WO2002064246A1 - Verfahren zur herstellung blauer mikrokapseln - Google Patents
Verfahren zur herstellung blauer mikrokapseln Download PDFInfo
- Publication number
- WO2002064246A1 WO2002064246A1 PCT/EP2002/000855 EP0200855W WO02064246A1 WO 2002064246 A1 WO2002064246 A1 WO 2002064246A1 EP 0200855 W EP0200855 W EP 0200855W WO 02064246 A1 WO02064246 A1 WO 02064246A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- oil
- capsules
- blue
- microcapsules
- mixture
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/11—Encapsulated compositions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q11/00—Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J13/00—Colloid chemistry, e.g. the production of colloidal materials or their solutions, not otherwise provided for; Making microcapsules or microballoons
- B01J13/02—Making microcapsules or microballoons
- B01J13/06—Making microcapsules or microballoons by phase separation
- B01J13/08—Simple coacervation, i.e. addition of highly hydrophilic material
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0097—Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/412—Microsized, i.e. having sizes between 0.1 and 100 microns
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/42—Colour properties
- A61K2800/43—Pigments; Dyes
Definitions
- the invention relates to a process for the production of uniformly colored blue microcapsules using oil-soluble dyes. These capsules are mainly used in the cosmetic industry and oral hygiene.
- the present invention describes the encapsulation of a mixture of an oil-soluble material and a dye, the capsules obtained having a blue to dark blue color.
- the preferred encapsulation method is here
- the capsules thus obtained which have a colorless, transparent shell and a blue core, are preferably incorporated into products in the field of oral hygiene.
- microcapsules with a transparent shell containing an oil and a dye or a dye suspension
- the oily material mainly serves as a solvent or vehicle for the dye.
- EP-A-711 544 describes a toothpaste using capsules containing
- the capsules have an average size of 0.3 to 3 mm.
- WO 99/59535 A special form of encapsulation for oral hygiene products is described in WO 99/59535, in which the focus is on the aspects of the stability of the capsules in the presence of surface-active substances and foaming.
- WO 00/48560 deals with the encapsulation of a mixture of a liquid oil and a copper chlorophyll extract. These green microcapsules are preferably used in oral hygiene products. Typical oils are sunflower oil or paraffin oil.
- microcapsules are usually produced by means of coacervation and the oil core is colored, if necessary. There are basically two options for producing blue capsules.
- the capsule is coated with a water-soluble dye, the capsule becomes discolored due to so-called bleeding of the color or due to instability of the color in the preparation or formulation of the application product.
- oil-soluble dyes or pigment dyes come into consideration for this type of coloring.
- pigment dyes the problem of sedimentation occurs very often, i.e. that the dye is not homogeneously distributed in the capsule and optically the
- the invention therefore relates to a method for producing blue
- Microcapsules by encapsulating a mixture of a lipophilic core material and an oil-soluble dye, characterized in that D&C Green No. 6 or guaiazulene or a mixture of these two dyes is used as the dye.
- guaiazulene (7-isopropyl-l, 4-dimethylazulene) has proven itself, on the other hand D&C Green No. 6 (1,4-bis (4-methylphenyl) amino) -9,10-anthracendione; 1,4-p-toluidinoanthraquinone; CI. 61565).
- D&C Green No. 6 (1,4-bis (4-methylphenyl) amino) -9,10-anthracendione; 1,4-p-toluidinoanthraquinone; CI. 61565).
- the latter is particularly surprising since it is listed as a green oil-soluble dye in the dye lists. Both substances are commercially available dyes.
- the dyes are in 0.02% to 2%, preferably in 0.05% to 1.5%, particularly preferably in 0.1% to 1% and very particularly preferably in 0 , 1% to 0.5% added to the core material.
- the figures are percentages by weight and relate to the amount used
- Encapsulation materials that are typically used include: Cyclodextrins, gum arabic, gelatin, casein, albumin, fibrinogen, xanthan gum, soluble peptides, sodium alginate, carboxymethyl cellulose, polyvinylpyrrolidone and other natural or synthetic polymeric materials.
