WO2019233835A1 - Internally coated syringe body and method for the internal coating of syringe bodies - Google Patents

Internally coated syringe body and method for the internal coating of syringe bodies Download PDF

Info

Publication number
WO2019233835A1
WO2019233835A1 PCT/EP2019/063901 EP2019063901W WO2019233835A1 WO 2019233835 A1 WO2019233835 A1 WO 2019233835A1 EP 2019063901 W EP2019063901 W EP 2019063901W WO 2019233835 A1 WO2019233835 A1 WO 2019233835A1
Authority
WO
WIPO (PCT)
Prior art keywords
sliding surface
sliding
coating
syringe body
glass
Prior art date
Application number
PCT/EP2019/063901
Other languages
German (de)
French (fr)
Inventor
Andreas Pfuch
Tina TÖLKE
Jenny Rudolf
Original Assignee
Innovent E.V.
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 Innovent E.V. filed Critical Innovent E.V.
Priority to EP19727652.0A priority Critical patent/EP3801696A1/en
Publication of WO2019233835A1 publication Critical patent/WO2019233835A1/en

Links

Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/22Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to internal surfaces, e.g. of tubes
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61MDEVICES 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
    • A61M5/00Devices for bringing media into the body in a subcutaneous, intra-vascular or intramuscular way; Accessories therefor, e.g. filling or cleaning devices, arm-rests
    • A61M5/178Syringes
    • A61M5/31Details
    • A61M5/3129Syringe barrels
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D5/00Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
    • B05D5/08Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain an anti-friction or anti-adhesive surface
    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/001General methods for coating; Devices therefor
    • C03C17/003General methods for coating; Devices therefor for hollow ware, e.g. containers
    • C03C17/004Coating the inside
    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C17/00Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/28Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
    • C03C17/30Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C23/00Other surface treatment of glass not in the form of fibres or filaments
    • C03C23/0075Cleaning of glass
    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C23/00Other surface treatment of glass not in the form of fibres or filaments
    • C03C23/0085Drying; Dehydroxylation
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2201/00Polymeric substrate or laminate
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2203/00Other substrates
    • B05D2203/30Other inorganic substrates, e.g. ceramics, silicon
    • B05D2203/35Glass
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2350/00Pretreatment of the substrate
    • B05D2350/60Adding a layer before coating
    • B05D2350/63Adding a layer before coating ceramic layer
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2518/00Other type of polymers
    • B05D2518/10Silicon-containing polymers
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2518/00Other type of polymers
    • B05D2518/10Silicon-containing polymers
    • B05D2518/12Ceramic precursors (polysiloxanes, polysilazanes)
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/02Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
    • B05D3/0254After-treatment
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/10Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by other chemical means
    • B05D3/107Post-treatment of applied coatings
    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C2217/00Coatings on glass
    • C03C2217/70Properties of coatings
    • C03C2217/76Hydrophobic and oleophobic coatings
    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C2218/00Methods for coating glass
    • C03C2218/10Deposition methods
    • C03C2218/11Deposition methods from solutions or suspensions
    • C03C2218/113Deposition methods from solutions or suspensions by sol-gel processes
    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C2218/00Methods for coating glass
    • C03C2218/10Deposition methods
    • C03C2218/15Deposition methods from the vapour phase
    • C03C2218/152Deposition methods from the vapour phase by cvd
    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
    • C03C2218/00Methods for coating glass
    • C03C2218/10Deposition methods
    • C03C2218/15Deposition methods from the vapour phase
    • C03C2218/152Deposition methods from the vapour phase by cvd
    • C03C2218/153Deposition methods from the vapour phase by cvd by plasma-enhanced cvd

