Radiation imagery chemistry: process – composition – or product th – Dye image from radiation sensitive dye or dye former by dry... – Composition or product
Patent
1983-04-21
1984-11-27
Kittle, John E.
Radiation imagery chemistry: process, composition, or product th
Dye image from radiation sensitive dye or dye former by dry...
Composition or product
430 19, 430962, 428913, G03C 1733
Patent
active
044851685
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
1. Technical Field
This invention relates to a photochromic photosensitive composition, and more particularly to a photochromic photosensitive composition which takes on color upon exposure to ultraviolet rays and regains its initial colorless state upon application of heat or exposure to intensive visible rays.
2. Background Art
Among organic substances showing photochromism, spiropyran compounds have been investigated most intensively. When used as an actual photosensitive material, a spiropyran compound is generally dispersed in a desired binder resin and the resultant mixture is formed into a film or coated on a desired base. The photosensitive material has such properties that it takes on color upon exposure to ultraviolet rays and regains its initial colorless state upon application of heat or exposure to visible rays.
Owing to the above-described interesting characteristics of the photochromic photosensitive material which makes use of the spiropyran compound, it has been attempted to apply it to various recording or memory materials, copying materials, or the like. However, conventional photochromic photosensitive materials were difficult to use as recording materials because they were thermally unstable when colored by virtue of light and undesirably regained their initial colorless state gradually when allowed to stand, thereby limiting the storable time of developed color to 2 weeks or so at most.
When using the photochromic photosensitive material as a recording material, it is ideal that the developed color image will remain semipermanently when allowed to stand in a dark place at room temperature and it may be erased by a suitable means such as heating whenever desired. Indolinospiropyran compounds represented by the following general formula (I): ##STR2## have been used predominantly among such conventionally-used spiropyran compounds. However, such indolinospiropyran compounds suffered, as mentioned above, from their insufficient thermal stability in a colored state.
DISCLOSURE OF THE INVENTION
An object of this invention is to provide a photochromic photosensitive composition which overcomes such drawbacks of the conventional photochromic photosensitive compositions, is extremely stable to heat in a colored state, is capable of storing a developed color image for an extremely long period of time and is thus suitable for long-time recording.
In the photochromic and photosensitive composition according to this invention, a spiropyran compound represented by the following general formula (II): ##STR3## wherein R.sub.1 represents an alkyl group containing 1 to 10 carbon atoms, R.sub.2 represents an alkyl group containing 1 to 10 carbon atoms or a phenyl group, R.sub.3 represents a hydrogen atom, a halogen atom, a methoxy group or an alkyl group containing 1 to 5 carbon atoms, and R.sub.4 represents a hydrogen atom, an alkyl group containing 1 to 5 carbon atoms, a methoxy group or a methylthio group, dissolved and dispersed in a bisphenol A type polyether resin for enhancing thermal stability of the compound in a colored state.
In the above general formula (II), the alkyl group means the monovalent residue of a saturated straight chain or branched hydrocarbon, the examples of which may include methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl, hexyl, octyl and decyl groups and the like. Examples of the halogen atom may include chlorine atom, bromine atom and the like.
The bisphenol A type polyether resin used in this invention is obtainable by reacting bisphenol A or its analogues with a halogenated alkylene oxide in the presence of an alkali such as sodium hydroxide. The analogues of bisphenol A may include, for example 2,2-bis(4'-oxyphenyl)propane (bisphenol A) or its derivatives. The halogenated alkylene oxide may include, for example, epichlorohydrin, 1-chloro-2-methyl-2,3-epoxypropane or the like. In addition, it is also feasible to incorporate a saturated aliphatic dicarboxylic acid such as glutaric acid, adipic acid, pimelic acid, suberic acid, azelaic acid or s
REFERENCES:
patent: 4180405 (1979-12-01), Lawton
patent: 4237207 (1980-12-01), Ceintrey
W. J. Roff (compiler), Handbook of Common Polymers, CRC Press, (The Chemical Rubber Company, 1971), p. 273.
A. Samat et al., "Structure Effect on the Fading Rate of Photochromic 3-Substituted Benzothiazolinic Spiropyrans", The Journal of Physical Chemistry, vol. 76, No. 24, 1972, pp. 3554-3558.
Arakawa Seiichi
Kawasumi Koichi
Seto Junetsu
Hamilton Cynthia
Kittle John E.
Sony Corporation
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