- the encapsulation materials are preferably additionally crosslinked.
- the crosslinking can be inherent to the encapsulation material or can be brought about by adding so-called crosslinking agents, such as, for example, glutaraldehyde.
- the encapsulation can be carried out according to methods known per se and described in the literature. Coacervation is preferred in the method according to the invention.
- Crosslinking with a crosslinking agent, preferably glutardialdehyde, in order to achieve the desired hardness of the capsules.
- a crosslinking agent preferably glutardialdehyde
- the manufacturing process can be carried out as follows, for example:
- the mostly liquid core material is mixed with the dye.
- This mixture is then introduced into an aqueous solution of the shell material, preferably containing gelatin, at 40-60 °.
- another casing material can be added, preferably gum arabic.
- a stabilizer or preservative can be added to the aqueous solution; potassium sorbate is preferred.
- This emulsion is adjusted to a pH in the range from 3.8 to 4.8, a pH range from 4.0 to 4.5 is preferred.
- the coacervates form, i.e. the dye-containing liquid core material is surrounded by a film of shell material and water, the microcapsules being formed. After cooling, usually to temperatures below 15 ° C, can
- a crosslinker preferably glutardialdehyde, is added to harden the shell.
- the order of processing can be modified in such a way that the dye-containing core material is added to an aqueous solution of gelatin and gum arabic and finally the pH is adjusted.
- the processing temperatures are lower, usually 30 to 45 ° C.
- the capsules are in the form of a slurry that can be used as such. It can, depending on your needs and
- Thickeners preferably carboxymethyl cellulose, preservatives and stabilizers, for example potassium sorbate and citrates, can be added to the slurry. If necessary, the slurry can also be subjected to drying, after which the microcapsules are in flowable form.
- the microcapsules have a transparent or translucent capsule shell and contain a blue liquid or a blue low-melting core material.
- the capsules produced according to the invention are thus clearly visible in the application product, for example an oral hygiene product.
- properties such as hardness, size, wall thickness, color depth or stability of the capsules can be significantly influenced.
- the hardness of the capsules can be adjusted by the method according to the invention in such a way that the capsules are neither too hard to survive the cleaning process nor too soft to be destroyed during the manufacturing process of the oral hygiene product become. In such a case, the aim is rather that the capsules are gradually destroyed over the entire period of the cleaning process and so one controlled release of the lipophilic material contained in the capsules can take place.
- the particle size of the blue capsules produced by the process according to the invention is typically in the range from 0.3 to 2.5 mm, preferably in the range from 0.5 to 1.8 mm and particularly preferably in the range from 0.8 to 1.2 mm ,
- the particle size can be measured using conventional methods, such as, for example, by sieving or microscopy.
- the oil-soluble core material to be encapsulated according to the invention can consist of a single substance or a mixture of substances. Some of the following are examples of suitable core materials.
- Proteins Proteins, keratin, collagen, casein, lecithin, sorbitol, antioxidants, phenol derivatives, antimicrobial agents, anti-inflammatory substances, anti-caries
- Substances vitamins, enzymes, plant extracts, preservatives, pH regulators, sweeteners, starches, flavors and aromas.
- ethereal oils and extracts, tinctures and balms such as, for example, anise oil, is particularly suitable as core material in the sense of the invention.
- substances with a cooling, refreshing effect in the mouth, throat or nose are particularly suitable as core material.
- Menthol, menthone, carboxamides, methacetals, menthol carbonates, menthol succinates, 1,8-cineol (eucalyptol), carvone, alpha-terpineol, thyol, methyl salicylate, 2'-hydroxypropiophenone may be mentioned here, for example.
- the optically active compounds can be used in enantiomerically pure form or as any mixtures of the two enantiomers.
- capsules according to the invention in cosmetics and oral hygiene: creams, gels, foams, dispersions, chewing gums, lozenges and candies.
- the area of application of dental care products is particularly preferred, in particular that of toothpastes, toothpastes, tooth gels.
- the capsules are added to the oral hygiene application in 0.05% to 5%, preferably in 0.2% to 3% and particularly preferably in 0.5% to 1.5%.
