WO2011115281A1 - Corps moulé à base de fibres - Google Patents

Corps moulé à base de fibres Download PDF

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Publication number
WO2011115281A1
WO2011115281A1 PCT/JP2011/056682 JP2011056682W WO2011115281A1 WO 2011115281 A1 WO2011115281 A1 WO 2011115281A1 JP 2011056682 W JP2011056682 W JP 2011056682W WO 2011115281 A1 WO2011115281 A1 WO 2011115281A1
Authority
WO
WIPO (PCT)
Prior art keywords
fiber
molded body
fiber molded
polymer
fibrin glue
Prior art date
Application number
PCT/JP2011/056682
Other languages
English (en)
Japanese (ja)
Inventor
由佳子 景山
真 佐竹
博章 兼子
Original Assignee
帝人株式会社
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 帝人株式会社 filed Critical 帝人株式会社
Priority to JP2012505779A priority Critical patent/JPWO2011115281A1/ja
Publication of WO2011115281A1 publication Critical patent/WO2011115281A1/fr

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Classifications

    • D—TEXTILES; PAPER
    • D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
    • D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
    • D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
    • D04H1/70—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres
    • D04H1/72—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres the fibres being randomly arranged
    • D04H1/728—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres characterised by the method of forming fleeces or layers, e.g. reorientation of fibres the fibres being randomly arranged by electro-spinning
    • 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
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01D—MECHANICAL METHODS OR APPARATUS IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS
    • D01D5/00—Formation of filaments, threads, or the like
    • D01D5/0007—Electro-spinning
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F1/00—General methods for the manufacture of artificial filaments or the like
    • D01F1/02—Addition of substances to the spinning solution or to the melt
    • D01F1/10—Other agents for modifying properties
    • D—TEXTILES; PAPER
    • D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
    • D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
    • D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
    • D01F6/58—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products
    • D01F6/62—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters
    • D01F6/625—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from homopolycondensation products from polyesters derived from hydroxy-carboxylic acids, e.g. lactones

