USRE34716E - Aqueous dispersions of polyester and polyester-amides cross-linked with metallic ions and casts made therefrom - Google Patents
Aqueous dispersions of polyester and polyester-amides cross-linked with metallic ions and casts made therefrom Download PDFInfo
- Publication number
- USRE34716E USRE34716E US08/016,808 US1680893A USRE34716E US RE34716 E USRE34716 E US RE34716E US 1680893 A US1680893 A US 1680893A US RE34716 E USRE34716 E US RE34716E
- Authority
- US
- United States
- Prior art keywords
- composition
- amount
- water
- percent
- total weight
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
- C08K5/098—Metal salts of carboxylic acids
-
- 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
- A61K8/0212—Face masks
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
- A61K8/27—Zinc; Compounds thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/85—Polyesters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- 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
- C08J3/24—Crosslinking, e.g. vulcanising, of macromolecules
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/01—Use of inorganic substances as compounding ingredients characterized by their specific function
- C08K3/011—Crosslinking or vulcanising agents, e.g. accelerators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/10—Metal compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K3/00—Use of inorganic substances as compounding ingredients
- C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
- C08K3/20—Oxides; Hydroxides
- C08K3/22—Oxides; Hydroxides of metals
Definitions
- This invention relates generally to cross-linking an aqueous dispersion of polyester or polyesteramide with the water soluble multivalent metallic ions.
- the aqueous dispersion of polyester or polyesteramides containing ether and sulfonate groups can also contain humectants and/or emollients which when cross-linked with metallic ions and poured into any desirable shaped mold form a clear or opaque cast of therapeutic functional nature.
- This invention also relates to the process of cross-linking the polyester or polyesteramide aqueous dispersion with metallic ions.
- compositions used for skin treatment contain emollients or humectants in lotion, cream or gel form. Such product are applied by evenly spreading the product on the skin. Upon loss of water, the product dries providing humectants and emollients to the epidermis.
- Water soluble gels that form protective films of various types are known.
- U.S. Pat. No 4,393,048 discloses a water soluble hydrogel of alkali metal alginate and glycerine that dries to a non-toxic, pliable protective film.
- U.S. Pat. No. 3,949,742 discloses a transparent medical dressing which performs as a synthetic film over skin wounds.
- Water soluble polyesters for example U.S. Pat. No. 4,502,976, are used to form cross-linked bioerodible hydrogels.
- the hydrogels, suitable for carrying water soluble therapeutic macromolecules and for implantation in living mammals, are produced by a complex polymerization process without using water soluble metallic ions.
- U.S. Pat. No. 3,879,168 to Franklin discloses a surgical dressing made of partially soluble alginic materials in the form of gauze or wool characterized by a pH of 4 to 7 and a calcium content of 2-6% by weight comprised of a laminate of a thin layer of non-porous segmented polyurethane sewn to foam.
- U.S. Pat. Nos. 3,734,874, 4,233,196, 4,335,220, 4,304,900, 4,304,901, and 4,300,580 describe water-dissipatable, metalable polyesters that are useful as adhesives, coating materials, films, packaging materials and other products that can be dissolved, dispersed or otherwise dissipated in water or aqueous solutions. These polyesters, however, are not cross-linked using metallic ions and cast into shapes to entrap water, humectants and/or emollients within the hardened cast.
- a further object of the present invention is to provide a convenient process of cross-linking the humectant and emollients with the polyester polymer in the presence of water soluble metallic ions.
- a further object of this invention is to provide such casted patches containing water soluble medicaments and oil soluble medicaments. Such patches can be used as controlled release transdermal delivery patches.
- the objectives of this invention may be realized by forming a cast containing humectants and/or emollient oils, water, water dissipatable polyesters, and by cross-linking with water soluble multivalent metal ions.
- Such compositions when poured int a mold harden without pressure and have utility in wound treatment, skin treatments and controlled release drug and fragrance patches.
