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WO1996003164A1 - Materiau de revetement hydrophile a usage intracorporel - Google Patents

Materiau de revetement hydrophile a usage intracorporel Download PDF

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Publication number
WO1996003164A1
WO1996003164A1 PCT/US1995/009267 US9509267W WO9603164A1 WO 1996003164 A1 WO1996003164 A1 WO 1996003164A1 US 9509267 W US9509267 W US 9509267W WO 9603164 A1 WO9603164 A1 WO 9603164A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrophilic
coating
plasticizer
monomer
hydrogen
Prior art date
Application number
PCT/US1995/009267
Other languages
English (en)
Inventor
Eugene Michal
Original Assignee
Advanced Cardiovascular Systems, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Advanced Cardiovascular Systems, Inc. filed Critical Advanced Cardiovascular Systems, Inc.
Priority to EP95928107A priority Critical patent/EP0772467A1/fr
Priority to JP08505890A priority patent/JP2000511946A/ja
Publication of WO1996003164A1 publication Critical patent/WO1996003164A1/fr

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
    • A61L29/14—Materials characterised by their function or physical properties, e.g. lubricating compositions
    • 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

Definitions

  • This invention generally relates to intraluminal catheters, such as guiding catheters and balloon dilatation catheters used in percutaneous transluminal coronary angioplasty (PTCA).
  • PTCA percutaneous transluminal coronary angioplasty
  • a guiding catheter having a preshaped distal tip is percutaneously introduced by a Seldinger technique into the cardiovascular system of a patient and advanced within the ⁇ system until the preshaped distal tip of the guiding catheter is disposed within the ascending aorta adjacent the ostium of the desired coronary artery.
  • the guiding catheter is twisted or torqued from its proximal end, which extends outside the patient, to turn the distal tip of the guiding catheter so that it can be guided into the desired coronary ostium.
  • balloon dilatation catheter are introduced into and advanced through the guiding catheter to the distal tip thereof out of the distal tip of the guiding catheter until the balloon on the distal extremity of the dilatation catheter is properly positioned across the lesion.
  • the balloon is inflated to a predetermined size with radiopaque liquid at relatively high pressures ⁇ e.g., generally 4-12 atmospheres) to dilate the stenotic region of the diseased artery.
  • radiopaque liquid at relatively high pressures ⁇ e.g., generally 4-12 atmospheres
  • One or more inflations may be necessary to effectively dilate the stenosis.
  • Additional stenoses may be dilatated with the same catheter.
  • the balloon is deflated so that the dilatation catheter can be removed from the dilated stenosis and normal blood flow will resume through the dilated artery.
  • balloon dilatation catheters which are suitable for coronary angioplasty. They include conventional over-the-wire catheters, fixed-wire catheters, rapid exchange type catheters and perfusion type catheters.
  • Lubricous coatings have been applied to the surfaces of guiding catheters, dilatation catheters and other intraluminal catheters in order to reduce the coefficient of friction of the surfaces of these catheters and to facilitate the advancement and withdrawal of these catheters through various body lumens.
  • silicone coatings have been applied to the exterior of various catheters in order to reduce the coefficient of friction of the catheter surface, but these coatings are frequently not very durable and lose substantial portions of their lubricity during an intraluminal or intravascular procedure.
  • Durable, lubricous silicone coatings are described in copending application Serial No. 07/913,775, filed July 13, 1992, but the application of these lubricous coatings and linings described in the copending application are for the most part complicated manufacturing procedures.
  • This invention is directed to an improved intracorporeal device, such as a catheter, having a durable, flexible coating which is
  • the durable, flexible coating of the invention is generally formed at least in part from a copolymer product comprising a hydrophilic monomeric material and a plasticizing monomeric material.
  • the copolymer product comprises at least about 50% of the hydrophilic monomer and from about 2% to about 50%, preferably about 5% to about 30%, of the plasticizing monomer.
  • all references to percent refer to percent by weight unless otherwise noted.
  • the co- polymer is treated to attach latent photoactive groups to facilitate the bonding of the reacted copolymer to the desired substrate, as taught in U.S. Patent 5,002,582, which is incorporated herein by reference. Additional disclosures are found in U.S. Patent 4,722,906, U.S. Patent 4,973,493 and U.S.
  • the coating formed is a durable, flexible hydrophilic coating. At least about 30%, preferably at least about 40%, of the coating should comprise the copolymer of the hydrophilic monomer and the plasticizing monomer. Other hydrophilic polymers may be incorporated into the coating to modify coating properties. The additional hydrophilic polymers should likewise be treated to attach latent photoactive groups as previously described.
  • hydrophilic monomeric material forming the copolymer and the hydrophilic monomeric material forming any hydrophilic polymer incorporated into the coating with the copolymer are preferably selected from one or more hydrophilic monomers having the general formula
  • ⁇ CH CR2R3
  • R 1 is a hydrogen or pyrrolidone
  • R 2 is a hydrogen or a methyl group
  • R 3 is a hydrogen or -COR 4
  • R 4 is -NH 2 , -OH, -NHC(CH 3 ) 2 CH 2 CO R 5,
  • hydrophilic monomers include acrylamide and N-vinyl
  • a suitable hydrophilic plasticizing monomer may at least in part be selected from the group consisting of (methoxy)poly(ethylene glycol) monomethacrylate, poly.ethylene glycol) monomethacrylate,
  • the plasticizer material may also be at least in part a hydrophobic plasticizing monomer having the general structure
  • CH 2 C COOR 7 where R 7 is a straight chain or branched alkyl group having from 2 to 22 carbon atoms, and particularly is a plasticizing monomer selected from at least one of the
  • plasticizing monomers are particularly suitable for use by incorporating with the hydrophilic monomer before the mixture is polymerized. It is sometimes desirable to partially polymerize the hydrophilic monomeric material, incorporate a water soluble, relatively non-volatile (at room temperature) polyol in amounts of about 1 to about 20% (by weight), preferably about 3% to about 8% (by weight). Suitable
  • polyols include polyethylene glycol, polypropylene glycol and copolymers of ethylene oxide and propylene oxide and glycerol.
  • the copolymers of ethylene oxide and propyiene oxide should be of the general formula HO(-CH 3 CHCH 2 O-) m -(CH 2 CH 2 O) n -CH 2 CH 2 OH where m and n are positive integers.
  • the invention is generally directed to a coating for an intracorporeal device and particularly to an expandable portion of intraluminal catheter such as the balloon on a dilatation catheter for coronary angioplasty.