Definitions

  • the invention relates to a method for coating inner surfaces of syringe bodies.
  • These syringe bodies are primary packaging means of glass or plastic, in which a movable piston along a
  • the invention further relates by means of such
  • Documents are essentially described glass syringes.
  • prefillable syringes made of plastic are known, wherein the plastic may be formed, for example, as a cycloolefin copolymer (COC) or as a cycloolefin polymer (COP).
  • COC cycloolefin copolymer
  • COP cycloolefin polymer
  • silicone oil is applied by means of spray nozzles in the syringe body. Excess silicone oil is removed in a "final rinse” wash with purified and sterilized water.
  • a silicone oil emulsion is introduced into the syringe body and bonded to the glass surface in a furnace by defined temperature treatment.
  • Silicone oil droplets act as impurities in the filling of the syringe body or be recognized as such and thus lead to rejects. Furthermore, free silicone oil droplets can act as nuclei for the aggregation of the contents of the contents. Such aggregations can in turn trigger unwanted immune reactions.
  • Siliconization of the syringe body can not be completely dispensed with.
  • Dimethoxydimethylsilane is by the structural formula
  • the invention is based on the object, an improved method for
  • the invention is based on the object to provide a simplified method that requires no thermal post-treatment step and avoids contamination of the filling material in the syringe body.
  • the invention is based on the object, a syringe body with improved sliding behavior of a guided therein piston, in particular with a particularly low breakout force and particularly uniform sliding friction when operating the piston indicate.
  • the object is achieved in terms of the method according to the invention by a method having the features of claim 1.
  • the object is achieved with regard to the syringe body by a syringe body having the features of claim 7.
  • a method for coating a sliding surface of a syringe body made of glass or plastic with an omniphobic sliding layer the sliding surface is cleaned in a first step.
  • a thin adhesion-promoting silicon oxide (SiOx) layer to the sliding surface is necessary, to which the omniphobic sliding layer can bond.
  • the thin adhesion-promoting SiOx layer can be applied, for example, by means of sol-gel technology, flame treatment (C-CVD) or plasma coating.
  • C-CVD flame treatment
  • plasma coating both vacuum and atmospheric pressure methods can be considered.
  • the sliding surface according to the invention with a wetting solution which is a silane and / or a siloxane with a weight fraction of between 0.1% and 25% in acidic solution in an organic solvent contains, wetted.
  • a wetting solution which is a silane and / or a siloxane with a weight fraction of between 0.1% and 25% in acidic solution in an organic solvent contains, wetted.
  • silane for example, dimethoxydimethylsilane,
  • Methyltrimethoxysilane or n-propyltrimethoxysilane can be used.
  • siloxane for example, polydimethylsiloxane having various viscosities can be used.
  • organic solvents for example, isopropanol or ethanol can be used.
  • Dimethoxydimethylsilane which is suitable for wetting glass surfaces, is known in the art.
  • the wetting solution acts on the sliding surface during a wetting time of at least 1 to 30 seconds, preferably 5 to 10 seconds.
  • the drying time is dependent on the temperature.
  • the drying time is at least 10 minutes, preferably 15 minutes at a temperature of between 18 ° C and 25 ° C.
  • the drying time is at least 30 seconds, preferably one minute at a temperature of 75 ° C.
  • the sliding surface is rinsed with bidistilled water or first with the organic solvent and then with bidistilled water and dried again.
  • the thickness of the thus applied lubricious coating was determined to be at most 10 nanometers.
  • breakaway and sliding friction forces were determined on the glass syringe bodies treated in this way, which are comparable to
  • Glaspritzenkörpem are whose sliding surfaces were siliconized silicon oily according to the prior art. In particular, breakaway and sliding friction forces of at most 5 Newton were determined.
  • an advantage of the method according to the invention is that free silicone oil droplets are avoided in the glass syringe body and yet the important for the intended use of the glass syringe body reduction of friction is achieved. As a result, contamination of the contents and an aggregation of the contents of the contents of such silicone oil droplets are avoided and allows a safer use of the glass syringe body.
  • Another advantage of the method according to the invention is that no burn-in step is required. At most, a drying step may occur at elevated temperature, wherein the temperature is below 100 ° C.
  • the sliding surface is activated prior to wetting.
  • the activation can be carried out by means of microwave plasma treatment and / or by means of radio-frequency plasma treatment and / or by means of atmospheric pressure plasma treatment and / or by means of flame treatment.
  • the plasma treatment may comprise a plasma pretreatment and / or a plasma coating.
  • the plasma treatment may be carried out at low pressure or at atmospheric pressure.
  • Plastic syringes is first necessary to apply a thin glassy layer to achieve sufficient adhesion. This can be done by means of
  • Atmospheric pressure plasma treatment combustion chemical vapor deposition (C-CVD) or carried out by sol-gel coating.
  • C-CVD combustion chemical vapor deposition
  • sol-gel coating In a syringe body adapted to receive a piston sliding along a sliding surface, the sliding surface according to the invention is at least partially coated with an omniphobic lubricious coating comprising a silane and / or a siloxane.
  • a corresponding coating of the piston stopper with an adhesion-promoting SiOx layer and then the omniphobic lubricious coating comprising a silane and / or siloxane is also possible.
  • the silane of the list is dimethoxydimethylsilane
  • the siloxane can be formed as polydimethylsiloxane with different viscosities.
  • the sliding coating on the sliding surface has a thickness of at most 50 nanometers, preferably between 5 and 10 nanometers, and a water contact angle between 90 ° and 120 °, preferably between 100 ° and 110 °. This embodiment allows a particularly good reduction of the breakaway force and the sliding friction between the piston and the sliding surface.
  • Figure 1 shows schematically a glass syringe body 1, in which a piston 2 is slidably guided.
  • the glass-body 1 is made of glass substrate and cylindrically shaped.
  • the inner wall of the cylinder forms the sliding surface 1.1, along which the piston 2 slides.
  • Slip coating 3 applied, which contains dimethoxydimethylsilane.
  • the sliding coating 3 has a thickness of at most 10 nanometers.
  • the layer thickness can be determined, for example, by means of ellipsometry.
  • the sliding coating 3 is designed so that the water contact angle is above 90 °. Preferably, the water contact angle is at least 100 °.
  • the wetting solution was prepared from dimethoxydimethylsilane (10w%) in isopropanol, acidification with sulfuric acid.
  • a glass syringe body 1 was wetted for 15 seconds on the sliding surface 1.1 with the prepared wetting solution, then dried for 15 minutes at a room temperature of 2l ° C and then rinsed with bidistilled water.
  • the sliding friction between the glass-body 1 and a piston 2 was determined to 3.2 N ⁇ 0.6 N (average of 10 samples).
  • the measurement of unfilled glass syringe bodies 1 was carried out with an Inspect Table 50 universal testing machine (Hegewald and Peschke), as piston 2 NovaPure® plunger stoppers were used.
  • the layer thickness of the applied lubricious coating 3 was determined on similarly coated silicon wafers by means of ellipsometry below 10 nm. The determination of the water contact angle was carried out on coated

Landscapes

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

Abstract

The invention relates to a method for coating a sliding surface (1.1) of a syringe body (1) made of glass or plastic having an omniphobic sliding layer (3), wherein the sliding surface (1.1) is cleaned and wetted with a wetting solution containing silane and/or a siloxane with a proportion by weight of between 0.1% and 25% in acid solution in an organic solvent, then dried, rinsed with twice-distilled water and dried again. The invention also relates to a syringe body (1) made of glass or plastic, set up to receive a piston (2) sliding along a sliding surface (1.1), wherein the sliding surface (1.1) is at least partly coated with an omniphobic sliding coating (3) containing a silane and/or a siloxane.

