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WO1999036501A1 - Procede de preparation de compositions de detergence - Google Patents

Procede de preparation de compositions de detergence Download PDF

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Publication number
WO1999036501A1
WO1999036501A1 PCT/EP1999/000248 EP9900248W WO9936501A1 WO 1999036501 A1 WO1999036501 A1 WO 1999036501A1 EP 9900248 W EP9900248 W EP 9900248W WO 9936501 A1 WO9936501 A1 WO 9936501A1
Authority
WO
WIPO (PCT)
Prior art keywords
absorber
alkyl
solvent
premix
process according
Prior art date
Application number
PCT/EP1999/000248
Other languages
English (en)
Inventor
Marcia Regina Domingues Mobaier
Robert Jan Reinier Uhlhorn
Original Assignee
Unilever N.V.
Unilever Plc
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 Unilever N.V., Unilever Plc filed Critical Unilever N.V.
Priority to AU22798/99A priority Critical patent/AU2279899A/en
Publication of WO1999036501A1 publication Critical patent/WO1999036501A1/fr

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
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/16—Organic compounds
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2068—Ethers
    • 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
    • C11D11/00—Special methods for preparing compositions containing mixtures of detergents
    • C11D11/0094—Process for making liquid detergent compositions, e.g. slurries, pastes or gels
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2003—Alcohols; Phenols
    • C11D3/2006—Monohydric alcohols
    • C11D3/201—Monohydric alcohols linear
    • 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
    • C11D3/20—Organic compounds containing oxygen
    • C11D3/2072—Aldehydes-ketones
    • 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

