EP0996661A1 - Emulsions contenant des polysiloxanes organo-hydrogenes aqueux - Google Patents

Emulsions contenant des polysiloxanes organo-hydrogenes aqueux

Info

Publication number
EP0996661A1
EP0996661A1 EP98940121A EP98940121A EP0996661A1 EP 0996661 A1 EP0996661 A1 EP 0996661A1 EP 98940121 A EP98940121 A EP 98940121A EP 98940121 A EP98940121 A EP 98940121A EP 0996661 A1 EP0996661 A1 EP 0996661A1
Authority
EP
European Patent Office
Prior art keywords
organopolysiloxanes
weight
radicals
groups
units
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Withdrawn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
EP98940121A
Other languages
German (de)
English (en)
Inventor
Michael Geck
Enno Funk
Petra Stinglhammer
Bernward Deubzer
Gerhard Preiner
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.)
Wacker Chemie AG
Original Assignee
Wacker Chemie AG
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 Wacker Chemie AG filed Critical Wacker Chemie AG
Publication of EP0996661A1 publication Critical patent/EP0996661A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
    • C08J2383/04—Polysiloxanes

Definitions

  • the invention relates to aqueous stable emulsions which contain organohydrogenpolysiloxanes and to a process for their preparation.
  • Aqueous emulsions which contain organohydrogenpolysiloxanes and their applications are widely known, for example for the production of non-stick silicone coatings on paper or film by means of a crosslinking reaction (hydrosilylation), the production of water-repellent coatings by means of a crosslinking reaction (condensation), and hydrophobic impregnation of Textiles, leather or paper, as a release agent for bladder (bladder) coating in tire manufacture and for the hydrophobization of building materials.
  • organohydrogenpolysiloxane emulsions The stability of organohydrogenpolysiloxane emulsions is problematic due to the susceptibility to hydrolysis of the Si-H bond.
  • the reaction with water often creates silanol groups and gaseous hydrogen. Measures to improve the stability of organohydrogenpolysiloxane emulsions and to reduce the elimination of hydrogen have already been described.
  • Me ⁇ liand Textile Reports 41, 1125 (1960) discloses that methyl hydrogen polysiloxane emulsions, depending on the acid used, show an optimum stability at a set pH of 3.5-4.
  • EP-B 314 955 (General Electric Co., issued on January 11, 1995) claims the stabilization of emulsions of organopolysiloxanes containing hydrogen groups by adding hydroxy-functional organopolysiloxanes, preferably at neutral pH.
  • the invention relates to aqueous emulsions containing
  • organopolysiloxanes should also include polymeric, oligomeric and dimeric siloxanes.
  • the emulsions according to the invention have an average particle diameter of preferably 0.05-10 ⁇ m, particularly preferably 0.1-3 ⁇ m. All previously known organohydrogensiloxanes and optionally other organopolysiloxanes which have neither Si-bonded hydrogen nor organyloxy groups can be used as component A.
  • organohydrogenpolysiloxanes contained in the emulsions according to the invention are preferably those of units of the general formula
  • R may be the same or different and denotes SiC-bonded, optionally substituted hydrocarbon radicals having 1 to 18 carbon atoms, a is 0, 1, 2 or 3, on average 0.5 to 2, and b is 0, 1 or 2, on average 0.005 to 1, with the proviso that the sum of a + b is less than or equal to 3 and that at least one Si-bonded hydrogen atom is present per molecule.
  • R examples of R are alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, 1-n-butyl, 2-n-butyl, iso-butyl, tert. Butyl, n-pentyl, iso-pentyl, neo-pentyl, tert-pentyl; Hexyl radicals, such as the n-hexyl radical; Heptyl residues, such as the n-heptyl residue; Octyl radicals, such as the n-octyl radical and iso-octyl radicals, such as the 2, 2, 4-trimethylpentyl radical; Nonyl radicals, such as the n-nonyl radical; Decyl radicals, such as the n-decyl radical; Dodecyl radicals, such as the n-dodecyl radical; Octadecyl radicals, such as the
  • substituted radicals R are haloalkyl radicals, such as the 3, 3, 3-trifluoro-n-propyl radical, the 2, 2, 2, 2 ', 2', 2 '-hexafluoroisopropyl radical, the heptafluoroisopropyl radical and haloaryl radicals, such as the o-, m- and p-chlorophenyl radical.
  • the radical R is preferably the methyl, vinyl and the phenyl radical, the methyl radical being particularly preferred.
  • At least 75% of the Si-bonded radicals R in the organohydrogenpolysiloxane composed of units of the formula (I) are preferably methyl radicals.
  • the content of Si-bonded hydrogen in the organohydrogenpolysiloxane used according to the invention is preferably 0.001 to 2% by weight.
  • the organohydrogenpolysiloxane which is contained in the emulsions according to the invention can be a resin which is liquid at room temperature or an oil.
