WO2006022430A1 - Structure fibreuse contenant un phospholipide - Google Patents

Structure fibreuse contenant un phospholipide Download PDF

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Publication number
WO2006022430A1
WO2006022430A1 PCT/JP2005/015958 JP2005015958W WO2006022430A1 WO 2006022430 A1 WO2006022430 A1 WO 2006022430A1 JP 2005015958 W JP2005015958 W JP 2005015958W WO 2006022430 A1 WO2006022430 A1 WO 2006022430A1
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WO
WIPO (PCT)
Prior art keywords
fiber structure
weight
solution
parts
phospholipid
Prior art date
Application number
PCT/JP2005/015958
Other languages
English (en)
Japanese (ja)
Inventor
Yukako Fukuhira
Eiichi Kitazono
Hiroaki Kaneko
Original Assignee
Teijin Limited
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 Teijin Limited filed Critical Teijin Limited
Priority to JP2006532769A priority Critical patent/JP4354996B2/ja
Publication of WO2006022430A1 publication Critical patent/WO2006022430A1/fr

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Classifications

    • 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
    • D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
    • D01F6/92—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of polyesters
    • 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
    • D01D5/0015—Electro-spinning characterised by the initial state of the material
    • D01D5/003—Electro-spinning characterised by the initial state of the material the material being a polymer solution or dispersion
    • D01D5/0038—Electro-spinning characterised by the initial state of the material the material being a polymer solution or dispersion the fibre formed by solvent evaporation, i.e. dry electro-spinning

