EP0861036B1 - Verfahren zur herstellung von biologisch abbaubarem filtermaterial - Google Patents

Verfahren zur herstellung von biologisch abbaubarem filtermaterial Download PDF

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Publication number
EP0861036B1
EP0861036B1 EP96933415A EP96933415A EP0861036B1 EP 0861036 B1 EP0861036 B1 EP 0861036B1 EP 96933415 A EP96933415 A EP 96933415A EP 96933415 A EP96933415 A EP 96933415A EP 0861036 B1 EP0861036 B1 EP 0861036B1
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EP
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Prior art keywords
zone
filter
starch
die
melt
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EP96933415A
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German (de)
English (en)
French (fr)
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EP0861036A1 (de
Inventor
Jürgen Lörcks
Harald Schmidt
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BioTec Biologische Naturverpackungen GmbH and Co KG
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BioTec Biologische Naturverpackungen GmbH and Co KG
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    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/06—Use of materials for tobacco smoke filters
    • A24D3/067—Use of materials for tobacco smoke filters characterised by functional properties
    • A24D3/068—Biodegradable or disintegrable
    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24D—CIGARS; CIGARETTES; TOBACCO SMOKE FILTERS; MOUTHPIECES FOR CIGARS OR CIGARETTES; MANUFACTURE OF TOBACCO SMOKE FILTERS OR MOUTHPIECES
    • A24D3/00—Tobacco smoke filters, e.g. filter-tips, filtering inserts; Filters specially adapted for simulated smoking devices; Mouthpieces for cigars or cigarettes
    • A24D3/06—Use of materials for tobacco smoke filters
    • A24D3/08—Use of materials for tobacco smoke filters of organic materials as carrier or major constituent
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S264/00—Plastic and nonmetallic article shaping or treating: processes
    • Y10S264/48—Processes of making filters

Definitions

  • the invention relates to a method for producing Biodegradable filter material made from renewable raw materials for use as a tobacco smoke filter element of cigarettes, Cigars or pipes.
  • Cigarettes are cylindrical Form in which the smokable tobacco material is shredded Form is surrounded by a paper envelope. Usually own these cigarettes at one end a filter that with the cigarette is connected by a sleeve. Filter elements and cigarette filters are extensive in the literature described as a filter tow. For the manufacture of cigarette filters usually becomes a fiber material from the materials Cellulose-2.5-acetate or polypropylene is used. The use of paper or cotton is also known. According to known method is in cellulose acetate fiber material essentially manufactured by the nozzle spinning process.
  • the crimped or crimped the filter tows are first manufactured as filter rods, by stretching the curled ribbon, in volume enlarged and in a formatting device to the desired one Dimension brought and wrapped with paper.
  • the cellulose-2,5-acetate raw materials are usually included Glycerin acetate compounded as a plasticizer, which is not is easily contained in tobacco smoke.
  • Glycerin acetate compounded as a plasticizer which is not is easily contained in tobacco smoke.
  • DE-A-43 25 352 proposes a Cellulose acetate modified with ⁇ -caprolactone for the production of filaments to use.
  • EP-A-0 632 969 shows a degradable cellulose acetate with a low degree of substitution (Cellulose acetate with a degree of substitution of > 2 is considered to be difficult to degrade).
  • EP-A-0 597 478 discloses a cellulose acetate with a degree of substitution ⁇ 2.15 and degradation-accelerating additives such as polycaprolactone.
  • EP-A-0 634 113 describes a tobacco filter and method its production based on cellulose ester monofilaments using up to 30% water-soluble polymers, e.g. Strengths to reduce the degradability of the filter tow improve.
  • EP-A-0 641 525 proposes to improve the Degradability of cigarette filters based on cellulose acetate (fibers) the use of wood pulp.
  • US-A-5 396 909 describes a cigarette filter with a Filter tow made of cellulose acetate.
  • WO 93/07771 describes a method of making a cigarette filter Cellulose-2,5-acetate, for which by shared use the rate of degradation can be accelerated by starch should.
  • E-A-0 597 478 relates to a biodegradable Cellulose acetate with a degree of substitution of 1.0 to 2.15 for use as a raw material for the production of Cigarette filters.
