Polycyclic aromatic hydrocarbon silane coupling agent with strong fluorescence characteristic as well as green and efficient preparation and application thereof

A technology of polycyclic aromatic hydrocarbon silane coupling agent and fluorescence characteristics, which is applied in the engineering field to achieve the effects of simplified post-processing steps, broad industrialization prospects, and good fluorescence stability

Pending Publication Date: 2021-11-05
SHANDONG GUIKE NEW MATERIAL CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there is no report on the efficient preparation of polycyclic aromatic hydrocarbon silane coupling agents with strong fluorescent properties by using non-fluorescent commercial vinyl silane coupling agents as basic raw materials through Diels-Alder reaction

Method used

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  • Polycyclic aromatic hydrocarbon silane coupling agent with strong fluorescence characteristic as well as green and efficient preparation and application thereof
  • Polycyclic aromatic hydrocarbon silane coupling agent with strong fluorescence characteristic as well as green and efficient preparation and application thereof
  • Polycyclic aromatic hydrocarbon silane coupling agent with strong fluorescence characteristic as well as green and efficient preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] A green and high-efficiency preparation method of a polycyclic aromatic hydrocarbon silane coupling agent with strong fluorescence properties, comprising the following steps:

[0067] Disperse vinylmethyldimethoxysilane coupling agent and 7,9-diphenyl-8H-cyclopenta[a]acenaphthylen-8-one (2:1 molar ratio) in acetophenone solvent (The mass ratio of solid to liquid is 1:5), and transferred to the polytetrafluoro reactor, and nitrogen was introduced to remove the excess air in the reactor. Put the sealed reaction kettle in an oven and react at 180°C for 10 hours. After the reaction is completed, wait until the temperature drops to room temperature, and distill under reduced pressure to remove excess solvent and unreacted raw materials. The product is washed repeatedly with absolute ethanol for several times. The obtained polycyclic aromatic hydrocarbon silane coupling agent with strong fluorescent properties is an acenaphthyl dimethoxy functionalized silane coupling agent. ...

Embodiment 2

[0072] The preparation method of acenaphthene functionalized fluorescent polysiloxane comprises the following steps:

[0073] The acenaphthene-type dimethoxy functionalized silane coupling agent and vinylmethyldimethoxysilane (molar ratio is 1:8) prepared in Example 1 are mixed in ethanol / water solution (v:v is 1: 3) hydrolysis, the solid-to-liquid mass ratio is 1:5, the pH value of the solution is adjusted to 9 by 0.1M sodium hydroxide solution, after hydrolysis for 5h under reflux, the excess solvent is removed under reduced pressure, and the product is treated with chloroform Extraction is carried out to finally obtain the acenaphthene-type functionalized fluorescent polysiloxane.

Embodiment 3

[0075] A green and high-efficiency preparation method of a polycyclic aromatic hydrocarbon silane coupling agent with strong fluorescence properties, comprising the following steps:

[0076] Vinylmethyldiethoxysilane coupling agent and tetraphenylcyclopentadienone (molar ratio is 2.5:1) are dispersed in xylene solvent (solid-liquid ratio is 1:8), and transferred to In the PTFE reactor, feed nitrogen to get rid of excess air in the reactor. Put the sealed reaction kettle in an oven and react at 200°C for 12 hours. After the reaction is completed, wait until the temperature drops to room temperature, distill under reduced pressure to remove excess solvent and unreacted raw materials, and wash the product repeatedly with absolute ethanol several times; The obtained polycyclic aromatic hydrocarbon silane coupling agent with strong fluorescent properties is a diethoxytetraphenylbenzene functionalized silane coupling agent.

[0077] The reaction scheme of the present embodiment is ...

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Abstract

The invention relates to a polycyclic aromatic hydrocarbon silane coupling agent with a strong fluorescence characteristic as well as green and efficient preparation and application thereof. The polycyclic aromatic hydrocarbon functionalized silane coupling agent with a strong fluorescence characteristic is efficiently prepared by utilizing a Diels-Alder reaction between a vinyl silane coupling agent and 7,9-diphenyl-8H-cyclopenta[a]acenaphthylen-8-one containing unsaturated bonds, tetraphenyl cyclopentadiene ketone and 1,3,6,8-tetraethynylpyrene, a catalyst does not need to participate in the reaction process, and the reaction process can be realized by only depending on the temperature. The method has a great industrial application prospect. The silane coupling agent can be used for preparing fluorescent polysiloxane and fluorescent cross-linked porous organic silicon resin, has wide application prospects in the aspects of fluorescent rubber, fluorescent porous membranes, super-hydrophobic porous silicon resin and the like, and is high in research and development value. According to the method disclosed by the invention, green and clean production of the functionalized silane coupling agent is realized by utilizing a catalyst-free Diels-Alder reaction, and a low-energy-consumption mild reaction technical approach is developed in the aspects of eliminating catalyst residues, simplifying post-treatment, increasing functionalized silane types and the like.

Description

technical field [0001] The invention relates to the green and high-efficiency preparation and application of a polycyclic aromatic hydrocarbon silane coupling agent with strong fluorescence characteristics, and belongs to the field of engineering technology. Background technique [0002] Silane coupling agent is a kind of organosilicon monomer with two or more different reactive groups in the molecule. Its structural formula can be expressed as Y-Si(OR)n(n=0-3), where OR represents the ability to undergo hydrolysis - The polycondensation reaction group (such as: methoxyl or ethoxyl group) can be hydrolyzed to form an active hydroxyl group, and Y represents an organic functional group (such as vinyl group, amino group, carboxyl group, isocyano group, etc.), which can realize the silane coupling agent in the applications in different fields. Because silane coupling agents can chemically bond (couple) with organic materials and inorganic materials, they can be used as dispersa...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/18C08G77/04C08G77/06C09K11/06
CPCC07F7/1804C07F7/1892C08G77/04C08G77/06C09K11/06C09K2211/1416C09K2211/1425
Inventor 孔凡振渠源李杭杭孔令刚杨甜甜贾玲晓
Owner SHANDONG GUIKE NEW MATERIAL CO LTD
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