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WO2022202805A1 - Copolymère hydrophile et instrument médical - Google Patents

Copolymère hydrophile et instrument médical Download PDF

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Publication number
WO2022202805A1
WO2022202805A1 PCT/JP2022/013126 JP2022013126W WO2022202805A1 WO 2022202805 A1 WO2022202805 A1 WO 2022202805A1 JP 2022013126 W JP2022013126 W JP 2022013126W WO 2022202805 A1 WO2022202805 A1 WO 2022202805A1
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group
carbon atoms
linear
branched
oso
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PCT/JP2022/013126
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English (en)
Japanese (ja)
Inventor
政則 倉本
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Terumo Corp
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Terumo Corp
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Publication date
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    • 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
    • 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
    • A61L31/00—Materials for other surgical articles, e.g. stents, stent-grafts, shunts, surgical drapes, guide wires, materials for adhesion prevention, occluding devices, surgical gloves, tissue fixation devices
    • A61L31/08—Materials for coatings
    • A61L31/10—Macromolecular materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—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 a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/38—Esters containing sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon

Definitions

  • the present invention relates to a medical device having a hydrophilic copolymer and a surface lubricating layer formed using the hydrophilic copolymer.
  • An object of the present invention is to provide a new hydrophilic copolymer capable of forming a surface lubricating layer exhibiting durability (lubricity maintaining property).
  • R 51 is a hydrogen atom or a methyl group
  • Z 3 is an oxygen atom or -NH-
  • R 52 is a linear or branched alkylene group having 1 to 12 carbon atoms
  • R 53 is —OR 2
  • R 54 and R 55 are each independently —R 1 or —OR 2 , wherein R 1 and R 2 each independently have 1 carbon atom ⁇ 4 straight or branched chain alkyl groups, straight or branched chain acyl groups of 2 to 5 carbon atoms, or straight or branched chain ether groups of 2 to 5 carbon atoms.
  • sulfonic acid group/salt at least one group selected from the group consisting of a sulfonic acid group (--SO 3 H), a sulfate group (--OSO 3 H) and a sulfite group (--OSO 2 H), and groups of salts thereof ” is also simply referred to as “sulfonic acid group/salt, etc.”.
  • alkylene groups having 1 to 30 carbon atoms examples include methylene group, ethylene group, trimethylene group, propylene group, isopropylene group, butylene group, isobutylene group, sec-butylene group, tert-butylene group, pentamethylene group, A hexamethylene group and the like can be mentioned.
  • aryl groups having 6 to 30 carbon atoms include phenyl, biphenyl, terphenyl, pentalenyl, indenyl, naphthyl, azulenyl, heptalenyl, and biphenylenyl groups.
  • the monomer (A) is preferably a compound represented by the following formula (1), from the viewpoint of further improving durability (lubricity maintenance) (and lubricity). That is, in a preferred embodiment of the present invention, the polymerizable monomer (A) is represented by the following formula (1).
  • R 11 is a hydrogen atom or a methyl group
  • Z 1 is an oxygen atom (—O—) or —NH—
  • R 15 are each independently a linear or branched alkylene group having 1 to 8 carbon atoms
  • R 13 and R 14 are each independently a linear or branched chain having 1 to 8 carbon atoms is represented by the above formula (1), which is an alkyl group of
  • R 11 is a hydrogen atom or a methyl group
  • Z 1 is an oxygen atom (—O—) or —NH—
  • R 15 are each independently a linear or branched alkylene group having 1 to 6 carbon atoms
  • R 13 and R 14 are each independently a linear or branched chain having 1 to 4 carbon atoms is represented by the above formula (1), which is an alkyl group of
  • R 11 is a hydrogen atom or a methyl group
  • Z 1 is an oxygen atom (-O-)
  • R 12 and R 15 are Each independently represents a methylene group, an ethylene group or a trimethylene group
  • R 13 and R 14 each independently represent a methyl group or an ethyl group, represented by the above formula (1).
  • R 21 is a hydrogen atom or a methyl group
  • Z 2 is -NH-
  • X is a group selected from the group consisting of a sulfonic acid group, a sulfate group, and sodium salt groups and potassium salt groups thereof, represented by the above formula (2).
  • Examples of the compound represented by the above formula (2) include 2-(meth)acrylamido-2-methyl-1-propanesulfonic acid, 1-[(meth)acryloyloxymethyl]-1-propanesulfonic acid, 2 -[(meth)acryloyloxy]-2-propanesulfonic acid, 3-[(meth)acryloyloxy]-1-methyl-1-propanesulfonic acid, 2-sulfoethyl (meth)acrylate, 3-sulfopropyl (meth) Examples include acrylates and salts thereof (especially sodium salts).
  • 2-(meth)acrylamido-2-methyl-1-propanesulfonic acid and salts thereof are preferred, and 2-(meth)acrylamido-2-methyl-1-propanesulfonic acid and 2-(meth)acrylamide -2-Methyl-1-propanesulfonic acid sodium salt is more preferred.
  • These compounds may be used alone or in combination of two or more.
  • R 42 is a linear or branched alkylene group having 1 to 20 carbon atoms, preferably a linear or branched alkylene group having 1 to 12 carbon atoms, and more A linear or branched alkylene group having 1 to 8 carbon atoms is preferable, and a linear or branched alkylene group having 1 to 6 carbon atoms is more preferable.
  • specific examples of the alkylene group are the same as those of the above formula (3), description thereof is omitted here.
  • each R 1 is independently a linear or branched alkyl group having 1 to 20 carbon atoms, It is a linear or branched acyl group, or a linear or branched ether group having 2 to 21 carbon atoms. When a is 2, each R 1 may be the same or different.
  • Alkylene groups for R5 include methylene, ethylene, trimethylene, triethylene, propylene, isopropylene, butylene, isobutylene, sec-butylene, tert-butylene, pentylene groups, and the like. is mentioned.
  • R 52 is a single bond or a linear or branched alkylene group having 1 to 12 carbon atoms, preferably a linear or branched chain having 1 to 12 carbon atoms.
  • —Si—(R 53 )(R 54 )(R 55 ) is —Si(R 1 ) a (OR 2 ) 3-a .
  • a in the —Si(R 1 ) a (OR 2 ) 3-a group is preferably 0 or 1.
  • R 53 is —OR 2
