WO2012146703A1 - Procédé de préparation d'une composition à base d'un polymère conducteur - Google Patents

Procédé de préparation d'une composition à base d'un polymère conducteur Download PDF

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WO2012146703A1
WO2012146703A1 PCT/EP2012/057735 EP2012057735W WO2012146703A1 WO 2012146703 A1 WO2012146703 A1 WO 2012146703A1 EP 2012057735 W EP2012057735 W EP 2012057735W WO 2012146703 A1 WO2012146703 A1 WO 2012146703A1
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polymer
conductive
polymer composition
process according
conductive particles
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PCT/EP2012/057735
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English (en)
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Cornelis Eme Koning
Evgeniy Tkalya
Paul SCHOOT VAN DER
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Stichting Dutch Polymer Institute
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/20—Compounding polymers with additives, e.g. colouring
    • C08J3/205—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase
    • C08J3/21—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase the polymer being premixed with a liquid phase
    • C08J3/215—Compounding polymers with additives, e.g. colouring in the presence of a continuous liquid phase the polymer being premixed with a liquid phase at least one additive being also premixed with a liquid phase
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/005—Processes for mixing polymers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/005—Reinforced macromolecular compounds with nanosized materials, e.g. nanoparticles, nanofibres, nanotubes, nanowires, nanorods or nanolayered materials
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L1/00—Compositions of cellulose, modified cellulose or cellulose derivatives
    • C08L1/02—Cellulose; Modified cellulose
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/122—Ionic conductors
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/124—Intrinsically conductive polymers
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/124—Intrinsically conductive polymers
    • H01B1/127—Intrinsically conductive polymers comprising five-membered aromatic rings in the main chain, e.g. polypyrroles, polythiophenes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2300/00—Characterised by the use of unspecified polymers
    • C08J2300/12—Polymers characterised by physical features, e.g. anisotropy, viscosity or electrical conductivity
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2301/00—Characterised by the use of cellulose, modified cellulose or cellulose derivatives
    • C08J2301/02—Cellulose; Modified cellulose
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2365/00—Characterised by the use of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Derivatives of such polymers

