WO2012060592A2 - Film de revêtement composite nanotubes de carbone-polymère qui diminue la toxicité et l'inflammation et présente une biocompatibilité améliorée et une résistance de surface ajustée - Google Patents

Film de revêtement composite nanotubes de carbone-polymère qui diminue la toxicité et l'inflammation et présente une biocompatibilité améliorée et une résistance de surface ajustée Download PDF

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WO2012060592A2
WO2012060592A2 PCT/KR2011/008193 KR2011008193W WO2012060592A2 WO 2012060592 A2 WO2012060592 A2 WO 2012060592A2 KR 2011008193 W KR2011008193 W KR 2011008193W WO 2012060592 A2 WO2012060592 A2 WO 2012060592A2
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coating film
carbon nanotubes
polymer
thickness
biocompatible polymer
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PCT/KR2011/008193
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English (en)
Korean (ko)
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WO2012060592A3 (fr
WO2012060592A9 (fr
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강동우
남태현
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경상대학교 산학협력단
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/40—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
    • A61L27/42—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having an inorganic matrix
    • A61L27/422—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having an inorganic matrix of carbon
    • 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
    • A61L31/12—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material
    • A61L31/121—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having an inorganic matrix
    • A61L31/122—Composite materials, i.e. containing one material dispersed in a matrix of the same or different material having an inorganic matrix of carbon

