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WO1996003163A1 - Materiau polyester composite dote d'une surface glissante - Google Patents

Materiau polyester composite dote d'une surface glissante Download PDF

Info

Publication number
WO1996003163A1
WO1996003163A1 PCT/US1995/008836 US9508836W WO9603163A1 WO 1996003163 A1 WO1996003163 A1 WO 1996003163A1 US 9508836 W US9508836 W US 9508836W WO 9603163 A1 WO9603163 A1 WO 9603163A1
Authority
WO
WIPO (PCT)
Prior art keywords
lubricous
particulate
composite material
catheter
polyester
Prior art date
Application number
PCT/US1995/008836
Other languages
English (en)
Inventor
Tai C. Cheng
Douglas C. Harrington
Robert D. Ainsworth
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 JP8505788A priority Critical patent/JPH10503103A/ja
Priority to EP95927163A priority patent/EP0773803A1/fr
Publication of WO1996003163A1 publication Critical patent/WO1996003163A1/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
    • A61L29/12—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
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M25/00—Catheters; Hollow probes
    • A61M25/0043—Catheters; Hollow probes characterised by structural features
    • A61M25/0045—Catheters; Hollow probes characterised by structural features multi-layered, e.g. coated
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
    • A61M25/00—Catheters; Hollow probes
    • A61M25/10—Balloon catheters
    • A61M25/104—Balloon catheters used for angioplasty