Definitions

  • the present invention relates to a process for the preparation of a conductive polymer composition and the polymer composition obtainable by this process.
  • WO2004/072159 discloses a process for the preparation of a CNT reinforced polymer.
  • a conductive polymer composition was obtained from an aqueous dispersion of CNTs and sodium dodecyl sulphate (SDS) and an aqueous latex of polystyrene (PS).
  • SDS sodium dodecyl sulphate
  • PS polystyrene
  • WO2009/033933 discloses a process for the preparation of a conductive polymer composition.
  • a conductive single wall nanotubes dispersion stabilized with a commercially available aqueous dispersion of a mixture of poly (3,4 ethylene dioxy thiophene) (PEDOT) and polystyrenesulphonate (PSS) is used to make a composite with a polystyrene latex.
  • PEDOT poly (3,4 ethylene dioxy thiophene)
  • PSS polystyrenesulphonate
  • Conductive polymer compositions comprising graphene are also known.
  • WO2010/086176 discloses a process for the preparation of a conductive polymer composition comprising a polymer and graphene.
  • Use of a water-soluble surfactant for the stabilization of the graphene dispersion is mentioned.
  • a commercially available dispersion of a mixture of PEDOT and PSS is mentioned.
  • the present invention provides a process for the preparation of a polymer composition, comprising the following steps:
  • step B) mixing the resulting product from step A) with either an aqueous latex of a second polymer, or with (a) water-soluble precursor(s) of the second polymer;
  • step D) heating the product from step C) to a temperature at which the second polymer flows or where the second polymer is formed from its precursor(s); and E) processing and/or solidifying the product of step D) into a desired form.
  • the term 'aspect ratio' is herein understood to mean the ratio of the longer dimension to its shorter dimension of the particles.
  • the ratio can be determined by e.g. optical or electronic microscopy.
  • the aspect ratio is understood as the ratio of the length to the diameter of the particles.
  • the aspect ratio is understood as the ratio of the width of the particles to the thickness of the particles.
  • the aspect ratio of the non-conductive particles is at least 10, preferably at least 30, preferably at least 40, more preferably at least 50, more preferably at least 60, even more preferably at least 100.
  • non-conductive particles' is herein understood to mean particles with an intrinsic conductivity below 10 2 S/m.
  • non- conductive particles with an intrinsic conductivity below 10 2 S/m, below 10 S/m, below 1 S/m, below 10 "1 S/m, below 10 ⁇ 2 S/m, below 10 "3 S/m, below 10 "4 S/m, below 10 "5 S/m, below 10 ⁇ 6 S/m or below 10 ⁇ 7 S/m may also be used.
  • conductive polymer' is herein understood to mean a polymer having an intrinsic conductivity of at least 10 2 S/m.
  • conductive polymer with an intrinsic conductivity of at least 10 2 S/m or e.g. at least 5 x 10 2 S/m, at least 10 3 S/m, at least 5 x 10 3 S/m or at least 10 4 S/m may be used.
  • the inventors have found that the polymer composition obtained by the process according to the present invention shows a high electrical conductivity despite the use of the non-conductive particles.
  • the inventors predict that the anisotropic non-conductive particles form a percolating network which serves as a template for the conductive first polymer.
  • a high electrical conductivity was obtained at low loadings of the non- conductive particles and the conductive first polymer.
  • the invention is extremely advantageous in that inexpensive materials can be used in place of the expensive conductive materials such as CNTs.
  • non-conductive particles significantly lowers the percolation threshold of the expensive conductive polymer such as PEDOT-PSS, thus lowering the amount of the conductive polymer used.
  • the inventors have
  • a high conductivity and a low percolation threshold can be obtained by the simultaneous presence of a low amount of the anisotropic non- conductive particles and a low amount of the first, conductive polymer in the second, matrix polymer.
  • the particles of the latex of the second polymer after brought to flow by e.g. compression molding, form a continuous matrix in which the non-conductive particles and the first, conductive polymer are dispersed.
  • step A) may be performed by contacting the non-conductive particles with (an aqueous latex or solution of) the first polymer which acts as a surfactant for obtaining an aqueous dispersion of the non-conductive particles.
  • the aqueous dispersion of the non- conductive particles may also be provided by first providing an aqueous dispersion of the non-conductive particles and subsequently contacting it with (an aqueous latex or solution of) the first polymer.
  • non-conductive particles examples include inorganic nanofibers of titanium dioxide, silicon dioxide, zirconium dioxide, aluminum oxide, lithium titanate, titanium nitride or platinum.
  • Sepiolite nanofibers, halloysites nanotubes, boehmite whiskers and crystalline needles of inorganic salts and organic salts are also suitable examples.
  • Sepiolite is a clay mineral, a complex magnesium silicate, a typical formula for which is Mg 4 Si 6 0i 5 (OH)2-6H 2 0.
  • Sepiolite fibers are available from Sivomatic and can have a length of a few hundred nm and a diameter of 10-30nm (see D.P.N. Vlasveld "Fibre reinforced nanocomposites” ISBN-10: 90-9019883-0, page 100 and 102).
  • Halloysite is a 1 :1 aluminosilicate clay mineral with the empirical formula
  • organic nanowhiskers and nanofibers such as cellulose nanowhiskers and polyamide nanofibers.
  • Cellulose nanowhiskers have an advantage that they are bio-based.
  • Polyamide nanofibers have an advantage that they allow use in high temperature applications.
