+

WO2009053947A2 - Revêtement de surface pour empêcher la lixiviation cationique - Google Patents

Revêtement de surface pour empêcher la lixiviation cationique Download PDF

Info

Publication number
WO2009053947A2
WO2009053947A2 PCT/IB2008/054475 IB2008054475W WO2009053947A2 WO 2009053947 A2 WO2009053947 A2 WO 2009053947A2 IB 2008054475 W IB2008054475 W IB 2008054475W WO 2009053947 A2 WO2009053947 A2 WO 2009053947A2
Authority
WO
WIPO (PCT)
Prior art keywords
ppb
syringe
equal
cations
oil
Prior art date
Application number
PCT/IB2008/054475
Other languages
English (en)
Other versions
WO2009053947A3 (fr
Inventor
Laurence Boulange
David Benjamin Montgomery
Sébastien JANVIER
Julie Haguet
Frédérique CROZET
Florestan Desmaris
Delphine Brissaud
Charlène SOULET
Estelle Appert
Jean Charles Joud
Original Assignee
Becton Dickinson France
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 Becton Dickinson France filed Critical Becton Dickinson France
Publication of WO2009053947A2 publication Critical patent/WO2009053947A2/fr
Publication of WO2009053947A3 publication Critical patent/WO2009053947A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C26/00—Coating not provided for in groups C23C2/00 - C23C24/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M5/00—Devices for bringing media into the body in a subcutaneous, intra-vascular or intramuscular way; Accessories therefor, e.g. filling or cleaning devices, arm-rests
    • A61M5/178—Syringes
    • A61M5/31—Details
    • A61M5/3129—Syringe barrels
    • 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
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • 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
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/12—Chemical modification
    • C08J7/123—Treatment by wave energy or particle radiation
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M5/00—Devices for bringing media into the body in a subcutaneous, intra-vascular or intramuscular way; Accessories therefor, e.g. filling or cleaning devices, arm-rests
    • A61M5/178—Syringes
    • A61M5/31—Details
    • A61M5/3129—Syringe barrels
    • A61M2005/3131—Syringe barrels specially adapted for improving sealing or sliding
    • 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
    • C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
    • C08J2323/10—Homopolymers or copolymers of propene
    • 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
    • C08J2365/00—Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Derivatives of such polymers
    • 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
    • C08J2483/00—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

