WO2000014146A1 - Method of bonding polymers and medical devices comprising materials bonded by said method - Google Patents
Method of bonding polymers and medical devices comprising materials bonded by said method Download PDFInfo
- Publication number
- WO2000014146A1 WO2000014146A1 PCT/US1999/020318 US9920318W WO0014146A1 WO 2000014146 A1 WO2000014146 A1 WO 2000014146A1 US 9920318 W US9920318 W US 9920318W WO 0014146 A1 WO0014146 A1 WO 0014146A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- polymeric body
- adhesive
- silicone
- polymeric
- medical device
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
- C08J7/123—Treatment by wave energy or particle radiation
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
- C08J5/124—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives using adhesives based on a macromolecular component
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L77/00—Compositions of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Compositions of derivatives of such polymers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
- A61M25/0009—Making of catheters or other medical or surgical tubes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2383/04—Polysiloxanes
Definitions
- the present invention relates to an improved method of bonding polymeric materials, in particular, polymeric materials comprising silicone, and further, to medical devices comprising materials bonded together by said method More specifically, the present invention relates to a method of surface treating such materials so that the bondability of the materials is improved The present invention further relates to medical devices formed at least in part from materials so treated and subsequently bonded together Medical devices incorporating materials that are so treated exhibit increased bond strength and integrity
- medical devices having a wide variety of clinical uses have been developed in recent years
- medical devices have been developed that can be used to replace indigenous mammalian organs that have become damaged and/or deteriorated, such as artificial heart valves or artificial joints, to help control or regulate defective organs, such as pacemakers, to replace damaged tissue, such as artificial skin grafts or breast implants, or to provide a less-invasive alternative to traditional treatment modalities, as is the case with intravascular therapeutic and diagnostic catheters
- Such medical devices in the least often times represent a less traumatic treatment alternative, and often times, as is the case with artificial joints, represent the only viable treatment available
- medical devices require exacting specifications in order to perform adequately under the rigorous conditions in which they are required to perform
- such medical devices may be primarily comprised of polymeric materials that are non-thrombogenic, non-immunogenic, flexible, manipulatable, that exhibit both radial and longitudinal strength and/or, in certain applications, that are biodegradable Inasmuch as there
- the bond sites of such medical devices are subject to the same exacting specifications of the overall device and thus, desirably exhibit a high degree of strength and integrity.
- the bond sites must be able to withstand the handling and motion required to insert the device.
- Such bond sites also must be able to withstand the rigorous sterilization regimens, e.g., autoclave, ethylene oxide and gamma radiation sterilization regimens, to which medical devices are typically subjected.
- the bond sites must be able to withstand any external pressure applied by the tissue into which it may be implanted or utilized.
- the bond sites In medical devices such as intravascular catheters, the bond sites must be able to withstand the relatively high internal pressures, e.g., as high as 10 atmospheres to about 20 or more atmospheres, utilized to inflate the balloon portion of such catheters.
- Such high internal pressure not only affects the bond between the shaft portion of a catheter and the balloon, but also, since such high pressures can cause the shaft portion of the catheter to stretch and constrict, may affect other bonds present along the length of the catheter.
- bond sites must be strong enough to resist failure.
- bond failure or weakness can result from a variety of circumstances. For example, the application of inadequate amounts of adhesive, as well as uneven application of adhesive, to a bond site can result in weakness or failure of the bond.
- silicone rubber has desirably low thrombogenicity, and is flexible and manipulatable
- the incorporation of silicone and silicone-containing polymers into medical devices is problematic as such polymers generally do not adhere adequately with other materials typically used in medical device applications.
- functionalized monomers may be incorporated into a polymer to improve the adhesion of polymeric materials, such monomeric formulation modifications may fundamentally alter other desirable properties of the material.
- the present invention relates to an improved method of bonding polymeric materials, in particular, polymeric materials comprising silicone, and further, to medical devices comprising polymeric materials bonded together by said method. More specifically, the method of the present invention involves surface treating a polymeric body, preferably a polymeric body comprising silicone, such that the character of the surface of the polymeric body changes in a manner such that bondability is enhanced. Furthermore, the method of the present invention enhances the bondability of the polymeric materials, while leaving the remaining, mechanical, physical and biological properties of the polymeric material substantially unchanged. It has now been discovered that the bondability of a polymeric material may be enhanced by surface treating the polymeric material in a manner that changes the character of the surface of the polymeric material.
