CA2212181A1 - Medical apparatus with scratch-resistant coating and method making same - Google Patents
Medical apparatus with scratch-resistant coating and method making sameInfo
- Publication number
- CA2212181A1 CA2212181A1 CA002212181A CA2212181A CA2212181A1 CA 2212181 A1 CA2212181 A1 CA 2212181A1 CA 002212181 A CA002212181 A CA 002212181A CA 2212181 A CA2212181 A CA 2212181A CA 2212181 A1 CA2212181 A1 CA 2212181A1
- Authority
- CA
- Canada
- Prior art keywords
- medical apparatus
- providing
- coating
- accordance
- reinforcing agent
- 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
Links
Classifications
-
- 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
- A61L29/12—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
- A61L29/126—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having a macromolecular matrix
-
- 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
-
- 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
- A61L29/16—Biologically active materials, e.g. therapeutic substances
-
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
-
- 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
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/60—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a special physical form
- A61L2300/606—Coatings
Abstract
A method for providing a medical apparatus with a protective surface coating is described. The method comprises applying to a medical apparatus a coating solution that contains a matrix polymer such as a urethane, and a reinforcing agent such as lamellar platelet and fiber additives, as micaceous pigments, flake pigments, tungsten powder and glass fiber, to increase the resistance of the medical apparatus to injury, such that the surface coating forms a protective, scratch- and puncture-resistant layer on the medical apparatus. The particles or fibers of the reinforcing agent may be oriented to provide the medical apparatus with additional resistance to injury. The coating is well suited to provide balloon catheters, particularly PET balloons, and the like with the toughness desirable for use in stent delivery and placement.
Description
-CA 02212181 1997-08-0~
W 096124393 PCT~DS96101624 MEDICAL APPARATUS WITH SCRATCH-RESISTANT COATING
AND M[ETHOD MAKING SAME
Background of the Invention As medical science delves into smaller areas of the body, such as blood vessels, it has become increasingly difficult to reach these areas with an effective convell~;onal apparatus. In part, this is due to the materials from which the apparatus is made, and the dangers to the apparatus due to the method of introduction into the body and in particular, the small areas of the body.
Particularly, ~theters having infl~t~hle balloon att~rhm~ntc have been used for re~hing these small and related areas, such as in coronary angioplasty. More particularly, stent deliver,v and pl~cem~nt devices useful for opening ocrlllclec~ or blocked vessels have been used in coronary and peripheral angioplasty, urology and reproductive surgeries, among others.
~,alloon catheters are produced from materials that can sustain large amounts of pressure. However, the profile of balloon r~theters and related devices must be small in order to be introduced into the small areas of the bodies, such as blood vessels. Therefore, materials with high strength relative to film thirkn~ss are chosen. An example of these materials is PET (poly-ethylene terephth~l~te), which is useful for providing a non-compliant, high-pressure device for delivering a stent to a vessel. Unfortunately, PET and other materials with high strength to film thirkness ratios tend to be scratch and puncture sensitive. Polymers that tend to be less sensitive to scratches, such as polyethylene, nylon, and urethane are compliant, and at the same film thickness as the non-compliant PET, do not provide the strength required to withstand the pressure used for delivering a stent into a vessel wall. ]!~on-compliance, or the ability not to expand beyond a predetermined size on pressure and to m~int~in subst~nti~lly a profile, is a desired characteristic for balloon catheters, particularly for use in small vessels, so as not to rupture or dissect the vessel as the balloon expands. A layer added on the substrate may provide some protective characteristics to a m~-lir~l apparatus by virtue of the added thirkness, and rnany resins may be used for this purpose. However, such a physical barrier, provides only limited protection.
CA 02212181 1997-08-0~
W 096/24393 PCT~US96/01624 Further ~iffiçl~lti~c often arise in guiding a c~rheter into a desired location in a patient due to the friction between the apparatus and the vessel through which the apparatus passes. The result of this friction is failure of the balloon due to abrasion and puncture during handling and use and also from over-inflation. There 5 has been attention in the field to providing lubricous coatings to the medicalapparatus to riiminich friction that causes apparatus failure. One such lubricous coating for balloon catheters is described in U.S. Patent No. 5,272,012 to Opolski, wherein the use of a slip additive such as a siloxane is disclosed. These coatings improve the success rates of balloon catheters by altering the friction coefficient by 10 use of lubricous coatings. However, they do not address the scratch and puncture-resict~nce of the apparatus other than by building film thirknecs, which is inadequate protection against destruction of the balloon by tears, scratches, punctures and the like, particularly for the delivery of stPnting devices.
Sul,llllal.y of the Invention The present invention relates to a medical apparatus having and a method for providing a medical apparatus with a protective surface coating com~ining a matrix polymer and a reinforcing agent to decrease the sensitivity of the m~
apparatus to injuries, such as scratches, punctures, and the like. The reinforcing agent may be oriented in the coating to provide ~nh~n~e~l injury r~cict~nce- Thesurface coating forms a protective layer on the medical apparatus to provide resistance to scratches, punctures and the like, and is well suited to an apparatus that is required to withct~nci pressure and m~int~in a small profile.
Detailed Description of the Invention As used herein, the term "medical apparatus" means apparatus suited for use in medical applications, particularly in in vzvo applications. Such apparatus spe~ific~lly includes, but is not limited to, balloons, catheters, guidewires, stylets and introducers. Of particular note for use with the invention are catheters having infl~t~hle balloons such as those developed for use in angioplasty and valvuloplasty, urology, gynecology, neurology and the like.
CA 02212181 1997-08-0~
W 096l24393 PCT~US90~1~24 As used herein, the term "reinforcing agent" means a substance capable, when in a coating, of increasing the hardness of the surface of a m~lic~l apparatus and allowing a fracture plane within the coating without loss of coating from the substrate. Preferably, the reinforcing agent has a higher surface hardness than the 5 surface hardness of the medical apparatus. Preferred reinforcing agents include mt ll~r platelet and fiber additives, such as micaceous pigm~ntc, flake pigm~ntc, and glass. Glass fibers may be obtained pretreated with silane, such as 737BC, available from Owens-Corning, Toledo, OH.
As used herein) the term "matrix polymer" means a polymer capable of 10 forming a coating on the surface of a medical apparatus and providing a network for conrlining a reinforcing agent such as a solvent, water, W curing or 100%
solids polymer. The rrlatrix polymer preferably has functional moieties capable of crosslinking to other m~oieties within the matrix polymer and with moieties derived from the medical apparatus to Pnh~nce the strength, adhesion and toughness of the 15 coating. Examples of matrix polymers include resin systems such as urethane, acrylics, and epoxies or others selectecl for non-substrate attack and curing temperature properties. Water-based urethanes are particularly desirable due to their protective qualities allowing crosslinking within the urethane itself and binding with carboxyl groups present on the surface of the medical apparatus or derived at 20 the surface with pretre~tments or primers.
The language "moieties derived from the m~orlir~l apparatus" is intended to include functional moieties from the material of which the m~ic~l apparatus is made, rnoieties from a primer layer disposed between the coating and the medicalapparatus or moieties generated or formed by subjecting the primer layer to a 25 pl~Llc:~LJ~llent step, e.g., plasma or corona discharge.
In the case of most water-based coatings, e.g. urethane based, bonding of the coating to the substrate surface upon which it is applied can be achieved by use of an optional crosclinking agent, such that there is reaction between carboxyl functional groups present in the coating, e.g., urethane, and carboxyl functional 30 groups present on the substrate surface. One method by which such bonding canbe achieved involves a crosslinking reaction using polyfunctional aziridine through CA 02212181 1997-08-0~
W 096/24393 PCTrUS96101624 which the linkage will occur. Crosclinking agents are added optionally to provide improved hardness, adhesion and chemical and water resistance.
As used herein, the term "crosslinking agent" is inten~l.orl to include agents capable of enh~nfing the molecular weight of the matrix polymer. The crosslinking 5 agent further may enhance the adhesion of the coating to the medical apparatus.
For example, functional moieties of the matrix polymer may be crosslinke~ to thefunction moieties derived from the medical apparatus. The functional moieties are intended to include groups capable of binding to one another. The matrix polymermay be selectecl for such functional moieties. Examples of crosclinking agents useful 10 within this invention are aziridine, carbodiimides, urea formaldehyde and m~l~min~
form~ f hyde con~lenc~tes, apoxies, isocyanates, tit~n~tes, zircoalllmin~t~s, zinc crosslink~rs, and silanes. One skilled in the art would be able to select the crosslinking agent based upon the functional moieties desired to be crosslinke~ and the substrate temperature limit~tions.
As used herein, the term "primer layer" is intf-ncle~l to include a layer capable of providing the desired adhesion to substrate and/or functional moieties for crosclinking to the matrix polymer or reinforcing agent. The primer layer is disposed between the medical apparatus and the matrix polymer. A material that is useful and desirable for m~king m~ l apparatus may not possess adhesion or 20 functional moieties capable of crosclinking sufficiently with a desired matrix polymer or reinforcing agent. In this situation, the desired adhesion or functional moieties can be provided to the surface of the medial apparatus by coating the apparatus with a primer layer. An example of such a layer is a dispersion of ethylene acrylic acid (EAA), such as Primacor 5980 available from Dow-Corning 25 Corporation (Midland, l\/~ichig~n)~ or MICHEMPRIME 4983R available from ~ichelm~n (cincinn~tti~ OH), or which is capable of providing carboxyl moieties to the surface.
As an alternative to the use of a primer, a surface functionality can be obtained using a plasma or corona discharge or by exposing the surface to a flame.
30 In the case of plasma or corona discharge, the functionality obtained on the surface can be tailored through the use of process atmosphere variation. Thus when an oxygen-derived functionality (i.e. -OH or-COOH~ is desired, the surface can be W 096/24393 rCTAUS9G~0~62 plasma treated in an oxygen-cont~ining atmosphere. Alternatively, if an amine functionality is preferred, the treating process can be carried out in a nitrogen contlining atmosphere.
