WO2013176084A1 - Agent de couplage de type silane contenant un composé silylalkyl phosphoramidate - Google Patents

Agent de couplage de type silane contenant un composé silylalkyl phosphoramidate Download PDF

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Publication number
WO2013176084A1
WO2013176084A1 PCT/JP2013/063943 JP2013063943W WO2013176084A1 WO 2013176084 A1 WO2013176084 A1 WO 2013176084A1 JP 2013063943 W JP2013063943 W JP 2013063943W WO 2013176084 A1 WO2013176084 A1 WO 2013176084A1
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Prior art keywords
silane coupling
coupling agent
substrate
group
silylalkyl
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PCT/JP2013/063943
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English (en)
Japanese (ja)
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義和 大塚
武久 岩間
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日産化学工業株式会社
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Priority to JP2014516791A priority Critical patent/JPWO2013176084A1/ja
Publication of WO2013176084A1 publication Critical patent/WO2013176084A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/22—Amides of acids of phosphorus
    • C07F9/24—Esteramides
    • C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/2458—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic of aliphatic amines
    • 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
    • A61L27/50—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L27/54—Biologically active materials, e.g. therapeutic substances
    • 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
    • A61L29/16—Biologically active materials, e.g. therapeutic substances
    • 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
    • A61L31/14—Materials characterised by their function or physical properties, e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
    • A61L31/16—Biologically active materials, e.g. therapeutic substances
    • 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
    • A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
    • A61L33/0005—Use of materials characterised by their function or physical properties
    • A61L33/0011—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate
    • A61L33/0041—Anticoagulant, e.g. heparin, platelet aggregation inhibitor, fibrinolytic agent, other than enzymes, attached to the substrate characterised by the choice of an antithrombatic agent other than heparin
    • 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
    • A61L33/00—Antithrombogenic treatment of surgical articles, e.g. sutures, catheters, prostheses, or of articles for the manipulation or conditioning of blood; Materials for such treatment
    • A61L33/04—Use of organic materials, e.g. acetylsalicylic acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
    • C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/20—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials
    • A61L2300/216—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices containing or releasing organic materials with other specific functional groups, e.g. aldehydes, ketones, phenols, quaternary phosphonium groups
    • 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
    • A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
    • A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
    • A61L2300/424—Anti-adhesion agents

