Organic compounds -- part of the class 532-570 series – Organic compounds – Chalcogen in the nitrogen containing substituent
Patent
1995-02-27
1998-09-01
Raymond, Richard L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Chalcogen in the nitrogen containing substituent
544 95, 544101, 544105, C07D26512, C07D26534, C07D26536
Patent
active
058012435
DESCRIPTION:
BRIEF SUMMARY
DESCRIPTION
This application is a 371 of PCT/DE94/00744, filed Jun. 28, 1994.
1. Technical Field
The present invention relates to photochromic compounds, in particular, for the tinting of optical elements made of plastic material.
2. State of the Art
Pyrans are a class of photochromic compounds that have been known for some time and have been extensively investigated. For instance, recently developed photochromic dyes such as the diphenyl-naphthopyrans described in U.S. Pat. No. 5,066,818, the PCT publication WO 92/09593 or U.S. Pat. No. 4,818,096 have within wide bounds adjustable kinetic properties. Their lifetime, i.e. their light stability in continuous use is however insufficient for many applications.
Spiropyrans, which are spiro-linked in the 2-position also show insufficient light stability. This is also the case with the adamantan derivatives described in the U.S. Pat. No. 4,818,096 as well as with the derivatives described in U.S. Pat. No. 5,106,998 principally tricyclic hydrocarbons.
The compounds of the class of indolino-(spirobenz- or naphthoxazines) hitherto preferred for their excellent stability such as those , e.g., described in U.S. Pat. No. 3,652,172, U.S. Pat. No. 3,578,602, U.S. Pat. No. 4,215,010 or U.S. Pat. No. 4,637,698 can be minimally influenced with regard to their darkening and lighting speed.
DESCRIPTION OF THE INVENTION
The object of the present invention is to describe photochromic compounds and to provide a mode of synthesis of these compounds having the advantageous properties of pyrans and, in particular of diphenylnaphthopyrans with a lifetime respectively a light stability comparable to that of oxazines known, in particular, from indolinospironaphtho or indolinospirobenz derivatives.
According to the present invention, the object is solved by the condensation of substituted diphenylacetaldehydes (reacting agent 1) with (substituted) ortho-aminohydroxy aromatic compounds (reacting agent 2). This yields a new class of substances having the needed positive properties. Especially preferred is a halogen or hydroxy group which is located in the .alpha.-position to the aldehyde group and condenses with the hydroxy group of the reacting agent 2 releasing water or halogen hydrogen. One or both phenyl residues may, of course, also be further substituted.
The reaction can also be conducted with (substituted) dinaphthyl derivatives or phenylnaphthyl derivatives as reacting agent 1; heteroaromatic compounds may also be employed.
Both phenyl rings of reacting agent 1 may also be chemically rigidly linked (e.g., fluorene, dibenzosuberone, anthrone, xanthene or thioxanthene derivatives) as was described in an application filed on the same day of the same applicant.
The kinetic properties of the invented compounds may be influenced in an analogous manner to the method according to WO 92/09593 in particular via subtituents in the 2-position of the aromatic rings of reacting agent 1.
The second reacting agent especially preferably possesses an ortho-amino-hydroxy group at an aromatic ring system. This may be another substituted benzene, naphthalene, phenanthrene, anthracene or, by way of illustration, quinoline respectively isoquinoline from the series of heteroaromatic compounds.
Preferred are 1-amino-2-naphtholes, with the kinetic properties being easily influenced by means of suited substitution in the 3-position analog to U.S. Pat. No. 5,066,818.
The condensation itself can be conducted with the free base, the hydrochloride or with modification of the specifications also with by way of illustration amino groups protected by an acetyl group.
Suited as solvents are, in particular, such solvents that form with water a low-boiling azeotrope so that the reaction water can be easily removed, by way of illustration, by means of a Dean-Stark apparatus. The hydrohalogen is extracted or bound, by way of illustration, in an extractor by a stable alkali hydroxide. Depending on the utilized reacting agents, the reaction is preferably catalyzed with a base or an acid (p-toluol-sulfonic acid).
REFERENCES:
patent: 3562172 (1971-02-01), Oho et al.
Grummt et al, Tetrahedron Letters, vol. 22, No. 40, pp. 3945-3948 (1981).
Nakamura et al, Chem. Abstracts 120: 257519p for JP 05-98,252 (Apr. 20, 1993).
Reichenbaecher et al, Chem. Abst. 98: 135279s for DD 156,372 (Aug. 18, 1982).
Reichenbaecher et al, Chem. Abst. 97: 164536h for DD 153,690 (Jan. 27, 1982).
Melzig Manfred
Zinner Herbert
Optische Werke G. Rodenstock
Raymond Richard L.
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