  • These non-conductive particles mentioned above have an advantage that they are inexpensive, except for platinum. Further, these particles give a light, whitish color to the resulting composition, unlike CNTs and graphene which give a black color to the resulting composition. This is advantageous in that the color of the resulting composition can be easily controlled, since the color of white compositions can be tuned by suitable colorants.
  • the cellulose nanowhiskers may be surface modified.
  • the surface of the nanowhiskers may have sulphonate or Na-sulphonate groups. They may be used in the process having the surface modification, or they may be neutralized before being mixed with the other components in step A).
  • the first polymer is selected from poly(3,4- ethylenedioxythiophene) poly(styrenesulfonate), polyphenylene-vinylenes,
  • polythiophenes polyaniline, polypyrrole or polyacetylene.
  • Each of these polymers can be used in combination with suitable non-conductive particles and second polymer to improve the dispersibility of the non-conductive particles in the second polymer which acts as the matrix.
  • An example of the combination is poly(3,4-ethylenedioxythiophene) poly(styrenesulfonate), cellulose nanowhiskers and polystyrene.
  • the resulting product from step A) can contain up to 75 weight% of the particles.
  • the mass ratio of the first polymer to the particles can range from 0.05 to 20, preferably between 0.1 and 10.
  • the temperature at which this step A) is performed is not critical. Temperatures between room temperature and 75°C are very well suited.
  • the residence time needed for an effective exfoliation of the particles can be easily determined by a man skilled in the art. Residence times below 1 hour have proven to be sufficient for that purpose.
  • This second polymer is the polymer which constitutes the matrix of the final polymer composition, in which the particles are well-dispersed. Every aqueous polymer latex known to the skilled man can be used.
  • a polymer being selected from the group comprising polyacrylates, styrene-based (copolymers, butadiene-based (co-)polymers, polycarbonate, acrylonitrile-based (copolymers, (halogen-containing) polyolefins (like polyethylene or polypropylene), polyvinylchloride, polyurethanes and polyamides.
  • precursor(s) for such a second polymer can be used, as they are, or in the form of an aqueous solution thereof which can be converted to the polymer via an emulsion polymerization.
  • Preference can be given, for instance when a nylon is used as the polymer, to the use in this step B) of either the monomer of said polymer (like ⁇ -caprolactam when using nylon 6 as the final matrix material), or to the use of a salt of adipic acid and hexamethylene diamine, or diaminobutane, when nylon 6,6 or nylon 4,6 as the matrix material is aimed at.
  • the skilled man is aware of the precursor(s) needed for such a second polymer.
  • a preference is given to the use in this step B) of ((a) precursor(s) of) a polyamide or a polystyrene based polymer.
  • the temperature of this step B) generally lies between 10 and 150°C.
  • the pressure is generally atmospheric, but may be increased in order to accommodate for processability in this step B) or in the following step C).
  • the residence time for this step B) is not critical, and generally does not exceed 1 hour.
  • thermoset polymers as well as thermoplastic polymers can be used as the matrix of the polymer composition, the preference is given to the use of a (semi-) crystalline or amorphous thermoplastic polymer.
  • remove substantially all of the water.
  • step C) by means of evaporation, freeze-drying, or flash-drying.
  • Step D) is intended to realize a homogeneous dispersion of the particles in the second polymer.
  • this step D) is also intended to form the polymer from this/these precursor(s).
  • the temperature in this step D is chosen such that it is 10-100°C above the melting point (in case of a (semi-)crystalline second polymer), or above the glass point (in case of an amorphous polymer).
  • step D) the temperature in this step D) is chosen such that this polymer can be formed from its precursor(s), during which formation also step E) of the process of the present invention is applied. It was found that performing step D) at a higher temperature generally results in a lowering of the percolation threshold. Step D) may be performed under an elevated pressure, e.g. under a pressure of 1 -100 MPa. It was also found that performing step D) for a longer time at a certain temperature generally results in a lowering of the percolation threshold.
  • Step E) of the process of the present invention is the processing and/or solidification of the product of step D) in a desired form.
  • This step E) can be a molding step, a pelletizing step, an injection or compression molding step, or any known step to form a solidified polymer object.
  • the process of the present invention results in a polymer composition in which the particles are hardly or not damaged, as a result of which they retain their original length as well as their original aspect ratio (AR).
  • the anisotropic non- conductive particles presumably, although not wishing to be bound by any theory, form an (almost) percolating network. This network presumably serves as a template for the conductive surfactant to form a percolating network.
  • the invention also relates to a polymer composition obtainable by the process of the present invention.
  • polymer compositions are obtainable comprising a conductive polymer and a non-conductive polymer, wherein the conductive polymer is PEDOT/PSS and the polymer composition has a conductivity percolation threshold below 2.3 wt.% of PEDOT/PSS.
  • PEDOT/PSS particles themselves percolate at 2.3 wt% in a PS matrix.
