CN103771400A - Method for preparing graphene dispersion liquid by utilizing pyrenyl benzoic acid polyether ester parent reagent - Google Patents
Method for preparing graphene dispersion liquid by utilizing pyrenyl benzoic acid polyether ester parent reagent Download PDFInfo
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- CN103771400A CN103771400A CN201310701060.1A CN201310701060A CN103771400A CN 103771400 A CN103771400 A CN 103771400A CN 201310701060 A CN201310701060 A CN 201310701060A CN 103771400 A CN103771400 A CN 103771400A
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Abstract
The invention relates to a method for preparing a graphene dispersion liquid by utilizing a pyrenyl benzoic acid polyether ester parent reagent. The method comprises the steps: with methoxy polyethylene glycol, p-aminobenzoic acid and 1-pyrenylboronicacid as raw materials, carrying out esterification reaction to obtain p-aminobenzoic acid polyether ester of a hydrophilic long chain, then introducing HBr which is reacted with the 1-pyrenylboronicacid to prepare 3, 5-dibromo benzoic acid methoxy polyethylene glycol, and carrying out reaction on the 3, 5-dibromo benzoic acid methoxy polyethylene glycol and the pyrenylboronicacid to synthesize amphoteric (hydrophilic and oleophylic) graphite remover; and dissolving the compound and graphene in a H2O/Et solution, carrying out twice ultrasonic treatment, standing, and carrying out centrifugation to obtain the stable a graphene dispersion liquid. With the adoption of the method, as the graphene does not need oxidation reduction, the destructive effect on a graphene structure is very small, and the unique electric and thermal conductivities of the graphene can be fully exerted; as the prepared dispersion liquid has good aqueous phase stability, an effective way is provided for the application of the graphene in the field of composites.
Description
Technical field
The present invention relates to a kind of method of utilizing pyrenyl phenylformic acid polyethers fat parents reagent to prepare graphene dispersing solution, definite saying relates to the synthetic of a kind of pyrenyl phenylformic acid polyethers fat parents reagent and utilizes its preparation to stablize the method for graphene dispersing solution.
Background technology
Graphene is a kind of Novel carbon material of monoatomic layer two dimension conjugated structure, and its theoretical specific surface area is up to 2630m
2/ g.For a long time, scientific circles infer that single-layer graphene crystal cannot stable existence theoretically.Until teaching the team leading, the Geim of Univ Manchester UK in 2004 successfully prepares first single-layer graphene, this not only allows scientists re-recognize Graphene, the more important thing is and makes people recognize that Graphene compares with nano carbon materials such as carbon nanotubes with soccerballene and have more excellent performance as Graphene has ultra-high conducting hot (thermal conductivity is up to 5300w/m.k), (electronic mobility exceedes 15000cm to splendid electroconductibility
2/ VS), excellent optical property (absorptivity is 2.3%) and superpower mechanical strength (130GPa).According to the research and development situation of current various countries Graphene, although Graphene is applied to some extent in microelectronic device, new chemical battery and photovoltaic field, but also fail to form so far industrialization, the essence factor that hinders Graphene industry development be current Graphene technology of preparing with and dispersion technology in liquid-phase system still there is significant limitation.
At present thereby first the preparation method who generally uses in the scientific research of Graphene and actual trace production is increased to its interlamellar spacing by strong oxidizer graphite oxide, make graphene oxide by high temperature or the method such as ultrasonic, then above-mentioned graphene oxide is become to Graphene by reductive agent or high temperature reduction.This method can be prepared the Graphene of gram rank, but there are two unavoidable problems in redox reaction method, first Graphene has destroyed π key and its crystalline structure in the process of oxidation, and its conductivity is declined rapidly, even changes semi-conductor and isolator into.Its two, although can recover the electric property of its part by the method for reduction, due to the minimizing of hydrophobic grouping, there is irreversible weakening in the hydrophilicity of graphene oxide, reunion rapidly in liquid-phase system.This two large problems has hindered the further application of the graphene preparation method take Hummers method as representative just.