Definitions

  • the present invention relates to a cocoon structure containing a phospholipid. More preferably, the present invention relates to a fiber structure having a hole on the fiber surface and serving as a base material suitable for cell culture.
  • a porous material is used as a base material for culturing cells.
  • porous body a foam and a fiber structure obtained by freeze-drying are known. These porous bodies are required to have affinity with cells, biodegradability and safety.
  • Polylactic acid is available at a relatively low cost among these materials that are known for biodegradability and safety.
  • polylactic acid mainly composed of L-lactic acid component has been produced in large quantities recently.
  • an electrostatic spinning method As a method for producing a fiber structure having a small fiber diameter, an electrostatic spinning method is known (see, for example, JP-A-63-145465 and JP-A-2002-249966).
  • the electrospinning method includes a step of introducing a liquid, for example, a solution containing a fiber-forming substance into an electric field, thereby causing the liquid to flow toward an electrode to form a fibrous substance.
  • Normally, hard-to-form substances are cured while being squeezed out of solution. Curing is performed, for example, by cooling (for example, when the spinning liquid is a solid at room temperature), chemical curing (for example, treatment with curing steam), or evaporation of the solvent.
  • the resulting fibrous material is collected on an appropriately placed receptor and can be peeled off if necessary.
  • the electrospinning method can directly obtain a nonwoven fabric-like material, it is not necessary to form a structure once the fibers are produced once, and the operation is simple.
  • a structure obtained by an electrospinning method as a substrate for culturing cells.
  • a fiber structure made of polylactic acid is formed by electrostatic spinning, and smooth muscle cells are cultured on the fiber structure.
  • An object of the present invention is to provide a substrate suitable for cell culture in the field of regenerative medicine.
  • the present invention contains 0.01 to: 100 parts by weight of phospholipid with respect to 100 parts by weight of aliphatic polyester, and the average fiber diameter is 0.05 to 50 ⁇ m. It relates to a structure characterized by this. More preferably, the present invention relates to a fiber structure in which the average porosity of the fiber surface of the H! Structure is 3% to 90%.
  • FIG. 1 shows an example of an apparatus for use in an electrostatic spinning method in which a spinning solution is discharged into an electrostatic field in the production method of the present invention.
  • FIG. 2 shows an example of an apparatus used in the electrospinning method in which fine droplets of a spinning solution are introduced into an electrostatic field in the production method of the present invention.
  • FIG. 9 shows Alamarblue measurement results of Example 6 and Comparative Example 2.
  • the present invention is a fiber structure containing 0.001 to 100 parts by weight of phospholipid with respect to 100 parts by weight of aliphatic polyester.
  • the content of phospholipid with respect to 100 parts by weight of aliphatic polyester is preferably 0.1 to 20 parts by weight, more preferably 0.1 to 10 parts by weight. If the phospholipid content is 100 parts by weight or more, the fiber may lack stability.
  • the average diameter of the fiber structure used in the present invention is preferably 0.05 to 50 ⁇ .
  • An average fiber diameter of less than 0.05 zm is not preferable because degradation is too rapid during cell culture or transplanted in vivo after cell culture. Further, if the average diameter is larger than 50 ⁇ m, it is not preferable because a sufficient surface area for cell culture cannot be obtained.
  • the average fiber diameter is 0.:! ⁇ 20 ⁇ is more preferable.
  • the average porosity of the structure used in the present invention is preferably 3 to 90%, more preferably 11 to 90%, and still more preferably 30 to 90%.
  • the average porosity ratio here means the ratio of the pore area to the entire mi surface area. Scanning electron micrographs of the fiber structure using a scanning electron micrograph (image processing software (next New Qube)) are used. This is the result of binarization processing.
  • the average porosity is 3 to 11%, a sufficient cell adhesion effect may not be obtained. Therefore, by providing unevenness on the surface, a sufficient cell adhesion effect can be preferably provided. Even in the case where the average porosity is 11% or more, it is preferable that the surface further has irregularities because a further excellent cell adhesion effect can be obtained.
  • the average porosity is greater than 30%, a better cell adhesion effect can be obtained. Further, if the average porosity is more than 90%, the strength as a film may not be maintained.
  • Examples of the aliphatic polyester used in the present invention include polylactic acid, polydaricholic acid, polystrength prolacton, polybutylene succinate, polyethylene succinate, and copolymers thereof.
  • polylactic acid, polyglycol monooleic acid, lactic acid monoglycolic acid copolymer, polycaplatatotone, and lactic acid monostrength prolactone copolymer are preferable. Force prolacton is preferred.
  • the weight average molecular weight of the aliphatic polyester is preferably 20,000 to 100,000. More preferably, the weight average molecular weight is 50,000 to 500,000.
