Photochromic naphthopyran compounds: compositions and articles containing those naphthopyran compounds

A photochromic naphthopyran having a central nucleus of the formula:

• wherein F is a dihydrofuran group fused to the g, h, or i side;
• R1 and R2 are the atoms or groups providing photochromic properties to the naphthopyran, and the 13-position may be substituted
• wherein the 13-position has substituents R3 and R4, wherein R3 and R4 individually represent
• a hydrogen atom,
• a hydroxy group,
• a halogen atom,
• a linear, branched, or cyclic C1–C6 alkyl, alkenyl, or alkynyl group,
• a linear, branched, or cyclic C1–C6 alkoxy or alkenoxy group,
• an amino group:
• in which R8 and R9, which are the same or different, independently representing a hydrogen, a linear, branched, or cyclic alkyl group comprising 1 to 6 carbon atoms, an aryl or heteroaryl group, or representing (together with the nitrogen atom to which they are bound) a 5- to 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulfur and nitrogen, said nitrogen being optionally substituted with an R10 group, which is a linear or branched alkyl group comprising 1 to 6 carbon atoms, a phenyl, a benzyl, or a naphthyl,
• an aryl or heteroaryl group selected from the group consisting of phenyl, naphthyl, phenanthryl, pyrenyl, quinolyl, isoquinolyl, benzofuranyl, thienyl, benzothienyl, dibenzofuranyl, dibenzothienyl, carbazolyl, indolyl,
• a mono-substituted phenyl having a substituent at the para position that is a linking group, —(CH2)t— or —O—(CH2)t—, wherein t is the integer 1, 2, 3, 4, 5 or 6, connected to an aryl group, which is a member of another photochromic naphthopyran,
• an aralkyl or heteroaralkyl group, the alkyl part of which is linear or branched, comprising 1 to 4 carbon atoms,
• a —C(O)R11, —OC(O)R11, or COOR11 group, wherein R11 is hydrogen, hydroxy, linear or branched C1–C6 alkyl, linear or branched C1–C6 alkoxy, phenyl, mono-substituted phenyl, naphthyl, mono-substituted naphthyl, amino, mono(C1–C6) alkylamino or di(C1–C6)alkylamino, e.g., N,N-dimethyl amino, N-methyl-N-propyl amino, morpholino, piperidino or pyrrolidyl, said amino substituents being selected from the group consisting of C1–C6 alkyl, phenyl, benzyl and naphthyl, and said benzyl and phenyl substituents being C1–C6 alkyl or C1–C6 alkoxy,
• a group —OR12, wherein R12 is a C1–C6 acyl, an aralkyl or heteroaralkyl group with a C1–C3 alkyl portion, a (C3–C7)cycloalkyl group, a (C2–C4)alkyl group, or R12 is the group, —CH(R13)R14, wherein R13 is hydrogen or C1–C3 alkyl and R14 is —CN, —CF3, or —COOR15, wherein R15 is hydrogen or linear, branched, or cyclic alkyl, aralkyl or heteroaralkyl,
• a group —CH(R16)2 wherein R16 is —CN or —COOR15,
• a group CH(R15)R17, wherein R17 is —COOR11, —C(O)R18 or —CH2OR19, wherein R18 is hydrogen, linear, branched, or cyclo-alkyl, aryl groups, amino group of formula
• R19 is hydrogen, —C(O)R11, alkyl, alkoxyalkyl, phenylalkyl, mono-alkoxy substituted phenyl-alkyl, or aryl groups,
• a polyether, polyamide, polycarbonate, polycarbamate, polyurea, polyester residue, or a group ended by a polymerizable residue;
• or R3 and R4 may together form a 3- to 7-member spiro-cyclic ring which can comprise at least one heteroatom selected from oxygen, sulfur, and nitrogen.