Definitions

  • the present invention includes a silylalkyl phosphoramide compound capable of suppressing the adhesion of biological materials such as proteins, cells, and platelets by performing a surface treatment on an inorganic material such as silicon or glass, or a resin such as polyethylene.
  • the present invention relates to a silane coupling agent.
  • an anticoagulant such as heparin or a drug such as an immunosuppressant must be used in combination.
  • MPC polymer poly (2-methacryloyloxyethyl phosphorylcholine) (hereinafter referred to as MPC polymer) having phosphorylcholine, which is the same amphoteric phospholipid as the biological membrane, in the side chain of the polymer chain is used Medical materials that have been proposed have been proposed (see, for example, Patent Document 1 and Patent Document 2).
  • CMB polymer N-methacryloyloxyethyl-N, N-dimethylammonium- ⁇ -N-methylcarboxybetaine
  • An object of the present invention is a compound that is a non-polymer that is easy to produce, and the compound is directly applied to the surface of a substrate by applying the solution in which the compound is dissolved to the substrate or immersing the substrate in the solution. It is another object of the present invention to provide a compound capable of firmly covering the surface of the body and exhibiting the same biological substance adhesion inhibitory effect as the conventional MPC polymer and CMB polymer.
  • silylalkyl phosphoramidade compounds are useful as silane coupling agents, and silane coupling agents containing such compounds are proteins, cells, It has been found that it has an effect of suppressing adhesion of biological substances such as platelets. That is, the present invention 1. Following formula (1):
  • a silane coupling agent composition comprising the silylalkyl phosphoramidade compound according to 1 above, 3.
  • a silane coupling agent comprising a step of applying and baking the silane coupling agent composition described in 2 or 3 above on a substrate, a step of washing the substrate with a polar solvent, and a step of drying the substrate.
  • Immobilization method 5. Immobilization of a silane coupling agent comprising a step of immersing a substrate in the silane coupling agent composition described in 2 or 3 above, a step of washing the substrate with a polar solvent, and a step of drying the substrate.
  • Conversion method 6).
  • silane coupling agent surface treatment agent
  • a base material a resin such as polyethylene
  • the surface is coated with a silylalkyl phosphoramidade compound having both stable positive and negative charges in one molecule. Therefore, adhesion of biological substances such as proteins, cells, and platelets to the inorganic substance or resin surface can be suppressed without using a polymer such as MPC polymer or CMB polymer.
  • FIG. 1 is a diagram showing the cell adhesion inhibitory action of 2- (trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) phosphoramidate on a glass substrate.
  • Cell free represents a glass substrate treated with 2- (trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) phosphoramidate (30 mg / ml), and the control was controlled with the silane coupling agent of the present invention. Represents the result when no processing is performed.
  • FIG. 2 is a diagram showing the results of measurement of living cells attached to a glass substrate of a silylalkyl phosphoramidade compound. Control represents the result when the treatment with the silane coupling agent of the present invention is not performed.
  • silylalkyl phosphoramidade compound of the present invention represented by the formula (1) is 0.8 to 1.2 equivalents, preferably 1 equivalent of the formula (II) to the aminoalkylsilane represented by the formula (I). ) Is reacted at 20 to 80 ° C. in the presence of a base to obtain a compound represented by the formula (III). It can be obtained by reacting 8 to 1.2 equivalents, preferably 1 equivalent of a tertiary amine represented by the formula (IV) at 0 to 50 ° C.
  • an organic base such as triethylamine is preferable.
  • R 1 , R 2 and R 3 are methyl, ethyl, n-propyl, isopropyl, cyclopropyl, n-butyl.
  • Group, isobutyl group, s-butyl group, t-butyl group, cyclobutyl group, n-pentyl group, and cyclopentyl group, and methyl group and ethyl group are particularly preferable.
  • R 4 is methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, s -Butyl group, t-butyl group, cyclobutyl group, n-pentyl group, and cyclopentyl group can be mentioned, and methyl group and ethyl group are particularly preferable.
  • R 5 represents methyl group, ethyl group, n-propyl group, isopropyl group, cyclopropyl group, n-butyl group, isobutyl group, s -Butyl group, t-butyl group, cyclobutyl group, n-pentyl group, and cyclopentyl group can be mentioned, and methyl group and ethyl group are particularly preferable.
  • n may be an integer of 1 to 5, and 2 or 3 is particularly preferable.
  • p may be an integer of 1 to 5, but 2 or 3 is particularly preferable.
  • q is an integer of 1 to 3.
  • the silylalkyl phosphoramariae compound of the present invention is used for surface treatment of an inorganic substance as a base material
  • the inorganic substance is not particularly limited.
  • silicon, copper, iron, aluminum, zinc or an alloy thereof, glass, silica, aluminum oxide, aluminum hydroxide, and magnesium oxide can be given.
  • the resin is not particularly limited.
  • examples include poly (meth) acrylamide, poly (meth) acrylamide derivatives, polysulfone, polycarbonate, cellulose, and cellulose derivatives.
  • the silylalkyl phosphoramidade compound of the present invention can be used for surface treatment of pharmaceuticals, quasi drugs, medical instruments and the like.
  • medical devices include drug delivery system materials, molding aids, packaging materials, artificial blood vessels, hemodialysis membranes, catheters, guard wires, contact lenses, blood filters, blood storage packs, endoscopes, artificial organs, biotechnology A chip, a cell culture sheet, and a sugar chain synthesizer can be mentioned, but there are no particular limitations on the medical instrument.