Definitions

  • the invention generally relates to drug holding components of drug delivery systems implementing an injection like process for delivering a drug or drug formulation directly to a patient or through a fluid administration circuit.
  • the invention relates to pre-fillable and pre- filled components of such drug delivery systems.
  • Many drug delivery systems like syringes, pre-filled syringes, drug cartridge and needless injectors include an internal chamber for receiving a medicament and a piston, the piston being slidable within the interior chamber.
  • Such drug delivery systems are often made of glass so two problems are to be solved, the first one is to improve gliding properties in syringe barrels and the second one is to obtain a good stability of the active principles contained in such barrels.
  • the siliconization of the inner wall of the chamber allows a smooth movement or gliding of the piston within the chamber.
  • the silicone oil used for pharmaceutical applications is a polydimethylsiloxane polymer, sprayed inside the barrel.
  • silicone oil is an apolar molecule that can mostly generate hydrophobic interactions with other molecules or particles in solutions. When an emulsion with silicone oil comes in contact with proteins, it generates some changes in their structure leading to a loss of protein activity and/or a protein aggregation.
  • the aim of the invention is to create surface coatings that prevent cation leaching from glass and stabilize the silicone oil onto the syringe barrel reducing further interactions with proteins stored in the syringe barrel.
  • the current solution developed by the biotech market is a baked silicone syringe with a Flurotec stopper.
  • the baked silicone syringe displays a lower content of silicone by a factor 10 in comparison with a standard sprayed silicone.
  • the current solution is not completely satisfactory as there is some limitation in the process. Indeed, only luer syringes can be produced by using this process, secondly, there are some therapeutic proteins that can aggregate when stored in a baked silicone syringe.
  • thermal barrier coating adapted to provide a thermally insulating protective barrier on a component was patented by Rolls-Royce (US patent 4,332,618).
  • the coating was applied to the components by spraying methods and being ductile when exposed to high temperatures.
  • the coating comprises a mixture containing constituents of glass microspheres; a ceramic frit of finely divided particles of alkali silicate titanate glass; and a refractory filler material of finely divided particles (micronized mica; aluminum oxide of mullite). All of the constituents of the mixture were suspended in a high temperature resistant binder material such as potassium silicate, sodium silicate or aluminum orthophosphate.
  • Pilkington pic. proposed a coating, which acted as barrier layers to inhibit migration of alkali metal ions from a glass surface (Na leaching between 40 and 700 ng/cm 2 ). It acted as color suppressing underlayers for overlying infra-red reflecting or electrically conducting layers.
  • the coating was deposited by pyrolysis of a gaseous mixture of a silane, an unsaturated hydrocarbon and an oxygen-containing gas other than carbon dioxide which does not react with the silane at room temperature on a hot glass surface at a temperature of 600 0 C to 750 0 C (US patent 4,995,89 3 and US 5,165,972).
  • the hollow glass body had an interior coating preferably composed by oxides such as SiO2, AI2O3, TiO2. There was a predetermined coating thickness according to the required chemical resistance or working conditions for forming the glass body.
  • the coating is advantageously provided by means of a PICVD process (US patent 6,200,658 B1 ).
  • PPG Industries patented amorphous metal oxide barrier layers of titanium oxide, zirconium oxide and zinc/tin oxide that acted as alkali metal ion barrier layers at thicknesses below 18 nm.
  • the amorphous metal oxide barrier layers are most effective when the density of the layer is equal to or greater than 75% of the crystalline density.
  • the barrier layers prevent migration of alkali metal ions such as sodium ions from glass substrates into a medium e.g. electrolyte of a photochromic cell, liquid material of a liquid crystal display device contacting the glass surface and a photocatalytic coating.
  • the properties of the medium, particularly electroconductive metal oxide coatings, are susceptible to deterioration by the presence of sodium ions migrating from the glass (US patent 6,352,755 B1 ).
  • Becton Dickinson proposed a method to reduce high breakout and sustaining forces between slidable surfaces.
  • a film of lubricant applied at least to one of the surfaces was then subjected to an ionizing plasma.
  • the invention includes articles having slidable surfaces of low breakout and sustaining forces. This treatment was applied on silicone oils (US patents 4,767,414 & 4,822,632).
  • Becton Dickinson also protected a method for preparing stable coatings of a silicone lubricant on a low surface energy polymeric surface. It included plasma treatment of the surface in an atmosphere of a siloxane monomer.
  • a layer of polysiloxane was deposited on the low energy surface to give a polysiloxane surface.
  • a film of a polysiloxane lubricant having a surface tension substantially the same as or less than the surface energy of the polysiloxane surface was applied to the polysiloxane layer (US 4,844,986).
  • Becton Dickinson also developed a multi component system.
  • a first crosslinked basement lubricant was coated onto a syringe barrel.
  • a second lubricant was coated over the crosslinked lubricant.
  • a low viscosity prebasement lubricant was evenly coated onto the inside surface of the syringe barrel and then crosslinked by a plasma to a viscous liquid or substantially solid basement lubricant.
  • a second surface lubricant is then applied over the basement lubricant (US patent 5,338,312).
  • NovoNordisk proposed a coating system for articles where plastic materials slide against flexible rubber materials.
  • the coating system was a silicone oil based coating having a viscosity of at least 200,000 centistokes.
  • the coating comprises in a preferred embodiment a silicone oil based block or graft copolymer, or segmented copolymer.
  • Such an article was preferably a medical article, such as a container or an injection cylinder and a stopper.
  • the coatings were particularly useful for coating containers for storage and administration of liquid protein solutions, such as insulin formulations (US 6,482,509 B2).
  • One aspect of the present invention comprises a method to prepare a syringe comprising the steps of: a. creating an homogeneous and continuous inner oil layer inside a syringe, b. exposing said inner oil layer to an oxidative plasma gas, said oil being a non reactive oil.
  • the method according to the invention further comprises before the step of creating said inner oil layer a preliminary step of oxidative plasma.
  • the method according to the invention comprises a step of sterilization.
  • non reactive oil is silicon oil.
  • the silicon oil is chosen amongst the alkyl polysiloxane.
  • the alkylpolysiloxane are chosen in the group comprising polydimethylsiloxane, polydiethylesiloxane and polydipropylsiloxane.
  • the oil has a viscosity from preferably around 100O cSt.
  • the homogeneous and continuous oil layer is 0,5 to 1 ,5 ⁇ m
  • the oxidative plasma gas is oxygen, or an oxygen containing gas.
  • the oxidative plasma is generated under atmospheric pressure or vacuum.
  • the oxidative plasma is generated by microwaves, audio frequencies, radio-frequencies, low frequencies, DC glow discharge, Corona discharge or arc discharge.
  • the syringe is glass based, such as borosilicate
  • the ionizing plasma was done by using an oxidative gas such as air but pure oxygen or other oxidative gases can also be used.
  • the method can be applied or used on on Luer syringes and for syringes in polymers.
  • the silicone oil used for pharmaceutical applications is a polydimethylsiloxane polymer. This polymer is directly exposed to a plasma gas after spraying inside the barrel. The plasma is done in a chamber by adding an oxidative gas such as air or oxygen or a mixture of oxygen with an inert gas assuring a barrier effect whereas an outer layer can assure the gliding effect.
  • the inner layer is an effective barrier against monovalent, divalent, thvalent and tetravalent cations extracted from glass.
  • Another aspect of the invention is the use of a non-reactive oil exposed to an oxidative plasma treatment as a surface coating of a syringe barrel to be filled with a pharmaceutical preparation, to inhibit leaching of chemical species from syringe raw material into the said pharmaceutical preparation.
  • the chemical species are cations.