  • R 54 and R 55 are each independently preferably —R 1 or —OR 2 , more preferably —OR 2 .
  • the monomer (C) is preferably a compound represented by the following formula (5), from the viewpoint of further improving durability (lubricity maintaining property) (further lubricity). That is, in a preferred embodiment of the present invention, the polymerizable monomer (C) is represented by the following formula (5).
  • R 51 is a hydrogen atom or a methyl group
  • Z 3 is an oxygen atom (—O—)
  • R 52 is a trimethylene group
  • the terminal of the hydrophilic copolymer according to the present invention is not particularly limited, and is appropriately defined depending on the type of raw material used, but is usually a hydrogen atom.
  • the structure of the copolymer is also not particularly limited, and may be any of random copolymer, alternating copolymer, periodic copolymer and block copolymer.
  • polymerization solvent examples include water; alcohols such as methanol, ethanol, propanol, n-butanol and 2,2,2-trifluoroethanol; polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol and dipropylene glycol; is preferably an aqueous solvent of From the viewpoint of dissolving raw materials used for polymerization, these may be used alone or in combination of two or more.
  • the copolymer may precipitate during the polymerization reaction.
  • the copolymer after polymerization can be purified by general purification methods such as reprecipitation, dialysis, ultrafiltration and extraction.
  • the copolymer after purification can be dried by any method such as freeze drying, vacuum drying, spray drying, or heat drying. Drying is preferred.
  • the unreacted monomer contained in the resulting copolymer is preferably 0.01% by weight or less with respect to the entire copolymer.
  • the content of residual monomers can be measured by known means such as high performance liquid chromatography.
  • the present invention also provides a medical device having a substrate layer and a surface lubricating layer formed on at least a portion of the surface of the substrate layer and containing the above crosslinked hydrophilic copolymer.
  • a hydrophilic copolymer according to the present invention has a structural unit (A) derived from a polymerizable monomer (A) having a sulfobetaine structure. Therefore, the medical device (surface lubricating layer) according to the present invention can exhibit excellent lubricity. Further, the hydrophilic copolymer according to the present invention has structural units (C) derived from polymerizable monomers (C) having a —Si(R 1 ) a (OR 2 ) 3-a group.
  • a silanol group silanol group of a hydrophilic copolymer, etc.
  • converted by a covalent bond silanol group of another hydrophilic copolymer, etc.
  • the substrate layer used in the present embodiment may be composed of any material as long as it can react (for example, dehydration condensation) with a silanol group of a hydrophilic copolymer to form a chemical bond. good.
  • the material that constitutes (forms) the base material layer 1 includes metal materials, polymer materials, ceramics, and the like.
  • the base layer 1 may be entirely (whole) composed (formed) of any of the above materials, or as shown in FIG.
  • the surface of the base layer core portion 1a composed (formed) of any of the above materials is covered (coated) with any other material by an appropriate method to constitute (form) the base material surface layer 1b.
  • the surface of the base material layer core portion 1a made of a resin material or the like is coated with a metal material by an appropriate method (plating, metal vapor deposition, sputtering, or other conventionally known method).
  • a base material surface layer 1b formed; a high-strength material, which is flexible compared to a reinforcing material such as a metal material, is formed on the surface of the base material layer core part 1a formed of a hard reinforcing material such as a metal material or a ceramic material;
  • the molecular material is coated by an appropriate method (a conventionally known method such as immersion (dipping), spraying (spraying), application/printing, etc.), or the reinforcing material of the base material layer core part 1a and the base material surface layer 1b are coated.
  • a base material surface layer 1b is formed by combining with a molecular material (appropriate reaction treatment).
  • styrene resin cyclic polyolefin resin, modified polyolefin resin, epoxy resin, urethane resin, diallyl phthalate resin (allyl resin), polycarbonate resin, fluorine resin, amino resin (urea resin, melamine resin, benzoguanamine resin), acrylic resin, polyacetal resin , vinyl acetate resin, phenol resin, vinyl chloride resin, silicone resin (silicon resin), polyether resin, polyimide resin, and the like.
  • the polymer material a polymer material suitable for use as a base layer for catheters, stents, guide wires, and the like may be appropriately selected.
  • the concentration of the hydrophilic copolymer exceeds 50% by weight, the viscosity of the coating liquid becomes too high, and it may not be possible to obtain a surface lubricating layer having a uniform thickness.
  • it can be used sufficiently as long as it does not affect the effects of the present invention.
  • a surface lubricating layer can be formed on a desired surface portion of the substrate layer.
  • the conditions (reaction conditions) for such heat treatment may be those that allow the desired dehydration condensation reaction to proceed (accelerate).
  • the heat treatment temperature set temperature of a heating device such as an oven
  • the heat treatment time is, for example, 1 hour or more and 48 hours or less, preferably 3 hours or more and 24 hours or less. Under such conditions, the dehydration-condensation reaction proceeds sufficiently, the surface lubricating layer is more firmly fixed to the substrate layer, and the film strength of the surface lubricating layer can be further improved.
  • the pressure conditions during the heat treatment are not particularly limited, and the heat treatment can be performed under normal pressure (atmospheric pressure) or under increased pressure or reduced pressure.
  • a heating means for example, an oven, a dryer, a microwave heating apparatus, or the like can be used.
  • the surface of the substrate layer may be washed with a solvent (for example, the solvent used for preparing the coating liquid) to remove unreacted hydrophilic copolymer.
  • a solvent for example, the solvent used for preparing the coating liquid
  • 10/0 indicates the solubility of each copolymer in water alone