Description

Innenbeschichteter Spritzenkörper und Verfahren zur Innenbeschichtung von  Internal coated syringe body and method for internal coating of
Spritzenkörpem  Spritzenkörpem
Die Erfindung betrifft ein Verfahren zur Beschichtung von Innenoberflächen von Spritzenkörpem. Bei diesen Spritzenkörpem handelt es sich um Primärpackmittel aus Glas oder Kunststoff, bei denen ein beweglicher Kolben entlang einer The invention relates to a method for coating inner surfaces of syringe bodies. These syringe bodies are primary packaging means of glass or plastic, in which a movable piston along a
Innenoberfläche bewegt wird. Die Erfindung betrifft ferner mittels solcher Inner surface is moved. The invention further relates by means of such
Beschichtungsverfahren beschichtete Spritzenkörper. Coating method coated syringe body.
Aus dem Stand der Technik sind Verfahren zur Innensilikonisierung von The prior art discloses methods of internal siliconizing
Spritzenkörpem bekannt, mit denen eine geringe Losbrechkraft und eine möglichst konstante Gleitkraft beim Betätigen des Kolbens erzielt werden. Syringe bodies known, with which a low breakout force and a constant sliding force when operating the piston can be achieved.
Aus dem Dokument Reuter, B.; Petersen, C.: Die Silikonisierung von Spritzen, Techno. Pharm. 2 (4) (2012) Seiten 238-244 sowie aus dem Dokument Zeiß, B.; Petersen, C.: Pre-fillable syringes for the biotechnological requirements of the present and future, Pharm.Ind. 78 (1) (2016) Seiten 121-130 sind Verfahren der öligen Silikonisiemng und der Einbrennsilikonisiemng bekannt. In diesen From the document Reuter, B .; Petersen, C .: The Siliconization of Syringes, Techno. Pharm. 2 (4) (2012) pages 238-244 as well as from the document Zeiss, B .; Petersen, C .: Pre-fillable syringes for the biotechnological requirements of the present and future, Pharm. 78 (1) (2016) pages 121-130, methods of oily silicone molding and stoving silicone molding are known. In these
Dokumenten werden im Wesentlichen Glasspritzen beschrieben. Documents are essentially described glass syringes.
Zudem sind vorfüllbare Spritzen aus Kunststoff bekannt, wobei der Kunststoff beispielsweise als Cycloolefin-Copolymer (COC) oder als Cycloolefin-Polymer (COP) ausgebildet sein kann. Auch diese Spritzen werden nach dem Stand der Technik mit einer Innensilikonisiemng versehen, wie im Dokument Vorfüllbare Spritzen aus COC - Ein Nischenmarkt mit Potential, Kunststoffe extra 5/2017, S. 8- 10 sowie im bereits genannten Dokument von Reuter und Petersen beschrieben wird. In addition, prefillable syringes made of plastic are known, wherein the plastic may be formed, for example, as a cycloolefin copolymer (COC) or as a cycloolefin polymer (COP). These syringes are provided according to the prior art with a Innensilikonisiemng, as described in the document prefillable syringes from COC - A niche market with potential, plastics extra 5/2017, p 8- 10 and in the aforementioned document by Reuter and Petersen.
Bei der öligen Silikonisiemng wird Silikonöl mittels Sprühdüsen im Spritzenkörper aufgebracht. Überschüssiges Silikonöl wird in einem als„final rinse“ bezeichneten Waschgang mit gereinigtem und sterilisiertem Wasser entfernt. Bei der Einbrennsilikonisierung wird eine Silikonölemulsion in den Spritzenkörper eingebracht und in einem Ofen durch definierte Temperaturbehandlung an die Glasoberfläche angebunden. In the case of the oily silicone coating, silicone oil is applied by means of spray nozzles in the syringe body. Excess silicone oil is removed in a "final rinse" wash with purified and sterilized water. In the case of stoving siliconization, a silicone oil emulsion is introduced into the syringe body and bonded to the glass surface in a furnace by defined temperature treatment.
Ein Nachteil dieser Silikonisierungsverfahren besteht darin, dass freie A disadvantage of this siliconization process is that free
Silikonöltröpfchen als Verunreinigungen im Füllgut des Spritzenkörpers wirken oder als solches erkannt werden und damit zu Ausschuss führen. Ferner können freie Silikonöltröpfchen als Keime für die Aggregation der Inhaltsstoffe des Füllguts wirken. Derartige Aggregationen können wiederum Auslöser unerwünschter Immunreaktionen sein. Silicone oil droplets act as impurities in the filling of the syringe body or be recognized as such and thus lead to rejects. Furthermore, free silicone oil droplets can act as nuclei for the aggregation of the contents of the contents. Such aggregations can in turn trigger unwanted immune reactions.
Ebenfalls bekannt sind Verfahren zur Behandlung der Gleitfläche eines Kolbens, der beweglich in einem Spritzenkörper geführt ist. Das Dokument Melamies, I.A.: Also known are methods for treating the sliding surface of a piston which is movably guided in a syringe body. The document Melamies, I.A .:
Barrieren und Schutz vor Bakterien, medizin&technik (5) (2012) Seiten 44-45 beschreibt ein Plasmaverfahren zur Gleitflächenbehandlung der Gummidichtung des Kolbens. Das Dokument Janssen, R.; Dounce, S.: Biotech-Medikamente sicher verpackt, medizin&technik (4) (2016) Seiten 48-49 beschreibt ein nass-chemisches Verfahren zur Gleitflächenbeschichtung des Kolbenstopfens. Nachteilig bei beiden Verfahren ist, dass zum Erzielen einer geforderten Gleitwirkung auf eine Barriers and Protection against Bacteria, Medicine & Technology (5) (2012) pages 44-45 describes a plasma process for sliding surface treatment of the rubber seal of the piston. The Document Janssen, R .; Dounce, S .: Biotech drugs safely packaged, medical & technology (4) (2016) pages 48-49 describes a wet-chemical method for sliding surface coating of the piston stopper. A disadvantage of both methods is that to achieve a required sliding effect on a
Silikonisierung des Spritzenkörpers nicht vollständig verzichtet werden kann. Siliconization of the syringe body can not be completely dispensed with.