For these distinct issues, people have explored the method for three class non covalent bond legal systems for graphene dispersing solution.One class be by with surface can and the approaching organic solvent for ultrasonic of Graphene peel off Graphene, but this method solvent generally has larger toxicity and price is more expensive, is not suitable for heavy industrialization and applies.Another kind of is that Van der Waals force by utilizing tensio-active agent and graphite ethylene linkage makes surfactant molecule be adsorbed in Graphene surface, again by stirring supersound process, in the aqueous solution, form stable disperse phase, Graphene defect prepared by this method is less, but in the Graphene of preparation, tensio-active agent is difficult to thoroughly remove, not removed surfactant molecule has affected the performance of Graphene to a certain extent, and the Graphene concentration that this method is prepared is lower.Also having a class is non covalent bond effect (electrostatic interaction, hydrogen bond, coordinate bond and pi-pi bond effect) between low molecule by functional group or polymer and Graphene form layers, then passes through supersound process, peels off graphite and prepares single-layer graphene.Graphene prepared by these class methods can stable existence and water and oil phase in, and Graphene defect is very low.Because Graphene is higher with other non covalent bonds of strength ratio (electrostatic interaction, hydrogen bond and coordinate bond) of the pi-pi bond effect forming through the nonpolar thick aromatic ring of high (surpassing) molecular chain modification, what Graphene more can be stable is present in water or oil-based system.Comprehensive each class methods and its effect, it is comparatively ideal method in current graphene preparation method that this kind utilizes the ultrasonic graphite of peeling off of pi-pi bond effect, so more and more cause people's attention.As the people such as Dong-woo (Chem.Comm., 2011,47:8259-8261) prepare selectivity graphene solution by modification four pyrenyl polyethers take graphite as raw material.And for example people (the J.Polym.Sci. such as Liu, PartA:Polym.Chem., 2010,48:425-433) utilize the synthetic controlled graphene solution of temperature and the graphene-polymer matrix material prepared of reversible addition-fracture chain transfer polymerization reaction (RAFT), this graphene solution and graphene-polymer matrix material can form stabilizing solution being less than under 24 ℃ of conditions, exceed 24 ℃ and form astable solution.Because these class methods need to be synthesized the π-π stacking organic molecule that designs special construction, therefore appropriate design the thick aromatic ring organism that synthesizes such polymer modification are key and the difficult problems that Graphene (solution) is prepared in pi-pi bond effect.
Summary of the invention
Technical barrier to be solved by this invention is, overcomes the easily destroyed and poor problem of Graphene liquid phase dispersion stability of graphene-structured in prior art, and a kind of method of utilizing pyrenyl phenylformic acid polyethers fat parents reagent to prepare stone sulfuric acid China ink alkene dispersion liquid is provided.The inventive method synthesizes in two polyether-modified pyrenyl compounds is not destroying graphene layer structure simultaneously, and the pyrenyl group of two dimensional structure is closely fitted with Graphene, both at grade direction form stronger π-π effect; Pfpe molecule chain can form intermolecular hydrogen bonding with the aqueous solution, has significantly improved consistency and the stability of Graphene in water.
Technical solution of the present invention is, with poly glycol monomethyl ether, para-amino benzoic acid and 1-pyrene boric acid are raw material, obtain the para-amino benzoic acid polyether acid fat of hydrophilic long-chain by esterification, introduce again the HBr with 1-pyrene acid reaction, prepare 3,5-dibromo-benzene formic acid poly glycol monomethyl ether fat, then synthesized again the graphite stripper of two property (hydrophilic and oleophilic) with pyrene acid reaction; This compound and Graphene are dissolved in H2O/Et solution, carry out twice ultrasonic, after leaving standstill and processing, then obtain stable graphene dispersing solution through centrifugal.
Concrete preparation method's step of the present invention is as follows:
(1) polyoxyethylene glycol monoether and para-amino benzoic acid are dissolved in to solvent S
1in, then add wherein the 1mL vitriol oil, generate precipitation, reflux.Then reaction mixture is proceeded in 250mL beaker, add 10% sodium carbonate to pH ≈ 9, suction filtration, washing, by extracted with diethyl ether, purifies and obtains product A.By A, deionized water, 40%HBr and a certain amount of 30%H
2o
2mixed at room temperature is even, purifies and obtains product B.B and 1-boric acid pyrene are dissolved in solvent THF, add wherein Na
2cO
3the aqueous solution, then add wherein tetrakis triphenylphosphine palladium, under nitrogen atmosphere by mixture vigorous stirring, reflux certain hour, demixing, cleans twice by methylene dichloride for aqueous phase layer, purifies and obtains solid product C.