As used herein t;he term "coating solution" is intencle~1 to include a solution cont~ini1~g both the matrix polymer and the reinforcing agent capable of being J coated on a surface of a m~lic~l apparatus. The coating solution also may include other materials that do not detriment~lly effect the protective compouncl and reinforcing agent netwa,rk. These materials include radiopacifiers, anti-slip additives, anti-mar additives, therapeutic agents, and ~ntimicrobial agents. The term therapeutic agent for purposes of this invention is intçnc~ec~ to include substances capable of providing a therapeutic effect in the environment of use of the medical apparatus. The therapeutic agents may be anti-infl~mm~tory agents, antibiotics, immlln~-suppressible stim~ tory agents, anti-thrombolytic agents, growth factors, agents that locally effect blood pressure, agents that promote cell survival andhe~ling, and the like. ~ntimicrobial agents are agents capable of suppressing the gr~ffEh c;r ~ ity of .~icrocirganisrll allo w-ing thelll to colllba~ infec;Lions. ~xamples of classes of antimicrobial agents include antibiotics, iodine solutions, mercurials nitroimi~l~701es, bisg~l~nic~escilier, phenolics, ammonium salts, silver compounds and the like. Specific examples of agents within classes include metronidazole and chlorhç~i~inç. One of ordinar,v skill in the art would be able to select agents capable of ~ttaining a desired function or result.
The surface of the apparatus may be prepared for application of the coating solution by pr~l~~ rlt as needed for adhesion. Such preparation includes corona,plasma, flame and primer pr~ nts The coating can be applied to a substrate using any of a variety of methods.
Preferred arnong these are dipping, spraying, flowing, rolling and brushing.
Orienting the particles or fibers of the reinforcing agent in the coating solution as it is app]ied to the m~l~ic~l apparatus is desired. Orientation of the particles or fibers of the reinforcing agent so as to be aligned in a direction perpçnciic~ r to the direction of likely injury, and may be accomplished by application shear, incl~l~ling dip pull-out, direction rotation through solution, flow and spin orientation, surface tension and evaporati~- effects. A low solids coating may be dipped more than CA 02212181 1997-08-0~
W O 96/24393 PCTrUS96/01624 once and may be most uniform for thickness, especially if oriented to allow sag to one end on one dip, and to a different orientation on a second clip. Possibilities exist for orienting by rotating through the coating on the axis of the apparatus and then drying in this configuration. Agitation may be needed during application tom~int~in adequate consistency and inhibit ckinning at the surfaces. Such agitation will be required in accordance with manufacturer's instructions in connection with the raw materials used, and may be based on the stability to shear of the reinforcing agent.
Film thickness of the coating is preferably in the range of about 0.1 to about 3 mils, and most preferred in the range of about 0.5 to about 2 mils. Adjustments to the viscosity and solids of the coating solution will accomplish the desired thickness and will be apparent to one of ordinary skill in the art. In the embodiment cont~ining micaceous pigment as the reinforcing agent, the micaceous pigment concentration should be increased with decreasing thic:kness of film to allow increased scratch and puncture resict~nfe The concen-l~Lion of the reinforcing agent may be in the range of from about 1% to abou~ 95% by weight of solids. The preferred concentration of reinforcing agent is in the range of about 10% to about 50% by weight of solids. However, too great a concellLl~Lion may degrade polymer properties and begin to affect performance.
The curing may be carried out by first holding the coated apparatus at ambient temperature to allow equilibration and foam to break. Air drying is possible for ambient cure systems, and can be accelerated by heat cure at elevated temperature. Certain crosslinking agents may need a certain time at an elevated temperature to allow cure and this may be accomplished by placing the coated apparatus in an oven, e.g. at appro~im~tely 50O for a PET substrate, until the matrix polymer is fully dried. The temperature selected for the curing step may depend on the temperature limit~tions of the substrate and the reactivity of thecrosslinking agent.
The resulting coating provides resict~nce to scratches, punctures and the like, thereby decreasing the sensitivity of the medical apparatus to injury. This decreased sensitivity is the result of the matrix polymer and the reinforcing agent in thecoating solution. The coating solution com~ining a matrix polymer and a CA 02212181 1997-OX-0~
W O 96/24393 PCTnUS96J01624 reinforcing agent provides the coating or the present invention with resict~nce to scratches, punctures and the like that is enh~ncecl over that which is provided by the matrix polymer alone. A reinforcing agent with a surface hardness that is y higher than that of the surface hardness of the apparatus is preferred. Orientation of the fibers of the reiniorcing agent so as to be aligned in a direction perpen~ r to the direction of inse~tion into the body and small areas of the body is preferred.
Micaceous or flake pi~rn~nts used as the reinforcing agent may be oriented parallel to the surface of the device.
A coating solultion prepared in accordance with the te~hing.c of this inventio]l and having tl~e following formulation is provided:
Component Supplier/Design~tionWeight (%) Urethane R9621/Zeneca Resins 82.2 Micaceous pigment 110 Silver Pearl/ 6.5 EM Industries Crosslinking Agent CX100/Zeneca Resins 3.7 Acetone ~ 3.7 Water -- 3.7 The coating solution is prepared by prewetting and dispersing the mic~ceous pigment (3.5g) (110 Silver Pearl obtained from EM Industries, Hawthorne, NY~ into a solution of distilled water (2g) and acetone (2g) to reduce the tendency to foam.
The urethane dispersion (44g) (R9621 obtained from Zeneca Resins, Wilmington, 25 MA) was added with agitation provided by a magnetic stirrer. Finally, the crosclinking agent (2g) (CX100 obtained from Zeneca Resins) was added dropwise and allowed to stir for 30 minutes prior to application.
A PET balloon had been plasma treated (300W, 0.25 Torr oxygen for 5 min~ltes) and dipped into a 15% solids emulsion of primer (MICHEMPRIME 4983R
CA 02212181 1997-08-0~
W 096/24393 PCTrUS96/01624 obtained from Michelm~n, Cin~inn~ti, OH), and the then dried for 5 mimlteS at 46~C before the coating solution was applied. The coating solution was applied by dip, then cured and dried for 1 hour at 46~C.
A coating solution prepared in accordance with the teachingc of this invention and having the following formulation is provided:
Component Supplier/Design~tiQn Weight (%) Urethane R972 (Zeneca Resins) 50 Glass fiber 737BC (Owens-Corning) 5.1 Crosclinking agent CX100/Zeneca Resins 2 Water -- 42.9 The urethane dispersion, glass fiber (737BC obtained from Owens-Corning, Toledo, OH~ and water were mixed with agitation provided by a rn~gn~tic stirrer.25 The crosslinking agent was added dropwise and allowed to stir for 30 minutes prior to application.
The coating solution was applied to a PET balloon that had been corona treated achieved by rotating the balloon for 1 minute within 1/2" of corona generated by a Model BD-20 with a 3" electrode, BD-20 supplied by Electro-30 Technics, Chicago, IL) and dipped into a 15% solids emulsion of primer (Primacor5980, Dow Chemical, Mi~l~n~, Michigan), and dried for 5 minutes at 46~C. The coating solution was applied by flow coating, then cured and dried for 1 hour at46~C.
CA 02212181 1997-08-0~
WO 96124393 PCT/~7S96~01G24 A coating sohltion prepared in accordance with the teac hings of this invention and having the following formula~ion is provided:
Compoment Supplier/D~sign~tion Weight (%) Urethane R9621/Zeneca Resins 6.8 Water 67.9 Tllngcten Powder M10/GTE Osram Z3.2 Thickening Agent ASE-60 Acr,vsol/Rohm & Haas 2.0 The coating solution was prepared by combining the urethane and water.
20 The thickener may be added dropwise with agitation and the solution pH adjusted to 9 with ammonium hydroxide to allow the viscosity to increase. The tllngcten powder was added and stirred into the thickened solution.
A PET balloon prepared with a corona tre~tm~nt (as in Example 2) and primer clipped (MICHl_MPRIME 4983 as in Example 1) was flow coated with the 25 tllng~cten reinforced coating solution and dried for 1 hour at 46~C.
C'oated and uncoated balloons were scratch tested with the results that the testing of uncoated balloons resulted in complete destruction of the balloon, whereas the coated balloons resisted the injury, resulting in only discrete damage to the effected area.
W 096124393 PCT~DS96101624 MEDICAL APPARATUS WITH SCRATCH-RESISTANT COATING
AND M[ETHOD MAKING SAME
Background of the Invention As medical science delves into smaller areas of the body, such as blood vessels, it has become increasingly difficult to reach these areas with an effective convell~;onal apparatus. In part, this is due to the materials from which the apparatus is made, and the dangers to the apparatus due to the method of introduction into the body and in particular, the small areas of the body.
Particularly, ~theters having infl~t~hle balloon att~rhm~ntc have been used for re~hing these small and related areas, such as in coronary angioplasty. More particularly, stent deliver,v and pl~cem~nt devices useful for opening ocrlllclec~ or blocked vessels have been used in coronary and peripheral angioplasty, urology and reproductive surgeries, among others.
~,alloon catheters are produced from materials that can sustain large amounts of pressure. However, the profile of balloon r~theters and related devices must be small in order to be introduced into the small areas of the bodies, such as blood vessels. Therefore, materials with high strength relative to film thirkn~ss are chosen. An example of these materials is PET (poly-ethylene terephth~l~te), which is useful for providing a non-compliant, high-pressure device for delivering a stent to a vessel. Unfortunately, PET and other materials with high strength to film thirkness ratios tend to be scratch and puncture sensitive. Polymers that tend to be less sensitive to scratches, such as polyethylene, nylon, and urethane are compliant, and at the same film thickness as the non-compliant PET, do not provide the strength required to withstand the pressure used for delivering a stent into a vessel wall. ]!~on-compliance, or the ability not to expand beyond a predetermined size on pressure and to m~int~in subst~nti~lly a profile, is a desired characteristic for balloon catheters, particularly for use in small vessels, so as not to rupture or dissect the vessel as the balloon expands. A layer added on the substrate may provide some protective characteristics to a m~-lir~l apparatus by virtue of the added thirkness, and rnany resins may be used for this purpose. However, such a physical barrier, provides only limited protection.