  • the dilatation catheters have an elongated catheter shaft with at least one inner lumen which is adapted to direct inflation liquid therethrough and an inflatable member or balloon on the distal extremity of the catheter shaft which has an interior in fluid communication with the inner lumen within the shaft.
  • the inflatable member or balloon is adapted to dilate body lumens such as stenotic coronary and peripheral arteries, prostatic urethras and the like.
  • the balloon material is a thermoplastic polymer or a blend of thermoplastic polymers such as polyethylene, polyethylene terephthalate, polyesters (e.g. Nylon) and suitable ionomers.
  • the balloon of the invention is made by forming a tubular product of the desired polymeric material using conventional melt processing techniques, such as extruding. After the tubular product of the desired composition is formed, it may be blown in a conventional fashion into a relatively inelastic balloon.
  • the polymers from which the balloon is made may be cross- linked by the use of a suitable cross-linking agent such as a peroxide or an amine, or by irradiation with gamma or electron beam radiation. It is
  • a cross linking agent in amounts ranging from about 0.1 to about 2 %, preferably about 0.1 to about 1 % into the polymer from which the balloon is made before it is formed to facilitate cross-linking upon irradiation.
  • Suitable cross-linking agents include components having carbon-carbon unsaturation, e.g. ethylenic double bonds, such as allyl, methallyl, propargyl or vinyl groups.
  • Preferred cross linking agents include triallyl cyanurate, triallyl isocyanurate, triallyl trimellitate, triallyl trimesate, tetraallyl pyromellitate and the diallyl ester of 1 ,1 ,3-trimethyl-5-carboxy-3-(p-carboxyphenyl) indane.
  • the catheter is dipped into an aqueous solution containing about 0.5 to about 20% (by wt.), preferably about 2 to about 7%, polymer solids, which includes the reacted copolymer of the hydrophilic monomeric material and the plasticizing monomeric material and an additional hydrophilic polymer.
  • the catheter is dipped at a rate of about 5 to about 40 cm per minute.
  • the catheter is irradiated to cross link the polymeric coating material, e.g. ultraviolet radiation from a mercury lamp for about 10 seconds to about 10 minutes at an intensity of about 5 to about 260 milliwatts, preferably about 10 to about 50 milliwatts, per cm 2 of catheter surface.
  • the coating of the invention on the catheter surface is quite durable, exhibits good flexibility and is characterized by very low coefficients of friction.
  • the catheter can be readily advanced through guiding catheters and tortuous coronary anatomy.
  • the coating also eases the passage of the balloon into tight stenoses.
  • FIG. 1 is an elevational view of an over-the-wire dilatation catheter embodying features of the invention.
  • Fig. 1 illustrates a dilatation catheter 10 which includes an elongated catheter shaft 1 comprising an inner tubular member 12 and an outer tubular member 13, a balloon or inflatable member 14 and an adapter 15.
  • the inner tubular member 12 has an inner lumen 16 which is adapted to receive the guidewire 17 and defines with the outer tubular member 13 an annular lumen 18 which is adapted to direct inflation fluid to the interior of the balloon 14.
  • the arm 19 of the adapter 15 directs inflation fluid from a source not shown into the annular lumen.
  • the balloon 14 are provided with a durable yet flexible hydrophilic coating 20 in accordance with the present invention.
  • the balloon 14 alone may be provided with the flexible hydrophilic coating of the invention.
  • the dry coating thickness of the hydrophilic coating generally will range from about 0.00002 to about 0.001 inch (0.0005- 0.025 mm), preferably about 0.00005 to about 0.0005 inch (0.0013-
  • the various catheter components may be formed of conventional materials, e.g. polyethylene, polyvinyl chloride, polyamide and the like.
  • the means used to join the various catheter components may be conventional such as by heat or laser bonding, heat shrinking or use of a suitable adhesive.
  • the various catheter components will generally be of conventional size depending upon the intended end use. The following is a example of applying a coating to the distal portion of a balloon dilatation catheter for angioplasty procedures. The catheter surface was first cleaned with 2-propanol and plasma treated with oxygen to prepare the surface for optimal coating adhesion.
  • the catheter was dipped into an aqueous bath containing 3% polymer solids which includes about 50% of a first hydrophilic polymer and about 50% of a second hydrophilic polymer which is a copolymer of a hydrophilic monomer and a plasticizer monomer in accordance with the invention.
  • the bath was maintained at a temperature of about 20 * C.
  • the catheter surface was then subjected to ultraviolet radiation from a mercury lamp at an intensity of 12 milliwatts/cm 2 for about 3 minutes to cure the coating. Two coats were applied in essentially the same manner.
  • the coating was found to be durable, very flexible and lubricous. When subjected to an aqueous based liquid, the coating had a coefficient of friction of about 0.03. No cracks or delaminations of the coating were noted.
  • the first hydrophilic polymer was a polymer material sold by the Bio-Metric Systems, Inc. (BSD, under the designation PV05 which is a polymer primarily formed of n-vinyl pyrrolidone.
  • BSD Bio-Metric Systems, Inc.
  • PV05 a polymer primarily formed of n-vinyl pyrrolidone.
  • the second hydrophilic polymer was a polymer material sold by BSI under the designation PA05 which is a polymer primarily formed of acrylamide, but which included 7.2% methoxy polyethylene glycol (1000 mol. wt.) mono methacrylate (Methoxy PEG 1000 MMA).
  • PA05 polymer material sold by BSI under the designation PA05 which is a polymer primarily formed of acrylamide, but which included 7.2% methoxy polyethylene glycol (1000 mol. wt.) mono methacrylate (Methoxy PEG 1000 MMA).
  • PA05 methoxy polyethylene glycol (1000 mol. wt.) mono methacrylate
  • the second polymer as sold had likewise been treated to attach latent photoactive groups to facilitate the bonding of the reacted polymer to the desired substrate as previously described.
  • a 3% polymer solids bath was prepared containing 1.5% PV05 and 1.5% PA03 which is the same as PA05 but without the Methoxy PEG 1000 MMa plasticizing monomer.
  • a coating was prepared on the balloon of a dilatation catheter in the same manner as in the previous example. The dry, cured coating formed cracks and some coating segments delaminated from the underlying balloon surface which potentially can reduce performance and result in in-vivo particle generation.
  • the coating of the invention may be employed in a wide variety of devices in contact with various body fluids both intracorporeally and extracorporeally.
  • the coating may be utilized on catheters adapted to dilate prostatic urethras and other body lumens and the coating can be utilized on dialysis machines.
  • other body fluids both intracorporeally and extracorporeally.