Definitions

  • the present invention relates to a bio-insertable polymer coating film comprising a biocompatible polymer and carbon nanotubes and having a thickness of nanometer and submicron meter and a method of manufacturing the same. More specifically, the present invention has an ultra-thin film thickness of less than a micron manufactured by synthesizing carbon nanotubes in a biocompatible polymer, and can improve biocompatibility and control surface strength, and inhibit coating toxicity and inflammation. And a method for producing the same.
  • carbon nanotubes have a graphite sheet rounded to a nano-sized diameter to form a tubular shape, and the diameter of the tube is a very small region of several to several tens of nanometers. While these carbon nanotubes are known as new materials having excellent mechanical strength, electrical conductivity and thermal conductivity, excellent field emission characteristics, and highly efficient hydrogen storage medium characteristics, efforts to manufacture high-performance advanced materials using these characteristics are active. Do.
  • the present inventors have made efforts to manufacture a coating film having an ultra-thin thickness that can be applied to a medical device inserted into a microvascular in vivo.
  • the inventors have developed a coating film having a thickness of 200 nm or less by mixing carbon nanotubes with a biocompatible polymer.
  • the biocompatibility of the coating film having the ultra-thin film thickness can be increased, the mechanical strength can be adjusted, and toxicity and inflammation can be suppressed.
  • Another object of the present invention is to provide a method of manufacturing the coating film and a method of controlling the nano-surface roughness and surface tension of the coating film.
  • the present invention provides a polymer composite coating film comprising a biocompatible polymer and carbon nanotubes and has a thickness of nano (nanometer) and submicron (meter) and suppresses toxicity and inflammation to provide.
  • biocompatible polymer has affinity with blood or cellular tissues, and when applied to a living body, is not recognized as an external foreign substance and has undesirable long-term effects such as clot formation, inflammation, and physical property change. It means a polymer that does not induce. In general, when the polymer material is in contact with blood, the adsorption of blood protein components occurs on the surface of the material within a few seconds after contact with the blood, and platelet thrombosis reaction and red thrombus appear.
  • the biocompatible polymer of the present invention has a surface modification to improve blood compatibility. Included polymers. Biocompatible polymers that can be used in the present invention include polymers surface-modified with high hydrophilic polymer materials such as polyethylene glycol and polyacrylamide.
  • the biocompatible polymer includes a polymer having cell compatibility, and includes a polymer having little or no effect on the number or growth of cells, cell membrane maintenance, biosynthesis process or enzyme activity.
  • the biocompatible polymer of the present invention may mean a non-degradable polymer, polyolefin, polystyrene, polyethylene oxide, polyvinyl chloride, polyamide, polymethyl methacrylate, polyurethane, polyester or these Combinations of but are not limited to.
  • it has excellent blood compatibility and is widely used in artificial blood vessels, artificial heart, etc., which are in direct contact with blood, and has excellent mechanical and thermal resistance, and polycarbonates, which are applied to heart, lung assistive devices, artificial heart valve switch, etc. to be.
  • the biocompatible polymer of the present invention may be polycarbonate urethane (hereinafter referred to as PCU).
  • the PCU is an FDA approved polymer medical polymer for clinical applications such as heart valves, meniscus or artificial blood, and because it is not degraded by oxygen, it can maintain a constant mechanical strength even in body fluids.
  • the PCU may be synthesized with carbon nanotubes as a matrix to exhibit good dispersibility.
  • carbon nanotube is a honeycomb-shaped planar carbon structure in which one carbon atom is bonded to three other carbon atoms is rolled to have a tube shape, and generally has a diameter of 1 to 100 nanometers (nm) and a length.
  • a carbon material having a high aspect ratio ranging from several nanometers (nm) to several tens of micrometers ( ⁇ m).
  • MWCNTs multi-walled nanotubes
  • SWCNT single-walled nanotube
  • carbon nanotubes include all of them without limitation, but are preferably multi-walled carbon nanotubes.
  • the diameter of the carbon nanotubes usable in the present invention may be 1 to 100nm.
  • the polymer composite coating film of the present invention can be used to coat a living body implantable medical device.