  • the phospholipid used in the present invention can be used regardless of its origin, whether it is extracted from animal tissue or artificially synthesized.
  • a phospholipid selected from the group consisting of phosphatidylethanolamine, phosphatidylcholine, phosphatidylserine, phosphatidylglyceride and derivatives thereof.
  • Preferred is phosphatidylethanolamine or phosphatidylcholine. More preferred is L-one phosphatidylethanolamine dioleo oil or L-one phosphatidinorecorin dioleoyl.
  • the fiber structure used in the present invention refers to a three-dimensional structure in which one or more kinds of ⁇ are laminated and formed by weaving, knitting, or other methods. It shall also include multiple collected yarns. Specific examples of the form of the fiber structure preferably include a nonwoven fabric, a woven fabric, a knitted fabric, a tube, a mesh, and the like. A more preferable form is a nonwoven fabric. Also included are composites of fibers containing phospholipids and fibers not containing phospholipids.
  • the average apparent density of the fiber structure is preferably 10 to 3500 kg / m 3 .
  • the average apparent density means the density calculated from the area, average thickness, and mass of the structure. If the average apparent density is greater than 3500 kg Zm 3 , the solution containing nutrients may not sufficiently penetrate into the fiber structure during cell culture, and the cells may be cultured only on the fiber structure surface. If the average apparent density is less than 10 kg Zm 3 , the mechanical strength required during cell culture may not be maintained.
  • the preferred average apparent density is 1 0 to 2 5 0 kg Roh m 3.
  • Examples of methods for producing the structure include an electrostatic spinning method, a spunbond method, a melt blow method, and a flash spinning method.
  • the electrostatic spinning method is preferable from the viewpoint of operability and simplicity.
  • the method for producing by the electrospinning method will be described in detail below.
  • a solution in which aliphatic polyester is dissolved in a volatile solvent is discharged into an electrostatic field formed between electrodes, and the solution is spun toward the electrodes to form a »form
  • a fiber structure can be obtained by accumulating substances on the collection substrate.
  • the fibrous substance indicates not only a state in which the solvent of the solution has been completely distilled off to form a structure, but also a state in which the solvent of the solution is still contained.
  • any metal, inorganic, or organic material only needs to exhibit conductivity.
  • a conductive metal, inorganic, or organic thin film may be provided over the insulator.
  • the electrostatic field in the present invention is formed between a pair or a plurality of electrodes, and even if a high voltage is applied to the electrodes that are misaligned. This includes, for example, the use of two high voltage electrodes with different voltage values (for example, 15 kV and 10 kV) and a total of three electrodes connected to earth, or a number exceeding three. This includes the use of other electrodes.
  • the first step is to produce a solution consisting of aliphatic polyester, phospholipid, and volatile solvent.
  • the concentration of the aliphatic polyester in the solution in the production method of the present invention is preferably 1 to 30% by weight. If the concentration of the aliphatic polyester is less than 1% by weight, it is not preferable because the concentration is too low, making it difficult to form a structure. On the other hand, if it exceeds 30% by weight, the viscosity of the solution increases. This is not preferable because a high voltage needs to be applied between the electrodes.
  • the concentration of the aliphatic polyester is more preferably 2 to 25% by weight.
  • the volatile solvent of the present invention is not particularly limited as long as the aliphatic polyester can be dissolved.
  • volatile solvents include non-water soluble halogen-containing hydrocarbons such as methylene chloride, black mouth form, and carbon tetrachloride, and acetone, methanol, ethanol, propanol, which can dissolve water in any proportion. Isopropanol, Toluene, Tetrahydrofuran, 1, 1, 1, 3, 3, 3_Hexafluoroisopropanol, Water, 1,4-Dioxane, Cyclohexane, Cyclohexanone, N, N-Dimethyl For example, formamide and acetonitrile.
  • methylene chloride, chloroform, acetone, and tetrahydrofuran which are particularly highly volatile, are particularly preferred for promoting the surface porosity.
  • solvents may be used alone, or a plurality of solvents may be combined. Further, other solvents may be used in combination as long as the object of the present invention is not impaired.
  • any method can be used to discharge the solution into the electrostatic field.
  • any method can be used to discharge the solution into the electrostatic field.
  • an appropriate device can be used, for example, an injection needle-like solution ejection nozzle in which a voltage is applied by an appropriate means, for example, a high voltage generator 6 to the tip of the cylindrical solution holding tank 3 of the syringe. Place 1 and guide the solution to its tip.
  • the tip of the ejection nozzle 1 is placed at an appropriate distance from the grounded fibrous material collection electrode 5, and when the solution 2 exits the tip of the ejection nozzle 1, this tip and the H t-like substance collection electrode 5 A fibrous material is formed between them.
