CA2162008C - Polyolefin molding composition with a reduced tendency to peel - Google Patents
Polyolefin molding composition with a reduced tendency to peel Download PDFInfo
- Publication number
- CA2162008C CA2162008C CA002162008A CA2162008A CA2162008C CA 2162008 C CA2162008 C CA 2162008C CA 002162008 A CA002162008 A CA 002162008A CA 2162008 A CA2162008 A CA 2162008A CA 2162008 C CA2162008 C CA 2162008C
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- CA
- Canada
- Prior art keywords
- oxidized
- wax
- molding composition
- polyolefin
- ene
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/02—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers not modified by chemical after-treatment
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L23/00—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers
- C08L23/26—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment
- C08L23/30—Compositions of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Compositions of derivatives of such polymers modified by chemical after-treatment by oxidation
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Extrusion Moulding Of Plastics Or The Like (AREA)
- Processing And Handling Of Plastics And Other Materials For Molding In General (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
A polyolefin molding composition which "peels" relatively little or not at all during extrusion comprises an olefin polymer and 0.001 to 5 phr of an oxidized wax which is an oxidized synthetic or semi-synthetic natural wax or an oxidized polyolefin wax.
Description
HOECHST ARTIENGESELLSCHAFT HOE 94/F 332 Dr.DA/we DESCRIPTION
Polyolef in molding composition with a reduced tendency to peel The invention relates to a polyolef in molding composition which "peels" relatively little or not at all during extrusion.
After preparation in the form of granules or grit, olef in polymers are processed to a finished component (product) by the extrusion or injection molding process. This finished component can be a film, a tube or a large or small hollow body. The problem of "peeling" occurs specifically during the processing of higher molecular weight polyolefins to give large hollow bodies (drums, tanks and the like).
"Peeling" is understood as meaning the phenomenon of filaments of the same material forming on the inside or outside of the plastic tube and later large hollow body on delivery of the polymer melt. These filaments inter-fere with the use of the vessel as intended, since, for example, they can become detached from an inner surface of the drum and contaminate the product contained there-in.
To eliminate peeling, it is customary to change the molecular weight distribution of the polymer or to adapt the processing machines to suit a given product, for example by changing the nozzle geometry.
A change in the molecular weight distribution is in general undesirable, since it leads to a change in the product properties. Modification of the processing machines is likewise usually not possible, since products from different manufacturers are used and the machines cannot be optimized for a certain product.
Polyolef in molding composition with a reduced tendency to peel The invention relates to a polyolef in molding composition which "peels" relatively little or not at all during extrusion.
After preparation in the form of granules or grit, olef in polymers are processed to a finished component (product) by the extrusion or injection molding process. This finished component can be a film, a tube or a large or small hollow body. The problem of "peeling" occurs specifically during the processing of higher molecular weight polyolefins to give large hollow bodies (drums, tanks and the like).
"Peeling" is understood as meaning the phenomenon of filaments of the same material forming on the inside or outside of the plastic tube and later large hollow body on delivery of the polymer melt. These filaments inter-fere with the use of the vessel as intended, since, for example, they can become detached from an inner surface of the drum and contaminate the product contained there-in.
To eliminate peeling, it is customary to change the molecular weight distribution of the polymer or to adapt the processing machines to suit a given product, for example by changing the nozzle geometry.
A change in the molecular weight distribution is in general undesirable, since it leads to a change in the product properties. Modification of the processing machines is likewise usually not possible, since products from different manufacturers are used and the machines cannot be optimized for a certain product.
The object of the present invention was to prevent the occurrence of the "peeling effect" during processing of polyolefins without a change having to be made to the molecular weight distribution of the polymer or to the processing machines.
This object was achieved by addition of an oxidized wax during granulation of the polyolefin powder.
The invention thus relates to a polyolefin molding composition with a reduced tendency to peel, comprising an olefin polymer and 0.001 to 5 phr of an oxidized wax.
