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US 5,166,345 AGranted
Photochromic compound
AssigneeToray Industries, Inc.
InventorsRyojiro Akashi, Takashi Taniguchi
Life of this patent
Estimating the term…
Abstract
A novel photochromic compound and a polymer comprising the photochromic compound are disclosed. The novel photochromic compound of the present invention is a spirooxazine compound having an addition polymerizable organic functional group or a ring-opening polymerizable organic functional group therein.
Claims6
A photochromic compound comprising a photochromic spirooxazine compound of the formula:
- ##STR10## wherein R.sup.1 represents a radial polymerizable unsaturated group selected from the group consisting of acrylic acid ester, methacrylic acid ester, acrylic acid amide, methacrylic acid amide and vinyl benzoic acid ester, 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 meaning 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.sup.9 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.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 methacryloxyalkyl 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 [I];
- X represents N or CH;
- m' represents an integer of 0-10;
- and n has the same meaning as in formula [I], 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 [I];
- 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 [I];
- R.sup.16 and R.sup.17 are the same or different, and represent an organic amino group, C.sub.1 -C.sub.6 allkoxyl 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, 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.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.120 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 alkoxyl group, carboxyl group, nitro 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 [II], 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.
18 more elements
Dependencies are inferred from the claim text.