- bonds formed in the practice of the present invention provide the advantage of being based upon both physical and chemical interactions, and thus, are stronger bonds.
- the method of the present invention has been found to work particularly well in enhancing the bondability of silicone, pa ⁇ icularly medical grade silicone elastomers. Silicone is generally difficult to bond to other materials, including other silicone materials. However, surface treatment in accordance with the method of the present invention results in sufficient modification of the character of the surface of a silicone such that the bondability of silicone is enhanced. In the case of silicone, it is believed that surface treatment in accordance with the method of the present invention at least partially functionalizes the surface of the silicone body with hydroxyl groups, carboxyl groups, or both. By then choosing a material or an adhesive with functionality capable of reacting with the hydroxyl or carboxyl groups, the silicone body is then capable of forming covalent bonds with enhanced integrity and strength to such compatible materials and adhesives.
- the surface treatment results in the surface of the polymeric body comprising silicone becoming at least partially functionalized with chemically reactive moieties. More preferably, the surface treatment results in the surface of the polymeric body comprising silicone becoming at least partially functionalized with hydroxyl functionality, carboxyl functionality, or a combination thereof.
- a compatible adhesive is then applied to at least a portion of the surface of the polymeric body comprising silicone, or alternatively to at least a portion of the surface of the polymeric body to which it is to be bonded, at least one of said surfaces and the surfaces of the two polymeric bodies are brought into contact under conditions effective to bond the surfaces.
- the adhesive is a UV-curable adhesive with functionality capable of reacting with the hydroxyl functionality or carboxyl functionality on the surface of the polymeric body comprising silicone, e.g., the growing chain derived from acrylic functionality.
- the surface of the polymeric body comprising silicone may simply be brought into contact with the surface of a second, compatible polymeric body under conditions effective to bond the surfaces without the use of an adhesive.
- the present invention is well suited to enhance the bondability of polymeric materials such as polyethylene terephthalates; polyether/polyester block copolymers; polyether/amide block copolymers; polyamides; polyimides; polyurethanes; hydrocarbon polymers such as polyethylene and propylene; synthetic hydrocarbon elastomers; natural rubber; fluorinated silicone polycarbonate; urethane; combinations of these and the like.
- polymeric materials such as polyethylene terephthalates; polyether/polyester block copolymers; polyether/amide block copolymers; polyamides; polyimides; polyurethanes; hydrocarbon polymers such as polyethylene and propylene; synthetic hydrocarbon elastomers; natural rubber; fluorinated silicone polycarbonate; urethane; combinations of these and the like.
- Many of these polymeric materials find use in medical devices such as various types of catheters, and catheter devices for coronary angioplasty, including balloon catheters.
- the present invention provides a medical device incorporating
- the present invention provides a medical device that comprises a first polymeric body comprising a first surface that has been subjected to a surface treatment such that the bondability of the first surface is enhanced relative to a similar, untreated first surface, a second polymeric body comprising a second surface comprising functionality compatible with the first surface, said second surface being in a confronting relationship to the first surface such that the first surface and second surface directly bond by virtue of the formation of covalent bonds.
- the first surface is at least partially functionalized with chemically reactive moieties by virtue of the surface treatment.
- the adhesive has functionality capable of reacting with the functionality on the first surface.
- the present invention provides a medical device that comprises a first polymeric body comprising a first surface that has been subjected to a surface treatment such that the bondability of the first surface is enhanced relative to a similar, untreated first surface, a second polymeric body comprising a second surface, said second surface being in a confronting relationship to the first surface and a cured adhesive bonding said first surface to said second surface.
- the first surface is at least partially functionalized with chemically reactive moieties by virtue of the surface treatment.
- the adhesive has functionality capable of reacting with the functionality on the first surface.
- Figure 1 shows a perspective view of an apparatus that may be used in the method of the present invention.
- Figure 2 shows a perspective view of a first representative medical device in accordance with the present invention.
- Figure 3 shows a perspective view of a second representative medical device in accordance with the present invention.