CA 02212181 1997-08-0~
W 096/24393 PCT~US96/01624 Further ~iffiçl~lti~c often arise in guiding a c~rheter into a desired location in a patient due to the friction between the apparatus and the vessel through which the apparatus passes. The result of this friction is failure of the balloon due to abrasion and puncture during handling and use and also from over-inflation. There 5 has been attention in the field to providing lubricous coatings to the medicalapparatus to riiminich friction that causes apparatus failure. One such lubricous coating for balloon catheters is described in U.S. Patent No. 5,272,012 to Opolski, wherein the use of a slip additive such as a siloxane is disclosed. These coatings improve the success rates of balloon catheters by altering the friction coefficient by 10 use of lubricous coatings. However, they do not address the scratch and puncture-resict~nce of the apparatus other than by building film thirknecs, which is inadequate protection against destruction of the balloon by tears, scratches, punctures and the like, particularly for the delivery of stPnting devices.
Sul,llllal.y of the Invention The present invention relates to a medical apparatus having and a method for providing a medical apparatus with a protective surface coating com~ining a matrix polymer and a reinforcing agent to decrease the sensitivity of the m~
apparatus to injuries, such as scratches, punctures, and the like. The reinforcing agent may be oriented in the coating to provide ~nh~n~e~l injury r~cict~nce- Thesurface coating forms a protective layer on the medical apparatus to provide resistance to scratches, punctures and the like, and is well suited to an apparatus that is required to withct~nci pressure and m~int~in a small profile.
Detailed Description of the Invention As used herein, the term "medical apparatus" means apparatus suited for use in medical applications, particularly in in vzvo applications. Such apparatus spe~ific~lly includes, but is not limited to, balloons, catheters, guidewires, stylets and introducers. Of particular note for use with the invention are catheters having infl~t~hle balloons such as those developed for use in angioplasty and valvuloplasty, urology, gynecology, neurology and the like.
CA 02212181 1997-08-0~
W 096l24393 PCT~US90~1~24 As used herein, the term "reinforcing agent" means a substance capable, when in a coating, of increasing the hardness of the surface of a m~lic~l apparatus and allowing a fracture plane within the coating without loss of coating from the substrate. Preferably, the reinforcing agent has a higher surface hardness than the 5 surface hardness of the medical apparatus. Preferred reinforcing agents include mt ll~r platelet and fiber additives, such as micaceous pigm~ntc, flake pigm~ntc, and glass. Glass fibers may be obtained pretreated with silane, such as 737BC, available from Owens-Corning, Toledo, OH.
As used herein) the term "matrix polymer" means a polymer capable of 10 forming a coating on the surface of a medical apparatus and providing a network for conrlining a reinforcing agent such as a solvent, water, W curing or 100%
solids polymer. The rrlatrix polymer preferably has functional moieties capable of crosslinking to other m~oieties within the matrix polymer and with moieties derived from the medical apparatus to Pnh~nce the strength, adhesion and toughness of the 15 coating. Examples of matrix polymers include resin systems such as urethane, acrylics, and epoxies or others selectecl for non-substrate attack and curing temperature properties. Water-based urethanes are particularly desirable due to their protective qualities allowing crosslinking within the urethane itself and binding with carboxyl groups present on the surface of the medical apparatus or derived at 20 the surface with pretre~tments or primers.
The language "moieties derived from the m~orlir~l apparatus" is intended to include functional moieties from the material of which the m~ic~l apparatus is made, rnoieties from a primer layer disposed between the coating and the medicalapparatus or moieties generated or formed by subjecting the primer layer to a 25 pl~Llc:~LJ~llent step, e.g., plasma or corona discharge.
In the case of most water-based coatings, e.g. urethane based, bonding of the coating to the substrate surface upon which it is applied can be achieved by use of an optional crosclinking agent, such that there is reaction between carboxyl functional groups present in the coating, e.g., urethane, and carboxyl functional 30 groups present on the substrate surface. One method by which such bonding canbe achieved involves a crosslinking reaction using polyfunctional aziridine through CA 02212181 1997-08-0~
W 096/24393 PCTrUS96101624 which the linkage will occur. Crosclinking agents are added optionally to provide improved hardness, adhesion and chemical and water resistance.
As used herein, the term "crosslinking agent" is inten~l.orl to include agents capable of enh~nfing the molecular weight of the matrix polymer. The crosslinking 5 agent further may enhance the adhesion of the coating to the medical apparatus.
For example, functional moieties of the matrix polymer may be crosslinke~ to thefunction moieties derived from the medical apparatus. The functional moieties are intended to include groups capable of binding to one another. The matrix polymermay be selectecl for such functional moieties. Examples of crosclinking agents useful 10 within this invention are aziridine, carbodiimides, urea formaldehyde and m~l~min~
form~ f hyde con~lenc~tes, apoxies, isocyanates, tit~n~tes, zircoalllmin~t~s, zinc crosslink~rs, and silanes. One skilled in the art would be able to select the crosslinking agent based upon the functional moieties desired to be crosslinke~ and the substrate temperature limit~tions.
As used herein, the term "primer layer" is intf-ncle~l to include a layer capable of providing the desired adhesion to substrate and/or functional moieties for crosclinking to the matrix polymer or reinforcing agent. The primer layer is disposed between the medical apparatus and the matrix polymer. A material that is useful and desirable for m~king m~ l apparatus may not possess adhesion or 20 functional moieties capable of crosclinking sufficiently with a desired matrix polymer or reinforcing agent. In this situation, the desired adhesion or functional moieties can be provided to the surface of the medial apparatus by coating the apparatus with a primer layer. An example of such a layer is a dispersion of ethylene acrylic acid (EAA), such as Primacor 5980 available from Dow-Corning 25 Corporation (Midland, l\/~ichig~n)~ or MICHEMPRIME 4983R available from ~ichelm~n (cincinn~tti~ OH), or which is capable of providing carboxyl moieties to the surface.
As an alternative to the use of a primer, a surface functionality can be obtained using a plasma or corona discharge or by exposing the surface to a flame.
30 In the case of plasma or corona discharge, the functionality obtained on the surface can be tailored through the use of process atmosphere variation. Thus when an oxygen-derived functionality (i.e. -OH or-COOH~ is desired, the surface can be W 096/24393 rCTAUS9G~0~62 plasma treated in an oxygen-cont~ining atmosphere. Alternatively, if an amine functionality is preferred, the treating process can be carried out in a nitrogen contlining atmosphere.
As used herein t;he term "coating solution" is intencle~1 to include a solution cont~ini1~g both the matrix polymer and the reinforcing agent capable of being J coated on a surface of a m~lic~l apparatus. The coating solution also may include other materials that do not detriment~lly effect the protective compouncl and reinforcing agent netwa,rk. These materials include radiopacifiers, anti-slip additives, anti-mar additives, therapeutic agents, and ~ntimicrobial agents. The term therapeutic agent for purposes of this invention is intçnc~ec~ to include substances capable of providing a therapeutic effect in the environment of use of the medical apparatus. The therapeutic agents may be anti-infl~mm~tory agents, antibiotics, immlln~-suppressible stim~ tory agents, anti-thrombolytic agents, growth factors, agents that locally effect blood pressure, agents that promote cell survival andhe~ling, and the like. ~ntimicrobial agents are agents capable of suppressing the gr~ffEh c;r ~ ity of .~icrocirganisrll allo w-ing thelll to colllba~ infec;Lions. ~xamples of classes of antimicrobial agents include antibiotics, iodine solutions, mercurials nitroimi~l~701es, bisg~l~nic~escilier, phenolics, ammonium salts, silver compounds and the like. Specific examples of agents within classes include metronidazole and chlorhç~i~inç. One of ordinar,v skill in the art would be able to select agents capable of ~ttaining a desired function or result.
The surface of the apparatus may be prepared for application of the coating solution by pr~l~~ rlt as needed for adhesion. Such preparation includes corona,plasma, flame and primer pr~ nts The coating can be applied to a substrate using any of a variety of methods.
Preferred arnong these are dipping, spraying, flowing, rolling and brushing.
Orienting the particles or fibers of the reinforcing agent in the coating solution as it is app]ied to the m~l~ic~l apparatus is desired. Orientation of the particles or fibers of the reinforcing agent so as to be aligned in a direction perpçnciic~ r to the direction of likely injury, and may be accomplished by application shear, incl~l~ling dip pull-out, direction rotation through solution, flow and spin orientation, surface tension and evaporati~- effects. A low solids coating may be dipped more than CA 02212181 1997-08-0~
W O 96/24393 PCTrUS96/01624 once and may be most uniform for thickness, especially if oriented to allow sag to one end on one dip, and to a different orientation on a second clip. Possibilities exist for orienting by rotating through the coating on the axis of the apparatus and then drying in this configuration. Agitation may be needed during application tom~int~in adequate consistency and inhibit ckinning at the surfaces. Such agitation will be required in accordance with manufacturer's instructions in connection with the raw materials used, and may be based on the stability to shear of the reinforcing agent.
Film thickness of the coating is preferably in the range of about 0.1 to about 3 mils, and most preferred in the range of about 0.5 to about 2 mils. Adjustments to the viscosity and solids of the coating solution will accomplish the desired thickness and will be apparent to one of ordinary skill in the art. In the embodiment cont~ining micaceous pigment as the reinforcing agent, the micaceous pigment concentration should be increased with decreasing thic:kness of film to allow increased scratch and puncture resict~nfe The concen-l~Lion of the reinforcing agent may be in the range of from about 1% to abou~ 95% by weight of solids. The preferred concentration of reinforcing agent is in the range of about 10% to about 50% by weight of solids. However, too great a concellLl~Lion may degrade polymer properties and begin to affect performance.