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  • Health & Medical Sciences (AREA)
  • Chemical & Material 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)
  • Heart & Thoracic Surgery (AREA)
  • Surgery (AREA)
  • Vascular Medicine (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Materials For Medical Uses (AREA)

Abstract

L'objectif de la présente invention est de fournir un nouveau copolymère hydrophile capable de former une couche de lubrification de surface qui présente une durabilité (propriétés de maintien du pouvoir lubrifiant). La présente invention concerne un copolymère hydrophile qui contient un motif structural dérivé d'un monomère polymérisable (A) ayant une structure de sulfobétaïne, un motif structural dérivé d'un monomère polymérisable (B) ayant au moins un groupe choisi dans le groupe constitué par un groupe acide sulfonique (-SO3H), un groupe acide sulfurique (-OSO3H), un groupe acide sulfureux (-OSO2H) et des sels de ceux-ci, et un motif structural dérivé d'un monomère polymérisable (C) ayant un groupe -Si(R1)a(OR2)3-a (les R1 représentent indépendamment un groupe alkyle linéaire ou ramifié ayant de 1 à 20 atomes de carbone, un groupe acyle linéaire ou ramifié ayant de 2 à 21 atomes de carbone ou un groupe éther linéaire ou ramifié ayant de 2 à 21 atomes de carbone ; les R2 représentent indépendamment un atome d'hydrogène, un groupe alkyle linéaire ou ramifié ayant de 1 à 20 atomes de carbone, un groupe acyle linéaire ou ramifié ayant de 2 à 21 atomes de carbone ou un groupe éther linéaire ou ramifié ayant de 2 à 21 atomes de carbone ; et a est un nombre entier de 0 à 2).
PCT/JP2022/013126 2021-03-22 2022-03-22 Copolymère hydrophile et instrument médical Ceased WO2022202805A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2021047162A JP2024060627A (ja) 2021-03-22 2021-03-22 親水性共重合体および医療用具
JP2021-047162 2021-03-22

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Publication Number Publication Date
WO2022202805A1 true WO2022202805A1 (fr) 2022-09-29

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016052346A (ja) * 2014-09-02 2016-04-14 住友ゴム工業株式会社 金属医療用具
JP2016123491A (ja) * 2014-12-26 2016-07-11 住友ゴム工業株式会社 表面改質金属及び金属表面の改質方法
WO2017022815A1 (fr) * 2015-08-04 2017-02-09 Jsr株式会社 Composition polymère, article, dispositif médical, procédé de production d'article, et procédé de production d'amas cellulaire
WO2018038063A1 (fr) * 2016-08-25 2018-03-01 テルモ株式会社 Copolymère hydrophile et dispositif médical

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2016052346A (ja) * 2014-09-02 2016-04-14 住友ゴム工業株式会社 金属医療用具
JP2016123491A (ja) * 2014-12-26 2016-07-11 住友ゴム工業株式会社 表面改質金属及び金属表面の改質方法
WO2017022815A1 (fr) * 2015-08-04 2017-02-09 Jsr株式会社 Composition polymère, article, dispositif médical, procédé de production d'article, et procédé de production d'amas cellulaire
WO2018038063A1 (fr) * 2016-08-25 2018-03-01 テルモ株式会社 Copolymère hydrophile et dispositif médical

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