  • Another aspect of the invention is to provide a syringe to be filled with a pharmaceutical preparation, characterized in that the barrier effect for all the cation elements is inferior or equal to 250 ng/cm 2 , preferably inferior or equal to 200 ng/cm 2 , more preferably inferior or equal to 150 ng/cm 2
  • cation is inferior or equal to 150 ng/cm 2 , preferably inferior or equal to 100 ng/cm 2 , more preferably inferior or equal to 90 ng/cm 2
  • the effect achieved by the method of the invention is of long duration and syringes retain the advantages of good gliding properties and leaching inhibition of chemical species.
  • the homogeneous and continuous inner oil layer is created inside a syringe.
  • Application of said continuous inner layer may be accomplished by any suitable method, such as, for example dipping, brushing spraying and the like.
  • the oil layer may be applied in a pure form or in water emulsion with surfactant.
  • the non reactive oil chosen amongst the alkylpolysiloxane in some embodiments is a polydimethyl siloxane, such as DOW CORNINGS360 ® polydimethylsiloxane or NuSiL ® polydimethylsiloxane having a viscosity ranging from about 100 to about 1 ,000,000 cst.
  • the syringe is exposed to an oxidative plasma gas.
  • the plasma treatment may be carried out in any plasma generator as for example those described in US3847652 or French patent applications 08FR51900 or 08FR51901.
  • the best embodiment is a Hypak ® syringe formed by an inner layer obtained by CVD technology and an outer layer composed by a sprayed silicone with a viscosity of 1000 cSt plasma treated using an ionizing gas (oxygen) for 15 sec.
  • Example 1 Barrier effect of the coatings against cations coming from glass
  • Si Silicon (Si) is present in the glass as SiO2 and constitutes the basis of the glass,
  • Sodium (Na) is present in the glass as Na2 ⁇ and lowers the melting temperature
  • Boron (B) is present in the glass as B 2 O 3 and used to get a better thermal resistance
  • Aluminum (Al) is present in the glass as AI 2 O 3 in order to get better mechanical properties
  • Magnesium (Mg) is present in the glass as MgO and used to lower the melting temperature.
  • Sodium is analyzed by Flamme - Atomic Absorption Spectrometry (Flamme-AAS), using an air/acetylene flamme, a sodium hallow cathode and a detection at 589nm. An external calibration was performed between 0.3 and 2.0 ppm. Solutions of three syringes were pooled together for analysis.
  • Flamme-AAS Flamme - Atomic Absorption Spectrometry
  • Method 2 for Boron, Aluminum and Magnesium Nitric acid extracts using ultrasonic bath. A rigid needle shield was placed on the syringes, which are filled with 1 mL of 1 % nitric acid, stoppered with a Flurotec® plunger stopper and placed for 2 hours in an ultrasonic bath at room temperature. Boron, Aluminum, Magnesium were analyzed by ICP/MS in one single method, using an argon plasma and a mass spectrometer for the detection, with the specific masses of 11 for Boron, 27 for Aluminum and 24 for Magnesium. An external calibration was performed using one single level at 10ppb for all elements and a check at 5ppb for all elemnts. The calibration was validated between 1 and 10 ppb for Boron, 2 and 10 ppb for Aluminum and 4 and 10 ppb for Magnesium. Solutions of four syringes are pooled together for analysis.
  • Method 3 for Silicium Purified water extracts using autoclave plus 24 hour agitation: A rigid needle shield was placed on the syringes, which were filled with 1 mL of deionized water and stoppered with unsiliconized parylene coated plunger stoppers and autoclaved for 1 hour at 121 O. They w ere then agitated for 24 hours before analysis.
  • Silicium was analyzed by ICP/MS using an argon plasma and a mass spectrometer for the detection, with the specific mass of 28 for silicium. Silicium extracted from the glass as well as silicium extracted from the coatings (referred as to C1 to C6 and P1 to P5) were quantified together. An external calibration was performed between 10 and 35 ppb. Solution from a single syringe was diluted in 1 % nitric acid to reach the range of the calibration curve. [0067] For all the cation elements, the barrier effect measured by analytical tools was then expressed in ng/cm 2 .
  • A1 bis C2+P2 0.8 ppm 15% 80
  • A1 C1 +P2 5 ppb 25% 0.5
  • A2 P2 5 ppb 1 1% 0.5
  • A1 bis C2+P2 4ppb 0% 0.4
  • C1 provide a filter effect against divalent magnesium cation. It corresponds to a CVD process using pure HMDSO. The presence of oxygen in the reaction chamber decreases the filter effect against Mg 2+ .
  • PTS systems are efficient barriers for divalent cations and bilayers can improve the filter effect against divalent magnesium cation compared to solid coatings alone.
  • A1 C1 +P2 23ppb 25% 2.3
  • A1 bis C2+P2 10ppb 0% 1.0
  • A2 P2 30 ppb 0% 3.0
  • A1 bis C2+P2 20 ppb 0% 2.0
  • Silicium quantified by ICP/MS can come from both the glass or the coating : polymerized HMDSO by CVD or silicone (DC360 10OOcSt - PDMS) oil.
  • Silicon element quantified by ICP/MS can come from both the glass or the coating : polymerized HMDSO by CVD or silicone (DC360 100OcSt - PDMS) oil.
  • the secondary structure content are based on the following structures deposited in the Protein Databank (http://www.rcsb.org/pdb/), Protein references are given in bracket and given for a monomer
  • Insulin is a polypeptide hormone that regulates glucose metabolism.
  • Bovine Serum Albumin is a serum albumin that is used to stabilize some enzymes and plays a role in transport of low hydrosoluble proteins.
  • the protein stability was studied at 37O and the h ydrodynamic diameter of the protein (nm) was measured by Dynamic Light Scattering (DLS). The measurements were made with a He Ne laser 633 nm at 173° in order to verify the presence of aggregates and to minimize the effects of dust contamination.
  • Each native protein has a specific hydrodynamic diameter that is typically less than 20 nm.
  • a study of the kinetics was performed at 37°C and the hydrodynamic diameter was measured after 7, 15 and 30 days. When proteins formed aggregates, large hydrodynamic diameters were measured.
  • A1 C1 +P2 Peak 2 260 15 320 38 215 45
  • Bilayer A2 P2 Peak 2 260 15 260 35 710 19
  • A1 bis C2+P2 Peak 2 260 15 580 32 490 43
  • Peak 1 corresponds to the hydrodynamic diameter of the native protein and peaks 2 to the protein aggregates. For each peak the diameter (nm) and the percentage of light intensity is mentioned.
  • A1 C1+P2 Peak 2 280 76 600 45 110 53
  • Bilayer A2 P2 Peak 2 280 76 720 40 490 52
  • A1 bis C2+P2 Peak 2 280 76 580 41 310 61
  • Peak 1 Percentage of native protein (Insulin) after stabilization (days) at 37O obtained by DLS. Peak 1 corresponds to the hydrodynamic diameter of the native protein and peaks 2 to the protein aggregates. For each peak the diameter (nm) and the percentage of light intensity is mentioned.
  • Tests were performed to determine the necessary forces to move a piston inside a treated or untreated syringe barrel. These tests were performed using a LLOYD-CB190 tensile testing machine dynamometer using NEXYGEN operating software, according to two test protocols outlined briefly below.
  • Activation Gliding Force (AGF) tests were applied on containers filled with 1 ml_ of demineralised water and each plugged with one piston. Each container-piston system was tested 24 times in order to ensure the reproducibility and to validate the results. To prepare the 24 syringes for a system, and particularly to insert the piston in the container, a SPV machine was used.
  • the friction force S is the force required, under dynamic conditions, to move the piston in the container.
  • the friction force S is measured half way of the piston travel. In order to measure the friction force S, the barrel was filled with water,
  • the friction force F is the force required, again in dynamic mode, to move the piston when it reaches the end of its travel in the container. Just like the friction force S, the friction force F is measured with a container initially filled with water.
  • A1 C1 +P2 3.2 ( ⁇ 0.6) 4.6 ( ⁇ 0.2) 4.6 ( ⁇ 0.3)
  • Bi layer A2 P2 2.9 ( ⁇ 0.2) 4.5 ( ⁇ 0.2) 4.6 ( ⁇ 0.2)
  • the friction force in the static mode was the lowest on the reference R2 and after 5s of plasma treatment (typically less than 2.5 N on P1 ), intermediary after 15 s of treatment (3.5N on P2) and reached 6N after 30s of treatment on P3.
  • the sustainable force was less than 5N for the reference R2 or after 5 or 15 s of plasma treatment on P1 and P2 whereas it grew up to 5.1 N or more than 6N after 30s of treatment on P3, P4 and P5.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Metallurgy (AREA)
  • Mechanical Engineering (AREA)
  • Materials Engineering (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Anesthesiology (AREA)
  • Vascular Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Infusion, Injection, And Reservoir Apparatuses (AREA)