The curing may be carried out by first holding the coated apparatus at ambient temperature to allow equilibration and foam to break. Air drying is possible for ambient cure systems, and can be accelerated by heat cure at elevated temperature. Certain crosslinking agents may need a certain time at an elevated temperature to allow cure and this may be accomplished by placing the coated apparatus in an oven, e.g. at appro~im~tely 50O for a PET substrate, until the matrix polymer is fully dried. The temperature selected for the curing step may depend on the temperature limit~tions of the substrate and the reactivity of thecrosslinking agent.
The resulting coating provides resict~nce to scratches, punctures and the like, thereby decreasing the sensitivity of the medical apparatus to injury. This decreased sensitivity is the result of the matrix polymer and the reinforcing agent in thecoating solution. The coating solution com~ining a matrix polymer and a CA 02212181 1997-OX-0~
W O 96/24393 PCTnUS96J01624 reinforcing agent provides the coating or the present invention with resict~nce to scratches, punctures and the like that is enh~ncecl over that which is provided by the matrix polymer alone. A reinforcing agent with a surface hardness that is y higher than that of the surface hardness of the apparatus is preferred. Orientation of the fibers of the reiniorcing agent so as to be aligned in a direction perpen~ r to the direction of inse~tion into the body and small areas of the body is preferred.
Micaceous or flake pi~rn~nts used as the reinforcing agent may be oriented parallel to the surface of the device.
A coating solultion prepared in accordance with the te~hing.c of this inventio]l and having tl~e following formulation is provided:
Component Supplier/Design~tionWeight (%) Urethane R9621/Zeneca Resins 82.2 Micaceous pigment 110 Silver Pearl/ 6.5 EM Industries Crosslinking Agent CX100/Zeneca Resins 3.7 Acetone ~ 3.7 Water -- 3.7 The coating solution is prepared by prewetting and dispersing the mic~ceous pigment (3.5g) (110 Silver Pearl obtained from EM Industries, Hawthorne, NY~ into a solution of distilled water (2g) and acetone (2g) to reduce the tendency to foam.
The urethane dispersion (44g) (R9621 obtained from Zeneca Resins, Wilmington, 25 MA) was added with agitation provided by a magnetic stirrer. Finally, the crosclinking agent (2g) (CX100 obtained from Zeneca Resins) was added dropwise and allowed to stir for 30 minutes prior to application.
A PET balloon had been plasma treated (300W, 0.25 Torr oxygen for 5 min~ltes) and dipped into a 15% solids emulsion of primer (MICHEMPRIME 4983R
CA 02212181 1997-08-0~
W 096/24393 PCTrUS96/01624 obtained from Michelm~n, Cin~inn~ti, OH), and the then dried for 5 mimlteS at 46~C before the coating solution was applied. The coating solution was applied by dip, then cured and dried for 1 hour at 46~C.
A coating solution prepared in accordance with the teachingc of this invention and having the following formulation is provided:
Component Supplier/Design~tiQn Weight (%) Urethane R972 (Zeneca Resins) 50 Glass fiber 737BC (Owens-Corning) 5.1 Crosclinking agent CX100/Zeneca Resins 2 Water -- 42.9 The urethane dispersion, glass fiber (737BC obtained from Owens-Corning, Toledo, OH~ and water were mixed with agitation provided by a rn~gn~tic stirrer.25 The crosslinking agent was added dropwise and allowed to stir for 30 minutes prior to application.
The coating solution was applied to a PET balloon that had been corona treated achieved by rotating the balloon for 1 minute within 1/2" of corona generated by a Model BD-20 with a 3" electrode, BD-20 supplied by Electro-30 Technics, Chicago, IL) and dipped into a 15% solids emulsion of primer (Primacor5980, Dow Chemical, Mi~l~n~, Michigan), and dried for 5 minutes at 46~C. The coating solution was applied by flow coating, then cured and dried for 1 hour at46~C.
CA 02212181 1997-08-0~
WO 96124393 PCT/~7S96~01G24 A coating sohltion prepared in accordance with the teac hings of this invention and having the following formula~ion is provided:
Compoment Supplier/D~sign~tion Weight (%) Urethane R9621/Zeneca Resins 6.8 Water 67.9 Tllngcten Powder M10/GTE Osram Z3.2 Thickening Agent ASE-60 Acr,vsol/Rohm & Haas 2.0 The coating solution was prepared by combining the urethane and water.
20 The thickener may be added dropwise with agitation and the solution pH adjusted to 9 with ammonium hydroxide to allow the viscosity to increase. The tllngcten powder was added and stirred into the thickened solution.
A PET balloon prepared with a corona tre~tm~nt (as in Example 2) and primer clipped (MICHl_MPRIME 4983 as in Example 1) was flow coated with the 25 tllng~cten reinforced coating solution and dried for 1 hour at 46~C.
C'oated and uncoated balloons were scratch tested with the results that the testing of uncoated balloons resulted in complete destruction of the balloon, whereas the coated balloons resisted the injury, resulting in only discrete damage to the effected area.
Claims (23)
1. A method for providing a protective coating on a surface of a medical apparatus adapted for use within a patient, comprising:
applying a coating solution to a surface of an implantable medical apparatus, such that a protective layer is formed upon the apparatus surface, wherein the coating solution comprises a matrix polymer which contains a reinforcing agent, the reinforcing agent having a higher surface hardness thanthe surface hardness of the medical apparatus, wherein a total coating thicknesson the medical apparatus is no greater than about 3 mil (0.003 inch).
applying a coating solution to a surface of an implantable medical apparatus, such that a protective layer is formed upon the apparatus surface, wherein the coating solution comprises a matrix polymer which contains a reinforcing agent, the reinforcing agent having a higher surface hardness thanthe surface hardness of the medical apparatus, wherein a total coating thicknesson the medical apparatus is no greater than about 3 mil (0.003 inch).
2. Cancelled.
3. A method for providing a providing a protective coating on a surface of a medical apparatus in accordance with Claim 1, wherein the matrix polymer is urethane.
4. A method for providing a protective coating on a surface of a medical apparatus in accordance with Claim 1, wherein the matrix polymer is epoxy.
5. A method for providing a providing a protective coating on a surface of a medical apparatus in accordance with Claim 1, wherein the reinforcing agent of the coating solution comprises a lamellar material.
6. A method for providing a providing a protective coating on a surface of a medical apparatus in accordance with Claim 5, wherein the lamellar reinforcing agent of the coating solution comprises a micaeous pigment.
7. A method for providing a providing a protective coating on a surface of a medical apparatus in accordance with Claim 1, wherein the reinforcing agent of the coating solution comprises a fiber.
8. A method for providing a providing a protective coating on a surface of a medical apparatus in accordance with Claim 7, wherein the fiber reinforcing agent of the coating solution comprises glass.
9. A method for providing a providing a protective coating on a surface of a medical apparatus in accordance with Claim 1, wherein the reinforcing agent is selected from the group consisting of lamellar platelets, flake pigments and fibers.
10. A method for providing a protective coating on a surface of a medical apparatus in accordance with Claim 1, further comprising applying a primer to the surface of the medical apparatus.
11. A method for providing a providing a protective coating on a surface of a medical apparatus in accordance with Claim 1, wherein the coating solution further comprises a crosslinking agent.
12. A method for providing a protective coating on a medical apparatus in accordance with Claim 11, wherein the crosslinking agent is aziridine.
13. A method for providing a protective coating on a surface of a medical apparatus in accordance with Claim 1, wherein the medical apparatus comprises a catheter.
14. A method for providing a protective coating on a surface of a medical apparatus in accordance with Claim 1, wherein the medical apparatus comprises a balloon.
15. A method for providing a protective coating on the surface of an implantable medical apparatus adapted for use within a patient, comprising:
applying a coating solution to a surface of the medical apparatus, the coating solution comprising a reinforcing agent, the reinforcing agent containing fibers, such that a protective coating is formed on the apparatus surface; and aligning the fibers on the surface of the medical apparatus in a direction parallel to the apparatus surface.
applying a coating solution to a surface of the medical apparatus, the coating solution comprising a reinforcing agent, the reinforcing agent containing fibers, such that a protective coating is formed on the apparatus surface; and aligning the fibers on the surface of the medical apparatus in a direction parallel to the apparatus surface.
16. An implantable medical apparatus having a protective surface coating, the coating comprising a matrix polymer and a reinforcing agent, the reinforcing agent having a higher surface hardness than the surface hardness of the medical apparatus, wherein the total coating thickness on the medical aparatus is no greater than about 3 mils (0.003 inch).
17. A medical apparatus in accordance with Claim 16, wherein the coating further comprises a crosslinking agent.
18. A medical apparatus in accordance with Claim 16, the medical apparatus comprising a balloon for use with a catheter.
19. A method for providing a protective coating on the surface of an implantable medical apparatus adapted for use within a patient, comprising:
applying a coating solution to a surface of the medical apparatus, such that a protective layer is formed upon the apparatus surface, such that a total coating thickness on the medical apparatus is no greater than about 3 mil, wherein the coating solution comprises a matrix polymer which contains a reinforcing agent, the reinforcing agent containing particles having a higher surface hardness than the surface hardness of the medical apparatus; and aligning the particles on the surface of the medical apparatus in a direction parallel to the apparatus surface.
applying a coating solution to a surface of the medical apparatus, such that a protective layer is formed upon the apparatus surface, such that a total coating thickness on the medical apparatus is no greater than about 3 mil, wherein the coating solution comprises a matrix polymer which contains a reinforcing agent, the reinforcing agent containing particles having a higher surface hardness than the surface hardness of the medical apparatus; and aligning the particles on the surface of the medical apparatus in a direction parallel to the apparatus surface.
20. A method for providing a protective coating on the surface of a medical apparatus in accordance with any one of Claims 1, 15 and 19, wherein said implantable medical apparatus is temporarily implantable.
21. A method for providing a protective coating on the surface of a medical apparatus in accordance with Claim 1, wherein said protective layer has a thickness in the range of about 0.1 mil to about 3 mil.
