EP0988283A2 - Peroxyacides - Google Patents

Peroxyacides

Info

Publication number
EP0988283A2
EP0988283A2 EP98933627A EP98933627A EP0988283A2 EP 0988283 A2 EP0988283 A2 EP 0988283A2 EP 98933627 A EP98933627 A EP 98933627A EP 98933627 A EP98933627 A EP 98933627A EP 0988283 A2 EP0988283 A2 EP 0988283A2
Authority
EP
European Patent Office
Prior art keywords
diperoxyacid
cationic
acid
alkyl
yield
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Withdrawn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
EP98933627A
Other languages
German (de)
English (en)
Inventor
John Unilever Research Port Sunlight Oakes
David William Unilever Research THORNTHWAITE
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
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 PLC, Unilever NV filed Critical Unilever PLC
Priority to EP98933627A priority Critical patent/EP0988283A2/fr
Publication of EP0988283A2 publication Critical patent/EP0988283A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C409/00—Peroxy compounds
    • C07C409/40—Peroxy compounds containing nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • C07D209/48—Iso-indoles; Hydrogenated iso-indoles with oxygen atoms in positions 1 and 3, e.g. phthalimide
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39—Organic or inorganic per-compounds
    • C11D3/3945—Organic per-compounds

Definitions

  • the present invention relates to cationic peroxyacids and to compositions including these peroxyacids as bleaches, in particular detergent compositions used for washing fabrics.
  • organic peroxyacids can be used as bleacnmg agents m detergent compositions.
  • Many different types of organic peroxyacids have oeen proposed such as peroxyoenzoic acid, peroxyphthalic acid, peroxyalkanoic acid and d ⁇ peroxyal ⁇ aned ⁇ o ⁇ c acids, described m US patents 4,110,095, 4,170,453, and 4,325,828.
  • peroxy acids which have been disclosed include amidoperoxyacids which contain a polar amide linkage part way along a hydrocarbon cnain (US Patents 4,634,551 and 4,686,063) and phthalimido-substituted peroxyalkanoic acids (EP-A-325,288) .
  • Suitable example optional substituents for R x and R 2 include one or more halide groups, C x -C 4 alkyl groups and Ci-C, alkoxy groups.
  • R 3 and R 4 are each a methyl group.
  • z is conveniently at least 1, and possibly 2 or 3. If w is 0 and R 2 is an optionally substituted aryl group, then y is suitably at least 1 and may be 2 , 3, 4 or 5.
  • R x and R 2 are preferably selected from optionally substituted aryl groups and C 5 -C 10 alkyl or alkenyl groups. In some embodiments it may be preferred for an aryl group of R x and/or R 2 to be unsubstituted.
  • X may be any suitable counter anion, particularly N0 3 " , HS0 4 ", S0 4 2 “, CH 3 S0 4 " , and R 5 - (O) q -S0 3 " , wherein R 5 is a C 2 -C 20 alkyl group, alkenyl group, or alkyl substituted or unsubstituted aryl group, and q is 0 or 1. It is particularly advantageous to employ a counter anion selected from sodium dodecyl sulphate (SDS) , sodium fatty acid alpha sulphonate (SFA ⁇ ) and tosylate, especially SDS and tosylate.
  • SDS sodium dodecyl sulphate
  • SFA ⁇ sodium fatty acid alpha sulphonate
  • the invention also provides a bleaching detergent composition, comprising from 3 to 40% by weight of one or more surface-active compounds, from 5 to 80% by weight of one or more detergency builders and an effective amount of a cationic diperoxyacid according to the present invention, as the bleach component.
  • the term "effective amount”, as used herein, means that the cationic diperoxyacid is present in a quantity such that it is operative for its intended purpose, i.e as a bleaching agent, when the detergent composition is combined with water to form an aqueous medium which may be used to wash and clean clothes, fabrics and other articles.
  • the cationic diperoxyacids of the present invention when present as the bleach component, will be present in bleaching detergent compositions in amounts of from 0.5 to 15% by weight, more preferably from 2 to 10% by weight.
  • the present invention provides a bleaching additive composition comprising from 50 to 90% by weight of a cationic diperoxyacid according to the present invention, as the bleach component.
  • the cationic diperoxyacids of the present invention were found to exhibit superior bleach performance, particularly under conditions of alkaline pH.
  • the present cationic diperacids were found to be highly weight-effective (caused by the presence of two peracid groups per molecule) .
  • the present cationic diperacids are expected to be biodegradable to a commercially useful level.
  • Another advantage of the peroxy acids according to the present invention is that the route by which several of the materials are made is simple in that it is capable of utilising available starting materials.
