CN101613534A - Water-soluble nano-carrier and preparation method thereof - Google Patents
Water-soluble nano-carrier and preparation method thereof Download PDFInfo
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Abstract
Water-soluble nano-carrier of a kind of technical field of nano material and preparation method thereof, comprise: add hexachlorocyclotriphosphazene, compound monomer and acid binding agent successively after carbon nanotube is distributed to organic solvent, carry out ultrasonic even processing then, then carbon nano tube suspension being carried out vacuum filtration handles, with the filtering medium that obtains after filtering with tetrahydrofuran (THF) or water washing repeatedly to remove polymkeric substance or some oligopolymer that is not wrapped, last vacuum-drying obtained water-soluble nano-carrier in 12 hours.The present invention obtains to have the controlled nano material of the uniform thickness of coating by simple preparation process, can be used as a kind of preparation material or soluble pharmaceutical carrier of safety of super capacitor when having good dispersion.
Description
Technical field
What the present invention relates to is mixture of a kind of technical field of nano material and preparation method thereof, specifically is a kind of water-soluble nano-carrier and preparation method thereof.
Background technology
In found carbon nanotube in 1991 was the carbon material that a class has perfect graphite-structure, and diameter is generally from several nanometers to tens nanometer.Carbon nanotube has unique optics, electricity, machinery and thermal characteristics, and these special performances make it cause the very big concern of researcher in fields such as materialogy, electronics, biomedicines.Yet, not processed carbon nanotube has huge specific surface area, has very strong agglomeration each other, makes carbon nanotube be dissolved in any solvent hardly, therefore be difficult to be distributed in matrices of composite material or the various application system, limited it in industrial extensively quoting.The deliquescent measure in solvent of wherein a kind of increase carbon nanotube is exactly at the peripheral one layer of polymeric that coats of carbon nanotube, overcomes the Van der Waals force between carbon nanotube.
Carbon nanotube is carried out polymer overmold two kinds of schemes are arranged usually: a kind of is the covalent linkage method, and another kind is the non covalent bond method.The covalent linkage method is a kind of chemical process, this method is earlier carbon nanotube to be carried out acid treatment, on tube wall, produce active site such as hydroxyl or carboxyl, high reactivity by active site passes through polymkeric substance in the way grafting of " Graft to " or " Graft through " then, thereby improves the solvability of carbon nanotube.
Find through retrieval prior art; put down in writing a kind of " preparation method of block polymer grafted carbon nanotube " among the patent publication No. CN1513757A; this method is with the carbon nanotube acidifying; make its surface be with hydroxyl or amino with polyalcohols or the reaction of polynary amine after the acidylate; react with the alpha-halogen carboxylic acid halides again; obtain the carbon nanotube that the surface has initiating group; in the presence of catalyzer and part, contain the double bond monomer polymerization then with the atom transition free radical polymerization reaction initiation; obtain the macromolecular grafted carbon nanotube of single hop; the carbon nanotube that single hop is macromolecular grafted continues to cause another kind with atom transition free radical polymerization reaction and contains the double bond monomer polymerization; obtain block polymer grafted carbon nanotube, products obtained therefrom has fabulous solvability.This method applicable surface is wider, can be on carbon nanotube the polymkeric substance of the various opposed polarities of grafting, yet the critical defect of this method is to make the structure of carbon nanotube produce permanent destruction in the acid treatment process, finally causes its electric property and physical strength impaired.