  • organohydrogenpolysiloxane of units of the formula (I) are those which hsi0 l ⁇ S units, HSiCH 3 0 units, HSi (CH 3) 2 O 0 _ 5 units and H 2 SiO units and ( CH 3 ) 3 SiO 05 -, (CH 3 ) 2 SiO and CH 3 Si0 ls units.
  • the organohydrogenpolysiloxane contained in the emulsions according to the invention is preferably essentially linear with a viscosity of preferably 1 to 100,000 mm 2 / s, particularly preferably 5 to 20,000 mm 2 / s, in each case at 25 ° C.
  • organohydrogenpolysiloxanes from units of the formula (I) are:
  • organopolysiloxanes which can be used in addition to the organohydrogenpolysiloxanes are preferably units of the formula
  • R 1 can be the same or different and means SiC-bonded, optionally substituted, aliphatic saturated hydrocarbon radicals with 1 to 18 carbon atoms
  • R 2 can be the same or different and means SiC-bonded, aliphatic unsaturated hydrocarbon radicals with 2 to 6 carbon atoms
  • c is 0 , 1, 2 or 3, on average 1 to 2.1
  • d is 0 or 1, on average 0 to 1, with the proviso that the sum of c + d is less than or equal to 3.
  • radicals R 1 are the examples given for R for aliphatically saturated, optionally substituted hydrocarbon radicals, methyl, ethyl, n- and iso-propyl radicals and the n-hexyl radical being preferred and the methyl radical being particularly preferred.
  • radicals R 2 are alkenyl radicals, such as the vinyl, allyl, 1-propenyl, 2-propenyl and 1-hexenyl radical, and also cyclopentenyl and cyclohexenyl radicals, vinyl and
  • 1-hexenyl radicals are preferred and the vinyl radical is particularly preferred.
  • At least 75% of the Si-bonded radicals R 1 in the organopolysiloxane from units of the formula (II) are methyl radicals.
  • organopolysiloxanes from units of the formula (II) which may be present in component A are those with a viscosity of preferably 10 to 110 7 mm 2 / s at 25 ° C.
  • the organopolysiloxane composed of units of the formula (II) is preferably essentially linear.
  • organopolysiloxanes from units of the formula (II) are examples of organopolysiloxanes from units of the formula (II).
  • the organopolysiloxanes used as stabilizers (B) can be any organopolysiloxanes which have been known to date and have organyloxy groups.
  • organopolysiloxanes used as stabilizers (B) are preferably those of units of the formula (III)
  • R 3 can be the same or different and has a meaning given for R above,
  • R 4 may be the same or different and may be substituted hydrocarbon radicals having 1 to 6 carbon atoms which may be substituted by alkyloxy groups, e is 0, 1, 2 or 3, preferably on average 0.5 to 2, particularly preferably on average 0, 7 to 1.9, and f is 0, 1, 2 or 3, preferably an average of 0.01 to 1.5, particularly preferably an average of 0.3 to 1.2, with the proviso that the sum e + f is less than or equal to 3 and at least one unit of the formula (III) with f different from 0 is present per molecule.
  • radicals R 3 are the examples given for R, the methyl, ethyl, propyl, butyl, cyclohexyl, Methylcyclohexyl, phenyl and vinyl radicals are preferred and the methyl, phenyl and vinyl radicals are particularly preferred.
  • radicals R 4 are the examples given for R for optionally substituted hydrocarbon radicals having 1 to 6 carbon atoms, the methyl, ethyl, methoxyethyl, propyl, butyl and phenyl radical being preferred and the methyl, ethyl, Propyl and butyl are particularly preferred.
  • the organopolysiloxanes containing organanyloxy groups used according to the invention as component B are preferably liquid at room temperature and have a viscosity of preferably 1 to 100,000 mm 2 / s, particularly preferably 5 to 20,000 mm 2 / s, in each case at 25 ° C.
  • organopolysiloxanes from units of the formula (III) are examples of organopolysiloxanes from units of the formula (III).
  • organopolysiloxanes used according to the invention as component A and the organopolysiloxanes used according to the invention as component B are commercially available products or can be prepared by processes customary in silicone chemistry.
  • emulsifiers which have also been used in organopolysiloxane emulsions, such as anionic, cationic or nonionic emulsifiers, can be used as component C in the emulsions according to the invention.
  • emulsifiers that can be used as component C are
  • alkyl sulfates e.g. with a chain length of 8 to 18 carbon atoms
  • EO ethylene oxide
  • PO propylene oxide
  • sulfonates for example alkyl sulfonates with 8 to 18 Carbon atoms, alkylarylsulfonates with 8 to 18 carbon atoms, esters and half esters of sulfosuccinic acid with monohydric alcohols or alkylphenols with 4 to 15 carbon atoms; optionally these alcohols or alkyl phenols can also be ethoxylated with 1 to 40 EO units.
  • partial phosphoric acid esters and their alkali and ammonium salts e.g. Alkyl and alkaryl phosphates with 8 to 20 carbon atoms in the organic radical, alkyl ether or alkaryl ether phosphates with 8 to 20 carbon atoms in the alkyl or alkaryl radical and 1 to 40 EO units.
