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Reversible temperature-sensitive allochroic dye, and preparation method and application thereof

A temperature-sensitive color-changing and dye technology, applied in applications, organic dyes, household appliances, etc., can solve the problems of low stability, reduce dye toxicity, and high toxicity, achieve reduced toxicity, structural adjustment and enhanced design capabilities, and biocompatibility Sex-reducing effect

Active Publication Date: 2015-11-04
苏州雄鹰笔墨新材料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention aims at the problems of low stability and high toxicity due to the use of hydroxyl-containing phenol, naphthol or bisphenol A and their derivatives as electron-accepting chromogenic agents in current reversible thermosensitive color-changing dyes, and provides a reversible thermochromic dye. Sensitive color-changing dyes, preparation methods and applications thereof, using biocompatible and low-toxicity polyphosphate as an electron-accepting chromogenic agent, used to prepare reversible thermosensitive color-changing dyes, greatly reducing the toxicity of dyes, and is expected to expand reversible thermosensitive color-changing dyes The application fields of dyes, especially those that can be used in close contact with the human body

Method used

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  • Reversible temperature-sensitive allochroic dye, and preparation method and application thereof
  • Reversible temperature-sensitive allochroic dye, and preparation method and application thereof
  • Reversible temperature-sensitive allochroic dye, and preparation method and application thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0032] 1. Dissolve 2-methoxyethanol (7.67g, 100.8mmol) and equimolar amount of triethylamine (10.20g, 100.8mmol) in 100mL tetrahydrofuran, and cool to -5°C. Under stirring condition, 100 mL of 2-chloro-2-oxo-1,3,2-dioxaphospholane (14.36 g, 100.8 mmol) in tetrahydrofuran was slowly added dropwise thereto. After the dropwise addition, continue to react at -5°C for 12 hours, under N 2 Under the protection of the atmosphere, filter and remove the precipitate. The filtrate was concentrated and distilled under reduced pressure twice to give the product 2-methoxyethyl-2-oxo-1,3,2-dioxaphospholane as a colorless liquid.

[0033] See attached figure 1 , which is the NMR spectrum of the product 2-methoxyethyl-2-oxo-1,3,2-dioxaphospholane in this example, the chemical shift in the spectrum is consistent with the expected structure, confirming that The compound was successfully prepared.

[0034] 2. Aluminum triisopropoxide (155mmol) was dissolved in 92mL of tetrahydrofuran, and the ...

Embodiment 2

[0037] 1. Dissolve 2-ethoxyethanol (9.07g, 100.8mmol) and equimolar amount of triethylamine (10.20g, 100.8mmol) in 100mL tetrahydrofuran, and cool to -5°C. Under stirring condition, 100 mL of 2-chloro-2-oxo-1,3,2-dioxaphospholane (14.36 g, 100.8 mmol) in tetrahydrofuran was slowly added dropwise thereto. After the dropwise addition, continue to react at -5°C for 12 hours, under N 2Under the protection of the atmosphere, filter and remove the precipitate. The filtrate was concentrated and distilled under reduced pressure twice to give the product 2-ethoxyethyl-2-oxo-1,3,2-dioxaphospholane as a colorless liquid.

[0038] 2. Aluminum triisopropoxide (155mmol) was dissolved in 92mL of tetrahydrofuran, and the 2-ethoxyethyl-2-oxo-1,3,2-dioxaphospholane (2.99 g, 13.1 mmol) was dissolved in tetrahydrofuran (22.51 g) solution, mixed, and reacted at 20°C. After 4 h of reaction, excess acetic acid was added to the solution to terminate the reaction. The reaction solution was concent...

Embodiment 3

[0041] 1. Dissolve 2-butoxyethanol (13.07g, 100.8mmol) and equimolar amount of triethylamine (10.20g, 100.8mmol) in 100mL tetrahydrofuran, and cool to -5°C. Under stirring condition, 100 mL of 2-chloro-2-oxo-1,3,2-dioxaphospholane (14.36 g, 100.8 mmol) in tetrahydrofuran was slowly added dropwise thereto. After the dropwise addition, continue to react at -5°C for 12 hours, under N 2 Under the protection of the atmosphere, filter and remove the precipitate. The filtrate was concentrated and distilled under reduced pressure twice to give the product 2-butoxyethyl-2-oxo-1,3,2-dioxaphospholane as a colorless liquid.

[0042] 2. Dissolving aluminum triisopropoxide (155mmol) in 92mL tetrahydrofuran, the 2-butoxyethyl-2-oxo-1,3,2-dioxaphospholane (3.49 g, 13.1 mmol) was dissolved in tetrahydrofuran (22.51 g) solution, mixed, and reacted at 20°C. After 4 h of reaction, excess acetic acid was added to the solution to terminate the reaction. The reaction solution was concentrated, p...

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Abstract

The invention relates to a reversible temperature-sensitive allochroic dye, and a preparation method and application thereof. The preparation method comprises the following steps: carrying out ring-opening polymerization on a cyclic phosphate monomer to prepare polyphosphate which is used as an electron receiving developer; using a fluorane dye or triaryl methane dye as an electron donating procrypsis dye, adding an organic solvent, heating to a molten state, stirring uniformly, keeping the temperature, and cooling at room temperature to obtain the reversible temperature-sensitive allochroic dye. The biocompatible low-toxicity polyphosphate is synthesized as the electron receiving developer and used for blending the reversible temperature-sensitive allochroic dye, thereby greatly lowering the toxicity of the dye. The reversible temperature-sensitive allochroic dye provided by the invention is hopeful to widen the application range of the reversible temperature-sensitive allochroic dye, and especially can be used in the occasions of intimate contact of human bodies. Meanwhile, the polyphosphate has the chain macromolecule structure, and thus, provides abundant space for subsequent functionalization and color development / fading property regulation.

Description

technical field [0001] The invention relates to a reversible temperature-sensitive color-changing dye that can be used in ink for pens and a preparation method thereof, belonging to the technical field of fine chemicals. Background technique [0002] Temperature-sensitive color-changing materials have the characteristic of changing color with temperature, and have been widely used in the fields of temperature display, medical and health, advertising, textile and clothing, printing ink and pen ink. Temperature-sensitive color-changing materials can be mainly divided into three categories: inorganic, organic and liquid crystal. Due to the limited variety of inorganic reversible color-changing materials, the limited thermochromic effect and high toxicity limit its wide-scale application. The advantage of liquid crystal thermosensitive color-changing materials is that the color-changing sensitivity is high. In most cases, the color change will occur when the temperature changes...

Claims

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Application Information

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IPC IPC(8): C09B67/00C09D11/50C08G79/04C09D11/17
Inventor 金桂英朱健丁春来
Owner 苏州雄鹰笔墨新材料有限公司
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