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Photochromic spiro(indoline)naphthoxazine compounds

  • US 5,405,958 A
  • Filed: 12/21/1992
  • Issued: 04/11/1995
  • Est. Priority Date: 12/21/1992
  • Status: Expired due to Term
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1. A naphthoxazine compound represented by the following graphic formula:

  • ##STR4## wherein;

    (a) R1 is C1 -C8 alkyl, phen(C1 -C4)alkyl, naphth (C1 -C4)alkyl, allyl, acrylyloxy(C2 -C6 )alkyl, methacrylyloxy(C2 -C6 )alkyl, C1 -C4 acyloxy(C2 -C6 )alkyl, carboxy(C2 -C6 )alkyl, cyano(C2 -C6 )alkyl, hydroxy(C2 -C6 )alkyl, C1 -C6 alkoxy(C2 -C4)alkyl or (C2 H4 O)m.CH3, wherein m is an integer from 1 to 6;

    (b) each R2 is C1 -C5 alkyl, C1 -C5 alkoxy, nitro, cyano, C1 -C8 alkoxycarbonyl, C1 -C4 acyloxy, halo, C1 -C4 monohaloalkyl or C1 -C4 polyhaloalkyl;

    (c) R3 and R4 are each C1 -C5 alkyl, benzyl, phenyl, mono- or di-substituted phenyl, said phenyl substituents being C1 -C5 alkyl or C1 -C5 alkoxy, or R3 and R4 taken together form a group selected from a cyclic ring of from 5 to 8 carbon atoms which includes the spiro carbon atom, norbornyl or adamantyl;

    (d) R5 is the group --C(O)X, X being --OR7 or --N(R8)R9, wherein R7 is allyl, C1 -C6 alkyl, benzyl, C1 -C6 alkyl substituted benzyl, C1 -C6 alkoxy substituted benzyl, C1 -C6 alkoxy(C2 -C4)alkyl, or C1 -C6 haloalkyl, and wherein R8 and R9 are each selected from hydrogen, C1 -C5 alkyl, C5 -C7 cycloalkyl, phenyl and substituted phenyl, or R8 and R9 together with the nitrogen form a substituted or unsubstituted saturated heterocyclic ring containing from 5 to 6 ring atoms, which ring includes as the hetero atom said nitrogen atom alone or one additional hetero atom of nitrogen or oxygen, said phenyl and heterocyclic ring substituents being selected from C1 -C5 alkyl and C1 -C6 alkoxy;

    (e) R6 is the group, --O--Y, wherein Y is hydrogen, C1 -C6 alkyl, benzyl, C1 -C6 alkyl substituted benzyl, C1 -C6 alkoxy substituted benzyl, C1 -C6 alkoxy (C2 -C4) alkyl, C1 -C6 haloalkyl, allyl or the group, --C(O)Z, wherein Z is C1 -C6 alkyl, phenyl, C1 -C6 alkyl substituted phenyl, C1 -C6 alkoxy substituted phenyl, C1 -C6 alkoxy, phenoxy, C1 -C6 alkyl substituted phenoxy, C1 -C6 alkoxy substituted phenoxy, C1 -C6 alkylamino, phenylamino, C1 -C6 alkyl substituted phenylamino, or C1 -C6 alkoxy substituted phenylamino; and

    (f) n is the integer 0, 1, or 2, said halo substituents being chloro, fluoro, iodo or bromo.

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