The invention furthermore relates to a process for reducing peeling during extrusion of polyolefin molding compositions. This process includes adding 0.001 to 5phr of an oxidized wax to the molding composition comprising an olefin polymer.
The polyolefin molding composition according to the invention comprises an olefin polymer, for example one of the following:
1. Polymers of mono- and diolefins, for example polyethylene of high, medium or low density (which can be optionally cross-linked), polypropylene, polysiobutylene, polybut-l-ene, polymethylpent-l-ene, polyisoprene or polybutadiene, and polymers of cycloolefins, such as, for example, cyclopentene or norbornene.
2. Mixtures of the polymers mentioned under 1), for example mixtures of polypropylene with polyethylene or with polyisobutylene.
This object was achieved by addition of an oxidized wax during granulation of the polyolefin powder.
The invention thus relates to a polyolefin molding composition with a reduced tendency to peel, comprising an olefin polymer and 0.001 to 5 phr of an oxidized wax.
The invention furthermore relates to a process for reducing peeling during extrusion of polyolefin molding compositions. This process includes adding 0.001 to 5phr of an oxidized wax to the molding composition comprising an olefin polymer.
The polyolefin molding composition according to the invention comprises an olefin polymer, for example one of the following:
1. Polymers of mono- and diolefins, for example polyethylene of high, medium or low density (which can be optionally cross-linked), polypropylene, polysiobutylene, polybut-l-ene, polymethylpent-l-ene, polyisoprene or polybutadiene, and polymers of cycloolefins, such as, for example, cyclopentene or norbornene.
2. Mixtures of the polymers mentioned under 1), for example mixtures of polypropylene with polyethylene or with polyisobutylene.
3. Copolymers of mono- and diolefins with one another or with other vinyl monomers, such as, for example, ethylene/propylene copolymers, propylene/but-l-ene copolymers, propylene/isobutylene copolymers, ethylene/but-1-ene copolymers, propylene/butadiene copolymers, isobutylene/isoprene copolymers, ~162408 ethylene/alkyl acrylate copolymers, ethylene/alkyl methacrylate copolymers, ethylene/vinyl acetate copolymers or ethylene/acrylic acid copolymers and salts thereof (ionomers), as well as terpolymers of ethylene with propylene and a diene, such as hexadiene, dicyclopentadiene or ethylidenenorbornene.
Polyethylene, polypropylene, polybut-l-ene, polyhex-l-ene, poly-4-methylenepent-l-ene, polyoct-l-ene or copolymers thereof are preferred.
In addition to the olefin polymer, the molding composi-tion comprises waxes. These waxes are oxidized fully synthetic or semi-synthetic waxes or polyolefin waxes.
Preferred waxes are oxidized semi-synthetic waxes based on crude montan wax and polyolefin waxes.
The preferred oxidized semi-synthetic wax based on crude montan wax has the following characteristic data:
drop point 79 to 90 C
acid number 115 to 155 mg of ROH/g hydrolysis number 140 to 175 mg of KOH/g density 0.97 to 1.03 g/cm3 The preferred oxidized wax based on polyolefin wax has the following characteristic data:
drop point 95 to 130 C
acid number 15 to 70 mg of ROH/g hydrolysis number 25 to 115 mg of ROH/g density 0.90 to 1.03 g/cm3 The preferred oxidized semi-synthetic wax based on crude montan wax is formed by oxidative bleaching of crude montan wax. Waxes of this type have been commercially obtainable for many years.
The preferred oxidized wax based on polyolefin wax is formed by bulk polymerization in the Ziegler low pressure process. The resulting polyolefin wax is converted into oxidized products by treatment of the melt with air.
These waxes have also been commercially obtainable for many years.
