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Synthesis method of spiro reverse photochromic reactive dye

A photochromic and reactive dye technology, applied in the direction of reactive dyes, color-changing fluorescent materials, azo dyes, etc., can solve the problems of water solubility and poor color fastness, and achieve improved color fastness, good dyeing effect, water soluble sex improvement effect

Active Publication Date: 2017-12-08
JIANGNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In order to solve the above-mentioned problems such as water solubility and poor color fastness, the present invention provides a novel photochromic compound and its synthesis route. The present invention increases the water solubility of the color-changing compound by introducing polyethylene glycol monomethyl ether chains, and then passes Introduce s-triazine active groups to obtain photochromic reactive dyes that are reactive to fibers, and dye cotton fabrics according to the dyeing process of conventional reactive dyes to endow the fabric with photochromic function

Method used

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  • Synthesis method of spiro reverse photochromic reactive dye
  • Synthesis method of spiro reverse photochromic reactive dye
  • Synthesis method of spiro reverse photochromic reactive dye

Examples

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Embodiment 1

[0040] Embodiment 1: the synthesis of photochromic reactive dye 1

[0041] Prepare photochromic reactive dyes as follows:

[0042] (1) In the THF solution that is dissolved with 31.2g tetraethylene glycol monomethyl ether, add 50ml 1M NaOH solution, the THF solution that is dissolved with 54g p-benzenesulfonyl chloride is added dropwise, the reaction time is 2h, and the reaction temperature is 25 ℃. Afterwards, it was washed with anhydrous ether, 1M NaOH solution and distilled water, dried and then concentrated by rotary evaporation.

[0043] (2) 2.4g of activated compound and 1.05g of 2,3,3-trimethyl-indole were mixed and reacted, the reaction time was 12h, the reaction temperature was 110°C, and then washed with petroleum ether and distilled water. MS-EI: calculated for[M]+(C 20 h 32 NO 4 +): m / z 350.23, found: m / z 350.2.

[0044] (3) Dissolve 1.53g of the modified indole and 0.44g of 4-nitrosalicylaldehyde respectively, then slowly drop them into the mixed reaction, a...

Embodiment 2

[0049] Embodiment 2: the synthesis of photochromic reactive dye 2

[0050] Prepare photochromic reactive dyes as follows:

[0051] (1) Activation: In the THF solution that is dissolved with 30.5g triethylene glycol monomethyl ether, add the NaOH solution of 50ml 1M, the THF solution that is dissolved with 50g p-benzenesulfonyl chloride is added dropwise, the reaction time is 1.5h, the reaction The temperature was 25°C. After that, it was washed with anhydrous ether, 1M NaOH solution and distilled water, dried and then concentrated by rotary evaporation.

[0052] (2) Modification of the indole N atom: 2.4g of activated compound and 0.96g of 2,3,3-trimethyl-indole were mixed and reacted, the reaction time was 10h, the reaction temperature was 100°C, and then petroleum ether, distilled water washing.

[0053] (3) Spirocyclization: Dissolve 1.50g of modified indole and 0.41g of 4-nitrosalicylaldehyde respectively, then slowly drop them in for a mixed reaction, add an acid-bindin...

Embodiment 3

[0056] Embodiment 3: the synthesis of photochromic reactive dye 3

[0057] Prepare photochromic reactive dyes as follows:

[0058] (1) Activation: In the THF solution that is dissolved with 35.1g pentaethylene glycol monomethyl ether, add the NaOH solution of 50ml 1M, the THF solution that is dissolved with 55g p-benzenesulfonyl chloride is added dropwise, the reaction time is 2.5h, the reaction The temperature was 25°C. After that, it was washed with anhydrous ether, 1M NaOH solution and distilled water, dried and then concentrated by rotary evaporation.

[0059] (2) Modification of the N atom of indole: 3.0g of the activated compound and 1.21g of 2,3,3-trimethyl-indole were mixed and reacted, the reaction time was 15h, the reaction temperature was 120°C, and then petroleum ether, distilled water washing.

[0060] (3) Spirocyclization: Dissolve 1.86g of modified indole and 0.56g of 4-nitrosalicylaldehyde respectively, then slowly drop them into the mixed reaction, add an ac...

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Abstract

The invention discloses a synthesis method of a spiro reverse photochromic reactive dye and belongs to the field of light chemical industry. The method comprises the following steps: firstly activating polyethylene glycol monomethyl ether, then modifying polyethylene glycol monomethyl ether onto N atom of 2,3,3-trimethylindole, forming a photochromic dye intermediate with a spiropyrane structure with 4-nitrosalicylaldehyde and finally reducing, then introducing s-triazine reactive functional groups to prepare the photochromic reactive dye. The color of the photochromic reactive dye solution is gradually faded under illumination of sunshine, is even faded to be colorless, can also gradually restore the color indoors, and has reversibility; the dye is capable of dyeing and processing according to the conventional process of dyeing cotton via the reactive dye, is capable of effectively dyeing cotton fabrics, and is high in color fastness; meanwhile, the fabrics dyed by the photochromic reactive dye have certain photochromic effects.

Description

technical field [0001] The invention relates to the synthesis of a spiro-type reverse photochromic reactive dye, which belongs to the field of light chemical industry. Background technique [0002] With the continuous development of human society, people have higher and higher requirements for high-grade, personalized and functional textiles. In order to cater to people's new consumption psychology, color-changing textiles with high added value and high efficiency have emerged as the times require. Photochromic compounds are divided into two categories according to chemical composition: organic photochromic compounds and inorganic photochromic compounds, organic photochromic compounds include azobenzenes, spiropyrans, spirooxazines, fulgid anhydride Classes, benzonaphthoquinones, dithiazolates, etc., in which the spiropyran structure is an important class of organic photochromic dyes, usually the spiro carbon atoms on the spiropyran structure, through ultraviolet light irrad...

Claims

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Application Information

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IPC IPC(8): C09B62/04C07D491/107C09K9/02D06P1/382D06P1/673D06P3/66
CPCC07D491/107C09B62/04C09K9/02C09K2211/1029C09K2211/1059C09K2211/1088D06P1/004D06P1/382D06P1/6735D06P3/663
Inventor 孙昌赵春燕倪佳东杜金梅许长海
Owner JIANGNAN UNIV
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