EP0598693B1 - Emulsions stables d'agents tensioactifs non-ioniques contenant un agent de contrÔle de la viscosité - Google Patents
Emulsions stables d'agents tensioactifs non-ioniques contenant un agent de contrÔle de la viscosité Download PDFInfo
- Publication number
- EP0598693B1 EP0598693B1 EP93870134A EP93870134A EP0598693B1 EP 0598693 B1 EP0598693 B1 EP 0598693B1 EP 93870134 A EP93870134 A EP 93870134A EP 93870134 A EP93870134 A EP 93870134A EP 0598693 B1 EP0598693 B1 EP 0598693B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- hydrophilic
- hydrophobic
- emulsion
- ethylenediamine
- nonionic surfactant
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/66—Non-ionic compounds
- C11D1/825—Mixtures of compounds all of which are non-ionic
-
- 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
- C11D3/33—Amino carboxylic acids
-
- 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
- C11D3/3947—Liquid compositions
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- 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
- the present invention relates to cleaning compositions. More particularly, the cleaning compositions according to the present invention are stable aqueous emulsions of nonionic surfactants which comprise a viscosity control system.
- such emulsions can be used to formulate products which do not contain hydrogen peroxide.
- such emulsions can be useful because they allow to keep a given hydrophobic ingredient separate from the aqueous phase, with which said hydrophobic ingredient could react, e.g., by hydrolysis.
- cleaning compositions be more or less viscous. Indeed, viscous compositions do not run like thin liquids, and their pouring, dispensing, i.e. their overall handling is therefore easier to control. This aspect is particularly important when cleaning compositions are used to clean hard surfaces, especially on inclined or vertical surfaces such as toilet bowls, or in the context of laundry. In those instances, the cleaning compositions must be thick enough for a controlled application onto fabrics, and for a good cling onto surfaces.
- thickening compounds are available for this purpose.
- thickening compounds it is meant herein compounds whose sole function is to thicken the compositions.
- Such compounds typically polymers, are however rather undesirable for a variety of reasons. Indeed, they can significantly increase formula cost without participating to the overall cleaning performance, they may involve processing issues, they may affect product stability, particularly in extreme acidic conditions, and they may affect the cleaning performance of the compositions.
- Another advantage of the present invention is that it is only required to use a very small amount of ethylenediamine-N,N'-disuccinic acid in order to obtain the desired effect, which makes the present invention particularly cost-efficient.
- ethylenediamine-N,N'-disuccinic acid also acts as a builder in the compositions of the present invention.
- ethylenediamine-N,N'-disuccinic acid plays has a dual function in the compositions of the present invention.
- Yet another advantage of the present invention is that ethylenediamine-N,N'-disuccinic acid has been found to provide additional stability to the preferred compositions herein which may comprise hydrogen peroxide as an optional but preferred compound.
- Yet another advantage of the present invention is that it allows to achieve a given viscosity target with a lower surfactant level, compared to a composition without ethylenediamine-N,N'-disuccinic acid.
- US-A-4 704 233 discloses laundry detergent compositions comprising a surfactant, a detergent builder and ethylenediamine-N,N'-disuccinic acid or alkali metal, alkaline earth, ammonium or substituted ammonium salts thereof or mixtures thereof. No emulsions of hydrophilic and hydrophobic nonionic surfactants are disclosed.
- EP-A-497 337 discloses stable aqueous suspensions of organic peracids containing surfactant mixtures consisting of C8-C22 fatty alcohol oxyethylated with 1-5 ethylene oxide (EO) units and C8-C22 fatty alcohol oxyethylated with 6-25 ethylene oxide units optionally together with other conventional component. No ethylenediamine-N,N'-disuccinic acid or alkali metal, alkaline earth, ammonium or substituted ammonium salts thereof or a mixture thereof is disclosed therein.
- a stable aqueous emulsion comprising from 2% to 70% by weight of the total emulsion of a hydrophilic nonionic surfactant with an HLB (hydrophilic-lipophilic balance) above 11 and a hydrophobic nonionic surfactant with an HLB below 10, and from 10% to 95% by weight of water, said emulsion further comprising from 0,01% to 10% by weight of the total emulsion of ethylenediamine-N,N'-disuccinic acid, or the alkali metal, alkaline earth metal, ammonium, or substituted ammonium salts thereof or mixtures thereof.