Ferner ist aus dem Dokument Wang, L.; McCarthy, T.J.: Covalently Attached Liquids: Instant Omniphobic Surfaces with Unprecedented Repellency, Angewandte Chemie 128 (2016) Seiten 252-256 ein Verfahren zur Herstellung einer Further, from the document Wang, L .; McCarthy, T.J .: Covalently Attached Liquids: Instant Omniphobic Surfaces with Unprecedented Repellency, Angewandte Chemie 128 (2016) pp. 252-256 discloses a method of making a
Beschichtungslösung, enthaltend Dimethoxydimethylsilan bekannt, welches zur Benetzung von Glasoberflächen geeignet ist. Dimethoxydimethylsilan ist durch die Strukturformel Coating solution containing dimethoxydimethylsilane, which is suitable for wetting glass surfaces. Dimethoxydimethylsilane is by the structural formula
OCH3 OCH 3
H3C-S!-OCH3 H 3 CS! -OCH 3
CH3 CH 3
gegeben. Der Erfindung liegt die Aufgabe zu Grunde, ein verbessertes Verfahren zur given. The invention is based on the object, an improved method for
Beschichtung der Gleitfläche eines Spritzenkörpers anzugeben, das eine Specify coating of the sliding surface of a syringe body, the one
gleichmäßige Gleitreibung und eine geringe Losbrechkraft beim Betätigen eines entlang dieser Gleitfläche relativ zum Spritzenkörper gleitenden Kolbens ermöglicht. Weiterhin liegt der Erfindung die Aufgabe zu Grunde, ein vereinfachtes Verfahren anzugeben, das keinen thermischen Nachbehandlungsschritt erfordert und das Verunreinigungen des Füllguts im Spritzenkörper vermeidet. uniform sliding friction and a low breakout force when operating a sliding along this sliding surface relative to the syringe body piston allows. Furthermore, the invention is based on the object to provide a simplified method that requires no thermal post-treatment step and avoids contamination of the filling material in the syringe body.
Ferner liegt der Erfindung die Aufgabe zu Grunde, einen Spritzenkörper mit verbessertem Gleitverhalten eines darin geführten Kolbens, insbesondere mit besonders geringer Losbrechkraft und besonders gleichmäßiger Gleitreibung beim Betätigen des Kolbens, anzugeben. Furthermore, the invention is based on the object, a syringe body with improved sliding behavior of a guided therein piston, in particular with a particularly low breakout force and particularly uniform sliding friction when operating the piston indicate.
Die Aufgabe wird hinsichtlich des Verfahrens erfindungsgemäß durch ein Verfahren mit den Merkmalen des Anspruchs 1 gelöst. Die Aufgabe wird hinsichtlich des Spritzenkörpers durch einen Spritzenkörper mit den Merkmalen des Anspruchs 7 gelöst. The object is achieved in terms of the method according to the invention by a method having the features of claim 1. The object is achieved with regard to the syringe body by a syringe body having the features of claim 7.
Vorteilhafte Ausgestaltungen der Erfindung sind Gegenstand der Unteransprüche. Advantageous embodiments of the invention are the subject of the dependent claims.
Bei einem Verfahren zur Beschichtung einer Gleitfläche eines Spritzenkörpers aus Glas oder Kunststoff mit einer omniphoben Gleitschicht wird in einem ersten Schritt die Gleitfläche gereinigt. Im Falle eines Kunststoffsubstrates ist das Aufbringen einer dünnen haftvermittelnden Siliziumoxid (SiOx) - Schicht auf die Gleitfläche notwen dig, an der die omniphobe Gleitschicht anbinden kann. Die dünne haftvermittelnde SiOx-Schicht kann beispielsweise mittels Sol-Gel-Technik, Beflammungsverfahren (C-CVD) oder Plasmabeschichtung aufgebracht werden. Als Plasmaverfahren können sowohl Vakuum- als auch Atmosphärendruck- Verfahren in Betracht gezogen werden. Anschließend wird die Gleitfläche erfindungsgemäß mit einer Benetzungs lösung, welche ein Silan und/oder ein Siloxan mit einem Gewichtsanteil von zwischen 0,1% und 25% in saurer Lösung in einem organischen Lösungsmittel enthält, benetzt. Als Silan kann beispielsweise Dimethoxydimethylsilan, In a method for coating a sliding surface of a syringe body made of glass or plastic with an omniphobic sliding layer, the sliding surface is cleaned in a first step. In the case of a plastic substrate, the application of a thin adhesion-promoting silicon oxide (SiOx) layer to the sliding surface is necessary, to which the omniphobic sliding layer can bond. The thin adhesion-promoting SiOx layer can be applied, for example, by means of sol-gel technology, flame treatment (C-CVD) or plasma coating. As a plasma method, both vacuum and atmospheric pressure methods can be considered. Subsequently, the sliding surface according to the invention with a wetting solution, which is a silane and / or a siloxane with a weight fraction of between 0.1% and 25% in acidic solution in an organic solvent contains, wetted. As silane, for example, dimethoxydimethylsilane,
Methyltrimethoxysilan oder n-Propyltrimethoxysilan verwendet werden. Methyltrimethoxysilane or n-propyltrimethoxysilane can be used.
Als Siloxan kann beispielsweise Polydimethylsiloxan mit verschiedenen Viskositäten verwendet werden. Als organische Lösungsmittel können beispielsweise Isopropanol oder Ethanol verwendet werden. As the siloxane, for example, polydimethylsiloxane having various viscosities can be used. As organic solvents, for example, isopropanol or ethanol can be used.
Ein Verfahren zum Herstellen einer Benetzungslösung enthaltend A method for producing a wetting solution containing
Dimethoxydimethylsilan, welche zur Benetzung von Glasoberflächen geeignet ist, ist aus dem Stand der Technik bekannt. Dimethoxydimethylsilane, which is suitable for wetting glass surfaces, is known in the art.
In einer Ausführungsform des Verfahrens wirkt die Benetzungslösung während einer Benetzungsdauer von mindestens 1 bis 30 Sekunden, bevorzugt 5 bislO Sekunden, auf die Gleitfläche ein. In one embodiment of the method, the wetting solution acts on the sliding surface during a wetting time of at least 1 to 30 seconds, preferably 5 to 10 seconds.