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 therein until the preshaped distal tip of the guiding catheter is disposed within the aorta adjacent the ostium of the desired coronary artery.
  • the guiding catheter is twisted or torqued from the proximal end to turn the distal tip of the guiding catheter so that it can be guided into the desired coronary ostium.
  • a guidewire and a balloon dilatation catheter are introduced into and advanced through the guiding catheter to the distal
  • the dilatation catheter is then advanced out of the distal tip of the guiding catheter, over the previously advanced guidewire, until the
  • the balloon on the distal extremity of the dilatation catheter is properly positioned across the lesion. Once properly positioned, the balloon is
  • pressures e.g. , generally 4-1 2 atmospheres
  • One or more inflations may be necessary to
  • Additional stenoses may be dilatated with
  • Patent 4,554,929 (Samson et al. ); U.S. Patent 4,582, 185 (Samson);
  • Patent 4,748,986 (Morrison et al. ); U.S. Patent 4,898,577 (Badger et
  • the fixed-wire dilatation catheters generally have an outer tubular member with an inflatable balloon on the distal section thereof which is capable of dilating a stenosis, and a guiding member extending out through the distal end of the balloon which aids in advancing the catheter to a desired location within the patient's vasculature. They also usually have no inner tubular member and therefore have lower profiles, e.g. transverse dimensions, than over-the-wire dilatation catheters having the same inflated balloon size. Moreover, because the fixed-wire catheters have the guidewire or guiding member fixed or at least restricted as to longitudinal movement, these catheters generally have greater pushability than over-the-wire type
  • the rapid exchange type dilatation catheter has a short guidewire receiving sleeve or inner lumen extending through the flexible distal portion of the catheter which extends out of the guiding catheter into the patient's coronary artery during the angioplasty procedure.
  • the sleeve extends proximally a distance of at least 10 cm and usually not more than about 50 cm from a first guidewire port in the
  • the catheter wall which extends distally from the second guidewire port, preferably to a location proximal to the proximal end of the inflatable balloon to aid in the removal of the catheter from a guidewire.
  • the structure of the catheter allows for the rapid exchange of the catheter without the need for the use of an exchange wire or adding a guidewire extension to the proximal end of the guidewire.
  • the design of this catheter has been widely praised by the medical profession and has met with much commercial success in the market place because of its unique design. A substantial improvement in the rapid exchange type
  • perfusion ports are provided in the catheter shaft, proximal and distal to the balloon, which are in fluid communication with the guidewire receiving inner lumen to allow blood to perfuse distal to the catheter when the balloon is inflated.
  • Lubricous coatings have been applied to the surfaces of guiding catheters, dilatation catheters and other intraluminal catheters in order to reduce the friction between the surfaces of these catheters and other components of the catheter systems in which the catheters are employed during the intravascular procedures.
  • fluoropolymer linings such as Teflon ® are very frequently employed as the inner linings of guiding catheters in order to reduce the friction between the inner lining of the guiding catheter and the guidewire and the catheters which might be advanced through the inner lumen of the guiding catheter.
  • Lubricous silicone coatings have been applied to the surfaces of guidewires and of dilatation catheters to likewise reduce the frictional characteristics of these devices.
  • the application of these lubricous coatings and linings are for the most part complicated manufacturing processes.
  • very frequently these coatings and linings are not very durable and lose substantial portions of their lubricity during the intraluminal or intravascular procedure.
  • the present invention is directed to an improved composite plastic material having a very durable lubricous surface and particularly to tubular products for intraluminal catheter procedures within a human patient made from such composite materials.
  • the material of the invention generally includes a biocompatible polymer matrix having finely divided lubricous particulate matter incorporated within the matrix.
  • the polymer matrix can be formed of thermoplastic materials, particularly thermoplastic polyesters are preferred when the final product has a tubular shape because thermoplastic polyesters can be easily extruded or otherwise formed in a conventional fashion and can be more readily joined to other components.
  • thermoplastic polyesters can be easily extruded or otherwise formed in a conventional fashion and can be more readily joined to other components.
  • the tubular products of the invention can be formed into the shafts for intraluminal catheters such as balloon dilatation catheters for angioplasty procedures in a conventional manner.
  • the presently preferred polyester matrix is a polyester sold under the trademark HYTREL ® by DuPont, particularly grades 7246 and 8238.
  • HYTREL is believed to be a copolymer of predominantly polybutylene terephthalate and a lesser amount of polytetramethylene ether glycol esterified with dimethyl terephthalate. Other minor components may be included.
  • Fig. 1 is an elevational view, partially in section of a balloon dilatation catheter embodying features of the invention.