Find by retrieval again, Yuan W. is at Macromolecules, (2006,39,8011-8020) and PetrovP. at Chem.Commun (2003,23,2904-2905) going up disclosed technology contents can know: non covalent bond coating method is a kind of physical method, can the long-range π key of carbon nanotube not damaged.The polymkeric substance that this method general requirement is wrapped up has big π system, interacts and polymkeric substance is covered carbon nano tube surface by the π system of polymkeric substance and the π between carbon nanotube graphite aspect-π.For now, this base polymer of being reported generally has structure linear or a chain, because interacting, the π between this base polymer and carbon nanotube-π belongs to weak interaction, the dispersion of carbon nanotube in solvent is unsettled, in case this base polymer is dissociated in solvent, be polymkeric substance and the solvent phase mutual effect interaction greater than polymkeric substance and carbon nanotube, the performance of drying of carbon nanotube still causes himself being wrapped in decreased solubility.Just think,, will overcome this predicament greatly, yet seldom be in the news with the research of cross-linked polymer as the carbon nanotube integument if what twine in carbon nano tube surface is cross-linked polymer.Kang Y.et al., J.Am.Chem.Soc. (2003,125, delivered on 5650-5651) a kind of crosslinkable surfactant micelle to the carbon nanotube successful implementation non covalent bond parcel, and improved the solubility property of carbon nanotube greatly, yet this encapsulation process is very complicated.Therefore, if find a simple path, with cross-linked high polymer carbon nanotube being carried out the non covalent bond embedding must be a kind of promising method.
Summary of the invention
The present invention is directed to the prior art above shortcomings, a kind of water-soluble nano-carrier and preparation method thereof is provided, obtain to have the controlled nano material of the uniform thickness of coating by simple preparation process, as a kind of preparation material or soluble pharmaceutical carrier of safety of super capacitor.
The present invention is achieved by the following technical solutions:
The present invention relates to water-soluble nano-carrier is coaxial configuration, comprising: cross-linked polymer and carbon nanotube, and wherein: cross-linked polymer is coated on the outside of carbon nanotube, and the mean thickness of this cross-linked polymer is 6～32nm.
The component of described cross-linked polymer and mass percent thereof are: poly-hexachlorocyclotriphosphazene 27.86%～36.36% and compound monomer 63.64%～72.14%.
Described compound monomer is 4,4 '-dihydroxy diphenylsulphone, 4,4,4,4 ' dioxydiphenyl methane, 4,4 '-diaminodiphenylmethane, 4,4,4 '-dihydroxyl-3,3 ', 5,5 '-tetrabromo sulfobenzide, 4,4 '-dihydroxyl-3,3 ', 5,5 '-a kind of in tetrabromo ditane, Ursol D or the Resorcinol.
Described carbon nanotube is: Single Walled Carbon Nanotube, double-walled carbon nano-tube or multi-walled carbon nano-tubes, the external diameter of this carbon nanotube are 1～100nm, and length is 0.1～50 μ m.
The present invention relates to the preparation method of above-mentioned water-soluble nano-carrier, may further comprise the steps:
Add hexachlorocyclotriphosphazene, compound monomer and acid binding agent successively after under the first step, the room temperature condition carbon nanotube being distributed to organic solvent, carry out ultrasonic even processing then, make carbon nano tube suspension.
The consumption of described carbon nanotube is 1～5 weight part, and the consumption of hexachlorocyclotriphosphazene is 4～20 weight parts, and the consumption of compound monomer is 8～45 weight parts, and the consumption of acid binding agent is 20～100 weight parts.
Described carbon nanotube is for adopting single wall, double-walled or the multi-walled carbon nano-tubes of catalyse pyrolysis, arc-over, template and the preparation of laser evaporation method, and its external diameter is 1～100nm, and length is 0.1～50 μ m.
Described organic solvent is tetrahydrofuran (THF), ethanol, dimethyl sulfoxide (DMSO), N, a kind of or its combination in dinethylformamide, acetone, acetonitrile, butanone, methyl alcohol or the propyl alcohol, and the consumption of this organic solvent is 2000～10000 times of carbon nanotube quality.
Described compound monomer is 4,4 '-dihydroxy diphenylsulphone, 4,4,4,4 '-dioxydiphenyl methane, 4,4 '-diaminodiphenylmethane, 4,4,4 '-dihydroxyl-3,3 ', 5,5 '-tetrabromo sulfobenzide, 4,4 '-dihydroxyl-3,3 ', 5,5 '-a kind of in tetrabromo ditane, Ursol D or the Resorcinol.