Anschließend wird die Gleitfläche getrocknet, wobei die Trocknungszeit von der Temperatur abhängig ist. In einer Ausführungsform des Verfahrens beträgt die Trocknungsdauer mindestens 10 Minuten, bevorzugt 15 Minuten bei einer Tempe- ratur von zwischen l8°C und 25°C. In einer weiteren Ausführungsform beträgt die Trockenzeit mindestens 30 Sekunden, bevorzugt eine Minute bei einer Temperatur von 75°C. Subsequently, the sliding surface is dried, the drying time is dependent on the temperature. In one embodiment of the process, the drying time is at least 10 minutes, preferably 15 minutes at a temperature of between 18 ° C and 25 ° C. In a further embodiment, the drying time is at least 30 seconds, preferably one minute at a temperature of 75 ° C.
Anschließend wird die Gleitfläche mit bidestilliertem Wasser oder zunächst mit dem organischen Lösungsmittel und anschließend mit bidestilliertem Wasser gespült und erneut getrocknet. Subsequently, the sliding surface is rinsed with bidistilled water or first with the organic solvent and then with bidistilled water and dried again.
Bei den derart mit einer Gleitbeschichtung versehenen Gleitflächen wurden Wasser- Kontaktwinkel von 100° bis 110° ermittelt. In the sliding surfaces provided with such a sliding coating water contact angle of 100 ° to 110 ° were determined.
Mittels Ellipsometrie wurde die Dicke der so aufgebrachten Gleitbeschichtung zu höchstens 10 Nanometern bestimmt. Mittels Gleitreibungsuntersuchungen wurden an den derart behandelten Glasspritzen- körpem Losbrech- und Gleitreibungskräfte ermittelt, welche vergleichbar zu By means of ellipsometry, the thickness of the thus applied lubricious coating was determined to be at most 10 nanometers. By means of sliding friction tests, breakaway and sliding friction forces were determined on the glass syringe bodies treated in this way, which are comparable to
Glasspritzenkörpem sind, deren Gleitflächen nach dem Stand der Technik ölig silikonisiert waren. Insbesondere wurden Losbrech- und Gleitreibungskräfte von höchstens 5 Newton ermittelt. Glaspritzenkörpem are whose sliding surfaces were siliconized silicon oily according to the prior art. In particular, breakaway and sliding friction forces of at most 5 Newton were determined.
Somit besteht ein Vorteil des erfindungsgemäßen Verfahrens darin, dass freie Silikonöltröpfchen im Glasspritzenkörper vermieden werden und dennoch die für die bestimmungsgemäße Verwendung des Glasspritzenkörpers wichtige Reduktion der Reibung erzielt wird. Dadurch werden eine Verunreinigung des Füllguts und eine Aggregation der Inhaltsstoffe des Füllguts an derartigen Silikonöltröpfchen vermieden und eine sicherere Verwendung des Glasspritzenkörpers ermöglicht. Thus, an advantage of the method according to the invention is that free silicone oil droplets are avoided in the glass syringe body and yet the important for the intended use of the glass syringe body reduction of friction is achieved. As a result, contamination of the contents and an aggregation of the contents of the contents of such silicone oil droplets are avoided and allows a safer use of the glass syringe body.
Ein weiterer Vorteil des erfindungsgemäßen Verfahrens besteht darin, dass kein Einbrennschritt erforderlich ist. Allenfalls kann ein Trockenschritt bei erhöhter Temperatur anfallen, wobei die Temperatur unter l00°C liegt. Another advantage of the method according to the invention is that no burn-in step is required. At most, a drying step may occur at elevated temperature, wherein the temperature is below 100 ° C.
Bei einer Ausführungsform des Verfahrens wird die Gleitfläche vor dem Benetzen aktiviert. Die Aktivierung kann mittels Mikrowellenplasmabehandlung und/oder mittels Radiofrequenz-Plasmabehandlung und/oder mittels Atmosphärendruck plasmabehandlung und/oder mittels Beflammung erfolgen. Die Plasmabehandlung kann eine Plasmavorbehandlung und/oder eine Plasmabeschichtung umfassen. Die Plasmabehandlung kann bei Niederdruck oder bei Atmosphärendruck durchgeführt werden. In one embodiment of the method, the sliding surface is activated prior to wetting. The activation can be carried out by means of microwave plasma treatment and / or by means of radio-frequency plasma treatment and / or by means of atmospheric pressure plasma treatment and / or by means of flame treatment. The plasma treatment may comprise a plasma pretreatment and / or a plasma coating. The plasma treatment may be carried out at low pressure or at atmospheric pressure.
Mit einer solchen Aktivierung wird eine bessere Benetzung und Haftung der With such an activation, a better wetting and adhesion of the
Benetzungslösung auf der Gleitfläche des Spritzenkörpers erzielt. Bei Wetting solution achieved on the sliding surface of the syringe body. at
Kunststoffspritzen ist zur Erzielung einer ausreichenden Haftung zunächst das Aufbringen einer dünnen glasartigen Schicht nötig. Dies kann mittels Plastic syringes is first necessary to apply a thin glassy layer to achieve sufficient adhesion. This can be done by means of
Atmosphärendruckplasmabehandlung, Beflammungsverfahren (combustion Chemical vapor deposition, C-CVD) oder mittels Sol-Gel-Beschichtung erfolgen. Bei einem Spritzenkörper, der zur Aufnahme eines entlang einer Gleitfläche gleitenden Kolbens eingerichtet ist, ist die Gleitfläche erfindungsgemäß mindestens teilweise mit einer omniphoben Gleitbeschichtung, umfassend ein Silan und/oder ein Siloxan, beschichtet. Atmospheric pressure plasma treatment, combustion chemical vapor deposition (C-CVD) or carried out by sol-gel coating. In a syringe body adapted to receive a piston sliding along a sliding surface, the sliding surface according to the invention is at least partially coated with an omniphobic lubricious coating comprising a silane and / or a siloxane.
Alternativ zur Beschichtung des Spritzenkörpers ist auch eine entsprechende Beschichtung des Kolbenstopfens mit einer haftvermittelnden SiOx-Schicht sowie anschließend der omniphoben Gleitbeschichtung, umfassend ein Silan und/oder Siloxan, möglich. Alternatively to the coating of the syringe body, a corresponding coating of the piston stopper with an adhesion-promoting SiOx layer and then the omniphobic lubricious coating comprising a silane and / or siloxane is also possible.