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  • Health & Medical Sciences (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Materials For Medical Uses (AREA)
  • Paints Or Removers (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Revêtement hydrophile souple placé sur un dispositif destiné à venir en contact avec un liquide biologique et en particulier pour substrats souples faisant partie de dispositifs intracorporels tels que des ballonnets sur un cathéter de dilatation. Ledit revêtement comprend au moins 30 % d'un copolymère d'un monomère hydrophile et d'un monomère plastifiant. Un monomère hydrophile actuellement préféré est l'acrylamide, et le monomère plastifiant actuellement préféré est le méthoxy (polyéthylène-glycol) monométhacrylate dans lequel la fraction polyéthylène-glycol possède un poids moléculaire d'environ 1.000. D'autres polymères hydrophiles, tels que la n-vinylpyrrolidone, peuvent également être incorporés dans ledit revêtement. Ces deux polymères sont traités de sorte qu'ils se lient à des groupes photoactifs latents et facilitent l'adhésion desdits polymères à un substrat.
PCT/US1995/009267 1994-07-22 1995-07-21 Materiau de revetement hydrophile a usage intracorporel WO1996003164A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
EP95928107A EP0772467A1 (fr) 1994-07-22 1995-07-21 Materiau de revetement hydrophile a usage intracorporel
JP08505890A JP2000511946A (ja) 1994-07-22 1995-07-21 体内使用のための親水性被覆材料

