WO1992019289A1 - Traitement de surfaces en polyurethane - Google Patents

Traitement de surfaces en polyurethane Download PDF

Info

Publication number
WO1992019289A1
WO1992019289A1 PCT/EP1992/000918 EP9200918W WO9219289A1 WO 1992019289 A1 WO1992019289 A1 WO 1992019289A1 EP 9200918 W EP9200918 W EP 9200918W WO 9219289 A1 WO9219289 A1 WO 9219289A1
Authority
WO
WIPO (PCT)
Prior art keywords
polymethacrylamide
article according
polyacrylamide
polyurethane
poly
Prior art date
Application number
PCT/EP1992/000918
Other languages
English (en)
Inventor
Ian Philip Middleton
Ian Michael Harrison
Dennis Keith Gilding
Original Assignee
Polymedica Industries, 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 Polymedica Industries, Inc. filed Critical Polymedica Industries, Inc.
Publication of WO1992019289A1 publication Critical patent/WO1992019289A1/fr

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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
    • A61L29/08—Materials for coatings
    • A61L29/085—Macromolecular materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight compounds
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6216—Polymers of alpha-beta ethylenically unsaturated carboxylic acids or of derivatives thereof
    • C08G18/6266—Polymers of amides or imides from alpha-beta ethylenically unsaturated carboxylic acids
    • 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
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • 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
    • C08J7/04—Coating
    • C08J7/046—Forming abrasion-resistant coatings; Forming surface-hardening coatings
    • 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
    • C08J7/04—Coating
    • C08J7/056—Forming hydrophilic coatings
    • 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
    • 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
    • C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
    • C08J2375/04—Polyurethanes
    • 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
    • C08J2433/00—Characterised by the use of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Derivatives of such polymers