  • Fig. 2 is a transverse cross-sectional view of the catheter shown in Fig. 1 taken along the lines 2-2.
  • Fig. 3 is a transverse cross-sectional view of the catheter shown in Fig. 1 taken along the lines 3-3.
  • Figs. 1 -3 illustrate a balloon dilatation catheter
  • the dilatation catheter generally includes an outer tubular member 10, a dilatation balloon 11 on the distal portion of the outer tubular member, an inner member 12 disposed within the outer tubular member and the balloon and a multi-arm adapter 13 mounted on the proximal ends of the inner and outer tubular members.
  • the distal end of the balloon 1 1 is sealed about the distal end of the inner tubular member 12 so that injection of inflation fluid under significant pressure through annular lumen 14 to the interior of the balloon will result in the inflation thereof.
  • a guidewire 15 is slidably disposed within the inner lumen 16 of the inner tubular member 12.
  • the distal end of the catheter is provided with a self venting means such as described in U.S. Patent 4,638,805 (Powell).
  • a radiopaque marker 17 is disposed about the inner tubular member 12 at the mid-point of the balloon 1 1 to facilitate the
  • the brachial marker 20 and femoral marker 21 are provided on the proximal end of the inner tubular member 12.
  • composite material which generally includes a polymer matrix, preferably a readily extrudable thermoplastic polyester and
  • a finely divided lubricous particulate matter which range on the average from about 0.1 to about 100 microns, preferably about 0.5 to about 20 microns, in maximum dimensions.
  • the amount of particulate matter in the polymer matrix is a finely divided lubricous particulate matter which range on the average from about 0.1 to about 100 microns, preferably about 0.5 to about 20 microns, in maximum dimensions.
  • SUBSTITUTE ⁇ -E fR' LE 2 thereof may range from about 0.5 to about 50%, preferably about 2 to about 20%, of the precured mixture thereof. As used herein all percentages are weight percent unless noted otherwise. Up to about 1 % of a dispersing agent, such as lecithin, silicone oil, vegetable oil, polyethylene wax or mixtures thereof, may be incorporated into the mixture to facilitate effective mixing of the particulate within the polymer resin.
  • HYTREL it has been found that the graphite particles can be fed into the extruder along with the HYTREL to provide
  • Particularly suitable lubricous particulate materials include graphite, fluoropolymers such as Teflon ® , molybdenum disulfide, titanium carbide, molybdenum carbide, graphite difluoride or mixtures thereof.
  • Presently preferred lubricous particulate include Micro 850 and Micro 250 graphite available from the Asbury Graphite Mills, located in Asbury
  • This graphite has an average maximum particle size from about 3 to about 10 microns in maximum dimension.
  • silicone oils such as dimethylsiloxane polymers with a viscosity between about 300 and 100,000 centipoise, preferably about 1000 to about 30,000 centipoise, can be incorporated along with the solid lubricous particulate in amounts of up to 10%, preferably about 0.5 to about 4%.
  • Formation of the products of the invention typically involve intimately mixing the lubricous particulate into the uncured or partially cured polymer resin which forms the matrix of the cured product. If needed, a dispersant may be first mixed with the lubricous particulate to
  • the dispersant may be advantageously added to the lubricous particulate as a solution of isopropyl alcohol or other suitable solvent to facilitate the incorporation thereof.
  • the finely divided lubricous particulate has a tendency to agglomerate and an intimate and uniform mixture of the particulate within the polymer matrix can be very difficult to obtain without a dispersant.
  • the polymer-particulate mixture is then preferably extruded in a conventional manner into a tubular product having the desired dimensions. After extruding, the tubular product is then cured.
  • a mixture was prepared containing 96% of HYTREL (Grade 7246) and 4% graphite powder and extruded into pellets.
  • the pellets are extruded into a tubular product.
  • the tubular member is then cut to length and used in the manufacture of a prototype dilatation catheter as shown in Figs. 1-3.
  • the tubular member will have a low coefficient of friction.
  • the composite material of the invention can be utilized in a wide variety intraluminal catheter components.
  • the material can be used to form the outer tubular member in an over-the-wire dilatation catheter or a fixed-wire dilatation catheter. All or a portion of the outer tubular member may be formed of the polymer
  • the material can also be used to form the inflatable member or balloon of a dilatation catheter.
  • Guidewire receiving inner tubular members such as described in the Yock and Horzewski et al. patents, which have been incorporated herein, may be made of the composite material formed of polymer and low friction particulate.
  • Another use is the formation of guiding catheters in which the composite material is used to form at least the inner liner of the catheter to provide the lubricous inner lumen required in this type of intravascular catheter.
  • Other uses include shafts and inflatable members of urethral dilatation catheters and Foley type catheters.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Engineering & Computer Science (AREA)
  • Anesthesiology (AREA)
  • Composite Materials (AREA)
  • Materials Engineering (AREA)
  • Biophysics (AREA)
  • Pulmonology (AREA)
  • Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Hematology (AREA)
  • Materials For Medical Uses (AREA)
  • Media Introduction/Drainage Providing Device (AREA)
  • Compositions Of Macromolecular Compounds (AREA)

