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Nano composite materials and products of photochromism of heterocyclic ring substituted spirooxazine compounds

A nano-composite material and photochromic technology, applied in the direction of color-changing fluorescent materials, optics, optical components, etc., can solve the problems of inability to dissolve photochromic materials, affect defoaming, bond strength, increase processing costs, etc., to achieve Excellent photochromic performance, adjustable fading rate, fast fading effect

Inactive Publication Date: 2006-11-08
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In addition, they still have not been able to directly dissolve the photochromic material in PMMA, but can only be polymerized and extruded by MMA (methyl methacrylate) monomer.
This will not only increase the processing cost, but also affect the defoaming and bonding strength of the processing process.

Method used

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  • Nano composite materials and products of photochromism of heterocyclic ring substituted spirooxazine compounds
  • Nano composite materials and products of photochromism of heterocyclic ring substituted spirooxazine compounds
  • Nano composite materials and products of photochromism of heterocyclic ring substituted spirooxazine compounds

Examples

Experimental program
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Effect test

Embodiment 1

[0044] For the preparation of photochromic compounds 1-6, take the preparation of 5-chloro-1,3,3-trimethyl-6'-morpholine-spirooxazine (compound 1) as an example. The preparation methods of compounds 2-6 are similar. Compounds 1-6 are listed in Table 1.

[0045] Preparation of 5-chloro-1,3,3-trimethyl-6'-morpholine-spirooxazine (compound 1)

[0046] The first step, the preparation of 5-chloro-1,3,3-trimethyl-2-methylene indoline

[0047] In a 1000mL three-neck flask, add 26g of p-chloroaniline and 150mL of 6M HCl, heat to dissolve, then cool it to about 0°C with an ice bath, control the temperature and add dropwise 15g of NaNO 2 60mL of aqueous solution, continue to stir for 30 minutes, filter, add Na to the filtrate 2 SO 3 solution (70g Na 2 SO 3 +400mL water), after the addition, stir again until the temperature rises to room temperature, add concentrated HCl to acidify. The solid was obtained by suction filtration, and after drying thoroughly, weighed 35 g of the soli...

Embodiment 2

[0058] Blue (1,3,3-trimethyl-6'-indoline-spiroindoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine) Preparation of Photochromic PMMA Sunglasses for Radiation Protection:

[0059] Weigh 930g of PMMA resin powder and add it into 5580mL of anhydrous toluene, heat and stir, and dissolve to obtain a colorless transparent solution. To this solution was added 1,3,3-trimethyl-6'-indoline-spiroindoline-2,3'-[3H]naphtho[2,1-b][1,4]oxa 50g of oxazine photochromic nanocomposite material, 5g of light stabilizer, 5g of oxygen quencher and 10g of antioxidant, after fully stirring and dissolving, pour evenly into a Petri dish and store in a dark room. After the solvent was completely evaporated, it was dried in an oven at 60 °C for 20 min. Then, the membrane is peeled off from the dish. The prepared membranes were kept in a dark room.

Embodiment 3

[0061] Violet (1,3,3-trimethyl-6'-piperidine-spiroindoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine) radiation protection Preparation of Sunglasses with Photochromic PMMA:

[0062] Weigh 930g of PMMA resin powder and add it into 5580mL of anhydrous toluene, heat and stir, and dissolve to obtain a colorless transparent solution. To this solution was added 1,3,3-trimethyl-6'-piperidine-spiroindoline-2,3'-[3H]naphtho[2,1-b][1,4]oxazine 50g of photochromic nano-composite material, 5g of light stabilizer, 5g of single-line oxygen quencher and 10g of antioxidant, after fully stirring and dissolving, pour evenly into a Petri dish and store in a dark room. After the solvent was completely evaporated, it was dried in an oven at 60 °C for 20 min. Then, the membrane is peeled off from the dish. The prepared membranes were kept in a dark room.

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Abstract

The invention relates to a photochromic heterocyclic substituted spiro-azine compound nanocomposite material, which comprises the following composition in weight percent: 2-20% of a photochromic heterocyclic substituted spiro-azine compound nanocomposite, PMMA resin powder 76~94%, light stabilizer: bis(2,2,6,6-tetramethyl-4-hydroxypiperidine) sebacate 0.01~1%, singlet oxygen quencher: N,N-di Nickel n-butyldithiocarbamate 0.01-1%, antioxidant: 2,2'-methylene bis(4-methyl-6-tert-butylphenol) 0.02-2%. The photochromic nano-composite material of the present invention has excellent photochromic properties, and under the irradiation of visible light or ultraviolet light, it has fast color development, high chroma, fast fading, good fatigue resistance, simple synthesis process, low price and high color rate. Relatively high, the fading rate is adjustable. And it can be well dissolved in various polymer media, and can be used to prepare photochromic PMMA sun lens materials for radiation protection.

Description

technical field [0001] The invention relates to an organic photochromic material, in particular to a photochromic heterocyclic substituted spirooxazine compound nanocomposite material and its product. Background technique [0002] Organic photochromic material is a new type of material with a wide range of applications, which has attracted everyone's attention. However, there are often some limitations in practical applications. First of all, in most cases, photochromic compounds must have good photochromic properties in the molecular state, and only when they are effectively and uniformly dispersed in a medium (in most cases, polymers) can they have application value. This requires them to have good solubility, uniformity, compatibility and coordination in the medium. Otherwise, crystallization will occur in the medium, or fogging will ooze out on its surface, and the photochromic properties will be lost. Secondly, it is required to have stable performance in the medium,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K9/02G02C7/10
Inventor 孟继本谈廷风黄华鸣陈培丽高用彬
Owner NANKAI UNIV
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