Polyalkoxylated naphthopyrans

A naphthopyran compound represented by the following graphic formulae:

• ##STR12## wherein, (a) R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 or R.sub.6 is the group R represented by the formula:
• --A›(C.sub.2 H.sub.4 O).sub.x (C.sub.3 H.sub.6 O).sub.y (C.sub.4 H.sub.8 O).sub.z !D,
• wherein --A is --C(O)O, --CH.sub.2 O or --O, D is C.sub.1 -C.sub.3 alkyl, x, y and z are each a number between 0 and 50, and the sum of x, y and z is between 2 and 50, provided that only one R group is present on the naphtho or indeno portion of said naphthopyran;
• and provided further, that if R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 or R.sub.6 is not R, then:
• (b) R.sub.1 is hydrogen, C.sub.1 -C.sub.3 alkyl or the group, --C(O)W, W being --OR.sub.7, --N(R.sub.8)R.sub.9, piperidino or morpholino, wherein R.sub.7 is allyl, C.sub.1 -C.sub.6 alkyl, phenyl, mono(C.sub.1 -C.sub.6)alkyl substituted phenyl, mono(C.sub.1 -C.sub.6)alkoxy substituted phenyl, phenyl(C.sub.1 -C.sub.3)alkyl, mono(C.sub.1 -C.sub.6)alkyl substituted phenyl(C.sub.1 -C.sub.3)alkyl, mono(C.sub.1 -C.sub.6)alkoxy substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 alkoxy(C.sub.2 -C.sub.4)alkyl or C.sub.1 -C.sub.6 haloalkyl;
• R.sub.8 and R.sub.9 are each selected from the group consisting of C.sub.1 -C.sub.6 alkyl, C.sub.5 -C.sub.7 cycloalkyl, phenyl, mono-substituted phenyl and di-substituted phenyl, said phenyl substituents being C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy, and said halo substituent being chloro or fluoro;
• (c) R.sub.2, each R.sub.3, and R.sub.4 are selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, phenyl, mono-substituted phenyl, di-substituted phenyl and the groups --OR.sub.10 and --OC(O)R.sub.10, wherein R.sub.10 is C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.3)-alkyl, mono(C.sub.1 -C.sub.6)alkyl substituted phenyl(C.sub.1 -C.sub.3)alkyl, mono(C.sub.1 -C.sub.6)alkoxy substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 alkoxy(C.sub.2 -C.sub.4)alkyl, C.sub.3 -C.sub.7 cycloalkyl or mono(C.sub.1 -C.sub.4)alkyl substituted C.sub.3 -C.sub.7 cycloalkyl, said phenyl substituents being C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy, and n is selected from the integers 0, 1 and 2;
• (d) R.sub.5 and R.sub.6 together form an oxo group, a spiro heterocyclic group having 2 oxygen atoms and from 3 to 6 carbon atoms including the spirocarbon atom, or R.sub.5 and R.sub.6 are each hydrogen, hydroxy, C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.7 cycloalkyl, allyl, phenyl, mono-substituted phenyl, benzyl, mono-substituted benzyl, chloro, fluoro, the group, --C(O)X, wherein X is hydroxy, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, phenyl, mono-substituted phenyl, amino, mono(C.sub.1 -C.sub.6)alkylamino, or di(C.sub.1 -C.sub.6)alkylamino, or R.sub.5 and R.sub.6 are each the group, --OR.sub.11, wherein R.sub.11 is C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.3)alkyl, mono(C.sub.1 -C.sub.6)alkyl substituted phenyl(C.sub.1 -C.sub.3)alkyl, mono(C.sub.1 -C.sub.6)alkoxy substituted phenyl(C.sub.1 -C.sub.3)alkyl, C.sub.1 -C.sub.6 alkoxy(C.sub.2 -C.sub.4)alkyl, C.sub.3 -C.sub.7 cycloalkyl, mono(C.sub.1 -C.sub.4)alkyl substituted C.sub.3 -C.sub.7 cycloalkyl, C.sub.1 -C.sub.6 chloroalkyl, C.sub.1 -C.sub.6 fluoroalkyl, allyl, the group, --CH(R.sub.12)Y, wherein R.sub.12 is hydrogen or C.sub.1 -C.sub.3 alkyl and Y is CN, CF.sub.3, or