  • bioinsertion medical device is a medical device for artificial blood vessels, artificial vessel support, fusion power electrode source or power supply wire in the blood vessel, biochip, nano robot, implant, artificial heart valve, artificial bladder and artificial urinary tract, artificial It may be selected from the group consisting of meniscus, artificial blood vessel, artificial heart, pacemaker insulator, catheter, and stent, but is not limited thereto.
  • the biocompatible polymer and the carbon nanotube content included in the coating film of the present invention may be included in a ratio of 1: 1 to 1:10 wt%.
  • the coating film is composed of a polymer-nanocomposite obtained by synthesizing the biocompatible polymer and carbon nanotubes.
  • the polymer-nanocomplex has all the features of the coating film disclosed in the present invention.
  • composite means that two or more individual materials are synthesized.
  • the polymer composite coating film of the present invention may have a thickness of nano (nanometer) and submicron (submicron-meter), preferably has a thickness of 30 to 200 nm and is characterized in that the transparent.
  • the nanometer thickness refers to one millionth of one meter, and means a thickness range of 100 nm or less for the purposes of the present invention.
  • the submicron means a thickness range of 100nm to 1 ⁇ m.
  • the biocompatible polymer and carbon nanotubes to the thickness of the nano and submicron meters, preferably 100nm or less, it is possible to form a coating of the biomedical device to be inserted into the microvascular and coronary artery, transparent It can be used to analyze the activity of living cells.
  • the coating film is toxic (NO: Nitrite) and anti-inflammatory factors (TNF-alpha, IL-1beta) is reduced as the carbon carbon nanotubes (CNT) is added, the synthesis of CNTs to make nanotopoes of immune cells Activity can also be inhibited (see FIGS. 12 and 13).
  • the coating film is characterized in that the carbon nanotubes have a structure that is not directly exposed to the surface of the biocompatible polymer. Since the carbon nanotubes are not directly exposed to the surface, the chemical composition of the biocompatible polymer is maintained, but the biocompatibility and toxicity are improved compared to the existing biopolymer materials by generating the carbon nanotube-like nanoforms in the biocompatible polymer. The mechanical strength can be controlled by the synthesis ratio of carbon nanotubes. As shown in FIG. 6, when the polymer sphere generated when the heat is applied is also generated on the carbon nanotubes (30 nm thick), the carbon nanotubes are not exposed on the surface and covered with an ultra-thin film of about 30 nm. I could confirm it.
  • the coating film has insulation unlike a polymer-carbon nanotube composite used in an information and communication device for medical use.
  • the present invention comprises the steps of sonicating each of the biocompatible polymer and carbon nanotubes in each solvent in a synthesis ratio of 1: 1 to 1:10 wt%; Mixing the two sonicated solutions; Coating the mixed solution on glass using a spin coater; Drying the glass coated with the mixed solution at room temperature; And to provide a method for producing a polymer composite coating film having a thickness of nano (nanometer) and submicron (submicron-meter), comprising the step of sterilizing and disinfecting the dried glass by ultraviolet rays.
  • biocompatible polymer in the production method of the present invention is the same as described above, preferably polycarbonate-based, more preferably may be a polycarbonate urethane.
  • the solvent of the carbon nanotube may be any one or more selected from the group consisting of water, 1,2-dichloroethane, tetrahydrofuran, dimethylformamide, toluene, ethanol, and mixtures thereof. And preferably 1,2-dichloroethane.
  • the solvent of the polycarbonate urethane is preferably chloroform.
  • tip and bath ultrasonic equipment may be used, and the sonication time may be 1 to 24 hours, but is not limited thereto and may be easily selected by those skilled in the art according to the purpose.
  • polycarbonate urethane is mixed with chloroform
  • carbon nanotubes are mixed with 1,2-dichloroethane
  • each solution is sonicated and dispersed, and then coated on glass using a spin coater. It was dried at room temperature, sterilized and disinfected with ultraviolet rays to prepare a coating film having a thickness of 100 nm or less.
  • the coating film may be used as a coating material of a bio-invasive medical device, and the above-described bio-invasive medical device may be applied in the same manner, and preferably, a microvascular medical device, an artificial vessel support, a source of fusion power electrode in a blood vessel, or Power supply wire, nanorobot, implant, artificial heart valve, artificial bladder and urinary tract, artificial meniscus, artificial blood vessel, artificial heart, heart pacemaker insulator.
  • the manufacturing method of the present invention may further include adjusting the surface strength of the coating film by adjusting the synthesis ratio of the biocompatible polymer and the carbon nanotubes.
  • the manufacturing method of the present invention may further comprise the step of checking the biocompatibility by controlling the roughness at the nanoscale of the coating film by adjusting the synthesis ratio of the biocompatible polymer and the carbon nanotubes.