- the casts of this invention comprise water dissipatable polyester or polyesteramide in an amount from 18 to percent by weight, water in an amount from .[.67.]. .Iadd.30 .Iaddend.to 80%, humectants in an amount from 0.01 to 40% by weight, and a source of multivalent metal ions for crosslinking purposes in an amount from 0.01 to 5 percent.
- Casts of this invention can also be formulated using emollient oils in an amount from 0.01 to 15% by weight based on the total weight of the composition, water dissipatable polyester in an amount from 18-30% by weight, water in an amount from .[.67.].
- the composition also contains fragrance oils, medical agents or color.
- Cross-linked clear casts of the present invention comprise (a) a water dissipatable polyester polymer in an amount from 18-30% by weight based on the total weight of the composition: (b) water in an amount from .[.67.]. .Iadd.30-.Iaddend.80% by weight based on the total weight of the composition; (c) a source of multivalent metallic ions in an amount of 0.1-5% by weight based on the total weight of the composition; (d) humectant such as propylene glycol, glycerine in an amount from 0.1-40% by weight based on the total weight of the composition.
- the cross-linked cast of the present invention can also be in the form of an opaque emulsion system.
- emulsion cast of the present invention comprise (a) a water dissipatable polymer in an amount from 18 to 30% by weight based on the total weight of the composition; (b) water in am amount from .[.67.].
- emollient oils in an amount from 0.1 to 25% by weight based on the total weight of the composition
- a source of multivalent metallic ions in an amount from 0.1 to 5% by weight based on the total weight of the composition
- humectants in an amount from 0.01 to 40% by weight based on the total weight of the composition
- any suitable oil-in-water emulsifier in an amount from 0.01 to 5% by weight based on the total weight of the composition.
- Polymers useful in the present invention must be capable of cross-linking with water soluble metal ions, and, when poured in liquid form into a mold hardening without pressure to form a cast of any desirable shape.
- Polymers suitable for use in this invention include the water-dissipatable polyester and polyesteramides described in U.S. Pat. No. 3,734,874 to Kibler, et al., U.S. Pat. No. 4,233,196 to Sublet and U.S. Pat. No. 4,304,901 to O'Neill, et al.
- a preferred water dissipatable polyester is commercially available on Eastman AQ 5S polymers.
- organic and inorganic sources of the multivalent metal ions used to cross-link the polymers in this invention include magnesium chloride, zinc acetate, zinc gluconate, zinc oxide, titanium dioxide and magnesium acetate.
- the preferred sources of multivalent metal ions are water soluble and include zinc gluconate and magnesium chloride.
- water by itself or in combination with humectant such as propylene glycol and glycerine may be used.
- Emollient oil in forming cross-linked emulsion casts of this invention any emollient oil may be used.
- Emollients useful in this invention include hydrocarbon oils and semi-solid hydrocarbons, lanolin and derivatives, silicone oils and esters commonly used in the cosmetic and dermatological fields.
- cross-linking of polymer containing emulsion systems by means of multivalent metallic ions can be achieved with or without the additional emulsifiers.
- the selection of an appropriate emulsifier for a given system is within the purview of one skilled in the art.
- agents may be incorporated into the compositions of this invention for a variety of purposes.
- medicaments such as benzoyl peroxide, methyl nicolinate, salicyclic acid, benzocaine and menthol can be cast into desirable shapes for therapeutic use.
- the cross-linked hydrogels and emulsions can be cast into any desirable shape and sued for various purposes.
- casts in the form of face masks may be used for treating dry skin.
- Casts in the form of patches or pads may be sued to cover burns and wounds for soothing and comforting the inflamed area, or for delivering active medicaments to the damaged skin as a controlled release, transdermal patch.
- Both the clear and opaque emollient casts may also contain fragrance, insect repellents, such screens and like chemicals.