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US27923994A 1994-07-22 1994-07-22
US08/279,239 1994-07-22

Publications (1)

Publication Number Publication Date
WO1996003164A1 true WO1996003164A1 (fr) 1996-02-08

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ID=23068189

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/009267 WO1996003164A1 (fr) 1994-07-22 1995-07-21 Materiau de revetement hydrophile a usage intracorporel

Country Status (4)

Country Link
EP (1) EP0772467A1 (fr)
JP (1) JP2000511946A (fr)
CA (1) CA2195744A1 (fr)
WO (1) WO1996003164A1 (fr)

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5998534A (en) * 1998-06-19 1999-12-07 Ppg Industries Ohio, Inc. Water-soluble or water-dispersible addition copolymer
US6455500B1 (en) 1998-03-10 2002-09-24 University Of Southern California Radiation therapy methods
US6951642B2 (en) 2001-09-28 2005-10-04 3M Innovative Properties Company Water-in-oil emulsions with anionic groups, compositions, and methods
US7030203B2 (en) 2001-09-28 2006-04-18 3M Innovative Properties Company Water-in-oil emulsions with ethylene oxide groups, compositions, and methods
EP1961429A3 (fr) * 1998-11-20 2008-09-24 Coloplast A/S Procédé de stérilisation d'un dispositif médical comportant un revêtement hydrophile
US7442402B2 (en) 1998-04-27 2008-10-28 Surmodics, Inc. Bioactive agent release coating
GB2448871A (en) * 2007-04-30 2008-11-05 Inion Ltd Modulation of inflammatory and immune responses in the treatment of inflammation using substituted heterocyclic compounds
US7541048B2 (en) 2004-04-06 2009-06-02 Surmodics, Inc. Coating compositions for bioactive agents

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7097850B2 (en) 2002-06-18 2006-08-29 Surmodics, Inc. Bioactive agent release coating and controlled humidity method
US20040111144A1 (en) * 2002-12-06 2004-06-10 Lawin Laurie R. Barriers for polymeric coatings