  • the weight percent content ratio of the carbon nanotubes is increased during the synthesis between the biocompatible polymer and the carbon nanotubes, the roughness at the nanoscale of the nanocoating film is increased and the surface energy is increased. It was confirmed that biocompatibility can be increased by controlling the adsorption of proteins in vivo by increasing the surface energy in the polymer-nano composite coating film having a thickness of.
  • the roughness of the nano-surface can be controlled to adjust the adsorption of the protein in the living body can be prepared to suit the biocompatibility of the polymer-nanocomplex.
  • vitronectin which is a cell-adhesive glycoprotein present in plasma and serum connective tissue, and animals
  • FBS a cell-adhesive glycoprotein present in plasma and serum connective tissue
  • the present invention can be improved in comparison with the present invention, and can be applied to more implant polymer applications by controlling the mechanical properties by controlling the mechanical strength by the synthesis ratio of the nanotubes.
  • a coating film having a thickness of nano and submicron meters manufactured by the manufacturing method may be used for artificial blood vessel support, artificial bladder and urinary tract, coating of fusion power electrode source in blood vessel and power supply wire of power source. It can be used as a bio coating material.
  • the ultra-thin structure has the effect of inhibiting human immune toxicity
  • the method of the present invention improves the biocompatibility of tissue cells (or stem cells) and immune by inhibiting the activity of macrophage (macrophage) which is a representative immune active cell Toxicity can be reduced, more specifically, the addition of carbon carbon nanotubes (CNT) reduces the toxicity (NO: Nitrite) and anti-inflammatory factors (TNF-alpha, IL-1beta), and also synthesizes CNTs Making a topo may inhibit the activity of immune cells (see FIGS. 12 and 13).
  • the polymer-nanocomposite or coating film may be used in all bio-invasive medical devices, and may be suitable for an environment such as capillary and micro-vessel insertion that requires ultra-thin thickness while maintaining nanotopos.
  • the present invention relates to a coating film having a thickness of nano (nanometer) and submicron (submicron-meter) by mixing carbon nanotubes with a biocompatible polymer, and a method of manufacturing the same, by controlling the synthesis ratio of the polymer and carbon nanotubes It has been found that it is possible to increase the biocompatibility and control the mechanical strength of the coating film having the ultra-thin film thickness, and to suppress toxicity and inflammation, and to use such features to insert a medical device that is inserted into microvascular vessels such as nano medical devices and wire coatings. There is an effect that can be applied to.
  • Figure 1 shows a coating of the surface of the power supply wire and the electrode source module as an application example of the coating film according to the present invention.
  • Figure 2 schematically shows the manufacturing process of the coating film according to the present invention.
  • Figure 3 shows a sample of the coating film prepared while varying the synthesis ratio of CNT and PCU.
  • Figure 4 shows an example of the result of measuring the thickness of the polymer coating film according to the present invention.
  • the lower figure shows the thickness of the carbon nanotube and polymer composite (AFM analysis) and has a thickness of about 31 nm.)
  • Figure 5 shows another example of the results of measuring the thickness of the polymer coating film according to the present invention.
  • the lower figure shows the thickness of the carbon nanotube and polymer composite (AFM analysis) and has a thickness of about 31 nm.)
  • FIG. 6 shows that the polymer sphere generated when the heat is applied is also generated on the carbon nanotubes (30 nm thick), and the carbon nanotubes are not exposed on the surface and are covered with an ultra-thin film of about 30 nm. .
  • Figure 7 shows the nano-scale surface roughness of the coating film prepared by varying the synthesis ratio of CNT and PCU by atomic microscope (AFM).
  • the bottom plot shows the change in surface tension due to the synthesis of carbon nanotubes (the y-axis represents the angle). As the nanotubes increase, the surface roughness increases and thus the surface tension increases.
  • Figure 8 shows the results of measuring the dynamic hardness of the coating film prepared while varying the synthesis ratio of the weight of the CNT and PCU. It can be seen that as the carbon nanotubes increase, the surface hardness increases (the surface hardness increases more than twice when the CNT weight is increased by 10 times).