  • the present invention relates to the manufacture of detergent compositions which contain a UV absorbing agent .
  • EP697481 (CIBA-GEIGY: 1995) concerns textile treatment with a composition comprising UV-A compound, emulsifying agent, water and polysiloxane (i.e. silicone) in an otherwise aqueous textile treatment composition which comprises : a) a non-reactive UVA compound b) an emulsifying or dispersing agent for the UVA compound c) water d) optionally, a polysiloxane based product.
  • UV adsorbing agents such as benzophenone derivatives
  • benzophenone derivatives can be difficult to incorporate in compositions due to their insolubility, cross-reaction with other components etc.
  • UV adsorbing agents can be difficult to incorporate in compositions due to their insolubility, cross-reaction with other components etc.
  • Single phase or at least non-macro-emulsion liquid products are preferred to macro-emulsions for reasons of product stability and appearance.
  • the present invention provides a process for the manufacture of a detergent composition comprising a UV absorbing agent, said process comprising the steps of:
  • the process of the invention is suitable for making all kinds of detergent compositions containing a UV absorbing agent. It is particularly suitable for hard surface and window cleaning compositions.
  • suitable solvents for forming the premix are such solvents which are also suitably added to detergent compositions in their own right e.g. because they will improve the cleaning or other properties of such compositions .
  • Particularly suitable are glycol ether and alkanol solvents of the general formula:
  • Rl and R2 are independently Cl-6 alkyl or H, but not both hydrogen, and n are independently 0-5, E stands for an ethylene group and P stands for a propylene group.
  • the alcohol solvents are selected from the C1-C6 branched or straight chain alkanols, more preferably one or more of methanol, ethanol, propanols or butanols. Ethanol and iso-propanol are particularly preferred.
  • the solvent comprises at least one glycol ether solvent selected from the group comprising di- ethylene glycol mono-n-butyl ether (available in the marketplace as Butyl Digol TM, ethylene glycol mono-n- butyl ether and propylene glycol mono-n-butyl ether and mixtures .
  • glycol ether solvent selected from the group comprising di- ethylene glycol mono-n-butyl ether (available in the marketplace as Butyl Digol TM, ethylene glycol mono-n- butyl ether and propylene glycol mono-n-butyl ether and mixtures .
  • Mixtures of both glycol ethers and alcohols can also be used, both for the premix as well as in the final composition.
  • a mixture of di- ethylene glycol mono-n-butyl ether and ethanol, or a mixture of di-ethylene glycol mono-n-butyl ether and iso-propanol is very suitable as a solvent mix and particularly suitable for the final composition.
  • the total level of these solvents in the detergent compositions prepared according to the invention is preferably not more than 25% by weight, more preferably 20% or less, most preferably 10% or less.
  • the compositions preferably contain at least l%wt of these solvents, more preferably at least 2% and most preferably at least 5%.
  • the glycol ether solvents are particularly suitable to form the pre-mix.
  • the pre-mix will comprise a mixture of the UV absorber material and the solvent in a weight ratio of 1:1 - 1:20 (absorber material : solvent), i.e. a 5-50%wt concentration of the UV absorber in the premix is suitable, preferably a concentration of 5-20%wt is used.
  • the UV absorber premix is particularly suitable for the manufacture of detergent compositions having a pH in the range 1.0-12 more preferably the pH is at least 2.0, most preferably at least 3.0. Above pH 8.5 the benefit of some UV-absorbers falls off although others are effective up to pH 12. Below pH 3.0 surface damage may occur with hard surface cleaners, especially of enamel surfaces. The most preferred pH is from 3.0 to 8.5. Acids such as citric acid and bases such as sodium hydroxide or ammonia are generally used to regulate the pH to the required level .
  • UV adsorbing agents
  • UV-adsorbing agents effective in the UV-B range
  • Typical UV-adsorbers are benzophenone derivatives, more specifically 2-hydroxy-4-methoxybenzophenone (benzophenone- 3) .
  • Suitable materials are available in the marketplace from BASF and Haarmann & Reimer (H&R) .
  • UV absorbers include phenyl -benzimidazole sulfonic acid and methoxycinnamic acid esters such as octyl methoxycinnamate .
  • laundry detergent compositions comprise so called optical whiteners or brighteners, i.e. fluorescent compounds which absorb UV light and re-emit this as visible, particularly blue, light.
  • optical whiteners or brighteners i.e. fluorescent compounds which absorb UV light and re-emit this as visible, particularly blue, light.
  • Such compounds have no use in the hard surface cleaning compositions of the present invention and are therefore not comprised in the term UV absorbing agent ' and UV absorber .
  • Suitable levels of UV adsorbing agents are from 0.01%wt upwards, preferably at least 0.05%, more preferably at least 0.08%.
  • the maximum amount is generally 5%wt .
  • Higher amounts than 2%wt rarely serve a useful purpose and the amounts are preferably at most 1%, more preferably at most 0.5%.
  • the UV-adsorbing agent is water insoluble or substantially water insoluble.
  • compositions manufactured according to the present invention comprise at least one surfactant component.
  • Surfactants are selected from the nonionic, anionic, cationic or amphoteric surfactant materials .
  • the surfactant preferably comprises one or more of non- ionic and/or anionic surfactant components.
  • Nonionic surfactants show particular efficacy on fatty soils and are most preferred.