Durch eine derartige Beschichtung werden die Losbrechkraft und die Gleitreibung zwischen dem Kolben und der Gleitfläche so weit reduziert, dass keine zusätzliche Silikonisierung der Gleitfläche erforderlich ist. Dadurch werden eine Verunreinigung des Füllguts und eine Aggregation der Inhaltsstoffe des Füllguts an derartigen Silikonöltröpfchen vermieden und eine sicherere Verwendung des By such a coating, the breakaway force and the sliding friction between the piston and the sliding surface are reduced so much that no additional siliconization of the sliding surface is required. This avoids contamination of the contents and aggregation of the contents of the contents of such silicone oil droplets and a safer use of the
Glasspritzenkörpers ermöglicht. Glass injection body allows.
In einer Ausführungsform ist das Silan der Liste Dimethoxydimethylsilan, In one embodiment, the silane of the list is dimethoxydimethylsilane,
Methyltrimethoxysilan oder n-Propyltrimethoxysilan entnommen. Das Siloxan kann als Polydimethylsiloxan mit verschiedenen Viskositäten ausgebildet sein. Methyltrimethoxysilane or n-propyltrimethoxysilane removed. The siloxane can be formed as polydimethylsiloxane with different viscosities.
In einer Ausführungsform eines Glasspritzenkörpers weist die Gleitbeschichtung auf der Gleitfläche eine Dicke von höchstens 50 Nanometern, bevorzugt zwischen 5 und 10 Nanometern, und einen Wasser-Kontaktwinkel zwischen 90° und 120°, bevorzugt zwischen 100° und 110°, auf. Diese Ausführungsform ermöglicht eine besonders gute Reduktion der Losbrechkraft und der Gleitreibung zwischen dem Kolben und der Gleitfläche. In one embodiment of a glass injection body, the sliding coating on the sliding surface has a thickness of at most 50 nanometers, preferably between 5 and 10 nanometers, and a water contact angle between 90 ° and 120 °, preferably between 100 ° and 110 °. This embodiment allows a particularly good reduction of the breakaway force and the sliding friction between the piston and the sliding surface.
Ausführungsbeispiele der Erfindung werden im Folgenden anhand einer Zeichnung näher erläutert. Embodiments of the invention will be explained in more detail below with reference to a drawing.
Darin zeigt: Figur 1 schematisch einen beschichteten Glasspritzenkörper. It shows: 1 shows schematically a coated glass syringe body.
Figur 1 zeigt schematisch einen Glasspritzenkörper 1, in dem ein Kolben 2 gleitend geführt ist. Der Glasspritzenkörper 1 ist aus Glassubstrat gefertigt und zylindrisch geformt. Die Innenwand des Zylinders bildet die Gleitfläche 1.1, entlang welcher der Kolben 2 gleitet. Figure 1 shows schematically a glass syringe body 1, in which a piston 2 is slidably guided. The glass-body 1 is made of glass substrate and cylindrically shaped. The inner wall of the cylinder forms the sliding surface 1.1, along which the piston 2 slides.
Auf der Gleitfläche 1.1 ist mittels des erfindungsgemäßen Verfahrens eine On the sliding surface 1.1 is by means of the method according to the invention a
Gleitbeschichtung 3 aufgebracht, welche Dimethoxydimethylsilan enthält. Die Gleitbeschichtung 3 weist eine Dicke von höchstens 10 Nanometern auf. Die Schichtdicke kann beispielsweise mittels Ellipsometrie bestimmt werden. Die Gleitbeschichtung 3 ist so ausgebildet, dass der Wasser-Kontaktwinkel über 90° liegt. Vorzugsweise liegt der Wasser-Kontaktwinkel bei mindestens 100°. Slip coating 3 applied, which contains dimethoxydimethylsilane. The sliding coating 3 has a thickness of at most 10 nanometers. The layer thickness can be determined, for example, by means of ellipsometry. The sliding coating 3 is designed so that the water contact angle is above 90 °. Preferably, the water contact angle is at least 100 °.
Ausführungsbeispiel zur Herstellung einer Gleitbeschichtung 3: Exemplary embodiment for producing a sliding coating 3:
Die Benetzungslösung wurde aus Dimethoxydimethylsilan (10 w%) in Isopropanol hergestellt, das Ansäuern erfolgte mit Schwefelsäure. Ein Glasspritzenkörper 1 wurden über 15 Sekunden hinweg auf der Gleitfläche 1.1 mit der hergestellten Benetzungslösung benetzt, anschließend 15 Minuten bei einer Raumtemperatur von 2l°C getrocknet und im Anschluss mit bidestilliertem Wasser gespült. Nach  The wetting solution was prepared from dimethoxydimethylsilane (10w%) in isopropanol, acidification with sulfuric acid. A glass syringe body 1 was wetted for 15 seconds on the sliding surface 1.1 with the prepared wetting solution, then dried for 15 minutes at a room temperature of 2l ° C and then rinsed with bidistilled water. After
Trocknung der beschichteten Gleitfläche 1.1 wurde die Gleitreibung zwischen dem Glasspritzenkörper 1 und einem Kolben 2 zu 3,2 N ± 0,6 N bestimmt (Mittelwert aus 10 Proben). Dabei erfolgte die Messung der ungefüllten Glasspritzenkörper 1 mit einer Universalprüfmaschine Inspect Table 50 (Fa. Hegewald und Peschke), als Kolben 2 wurden NovaPure®-Kolbenstopfen verwendet. Drying of the coated sliding surface 1.1, the sliding friction between the glass-body 1 and a piston 2 was determined to 3.2 N ± 0.6 N (average of 10 samples). In this case, the measurement of unfilled glass syringe bodies 1 was carried out with an Inspect Table 50 universal testing machine (Hegewald and Peschke), as piston 2 NovaPure® plunger stoppers were used.
Die Schichtdicke der aufgebrachten Gleitbeschichtung 3 wurde an ebenso beschichteten Silizium- Wafern mittels Ellipsometrie zu unter 10 nm bestimmt. Die Bestimmung des Wasser-Kontaktwinkels erfolgte an beschichteten The layer thickness of the applied lubricious coating 3 was determined on similarly coated silicon wafers by means of ellipsometry below 10 nm. The determination of the water contact angle was carried out on coated
Flachglasssubstraten zu 105° ± 1°. BEZUGSZEICHENLISTE Flat glass substrates at 105 ° ± 1 °. LIST OF REFERENCE NUMBERS
Glasspritzenkörper Glass syringe body
Gleitfläche sliding surface
Kolben piston
Gleitbeschichtung slide coating