  • the distance between the electrodes depends on the charge amount, nozzle dimensions, spinning fluid flow rate, spinning fluid concentration, etc., but a distance of 5 to 20 cm was appropriate when it was about 10 kV.
  • the applied electrostatic potential is generally 3 to 100 kV, preferably 5 to 50 kV, and more preferably 5 to 30 kV.
  • the desired potential can be generated by any appropriate method.
  • the electrode also serves as a collection substrate, but by installing an object that can be a collection substrate between the electrodes, a collection substrate is provided separately from the electrode, and the structure can be collected there. I can do it.
  • a collection substrate is provided separately from the electrode, and the structure can be collected there. I can do it.
  • continuous production becomes possible.
  • the relative humidity between the nozzle and the collection substrate is maintained at 20% or more, it is preferable because the fiber having the surface structure can be easily obtained.
  • a more preferable relative humidity is 25 to 95%.
  • the step of obtaining the fiber laminate accumulated on the collection substrate will be described.
  • the solvent evaporates depending on the conditions to form a soot-like substance.
  • the solvent completely evaporates until it is collected on the collection substrate, but if the solvent evaporation is insufficient, it may be spun under reduced pressure.
  • the temperature at which the spinning is performed depends on the evaporation behavior of the solvent and the viscosity of the spinning solution. Usually, it is 0 to 50 ° C.
  • the fiber structure of the present invention may be composed of the fiber structure alone, but may be combined with other members. Further, the cell culture substrate of the present invention may be combined with proteins such as cell growth factor and cell growth factor, extracellular matrix such as collagen, etc., as long as the characteristics are not impaired.
  • Polylactic acid (Shimadzu Corporation: trade name “La cty 9031”, weight average molecular weight 1 68,000) 100 parts by weight and phosphatidylethanolamine dioleoyl oil (Wako Pure Chemical Industries) 0.5 parts by weight Special grade) 899. Dissolved in 5 parts by weight at room temperature (29 ° C) to prepare a solution. Using the apparatus shown in FIG. 1, the solution was discharged to the fibrous material collecting electrode 5 for 15 minutes. The inner diameter of the ejection nozzle 1 was 0.8 mm, ® was 12 kV, the distance from the ejection nozzle 1 to the fibrous material collecting electrode 5 was 20 cm, and the relative humidity was 39%.
  • Polylactic acid (Shimadzu Corporation: trade name “La cty 9031”, weight average molecular weight 1 68,000) 100 parts by weight and phosphatidylcholine dioleoyl oil (Wako Pure Chemical Industries) 0.5 parts by weight of methylene chloride (Wako Pure Chemical Industries, special grade) 899 Dissolved in 5 parts by weight at room temperature (29 ° C) to prepare a solution.
  • the solution was discharged to the fibrous material collecting electrode 5 for 15 minutes.
  • the inner diameter of the ejection nozzle 1 was 0.8 mm
  • the voltage was 12 kV
  • the distance from the ejection nozzle 1 to the fibrous material collecting electrode 5 was 20 cm
  • the relative humidity was 39%.
  • Polylactic acid (Shimadzu Corporation: trade name “L acty 9031”, weight average molecular weight 1 68, 000) 100 parts by weight and phosphatidylethanolamine dioleoyl oil (Wako Pure Chemical Industries) 0.5 parts by weight Special grade) 449.75 parts by weight, N, N-dimethylformamide 449.75 parts by weight was dissolved at room temperature (29 ° C) to prepare a solution.
  • the solution was discharged to the fibrous material collecting electrode 5 for 15 minutes.
  • the inner diameter of the ejection nozzle 1 was 0.8 mm
  • the voltage was 12 kV
  • the distance from the ejection nozzle 1 to the fibrous material collecting electrode 5 was 10 cm
  • the relative humidity was 39%.
  • the obtained fiber structure was measured with a scanning electron microscope (Hitachi S-240 0).
  • the average fiber diameter was 0.7 ⁇ 111, the average porosity was 3%, and the average pore diameter was 0.032 1 ⁇
  • the apparent density was 210 kg / m 3 .
  • Figure 6 shows a scanning electron micrograph.
  • Example 2 The fiber structure obtained in Example 1 was cut into a circle with a diameter of 12 mm, immersed in a 70% ethanol aqueous solution (Wako Pure Chemical Industries) for air sterilization, air-dried, and then 0.25 in a cell culture vessel.
  • PAE pig aorta-derived vascular endothelial cells
  • Cell proliferation ability was measured on Alamarblue on day 1 and day 4. In the measurement, fluorescence 590 nm that appeared using excitation light with a wavelength of 530 nm was detected. The results are shown in Fig. 9, Comparative Example 2.
  • Example 6 The same operation as in Example 6 was performed except that the fiber structure of Comparative Example 1 was used. The results are shown in Fig. 9.
  • Example 6 As a result of performing a significant difference test using two specimens, one day after culturing, Example 6 was statistically significant at a risk rate of 0.0 0 1% between the two specimens of Comparative Example 2. As a result, it was found that adhesion and proliferation were good. After 4 days of culturing, the results of Example 6 were good in adhesion and proliferation with a statistically significant difference between the two specimens of Comparative Example 2 and that of Comparative Example 2 with a risk factor of 0.001%.