Definitions

  • the present invention relates to an article having a polyurethane surface which has been rendered hydrophilic as well as to a method of rendering a polyurethane surface hydrophilic.
  • Articles having a polyurethane surface which has been rendered hydrophilic are useful in a number of applications.
  • various devices are used for insertion into the human body, e.g. catheters (such as urinary catheters, cardiovascular catheters, and radiological catheters), and anaesthia tubes (e.g. endotrachial tubes).
  • catheters such as urinary catheters, cardiovascular catheters, and radiological catheters
  • anaesthia tubes e.g. endotrachial tubes.
  • Such devices may be manufactured (over at least that part of their length which is inserted in the body) either of polyurethane or with a polyurethane coating and it is desirable that the polyurethane has a low coefficient of friction when in contact with aqueous body fluids. In other words, the wetted surface should feel "slippery" so that insertion of the device into the body is facilitated.
  • an article having a polyurethane surface provided with a coating of hydrophilic polyacrylamide or polymethacrylamide (other than poly(N-(monohydroxy)propyl methacrylamide) bonded to the polyurethane by residues of a compound having a first functional group reactive with the polyurethane and a second functional group reactive with the polyacrylamide or polymethacrylamide.
  • a method of rendering a polyurethane surface hydrophilic comprising treating the surface with a compound having first and second functional groups as defined in the preceding paragraph and with a hydrophilic polyacrylamide or polymethacrylamide (other than poly(N-(monohydroxy)propyl methacrylamide) whereby the latter is bonded to said surface by residues of said compound so as to provide a coating on the surface.
  • (N-(monohydroxy)propyl methacrylamide ) is intended to cover the compound having a propyl group which group has a hydroxy group as the sole substituent, which hydroxy group may be at the 1-, 2-, or 3- position.
  • poly(meth)acrylamide will be used herein as meaning either a polyacrylamide or polymethacrylamide.
  • poly(meth)acrylamide is also to be understood as covering homopoiymers of an acrylamide or methacrylamide monomer as well as (i) copolymers of such monomers with a further acrylamide or methacrylamide (thus a copolymer of an acrylamide and methacrylamid is covered), and (ii) copolymers with at least one monomer ether than an acrylamide or methacrylamide.
  • the amount of "non-(meth)acrylamide" comonomer preferably does not exceed 50% by mole.
  • the preferred poly(meth)acrylamides are homopoiymers.
  • the (meth)acrylamide from which this poly(meth)acrylamide is preferred is preferably a N-hydroxyalkyl (meth)acrylamide (other than N-(mono hydroxy) propyl methacrylamide.
  • the alkyl group has 1 to 4 carbon atoms.
  • the alkyl group is preferably bended by a terminal carbon atom to the nitrogen atom. It is also preferred that only one such N-hydroxyalkyl group is provided in the molecule.
  • the N-hydroxyalkyl group may contain more than one hydroxy group.
  • hydrophilicity of the poly(N-hydroxyalkyl (meth)acrylamide) will depend on the number of carbon atoms in the alkyl group and the number of hydroxy substituents. It is thus possible to "tailor" the poly(meth)acrylamide to the particular application.
  • N-hydroxyalkyl (meth)acrylamide monomers which may be used include the hydroxymethyl, hydroxy ethyl. and trishydroxyethyl compounds. Other hydroxy substituted alkyl groups may be used.
  • (meth)acrylamide monomers which may be used for producing the hydrophilic polymers include amino and carboxyl analogs of the hydroxy compounds.
  • one suitable monomer is N- aminopropyl (meth)acrylamide.
  • the poly(meth)acrylamide provides a coating which is a "glassy material" when dry and a hydrogel when wetted with aqueous fluids.
  • the invention is thus applicable particularly to devices (e.g. catheters; which are for insertion in the human body. Upon wetting of such a catheter by aqueous body fluids, the poly(meth)acrylamice provides the necessary low-friction coating which facilitates insertion and withdrawal of the catheter and prevents damage from "rubbing" between the catheter and the body of the patient.
  • catheter to which the present invention is applicable is a Foley balloon catheter in which the elongate body of the catheter is of a polyurethane material and the inflatable sleeve or balloon is of a natural or synthetic rubber coated with a layer of a soft polyurethane.
  • Other catheters to which the present invention is applicable are cardiovascular catheters, and radiological catheters.
  • the invention is also applicable to anaesthia tubes (e.g. endotrachial tubes).
  • the poly(meth)acrylamide provides several advantages. In particular, the wetted poly(meth)acrylamide provides low friction for insertion and low mechanical trauma to biological tissue. Additional advantages are better blood, urine and tissue compatibility as well as reduction of infection rates.
  • the poly(me th)acrylamide has a molecular weight (M n ) of at least 20,000 daltons as measured by GPC using polystyrene standard calibration.
  • M n molecular weight
  • the poly(meth)acrylamide is a homopolymer although comonomers can be included, preferably in an amount less than 10% by mole, or preferably less than 2% by mole.
  • a preferred such comonomer is methacrylic acid.
  • the compound (hereinafter referred to as the bridging agent) used for bonding the poly(meth)acrylamide to the polyurethane surface is preferably a compound having two or more functional groups each of which is capable of reaction with the polyurethane and the poly(meth)acrylamide.
  • the bridging agent may be an aliphatic, alicyclic aromatic or alicyclic compound.
  • bridging agents are di - or higher functionality isocyanates.
  • Suitable isocyanates are aliphatic diisocyanates having 3 to 10 carbon atoms, more preferably 5 to 7 carbon atoms.
  • a preferred aliphatic diisocyanate is hexamethylene diisocyanate (HDI).
  • HDI hexamethylene diisocyanate
  • the preferred compound is pure MDI or HMDI.
  • bridging agents which may be used include diacid halides (particularly diacid chlorides, e.g. ⁇ iacipcyl chloride and phthaloyl dichloride).
  • diimidazoies e.g. carbonyl diimidazole
  • carbodiimides e.g dicyclohexyl carbodiimide.
  • a further compound which is useful is cyanogen bromide.
  • the poiy(methiacrylamide coating may be applied to the polyurethane surface in a number of ways, examples of which are given below.
  • a solution of the isocyanate (eg. MDI) and poly(meth)acrylamide is formulated in a suitable solvent.
  • concentration of the diisocyanate in the solution will be in the range 0.5-5% whereas the concentration of the poly(meth)acrylamide will generally be 1-5%.
  • Suitable solvents include dimethyl formamide (DMF) as well as mixtures of DMF with lower boiling solvents eg. tetrahydrofuran or methyl ethyl ketone.
  • DMAC, DMSO and NMP may also be used.
  • the polyurethane surface is dipped into the abovedescribed solution, typically for a time of less than 10 seconds. After this dipping process, the surface is "dried” to leave the surface coating of poly(meth)acrylamide bonded to the polyurethane. surface by isocyanate compound residues. Typically the drying condition includes IR drying (eg. 4-8 mins at 65-70°C) followed by drying (in a fan oven) for several hours at 50-70°C, (e.g. 3-8 hrs at 60°C).
  • the polyurethane surface is initially dipped into a solution of the isocyanate (the isocyanate solution) so that isocyanate compound residues become bonded to the polyurethane surface, followed by dipping into a solution of the poly(meth)acrylamide (the poly(meth)acrylamide solution), preferably containing a catalyst for forming polyurethanes.
  • the solvent for the isocyanate solution is preferably a halocarbon, preferably one containing chlorine and/or fluorine.
  • Preferred examples of such solvents are low boiling liquids such as methylene chloride, chloroform etc.
  • the concentration of the isocyanate is preferably 1-5%.
  • the dipping time of the polyurethane surface in the isocyanate solution is preferably less than 10 seconds.
  • the polyurethane surface is removed from the solution and the solvent is allowed to evaporate in air prior to the surface being dipped in the poly(meth)acrylamide solution containing a polyurethane formation catalyst.
  • a suitable concentration range for the poly(meth)acrylamide is 0.5-5% and the preferred solvent is a mixture of DMF (50-75%) and THF (25-50%).
  • Other solvents which can be used include DMAC, DMSO, and NMP.
  • the polyurethane formation catalyst is preferably used in an amount of 1 part of catalyst per 500-10000 parts of poly(meth)acrylamide.
  • the catalyst may for example be stannous octoate, stannous chloride, diethyl zinc, diphenyl zinc, and other common organometallic catalysts used in polyurethane formation reactions. This dipping process is preferably effected for less than 10 seconds.
  • the surface Upon removal of the polyurethane surface from the poly(meth)acrylamide solution, the surface is dried preferably at a temperature of 65-70°C for 8-12 minutes. Finally the surface is washed with water and dried in warm air.
  • the poly(meth)acrylamide coating may include an antimicrobial agent or a drug for delivery to the body of the patient, eg. copper or silver compounds, chlorhexidine or other antiseptic, or an antibiotic.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Materials For Medical Uses (AREA)