The oxidized wax is added to the polymer in a concentra-tion of 0.001 to 5 phr (parts per 100 parts of resin), preferably 0.01 to 0.5 phr. In addition, the molding composition according to the invention can also comprise further additives, such as, for example, antioxidants, for example alkylated monophenols, alkylated hydro-quinones, hydroxylated diphenyl thioethers, alkylidene-bisphenols, benzyl compounds, acylaminophenols, esters of g-(5-t-butyl-4-hydroxy-3-methylphenyl)propionic acid, amides of g-(3,5-di-t-butyl-4-hydroxyphenyl)propionic acid, UV absorbers and light stabilizers, for example 2-(2'-hydroxyphenyl)benzotriazoles, 2-hydroxybenzophenones, oxalic diamides, esters of unsubstituted or substituted benzoic acids, acrylates, nickel compounds, sterically hindered amines (HALS), metal deactivators, phosphates and phosphites, peroxide-destroying compounds, basic costabilizers, nucleating agents, fillers and reinforcing materials, plasticizers, optical brighteners, flameproofing agents, antistatics, blowing agents, lubricants and pigments.
The oxidized waxes to be used according to the invention and, if appropriate, the other additives are incorporated by the methods customary for compounding polyolefins.
They are preferably added during the granulation.
The polyolefin molding composition according to the invention results in finished components which no longer show a peeling effect.
The following examples are intended to illustrate the invention. The "peeling effect" is characterized in the following manner. Drums having a capacity of 200 1 are produced from a polyolefin molding composition according to the invention at different throughputs on an extrusion ~161 0 blow molding machine. The drums are then assessed visu-ally with a classification into a"peel rating" of between 1 and 5. The rating 1 means that no filaments at all are to be observed on the drum surface. The drum surface is smooth and intact. Classification into ratings 2-5 is made according to the frequency of the occurrence of polymer filaments on the drum surface and the thick-ness thereof.
Example 1 A polyethylene having an MFR 190/21.6 of 2.0 g/10 minutes and a density of 0.950 g/cm3 was mixed in a mixing con-tainer with 0.12 phr of pentaerythritol tetrakis [3- (3-, 5-di-t-butyl-4-hydroxyphenyl)propionate] and 0.2 phr of an oxidized polyethylene wax (density 0.97 - 0.99 g/cm3, AN
15 - 17 mg of KOH/g, HN 20 - 35 mg of KOH/g) and the mixture was granulated at 290 C by means of an extruder.
400 kg of these granules were processed to give 200 1 drums on an extrusion blow molding line. The drums thus obtained had a smooth inner and outer surface. The "peel rating" was 1.
Example 2 A polyethylene having an MFR 190/21.6 of 2.0 g/10 minutes and a density of 0.950 g/cm3 was mixed in a mixing con-tainer with 0.12 phr of pentaerythritol tetrakis [3- (3-, 5-di-t-butyl-4-hydroxyphenyl)propionate] and 0.2 phr of an oxidized polyethylene wax (density 0.97 - 0.99 g/cm3, AN
15 - 17 mg of KOH/g, HN 20 - 35 mg of KOH/g) and the mixture was granulated together with 0.8 phr of a blue batch (masterbatch with blue pigment) at 290 C by means of an extruder. 400 kg of these blue granules were processed to give 200 1 drums on an extrusion blow molding line. The blue drums thus obtained had a smooth inner and outer surface. The "peel rating" was 1.
f416200s Comparison example A
The same polyethylene as in Examples 1 and 2 was stabilized in a mixing container with 0.12 phr of pentaerythritol tetrakis[3-(3-,5-di-t-butyl-4-hydroxyphenyl)propionate] and the mixture was granulated at 290 C by means of an extruder. 400 kg of these granules were extruded to give 200 1 drums on an extrusion blow molding line. The drums thus obtained had a "peeling effect" of rating 3, 4 or 5 on the inner or outer surface.