22. A method for providing a protective coating on the surface of a medical apparatus in accordance with Claim 1, wherein said protective layer has a thickness in the range of about 0.2 mil to about 2 mil.
23. A method for providing a protective coating on the surface of a medical apparatus in accordance with Claim 1, wherein the step of applying a coating solution to the apparatus surface is performed two or more times.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US08/384,422 US5599576A (en) | 1995-02-06 | 1995-02-06 | Medical apparatus with scratch-resistant coating and method of making same |
US08/384,422 | 1995-02-06 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA2212181A1 true CA2212181A1 (en) | 1996-08-15 |
Family
ID=23517254
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002212181A Abandoned CA2212181A1 (en) | 1995-02-06 | 1996-02-05 | Medical apparatus with scratch-resistant coating and method making same |
Country Status (6)
Country | Link |
---|---|
US (2) | US5599576A (en) |
EP (1) | EP0808182A1 (en) |
JP (1) | JPH11503033A (en) |
AU (1) | AU691737B2 (en) |
CA (1) | CA2212181A1 (en) |
WO (1) | WO1996024393A1 (en) |
Families Citing this family (202)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6774278B1 (en) | 1995-06-07 | 2004-08-10 | Cook Incorporated | Coated implantable medical device |
US5780300A (en) * | 1995-09-29 | 1998-07-14 | Yale University | Manipulation of non-terminally differentiated cells using the notch pathway |
US5681477A (en) * | 1995-10-25 | 1997-10-28 | Praxair Technology, Inc. | Thermally-driven ion-exchange process for lithium recovery |
US5756145A (en) * | 1995-11-08 | 1998-05-26 | Baylor College Of Medicine | Durable, Resilient and effective antimicrobial coating for medical devices and method of coating therefor |
US6558686B1 (en) | 1995-11-08 | 2003-05-06 | Baylor College Of Medicine | Method of coating medical devices with a combination of antiseptics and antiseptic coating therefor |
US6746425B1 (en) * | 1996-06-14 | 2004-06-08 | Futuremed Interventional | Medical balloon |
US6174329B1 (en) * | 1996-08-22 | 2001-01-16 | Advanced Cardiovascular Systems, Inc. | Protective coating for a stent with intermediate radiopaque coating |
US5935164A (en) * | 1997-02-25 | 1999-08-10 | Pmt Corporaton | Laminated prosthesis and method of manufacture |
US5972015A (en) | 1997-08-15 | 1999-10-26 | Kyphon Inc. | Expandable, asymetric structures for deployment in interior body regions |
US6020397A (en) * | 1997-10-10 | 2000-02-01 | Westvaco Corporation | Two-component ink jet ink system |
US6273908B1 (en) | 1997-10-24 | 2001-08-14 | Robert Ndondo-Lay | Stents |
US6021524A (en) * | 1997-12-31 | 2000-02-08 | The University Of Akron | Cut resistant polymeric films |
US6096726A (en) | 1998-03-11 | 2000-08-01 | Surface Solutions Laboratories Incorporated | Multicomponent complex for use with substrate |
US6024918A (en) * | 1998-03-13 | 2000-02-15 | Medtronic, Inc. | Method for attachment of biomolecules to surfaces of medical devices |
US6203505B1 (en) * | 1998-06-05 | 2001-03-20 | Advanced Cardiovascular Systems, Inc. | Guidewires having a vapor deposited primer coat |
US6743244B2 (en) | 1999-04-16 | 2004-06-01 | Integrated Vascular Interventional Technologies, L.C. | Soft anvil apparatus for cutting anastomosis fenestra |
US6551334B2 (en) | 1999-04-16 | 2003-04-22 | Integrated Vascular Interventional Technologies, Lc | Externally directed anastomosis systems and externally positioned anastomosis fenestra cutting apparatus |
US6726694B2 (en) | 1999-04-16 | 2004-04-27 | Integrated Vascular Interventional Technologies, L.C. (Ivit, Lc) | Intraluminally directed anvil apparatus and related methods and systems |
US6623494B1 (en) * | 1999-04-16 | 2003-09-23 | Integrated Vascular Interventional Technologies, L.C. (Ivit, Lc) | Methods and systems for intraluminally directed vascular anastomosis |
US6652542B2 (en) | 1999-04-16 | 2003-11-25 | Integrated Vascular Interventional Technologies, L.C. (Ivit, Lc) | External anastomosis operators and related systems for anastomosis |
US7160311B2 (en) * | 1999-04-16 | 2007-01-09 | Integrated Vascular Interventional Technologies, L.C. (Ivit Lc) | Locking compression plate anastomosis apparatus |
US6248117B1 (en) | 1999-04-16 | 2001-06-19 | Vital Access Corp | Anastomosis apparatus for use in intraluminally directed vascular anastomosis |
US7981126B2 (en) | 1999-04-16 | 2011-07-19 | Vital Access Corporation | Locking compression plate anastomosis apparatus |
DE19921088C2 (en) * | 1999-04-30 | 2003-08-07 | Magforce Applic Gmbh | Stent to keep aisle-like structures open |
US6585757B1 (en) | 1999-09-15 | 2003-07-01 | Advanced Cardiovascular Systems, Inc. | Endovascular stent with radiopaque spine |
US7479128B1 (en) * | 2000-01-04 | 2009-01-20 | Boston Scientific Scimed, Inc. | Protective coatings for medical devices |
US6656151B1 (en) | 2000-01-11 | 2003-12-02 | Integrated Vascular Interventional Technologies, L.C. (Ivit, Lc) | Vascular access devices and systems |
US7118546B2 (en) * | 2000-01-11 | 2006-10-10 | Integrated Vascular Interventional Technologies, L.C. | Apparatus and methods for facilitating repeated vascular access |
WO2001051117A1 (en) | 2000-01-11 | 2001-07-19 | Blatter Duane D | Vascular occlusal balloons and related vascular access devices and systems |
US6595941B1 (en) | 2000-01-11 | 2003-07-22 | Integrated Vascular Interventional Technologies, L.C. | Methods for external treatment of blood |
US7131959B2 (en) * | 2003-01-23 | 2006-11-07 | Integrated Vascular Interventional Technologies, L.C., (“IVIT LC”) | Apparatus and methods for occluding an access tube anastomosed to sidewall of an anatomical vessel |
US7803149B2 (en) * | 2002-07-12 | 2010-09-28 | Cook Incorporated | Coated medical device |
DE10105592A1 (en) * | 2001-02-06 | 2002-08-08 | Achim Goepferich | Placeholder for drug release in the frontal sinus |
DE10115740A1 (en) * | 2001-03-26 | 2002-10-02 | Ulrich Speck | Preparation for restenosis prophylaxis |
US6739033B2 (en) * | 2001-03-29 | 2004-05-25 | Scimed Life Systems, Inc. | Thermal regulation of a coated work-piece during the reconfiguration of the coated work-piece |
US7169785B2 (en) * | 2001-09-21 | 2007-01-30 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US7112587B2 (en) * | 2001-09-21 | 2006-09-26 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US7163943B2 (en) * | 2001-09-21 | 2007-01-16 | Reddy Us Therapeutics, Inc. | Methods and compositions of novel triazine compounds |
US6844374B2 (en) * | 2001-10-03 | 2005-01-18 | Lord Corporation | Enhanced scratch resistant coatings using inorganic fillers |
WO2003089026A1 (en) * | 2002-04-17 | 2003-10-30 | Genzyme Corporation | Aziridine compounds and their use in medical devices |
US7008979B2 (en) * | 2002-04-30 | 2006-03-07 | Hydromer, Inc. | Coating composition for multiple hydrophilic applications |
DE10244847A1 (en) | 2002-09-20 | 2004-04-01 | Ulrich Prof. Dr. Speck | Medical device for drug delivery |
US8317816B2 (en) | 2002-09-30 | 2012-11-27 | Acclarent, Inc. | Balloon catheters and methods for treating paranasal sinuses |
US7124570B2 (en) * | 2003-01-23 | 2006-10-24 | Integrated Vascular Interventional Technologies, L.C. | Apparatus and methods for fluid occlusion of an access tube anastomosed to an anatomical vessel |
US8715771B2 (en) * | 2003-02-26 | 2014-05-06 | Abbott Cardiovascular Systems Inc. | Coated stent and method of making the same |
US7255891B1 (en) * | 2003-02-26 | 2007-08-14 | Advanced Cardiovascular Systems, Inc. | Method for coating implantable medical devices |
GB0318353D0 (en) * | 2003-08-05 | 2003-09-10 | Phoqus Pharmaceuticals Ltd | Coating of surgical devices |
DE10352627A1 (en) * | 2003-11-11 | 2005-06-09 | Merck Patent Gmbh | Finely divided hard moldings for abrasion-resistant polymer matrices |
US20050123702A1 (en) * | 2003-12-03 | 2005-06-09 | Jim Beckham | Non-compliant medical balloon having a longitudinal fiber layer |
US7713233B2 (en) * | 2004-04-12 | 2010-05-11 | Boston Scientific Scimed, Inc. | Balloons having a crosslinkable layer |
US8894614B2 (en) * | 2004-04-21 | 2014-11-25 | Acclarent, Inc. | Devices, systems and methods useable for treating frontal sinusitis |
US9351750B2 (en) | 2004-04-21 | 2016-05-31 | Acclarent, Inc. | Devices and methods for treating maxillary sinus disease |
US20070167682A1 (en) | 2004-04-21 | 2007-07-19 | Acclarent, Inc. | Endoscopic methods and devices for transnasal procedures |
