 75 %, more preferred from 40 to 60 %. especially preferred about 50 %.
  • the weight of the amine is not more than 70%, preferably between 10 and 60%, more preferred between 15 and 40 %, especially preferred about 25 %.
  • the weight of the amphoteric material is not more than 60 %. If the amphoteric material is an amine oxide then this constitutes preferably less than 60 %, more preferred between 10 and 50 %, especially preferred between 15 and 40 %, most preferred about 25 % based on the weight of the three actives.
  • the optimum weight ratio of the three active components in the fabric conditioning composition depends on the level of anionic carried over from the wash cycle. We have found that a weight ratio of cationic fabric softener to amine to amine oxide of about 2:1:1 provides good results under most conditions of use.
  • liquid compositions according to the inventions may be prepared by a variety of methods.
  • One suitable method is to form a molten mixture of the cationic fabric softening agent, amine and amphoteric material, which is then added to water with stirring to form a dispersion and thereafter adding any optional ingredients.
  • the fabric conditioning composition of the invention may be added to a large volume of water to form a liquor with which the fabrics to be treated are contacted.
  • the total concentration of the cationic fabric softening agent, the amine and the amine oxide in this liquor will be between about 30 ppm and 500 ppm.
  • the weight ratio of the fabrics to liquor will generally be between 40:1 and 4:1.
  • compositions of the invention are added to water which contains high levels of anionic surface active materials, a further improvement can be obtained if the compositions contain anionic scavengers such as low molecular weight cationics.
  • Suitable materials include cationic compounds which have a solubility in water at pH 2.5 and 20°C of more than 5 g/l, preferably more than 10 g/l.
  • Arquad 18 is a particularly preferred material. (Arquad 18 is a commercially available form of hardened tallow trimethyl ammonium chloride).
  • compositions were prepared according to the formulations in the following tables.
  • the compositions were prepared by comelting the cationic fabric softening agent, amine and amine oxide at 80°C. (When the amine was Armeen M2HT, the ortho phosphoric acid was added to the water prior to forming the co-melt. In contrast when ceranine HC39 was used, the acid was added after the components were dispersed). The comelt thus formed was added to water at 80°C and then soniprobed for a few minutes to form a disperion which was then cooled to room temperature.
  • compositions were tested as follows - 40 grams of cotton terry toweling were washed for 5 minutes at 50°C with a commercially available washing powder product, UK Persil Automatic, in a litre of Wirral water (10°FH) in a tergotometer. 5 grams of the washing powder product was used. After separating the wash liquor, the fabric load was rinsed twice at 25°C with Wirral water. 4ml of a test composition was added to the second rinse. After line drying, the fabric load was assessed for softness by a panel of experts using a paired comparison test. EXAMPLE NO.
  • compositions 1A and 1B ie. the ternary system, containing the cationic, amine and amine oxide, gave the best softening.
  • compositions 2, 2A and 2B were compared.
  • compositions 1 and 2 were also compared. The results showed a preference for the product containing Ceranine HC39.
  • compositions were prepared according to the formulations in the table by the method described above.
  • Example 3 4 5 6 Arquad 2HT 2.5 2.5 2.5 2.5 2.5 Armeen M2HT (i) protonated with 1.25 - - - OPA (ii) not protonated - 1.25 - - DHTMAO 1.25 1.25 1.25 1.25 Ceranine HC39 (i) protonated with - - 1.25 - OPA (ii) not protonated - - - 1.25 OPA 0.25 - 0.25 - Water -----balance--------
  • compositions were tested according to the method described in Examples 1 and 2.
  • composition 3 which contained a protonated amine
  • compositions according to the invention were prepared by the method described above Example 16 17 18 19 20 21 Arquad 2HT 7.5 6.75 7.50 8.5 7.5 5.1 Ceranine HC39 3.75 3.375 3.75 - - 8.5 Ceranine HCA - - - 4.25 3.75 - DHTMAO 3.75 3.375 3.75 4.25 3.75 3.4

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Treatment Of Fiber Materials (AREA)
  • Chemical Or Physical Treatment Of Fibers (AREA)
  • Detergent Compositions (AREA)

Claims (4)