Comparison example B
The same polyethylene as in Examples 1 and 2 was mixed in a mixing container with 0.12 phr of pentaerythritol-tetrakis[3-(3-,5-di-t-butyl-4-hydroxyphenyl)propionate]
and together with 0.8 phr of a blue batch (masterbatch with blue pigment), and the mixture was granulated at 290 C by means of an extruder. 400 kg of these blue granules were extruded to give 200 1 drums on an extrusion blow molding unit. The blue drums thus obtained had a "peeling effect" of rating 3, 4 or 5 on the inner or outer surface.
Polyethylene, polypropylene, polybut-l-ene, polyhex-l-ene, poly-4-methylenepent-l-ene, polyoct-l-ene or copolymers thereof are preferred.
In addition to the olefin polymer, the molding composi-tion comprises waxes. These waxes are oxidized fully synthetic or semi-synthetic waxes or polyolefin waxes.
Preferred waxes are oxidized semi-synthetic waxes based on crude montan wax and polyolefin waxes.
The preferred oxidized semi-synthetic wax based on crude montan wax has the following characteristic data:
drop point 79 to 90 C
acid number 115 to 155 mg of ROH/g hydrolysis number 140 to 175 mg of KOH/g density 0.97 to 1.03 g/cm3 The preferred oxidized wax based on polyolefin wax has the following characteristic data:
drop point 95 to 130 C
acid number 15 to 70 mg of ROH/g hydrolysis number 25 to 115 mg of ROH/g density 0.90 to 1.03 g/cm3 The preferred oxidized semi-synthetic wax based on crude montan wax is formed by oxidative bleaching of crude montan wax. Waxes of this type have been commercially obtainable for many years.
The preferred oxidized wax based on polyolefin wax is formed by bulk polymerization in the Ziegler low pressure process. The resulting polyolefin wax is converted into oxidized products by treatment of the melt with air.
These waxes have also been commercially obtainable for many years.
The oxidized wax is added to the polymer in a concentra-tion of 0.001 to 5 phr (parts per 100 parts of resin), preferably 0.01 to 0.5 phr. In addition, the molding composition according to the invention can also comprise further additives, such as, for example, antioxidants, for example alkylated monophenols, alkylated hydro-quinones, hydroxylated diphenyl thioethers, alkylidene-bisphenols, benzyl compounds, acylaminophenols, esters of g-(5-t-butyl-4-hydroxy-3-methylphenyl)propionic acid, amides of g-(3,5-di-t-butyl-4-hydroxyphenyl)propionic acid, UV absorbers and light stabilizers, for example 2-(2'-hydroxyphenyl)benzotriazoles, 2-hydroxybenzophenones, oxalic diamides, esters of unsubstituted or substituted benzoic acids, acrylates, nickel compounds, sterically hindered amines (HALS), metal deactivators, phosphates and phosphites, peroxide-destroying compounds, basic costabilizers, nucleating agents, fillers and reinforcing materials, plasticizers, optical brighteners, flameproofing agents, antistatics, blowing agents, lubricants and pigments.
The oxidized waxes to be used according to the invention and, if appropriate, the other additives are incorporated by the methods customary for compounding polyolefins.
They are preferably added during the granulation.
The polyolefin molding composition according to the invention results in finished components which no longer show a peeling effect.
The following examples are intended to illustrate the invention. The "peeling effect" is characterized in the following manner. Drums having a capacity of 200 1 are produced from a polyolefin molding composition according to the invention at different throughputs on an extrusion ~161 0 blow molding machine. The drums are then assessed visu-ally with a classification into a"peel rating" of between 1 and 5. The rating 1 means that no filaments at all are to be observed on the drum surface. The drum surface is smooth and intact. Classification into ratings 2-5 is made according to the frequency of the occurrence of polymer filaments on the drum surface and the thick-ness thereof.
Example 1 A polyethylene having an MFR 190/21.6 of 2.0 g/10 minutes and a density of 0.950 g/cm3 was mixed in a mixing con-tainer with 0.12 phr of pentaerythritol tetrakis [3- (3-, 5-di-t-butyl-4-hydroxyphenyl)propionate] and 0.2 phr of an oxidized polyethylene wax (density 0.97 - 0.99 g/cm3, AN
15 - 17 mg of KOH/g, HN 20 - 35 mg of KOH/g) and the mixture was granulated at 290 C by means of an extruder.
