Photochromic spiro(indoline)benzoxazines
AssigneePPG Industries, Inc.
InventorsWon S. Kwak, Chin-Wen Chen
Life of this patent
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Abstract
Described are photochromic spiro(indoline)benzoxazine compounds having substituents on the benzoxazine portion of the compound, and their use in plastic hosts to impart a photochromic response thereto.
Claims17
A compound represented by the following graphic formula:
- ##STR9## wherein:
- (a) R.sub.1 is selected from the group consisting of C.sub.1 -C.sub.8 alkyl, phenyl, phen(C.sub.1 -C.sub.4)alkyl, naphth(C.sub.1 -C.sub.4)alkyl, allyl, acrylyl, methacrylyl, C.sub.1 -C.sub.4 acyloxy (C.sub.2 -C.sub.6) alkyl, carboxy (C.sub.2 -C.sub.6) alkyl, cyano(C.sub.2 -C.sub.6)alkyl, hydroxy (C.sub.2 -C.sub.6) alkyl, (C.sub.2 H.sub.4 O).sub.m.CH.sub.3, and mono- and di-substituted phenyl, said phenyl substituents being selected from C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.5 alkoxy, and m is a number from 1 to 6;
- (b) R.sub.2 and R.sub.3 are each selected from the group consisting of C.sub.1 -C.sub.5 alkyl, phenyl, and mono- and di- substituted phenyl, benzyl or combine to form a cyclic ring selected from the group consisting of an alicyclic ring containing from 6 to 8 carbon atoms (including the spiro carbon atoms), norbornyl and adamantyl, said phenyl substituents being selected from C.sub.1 -C.sub.4 alkyl and C.sub.1 -C.sub.5 alkoxy;
- (c) each R.sub.4 is selected from the group consisting of C.sub.1 -C.sub.5 alkyl, halogen, C.sub.1 -C.sub.5 alkoxy, nitro, cyano, C.sub.1 -C.sub.4 monohaloalkyl, C.sub.1 -C.sub.4 polyhaloalkyl, C.sub.1 -C.sub.8 alkoxycarbonyl, and C.sub.1 -C.sub.4 acyloxy;
- (d) each R.sub.5 is selected from the group consisting of halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.5 alkoxy, nitro, cyano, thiocyano, C.sub.1 -C.sub.4 monohaloalkyl, and C.sub.1 -C.sub.2 polyhaloalkyl, and
- (e) the letters "c" and "e" are numbers of from 0 to 4 and 1 to 4 respectively.
7-methoxy-1',3',3',4',5'-pentamethylspiro [2H-1,4-benzoxazine-2,2'-iodoline].
5,7-dimethoxy-1',3',3',4',5'-pentamethylspiro [2H1,4-benzoxazine-2,2'-iodoline).
5,7-dimethoxy-1',3',3'-trimethyl-5'-methoxyspiro [2H-1,4-benzoxazine-2,2'-indoline].
5,7-dimethoxy-1',3'-dimethyl-3,- ethylspiro[2H-1,4-benzoxazine-2,2'-indoline].
5,7-dimethoxy-1'-n-butyl-3',3'-dimethylsp iro[2H-1,4-benzoxazine-2,2'-indoline].
5,7-dimethoxy-,1 -isopropyl-3',3'-dimethyl-5'-methoxyspiro [2H-1,4-benzoxazine-2,2'-indoline].
5-chloro-7 methoxy-1',3',3'(and 6'),5'-pentamethylspiro[2H-1,4-benzoxazine-2,2'-indoline).
5,7-dimethoxy-1',3',3-trimethyl-4'(and 6')-fluoro spiro[2H-1,4-benzoxazine-2,2'-indoline].
5,7-dimethoxy-1',3',3-trimethyl-4'(and 6')-chloro spiro[2H1,4-benzoxazine-2,2'-indoline].
Dependencies are inferred from the claim text.