  • Cationic surfactants can be included in the compositions of the invention as hygiene agents.
  • compositions can include one or more amphoteric surfactants, preferably betaines, or other surfactants such as amine-oxide and alkyl-amino- glycinates.
  • amphoteric surfactants preferably betaines, or other surfactants such as amine-oxide and alkyl-amino- glycinates.
  • Betaines are preferred for reasons of cost, low toxicity (especially as compared to amine-oxide) and wide availability. It is believed that amphoteric surfactants show a slight synergy with some organic acids (when present) as regards antimicrobial effects.
  • the overall level of surfactant in the compositions is 0.1-10%wt, more preferably 0.5-8%wt, most preferably 0.5-4%wt.
  • alkoxylated alcohols alkoxylated phenols, alkyl-polyglucoside (APG) and amine oxides are very suitable for use in the compositions of the present invention e.g. in amounts of 0.1-5%wt.
  • APG is preferred for its non-streaking and good foaming properties.
  • Preferred levels of APG are such that the composition comprises 0.1-5%wt of APG, preferably 0.1-3 %wt , most preferably 0.2-2 %wt .
  • Preferred APGs contain C8-C16 alkyl chains and it is preferred that more than 50%wt of the APG present in the compositions of the invention comprises C12- C14 alkyl APG and that the majority of the remaining APG contains C8-C16.
  • the preferred degree of polymerization is 1.1-1.6, more preferably 1.3-1.5.
  • Suitable materials include GLUCOPON 425 CS TM (ex HENKE ) .
  • nonionics are alkoxylated alcohols, alkoxylated alkyl -phenols or amine oxides. Of these, alkoxylated alcohols are preferred as surfactants.
  • Suitable nonionic detergent active compounds can be broadly described as compounds produced by the condensation of alkylene oxide groups, which are hydrophilic in nature, with an organic hydrophobic compound which may be aliphatic or alkyl aromatic in nature. The length of the hydrophilic or polyoxyalkylene radical which is condensed with any particular hydrophobic group can be readily adjusted to yield a water-soluble compound having the desired degree of balance between hydrophilic and hydrophobic elements. Ethoxylated aliphatic alcohols are particularly preferred.
  • Particular examples include the condensation product of aliphatic alcohols having from 8 to 22 carbon atoms in either straight or branched chain configuration with ethylene oxide, such as a coconut alcohol ethylene oxide condensate having from 1 to 15 moles of ethylene oxide per mole of coconut alcohol; condensates of alkylphenols whose alkyl group contains from 6 to 12 carbon atoms with 1 to 25 moles of ethylene oxide per mole of alkylphenol .
  • Particularly preferred nonionic surfactants include the condensation products of C8-C18 alcohols with 2-12 moles of ethylene oxide.
  • the most preferred alkoxylated alcohol nonionic surfactants are ethoxylated alcohols having a chain length of C9-C11 and an EO value of at least 5 but less than 10.
  • Particularly preferred nonionic surfactants include the condensation products of CIO alcohols with 5-8 moles of ethylene oxide.
  • the preferred ethoxylated alcohols have a calculated HLB of 10-16. While mixtures of nonionic surfactants can be used it is preferred to use a single commercially available surfactant .
  • Anionic surfactants are also suitable.
  • anionic surfactants primary alkyl sulphates and/or alkyl ether sulphates are preferred components of compositions according to the invention.
  • alkyl ether sulphates are materials of the general formula :
  • Rl is linear or branched, C8-C18 alkyl and m is 1- 10.
  • M is a sodium, potassium or ammonium counterion. More preferably the alkyl chain length of the AES falls in the range C8-C16. Preferably the AES has a C12-C13 average alkyl chain length. Preferably the AES alkyl chain is linear. Suitable materials include DOBANOL-23-3S (RTM, ex SHELL) and sodium laurylether sulphate .
  • Antimicrobials include DOBANOL-23-3S (RTM, ex SHELL) and sodium laurylether sulphate .
  • antimicrobial agents can be used in the compositions prepared according to the present invention.
  • the preferred antimicrobials are quaternary ammonium compounds and/or phenolic compounds.
  • Typical levels of the antimicrobial agent in formulations range from 0.01 to 8%, with levels of 0.05-4wt%, particularly around 2% being preferred for normal compositions and up to two or four times that concentration being present in so called, 'concentrated' products .
  • concentration of the antimicrobial agent will be in the range 0.05-0.5%wt.
  • the ratio of the nonionic surfactant to the antimicrobial agent will preferably be in the range 50:1 to >1:1, more preferably 30:1 to >1:1 i.e. an excess of nonionic will be present relative to the antimicrobial.
  • compositions comprise a preservative.
  • a suitable preservative is PROXEL LV TM or FORMOL.
  • compositions prepared according to the invention can contain other minor ingredients which are not essential, but aid in their cleaning performance and in maintaining the physical and chemical stability of the product.
  • the composition can contain detergent builders.
  • a builder when employed, preferably will form from 0.1 to 25% by weight of the composition.
  • Metal ion sequestrants including ethylenediamine- tetraacetates, aminopolyphosphonates (such as those in the DEQUEST range) and phosphates and a wide variety of other poly-functional organic acids and salts, can also optionally be employed. It is believed that the hygiene performance of a composition is improved by the presence of a metal ion sequesterant .