  • Alkylaryl polyglycol ether having 2 to 40 EO units and 8 to 20 carbon atoms in the alkyl and aryl radicals.
  • Ethylene oxide / propylene oxide (EO / PO) block copolymers with 8 to 40 EO or PO units.
  • Alkyl polyglycosides of the general formula R'-0-Z o (IV), in which R 'is a linear or branched, saturated or unsaturated alkyl radical with an average of 8 to 24 carbon atoms and Z 0 is an oligoglycoside radical with an average of o 1 to 10 mean hexose or pentose units or mixtures thereof.
  • Quaternary ammonium salts (halides, sulfates, phosphates, acetates or hydroxides), the alkyl groups of which independently have 1 to 24 carbon atoms; optionally the alkyl or alkaryl or aralkyl groups of the quaternary ammonium compounds can also be partially ethoxylated (1 to 40 EO units).
  • the emulsifiers used according to the invention are preferably nonionic emulsifiers, such as the alkyl polyglycol ethers, alkylaryl polyglycol ethers, fatty acid polyglycol esters, alkyl polyglycosides and polyvinyl alcohols mentioned, alkyl polyglycol ethers having 2 to 40 EO units and alkyl radicals having 4 to 20 carbon atoms and polyvinyl alcohols
  • nonionic emulsifiers such as the alkyl polyglycol ethers, alkylaryl polyglycol ethers, fatty acid polyglycol esters, alkyl polyglycosides and polyvinyl alcohols mentioned, alkyl polyglycol ethers having 2 to 40 EO units and alkyl radicals having 4 to 20 carbon atoms and polyvinyl alcohols
  • Hoeppler viscosities of the 4% aqueous solutions of 3 to 70 mPas and a degree of saponification of 70 to 95% are particularly preferred.
  • additives (E) which have also been used to date to prepare emulsions, such as, for example, acids for adjusting the pH, organic solvents, biocides, such as bactericides, fungicides, algicides and microbicides, fragrances, wetting agents , Inhibitors, pigments, thickeners and fillers.
  • the acids optionally used as additives (E) are preferably acetic acid.
  • the organic solvents optionally used as additives (E) are preferably alkanols with 1-4 C atoms and toluene.
  • the emulsions according to the invention preferably contain no further components.
  • the components used to produce the emulsions according to the invention can each be a type of such a component or a mixture of at least two types of a respective component.
  • aqueous emulsions according to the invention are preferably those which
  • the quantitative ratio of component (A) to component (C) is preferably greater than 3, particularly preferably greater than 5.
  • the quantitative ratio of component (A) to component (B) is preferably greater than 5, particularly preferably greater than 10.
  • the quantitative ratio of component (A) to component (D) is preferably from 3: 1 to 1:20.
  • the pH of the emulsions according to the invention is preferably in the neutral to acidic pH range, particularly preferably at a pH of 3 to 4.
  • the emulsions according to the invention can be prepared by mixing components (A) to (D) and, if appropriate, (E) in any order, per se, using equipment which has hitherto been used to prepare emulsions.
  • Another object of the invention is a process for the preparation of emulsions, characterized in that (A) organohydrogenspolysiloxanes optionally in a mixture with organopolysiloxanes free from Si-bonded hydrogen and organyloxy groups, (B) organopolysiloxanes containing organanyloxy groups, emulsifiers, (D) water and optionally (E) additives are mixed together.
  • the emulsions according to the invention are preferably prepared by introducing the emulsifiers (C) and, if appropriate, mixing them with a little water and then incorporating the emulsion constituents (A) and (B); the (residual) water (D) is then incorporated.
  • the additives (E) are preferably added together with the (residual) water (D), but if appropriate already introduced together with the emulsifiers (C).
  • organopolysiloxanes (B) containing organyloy groups which are liquid at room temperature and has a low viscosity is advantageous, since the organopolysiloxanes containing organyloxy groups can thus be metered in easily during the production process; it is not necessary to prepare a pre-mix from component A and organopolysiloxanes containing organyloxy groups.
  • mixing devices which can be used in the process according to the invention are stirrers, such as blade, bar, anchor, grid, screw, propeller, disk, impeller, turbine and planetary stirrers, and twin-screw mixers, mixing turbines, colloid mills, ultrasonic mixers, in-line mixers, gear rim dispersers, pumps, homogenizers, such as high-pressure, turbine and rotary homogenizers.
  • stirrers such as blade, bar, anchor, grid, screw, propeller, disk, impeller, turbine and planetary stirrers
  • twin-screw mixers mixing turbines, colloid mills, ultrasonic mixers, in-line mixers, gear rim dispersers, pumps, homogenizers, such as high-pressure, turbine and rotary homogenizers.
  • the process according to the invention is preferably carried out at a temperature of 10 to 50 ° C. and the pressure of the surrounding atmosphere, ie 900 to 1100 hPa.
