石墨烯衍生物及其聚酰亚胺纳米复合膜的制备
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摘要
石墨烯及其衍生物因其独特的蜂窝状二维结构，表现出优异的物理化学性能，如优异的力学性能、高的透光率、极大的比表面积和阻隔性等。这些优异的性质使石墨烯及其衍生物在多个领域具有广泛的应用前景，其中与聚合物复合制备高性能和多功能化复合材料是近年来一个重要的研究方向。氟化石墨烯和氧化石墨烯是受到最多关注的两种石墨烯衍生物。氟化石墨烯的低成本、高效率制备以及在聚合物纳米复合材料中的应用仍是一个有待深入研究的课题。而有关氧化石墨烯的基础研究、有机功能化以及应用等仍具有较大的研究空间。将石墨烯及其衍生物应用于高性能、多功能化聚酰亚胺（PI）复合膜制备是近几年来聚酰亚胺无机纳米改性的研究热点之一。本文基于以上研究背景，开展了氟化石墨烯和氧化石墨烯及其有机功能化的制备工作，同时将制备获得的石墨烯衍生物应用于聚酰亚胺纳米复合膜中，详细研究了PI复合膜的力学、耐热、介电和吸水性等性能。
本文对氟化石墨烯的简便、低成本和高效制备方法进行了探索。以F/C比分别为0.6和1.08的氟化石墨（记作GIF-L、GIF-H）为原料，分别通过改进Hummers法和NaOH强碱溶液方法，制备了含氧氟化石墨，再以氧氟化石墨为前驱体，通过液相超声剥离过程制备了氧氟化石墨烯。相比强碱改性-剥离过程，氧化-剥离过程更易制备获得F/C比基本保持不变、易在有机溶剂中稳定分散且层数更少（1-5层）的氧氟化石墨烯。这是源于氧化-剥离过程能在GIF-L结构中更为有效地引入含氧基团，从而增大了氧氟化石墨烯与极性有机溶剂间强的界面作用。
采用三种不同粒径的石墨为原料，通过氧化-剥离制备了氧化石墨烯(GO)。详细研究原料尺寸、超声条件（功率、时间和介质）等因素对GO横向尺寸大小及分布的影响。结果表明，在水和NMP介质中均可超声剥离制备GO，GO横向尺寸随超声功率、超声时间的增加以及原料粒径的减小而降低。在超声时间为60min时，不同原料制得的GO横向尺寸差别不大，平均横向长度都在1μm左右。
将葵二酸和1,5-二-(4-胺基苯基)-1,4-戊二烯-3-酮（DAPD）作为有机修饰剂，对GO进行有机功能化，制备了两种功能化氧化石墨烯（记为MGO-1和MGO-2）。两种有机分子的成功引入，增加了其在有机溶剂中的溶解性。DAPD分子赋予了MGO-2良好的光敏性，紫外（UV）光辐照338s时，DAPD分子间的α,β-不饱和酮结构中C=C键的[2+2]光环化反应程度达到平衡，约为41%。
探索了氧氟化石墨烯（GFO）和功能化氧化石墨烯（MGO-1）分别改性聚酰亚胺复合膜。以4,4’-二氨基二苯醚(ODA)和均苯四甲酸酐（PMDA）为单体，采用原位聚合法分别制备了聚酰亚胺/氧氟化石墨烯（PI/GFO）和聚酰亚胺/功能化氧化石墨烯（PI/MGO）复合膜。研究表明，在改性石墨烯较低含量（≤2wt%）时，可以均匀分散于PI基体中，且与PI链间存在较强的界面作用(包括氢键和共价键)，因而有效改善了PI复合膜的力学、玻璃化转变温度、吸水性等综合性能。改性石墨烯含量的增加会导致其发生团聚以及与PI间界面作用下降，因而复合膜综合性能下降。两种复合膜在介电性能和热膨性能上存在较大差异，低极化率、易受热运动的C-F键的存在致使PI/GFO复合膜的介电常数下降（低GFO含量时），但线膨胀系数（CTE）升高；而MGO-1自身较多的极性基团、热亚胺化过程造成的MGO-1发生部分还原和团聚，以及MGO-1对PI分子链的热运动的限制作用等因素，使PI/MGO复合膜的介电常数升高、CTE降低。
For the unique2D-dimensional honeycomb structure, graphene and itsderivatives exhibits excellent physical and chemical properties, such as excellentmechanical properties, high transmittance, huge specific surface area and barrierproperties, etc. These excellent properties make graphene and its derivatives have awide range of applications in many fields, and the usage of graphenen and itsderivatives in fabrication of polymer composites with high performance andmulti-function is one of the important researches in recent years. Graphene fluorideand graphene oxide are the most concerned grahene derivatives. However, preparationof graphene fluoride by a low cost and high efficiency method, and the application ofgraphene fluoride in polymer nanocomposites are needed further study. Furthermore,the basic research, organic functionalization and application researches on thegraphene oxide still have a large research space. On the field of the modifiedpolyimide by nano-inorganic materials, the application of graphene and its derivativeshas become a research hotspot. Based on the above research background, we carriedout some research work, including preparation of graphene fluoride, graphene oxideand its organic functional products. Meantime, the graphene derivatives above wereused in preparation of polyimide nanocomposite films, and the properties of polymercomposites, including mechanical properties, thermal stability, dielectric propertiesand water absorption rate, were studied in details.