Abstract

La présente invention a pour objet une seringue destinée à être remplie avec une préparation pharmaceutique, caractérisée en ce que l'effet barrière pour tous les éléments cationiques est inférieur ou égal à 250 ng/cm2, de préférence inférieur ou égal à 200 ng/cm2, de manière davantage préférée inférieur ou égal à 150 ng/cm2. La présente invention concerne également un procédé pour préparer une telle seringue comprenant les étapes consistant à : • créer une couche huileuse interne homogène et continue à l'intérieur d'une seringue, • exposer ladite couche huileuse interne à un gaz plasma oxydant, ladite huile étant une huile non réactive.
PCT/IB2008/054475 2007-10-22 2008-08-20 Revêtement de surface pour empêcher la lixiviation cationique WO2009053947A2 (fr)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US99992107P 2007-10-22 2007-10-22
US60/999,921 2007-10-22
US99997507P 2007-10-23 2007-10-23
US60/999,975 2007-10-23
US17007P 2007-10-24 2007-10-24
US61/000,170 2007-10-24

Publications (2)

Publication Number Publication Date
WO2009053947A2 true WO2009053947A2 (fr) 2009-04-30
WO2009053947A3 WO2009053947A3 (fr) 2009-07-09

Family

ID=40580181

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/IB2008/054475 WO2009053947A2 (fr) 2007-10-22 2008-08-20 Revêtement de surface pour empêcher la lixiviation cationique

