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US20120318677A1 - Method for treating the surface of a device for dispensing a fluid product - Google Patents

Method for treating the surface of a device for dispensing a fluid product Download PDF

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Publication number
US20120318677A1
US20120318677A1 US13/514,369 US201013514369A US2012318677A1 US 20120318677 A1 US20120318677 A1 US 20120318677A1 US 201013514369 A US201013514369 A US 201013514369A US 2012318677 A1 US2012318677 A1 US 2012318677A1
Authority
US
United States
Prior art keywords
vinyl
acrylic
terminated
fluid
component part
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Abandoned
Application number
US13/514,369
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English (en)
Inventor
Pascal Bruna
Serge Herry
Sébastien Roussel
Matthieu Laurent
Fabien Nekelson
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Aptar France SAS
Original Assignee
Valois SAS
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 Valois SAS filed Critical Valois SAS
Assigned to VALOIS SAS reassignment VALOIS SAS ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: BRUNA, PASCAL, HERRY, SERGE, LAURENT, MATTHIEU, NEKELSON, FABIEN, ROUSSEL, SEBASTIEN
Assigned to APTAR FRANCE SAS reassignment APTAR FRANCE SAS CHANGE OF NAME (SEE DOCUMENT FOR DETAILS). Assignors: VALOIS
Publication of US20120318677A1 publication Critical patent/US20120318677A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • 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
    • C08J7/16—Chemical modification with polymerisable compounds
    • 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
    • A61M15/00—Inhalators
    • 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
    • A61M2205/00—General characteristics of the apparatus
    • A61M2205/02—General characteristics of the apparatus characterised by a particular materials
    • A61M2205/0238—General characteristics of the apparatus characterised by a particular materials the material being a coating or protective layer
    • 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
    • A61M2207/00—Methods of manufacture, assembly or production
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/18—Processes for applying liquids or other fluent materials performed by dipping
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2201/00—Polymeric substrate or laminate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D2202/00—Metallic substrate
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
    • B05D5/08—Processes 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
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D83/00—Containers or packages with special means for dispensing contents
    • B65D83/14—Containers or packages with special means for dispensing contents for delivery of liquid or semi-liquid contents by internal gaseous pressure, i.e. aerosol containers comprising propellant for a product delivered by a propellant
    • B65D83/75—Aerosol containers not provided for in groups B65D83/16 - B65D83/74

Definitions

  • the present invention relates to a surface treatment method for fluid dispenser devices.
  • Fluid dispenser devices are well known. They may comprise: one or more reservoirs; a dispenser member, such as a pump, a valve, or a piston that is movable in the reservoir; and a dispenser head that is provided with a dispenser orifice.
  • the dispenser devices generally include component parts that are made out of various materials.
  • the reservoir may be made out of plastics or synthetic material, out of glass, or out of metal.
  • Various parts, such as pistons or gaskets may be made out of flexible plastics materials such as elastomers.
  • Other parts e.g. crimping caps, springs, or valve-forming balls, are generally made out of metal.
  • any risk of interaction between the fluid to be dispensed and the various materials may be harmful to said fluid.
  • the interactions may include molecules of the materials leaching into the fluid. For example, the interactions may degrade certain active principles, such as hormones, peptides, or enzymes, in particular in nasal-spray devices.
  • An object of the present invention is to propose a surface treatment method that avoids the above-mentioned drawbacks.
  • an object of the present invention is to provide a surface treatment method that is effective, long-lasting, non-polluting, and simple to perform.
  • the present invention thus provides a treatment method for treating the surface of a fluid dispenser device, said method comprising the step of using chemical grafting to form a thin film on at least one support surface of at least one component part that is in contact with said fluid, said thin film preventing interactions between said fluid and said component part.
  • said grafting step comprises putting said surface that is in contact with the fluid into contact with a solution that includes at least one adhesive primer, said adhesive primer being a cleavable aryl salt, and at least one monomer or polymer selected from the group constituted by vinyl- or acrylic-terminated siloxanes and vinyl or acrylic monomers.
  • said chemical grafting creates covalent bonds between the molecules of said thin film and said support surface. This creates a strong and long-lasting connection.
  • said chemical grafting is performed in an aqueous medium. This makes it possible to use chemistry that is non-polluting or green and that does not present any risk to the environment.
  • the cleavable aryl salt is selected from the group constituted by: aryl diazonium salts; aryl ammonium salts; aryl phosphonium salts; aryl sulfonium salts; and aryl iodonium salts.
  • the cleavable aryl salts are selected from compounds of general formula ArN 2 + , X ⁇ in which Ar represents the aryl group and X ⁇ represents an anion.
  • the aryl group in an organic compound is a functional group derived from an aromatic ring.
  • X ⁇ anions are selected from: inorganic anions such as halides, such as I—, Cl—, and Br—; halogenoborates such as tetrafluoroborate; and organic anions such as alcoholates, carboxylates, perchlorates, and sulfonates.
  • inorganic anions such as halides, such as I—, Cl—, and Br—
  • halogenoborates such as tetrafluoroborate
  • organic anions such as alcoholates, carboxylates, perchlorates, and sulfonates.
  • the aryl groups Ar are selected from possibly mono- or poly-substituted aromatic or heteroaromatic groups constituted by one or more aromatic rings of 3 to 8 carbons.
  • the heteroatoms of the heteroaromatic compounds are selected from N, O, P, and S.
  • the substituents may contain alkyl groups and one or more heteroatoms such as N, O, F, Cl, P, Si, Br, or S.
  • the aryl groups are selected from: aryl groups substituted by attractor groups such as NO 2 ; COH; CN; CO 2 H; ketones; esters; amines; and halogens.
  • the aryl groups are selected from the group constituted by: phenyl and nitrophenyl groups.
  • the cleavable aryl salt is selected from the group constituted by: phenyldiazonium tetrafluoroborate; 4-nitrophenyldiazonium tetrafluoroborate; 4-bromophenyldiazonium tetrafluoroborate; 4-aminophenyldiazonium chloride; 4-aminomethylphenyldiazonium chloride; 2-methyl-4-chlorophenyldiazonium chloride; 4-benzoylbenzenediazonium tetrafluoroborate; 4-cyanophenyldiazonium tetrafluoroborate; 4-carboxyphenyldiazonium tetrafluoroborate; 4-acetamidophenyldiazonium tetrafluoroborate; 4-phenylacetic acid diazonium tetrafluoroborate; 2-methyl-4-[(2-methylphenyl)diazenyl]benzenediazon
  • the cleavable aryl salt is selected from the group constituted by: 4-nitrophenyldiazonium tetrafluoroborate; 4-aminophenyldiazonium chloride; 2-methyl-4-chlorophenyldiazonium chloride; and 4-carboxyphenyldiazonium tetrafluoroborate.
  • the cleavable aryl salt concentration lies in the range 5 ⁇ 10 ⁇ 3 molar (M) to 10 ⁇ 1 M.
  • the cleavable aryl salt concentration is about 5 ⁇ 10 ⁇ 2 M.
  • the cleavable aryl salt is prepared in situ.
  • said chemical-grafting step is initiated by chemically activating a diazonium salt so as to form an anchor layer for said thin film.
  • said chemical-grafting step is initiated by chemical activation.
  • said chemical activation is initiated by the presence of a reducing agent in the solution.
  • the solution comprises a reducing agent.
  • reducing agent means a compound that donates electrons during a redox reaction.
  • the reducing agent presents a redox potential difference relative to the redox potential of the cleavable aryl salt, that lies in the range 0.3 volts (V) to 3 V.
  • the reducing agent is selected from the group constituted by: reducing metals that are possibly finely divided, such as iron, zinc, or nickel; a metal salt that is possibly in the form of a metallocene; and an organic reducing agent such as hypophosphorus acid, or ascorbic acid.
  • the reducing agent concentration lies in the range 0.005 M to 2 M.
  • the reducing agent concentration is about 0.6 M.
  • said thin film has a thickness that is less than 1 micrometer ( ⁇ m), and that lies in the range 10 angstroms ( ⁇ ) to 2000 ⁇ , advantageously lies in the range 10 ⁇ to 800 ⁇ , preferably lies in the range 400 ⁇ to 1000 ⁇ .
  • No conventional coating technique makes it possible to obtain chemically-grafted layers that are as thin.
  • vinyl- or acrylic-terminated siloxane means a saturated silicon and oxygen hydride that is formed with straight or branched chains of alternating silicon and oxygen atoms and including terminating vinyl or acrylic motifs.
  • vinyl- or acrylic-terminated siloxanes are selected from the group constituted by: vinyl- or acrylic-terminated polyalkylsiloxanes such as vinyl- or acrylic-terminated polymethylsiloxane; vinyl- or acrylic-terminated polydimethylsiloxane such as polydimethylsiloxane-acrylate (PDMS-acrylate); vinyl- or acrylic-terminated polyarylsiloxanes such as vinyl- or acrylic-terminated polyphenylsiloxane such as polyvinylphenylsiloxane; and vinyl- or acrylic-terminated polyarylalkylsiloxanes such as vinyl- or acrylic-terminated polymethylphenylsiloxane.
  • vinyl- or acrylic-terminated polyalkylsiloxanes such as vinyl- or acrylic-terminated polymethylsiloxane
  • vinyl- or acrylic-terminated polydimethylsiloxane such as polydimethylsiloxane-acrylate (PDMS-acrylate)
  • the vinyl or acrylic monomer is selected from the group constituted by: vinyl acetate; acrylonitrile; methacrylonitrile; methyl methacrylate; ethyl methacrylate; butyl methacrylate; propyl methacrylate; hydroxyethyl methacrylate; hydroxpropyl methacrylate; glycidyl methacrylate; and derivatives thereof; acrylamides such as aminoethyl methacrylamides, propyl, butyl, pentyl, and hexyl; cyanoacrylates; diacrylates; dimethacrylates; triacrylates; trimethacrylates; tetraacrylates; tetramethacrylates; styrene and its derivatives; parachlorostyrene; pentafluorostyrene; N-vinyl pyrrolidone; 4-vinyl pyridine; 2-vinyl pyridine; vinyl, acryloyl, and methacryl
  • a potential difference is applied in said solution.
  • the potential difference is applied by a generator that is connected to two electrodes that are identical or different and that are dipped in the solution during the dipping step.
  • the electrodes are selected from: stainless steel; steel; nickel; platinum; gold; silver; zinc; iron; and copper; in pure form or in alloy form.
  • the electrodes are made of stainless steel.
  • the potential difference applied by a generator lies in the range 0.1 V to 2 V.
  • it is about 0.7 V.
  • the potential difference is generated by a chemical cell.
  • the term “chemical cell” means a cell that is made up of two electrodes that are interconnected via an ionic bridge.
  • the two electrodes are selected appropriately for the potential difference to lie in the range 0.1 V to 2.5 V.
  • the chemical cell is created between two different electrodes that are dipped in the solution.
  • the electrodes are selected from: nickel; zinc; iron; copper; and silver; in pure form or in alloy form.
  • the potential difference generated by the chemical cell lies in the range 0.1 V to 1.5 V.
  • the potential difference is about 0.7 V.
  • the electrodes are chemically isolated so as to avoid any contact between the substrate that is immersed in the bath of step b) and the electrodes that are also dipped in the bath of step b).
  • said component part in particular a crimping cap, a spring, or a valve-forming ball, is made out of metal.
  • said component part in particular a piston or a gasket, is made out of a flexible material such as an elastomer.
  • said component part is made out of a synthetic material such as polyethylene or polypropylene.
  • said component part in particular a reservoir, is made out of glass.
  • the method further comprises the step of using chemical grafting to form at least one additional thin film on said support surface.
  • the method comprises the step of using chemical grafting to form a first additional thin film on said support surface, said first additional thin film preventing interactions between said support surface and said fluid.
  • the method comprises the step of using chemical grafting to form a second additional thin film on said support surface, said second additional thin film limiting friction between two component parts that move relative to each other while the fluid dispenser device is being actuated.
  • said at least one additional thin film is deposited on said support surface during at least one successive chemical-grafting step, each step being performed in a single-component bath.
  • said at least one additional thin film is deposited on said support surface simultaneously during a single chemical-grafting step in a multi-component bath.
  • said fluid is a pharmaceutical for spraying, in particular in nasal or oral manner.
  • the present invention makes provision for using a method similar to the method described in document WO 2008/078052, which describes a method of preparing an organic film on the surface of a solid support under non-electrochemical conditions.
  • the method seeks to prepare a thin film, that may be made out of various materials, such as hard plastics, soft plastics, metal, or glass, on the surface of a support.
  • the method mainly comprises putting said support surface into contact with a liquid solution.
  • the liquid solution includes at least one solvent and at least one adhesive primer, enabling radical entities to be formed from the adhesive primer.
  • the “thin film” may be any polymeric film, in particular of organic nature, e.g. resulting from a plurality of units of organic chemical species, and bonded in covalent manner to the surface of the support on which the method is performed.
  • it is a film that is bonded in covalent manner to the surface of a support, and that includes at least one layer of structural units of similar nature.
  • its cohesion is provided by covalent bonds that develop between the various units.
  • the solvent used in the context of the method may be of protic or aprotic nature. It is preferable for the primer to be soluble in said solvent.
  • protic solvent means a solvent that includes at least one hydrogen atom that is capable of being released in the form of a proton.
  • the protic solvent may be selected from the group constituted by: water; deionized water; optionally-acidified distilled water; acetic acid; hydroxylated solvents such as methanol and ethanol; liquid glycols of small molecular weight such as ethyleneglycol; and mixtures thereof.