Described acid binding agent is a kind of in triethylamine, tripropyl amine, Tributylamine, triamylamine, trihexylamine, three heptyl amices, trioctylamine, yellow soda ash or the salt of wormwood.
Described ultrasonic even processing is meant: setting ultrasonic power under 10～80 ℃ of conditions is 10～150w, and ultrasonic frequency is that 40kHz carried out ultrasonic reaction 3～6 hours.
Second step, carbon nano tube suspension carried out vacuum filtration handle, with the filtering medium that obtains after filtering with tetrahydrofuran (THF) or water washing repeatedly to remove polymkeric substance or some oligopolymer that is not wrapped, last vacuum-drying obtained water-soluble nano-carrier in 12 hours.
Described vacuum filtration is handled and is meant: adopt the polycarbonate membrane of 0.2 μ m micropore to carry out vacuum filtration.
Preparation technology of the present invention is simple, preparation process is not used any tensio-active agent or synergist, simplified finishing sequence, the products obtained therefrom water-soluble nano-carrier has the structure of concentric cable, shell material cross-linked polymer coating layer is even, coating thickness is controlled, and is suitable to extraordinary nano-device such as super capacitor etc.; The surface coating layer polymkeric substance that the present invention prepares the carbon nanotube of gained has good dispersiveness, has effectively improved the workability of carbon nanotube, can be used as the specialist additive of water-soluble high-molecular material; By changing the monomeric proportioning of copolycondensation, can realize that polymer covering layer is rich in hydroxyl or amino, like this, be can be used as the carrier of material transfer and transfer between different system by water-soluble nano-carrier.
Description of drawings
Fig. 1 is the transmission electron microscope photo of the prepared cross-linked polymer enveloped carbon nanometer tube of embodiment 1.
Fig. 2 is that embodiment 1 disperses the contrast synoptic diagram.
Fig. 3 is the transmission electron microscope photo of the prepared cross-linked polymer enveloped carbon nanometer tube of embodiment 2.
Fig. 4 is prepared cross-linked polymer enveloped carbon nanometer tube of embodiment 3 and the contrast infrared spectra before and after the paranitrobenzoyl chloride generation acylation reaction.
Embodiment
Below embodiments of the invention are elaborated: present embodiment is being to implement under the prerequisite with the technical solution of the present invention, provided detailed embodiment and concrete operating process, but protection scope of the present invention is not limited to following embodiment.
Embodiment 1
In the 100mL round-bottomed flask, add 5.0mg multi-walled carbon nano-tubes and 50mL tetrahydrofuran (THF) and alcohol mixed solvent (the two volume ratio is 20: 1), ultra-sonic dispersion 10 minutes; Add 20.0mg hexachlorocyclotriphosphazene, 43.2mg 4,4 '-dihydroxy diphenylsulphone and 100.0mg triethylamine; Ultrasonic radiation reaction 6 hours under the room temperature condition (100W, 40kHz); Then with solution with 0.2 μ m microporous polycarbonate film vacuum filtration, repeatedly to remove polymkeric substance or some oligopolymer that is not wrapped, last vacuum-drying diel obtains water-soluble nano-carrier to filtering medium with tetrahydrofuran (THF) and water washing.
Fig. 1 has shown the transmission electron microscope photo of cross-linked polymer enveloped carbon nanometer tube prepared under embodiment 1 condition, the result shows that the gained water-soluble nano-carrier has the structure of concentric cable, sandwich layer is a carbon nanotube, its diameter is 8～12 nanometers, the shell material is the cross-linked polymer of about 7 nanometers of mean thickness, and shell thickness is comparatively even.Fig. 2 has shown that cross-linked polymer enveloped carbon nanometer tube prepared under embodiment 1 condition is at different solvents (D: water; E: ethanol; F: deployment conditions tetrahydrofuran (THF)) and independent carbon nanotube are at coordinative solvent (A: water; B: ethanol; C: the contrast photo of the deployment conditions tetrahydrofuran (THF)), clearly carbon nanotube be crosslinked after the polymer overmold can be in solvent good distribution.