(2) powdered graphite of 100mg and a certain amount of Compound C are dissolved in to the H of 50ml
2in O/EtOH mixed solvent, ultrasonic 24hrs in ice-water bath, then leaves standstill 12hrs by mixing solutions.Then in solution, slowly drip 2ml water, make solution solubility be diluted to 0.1wt%, and then supersound process 12 hours, leave standstill 12hrs, finally by obtaining single-layer graphene dispersion liquid after centrifugal disgorging.
The molecular weight of described poly glycol monomethyl ether is 400～2000, is preferably 550～1500, more preferably 750～1000.
Described solvent S1 is one or several in chloroform, DMF, THF and NMP.
In above-mentioned steps (1), the molar ratio of polyoxyethylene glycol monoether and para-amino benzoic acid is 1:1～1.5; HBr and H
2o
2molar ratio be 1:1～1.2; The molar ratio of product B and 1-boric acid pyrene is 1:2～4.
In above-mentioned steps (2), the molar ratio of product C and Graphite Powder 99 is 1:500～1000.
Compared with prior art, the advantage possessing is in the present invention:
(1) raw material sources of synthesis of amphoteric reagent C are extensive; The parents' reagent dosage synthesizing is very little, is about 1/500～1/1000 of graphite mole dosage;
(2) synthetic parents' reagent C can be directly used in peeling off of Graphene, without loaded down with trivial details redox step, and exchanges its dispersiveness in water for without structure and the electrical property of sacrificing Graphene in the process of peeling off;
(3) synthetic parents' reagent can form strong effect by π-π effect with Graphene, can make Graphene long-term stable existence in the aqueous solution.
Accompanying drawing explanation
Fig. 1 is the reacting flow chart of synthetic pyrenyl phenylformic acid polyethers fat parents reagent in embodiment 3.
Fig. 2 is TEM and the electron diffraction photo that utilizes graphene dispersing solution prepared by pyrenyl phenylformic acid polyethers fat parents reagent in embodiment 3.
Embodiment
Embodiment 1
(1) para-amino benzoic acid of 8g poly glycol monomethyl ether (Mn=750) and 1.75g is dissolved in solvent THF, above-mentioned solution is transferred in 100mL round-bottomed flask, then add wherein the 1mL vitriol oil, generate precipitation, reflux 30 minutes.Then reaction mixture is proceeded in 250mL beaker, add 10% sodium carbonate to pH ≈ 9, suction filtration, washing, by extracted with diethyl ether twice, purifies and obtains product A.By the A of 3g, 40ml water, 40%20mmolHBr and a certain amount of 30%20mmolH
2o
2mixed at room temperature is even, purifies and obtains product B.The 1-boric acid pyrene of the B of 1.00g and 0.25g is dissolved in solvent THF, adds wherein the Na of 40ml
2cO
3the aqueous solution.Then add wherein the tetrakis triphenylphosphine palladium of 0.10g, under nitrogen atmosphere by mixture vigorous stirring, reflux 24 hours, demixing, cleans twice by methylene dichloride for aqueous phase layer, purifies and obtains solid product C.
(2) 100mg powdered graphite and 20mg Compound C are dissolved in to H
2in O/ alcohol mixed solvent, ultrasonic 24hrs in ice-water bath, then leaves standstill 12hrs by mixing solutions.Then in solution, slowly drip 2ml water, make solution solubility be diluted to 0.1wt%, and then supersound process 12 hours, leave standstill 12hrs, finally by obtaining single-layer graphene dispersion liquid after centrifugal disgorging.
(1) para-amino benzoic acid of 8g poly glycol monomethyl ether (Mn=1000) and 1.64g is dissolved in solvent THF, above-mentioned solution is transferred in 100mL round-bottomed flask, then add wherein the 1mL vitriol oil, generate precipitation, reflux 30 minutes.Then reaction mixture is proceeded in 250mL beaker, add 10% sodium carbonate to pH ≈ 9, suction filtration, washing, by extracted with diethyl ether twice, purifies and obtains product A.By the A of 3.00g, 40ml water, 40%20mmolHBr and a certain amount of 30%20mmolH
2o
2mixed at room temperature is even, purifies and obtains product B.The 1-boric acid pyrene of the B of 1.00g and 0.25g is dissolved in solvent THF, adds wherein the Na of 40ml
2cO
3the aqueous solution.Then add wherein the tetrakis triphenylphosphine palladium of 0.10g, under nitrogen atmosphere by mixture vigorous stirring, reflux 24 hours, demixing, cleans twice by methylene dichloride for aqueous phase layer, purifies and obtains solid product C.