- the data are percentages by weight and relate to the finished product formulation or the overall recipe.
- a mixture of peppermint oil and 0.25% guaiazulen was made. This was added to an aqueous gelatin solution at 50 ° C. An aqueous solution of gum arabic was then added to this emulsion. The pH of the mixture was adjusted to 4.5 with stirring with aqueous acetic acid solution. The mixture was slowly cooled to room temperature and then glutardialdehyde was added. The supernatant solution was decanted off and the microcapsules were washed several times with water. The capsules thus produced had a diameter of 0.5 to 1.4 mm. These microcapsules had a transparent shell and a blue colored core material.
- Example 3 Example 3:
- a transparent tooth gel was produced with the following basic recipe, into which the blue capsules produced using different staining methods or with different dyes were incorporated.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Dispersion Chemistry (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Cosmetics (AREA)
- Manufacturing Of Micro-Capsules (AREA)
- Medicinal Preparation (AREA)
- General Preparation And Processing Of Foods (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BRPI0207119-3A BR0207119B1 (pt) | 2001-02-09 | 2002-01-28 | processo para produzir microcápsulas azuis, e uso das mesmas. |
EP02708317A EP1363731B1 (de) | 2001-02-09 | 2002-01-28 | Verfahren zur herstellung blauer mikrokapseln |
JP2002564034A JP2004526558A (ja) | 2001-02-09 | 2002-01-28 | 青色マイクロカプセルの製造方法 |
AT02708317T ATE306315T1 (de) | 2001-02-09 | 2002-01-28 | Verfahren zur herstellung blauer mikrokapseln |
DE50204524T DE50204524D1 (de) | 2001-02-09 | 2002-01-28 | Verfahren zur herstellung blauer mikrokapseln |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10106446A DE10106446A1 (de) | 2001-02-09 | 2001-02-09 | Verfahren zur Herstellung blauer Mikrokapseln |
DE10106446.2 | 2001-02-09 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002064246A1 true WO2002064246A1 (de) | 2002-08-22 |
Family
ID=7673748
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2002/000855 WO2002064246A1 (de) | 2001-02-09 | 2002-01-28 | Verfahren zur herstellung blauer mikrokapseln |
Country Status (8)
Country | Link |
---|---|
US (1) | US6506368B2 (de) |
EP (1) | EP1363731B1 (de) |
JP (1) | JP2004526558A (de) |
AT (1) | ATE306315T1 (de) |
BR (1) | BR0207119B1 (de) |
DE (2) | DE10106446A1 (de) |
ES (1) | ES2249560T3 (de) |
WO (1) | WO2002064246A1 (de) |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006077394A2 (en) * | 2005-01-19 | 2006-07-27 | The Central Science Laboratory (Csl) Representing The Secretary Of State For Environment, Food And Rural Affairs | Formulation |
WO2009112378A2 (de) * | 2008-03-03 | 2009-09-17 | Basf Se | Mikrokapseln, ihre herstellung und verwendung |
EP2865372A1 (de) * | 2013-10-22 | 2015-04-29 | Symrise AG | Wirkstoffkapseln |
WO2015158635A1 (de) * | 2014-04-14 | 2015-10-22 | Symrise Ag | Kapseln mit hoher wirkstoffbeladung |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR0312341A (pt) | 2002-08-02 | 2005-04-12 | Gillette Co | Composição antitransparente ou desodorante para aplicação tópica à pele, método para fabricação de uma composição para cuidado pessoal contendo cápsulas visìveis, e, método para aumentar a quantidade de fragrância de uma composição em gel clara |
