Photochromic compound

A photochromic polymer comprising a photochromic spirooxazine compound of the formula:

• ##STR10## wherein R.sup.1 represents an addition polymerizable or a ring-opening polymerizable organic functional group;
• R.sup.2, R.sup.5 and R.sup.6 are the same or different, and represent a hydroxyl group, amino group, organic substituted amino group, C.sub.1 -C.sub.6 alkoxyl group, C.sub.1 C.sub.20 alkyl group, halogen, carboxyl group, C.sub.2 -C.sub.10 acyl group, nitro group or hydrogen;
• R.sup.3 and R.sup.4 are the same or different, and represent a C.sub.1 -C.sub.10 alkyl group, C.sub.7 -C.sub.12 aralkyl group, or R.sup.3 and R.sup.4 cooperatively represent a C.sub.6 -C.sub.8 alicyclic ring with a spiro carbon atom, norbornyl group or adamantyl group;
• m is an integer of 1-30;
• and n is an integer of 0-4, ##STR11## wherein R.sup.1 has the same as in formula;
• [I];
• R.sup.7, R.sup.8 and R.sup.10 are the same or different, and represent an organic substituted amino group, C.sub.1 -C.sub.6 alkoxy group, C.sub.1 -C.sub.20 alkyl group, halogen, carboxyl group, C.sub.2 -C.sub.10 acyl group, nitro group or hydrogen;
• R.sub.9 represents C.sub.1 -C.sub.30 alkyl group, phenyl group, substituted phenyl group, C.sub.7 -C.sub.12 aralkyl group, C.sub.7 -C.sub.12 substituted aralkyl group, C.sub.1 -C.sub.30 hydroxyalkyl group, C.sub.1 -C.sub.30 aminoalkyl group, C.sub.4 -C.sub.30 acryloxyalkyl group, C.sub.4 -C.sub.30 acrylamidoalkyl group, C.sub.5 -C.sub.30 metacryloxyalkyl group or C.sub.5 -C.sub.30 methacrylamidoalkyl group;
• R.sup.3 and R.sup.4 have the same meaning as R.sup.3 and R.sup.4 in formula;
• X represents N or CH;
• m' represents an integer of 0-10;
• and n has the same meaning as in formula, with the proviso that when X is nitrogen, the (CH.sub.2).sub.m' -R.sup.1 group does not bond to this nitrogen atom, ##STR12## wherein R.sup.1 has the same meaning as in formula;
• R.sup.11, R.sup.12 and R.sup.15 are the same or different, and represent an organic substituted amino group, C.sub.1 -C.sub.6 alkoxy group, C.sub.1 -C.sub.20 alkyl group, halogen, carboxyl group, C.sub.2 -C.sub.10 acyl group, hydroxyl group, nitro group, C.sub.1 -C.sub.10 hydroxyalkyl group or hydrogen;
• R.sup.13 and R.sup.14 are the same or different, and represent a C.sub.1 -C.sub.10 alkyl group, aryl group, C.sub.7 -C.sub.12 aralkyl group, or R.sup.13 and R.sup.14 cooperatively represent a C.sub.6 -C.sub.8 alicyclic ring with a spiro carbon atom, norbornyl group or adamantyl group;
• A represents a C.sub.1 -C.sub.30 alkylene group, C.sub.1 -C.sub.30 alkylene(poly)oxyalkylene group, or C.sub.8 -C.sub.20 alkylenearylalkylene group;
• a and b are the same or different, and are 0 or 1 and (a+b) is 1 or 2;
• m' and n have the same meaning as in formula, [II], respectively or ##STR13## wherein R.sup.1 has the same meaning as in formula;
• R.sup.16 and R.sup.17 are the same or different, and represent an organic amino group, C.sub.1 -C.sub.6 alkoxyl group, C.sub.1 -C.sub.20 alkyl group, halogen, carboxyl group, C.sub.2 -C.sub.10 acyl group, cyano group, nitro group or hydrogen;
• R.sup.18 is a C.sub.1 -C.sub.30 alkyl group, phenyl group, substituted phenyl group, C.sub.7 -C.sub.12 aralkyl group or C.sub.7 -C.sub.12 substituted aralkyl group;
• R.sup.19 to R.sup.26 are the same or different and represent a C.sub.1 -C.sub.30 alkyl group, phenyl group, substituted phenyl group, C.sub.7 -C.sub.12 aralkyl group, C.sub.7 -C.sub.12 substituted aralkyl group, C.sub.1 -C.sub.6 alkoxyl group, carboxyl group, nitro group or hydrogen;
• R.sup.27 represents a C.sub.1 -C.sub.30 alkyl group, phenyl group, substituted phenyl group, C.sub.7 -C.sub.12 aralkyl group, C.sub.7 -C.sub.12 substituted aralkyl group, C.sub.1 -C.sub.6 alkoxy group, carboxyl group, or hydrogen;
• Y represents N or C--R.sup.16 (wherein R.sup.16 has the same meaning as mentioned above);
• and m' has the same meaning as in formula, with the proviso that when Y is nitrogen, the --(CH.sub.2).sub.m' R.sup.1 group does not bond to this nitrogen atom,
• said photochromic polymer is prepared by polymerization of said photochromic spirooxazine compound, wherein the polymerization occurs through R.sup.1 of each of formulae [I], [II], [III] and [IV].