  • Hydrotropes are useful optional components. It is believed that the use of hydrotropes enables the cloud point of the compositions to be raised without requiring the addition of anionic surfactants . The presence of both anionic surfactants and betaine at the same time is believed to be less desirable as these surfactants interact and form a complex which inhibits the synergistic hygiene activity of the amphoterics with the organic acid.
  • the formations according to the invention are free of anionic surfactants when betaine is present, or contain low levels of anionic surfactants, i.e. less than 50% of the total weight of surfactant present and preferably less than 50% of the weight of the betaine in the product.
  • Anionics are compatible with the solely alcohol ethoxylate based compositions of the present invention when the level is below 50%wt of the total surfactant present, but their level should be minimized in view of their interaction with the polymers.
  • the level of anionic is below 30%wt of the total surfactant content of the composition and more preferably below 10% of the surfactant content. It is possible to make compositions which contain little or no anionic surfactant.
  • Suitable hydrotropes include, alkali metal toluene sulphonates, urea, alkali metal xylene and cumene sulphonates, polyglycols, >20EO ethoxylated alcohols, short chain, preferably C2-C5 alcohols and glycols. Preferred amongst these hydrotropes are the sulphonates, particularly the cumene, xylene and toluene sulphonates. For the purposes of this invention the aromatic sulphonate hydrotropes are non considered anionics.
  • Typical levels of hydrotrope range from 0-5% for the sulphonates. Correspondingly higher levels of urea and alcohols are required. Hydrotropes are not always required for dilute, sprayable products, but may be required if lower EO or longer alkyl ethoxylates are used or the cloud point needs to be raised considerably. Typically, the cloud point of the final composition should preferably be in the range 45-50°C. The cumene sulphonate is the most preferred hydrotrope.
  • ethoxylated nonionic levels of around 7%wt corresponding levels of SCS will generally be in the range 0.6-0.8wt%, whereas for ethoxylated nonionic levels of around 14%wt corresponding levels of SCS will generally be in the range 1.0-1.2wt%.
  • compositions prepared according to the invention can also contain, in addition to the ingredients already mentioned, various other optional ingredients such as, colourants, optical brighteners, soil suspending agents, viscosity modifiers, detersive enzymes, compatible bleaching agents, gel-control agents, freeze-thaw stabilisers, and perfumes.
  • various other optional ingredients such as, colourants, optical brighteners, soil suspending agents, viscosity modifiers, detersive enzymes, compatible bleaching agents, gel-control agents, freeze-thaw stabilisers, and perfumes.
  • a pre-mix is prepared by dissolving at least one UV absorber, preferably a benzophenone derivative, in one or a mixture of C1-C6 alkanol solvent or glycol ether solvent of the general formula:
  • Rl and R2 are independently Cl-6 alkyl or H, but not both hydrogen, m and n are independently 0-5, to a concentration of 5-20%wt of the premix.
  • This premix is thereafter mixed with the remaining components of the detergent composition to obtain a preferred compositions having a pH of 3-12 and comprising:
  • Typical window cleaners (such as Vidrex [TM] ) available in the, for example, the Brazilian market contain ammonia and are of high pH, typically around 12-13. As will be described in more detail below, at these pH ' s benzophenone UV-absorbers are unstable in the commercially available products. For comparative purposes the present invention was also therefore compared below with a window cleaner available in Brazil as Vidrex Crystal TM, which is formulated without ammonia and with a pH of 7.
  • a pre-mixture of UV absorber/Butyl Digol at 10% concentration (0.5 g UV absorber in 5 g Butyl Digol) is prepared and the remaining components are admixed before the UV absorber/solvent is added.
  • the order of addition is water, Butyl Digol, ethanol, APG and then the pre- mixture
  • Table 2 demonstrates the results for the BASF and H&R UV absorber material in freshly prepared samples. Formulations as given in Table 1 are identified as " V (whether UV absorber material is present or not) .
  • the high pH (12) Vidrex product is identified as VR12 and the low pH (7) Vidrex product as VR7.
  • the UV B region is identified by bold text, and the figures given are
  • Table 2 shows that if no absorber is present (le) there is no significant absorbance in the UV B wavelength.
  • the embodiments of the invention with UV absorber all exhibit high absorbance, demonstrating compatibility of absorber and product. As soon as the pH of the product was increased by adding ammonia (to pH 12-13) , the absorbance decreases, demonstrating the preference for the lower pH formulations.
  • a typical window cleaner from the market (Vidrex pH 12 : examples lf-lg) to which the UV adsorber had been added shows the same behaviour especially at a wavelength of around 320nm: relatively low absorbance is seen at this high pH.
  • the colour turned from transparent to yellow, indicating a chemical reaction had taken place.
  • Table 2 also show the absorbance of the UV absorber in the low pH commercially available window cleaner (Vidrex pH 7) . With this sample precipitation occurred upon addition of the UV absorber, resulting in a white "cotton like" sediment.
  • compositions prepared according to the invention were compared with products which were available in the Brazilian market.
  • a typical heavy duty cleaners in this market is “Veja' (TM) , available from Reckitt & Colman.
  • a further known product is “Domex 1 (TM) and is manufactured by Lever.
  • the Domex product was formulated as follows (Table 3) : Table 3
  • UV light absorbance was measured with a spectrophotometer .
  • Table 4 shows the results.