  • the addition of the anisotropic particles lowers the percolation threshold of PEDOT/PSS in a PS matrix to a much lower level, e.g. to 2.0 wt%, more preferably to 1 .5 wt%, even more preferably to 1 .0 wt%, even more preferably to around or below 0.75 wt%.
  • the polymer composition of the present invention can be used for several applications in which the conductivity properties can be exploited. Reference can be given to shielding applications (like electromagnetic interference shielding); high modulus conducting, in-line paintable body panels for the automotive industry with a better surface appearance than glass fibre filled polymers; nano-electric devices (such as thin-film transitors), and others.
  • shielding applications like electromagnetic interference shielding
  • nano-electric devices such as thin-film transitors
  • cellulose nanowhiskers for lowering the conductivity percolation threshold of a polymer composition, such as a PS based polymer composition.
  • the invention is illustrated by the following non-limiting examples and comparative experiment.
  • Figure 1 shows the result of conductivity measurements for a comparative example in which the PS matrix comprises PEDOT:PSS;
  • Figure 2 shows the result of conductivity measurements for an example of the present invention in which the PS matrix comprises PEDOT:PSS and cellulose whisker and
  • Figure 3 shows the result of conductivity measurements for a further example of the present invention in which the PS matrix comprises PEDOT:PSS and cellulose whisker.
  • Sisal cellulose nanowhiskers made according to the method described in Lis et.al., Cellulose (2006) 13:261 -270 were used.
  • the nanowhiskers have the geometric average diameter and length of approximately 4 ⁇ 1 and 250 ⁇ 100 nm (an aspect ratio of around 60).
  • a polystyrene latex was synthesized via conventional free radical emulsion polymerization. Emulsion polymerization runs were carried out in an oxygen free atmosphere. 252 g styrene was mixed with 712 g water in the presence of 26 g SDS surfactant and 0.7 g Na 2 C0 3 buffer. The reaction mixture was degassed, by purging with argon, for 30 min. The reaction was initiated by adding 0.45 g SPS (sodium per sulphate) dissolved in 10g of water which was also preliminary degassed. The polymerization took place at constant temperature of 70 'C.
  • SPS sodium per sulphate
  • Baytron®P was purchased from H C Starck (Bayer(R)) and contains
  • poly(3,4-ethylened[iota]oxyth[iota]ophene) PEDOT
  • PSS poly(styrene sulfonate)
  • Sonication was performed using a Sonics Vibracell VC750 horn sonicator with a 10mm tip diameter. The sonication power was maintained at 20 W during the exfoliation, and the solution was cooled in an ice-bath to prevent any excessive nanofiller damage. Solution volumes for the sonication process were limited to 25 ml_ and all weight percentages of the cellulose whiskers within these solutions were kept at 0.1 wt% ((relative to the total composition including water))
  • Compression moulding of dried composite powders was performed on a 300G Collins Press.
  • the powders were heated to a temperature between 160 ⁇ to leO' within 20 min between two PET sheets, degassed (by opening and closing the compression mold) and twice pressed together for 20 seconds at a pressure of 4 MPa, followed by pressing the powder with 10 MPa for 2 minutes at 180°C. They are allowed to cool to room temperature at atmospheric pressure.
  • Conductivity measurements are performed via a standard 4-point technique. Graphite contacts are painted on the surface of the compression moulded films, and volume resistivites are measured using a Keithley 6512 programmable electrometer and a Keithely 220 Programmable current source.
  • Blends of purchased Baytron®P and prepared PS were prepared.
  • the Baytron®P latex was simply mixed with the PS latex such that the weight percentage of Baytron®P in the final dried polymer blend was between 0 and 6 wt%, or 30 wt%.
  • the mixed colloid PS and Baytron®P particles in water
  • PS and Baytron®P particles in water were freeze- dried and then the resultant powder was compression molded (see method in Materials and techniques) into a homogeneous film.
  • One standard PS latex prepared via emulsion polymerization, see Materials and techniques
  • the number average particle size according to data from the supplier of Baytron®P is in the range of 80 nm.
  • the conductivity was measured for the series of PS/Baytron®P films (see method in Materials and techniques)
  • the conductivity profile is given in figure 1 , and a percolation threshold can be identified.
  • the observed percolation threshold is around 2.3 wt%.
  • Blends of cellulose nanowhiskers, purchased Baytron®P and prepared PS were prepared.
  • the cellulose nanowhiskers were dispersed in water by 15 minutes sonication, with energy supplied about 30000 Joules to 25 mg of whiskers in 25 ml of Water.
  • the Baytron®P was added such that the weight ratio of the whiskers to Baytron®P was 1 :4. The mixture was sonicated for additional 5 minutes for better mixing.
  • the PS latex was added drop-wise to an appropriate volume of the dispersion (such that loading of cellulose in final composite, i.e. polymer, surfactant and cellulose only, is between 0.1 and 6.0 wt%). These mixed colloids were freeze-dried and compression molded in the same way as the comparative experiment 1 , giving a resultant homogeneous film.
  • the conductivity profile is given in figure 2.
  • the observed percolation threshold is around 0.4 wt% of cellulose loading, which means 1 .6 wt% of Baytron P. Also the maximum conductivity is high.
  • Example 2
  • Example 1 was repeated except for that such that the weight ratio of the whiskers to Baytron®P was 1 :1 .
  • the conductivity profile is given in figure 3.
  • the observed percolation threshold is around 0.7 wt% of cellulose loading, which means 0.7 wt% of Baytron P. Also the maximum conductivity is very high.

