WO2008068868A1 - (メタ)アクリレート共重合体及びその製造方法及び医療用具 - Google Patents
(メタ)アクリレート共重合体及びその製造方法及び医療用具 Download PDFInfo
- Publication number
- WO2008068868A1 WO2008068868A1 PCT/JP2006/324427 JP2006324427W WO2008068868A1 WO 2008068868 A1 WO2008068868 A1 WO 2008068868A1 JP 2006324427 W JP2006324427 W JP 2006324427W WO 2008068868 A1 WO2008068868 A1 WO 2008068868A1
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- WO
- WIPO (PCT)
- Prior art keywords
- meth
- acrylate
- copolymer
- acrylate copolymer
- alkyl
- Prior art date
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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
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/16—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- A61L29/04—Macromolecular materials
- A61L29/041—Macromolecular materials obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
-
- 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
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/003—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L51/00—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
- C08L51/08—Compositions of graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds
Definitions
- Patent Document 3 Japanese Patent Laid-Open No. 11-35605
- R is an alkyl or aralkyl group having 2 to 30 carbon atoms, and R is a hydrogen atom.
- the reprecipitation poor solvent is preferably a mixture of alcohol having 1 to 10 carbon atoms and water in a weight ratio of 0.1 to 99.9: 99.9 to 0.1. .
- the number average molecular weight of the (meth) acrylate copolymer is preferably 2,000 or more from the viewpoint of ease of purification by reprecipitation after polymerization.
- the higher the molecular weight the higher the viscosity when the coating solution is prepared, so that there is a secondary effect that the adhesion to the substrate is improved. Therefore, the number average molecular weight of the (meth) acrylate copolymer is more preferably 5,000 or more, and more preferably 7,000 or more.
- the glass transition temperature of the polymer decreases and tends to increase after reaching a certain minimum.
- the minimum value is 8 carbon atoms for ⁇ -alkyl acrylate, and 12 carbon atoms for ⁇ -alkyl methacrylate.
- the glass transition temperature of the copolymer can be lowered by incorporating an alkyl acrylate having 8 carbon atoms as a copolymerization component.
- the (meth) acrylate copolymer is preferably soluble in any one of alcohols having 1 to 6 carbon atoms. It is more preferable that it is soluble in an alcohol having 1 to 3 carbon atoms because drying after coating becomes easy.
- the term “soluble” means that when (meth) acrylate copolymer lg is immersed in 10 ml of the above alcohol at 25 ° C., at least 90% by weight of (meth) acrylate copolymer is within 48 hours at room temperature. Says that the coalescence dissolves.
- the glass transition temperature of the (meth) acrylate copolymer of the present invention is preferably -100 to 20 ° C. It is more preferable that the temperature is 85 to 0 ° C, and 70 to 20 ° C is more preferable. If the glass transition temperature is too high, the copolymer coated on the substrate may be physically separated from the substrate. If the glass transition temperature is too low, the fluidity of the copolymer increases, and the workability of the coating may decrease.
- the copolymer of the present invention may be any of a random copolymer, a block copolymer, and a graft copolymer.
- a known method such as radical polymerization, ionic polymerization, photopolymerization, or polymerization using a macromer can be used without any particular limitation on the copolymerization reaction itself for producing the copolymer of the present invention.
- a production method by radical polymerization is shown below as an example for producing the (meth) acrylate copolymer of the present invention.
- the weight ratio of the polymerization solvent to the monomer is preferably 20 to 90Z80 to 10 and more preferably 30 to 90 to 70 to 10 and more preferably 35 to 85 to 65 to 15. If the charging ratio is within the above range, the polymerization reaction rate can be maximized.
- a peroxide-based or azo-based radical initiator generally used in radical polymerization is used.
- peroxy radical radical initiators include inorganic peroxides such as persulfuric power, ammonium persulfate, and hydrogen peroxide, benzoyl peroxide, and t-ptyl hydride mouth peroxide.