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2022120A6 (fr) * 1968-08-13 1970-07-31 Nat Patent Developm
US4055682A (en) * 1971-11-19 1977-10-25 High Voltage Engineering Corporation Catheter and the method of making
US4111922A (en) * 1972-07-10 1978-09-05 Johnson & Johnson Hydrophilic random interpolymer from quaternary ammonium monomers and method for making same
GB2064556A (en) * 1979-12-05 1981-06-17 Kendall & Co Water absorptive polymer composition
US4373009A (en) * 1981-05-18 1983-02-08 International Silicone Corporation Method of forming a hydrophilic coating on a substrate
GB2190387A (en) * 1986-05-15 1987-11-18 Yarsley Technical Centre Limit Hydrophilic copolymers for wound dressings and other biomedical uses
EP0389632A1 (fr) * 1988-08-09 1990-10-03 Toray Industries, Inc. Materiau medical glissant et son procede de production
EP0521605A2 (fr) * 1991-05-16 1993-01-07 Ioptex Research Inc. Polymères sreffés lubrifiants biocompatibles
WO1994026336A1 (fr) * 1993-05-12 1994-11-24 Target Therapeutics, Inc. Catheters lubrifies

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5538512A (en) * 1993-02-25 1996-07-23 Zenzon; Wendy J. Lubricious flow directed catheter

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2022120A6 (fr) * 1968-08-13 1970-07-31 Nat Patent Developm
US4055682A (en) * 1971-11-19 1977-10-25 High Voltage Engineering Corporation Catheter and the method of making
US4111922A (en) * 1972-07-10 1978-09-05 Johnson & Johnson Hydrophilic random interpolymer from quaternary ammonium monomers and method for making same
GB2064556A (en) * 1979-12-05 1981-06-17 Kendall & Co Water absorptive polymer composition
US4373009A (en) * 1981-05-18 1983-02-08 International Silicone Corporation Method of forming a hydrophilic coating on a substrate
GB2190387A (en) * 1986-05-15 1987-11-18 Yarsley Technical Centre Limit Hydrophilic copolymers for wound dressings and other biomedical uses
EP0389632A1 (fr) * 1988-08-09 1990-10-03 Toray Industries, Inc. Materiau medical glissant et son procede de production
EP0521605A2 (fr) * 1991-05-16 1993-01-07 Ioptex Research Inc. Polymères sreffés lubrifiants biocompatibles
WO1994026336A1 (fr) * 1993-05-12 1994-11-24 Target Therapeutics, Inc. Catheters lubrifies

Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6455500B1 (en) 1998-03-10 2002-09-24 University Of Southern California Radiation therapy methods
US7442402B2 (en) 1998-04-27 2008-10-28 Surmodics, Inc. Bioactive agent release coating
US5998534A (en) * 1998-06-19 1999-12-07 Ppg Industries Ohio, Inc. Water-soluble or water-dispersible addition copolymer
EP2065061A3 (fr) * 1998-11-20 2009-08-26 Coloplast A/S Procédé de stérilisation d'un dispositif médical comportant un revêtement hydrophile
US9138510B2 (en) 1998-11-20 2015-09-22 Coloplast A/S Sterilized ready-to-use catheter
EP1961429A3 (fr) * 1998-11-20 2008-09-24 Coloplast A/S Procédé de stérilisation d'un dispositif médical comportant un revêtement hydrophile
US7030203B2 (en) 2001-09-28 2006-04-18 3M Innovative Properties Company Water-in-oil emulsions with ethylene oxide groups, compositions, and methods
US8026327B2 (en) 2001-09-28 2011-09-27 3M Innovative Properties Company Water-in-oil emulsions with ethylene oxide groups, compositions, and methods
US8636993B2 (en) 2001-09-28 2014-01-28 3M Innovative Properties Company Water-in-oil emulsions with anionic groups, compositions, and methods
US6951642B2 (en) 2001-09-28 2005-10-04 3M Innovative Properties Company Water-in-oil emulsions with anionic groups, compositions, and methods
US7541048B2 (en) 2004-04-06 2009-06-02 Surmodics, Inc. Coating compositions for bioactive agents
US7544673B2 (en) 2004-04-06 2009-06-09 Surmodics, Inc. Coating compositions for bioactive agents
GB2448871A (en) * 2007-04-30 2008-11-05 Inion Ltd Modulation of inflammatory and immune responses in the treatment of inflammation using substituted heterocyclic compounds

Also Published As

Publication number Publication date
JP2000511946A (ja) 2000-09-12
CA2195744A1 (fr) 1996-02-08
EP0772467A1 (fr) 1997-05-14

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