(2) 100mg powdered graphite and 12mg Compound C are dissolved in to H
2in O/ alcohol mixed solvent, ultrasonic 24hrs in ice-water bath, then leaves standstill 12hrs by mixing solutions.Then in solution, slowly drip 2ml water, make solution solubility be diluted to 0.1wt%, and then supersound process 12 hours, leave standstill 12hrs, finally by obtaining single-layer graphene dispersion liquid after centrifugal disgorging.
Embodiment 3
(1) para-amino benzoic acid of 8g poly glycol monomethyl ether (Mn=550) and 2.19g is dissolved in solvent THF, above-mentioned solution is transferred in 100mL round-bottomed flask, then add wherein the 1mL vitriol oil, generate precipitation, reflux 30 minutes.Then reaction mixture is proceeded in 250mL beaker, add 10% sodium carbonate to pH ≈ 9, suction filtration, washing, by extracted with diethyl ether twice, purifies and obtains product A.By the A of 3.00g, 40ml water, 40%20mmolHBr and 30%24mmolH
2o
2mixed at room temperature is even, purifies and obtains product B.The 1-boric acid pyrene of the B of 1.00g and 0.93g is dissolved in solvent THF, adds wherein the Na of 40ml
2cO
3the aqueous solution.Then add wherein the tetrakis triphenylphosphine palladium of 0.10g, under nitrogen atmosphere by mixture vigorous stirring, reflux 24 hours, demixing, cleans twice by methylene dichloride for aqueous phase layer, purifies and obtains solid product C.
(2) 100mg powdered graphite and 9mg Compound C are dissolved in to 50mlH
2in O/ alcohol mixed solvent, ultrasonic 24hrs in ice-water bath, then leaves standstill 12hrs by mixing solutions.Then in solution, slowly drip 2ml water, make solution solubility be diluted to 0.1wt%, and then supersound process 12 hours, leave standstill 12hrs, finally by obtaining single-layer graphene dispersion liquid after centrifugal disgorging.
Claims (6)
1. a method of utilizing pyrenyl phenylformic acid polyethers fat parents reagent to prepare graphene dispersing solution, it is characterized in that: with poly glycol monomethyl ether, para-amino benzoic acid and 1-pyrene boric acid are raw material, obtain the para-amino benzoic acid polyether acid fat of hydrophilic long-chain by esterification, introduce again the HBr with 1-pyrene acid reaction, prepare 3,5-dibromo-benzene formic acid poly glycol monomethyl ether fat, then synthesized again the graphite stripper of two property (hydrophilic and oleophilic) with pyrene acid reaction; This compound and Graphene are dissolved in H2O/Et solution, carry out twice ultrasonic, after leaving standstill and processing, then obtain stable graphene dispersing solution through centrifugal.
2. a kind of method of utilizing pyrenyl phenylformic acid polyethers fat parents reagent to prepare graphene dispersing solution as claimed in claim 1, is characterized in that: concrete technology step is as follows:
1) polyoxyethylene glycol monoether and para-amino benzoic acid are dissolved in to solvent S
1in, then add wherein the 1mL vitriol oil, generate precipitation, reflux; Then reaction mixture is proceeded in 250mL beaker, add 10% sodium carbonate to pH ≈ 9, suction filtration, washing, by extracted with diethyl ether, purifies and obtains product A; By A, deionized water, 40%HBr and a certain amount of 30%H
2o
2mixed at room temperature is even, purifies and obtains product B; B and 1-boric acid pyrene are dissolved in solvent THF, add wherein Na
2cO
3the aqueous solution, then add wherein tetrakis triphenylphosphine palladium, under nitrogen atmosphere by mixture vigorous stirring, reflux certain hour, demixing, cleans twice by methylene dichloride for aqueous phase layer, purifies and obtains solid product C;
2) powdered graphite and a certain amount of Compound C are dissolved in to the H of 50ml
2in O/EtOH mixed solvent, ultrasonic 24hrs in ice-water bath, then leaves standstill 12hrs by mixing solutions; Then in solution, slowly drip 2ml water, make solution solubility be diluted to 0.1wt%, and then supersound process 12 hours, leave standstill 12hrs, finally by obtaining single-layer graphene dispersion liquid after centrifugal disgorging.
