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Mercapto-containing naphthopyran photochromic compound and its preparation method and application

A technology of naphthopyrans and photochromism, which is applied in the field of polymer chemistry, can solve problems such as premature termination of the reaction, and achieve the effect of broadening the application field and the synthesis method is simple and efficient

Active Publication Date: 2021-10-19
SHANGHAI GANTIAN OPTICAL MATERIALS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In addition, photo- or heat-initiated polymerization reactions are widely used in nanotechnology, biomaterials, and materials science, but common photo- or heat-initiated reactions are prone to premature termination due to the presence of oxygen

Method used

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  • Mercapto-containing naphthopyran photochromic compound and its preparation method and application
  • Mercapto-containing naphthopyran photochromic compound and its preparation method and application
  • Mercapto-containing naphthopyran photochromic compound and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067]

[0068] In a 1000mL three-neck flask, the compound shown in the dry formula III-1 (see US Patent US5645767 for the preparation method) (20.5g, 37.9mmol) was dissolved in 300mL of anhydrous toluene, and then mercaptoethanol (5.9g, 75.5mmol) was added , Stir at room temperature for 1 hour, then slowly add 5ml of concentrated sulfuric acid dropwise, after the concentrated sulfuric acid is added dropwise, connect the water separation condensing device, raise the temperature to 115°C for reflux reaction and water separation for 4 hours, turn off the heating and cool to room temperature, add water to wash And separate the liquid (3 × 500mL), dry the toluene layer with anhydrous sodium sulfate, spin the solvent to dry, and then purify by column chromatography (200-300 mesh silica gel), use toluene and ethyl acetate with a volume ratio of 100:1 for development agent to obtain 18.7g of pale yellow solid compound I-1. 1 H NMR (300MHz, CDCl 3 )δ8.22(s,1H),8.19(d,1H),7.65(m,4H...

Embodiment 2

[0074]

[0075] In a 1000mL three-neck flask, dissolve the dried formula III-2 (20.2g, 46.1mmol) (20.2g, 46.1mmol) in anhydrous toluene, add mercaptoethanol (7.2g, 92.1mmol), and stir at room temperature After 1 hour, slowly add 5ml of concentrated sulfuric acid dropwise. After the concentrated sulfuric acid is added dropwise, connect the water separation condensing device, raise the temperature to 115°C for reflux reaction and water separation for 4 hours, turn off the heating, and cool to room temperature. Add water to wash and separate (3×500mL), dry the toluene layer with anhydrous sodium sulfate, spin the solvent to dryness, and purify by column chromatography (200-300 mesh silica gel), use toluene and ethyl acetate with a volume ratio of 100:1 As a developer, 17.1 g of white solid compound II-1 was obtained. 1 H NMR (300MHz, CDCl 3 )δ8.15(s,1H),7.65(d,1H),7.28(d,4H),7.26(s,H),6.89(m,5H),6.58(d,2H),4.91(s,2H ),3.81(s,6H),3.67(t,2H),2.73(t,2H),2.66(s,3H),1.4(s,1H,-SH)...

Embodiment 3

[0080]

[0081] In a 1000mL three-neck flask, dissolve the dried formula III-3 (see US Patent US5645767 for the preparation method) (20.8g, 36.9mmol) in 300mL of anhydrous toluene, then add mercaptoethanol (5.8g, 73.8mmol), and stir at room temperature After 1 hour, slowly add 5ml of concentrated sulfuric acid dropwise. After the concentrated sulfuric acid is added dropwise, connect the water separation condensing device, raise the temperature to 115°C for reflux reaction and water separation for 4 hours, turn off the heating, and cool to room temperature. Add water to wash and separate (3×500mL), dry the toluene layer with anhydrous sodium sulfate, spin the solvent to dryness, and then purify by column chromatography (200-300 mesh silica gel), use toluene and ethyl acetate with a volume ratio of 100:1 As a developer, 18.1 g of white solid compound I-2 was obtained. 1 H NMR (300MHz, CDCl 3 )δ8.22(s,1H),8.18(d,1H),7.62(m,4H),7.28(d,2H),7.30(m,3H),7.10(d,2H),6.71(m,2H ),6.3...

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Abstract

The invention discloses a naphthopyran photochromic compound containing a mercapto group, the structure of which is shown in formula I or II: for the definition of each substituent, please refer to the description. The invention also discloses a water-soluble photochromic composition prepared from the above-mentioned naphthopyran photochromic compound containing mercapto groups, which is made of the following components in parts by weight: 1-20 parts of photochromic units , 40-500 parts of water-soluble polymer, 10-500 parts of solvent, the photochromic unit is the mercapto-containing naphthopyran photochromic compound. The present invention also provides an application of the water-soluble photochromic composition in preparing water-based photochromic nail polish. The water-soluble photochromic composition prepared by the invention can be applied to water-based photochromic nail polish, anti-counterfeiting ink, cosmetics, clothing, handicrafts, outdoor decoration materials and optical lenses.

Description

technical field [0001] The invention belongs to the technical field of polymer chemistry, and in particular relates to a mercapto-containing naphthopyran photochromic compound and a preparation method and application thereof. Background technique [0002] Photochromism is a light-induced reversible discoloration reaction based on the principle of chemical reaction. Light energy is a clean and renewable energy source, so the development and application of this kind of material has very broad prospects. At present, the most widely used commercial applications are color-changing glasses, high-end cosmetics, and color-changing clothing. Potential applications include intelligent window film coatings, organic photoelectric information storage units, and color-changing anti-counterfeiting inks. [0003] Photochromic materials can be divided into T-type and P-type photochromic materials according to the driving force of the reverse reaction. Among them, the T-type material is the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/94C09K9/02A61K8/49A61Q3/02A61K8/87C08G18/87C08G59/14
CPCA61K8/498A61K8/87A61K2800/438A61Q3/02C07D311/94C08G18/87C08G59/1483C09K9/02C09K2211/1029C09K2211/1088
Inventor 甘家安宋熊荣
Owner SHANGHAI GANTIAN OPTICAL MATERIALS