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  • Engineering & Computer Science (AREA)
  • Chemical & Material Sciences (AREA)
  • Textile Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Dispersion Chemistry (AREA)
  • Mechanical Engineering (AREA)
  • Artificial Filaments (AREA)
  • Nonwoven Fabrics (AREA)
  • Spinning Methods And Devices For Manufacturing Artificial Fibers (AREA)
  • Woven Fabrics (AREA)

Abstract

L'invention décrit une structure fibreuse caractérisée en ce qu’elle contient de 0,01 à 100 parties en poids d'un phospholipide pour 100 parties en poids d'un polyester aliphatique et ayant un diamètre moyen de fibre de 0,05 à 50 µm. De préférence, la structure fibreuse possède des pores dans la surface fibreuse et convient pour servir de base pour une culture cellulaire.
PCT/JP2005/015958 2004-08-26 2005-08-25 Structure fibreuse contenant un phospholipide WO2006022430A1 (fr)

Priority Applications (1)

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JP2006532769A JP4354996B2 (ja) 2004-08-26 2005-08-25 リン脂質を含有する繊維構造体

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JP2004246432 2004-08-26
JP2004-246432 2004-08-26

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101949071A (zh) * 2010-09-16 2011-01-19 扬州大学 一种生物可降解复合纤维及其生产方法
WO2011059102A1 (fr) 2009-11-11 2011-05-19 帝人株式会社 Article à base de fibres moulées
WO2011115281A1 (fr) * 2010-03-16 2011-09-22 帝人株式会社 Corps moulé à base de fibres
JP2011246524A (ja) * 2010-05-24 2011-12-08 Teijin Ltd 繊維成形体
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
WO2012029971A1 (fr) * 2010-08-31 2012-03-08 帝人株式会社 Matériau composite de colle à la fibrine et de moulage de fibres
WO2012118236A1 (fr) * 2011-03-03 2012-09-07 帝人株式会社 Corps moulé fibreux
JP2013066536A (ja) * 2011-09-21 2013-04-18 Teijin Ltd 止血効果に優れたシート状止血材
JP2014004705A (ja) * 2012-06-22 2014-01-16 Teijin Ltd 柔軟性と保水性に優れた不織布およびその製造方法

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5542080B2 (ja) * 2011-03-30 2014-07-09 帝人株式会社 柔軟性と保水性に優れた不織布およびその製造方法
CN105839292A (zh) * 2014-11-07 2016-08-10 蔡留凤 一种基于医用高分子材料的生物医用静电纺丝膜

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JPH10504583A (ja) * 1994-06-13 1998-05-06 モンサント・カンパニー 脂肪族ポリエステル組成物
JP2002249966A (ja) * 2001-01-26 2002-09-06 Korea Inst Of Science & Technology 微細繊維状高分子ウェブの製造方法
JP2002371174A (ja) * 2001-06-13 2002-12-26 Mitsui Chemicals Inc 農薬含有樹脂組成物
US20040013873A1 (en) * 2000-08-18 2004-01-22 Wendorff Joachim H Production of polymer fibres having nanoscale morphologies

Patent Citations (4)

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Publication number Priority date Publication date Assignee Title
JPH10504583A (ja) * 1994-06-13 1998-05-06 モンサント・カンパニー 脂肪族ポリエステル組成物
US20040013873A1 (en) * 2000-08-18 2004-01-22 Wendorff Joachim H Production of polymer fibres having nanoscale morphologies
JP2002249966A (ja) * 2001-01-26 2002-09-06 Korea Inst Of Science & Technology 微細繊維状高分子ウェブの製造方法
JP2002371174A (ja) * 2001-06-13 2002-12-26 Mitsui Chemicals Inc 農薬含有樹脂組成物

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102597350A (zh) * 2009-11-11 2012-07-18 帝人株式会社 纤维成形体
WO2011059102A1 (fr) 2009-11-11 2011-05-19 帝人株式会社 Article à base de fibres moulées
JP5563590B2 (ja) * 2009-11-11 2014-07-30 帝人株式会社 繊維成形体
WO2011115281A1 (fr) * 2010-03-16 2011-09-22 帝人株式会社 Corps moulé à base de fibres
JPWO2011115281A1 (ja) * 2010-03-16 2013-07-04 帝人株式会社 繊維成形体
JP2011246524A (ja) * 2010-05-24 2011-12-08 Teijin Ltd 繊維成形体
CN103025933A (zh) * 2010-08-16 2013-04-03 帝人株式会社 低带电性纤维及其制造方法
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
RU2557623C2 (ru) * 2010-08-16 2015-07-27 Тейдзин Лимитед Низкозаряженное волокно и способ его производства
WO2012029971A1 (fr) * 2010-08-31 2012-03-08 帝人株式会社 Matériau composite de colle à la fibrine et de moulage de fibres
CN101949071A (zh) * 2010-09-16 2011-01-19 扬州大学 一种生物可降解复合纤维及其生产方法
WO2012118236A1 (fr) * 2011-03-03 2012-09-07 帝人株式会社 Corps moulé fibreux
JPWO2012118236A1 (ja) * 2011-03-03 2014-07-07 帝人株式会社 繊維成形体
JP5698339B2 (ja) * 2011-03-03 2015-04-08 帝人株式会社 繊維成形体
JP2013066536A (ja) * 2011-09-21 2013-04-18 Teijin Ltd 止血効果に優れたシート状止血材
JP2014004705A (ja) * 2012-06-22 2014-01-16 Teijin Ltd 柔軟性と保水性に優れた不織布およびその製造方法

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JP4354996B2 (ja) 2009-10-28
TW200613016A (en) 2006-05-01

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