EP0559693A1 - Compositions detergentes liquides - Google Patents

Compositions detergentes liquides

Info

Publication number
EP0559693A1
EP0559693A1 EP91920387A EP91920387A EP0559693A1 EP 0559693 A1 EP0559693 A1 EP 0559693A1 EP 91920387 A EP91920387 A EP 91920387A EP 91920387 A EP91920387 A EP 91920387A EP 0559693 A1 EP0559693 A1 EP 0559693A1
Authority
EP
European Patent Office
Prior art keywords
detergent composition
composition according
built detergent
liquid built
liquid
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.)
Withdrawn
Application number
EP91920387A
Other languages
German (de)
English (en)
Inventor
Sean Geoffrey Grove Hill 13 Dromore Road Hall
John Thomas Mccullins
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.)
Sb Chemicals Ltd
Original Assignee
Sb Chemicals Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Sb Chemicals Ltd filed Critical Sb Chemicals Ltd
Publication of EP0559693A1 publication Critical patent/EP0559693A1/fr
Withdrawn legal-status Critical Current

Links

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
    • C11D17/00—Detergent materials or soaps characterised by their shape or physical properties
    • C11D17/0004—Non aqueous liquid compositions comprising insoluble particles
    • 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
    • C11D1/83—Mixtures of non-ionic with anionic 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/14—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aliphatic hydrocarbons or mono-alcohols
    • C11D1/143—Sulfonic acid esters
    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/22—Sulfonic acids or sulfuric acid esters; Salts thereof derived from aromatic 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
    • C11D1/38—Cationic compounds
    • C11D1/52—Carboxylic amides, alkylolamides or imides or their condensation products with alkylene oxides
    • C11D1/523—Carboxylic alkylolamides, or dialkylolamides, or hydroxycarboxylic amides (R1-CO-NR2R3), where R1, R2 or R3 contain one hydroxy group per alkyl group
    • 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
    • C11D1/72—Ethers of polyoxyalkylene glycols