  • EP-A-0 539 191 shows a lightweight Cigarette filter, in which the filter material partially consists of a closed-cell foam. This will achieved a reduction in weight of the filter.
  • An improved one Biodegradability is disclosed in DE-A-40 13 293 and DE-A-40 13 304 by using the biopolymer polyhydroxybutyric acid and / or the copolymer polyhydroxybutyric acid / polyhydroxyvaleric acid (PHB / PHV) as a fiber raw material for the production of a filter tow.
  • EP-A-0 614 620 describes a biodegradable filter element in the form of a foam or a foil based on Strength.
  • the filter material is made by extrusion.
  • the extruder system has several temperature zones.
  • GB-A-2 205 102 describes a process for the production of Cigarette filters made of extruded polysaccharide material such as e.g. Starch, in the form of foil, foam or strand.
  • Biological degradable starch fibers and their use in cigarette filters are known from EP-A-0 541 050.
  • the object of the invention is a filter tow or a filter material from renewable raw materials for the production of To provide cigarette filters or filters for smokers' goods, which has good filter properties, no interference of smoking pleasure or loss of aroma and its biodegradability is improved.
  • the invention proceeds from Basic idea, a filter tow or filter material made of fibers and filaments made of biopolymers based on thermoplastic To produce starch and its polymer mixtures.
  • Biopolymer materials made from renewable agricultural raw materials have become the focus of public interest in recent years for several reasons. The reasons for this are, for example, the innovation in the development of materials made from biopolymers, the conservation of fossil raw materials, the reduction of waste through rapid, complete biodegradability in the natural cycle, climate protection by reducing CO 2 release, and possible uses for agriculture.
  • Cigarette filters provided with the method according to the invention made of biopolymers are rapidly biodegraded after use by natural decomposition processes and represent a problem solution, for example with regard to the prevention of blockages and malfunctions in sewage treatment plants, which are caused by smoked cigarette residues, mainly via the public sewer network be washed in.
  • biopolymers used consisting essentially of starch materials with thermoplastic properties, disintegrate into the starting products carbon dioxide and water in a short time if they are exposed to the weather with the further action of microorganisms or get into the wastewater. It is also particularly advantageous that such a tobacco smoke filter reduces the tar and condensate contents in tobacco smoke without affecting the taste of smoking.
  • the for the production of filter elements from the invention Process produced filter tow or filter material used starch materials have thermoplastic properties that a Processing after adaptation of the operating conditions similar of the synthetic polymers and / or cellulose acetates in Enable "melt blown” process or spunbond process.
  • the "melt blown” process for the production of biopolymers An extrusion line uses fibers from a melt spinning mass, preferably with a melt pump and special "melt blown" nozzles, which are arranged in rows on a Nozzle bar with approx. 1000 nozzles are arranged.
  • the extruded Fibers based on the starch polymer materials BIOPLAST® GF 102 and / or GF 105 are made up of endless threads swirled by air with a fiber diameter of 1 to 35 ⁇ m, cooled and finished if necessary. Under in Axial direction blowing air streams that initially range from 40 to Are heated to 120 ° C and by variation with cold air Affecting fiber shape, the fibers are in the following Process steps combined to form a fiber bundle or fiber strand, placed on a circulating belt and in one Calenders with partly heatable, partly coolable rollers an endless filter or filter tow rod pressed and calibrated. These fibers are not particularly stretched and therefore have a soft fluffy structure with a for a large filter surface necessary filtertow.
  • starch thermoplastics are made based on the starch polymer materials BIOPLAST® GF 102 and / or GF 105 with MFI (melt index according to DIN 53 735) 18-200 in the extruder with spinning pump and spinneret with die plate and more than 1000 nozzle openings to fine fibers and processed a spunbond.
  • the individual becomes Filaments made a thread curtain in which the cooling air supplied laterally to the nozzle is accelerated so that the filaments are drawn.
  • the extruded threads fall 3 - 10 m deep into a chute the depth of fall at low melt viscosity and through the axial air flow is a stretch (1: 5 to 1: 100) of the fibers reached, which thereby increased considerably Strength and a thread diameter of 1 to 30 microns obtained.
  • At the bottom of the shaft are air and threads evenly swirled so that the filaments formed the starch material combined into an unconsolidated band are crimped in a stuffer box crimping machine and processed to filter rods on a filter rod machine become.