  • cationic diperoxyacids of the present invention may be prepared by reaction of an amine containing an acid or ester group (as appropriate) with a halide containing an acid or ester group (as appropriate) to form a quaternary ammonium diacid ester salt. This is subsequently peroxidised to form the desired cationic diperoxyacid.
  • diperoxyacids of the present invention may find use in a wide range of industrial applications and processes, for example in the field of plastics as polymerisation initiators, or as oxidants for olefin epoxidation, or as bleaching agents in the paper industry.
  • bleaching or cleaning agents are also particularly useful as bleaching or cleaning agents in washing, cleaning and disinfecting compositions, such as laundry bleaches, hard surface cleaners, toilet bowl cleansers, automatic dishwashing compositions, denture cleaners and other sanitizing compositions.
  • the cationic diperoxyacids of the present invention find particular application in detergent compositions since they show good bleach performance at medium to low washing temperatures, that is 60 to 20° C. This means that detergent compositions containing such peroxyacids may readily be used at the medium to low wash temperatures which are becoming increasingly common.
  • the bleaching detergent compositions of the invention will contain at least one surface-active compound, which may be anionic, cationic, nonionic or amphoteric in character, present in an amount from about 3 to about 40%, pref-erably from 5 to 35% by weight.
  • mixtures of the above surface-active compounds are used.
  • mixtures of anionic and nonionic surface-active compounds are commonly used.
  • Amounts of amphoteric or zwitterionic surface-active compounds may also be used but this is not generally desired owing to their relatively high cost. If used, they will be present in small amounts.
  • the surface-active material may be naturally derived, such as soap, or a synthetic material selected from anionic, nonionic, amphoteric, zwitterionic, cationic actives and mixtures thereof.
  • suitable actives are commercially available and are fully described in the literature, for example in "Surface Active Agents and Detergents", Volumes I and II, by Schwartz, Perry and Berch.
  • Synthetic anionic surfactants are well known to those skilled in the art. Examples include alkylbenzene sulphonates, particularly sodium linear alkylbenzene sulphonates having an alkyl chain length of C 8 -C 15 ; primary (C 12 - 15 ) and secondary alkyl sulphates (C 14 - 18 ) , particularly sodium C 12 - 15 primary alcohol sulphates; olefin sulphonates; alkane sulphonates; dialkyl sulphosuccinates; and fatty acid ester sulphonates.
  • alkylbenzene sulphonates particularly sodium linear alkylbenzene sulphonates having an alkyl chain length of C 8 -C 15 ; primary (C 12 - 15 ) and secondary alkyl sulphates (C 14 - 18 ) , particularly sodium C 12 - 15 primary alcohol sulphates; olefin sulphonates; alkane sulphonates; dialky
  • soaps of fatty acids are preferably sodium soaps derived from naturally occurring fatty acids, for example, the fatty acids from coconut oil, beef tallow, sunflower or hardened rapeseed oil .
  • Soaps may be incorporated in the compositions of the invention, preferably at a level, of less than 25% by weight. They are particularly useful at low levels in binary (soap/anionic) or ternary mixtures together with nonionic or mixed synthetic anionic and nonionic compounds .
  • Soaps which may be used are preferably the sodium, or, less desirably, potassium salts of saturated or unsaturated C 10 -C 24 fatty acids or mixtures thereof.
  • soaps may be present at levels between about 0.5% and about 25% by weight, with lower levels of between about 0.5% to about 5% being generally sufficient for lather control. If the soap is present at a level between about 2% and about 20%, particularly between about 5% and about 10%, this can give beneficial detergency effects.
  • the inclusion of soap is particularly valuable in detergent compositions to be used in hard water since the soap acts as a supplementary builder.
  • Suitable nonionic detergent compounds which may be used include the reaction products of compounds having a hydrophobic group and a reactive hydrogen atom, for example, aliphatic alcohols, acids, amides or alkyl phenols with alkylene oxides, especially ethylene oxide either alone or with propylene oxide.
  • nonionic detergent compounds are alkyl (C 6 _ 22 ) phenol-ethylene oxide condensates, the condensation products of linear or branched aliphatic 8 - 2o primary or secondary alcohols with ethylene oxide, and products made by condensation of ethylene oxide with the reaction products of propylene oxide and ethylenediamine .
  • Other so-called nonionic detergent compounds include long-chain tertiary amine oxides and tertiary phosphine oxides.