3. a kind of method of utilizing pyrenyl phenylformic acid polyethers fat parents reagent to prepare graphene dispersing solution as claimed in claim 2, is characterized in that: in step 1), the molecular weight of poly glycol monomethyl ether is 550～1000.
4. a kind of method of utilizing pyrenyl phenylformic acid polyethers fat parents reagent to prepare graphene dispersing solution as claimed in claim 1, is characterized in that: the solvent S described in step 1)
1for one or several in chloroform, DMF, THF and NMP.
5. a kind of method of utilizing pyrenyl phenylformic acid polyethers fat parents reagent to prepare graphene dispersing solution as claimed in claim 1, is characterized in that: in step 1), the molar ratio of poly glycol monomethyl ether and para-amino benzoic acid is 1:1～1.5; HBr and H
2o
2molar ratio be 1:1～1.2; The molar ratio of product B and 1-boric acid pyrene is 1:2～4.
6. a kind of method of utilizing pyrenyl phenylformic acid polyethers fat parents reagent to prepare graphene dispersing solution as claimed in claim 1, is characterized in that: step 2) in the molar ratio of product C and Graphite Powder 99 be 1:500～1:1000.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN104761715A (en) * | 2014-01-06 | 2015-07-08 | 江苏悦达新材料科技有限公司 | Preparation method of bispyrenyl benzoic acid polyether ester amphiphilic reagent |
| CN108003041A (en) * | 2016-10-28 | 2018-05-08 | 中国石油化工股份有限公司 | A kind of method for separating Aethoxy Sklerol and polyetheramine |
| CN108394892A (en) * | 2018-05-11 | 2018-08-14 | 西安交通大学 | A kind of graphene dispersion liquid and preparation method thereof that directly graphene is modified |
| CN110194838A (en) * | 2019-05-28 | 2019-09-03 | 上海大学 | 1- pyrenyl is functionalized polysulfone material and preparation method thereof |
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| CN102320599A (en) * | 2011-08-02 | 2012-01-18 | 同济大学 | Method for functionalizing polymer on surface of nano graphene oxide |
| CN102502607A (en) * | 2011-11-10 | 2012-06-20 | 郑州大学 | Method for preparing graphene solution based on supercritical carbon dioxide and pyrenyl polymers |
| CN102976314A (en) * | 2012-11-29 | 2013-03-20 | 中国科学院宁波材料技术与工程研究所 | Novel titanium dioxide-graphene nano-composite material as well as manufacturing method and application thereof |
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2013
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102320599A (en) * | 2011-08-02 | 2012-01-18 | 同济大学 | Method for functionalizing polymer on surface of nano graphene oxide |
| CN102502607A (en) * | 2011-11-10 | 2012-06-20 | 郑州大学 | Method for preparing graphene solution based on supercritical carbon dioxide and pyrenyl polymers |
| CN102976314A (en) * | 2012-11-29 | 2013-03-20 | 中国科学院宁波材料技术与工程研究所 | Novel titanium dioxide-graphene nano-composite material as well as manufacturing method and application thereof |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104761715A (en) * | 2014-01-06 | 2015-07-08 | 江苏悦达新材料科技有限公司 | Preparation method of bispyrenyl benzoic acid polyether ester amphiphilic reagent |
| CN108003041A (en) * | 2016-10-28 | 2018-05-08 | 中国石油化工股份有限公司 | A kind of method for separating Aethoxy Sklerol and polyetheramine |
| CN108394892A (en) * | 2018-05-11 | 2018-08-14 | 西安交通大学 | A kind of graphene dispersion liquid and preparation method thereof that directly graphene is modified |
| CN110194838A (en) * | 2019-05-28 | 2019-09-03 | 上海大学 | 1- pyrenyl is functionalized polysulfone material and preparation method thereof |
| CN110194838B (en) * | 2019-05-28 | 2021-07-06 | 上海大学 | 1-pyrenyl functionalized polysulfone material and preparation method thereof |
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Address after: Room j653, building 6, 1288 Yecheng Road, Jiading District, Shanghai, 201822 Patentee after: Zhongke Yueda (Shanghai) material technology Co.,Ltd. Address before: 201822 J3330 room 912, Yecheng Road, Jiading Industrial Zone, Jiading District, Shanghai. Patentee before: Shanghai Ewang Material Technology Co.,Ltd. |