  • the silane coupling agent (surface treatment agent) composition containing the silylalkyl phosphoramidade compound of the present invention includes, for example, water and a polar organic solvent such as methanol, ethanol, propylene glycol monomethyl ether and the like on the silylalkylphosphoramidade compound. In addition, it is prepared by diluting to 0.001 to 20% by mass.
  • a polar organic solvent such as methanol, ethanol, propylene glycol monomethyl ether and the like on the silylalkylphosphoramidade compound.
  • an organic acid may be further added. Examples of the organic acid include acetic acid, formic acid, lactic acid, and oxalic acid.
  • the surface treatment of the substrate with the silane coupling agent composition of the present invention is not particularly limited, and for example, the substrate can be treated by dipping, coating (spin coating, spray coating, etc.) or vapor deposition.
  • silane coupling is performed through a step of applying and baking the silane coupling agent composition of the present invention on a substrate, a step of washing the substrate with a polar solvent, and a step of drying the substrate. Immobilize the agent.
  • the silane coupling agent is immobilized through a step of immersing the substrate in the silane coupling agent composition, a step of washing the substrate with a polar solvent, and a step of drying the substrate.
  • the polar solvent used in the washing step for example, water or a polar organic solvent contained in the silane coupling agent composition can be used.
  • 2-Chloro-2-oxo-1,3,2-dioxaphospholane (3.37 g) was dissolved in tetrahydrofuran (20 mL), cooled to 0 ° C., triethylamine (2.88 g, 1.2 molar equivalent) was added, and the mixture was stirred. . 3.82 g (1.0 molar equivalent) of (3-aminopropyl) dimethylethoxysilane was added dropwise, and the temperature was gradually raised to 25 ° C. After stirring overnight, the insoluble material was filtered under reduced pressure.
  • Example 4 Treatment of 2- (trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) phosphoramidate on a glass substrate
  • 2- (Trimethylammonio) ethyl (3- (ethoxy) synthesized in Example 2 10 mg of dimethylsilyl) propyl) phosphoramidate is dissolved in 1 mL of 70% ethanol aqueous solution, and 0.1 mL is dropped on a glass substrate (a square with a side of 2 cm) attached to a spin coater, and 300 rpm for 5 seconds, followed by 2500 rpm, 25 Spin coating was performed for 2 seconds. Then, it heat-processed for 60 second with a 100 degreeC hotplate, and was fixed.
  • a similar treatment was performed on a solution of 30 mg of 2- (trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) phosphoramidate in 1 mL of 70% ethanol aqueous
  • Example 5 Treatment of 2- (trimethylammonio) ethyl (3- (triethoxysilyl) propyl) phosphoramidate on a glass substrate
  • 2- (trimethylammonio) ethyl (3- (tri 30 mg of ethoxysilyl) propyl) phosphoramidate is dissolved in 1 mL of 70% ethanol aqueous solution, and 0.1 mL is dropped on a glass substrate (a square with a side of 2 cm) mounted on a spin coater, and 300 rpm for 5 seconds, followed by 2500 rpm, 25 Spin coating was performed for 2 seconds. Furthermore, it was fixed by heat treatment for 60 seconds on a 100 ° C. hot plate.
  • Comparative Example 1 Treatment of MPC polymer on glass substrate 15 mg of MPC (2-methacryloyloxyphosphorylcholine) polymer (PUREBRIGHT MB, registered by NOF Corporation) was dissolved in 0.5 mL of 70% aqueous ethanol solution, and 0.1 mL was spinned. It was dropped on a glass substrate (a square having a side of 2 cm) mounted on the coater, and spin coating was performed at 300 rpm for 5 seconds followed by 2500 rpm for 25 seconds. Furthermore, it was fixed by heat treatment for 60 seconds on a 100 ° C. hot plate.
  • MPC (2-methacryloyloxyphosphorylcholine) polymer PUREBRIGHT MB, registered by NOF Corporation
  • Example 6 Confirmation of Cell Adhesion Inhibition Action on Glass Substrate Treated with 2- (Trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) Phosphoramidate HEK293 cells (human kidney-derived cell line Human Embryonic Kidney ( 2 ⁇ 10 6 cells / ml) was pre-cultured in a Dulbecco's Modified Eagle Medium (D-MEM) medium at 37 ° C. for 2 days, and 3 mL seeded in a 12-well plate containing a glass substrate treated by the method of Example 4 Then, 0.8 mL of D-MEM was added and cultured for 1 day at 37 ° C.
  • D-MEM Dulbecco's Modified Eagle Medium
  • the glass substrate was then transferred to another 12-well plate and 1 mL phosphate buffer (Dulbecco phosphate buffered saline, Dulbecco's Phosphate Buffered Sali
  • phosphate buffer Dulbecco phosphate buffered saline, Dulbecco's Phosphate Buffered Sali
  • the cells were detached from the glass substrate by adding 0.3 mL of a 0.1% trypsin solution (manufactured by SIGMA), to which 3 mL of D-MEM was added, and WST was further added.
  • 0.3 mL of -8 Korean (registered trademark) was added to each well and incubated at 37 ° C. for 4 hours, and then 0.11 mL was transferred to a 96-well plate and the absorbance was measured.
  • 2- (trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) phosphoramidate is obtained by treating 0.1 mL of 10 mg / mL and 30 mg / mL solutions on a glass substrate. The adhesion of HEK cells to the glass substrate was suppressed.
  • Example 7 Measurement of living cells attached to a treated glass substrate.
  • HEK293 cells human kidney-derived cell line Human Embroidic Kidney (2 ⁇ 10 6 cells / ml) pre-cultured in Dulbecco's Modified Eagle Medium (D-MEM) medium at 37 ° C. for 2 days were treated in Example 4.
  • D-MEM Dulbecco's Modified Eagle Medium
  • these glass substrates were transferred to another 6-well plate and washed with 1 mL of phosphate buffer (Dulbecco's phosphate buffered saline, Dulbecco's Phosphate Buffered Saline), respectively, and 1 mL of D-MEM was then removed.
  • phosphate buffer Dulbecco's phosphate buffered saline, Dulbecco's Phosphate Buffered Saline
  • WST-8 Wooda Chemical
  • 2- (trimethylammonio) ethyl (3- (ethoxydimethylsilyl) propyl) phosphoramidate and 2- (trimethylammonio) ethyl (3- (triethoxysilyl) propyl) phosphoramidate are By treating 0.1 mL of a 30 mg / mL solution on a glass substrate, HEK cell adhesion to the glass substrate was suppressed. This inhibitory effect was equivalent to or better than that of MPC polymer.