Definitions

  • This invention relates to liquid built detergent compositions and to their production and use.
  • aqueous heavy duty built liquid detergents have made in-roads into the spray dried washing powder market with the result that much work has taken place both in relation to the physics and also to the chemistry of product formulation.
  • built liquid detergents are often sold in 2 litre plastics bottles. Typical of such products are those described in GB-B-2123846, GB-B-2153839, EP-B- 0086614 and EP-B-0151884.
  • this sector has basically been forced to formulate its products either as dispersions of inorganic builders in non-aqueous mixtures of non-ionic surfactants, as in EP-B-0030096 or EP-B-0120659, or as formulations of a non-ionic surfactant mixture in the emulsion state with a saturated solution of one or more builders using vegetable gums, or other emulsifying agents, as stabilisers, as in GB-A-2148926.
  • the surfactants in the emulsion are non-ionic surfactants whereas, in the case of EP-B-0120659, claim 9 cites the presence of an anionic surfactant in the composition but the specification completely omits to teach its use in any of its Examples. This omission is because it is difficult in commerce to acquire anionic surfactants, such as sodium dodecyl benzene sulphonate, in the non-pasty solid state (any that do exist are normally offered in admixture with sodium sulphate to prevent the material from being sticky and balling together
  • the water analogue of the built system of, for example, GB-B-2153839 is the class of anhydrous solvents known as the polyethylene glycols (P.E.Gs).
  • Liquid members of this class are those with a molecular weight between about 100 and about 600, commonly called PEG.100, PEG.200, PEG.300 and so forth.
  • non-aqueous heavy duty built liquid detergent composition with an anionic surfactant as an integral part of the liquid phase in which the builders are dispersed by either rod, bead or ball milling. It would further be desirable to produce a non-aqueous heavy duty built liquid detergent composition which does not gel upon dispersion in water.
  • the present invention accordingly seeks to provide a substantially anhydrous liquid built detergent composition containing an anionic surfactant. It further seeks to provide a substantially anhydrous liquid built detergent composition which shows little or no tendency to gel upon dispersion in water.
  • a liquid built detergent composition comprising a substantially anhydrous organic liquid phase having uniformly distributed therein (i) an amine salt of an anionic surfactant acid which contains one or more sulphonic acid groups and (ii) a finely divided particulate builder.
  • the organic liquid phase is substantially anhydrous.
  • it is preferably devoid of added water and contains only that amount of water which is normally present in the ingredients used in production of the liquid built detergent composition oi the invention.
  • a composition in accordance with the invention typically contains less than about 5% w/w water, more preferably less than about 2% w/w water, and even more preferably less than about 1% w/w water, e.g. about 0.5% w/w or less, down to about 0.1% w/w or less of water, based upon the total weight of the composition.
  • the organic liquid phase may include a water- soluble organic solvent.
  • a liquid built detergent composition comprising a water- soluble organic solvent phase having uniformly distributed therein (i) an amine salt of an anionic surfactant acid which contains one or more sulphonic acid groups and (ii) a finely divided particulate builder.
  • amine salt of the anionic surfactant acid Normally a significant proportion of the amine salt of the anionic surfactant acid, and preferably all of it, is dissolved in the organic liquid phase, presumably in a form akin to the micelles typically found in aqueous detergent solutions, while the builder is insoluble in the organic liquid phase.
  • the water-soluble organic solvent may comprise a lower molecular weight alcohol, for example an alkanol containing from 1 to 6, or more preferably 2 to 4 carbon atoms, such as ethanol, n-propanol, iso-propanol, n-butanol or the like.
  • a lower molecular weight alcohol for example an alkanol containing from 1 to 6, or more preferably 2 to 4 carbon atoms, such as ethanol, n-propanol, iso-propanol, n-butanol or the like.
  • Another suitable class of water-soluble organic solvents is liquid water-soluble organic compounds containing two or more hydroxy groups.
  • Examples of such compounds include ethylene glycol, jpropylene glycol, 1,4- butylene glycol, 1,5-pentamethylene glycol, glycerol, polyalkylene glycols such as polyethylene glycol, polypropylene glycol, and mixed polyoxyalkylene ether glycols, such as polyoxyethylene-polyoxypropylene glycols, as well as mixtures of two or more thereof.
  • a preferred type of water-soluble organic solvent is the polyethylene glycols, of which those having molecular weights of at least about 150, for example molecular weights in the range of from about 200 to about 600, are preferred.
  • any solvent that is liquid at ambient temperatures and below (e.g. down to about -10°C), that is water miscible, and that will allow dispersion of the amine salt of the anionic surfactant acid and of the builder can be used.
  • Mixtures of water-soluble organic solvents can be used, if desired.
  • a mixture of an alkanol, such as ethanol or iso-propanol, and a polyethylene glycol can be used.
  • an organic water-soluble solvent or of a mixture of organic solvents for example, up to about 20% w/w of solvent based upon the total weight of the composition.
  • a preferred range is from about 1% w/w up to about 15% w/w of solvent based upon the total weight of the composition.