Country Status (1)

Country Link
WO (1) WO2009053947A2 (fr)

Cited By (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7985188B2 (en) 2009-05-13 2011-07-26 Cv Holdings Llc Vessel, coating, inspection and processing apparatus
FR2962136A1 (fr) * 2010-07-02 2012-01-06 Valois Sas Procede de traitement de surface d'un dispositif de distribution de produit fluide.
FR2962139A1 (fr) * 2010-07-02 2012-01-06 Valois Sas Procede de traitement de surface d'un dispositif de distribution de produit fluide.
WO2012001326A3 (fr) * 2010-07-02 2012-03-29 Valois Sas Procede de traitement de surface d'un dispositif de distribution de produit fluide
WO2012001328A3 (fr) * 2010-07-02 2012-03-29 Valois Sas Procede de traitement de surface d'un dispositif de distribution de produit fluide
US8512796B2 (en) 2009-05-13 2013-08-20 Si02 Medical Products, Inc. Vessel inspection apparatus and methods
WO2013178647A1 (fr) * 2012-05-29 2013-12-05 Becton Dickinson France Revêtement lubrifiant et dispositif d'injection médical comprenant un tel revêtement
US8802603B2 (en) 2010-06-17 2014-08-12 Becton, Dickinson And Company Medical components having coated surfaces exhibiting low friction and low reactivity
US20140341883A1 (en) * 2013-04-24 2014-11-20 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
WO2015181173A1 (fr) * 2014-05-26 2015-12-03 Becton Dickinson France Procédé de stockage de vaccin à adjuvant en émulsion dans un dispositif d'injection médical lubrifié
US9272095B2 (en) 2011-04-01 2016-03-01 Sio2 Medical Products, Inc. Vessels, contact surfaces, and coating and inspection apparatus and methods
US9458536B2 (en) 2009-07-02 2016-10-04 Sio2 Medical Products, Inc. PECVD coating methods for capped syringes, cartridges and other articles
US9545360B2 (en) 2009-05-13 2017-01-17 Sio2 Medical Products, Inc. Saccharide protective coating for pharmaceutical package
US9554968B2 (en) 2013-03-11 2017-01-31 Sio2 Medical Products, Inc. Trilayer coated pharmaceutical packaging
US9603775B2 (en) 2013-04-24 2017-03-28 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9664626B2 (en) 2012-11-01 2017-05-30 Sio2 Medical Products, Inc. Coating inspection method
US9662450B2 (en) 2013-03-01 2017-05-30 Sio2 Medical Products, Inc. Plasma or CVD pre-treatment for lubricated pharmaceutical package, coating process and apparatus
US9700485B2 (en) 2013-04-24 2017-07-11 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9707155B2 (en) 2013-04-24 2017-07-18 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9707154B2 (en) 2013-04-24 2017-07-18 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9707153B2 (en) 2013-04-24 2017-07-18 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9713572B2 (en) 2013-04-24 2017-07-25 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9717648B2 (en) 2013-04-24 2017-08-01 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9717649B2 (en) 2013-04-24 2017-08-01 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9764093B2 (en) 2012-11-30 2017-09-19 Sio2 Medical Products, Inc. Controlling the uniformity of PECVD deposition
US9839579B2 (en) 2013-04-24 2017-12-12 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9849066B2 (en) 2013-04-24 2017-12-26 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9863042B2 (en) 2013-03-15 2018-01-09 Sio2 Medical Products, Inc. PECVD lubricity vessel coating, coating process and apparatus providing different power levels in two phases
US9878101B2 (en) 2010-11-12 2018-01-30 Sio2 Medical Products, Inc. Cyclic olefin polymer vessels and vessel coating methods
US9903782B2 (en) 2012-11-16 2018-02-27 Sio2 Medical Products, Inc. Method and apparatus for detecting rapid barrier coating integrity characteristics
US9937099B2 (en) 2013-03-11 2018-04-10 Sio2 Medical Products, Inc. Trilayer coated pharmaceutical packaging with low oxygen transmission rate
US10189603B2 (en) 2011-11-11 2019-01-29 Sio2 Medical Products, Inc. Passivation, pH protective or lubricity coating for pharmaceutical package, coating process and apparatus
US10201660B2 (en) 2012-11-30 2019-02-12 Sio2 Medical Products, Inc. Controlling the uniformity of PECVD deposition on medical syringes, cartridges, and the like
EP3378514A4 (fr) * 2015-11-19 2019-07-10 Terumo Kabushiki Kaisha Cylindre pour seringue, seringue préremplie, et procédés de fabrication de ceux-ci
US10413482B2 (en) 2011-10-25 2019-09-17 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US11066745B2 (en) 2014-03-28 2021-07-20 Sio2 Medical Products, Inc. Antistatic coatings for plastic vessels
US11077233B2 (en) 2015-08-18 2021-08-03 Sio2 Medical Products, Inc. Pharmaceutical and other packaging with low oxygen transmission rate
US11116695B2 (en) 2011-11-11 2021-09-14 Sio2 Medical Products, Inc. Blood sample collection tube
IT202300010506A1 (it) 2021-09-24 2023-03-24 Stevanato Group Spa Apparato per la fabbricazione di un dispositivo medico per iniezione
IT202100024574A1 (it) 2021-09-24 2023-03-24 Stevanato Group Spa Metodo per la fabbricazione di un dispositivo medico per iniezione e dispositivo medico così ottenuto
EP2760509B1 (fr) 2011-09-27 2023-04-05 Becton Dickinson France Utilisation d'huile de silicone traitée au plasma comme revêtement dans un dispositif médical d'injection
US11624115B2 (en) 2010-05-12 2023-04-11 Sio2 Medical Products, Inc. Syringe with PECVD lubrication
IT202200003761A1 (it) 2022-03-01 2023-09-01 Stevanato Group Spa Metodo per la fabbricazione di un dispositivo medico per iniezione
US12257371B2 (en) 2012-07-03 2025-03-25 Sio2 Medical Products, Llc SiOx barrier for pharmaceutical package and coating process