Abstract

Elément présentant une surface en polyuréthane qui a été rendue hydrophile et méthode consistant à rendre hydrophile ladite surface en polyuréthane. L'invention porte sur un élément présentant une surface en polyuréthane enduite d'un revêtement de polyacrylamide ou de polyméthacrylamide hydrophile (autre que que le poly(N-(mono hydroxy)propyl méthacrylamdide) lié au polyuréthane par le résidu d'un composé renfermant un premier groupe fonctionnel qui réagit avec le polyuréthane et un deuxième groupe fonctionnel qui réagit avec le polyacrylamide ou le polyméthacrylamide.
PCT/EP1992/000918 1991-04-25 1992-04-27 Traitement de surfaces en polyurethane WO1992019289A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB919109122A GB9109122D0 (en) 1991-04-25 1991-04-25 Treatment of polyurethane surfaces
GB9109122.3 1991-04-25

Publications (1)

Publication Number Publication Date
WO1992019289A1 true WO1992019289A1 (fr) 1992-11-12

Family

ID=10694076

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1992/000918 WO1992019289A1 (fr) 1991-04-25 1992-04-27 Traitement de surfaces en polyurethane

Country Status (3)

Country Link
AU (1) AU1650792A (fr)
GB (1) GB9109122D0 (fr)
WO (1) WO1992019289A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0611576A1 (fr) * 1993-02-08 1994-08-24 Terumo Kabushiki Kaisha Outil médical avec une surface lubrifiante dans un milieu humide et méthode pour sa fabrication
EP0892008A1 (fr) * 1997-07-18 1999-01-20 Ucb, S.A. Composition de revêtement pour un film en plastique
US5869127A (en) * 1995-02-22 1999-02-09 Boston Scientific Corporation Method of providing a substrate with a bio-active/biocompatible coating
US6179817B1 (en) 1995-02-22 2001-01-30 Boston Scientific Corporation Hybrid coating for medical devices
US6197051B1 (en) 1997-06-18 2001-03-06 Boston Scientific Corporation Polycarbonate-polyurethane dispersions for thromobo-resistant coatings
US6723121B1 (en) 1997-06-18 2004-04-20 Scimed Life Systems, Inc. Polycarbonate-polyurethane dispersions for thrombo-resistant coatings
US20130323291A1 (en) * 2012-05-31 2013-12-05 Biocoat Incorporated Hydrophilic and non-thrombogenic polymer for coating of medical devices
WO2018126796A1 (fr) * 2017-01-05 2018-07-12 华南理工大学 Procédé de préparation d'une surface antibactérienne sur une surface de matériau à usage médical
US20180361031A1 (en) * 2015-06-15 2018-12-20 Rheinisch-Westfalische Technische Hochschule (Rwth) Aachen Method for Bonding a Polyurethane Polymer to a Substrate, in Particular for the Manufacturing of Stents
US11167064B2 (en) 2016-07-14 2021-11-09 Hollister Incorporated Hygienic medical devices having hydrophilic coating