Definitions

  • the present invention relates to a fiber molded body made of fibers having high affinity with fibrin glue. Specifically, the present invention relates to a fiber molded body containing a phospholipid in an amount of 0.1 to 10 wt% and a fiber having a smooth fiber surface.
  • the fiber molded body of the present invention is used, for example, as a medical product, particularly a medical product expected to be used in combination with fibrin glue.
  • the needle hole once opened is difficult to close, and when the tension is applied, the needle hole through which the thread passes may be stretched, and there is a problem that cerebrospinal fluid can easily leak from this needle hole. . Therefore, a filling method in which fibrin glue is applied to the sutured portion of the artificial substitute dura is employed.
  • the artificial substitute dura mater has PTFE (polytetrafluoroethylene) as a main component, and therefore has a problem that the affinity for fibrin glue is low and the needle hole cannot be completely closed.
  • Seam Dura registered trademark
  • stitching is necessary to prevent liquid leakage, which is troublesome for the operator.
  • an artificial dura mater that does not require suturing and has high affinity with fibrin glue has been desired.
  • the method of using fibrin glue is to install an artificial dura on the dural defect, then apply fibrinogen solution to the artificial dura to improve the familiarity between the artificial dura and the dura, and then fibrinogen solution and calcium.
  • a thrombin solution containing the solution is applied to an artificial dura mater and gelled by a two-component reaction to form a fibrin glue. Therefore, when the artificial dura is attached to the dura using fibrin glue, the fibrin glue may easily penetrate into the artificial dura because the artificial dura and the dura adhere without leaking. It has been demanded.
  • the electrospinning method is a method for producing a fiber, which is also called an electrostatic spinning method, an electrospinning method, or an electrospray method. Since the electrospinning method can easily produce a yarn having a small fiber diameter, it is used to obtain a fiber molded body having an increased fiber surface area.
  • Japanese Patent Application Laid-Open No. 2002-253322 describes an artificial dura mater in which the surface of PTFE is modified by an ion beam to improve the affinity with fibrin glue and a method for producing the same. As a result, it can be used without suturing, but PTFE is still non-degradable and has a problem of remaining in the body for a long time.
  • WO2006 / 025150 describes an intestinal defect occlusion device comprising a polyglycolic acid fiber molded article and a fibrin glue.
  • this device has a problem that the affinity between the fiber molded body and the fibrin glue is low, there is no description that the affinity with the fibrin glue is improved by containing a phospholipid.
  • International Publication WO2006 / 022430 describes a nanofiber containing a phospholipid. And it is described that the fiber surface becomes uneven by adding phospholipid, thereby improving the adhesion of cells.
  • the affinity with fibrin glue is improved by smoothing the fiber surface.
  • US Published Application 2004/0013873 describes nanofibers having irregularities on the surface. The effect is that the strength is increased when the composite is formed, but there is no description about the improvement of the affinity with the fibrin glue by the smoothing of the fiber surface or the addition of phospholipid.
  • the problem to be solved by the present invention is to provide a fiber molded article excellent in affinity with fibrin glue.
  • a fiber molded body used as an artificial dura mater will be described.
  • the fibrin glue easily penetrates into the artificial dura mater.
  • the ease of soaking of the fibrin glue into the artificial dura can be evaluated by the wettability of the artificial dura. If the wetness of the artificial dura is high, the fibrin glue penetrates into the artificial dura and a strong composite of the artificial dura and the fibrin glue is formed.
  • the dura tissue and the artificial dura mater can be used as an artificial dura mater without suturing by adhering via a fibrin glue.
  • the inventors of the present invention have intensively studied a fiber molded article having excellent affinity with fibrin glue, and as a result, a fiber molded article containing fibers containing phospholipid and having a smooth surface has an affinity for fibrin glue. As a result, the present invention was completed. It has been found that when a fiber molded article containing a phospholipid is produced by an electrospinning method under specific conditions, the amphiphilic phospholipid is segregated on the fiber surface. Therefore, wettability is improved.
  • the present invention is a fiber molding comprising a fiber comprising a polymer containing phospholipid, the fiber surface having a smoothness of 1.07 or less, and comprising a fiber containing 0.1 to 10 wt% of phospholipid with respect to the polymer. Is the body.
  • a fiber molded body has an effect that the affinity with the fibrin glue is particularly excellent.
  • the fiber molded body of the present invention contains 0.1 to 10 wt% of phospholipid with respect to the polymer.
  • the preferred content is 0.2-5 wt%, more preferably 0.3-3 wt%.