- Organic peroxides such as cumme oxide, azo radical initiators such as 2, 2'-azobisisobutyoxy-tolyl, 2,2'-azobis (2-amidinopropane) dihydride, dimethyl 2 2, 2-azobisbutyrate, dimethyl 2, 2, -azobis (2-methylpropionate), etc. are used.
- the (meth) acrylate copolymer is formed by copolymerizing hydrophilic and hydrophobic monomers, and thus has intermediate properties between hydrophilic and hydrophobic. Therefore, in the solution after copolymerization, hydrophilic monomers (methoxypolyethylene glycol (meth) acrylate), hydrophobic monomers (alkyl (meth) acrylate), and (meth) acrylate copolymers that are unreacted monomers are contained. Exist. In order to isolate a water-insoluble (meth) acrylate copolymer from these mixtures, for example, the copolymer solution is dropped into a reprecipitation solution in which a hydrophilic monomer is dissolved, and purification is performed!
- a mixed solution of an alcohol having 1 to C: LO and water as a poor solvent for reprecipitation.
- Any good solvent may be used as long as the (meth) acrylate copolymer is dissolved and can be mixed with the poor solvent.
- the coating method by the coating method is based on a coating solution obtained by dissolving the (meth) acrylate copolymer of the present invention in an appropriate organic solvent such as alcohol, black mouth form, acetone, tetrahydrofuran, dimethylformamide or the like. After immersing the material, it can be performed by a simple operation such as removing excess solution and then air-drying. It is also preferable to dry the substrate after coating by applying heat. As a result, the adhesion between the substrate and the copolymer of the present invention can be further enhanced and supported more firmly.
- an appropriate organic solvent such as alcohol, black mouth form, acetone, tetrahydrofuran, dimethylformamide or the like.
- the organic solvent for coating the base material with the copolymer of the present invention is selected from those which do not damage the medical device as a base material as much as possible, specifically, methanol, ethanol, ISOPROPINOLENORECONORE, NONOREMANOREPROPINORENORECONOLE, Acetone, NONOREMANOLEHEXAN, CYCLOHEXANEL, TETRAHYROGEN, 1, 4-DIOXANEL, CYCLOHEXANONE, ⁇ , ⁇ -Dimethylformamide, ⁇ , ⁇ -The ability to use dimethylacetamide, ⁇ -methylpyrrolidone, etc.
- methanol, ethanol, and isopropyl alcohol which have a low boiling point and are easy to dry after coating, are more preferred.
- the medical device of the present invention is in contact with at least a part of the surface, preferably blood on the surface. It is preferred that all of the parts have been treated with the (meth) acrylate copolymer of the present invention. In particular, it is one of the preferred embodiments that the copolymer of the present invention is supported on a medical device or the like that is required to have excellent antithrombogenicity.
- medical devices include blood filters, blood storage containers, blood circuits, indwelling needles, catheters, guide wires, stents, artificial lung devices, dialysis devices, adhesion prevention materials, wound dressings, and adhesive materials for living tissues. And repair materials for living tissue regeneration.
- the materials for medical devices include all materials that are normally used. That is, silicone rubber such as polysalt vinyleneol, polycarbonate, polyethylene terephthalate, polyethylene, polypropylene, polymethylpentene, thermoplastic polyether polyurethane, thermosetting polyurethane, polydimethylsiloxane having a crosslinked part, Examples include polymethyl methacrylate, poly (vinylidene fluoride), polytetrafluoroethylene, polysulfone, polyether sulfonate, polyacetal, polystyrene, ABS resin and mixtures of these resins, metals such as stainless steel, titanium, and aluminum. It is done.
- silicone rubber such as polysalt vinyleneol, polycarbonate, polyethylene terephthalate, polyethylene, polypropylene, polymethylpentene, thermoplastic polyether polyurethane, thermosetting polyurethane, polydimethylsiloxane having a crosslinked part
- examples include polymethyl methacrylate, poly (vin
- methoxypolyethylene glycol (meth) acrylate with high hydrophilicity protrudes on the surface. It exhibits antithrombogenicity, and alkyl (meth) acrylate is considered to prevent direct contact between blood and medical devices by staying in the vicinity of the base material.