In this paper, we had explored the simple, low cost and efficient methods topreparation graphene fluoride. The graphite fluoride with the F/C atomic ratio of o.6and1.08was used as stating materials (denoted as GIF-L and GIF-H, respetively).The GIF-L and GIF-H were both firstly modified by improved Hummers methods andNaOH solution with high concentration, respectively, and then the correspondingproducts were liquid-phase exfoliation into graphene fluoroxide by ultrasonication.Compared to alkali modification–exfoliation process, the oxidation-exfoliationprocess offered more advantages in preparing graphene fluoride, because the later method could obtain graphene fluoride with F content ramainning, better dispersion inorganic solvents and fewer layers (layers1-5). This result is due to the more effectiveto introduce oxygen-containing groups in the GIF-L configuration by the oxidation-exfoliation process,which led to enhencing the interface interaction between modifiedgraphene fluoride and polar organic solvents.
Graphene oxide was preparation through the processes of oxidization andexfoliation by using three particle sizes of graphite as the raw materials. The effects offactors on the lateral size and lateral size distribution of GO were studied in details,and the factors included the particle size of graphite, ultrasonication conditions(power, time and solvents). The results shown that the lateral size of GO decreasedwith increasing the ultrasonication power, time and decreasing the particle size of theraw materials, but when the ultrasonication time was up to60min, the average oflateral size of GO was similar and less than1μm. The changes of lateral size of GOobtained by ultrasonication in NMP was similar to in water, whereas, the yield of GOin NMP is smaller than in water.
The sebacic acid and1,5-bis(4-aminophenyl)-1,4-pentadiene-3-ketone (DAPD)were used as organic modifiers, and two type of organic functional GO (MGO-1andMGO-2) were preparation by the reaction between the modifiers and GO. Introducingthe organic molecules onto the GO flakes lead to the increasing the solubility offunctional GO in organic solvents. The DAPD molecules endowed MGO-2a goodphotosensitivity. The [2+2] photocycloaddition reaction between the C=C from theα,β-unsaturated ketone structure in the DAPD occurred under the ultraviolet (UV)light irradiation, and when the irradiation time was338s, the equilibrium extent ofphotocycloaddition reached up to41%
We had explored the effects of the fillers, modified graphene fluoride (GFO) andfunctional graphene oxide (MGO-1), on the properties of polyimide composite films.The polyimide/modified graphene fluoride (PI/GFO) and polyimide/functionalgraphene oxide (PI/MGO) composite films were preparation by in situpolymerization, in which the4,4’-diaminodiphenyl ether (ODA) and pyromelliticanhydride (PMDA) were used as monomers. The study demonstrated that the fillers could be uniformly dispersed in the PI matrix when the filler content was low (≤2wt%), and there existed strong interface interaction (hydrogen bonding and covalentbonding) between the filler and PI matrix.Therefore, the over performance includingmechanical properties, glass-transition temperature and water absorption of PIcomposite films were effectively improved. However, adding fillers content resultedin agglomeration of fillers and weakening the interface interaction between thefillers and matrix, and finally led to decreasing the overall performance of PIcomposite films. There were big differences in dielectric properties and thermalexpansion properties between these two types of PI composite films. The presence ofC-F bonds, which possess the properties of low polarizability and susceptible tothermal motion, caused reduction of dielectric constant (only for the low GFOcontent) but giving rise to the increasing line expansion coefficient (CTE) of thePI/GFO composite films. For PI/MGO composite films, because of being affected bythe following factors, the more polar groups existing in MGO-1structure, theagglomeration of partially reduction of MGO-1resulting from thethermalimidization and the limitation of MGO-1for the thermal motion of PI molecules, sothe dielectric constant and CTE of PI/MGO composite films obviously increased anddecreased, respectively.