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0201915A2 (fr) * 1985-05-16 1986-11-20 Becton Dickinson and Company Procédé pour lubrifier faisant usage d'un plasma ionisant
US5338312A (en) * 1992-10-02 1994-08-16 Becton, Dickinson And Company Article having multi-layered lubricant and method therefor
WO1999044754A1 (fr) * 1998-03-06 1999-09-10 Novo Nordisk A/S Systeme de revetement a frottement reduit
WO1999044755A1 (fr) * 1998-03-06 1999-09-10 Novo Nordisk A/S Article medical avec surfaces recouvertes d'un revetement a faible frottement et a faible adsorption proteique

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0201915A2 (fr) * 1985-05-16 1986-11-20 Becton Dickinson and Company Procédé pour lubrifier faisant usage d'un plasma ionisant
US5338312A (en) * 1992-10-02 1994-08-16 Becton, Dickinson And Company Article having multi-layered lubricant and method therefor
WO1999044754A1 (fr) * 1998-03-06 1999-09-10 Novo Nordisk A/S Systeme de revetement a frottement reduit
WO1999044755A1 (fr) * 1998-03-06 1999-09-10 Novo Nordisk A/S Article medical avec surfaces recouvertes d'un revetement a faible frottement et a faible adsorption proteique

Cited By (79)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8834954B2 (en) 2009-05-13 2014-09-16 Sio2 Medical Products, Inc. Vessel inspection apparatus and methods
US9545360B2 (en) 2009-05-13 2017-01-17 Sio2 Medical Products, Inc. Saccharide protective coating for pharmaceutical package
US10537273B2 (en) 2009-05-13 2020-01-21 Sio2 Medical Products, Inc. Syringe with PECVD lubricity layer
US7985188B2 (en) 2009-05-13 2011-07-26 Cv Holdings Llc Vessel, coating, inspection and processing apparatus
US8512796B2 (en) 2009-05-13 2013-08-20 Si02 Medical Products, Inc. Vessel inspection apparatus and methods
US10390744B2 (en) 2009-05-13 2019-08-27 Sio2 Medical Products, Inc. Syringe with PECVD lubricity layer, apparatus and method for transporting a vessel to and from a PECVD processing station, and double wall plastic vessel
US9572526B2 (en) 2009-05-13 2017-02-21 Sio2 Medical Products, Inc. Apparatus and method for transporting a vessel to and from a PECVD processing station
US9458536B2 (en) 2009-07-02 2016-10-04 Sio2 Medical Products, Inc. PECVD coating methods for capped syringes, cartridges and other articles
US11624115B2 (en) 2010-05-12 2023-04-11 Sio2 Medical Products, Inc. Syringe with PECVD lubrication
US8802603B2 (en) 2010-06-17 2014-08-12 Becton, Dickinson And Company Medical components having coated surfaces exhibiting low friction and low reactivity
CN103097573A (zh) * 2010-07-02 2013-05-08 阿普塔尔法国简易股份公司 流体产品的分配设备的表面处理方法
WO2012001328A3 (fr) * 2010-07-02 2012-03-29 Valois Sas Procede de traitement de surface d'un dispositif de distribution de produit fluide
WO2012001326A3 (fr) * 2010-07-02 2012-03-29 Valois Sas Procede de traitement de surface d'un dispositif de distribution de produit fluide
FR2962139A1 (fr) * 2010-07-02 2012-01-06 Valois Sas Procede de traitement de surface d'un dispositif de distribution de produit fluide.
FR2962136A1 (fr) * 2010-07-02 2012-01-06 Valois Sas Procede de traitement de surface d'un dispositif de distribution de produit fluide.
US11123491B2 (en) 2010-11-12 2021-09-21 Sio2 Medical Products, Inc. Cyclic olefin polymer vessels and vessel coating methods
US9878101B2 (en) 2010-11-12 2018-01-30 Sio2 Medical Products, Inc. Cyclic olefin polymer vessels and vessel coating methods
US9272095B2 (en) 2011-04-01 2016-03-01 Sio2 Medical Products, Inc. Vessels, contact surfaces, and coating and inspection apparatus and methods
EP2760509B1 (fr) 2011-09-27 2023-04-05 Becton Dickinson France Utilisation d'huile de silicone traitée au plasma comme revêtement dans un dispositif médical d'injection
US10413481B2 (en) 2011-10-25 2019-09-17 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US10441505B2 (en) 2011-10-25 2019-10-15 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US11707410B2 (en) 2011-10-25 2023-07-25 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US11707408B2 (en) 2011-10-25 2023-07-25 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US11707409B2 (en) 2011-10-25 2023-07-25 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US10413483B2 (en) 2011-10-25 2019-09-17 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US10413482B2 (en) 2011-10-25 2019-09-17 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US11724860B2 (en) 2011-11-11 2023-08-15 Sio2 Medical Products, Inc. Passivation, pH protective or lubricity coating for pharmaceutical package, coating process and apparatus
US11116695B2 (en) 2011-11-11 2021-09-14 Sio2 Medical Products, Inc. Blood sample collection tube
US11884446B2 (en) 2011-11-11 2024-01-30 Sio2 Medical Products, Inc. Passivation, pH protective or lubricity coating for pharmaceutical package, coating process and apparatus
US10577154B2 (en) 2011-11-11 2020-03-03 Sio2 Medical Products, Inc. Passivation, pH protective or lubricity coating for pharmaceutical package, coating process and apparatus
US11148856B2 (en) 2011-11-11 2021-10-19 Sio2 Medical Products, Inc. Passivation, pH protective or lubricity coating for pharmaceutical package, coating process and apparatus
US10189603B2 (en) 2011-11-11 2019-01-29 Sio2 Medical Products, Inc. Passivation, pH protective or lubricity coating for pharmaceutical package, coating process and apparatus
US11135370B2 (en) 2012-05-29 2021-10-05 Becton Dickinson France Lubricant coating and medical injection device comprising such a coating