- the method of the present invention comprises the steps of subjecting the surface of the polymeric material of which it is desired to enhance bondability to a surface treatment under conditions effective to change the character of the surface of the polymeric material. More specifically, the surface treatment in accordance with the method of the present invention results in the surface of the polymeric material becoming at least partially functionalized with chemically reactive moieties, e.g., hydroxyl groups, amide groups, amino groups, epoxy groups, carboxyl groups, ester groups, carbonyl groups, combinations of these and the like. Subsequent to the treatment, the polymeric material may be bonded to another material, e.g. by direct bonding to a compatible material or by applying a compatible adhesive to at least a portion of the surface of one of the materials.
- chemically reactive moieties e.g., hydroxyl groups, amide groups, amino groups, epoxy groups, carboxyl groups, ester groups, carbonyl groups, combinations of these and the like.
- the polymeric material may be bonded to another material, e.g
- a plasma is generated by creating an electrical discharge in a gaseous atmosphere maintained at a suitable pressure
- plasma treatment systems comprise a chamber which is capable of being maintained at a desired pressure, e g , sub-atmospheric or atmospheric pressure, within which the polymeric materials to be surface treated are placed and the appropriate electrical discharge is created
- a desired pressure e g , sub-atmospheric or atmospheric pressure
- gas plasma treatment systems suitable for use in the practice of the present invention are commercially available and such systems are generally known
- One specific example of a preferred gas plasma treatment system is commercially available as a Plasma Science 350 from Himont/Plasma Science, Foster City, California This system is equipped with an RF solid-state generator operating at 13 56 MHz and from 0 to 500 watts power output It also includes a microprocessor controller and a complete vacuum pump package
- the system further includes a treatment chamber having an unimpeded work volume of 42.5 cm by 34 3 cm by 17.5 cm.
- oxidative gas 18 is a mixture of pure oxygen in air
- apparatus 10 is operated at a base gas pressure of from about 30 mTorr to about 100 mTorr.
- the O 2 :Air ratio is preferably maintained at from about 0.5: 1 to about 5: 1, more preferably at about 1 : 1.
- the air gas flow rate is preferably from about 80 standard mL per minute to about 100 standard mL per minute and the oxygen gas flow rate is preferably from about 80 standard mL per minute to about 100 standard mL per minute.
- the plasma treatment and post oxidative gas treatment are desirably carried out long enough to achieve the desired degree of surface treatment, i.e., forming bondable functionality on the surface of the polymeric material.
- such direct bonding may be catalyzed by application of energy from an appropriate energy source, e.g., electromagnetic radiation, electron beam irradiation, and the like, or by the utilization of appropriate chemical reagents, e.g., moisture, acids, bases, and the like.
- an appropriate energy source e.g., electromagnetic radiation, electron beam irradiation, and the like
- chemical reagents e.g., moisture, acids, bases, and the like.
- the adhesive may be applied to the surface of the treated polymeric material, the surface of the material to which the treated polymeric material is to be bonded, or to both. If the adhesive is to be applied to the surface treated polymeric material, it is preferred that the adhesive be applied to the surface treated polymeric material within about 60 minutes, more preferably within about 30 minutes, of plasma treatment.
- Either one or both of the polymeric materials to be bonded may be surface treated in accordance with the method of the present invention. Specifically, if both of the polymeric materials to be bonded are known to be difficult to bond, both surfaces are advantageously surface treated in accordance with the method of the present invention. If, however, only one of the materials is known to be difficult to bond, surface treatment of only the material known to be difficult to bond will result in the enhanced bondability of the material and thus, enhanced bond strength between the two materials.
- the method of the present invention may be applied to any polymeric material for which it is desired to enhance the bondability thereof, e.g., any material that is difficult to bond, and that comprises, or is capable of having imparted thereto, chemically reactive moieties.
- the term “bondability” is meant to indicate the ability of a material to form chemical covalent bonds with another material or an adhesive.
- the phrases “enhanced bondability” or “enhanced bond strength” are meant to indicate an improvement in the ability of a material to form a covalent bond, or an improved covalent bond strength, respectively, relative to the ability of a similar, untreated material to form a covalent bond, or to the covalent bond formed by a similar, untreated material, respectively.