  • a starch polymer granulate 2 which serves as a starting material, with the addition of selected additives in an extruder system 3 processed into a melt and in the form of a film of individual fibers 4 through a nozzle plate with a corresponding one Number of openings extruded.
  • the fibers 4 pass through a rotating spinning plate 5, become a fiber bundle summarized, then by a Guide 6, for example compression rollers, pulled and closed an endless filter 7 formed.
  • a configuration system 8 is the final shaping, the endless filter 7 if necessary again a stuffer box crimping machine fed and in a filter rod machine individual filter elements 1 is processed.
  • Figures 1a and 1b each show a cross section and a longitudinal section of a filter element 1 made of fibers 4 of a starch polymer.
  • 1c shows a longitudinal section of a cigarette 10 with the filter element 12 produced according to the invention, a section containing tobacco 11 and a section containing the filter element 1 being wrapped and connected with cigarette paper 12, and the filter element 1 and the transition area to the tobacco 11 containing section are wrapped with a further band 13 for reinforcement.
  • Biopolymers based on renewable raw materials described are for the production of fibers, filaments, fiber filters and cotton wool are essentially based on Starch and include in particular thermoplastic starch and the group of polymer blends from thermoplastic Starch and other degradable polymer components, such as polylactic acid, Polyvinyl alcohol, polycaprolactone, aliphatic and aromatic polyesters and their copolymers. More used Additives are plasticizers, such as glycerin and their derivatives, hexavalent sugar alcohols, such as sorbitol and their derivatives.
  • thermoplastic Starch occurs in a first stage of the process with the help a swelling or plasticizing agent without Adding water and using dry or dried starch and / or starch by degassing the processing is dried.
  • Starches usually contain 14% water as native starches, Potato starch even as 18% natural moisture Initial moisture. If a starch with more than 5% moisture plasticized or gelatinized under pressure and / or temperature becomes a destructured strength, whose Manufacturing process is endothermic. The manufacturing process In contrast, the thermoplastic starch is a exothermic process. In addition, the crystalline proportions are less than 5% in the thermoplastic starch and remain unchanged.
  • destructurized starch In the case of destructurized starch, they are crystalline Proportions also immediately low after production, however, these take on destructured storage Strength again. The is also subject to change Glass transition point, which with thermoplastic starch remains at -40 ° C, while comparatively at destructured Starch rises again to above 0 ° C (see also EP-A-0 397 819). For these reasons, they are being restructured Starch and materials based on destructurized starch Storage gradually becomes relatively brittle. When producing the Polymer mixtures become phase mediators for homogenization the hydrophilic and polar starch polymer phase and the hydrophobic and non-polar polymer phase used either added or preferably during manufacture the polymer mixture arise in situ.
  • phase mediator block copolymers which include in the WO 91/16375, EP-A-0 539 544, US-A-5 280 055 and EP-A-0 596 437 are described.
  • the intermolecular compounding of these different polymers takes place under differentiated Processable temperature and shear conditions Granules.
  • These thermoplastic blends are made by coupling the phase interfaces between the less tolerable Polymers technologically manufactured so that the distribution structure the disperse phase during processing through the optimal processing window (temperature and Shear conditions) is reached.
  • cellulose acetate fiber filters and other low molecular weight filters Biopolymers such as polyhydroxybutyric acid (PHB) and polylactic acid (PLA) and filtering with the Distinguish filter material made from starch polymer fibers due to the different chemical structure of the Polymer surfaces from each other.
  • PHB polyhydroxybutyric acid
  • PLA polylactic acid
  • the strengths used as Macromolecules have a molecular weight of> 1 million the dominant amylopectin fraction with more than 75%. This leads together with the hydrophilic polymer surface improved adhesion properties of the filter Pollutant particles in tobacco smoke.
  • the Comparison of condensate concentration in inhalable tobacco smoke reduced to cellulose acetate filter. This effect is determined by the share of starch polymer fine fibers and the hydrophilicity affects the fiber.
  • Suitable polymer blends based on thermoplastic starch and methods of making them are from DE-A-43 17 696, WO 90/05161, DE-A-41 16 404, EP-A-0 542 155, DE-A-42 37 535 and DE-A-195 13 235 are known and have also been described in PCT / EP 94/01946, DE-A-196 24 641, DE-A-195 13 237, DE-A-195 15 013, CH 1996-1965 / 96 and DE-A-44 46 054 proposed.
