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Carbon nanotube dispersing phenylacetylene-based polyfunctional group polymer and preparation method thereof

A technology of functional polymers and carbon nanotubes, applied in the field of phenylacetylene-based polyfunctional polymers and their preparation, can solve the problems of restricting the use of carbon nanotubes, agglomeration of carbon nanotubes, entanglement or knotting, etc., and it is convenient to achieve process parameters. The effect of simple control and synthesis method and low cost of use

Inactive Publication Date: 2019-04-23
NEW MATERIAL INST OF SHANDONG ACADEMY OF SCI +1
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  • Abstract
  • Description
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  • Application Information

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Problems solved by technology

Due to the strong van der Waals force between carbon nanotubes, single-wall or multi-wall carbon nanotubes are prone to agglomeration, entanglement or knotting, and cannot be uniformly dispersed, thus restricting the use of carbon nanotubes.
[0003] Sun Xiaoyan and others pointed out in "Research on the Dispersion of Carbon Nanotubes" that carbon nanotubes have a unique structure and excellent physical and chemical properties, but carbon nanotubes are easily entangled and agglomerated

Method used

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  • Carbon nanotube dispersing phenylacetylene-based polyfunctional group polymer and preparation method thereof
  • Carbon nanotube dispersing phenylacetylene-based polyfunctional group polymer and preparation method thereof
  • Carbon nanotube dispersing phenylacetylene-based polyfunctional group polymer and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] figure 1 Preparation method of phenylethynyl polyfunctional polymer 5a.

[0033] Intermediate 2a: Add 1,3-dibutoxybenzene (22.2g, 100mmol) to a dry 1000Ml three-neck flask placed in an ice-salt bath at -5°C, add 500Ml of dry dichloromethane, and stir for 20 minutes Then add bromine water (40.0g, 250mmol) dichloromethane solution 200Ml dropwise, dropwise in 60 minutes, remove the ice-salt bath after dropping, stir at room temperature for 24 hours, add an appropriate amount of sodium bicarbonate solution to neutralize the reaction system, Then it was extracted, dried, concentrated by rotary evaporation, and purified by column chromatography to obtain 31.4 g of white powdery solid with a yield of 83%. 1 H NMR (400MHz, Chloroform-d) δ7.08(s, 2H), 3.94(t, J=6.5Hz, 4H), 1.85–1.70 (m, 4H), 1.58–1.45(m, 4H), 0.98( t,J=7.4Hz,6H). 13 C NMR (100MHz, Chloroform-d) δ150.1, 118.5, 111.2, 70.0, 31.2, 19.2, 13.8.

[0034] Intermediate 3a: Under nitrogen protection, add ...

Embodiment 2

[0038]

[0039] Intermediate 2b: Add 1,3-dihexyloxybenzene (27.8 g, 100 mmol) into a dry 1000Ml three-neck flask placed in an ice-salt bath at -5°C, add 500Ml of dry dichloromethane, and stir for 20 minutes Add 200Ml of dichloromethane solution of bromine water (40.0g, 250mmol) dropwise, drop it in 60 minutes, remove the ice-salt bath after dropping, stir at room temperature for 24 hours, add an appropriate amount of sodium bicarbonate solution to neutralize the reaction system, Then it was extracted, dried, concentrated by rotary evaporation, and purified by column chromatography to obtain 36.9 g of white powdery solid with a yield of 85%. 1 H NMR (400MHz, Chloroform-d) δ7.08(s,2H),3.94(t,J=6.5Hz,4H), 1.86–1.71(m,4H),1.61–1.41(m,4H),1.40– 1.24(m,8H),0.97–0.79(m,6H). 13 CNMR (100 MHz, Chloroform-d) δ150.1, 118.4, 111.1, 70.3, 31.5, 29.1, 25.6, 22.6, 14.0.

[0040] Intermediate 3b: Under nitrogen protection, add Intermediate 2b (8.7g, 20mmol) to a dry 250Ml three-necked fl...