- polymeric bodies to be bonded may further comprise additional constituents such as antioxidants, ultraviolet and other light stabilizers, catalyst residues from manufacture, organic and inorganic fillers such as calcium carbonates, clays, barium sulfate used as the radioopaque filler for medical devices, carbon blacks and other pigments. If present, any such additional constituents may be used in accordance with conventional practices.
- additional constituents such as antioxidants, ultraviolet and other light stabilizers, catalyst residues from manufacture, organic and inorganic fillers such as calcium carbonates, clays, barium sulfate used as the radioopaque filler for medical devices, carbon blacks and other pigments. If present, any such additional constituents may be used in accordance with conventional practices.
- Examples of such medical device applications include, but are not limited to, bonding a silicone catheter segment to a silicone or non-silicone catheter segment; bonding a silicone balloon to a silicone or non-silicone catheter shaft; bonding a silicon catheter tip to a silicone or non-silicone catheter segment (e.g., guiding angiographic and angioplasty catheters); bonding a silicone implant component to a silicone or non-silicone implant component; bonding a non-silicone catheter hub to a segment of silicone catheter tubing; and bonding a silicone film to a non-silicone or another silicone film.
- Figure 2 One specific example of a representative medical device in accordance with the present invention is illustrated in Figure 2.
- Figure 2 is a perspective view of a balloon catheter 20, e.g., as is used in coronary dilations.
- Balloon catheter 20 comprises shaft 22 and balloon 24.
- Shaft 22 may comprise any of the suitable materials listed hereinabove, or may be a multilayer tubing comprising combinations thereof.
- Balloon 24 preferably comprises a silicone rubber elastomer, and furthermore, preferably has a burst pressure of at least 10 pounds per square inch (psi).
- psi pounds per square inch
- adhesive may be used to bond different components of the medical device. This embodiment of the invention is illustrated in Figure 3.
- Figure 3 is a perspective view of a balloon catheter 30, comprising shaft 32 and balloon 34.
- Shaft 32 is bonded to balloon 34 with adhesive 36.
- Shaft 32 may comprise any of the suitable polymeric materials discussed hereinabove, or may be a multi-layer tubing comprising combinations of such polymeric materials.
- Balloon 34 preferably comprises a silicon rubber elastomer and furthermore, preferably has a burst pressure of at least 10 psi.
- the surface treated polymeric material may be directly bonded to another compatible material, or alternatively, may be bonded to another material by the application of a compatible adhesive. If an adhesive bond is desired, any adhesive capable of chemically interacting with the chemically reactive moieties present on the surface of the surface treated polymeric material may be utilized in the practice of the method of the present invention. Preferably, the adhesive chosen will be capable of chemically interacting with the surface of the surface treated polymeric material, i.e., as by forming covalent bonds with the chemically reactive moieties on the surface of the polymeric material.
- suitable adhesives include UV curable adhesives (such as that commercially available under the trade designation "Dymax 189-MT” from Dymax, Torrington, CT), cyanoacrylate adhesives (such as that commercially available under the trade designation "Sicomet” from Henkels, Kanakee, Illinois), two part epoxy adhesives (such as that commercially available under the trade designation "Fusor” from Lord Company, Raleigh, NC).
- UV curable adhesives such as that commercially available under the trade designation "Dymax 189-MT” from Dymax, Torrington, CT
- cyanoacrylate adhesives such as that commercially available under the trade designation "Sicomet” from Henkels, Kanakee, Illinois
- two part epoxy adhesives such as that commercially available under the trade designation “Fusor” from Lord Company, Raleigh, NC
- Urethane adhesives such as that commercially available under the trade designation “Tyrite” from Lord Company, Raleigh, NC
- silicone adhesives such as that commercially available under the trade designation "Med-151 1” from
- Typical solvents which can be used for this purpose include alcohols such as methanol, ethanol, isopropanol, and the like; ketones such as acetone, methylethyl ketone, and the like; chlorinated hydrocarbons such as methytene chloride, 1,1, 1- trichloroethane, and the like; hydrocarbons such as pentanes, n-hexane, petroleum ethers, other cleaning spirits, and the like; ethers such as diisopropyl ether, dioxane, tetrahydrofuran, and the like; and mixtures thereof.