Claims

P A T E N T A N S P R Ü C H E PATENT APPLICATIONS
1. Verfahren zur Beschichtung einer Gleitfläche (1.1) eines Spritzenkörpers (1) aus Glas oder Kunststoff mit einer omniphoben Gleitschicht (3) umfassend die Schritte: 1. A method for coating a sliding surface (1.1) of a syringe body (1) made of glass or plastic with an omniphobic sliding layer (3) comprising the steps:
Reinigen der Gleitfläche (1.1),  Cleaning the sliding surface (1.1),
Aufbringen einer dünnen Siliziumoxid (SiOx) - Schicht auf die  Applying a thin silicon oxide (SiOx) layer to the
Gleitfläche (1.1), wenn der Spritzenkörper (1) aus Kunststoff ist,  Sliding surface (1.1), when the syringe body (1) is made of plastic,
Benetzen der Gleitfläche (1.1) mit einer Benetzungslösung enthaltend ein Silan und/oder ein Siloxan mit einem Gewichtsanteil von zwischen 0,1% und 25% in saurer Lösung in einem organischen Lösungsmittel,  Wetting the sliding surface (1.1) with a wetting solution comprising a silane and / or a siloxane with a weight fraction of between 0.1% and 25% in acidic solution in an organic solvent,
Trocknen der Gleitfläche (1.1),  Drying the sliding surface (1.1),
Spülen der Gleitfläche (1.1) mit einem organischen Lösungsmittel und an schließend mit bidestilliertem Wasser oder nur mit bidestilliertem Wasser und Trocknen der Gleitfläche (1.1).  Rinsing the sliding surface (1.1) with an organic solvent and closing with bidistilled water or only with bidistilled water and drying the sliding surface (1.1).
2. Verfahren nach Anspruch 1, dadurch gekennzeichnet, dass die Benetzungslösung Dimethoxydimethylsilan, Methyltrimethoxysilan, 2. The method according to claim 1, characterized in that the wetting solution dimethoxydimethylsilane, methyltrimethoxysilane,
n-Propyltrimethoxysilan oder Polydimethylsiloxan oder eine Mischung daraus enthält.  n-propyltrimethoxysilane or polydimethylsiloxane or a mixture thereof.
3. Verfahren nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass das organische Lösungsmittel Isopropanol oder Ethanol enthält. 3. The method according to any one of the preceding claims, characterized in that the organic solvent contains isopropanol or ethanol.
4. Verfahren nach einem der vorhergehenden Ansprüche, dadurch gekennzeichnet, dass die Gleitfläche (1.1) vor dem Benetzen aktiviert wird. 4. The method according to any one of the preceding claims, characterized in that the sliding surface (1.1) is activated before wetting.
5. Verfahren nach Anspruch 4, dadurch gekennzeichnet, dass die Gleitfläche (1.1) mittels Plasmabehandlung im Niederdruck oder bei Atmosphärendruck aktiviert oder beschichtet wird. 5. The method according to claim 4, characterized in that the sliding surface (1.1) is activated or coated by means of plasma treatment in low pressure or at atmospheric pressure.
6. Verfahren nach Anspruch 4, dadurch gekennzeichnet, dass die Gleitfläche (1.1) mittels Beflammung oder mittels combustion Chemical vapor deposition (C- CVD)-Beschichtung oder mittels Sol-Gel-Beschichtung aktiviert oder beschichtet wird. 6. The method according to claim 4, characterized in that the sliding surface (1.1) is activated or coated by means of flame treatment or by combustion chemical vapor deposition (C-CVD) coating or by means of sol-gel coating.
7. Spritzenkörper (1) aus Glas oder Kunststoff, eingerichtet zur Aufnahme eines entlang mindestens einer Gleitfläche (1.1) gleitenden Kolbens (2), dadurch gekennzeichnet, dass die mindestens eine Gleitfläche (1.1) mindestens teilweise mit einer omniphoben Gleitbeschichtung (3) enthaltend ein Silan und/oder ein Siloxan beschichtet ist. 7. syringe body (1) made of glass or plastic, adapted for receiving a along at least one sliding surface (1.1) sliding piston (2), characterized in that the at least one sliding surface (1.1) at least partially with an omniphobic sliding coating (3) containing a Silane and / or a siloxane is coated.
8. Spritzenkörper (1) nach Anspruch 7, dadurch gekennzeichnet, dass die 8. syringe body (1) according to claim 7, characterized in that the
Gleitbeschichtung (3) Dimethoxydimethylsilan und/oder Methyltrimethoxysilan und/oder n-Propyltrimethoxysilan und/oder Polydimethylsiloxan enthält.  Sliding coating (3) Dimethoxydimethylsilan and / or methyltrimethoxysilane and / or n-propyltrimethoxysilane and / or polydimethylsiloxane contains.
9. Spritzenkörper (1) nach Anspruch 7 oder 8, dadurch gekennzeichnet, dass die Gleitbeschichtung (3) eine Dicke von höchstens 50 Nanometern, bevorzugt zwischen 5 und 10 Nanometern, und einen Wasser-Kontaktwinkel von mindestens 90°, bevorzugt von mindestens 100°, aufweist. 9. syringe body (1) according to claim 7 or 8, characterized in that the lubricious coating (3) has a thickness of at most 50 nanometers, preferably between 5 and 10 nanometers, and a water contact angle of at least 90 °, preferably of at least 100 ° , having.
PCT/EP2019/063901 2018-06-08 2019-05-29 Internally coated syringe body and method for the internal coating of syringe bodies WO2019233835A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP19727652.0A EP3801696A1 (en) 2018-06-08 2019-05-29 Internally coated syringe body and method for the internal coating of syringe bodies

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102018113686.2 2018-06-08
DE102018113686.2A DE102018113686B3 (en) 2018-06-08 2018-06-08 Internal coated syringe body and method for internal coating of syringe bodies