Embodiment 2
In the 100mL round-bottomed flask, add 5.0mg multi-walled carbon nano-tubes and 50mL tetrahydrofuran (THF) and alcohol mixed solvent (the two volume ratio is 20: 1), ultra-sonic dispersion 10 minutes; Add 50.0mg hexachlorocyclotriphosphazene, 108.0mg 4,4 '-dihydroxy diphenylsulphone and 250.0mg triethylamine; Ultrasonic radiation reaction 6 hours under the room temperature condition (100W, 40kHz); Then with solution with 0.2 μ m microporous polycarbonate film vacuum filtration, repeatedly to remove polymkeric substance or some oligopolymer that is not wrapped, last vacuum-drying diel obtains water-soluble nano-carrier to filtering medium with tetrahydrofuran (THF) and water washing.
Fig. 3 has shown the transmission electron microscope photo of cross-linked polymer enveloped carbon nanometer tube prepared under embodiment 2 conditions, the result shows that the gained water-soluble nano-carrier has the structure of concentric cable, sandwich layer is a carbon nanotube, its diameter is 8～12 nanometers, the shell material is the cross-linked polymer of about 32 nanometers of mean thickness, and shell thickness is comparatively even, does not have adhesion between different root concentric cable.
Embodiment 3
In the 100mL round-bottomed flask, add 5.0mg multi-walled carbon nano-tubes and 50mL tetrahydrofuran (THF) and alcohol mixed solvent (the two volume ratio is 20: 1), ultra-sonic dispersion 10 minutes; Add 20.0mg hexachlorocyclotriphosphazene, 51.8mg 4,4 '-dihydroxy diphenylsulphone and 100.0mg triethylamine; Ultrasonic radiation reaction 6 hours under the room temperature condition (100W, 40kHz); Then with solution with 0.2 μ m microporous polycarbonate film vacuum filtration, repeatedly to remove polymkeric substance or some oligopolymer that is not wrapped, last vacuum-drying diel obtains water-soluble nano-carrier to filtering medium with tetrahydrofuran (THF) and water washing.
Fig. 4 has shown the contrast infrared spectra before and after the cross-linked polymer enveloped carbon nanometer tube for preparing under embodiment 3 conditions and the paranitrobenzoyl chloride generation acylation reaction, and wherein CNT@PZS-OH is the infrared spectra before the acidylate, CNT@PZS-OOC-Ph-NO
2Be the infrared spectra after the acidylate, clearly 1739cm after the acidylate
-1Place's carbonyl, 1532 and 1264cm
-1The existence of place's nitro characteristic peak shows that acylation reaction has taken place for this water-soluble nano-carrier and paranitrobenzoyl chloride, also is that activity hydroxy is rich on the water-soluble nano-carrier surface; The transmission electron microscope characterization result shows that it is the cross-linked polymer of 7.5 nanometers that carbon nano tube surface has been coated one deck mean thickness.
Embodiment 4
In the 100mL round-bottomed flask, add 5.0mg multi-walled carbon nano-tubes and 50mL tetrahydrofuran (THF) and alcohol mixed solvent (the two volume ratio is 20: 1), ultra-sonic dispersion 10 minutes; Add 20.0mg hexachlorocyclotriphosphazene, 51.5mg 4,4 and 100.0mg triethylamine; Ultrasonic radiation reaction 6 hours under 55 ℃ of conditions (100W, 40kHz); Then with solution with 0.2 μ m microporous polycarbonate film vacuum filtration, repeatedly to remove polymkeric substance or some oligopolymer that is not wrapped, last vacuum-drying diel obtains water-soluble nano-carrier to filtering medium with tetrahydrofuran (THF) and water washing.The results of FT-IR shows that the water-soluble nano-carrier surface for preparing under this condition is rich in active amine; The transmission electron microscope characterization result shows that it is the cross-linked polymer of 6 nanometers that carbon nano tube surface has been coated one deck mean thickness.