Abstract

Un élément de cathéter intravasculaire à faible friction est constitué d'une matrice de polyester dans laquelle est incorporé un granulé fin et glissant comprenant de préférence une ou plusieurs particules glissantes appropriées choisies dans le groupe consistant en graphite, disulfure de molybdène, TiC, MoC, difluorure de graphite et des fluoropolymères. Ce polyester est de préférence un copolymère contenant une quantité prédominante de térephtalate de polybutylène et de moindres quantités de composants telles que du polytétraméthylène éther glycol qui a été estérifié avec un téréphtalate de diméthyle, de l'HYTREL® par exemple. Avec ce matériau à faible friction on fabrique généralement des éléments tubulaires internes ou externes de cathéters de dilatation à fil fixe ou entourant le fil. En plus de ce granulé glissant, ou peut incorporer dans cette matrice un fluide à base de polysiloxane.
PCT/US1995/008836 1994-07-25 1995-07-17 Materiau polyester composite dote d'une surface glissante WO1996003163A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP8505788A JPH10503103A (ja) 1994-07-25 1995-07-17 潤滑性表面を有する複合体ポリエステル材料
EP95927163A EP0773803A1 (fr) 1994-07-25 1995-07-17 Materiau polyester composite dote d'une surface glissante

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US28029194A 1994-07-25 1994-07-25
US08/280,291 1994-07-25

Publications (1)

Publication Number Publication Date
WO1996003163A1 true WO1996003163A1 (fr) 1996-02-08

Family

ID=23072457

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US1995/008836 WO1996003163A1 (fr) 1994-07-25 1995-07-17 Materiau polyester composite dote d'une surface glissante

Country Status (4)

Country Link
EP (1) EP0773803A1 (fr)
JP (1) JPH10503103A (fr)
CA (1) CA2195948A1 (fr)
WO (1) WO1996003163A1 (fr)

Cited By (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996034635A3 (fr) * 1995-05-05 1997-02-13 Advanced Cardiovascular System Dispositif intraluminal a surface glissante
WO1997026027A1 (fr) * 1996-01-16 1997-07-24 Advanced Cardiovascular Systems, Inc. Corps axial de catheter, glissant et a fixation facile
WO1999000153A1 (fr) * 1997-06-30 1999-01-07 Becton Dickinson And Company Lubrifiant contenant de la lecithine pour instrument medical
WO1999055403A1 (fr) * 1998-04-28 1999-11-04 Scimed Life Systems, Inc. Elements tubulaires a surface lubrifiee pour dispositifs medicaux
US6217547B1 (en) 1996-01-16 2001-04-17 Advanced Cardiovascular Systems, Inc. Lubricous and readily bondable catheter shaft
US6503353B1 (en) 1996-05-13 2003-01-07 Schneider (Usa) Inc. Method for making a catheter
WO2006055198A1 (fr) 2004-11-12 2006-05-26 Eastman Chemical Company Compositions polymeres et copolymeres de polyester contenant des particules de carbure de titane
WO2006104724A1 (fr) 2005-03-31 2006-10-05 Eastman Chemical Company Compositions de polymeres et de copolymeres de polyester contenant des particules d'un ou de plusieurs composes de metaux de transition
WO2007086855A3 (fr) * 2005-01-27 2007-11-15 Boston Scient Ltd Dispositifs medicaux comprenant des nanocomposites
US7300967B2 (en) 2004-11-12 2007-11-27 Eastman Chemical Company Polyester polymer and copolymer compositions containing metallic titanium particles
US7355068B2 (en) 2006-01-04 2008-04-08 Eastman Chemical Company Oxidation system with internal secondary reactor
US7358389B2 (en) 2006-01-04 2008-04-15 Eastman Chemical Company Oxidation system employing internal structure for enhanced hydrodynamics
US7361784B2 (en) 2004-09-02 2008-04-22 Eastman Chemical Company Optimized liquid-phase oxidation
