CN1562738A - Functional nano carbon tubes possessing isocyanate radical on its surface and preparation method - Google Patents
Functional nano carbon tubes possessing isocyanate radical on its surface and preparation method Download PDFInfo
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- CN1562738A CN1562738A CN 200410017699 CN200410017699A CN1562738A CN 1562738 A CN1562738 A CN 1562738A CN 200410017699 CN200410017699 CN 200410017699 CN 200410017699 A CN200410017699 A CN 200410017699A CN 1562738 A CN1562738 A CN 1562738A
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Abstract
Carbon nanometre tube is reacted with sulphoxide chloride after being processed by strong oxidability acid, the obtained product is reacted with binary ammonia or binary alcohol to be changed to modified carbon nanometre tube with azyl or hydroxyl on the surface, which is reacted with binary or polyatomic isocyanic esters to be functionality carbon nanometre tube with isocyanic esters perssad on the surface, which has good reaction activity and can be further reacted with substance containing azyl or hydroxy, thus to be used as an intermediate to connect other substances (e.g. polyure, polyurethane etc.) on surface of the carbon nanometre tube by chemical reaction to realize design, prepn. and application of new nanometre material.
Description
Technical field: the present invention relates to a kind of preparation method of functionalized carbon nano-tube, particularly the surface has functionalized carbon nano-tube of isocyanate groups and preparation method thereof.
Background technology: carbon nanotube (Carbon Nanotube is called for short CNT) is just found a kind of novel carbon structure in 1991, is the body that is rolled into by the graphite flake layer that carbon atom forms.Quantity according to its graphite flake layer, carbon nanotube is divided into Single Walled Carbon Nanotube (Single-walled Carbon Nanotube, SWNT), double-walled carbon nano-tube (Double-walled Carbon Nanotube, DWNT), and multi-walled carbon nano-tubes (Multi-walledCarbon Nanotube, MWNT).
Because diameter is very little, length-to-diameter ratio is big, carbon nanotube is regarded as quasi-one-dimensional nanometer material.Confirmed now that carbon nanotube has peculiar electric property, superpower mechanical property, good adsorption property, thereby caused very big attention in the material field.The transistor and the indicating meter that have now had carbon nanotube to make come out.
On the other hand, because carbon nanotube does not dissolve, make its processing difficulties in organic solvent and water, this has limited its application in a lot of fields greatly, also makes troubles for deeply understanding carbon nanotube chemical.For this reason, arise at the historic moment (Science, 1998,280 (22): 1253-1255) of the organic functional of carbon nanotube research.
At present, with synthetic polymer, biomacromolecule and contain the organic molecule or the metal complex of functional group, the method that connects by physical adsorption or covalency has been carried out modification or functionalization work to the pipe end of carbon nanotube outside surface or single-wall carbon tube.But also there is not the surface to contain the report of the functionalized carbon nano-tube of isocyanate groups at present.Because isocyanate groups has very high reactive behavior, if can allow the surface of carbon nanotube connect this group, then as intermediate, can prepare many new function carbon nano tube materials.
Summary of the invention: the objective of the invention is to pass through chemical reaction, make the organic compound that has isocyanate groups be connected to carbon nano tube surface, the preparation surface has the functionalized carbon nano-tube of isocyanate groups, thereby can be used as a kind of important intermediate nano material, satisfy the needs of different research work and Application Areas.
Technical scheme of the present invention is as follows:
By molecular designing, the surface is had the modified carbon nano-tube of amino or hydroxyl and excessive binary or multicomponent isocyanate reaction, obtain the functionalized carbon nano-tube that the surface has isocyanate groups.
The concrete preparation method of the functionalized carbon nano-tube of the present invention surface isocyanate groups is as follows:
Step (a): carbon nanometer tube material is mixed with acid with strong oxidizing property with 0.1~100 weight ratio, with 0~100kHz ultrasonication after 2 minutes to 2 hours, 20~200 ℃ are stirred down, reaction 0.5~100hr, suction filtration, the water repetitive scrubbing repeatedly is neutral to filtrate, obtains the acidifying carbon nanotube after the vacuum-drying;
Step (b): add step (a) gained acidifying carbon nanotube 1 weight part and acylating agent thionyl chloride 1~100 weight part, behind 0~100kHz ultrasonication, 3~60min, be heated to 20~160 ℃, stir reaction 5~100hr down, suction filtration and repetitive scrubbing are removed acylating agent, obtain acylated carbon nano-tube; With gained acidylate carbon nanotube 1 weight part and dibasic alcohol, polyvalent alcohol, diamine or polyamine 1~50 weight part mix, behind 0~100kHz ultrasonication, 3~100min, react 1~50hr down at 0~200 ℃, suction filtration is behind the repetitive scrubbing, vacuum-drying obtains the carbon nanotube that the surface has hydroxyl or amido;
Step (c): it is 20/1~1/100 reinforced with weight ratio that above gained surface is had the modified carbon nano-tube of amino or hydroxyl and binary or multicomponent isocyanate, react 2~120h down in-30~100 ℃, after filtration, washing, vacuum-drying obtains the functionalized carbon nano-tube that the surface has isocyanate groups.