- HLB hydrophilic-lipophilic balance
- compositions according to the present invention are aqueous. Accordingly, the compositions according to the present invention comprise from 10% to 95% by weight of the total composition of water, preferably from 30% to 90%, most preferably from 60% to 85%. Deionized water is preferably used.
- compositions according to the present invention are emulsions of nonionic surfactants.
- Said emulsions of nonionic surfactants comprise at least two nonionic surfactants.
- said two nonionic surfactants In order to form emulsions which are stable, said two nonionic surfactants must have different HLB values (hydrophilic lipophilic balance), and the difference in value of the HLBs of said two surfactants is more than 1, preferably at least 3.
- HLB values hydrophilic lipophilic balance
- compositions according to the present invention comprise from 2 % to 70 % by weight of the total composition of said hydrophilic and hydrophobic nonionic surfactants, preferably from 3 % to 40 %, most preferably from 4 % to 30 %.
- compositions according to the present invention further comprise as an essential element an ethylenediamine-N,N'-disuccinic acid.
- compositions herein are not limited to any specific viscosity, and depending on the exact use envisioned, various viscosities may be achieved.
- compositions according to the present invention comprise from 0.01 % to 10 % by weight of the total composition of ethylenediamine-N,N'-disuccinic acid, preferably from 0.01 % to 1 %.
- Ethylenediamine-N,N'-disuccinic acid can be synthesised, for example, from readily available, inexpensive starting materials such as maleic anhydride and ethylenediamine as follows.
- the magnesium complexes are the most preferred for inclusion in compositions according to the invention. These complexes may be added to the compositions as such, or they may be formed during the process for making the composition by the reaction of an inert magnesium salt such as MgCl 2 or Mg SO 4 with an ethylenediamine-N,N'-disuccinic acid compound added as either the acid, or as a salt or complex. Where the ethylenediamine-N,N'-disuccinic acid compound is added in the making process, together with the inert magnesium salt, it is preferred that the molar ratio of magnesium to ethylenediamine-N,N'-disuccinic acid should be greater than 1:1, preferably greater than 3:1, to ensure formation of the desired magnesium complexes.
- the pH of the formulation influences its stability.
- bleaching ingredients being optional but preferred ingredients of the compositions herein, it is of course necessary, for chemical stability purposes to formulate the compositions herein with bleaches at a pH as is of from 0 to 6, preferably of from 0.5 to 5.
- the pH of the can be trimmed by all means available to the man skilled in the art.
- compositions according to the present invention comprise bleaches, i.e. hydrogen peroxide or water-soluble sources thereof.
- Suitable water-soluble sources of hydrogen peroxide include perborate, percarbonate and persilicate salts.
- Hydrogen peroxide is most preferred to be used in the compositions according to the present invention.
- the compositions according to the present invention comprise from 0.5% to 20% by weight of the total composition of hydrogen peroxide, preferably from 2% to 15%, most preferably from 3% to 10%.
- compositions according to the present invention may further comprise a bleach activator as an optional ingredient.
- bleach activator it is meant herein any compound which reacts with hydrogen peroxide to form a peracid.
- Suitable bleach activators for use herein typically belong to the class of esters, amides, imides, or anhydrides.
- a particular family of bleach activators of interest in the present invention were disclosed in EP-A-0 624 154. Particularly preferred in that family is acetyl triethyl citrate which was also disclosed in the context of bar soaps in FR-A-2 362 210.
- Acetyl triethyl citrate has the advantages that it is environmentally friendly as it eventually degrades into citric acid and alcohol.
- acetyl triethyl citrate has a good hydrolytical stability in the product upon storage and it is an efficient bleach activator.
- the term bleach activator includes mixtures of bleach activators.
- the nonionic surfactant system to be chosen to emulsify said bleach activator depends on the HLB value of said bleach activator. Accordingly, a suitable way to proceed is to determine the HLB value of the hydrophobic liquid ingredient (bleach activator), then select both the hydrophobic nonionic surfactants which have HLB values below said HLB value of said hydrophobic liquid ingredient and the hydrophilic nonionic surfactants which have HLB values above said HLB value of said hydrophobic liquid ingredient, wherein the difference in the HLB values of said hydrophobic and hydrophilic nonionic surfactants is preferably at least 3.