  • Figure 2a shows an enlarged cross section and Figure 2b shows an enlarged longitudinal section of a filter element 1 from a crimped biopolymer film 16.
  • FIG. 2 c shows a longitudinal section of a cigarette 10 produced according to a method shown in Figure 2 Filterlement 1.
  • a section containing tobacco 11 and a section of the cigarette containing the filter element 1 10 are wrapped with cigarette paper 12.
  • the filter element 1 up to the transition area to the tobacco 11 containing section with a reinforcing band 13 envelops.
  • Fig. 3 shows a process scheme for the production of a filter tow or filter material according to the invention for use as cigarette filters and filters for tobacco products an extruded foam from renewable raw materials such as Strength.
  • starch foam by extrusion is fundamental e.g. known from DE-A-32 06 751 and DE-A-43 17 697. So-called cooking extrusion has been around since around 1930 known of strength. It is preferably in one Twin-screw extruder gelatinized the starch under pressure and temperature, destructured and extruded as a foam strand. This process technology is used primarily in the production of foamed snack products. Also extruded starch foams are known as packaging chips.
  • EP-A-0 447 792 discloses a method of manufacturing of paper foam made of paper fibers, starch and fully saponified Extruded polyvinyl alcohol for use as an insulating material.
  • starch foam 20 is compressed in an extrusion system 3 from a starting mixture 21 of starch, preferably native potato starch, and plasticizing and film-forming additives by thermal and mechanical introduction of energy, modified if necessary, plasticized and expanded by a drop in temperature and pressure, produced as a foamed round profile with a diameter of 10 mm and rolled in the formatting process to a diameter of 7.8 mm and processed into filter rods with a length of 12.6 mm.
  • the specific density of the foam filter elements is 12 kg / m 3 .
  • the extruded starch foam 29 is essentially open-pore, so that the foamed filter material made of destructured starch with a crystalline fraction of less than 5% is able to contain the liquids and liquid pollutants contained in tobacco smoke, such as condensate and tar products to adsorb, the starch foam itself not emitting inhalable, volatile products in the tobacco smoke.
  • Figure 3a shows an enlarged cross section and Figure 3b shows an enlarged longitudinal section of a filter element 1 from a starch foam 20.
  • FIG. 3c shows a longitudinal section of a cigarette 10 with a filter element 1 as shown in FIG Process is made.
  • the tobacco 11 and the filter element Portions of cigarette 10 containing 1 are common wrapped with cigarette paper 12. Furthermore, the filter element 1 to the transition area to tobacco 11 containing section with an outer, reinforcing band 13 wrapped.
  • the starch foam 20 is produced by extrusion using a Continua 37® twin-screw extruder and compressed in a compression step, wherein it is processed in a calender system 22 to form an endless filter 7.
  • the final shaping and separation into filter elements 1 takes place in a configuration system 8.
  • the process conditions and recipes for the one-step process design for the production of the filter tow or filter material from starch foam are shown in Tables I and IA using 4 examples each.
  • An essentially elastic and compressible filter tow with an open-pore foam structure represents a satisfactory process result (Examples 1 to 3 and 5 to 8).
  • Tables I and Ia Tables I and Ia
  • a twin-screw extruder of the type Continua C 37 from Werner & Pfleiderer is used to extrude the starch foam material. It has a nozzle plate, which can be equipped with 1 to 4 nozzle openings, each with a diameter of 1.5 to 4 mm.
  • the temperature setting of the extruder system is carried out by external cooling and heating devices.
  • the extruder system has six temperature zones, the first four zones being kept at temperatures from 25 to 140 ° C. Temperature zones 5 and 6 can be operated with temperature settings from 140 to 165 ° C.
  • the preferred temperature settings can be found in Tables I and Ia:
  • the speeds of the twin-screw extruder preferably move between 200 and 300 rpm.
  • the speed determines together with the dosing amount of the starting materials also that Torque of the extruder system essential.
  • a speed of 350 rpm was selected.
  • An optimal expansion of the starch foam 20 is the melt temperature Melt from 160 to 195 ° C achieved. These melt temperatures were realized during the tests.
