Chromene compounds

Details Chromene compounds Chromene compounds

2001-04-30

2002-10-22

Ramsuer, Robert W. (Department: 1626)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

C524S087000, C524S089000, C524S107000, C525S185000, C525S186000, C525S330300, C525S330500, C526S328000, C544S070000, C549S060000, C549S331000

Reexamination Certificate

active

06469076

ABSTRACT:

TECHNICAL FIELD
The present invention relates to a novel chromene compound and to a photochromic polymerizable composition containing the chromene compound.
The invention further relates to a photochromic material containing the chromene compound and, particularly, to a photochromic optical material.
BACKGROUND ART
Photochromism is a phenomenon that is drawing attention in these several years, and is a reversible action of a compound which quickly changes its color when it is irradiated with light containing ultraviolet rays such as sunlight or light of a fluorescent lamp 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 without, however, any particular common nature in their structures.
The specification of PCT Patent Application Laid-Open Specification WO 96/14596 discloses a chromene compound represented by the following formula (A),
This chromene compound, however, has a small color fading rate, is colored to a considerable degree (also called coloring after aged) in a state of not being irradiated with light after it is used as a photochromic material for extended periods of time, and loses color density when it is irradiated with light.
Further, the specification of PCT Patent Application Laid-Open Specification WO 97/48762 discloses a chromene compound represented by the following formula (B),
This chromene compound, however, has a problem of a low fading rate.
Further, Examples 4, 7 and 5 of German Patent Application Laid-Open DE 19902771 A1 disclose chromene compounds represented by the following formulas (C), (D) and (E).
However, these chromene compounds have low color-developing sensitivities, and their fading rates are not of satisfactory levels, either.
The compounds disclosed in the above-mentioned publications exhibit bluish color tones by themselves. When it is desired to obtain neutral tints such as grey and brown that are preferred in, for example, the photochromic lenses, it is necessary to use in combination other photochromic compounds that exhibit yellow or red color tones.
DISCLOSURE OF THE INVENTION
It is therefore an object of the present invention to provide a chromene compound which by itself develops a color tone of a neutral tint, exhibits further improved photochromic properties compared with the above-mentioned compounds, exhibits a fast fading rate, shows less color after aged, permits a small decrease in the photochromic properties as represented by a decrease in the color density, i.e., exhibits excellent photochromic fatigue resistance.
The present invention was proposed to accomplish the above object, and a novel chromene compound was completed by the present inventors based on a knowledge that it exhibits a color tone of a neutral tint by itself, exhibits a fast fading rate, is colored little after aged, and exhibits excellent photochromic fatigue resistance.
That is, the present invention is concerned with a chromene compound represented by the following general formula (1),
wherein a divalent group represented by the following formula (2),
and a divalent group represented by the following formula (3),
are aromatic hydrocarbon groups or unsaturated heterocyclic groups independently from each other;
a substituent R1 of the group represented by the above formula (2) is an alkyl group, a hydroxyl group, an alkoxyl group,an aralkoxyl group, an amino group, a substituted amino group, a cyano group, a nitro group, substituted or unsubstituted aryl group, a halogen atom, a trifluoromethyl group, an aralkyl group, a monovalent heterocyclic group bonded to the ring of the group represented by the above formula (2) through the carbon atom, a monovalent substituted or unsubstituted heterocyclic group having a nitrogen atom as a hetero atom and bonded to the ring of the group represented by the above formula (2) through said nitrogen atom, or a monovalent condensed heterocyclic group in which said heterocyclic group is condensed with an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and p is an integer of 0 to 3;
a substituent R2 of the group represented by the above formula (3) is an alkyl group, a hydroxyl group, an alkoxyl group, an aralkoxyl group, an amino group, a substituted amino group, a cyano group, a nitro group, substituted or unsubstituted aryl group, a halogen atom, a trifluoromethyl group, an aralkyl group, a monovalent heterocyclic group bonded to an indene ring through the carbon atom, a monovalent substituted or unsubstituted heterocyclic group having a nitrogen atom as a hetero atom and bonded to the ring of the group represented by the above formula (3)through said nitrogen atom, or a monovalent condensed heterocyclic group in which said heterocyclic group is condensed with an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and q is an integer of 0 to 3;
a substituent R3 of the indene ring is an alkyl group, a hydroxyl group, an alkoxyl group, an aralkoxyl group, an amino group, a substituted amino group, a cyano group, a nitro group, substituted or unsubstituted aryl group, a halogen atom, a trifluoromethyl group, an aralkyl group, a monovalent heterocyclic group bonded to the indene ring through the carbon atom, a monovalent substituted or unsubstituted heterocyclic group having a nitrogen atom as a hetero atom and bonded to the indene ring through said nitrogen atom, or a monovalent condensed heterocyclic group in which said heterocyclic group is condensed with an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and r is an integer of 0 to 3;
a substituent R4 of the pyran ring is an alkyl group, a hydroxyl group, an alkoxyl group, an aralkoxyl group, an amino group, a substituted amino group, a cyano group, a nitro group, a substituted or unsubstituted aryl group, a halogen atom, a trifluoromethyl group, an aralkyl group a monovalent heterocyclic group bonded to the pyran ring through the carbon atom, is a monovalent substituted or unsubstituted heterocyclic group having a nitrogen atom as a hetero atom and bonded to the pyran ring through said nitrogen atom, or a monovalent condensed heterocyclic group in which said heterocyclic group is condensed with an aromatic hydrocarbon ring or an aromatic heterocyclic ring, and s is an integer of 0 to 3;
each of R5 and R6 is, independently from each other, groups represented by the following formula (4),
wherein R7 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heteroaryl group, R8 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 (5),
wherein R9 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, substituted or unsubstituted heteroaryl group, or an alkyl group, wherein R5 and R6 together may constitute an aliphatic hydrocarbon ring or an aromatic hydrocarbon ring.
As represented by the above general formula (1), the chromene compound of the present invention has a basic structure in which:
{circle around (1)} a condensed ring which is formed by bonding a divalent group represented by the above general formula (2) to the pyran ring at it's fifth and sixth position is spiro-bonded to the indene ring at it's first position;
{circle around (2)} a divalent group represented by the above formula (3) is bonded to carbon atoms at the fifth and sixth positions of the chromene ring to form a condensed ring; and
{circle around (3)} particular substituents represented by R5 and R6 are bonded to a carbon atom at the second position of the chromene compound.
The above-mentioned excellent effects are obtained by the combination of the above three features.
In particular, the chromene compound of the present invention is preferably the one represented by the following general formula (6),
wherein a divalent group represented by the following formula (2),

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