  • the phospholipid may be extracted from animal tissue or artificially synthesized. Examples of the phospholipid include phosphatidylcholine, phosphatidylethanolamine, phosphatidylserine, and phosphatidylglycerol.
  • the polymer used in the present invention is preferably a biodegradable polymer, specifically, polylactic acid, polyglycolic acid, polycaprolactone, polydioxanone, lactic acid-glycolic acid copolymer, lactic acid-caprolactone copolymer, polyglycerol.
  • Aliphatic polyesters such as sebacic acid, polyhydroxyalkanoic acid and polybutylene succinate, aliphatic polycarbonates such as polymethylene carbonate, polysaccharides such as cellulose diacetate, cellulose triacetate, methylcellulose, propylcellulose, benzylcellulose and carboxymethylcellulose Derivatives, proteins such as fibroin, gelatin, collagen, and derivatives thereof. More preferred are aliphatic polyesters such as polylactic acid, polyglycolic acid, and lactic acid-glycolic acid copolymer, and most preferred are polylactic acid or lactic acid-glycolic acid copolymer. When using a copolymer of polylactic acid, it is preferable that the monomer component imparting stretchability is small.
  • the monomer component imparting stretchability is caprolactone monomer, ethylene glycol, 1,2-propylene glycol, 1,3-propylene glycol, 1,2-butanediol, 1,4-butanediol, polycaprolactone diol.
  • soft components such as polyalkylene carbonate diol and polyethylene glycol unit. These soft components are preferably less than 20% by weight of the polymer. When there is more soft component than this, it becomes easy to lose self-supporting property, and it becomes a fiber molded body which is too soft and difficult to handle.
  • monomers constituting the polymer include L-lactic acid and D-lactic acid, but there is no particular limitation.
  • the optical purity, molecular weight, composition ratio of L-form and D-form, and arrangement are not particularly limited, but a polymer having many L-forms is preferable.
  • a stereocomplex of poly L lactic acid and poly D lactic acid may be used.
  • the molecular weight of the polymer is 1 ⁇ 10 3 to 5 ⁇ 10 6 , preferably 1 ⁇ 10 4 to 1 ⁇ 10 6 , more preferably 5 ⁇ 10 4 to 5 ⁇ 10 5 .
  • the terminal structure of the polymer and the catalyst for polymerizing the polymer can be arbitrarily selected. In the fiber molded body of the present invention, other polymers and other compounds may be used in combination as long as the purpose is not impaired.
  • a fiber having a smooth fiber surface refers to a fiber in which unevenness or the like is not observed on the surface when the fiber surface is observed with an electron scanning line microscope or the like. For example, in International Publication WO2006 / 022430, a fiber molded body having an uneven fiber surface is shown, but the fiber does not have such an unevenness.
  • the surface morphology of the fiber is evaluated by the surface area ratio in the AFM observation visual field range 1 ⁇ 1 ⁇ m 2 using an atomic force microscope AFM, and is 1.07 or less, preferably 1.05 or less, more preferably The fiber which is 1.03 or less.
  • Nano Scope IIIa manufactured by Digital Instruments was used as the AFM.
  • the cantilever used was AC-240TS (made of silicon: spring constant 2 N / m). In order to prevent resolution degradation during observation, a new cantilever with no contamination or wear of the probe was used. In addition, the force acting between the probe and the sample surface was set to the minimum necessary force to prevent sample breakage and probe wear during scanning.
  • the observation was performed with an observation field of view of 1 ⁇ 1 ⁇ m 2 so that the probe was in contact with the center of the fiber and the scanning direction of the probe coincided with the fiber axis.
  • the scanning speed was 0.7 Hz.
  • the resolution was 256 ⁇ 256 pixels or higher. Since the fiber has a curvature, after the AFM observation, the curvature of the fiber and the undulation on the macro form were canceled using inclination correction software attached to the apparatus. In the tilt correction, when the probe contacted the fiber center completely and the scanning direction coincided with the fiber axis direction, the secondary tilt correction was performed. Otherwise, the tertiary tilt correction processing and flat processing were performed. .
  • the evaluation was performed with an average value of 20 observation visual fields performed at random.
  • the fiber diameter of the fiber in the present invention is 0.1 to 10 ⁇ m.
  • the average fiber diameter is preferably 1.0 to 8.0 ⁇ m, more preferably 2.0 to 7.0 ⁇ m.
  • a fiber diameter represents the diameter of a fiber cross section.
  • the shape of the fiber cross section is not limited to a circle, and may be an ellipse or an irregular shape. With respect to the fiber diameter in this case, the average of the length in the major axis direction and the length in the minor axis direction of the ellipse is calculated as the fiber diameter. When the fiber cross section is neither circular nor elliptical, the fiber diameter is calculated by approximating a circle or ellipse.
  • the fiber molded body is made of long fibers. Specifically, long fiber refers to a fiber molded body that is formed without adding a fiber cutting step in the process from spinning to processing into a fiber molded body.
  • the electrospinning method is a method of obtaining a fiber molded body on an electrode by applying a high voltage to a solution in which a polymer is dissolved in a solvent.
