Compositions – Light transmission modifying compositions – Displaying color change
Patent
1998-08-26
2000-08-29
Tucker, Philip
Compositions
Light transmission modifying compositions
Displaying color change
548407, G02B 523, C07D20700
Patent
active
061104000
DESCRIPTION:
BRIEF SUMMARY
TECHNICAL FIELD
The present invention relates to a novel fulgimide compound having a photochromic action and to its use. More specifically, it relates to a novel fulgimide compound which changes its color from a colorless state to a colored state, the color change being reversible, when irradiated with a light containing ultraviolet rays, such as sunlight or light from a mercury lamp, and which has excellent durability, and to its use.
BACKGROUND ART
Photochromism is a phenomenon which has drawn attention for the last several years, and refers to a reversible action in which a certain compound rapidly changes its color when irradiated with a light containing ultraviolet rays, such as sunlight or light from a mercury lamp and returns to its original color when the irradiation is stopped and the compound is placed in a dark place. Compounds having this property are called photochromic compounds. Photochromic compounds of various structures have been synthesized and proposed, but no particular common skeleton has been observed in the structures.
Understanding the above background, JP-A Sho 60-155179 discloses a photochromic compound represented by the following general formula: ##STR4## [wherein the group ##STR5## is an aromatic group, an unsaturated heterocyclic group, or a heterocyclic group in which a benzene ring is fused; and or a heterocyclic group; ##STR6## (wherein R is a hydrogen atom, an aryl group, an alkyl group or an aralkyl group)] and its use in a photoreactive lens. specific photochromic compound: ##STR7##
Also, JP-A Hei 2-28154 and U.S. Pat. No. 4,882,438 corresponding thereto disclose a fulgide or fulgimide compound represented by the following general formula: ##STR8## [wherein the group ##STR9## is a divalent aromatic hydrocarbon group or a divalent unsaturated heterocyclic group each of which may have a substituent (s); R.sup.5 is a monovalent hydrocarbon group or a monovalent heterocyclic group each of which may have a substituent(s); the group ##STR10## is a norbornylidene group or an adamantylidene group each of which may have a substituent(s); and Y' is an oxygen atom, ##STR11## The fulgide or fulgimide compound has an excellent photochromic property because it remains stably colorless under normal condition, quickly develops a color when irradiated with sunlight or ultraviolet rays, returns to a colorless state when the irradiation is stopped, and repeats the above color change with good durability. The following compound is disclosed in the Examples of this literature as a specific fulgide or fulgimide compound: ##STR12##
TECHNICAL PROBLEMS TO BE SOLVED BY THE INVENTION
The above fulgide or fulgimide compound is, as mentioned above, an excellent photochromic compound in that it repeats reversible color change between coloration and discoloration with good durability. The compound, however, must be used in a large amount to give a sufficiently high color density in a color-developing state. Consequently, as the compound deteriorates in proportional to the amount used, the color of the compound is not sufficiently removed in a conversion to a colorless state, with the result that the color still remains, which is a problem.
DISCLOSURE OF THE INVENTION
It is therefore an object of the present invention to provide a novel fulgimide compound which is useful as a photochromic compound.
It is another object of the present invention to provide a fulgimide compound which gives a sufficiently high color density in a color-developing state.
It is still another object of the present invention to provide a fulgimide compound which gives a sufficiently high color density for practical application even in a small amount.
A study conducted by the present inventors has revealed that the above objects of the present invention could be achieved by a fulgimide compound represented by the following general formula (I): ##STR13## [wherein the group (a) ##STR14## is a divalent aromatic hydrocarbon group or a divalent unsaturated heterocyclic group each of which may have a substituent(s); ##STR15
REFERENCES:
patent: 4882438 (1989-11-01), Tanaka et al.
patent: 5130058 (1992-07-01), Tanaka et al.
patent: 5683628 (1997-11-01), Mizuno et al.
Momoda Junji
Nagoh Hironobu
Tanizawa Tsuneyoshi
Tokuyama Corporation
Tucker Philip
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