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Abstract

L'invention a pour but de proposer un nouvel agent de couplage de type silane. A cet effet, l'invention concerne un composé silylalkyl phosphoramidate représenté par la formule (1), et une composition d'agent de couplage de type silane qui contient le composé. (Dans la formule, chacun parmi R1, R2 et R3 représente indépendamment un groupe alkyle ayant 1-5 atomes de carbone ; chacun parmi R4 et R5 représente indépendamment un groupe alkyle ayant 1-5 atomes de carbone ; chacun de n et p représente indépendamment un entier de 1-5 ; et q représente un entier de 1-3).
PCT/JP2013/063943 2012-05-22 2013-05-20 Agent de couplage de type silane contenant un composé silylalkyl phosphoramidate WO2013176084A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2014516791A JPWO2013176084A1 (ja) 2012-05-22 2013-05-20 シリルアルキルホスホラミダード化合物を含むシランカップリング剤

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JP2012116353 2012-05-22
JP2012-116353 2012-05-22

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015193504A1 (fr) * 2014-06-19 2015-12-23 Pentracor Gmbh Matériau de séparation comprenant des dérivés phosphorylcholine

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08507293A (ja) * 1993-01-28 1996-08-06 バイオコンパテイブルズ・リミテツド 新規な材料
JP2005187456A (ja) * 2003-12-02 2005-07-14 Shiseido Co Ltd ホスホリルコリン基含有化合物及び該化合物からなる表面改質剤
CN101195638A (zh) * 2007-12-24 2008-06-11 常州市绿空能源设备有限公司 一种含替加氟和氮杂硅三环的磷酰胺酯化合物
JP2011236345A (ja) * 2010-05-11 2011-11-24 Shiseido Co Ltd 表面改質方法及び表面改質材料
WO2013038901A1 (fr) * 2011-09-16 2013-03-21 日産化学工業株式会社 Composé de silicium organique et agent de couplage silane le contenant

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08507293A (ja) * 1993-01-28 1996-08-06 バイオコンパテイブルズ・リミテツド 新規な材料
JP2005187456A (ja) * 2003-12-02 2005-07-14 Shiseido Co Ltd ホスホリルコリン基含有化合物及び該化合物からなる表面改質剤
CN101195638A (zh) * 2007-12-24 2008-06-11 常州市绿空能源设备有限公司 一种含替加氟和氮杂硅三环的磷酰胺酯化合物
JP2011236345A (ja) * 2010-05-11 2011-11-24 Shiseido Co Ltd 表面改質方法及び表面改質材料
WO2013038901A1 (fr) * 2011-09-16 2013-03-21 日産化学工業株式会社 Composé de silicium organique et agent de couplage silane le contenant

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
YONG-ZHI OIU ET AL.: "A NOVEL ZWITTERIONIC SILANE COUPLING AGENT FOR NONTHROMBOGENIC BIOMATERIALS", CHINESE JOURNAL OF POLYMER SCIENCE, vol. 23, no. 6, 2005, pages 611 - 617 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015193504A1 (fr) * 2014-06-19 2015-12-23 Pentracor Gmbh Matériau de séparation comprenant des dérivés phosphorylcholine
EP2957563A1 (fr) * 2014-06-19 2015-12-23 Pentracor GmbH Matériau de séparation comprenant des dérivés de la phosphorylcholine
CN106459108A (zh) * 2014-06-19 2017-02-22 彭特科尔有限公司 包含磷酰胆碱衍生物的分离材料
RU2666357C2 (ru) * 2014-06-19 2018-09-07 Пентракор Гмбх Сепарационный материал, включающий производные фосфорилхолина
CN106459108B (zh) * 2014-06-19 2019-10-15 彭特科尔有限公司 包含磷酰胆碱衍生物的分离材料

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