400 kg of these granules were processed to give 200 1 drums on an extrusion blow molding line. The drums thus obtained had a smooth inner and outer surface. The "peel rating" was 1.
Example 2 A polyethylene having an MFR 190/21.6 of 2.0 g/10 minutes and a density of 0.950 g/cm3 was mixed in a mixing con-tainer with 0.12 phr of pentaerythritol tetrakis [3- (3-, 5-di-t-butyl-4-hydroxyphenyl)propionate] and 0.2 phr of an oxidized polyethylene wax (density 0.97 - 0.99 g/cm3, AN
15 - 17 mg of KOH/g, HN 20 - 35 mg of KOH/g) and the mixture was granulated together with 0.8 phr of a blue batch (masterbatch with blue pigment) at 290 C by means of an extruder. 400 kg of these blue granules were processed to give 200 1 drums on an extrusion blow molding line. The blue drums thus obtained had a smooth inner and outer surface. The "peel rating" was 1.
f416200s Comparison example A
The same polyethylene as in Examples 1 and 2 was stabilized in a mixing container with 0.12 phr of pentaerythritol tetrakis[3-(3-,5-di-t-butyl-4-hydroxyphenyl)propionate] and the mixture was granulated at 290 C by means of an extruder. 400 kg of these granules were extruded to give 200 1 drums on an extrusion blow molding line. The drums thus obtained had a "peeling effect" of rating 3, 4 or 5 on the inner or outer surface.
Comparison example B
The same polyethylene as in Examples 1 and 2 was mixed in a mixing container with 0.12 phr of pentaerythritol-tetrakis[3-(3-,5-di-t-butyl-4-hydroxyphenyl)propionate]
and together with 0.8 phr of a blue batch (masterbatch with blue pigment), and the mixture was granulated at 290 C by means of an extruder. 400 kg of these blue granules were extruded to give 200 1 drums on an extrusion blow molding unit. The blue drums thus obtained had a "peeling effect" of rating 3, 4 or 5 on the inner or outer surface.
Claims (6)
1. A process for reducing peeling during extrusion of a polyolefin molding composition, which comprises adding 0.001 to 5 phr of an oxidized wax to the molding composition comprising an olefin polymer.
2. The process as claimed in claim 1, wherein the oxidized wax is an oxidized polyolefin wax.
3. The process as claimed in claim 1, wherein the oxidized wax is an oxidized fully synthetic wax or an oxidized semi-synthetic wax.
4. The process as claimed in claim 1, wherein the olefin polymer is polyethylene, polypropylene, polybut-1-ene, polyhex-1-ene, poly-4-methylenepent-1-ene, polyoct-1-ene or a copolymer thereof.