- a clear cross-linked cast was produced having the following composition:
- the cross-linked cast of Example 1 was prepared by placing the appropriate amounts of water and propylene glycol into a suitable container and heating the mixture to 80° C. The appropriate amount of polymer was gradually added with a high shear mixing to dissolve the solids. When all the solid were added, high shear mixing is continued, until a clear, straw colored, thick gel was produced. The gel was then cooled to room temperature and an appropriate amount of zinc gluconate aqueous solution added by high shear mixing until cross-linking occurred. The liquid was poured into a mold of desirable shape to produce a cast of hydrogel.
- the metallic cross-linking can be done either at room temperature or at elevated temperatures depending on the composition.
- An emulsion crosslinked cast was produced having the following composition:
- Polysorbate 20 1.0
- the cross-linked emulsion casts of Example 2 were formed by placing appropriate amounts of water and propylene glycol in a suitable container and heating the mixture to 80° C. The appropriate amount of polymer was gradually added with a high shear mixing until a clear viscous liquid was produced. The polysorbate 20 was added to the clear liquid and mixing continued. The melted oil phase as then added to the aqueous phase and homogenized to form a smooth emulsion. To this emulsion the appropriate amount of aqueous solution of zinc gluconate was added with continued mixing. Pouring into a mold at appropriate viscosity formed a cast of the desired shape. The cross-linking of the emulsion can be carried out between 50° C. to 70° C., as desired, for manufacturing and suitable for pouring into the molds for casting purposes.
- Water insoluble sources of multivalent metallic ions such as, for example, zinc oxide or titanium dioxide can be added to form more rigid cross-linked casts.
- Microcrystalline Wax 5.00
- Polysorbate 20 1.0
- Polysorbate 20 1.0
- Polysorbate 20 1.0
- Polysorbate 20 1.0
- Zinc gluconate 1.0
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Inorganic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Description
Claims (3)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/016,808 USRE34716E (en) | 1989-06-16 | 1993-02-11 | Aqueous dispersions of polyester and polyester-amides cross-linked with metallic ions and casts made therefrom |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/367,183 US4992508A (en) | 1989-06-16 | 1989-06-16 | Aqueous dispersions of polyester and polyesteramides cross-linked with metallic ions and casts made therefrom |
US57801890A | 1990-09-05 | 1990-09-05 | |
US07/652,233 US5110862A (en) | 1989-06-16 | 1991-02-05 | Aqueous dispersions of polyester and polyester-amides cross-linked with metallic ions and casts made therefrom |
US08/016,808 USRE34716E (en) | 1989-06-16 | 1993-02-11 | Aqueous dispersions of polyester and polyester-amides cross-linked with metallic ions and casts made therefrom |
Related Parent Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US57801890A Continuation | 1989-06-16 | 1990-09-05 | |
US07/652,233 Reissue US5110862A (en) | 1989-06-16 | 1991-02-05 | Aqueous dispersions of polyester and polyester-amides cross-linked with metallic ions and casts made therefrom |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE34716E true USRE34716E (en) | 1994-09-06 |
Family
ID=23446235
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/367,183 Expired - Lifetime US4992508A (en) | 1989-06-16 | 1989-06-16 | Aqueous dispersions of polyester and polyesteramides cross-linked with metallic ions and casts made therefrom |