  • One of the purposes for which this solvent, if present, is added may be to adjust the viscosity of the composition to a desired value.
  • a useful degree of control over the viscosity of the composition can be achieved, in particular, by addition of a glycol such as a polyethylene glycol (e.g. polyethylene glycol PEG 200).
  • Amine salts useful in the practice of the present invention can be prepared by reacting an organic amine with an anionic surfactant acid containing one or more sulphonic acid groups.
  • Particularly preferred amines are alkanolamines, such as monoethanolamine, diethanolamine and triethanolamine, and heterocyclic monocyclic amines, such as morpholine.
  • liquid built detergent compositions of the invention will be diluted with water. This dilution step may take place in the wash cycle of an automatic washing machine, for example. Since the builder is normally alkaline in nature and may typically contain an alkali metal ion, exchange of cations may occur upon dilution of the liquid built detergent composition with water. Thus the quaternary ammonium ion of the salt of the anionic surfactant acid present in the composition may, for example, undergo exchange with sodium ions from the builder.
  • the anions of the anionic surfactant acid may be associated in the resulting aqueous solution with, for example, sodium ions or the ions of another alkali metal, whilst the quaternary ammonium ion, may undergo hydrolysis to yield the free amine. Since some amines have pungent or unpleasant odours, it will normally be preferred to select as the amine salt of the anionic surfactant acid a material which upon hydrolysis of the quaternary ammonium ion does not release an amine with an unpleasant odour.
  • preferred salts of anionic surfactant acids for use in the compositions of the invention contain alkanolammonium ions or morpholinium ions such as monoalkanolammonium, dialkanolammonium and trialkanolammoniu salts of anionic surfactant acids, such as monoethanolammonium, diethanolammonium and triethanolammonium salts of anionic surfactant acids, and morpholinium salts of anionic surfactant acids.
  • any of the known builders such as sodium metaphosphate, sodium paraphosphate , sodium tripolyphosphate, sodium silicate, sodium carbonate, a zeolite, a layer silicate, trisodium citrate, or a mixture of two or more thereof.
  • an anhydrous material such as anhydrous sodium carbonate
  • the anhydrous material absorbs water to form a solid hydrate of sodium carbonate. In this way any water present or formed in the composition, can be absorbed and the substantially non-aqueous nature of the composition is retained, in addition to the sodium carbonate being available to act as an alkaline builder.
  • surfactant acids include alkyl benzene sulphonic acids, in which the alkyl group contains from about 6 to about 20 carbon atoms, for example from 10 to 14 carbon atoms, primary or secondary alkyl sulphonic acids containing from about 10 to about 26 carbon atoms, for example from 10 to 14 carbon atoms, and alpha-olefin sulphonic acids obtained by sulphonation of an alpha-olefin containing, for example from about 10 to about 22 carbon atoms, such as a C- ⁇ g to C ⁇ g olefin or a mixture containing same.
  • a material containing a sulphonic acid group there may also be used for the production of the amine salt or salts, usually in admixture with a material containing a sulphonic acid group, a sulphated fatty alcohol;
  • typical sulphated fatty alcohols include those containing from about 10 to about 26 carbon atoms, for example a sulphated fatty alcohol mixture containing C- IQ , C-- ⁇ , C- ⁇ , - ⁇ - and C- ⁇ g fatty alcohols.
  • Typical of such a fatty alcohol mixture is one containing alcohols in the following proportions: C 10 3.0%, C 12 57.0%, C 14 20.0%, C- - 9.0% and C 18 11.0%.
  • composition of the invention may further include one or more non-ionic surfactants.
  • Typical non- ionic surfactants include fatty acid monoethanolamides such as coconut fatty acid monoethanolamide, a typical formulation for which is a mixture of monoethanolamides of fatty acids as follows: Cg 0.5%, Cg 6.5%, C 1Q 6.0%, C 12 49.5%, C 14 19.5%, C 16 8.5%, C 18 (stearic) 2.0%, C 18 (oleic) 6.0%, and C ⁇ (linoleic) 1.5%.
  • non-ionic surfactants include polyoxyalkylene ethers of alkanols, typically polyoxyethylene ethers of alkanols containing typically 3 or more ethylene oxide groups, for example from about 6 to about 20 ethylene oxide residues and based upon alkanols containing from about 6 to about 26 carbon atoms.
  • Mixed polyoxyethylene oxypropylene ethers of alkanols can also be used? these can also be based on C 6 to C 26 alkanols and can contain from about 3 up to about 20 alkylene oxide residues, i.e. a mixture of ethylene oxide and propylene oxide residues.
  • the alkanols and alkanol mixtures upon which such non-ionic surfactants are based can be produced by hydrogenation of methyl esters produced by transesterification of naturally occurring vegetable oils such as coconut oil, sunflower oil, palm oil, rape seed oil, and the like, or of animal fats, such as tallow or lard.
  • a typical polyoxyethylene ether of an alkanol is based upon lauryl alcohol condensed with approximately 8 moles of ethylene oxide.
  • Polyoxyalkylene ethers of alkylphenols are another type of non-ionic surfactant. Mixtures of non-ionic surfactants can be used.
  • compositions of the present invention may include an amphoteric surfactant or a mixture of amphoteric surfactants.
  • Typical amphoteric surfactants include dicarboxylated derivatives of oleic imidazoline, capryi ⁇ amphocarboxy glycinate, octyl imino dipropionate, octyl dimethyl betaine, complex coco i inodiglycinates, and fatty ampho polycarboxyglycinates.