  • the pressure exerted on the respective components or mixtures is particularly preferably the (atmospheric) pressure which may be increased by the action of the mixing elements, the corresponding prevailing temperature is particularly preferably the (room) temperature which may be increased by the action of the mixing elements.
  • the emulsions according to the invention have the advantage that they have excellent hydrolysis resistance and thus reduced hydrogen elimination.
  • the emulsions according to the invention also have the advantage that the stabilizers used are very well compatible with the other components and the emulsions according to the invention are accessible in a wide range.
  • the process according to the invention has the advantage that it is very simple to carry out.
  • emulsions according to the invention can be used wherever emulsions which contain organohydrogenpolysiloxanes have hitherto been used, such as the applications mentioned at the beginning.
  • Emulsifiers I isotridecyl polyglycol ether with an average of 10
  • Ethylene oxide units (commercially available under the Arkopal ® N 150 brand from Hoechst AG)
  • the emulsifier shown in Table 1 is initially charged, mixed with equal parts by weight of deionized water and mixed with glacial acetic acid. With homogenization using a so-called Ultra-Turrax (from Janke + Kunkel), organohydrogen polysiloxane and organopolysiloxane containing alkoxy groups are added in portions as a stabilizer. The remaining amount of fully demineralized water and the
  • Comparative Examples 1.1 to 1.10 The emulsifier shown in Table 1 is initially charged, mixed with equal parts by weight of fully demineralized water, and glacial acetic acid is added except for Comparative Examples 1.4 and 1.6. In addition, the procedure is as described in Example 1, with the difference that instead of a stabilizer according to the invention, instead silanol-terminated polydimethylsiloxane is used as the stabilizer (Comparative Examples 1.9 and 1.10) or, if appropriate, the additives listed in Table 1 are incorporated (Comparative Examples 1.1 to 1.8) . The emulsions thus obtained are examined with regard to hydrogen development and stability. The results can be found in Table 1.
  • the emulsifier (see Table 2) is added in portions with organohydrogenspolysiloxane, optionally further organopolysiloxane and organopolysiloxane containing alkoxy groups as a stabilizer. Demineralized water and, if necessary, glacial acetic acid and biocide are worked into the resulting homogeneous paste with the Ultra-Turrax. The emulsions thus obtained are examined for hydrogen evolution, stability and particle diameter. The results can be found in Table 2. Comparative Examples 2 and 3
  • the emulsifier given in Table 2 is initially charged, mixed with equal parts by weight of deionized water and mixed with glacial acetic acid. With homogenization using a so-called Ultra-Turrax (from Janke + Kunkel), organohydrogen polysiloxane, optionally further organopolysiloxanes and organopolysiloxane containing alkoxy groups are added in portions as a stabilizer. The remaining amount of deionized water and the Bioz d formaldehyde are incorporated into the resulting homogeneous paste with the Ultra-Turrax. The emulsions thus obtained are examined for hydrogen evolution, stability and particle diameter. The results can be found in Table 2.
  • the emulsions from Example 5 and Comparative Example 5 are each tested as an emulsion component (crosslinker component) in an aqueous preparation for producing an anti-adhesive silicone coating on paper.
  • an emulsion with the designation Dehesive ® 410 E commercially available from Wacker-Chemie GmbH
  • vinyl-functional organopolysiloxane and a platinum catalyst and water with a) 3 parts by weight of emulsion
  • the Preparation is described in Example 5, and 77 parts by weight of water and b) 3 parts by weight of emulsion, the preparation of which is described in Comparative Example 5, and 77 parts by weight of water are mixed.
  • Mixtures a) and b) thus obtained are each applied to paper using a 30 ⁇ m doctor blade (commercially available under the name “Bosso Buxil 925” from Bosso Carte Speciali SpA, 1-10075 Mathi (TO)) and applied for 30 Exposed to a temperature of 150 ° C for seconds. After aging for 30 minutes at room temperature, the anti-adhesive silicone coatings a) and b) obtained in each case are subjected to functional tests. Regarding separating force measurements, measurement of adhesive strength maintenance, rub-off and migration (non-crosslinked silicone components), completely identical results are obtained within the scope of the measuring accuracy.
  • Example 6 shows that the addition of the stabilizers according to the invention has no adverse effect Subsequent applications, such as the production of non-stick silicone coatings on paper / film.