COOR.sub.13 and R.sub.13 is hydrogen or C.sub.1 -C.sub.3 alkyl, or R.sub.11 is the group, --C(O)Z, wherein Z is hydrogen, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, the unsubstituted, mono- or di-substituted aryl groups phenyl or naphthyl, phenoxy, mono- or di-(C.sub.1 -C.sub.6)alkyl substituted phenoxy, mono- or di-(C.sub.1 -C.sub.6)alkoxy substituted phenoxy, amino, mono(C.sub.1 -C.sub.6)alkylamino, di(C.sub.1 -C.sub.6)alkylamino, phenylamino, mono- or di-(C.sub.1 -C.sub.6)alkyl substituted phenylamino, or mono- or di-(C.sub.1 -C.sub.6)alkoxy substituted phenylamino, each of said phenyl, benzyl and aryl group substituents being C.sub.1 -C.sub.6 alkyl or C.sub.1 -C.sub.6 alkoxy;
• and
• (e) B and B' are each selected from the group consisting of:
• (i) mono R-substituted phenyl;
• (ii) the unsubstituted, mono-, di- and tri-substituted aryl groups, phenyl and naphthyl;
• (iii) the unsubstituted, mono- and di-substituted hetroaromatic groups pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazolyl and fluorenyl, each of said aryl and heteroaromatic substituents in (e)(ii) and (iii) being selected from the group consisting of hydroxy, aryl, mono(C.sub.1 -C.sub.6)alkoxyaryl, di(C.sub.1 -C.sub.6)alkoxyaryl, mono(C.sub.1 -C.sub.6)alkylaryl, di(C.sub.1 -C.sub.6)alkylaryl, chloroaryl, fluoroaryl, C.sub.3 -C.sub.7 cycloalkylaryl, C.sub.3 -C.sub.7 cycloalkyl, C.sub.3 -C.sub.7 cycloalkyloxy, C.sub.3 -C.sub.7 cycloalkyloxy(C.sub.1 -C.sub.6)alkyl, C.sub.3 -C.sub.7 cycloalkyloxy(C.sub.1 -C.sub.6)alkoxy, aryl(C.sub.1 -C.sub.6)alkyl, aryl(C.sub.1 -C.sub.6)alkoxy, aryloxy, aryloxy(C.sub.1 -C.sub.6)alkyl, aryloxy(C.sub.1 -C.sub.6)alkoxy, mono- and di-(C.sub.1 -C.sub.6)alkylaryl(C.sub.1 -C.sub.6)alkyl, mono- and di-(C.sub.1 -C.sub.6)alkoxyaryl(C.sub.1 -C.sub.6)alkyl, mono- and di-(C.sub.1 -C.sub.6)alkylaryl(C.sub.1 -C.sub.6)alkoxy, mono- and di-(C.sub.1 -C.sub.6)alkoxyaryl(C.sub.1 -C.sub.6)alkoxy, amino, mono(C.sub.1 -C.sub.6)alkylamino, di(C.sub.1 -C.sub.6)alkylamino, diarylamino, N-(C.sub.1 -C.sub.6)alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, arylpiperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrryl, C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 chloroalkyl, C.sub.1 -C.sub.6 fluoroalkyl, C.sub.1 -C.sub.6 alkoxy, mono(C.sub.1 -C.sub.6)alkoxy(C.sub.1 -C.sub.4)alkyl, acryloxy, methacryloxy, bromo, chloro and fluoro;
• (iv) the groups represented by the following graphic formulae:
• ##STR13## wherein E is carbon or oxygen and G is oxygen or substituted nitrogen, provided that when G is substituted nitrogen, E is carbon, said nitrogen substituents being selected from the group consisting of hydrogen, C.sub.1 -C.sub.6 alkyl and C.sub.2 -C.sub.6 acyl;
• each R.sub.14 is C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkoxy, hydroxy, chloro or fluoro;
• R.sub.15 and R.sub.16 are each hydrogen or C.sub.1 -C.sub.6 alkyl;
• and q is the integer 0, 1 or 2;
• (v) C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 chloroalkyl, C.sub.1 -C.sub.6 fluoroalkyl, C.sub.1 -C.sub.6 alkoxy(C.sub.1 -C.sub.4)alkyl;
• and
• (vi) the group represented by the following graphic formula:
• ##STR14## wherein L is hydrogen or C.sub.1 -C.sub.4 alkyl and M is selected from the unsubstituted, mono-, and di-substituted members of the group consisting of naphthyl, phenyl, furanyl and thienyl, each of said group substituents being C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, fluoro or chloro.