- alcohols such as methanol, ethanol, isopropanol, and the like
- ketones such as acetone, methylethyl ketone, and the like
- chlorinated hydrocarbons such as methytene chloride, 1,1, 1- trichloroethane, and the like
- hydrocarbons such as pentanes, n-hexan
- Example 1 It is also within the scope of the present invention to utilize aqueous solutions of nonionic anionic, and cationic surfactants as washing fluids, if desired, followed by rinsing with water or distilled water to remove any surface impurities that could otherwise potentially interfere with the surface treatment in accordance with the present invention.
- aqueous solutions of nonionic anionic, and cationic surfactants as washing fluids, if desired, followed by rinsing with water or distilled water to remove any surface impurities that could otherwise potentially interfere with the surface treatment in accordance with the present invention.
- UV-curable adhesive (commercially available under the trade designation "Dymax 189-mt” from Dymax, Torrington, CT) was applied on the distal 2 - 4 mm of the PEBAX and Hytrel tubes.
- the PEBAX and Hytrel tubes were then quickly inserted 2 cm into respective silicone tubes The silicone and/or plastic tubes were rotated to ensure even distribution of the adhesive between the tubes
- Control samples were prepared in the same manner with the exception that the tubing was not surface treated prior to bonding.
- the surface treated tube assemblies were then subjected to a variety of post-bonding treatments. Specifically, one group was held for three days at room temperature. An additional group was subjected to wet aging, i.e., held for 7 days at 55°C and 80% relative humidity. Yet another group was dry aged; held for 7 days at 70°C at less than 20% relative humidity. Finally, two groups were subject to sterilization treatments, specifically, one group was sterilized twice by ethylene oxide (ETO) sterilization while another group was sterilized once with gamma radiation at 25-38 Kgy.
- ETO ethylene oxide
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE69917293T DE69917293T2 (en) | 1998-09-04 | 1999-09-03 | Method for joining polymers and medical devices containing materials bonded by this method |
EP99945504A EP1109854B1 (en) | 1998-09-04 | 1999-09-03 | Method of bonding polymers and medical devices comprising materials bonded by said method |
CA002343169A CA2343169A1 (en) | 1998-09-04 | 1999-09-03 | Method of bonding polymers and medical devices comprising materials bonded by said method |
JP2000568899A JP4580101B2 (en) | 1998-09-04 | 1999-09-03 | Method for manufacturing medical catheter and medical catheter |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US09/148,389 US6299596B1 (en) | 1998-03-20 | 1998-09-04 | Method of bonding polymers and medical devices comprising materials bonded by said method |
US09/148,389 | 1998-09-04 |
Publications (1)
Publication Number | Publication Date |
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WO2000014146A1 true WO2000014146A1 (en) | 2000-03-16 |
Family
ID=22525564
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1999/020318 WO2000014146A1 (en) | 1998-09-04 | 1999-09-03 | Method of bonding polymers and medical devices comprising materials bonded by said method |
Country Status (6)
Country | Link |
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US (1) | US6299596B1 (en) |
EP (1) | EP1109854B1 (en) |
JP (1) | JP4580101B2 (en) |
CA (1) | CA2343169A1 (en) |
DE (1) | DE69917293T2 (en) |
WO (1) | WO2000014146A1 (en) |
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WO2008003914A2 (en) * | 2006-07-07 | 2008-01-10 | Arkema France | Adhesion activator for thermoplastic polymer elastomer substrates or polyamide substrates, and corresponding adhesion method |
FR2903417A1 (en) * | 2006-07-07 | 2008-01-11 | Arkema France | Adhesion activator for improving bonding of thermoplastic elastomer or polyamide, e.g. in shoe soles, comprises agent reacting with groups and/or complexing chains of the polymer |
US20080187693A1 (en) * | 2004-09-06 | 2008-08-07 | Coloplast A/S | Silicone Urisheath with Integrated Adhesive |
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Also Published As
Publication number | Publication date |
---|---|
DE69917293D1 (en) | 2004-06-17 |
CA2343169A1 (en) | 2000-03-16 |
JP2002524597A (en) | 2002-08-06 |
US6299596B1 (en) | 2001-10-09 |
EP1109854A1 (en) | 2001-06-27 |
DE69917293T2 (en) | 2005-05-12 |
EP1109854B1 (en) | 2004-05-12 |
JP4580101B2 (en) | 2010-11-10 |
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