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0093093A1 (fr) * 1982-04-22 1983-11-02 Astra Meditec AB Préparation d'un revêtement hydrophile
EP0093094A1 (fr) * 1982-04-22 1983-11-02 Astra Meditec AB Procédé de préparation d'un revêtement hydrophile
EP0106004A1 (fr) * 1981-05-18 1984-04-25 Astra Tech Aktiebolag Procédé de façonnage d'un revêtement hydrophyle sur un substrat
EP0140854A2 (fr) * 1983-10-04 1985-05-08 Alfa-Laval Agri International Ab Surfaces répulsives à l'encontre des bactéries
EP0379156A2 (fr) * 1989-01-17 1990-07-25 UNION CARBIDE CHEMICALS AND PLASTICS COMPANY INC. (a New York corporation) Revêtements hydrophiles lubrifiés améliorés

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0106004A1 (fr) * 1981-05-18 1984-04-25 Astra Tech Aktiebolag Procédé de façonnage d'un revêtement hydrophyle sur un substrat
EP0093093A1 (fr) * 1982-04-22 1983-11-02 Astra Meditec AB Préparation d'un revêtement hydrophile
EP0093094A1 (fr) * 1982-04-22 1983-11-02 Astra Meditec AB Procédé de préparation d'un revêtement hydrophile
EP0140854A2 (fr) * 1983-10-04 1985-05-08 Alfa-Laval Agri International Ab Surfaces répulsives à l'encontre des bactéries
EP0379156A2 (fr) * 1989-01-17 1990-07-25 UNION CARBIDE CHEMICALS AND PLASTICS COMPANY INC. (a New York corporation) Revêtements hydrophiles lubrifiés améliorés

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5441488A (en) * 1993-02-08 1995-08-15 Terumo Kabushiki Kaisha Medical tool having lubricious surface in a wetted state and method for production thereof
EP0611576A1 (fr) * 1993-02-08 1994-08-24 Terumo Kabushiki Kaisha Outil médical avec une surface lubrifiante dans un milieu humide et méthode pour sa fabrication
US6099563A (en) * 1995-02-22 2000-08-08 Boston Scientific Corporation Substrates, particularly medical devices, provided with bio-active/biocompatible coatings
US6179817B1 (en) 1995-02-22 2001-01-30 Boston Scientific Corporation Hybrid coating for medical devices
US5869127A (en) * 1995-02-22 1999-02-09 Boston Scientific Corporation Method of providing a substrate with a bio-active/biocompatible coating
US6723121B1 (en) 1997-06-18 2004-04-20 Scimed Life Systems, Inc. Polycarbonate-polyurethane dispersions for thrombo-resistant coatings
US6197051B1 (en) 1997-06-18 2001-03-06 Boston Scientific Corporation Polycarbonate-polyurethane dispersions for thromobo-resistant coatings
WO1999003916A1 (fr) * 1997-07-18 1999-01-28 Ucb, S.A. Composition de revetement pour film plastique
AU737842B2 (en) * 1997-07-18 2001-08-30 Ucb Coating composition for a plastic film
EP0892008A1 (fr) * 1997-07-18 1999-01-20 Ucb, S.A. Composition de revêtement pour un film en plastique
US20130323291A1 (en) * 2012-05-31 2013-12-05 Biocoat Incorporated Hydrophilic and non-thrombogenic polymer for coating of medical devices
US20180361031A1 (en) * 2015-06-15 2018-12-20 Rheinisch-Westfalische Technische Hochschule (Rwth) Aachen Method for Bonding a Polyurethane Polymer to a Substrate, in Particular for the Manufacturing of Stents
US11167064B2 (en) 2016-07-14 2021-11-09 Hollister Incorporated Hygienic medical devices having hydrophilic coating
WO2018126796A1 (fr) * 2017-01-05 2018-07-12 华南理工大学 Procédé de préparation d'une surface antibactérienne sur une surface de matériau à usage médical
US11426496B2 (en) 2017-01-05 2022-08-30 South China University Of Technology Method for preparing anti-bacterial surface on medical material surface

Also Published As

Publication number Publication date
GB9109122D0 (en) 1991-06-12
AU1650792A (en) 1992-12-21

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