Photochromic compositions and light transmissible articles

A photochromic and composition technology, applied in the direction of color-changing fluorescent materials, silicon organic compounds, radiation-absorbing coatings, etc., can solve the problems of reversible color change or low efficiency, short chemical degradation life and so on

Inactive Publication Date: 2006-02-01
POLYMERS AUSTRALIA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Many photochromic compounds have a fairly short lifetime due to chemical degradation before fatigue and no longer undergo reversible color changes or become less efficient

Method used

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  • Photochromic compositions and light transmissible articles
  • Photochromic compositions and light transmissible articles
  • Photochromic compositions and light transmissible articles

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0350] 9'-(PEG(350)-succinyl)-1,3,3-trimethylspiro[indoline-2,3'-[3h]naphthalene[2,1-b][1,4] Oxazine] (PEG(350)-suc-SOX)

[0351]

[0352] 9'-Hydroxy-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphthalene[2,1-b][1,4]oxazine] (1.95g, 5.67mmol) and triethylamine (0.857g, 1.18mL, 8.5mmol) were added together in dichloromethane (30mL), then chlorosuccinic acid mono-PEG (350) ester (3.19g, 6.8 mmol) was added dropwise to the solution at room temperature under the protection of argon. When the reaction was complete, it was diluted and refined by washing with dichloromethane, washed with dilute sodium hydroxide, dilute HCl and brine, followed by final drying over magnesium sulfate to give a dark brown oil (4 g), which was purified by column chromatography , to give a brown oil. 1 H NMR (CDCl 3 )δ1.33(s, 6H, C(CH 3 ) 2 ), 2.75 (s, 3H, N-CH 3 ), 2.82 & 2.94 (multiplet, 4H, C=O-CH 2 CH 2 -C=O), 3.35(s, 3H, O-CH 3 ), 3.53 (multiplet, 2H, CH 2 -O-CH 3 ), 3.63 (s, PEG unit), 3.7...

Embodiment 2

[0354] 9'-(PEG(750)-succinyl)-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphthalene[2,1-b][1,4] Oxazine] (PEG(750)-suc-SOX)

[0355]

[0356] 9'-(PEG(750)-succinyl)-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphthalene[2,1-b][1,4] Oxazine] with 9'-(PEG(350)-succinyl)-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphthalene[2,1-b] [1,4]Oxazine] was synthesized in the same manner, using chlorosuccinic acid mono-PEG (750) ester instead of chlorosuccinic acid mono-PEG (350) ester, thus obtaining a product yield of 76%. That 1 The H NMR spectrum appears to be consistent with 9'-(PEG(350)-succinyl)-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphthalene[2,1-b ][1,4]oxazine], except that it has a larger singlet of one PEG unit at 3.63 ppm. 1 H NMR (CDCl 3 )δ1.33(s, 6H, C(CH 3 ) 2 ), 2.75 (s, 3H, N-CH 3 ), 2.82 & 2.94 (multiplet, 4H, C=O-CH 2 CH 2 -C=O), 3.35(s, 3H, O-CH 3 ), 3.53 (multiplet, 2H, CH 2 -O-CH 3 ), 3.63 (s, PEG unit), 3.71 (multiplet, 2H, CH 2 CH 2 O-C=O), 4.30 (multipl...

Embodiment 3

[0358] part (a)

[0359] 5,9'-Dihydroxy-1,3,3-trimethylspiro[indoline-2,3'-[3H]naphthalene[2,1-b][1,4]oxazine]

[0360]

[0361] 5-Hydroxy-1,2,3,3-tetramethylindolium iodide (1.65 g, 5.2 mmol) was dissolved in methanol (10 mL), and butanone (5 mL) and piperidine (0.5 mL) were added dropwise , let the solution stand. 2,7-Dihydroxy-1-nitrosonaphthalene (0.983 g) was then added and the solution was refluxed for 1 hour before it was stirred overnight at room temperature. The solvent was evaporated and the residue was chromatographed to give a dark blue product (300 mg 17%). 1 H NMR (DMSO-d 6 )δ1.20 & 1.27 (s, 3H, methyl), 2.57 (s, 3H, N-Me), 6.37-6.61 (multiple aromatic groups), 6.61-6.76 (multiple aromatic groups), 7.58-7.98 ( Multiple aryl groups), 8.80 (naphthyl aryl), 9.88 (naphthyl aryl) ppm.

[0362] part (b)

[0363] 5,9'-di(PEG(350)-succinyl)-1,3,3-trimethylspiro[induline-2,3'-[3H]naphthalene[2,1-b ][1,4]oxazine](bis PEG(350)-suc)+SOX)

[0364]

[0365] With ...

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Abstract

The invention relates to a photochromic polymeric composition comprising a polymer matrix and a photochromic compound which is an adduct comprising a photochromic moiety and at least one pendant oligomer group to provide a rate of fade of the photochromic polymeric composition which is significantly changed when compared with the corresponding composition comprising the photochromic compound without said pendent oligomer. The invention also relates to a photochromic compound which is an adduct comprising a photochromic moiety and at least one pendent oligomer.

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 articles exhibiting a photochromic response. Background technique [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 exposed to light and returns to its original color when the light is stopped. The use of photochromism in the production of spectacle lenses is particularly beneficial because it allows the efficiency of filtering radiation to vary with radiation intensity. Photochromic materials can also be used in other polymer composition areas in products or applications such as windows, automotive windshields, automotive and aircraft transparencies, polymer film coating compositions, optical switches, and data storage devices. Ph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K9/02C08K5/357C08K5/5465C08J3/20C08J7/00C09D5/32C07F7/21C07C245/08C07D311/92C07D498/10C08G77/388C08G65/333
Inventor 理查德·A·埃文斯梅利莎·A·斯基德莫尔拉克伦·H·伊特蕾西·L·汉利戴维·A·刘易斯
Owner POLYMERS AUSTRALIA
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