  • the steps include a step of producing a solution by dissolving a polymer in a solvent, a step of applying a high voltage to the solution, a step of ejecting the solution, and evaporating the solvent from the ejected solution to form a fiber molded body.
  • the concentration of the polymer with respect to the solvent in the solution in the production method of the present invention is preferably 1 to 30% by weight.
  • concentration of the polymer is less than 1% by weight, it is difficult to form a fiber molded body, which is not preferable.
  • concentration of the polymer with respect to the solvent in the solution is more preferably 2 to 20% by weight.
  • a solvent may be used individually by 1 type and may combine several solvent.
  • Such a solvent is not particularly limited as long as it can dissolve the polymer and the phospholipid and can evaporate at the spinning stage to form a fiber.
  • dichloromethane and ethanol are preferably used in view of handling properties and physical properties.
  • the step of applying a high voltage to the solution, the step of ejecting the solution, and the step of evaporating the solvent from the ejected solution to form a fiber molded body will be described.
  • the method for applying the voltage is not particularly limited as long as the solution in which the polymer is dissolved is ejected and a fiber molded body is formed.
  • the method for applying the voltage by inserting an electrode into the solution or the solution ejection nozzle For example, there is a method of applying a voltage.
  • An auxiliary electrode can be provided separately from the electrode applied to the solution.
  • the value of the applied voltage is not particularly limited as long as the fiber molded body of the present invention is formed, but is usually in the range of 5 to 50 kV.
  • the applied voltage is less than 5 kV, the solution is not ejected and a fiber molded body is not formed, which is not preferable.
  • the applied voltage is more than 50 kV, discharge is generated from the electrode toward the ground electrode, which is not preferable. More preferably, it is in the range of 10 to 30 kV.
  • the desired potential may be generated by any appropriate method known in the art. Thereafter, immediately after the solution in which the polymer is dissolved is ejected, the solvent in which the polymer is dissolved volatilizes and a fiber molded body is formed. Ordinary spinning is performed at room temperature in the atmosphere, but when volatilization is insufficient, it can be performed under negative pressure or in a high-temperature atmosphere. The spinning temperature depends on the evaporation behavior of the solvent and the viscosity of the spinning solution, but is usually in the range of 0 to 50 ° C. A fiber having a smooth fiber surface can be produced by setting the atmosphere during spinning to low humidity. The relative humidity during spinning is preferably 25% or less, more preferably 20% or less.
  • the total thickness of the fiber molded body is not particularly limited, but is preferably 25 ⁇ m to 200 ⁇ m, more preferably 50 to 100 ⁇ m.
  • the processing of laminating a cotton-like fiber structure on the surface of the fiber molded body of the present invention or forming a sandwich structure with the cotton-like structure sandwiched between the fiber molded bodies of the present invention is an object of the present invention. Can be arbitrarily implemented within a range that does not impair the process.
  • the fiber molded body of the present invention may be subjected to a surface treatment with a chemical such as a surfactant in order to modify the hydrophilicity and hydrophobicity of the surface, electrical characteristics and chargeability.
  • coating treatment for imparting antithrombogenicity and surface coating with an antibody or a physiologically active substance can be optionally performed.
  • the coating method and treatment conditions at this time, and the chemicals used for the treatment can be arbitrarily selected within a range that does not damage the fiber structure and impair the purpose of the present invention.
  • a drug can be optionally contained inside the fiber of the fiber molded body of the present invention.
  • the drug used is not particularly limited as long as it is soluble in a volatile solvent and does not impair the physiological activity by dissolution.
  • Specific examples of such drugs include tacrolimus or its analogs, statins, and taxane anticancer agents.
  • a protein formulation and a nucleic acid medicine may be sufficient as long as it can maintain activity in a volatile solvent.
  • it may include substances other than drugs, and may be metals, polysaccharides, fatty acids, surfactants, and volatile solvent-resistant microorganisms.
  • Average fiber diameter Measure the diameter of the fiber by randomly selecting 20 points from the photograph obtained by photographing the surface of the obtained fiber molded body with a scanning electron microscope (Keyence Corporation: trade name “VE8800”) at a magnification of 2000 times. And the average value of all the fiber diameters was calculated
  • required, and it was set as the average fiber diameter. n 20.
  • the inner diameter of the ejection nozzle was 0.8 mm, the voltage was 15 kV, the distance from the ejection nozzle to the electrode plate was 15 cm, and the humidity was 20%.
