Photochromic polymer compositions and articles thereof

A photochromic, polymer technology, applied in color-changing fluorescent materials, spirally condensed pyran compound components, optics, etc., can solve the problems of fading, slow photochromic activation rate, etc.

Inactive Publication Date: 2007-08-01
TRANSITIONS OPTICAL INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

According to Claus D. Eisenbach, one of the main obstacles to the large-scale commercial application of photochromic systems is the slow rate of photochromic activation and fading in solid polymer matrices.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0116] step 1

[0117] Potassium tert-butoxide (75 grams, 0.67 moles) was added to the reaction flask containing 200 milliliters (ml) of toluene. The reaction flask was equipped with an overhead stirrer, dropping funnel, and condenser with nitrogen inlet. The contents of the reaction flask were heated to reflux temperature and 4,4'-dimethylbenzophenone (105 g, 0.5 mol), dimethyl succinate (90 g, 0.62 moles) and toluene (200 g). The resulting pasty mixture was refluxed for a further 2 hours, cooled, about 400 ml of water added and mixed vigorously. The aqueous layer was separated, acidified with dilute hydrochloric acid, and extracted with 200 ml of toluene. Solvent, toluene and residual tert-butanol were removed on a rotary evaporator to give the half ester, 4,4-bis(4-methylphenyl)-3-methoxycarbonyl-3-butenoic acid. This material was used directly in the next step without further purification.

[0118] step 2

[0119] The half ester from step 1 was added to a reactio...

Embodiment 2

[0146] The procedure of Step 9 of Example 1 was followed, except that Feed 2 was as follows:

[0147] Feed 2

[0148] Material

weight / gram)

The product of step 8 in embodiment 1

1.5

EEEA (3)

1.75

CD-552 (1)

1.75

AIBN (2)

0.15

toluene

5.0

[0149] (3) The reported Tg is -54°C and is derived from Aldrich's 2-(2-ethoxyethoxy)ethylacrylate

[0150] The obtained polymer had a weight average molecular weight of about 6800 as determined by gel permeation chromatography using polystyrene as a standard.

Embodiment 3

[0152] The procedure of Step 9 of Example 1 was followed, except that Feed 2 was as follows:

[0153] Feed 2

[0154] Material

[0155] The weight average molecular weight of the obtained polymer was about 8900 as determined by gel permeation chromatography using polystyrene as a standard.

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Abstract

Described is a photochromic polymer composition including the reaction product of at least one polymerizable photochromic material and at least one other copolymerizable material having a glass transition temperature of less than 23 DEG C upon polymerization. The photochromic polymer composition is adapted to provide an increased Fade Half Life in the Photochromic Polymer Performance Test as compared to the same photochromic compound used in the reaction product, but free of polymerizable groups. Also described are photochromic articles including the photochromic polymer composition.

Description

[0001] References to related applications [0002] This application claims priority to provisional application Ser. No. 60 / 345,166, filed December 21, 2001. technical field [0003] The present invention relates to a photochromic polymer composition that can be used in various polymer substrates. In particular, the present invention relates to a photochromic polymer composition having chemical groups that render the photochromic polymer composition reactive or compatible with a different polymer matrix, such as hydrophilic or hydrophobic Polymer matrix, more compatible. The present invention also relates to compositions and articles containing and / or coated with compositions comprising the photochromic polymer composition. [0004] Photochromic substances exhibit a reversible change in color when exposed to light containing ultraviolet light, such as under sunlight or mercury lamps. Various kinds of photochromic substances have been synthesized and proposed for use in appli...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K9/02C09K11/06G02B5/23G03C1/73G03C1/685
CPCC09K9/02C09K11/06
Inventor R·W·沃尔特斯A·库马尔F·R·布苯克本K·J·斯图尔特
Owner TRANSITIONS OPTICAL INC
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