US7147466B1 (en) * | 2003-10-24 | 2006-12-12 | Dentsply International, Inc. | Pressure indicator gel system and method therefore |
ES2313314T3 (es) * | 2004-03-04 | 2009-03-01 | Quest International Services B.V. | Composicion aromatizante en forma de particulas. |
NZ550152A (en) * | 2004-04-05 | 2009-04-30 | Pfizer Prod Inc | Microfluidized oil-in-water emulsions and vaccine compositions |
GB0510498D0 (en) * | 2005-05-23 | 2005-06-29 | Glaxo Group Ltd | Microcapsule composition |
WO2007009023A2 (en) * | 2005-07-13 | 2007-01-18 | Engineered Release Systems, Inc. | Chemically cross-linked elastomeric microcapsules |
US20080292692A1 (en) * | 2007-05-21 | 2008-11-27 | Shira Pilch | Impermeable Capsules |
ES2536232T3 (es) * | 2009-12-21 | 2015-05-21 | Unilever N.V. | Producto de confitería helado en partículas |
EP2347659B1 (de) * | 2010-01-22 | 2012-08-22 | Unilever PLC | Verfahren zur Herstellung gefrorener Teilchen |
DE102013210188A1 (de) * | 2013-05-31 | 2014-12-04 | Beiersdorf Ag | Naturkosmetik-konforme Mehr-Phasen-Zubereitungen enthaltend Guaiazulen |
WO2015138319A1 (en) * | 2014-03-10 | 2015-09-17 | Isp Investments Inc. | Oral care compositions comprising microcapsules with effective breakage characteristics |
CN107771205B (zh) * | 2015-04-09 | 2021-03-23 | 沙特阿拉伯石油公司 | 用于提高烃采收的胶囊型纳米组合物 |
CN108024927A (zh) * | 2015-09-03 | 2018-05-11 | 莱雅公司 | 用于对角蛋白材料进行护理和/或化妆的包含包封至少一种反射剂的油性分散体的微胶囊的含水凝胶 |
CN116507204A (zh) * | 2020-08-06 | 2023-07-28 | 西姆莱斯股份公司 | 用于制备微胶囊的方法 |
Citations (4)
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---|---|---|---|---|
GB1381444A (en) * | 1972-08-04 | 1975-01-22 | Blendax Werke Schneider Co | Toothpaste |
US3864275A (en) * | 1963-10-21 | 1975-02-04 | Pilot Pen Co Ltd | Process for enveloping fine drops of dispersed liquids |
US3893933A (en) * | 1973-02-23 | 1975-07-08 | Xerox Corp | Process for producing encapsulated toner composition |
US4459277A (en) * | 1980-10-07 | 1984-07-10 | Kosti Carl M | Plaque disclosing dentifrice compositions with solid microcapsules of dye |
Family Cites Families (13)
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US3341466A (en) | 1966-10-31 | 1967-09-12 | Brynko Carl | Process for making capsules |
US3957964A (en) * | 1974-01-30 | 1976-05-18 | Colgate-Palmolive Company | Dentifrice containing encapsulated flavoring |
US4071614A (en) * | 1975-06-03 | 1978-01-31 | Colgate Palmolive Company | Dentifrice containing encapsulated flavoring |
US4348378A (en) * | 1979-08-09 | 1982-09-07 | Kosti Carl M | Plaque disclosing dentifrice compositions with semi-solid microcapsules of dye |
EP0436729A4 (en) * | 1989-08-01 | 1991-09-11 | Kanebo, Ltd. | Microcapsule, treatment liquid containing microcapsules, and textile structure having microcapsules stuck thereto |
DE4040907A1 (de) * | 1990-12-20 | 1992-06-25 | Basf Ag | Verdoppelte azulenquadratsaeurefarbstoffe, deren zwischenprodukte sowie optisches aufzeichnungsmedium |
US5278693A (en) * | 1992-01-13 | 1994-01-11 | Gentex Corporation | Tinted solution-phase electrochromic devices |
US5237769A (en) * | 1992-06-29 | 1993-08-24 | Navarro Kenneth D | Fishing rod balance device |
US5411802A (en) * | 1993-10-29 | 1995-05-02 | Minnesota Mining And Manufacturing Company | Colorant compositions and processes |
TW412425B (en) | 1994-10-18 | 2000-11-21 | Kao Corp | Dentifrice composition having capsule particles |