  1. Composition liquide aqueuse de conditionnement pour tissu comprenant de 1 à 60% en poids d'un mélange de:
    (i) de 20% à 90% en poids d'un agent d'adoucissement pour tissu à base d'ammonium quaternaire cationique ayant deux chaínes hydrocarbyle en C12 à C24 et une solubilité dans l'eau à un pH de 2,5 et à 20°C inférieure à 10g/l:
    (ii) de 5% à 70% en poids d'une amine; et
    (iii) de 5% à 60% en poids d'une matière de conditionnement amphotère pour tissu dans lequel ladite matière de conditionnement amphotère pour tissu est choisie parmi des oxydes d'amines tertiaires de formule suivante:
    Figure 00150001
    dans laquelle :
    a) R25 et R26 sont des chaínes hydrocarbyle en C8 à C24, R27 est un groupe hydrocarbyle contenant de 1 à 4 atomes de carbone ou un groupe -(CH2CH2O)nH où n est un nombre entier de 1 à 6;
    le pourcentage en poids de (i), (ii) et (iii) étant fondé sur le poids total des composants (i), (ii) et (iii) dans la composition.
  2. Composition de conditionnement pour tissu selon la revendication 1, comprenant, fondée sur le poids total des trois composants de (i) à (iii):
    (i) de 40 à 60% d'un agent d'adoucissement cationique
    (ii) de 15 à 40% d'amine
    (iii) de 15 à 40% d'oxyde d'amine.
  3. Composition de conditionnement pour tissu selon l'une des quelconques revendications 1 ou 2, comprenant de 3 à 30% en poids de matière active.
  4. Procédé de conditionnement pour tissu comprenant l'étape consistant à mettre en contact des tissus avec un bain aqueux comprenant une composition de conditionnement pour tissu selon l'une quelconques des revendications de 1 à 3, la concentration totale en agent d'adoucissement cationique pour tissu, l'amine et l'oxyde d'amine étant comprise entre 30 et 500 ppm.
EP89200545A 1988-03-11 1989-03-06 Composition de conditionnement pour le linge Expired - Lifetime EP0332270B2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB888805837A GB8805837D0 (en) 1988-03-11 1988-03-11 Fabric conditioning composition
GB8805837 1988-03-11

Publications (4)

Publication Number Publication Date
EP0332270A2 EP0332270A2 (fr) 1989-09-13
EP0332270A3 EP0332270A3 (en) 1990-05-16
EP0332270B1 EP0332270B1 (fr) 1996-06-05
EP0332270B2 true EP0332270B2 (fr) 2001-07-04

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EP (1) EP0332270B2 (fr)
JP (1) JP2551479B2 (fr)
AU (1) AU620082B2 (fr)
BR (1) BR8901135A (fr)
CA (1) CA1341483C (fr)
DE (1) DE68926584T3 (fr)
ES (1) ES2087861T5 (fr)
GB (1) GB8805837D0 (fr)
ZA (1) ZA891845B (fr)

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GB9810656D0 (en) * 1998-05-18 1998-07-15 Unilever Plc Stable ammonium compositions
EP0990695A1 (fr) * 1998-09-30 2000-04-05 Witco Surfactants GmbH Composition adoucissante inhibitant le transfert de colorants
WO2001036736A1 (fr) * 1999-11-12 2001-05-25 Kao Corporation Composition adoucissante
GB2375356A (en) * 2001-05-11 2002-11-13 Reckitt Benckiser Nv Cationic fabric softening compositions
US6887542B2 (en) * 2002-12-11 2005-05-03 Kimberly-Clark Worldwide, Inc. Method for treating an elastomeric article
US20230147510A1 (en) 2021-11-05 2023-05-11 Nouryon Chemicals International B.V. Liquid fabric softener compositions comprising hydroxypropyl starch phosphate

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EP0125031A1 (fr) † 1983-04-08 1984-11-14 Unilever Plc Composition liquide d'assouplissement de tissus
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Also Published As

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ES2087861T5 (es) 2001-10-16
ZA891845B (en) 1990-11-28
AU620082B2 (en) 1992-02-13
DE68926584T2 (de) 1996-10-02
EP0332270A3 (en) 1990-05-16
ES2087861T3 (es) 1996-08-01
DE68926584T3 (de) 2001-09-27
JPH026662A (ja) 1990-01-10
EP0332270A2 (fr) 1989-09-13
DE68926584D1 (de) 1996-07-11
CA1341483C (fr) 2005-05-17
AU3124389A (en) 1989-09-14
EP0332270B1 (fr) 1996-06-05
GB8805837D0 (en) 1988-04-13
BR8901135A (pt) 1989-10-31
JP2551479B2 (ja) 1996-11-06

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