- an adequate nonionic surfactant system would comprise a hydrophobic nonionic surfactant with an HLB from 1 to below 10, and a hydrophilic nonionic surfactant with an HLB of above 11.
- a particularly suitable system comprises a hydrophobic nonionic surfactant with an HLB of 6, for instance a Dobanol @ 23-2 and a hydrophilic nonionic surfactant with an HLB of 15, for instance a Dobanol @ 91-10.
- Another suitable nonionic surfactant system comprises a Dobanol @ 23-6.5 (HLB about 12) and a Dobanol @ 23 (HLB below 6). All these Dobanol @ surfactants are commercially available from Shell.
- compositions according to the present invention may further comprise the usual optional ingredients such as perfumes, dyes, optical brighteners, builders and chelants, pigments, enzymes, dye transfer inhibitors, solvents, buffering agents and the like.
- compositions according to the present invention are particularly useful as laundry pretreaters, i.e compositions which are dispensed and left to act onto fabrics before they are washed, or as laundry additives to be used together with detergents to boost their performance, or as dishwashing compositions to be used either in the dishwashing machines or by hand, or as hard surface cleaners, or as toilet bowl cleaners, or as carpet cleaners to be used either by direct application onto the carpets or in carpet cleaning machines.
- the present invention further encompasses a process for the manufacture of the composition described herein.
- the process according to the present invention comprises at least three steps:
- a hydrophobic mixture which comprises said hydrophobic nonionic surfactant, ethylenediamine-N,N'-disuccinic acid, together with other, optional, hydrophobic ingredients which are to be formulated in the composition, such as perfumes, solvents, enzymes, bleach activators and polymers.
- a hydrophilic mixture which comprises at least said water, and said hydrophilic nonionic surfactant.
- Said hydrophilic mixture preferably further comprises other hydrophilic ingredients which are to be formulated in the composition such as dyes, optical brighteners, builders, chelants, hydrogen peroxide and buffering agents.
- first and said second steps can be performed in any order, i.e second step first is also suitable.
- said hydrophobic mixture and said hydrophilic mixture are mixed together.
- compositions are made which comprise the listed ingredients in the listed proportions (weigh %).
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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)
- Inorganic Chemistry (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
- Colloid Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Claims (8)
- Emulsion aqueuse stable comprenant de 2% à 70%, en poids de l'émulsion totale, d'un tensioactif non ionique hydrophile ayant une BHL (balance hydrophile-lipophile) supérieure à 11 et d'un tensioactif non ionique hydrophobe ayant une BHL inférieure à 10, et de 10% à 95% en poids d'eau, caractérisée en ce que ladite émulsion comprend, en outre, de 0,01% à 10%, en poids de l'émulsion totale, d'acide éthylènediamine-N,N'-disuccinique, ou de ses sels de métal alcalin, de métal alcalino-terreux, d'ammonium ou d'ammonium substitué, ou leurs mélanges.
- Emulsion selon la revendication 1, qui comprend 0,01% à 1%, en poids de l'émulsion totale, d'acide éthylènediamine-N,N'-disuccinique ou de ses sels de métal alcalin, de métal alcalino-terreux, d'ammonium ou d'ammonium substitué, ou leurs mélanges.
- Emulsion selon l'une quelconque des revendications précédentes, dans laquelle le tensioactif non ionique représente de 3% à 40% du poids de l'émulsion totale, de préférence de 4% à 30%.
- Emulsion selon l'une quelconque des revendications précédentes, dans laquelle la différence entre les BHL des tensioactifs non ioniques hydrophiles et des tensioactifs non ioniques hydrophobes est de 3.
- Emulsion selon l'une quelconque des revendications précédentes, qui comprend en outre de 0,5% à 20% de peroxyde d'hydrogène.
- Emulsion selon la revendication 5, qui comprend en outre un activateur de blanchiment.
- Emulsion selon la revendication 6, dans laquelle ledit activateur de blanchiment est le citrate d'acétyle et de triéthyle.