  • This electrode flat plate was used as a cathode during spinning.
  • the obtained fiber molded body had an average fiber diameter of 4.4 ⁇ m, a thickness of 106 ⁇ m, an average apparent density of 153 kg / m 3 , a fiber surface smoothness of 1.024, and a wetness with fibrin glue of 5.0. there were.
  • a fiber molded body was prepared in the same manner as in Example 1 except that 10 parts of polylactic acid (molecular weight: 137,000, manufactured by Taki Chemical) was dissolved in 90 parts by weight of a dichloromethane solution.
  • the obtained fiber molded body had an average fiber diameter of 5.7 ⁇ m, a thickness of 65 ⁇ m, an average apparent density of 197 kg / m 3 , a smoothness of the fiber surface of 1.004, and wettability with fibrin glue of 3.0. there were.
  • Example 2 Fiber molding as in Example 1 except that 10 parts by weight of polylactic acid (molecular weight 137,000, manufactured by Taki Chemical Co., Ltd.) added with 5% phosphatidylethanolamine dioleoyl was dissolved in 90 parts by weight of a dichloromethane solution. The body was prepared. The obtained fiber molded body had an average fiber diameter of 4.0 ⁇ m, a thickness of 99 ⁇ m, an average apparent density of 165 kg / m 3 , a fiber surface smoothness of 1.014, and a wetness with fibrin glue of 5.0. there were.
  • Example 3 A fiber molded body was prepared in the same manner as in Example 1 except that 1% phosphatidylethanolamine dioleoyl was used. The resulting fiber molded body had an average fiber diameter of 4.3 ⁇ m, a thickness of 63 ⁇ m, an average apparent density of 210 kg / m 3 , a fiber surface smoothness of 1.017, and a wetness with fibrin glue of 3.9. there were.
  • Comparative Example 2 The method described in International Publication No.
  • WO2006 / 022430 that is, polylactic acid to which 1% phosphatidylethanolaminedioleoyl oil is added under high humidity (42 to 55%) in which water is bubbled in a sheet production atmosphere
  • a fiber molded body having an uneven structure on the fiber surface was prepared.
  • the obtained fiber molded body had an average fiber diameter of 3.0 ⁇ m, a thickness of 50 ⁇ m, an average apparent density of 136 kg / m 3 , a fiber surface smoothness of 1.074, and a wetness with fibrin glue of 2.4. there were.
  • Example 4 A fiber molded body was prepared in the same manner as in Example 1 except that 10% phosphatidylethanolamine dioleoyl was used.
  • the obtained fiber molded body had an average fiber diameter of 4.3 ⁇ m, a thickness of 84 ⁇ m, an average apparent density of 142 kg / m 3 , a fiber surface smoothness of 1.018, and a wetness with fibrin glue of 5.0. there were.
  • 10 parts by weight of polylactic acid added with 0.1% phosphatidylcholine dilauroyl was dissolved in 90 parts by weight of a dichloromethane solution to obtain a uniform solution. Spinning was performed by electrospinning to obtain a sheet-like fiber molded body.
  • the inner diameter of the ejection nozzle was 0.8 mm, the voltage was 15 kV, the distance from the ejection nozzle to the electrode plate was 15 cm, and the humidity was 18%.
  • This electrode flat plate was used as a cathode during spinning.
  • the obtained fiber molded body had an average fiber diameter of 4.1 ⁇ m, a thickness of 78 ⁇ m, an average apparent density of 156 kg / m 3 , a fiber surface smoothness of 1.032, and wettability with fibrin glue of 4.0. there were.
  • Example 6 8.5 parts by weight of a lactic acid-glycolic acid copolymer to which 0.4% of phosphatidylcholine dilauroyl was added was dissolved in 86.4 parts by weight of dichloromethane and 5.1 parts by weight of an ethanol solution to obtain a uniform solution. . Spinning was performed by electrospinning to obtain a sheet-like fiber molded body. The inner diameter of the ejection nozzle was 0.8 mm, the voltage was 8 kV, the distance from the ejection nozzle to the electrode plate was 25 cm, and the humidity was 19%. This electrode flat plate was used as a cathode during spinning.
  • the obtained fiber molded body has an average fiber diameter of 4.0 ⁇ m, a thickness of 78 ⁇ m, an average apparent density of 153 kg / m 3 , a smoothness of the fiber surface of 1.009, and wettability with fibrin glue of 5.0. there were.
  • 10 parts by weight of polyglycolic acid to which 0.4% of phosphatidylcholine dilauroyl was added was dissolved in 90 parts by weight of a hexafluoropropanol solution to obtain a uniform solution. Spinning was performed by electrospinning to obtain a sheet-like fiber molded body.
  • the inner diameter of the ejection nozzle was 0.8 mm, the voltage was 15 kV, the distance from the ejection nozzle to the electrode plate was 15 cm, and the humidity was 20%.
  • This electrode flat plate was used as a cathode during spinning.
  • the obtained fiber molded body has an average fiber diameter of 2.5 ⁇ m, a thickness of 122 ⁇ m, an average apparent density of 156 kg / m 3 , a fiber surface smoothness of 1.022, and wettability with fibrin glue of 5.0. there were. As a result, it was found that the fiber molded body containing a phospholipid having a smooth fiber surface according to the present invention was excellent in affinity with fibrin glue.
  • the fiber molded body of the present invention has excellent affinity with fibrin glue, and is useful as a medical article, for example, a protective material for an organ surface or a wound site, a covering material, a sealing material, an artificial dura mater, an adhesion preventing material, or a hemostatic material. It is.