  • Figure 9 shows the degree of protein adsorption according to the synthesis ratio of CNT and PCU weight in the coating film of the present invention. It can be seen that the roughness of the nanosurface rather than the surface energy affects the protein adsorption. As carbon nanotubes increase, more proteins are adsorbed. The lower figure shows the degree of adsorption of Vitronectin according to the synthesis ratio of the coating film. As the carbon nanotube ratio increases, more protein is adsorbed.
  • Figure 10 shows the adsorption and proliferation of immune cells according to the synthesis ratio of CNTs and PCU in the coating film of the present invention (upper figure). As the surface tension increases, the adsorption of immune cells increases (3 hours). . In addition, it can be seen that the increase in growth (24 hours) by the increased adsorption. The lower figure shows the adsorption and proliferation of messengerchymal stem cells, and it can be seen that the self-renewal is regulated according to the increased degree of nanoroughness and the degree of protein adsorption.
  • FIG. 11 is a photograph showing comparison of the thickness and shape of the coating film of the pure PCU (left) and the PCU / CNT composite (right) synthesized with CNT, respectively.
  • FIG. 12 is a photograph and a graph showing an aspect of suppressing the activity of immune cells according to the synthesis ratio of CNT and PCU in the coating film of the present invention. Through this, it can be seen that the activity of immune cells is inhibited by making CNTs by synthesizing CNTs as in the present invention.
  • FIG. 13 is a graph showing that toxicity (NO: Nitrite) and anti-inflammatory factors (TNF-alpha, IL-1beta) decrease as carbon carbon nanotubes (CNT) are added in the coating film of the present invention. Through this, it can be seen that the present invention is inhibited toxic and anti-inflammatory factors.
  • NO Nitrite
  • TNF-alpha, IL-1beta carbon carbon nanotubes
  • a solution was prepared by injecting 1 g of polycarbonate urethane (Lubrizol, PC-3575A) into 16 ml of chloroform. 0.3g of carbon nanotubes were injected into 60 ml of 1,2-dichloroethane to prepare a solution. Then, polycarbonate urethane was subjected to ultrasonic waves at room temperature for 1 hour and carbon nanotubes for 24 hours, respectively. Then, the two solutions were mixed. Thus, the content of carbon nanotubes compared to the polycarbonate urethane is 100 and 1000% by weight. Then, two spin coaters were used to coat the glass, followed by drying in vacuo at room temperature. And CNT-PCU was prepared by sterilization and disinfection by exposing to UV. The mixing degree of chemcal solution to make a specific combination is as follows.
  • the carbon nanotubes are coated at 100 nm or less, thereby maintaining a transparent state.
  • the dynamic hardness is a hardness obtained from the test force and the indent depth of the process of pushing the indenter as a method of measuring how the indenter penetrates into the sample.
  • the test force P [mN] intruder penetrates into the sample.
  • Hardness was calculated
  • Example 3 In vivo protein adsorption regulation effect of CNT-PCU composite coating membrane
  • the degree of protein adsorption of the coating film was found to increase with the CNT / PCU ratio.
  • nanoscale surface roughness is very important in protein adsorption, and vitronectin adsorption also increased with the CNT / PCU ratio. Therefore, by adjusting the surface energy by adjusting the CNT / PCU ratio of the coating film, it was confirmed that the adsorption of protein in vivo can be adjusted to make it more suitable for living (see Figure 9).
  • Macrophages J774, ATCC were incubated at 100000 / cm 2 in each coated sample, and the number of cells was measured by MTT after 3 and 24 hours.
  • MTT MTT after 3 and 24 hours.
  • MSC stem cells
  • Lonza stem cells
  • TNF- ⁇ and IL-6 levels were measured using commercial ELISA kits (Quantikine: R & D system, Minneapolis, MN) of mouse TNF- ⁇ and IL-6.
  • each supernatant sample was collected and stored at -80 ° C, and also measured three times at the same time by a microplate reader and by the average sample error. Appeared.
  • Recombinant TNF- ⁇ and IL-6 were used as standard controls for each cytokine assay.
  • This analysis range is 15.6-1000 pg / ml for TNF- ⁇ and 7.8-500 pg / ml for IL-6.
  • macrophages medium was recovered and used for ELISA experiments for IL-6 and TNF- ⁇ . Data were calculated from the ELISA experiment, and the optical density unit was converted into pg / 10 4 cells divided by the number of viable cells obtained in the viability and apoptosis experiments.
  • macrophage-derived proinflammatory cytokines (TNF- ⁇ and IL-6) were synthesized at 37 ° C., 0-4 h, 4-12 h, 12-24 h, 24- Media was harvested at 36h and 48h and cells were washed with DPBS, provided fresh media and measured. All recovered media was stored at -80 ° C and measured simultaneously.
  • the composite coating film of the present invention reduces the toxicity (NO: Nitrite) and anti-inflammatory factors (TNF-alpha, IL-1beta) as carbon carbon nanotubes (CNT) is added, and synthesizes CNTs to nanotopo Making it was confirmed that it has an effect that can also inhibit the activity of immune cells (see Figure 12, 13).