Embodiment 5
In the 100mL round-bottomed flask, add 5.0mg multi-walled carbon nano-tubes and 50mL tetrahydrofuran (THF) and alcohol mixed solvent (the two volume ratio is 20: 1), ultra-sonic dispersion 10 minutes; Add 30.0mg hexachlorocyclotriphosphazene, 64.8mg 4,4 '-dihydroxy diphenylsulphone and 150.0mg triethylamine; Ultrasonic radiation reaction 6 hours under the room temperature condition (100W, 40kHz); Then with solution with 0.2 μ m microporous polycarbonate film vacuum filtration, repeatedly to remove polymkeric substance or some oligopolymer that is not wrapped, last vacuum-drying diel obtains water-soluble nano-carrier to filtering medium with tetrahydrofuran (THF) and water washing.The transmission electron microscope characterization result shows that it is the cross-linked polymer of 17 nanometers that the carbon nano tube surface for preparing under this condition has been coated one deck mean thickness.
Embodiment 6
In the 100mL round-bottomed flask, add 5.0mg multi-walled carbon nano-tubes and 50mL tetrahydrofuran (THF) and alcohol mixed solvent (the two volume ratio is 20: 1), ultra-sonic dispersion 10 minutes; Add 30.0mg hexachlorocyclotriphosphazene, 52.5mg 4 and 150.0mg triethylamine; Ultrasonic radiation reaction 6 hours under 55 ℃ of conditions (100W, 40kHz); Then with solution with 0.2 μ m microporous polycarbonate film vacuum filtration, repeatedly to remove polymkeric substance or some oligopolymer that is not wrapped, last vacuum-drying diel obtains water-soluble nano-carrier to filtering medium with tetrahydrofuran (THF) and water washing.The transmission electron microscope characterization result shows that it is the cross-linked polymer of 15 nanometers that the carbon nano tube surface for preparing under this condition has been coated one deck mean thickness.
Claims (10)
1, a kind of water-soluble nano-carrier is characterized in that, described nano-carrier is a coaxial configuration, comprising: cross-linked polymer and carbon nanotube, and wherein: cross-linked polymer is coated on the outside of carbon nanotube, and the mean thickness of this cross-linked polymer is 6～32nm.
2, water-soluble nano-carrier according to claim 1 is characterized in that, the component of described cross-linked polymer and mass percent thereof are: poly-hexachlorocyclotriphosphazene 27.86%～36.36% and compound monomer 63.64%～72.14%.
3, water-soluble nano-carrier according to claim 1 is characterized in that, described carbon nanotube is: Single Walled Carbon Nanotube, double-walled carbon nano-tube or multi-walled carbon nano-tubes, the external diameter of this carbon nanotube are 1～100nm, and length is 0.1～50 μ m.
4, a kind of preparation method of water-soluble nano-carrier according to claim 1 is characterized in that, may further comprise the steps:
Add hexachlorocyclotriphosphazene, compound monomer and acid binding agent successively after under the first step, the room temperature condition carbon nanotube being distributed to organic solvent, carry out ultrasonic even processing then, make carbon nano tube suspension;
Second step, carbon nano tube suspension carried out vacuum filtration handle, with the filtering medium that obtains after filtering with tetrahydrofuran (THF) or water washing repeatedly to remove polymkeric substance or some oligopolymer that is not wrapped, last vacuum-drying obtained water-soluble nano-carrier in 12 hours.
5, the preparation method of water-soluble nano-carrier according to claim 4, it is characterized in that, the consumption of described carbon nanotube is 1～5 weight part, the consumption of hexachlorocyclotriphosphazene is 4～20 weight parts, the consumption of compound monomer is 8～45 weight parts, and the consumption of acid binding agent is 20～100 weight parts.
6, the preparation method of water-soluble nano-carrier according to claim 4, it is characterized in that, described organic solvent is tetrahydrofuran (THF), ethanol, dimethyl sulfoxide (DMSO), N, a kind of or its combination in dinethylformamide, acetone, acetonitrile, butanone, methyl alcohol or the propyl alcohol, the consumption of this organic solvent is 2000～10000 times of carbon nanotube quality.