- a comparison of complement values is given as a method for evaluating the degree of immune activation of a (meth) acrylate copolymer.
- the Mayer method for measuring CH50 is preferable because it is simple and quick, and the measurement kit is easy to obtain and inexpensive. (See Non-Patent Document 5).
- the sensitized red blood cells are hemolyzed by the reaction between Hedge sensitized red blood cells and the complement in serum. To do. Since the degree of hemolysis decreases as the complement system is activated, it can be used significantly as an evaluation method.
- a 1 wt% ethanol (tetrahydrofuran only for comparative example 6) solution was prepared to obtain a surface treating agent.
- the surface treatment agent was applied to a 25 ⁇ 25xlmm PVC sheet and dried at 60 ° C. for 24 hours. Further, aging was performed in 37 ° C physiological saline for 30 days to obtain an aging sample for blood compatibility test. For sampnore after aging for 30 days, the weight loss rate of 20% by weight or less was marked as ⁇ , and those with a weight loss greater than 20% by weight were marked as X. When the weight loss is 20% or more, it can be determined that the sample dissolved significantly in physiological saline even if measurement errors were taken into account.
- 60 mL of fresh citrated blood exsanguinated from Usagi was divided into two 50 mL centrifuge tubes, which were centrifuged at 1 000 rpm for 10 minutes. The supernatant was equally divided into four 10 mL centrifuge tubes. After further centrifugation at 1500 rpm for 10 minutes, the supernatant is removed and platelets that are precipitated are removed. The pellet was separated. By diluting with the addition of HBSS (Hank's balanced salt solution) therein to obtain a platelet solution of platelet concentration 3.0xl0 8 ZmL. Platelet concentration was confirmed with a blood cell counter (KX-21 Sysmetas). This concentration of platelet solution was used as a test solution.
- Example 2 In the same manner as in Example 1, a crude (meth) acrylate copolymer was obtained. 2 g of the obtained crude (meth) acrylate copolymer was dissolved in 2 g of tetrahydrofuran, and dropped into 20 g of a poor solvent (weight ratio of methanol Z water: 90 ZlO) using a Pasteur pipette. The precipitate was collected by decantation, and the operation of adding the same weight of tetrahydrofuran and dissolving it, and dropping it in a poor solvent was repeated twice, followed by drying under reduced pressure at 60 ° C and 0.1 Torr for 4 days. The purified product 3 was obtained.
- a poor solvent weight ratio of methanol Z water: 90 ZlO
- a stirrable reactor equipped with a reflux tower is equipped with MTEGA (Shin-Nakamura Chemical Co., Ltd.) 22.2g and EHA (Tokyo Kasei Kogyo Co., Ltd.) 33.8g, Azobisisobutiguchi-Trill (AIBN) (Wako Pure Chemical Industries, Ltd.) 0 0543 g and ethanol (Tokyo Kasei Kogyo Co., Ltd.) 84.2 g were added, and the polymerization reaction was carried out at 80 ° C. for 20 hours. After the completion of the polymerization reaction, a crude (meth) acrylate copolymer was obtained in the same manner as in Example 1.
- the copolymer of the present invention can be used as a material having excellent blood compatibility and high hydrophilicity.
- the material is a viscous substance that is insoluble in water, it is possible to provide a material that can be coated on the entire blood circuit without impairing the physical properties of medical equipment.