5. The process as claimed in claim 4, wherein the olefin polymer is polyethylene.
6. The process as claimed in claim 1, wherein drums are produced during extrusion.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE4439248A DE4439248A1 (en) | 1994-11-03 | 1994-11-03 | Polyolefin molding compound with reduced tendency to peel |
| DEP4439248.6 | 1994-11-03 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2162008A1 CA2162008A1 (en) | 1996-05-04 |
| CA2162008C true CA2162008C (en) | 2008-01-22 |
Family
ID=6532383
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002162008A Expired - Fee Related CA2162008C (en) | 1994-11-03 | 1995-11-02 | Polyolefin molding composition with a reduced tendency to peel |
Country Status (12)
| Country | Link |
|---|---|
| EP (1) | EP0712890B1 (en) |
| JP (1) | JP3594713B2 (en) |
| KR (1) | KR100409142B1 (en) |
| AT (1) | ATE184621T1 (en) |
| AU (1) | AU697629B2 (en) |
| BR (1) | BR9505056A (en) |
| CA (1) | CA2162008C (en) |
| DE (2) | DE4439248A1 (en) |
| DK (1) | DK0712890T3 (en) |
| ES (1) | ES2139131T3 (en) |
| GR (1) | GR3031857T3 (en) |
| ZA (1) | ZA959242B (en) |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3222431A (en) * | 1956-07-18 | 1965-12-07 | Eastman Kodak Co | Printable polyethylene containing oxidized, thermally degraded polyethylene |
| US3367999A (en) * | 1965-10-22 | 1968-02-06 | Owens Illinois Inc | Method of making polyethylene surface hydrophilic and ink receptive by adding oxidized polyethylene |
| US4436863A (en) * | 1981-05-01 | 1984-03-13 | Allied Corporation | Use of ethylene-vinyl acetate copolymers and oxidized high density polyethylene homopolymers as processing aids for talc filled polypropylene compounds |
| JPS5845241A (en) * | 1981-09-10 | 1983-03-16 | Marubishi Yuka Kogyo Kk | Antistatic resin composition |
| JPS63225657A (en) * | 1986-10-28 | 1988-09-20 | Calp Corp | Composite polymer composition |
| DE3708384A1 (en) * | 1987-03-14 | 1988-09-22 | Hoechst Ag | POLYOLEFINE MOLD |
| DE3851256T2 (en) * | 1987-05-22 | 1994-12-15 | Mitsui Petrochemical Ind | Reinforced thermoplastic composition. |
| US5063446A (en) * | 1989-08-11 | 1991-11-05 | General Electric Company | Apparatus for transmitting auxiliary signal in a TV channel |
-
1994
- 1994-11-03 DE DE4439248A patent/DE4439248A1/en not_active Withdrawn
-
1995
- 1995-10-24 DE DE59506838T patent/DE59506838D1/en not_active Expired - Lifetime
- 1995-10-24 AT AT95116729T patent/ATE184621T1/en not_active IP Right Cessation
- 1995-10-24 ES ES95116729T patent/ES2139131T3/en not_active Expired - Lifetime
- 1995-10-24 DK DK95116729T patent/DK0712890T3/en active
- 1995-10-24 EP EP95116729A patent/EP0712890B1/en not_active Expired - Lifetime
- 1995-10-30 AU AU34562/95A patent/AU697629B2/en not_active Ceased
- 1995-11-01 BR BR9505056A patent/BR9505056A/en not_active IP Right Cessation
- 1995-11-02 CA CA002162008A patent/CA2162008C/en not_active Expired - Fee Related
- 1995-11-02 KR KR1019950039285A patent/KR100409142B1/en not_active IP Right Cessation
- 1995-11-02 ZA ZA959242A patent/ZA959242B/en unknown
- 1995-11-06 JP JP28732095A patent/JP3594713B2/en not_active Expired - Fee Related
-
1999
- 1999-11-17 GR GR990402951T patent/GR3031857T3/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JP3594713B2 (en) | 2004-12-02 |
| KR960017765A (en) | 1996-06-17 |
| KR100409142B1 (en) | 2004-02-11 |
| CA2162008A1 (en) | 1996-05-04 |
| DE4439248A1 (en) | 1996-05-09 |
| GR3031857T3 (en) | 2000-02-29 |
| AU697629B2 (en) | 1998-10-15 |
| ATE184621T1 (en) | 1999-10-15 |
| EP0712890A1 (en) | 1996-05-22 |
| BR9505056A (en) | 1997-10-14 |
| JPH08208897A (en) | 1996-08-13 |
| DK0712890T3 (en) | 2000-03-27 |
| EP0712890B1 (en) | 1999-09-15 |
| ZA959242B (en) | 1996-05-15 |
| AU3456295A (en) | 1996-05-09 |
| ES2139131T3 (en) | 2000-02-01 |
| DE59506838D1 (en) | 1999-10-21 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |