WO2017173114A1 - Lubricious coating for medical device - Google Patents
Lubricious coating for medical device Download PDFInfo
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- WO2017173114A1 WO2017173114A1 PCT/US2017/025079 US2017025079W WO2017173114A1 WO 2017173114 A1 WO2017173114 A1 WO 2017173114A1 US 2017025079 W US2017025079 W US 2017025079W WO 2017173114 A1 WO2017173114 A1 WO 2017173114A1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/08—Materials for coatings
- A61L29/085—Macromolecular materials
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L29/00—Materials for catheters, medical tubing, cannulae, or endoscopes or for coating catheters
- A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/10—Materials for lubricating medical devices
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2420/00—Materials or methods for coatings medical devices
- A61L2420/02—Methods for coating medical devices
Definitions
- the present disclosure relates to lubricious coatings. More specifically, the present disclosure relates to lubricious medical device coatings
- Medical devices include, amongst others, those that are chronically implanted, devices that are transitorily implanted, and those that not implanted at all. Many types of medical devices are enhanced by reducing the friction between the device and the environment that surrounds the medical device, particularly during insertion of a device.
- One example is catheters that are inserted, at least transitorily, into the body of a subject. Reduction of friction can lead to enhanced patient comfort, procedural ease for the care provider, reduced chances for infection, as well as reduced tissue disruption, amongst other benefits.
- One approach to reducing the friction between a medical device and the environment surrounding the medical device is to apply a lubricious coating onto the medical device.
- Embodiments of the invention are directed towards lubricious coatings for medical devices, methods of forming the coatings, and using the coated medical devices.
- the invention provides a medical device comprising a lubricious coating that has a coated layer comprising a first polymer that is an acrylic acid polymer, a second polymer that is an acrylamide copolymer comprising at least one photoreactive group, and a cross-linking agent comprising at least two photoreactive groups, wherein the coated layer is in contact with a medical device surface and also configured to contact a patient in use.
- the coating can include a third polymer which can include acrylamide, a photoreactive group, or both.
- the invention provides a method for forming a lubricious coating on a medical device, including steps of disposing a coating composition comprising a first polymer that is an acrylic acid polymer, a second polymer that is an acrylamide copolymer comprising at least one photoreactive group, and a cross-linking agent comprising at least two photoreactive groups, on a medical device surface. Disposing can be done using a dip-coating method. In some modes of practice the coating is performed in at a pH of less than about 6, such as about pH 5, which beneficially increases the viscosity of the coating composition and provides advantages. The coating can then be treated with UV light to activate the
- the form coating may also optionally be treated with a bicarbonate solution to provide salt groups on the coated surface.
- the invention provides a method for performing a medical procedure using the coated medical device, which comprises a step of inserting the coated medical device in a subject, wherein the lubricious coating reduces the friction associated with moving the device in a portion of the body.
- Coatings of the invention advantageously provide very good lubricity and a low amount of particulate release when exposed to an aqueous environment, which is very desirable for in vivo use.
- Figure 1 is a graph showing track force (g) over length for different device coatings.
- Figure 2 is a graph showing average particulate counts (10 um, 25 ⁇ ) for different device coatings.
- one approach to reducing the friction between a medical device and the environment surrounding the medical device is to apply a lubricious coating onto the medical device.
- many lubricious coatings are relatively ineffective in reducing the friction between the device and the environment surrounding the device (such as an intravascular space, as one example).
- many lubricious coatings lack sufficient durability leading to a rapid increase in friction during the course of use.
- the coating can be present as a single coated layer on the device.
- the single layer can be described as the coating.
- the coating can be formed using a single coating composition.
- a coating composition can include the first polymer, second polymer, and crosslinking agent, wherein the coating composition is disposed on a device surface and treated to form the coating.
- the coated layer is in contact with a medical device surface and also configured to contact a patient in use.
- the coating of the disclosure includes an acrylic acid polymer (e.g., used as the "first polymer” in the coating composition).
- an "acrylic acid polymer” refers to polymers including acrylic acid monomeric units.
- the acrylic acid polymer can be an acrylic acid homopolymer or an acrylic acid copolymer including acrylic acid and one or more (e.g., two, three, four, five, etc.) other monomeric units that are different than acrylic acid.
- the acrylic acid in a poly(acrylic acid) copolymer, can be the primary monomer (molar quantity), such as present in an amount of greater than 50% (mol), 55% (mol) or greater, 60% (mol) or greater, 65% (mol) or greater, 70% (mol) or greater, 75% (mol) or greater, 80% (mol) or greater, 85% (mol) or greater, 90% (mol) or greater, 92.5% (mol) or greater, 95% (mol) or greater, 97.5% (mol) or 99 % (mol) or greater.
- the primary monomer such as present in an amount of greater than 50% (mol), 55% (mol) or greater, 60% (mol) or greater, 65% (mol) or greater, 70% (mol) or greater, 75% (mol) or greater, 80% (mol) or greater, 85% (mol) or greater, 90% (mol) or greater, 92.5% (mol) or greater, 95% (mol) or greater, 97.5% (mol) or 99 % (mol) or greater.
- acrylic acid is present in the copolymer in the range of about 75% (mol) to about 99.99% (mol), about 85% (mol) to about 99.99% (mol), about 95% (mol) to about 99.99% (mol), or about 98% (mol) to about 99.99% (mol).
- some or all of the acrylic acid groups of the polymer are in salt form.
- the polymer can be partially or fully salted by adding a base salt to a polymer composition, such as sodium hydroxide or potassium hydroxide.
- An acrylic acid copolymer can include one or more co-monomers copolymerizable with acrylic acid.
- exemplary co-monomers that can be used to prepare an acrylic acid copolymer include those that have a carboxylic acid group, such as methacrylic acid, itaconic acid, monomethyl itaconic acid, maleic anhydride, fumaric acid, and crotonic acid, and salts thereof.
- exemplary co-monomers include sulfonic acid-group containing monomers such as acrylamido-2- methylpropanesulfonic acid (AMPS), 2-(meth)acrylamido-2-methylpropane sulfonic acid, vinyl sulfonic acid, 2-sulfoethyl methacrylate, and salts thereof.
- sulfonic acid-group containing monomers such as acrylamido-2- methylpropanesulfonic acid (AMPS), 2-(meth)acrylamido-2-methylpropane sulfonic acid, vinyl sulfonic acid, 2-sulfoethyl methacrylate, and salts thereof.
- Acrylic acid copolymers made from a combination of two or more different acid-group containing monomers can be used, or copolymers made from one or more acid-group containing monomers and one or more non-acid group containing monomers can be used.
- Acrylic acid copolymers can include random copolymers, block copolymers, graft copolymers, or blends thereof.
- Other exemplary carboxylic acid-containing monomers that can be used to prepare acrylic acid group-containing copolymers include styrene and maleic anhydride copolymerized to produce styrene-maleic anhydride copolymer (PSMA).
- PSMA styrene-maleic anhydride copolymer
- the acrylic acid polymer may optionally be described with reference to its pH.
- the acrylic acid polymer may have a pH in the range of about 1 to about 5, about 1.2 to about 5, about 1.5 to about 5, about 2.5 to about 5, about 2.75 to about 4.5, or about 3 to about 4.25.
- the acrylic acid polymer can have an average molecular weight of 150 kDa or greater. In yet other embodiments the acrylic acid polymer can have an average molecular weight of 500 kDa or greater, 750 kDa or greater, or 1000 kDa or greater, such as in the range of about 1000 kDa to about 2500 kDa, about 1000 kDa to about 2000 kDa, or about 1000 kDa to about 2000 kDa,.
- the acrylic acid polymer is prepared by free radical polymerization of acrylic acid at (e.g, about a 0.8 M concentration) in deionized water.
- a concentrated base such as NaOH is added to the acrylic acid solution.
- an initiator such as ammonium persulfate is added with stirring.
- the polymerization solution can be degassed with nitrogen and stirred for hours (e.g., 12-24 hours) at an elevated temperature (e.g., greater than 50°C).
- the polymer can then be polymerized against continuous flow deionized water using 12-14 K dialysis tubing, and then isolated by lyophilization.
- the coating also includes an acrylamide copolymer that has at least one photoreactive group (e.g., used as the "second polymer” in the coating composition).
- an "acrylamide polymer” refers to polymers including acrylamide or methacrylamide monomeric units, further including one or more pendent photoreactive groups from the acrylamide polymer backbone.
- the acrylamide copolymer can be an acrylamide homopolymer further modified to provide pendent photoreactive groups, or acrylamide co-polymer formed from the polymerization reaction of an acrylamide or methacrylamide monomer with one or more other comonomers, prepolymers, or mixtures thereof.
- acrylamide or methacrylamide in an acrylamide polymer, is the primary monomer (molar quantity), such as present in an amount of greater than 50% (mol), 55% (mol) or greater, 60% (mol) or greater, 65% (mol) or greater, 70% (mol) or greater, 75% (mol) or greater, 80% (mol) or greater, 85% (mol) or greater, 90% (mol) or greater in the copolymer.
- acrylamide or methacrylamide is present in the copolymer in the range of about 50% (mol) to about 99% (mol), about 75% (mol) to about 98% (mol), about 80% (mol) to about 97% (mol), or about 85% (mol) to about 95% (mol).
- the acrylamide polymer includes one or more comonomers that include an acid group.
- exemplary co-monomers with acid groups include sulfonic acid-group containing monomers such as acrylamido-2- methylpropanesulfonic acid (AMPS), 2-(meth)acrylamido-2-methylpropane sulfonic acid, vinyl sulfonic acid, 2-sulfoethyl methacrylate, and salts thereof, and monomers that include a carboxylic acid group, such as methacrylic acid, itaconic acid, monomethyl itaconic acid, maleic anhydride, fumaric acid, and crotonic acid, and salts thereof.
- AMPS acrylamido-2- methylpropanesulfonic acid
- 2-(meth)acrylamido-2-methylpropane sulfonic acid vinyl sulfonic acid
- 2-sulfoethyl methacrylate 2-sulfoethyl methacrylate
- an acid group-containing copolymer can be present in the acrylamide copolymer (second polymer) in an amount in the range of about 0.1% (mol) to about 20% (mol), about 0.5% (mol) to about 15% (mol), or about 1% (mol) to about 10% (mol).
- the acrylamide polymer includes one or more oxyalkylene monomers, or one or more segments of oxyalkylene polymer.
- the acrylamide polymer can include one or more ethylene oxide and/or propylene oxide units.
- the acrylamide polymer can be formed from an oxyalkylene prepolymer having one or more reactive chemistries that can allow it to be incorporated to form an acrylamide copolymer.
- the oxyalkylene segment can be based on an ethylene glycol polymer or oligomer having the structure HO-(CH2-CH2-0) shadow-H.
- n ranges from about 3 to about 150 and the number average molecular weight (Mn) of the poly(ethylene glycol) ranges from about 250 Da to about 40 kDa, more typically ranging from about 300 Da to about 20 kDa, from about 400 Da to about 10 kDa, from about 500 Da to about 5000 Da, or about 600 Da to about 1000 Da.
- An oxyalkylene polymer can be effectively derivatized to add polymerizable groups to produce oxyalkylene based pre-polymers. Polymerizable groups such as glycidyl acrylate, glycidyl methacrylate, or acrylic or methacrylic acid can be reacted with the terminal hydroxyl groups of these polymers to provide terminal polymerizable groups.
- alkylene oxide polymer-based prepolymers that can be used to form the acrylamide polymer include, poly(propylene glycol) 5 4o- diacrylate, poly(propylene glycol)475-dimethacrylate, poly(propylene glycoffeoo- diacrylate, poly(ethylene glycoi) 2 5o-diacrylate, poly(ethylene glycol)5 7 5-diacrylate, poly(ethylene glycol)55 0 -dimethacrylate, poly(ethylene glycol)75o-dimethacrylate, poly(ethylene glycol)7oo-diacrylate, and poly(ethylene glycol)iooo-diacrylate, poly(ethylene glycol) 2 ooo diacrylate, poly(ethylene glycol)iooo monomethyl ether monomethacrylate, and poly(ethylene glycol ⁇ monomethyl ether
- alkylene oxide polymer-based macromers are available from Sigma-Aldrich (St. Louis, MO) or Polysciences (Warrington, PA).
- oxyalkylene can be defined in terms of a molar amount in the polymer, or a weight percentage of the copolymer.
- an oxyalkylene prepolymer is reacted with other monomers to form the acrylamide copolymer, it can be convenient to describe the amount of oxyalkylene by a weight percentage in the copolymer.
- the oxyalkylene is present in an amount in the range of about 0.5% (wt) to about 25% (wt), about 2 % (wt) to about 20 % (wt), or about 5 % (wt) to about 15 % (wt).
- the acrylamide copolymer (second polymer) can also include a desired loading of photogroups.
- Reagents and methods for the preparation of an acrylamide copolymer with pendent photoreactive groups can be found in references such as U.S. Patent Nos. 4,979,959; 5,002,582; 5,263,992; 5,414,075; 5,512,329; and 5,637,460, the teaching of which are incorporated herein by reference.
- an acrylamide copolymer with photoreactive groups can be formed by the copolymerization of acrylamide, l-vinyl-2-pyrrolidone, and N-(3- aminopropyl(meth)acrylamide), optionally with one or more other copolymers or prepolymers, such as an oxyalkylene prepolymer.
- the resulting copolymer then can be derivatized with an acyl chloride (such as, for example, 4-benzoylbenzoyl chloride) under Schotten-Baumann conditions. That is, the acyl chloride reacts with the amino group of the N-(3-aminopropyl) moiety of the copolymer.
- An amide is formed resulting in the attachment of the aryl ketone to the polymer.
- An acrylamide copolymer comprising a photoreactive group can also be prepared by copolymerizing acrylamide (and optionally with one or more other copolymers or prepolymers) with a monomer derivatized with a photoreactive group.
- exemplary monomer derivatives include aryl ketone derivatives of hydrophilic free radically polymerizable monomers such as acrylamide, methacrylamide and AMPS.
- One exemplary methacrylamide-based monomer with a pendent photoreactive groups is N-[3-(4-benzoylbenzamido) propyl] methacrylamide (BBA-APMA), the synthesis which is described in Examples 1-3 of U.S. Patent No.
- the second polymer comprises acrylamide-2- acrylamido-2-methylpropanesulfonate (AMPS)- and poly(ethylene glycol)-containing subunits, and further comprises pendent photogroups, as described herein.
- AMPS acrylamide-2- acrylamido-2-methylpropanesulfonate
- poly(ethylene glycol)-containing subunits and further comprises pendent photogroups, as described herein.
- the coating also includes a third polymer that is different than the first and second polymers.
- the third polymer can be another acrylamide copolymer, which also optionally can include photoreactive groups.
- the third polymer is an acrylamide copolymer comprising pendent photoreactive groups, but that does not include an oxyalkylene segment.
- the third polymer is an acrylamide copolymer, wherein acrylamide or methacrylamide is the primary monomer (molar quantity), such as present in an amount of greater than 50% (mol), 55% (mol) or greater, 60% (mol) or greater, 65% (mol) or greater, 70% (mol) or greater, 75% (mol) or greater, 80% (mol) or greater, 85% (mol) or greater, 90% (mol) or greater in the copolymer.
- acrylamide or methacrylamide is present in the third polymer in the range of about 50% (mol) to about 99% (mol), about 75% (mol) to about 97% (mol), about 80% (mol) to about 100% (mol), or about 98% (mol) to about 100% (mol).
- An exemplary third copolymer can be prepared by copolymerizing acrylamide, (e.g., 95-99% mol) with APMA (e.g., 1-5% mol) to form an acrylamide- APMA copolymer, and then reacting with an excess of 4-benzoylbenzoyl chloride in chloroform to provide pendent photoreactive groups.
- acrylamide e.g., 95-99% mol
- APMA e.g., 1-5% mol
- the coating can include other biocompatible polymers.
- biocompatible polymers can be used as the optional third polymer, or can be used as fourth, fifth, etc. polymer.
- Exemplary biocompatible include those that contain ether groups such as poly(ethylene oxide) (PEO), poly(propylene oxide) (PPO), poly(propylene glycol) (PPG) polyvinyl methyl ether), polymeric alcohols such as poly(vinyl alcohol) (PVA), poly(2-hydroxyehtylacrylate) (PHEA) and poly(2-hydroxyethyl vinyl ether) PHEVE), poly(2-etbyl-2-oxazoline) (PEOX), poly(n-acetyliminoethylene) (PAIE) and water soluble polysaccharides such as methyl cellulose, hydroxypropylcellulose and hydroxyethylcellulose.
- PEO poly(ethylene oxide)
- PPO poly(propylene oxide)
- PPG poly(propylene glycol)
- PHEA poly(2-hydroxy
- the coating composition also includes a crosslinking agent having two or more photoreactive groups, which can react with the polymers in the composition, the device surface, or both.
- Suitable photoreactive groups include aryl ketones, such as acetophenone, benzophenone, anthraquinone, anthrone, quinone, and anthrone-like heterocycles.
- a crosslinking agent including a photoreactive group can be referred to as a photo-crosslinker or photoactivatable crosslinking agent.
- the photoactivatable crosslinking agent can be ionic, and can have good solubility in an aqueous composition. Thus, in some embodiments, at least one ionic photoactivatable crosslinking agent can be used to form the coating.
- the ionic crosslinking agent can include an acidic group or salt thereof, such as selected from sulfonic acids, carboxylic acids, phosphonic acids, salts thereof, and the like.
- exemplary counter ions include alkali, alkaline earths metals, ammonium, protonated amines, and the like.
- Exemplary ionic photoactivatable crosslinking agents include 4,5-bis(4- benzoylphenylmethyleneoxy) benzene- 1, 3 -disulfonic acid or salt; 2,5-bis(4- benzoylphenylmethyleneoxy)benzene-l,4-disulfonic acid or salt; 2,5-bis(4- benzoylmethyleneoxy)benzene-l -sulfonic acid or salt; N,N-bis[2-(4- benzoylbenzyloxy)ethyl]-2-aminoethanesulfonic acid or salt, and the like. See U.S. Patent Nos. 6,077,698 (Swan et al), 6,278,018 (Swan), 6,603,040 (Swan) and 7,138,541 (Swan) the disclosures of which are incorporated herein by reference.
- exemplary ionic photoactivatable crosslinking agents include ethylenebis(4-benzoylbenzyldimethylammonium) dibromide and
- restrained multifunctional reagents with photoactivable crosslinking groups can be used in association with device embodiments of the disclosure.
- these restrained multifunctional reagents include tetrakis (4-benzoylbenzyl ether) of pentaerthyritol and the tetrakis (4- benzoylbenzoate ester) of pentaerthyritol. See U.S. Patent Nos. 5,414,075 (Swan et al.) and 5,637,460 (Swan et al.) the disclosures of which are incorporated herein by reference.
- Crosslinking agents can include those having formula Photo -LG-Photo , wherein Photo 1 and Photo 2 independently represent at least one photoreactive group and LG represents a linking group comprising at least one silicon or at least one phosphorus atom.
- a degradable linking agent can include a covalent linkage between at least one photoreactive group and the linking group, wherein the covalent linkage between at least one photoreactive group and the linking group is interrupted by at least one heteroatom. See U.S. Patent No. 8,889,760 (Kurdyumov, et al), the disclosure of which is incorporated herein by reference.
- crosslinking agents can include those having a core molecule with one or more charged groups and one or more photoreactive groups covalently attached to the core molecule by one or more degradable linkers. See U.S. Pub. Pat. App. No. 2011/0144373 (Swan, et al. the disclosure of which is incorporated herein by reference.
- Crosslinking agents including at least two photoreactive groups can be used in association with coating embodiments of the disclosure.
- Exemplary crosslinking agents are described in U.S. Patent No. 8,889,760, the content of which is herein incorporated by reference in its entirety.
- a crosslinking agent having a molecular weight of less than about 1500 kDa can be used in association with coating embodiments of the disclosure.
- the crosslinking agent can have a molecular weight of less than about 1200, 1100, 1000, 900, 800, 700, 600, 500, or 400.
- a crosslinking agent comprising a linking agent having formula Photo '-LG-Photo 2 can be used in association with coating embodiments of the disclosure.
- Photo 1 and Photo 2 independently represent at least one photoreactive group and LG represents a linking group comprising at least one silicon or at least one phosphorus atom, there is a covalent linkage between at least one photoreactive group and the linking group, wherein the covalent linkage between at least one
- photoreactive group and the linking group is interrupted by at least one heteroatom.
- device embodiments of the disclosure can be associated with a crosslinking agent comprising a linking agent having a formula selected from:
- Rl, R2, R8 and R9 are any substitution;
- R3, R4, R6 and R7 are alkyl, aryl, or a combination thereof;
- R5 is any substitution; and each X, independently, is O, N, Se, S, or alkyl, or a combination thereof;
- Rl and R5 are any substitution;
- R2 and R4 can be any substitution, except OH;
- R3 can be alkyl, aryl, or a combination thereof;
- X independently, are O, N, Se, S, alkylene, or a combination thereof;
- Rl, R2, R4 and R5 are any substitution;
- R3 is any substitution;
- R6 and R7 are alkyl, aryl, or a combination thereof; and each X can independently be O, N, Se, S, alkylene, or a combination thereof;
- the crosslinking agent can be bis(4- benzoylphenyl) phosphate.
- an ionic photoactivatable crosslinking agent having good solubility in an aqueous composition can be used in association with coating embodiments of the disclosure.
- Any suitable ionic photoactivatable crosslinking agent can be used.
- the ionic photoactivatable crosslinking agent is a compound of formula I: Xi— Y— X 2 where Y is a radical containing at least one acidic group, basic group, or a salt of an acidic group or basic group.
- Xi and X 2 are each independently a radical containing a latent photoreactive group.
- the photoreactive groups can be the same as those described herein. Spacers can also be part of Xi or X 2 along with the latent photoreactive group.
- the latent photoreactive group includes an aryl ketone or a quinone.
- the radical Y in formula I provides the desired water solubility for the ionic photoactivatable crosslinking agent.
- the water solubility (at room temperature and optimal pH) is at least about 0.05 mg/rriL. In some embodiments, the solubility is about 0.1 to about 10 mg/mL or about 1 to about 5 mg/mL.
- Y is a radical containing at least one acidic group or salt thereof.
- a photoactivatable crosslinking agent can be anionic depending upon the pH of the coating composition.
- Suitable acidic groups include, for example, sulfonic acids, carboxylic acids, phosphonic acids, and the like.
- Suitable salts of such groups include, for example, sulfonate, carboxylate, and phosphate salts.
- the ionic crosslinking agent includes a sulfonic acid or sulfonate group.
- Suitable counter ions include alkali, alkaline earths metals, ammonium, protonated amines, and the like.
- a compound of formula I can have a radical Y that contains a sulfonic acid or sulfonate group; Xi and X 2 can contain photoreactive groups such as aryl ketones.
- Such compounds include 4,5-bis(4- benzoylphenylmethyleneoxy)benzene-l,3-disulfonic acid or salt; 2,5-bis(4- benzoylphenylmethyleneoxy)benzene-l,4-disulfonic acid or salt; 2,5-bis(4- benzoylmethyleneoxy)benzene-l -sulfonic acid or salt; N,N-bis[2-(4- benzoylbenzyloxy)ethyl]-2-aminoethanesulfonic acid or salt, and the like. See U.S. Pat. No. 6,278,018.
- the counter ion of the salt can be, for example, ammonium or an alkali metal such as sodium, potassium, or lithium.
- Y can be a radical that contains a basic group or a salt thereof.
- Y radicals can include, for example, an ammonium, a phosphonium, or a sulfonium group. The group can be neutral or positively charged, depending upon the pH of the coating composition.
- the radical Y includes an ammonium group.
- Suitable counter ions include, for example, carboxylates, halides, sulfate, and phosphate.
- compounds of formula I can have a Y radical that contains an ammonium group; Xi and X 2 can contain photoreactive groups that include aryl ketones.
- photoactivatable crosslinking agents include ethylenebis(4-benzoylbenzyldimethylammonium) salt;
- the ionic photoactivatable crosslinking agent can be a compound having the formula:
- X 1 includes a first photoreactive group
- X 2 includes a second photoreactive group
- Y includes a core molecule
- Z includes at least one charged group
- D 1 includes a first degradable linker
- D 2 includes a second degradable linker.
- a non-ionic photoactivatable crosslinking agent can be used.
- the non-ionic photoactivatable crosslinking agent has the formula XR1R2R3R4, where X is a chemical backbone, and R ls R 2 , R3, and R4 are radicals that include a latent photoreactive group.
- exemplary non-ionic crosslinking agents are described, for example, in U.S. Pat. Nos. 5,414,075 and 5,637,460 (Swan et al, "Restrained Multifunctional Reagent for Surface Modification"). Chemically, the first and second photoreactive groups, and respective spacers, can be the same or different.
- non-ionic photoactivatable crosslinking agent can be represented by the formula:
- PG 1 and PG 2 include, independently, one or more photoreactive groups, for example, an aryl ketone photoreactive group, including, but not limited to, aryl ketones such as acetophenone, benzophenone, anthraquinone, anthrone, anthrone-like heterocycles, their substituted derivatives or a combination thereof;
- LE 1 and LE 2 are, independently, linking elements, including, for example, segments that include urea, carbamate, or a combination thereof;
- X represents a core molecule, which can be either polymeric or non-polymeric, including, but not limited to a hydrocarbon, including a hydrocarbon that is linear, branched, cyclic, or a combination thereof; aromatic, non-aromatic, or a combination thereof; monocyclic, polycyclic, carbocyclic, heterocyclic, or a combination thereof; benzene or a derivative thereof; or a combination thereof.
- Non-ionic crosslinking agents are described, for example, in U.S. Application Number 13/316,030 filed December 9, 2011 (Publ. No. US 2012/0149934) (Kurdyumov, "Photocrosslinker"), the disclosure of which is incorporated herein by reference.
- non-ionic photoactivatable crosslinking agents can also include, for example, those described in U.S. Pat. Publication 2013/0143056 (Swan et al, "Photo- Vinyl Primers/Crosslinkers"), the disclosure of which is incorporated herein by reference.
- exemplary crosslinking agents can include non-ionic photoactivatable
- crosslinking agents having the general formula R - X - R , wherein R is a radical comprising a vinyl group, X is a radical comprising from about one to about twenty carbon atoms, and R 2 is a radical comprising a photoreactive group.
- a single photoactivatable crosslinking agent or any combination of photoactivatable crosslinking agents can be used in forming a coating associated with device embodiments of the disclosure.
- at least one nonionic crosslinking agent such as tetrakis(4-benzoylbenzyl ether) of pentaerythritol can be used with at least one ionic crosslinking agent.
- At least one non-ionic photoactivatable crosslinking agent can be used with at least one cationic photoactivatable crosslinking agent such as an ethylenebis(4-benzoylbenzyldi- methylammonium) salt or at least one anionic photoactivatable crosslinking agent such as 4,5-bis(4-benzoyl-phenylmethyleneoxy)benzene-l,3-disulfonic acid or salt.
- at least one nonionic crosslinking agent can be used with at least one cationic crosslinking agent and at least one anionic crosslinking agent.
- a least one cationic crosslinking agent can be used with at least one anionic crosslinking agent but without a non-ionic crosslinking agent.
- An exemplary crosslinking agent is disodium 4,5-bis[(4-benzoylbenzyl)oxy]- 1,3-benzenedisulfonate (DBDS).
- DBDS disodium 4,5-bis[(4-benzoylbenzyl)oxy]- 1,3-benzenedisulfonate
- This reagent can be prepared by combining 4,5- dihydroxylbenzyl-l,3-disulfonate (CHBDS) with 4-bromomethylbenzophenone (BMBP) in THF and sodium hydroxide, then refluxing and cooling the mixture followed by purification and recrystallization (also as described in U.S. Pat. No. 5,714,360, incorporated herein by reference).
- CHBDS 4,5- dihydroxylbenzyl-l,3-disulfonate
- BMBP 4-bromomethylbenzophenone
- crosslinking agents can include the crosslinking agents described in U.S. Pub. Pat. App. No. 2010/0274012 (to Guire et al.) and U.S. Pat. No. 7,772,393 (to Guire et al.) the content of which is herein incorporated by reference.
- a coating associated with coating embodiments of the disclosure can include boron-containing linking agents such as boron-containing linking agents disclosed in U.S. Pat. Publication 2013/0302529 ("Boron-Containing Linking Agents;"
- linking agents can include borate, borazine, or boronate groups and coatings and devices that incorporate such linking agents, along with related methods.
- the linking agent a compound having the structure (I):
- R 1 is a radical comprising a photoreactive group
- R 2 is selected from OH and a radical comprising a photoreactive group, an alkyl group and an aryl group
- R is selected from OH and a radical comprising a photoreactive group.
- the bonds B-R 1 , B-R 2 and B-R 3 can be chosen independently to be interrupted by a heteroatom, such as O, N, S, or mixtures thereof.
- Additional agents for use with device embodiments herein can include stilbene-based reactive compounds including, but not limited to, those disclosed in U.S. Pat. No. 8,487,137, entitled, "Stilbene-Based Reactive Compounds, Polymeric Matrices Formed Therefrom, and Articles Visualizable by Fluorescence" by
- the coating can include predetermined amounts of polymers to provide a lubricious coating.
- the first polymer (acrylic acid polymer) is the primary polymer in the coating by weight, meaning that it is present in an amount by weight that is greater than any other polymer in the coating composition.
- the first polymer (acrylic acid polymer) can be present in an amount by weight greater than the second polymer (acrylamide photopolymer), or the optional third polymer (e.g., another acrylamide polymer that is different than the second polymer), or present in an amount by weight greater than the combined amount of the first and second polymers.
- a combined amount of the second and third polymer by weight is approximately the same as the amount of the first polymer.
- the first and second polymers constitute about 90% (wt) or greater, 95% (wt) or greater, 98% (wt) or greater, or 100% (wt) of the polymeric materials of the coating composition, or of the total solids of the coating composition.
- the first, second, and third polymers constitute about 90% (wt) or greater, 95% (wt) or greater, 98% (wt) or greater, or 100% (wt) of the polymeric materials of the coating composition, or of the total solids of the coating composition.
- the first polymer (acrylic acid polymer) is present in an amount in the range of about 20 to about 80 % (wt), of about 30 to about 70 % (wt), or about 40 to about 60 % (wt), of the solids components in the coating composition.
- the second polymer (acrylamide photopolymer) is present in an amount in the range of about 10 to about 60 % (wt), of about 20 to about 50 % (wt), or about 30 to about 40 % (wt) of the solids components in the coating composition.
- the optional third polymer e.g., another acrylamide polymer that is different than the second polymer
- the optional third polymer is present in an amount in the range of about 1 to about 35 % (wt), of about 5 to about 25 % (wt), or about 10 to about 20 % (wt) of the solids components in the coating composition.
- the cross-linking agent is present in an amount in the range of about 0.1% to about 5 % (wt), of about 0.5% to about 4 % (wt), or about 0.75% to about 3 % (wt) of the solids components in the coating.
- a coating solution is formed including the first polymer (acrylic acid polymer), second polymer (acrylamide photopolymer), the cross-linking agent, and optionally a third polymer (e.g., another acrylamide photopolymer that is different than the second polymer), in a solvent or mixture of solvents.
- the solvent for the coating composition can include water, an alcohol, or a mixture of water an alcohol.
- An exemplary alcohol is isopropyl alcohol (IP A).
- Exemplary mixtures of water to alcohol include those where the proportion of water to alcohol (vohvol), such as IP A, is in the range of about 99:1 to about 95:5, in the range of about 95:5 to about 50:50, or in the range of about 90: 10 to about 75:25.
- vohvol proportion of water to alcohol
- the pH of the solution is not greater than about 6, such as in the range of about 2 to about 6, or in the range of about 3 to about 5.
- the solution can be adjusted with a compound to provide the desired pH.
- the coating composition includes the acrylamide polymer, this can increase the viscosity of the composition providing coating advantages.
- a more viscous coating composition can improve the coating process and permit a lower concentration of solids materials (polymers and crosslinker) in the coating composition, which provides economic as well as processing advantages.
- the viscosity of the coating composition is about 15 centipoise (cP) or greater, such as in the range of about 17 cP to about 200 cP.
- the concentration of solids in the composition is not greater than about 30 mg/mL, or not greater than about 25 mg/mL, such as in the range of about 5 mg/mL to about 30 mg/mL, or about 10 mg/mL to about 25 mg/mL.
- the coating solution can be applied to a substrate. Prior to application of the first coating solution to the substrate, one or more of many different pretreatment steps can be taken.
- the surface of the substrate can be cleaned. For example, the surface can be wiped or dipped into an alcohol such as isopropyl alcohol.
- the substrate can be put into a detergent solution such as a VALTRON solution and sonicated.
- a compound can be disposed on the surface of the substrate to act as a tie layer.
- the surface of the substrate can be sterilized.
- exemplary techniques can include drop coating, blade coating, dip coating, spray coating, and the like.
- the solution is applied by dip coating.
- a dip coating process can incudes steps of placing the substrate to be coated in the coating composition, letting the substrate sit (dwell) in the coating composition for a period of time, and then withdrawing the substrate from the coating composition.
- the dwell time can be very short, such as a second or seconds, or can be for longer periods of time, such as minutes.
- the speed of dip coating can vary.
- the substrate can be dipped into the coating solution and then withdrawn at a speed in the range of about 0.01 to about 10 cm/s, in the range of about 0.1 to about 4 cm/s, or in the range of about 0.5 to about 2 cm/s.
- actinic radiation such as UV radiation
- actinic radiation can be applied to activate photoreactive groups within the components of the coating solution forming the coating.
- Actinic radiation can be provided by any suitable light source that promotes activation of the photoreactive groups.
- Preferred light sources (such as those available from Dymax Corp.) provide UV irradiation in the range of 190 nm to 360 nm.
- An exemplary UV light source is a Dymax 2000-EC series UV flood lamp with a 400 Watt metal halide bulb.
- a suitable dose of radiation is in the range of from about 0.5 mW/cm 2 to about 2.0 mW/cm 2 .
- Exemplary irradiation times are in the range of seconds to several minutes, such as about 30 seconds to about 2 minutes.
- the coating solution can be dried, before or after application of the actinic radiation.
- some or all of the pendent acid groups from the acrylic acid polymer in the coating are converted to their corresponding salts. This can be accomplished after the coating is treated with UV light, and then by subjecting the coating to bicarbonate treatment. After the coating is treated with UV light it can be subjected to bicarbonate treatment. In an exemplary bicarbonate method the coated device is immersed in an aqueous sodium bicarbonate solution for a period of time and dried until complete. Materials and methods for bicarbonate treatment of coatings can be found in the commonly assigned U.S. Provisional Application Serial No. 62/272,440, entitled "Lubricious Coatings With Surface Salt Groups" filed December 29, 2015, the teaching of which is incorporated herein by reference.
- Substrates on which the coating can be formed can be partially or entirely fabricated from a metal, ceramic, glass, or the like, or a combination thereof.
- Substrates can include polymers such as polyurethanes and polyurethane copolymers, polyethylene, polyolefins, styrene-butadiene copolymers, polyisoprene, isobutylene- isoprene copolymers (butyl rubber), including halogenated butyl rubber, butadiene- styrene-acrylonitrile copolymers, silicone polymers, fluorosilicone polymers, polycarbonates, polyamides, polyesters, polyvinyl chloride, polyether-polyester copolymers, polyether-polyamide copolymers, and the like.
- the substrate can be made of a single material, or a combination of materials.
- Substrate polymers can also include those formed of synthetic polymers, including oligomers, homopolymers, and copolymers resulting from either addition or condensation polymerizations.
- suitable addition polymers include, but are not limited to, acrylics such as those polymerized from methyl acrylate, methyl methacrylate, hydroxyethyl methacrylate, hydroxyethyl acrylate, acrylic acid, methacrylic acid, glyceryl acrylate, glyceryl methacrylate, methacrylamide, and acrylamide; vinyls such as ethylene, propylene, vinyl chloride, vinyl acetate, vinyl pyrrolidone, vinylidene difluoride, and styrene.
- condensation polymers include, but are not limited to, nylons such as polycaprolactam, polylauryl lactam, polyhexamethylene adipamide, and polyhexamethylene dodecanediamide, and also polyurethanes, polycarbonates, polyamides, polysulfones, poly(ethylene
- the substrate includes a polymer selected from the group consisting of polyamide, polyimide, polyether block amide (PEBAX), polyether ether ketone (PEEK), high density polyethylene (HDPE), polyethylene, polyurethane, and polyethylene vinyl acetate.
- a polymer selected from the group consisting of polyamide, polyimide, polyether block amide (PEBAX), polyether ether ketone (PEEK), high density polyethylene (HDPE), polyethylene, polyurethane, and polyethylene vinyl acetate.
- Metals that can be used as substrates in medical articles include platinum, gold, or tungsten, as well as other metals such as rhenium, palladium, rhodium, ruthenium, titanium, nickel, and alloys of these metals, such as stainless steel, titanium/nickel, nitinol alloys, cobalt chrome alloys, non-ferrous alloys, and platinum/iridium alloys.
- One exemplary alloy is MP35.
- the methods and materials of the disclosure can be utilized to coat virtually any medical device for which it is desired to provide a lubricious coating on a surface.
- the coatings are particularly useful for medical articles that can be inserted into and moved within the body.
- the coating can be formed on many materials of the disclosure without requiring a primer layer, or requiring a separate top coat.
- the coating composition with the first polymer, second polymer, and crosslinking agent, and optional third polymer is in contact with a medical device surface and also configured to contact a patient in use.
- Exemplary medical articles include vascular implants and grafts, grafts, surgical devices; synthetic prostheses; vascular prosthesis including endoprosthesis, stent-graft, and endovascular-stent combinations; small diameter grafts, abdominal aortic aneurysm grafts; wound dressings and wound management device; hemostatic barriers; mesh and hernia plugs; patches, including uterine bleeding patches, atrial septic defect (ASD) patches, patent foramen ovale (PFO) patches, ventricular septal defect (VSD) patches, and other generic cardiac patches; ASD, PFO, and VSD closures; percutaneous closure devices, mitral valve repair devices; left atrial appendage filters; valve annuloplasty devices, catheters; central venous access catheters, vascular access catheters, abscess drainage catheters, drug infusion catheters, parenteral feeding catheters, intravenous catheters (e.g., treated with antithrombotic agents), stroke therapy catheters, blood pressure and stent graft
- neurological catheters neuropatches; orthopedic devices such as orthopedic joint implants, bone repair/augmentation devices, cartilage repair devices; urological devices and urethral devices such as urological implants, bladder devices, renal devices and hemodialysis devices, colostomy bag attachment devices; biliary drainage products, vena cava filters, and embolic protection filters and devices and
- coatings of the present disclosure can be used on exemplary medical devices such as braided catheters. In yet other embodiments the coatings can be used advantageously on braided catheters (e.g. PEBAX®).
- the coating is formed on a catheter selected from the group consisting of urethral catheters, renal catheters, intravenous catheters, artificial lung catheters, blood pressure and stent graft catheters, atherectomy catheters, clot extraction catheters, percutaneous transluminal coronary angioplasty (PTCA) catheters, drug infusion catheters, angiographic catheters, neurological catheters such as neurovascular balloon catheters, thoracic cavity suction drainage catheters, electrophysiology catheters, stroke therapy catheters, abscess drainage catheters, central venous access catheters, hemodialysis catheters, and parental feeding catheters.
- a catheter selected from the group consisting of urethral catheters, renal catheters, intravenous catheters, artificial lung catheters, blood pressure and stent graft catheters, atherectomy catheters, clot extraction catheters, percutaneous transluminal coronary angioplasty (PTCA) catheters, drug infusion catheters, angiographic catheters, neurological catheters such as neurovascular balloon catheter
- the thickness of the coating can be in the range of about 100 nm to about 5.0 ⁇ , about 250 nm to about 5.0 ⁇ , about 250 ran to about ⁇ . ⁇ , or about 1.0 ⁇ to about 5.0 ⁇ .
- the thickness can be determined using one or more technique, like microscopic techniques such as scanning electron micrography (SEM) or
- the coating can exhibit lubricity that may be observed as relative low friction.
- the coating can be lubricious after exposure to water.
- the coating may exhibit lubricity of between 0 and 30 grams of force when wetted as measured by a vertical pinch test, such as that described below.
- the coating may exhibit lubricity of less than about 20 grams of force when wetted. In some embodiments, the coating may exhibit lubricity of less than about 15 grams of force when wetted.
- the coating may be described in terms of durability of the lubricity.
- the lubricity may be retained over an extended period of time when the coating is exposed to frictional forces.
- lubricity may be maintained over a plurality of frictional testing cycles.
- the coating may exhibit a lubricity of between 0 and 30 grams of force when wetted for at least 10 consecutive testing cycles.
- the measured lubricity will increase no more than 30 % between the average of cycles 1-5 and the average of cycles 10-15 of the testing.
- the coating may exhibit a relatively low amount of particulate release when exposed to an aqueous environment.
- a medical device having a hydrophilic coating with low particulate levels is very desirable for in vivo use.
- a description of particulate levels can be based on a predetermined coating area and thickness.
- the particle counts are based on 600 mm 2 of coated surface having a coating thickness in the range of 500 nm to 10 ⁇ .
- the particle count can be based on coating areas of greater or less than 600 mm 2 .
- the coating will generate less than 15,000 particles of greater than 10 microns in size in an aqueous environment.
- the coating will generate less than 10,000 particles of greater than 10 microns in size in an aqueous environment.
- the coating will generate less than 5,000 particles of greater than 10 microns in size in an aqueous environment.
- the coating will generate less than 3,000 particles of greater than 10 microns in size in an aqueous environment. In some embodiments, the coating will generate less than 1,000 particles of greater than 10 microns in size in an aqueous environment. It will be appreciated that in accordance with various embodiments herein, the properties of lubricity and low particulate release are both present.
- PA-BBA-AMPS-PEG N-Acetylated poly[acrylamide 93 6% -co-sodium-2- acrylamido-2-methylpropanesulfonate 49% -co-N-(3-(4-benzoylbenzamido)propyl) methacrylamide 0 9% ]-co-methoxy poly(ethylene glycol)iooo monomethacrylate 0 6% (percentages are mole percents) was obtained (PA-BBA-AMPS-PEG). Reagents and methods for the preparation of PA-BBA-AMPS-PEG, and Photo-PA can be found in references such as U.S. Patent Nos.
- BPP The cross-linking agent sodium bis(4-benzoylphenyl) phosphate was prepared according to the methods described in U.S. Pub. No. 2012/0046384.
- PAA Poly(acrylic acid) having an average molecular weight in the range of 1200 - 1800 kDa was used.
- Coating solution A coating solution was prepared by mixing together PAA at 5 g/L; PA-BBA-AMPS-PEG at 3.5 g/L; photo-PA at 1.5 g/L; BPP at 0.15 g/L in a solvent of 15% isopropyl alcohol and 85% water.
- Bicarbonate treatment A bicarbonate treatment solution was prepared with 0.1 M NaHC0 3 in water. Substrates were dipped in the aqueous sodium bicarbonate solution for five seconds and dried until complete.
- PEBAX® tubes I.D. 0.018" O.D. 0.039"; 72D obtained from Medicine Lake Extrusion, Madison, MN; and Pebax/Nylon catheters (O.D.
- Dip coating The coating solution was applied to the substrate using a dip coat method.
- the substrate was immersed in the base coat coating solution with a dwell time of 2 seconds.
- the substrate was then extracted from the solution at a speed of 1.2 cm/s.
- the base layer was then air dried for 2 minutes.
- the coating was then UV cured. Specifically, the coated substrate was rotated in front of a Dymax 2000-EC series UV flood lamp with a 400 Watt metal halide bulb for 60 seconds, approximately 20 cm from the light source.
- Bicarbonate treatment The coating solution was applied to the substrate using a dip coat method. The substrate was immersed in the sodium bicarbonate solution with a dwell time of 5 seconds. The substrate was then extracted from the solution at a speed of 1.2 cm/s. The base layer was then air dried for at least 10 minutes.
- Friction (Lubricity) and Durability Testing Method The coated substrates of the examples were evaluated for lubricity/durability by friction measurements using a Vertical Pinch Method, as described in International Application Number WO 03/055611 with the following modifications.
- the coated substrate samples were hydrated in phosphate-buffered saline (PBS, pH 7.4) for > 1 minute and then inserted into the end of a rod holder, which was placed between the two jaws of a pinch tester and immersed in a cylinder of PBS.
- the jaws of the pinch tester were closed as the sample was pulled in a vertical direction for 10 cm at a travel rate of 1 cm/sec and opened when the coated sample was returned to the original position.
- Particulate Testing Method Testing of the particulates generated in aqueous solution for the examples herein was performed according to the following procedure. As a derivative of the procedures described in ASTM F2394, substrates were passed through a tortuous path in an aqueous solution described as follows. The distal portion of a 6 French guide catheter (Vista Brite Tip, Cordis) was cut off and discarded so that the catheter was 30 cm long. The guide catheter was inserted into the ASTM F2394-07 model. A hemostasis valve connector (Qosina) was attached to the guide catheter. The model was cleaned by flushing 120 mL Isoton (Becton, Dickinson, and Company) using a 60 mL syringe and discarding the flush.
- Isoton Becton, Dickinson, and Company
- a base line flush with 120mL Isoton was analyzed by light obscuration to determine background level of particulates.
- 90-cm tubes (1 mm diameter) with 20 cm coated were hydrated in Isoton for > 1 minute. The tubes were inserted into the guide catheter and advanced until the distal portion of the rod exited the model.
- a 120 mL flush with Isoton was performed and collected in a glass beaker. The collected Isoton was immediately analyzed by light obscuration for particulates > 10 microns. The tube was removed, and the model was cleaned with 120 ml Isoton and the next coated rod was tested.
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Abstract
Description
Claims
Priority Applications (5)
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MX2018011806A MX2018011806A (en) | 2016-03-31 | 2017-03-30 | Lubricious coating for medical device. |
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EP17716425.8A EP3436096A1 (en) | 2016-03-31 | 2017-03-30 | Lubricious coating for medical device |
CN201780033572.1A CN109195643A (en) | 2016-03-31 | 2017-03-30 | Lubricant coating for medical device |
JP2018550686A JP6947747B2 (en) | 2016-03-31 | 2017-03-30 | Lubricating coating for medical devices |
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Publication number | Priority date | Publication date | Assignee | Title |
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MX339181B (en) | 2010-03-30 | 2016-05-16 | Surmodics Inc | Degradable photo-crosslinker. |
US10315987B2 (en) | 2010-12-13 | 2019-06-11 | Surmodics, Inc. | Photo-crosslinker |
US20220184342A1 (en) * | 2015-07-20 | 2022-06-16 | Roivios Limited | Coated Urinary Catheter or Ureteral Stent and Method |
WO2021033763A1 (en) * | 2019-08-21 | 2021-02-25 | テルモ株式会社 | Medical instrument and method for manufacturing same |
US11359156B2 (en) | 2019-10-21 | 2022-06-14 | Biocoat, Inc. | UV cure basecoatings for medical devices |
WO2021081036A1 (en) * | 2019-10-21 | 2021-04-29 | Biocoat, Inc. | Uv cure coatings for medical devices |
Citations (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4979959A (en) | 1986-10-17 | 1990-12-25 | Bio-Metric Systems, Inc. | Biocompatible coating for solid surfaces |
US5002582A (en) | 1982-09-29 | 1991-03-26 | Bio-Metric Systems, Inc. | Preparation of polymeric surfaces via covalently attaching polymers |
US5263992A (en) | 1986-10-17 | 1993-11-23 | Bio-Metric Systems, Inc. | Biocompatible device with covalently bonded biocompatible agent |
US5414075A (en) | 1992-11-06 | 1995-05-09 | Bsi Corporation | Restrained multifunctional reagent for surface modification |
US5512329A (en) | 1982-09-29 | 1996-04-30 | Bsi Corporation | Substrate surface preparation |
US5714360A (en) | 1995-11-03 | 1998-02-03 | Bsi Corporation | Photoactivatable water soluble cross-linking agents containing an onium group |
US5858653A (en) | 1997-09-30 | 1999-01-12 | Surmodics, Inc. | Reagent and method for attaching target molecules to a surface |
US6156345A (en) | 1998-03-19 | 2000-12-05 | Surmodics, Inc. | Crosslinkable macromers bearing initiator groups |
US6278018B1 (en) | 1999-12-14 | 2001-08-21 | Surmodics, Inc. | Surface coating agents |
WO2003055611A1 (en) | 2001-12-21 | 2003-07-10 | Surmodics, Inc. | Reagent and method for providing coatings on surfaces |
WO2008104573A2 (en) * | 2007-02-28 | 2008-09-04 | Dsm Ip Assets B.V. | Hydrophilic coating |
US7772393B2 (en) | 2005-06-13 | 2010-08-10 | Innovative Surface Technologies, Inc. | Photochemical crosslinkers for polymer coatings and substrate tie-layer |
US20110144373A1 (en) | 2009-12-10 | 2011-06-16 | Surmodics, Inc. | Water-soluble degradable photo-crosslinker |
US20120046384A2 (en) | 2010-03-30 | 2012-02-23 | Surmodics, Inc. | Photoactivatable crosslinker |
US20120149934A1 (en) | 2010-12-13 | 2012-06-14 | Surmodics, Inc. | Photo-crosslinker |
US20130143056A1 (en) | 2011-06-08 | 2013-06-06 | Surmodics, Inc. | Photo-vinyl linking agents |
US20130302529A1 (en) | 2012-05-11 | 2013-11-14 | Surmodics, Inc. | Boron-containing linking agents |
WO2014107670A1 (en) * | 2013-01-04 | 2014-07-10 | Surmodics, Inc. | Low particulate lubricious coating with vinyl pyrrolidone and acidic polymer-containing layers |
US8809411B2 (en) | 2007-02-28 | 2014-08-19 | Dsm Ip Assets B.V. | Hydrophilic coating |
Family Cites Families (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2071279T3 (en) | 1990-10-04 | 1995-06-16 | Schneider Europ Ag | EXPANSION BALL CATHETER. |
JPH0783761B2 (en) * | 1990-10-04 | 1995-09-13 | テルモ株式会社 | Medical equipment |
US5061424A (en) | 1991-01-22 | 1991-10-29 | Becton, Dickinson And Company | Method for applying a lubricious coating to an article |
US5382234A (en) | 1993-04-08 | 1995-01-17 | Scimed Life Systems, Inc. | Over-the-wire balloon catheter |
US5531715A (en) | 1993-05-12 | 1996-07-02 | Target Therapeutics, Inc. | Lubricious catheters |
US5344402A (en) | 1993-06-30 | 1994-09-06 | Cardiovascular Dynamics, Inc. | Low profile perfusion catheter |
AU2359395A (en) | 1994-04-20 | 1995-11-16 | Ronald J. Solar | Active perfusion dilatation catheter |
US5667493A (en) | 1994-12-30 | 1997-09-16 | Janacek; Jaroslav | Dilation catheter |
JPH10110134A (en) * | 1996-10-07 | 1998-04-28 | Toyobo Co Ltd | Coating agent, readily slidable medical device and its production |
US6517515B1 (en) | 1998-03-04 | 2003-02-11 | Scimed Life Systems, Inc. | Catheter having variable size guide wire lumen |
WO1999059667A1 (en) | 1998-05-15 | 1999-11-25 | Medgination, Inc. | Enhanced balloon dilatation system |
US6818018B1 (en) * | 1998-08-14 | 2004-11-16 | Incept Llc | In situ polymerizable hydrogels |
JP4834916B2 (en) * | 2000-05-10 | 2011-12-14 | 東レ株式会社 | Surface-treated plastic molded product |
US6428839B1 (en) * | 2000-06-02 | 2002-08-06 | Bausch & Lomb Incorporated | Surface treatment of medical device |
US6623504B2 (en) | 2000-12-08 | 2003-09-23 | Scimed Life Systems, Inc. | Balloon catheter with radiopaque distal tip |
EP2061526B1 (en) | 2006-09-13 | 2015-07-29 | DSM IP Assets B.V. | Coated medical device |
US20080213334A1 (en) | 2006-09-29 | 2008-09-04 | Lockwood Nathan A | Polyelectrolyte media for bioactive agent delivery |
US20120077049A1 (en) | 2007-08-06 | 2012-03-29 | Abbott Cardiovascular Systems, Inc. | Medical devices having a lubricious coating with a hydrophilic compound in an interlocking network |
US20090123519A1 (en) * | 2007-11-12 | 2009-05-14 | Surmodics, Inc. | Swellable hydrogel matrix and methods |
DK2252661T3 (en) | 2008-03-12 | 2017-01-16 | Dsm Ip Assets Bv | HYDROPHIL COATING |
WO2012112624A2 (en) | 2011-02-15 | 2012-08-23 | Svaya Nanotechnologies, Inc. | Methods and materials for functional polyionic species and deposition thereof |
US9321030B2 (en) | 2012-01-04 | 2016-04-26 | The Trustees Of The Stevens Institute Of Technology | Clay-containing thin films as carriers of absorbed molecules |
EP2804915B1 (en) * | 2012-01-18 | 2016-03-30 | SurModics, Inc. | Lubricious medical device coating with low particulates |
EP2623215B1 (en) | 2012-02-01 | 2014-03-26 | Bioenergy Capital AG | Hydrophilic plasma coating |
JP5763565B2 (en) | 2012-02-02 | 2015-08-12 | 住友ゴム工業株式会社 | Surface modification method and surface modified elastic body |
US8956682B2 (en) * | 2012-04-02 | 2015-02-17 | Surmodics, Inc. | Hydrophilic polymeric coatings for medical articles with visualization moiety |
WO2013166358A1 (en) | 2012-05-03 | 2013-11-07 | Indiana University Research And Technology Corporation | Surface coatings for biological implants and prostheses |
MX351261B (en) | 2012-06-01 | 2017-10-06 | Surmodics Inc | Apparatus and method for coating balloon catheters. |
US9629945B2 (en) * | 2012-12-12 | 2017-04-25 | Surmodics, Inc. | Stilbene-based reactive compounds, polymeric matrices formed therefrom, and articles visualizable by fluorescence |
WO2015029625A1 (en) * | 2013-09-02 | 2015-03-05 | テルモ株式会社 | Medical instrument and method for manufacturing same |
-
2017
- 2017-03-30 JP JP2018550686A patent/JP6947747B2/en active Active
- 2017-03-30 MX MX2018011806A patent/MX2018011806A/en unknown
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Patent Citations (29)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5002582A (en) | 1982-09-29 | 1991-03-26 | Bio-Metric Systems, Inc. | Preparation of polymeric surfaces via covalently attaching polymers |
US5512329A (en) | 1982-09-29 | 1996-04-30 | Bsi Corporation | Substrate surface preparation |
US4979959A (en) | 1986-10-17 | 1990-12-25 | Bio-Metric Systems, Inc. | Biocompatible coating for solid surfaces |
US5263992A (en) | 1986-10-17 | 1993-11-23 | Bio-Metric Systems, Inc. | Biocompatible device with covalently bonded biocompatible agent |
US5414075A (en) | 1992-11-06 | 1995-05-09 | Bsi Corporation | Restrained multifunctional reagent for surface modification |
US5637460A (en) | 1992-11-06 | 1997-06-10 | Bsi Corporation | Restrained multifunctional reagent for surface modification |
US5714360A (en) | 1995-11-03 | 1998-02-03 | Bsi Corporation | Photoactivatable water soluble cross-linking agents containing an onium group |
US6077698A (en) | 1995-11-03 | 2000-06-20 | Surmodics, Inc. | Photoactivatable cross-linking agents containing charged groups for water solubility |
US5858653A (en) | 1997-09-30 | 1999-01-12 | Surmodics, Inc. | Reagent and method for attaching target molecules to a surface |
US6156345A (en) | 1998-03-19 | 2000-12-05 | Surmodics, Inc. | Crosslinkable macromers bearing initiator groups |
US6278018B1 (en) | 1999-12-14 | 2001-08-21 | Surmodics, Inc. | Surface coating agents |
US7138541B2 (en) | 1999-12-14 | 2006-11-21 | Surmodics, Inc. | Surface coating agents |
US6603040B1 (en) | 1999-12-14 | 2003-08-05 | Surmodics, Inc. | Surface coating agents |
US7348055B2 (en) | 2001-12-21 | 2008-03-25 | Surmodics, Inc. | Reagent and method for providing coatings on surfaces |
WO2003055611A1 (en) | 2001-12-21 | 2003-07-10 | Surmodics, Inc. | Reagent and method for providing coatings on surfaces |
US8487137B2 (en) | 2005-06-13 | 2013-07-16 | Innovative Surface Technologies, Llc | Photochemical crosslinkers for polymer coatings and substrate tie-layer |
US7772393B2 (en) | 2005-06-13 | 2010-08-10 | Innovative Surface Technologies, Inc. | Photochemical crosslinkers for polymer coatings and substrate tie-layer |
US20100274012A1 (en) | 2005-06-13 | 2010-10-28 | Innovative Surface Technologies, Inc. | Photochemical Crosslinkers for Polymer Coatings and Substrate Tie-Layer |
US8809411B2 (en) | 2007-02-28 | 2014-08-19 | Dsm Ip Assets B.V. | Hydrophilic coating |
US20100198168A1 (en) | 2007-02-28 | 2010-08-05 | Dsm Ip Assets B.V. | Hydrophilic coating |
WO2008104573A2 (en) * | 2007-02-28 | 2008-09-04 | Dsm Ip Assets B.V. | Hydrophilic coating |
US8513320B2 (en) | 2007-02-28 | 2013-08-20 | Dsm Ip Assets B.V. | Hydrophilic coating |
US20110144373A1 (en) | 2009-12-10 | 2011-06-16 | Surmodics, Inc. | Water-soluble degradable photo-crosslinker |
US20120046384A2 (en) | 2010-03-30 | 2012-02-23 | Surmodics, Inc. | Photoactivatable crosslinker |
US8889760B2 (en) | 2010-03-30 | 2014-11-18 | Surmodics, Inc. | Photoactivatable crosslinker |
US20120149934A1 (en) | 2010-12-13 | 2012-06-14 | Surmodics, Inc. | Photo-crosslinker |
US20130143056A1 (en) | 2011-06-08 | 2013-06-06 | Surmodics, Inc. | Photo-vinyl linking agents |
US20130302529A1 (en) | 2012-05-11 | 2013-11-14 | Surmodics, Inc. | Boron-containing linking agents |
WO2014107670A1 (en) * | 2013-01-04 | 2014-07-10 | Surmodics, Inc. | Low particulate lubricious coating with vinyl pyrrolidone and acidic polymer-containing layers |
Also Published As
Publication number | Publication date |
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JP7224409B2 (en) | 2023-02-17 |
CN109195643A (en) | 2019-01-11 |
CA3018188A1 (en) | 2017-10-05 |
MX2018011806A (en) | 2019-02-07 |
JP2019509843A (en) | 2019-04-11 |
EP3436096A1 (en) | 2019-02-06 |
US11278647B2 (en) | 2022-03-22 |
US20170281831A1 (en) | 2017-10-05 |
JP2021192838A (en) | 2021-12-23 |
JP6947747B2 (en) | 2021-10-13 |
US20220211917A1 (en) | 2022-07-07 |
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