  • the nozzle configuration were variations in diameter, the number of nozzles and the arrangement of the nozzle openings in the nozzle plate examined. The nozzle openings were with 1.5 to 3 mm in diameter tested, the number of nozzles was varied from 1 to 3 nozzles.
  • the arrangement of the nozzle opening was from the center of the nozzle plate over a medium diameter to largest diameter tested. From the tests carried out on the one-step process were each a nozzle with an opening diameter of 2.5 mm (Example 1) or 4 mm (Examples 2 to 4), which are central was placed, tested.
  • the starch-additive mixture serves a single-shaft, volumetric dosing device, whereby the dosing quantities from the operating parameters of the extruder system are directly dependent.
  • the device works with a Hollow shaft and has an application range of 1.5 kg / hour. to 35 kg / h
  • the preferred dosing amounts are from FIG. 4 evident.
  • a membrane metering device of the type is used for liquid metering Gamma / 5 from ProMint. In Examples 1-8 the amount of liquid from 0 to 5 liters / hour varies.
  • Table I lists the dosed volume of the liquid Stroke volume setting (in 0.1 ml / stroke) per stroke frequency setting of the dosing pump (in strokes per minute). At setting the dosing device from 5: 55 to 0.5 ml metered in at 55 strokes per minute. This gives one Dosage amount of 27.5 ml per minute.
  • the calender system 22 consists of four consecutive milled pulleys.
  • the diameter of the pulleys and the groove depth / groove width were in the experiments carried out varied. It continued to be the Tested the use of tension springs with different tensile strengths, which generate a pressure of the pulleys from 5 to 100 N. can.
  • the preferred contact pressures of the calender system are shown in Table I.
  • the endless filter 7 The starch foam 20 was reduced to different extents and finally to a standardized final diameter brought.
  • the starch foam 20 optionally adjusted to a certain residual moisture.
  • starch granules are first produced using a known process (for example DE-A-43 17 696 or WO 90/05161). The starch granules are then processed by renewed extrusion in a single-screw extruder to form a strand of starch foam and the manufacture of the filter tow or filter element 1 under conditions similar to those of the one-step process. A detailed description of the process is therefore omitted.
  • Tables II and IIa show process conditions and recipes for the production of thermoplastic starch-polymer granules (1st process stage) using four examples each:
  • Tables III and IIIa show the process conditions for the production of filter tows or filter material from thermoplastic starch-polymer granules processed into starch foam (2nd process stage): example number 1 No. 2 No. 3 No. 4 Single shaft extruder Extruder data Screw diameter 50 mm 50 mm 50 mm 50 mm Screw length 135 cm 135 cm 135 cm 135 cm Dwell time 45 s 45 s 45 s 45 s Temp. Zome 1 40 ° C 40 ° C 40 ° C 40 ° C Temp. Zone 2 70 ° C 70 ° C 70 ° C 70 ° C Temp. Zone 3 190 ° C 190 ° C 190 ° C 190 ° C Temp.
  • Zone 4 190 ° C 190 ° C 190 ° C 190 ° C Temp.
  • Zone 5 190 ° C 190 ° C 190 ° C 190 ° C Temp.
  • Zone 6 195 ° C 190 ° C 185 ° C 190 ° C Rpm 350 350 350 350 350 Power consumption 25 amps 26 amps 27 amps 26 amps Temp.
  • Zone 6 195 ° C 190 ° C 185 ° C 190 ° C Rpm 350 350 350 350 Power consumption 25 amps 26 amps 27 amps 26 amps Temp.
  • Pressure melt 280 bar 280 bar 260 bar 260 bar
  • FIG. 4 shows the results of biodegradability tests for the filter material according to the invention, where line a) starch foam, line b) fibers and films (starch material BIOFLEX® BF 102), line c) cellulose powder and line d) cellulose-2.5-acetate .
  • the essential property of the filter material according to the invention is the rapid biodegradation. This property was tested on the starch polymer material BIOLFELEX® BF 102 using the following method (at the OWS Institute in Ghent, Belgium): CEN Draft "Evaluation of the Ultimate Aerobic Biodegradability and Disintegration of Packing Materials under Controlled Composting Conditions - Method by Analysis of Released Carbon Dioxide "correspondingly modified ASTM D 5338-92.