EP3910046A1 (fr) * 2012-05-29 2021-11-17 Becton Dickinson France Procédé de fabrication d'un revêtement lubrifiant
US11779706B2 (en) 2012-05-29 2023-10-10 Becton Dickinson France Lubricant coating and medical injection device comprising such a coating
KR101634031B1 (ko) * 2012-05-29 2016-06-27 벡톤 디킨슨 프랑스 윤활제 코팅 및 그러한 코팅을 포함하는 의료용 주사 장치
RU2584421C1 (ru) * 2012-05-29 2016-05-20 Бектон Дикинсон Франс Смазочное покрытие и медицинское устройство, включающее данное покрытие
JP2015519136A (ja) * 2012-05-29 2015-07-09 ベクトン ディキンソン フランス 潤滑性コーティングおよび該コーティングを含む医用注射デバイス
KR20150013886A (ko) * 2012-05-29 2015-02-05 벡톤 디킨슨 프랑스 윤활제 코팅 및 그러한 코팅을 포함하는 의료용 주사 장치
US9993597B2 (en) 2012-05-29 2018-06-12 Becton Dickinson France Lubricant coating and medical injection device comprising such a coating
WO2013178647A1 (fr) * 2012-05-29 2013-12-05 Becton Dickinson France Revêtement lubrifiant et dispositif d'injection médical comprenant un tel revêtement
US12257371B2 (en) 2012-07-03 2025-03-25 Sio2 Medical Products, Llc SiOx barrier for pharmaceutical package and coating process
US9664626B2 (en) 2012-11-01 2017-05-30 Sio2 Medical Products, Inc. Coating inspection method
US9903782B2 (en) 2012-11-16 2018-02-27 Sio2 Medical Products, Inc. Method and apparatus for detecting rapid barrier coating integrity characteristics
US9764093B2 (en) 2012-11-30 2017-09-19 Sio2 Medical Products, Inc. Controlling the uniformity of PECVD deposition
US10363370B2 (en) 2012-11-30 2019-07-30 Sio2 Medical Products, Inc. Controlling the uniformity of PECVD deposition
US10201660B2 (en) 2012-11-30 2019-02-12 Sio2 Medical Products, Inc. Controlling the uniformity of PECVD deposition on medical syringes, cartridges, and the like
US11406765B2 (en) 2012-11-30 2022-08-09 Sio2 Medical Products, Inc. Controlling the uniformity of PECVD deposition
US9662450B2 (en) 2013-03-01 2017-05-30 Sio2 Medical Products, Inc. Plasma or CVD pre-treatment for lubricated pharmaceutical package, coating process and apparatus
US10016338B2 (en) 2013-03-11 2018-07-10 Sio2 Medical Products, Inc. Trilayer coated pharmaceutical packaging
US12239606B2 (en) 2013-03-11 2025-03-04 Sio2 Medical Products, Llc PECVD coated pharmaceutical packaging
US10537494B2 (en) 2013-03-11 2020-01-21 Sio2 Medical Products, Inc. Trilayer coated blood collection tube with low oxygen transmission rate
US9554968B2 (en) 2013-03-11 2017-01-31 Sio2 Medical Products, Inc. Trilayer coated pharmaceutical packaging
US10912714B2 (en) 2013-03-11 2021-02-09 Sio2 Medical Products, Inc. PECVD coated pharmaceutical packaging
US9937099B2 (en) 2013-03-11 2018-04-10 Sio2 Medical Products, Inc. Trilayer coated pharmaceutical packaging with low oxygen transmission rate
US11684546B2 (en) 2013-03-11 2023-06-27 Sio2 Medical Products, Inc. PECVD coated pharmaceutical packaging
US11298293B2 (en) 2013-03-11 2022-04-12 Sio2 Medical Products, Inc. PECVD coated pharmaceutical packaging
US11344473B2 (en) 2013-03-11 2022-05-31 SiO2Medical Products, Inc. Coated packaging
US9863042B2 (en) 2013-03-15 2018-01-09 Sio2 Medical Products, Inc. PECVD lubricity vessel coating, coating process and apparatus providing different power levels in two phases
US9707153B2 (en) 2013-04-24 2017-07-18 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9700486B2 (en) * 2013-04-24 2017-07-11 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9707154B2 (en) 2013-04-24 2017-07-18 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9713572B2 (en) 2013-04-24 2017-07-25 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9717648B2 (en) 2013-04-24 2017-08-01 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9717649B2 (en) 2013-04-24 2017-08-01 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US20140341883A1 (en) * 2013-04-24 2014-11-20 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9849066B2 (en) 2013-04-24 2017-12-26 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9707155B2 (en) 2013-04-24 2017-07-18 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9839579B2 (en) 2013-04-24 2017-12-12 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9603775B2 (en) 2013-04-24 2017-03-28 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US9700485B2 (en) 2013-04-24 2017-07-11 Corning Incorporated Delamination resistant pharmaceutical glass containers containing active pharmaceutical ingredients
US11066745B2 (en) 2014-03-28 2021-07-20 Sio2 Medical Products, Inc. Antistatic coatings for plastic vessels
CN106413782A (zh) * 2014-05-26 2017-02-15 贝克顿迪金森法国公司 在润滑的医用注射装置中储存乳化佐剂疫苗的方法
WO2015181173A1 (fr) * 2014-05-26 2015-12-03 Becton Dickinson France Procédé de stockage de vaccin à adjuvant en émulsion dans un dispositif d'injection médical lubrifié
US11077233B2 (en) 2015-08-18 2021-08-03 Sio2 Medical Products, Inc. Pharmaceutical and other packaging with low oxygen transmission rate
EP3378514A4 (fr) * 2015-11-19 2019-07-10 Terumo Kabushiki Kaisha Cylindre pour seringue, seringue préremplie, et procédés de fabrication de ceux-ci
IT202100024574A1 (it) 2021-09-24 2023-03-24 Stevanato Group Spa Metodo per la fabbricazione di un dispositivo medico per iniezione e dispositivo medico così ottenuto
IT202300010506A1 (it) 2021-09-24 2023-03-24 Stevanato Group Spa Apparato per la fabbricazione di un dispositivo medico per iniezione
IT202200003761A1 (it) 2022-03-01 2023-09-01 Stevanato Group Spa Metodo per la fabbricazione di un dispositivo medico per iniezione