The used carbon nanotube of the present invention comprises single wall, double-walled and multi-walled carbon nano-tubes.
The reaction solvent for use is an organic solvent in the step of the present invention (c), particularly middle dimethyl sulfoxide (DMSO), N, dinethylformamide, N, N-N,N-DIMETHYLACETAMIDE, N-N-methyl-2-2-pyrrolidone N-, tetramethylene sulfone, dioxy hexanaphthene, chloroform, tetrahydrofuran (THF), ethyl acetate, acetone, acetonitrile, butanone, benzene, toluene, oil of mirbane, chlorinated benzene, perhaps their mixture.
Used binary of the present invention or multicomponent isocyanate are the organic compound that contains two or more isocyanate groups, isophorone diisocyanate (IPDI) particularly, tolylene diisocyanate (TDI), 4,4 '-ditan-vulcabond (MDI), hexamethylene diisocyanate (HDI), fourth vulcabond (BDI), hot vulcabond (ODI), the last of the ten Heavenly stems vulcabond, naphthalene diisocyanate (NDI), three (to isocyanate phenyl) methane.
Surface provided by the invention has the functionalized carbon nano-tube of isocyanate groups in polar organic solvent such as dimethyl sulfoxide (DMSO), N, dinethylformamide, N, the N-N,N-DIMETHYLACETAMIDE, has good dispersiveness in the N-N-methyl-2-2-pyrrolidone N-etc., its surperficial isocyanate groups has reactive behavior, can be further and amino, hydroxyls etc. react, also can react with excessive diamines or glycol, surperficial isocyanate groups is converted into amino or hydroxyl, thereby can realize material and molecular designing in carbon nano tube surface easily, thereby obtain various functionalized carbon nano-tube and relevant nano-devices with special construction and performance, can also be used as linking agent, for the preparation high performance material provides a kind of reactive behavior high intermediate, have a wide range of applications.
Embodiment: the following examples are to further specify of the present invention, rather than limit the scope of the invention.
Embodiment 1: the multi-walled carbon nano-tubes with the catalytic pyrolysis method preparation is an initial raw material, in the single neck round-bottomed flask of the 100mL that the magnetic agitation rotor is housed, add 2g exsiccant carbon nanometer tube material and 20mL 60% weight ratio concentration concentrated nitric acid, with 40kHz ultrasonication 30min post-heating to 120 ℃, reaction 24hr down stirs and refluxes, with φ 0.22 μ m tetrafluoroethylene millipore filtration suction filtration, repeatedly to neutral, obtain acidifying carbon nanotube behind 80 ℃ of vacuum-drying 24hr with the deionized water repetitive scrubbing;
In the single neck round-bottomed flask of the 100mL that the magnetic agitation rotor is housed, add above gained acidifying carbon nanotube 1.5g and thionyl chloride 8g, behind 40kHz ultrasonication 30min, be heated to 60 ℃, reaction 24hr down stirs and refluxes, suction filtration and repetitive scrubbing are removed thionyl chloride, obtain acylated carbon nano-tube;
In the single neck round-bottomed flask of the 100mL that the magnetic agitation rotor is housed, add step (b) gained acidylate carbon nanotube 1.3g and quadrol 25g, seal with the turned welt soft rubber ball, take out inflated with nitrogen repeatedly three times, behind 40kHz ultrasonication 30min, react 24hr down at 100 ℃, suction filtration is removed unreacted reactant and byproduct of reaction, with behind the deionized water wash, 80 ℃ of vacuum-dryings obtain the carbon nanotube 1.1g that the surface has amido repeatedly;
In the single neck round-bottomed flask of the 100mL that the magnetic agitation rotor is housed, add 5g 4,4 '-ditan-vulcabond (MDI) and 50mL N, the N-N,N-DIMETHYLACETAMIDE, after treating the solid dissolving, flask is placed ice/water-bath, and the surface that adding 0.3g prepares in advance has amino modified carbon nano-tube.Stirring reaction 2h under ice/water-bath, ultrasonic 5 minutes, heat to 40 ℃, continue reaction 24h.Decompress filter is used 200mL N,N-dimethylacetamide washing leaching cake 4 times, uses tetrahydrofuran (THF) 200mL washing leaching cake 4 times again, obtains target product behind 40 ℃ of vacuum-drying 5h.