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  • Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

L'invention concerne des émulsions aqueuses contenant (A) des polysiloxanes organo-hydrogénés éventuellement en mélange avec des organopolysiloxanes dépourvus d'hydrogène à liaison Si et de groupes organyloxy, (B) des organopolysiloxanes, contenant des groupes organyloxy, comme stabilisants, (C) des émulsifiants ainsi que (D) de l'eau.
EP98940121A 1997-07-11 1998-07-02 Emulsions contenant des polysiloxanes organo-hydrogenes aqueux Withdrawn EP0996661A1 (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19729806 1997-07-11
DE19729806A DE19729806A1 (de) 1997-07-11 1997-07-11 Wäßrige Organowasserstoffpolysiloxane enthaltende Emulsionen
PCT/EP1998/004101 WO1999002581A1 (fr) 1997-07-11 1998-07-02 Emulsions contenant des polysiloxanes organo-hydrogenes aqueux

Publications (1)

Publication Number Publication Date
EP0996661A1 true EP0996661A1 (fr) 2000-05-03

Family

ID=7835435

Family Applications (1)

Application Number Title Priority Date Filing Date
EP98940121A Withdrawn EP0996661A1 (fr) 1997-07-11 1998-07-02 Emulsions contenant des polysiloxanes organo-hydrogenes aqueux

Country Status (6)

Country Link
US (1) US6184406B1 (fr)
EP (1) EP0996661A1 (fr)
JP (1) JP2000513407A (fr)
CA (1) CA2295523A1 (fr)
DE (1) DE19729806A1 (fr)
WO (1) WO1999002581A1 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2815049B1 (fr) * 2000-10-05 2002-12-20 Rhodia Chimie Sa Procede pour adoucir, rendre hydrophile et non jaunissante une matiere textile, dans lequel on utilise une composition comprenant un polyorganosiloxane
JP5128978B2 (ja) * 2008-02-07 2013-01-23 玉理化学株式会社 毛髪コンディショニング剤およびこれを用いた毛髪のコンディショニング方法
JP6387885B2 (ja) * 2015-04-06 2018-09-12 信越化学工業株式会社 剥離紙又は剥離フィルム用オルガノポリシロキサンエマルション組成物及びその製造方法、並びに剥離紙及び剥離フィルム

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1215929B (de) 1960-08-26 1966-05-05 Wacker Chemie Gmbh Stabilisatoren fuer waessrige Emulsionen, die Organowasserstoffpolysiloxane enthalten
NL286535A (fr) 1961-12-23
FR2114230A5 (fr) 1970-11-20 1972-06-30 Silicones Ste Indle
DE3026501A1 (de) 1980-07-12 1982-02-04 Bayer Ag, 5090 Leverkusen Polysiloxan-emulsionen mit verbesserter kaeltestabilitaet
FR2557121B1 (fr) * 1983-12-21 1986-10-10 Rhone Poulenc Spec Chim Compositions elastomeriques organopolysiloxaniques vulcanisables a chaud a caracteristiques physiques ameliorees
US4888384A (en) 1987-10-21 1989-12-19 General Electric Company Stable, two package water emulsions of silicone hydride fluids
DE19517346A1 (de) * 1995-05-11 1996-11-14 Wacker Chemie Gmbh Emulsionen von Organosiliciumverbindungen für die Hydrophobierung von Baustoffen
DE19628447A1 (de) 1996-07-15 1998-01-22 Bayer Ag Wäßrige Emulsionen, ein Verfahren zur Herstellung und deren Verwendung

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO9902581A1 *

Also Published As

Publication number Publication date
CA2295523A1 (fr) 1999-01-21
DE19729806A1 (de) 1999-03-18
WO1999002581A1 (fr) 1999-01-21
US6184406B1 (en) 2001-02-06
JP2000513407A (ja) 2000-10-10

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