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Abstract

Cette invention concerne un procédé de préparation d'une composition polymère, comprenant les étapes suivantes : A) préparation d'une dispersion de particules non conductrices ayant un rapport d'aspect d'au moins 10 dans un milieu aqueux comprenant un premier polymère conducteur soluble ou pouvant être dispersé dans l'eau ; B) mélange du produit obtenu à l'étape A) avec soit un latex aqueux d'un second polymère, soit avec (a) un ou des précurseurs solubles dans l'eau du second polymère ; C) élimination de l'eau du mélange ainsi obtenu ; D) chauffage du produit obtenu à l'étape C) à une température à laquelle le second polymère s'écoule ou à laquelle le second polymère est formé à partir de son ou de ses précurseurs ; et E) traitement et/ou solidification du produit de l'étape D) pour obtenir une forme recherchée.
PCT/EP2012/057735 2011-04-27 2012-04-27 Procédé de préparation d'une composition à base d'un polymère conducteur WO2012146703A1 (fr)

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CN105040089A (zh) * 2015-07-14 2015-11-11 江西理工大学 闭系耐酸耐压加热反应体系制备纳米石英多孔晶须工艺

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WO2004072159A1 (fr) 2003-02-13 2004-08-26 Stichting Dutch Polymer Institute Polymere renforce
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WO2009033933A2 (fr) 2007-09-13 2009-03-19 Stichting Dutch Polymer Institute Procédé de préparation d'une composition polymère conductrice
WO2009070240A2 (fr) * 2007-11-21 2009-06-04 Massachusetts Institute Of Technology Séparation de nanostructures
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WO2004072159A1 (fr) 2003-02-13 2004-08-26 Stichting Dutch Polymer Institute Polymere renforce
WO2004106420A2 (fr) * 2003-05-22 2004-12-09 Zyvex Corporation Nanocomposites et procedes
EP1777262A1 (fr) * 2005-10-24 2007-04-25 Basf Aktiengesellschaft Composition thermoplastique de moulage qui est renforcée avec des nanotubes, et sa production.
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WO2009070240A2 (fr) * 2007-11-21 2009-06-04 Massachusetts Institute Of Technology Séparation de nanostructures
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* Cited by examiner, † Cited by third party
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CN105040089A (zh) * 2015-07-14 2015-11-11 江西理工大学 闭系耐酸耐压加热反应体系制备纳米石英多孔晶须工艺

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