Also Published As

Publication number Publication date
WO2009053947A3 (fr) 2009-07-09

Similar Documents

Publication Publication Date Title
WO2009053947A2 (fr) Revêtement de surface pour empêcher la lixiviation cationique
US11779706B2 (en) Lubricant coating and medical injection device comprising such a coating
EP2796520B1 (fr) Récipient ayant de faibles émissions de particules et une surface lisse et sèche à friction contrôlée et son procédé de fabrication
EP2870273B1 (fr) Procédé de dépôt
EP2004249B1 (fr) Éléments d'étanchéité, articles associés et procédés permettant de réduire l'adhérence
WO2009030975A1 (fr) Dispositif médical comprenant une chambre siliconée et un moyen de fermeture pourvu d'un revêtement
US20130211344A1 (en) Medical components having coated surfaces exhibiting low friction and/or low gas/liquid permeability
WO2014052792A1 (fr) Revêtement de polymère halogéné ou de parylène
US20150297800A1 (en) SiOx BARRIER FOR PHARMACEUTICAL PACKAGE AND COATING PROCESS
KR20150022777A (ko) 유리 용기 및 그 제조 방법
KR20200003228A (ko) 플라즈마 처리된 실리콘 오일을 코팅물로서 활용한 의료 주사 장치 및 의료 주사 장치의 처리 방법
Funke et al. Optimization of the bake-on siliconization of cartridges. Part II: Investigations into burn-in time and temperature
US11167885B2 (en) Process for making a functionalized hollow body, having a layer of glass, including a superposition of one or more siloxanes and contacting with a plasma
JP7490829B2 (ja) 摩擦が低減されたピストンシリンダ装置用のガラスシリンダおよびピストンシリンダ装置用のガラスシリンダを処理する方法
EP3613711B1 (fr) Corps creux ayant une paroi de verre comportant une région de surface ayant des contenus de si et n
KR20250059989A (ko) 약물전달용 기구 제조 방법

Legal Events

Date Code Title Description
NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 08841233

Country of ref document: EP

Kind code of ref document: A2

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载