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BRPI0622191A BRPI0622191B8 (pt) | 2006-12-07 | 2006-12-07 | uso de um copolímero de metacrilato na fabricação de um dispositivo médico antitrombogênico, e uso de um copolímero de metacrilato como material antitrombogênico para tratamento de superfície |
EP06834182.5A EP2100627B1 (en) | 2006-12-07 | 2006-12-07 | (meth)acrylate copolymer, process for producing the same and medical device |
US12/517,521 US8236913B2 (en) | 2006-12-07 | 2006-12-07 | (Meth)acrylate copolymer, a method for producing the same and a medical device |
PCT/JP2006/324427 WO2008068868A1 (ja) | 2006-12-07 | 2006-12-07 | (メタ)アクリレート共重合体及びその製造方法及び医療用具 |
CN200680056535A CN101547708A (zh) | 2006-12-07 | 2006-12-07 | (甲基)丙烯酸酯共聚物及其制造方法以及医疗用具 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/JP2006/324427 WO2008068868A1 (ja) | 2006-12-07 | 2006-12-07 | (メタ)アクリレート共重合体及びその製造方法及び医療用具 |
Publications (1)
Publication Number | Publication Date |
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WO2008068868A1 true WO2008068868A1 (ja) | 2008-06-12 |
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Application Number | Title | Priority Date | Filing Date |
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PCT/JP2006/324427 WO2008068868A1 (ja) | 2006-12-07 | 2006-12-07 | (メタ)アクリレート共重合体及びその製造方法及び医療用具 |
Country Status (5)
Country | Link |
---|---|
US (1) | US8236913B2 (ja) |
EP (1) | EP2100627B1 (ja) |
CN (1) | CN101547708A (ja) |
BR (1) | BRPI0622191B8 (ja) |
WO (1) | WO2008068868A1 (ja) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014046158A1 (ja) * | 2012-09-20 | 2014-03-27 | 東洋紡株式会社 | 医療用ペレット状組成物及び成形体 |
WO2019031581A1 (ja) * | 2017-08-10 | 2019-02-14 | Jsr株式会社 | 免疫凝集の検出又は測定方法 |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103468085A (zh) * | 2013-09-13 | 2013-12-25 | 苏州蔻美新材料有限公司 | 一种含有磷脂聚合物仿生涂层的水质实时监控探头制备工艺 |
CN105884986B (zh) * | 2016-06-21 | 2018-03-16 | 苏州艾博迈尔新材料有限公司 | 一种生物相容性碳纳米管聚合物及其制备方法 |
CN109641097B (zh) * | 2016-08-31 | 2022-04-26 | 东丽株式会社 | 医疗用材料、医疗用分离膜、和血液净化器 |
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JPH1135605A (ja) | 1997-07-16 | 1999-02-09 | Nof Corp | 疎水性基及びホスホリルコリン基含有重合体の製造方法 |
JPH11287802A (ja) | 1998-04-03 | 1999-10-19 | Nippon Kayaku Co Ltd | 表面保護剤 |
JP2002105136A (ja) | 2000-09-29 | 2002-04-10 | Terumo Corp | 抗血栓性表面処理剤および医療用具 |
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- 2006-12-07 EP EP06834182.5A patent/EP2100627B1/en active Active
- 2006-12-07 WO PCT/JP2006/324427 patent/WO2008068868A1/ja active Application Filing
- 2006-12-07 CN CN200680056535A patent/CN101547708A/zh active Pending
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- 2006-12-07 BR BRPI0622191A patent/BRPI0622191B8/pt active IP Right Grant
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Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2014046158A1 (ja) * | 2012-09-20 | 2014-03-27 | 東洋紡株式会社 | 医療用ペレット状組成物及び成形体 |
JPWO2014046158A1 (ja) * | 2012-09-20 | 2016-08-18 | 東洋紡株式会社 | 医療用ペレット状組成物及び成形体 |
WO2019031581A1 (ja) * | 2017-08-10 | 2019-02-14 | Jsr株式会社 | 免疫凝集の検出又は測定方法 |
Also Published As
Publication number | Publication date |
---|---|
BRPI0622191B1 (pt) | 2019-01-08 |
BRPI0622191A2 (pt) | 2012-07-24 |
EP2100627A1 (en) | 2009-09-16 |
BRPI0622191B8 (pt) | 2021-06-22 |
US20100069595A1 (en) | 2010-03-18 |
US8236913B2 (en) | 2012-08-07 |
EP2100627A4 (en) | 2009-12-16 |
EP2100627B1 (en) | 2014-07-02 |
CN101547708A (zh) | 2009-09-30 |
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