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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)
  • Health & Medical Sciences (AREA)
  • Emergency Medicine (AREA)
  • Detergent Compositions (AREA)
  • Cosmetics (AREA)

Abstract

L'invention concerne un procédé de fabrication de compositions de détergence contenant un absorbeur U.V. Ce procédé comprend les étapes consistant à former un premier mélange de l'absorbeur U.V. et d'un ou de plusieurs solvants semi-polaires, puis à combiner ce premier mélange avec les constituants restants de la composition de détergence qui comporte au moins un tensioactif. Les solvants semi-polaires comprennent, de préférence, des éthers de glycol et/ou des alcanols. Ce procédé est notamment conçu pour préparer des compositions de nettoyage des surfaces dures et des vitres, contenant un absorbeur U.V. destiné à protéger la surface nettoyée ou des articles situés derrière des vitres, des dégradations provoquées par la lumière ultraviolette.
PCT/EP1999/000248 1998-01-19 1999-01-08 Procede de preparation de compositions de detergence WO1999036501A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU22798/99A AU2279899A (en) 1998-01-19 1999-01-08 Process for preparing detergent compositions

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9801082.0 1998-01-19
GBGB9801082.0A GB9801082D0 (en) 1998-01-19 1998-01-19 Improvements relating to hard surface cleaners

Publications (1)

Publication Number Publication Date
WO1999036501A1 true WO1999036501A1 (fr) 1999-07-22

Family

ID=10825509

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1999/000248 WO1999036501A1 (fr) 1998-01-19 1999-01-08 Procede de preparation de compositions de detergence

Country Status (6)

Country Link
AR (1) AR014416A1 (fr)
AU (1) AU2279899A (fr)
BR (1) BR9900074A (fr)
GB (1) GB9801082D0 (fr)
UY (1) UY25360A1 (fr)
WO (1) WO1999036501A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000036074A1 (fr) * 1998-12-16 2000-06-22 Unilever N.V. Compositions liquides transparentes/translucides contenues dans des bouteilles transparentes et renfermant des teintures colorante et fluorescente ou un absorbeur u.v.
WO2001083659A1 (fr) * 2000-05-02 2001-11-08 Unilever N.V. Composition et processus pour nettoyer des sols
US9951298B2 (en) 2014-01-20 2018-04-24 The Procter & Gamble Company Fluorescent brightener premix

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2130106A1 (fr) * 1971-03-15 1972-11-03 Colgate Palmolive Co
DE4333385A1 (de) * 1993-09-30 1995-04-06 Friedrich A Spruegel Flächendesinfektions- und Reinigungsmittel
WO1997044422A1 (fr) * 1996-05-23 1997-11-27 Unilever Plc Composition detergente

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2130106A1 (fr) * 1971-03-15 1972-11-03 Colgate Palmolive Co
DE4333385A1 (de) * 1993-09-30 1995-04-06 Friedrich A Spruegel Flächendesinfektions- und Reinigungsmittel
WO1997044422A1 (fr) * 1996-05-23 1997-11-27 Unilever Plc Composition detergente

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2000036074A1 (fr) * 1998-12-16 2000-06-22 Unilever N.V. Compositions liquides transparentes/translucides contenues dans des bouteilles transparentes et renfermant des teintures colorante et fluorescente ou un absorbeur u.v.
US6630437B1 (en) 1998-12-16 2003-10-07 Unilever Home & Personal Care Usa , Division Of Conopco, Inc. Transparent/translucent liquid compositions in clear bottles comprising colorant and fluorescent dye or UV absorber
WO2001083659A1 (fr) * 2000-05-02 2001-11-08 Unilever N.V. Composition et processus pour nettoyer des sols
US9951298B2 (en) 2014-01-20 2018-04-24 The Procter & Gamble Company Fluorescent brightener premix

Also Published As

Publication number Publication date
AU2279899A (en) 1999-08-02
GB9801082D0 (en) 1998-03-18
AR014416A1 (es) 2001-02-28
BR9900074A (pt) 2000-01-11
UY25360A1 (es) 1999-09-27

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