Publications (1)

Publication Number Publication Date
WO2019233835A1 true WO2019233835A1 (en) 2019-12-12

Family

ID=66677144

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2019/063901 WO2019233835A1 (en) 2018-06-08 2019-05-29 Internally coated syringe body and method for the internal coating of syringe bodies

Country Status (3)

Country Link
EP (1) EP3801696A1 (en)
DE (1) DE102018113686B3 (en)
WO (1) WO2019233835A1 (en)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2768947A1 (en) * 1997-09-29 1999-04-02 Gaz De France Treatment of surface of substrate
EP1221347A2 (en) * 2001-01-05 2002-07-10 Degussa Aktiengesellschaft Process for applying on a polymeric substrate a fluoroalkyl functional organopolysiloxane coating with water and oil repellent properties
US20130197451A1 (en) * 2012-01-31 2013-08-01 Terumo Kabushiki Kaisha Syringe for prefilled syringe

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10036832C1 (en) * 2000-07-28 2001-12-13 Schott Glas Applying heat fixed lubricant layer onto inner wall of cylindrical medical containers comprises applying lubricant, homogenizing to layer and selectively heat-fixing lubricant layer using IR radiation
DE102009042159B4 (en) * 2009-09-11 2017-09-28 Schott Ag Method for improving the tribological properties of a glass surface

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2768947A1 (en) * 1997-09-29 1999-04-02 Gaz De France Treatment of surface of substrate
EP1221347A2 (en) * 2001-01-05 2002-07-10 Degussa Aktiengesellschaft Process for applying on a polymeric substrate a fluoroalkyl functional organopolysiloxane coating with water and oil repellent properties
US20130197451A1 (en) * 2012-01-31 2013-08-01 Terumo Kabushiki Kaisha Syringe for prefilled syringe

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
JANSSEN, R.DOUNCE, S., BIOTECH-MEDIKAMENTE SICHER VERPACKT, MEDIZIN&TECHNIK, vol. 4, 2016, pages 48 - 49
LIMING WANG ET AL: "Covalently Attached Liquids: Instant Omniphobic Surfaces with Unprecedented Repellency", ANGEWANDTE CHEMIE, vol. 128, no. 1, 16 November 2015 (2015-11-16), DE, pages 252 - 256, XP055612039, ISSN: 0044-8249, DOI: 10.1002/ange.201509385 *
MELAMIES, I.A., BARRIEREN UND SCHUTZ VOR BAKTERIEN, MEDIZIN&TECHNIK, vol. 5, 2012, pages 44 - 45
PETERSEN, C.: "Pre-fillable syringes for the biotechnological requirements of the present and future", PHARM.IND., vol. 78, no. 1, 2016, pages 121 - 130
REUTER, B.PETERSEN, C.: "Die Silikonisierung von Spritzen", TECHNO.PHARM., vol. 2, no. 4, 2012, pages 238 - 244
WANG, L.MCCARTHY, T.J.: "Covalently Attached Liquids: Instant Omniphobic Surfaces with Unprecedented Repellency", ANGEWANDTE CHEMIE, vol. 128, 2016, pages 252 - 256

Also Published As

Publication number Publication date
DE102018113686B3 (en) 2019-06-27
EP3801696A1 (en) 2021-04-14

Similar Documents

Publication Publication Date Title
EP0920879B1 (en) Pharmaceutical packaging means having an elongated hollow body of plastics, and manufacturing process therefor
EP1175918B1 (en) Process and device for application of a heat secured lubricant layer
EP2796520B1 (en) Containers with low particle emission and friction-controlled dry sliding surface, and method for the production thereof
DE102011009057A1 (en) Plasma treatment device for the production of coatings
EP3593910A2 (en) Method for coating a glass syringe body for a hypodermic ready-for-use glass syringe, hypodermic ready-for-use glass syringe and plasma treatment device for glass syringe bodies of hypodermischer ready-for-use glass syringes
EP3434378A2 (en) Workpiece and method for coating
DE102018122001A1 (en) Packaging with sliding layer and process for pharmaceutical and cosmetic substances and preparation for its manufacture
DE19744367C1 (en) Simple application of thin, uniform silicone oil coating free from particles to medical cannula
DE2316192A1 (en) STORAGE DEVICE MADE OF PLASTIC
DE60003489T2 (en) Composition for non-wettable transparent coating and objects coated with it
DE4328657A1 (en) Organopolysiloxane mixture for the production of adhesive-repellent organopolysiloxane films
DE102018113686B3 (en) Internal coated syringe body and method for internal coating of syringe bodies
DE10329262B3 (en) Coating a paper substrate with a polymer, useful for producing semiconductor substrates, comprises contacting the surface with a solution of a phenol-functional (co)polymer
DE68922983T2 (en) Hardenable, silicone-coated seal.
DE69114097T2 (en) Method and means for introducing use properties into a body and the body thus produced.
DE3884711T2 (en) Process for the production of surfaces with good sliding behavior.
WO1996009993A1 (en) Mixture for treating silicon-containing substrates
DE4104515C1 (en)
EP1458820B1 (en) Surface treating agents for organic polymer bases of polymerizable aerobic (meth)acrylate systems
DE102005019488A1 (en) Component e.g. crankshaft, for use in internal combustion engine of motor vehicle, has oil-wetting free or oleophobic surface provided with coating, which has fluorine containing organic polymer e.g. fluorine containing alkyl polymer
DE102017114959A1 (en) Glass cylinder for a reduced friction piston-cylinder assembly and method of treating a glass cylinder for a piston-cylinder assembly
EP2501557B1 (en) Novel, impact-damped wheels or rollers and method for the production thereof
EP0018529A1 (en) Cold-setting solvent-free coating composition
DE2228183A1 (en) Method of treating upper flat
DE10334164A1 (en) Glass capillary for microinjection and method for making a glass capillary for microinjection

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19727652

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase

Ref country code: DE

ENP Entry into the national phase

Ref document number: 2019727652

Country of ref document: EP

Effective date: 20210111