Compositions – Light transmission modifying compositions – Displaying color change
Reexamination Certificate
1999-02-19
2001-03-06
Tucker, Philip (Department: 1721)
Compositions
Light transmission modifying compositions
Displaying color change
C549S389000, C549S331000, C549S060000, C549S058000, C548S525000
Reexamination Certificate
active
06197225
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a novel chromene compound which changes into a colored state upon irradiation with light containing ultraviolet rays such as of sunlight or light of a mercury lamp, the change being reversible, and exhibits excellent fading rate as well as excellent durability in the photochromic property, getting little colored even after it is aged. The invention further relates to a photochromic material, to a chromene composition, to a photochromic composition, to a photochromic polymerizable composition and to a photochromic lens, which contain the chromene compound.
BACKGROUND ART
Photochromism is a phenomenon which is drawing attention in these several years, and stands for a reversible action of a compound; i.e., a compound quickly changes its color when it is irradiated with light containing ultraviolet rays such as of sunlight or light of a mercury lamp, and resumes its initial color when it is no longer irradiated with light and is placed in a dark place. The compound having such a property is called photochromic compound. Though a variety of compounds have heretofore been synthesized, no common feature is particularly recognized among their structures.
U.S. Pat. No. 4,980,089 discloses a chromene compound represented by the following formula (A),
This chromene compound exhibits photochromic properties near room temperature (20 to 30° C.) but exhibits a slow fading rate when it is placed in a dark place after it has developed a color upon being irradiated with ultraviolet rays. When the colors are mixed upon being combined with photochromic compounds having other color tones, such as a fulgimide and a spirooxazine having relatively fast fading rates, the hue changes when the colors fade.
Furthermore, PCT Unexamined Patent Publication WO95/16215 discloses a chromene compound represented by the following formula (B),
wherein B1 is an aminocarbonyl group or an alkoxycarbonyl group, B2 and B3 are hydrogen atoms, alkyl groups, substituted or unsubstituted phenyl groups or alkoxyl groups, m is from 0 to 3, B4 and B5 are substituted or unsubstituted aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted adamantylidene groups, or substituted or unsubstituted norbornylidene groups.
This compound exhibits an increased fading rate compared to the compound disclosed in the above U.S. Pat. No. 4,980,089 but is not still capable of completely preventing a change in the hue when the mixed colors fade. When aged, furthermore, this compound is more colored than when the compound (A) is aged.
PCT Unexamined Patent Publication WO95/16215 further discloses, as a comparative example, a compound represented by the following formula (C),
exhibiting, however, a fading rate nearly the same as that of the above-mentioned compound (A).
As described above, the conventional chromene compounds are not still satisfactory with respect to the fading rate and the color after they are aged.
DISCLOSURE OF THE INVENTION
The object of the present invention therefore is to provide a chromene compound which exhibits improved photochromic property, increased fading rate, and is little colored after it is aged and exhibits excellent durability in the photochromic property compared with those of the conventional chromene compounds.
The present invention was proposed in order to accomplish the above-mentioned object, and is concerned with a chromene compound in which the fifth position of a naphthopyrane ring is substituted by an alkyl group. The chromene compound of the present invention exhibits a large fading rate, permits the hue to change little when the mixed colors are to be faded, is little colored after it is aged, and exhibits excellent durability in the photochromic property.
That is, the present invention is concerned with a chromene compound represented by the following general formula (1),
wherein
R1 is an alkyl group in which a carbon atom bonded to a naphthopyrane ring is a primary carbon atom, a secondary carbon atom or a tertiary carbon atom,
R2 and R3 are substituted or unsubstituted aryl groups or substituted or unsubstituted heteroaryl groups which may be different from each other, or R2 and R3 may be coupled to each other to form a substituted or unsubstituted adamantane ring, a substituted or unsubstituted bicyclononane ring, or a substituted or unsubstituted norbornane ring,
R4 is a substituent,
n is an integer of 0 to 4 representing the number of the substitutents R4 and, when n is 2 or larger, R4 may be the same or different substituents,
R5 is a hydrogen atom or a substituent, and wherein when R1 is an alkyl group in which a carbon atom bonded to the naphthopyrane ring is a primary carbon atom, R2 and R3 may be each a group represented by the following formula (2),
wherein X is an oxygen atom or a sulfur atom, or a group represented by the following formula (3),
wherein R6 is an alkoxyl group or a trifuloromethoxy group, and k is 0 or 1, and R2 and R3 may be different from each other, and at least either R2 or R3 is a group represented by the above formula (3), and R5 is a hydrogen atom.
Other inventions are concerned with a chromene composition containing a chromene compound represented by the above-mentioned general formula (1) and other chromene compounds; a photochromic composition containing a chromene compound represented by the above-mentioned general formula (1), other chromene compounds, a spirooxazine compound and a fulgimide compound; a photochromic polymerizable composition containing a polymerizable monomer and the compositions; and a photochromic lens obtained by curing the photochromic polymerizable composition.
REFERENCES:
patent: 5395566 (1995-03-01), Kobayakawa et al.
patent: 5623005 (1997-04-01), Rickwood et al.
patent: 5658501 (1997-08-01), Kumar et al.
patent: 5808100 (1998-09-01), Momoda et al.
patent: 6096246 (2000-08-01), Chan et al.
patent: 0246114 (1987-11-01), None
patent: 2762840 (1998-11-01), None
patent: 6-306354 (1994-11-01), None
patent: 95/16215 (1995-06-01), None
Research Disclosure, 36144, May 1994, pp. 267-268.
B. Van Gemert, et al., “Naphthopyrans. Structural Features and Photochromic Properties”, Mol. Cryst. Liq. Cryst. 1997, vol. 297, pp. 131-138.
Hara Tadashi
Kawabata Yuichiro
Momoda Junji
Nagoh Hironobu
Tanizawa Tsuneyoshi
Tokuyama Corporation
Tucker Philip
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