Organic compounds -- part of the class 532-570 series – Organic compounds – Heterocyclic carbon compounds containing a hetero ring...
Reexamination Certificate
2001-10-15
2004-04-20
Solola, Taofiq (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Heterocyclic carbon compounds containing a hetero ring...
C549S330000
Reexamination Certificate
active
06723859
ABSTRACT:
TECHNICAL FIELD
The present invention relates to novel chromene compounds and the use of the chromene compounds.
BACKGROUND ART
Photochromism is a reversible action of a compound which quickly changes its color when it is irradiated with light containing ultraviolet rays and resumes its initial color when it is no longer irradiated with light but is placed in a dark place. The compound having this property is called photochromic compound. Various compounds have so far been synthesized. Among these photochromic compounds, the chromene compounds exhibit good light resistance and develop colors of a wide variety of tones such as yellow color to blue color, and have been vigorously studied in recent years. Some of the chromene compounds that are developed have already been put into practice as photochromic materials for organic photochromic lenses.
The organic photochromic lens stands for a lens that develops color in an environment where it is irradiated with ultraviolet rays such as outdoors and can be used as sunglasses, and loses its color and returns to its colorless or slightly tinted state in an environment where it is irradiated with weak ultraviolet rays, such as indoors. The organic photochromic lens must satisfy such requirements that it develops a color quickly and densely upon the irradiation with ultraviolet rays and quickly loses color upon the interruption of ultraviolet rays, that it is not colored after faded, and that it exhibits excellent light resistance.
Some chromene compounds found so far exhibit excellent photochromic properties, such as quick color developing/fading rate and a high color density in a solution. When dispersed in a high-molecular matrix such as a plastic material, however, the chromene compound fails to exhibit its intrinsic excellent photochromic properties to a sufficient degree arousing such problems as decreased color density, decreased fading rate and decreased light resistance. These problems appear conspicuously when the chromene compound is dispersed in a rigid high-molecular matrix, deteriorating the fading rate to a conspicuous degree. No method for effectively solving the above problems has been known, and no chromene compound has, either, been known which can be dispersed in a plastic lens that must have a large strength and a hardness to exhibit photochromic properties to a sufficient degree.
For example, the specification of PCT Patent Application WO96/14596 discloses a chromene compound represented by the following formula (A),
When dispersed in a high molecular matrix, however, the above chromene compound exhibits a low color-developing sensitivity, a low fading rate, and is colored (also called coloring upon deterioration) even in a state of not irradiated with light when it is used as, for example, a photochromic material for extended periods of time and, further, develops color of a decreased density when irradiated with light.
The specification of PCT Patent Application WO97/48762 discloses a chromene compound represented by the following formula (B),
However, this chromene compound, too, has a problem of slow fading rate when it is dispersed in a high-molecular matrix.
Further, German Application Publication DE19902771A1 discloses a chromene compound represented by the following formula (C),
When dispersed in a high-molecular matrix, however, the above chromene compound exhibits a fading rate which is not of a satisfactory level.
U.S. Pat. No. 6,113,814 discloses a chromene compound represented by the following formula (D),
having a polyalkyleneoxy group with a polymerizable group bonded to one terminal thereof so as to be copolymerizable with a monomer that serves as a high-molecular matrix. This compound, however, has a problem of slow fading rate when it is copolymerized with a monomer that imparts a high hardness or is dispersed in a high-molecular matrix having a high hardness.
DISCLOSURE OF THE INVENTION
It is therefore an object of the present invention to provide a chromene compound which, when dispersed in a high-molecular matrix, exhibits further improved photochromic properties, a high color-developing sensitivity, a high fading rate, less color upon deterioration, and permits photochromic properties to be deteriorated little that is represented by a drop in the color density, i.e., exhibits photochromic properties maintaining excellent light resistance.
The present inventors have conducted keen study in an effort to develop a chromene compound that exhibits excellent photochromic properties in a high molecular matrix. As a result, the inventors have discovered a novel chromene compound which exhibits a high color-developing sensitivity and a high color density even when it is dispersed in a high-molecular matrix, and exhibits a high fading date, less color upon deterioration and exhibits photochromic properties maintaining excellent light resistance, and have completed the present invention.
That is, the present invention is concerned with a chromene compound represented by the following general formula (1),
wherein a group represented by the following formula (2),
is an aromatic hydrocarbon group or an unsaturated heterocyclic group;
R
1
is a hydroxyl group, an alkyl group, a trifluoromethyl group, an alkoxy group, an alkoxycarbonyl group, a carboxyl group, an alkoxymethyl group, a hydroxymethyl group, an aralkoxy group, an amino group, a substituted amino group, a cyano group, a nitro group, a halogen atom, an aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heterocyclic group having a nitrogen atom as a hetero atom and in which the nitrogen atom and an indene ring are coupled together, or a condensed heterocyclic group in which the heterocyclic group is condensed with an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and p is an integer of 0 to 3;
R
2
is a hydroxyl group, an alkyl group, a trifluoromethyl group, an alkoxy group, an alkoxycarbonyl group, a carboxyl group, an alkoxymethyl group, a hydroxymethyl group, an aralkoxy group, an amino group, a substituted amino group, a cyano group, a nitro group, a halogen atom, an aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, a substituted or unsubstituted heterocyclic group having a nitrogen atom as a hetero atom and in which the nitrogen atom and a ring of the group represented by the above formula (2) are bonded together, or a condensed heterocyclic group in which the heterocyclic group is condensed with an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and q is an integer of 0 to 3;
R
3
and R
4
are, independently from each other, a group represented by the following formula (3),
wherein R
5
is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, R
6
is a hydrogen atom, an alkyl group or a halogen atom, and n is an integer of 1 to 3,
a group represented by the following formula (4)
wherein R
7
is a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, and m is an integer of 1 to 3,
a substituted or unsubstituted aryl group, a substituted or unsubstituted heteroaryl group, or an alkyl group, or R
3
and R
4
together may constitute an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring; and
a cyclic group spiro-bonded to the first position of an indene ring represented by the following formula (5),
is an aliphatic hydrocarbon cyclic group which is an unsubstituted monocyclic ring having 7 to 20 carbon atoms in the ring, an aliphatic hydrocarbon cyclic group which is a monocyclic ring having 4 to 20 carbon atoms in the ring and has at least one substituent selected from alkyl group, alkoxy group, amino group, substituted amino group, substituted or unsubstituted aralkyl group and substituted or unsubstituted aryl group, a crosslinked cyclic spiro-cyclic aliphatic hydrocarbon cyclic group which may have at least one substituent selected from the group consisting of alkyl gr
Izumi Shinobu
Kawabata Yuichiro
Momoda Junji
Nagoh Hironobu
Takeda Yasuko
Sherman & Shalloway
Tokuyama Corporation
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