  • the weight ratio of amphoteric surfactant to non-ionic surfactant may vary within wide limits, for example in the range of from about 1:100 to about 100:1.
  • a liquid built detergent composition according to the invention contains at least about 0.1% w/w of an amine salt of an anionic surfactant acid up to about 20% w/w or more, e.g. up to about 25% w/w, even more preferably from about 2% w/w up to about 15% w/w, based on the total weight of said composition.
  • a liquid built detergent composition according to the invention comprises from about 0.1% w/w up to about 20% or more of a non-ionic surfactant or surfactants, of an amphoteric surfactant or surfactants, or of a mixture of non-ionic and amphoteric surfactants, even more preferably up to about 35% w/w or more, e.g. up to about 50% w/w, most preferably from about 2% up to about 35% w/w, based on the total weight of the composition.
  • a liquid built detergent composition according to the invention may further comprise a bleach and, optionally, a bleach activator.
  • a composition may contain from about 0.1% w/w up to about 10% w/w or more, e.g. up to about 15% w/w of a bleach and, optionally, from about 0.03% w/w up to about 3% w/w or more, e.g. up to about 5% w/w of a bleach activator, based upon the total weight of the composition.
  • minor ingredients which may be included in the composition of the invention include preservatives, optical brighteners, fragrances, foam depressants, foam boosters and/or stabilisers, soaps, dyes, pigments, buffers, corrosion inhibition agents, sequestration agents, anti- ingestion agents, humectants, enzymes, enzyme stabilisers, fabric softeners, fabric conditioners, and the like.
  • Typical sequestration agents include ethylene diamine tetraacetic acid, nitrilotrioacetic acid, and acrylic-maleic copolymers such as those sold under the trade mark Polycarboxylate AMC.
  • One or more of these minor ingredients can be included in the compositions of the invention as appropriate.
  • Such other minor ingredients typically comprise not more than about 5% w/w each of the compositions of the invention, for example in the range of from about 0.001% w/w up to about 2% w/w each based upon the total weight of the composition.
  • compositions of the invention may be formulated so as to have approximately the same laundering power as conventional aqueous heavy duty built liquid detergents.
  • the compositions of the invention will be formulated as concentrates which have several times, e.g. about 2 to about 5 times, the laundering power of conventional aqueous heavy duty built liquid detergents.
  • the solid components comprise in total at least about 30% w/w and preferably at least about 45% w/w up to about 50% w/w or even higher, based upon the weight of the composition.
  • the invention further provides a process for the production of a liquid built detergent composition which includes the step of reacting in an organic phase an anionic surfactant acid containing one or more free sulphonic acid groups with an amine.
  • an amine may be a primary amine, a secondary amine, or a tertiary amine.
  • the reaction is carried out in an organic phase which includes a water-soluble organic solvent.
  • a process for the production of a liquid built detergent composition which includes the step of reacting an anionic surfactant acid containing one or more free sulphonic acid groups in an organic solvent phase comprising a water-soluble solvent with an amine.
  • the amine may be a primary amine, a secondary amine, or a tertiary amine.
  • the invention contemplates producing in-situ quantities of organic base salts of anionic surfactant sulphonic acids.
  • highly successful built liquids can be produced from solutions of an acid such as dodecylbenzene sulphonic. acid in PEG 200 (polyethylene glycol 200), in alkylene oxide addition products, or in a blend of both.
  • Such solutions may further contain anhydrous non-ionic surfactants.
  • the organic bases which were used were mono-, di-, and triethanolamine and morpholine but any primary, secondary or tertiary amine without an unpleasant odour can be used. From these materials very transparent pale yellow syrups can be produced which are excellent vehicles for carrying the silicate, carbonate, phosphate and polyphosphate builders which are to be micronised to give the non-aqueous built laundry liquids.
  • a further series of similar syrups can be prepared by omitting the polyethylene glycol or the fatty alcohol ethoxylate.
  • a liquid built detergent concentrate is produced from the following ingredients:-
  • Alcohol ethoxylate polyethylene glycol ether (3 moles of ethylene oxide) of a c 12-15 alkanol mixture.
  • Alcohol alkoxylate polyethylene/propylene glycol ether (7 moles of alkylene oxide: 92% propylene oxide/8% ethylene oxide) of a c 12-15 alkanol mixture.
  • Liquid built detergent concentrates were produced by mixing the following ingredients and blending together all the liquid ingredients in each formulation listed, with the exception of the minor ingredients. Amine salt formation from the dodecylbenzene sulphonic acid was accomplished by stoichiometric addition of the relevant amine. Then all the solid ingredients were added, with the exception of any thermally labile enzyme present. The resulting mixture was then micronised in a ball mill to produce an easily flowable product which could then be inoculated with the appropriate quantity of enzyme or enzymes (if used) :
  • a small amount of a bitter tasting material such as Bitrex
  • Bitrex a bitter tasting material
  • a concentrate according to any one of Examples 10 to 26 in order to deter ingestion of the concentrate by, for example, small children.
  • Bitrex amounts as low as about 0.005 %w/w suffice for this purpose.