US7559925B2 (en) * | 2006-09-15 | 2009-07-14 | Acclarent Inc. | Methods and devices for facilitating visualization in a surgical environment |
US9101384B2 (en) | 2004-04-21 | 2015-08-11 | Acclarent, Inc. | Devices, systems and methods for diagnosing and treating sinusitis and other disorders of the ears, Nose and/or throat |
US8864787B2 (en) | 2004-04-21 | 2014-10-21 | Acclarent, Inc. | Ethmoidotomy system and implantable spacer devices having therapeutic substance delivery capability for treatment of paranasal sinusitis |
US9554691B2 (en) * | 2004-04-21 | 2017-01-31 | Acclarent, Inc. | Endoscopic methods and devices for transnasal procedures |
US7410480B2 (en) | 2004-04-21 | 2008-08-12 | Acclarent, Inc. | Devices and methods for delivering therapeutic substances for the treatment of sinusitis and other disorders |
US8702626B1 (en) | 2004-04-21 | 2014-04-22 | Acclarent, Inc. | Guidewires for performing image guided procedures |
US8932276B1 (en) | 2004-04-21 | 2015-01-13 | Acclarent, Inc. | Shapeable guide catheters and related methods |
US20070208252A1 (en) | 2004-04-21 | 2007-09-06 | Acclarent, Inc. | Systems and methods for performing image guided procedures within the ear, nose, throat and paranasal sinuses |
US20060063973A1 (en) | 2004-04-21 | 2006-03-23 | Acclarent, Inc. | Methods and apparatus for treating disorders of the ear, nose and throat |
US20190314620A1 (en) | 2004-04-21 | 2019-10-17 | Acclarent, Inc. | Apparatus and methods for dilating and modifying ostia of paranasal sinuses and other intranasal or paranasal structures |
US20110004057A1 (en) * | 2004-04-21 | 2011-01-06 | Acclarent, Inc. | Systems and methods for transnasal dilation of passageways in the ear, nose or throat |
US7654997B2 (en) | 2004-04-21 | 2010-02-02 | Acclarent, Inc. | Devices, systems and methods for diagnosing and treating sinusitus and other disorders of the ears, nose and/or throat |
US9089258B2 (en) * | 2004-04-21 | 2015-07-28 | Acclarent, Inc. | Endoscopic methods and devices for transnasal procedures |
US8747389B2 (en) | 2004-04-21 | 2014-06-10 | Acclarent, Inc. | Systems for treating disorders of the ear, nose and throat |
US7361168B2 (en) * | 2004-04-21 | 2008-04-22 | Acclarent, Inc. | Implantable device and methods for delivering drugs and other substances to treat sinusitis and other disorders |
US20060004323A1 (en) | 2004-04-21 | 2006-01-05 | Exploramed Nc1, Inc. | Apparatus and methods for dilating and modifying ostia of paranasal sinuses and other intranasal or paranasal structures |
US10188413B1 (en) | 2004-04-21 | 2019-01-29 | Acclarent, Inc. | Deflectable guide catheters and related methods |
US9399121B2 (en) | 2004-04-21 | 2016-07-26 | Acclarent, Inc. | Systems and methods for transnasal dilation of passageways in the ear, nose or throat |
US8146400B2 (en) | 2004-04-21 | 2012-04-03 | Acclarent, Inc. | Endoscopic methods and devices for transnasal procedures |
US7462175B2 (en) | 2004-04-21 | 2008-12-09 | Acclarent, Inc. | Devices, systems and methods for treating disorders of the ear, nose and throat |
US7803150B2 (en) | 2004-04-21 | 2010-09-28 | Acclarent, Inc. | Devices, systems and methods useable for treating sinusitis |
US7419497B2 (en) | 2004-04-21 | 2008-09-02 | Acclarent, Inc. | Methods for treating ethmoid disease |
US8764729B2 (en) * | 2004-04-21 | 2014-07-01 | Acclarent, Inc. | Frontal sinus spacer |
US7354419B2 (en) | 2004-10-15 | 2008-04-08 | Futuremed Interventional, Inc. | Medical balloon having strengthening rods |
US7682335B2 (en) | 2004-10-15 | 2010-03-23 | Futurematrix Interventional, Inc. | Non-compliant medical balloon having an integral non-woven fabric layer |
US7914487B2 (en) * | 2004-10-15 | 2011-03-29 | Futurematrix Interventional, Inc. | Non-compliant medical balloon having braided or knitted reinforcement |
US7309324B2 (en) * | 2004-10-15 | 2007-12-18 | Futuremed Interventional, Inc. | Non-compliant medical balloon having an integral woven fabric layer |
US8951225B2 (en) | 2005-06-10 | 2015-02-10 | Acclarent, Inc. | Catheters with non-removable guide members useable for treatment of sinusitis |
US7500982B2 (en) | 2005-06-22 | 2009-03-10 | Futurematrix Interventional, Inc. | Balloon dilation catheter having transition from coaxial lumens to non-coaxial multiple lumens |
US7544201B2 (en) * | 2005-07-05 | 2009-06-09 | Futurematrix Interventional, Inc. | Rapid exchange balloon dilation catheter having reinforced multi-lumen distal portion |
CA2615452C (en) | 2005-07-15 | 2015-03-31 | Micell Technologies, Inc. | Polymer coatings containing drug powder of controlled morphology |
US20090062909A1 (en) | 2005-07-15 | 2009-03-05 | Micell Technologies, Inc. | Stent with polymer coating containing amorphous rapamycin |
US8114113B2 (en) | 2005-09-23 | 2012-02-14 | Acclarent, Inc. | Multi-conduit balloon catheter |
US20070142772A1 (en) * | 2005-12-16 | 2007-06-21 | Medtronic Vascular, Inc. | Dual-Layer Medical Balloon |
US9901731B2 (en) * | 2006-01-31 | 2018-02-27 | Medtronic, Inc. | Medical electrical lead having improved inductance |
US20070179582A1 (en) * | 2006-01-31 | 2007-08-02 | Marshall Mark T | Polymer reinforced coil conductor for torque transmission |
US20070179518A1 (en) * | 2006-02-02 | 2007-08-02 | Becker Bruce B | Balloon Catheters and Methods for Treating Paranasal Sinuses |
CA2996768C (en) | 2006-04-26 | 2020-12-08 | Micell Technologies, Inc. | Coatings containing multiple drugs |
US9080061B2 (en) | 2006-05-03 | 2015-07-14 | Surface Solutions Laboratories | Coating resins and coating with multiple crosslink functionalities |
US8190389B2 (en) | 2006-05-17 | 2012-05-29 | Acclarent, Inc. | Adapter for attaching electromagnetic image guidance components to a medical device |
US9820688B2 (en) | 2006-09-15 | 2017-11-21 | Acclarent, Inc. | Sinus illumination lightwire device |
US8414526B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Medical device rapid drug releasing coatings comprising oils, fatty acids, and/or lipids |
US20080175887A1 (en) | 2006-11-20 | 2008-07-24 | Lixiao Wang | Treatment of Asthma and Chronic Obstructive Pulmonary Disease With Anti-proliferate and Anti-inflammatory Drugs |
US8430055B2 (en) | 2008-08-29 | 2013-04-30 | Lutonix, Inc. | Methods and apparatuses for coating balloon catheters |
US9737640B2 (en) | 2006-11-20 | 2017-08-22 | Lutonix, Inc. | Drug releasing coatings for medical devices |
US8425459B2 (en) | 2006-11-20 | 2013-04-23 | Lutonix, Inc. | Medical device rapid drug releasing coatings comprising a therapeutic agent and a contrast agent |
US8414525B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
US20080276935A1 (en) | 2006-11-20 | 2008-11-13 | Lixiao Wang | Treatment of asthma and chronic obstructive pulmonary disease with anti-proliferate and anti-inflammatory drugs |
US9700704B2 (en) | 2006-11-20 | 2017-07-11 | Lutonix, Inc. | Drug releasing coatings for balloon catheters |
US8998846B2 (en) | 2006-11-20 | 2015-04-07 | Lutonix, Inc. | Drug releasing coatings for balloon catheters |
US8414910B2 (en) | 2006-11-20 | 2013-04-09 | Lutonix, Inc. | Drug releasing coatings for medical devices |
US7610101B2 (en) * | 2006-11-30 | 2009-10-27 | Cardiac Pacemakers, Inc. | RF rejecting lead |
US8439687B1 (en) | 2006-12-29 | 2013-05-14 | Acclarent, Inc. | Apparatus and method for simulated insertion and positioning of guidewares and other interventional devices |
US11426494B2 (en) | 2007-01-08 | 2022-08-30 | MT Acquisition Holdings LLC | Stents having biodegradable layers |
CA2679712C (en) | 2007-01-08 | 2016-11-15 | Micell Technologies, Inc. | Stents having biodegradable layers |
RU2447901C2 (en) | 2007-01-21 | 2012-04-20 | Хемотек Аг | Medical device for treating lumen obturations and preventing threatening recurrent obturations |
JP5024367B2 (en) * | 2007-03-23 | 2012-09-12 | 富士通株式会社 | Electronic device, electronic device mounted with electronic device, article mounted with electronic device, and method of manufacturing electronic device |
US8118757B2 (en) | 2007-04-30 | 2012-02-21 | Acclarent, Inc. | Methods and devices for ostium measurement |
US8485199B2 (en) | 2007-05-08 | 2013-07-16 | Acclarent, Inc. | Methods and devices for protecting nasal turbinate during surgery |
US9192697B2 (en) | 2007-07-03 | 2015-11-24 | Hemoteq Ag | Balloon catheter for treating stenosis of body passages and for preventing threatening restenosis |
US20090030409A1 (en) * | 2007-07-27 | 2009-01-29 | Eric Goldfarb | Methods and devices for facilitating visualization in a surgical environment |
US8313601B2 (en) * | 2007-08-06 | 2012-11-20 | Bard Peripheral Vascular, Inc. | Non-compliant medical balloon |