- Procédé de fabrication d'une composition selon l'une quelconque des revendications précédentes, qui comprend les étapes consistant à:préparer un mélange hydrophobe comprenant ledit tensioactif non ionique hydrophobe, l'acide éthylènediamine-N,N'-disuccinique, ou un de ses sels de métal alcalin, de métal alcalino-terreux, d'ammonium ou d'ammonium substitué, ou leurs mélanges, ainsi que d'autres ingrédients hydrophobes facultatifs qui sont à formuler dans la composition, tels que parfums, solvants, enzymes, activateurs de blanchiment et polymères;préparer un mélange hydrophile comprenant au moins ladite eau et ledit tensioactif non ionique hydrophile et, le cas échéant, d'autres ingrédients hydrophiles facultatifs qui sont à formuler dans la composition, tels que colorants, azurants optiques, adjuvants, chélateurs, peroxyde d'hydrogène et agents tampons;mélanger ensuite l'un avec l'autre ledit mélange hydrophobe et ledit mélange hydrophile.
Priority Applications (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69322744T DE69322744T2 (de) | 1992-11-16 | 1993-07-12 | Stabile, nichtionische Tensidemulsionen, welche Viskositätskontrollmittel enthalten |
ES93870134T ES2125322T3 (es) | 1992-11-16 | 1993-07-12 | Emulsiones acuosas estables de tensioactivos no ionicos con un agente de control de la viscosidad. |
AT93870134T ATE174955T1 (de) | 1992-11-16 | 1993-07-12 | Stabile, nichtionische tensidemulsionen, welche viskositätskontrollmittel enthalten |
EP93870134A EP0598693B1 (fr) | 1992-11-16 | 1993-07-12 | Emulsions stables d'agents tensioactifs non-ioniques contenant un agent de contrÔle de la viscosité |
AU55891/94A AU5589194A (en) | 1992-11-16 | 1993-10-29 | Stable aqueous emulsions of nonionic surfactants with a viscosity controlling agent |
PCT/US1993/010444 WO1994011099A1 (fr) | 1992-11-16 | 1993-10-29 | Emulsions aqueuses stables de tensio-actifs non ioniques comprenant un agent regulant la viscosite |
Applications Claiming Priority (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP92870188 | 1992-11-16 | ||
EP92870188A EP0598170B1 (fr) | 1992-11-16 | 1992-11-16 | Compositions de nettoyage et de blanchiment |
EP93870104A EP0629690B1 (fr) | 1993-06-09 | 1993-06-09 | Emulsions aqueuses stables d'agents tensioactifs non-ioniques |
SG1996002630A SG52309A1 (en) | 1993-06-09 | 1993-06-09 | Stable aqueous emulsions of nonionic surfactants |
SG1996008330A SG55157A1 (en) | 1993-06-09 | 1993-06-09 | Stable aqueous emulsions of nonionic surfactants |
EP93870104 | 1993-06-09 | ||
EP93870103A EP0629691B1 (fr) | 1993-06-09 | 1993-06-09 | Emulsions aqueuses stables d'agents tensioactifs non-ioniques |
EP93870103 | 1993-06-09 | ||
EP93870134A EP0598693B1 (fr) | 1992-11-16 | 1993-07-12 | Emulsions stables d'agents tensioactifs non-ioniques contenant un agent de contrÔle de la viscosité |
Publications (2)
Publication Number | Publication Date |
---|---|
EP0598693A1 EP0598693A1 (fr) | 1994-05-25 |
EP0598693B1 true EP0598693B1 (fr) | 1998-12-23 |
Family
ID=27545649
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP93870134A Expired - Lifetime EP0598693B1 (fr) | 1992-11-16 | 1993-07-12 | Emulsions stables d'agents tensioactifs non-ioniques contenant un agent de contrÔle de la viscosité |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0598693B1 (fr) |
AT (1) | ATE174955T1 (fr) |
AU (1) | AU5589194A (fr) |
DE (1) | DE69322744T2 (fr) |
ES (1) | ES2125322T3 (fr) |
WO (1) | WO1994011099A1 (fr) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1996006908A1 (fr) * | 1994-08-26 | 1996-03-07 | The Procter & Gamble Company | Ethylenediamine disuccinate utilise comme detergent |
EP0791095A4 (fr) * | 1994-11-10 | 1997-10-15 | Procter & Gamble | Procede de nettoyage de moquette |