Landscapes

  • 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)
  • Detergent Compositions (AREA)

Abstract

Composition détergente liquide comportant une phase liquide organique sensiblement anhydre dans laquelle sont réparties de manière uniforme (i) un sel aminé d'un acide tensio-actif anionique renfermant un ou plusieurs groupes d'acide sulfonique; et (ii) un adjuvant particulaire finement divisé.
EP91920387A 1990-11-26 1991-11-26 Compositions detergentes liquides Withdrawn EP0559693A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB909025691A GB9025691D0 (en) 1990-11-26 1990-11-26 Liquid built detergent concentrates
GB9025691 1990-11-26

Publications (1)

Publication Number Publication Date
EP0559693A1 true EP0559693A1 (fr) 1993-09-15

Family

ID=10686003

Family Applications (1)

Application Number Title Priority Date Filing Date
EP91920387A Withdrawn EP0559693A1 (fr) 1990-11-26 1991-11-26 Compositions detergentes liquides

Country Status (10)

Country Link
EP (1) EP0559693A1 (fr)
JP (1) JPH06502662A (fr)
AU (1) AU8947191A (fr)
CA (1) CA2096955A1 (fr)
GB (1) GB9025691D0 (fr)
IE (1) IE914108A1 (fr)
NZ (1) NZ240753A (fr)
PT (1) PT99612A (fr)
WO (1) WO1992009677A1 (fr)
ZA (1) ZA919331B (fr)

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EP0688859A1 (fr) * 1994-06-22 1995-12-27 The Procter & Gamble Company Procédé de traitement de textiles et compositions utilisées à cet effet
EP0842256B1 (fr) * 1995-06-20 2003-01-22 The Procter & Gamble Company Compositions detergentes liquides non aqueuses contenant des particules et un agent tensioactif a base de sulfonate de benzene d'alkyle
DE19717687A1 (de) * 1997-04-28 1998-10-29 Schwarzkopf Gmbh Hans Zubereitung zur Behandlung keratinischer Fasern
BR0206353A (pt) * 2001-01-19 2003-12-23 Reckitt Benckiser Nv Aperfeiçoamentos em, ou relacionados a composições detergentes lìquidas
PA8662601A1 (es) 2005-02-15 2007-01-17 Colgate Palmolive Co Composiciones limpiadoras que proporcionan remocion de grasa y entrega de fragancia
DK1853689T3 (da) 2005-02-15 2012-11-12 Colgate Palmolive Co Duftsammensætninger, som reducerer eller eliminerer dårlig lugt, beslægtede fremgangsmåder og beslægtede rengøringssammensætninger
ATE534721T1 (de) * 2009-09-14 2011-12-15 Procter & Gamble Reinigungsmittelzusammensetzung
JP5868747B2 (ja) * 2012-03-19 2016-02-24 花王株式会社 界面活性剤混合物の製造方法
WO2015134827A1 (fr) * 2014-03-07 2015-09-11 The Procter & Gamble Company Compositions comprenant un agent d'amertume
RU2645217C1 (ru) 2014-03-07 2018-02-19 Дзе Проктер Энд Гэмбл Компани Композиции, содержащие агент, придающий горечь

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JPS62161990A (ja) * 1985-07-16 1987-07-17 Shimoyama Denka Kogyosho:Kk 有孔不導体粗表面へのメツキ装飾方法
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Also Published As

Publication number Publication date
JPH06502662A (ja) 1994-03-24
CA2096955A1 (fr) 1992-05-27
ZA919331B (en) 1992-09-30
NZ240753A (en) 1995-06-27
IE914108A1 (en) 1992-06-03
PT99612A (pt) 1992-10-30
GB9025691D0 (en) 1991-01-09
AU8947191A (en) 1992-06-25
WO1992009677A1 (fr) 1992-06-11

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