  • alkyl polyglycosides of general formula R 4 0 (R 5 0) t (G) y in which R 4 is an organic hydrophobic residue containing 10 to 20 carbon atoms, R 5 contains 2 to 4 carbon atoms, G is a saccharide residue containing 5 to 6 carbon atoms, t is in the range 0 to 25 and y is in the range from 1 to 10.
  • Alkyl polyglycosides of formula R 4 0(G) y ie . a formula as given above in which t is zero, are available from Horizon Chemical Co.
  • R 8 is preferably a saturated or unsaturated aliphatic residue .
  • the monoglyceryl ethers of alkanols are known materials and can be prepared, for example by the condensation of a higher alkanol and glycidol.
  • Glycerol monoesters are of course well known and available from various suppliers including Alkyril Chemicals Inc. Detergency Builders
  • Inorganic builders that may be present include alkali metal (generally sodium) carbonate; while organic builders include polycarboxylate polymers such as polyacrylates , acrylic/maleic copolymers, and acrylic phosphinates ; monomeric polycarboxylates such as citrates, gluconates, oxydisuccinates, glycerol mono-, di- and trisuccinates , carboxy ⁇ nethyloxysuccinates , carboxymethyloxymalonates , dipicolinates , hydroxyethyliminodiacetates ; and organic precipitant builders such as alkyl- and alkenylmalonates and succinates, and sulphonated fatty acid salts.
  • alkali metal generally sodium
  • organic builders include polycarboxylate polymers such as polyacrylates , acrylic/maleic copolymers, and acrylic phosphinates ; monomeric polycarboxylates such as citrates, gluconates, oxydisuccinates, g
  • Especially preferred supplementary builders are polycarboxylate polymers, more especially polyacrylates and acrylic/maleic copolymers, suitably used in amounts of from 0.5 to 15 wt% and monomeric polycarboxylates, more especially citric acid and its salts, suitably used in amounts of from 3 to 20 wt%.
  • compositions of the invention include polymers containing carboxylic or sulphonic acid groups in acid form or wholly or partially neutralised to sodium or potassium salts, the sodium salts being preferred.
  • the polymeric material is present at a level of from 0.1 to about 3% by weight and has a molecular weight of from 1000 to 2000000 and may be a homo- or co -polymer of acrylic acid, maleic acid or salt or anhydride thereof, vinyl pyrrolidone, methyl or ethyl -vinyl ethers and other poly erisable vinyl monomers.
  • Especially preferred materials are polyacrylic acid or polyacrylate, polymaleic acid/acrylic acid coplymer; 70:30 acrylic acid/hydroxyethyl maleate copolymer, 1:1 styrene/maleic acid coplymer; isobutylene/maleic acid and diisobutylene/maleic acid copolymers; methyl- and ethyl- -vinylether/maleic acid copolymers; ethylene/maleic acid copolymer; polyvinyl pyrrolidone; and vinyl pyrrolidone/maleic acid copolymer.
  • Other polymers which are especially preferred for use in liquid detergent compositions are deflocculating polymers such as for example disclosed in EP 346995.
  • an alkali metal silicate particularly sodium ortho-, meta- or preferably neutral or alkaline silicate, at a level of, for example, of 0.1 to 10 wt%
  • the cationic diperoxyacids of the present invention may be used in a variety of product forms including powders, on sheets or other substrates, in pouches, in tablets or in non-aqueous liquids, such as liquid nonionic detergent compositions .
  • the cationic diperoxyacids When incorporated in a bleach and or detergent bleach composition the cationic diperoxyacids will preferably be in the form of particulate bodies comprising said cationic diperoxyacid and a binder or agglomerating agent. In such a form the cationic diperoxycid is more stable and easier to handle.
  • the cationic diperoxyacids of the present invention may also be incorporated in detergent additive products.
  • Such additive products are intended to supplement or boost the performance of conventional detergent compositions and may contain any of the components of such compositions, although they will not comprise all of the components present in a fully formulated detergent composition.
  • Such additive products containing, for example, up to 90% by weight of the cationic diperoxyacid and a surface active material maybe particularly useful in hygiene applications eg hard surface cleaners.
  • Additive products in accordance with this aspect of the invention may comprise the cationic diperoxyacid alone or in combination with a carrier, such as a compatible particulate substrate, a flexible non-particulate substrate or a container (e.g. pouch or sachet) .
  • a carrier such as a compatible particulate substrate, a flexible non-particulate substrate or a container (e.g. pouch or sachet) .
  • compatible particulate substrates include inert materials, such as clays and other aluminosilicates, including zeolites both of natural and synthetic of origin.