US08/016,808 Expired - Lifetime USRE34716E (en) | 1989-06-16 | 1993-02-11 | Aqueous dispersions of polyester and polyester-amides cross-linked with metallic ions and casts made therefrom |
US08/016,806 Expired - Lifetime USRE34682E (en) | 1989-06-16 | 1993-02-11 | Aqueous dispersions of polyester and polyesteramides cross-linked with metallic ions and casts made therefrom |
Family Applications Before (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/367,183 Expired - Lifetime US4992508A (en) | 1989-06-16 | 1989-06-16 | Aqueous dispersions of polyester and polyesteramides cross-linked with metallic ions and casts made therefrom |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US08/016,806 Expired - Lifetime USRE34682E (en) | 1989-06-16 | 1993-02-11 | Aqueous dispersions of polyester and polyesteramides cross-linked with metallic ions and casts made therefrom |
Country Status (6)
Country | Link |
---|---|
US (3) | US4992508A (en) |
EP (1) | EP0413418B1 (en) |
AT (1) | ATE142663T1 (en) |
CA (1) | CA2019117C (en) |
DE (1) | DE69028463T2 (en) |
ES (1) | ES2091797T3 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5948400A (en) | 1997-11-20 | 1999-09-07 | Smith & Nephew Inc. | Method of applying a pressure-sensitive adhesive wound dressing and water-based skin treatment composition |
Families Citing this family (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5221254A (en) * | 1991-04-02 | 1993-06-22 | Alza Corporation | Method for reducing sensation in iontophoretic drug delivery |
US5386003A (en) * | 1993-03-15 | 1995-01-31 | Eastman Chemical Company | Oil absorbing polymers |
FR2765480B1 (en) * | 1997-07-07 | 1999-09-10 | Oreal | USE FOR THE COATING OF KERATIN MATERIALS WITH A HYBRID POLYMERIC MATERIAL; COSMETIC OR DERMATOLOGICAL COMPOSITIONS |
US5922782A (en) * | 1997-07-23 | 1999-07-13 | Eastman Chemical Company | Foamable copolyesters prepared from divalent metal containing co-ionomers |
US6274167B1 (en) * | 2000-09-14 | 2001-08-14 | Vincent Margiotta | Topical anesthetic patch |
US20030143264A1 (en) * | 2002-01-30 | 2003-07-31 | Vincent Margiotta | Topical anesthetic-antiseptic patch |
FR2850021A1 (en) * | 2003-01-20 | 2004-07-23 | Oreal | Foaming aqueous composition, e.g. useful for cleansing or removing make-up from the skin, scalp or hair, comprises an aromatic polyester sulfonate, a foaming nonionic surfactant and a polyvalent cation |
US6960748B2 (en) | 2003-10-09 | 2005-11-01 | Smurfit-Stone Container Enterprises, Inc. | Collapsible microwave popcorn box |
CN1893931B (en) | 2003-10-27 | 2011-07-20 | 陶氏康宁公司 | Preparations for topical application and methods of delivering an active agent to a substrate |
US20060084737A1 (en) * | 2004-10-15 | 2006-04-20 | Certainteed Corporation | Polyester resin binder |
US20070258935A1 (en) * | 2006-05-08 | 2007-11-08 | Mcentire Edward Enns | Water dispersible films for delivery of active agents to the epidermis |
US20070259029A1 (en) * | 2006-05-08 | 2007-11-08 | Mcentire Edward Enns | Water-dispersible patch containing an active agent for dermal delivery |
US20080057090A1 (en) * | 2006-09-01 | 2008-03-06 | Mcentire Edward Enns | Wrinkle masking film composition for skin |
US7879942B2 (en) * | 2006-10-05 | 2011-02-01 | Eastman Chemical Company | Switchable adhesive article for attachment to skin and method of using the same |
WO2016130881A1 (en) * | 2015-02-12 | 2016-08-18 | Eastman Chemical Company | Elastomeric compositions comprising ionomers |
Citations (24)
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---|---|---|---|---|
FR1545403A (en) * | 1966-11-28 | 1968-11-08 | Polymer Corp | Vulcanizates of diolefin polymers |
US3493350A (en) * | 1963-07-25 | 1970-02-03 | Phillips Petroleum Co | Carbon black feeding to a pelletizer using gas pulses in the flow control zone |