Embodiment 2: in the single neck round-bottomed flask of the 100mL that the magnetic agitation rotor is housed, add 5g hexamethylene diisocyanate (HDI) and 50mL N,N-dimethylacetamide, after the dissolving, flask is placed ice/water-bath, and the surface that adding 0.3g prepares in advance has amino modified carbon nano-tube.Stirring reaction two 2h under ice/water-bath, ultrasonic 5 minutes, heat to 40 ℃, continue reaction 48h.Decompress filter is used 200mL N,N-dimethylacetamide washing leaching cake 4 times, uses tetrahydrofuran (THF) 200mL washing leaching cake 4 times again, obtains target product behind 40 ℃ of vacuum-drying 5h.
Embodiment 3: in the single neck round-bottomed flask of the 100mL that the magnetic agitation rotor is housed, add 2g hexanediamine and 20mL N,N-dimethylacetamide, after the dissolving, flask is placed ice/water-bath, add the functionalized carbon nano-tube that 0.1g embodiment 1 prepared surface has isocyanate groups.Stirring reaction is two 10 minutes under ice/water-bath, and ultrasonic 5 minutes, heat to 50 ℃, continue reaction 48h.Decompress filter is used 200mL N,N-dimethylacetamide washing leaching cake 4 times, uses tetrahydrofuran (THF) 200mL washing leaching cake 4 times again, obtains the surface behind 40 ℃ of vacuum-drying 5h and has amino functionalized carbon nano-tube.This embodiment illustrates that the isocyanate groups that the prepared surface of the present invention has on the functionalized carbon nano-tube of isocyanate groups still has chemically reactive, can continue to take place chemical reaction.
Claims (4)
1. the surface has the preparation method of the functionalized carbon nano-tube of isocyanate groups, it is characterized in that its concrete preparation method is as follows:
Step (a): carbon nanometer tube material is mixed with acid with strong oxidizing property with 0.1~100 weight ratio, with 0~100kHz ultrasonication after 2 minutes to 2 hours, 20~200 ℃ are stirred down, reaction 0.5~100hr, suction filtration, the water repetitive scrubbing repeatedly is neutral to filtrate, obtains the acidifying carbon nanotube after the vacuum-drying;
Step (b): add step (a) gained acidifying carbon nanotube 1 weight part and acylating agent thionyl chloride 1~100 weight part, behind 0~100kHz ultrasonication, 3~60min, be heated to 20~160 ℃, stir reaction 5~100hr down, suction filtration and repetitive scrubbing are removed acylating agent, obtain acylated carbon nano-tube; With gained acidylate carbon nanotube 1 weight part and dibasic alcohol, polyvalent alcohol, diamine or polyamine 1~50 weight part mix, behind 0~100kHz ultrasonication, 3~100min, react 1~50hr down at 0~200 ℃, suction filtration is behind the repetitive scrubbing, vacuum-drying obtains the carbon nanotube that the surface has hydroxyl or amido;
Step (c): it is 20/1~1/100 reinforced with weight ratio that above gained surface is had the modified carbon nano-tube of amino or hydroxyl and binary or multicomponent isocyanate, react 2~120h down in-30~100 ℃, after filtration, washing, vacuum-drying obtains the functionalized carbon nano-tube that the surface has isocyanate groups.
2. surface according to claim 1 has the preparation method of the functionalized carbon nano-tube of isocyanate groups, it is characterized in that used carbon nanotube comprises single wall, double-walled and multi-walled carbon nano-tubes.
3. surface according to claim 1 has the preparation method of the functionalized carbon nano-tube of isocyanate groups, it is characterized in that the reaction solvent for use is an organic solvent in the step (c), particularly middle dimethyl sulfoxide (DMSO), N, dinethylformamide, N, N-N,N-DIMETHYLACETAMIDE, N-N-methyl-2-2-pyrrolidone N-, tetramethylene sulfone, dioxy hexanaphthene, chloroform, tetrahydrofuran (THF), ethyl acetate, acetone, acetonitrile, butanone, benzene, toluene, oil of mirbane, chlorinated benzene, perhaps their mixture.
4. the surface has the functionalized carbon nano-tube of isocyanate groups, it is characterized in that the surface of adopting the described preparation method of claim 1-3 to obtain has the functionalized carbon nano-tube of isocyanate groups, can mainly be used as the nanometer linking agent, nanometer membrane-forming agent, function nano material precursor and nano material intermediate.
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