US8002744B2 (en) | 2007-08-06 | 2011-08-23 | Bard Peripheral Vascular, Inc | Non-compliant medical balloon |
US20090099517A1 (en) * | 2007-10-10 | 2009-04-16 | C. R. Bard, Inc. | Reinforced, non-compliant angioplasty balloon |
US20090149700A1 (en) * | 2007-11-02 | 2009-06-11 | Ruben Garcia | Method and apparatus for pubic sling insertion |
WO2009076163A2 (en) | 2007-12-06 | 2009-06-18 | Cardiac Pacemakers, Inc. | Implantable lead having a variable coil conductor pitch |
US10206821B2 (en) | 2007-12-20 | 2019-02-19 | Acclarent, Inc. | Eustachian tube dilation balloon with ventilation path |
AU2009212697B2 (en) | 2008-02-06 | 2011-12-01 | Cardiac Pacemakers, Inc. | Lead with MRI compatible design features |
US8182432B2 (en) | 2008-03-10 | 2012-05-22 | Acclarent, Inc. | Corewire design and construction for medical devices |
EP2271294B1 (en) | 2008-04-17 | 2018-03-28 | Micell Technologies, Inc. | Stents having bioabsorbable layers |
US8103360B2 (en) | 2008-05-09 | 2012-01-24 | Foster Arthur J | Medical lead coil conductor with spacer element |
CA2727478A1 (en) * | 2008-06-13 | 2009-12-17 | Xy, Llc | Lubricious microfluidic flow path system |
JP2011528275A (en) | 2008-07-17 | 2011-11-17 | ミセル テクノロジーズ,インク. | Drug delivery medical device |
EP2664350B1 (en) | 2008-07-30 | 2019-08-28 | Acclarent, Inc. | Paranasal ostium finder devices |
WO2010033629A1 (en) | 2008-09-18 | 2010-03-25 | Acclarent, Inc. | Methods and apparatus for treating disorders of the ear nose and throat |
US8076529B2 (en) | 2008-09-26 | 2011-12-13 | Abbott Cardiovascular Systems, Inc. | Expandable member formed of a fibrous matrix for intraluminal drug delivery |
US8226603B2 (en) | 2008-09-25 | 2012-07-24 | Abbott Cardiovascular Systems Inc. | Expandable member having a covering formed of a fibrous matrix for intraluminal drug delivery |
US8049061B2 (en) | 2008-09-25 | 2011-11-01 | Abbott Cardiovascular Systems, Inc. | Expandable member formed of a fibrous matrix having hydrogel polymer for intraluminal drug delivery |
US20100094074A1 (en) * | 2008-10-10 | 2010-04-15 | Hologic Inc. | Brachytherapy apparatus and methods employing expandable medical devices comprising fixation elements |
US20100094075A1 (en) * | 2008-10-10 | 2010-04-15 | Hologic Inc. | Expandable medical devices with reinforced elastomeric members and methods employing the same |
TWI455734B (en) * | 2008-11-20 | 2014-10-11 | Alcon Res Ltd | Intraocular lens delivery device having a cartridge with an internal coating |
US8728110B2 (en) | 2009-01-16 | 2014-05-20 | Bard Peripheral Vascular, Inc. | Balloon dilation catheter shaft having end transition |
US9259559B2 (en) | 2009-02-23 | 2016-02-16 | Futurematrix Interventional, Inc. | Balloon catheter pressure relief valve |
US8814899B2 (en) | 2009-02-23 | 2014-08-26 | Futurematrix Interventional, Inc. | Balloon catheter pressure relief valve |
US9084883B2 (en) * | 2009-03-12 | 2015-07-21 | Cardiac Pacemakers, Inc. | Thin profile conductor assembly for medical device leads |
US20100241155A1 (en) | 2009-03-20 | 2010-09-23 | Acclarent, Inc. | Guide system with suction |
CA2756307C (en) * | 2009-03-23 | 2017-08-08 | Micell Technologies, Inc. | Peripheral stents having layers and reinforcement fibers |
WO2010111238A2 (en) * | 2009-03-23 | 2010-09-30 | Micell Technologies, Inc. | Improved biodegradable polymers |
US20100239635A1 (en) * | 2009-03-23 | 2010-09-23 | Micell Technologies, Inc. | Drug delivery medical device |
US8435290B2 (en) * | 2009-03-31 | 2013-05-07 | Acclarent, Inc. | System and method for treatment of non-ventilating middle ear by providing a gas pathway through the nasopharynx |
US7978742B1 (en) | 2010-03-24 | 2011-07-12 | Corning Incorporated | Methods for operating diode lasers |
CN102481195B (en) | 2009-04-01 | 2015-03-25 | 米歇尔技术公司 | Drug delivery medical device |
WO2010121187A2 (en) | 2009-04-17 | 2010-10-21 | Micell Techologies, Inc. | Stents having controlled elution |
WO2010124098A2 (en) * | 2009-04-24 | 2010-10-28 | Boston Scientific Scimed, Inc. | Use of drug polymorphs to achieve controlled drug delivery from a coated medical device |
CA2759817A1 (en) * | 2009-06-05 | 2010-12-09 | Entrigue Surgical, Inc. | Systems and devices for providing therapy of an anatomical structure |
WO2010151376A1 (en) * | 2009-06-26 | 2010-12-29 | Cardiac Pacemakers, Inc. | Medical device lead including a unifilar coil with improved torque transmission capacity and reduced mri heating |
EP3064230B1 (en) | 2009-07-10 | 2019-04-10 | Boston Scientific Scimed, Inc. | Use of nanocrystals for a drug delivery balloon |
EP2453834A4 (en) | 2009-07-16 | 2014-04-16 | Micell Technologies Inc | Drug delivery medical device |
EP2453938B1 (en) | 2009-07-17 | 2015-08-19 | Boston Scientific Scimed, Inc. | Nucleation of drug delivery balloons to provide improved crystal size and density |
WO2011028397A1 (en) | 2009-08-24 | 2011-03-10 | Cook Incorporated | Textile-reinforced high-pressure balloon |
US9211391B2 (en) * | 2009-09-24 | 2015-12-15 | Bard Peripheral Vascular, Inc. | Balloon with variable pitch reinforcing fibers |
US8335572B2 (en) * | 2009-10-08 | 2012-12-18 | Cardiac Pacemakers, Inc. | Medical device lead including a flared conductive coil |
WO2011049684A1 (en) * | 2009-10-19 | 2011-04-28 | Cardiac Pacemakers, Inc. | Mri compatible tachycardia lead |
US20110160740A1 (en) * | 2009-12-28 | 2011-06-30 | Acclarent, Inc. | Tissue Removal in The Paranasal Sinus and Nasal Cavity |
EP2519311A1 (en) * | 2009-12-30 | 2012-11-07 | Cardiac Pacemakers, Inc. | Mri-conditionally safe medical device lead |
CN102655908B (en) | 2009-12-31 | 2015-04-22 | 心脏起搏器公司 | MRI conditionally safe lead with multi-layer conductor |
US8391994B2 (en) | 2009-12-31 | 2013-03-05 | Cardiac Pacemakers, Inc. | MRI conditionally safe lead with low-profile multi-layer conductor for longitudinal expansion |
US11369498B2 (en) * | 2010-02-02 | 2022-06-28 | MT Acquisition Holdings LLC | Stent and stent delivery system with improved deliverability |
WO2011119536A1 (en) | 2010-03-22 | 2011-09-29 | Abbott Cardiovascular Systems Inc. | Stent delivery system having a fibrous matrix covering with improved stent retention |
US8795762B2 (en) | 2010-03-26 | 2014-08-05 | Battelle Memorial Institute | System and method for enhanced electrostatic deposition and surface coatings |
WO2011133655A1 (en) | 2010-04-22 | 2011-10-27 | Micell Technologies, Inc. | Stents and other devices having extracellular matrix coating |
CA2805631C (en) | 2010-07-16 | 2018-07-31 | Micell Technologies, Inc. | Drug delivery medical device |
TWI707926B (en) | 2010-07-30 | 2020-10-21 | 瑞士商愛爾康公司 | Readily-usable silicone hydrogel contact lenses |
US8825181B2 (en) | 2010-08-30 | 2014-09-02 | Cardiac Pacemakers, Inc. | Lead conductor with pitch and torque control for MRI conditionally safe use |
EP2611476B1 (en) | 2010-09-02 | 2016-08-10 | Boston Scientific Scimed, Inc. | Coating process for drug delivery balloons using heat-induced rewrap memory |
US9155492B2 (en) | 2010-09-24 | 2015-10-13 | Acclarent, Inc. | Sinus illumination lightwire device |
US8597240B2 (en) | 2011-02-02 | 2013-12-03 | Futurematrix Interventional, Inc. | Coaxial catheter shaft having balloon attachment feature with axial fluid path |
US20120312840A1 (en) * | 2011-05-13 | 2012-12-13 | Ayako Hasegawa | Container closure system with integral antimicrobial additives |
WO2012166819A1 (en) | 2011-05-31 | 2012-12-06 | Micell Technologies, Inc. | System and process for formation of a time-released, drug-eluting transferable coating |
CA2841360A1 (en) | 2011-07-15 | 2013-01-24 | Micell Technologies, Inc. | Drug delivery medical device |
US8669360B2 (en) | 2011-08-05 | 2014-03-11 | Boston Scientific Scimed, Inc. | Methods of converting amorphous drug substance into crystalline form |
WO2013028208A1 (en) | 2011-08-25 | 2013-02-28 | Boston Scientific Scimed, Inc. | Medical device with crystalline drug coating |
AU2012312239B2 (en) | 2011-09-21 | 2017-09-28 | Donaldson Company, Inc. | Fine fibers made from polymer crosslinked with resinous aldehyde composition |
JP6017572B2 (en) | 2011-10-12 | 2016-11-02 | ノバルティス アーゲー | Method for producing UV-absorbing ophthalmic lens by coating |
US10188772B2 (en) | 2011-10-18 | 2019-01-29 | Micell Technologies, Inc. | Drug delivery medical device |
US8666512B2 (en) | 2011-11-04 | 2014-03-04 | Cardiac Pacemakers, Inc. | Implantable medical device lead including inner coil reverse-wound relative to shocking coil |