US6046177A (en) * | 1997-05-05 | 2000-04-04 | Cydex, Inc. | Sulfoalkyl ether cyclodextrin based controlled release solid pharmaceutical formulations |
AU4143999A (en) | 1998-05-15 | 1999-12-06 | Unilever Plc | Oral composition comprising capsules |
WO2000048560A1 (en) * | 1999-02-15 | 2000-08-24 | Unilever N.V. | Encapsulation |
-
2001
- 2001-02-09 DE DE10106446A patent/DE10106446A1/de not_active Withdrawn
-
2002
- 2002-01-28 ES ES02708317T patent/ES2249560T3/es not_active Expired - Lifetime
- 2002-01-28 WO PCT/EP2002/000855 patent/WO2002064246A1/de active IP Right Grant
- 2002-01-28 JP JP2002564034A patent/JP2004526558A/ja active Pending
- 2002-01-28 DE DE50204524T patent/DE50204524D1/de not_active Expired - Lifetime
- 2002-01-28 AT AT02708317T patent/ATE306315T1/de not_active IP Right Cessation
- 2002-01-28 EP EP02708317A patent/EP1363731B1/de not_active Expired - Lifetime
- 2002-01-28 BR BRPI0207119-3A patent/BR0207119B1/pt not_active IP Right Cessation
- 2002-02-04 US US10/066,922 patent/US6506368B2/en not_active Expired - Lifetime
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
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US3864275A (en) * | 1963-10-21 | 1975-02-04 | Pilot Pen Co Ltd | Process for enveloping fine drops of dispersed liquids |
GB1381444A (en) * | 1972-08-04 | 1975-01-22 | Blendax Werke Schneider Co | Toothpaste |
US3893933A (en) * | 1973-02-23 | 1975-07-08 | Xerox Corp | Process for producing encapsulated toner composition |
US4459277A (en) * | 1980-10-07 | 1984-07-10 | Kosti Carl M | Plaque disclosing dentifrice compositions with solid microcapsules of dye |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2006077394A2 (en) * | 2005-01-19 | 2006-07-27 | The Central Science Laboratory (Csl) Representing The Secretary Of State For Environment, Food And Rural Affairs | Formulation |
WO2006077394A3 (en) * | 2005-01-19 | 2006-11-23 | Central Science Lab Csl Repres | Formulation |
AU2006207365B2 (en) * | 2005-01-19 | 2011-10-13 | The Secretary Of State For Environment, Food And Rural Affairs | Formulation |
WO2009112378A2 (de) * | 2008-03-03 | 2009-09-17 | Basf Se | Mikrokapseln, ihre herstellung und verwendung |
WO2009112378A3 (de) * | 2008-03-03 | 2010-05-06 | Basf Se | Mikrokapseln, ihre herstellung und verwendung |
US8349452B2 (en) | 2008-03-03 | 2013-01-08 | Basf Se | Microcapsules, their preparation and use |
EP2865372A1 (de) * | 2013-10-22 | 2015-04-29 | Symrise AG | Wirkstoffkapseln |
WO2015059062A1 (en) * | 2013-10-22 | 2015-04-30 | Symrise Ag | Active ingredient capsules |
US10299996B2 (en) | 2013-10-22 | 2019-05-28 | Symrise Ag | Active ingredient capsules |
WO2015158635A1 (de) * | 2014-04-14 | 2015-10-22 | Symrise Ag | Kapseln mit hoher wirkstoffbeladung |
US11471385B2 (en) | 2014-04-14 | 2022-10-18 | Symrise Ag | Capsules with a high active ingredient content |
Also Published As
Publication number | Publication date |
---|---|
DE10106446A1 (de) | 2002-10-10 |
BR0207119B1 (pt) | 2012-06-26 |
EP1363731B1 (de) | 2005-10-12 |
EP1363731A1 (de) | 2003-11-26 |
ES2249560T3 (es) | 2006-04-01 |
US20020159957A1 (en) | 2002-10-31 |
DE50204524D1 (de) | 2006-02-23 |
BR0207119A (pt) | 2004-02-10 |
ATE306315T1 (de) | 2005-10-15 |
JP2004526558A (ja) | 2004-09-02 |
US6506368B2 (en) | 2003-01-14 |
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