US7368523B2 (en) 2004-11-12 2008-05-06 Eastman Chemical Company Polyester polymer and copolymer compositions containing titanium nitride particles
US7390921B2 (en) 2004-09-02 2008-06-24 Eastman Chemical Company Optimized liquid-phase oxidation
US7399882B2 (en) 2004-09-02 2008-07-15 Eastman Chemical Company Optimized liquid-phase oxidation
US7482482B2 (en) 2004-09-02 2009-01-27 Eastman Chemical Company Optimized liquid-phase oxidation
US7495125B2 (en) 2004-09-02 2009-02-24 Eastman Chemical Company Optimized liquid-phase oxidation
US7498003B2 (en) 2004-09-02 2009-03-03 Eastman Chemical Company Optimized liquid-phase oxidation
US7507857B2 (en) 2004-09-02 2009-03-24 Eastman Chemical Company Optimized liquid-phase oxidation
US7563926B2 (en) 2004-09-02 2009-07-21 Eastman Chemical Company Optimized liquid-phase oxidation
US7582793B2 (en) 2004-09-02 2009-09-01 Eastman Chemical Company Optimized liquid-phase oxidation
US7586000B2 (en) 2004-09-02 2009-09-08 Eastman Chemical Company Optimized liquid-phase oxidation
US7608732B2 (en) 2005-03-08 2009-10-27 Eastman Chemical Company Optimized liquid-phase oxidation
US7608733B2 (en) 2004-09-02 2009-10-27 Eastman Chemical Company Optimized liquid-phase oxidation
US7659427B2 (en) 2004-09-02 2010-02-09 Eastman Chemical Company Optimized liquid-phase oxidation
US7662880B2 (en) 2004-09-03 2010-02-16 Eastman Chemical Company Polyester polymer and copolymer compositions containing metallic nickel particles
EP2068993A4 (fr) * 2006-07-28 2010-04-21 Taylor Medical Inc Composants de cathéter formés d'un mélange de polymère avec des particules ou fibres
US7745512B2 (en) 2005-09-16 2010-06-29 Eastman Chemical Company Polyester polymer and copolymer compositions containing carbon-coated iron particles
US7776942B2 (en) 2005-09-16 2010-08-17 Eastman Chemical Company Polyester polymer and copolymer compositions containing particles of titanium nitride and carbon-coated iron
US7884232B2 (en) 2005-06-16 2011-02-08 Eastman Chemical Company Optimized liquid-phase oxidation
US7901636B2 (en) 2004-09-02 2011-03-08 Eastman Chemical Company Optimized liquid-phase oxidation
US7910071B2 (en) 2004-09-02 2011-03-22 Eastman Chemical Company Optimized liquid-phase oxidation
US7960581B2 (en) 2004-09-02 2011-06-14 Grupo Petrotemex, S.A. De C.V. Optimized liquid-phase oxidation
US8114356B2 (en) 2004-09-02 2012-02-14 Grupo Pretrotemex, S.A. de C.V. Optimized liquid-phase oxidation
US8178054B2 (en) 2004-09-02 2012-05-15 Grupo Petrotemex, S. A. DE C. V. Optimized liquid-phase oxidation
US8501986B2 (en) 2004-11-29 2013-08-06 Grupo Petrotemex, S.A. De C.V. Optimized liquid-phase oxidation
US8901272B2 (en) 2007-02-02 2014-12-02 Grupo Petrotemex, S.A. De C.V. Polyester polymers with low acetaldehyde generation rates and high vinyl ends concentration
US8987408B2 (en) 2005-06-16 2015-03-24 Grupo Petrotemex, S.A. De C.V. High intrinsic viscosity melt phase polyester polymers with acceptable acetaldehyde generation rates
EP1502609B1 (fr) * 2003-07-29 2015-08-26 Terumo Kabushiki Kaisha Cathéter avec un élément expansible
US9267007B2 (en) 2005-09-16 2016-02-23 Grupo Petrotemex, S.A. De C.V. Method for addition of additives into a polymer melt
US11103272B2 (en) 2017-02-02 2021-08-31 Precision Thoracic, Llc Minimally invasive methods and apparatus for target-tissue excision
US11331087B2 (en) 2005-07-26 2022-05-17 Precision Thoracic, Llc Minimally invasive methods and apparatus
US12102372B2 (en) 2018-07-31 2024-10-01 Prana Thoracic, Inc. Tissue resection apparatus