US8825179B2 (en) | 2012-04-20 | 2014-09-02 | Cardiac Pacemakers, Inc. | Implantable medical device lead including a unifilar coiled cable |
US8954168B2 (en) | 2012-06-01 | 2015-02-10 | Cardiac Pacemakers, Inc. | Implantable device lead including a distal electrode assembly with a coiled component |
JP6069499B2 (en) | 2012-08-31 | 2017-02-01 | カーディアック ペースメイカーズ, インコーポレイテッド | Lead wire with low peak MRI heating |
JP6034499B2 (en) | 2012-10-18 | 2016-11-30 | カーディアック ペースメイカーズ, インコーポレイテッド | Inductive element for providing MRI compatibility in implantable medical device leads |
WO2014095690A1 (en) | 2012-12-17 | 2014-06-26 | Novartis Ag | Method for making improved uv-absorbing ophthalmic lenses |
KR102139254B1 (en) | 2013-03-09 | 2020-07-29 | 도널드선 컴파니 인코포레이티드 | Fine fibers made from reactive additives |
KR20150143476A (en) | 2013-03-12 | 2015-12-23 | 미셀 테크놀로지즈, 인코포레이티드 | Bioabsorbable biomedical implants |
US9629684B2 (en) | 2013-03-15 | 2017-04-25 | Acclarent, Inc. | Apparatus and method for treatment of ethmoid sinusitis |
US9433437B2 (en) | 2013-03-15 | 2016-09-06 | Acclarent, Inc. | Apparatus and method for treatment of ethmoid sinusitis |
KR102079613B1 (en) | 2013-05-15 | 2020-02-20 | 미셀 테크놀로지즈, 인코포레이티드 | Bioabsorbable biomedical implants |
US9708087B2 (en) | 2013-12-17 | 2017-07-18 | Novartis Ag | Silicone hydrogel lens with a crosslinked hydrophilic coating |
EP3110499B1 (en) | 2014-02-26 | 2018-01-24 | Cardiac Pacemakers, Inc. | Construction of an mri-safe tachycardia lead |
EP3186070B1 (en) | 2014-08-26 | 2019-09-25 | Novartis AG | Method for applying stable coating on silicone hydrogel contact lenses |
CA2978635A1 (en) | 2015-03-11 | 2016-09-15 | University Of Florida Research Foundation, Inc. | Mesh size control of lubrication in gemini hydrogels |
US11266776B2 (en) | 2015-10-30 | 2022-03-08 | Medtronic Xomed, Inc. | Method and apparatus for irrigation |
CN108367517A (en) | 2015-12-15 | 2018-08-03 | 诺华股份有限公司 | Method for producing the haptic lens with lubricated surface |
EP3391101B1 (en) | 2015-12-15 | 2020-07-08 | Alcon Inc. | Method for applying stable coating on silicone hydrogel contact lenses |
US10809181B2 (en) | 2017-08-24 | 2020-10-20 | Alcon Inc. | Method and apparatus for determining a coefficient of friction at a test site on a surface of a contact lens |
US11029446B2 (en) | 2017-12-13 | 2021-06-08 | Alcon Inc. | Method for producing MPS-compatible water gradient contact lenses |
US10595873B2 (en) * | 2018-04-19 | 2020-03-24 | Franklin Institute of Innovation, LLC | Surgical staplers and related methods |
EP4017346A1 (en) | 2019-11-04 | 2022-06-29 | Alcon Inc. | Contact lenses with surfaces having different softness |
EP4189469A1 (en) | 2020-07-28 | 2023-06-07 | Alcon Inc. | Contact lenses with softer lens surfaces |
WO2024038390A1 (en) | 2022-08-17 | 2024-02-22 | Alcon Inc. | A contact lens with a hydrogel coating thereon |
Family Cites Families (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2308443A1 (en) * | 1972-02-22 | 1973-08-30 | Univ Erasmus | EXAMINATION DEVICE WITH CATHETER FOR EXAMINING A HOLLOW ORGAN WITH THE AID OF ULTRASOUND WAVES AND METHOD OF MAKING THE CATHETER |
US3937990A (en) * | 1974-05-28 | 1976-02-10 | Winston Ronald H | Ultrasonic composite devices |
JPS5774369A (en) * | 1980-10-28 | 1982-05-10 | Mitsui Petrochem Ind Ltd | Coating composition |
US4345058A (en) * | 1981-07-29 | 1982-08-17 | Dettling Theodore J | Urethane prepolymer repair system |
JPS5852350A (en) * | 1981-09-21 | 1983-03-28 | Toray Silicone Co Ltd | Primer composition |
CA1218839A (en) * | 1982-10-28 | 1987-03-10 | Tokuzo Kanbe | Shielding material of electromagnetic waves |
JPS6037416A (en) * | 1983-08-11 | 1985-02-26 | Arai Pump Mfg Co Ltd | Sliding material |
FR2592404B1 (en) * | 1985-12-30 | 1989-06-09 | Pradom Ltd | NOVEL COMPOSITE MATERIALS FIBER-MATRIX WITH STRICTLY POSITIONED AND ORIENTED FIBERS AND THEIR PREPARATION METHOD. |
US4838876A (en) * | 1986-04-29 | 1989-06-13 | The Kendall Company | Silicone rubber catheter having improved surface morphology |
JP2541567B2 (en) * | 1987-07-21 | 1996-10-09 | 三井石油化学工業株式会社 | Fiber material for reinforcement |
US4994047A (en) * | 1988-05-06 | 1991-02-19 | Menlo Care, Inc. | Multi-layer cannula structure |
US4911718A (en) * | 1988-06-10 | 1990-03-27 | University Of Medicine & Dentistry Of N.J. | Functional and biocompatible intervertebral disc spacer |
US5165952A (en) * | 1989-01-18 | 1992-11-24 | Becton, Dickinson And Company | Anti-infective and antithrombogenic medical articles and method for their preparation |
US5272012A (en) * | 1989-06-23 | 1993-12-21 | C. R. Bard, Inc. | Medical apparatus having protective, lubricious coating |
US5026607A (en) * | 1989-06-23 | 1991-06-25 | C. R. Bard, Inc. | Medical apparatus having protective, lubricious coating |
US5261896A (en) * | 1990-01-10 | 1993-11-16 | Rochester Medical Corporation | Sustained release bactericidal cannula |
JPH0783761B2 (en) * | 1990-10-04 | 1995-09-13 | テルモ株式会社 | Medical equipment |
US5295978A (en) * | 1990-12-28 | 1994-03-22 | Union Carbide Chemicals & Plastics Technology Corporation | Biocompatible hydrophilic complexes and process for preparation and use |
CA2065092A1 (en) * | 1991-04-05 | 1992-10-06 | Masayoshi Kurisu | Curable coating resin composition and information recording medium using the same |
US5407612A (en) * | 1991-08-13 | 1995-04-18 | Gould; Arnold S. | Method for making puncture and cut resistant material and article |
US5200263A (en) * | 1991-08-13 | 1993-04-06 | Gould Arnold S | Puncture and cut resistant material and article |
JPH06507106A (en) * | 1992-02-10 | 1994-08-11 | アドヴァンスト・カーディオヴァスキュラー・システムズ・インコーポレイテッド | Composite material with smooth surface for catheter use |
US5354259A (en) * | 1993-01-25 | 1994-10-11 | Minnesota Mining And Manufacturing Company | Microfiber fillers for orthopedic casting tapes |
US5338773A (en) * | 1993-04-19 | 1994-08-16 | Dentsply Research & Development Corp. | Dental composition and method |
US5562653A (en) * | 1994-11-16 | 1996-10-08 | Hercules Incorporated | Medical devices composed of low ceiling temperature polymers |
-
1995
- 1995-02-06 US US08/384,422 patent/US5599576A/en not_active Expired - Lifetime
-
1996
- 1996-02-05 CA CA002212181A patent/CA2212181A1/en not_active Abandoned
- 1996-02-05 AU AU49164/96A patent/AU691737B2/en not_active Ceased
- 1996-02-05 EP EP96905391A patent/EP0808182A1/en not_active Withdrawn
- 1996-02-05 JP JP8524394A patent/JPH11503033A/en not_active Ceased
- 1996-02-05 WO PCT/US1996/001624 patent/WO1996024393A1/en not_active Application Discontinuation
- 1996-05-31 US US08/658,895 patent/US5766158A/en not_active Expired - Lifetime
Also Published As
Publication number | Publication date |
---|---|
AU691737B2 (en) | 1998-05-21 |
WO1996024393A1 (en) | 1996-08-15 |
US5599576A (en) | 1997-02-04 |
EP0808182A1 (en) | 1997-11-26 |
JPH11503033A (en) | 1999-03-23 |
AU4916496A (en) | 1996-08-27 |
US5766158A (en) | 1998-06-16 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CA2212181A1 (en) | Medical apparatus with scratch-resistant coating and method making same | |
US5272012A (en) | Medical apparatus having protective, lubricious coating | |
US5026607A (en) | Medical apparatus having protective, lubricious coating | |
US6048620A (en) | Hydrophilic coating and substrates, particularly medical devices, provided with such a coating | |
US6299980B1 (en) | One step lubricious coating | |
US6709706B2 (en) | Hydrophilic coating and substrates coated therewith having enhanced durablity and lubricity | |
US5558900A (en) | One-step thromboresistant, lubricious coating | |
EP0586324B1 (en) | An article with a coating having friction-reducing properties in wet condition as well as a method for the production of such a coated article | |
US7008979B2 (en) | Coating composition for multiple hydrophilic applications | |
EP0517890B1 (en) | Biocompatible abrasion resistant coated substrates | |
AU2009226708A1 (en) | Medical device having hydrophilic coatings | |
US20110021696A1 (en) | Hydrophilic polyurethane dispersions | |
US6160032A (en) | Biocompatible coating composition | |
EP0963796A2 (en) | Hydrogel coatings containing a polyurethane-urea polymer hydrogel commingled with at least one other dissimilar polymer hydrogel | |
JP2956033B1 (en) | Electrostatic flocking steel sheet and method of manufacturing the same | |
JP2000096027A (en) | Aqueous adhesive composition for flocking and its production |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
FZDE | Discontinued |