Abstract

L'invention porte sur un corps moulé à base de fibres qui est composé de fibres qui sont formées d'un polymère contenant un phospholipide et ont un lissé de surface de 1,07 ou moins. Les fibres contiennent le phospholipide dans une quantité de 0,1 à 10 % en poids par rapport au polymère. Le corps moulé à base de fibres présente une haute affinité pour une colle à la fibrine.
PCT/JP2011/056682 2010-03-16 2011-03-15 Corps moulé à base de fibres WO2011115281A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2012505779A JPWO2011115281A1 (ja) 2010-03-16 2011-03-15 繊維成形体

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2010059284 2010-03-16
JP2010-059284 2010-03-16

Publications (1)

Publication Number Publication Date
WO2011115281A1 true WO2011115281A1 (fr) 2011-09-22

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WO (1) WO2011115281A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012023594A1 (fr) * 2010-08-16 2012-02-23 帝人株式会社 Fibres à faible capacité de charge et leur procédé de fabrication

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006022430A1 (fr) * 2004-08-26 2006-03-02 Teijin Limited Structure fibreuse contenant un phospholipide
WO2006028244A1 (fr) * 2004-09-07 2006-03-16 Teijin Limited Objet poreux bioabsorbable

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006022430A1 (fr) * 2004-08-26 2006-03-02 Teijin Limited Structure fibreuse contenant un phospholipide
WO2006028244A1 (fr) * 2004-09-07 2006-03-16 Teijin Limited Objet poreux bioabsorbable

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2012023594A1 (fr) * 2010-08-16 2012-02-23 帝人株式会社 Fibres à faible capacité de charge et leur procédé de fabrication
US8802756B2 (en) 2010-08-16 2014-08-12 Teijin Limited Low-charging fiber and method for producing the same

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