本文对氟化石墨烯的简便、低成本和高效制备方法进行了探索。以F/C比分别为0.6和1.08的氟化石墨（记作GIF-L、GIF-H）为原料，分别通过改进Hummers法和NaOH强碱溶液方法，制备了含氧氟化石墨，再以氧氟化石墨为前驱体，通过液相超声剥离过程制备了氧氟化石墨烯。相比强碱改性-剥离过程，氧化-剥离过程更易制备获得F/C比基本保持不变、易在有机溶剂中稳定分散且层数更少（1-5层）的氧氟化石墨烯。这是源于氧化-剥离过程能在GIF-L结构中更为有效地引入含氧基团，从而增大了氧氟化石墨烯与极性有机溶剂间强的界面作用。
采用三种不同粒径的石墨为原料，通过氧化-剥离制备了氧化石墨烯(GO)。详细研究原料尺寸、超声条件（功率、时间和介质）等因素对GO横向尺寸大小及分布的影响。结果表明，在水和NMP介质中均可超声剥离制备GO，GO横向尺寸随超声功率、超声时间的增加以及原料粒径的减小而降低。在超声时间为60min时，不同原料制得的GO横向尺寸差别不大，平均横向长度都在1μm左右。
将葵二酸和1,5-二-(4-胺基苯基)-1,4-戊二烯-3-酮（DAPD）作为有机修饰剂，对GO进行有机功能化，制备了两种功能化氧化石墨烯（记为MGO-1和MGO-2）。两种有机分子的成功引入，增加了其在有机溶剂中的溶解性。DAPD分子赋予了MGO-2良好的光敏性，紫外（UV）光辐照338s时，DAPD分子间的α,β-不饱和酮结构中C=C键的[2+2]光环化反应程度达到平衡，约为41%。
探索了氧氟化石墨烯（GFO）和功能化氧化石墨烯（MGO-1）分别改性聚酰亚胺复合膜。以4,4’-二氨基二苯醚(ODA)和均苯四甲酸酐（PMDA）为单体，采用原位聚合法分别制备了聚酰亚胺/氧氟化石墨烯（PI/GFO）和聚酰亚胺/功能化氧化石墨烯（PI/MGO）复合膜。研究表明，在改性石墨烯较低含量（≤2wt%）时，可以均匀分散于PI基体中，且与PI链间存在较强的界面作用(包括氢键和共价键)，因而有效改善了PI复合膜的力学、玻璃化转变温度、吸水性等综合性能。改性石墨烯含量的增加会导致其发生团聚以及与PI间界面作用下降，因而复合膜综合性能下降。两种复合膜在介电性能和热膨性能上存在较大差异，低极化率、易受热运动的C-F键的存在致使PI/GFO复合膜的介电常数下降（低GFO含量时），但线膨胀系数（CTE）升高；而MGO-1自身较多的极性基团、热亚胺化过程造成的MGO-1发生部分还原和团聚，以及MGO-1对PI分子链的热运动的限制作用等因素，使PI/MGO复合膜的介电常数升高、CTE降低。
For the unique2D-dimensional honeycomb structure, graphene and itsderivatives exhibits excellent physical and chemical properties, such as excellentmechanical properties, high transmittance, huge specific surface area and barrierproperties, etc. These excellent properties make graphene and its derivatives have awide range of applications in many fields, and the usage of graphenen and itsderivatives in fabrication of polymer composites with high performance andmulti-function is one of the important researches in recent years. Graphene fluorideand graphene oxide are the most concerned grahene derivatives. However, preparationof graphene fluoride by a low cost and high efficiency method, and the application ofgraphene fluoride in polymer nanocomposites are needed further study. Furthermore,the basic research, organic functionalization and application researches on thegraphene oxide still have a large research space. On the field of the modifiedpolyimide by nano-inorganic materials, the application of graphene and its derivativeshas become a research hotspot. Based on the above research background, we carriedout some research work, including preparation of graphene fluoride, graphene oxideand its organic functional products. Meantime, the graphene derivatives above wereused in preparation of polyimide nanocomposite films, and the properties of polymercomposites, including mechanical properties, thermal stability, dielectric propertiesand water absorption rate, were studied in details.
