Patent FR-2837200-A1 (FR)
Title: New 3H-naphthopyran compounds including a condensed dihydronaphthalene system, used as photochromic compounds in polymeric matrices, e.g. for sunglasses, photochromic glazing and optical devices
Inventor: BREYNE OLIVIER
IPC: C07D311/92
Filed: 2002-03-14
Abstract: 3H-Naphthopyrans (I) with a condensed dihydronaphthalene ring system at positions 5 and 6 are new  Naphthopyran compounds of formula (I) are new. R1, R2  =  1-12C alkyl, 3-12C cycloalkyl, 6-14C aryl or 4-12C heteroaryl (optionally substituted with halogen (especially F, Cl or Br), hydroxyl, 1-12C alkyl or alkoxy (both optionally halogenated, especially fluoroalkyl), phenoxy or naphthoxy (both optionally substituted with 1-12C alkyl or alkoxy), 2-12C alkenyl (especially vinyl or allyl), -NH2, -NHR, -NHCOR, -NR'R'' or (meth)acryloyl, or two of these substituents may form an optionally aromatic ring system with one or two condensed 5- to 7-membered rings optionally containing oxygen, sulfur or nitrogen atom(s), in which the ring(s) may also be substituted with 1-12C alkyl, 1-12C alkoxy, aryl, phenyl or naphthyl groups, or (hetero)aralkyl with 1-4C alkyl groups and aryl or heteroaryl groups as defined above, or R1 and R2 together may form an adamantyl, norbornyl, fluorenylidene, di-(1-6C alkyl)-anthracenylidene or spiro-(5-6C cycloalkyl)-anthracenylidene group (all optionally substituted with groups as listed for (hetero)aryl above);  R3, R4  =  H, OH, 1-12C (preferably 1-6C) alkyl or alkoxy, 3-12C cycloalkyl, phenyl, naphthyl, phenoxy or naphthoxy (all four optionally substituted with 1-12C alkyl), (hetero)aralkyl with 1-4C alkyl groups and (hetero)aryl groups as above, -NH2, -NHR, -CONH2, -CONHR, -NR'R'' or -CONR'R'', or R3 and R4 together form a condensed ring system with 5- to 7-membered rings as above;  R5  =  OH, 1-12C (preferably 1-6C) alkyl or alkoxy, 3-12C cycloalkyl, phenyl or benzyl (optionally substituted as for (hetero)aryl groups in R1 and R2), phenoxy or naphthoxy (both optionally substituted with 1-12C alkyl or alkoxy), -COR, -COOR, -CONHR, -OCOR, -OCOOR or -OCONHR, or two adjacent R5 groups may form a 5- to 7-membered aromatic or non-aromatic ring, optionally with hetero-atom(s), i.e. O, S or N;  R  =  (a) 1-6C alkyl or phenyl (optionally substituted with 1-6C alkyl) (in R1-R4), or (b) 1-6C alkyl, 3-6C cycloalkyl, phenyl or benzyl (optionally substituted as in R1 and R2);  R', R''  =  1-6C alkyl or phenyl (optionally substituted with 1-6C alkyl), or R' plus R'' and the N atom may form a 5- to 7-membered ring (optionally with O, S or N atom(s), the N being optionally substituted with 1-6C alkyl);  m  =  0-3. Independent claims are also included for the following:  (1) preparation of (I); (2) new intermediates of formula (II), not including the compound in which R3 and R4 represent H and m is zero; (3) (co)polymers and/or crosslinked products obtained by polymerization and/or crosslinking and/or grafting of (I); (4) photochromic compositions consisting of (I) or mixtures of different (I) or mixtures of (I) with other types of photochromic and/or non-photochromic pigments; (5) photochromic compositions containing (I) and/or linear or crosslinked (co)polymer(s) with (I) in the structure and optionally other types of photochromic and/or non-photochromic pigments and/or stabilizers; (6)  a matrix containing (I) and/or a composition as in (5) and/or a (co)polymer and/or crosslinked product as in (3); and (7) ophthalmic or sun-screening articles containing (I) and/or a composition as in (5) and/or a (co)polymer or crosslinked product as in (3) and/or a matrix as in (6).