Embodiment 3

[0044]

[0045] Intermediate 2c: Add 1,3-dioctyloxybenzene (33.4 g, 100 mmol) into a dry 1000Ml three-necked flask placed in an ice-salt bath at -5°C, add 500Ml of dry dichloromethane, and stir for 20 minutes Add 200Ml of dichloromethane solution of bromine water (40.0g, 250mmol) dropwise, drop it in 60 minutes, remove the ice-salt bath after dropping, stir at room temperature for 24 hours, add an appropriate amount of sodium bicarbonate solution to neutralize the reaction system, Then it was extracted, dried, concentrated by rotary evaporation, and purified by column chromatography to obtain 38.7 g of white powdery solid with a yield of 79%. 1 H NMR (400MHz, Chloroform-d) δ7.07(s,2H),3.92(t,J=6.5Hz,4H), 1.85–1.73(m,4H),1.59–1.39(m,4H),1.41– 1.21(m,16H),0.95–0.77(m,6H). 13 C NMR (100 MHz, Chloroform-d) δ150.1, 118.4, 111.0, 71.4, 31.7, 29.5, 28.5, 27.1, 25.7, 22.6, 14.0.

[0046] Intermediate 3c: Under nitrogen protection, add Intermediate 2c (9.8g, 20mmol) to a dry 250Ml...

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Abstract

The invention discloses a carbon nanotube dispersing phenylacetylene-based polyfunctional group polymer and a preparation method thereof. The backbone chain of the carbon nanotube dispersing phenylacetylene-based polyfunctional group polymer is phenylacetylene, and the side chain of the carbon nanotube dispersing phenylacetylene-based polyfunctional group polymer is alkoxy. The preparation methodof the carbon nanotube dispersing phenylacetylene-based polyfunctional group polymer comprises taking 1, 4-dialkoxy substituted bisphenol ether 1 as the raw material for bromination to obtain dibromo-bisphenol ether 2, subjecting the dibromo-bisphenol ether 2 to reaction with trimethylsilylacetylene to obtain an intermediate 3, removing TMS (trimethylsilyl) of the intermediate 3 to obtain terminalalkyne 4, subjecting the terminal alkyne 4 to Sonogashira reaction with the dibromo-bisphenol ether 2 to produce a high-molecular polyfunctional group polymer containing functional backbone and sidechains. The prepared carbon nanotube dispersing phenylacetylene-based polyfunctional group polymer can produce backbone chain pi-pi adsorption and side chain entanglement with carbon nanotubes to achieve well dispersion of the carbon nanotubes under the premise of not damaging the carbon nanotubes; according to difference in the structure of the carbon nanotube dispersing phenylacetylene-based polyfunctional group polymer and the sizes of the carbon nanotubes, the dispersion degrees ranges between 2% and 7%.

Description

technical field [0001] The invention belongs to the field of organic macromolecules, and in particular relates to a phenylethynyl multifunctional polymer used for dispersing carbon nanotubes and a preparation method thereof. Background technique [0002] Carbon nanotubes are one-dimensional nanomaterials with perfectly connected hexagonal structures and possess excellent mechanical, electrical, and chemical properties. Common carbon nanotubes have a diameter of 2-100 nm and a length of 10-200 μm. Due to the strong van der Waals force between carbon nanotubes, single-wall or multi-wall carbon nanotubes are prone to agglomeration, entanglement or knotting, and cannot be uniformly dispersed, thus restricting the use of carbon nanotubes. [0003] Sun Xiaoyan and others pointed out in "Research on the Dispersion of Carbon Nanotubes" that carbon nanotubes have a unique structure and excellent physical and chemical properties, but carbon nanotubes are easy to entangle with each ot...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08F138/00C08K9/04C08K3/04
CPCC08F138/00C08K9/08C08K3/041
Inventor 孔彪李继超刘家庆魏化震王丹勇
Owner NEW MATERIAL INST OF SHANDONG ACADEMY OF SCI
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