US5928384A (en) * | 1994-11-10 | 1999-07-27 | The Procter & Gamble Company | Method of cleaning carpets |
US5905065A (en) * | 1995-06-27 | 1999-05-18 | The Procter & Gamble Company | Carpet cleaning compositions and method for cleaning carpets |
US5733858A (en) * | 1995-08-30 | 1998-03-31 | The Dow Chemical Company | Succinic acid derivative degradable chelants, uses and compositions thererof |
WO1997008288A1 (fr) * | 1995-08-30 | 1997-03-06 | The Dow Chemical Company | Chelatants degradables derives de l'acide succinique, leurs utilisations et compositions |
EP0779357A1 (fr) * | 1995-12-16 | 1997-06-18 | The Procter & Gamble Company | Emulsions stables contenant un ingrédient hydrophobe liquide |
CA2295233A1 (fr) * | 1997-06-27 | 1999-01-07 | Lorenzo Matteo Pierre Gualco | Compositions detergentes liquides non aqueuses contenant des particules enzymatiques |
EP0906950A1 (fr) * | 1997-10-03 | 1999-04-07 | The Procter & Gamble Company | Compositions contenant des agents de blanchiment péroxydés comprenant un système d'agent chélatant particulier |
DE19961659A1 (de) * | 1999-12-21 | 2001-07-12 | Henkel Kgaa | Mittel zur Behandlung von Substraten |
EP1233055A1 (fr) * | 2001-02-15 | 2002-08-21 | Givaudan SA | Composition de blanchissement |
CA2437170C (fr) † | 2001-03-20 | 2009-10-27 | The Procter & Gamble Company | Compositions convenant pour le traitement des cheveux comprenant des chelatants, et procede pour reduire la deterioration des cheveux par oxydation |
KR101615431B1 (ko) * | 2014-05-15 | 2016-04-25 | 코오롱인더스트리 주식회사 | 폴리이미드 및 이를 이용한 필름 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0497337A2 (fr) * | 1991-02-01 | 1992-08-05 | Hoechst Aktiengesellschaft | Suspensions aqueuses d'acides peroxycarboxyliques |
EP0598170A1 (fr) * | 1992-11-16 | 1994-05-25 | The Procter & Gamble Company | Compositions de nettoyage et de blanchiment |
EP0629690A1 (fr) * | 1993-06-09 | 1994-12-21 | The Procter & Gamble Company | Emulsions aqueuses stables d'agents tensioactifs non-ioniques |
EP0629691A1 (fr) * | 1993-06-09 | 1994-12-21 | The Procter & Gamble Company | Emulsions aqueuses stables d'agents tensioactifs non-ioniques |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4704233A (en) * | 1986-11-10 | 1987-11-03 | The Procter & Gamble Company | Detergent compositions containing ethylenediamine-N,N'-disuccinic acid |
DE3907131A1 (de) * | 1989-03-06 | 1990-09-13 | Henkel Kgaa | Bleichmittelsuspension |
-
1993
- 1993-07-12 ES ES93870134T patent/ES2125322T3/es not_active Expired - Lifetime
- 1993-07-12 AT AT93870134T patent/ATE174955T1/de not_active IP Right Cessation
- 1993-07-12 EP EP93870134A patent/EP0598693B1/fr not_active Expired - Lifetime
- 1993-07-12 DE DE69322744T patent/DE69322744T2/de not_active Expired - Fee Related
- 1993-10-29 WO PCT/US1993/010444 patent/WO1994011099A1/fr active Search and Examination
- 1993-10-29 AU AU55891/94A patent/AU5589194A/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0497337A2 (fr) * | 1991-02-01 | 1992-08-05 | Hoechst Aktiengesellschaft | Suspensions aqueuses d'acides peroxycarboxyliques |
EP0598170A1 (fr) * | 1992-11-16 | 1994-05-25 | The Procter & Gamble Company | Compositions de nettoyage et de blanchiment |
EP0629690A1 (fr) * | 1993-06-09 | 1994-12-21 | The Procter & Gamble Company | Emulsions aqueuses stables d'agents tensioactifs non-ioniques |
EP0629691A1 (fr) * | 1993-06-09 | 1994-12-21 | The Procter & Gamble Company | Emulsions aqueuses stables d'agents tensioactifs non-ioniques |
Also Published As
Publication number | Publication date |
---|---|
ES2125322T3 (es) | 1999-03-01 |
ATE174955T1 (de) | 1999-01-15 |
AU5589194A (en) | 1994-06-08 |
DE69322744T2 (de) | 1999-07-22 |
EP0598693A1 (fr) | 1994-05-25 |
WO1994011099A1 (fr) | 1994-05-26 |
DE69322744D1 (de) | 1999-02-04 |
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