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Abstract

La présente invention concerne un film de revêtement ayant une épaisseur de pas plus de 200 nm dans lequel des nanotubes de carbone sont mélangés avec un polymère biocompatible, et l'invention est avantageuse en ce qu'il a été confirmé que l'ajustement des proportions de la synthèse du polymère et des nanotubes de carbone peut augmenter la biocompatibilité et ajuster la résistance mécanique et peut diminuer la toxicité et l'inflammation du film de revêtement ayant une épaisseur de film ultra-mince, et ces caractéristiques peuvent être utilisées dans des articles d'équipement médical qui sont introduits dans des microvaisseaux dans le corps tels que des dispositifs médicaux de dimension nanométrique et des revêtements de fils.
PCT/KR2011/008193 2010-11-01 2011-10-31 Film de revêtement composite nanotubes de carbone-polymère qui diminue la toxicité et l'inflammation et présente une biocompatibilité améliorée et une résistance de surface ajustée WO2012060592A2 (fr)

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KR10-2010-0107561 2010-11-01
KR20100107561A KR101271535B1 (ko) 2010-11-01 2010-11-01 생체 적합성의 향상 및 표면 강도를 조절할 수 있는 탄소나노튜브 폴리머 복합체 코팅막 및 그의 제조방법

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2014118522A1 (fr) 2013-01-30 2014-08-07 Jaeger, Michael Nanostructures de carbone pour le renforcement d'un tissu oculaire
WO2015034930A1 (fr) * 2013-09-03 2015-03-12 William Marsh Rice University Traitement de maladies inflammatoires par des matériaux carbonés
US9312046B2 (en) 2014-02-12 2016-04-12 South Dakota Board Of Regents Composite materials with magnetically aligned carbon nanoparticles having enhanced electrical properties and methods of preparation
US9396853B2 (en) 2010-09-16 2016-07-19 Georgia Tech Research Corporation Alignment of carbon nanotubes comprising magnetically sensitive metal oxides in nanofluids

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KR20080096051A (ko) * 2007-04-26 2008-10-30 한국과학기술원 탄소나노튜브를 포함하는 고분자 복합체의 제조방법

Patent Citations (1)

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KR20080096051A (ko) * 2007-04-26 2008-10-30 한국과학기술원 탄소나노튜브를 포함하는 고분자 복합체의 제조방법

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KANG, DONG U ET AL.: 'Enhanced fibronectin adsorption on carbon nanotube/poly (carbonate) urethane: Independent role of surface nano-roughness and associated surface energy' BIOMATERIALS vol. 28, 2007, pages 4756 - 4768 *
SONG, HAO-JIE ET AL.: 'Surface-modified carbon nanobubes and the effect of their addition on the tribological behavior of a polyurethane coating' EUROPEAN POLYMER JOURNAL vol. 43, 2007, pages 4092 - 4102 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9396853B2 (en) 2010-09-16 2016-07-19 Georgia Tech Research Corporation Alignment of carbon nanotubes comprising magnetically sensitive metal oxides in nanofluids
US9892835B2 (en) 2010-09-16 2018-02-13 South Dakota Board Of Regents Composite materials with magnetically aligned carbon nanoparticles and methods of preparation
WO2014118522A1 (fr) 2013-01-30 2014-08-07 Jaeger, Michael Nanostructures de carbone pour le renforcement d'un tissu oculaire
WO2015034930A1 (fr) * 2013-09-03 2015-03-12 William Marsh Rice University Traitement de maladies inflammatoires par des matériaux carbonés
US9312046B2 (en) 2014-02-12 2016-04-12 South Dakota Board Of Regents Composite materials with magnetically aligned carbon nanoparticles having enhanced electrical properties and methods of preparation

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KR101271535B1 (ko) 2013-06-05
WO2012060592A3 (fr) 2012-08-16
WO2012060592A9 (fr) 2012-06-28

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