  • the starch material BIOFLEX® BF 102 from which the fibers and foils for producing the filter tow or filter material according to the invention are made, was mineralized to 96.6% under the test conditions after 45 days.
  • the filter material made of starch foam (line d)) is even more rapidly degradable due to its porous surface and polymer composition.
  • the very good biodegradability was determined by the COD (chemical oxygen demand in mg / l) and the BOD 5 (biological oxygen demand in mg / l), whereby a COD of 1050 mg / l and a BOD 5 of 700 mg / l were measured .
  • the quotient of BOD 5 / COD x 100 results in the very high biodegradability of 66%, with values of more than 50% being very easily degradable.
  • the filter material made of starch foam was more than 90% biodegraded under aerobic compost conditions. All filter materials produced by the process according to the invention meet the quality requirements of LAGA leaflet M 10: quality criteria and recommendations for use for compost as well as DIN 54 900: "testing the compostability of polymeric materials" and the "ok Compost” certificate.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biodiversity & Conservation Biology (AREA)
  • Extrusion Moulding Of Plastics Or The Like (AREA)
  • Biological Depolymerization Polymers (AREA)
  • Cigarettes, Filters, And Manufacturing Of Filters (AREA)
  • Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
  • Filtering Materials (AREA)
EP96933415A 1995-09-29 1996-09-27 Verfahren zur herstellung von biologisch abbaubarem filtermaterial Expired - Lifetime EP0861036B1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DE19536505 1995-09-29
DE19536505A DE19536505A1 (de) 1995-09-29 1995-09-29 Biologisch abbaubares Filtermaterial und Verfahren zu seiner Herstellung
PCT/EP1996/004234 WO1997012528A1 (de) 1995-09-29 1996-09-27 Biologisch abbaubares filtermaterial und verfahren zu seiner herstellung

Publications (2)

Publication Number Publication Date
EP0861036A1 EP0861036A1 (de) 1998-09-02
EP0861036B1 true EP0861036B1 (de) 2000-01-12

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US (1) US6062228A (zh)
EP (1) EP0861036B1 (zh)
JP (1) JP3266272B2 (zh)
KR (1) KR100261855B1 (zh)
CN (1) CN1113618C (zh)
AR (1) AR003751A1 (zh)
AT (1) ATE188599T1 (zh)
AU (1) AU696205B2 (zh)
BR (1) BR9611208A (zh)
CA (1) CA2233368C (zh)
CO (1) CO4750781A1 (zh)
DE (2) DE19536505A1 (zh)
ES (1) ES2141539T3 (zh)
GR (1) GR3032900T3 (zh)
ID (1) ID18221A (zh)
PL (1) PL180599B1 (zh)
PT (1) PT861036E (zh)
RU (1) RU2153828C2 (zh)
TR (1) TR199800561T1 (zh)
TW (1) TW546125B (zh)
WO (1) WO1997012528A1 (zh)
ZA (1) ZA968199B (zh)

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DE59604195D1 (de) 2000-02-17
KR19990044684A (ko) 1999-06-25
EP0861036A1 (de) 1998-09-02
CN1198080A (zh) 1998-11-04
AR003751A1 (es) 1998-09-09
DE19536505A1 (de) 1997-04-10
ES2141539T3 (es) 2000-03-16
CN1113618C (zh) 2003-07-09
US6062228A (en) 2000-05-16
ZA968199B (en) 1997-05-02
JPH11500629A (ja) 1999-01-19
AU7215996A (en) 1997-04-28
PL180599B1 (pl) 2001-03-30
BR9611208A (pt) 1999-04-06
WO1997012528A1 (de) 1997-04-10
CA2233368A1 (en) 1997-04-10
PT861036E (pt) 2000-06-30
ID18221A (id) 1998-03-19
JP3266272B2 (ja) 2002-03-18
RU2153828C2 (ru) 2000-08-10
AU696205B2 (en) 1998-09-03
GR3032900T3 (en) 2000-07-31
CO4750781A1 (es) 1999-03-31
KR100261855B1 (ko) 2000-08-01
PL325968A1 (en) 1998-08-17
TR199800561T1 (xx) 1998-06-22
TW546125B (en) 2003-08-11
ATE188599T1 (de) 2000-01-15

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