  • Other compatible particulate carrier substrates include hydratable inorganic salts, such as phosphates, carbonates and sulphates. Additive products enclosed in bags or containers can be manufactured such that the bags/containers prevent egress of their contents when dry but are adapted to release their contents on immersion in an aqueous solution.
  • Hnmr ( ⁇ CDC1 3 ) 4.14, q, 2H, CH 2 CH 3 ; 3.4, t, 2H, BrCH 2 ; 2.3, t, 2H, CH 2 CO; 1.9, p, 2H, CH 2 CH 2 CO; 1.68, p, 2H, BrCH 2 CH 2 ; 1.5, p, 2H, BrCH 2 CH 2 CH 2 ; 1.25, t, 3H, CH 2 CH 3 ppm.
  • 6-Bromoethylhexanoate (44g; 0.197mole) was dissolved in 33% dimethylamine/ethanol solution (150ml, large xs) and then refluxed for 7 hours. The brown solution was concentrated under reduced pressure to yield a brown oil .
  • x Hnmr ( ⁇ CDC1 3 ) 4.13, q, 2H, CH 2 CH 3 ; 3.4, t ; 2.4, t, 2H, CH 2 C0; 2.34, s, 6H, N(CH 3 ) 2 ; 2.3, t, 2H, CH 2 N; 1.65, p, 2H, CH 2 CH 2 CO; 1.6, p, 2H, NCH 2 CH 2 ; 1.38, p, 2H, NCH 2 CH 2 CH 2 ; 1.25, t, 3H, CH 2 CH 3 ppm.
  • p-Chloro-4-toluic acid (8.35g; 0.05mole) was dissolved in propan-2-ol (50ml) with warming and this was added to a solution of sodium hydroxide (2g; 0.05mole in 50ml water). This mixture was then heated to 50°C and 6-dimethylamino ethyl hexanoate from 1.2 above (9.35g; 0.05mole) dissolved in propan-2-ol (20ml) was added over 15 minutes with stirring. On complete addition the solution was heated at 80°C for 2 hours. The solution was then filtered to remove any insoluble material and the filtrate concentrated under reduced pressure to yield an orange oil.
  • the oil was then triturated with diethyl ether (3 x 100ml) decanted off and azeotrope with propan-2-ol to yield a sticky white solid.
  • the solid was dissolved in water (100ml) and to this was added a solution of p-toluene sulphonic acid (13g; 0.07mole; 100ml water) giving an immediate white precipitate.
  • the solid was filtered, transferred to a rotary flask and partially dried (2g removed for analysis) .
  • the remaining solid was then added to a 3% solution of sulphuric acid (50ml) and refluxed for 14 hours.
  • the yellow solution was then concentrated under reduced pressure to yield a viscous yellow oil.
  • ⁇ nmr ( ⁇ CDCl 3 ) 8.7, s, H, NH; 8.1, d, 2H, Ar-H, 7.8, " d, 2H, Ar-H; 3.94, s, 3H, CH 3 ; 3.6, q, 2H, CH 2 NH; 2.54, t, 2H, CH 2 NMe 2 ; 2.3, s, 6H, Me 2 ; 1.8, p, 2H, CH 2 CH 2 N ppm.
  • ⁇ nmr ( ⁇ D 2 0) 8.13, d, 2H, COAr-H; 7.89, d, 2H, COAr-H; 7.7, d, 2H, CH 3 Ar-H; 7.37, d, 2H, CH 3 Ar-H; 4.13, q, 2H, CH 2 CH 3 ; 4.0, s, 3H, Me-O; 3.54, t, 2H, CONHCH 2 ; 3.4, m, 2H, CONHCH 2 CH 2 CH 2 ; 3.3, m, 2H, N+CH 2 (CH 2 ) 4 ; 3.1, s, 6H, Me 2 ; 2.4, s, 3H, Me-Ar; 2.3, t, 2H, CH 2 COOH; 2.13 " , m, 2H, CONHCH 2 CH 2 ; 1.7, m, 2H, CH 2 CH 2 COOH; 1.5, p, 2H, N+CH 2 CH 2 (CH 2 ) 3 ; 1.
  • the diperoxyacid prepared according to Example 1 (0.5 x 10 "3 M) was added to 100ml demineralised water in the glass vessel. Thereafter tea-stained (BC-1) test cloths were immersed in the solution for 30 minutes. The liquor to cloth ratio was greater than 20:1. After rinsing with water, the cloths were dried in a tumble drier.
  • the tested cationic diperoxyacid compound of the invention gives a superior bleaching performance as compared to the peroxyacid compounds of comparative Examples B and C, especially under conditions of alkaline pH. This is especially useful for commercial applications. It is desirable for bleaching detergent compositions to provide effective bleaching in wash liquors of about pH 9 or 10. This experiment shows that a cationic diperoxyacid of the present invention shows greatly improved bleaching activity in this pH range. It is at this pH level that the prior art peroxyacid compounds were particularly ineffective.
  • the cationic diperoxyacid of the present invention also shows greatly improved bleaching activity over another diperacid, DPDA.
  • peroxyadipylphthalimide also known as phthalaylaminoperoxycaproic acid - PAP
  • Compound IV could not be tested due to its extremely unstable nature. It is predicted that there would be a total loss of activity after being heated at 40°C for six days .
  • Compound (VII) is expected to have similar solubility to compound (IV) but with less available oxygen (5.2 vs 11.6% respectively) . This means that compound (VII) would be expected to cause less dye damage than compound (IV) .
  • the test was carried out by adding lOmg of each solid peracid to the centre of a cotton test cloth (10cm 2 ) which had been dyed with sulphur green (immedial green) dye. Five drops of pH 10 buffer solution was added to the peracid on the test cloth and the cloths were left for 30 seconds to allow damage. The cloth was then thoroughly rinsed in demineralised water and air dried before being evaluated. The evaluation was carried out using a "Texican Spectroflash 500" spectrometer and the cloths were read against a white background using an average of 8 readings around the test area (or "spot") . The data is expressed as a difference in reflectance at 640 and 510nm. The results are presented below:

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Detergent Compositions (AREA)

Abstract

L'invention a trait à un diperoxyacide organique cationique de la formule générale (I) dans laquelle R1 et R2 représentent chacun indépendamment un groupe alcényle ou alkyle C3-C10 éventuellement substitué, linéaire ou ramifié, ou bien un groupe aryle éventuellement substitué; R3 et R4 représentent chacun indépendamment un groupe alkyle C1-C4 linéaire ou ramifié; p représente 0 ou 1; z représente un entier situé entre 0 et 3; y représente un entier situé entre 0 et 5; w représente 0 ou 1; et X- représente un contre-anion. Il a été prouvé que le peroxyacide présente de bonnes propriétés de blanchiment, notamment dans des conditions de pH alcalin.
EP98933627A 1997-06-10 1998-06-05 Peroxyacides Withdrawn EP0988283A2 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP98933627A EP0988283A2 (fr) 1997-06-10 1998-06-05 Peroxyacides

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP97304042 1997-06-10
EP97304042 1997-06-10
EP98933627A EP0988283A2 (fr) 1997-06-10 1998-06-05 Peroxyacides
PCT/EP1998/003666 WO1998056760A1 (fr) 1997-06-10 1998-06-05 Peroxyacides

Publications (1)

Publication Number Publication Date
EP0988283A2 true EP0988283A2 (fr) 2000-03-29

Family

ID=8229367

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98933627A Withdrawn EP0988283A2 (fr) 1997-06-10 1998-06-05 Peroxyacides

Country Status (7)

Country Link
EP (1) EP0988283A2 (fr)
AU (1) AU8338098A (fr)
BR (1) BR9809977A (fr)
CA (1) CA2292894A1 (fr)
TR (1) TR199902992T2 (fr)
WO (1) WO1998056760A1 (fr)
ZA (1) ZA985027B (fr)

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Publication number Priority date Publication date Assignee Title
US9994799B2 (en) 2012-09-13 2018-06-12 Ecolab Usa Inc. Hard surface cleaning compositions comprising phosphinosuccinic acid adducts and methods of use
US8871699B2 (en) 2012-09-13 2014-10-28 Ecolab Usa Inc. Detergent composition comprising phosphinosuccinic acid adducts and methods of use
US9752105B2 (en) 2012-09-13 2017-09-05 Ecolab Usa Inc. Two step method of cleaning, sanitizing, and rinsing a surface
US20140308162A1 (en) 2013-04-15 2014-10-16 Ecolab Usa Inc. Peroxycarboxylic acid based sanitizing rinse additives for use in ware washing
CN108707098B (zh) * 2018-07-04 2020-06-12 史清元 结构中含有季铵盐离子和过氧羧酸基团的化合物及其制备方法和应用

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Publication number Priority date Publication date Assignee Title
JPS6456797A (en) * 1987-08-26 1989-03-03 Kao Corp Bleaching detergent composition
DE69608465T2 (de) * 1995-10-30 2000-09-14 Unilever N.V., Rotterdam Persaüre

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9856760A1 *

Also Published As

Publication number Publication date
BR9809977A (pt) 2000-08-01
WO1998056760A1 (fr) 1998-12-17
TR199902992T2 (xx) 2000-06-21
AU8338098A (en) 1998-12-30
ZA985027B (en) 1999-12-10
CA2292894A1 (fr) 1998-12-17

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