  • the protic solvent is constituted solely by a protic solvent or by a mixture of different protic solvents.
  • the protic solvent or the mixture of protic solvents may be mixed with at least one aprotic solvent, it being understood that the resulting mixture should present the characteristics of a protic solvent.
  • Acidified water is the preferred protic solvent, and more particularly, acidified distilled water or acidified deionized water.
  • aprotic solvent means a solvent that is considered as not being protic. Under non-extreme conditions, such solvents are not suitable for releasing a proton or for accepting one.
  • the aprotic solvent is advantageously selected from: dimethylformamide (DMF); acetone; and dimethyl sulfoxide (DMSO).
  • adheresive primer corresponds to any organic molecule that is suitable, under certain conditions, for chemisorbing onto the support surface by a radical reaction, such as radical chemical grafting.
  • Such molecules include at least a functional group that is suitable for reacting with a radical, and also a reactive function that reacts with another radical after chemiabsorption.
  • the molecules after grafting a first molecule to the surface of the support, the molecules are capable of forming a polymeric film, and then of reacting with other molecules that are present in its environment.
  • radical chemical grafting refers, in particular, to the use of molecular entities that possess an unpaired electron in order to form bonds with a surface of the covalent-bond type, said molecular entities being generated independently of the support surface onto which they are to be grafted.
  • the radical reaction leads to covalent bonds being formed between the support surface under consideration and the derivative of the grafted adhesive primer, and then between a grafted derivative and molecules that are present in its environment.
  • the term “derivative of the adhesive primer” means a chemical unit resulting from the adhesive primer, after said adhesive primer has reacted by radical chemical grafting, in particular with the surface of the support, or with another radical.
  • the adhesive primer is a cleavable aryl salt selected from the group constituted by: aryl diazonium salts; aryl ammonium salts; aryl phosphonium salts; aryl sulfonium salts; and aryl iodonium salts.
  • chemical grafting is used to form at least one additional thin film on a single support surface, so as to give at least one other property to the support surface.
  • the fluid for dispensing may tend to stick to a surface with which it is in contact, and this may, in particular, have a harmful effect on the reproducibility of the dispensed dose.
  • the invention advantageously makes provision for using chemical grafting to form a first additional thin film that prevents the fluid from sticking to the support surface.
  • the invention advantageously makes provision for using chemical grafting to form a second additional thin film that limits the amount of friction between two component parts that move relative to each other during actuation.
  • the additional thin films may be applied during successive chemical-grafting steps. Each chemical-grafting step may then be performed in a single-component bath. It should be observed that the successive chemical-grafting steps may be performed in any order.
  • the additional thin films may alternatively be applied during a single chemical-grafting step that is thus performed in a multi-component bath. A combination of the two variants may also be envisaged.
  • the present invention applies to multidose devices, such as devices having a pump or a valve mounted on a reservoir, and that are actuated so as to dispense successive doses. It also applies to multidose devices that include a plurality of individual reservoirs, each containing a dose of fluid, such as pre-dosed powder inhalers. It also applies to uni-dose or bi-dose devices in which a piston moves directly in a reservoir on each actuation. In particular, the invention applies to nasal or oral spray devices, to opthalmic dispenser devices, and to needle devices of the syringe type.
  • the invention also provides the use of a grafting method of the invention in order to treat at least one surface of at least one component part of a fluid dispenser device that is in contact with said fluid, so as to prevent interactions between said fluid and said component part.
  • pump means a fluid dispenser device that is actuated manually, and that includes a pump body in which one or more pistons slide.
  • 4-aminobenzoic acid (0.686 g, 7.5 ⁇ 10 ⁇ 3 mol) was dissolved in a solution of hydrochloric acid (1.9 mL in 30 mL of mQ water) and of hypophosphorus acid (3.2 mL, 3.1 ⁇ 10 ⁇ 2 mol). That solution was added to the BUMA emulsion.
  • 4-aminobenzoic acid (2.058 g, 2.25 ⁇ 10 ⁇ 2 mol) was dissolved in a solution of hydrochloric acid (5.8 mL in 90 mL of mQ water) and of hypophosphorus acid (9.7 mL, 50%). That solution was added to the PDMS emulsion.
  • the strips were washed in ethanol, under ultrasound (power at 100 watts (W), temperature at 40° C.) for 5 minutes.
  • the biphasic solution was prepared in two stages. The following were added to a beaker (1), in order and under magnetic stirring (at 300 revolutions per minute (rpm)): PDMS-acrylate (1 g/L); Brij® 35 in solution in water at 8.5% by weight (% wt) (4.37 g/L); and 33 mL of deionized (DI) water. Emulsification then took place under ultrasound at 40° C. and at a power of 200 W (100%) for 15 minutes.
  • the content of beaker (2) was poured into the emulsion of beaker (1).
  • the two wires were connected to a potentiostat and an ammeter was connected in series. The potentiostat imposed a constant potential difference of 0.5 V and the current over time was measured by the ammeter.
  • hypophosphorus acid (0.7 mol/L) was added last, thereby marking the start of the reaction.
  • hypophosphorus acid 0.7 mol/L was added last, thereby marking the start of the reaction.
  • the stainless-steel strips were removed, then rinsed successively in water (a cascade), then in ethanol (a cascade), and finally in isopropanol, in a soxhlet extractor for 16 h.
  • the stainless-steel strips also successfully passed the passivation test.