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EP1794225A1 (fr) * 2004-09-03 2007-06-13 Eastman Chemical Company Compositions a base de polymere et de copolymere de polyester contenant des particules de molybdene metalliques
JP5295618B2 (ja) * 2008-04-09 2013-09-18 オリンパス株式会社 医療用チューブ
JP5331393B2 (ja) * 2008-06-30 2013-10-30 オリンパス株式会社 複合材料および医療用チューブ
JP5639354B2 (ja) * 2009-09-09 2014-12-10 株式会社潤工社 医療用チューブ

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WO1994000176A1 (fr) * 1992-06-26 1994-01-06 Advanced Cardiovascular Systems, Inc. Materiau composite a surface antifriction pour catheters

Cited By (54)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996034635A3 (fr) * 1995-05-05 1997-02-13 Advanced Cardiovascular System Dispositif intraluminal a surface glissante
US6390992B1 (en) 1995-05-05 2002-05-21 Advanced Cardiovascular Systems, Inc. Intraluminal device with lubricious surface
WO1997026027A1 (fr) * 1996-01-16 1997-07-24 Advanced Cardiovascular Systems, Inc. Corps axial de catheter, glissant et a fixation facile
US6217547B1 (en) 1996-01-16 2001-04-17 Advanced Cardiovascular Systems, Inc. Lubricous and readily bondable catheter shaft
US6277093B1 (en) 1996-01-16 2001-08-21 Advanced Cardiovascular Systems, Inc. Lubricious and readily bondable catheter shaft
US6503353B1 (en) 1996-05-13 2003-01-07 Schneider (Usa) Inc. Method for making a catheter
WO1999000153A1 (fr) * 1997-06-30 1999-01-07 Becton Dickinson And Company Lubrifiant contenant de la lecithine pour instrument medical
WO1999055403A1 (fr) * 1998-04-28 1999-11-04 Scimed Life Systems, Inc. Elements tubulaires a surface lubrifiee pour dispositifs medicaux
US6086970A (en) * 1998-04-28 2000-07-11 Scimed Life Systems, Inc. Lubricious surface extruded tubular members for medical devices
EP1502609B1 (fr) * 2003-07-29 2015-08-26 Terumo Kabushiki Kaisha Cathéter avec un élément expansible
US7910071B2 (en) 2004-09-02 2011-03-22 Eastman Chemical Company Optimized liquid-phase oxidation
US7977505B2 (en) 2004-09-02 2011-07-12 Eastman Chemical Company Optimized liquid-phase oxidation
US8470257B2 (en) 2004-09-02 2013-06-25 Grupo Petrotemex, S.A. De C.V. Optimized liquid-phase oxidation
US8178054B2 (en) 2004-09-02 2012-05-15 Grupo Petrotemex, S. A. DE C. V. Optimized liquid-phase oxidation
US8114356B2 (en) 2004-09-02 2012-02-14 Grupo Pretrotemex, S.A. de C.V. Optimized liquid-phase oxidation
US7361784B2 (en) 2004-09-02 2008-04-22 Eastman Chemical Company Optimized liquid-phase oxidation
US7960581B2 (en) 2004-09-02 2011-06-14 Grupo Petrotemex, S.A. De C.V. Optimized liquid-phase oxidation
US7390921B2 (en) 2004-09-02 2008-06-24 Eastman Chemical Company Optimized liquid-phase oxidation
US7399882B2 (en) 2004-09-02 2008-07-15 Eastman Chemical Company Optimized liquid-phase oxidation
US7902396B2 (en) 2004-09-02 2011-03-08 Eastman Chemical Company Optimized liquid-phase oxidation
US7482482B2 (en) 2004-09-02 2009-01-27 Eastman Chemical Company Optimized liquid-phase oxidation
US7901636B2 (en) 2004-09-02 2011-03-08 Eastman Chemical Company Optimized liquid-phase oxidation
US7495125B2 (en) 2004-09-02 2009-02-24 Eastman Chemical Company Optimized liquid-phase oxidation
US7498003B2 (en) 2004-09-02 2009-03-03 Eastman Chemical Company Optimized liquid-phase oxidation
US7498002B2 (en) 2004-09-02 2009-03-03 Eastman Chemical Company Optimized liquid-phase oxidation
US7507857B2 (en) 2004-09-02 2009-03-24 Eastman Chemical Company Optimized liquid-phase oxidation
US7563926B2 (en) 2004-09-02 2009-07-21 Eastman Chemical Company Optimized liquid-phase oxidation
US7582793B2 (en) 2004-09-02 2009-09-01 Eastman Chemical Company Optimized liquid-phase oxidation
US7586000B2 (en) 2004-09-02 2009-09-08 Eastman Chemical Company Optimized liquid-phase oxidation
US7659427B2 (en) 2004-09-02 2010-02-09 Eastman Chemical Company Optimized liquid-phase oxidation
US7608733B2 (en) 2004-09-02 2009-10-27 Eastman Chemical Company Optimized liquid-phase oxidation
US7662880B2 (en) 2004-09-03 2010-02-16 Eastman Chemical Company Polyester polymer and copolymer compositions containing metallic nickel particles
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EP0773803A1 (fr) 1997-05-21
CA2195948A1 (fr) 1996-02-08

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