7, the preparation method of water-soluble nano-carrier according to claim 4 is characterized in that, described compound monomer is 4,4 '-dihydroxy diphenylsulphone, 4,4,4,4 '-dioxydiphenyl methane, 4,4 '-diaminodiphenylmethane, 4,4,4 '-dihydroxyl-3,3 ', 5,5 '-tetrabromo sulfobenzide, 4,4 '-dihydroxyl-3,3 ', 5,5 '-a kind of in tetrabromo ditane, Ursol D or the Resorcinol.
8, the preparation method of water-soluble nano-carrier according to claim 4 is characterized in that, described acid binding agent is a kind of in triethylamine, tripropyl amine, Tributylamine, triamylamine, trihexylamine, three heptyl amices, trioctylamine, yellow soda ash or the salt of wormwood.
9, the preparation method of water-soluble nano-carrier according to claim 4 is characterized in that, described ultrasonic even processing is meant: setting ultrasonic power under 10～80 ℃ of conditions is 10～150w, and ultrasonic frequency is that 40kHz carried out ultrasonic reaction 3～6 hours.
10, the preparation method of water-soluble nano-carrier according to claim 4 is characterized in that, described vacuum filtration is handled and is meant: adopt the polycarbonate membrane of 0.2 μ m micropore to carry out vacuum filtration.
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| CN103877580A (en) * | 2013-11-11 | 2014-06-25 | 浙江大学 | Carbon nano tube complex gene vector system and preparation method thereof |
| CN106729971A (en) * | 2016-11-23 | 2017-05-31 | 上海纳米技术及应用国家工程研究中心有限公司 | A kind of modified calcium phosphate bone cement of water-soluble mono wall carbon nano tube and preparation and application |
| CN107126974A (en) * | 2017-06-07 | 2017-09-05 | 北京化工大学常州先进材料研究院 | ZIF 67 modifies Fe3O4The preparation and its application of ORR catalyst of@PZS core-shell particles |
| CN111100332A (en) * | 2019-12-02 | 2020-05-05 | 厦门大学 | Preparation method and application of dumbbell type fluorine-containing polyphosphazene modified halloysite nanotube |
| CN111248195A (en) * | 2020-02-24 | 2020-06-09 | 暨南大学 | Nano-silver-loaded polyphosphazene composite antibacterial agent and preparation method and application thereof |
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| CN102657898A (en) * | 2012-04-18 | 2012-09-12 | 暨南大学 | Degradable nanofiber anti-adhesive membrane with double-release performance and preparation method of same |
| CN103877580A (en) * | 2013-11-11 | 2014-06-25 | 浙江大学 | Carbon nano tube complex gene vector system and preparation method thereof |
| CN103877580B (en) * | 2013-11-11 | 2016-04-06 | 浙江大学 | A kind of CNT complex gene carrier system and preparation method thereof |
| CN106729971A (en) * | 2016-11-23 | 2017-05-31 | 上海纳米技术及应用国家工程研究中心有限公司 | A kind of modified calcium phosphate bone cement of water-soluble mono wall carbon nano tube and preparation and application |
| CN107126974A (en) * | 2017-06-07 | 2017-09-05 | 北京化工大学常州先进材料研究院 | ZIF 67 modifies Fe3O4The preparation and its application of ORR catalyst of@PZS core-shell particles |
| CN107126974B (en) * | 2017-06-07 | 2019-11-08 | 北京化工大学常州先进材料研究院 | ZIF-67 modifies Fe3O4The preparation of@PZS core-shell particles and its application of ORR catalyst |
| CN111100332A (en) * | 2019-12-02 | 2020-05-05 | 厦门大学 | Preparation method and application of dumbbell type fluorine-containing polyphosphazene modified halloysite nanotube |
| CN111100332B (en) * | 2019-12-02 | 2021-06-01 | 厦门大学 | Preparation method and application of dumbbell type fluorine-containing polyphosphazene modified halloysite nanotube |
| CN111248195A (en) * | 2020-02-24 | 2020-06-09 | 暨南大学 | Nano-silver-loaded polyphosphazene composite antibacterial agent and preparation method and application thereof |
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