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  • Chemical & Material Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Treatments Of Macromolecular Shaped Articles (AREA)
US13/514,369 2009-12-23 2010-12-22 Method for treating the surface of a device for dispensing a fluid product Abandoned US20120318677A1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0959512A FR2954330B1 (fr) 2009-12-23 2009-12-23 Procede de traitement de surface d'un dispositif de distribution de produit fluide.
FR0959512 2009-12-23
PCT/FR2010/052880 WO2011077049A1 (fr) 2009-12-23 2010-12-22 Procede de traitement de surface d'un dispositif de distribution de produit fluide.

Publications (1)

Publication Number Publication Date
US20120318677A1 true US20120318677A1 (en) 2012-12-20

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Application Number Title Priority Date Filing Date
US13/514,369 Abandoned US20120318677A1 (en) 2009-12-23 2010-12-22 Method for treating the surface of a device for dispensing a fluid product

Country Status (6)

Country Link
US (1) US20120318677A1 (de)
EP (1) EP2516521A1 (de)
JP (1) JP2013515803A (de)
CN (1) CN102639618A (de)
FR (1) FR2954330B1 (de)
WO (1) WO2011077049A1 (de)

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US11617716B2 (en) 2021-06-10 2023-04-04 Belhaven BioPharma Inc. Dry powder formulations of epinephrine and associated methods
US12005185B2 (en) 2021-12-17 2024-06-11 Belhaven BioPharma Inc. Medical counter measures including dry powder formulations and associated methods

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FR2969628B1 (fr) * 2010-12-22 2013-09-27 Pegastech Procede de revetement par greffage chimique electrocatalyse d'une surface d'un substrat par une couche polymere.

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US11617716B2 (en) 2021-06-10 2023-04-04 Belhaven BioPharma Inc. Dry powder formulations of epinephrine and associated methods
US11872308B2 (en) 2021-06-10 2024-01-16 Belhaven BioPharma Inc. Dry powder formulations of epinephrine and associated methods
US12097287B2 (en) 2021-06-10 2024-09-24 Belhaven BioPharma Inc. Dry powder formulations of epinephrine and associated methods
US12005185B2 (en) 2021-12-17 2024-06-11 Belhaven BioPharma Inc. Medical counter measures including dry powder formulations and associated methods

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WO2011077049A1 (fr) 2011-06-30
FR2954330B1 (fr) 2013-01-04
JP2013515803A (ja) 2013-05-09
EP2516521A1 (de) 2012-10-31
FR2954330A1 (fr) 2011-06-24
CN102639618A (zh) 2012-08-15

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