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Photochromic compounds comprising polymeric substituents and methods for preparation and use thereof

A photochromic and compound technology, applied in the field of polymer products that can transmit light, can solve problems such as increasing the fading speed

Inactive Publication Date: 2007-12-12
POLYMERS AUSTRALIA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These factors create very important commercial limitations to the technology, especially when fast fading is desired since there is a trade-off between increasing the speed of fading and optimizing color brightness in the activated state

Method used

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  • Photochromic compounds comprising polymeric substituents and methods for preparation and use thereof
  • Photochromic compounds comprising polymeric substituents and methods for preparation and use thereof
  • Photochromic compounds comprising polymeric substituents and methods for preparation and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0472] Synthesis of Photochromic Initiator 1 and Spirooxazine-Polystyrene Polymer Conjugates

[0473] Synthesis of the first step photochromic initiator 1

[0474]

[0475] 9'-(4-Chloromethylbenzoyloxy)-1,3,3-trimethylspiro[indoline 2,3'-[3H]naphtho[2,1-b][1 , 4] oxazine (1)

[0476] 9'-Hydroxy-1,3,3-trimethylspiro[indoline 2,3'-[3H]naphtho[2,1-b][1,4]oxazine (2.5g, 72.7 ×10 -4 mol) into 30 mL of dichloromethane in a 100 mL three-neck round bottom flask. Add triethylamine (1.10g, 10.9×10 -3 mol), and the reaction mixture was stirred for half an hour. Then 4-(chloromethyl)benzoyl chloride (1.65g, 87.2×10 -4mol) was dissolved in 10 mL of dichloromethane and added dropwise to the reaction mixture under argon, cooled to 0 °C. The reaction mixture was stirred for a further 1 hour at freezing temperature and then for a final hour at room temperature. The obtained product was confirmed by TLC with 1:1 diethyl ether and hexane. Wash the product with 100 mL 0.5M NaOH, 100 m...

Embodiment 2

[0487] Example 2 Synthesis of Photochromic Initiator 2

[0488]

[0489] 9'-(4-methylbenzoyloxy)-1,3,3-trimethylspiro[indoline 2,3'-[3H]naphtho[2,1-b][1, 4] Oxazine (2)

[0490] This compound was synthesized as in Example 1, but the acid chloride used was 2-bromo-isobutyl bromide. The product is purified by column chromatography. 1 H NMR ((CD 3 ) 2 CO) δ: 1.34, 1.36, 2.16, 2.78, 6.67, 6.87, 7.08, 7.16, 7.20, 7.36, 7.84, 7.86, 7.96, 8.38 ppm.

Embodiment 3

[0492] Synthesis of Photochromic Initiator 3

[0493]

[0494] Butane-1-thiol (1.06g, 1.17×10 -2 mol), carbon disulfide (2.14g, 2.81×10 -2 mol) and triethylamine (2.85g, 2.81×10 -2 nol) was added to 30 mL of chloroform and stirred overnight. Subsequently, 9'-(4-chloromethylbenzoyloxy)-1,3,3-trimethylspiro[indoline 2,3'-[3H]naphtho[2,1-b ][1,4]oxazine](5.82g, 1.17×10 -2 mol), and stirred at 60° C. until TLC (3:2 diethyl ether and hexane) confirmed the formation of the product. The product was purified by washing with water, brine, and drying over magnesium sulfate, followed by recrystallization from methanol / chloroform. 1 H NMR ((CD 3 ) 2 CO) δ: .94, 1.35, 1.36, 1.47, 1.71, 2.78, 3.46, 4.85, 6.67, 6.87, 7.07, 7.16, 7.20, 7.37, 7.68, 7.84, 7.86, 7.95, 8.23, 8.40ppm.

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Abstract

The present invention relates to a compound comprising a photochromic moiety and at least one substituent comprising a polymer chain having a carbon backbone and a plurality of functional moieties appended to the carbon backbone.

Description

field of invention [0001] The present invention relates to a class of functionalized photochromic dyes, compositions containing the functionalized dyes, and methods of forming polymeric compositions, and light-transmissive polymeric articles exhibiting a photochromic response. Background of the invention [0002] Photochromism is a property that has been used for many years to produce articles that transmit light. A compound is said to be photochromic if it changes color when irradiated at one wavelength and returns to its original color when irradiated at a second wavelength or thermally (without irradiation). The use of photochromism in the production of spectacle lenses is particularly beneficial because it enables the efficiency of filtering radiation to vary with the intensity of the radiation. Photochromic materials can also be used in other polymer composition fields in products or applications such as windows, automotive windshields, automotive and aircraft transpar...

Claims

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Application Information

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IPC IPC(8): C09K9/02C08F293/00G02B1/04G02B5/23G03C1/685C08F220/06C08F220/18
CPCG02B5/23C08F2438/01C08F230/08C08F220/56C09K9/02G03C1/733C08F220/14C08F220/18C08F2438/03C08F220/1804
Inventor 理查德·A·埃文斯乔治娜·K·萨奇托马斯·P·戴维斯尼诺·马利克戴维·A·刘易斯乔纳森·A·坎贝尔
Owner POLYMERS AUSTRALIA
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