Photochromic polymer

A photochromic and polymer technology, applied in the direction of color-changing fluorescent materials, optics, optical components, etc., can solve the problems of siloxane phase separation reduction, problems, etc.

Active Publication Date: 2014-01-08
詹姆斯罗宾逊特种原料有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Phase separation is reduced by substituting siloxanes with two or more photochromic moieties, but the inventors have found that the tendency to phase separate at high loadings can still be a problem
Another problem discovered by the inventors with regard to silicone photochromic polymers is their susceptibility to acid degradation, which requires specific synthetic methods which are not desired by industrial manufacturers

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0190] step 1

[0191]

[0192] Poly(propylene oxide) (2.52 g, average molecular weight = 2,000, Aldrich), succinic anhydride (0.365 g) and p-toluenesulfonic acid (0.05 g) were mixed and heated at 125° C. for 30 minutes under nitrogen with stirring. The mixture was then dissolved in diethyl ether / hexane (4:1) and washed twice with 2M HCl and brine. Separate the organic layer with MgSO 4 Drying, filtration, and evaporation of the solvent in vacuo gave the product di(succinate) end-functionalized poly(propylene oxide) as a viscous oil. pass 1 H NMR (CDCl 3 ) analysis confirmed the structure as well as confirmed the completion of the reaction of the hydroxyl end groups of the starting polymer. The average molecular weight was determined to be 2,444 by integration of the analytical resonance peaks.

[0193] step 2

[0194]

[0195] The parent naphthopyran used in this step, 3,3-bis(4-methoxyphenyl)-13-hydroxy-13-methyl-indeno[2,1-f]naphtho[1,2 -b] pyran, synthesized u...

Embodiment 2

[0198] step 1

[0199]

[0200] Poly(propylene oxide) (5.02 g, average molecular weight = 1,000, Aldrich), succinic anhydride (2.50 g) and p-toluenesulfonic acid (0.13 g) were mixed and heated at 130° C. under nitrogen with stirring for 30 minutes and then in Heat at 80°C for an additional 1.5 hours. Poly(ethylene glycol) monomethyl ether (5.25 g, average molecular weight = 350, Aldrich) was added, and the mixture was heated at 100° C. for 30 minutes. The mixture was then dissolved in diethyl ether and washed three times with dilute HCl and finally with brine. Separate the organic layer with MgSO 4 Drying, filtering through a plug of silica gel, and evaporation of the solvent in vacuo gave the product di(succinate) end-functionalized poly(propylene oxide) as a viscous oil. pass 1 H NMR (CDCl 3 ) analysis confirmed the structure as well as confirmed the completion of the reaction of the hydroxyl end groups of the starting polymer. The average molecular weight was deter...

Embodiment 3

[0205] step 1

[0206]

[0207] Glycerol propoxylate (5.09 g, average molecular weight = 1,500), succinic anhydride (1.50 g) and triethylamine (2.10 mL) were added to dry dichloromethane (ca. 50 mL) under nitrogen and stirred overnight at ambient temperature . Poly(ethylene glycol) monomethyl ether (1.68 g, MW=350) was then added, the mixture was stirred for another 30 minutes, then the solvent was evaporated in vacuo. The residue was dissolved in diethyl ether and washed three times with dilute HCl and finally with brine. Separate the organic layer with MgSO 4 Drying, filtration and evaporation of the solvent gave the product as a viscous oil (5.11 g). pass 1 H NMR (CDCl 3 ) analysis confirmed the structure as tri(succinic acid / ester) end-functionalized glycerol propoxylate. The average molecular weight was determined to be 2,175 (n PPO =10.2 / arm).

[0208] step 2

[0209]

[0210] The tri(succinate) end-functionalized glycerol propoxylate from step 1 (0.26 g) ...

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Abstract

A photochromic polymer comprising at least two photochromic moieties linked by a straight or branched chain polymer selected from the group consisting of poly (C2 to C4 alkylene oxide), poly [C1 to C10 alkoxy substituted (C2 to C4 alkylene oxide)] and poly [C1 to C-15 acyloxy substituted (C2 to C4 alkylene oxide)].

Description

technical field [0001] This application claims priority to US Provisional Patent Application 61 / 481830, filed May 3, 2011, the contents of which are incorporated herein by reference. [0002] The present invention relates to photochromic polymers, in particular to linear or branched poly(alkylene oxide) polymers linking at least two photochromic moieties, and to polymers comprising a host polymer and a photochromic polymer Compositions, and to methods of preparing photochromic polymers and polymer compositions comprising photochromic polymers. Background technique [0003] Photochromism is a property that has been used for many years in the manufacture of light permeable articles. 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 manufacture of soft focus lens assemblies is particularly beneficial as it enables the efficiency of filtering radiation to ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G65/00C08G65/04C08G65/329C09K9/02G02B5/23G02B1/04C07D311/92C07D311/96
CPCC09K2211/1475G02B1/041C09K2211/1416C07D311/92C09K2211/1466C09K2211/1433C08G65/33396C07D498/10C09K2211/1425C08G65/3315C08G65/3324C09K2211/145G02B5/23C09K9/02G02B1/04G02B1/043
Inventor R.A.埃文斯N.马利克
Owner 詹姆斯罗宾逊特种原料有限公司
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