US3562034A (en) * | 1966-11-28 | 1971-02-09 | Polymer Corp | Vulcanization of allylic halide terminated polymers of diolefinic hydrocarbons |
US3734874A (en) * | 1970-02-27 | 1973-05-22 | Eastman Kodak Co | Polyesters and polyesteramides containing ether groups and sulfonate groups in the form of a metallic salt |
FR2211474A1 (en) * | 1972-12-26 | 1974-07-19 | Exxon Research Engineering Co | |
US3879168A (en) * | 1971-11-29 | 1975-04-22 | Medical Alginates Limited | Manufacture of alginic material |
US3949742A (en) * | 1974-09-20 | 1976-04-13 | Frigitronics, Inc. | Medical dressing |
US4022880A (en) * | 1973-09-26 | 1977-05-10 | Lever Brothers Company | Anticalculus composition |
US4100269A (en) * | 1973-06-28 | 1978-07-11 | Lever Brothers Company | Anticalculus dentifrice |
US4233196A (en) * | 1979-04-30 | 1980-11-11 | Eastman Kodak Company | Polyester and polyesteramide compositions |
EP0022624A1 (en) * | 1979-06-21 | 1981-01-21 | The British Petroleum Company p.l.c. | Process for setting a polychloroprene-latex |
US4252885A (en) * | 1977-03-25 | 1981-02-24 | Bexford Limited | Polyester coated films using an aqueous polyester dispersion and photographic layer |
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US3493550A (en) * | 1967-07-03 | 1970-02-03 | American Cyanamid Co | Plasticized associated polymers |
CA1168157A (en) * | 1981-03-23 | 1984-05-29 | Eric S. Abrutyn | Polymer entrapped emollient-moisturizer composition |
-
1989
- 1989-06-16 US US07/367,183 patent/US4992508A/en not_active Expired - Lifetime
-
1990
- 1990-06-14 ES ES90306515T patent/ES2091797T3/en not_active Expired - Lifetime
- 1990-06-14 DE DE69028463T patent/DE69028463T2/en not_active Expired - Fee Related
- 1990-06-14 AT AT90306515T patent/ATE142663T1/en not_active IP Right Cessation
- 1990-06-14 EP EP90306515A patent/EP0413418B1/en not_active Expired - Lifetime
- 1990-06-15 CA CA002019117A patent/CA2019117C/en not_active Expired - Fee Related
-
1993
- 1993-02-11 US US08/016,808 patent/USRE34716E/en not_active Expired - Lifetime
- 1993-02-11 US US08/016,806 patent/USRE34682E/en not_active Expired - Lifetime
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EP0022624A1 (en) * | 1979-06-21 | 1981-01-21 | The British Petroleum Company p.l.c. | Process for setting a polychloroprene-latex |
US4393048A (en) * | 1980-02-15 | 1983-07-12 | The United States Of America As Represented By The Secretary Of The Army | Protective gel composition for wounds |
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US4409285A (en) * | 1980-11-10 | 1983-10-11 | Imperial Chemical Industries Plc | Surface-modifying coating compositions |
US4724240A (en) * | 1981-03-23 | 1988-02-09 | Wickhen Products, Inc. | Lattice-entrapped emollient-moisturizer composition |
US4335220A (en) * | 1981-04-06 | 1982-06-15 | Eastman Kodak Company | Sequestering agents and compositions produced therefrom |
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Cited By (1)
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US5948400A (en) | 1997-11-20 | 1999-09-07 | Smith & Nephew Inc. | Method of applying a pressure-sensitive adhesive wound dressing and water-based skin treatment composition |
Also Published As
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CA2019117A1 (en) | 1990-12-16 |
USRE34682E (en) | 1994-08-02 |
CA2019117C (en) | 1999-04-06 |
EP0413418A3 (en) | 1991-11-27 |
US4992508A (en) | 1991-02-12 |
DE69028463D1 (en) | 1996-10-17 |
EP0413418A2 (en) | 1991-02-20 |
ES2091797T3 (en) | 1996-11-16 |
DE69028463T2 (en) | 1997-02-06 |
ATE142663T1 (en) | 1996-09-15 |
EP0413418B1 (en) | 1996-09-11 |
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