Triarylethene photochromic material, method and application of triarylethene photochromic material as 3D printing ink

A photochromic material, triarylethene technology, applied in the field of color-changing materials, can solve problems such as narrow application range and difficulty in applying complex models, and achieve the effect of easy purification, good stability, and simple synthesis method

Pending Publication Date: 2021-03-26
NORTHWESTERN POLYTECHNICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

(Ou D, ChemicalScience, 2016.), however, the scope of application of this type of emerging materials is narrow, and photochromic films can only be simply produced. Such small molecular materials often exist in crystal or powder state, which is difficult to apply to various complex models construct

Method used

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  • Triarylethene photochromic material, method and application of triarylethene photochromic material as 3D printing ink
  • Triarylethene photochromic material, method and application of triarylethene photochromic material as 3D printing ink
  • Triarylethene photochromic material, method and application of triarylethene photochromic material as 3D printing ink

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Step 1: Synthesis of intermediate ylide reagent 4-methyl formate diethyl phenylphosphate

[0038]

[0039]Methyl 4-bromomethylbenzoate (4.60 g, 20.06 mmol) and triethyl phosphite (10.00 g, 60.18 mmol) were added to a 250 ml flask. The initial suspension in the flask was heated above 80°C to reflux on a magnetic stirrer. After refluxing for 12 hours, it was cooled to room temperature, and excess triethyl phosphite was removed by distillation under reduced pressure. After cooling, a solid precipitated from the remaining stock solution, which was washed with n-hexane, filtered and dried to obtain 5.05 g of ylide reagent 4-methyl formate diethyl phenylphosphate with a yield of 87.94%.

[0040] Failure case(1)

[0041] Methyl 4-bromomethylbenzoate (2.30 g, 10.03 mmol) and triethyl phosphite (5.00 g, 30.09 mmol) were added to a 250 ml flask. The initial suspension in the flask was heated to 50 degrees Celsius on a magnetic stirrer, and after 12 hours, it was cooled to r...

Embodiment 3

[0061] Mix the monomer of polyethylene glycol (diol) diacrylate (molecular weight 575) with the target product methyl methacrylate triarylethylene in Example 1 according to the mass fraction of 20:1, and then add a certain amount of tetrahydrofuran (THF ) solution and 5wt% photoinitiator diphenyl-(2,4,6-trimethylbenzoyl)phosphine (TPO) were fully stirred evenly as 3D printing ink. The prepared 3D inks are then used to print complex 3D structures on a custom-made high-resolution 3D printing system. The exposure time was 2 seconds, and the thickness of each layer was 50 mm. After the printing is completed, the unreacted monomer and crosslinking agent on the surface of the printed 3D structure are removed with a rubber suction ball. Finally, the structure was post-cured in a UV oven.

[0062] Table 1: final product in the embodiment in the maximum discoloration ultraviolet absorption wavelength and stimulus response condition

[0063] compound photochromic effect ...

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Abstract

The invention discloses a triarylethene photochromic material, a method and an application of the triarylethene photochromic material as 3D printing ink; the triarylethene photochromic material is a fast-response triarylethene photochromic material which is light-controllable in real time, good in memory storage function and excellent in erasability, and the triarylethene photochromic material issimple in process, high in yield and easy to purify by the aid of two synthesis methods (Corey-Funchs reaction and Wittig reaction); different functional groups are introduced, so that the photochromic property, the light emitting wavelength and other properties of a final product are adjusted. The triarylethene photochromic material containing the unsaturated polymerizable group derivative is applied to the field of 3D printing, and a photochromic three-dimensional structure with an excellent surface, a microstructure and a complex geometrical shape is obtained through a 3D printing technology. The synthesis method disclosed by the invention is simple in process, the obtained product is easy to purify, triarylethylene has no cis-trans isomerism and can be subjected to a pericyclization reaction under ultraviolet irradiation to form a closed loop structure, the closed loop structure has photochromic property, and the synthesized photochromic material has good stability.

Description

technical field [0001] The invention belongs to the field of color-changing materials, and in particular relates to a triarylethene-based photochromic material, a method and an application as a 3D printing ink. Background technique [0002] Photochromic materials refer to materials that can undergo reversible physical or chemical changes after being excited by a light source, resulting in changes in color and other physical properties. (H.Diirr, H.Bouas-Lament.Pure and Applied Chemistry, 2001) Photochromic phenomena can occur in both inorganic and organic compounds, and organic photochromic compounds are gradually Become the main research object of photochromic materials. (MINKIN VI. Chemical reviews, 2004) Organic photochromic materials mainly include the following types: spiropyrans, spirooxazines, benzopyrans, azos, fulginic anhydrides, triphenylmethanes, Diaryl vinyl compounds. However, most traditional organic photochromic materials have problems such as complex desi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K9/02C07C17/263C07C17/35C07C25/24C07C29/147C07C33/48C07C67/14C07C69/54C07C67/343C07C69/76C07F9/40C09D11/50
CPCC09K9/02C07F9/4056C07C67/343C07C29/147C07C67/14C07C17/2635C09D11/50C07C17/35C09K2211/1007C07C69/76C07C33/486C07C69/54C07C25/24
Inventor 于涛张夏宇谢宗良黄荣娟张彪王海兰黄成刘福康孙浩东肖雨欣黄维
Owner NORTHWESTERN POLYTECHNICAL UNIV
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