In this paper, we had explored the simple, low cost and efficient methods topreparation graphene fluoride. The graphite fluoride with the F/C atomic ratio of o.6and1.08was used as stating materials (denoted as GIF-L and GIF-H, respetively).The GIF-L and GIF-H were both firstly modified by improved Hummers methods andNaOH solution with high concentration, respectively, and then the correspondingproducts were liquid-phase exfoliation into graphene fluoroxide by ultrasonication.Compared to alkali modification–exfoliation process, the oxidation-exfoliationprocess offered more advantages in preparing graphene fluoride, because the later method could obtain graphene fluoride with F content ramainning, better dispersion inorganic solvents and fewer layers (layers1-5). This result is due to the more effectiveto introduce oxygen-containing groups in the GIF-L configuration by the oxidation-exfoliation process,which led to enhencing the interface interaction between modifiedgraphene fluoride and polar organic solvents.
Graphene oxide was preparation through the processes of oxidization andexfoliation by using three particle sizes of graphite as the raw materials. The effects offactors on the lateral size and lateral size distribution of GO were studied in details,and the factors included the particle size of graphite, ultrasonication conditions(power, time and solvents). The results shown that the lateral size of GO decreasedwith increasing the ultrasonication power, time and decreasing the particle size of theraw materials, but when the ultrasonication time was up to60min, the average oflateral size of GO was similar and less than1μm. The changes of lateral size of GOobtained by ultrasonication in NMP was similar to in water, whereas, the yield of GOin NMP is smaller than in water.
The sebacic acid and1,5-bis(4-aminophenyl)-1,4-pentadiene-3-ketone (DAPD)were used as organic modifiers, and two type of organic functional GO (MGO-1andMGO-2) were preparation by the reaction between the modifiers and GO. Introducingthe organic molecules onto the GO flakes lead to the increasing the solubility offunctional GO in organic solvents. The DAPD molecules endowed MGO-2a goodphotosensitivity. The [2+2] photocycloaddition reaction between the C=C from theα,β-unsaturated ketone structure in the DAPD occurred under the ultraviolet (UV)light irradiation, and when the irradiation time was338s, the equilibrium extent ofphotocycloaddition reached up to41%
We had explored the effects of the fillers, modified graphene fluoride (GFO) andfunctional graphene oxide (MGO-1), on the properties of polyimide composite films.The polyimide/modified graphene fluoride (PI/GFO) and polyimide/functionalgraphene oxide (PI/MGO) composite films were preparation by in situpolymerization, in which the4,4’-diaminodiphenyl ether (ODA) and pyromelliticanhydride (PMDA) were used as monomers. The study demonstrated that the fillers could be uniformly dispersed in the PI matrix when the filler content was low (≤2wt%), and there existed strong interface interaction (hydrogen bonding and covalentbonding) between the filler and PI matrix.Therefore, the over performance includingmechanical properties, glass-transition temperature and water absorption of PIcomposite films were effectively improved. However, adding fillers content resultedin agglomeration of fillers and weakening the interface interaction between thefillers and matrix, and finally led to decreasing the overall performance of PIcomposite films. There were big differences in dielectric properties and thermalexpansion properties between these two types of PI composite films. The presence ofC-F bonds, which possess the properties of low polarizability and susceptible tothermal motion, caused reduction of dielectric constant (only for the low GFOcontent) but giving rise to the increasing line expansion coefficient (CTE) of thePI/GFO composite films. For PI/MGO composite films, because of being affected bythe following factors, the more polar groups existing in MGO-1structure, theagglomeration of partially reduction of MGO-1resulting from thethermalimidization and the limitation of MGO-1for the thermal motion of PI molecules, sothe dielectric constant and CTE of PI/MGO composite films obviously increased anddecreased, respectively.
引文
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