US 4,792,224 AGranted

Photochromic compound and articles containing the same

AssigneePPG Industries, Inc.

InventorsPatricia L. Kwiatkowski, David A. Hunt

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Abstract

Described are photochromic spiro (oxazolidine) substituted benzoxazine photochromic compounds and their use in plastic hosts to impart a photochromic response thereto. More particularly, there are described spiro (oxazolidine) pyrido benzoxazine and spiro (oxazolidine) naphthoxazine compounds and their use in substrates such as polymerizates of allyl digylcol carbonate.

Claims19

Dependent claims

A compound represented by the following graphic formula:

##STR10## wherein:
(a) R.sub.1 is selected from the group consisting of C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.5 alkenyl, phenyl, benzyl, 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;
(b) R.sub.2, R.sub.2 ', R.sub.3 and R.sub.3 ' are each selected from the group consisting of hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.4 alkoxyalkyl, phenyl, 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;
or R.sub.2 and R.sub.2 ' or R.sub.3 and R.sub.3 ' combine to form a C.sub.3 -C.sub.6 cycloalkyl;
(c) R.sub.4 and R.sub.5 are each selected from the group consisting of hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, phenyl, phenoxy, mono- and di-substituted phenoxy, nitro, cyano, C.sub.1 -C.sub.4 monohaloalkyl, C.sub.1 -C.sub.4 polyhaloalkyl, C.sub.1 -C.sub.4 alkylsulfonyl, trihaloacetyl, benzoyl, benzoyloxy, and C.sub.1 -C.sub.4 acyloxy, said phenoxy substituents being selected from electron donating and electron withdrawing groups;
(d) R.sub.6 is selected from the group consisting of hydrogen C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkoxy-C.sub.1 -C.sub.5 alkoxy, phenoxy, benzyloxy, mono- and di-substituted phenoxy, halogen, C.sub.1 -C.sub.5 thioalkoxy, thiophenoxy, thiobenzyloxy, mono- and di-substituted phenyl and C.sub.1 -C.sub.6 dialkylamino, said phenoxy substituents being selected from electron donating and electron withdrawing groups, and said phenyl substituents being selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.2 alkoxy and C.sub.1 -C.sub.2 dialkylamino groups;
(e) X is nitrogen or carbon;
and
(f) the letters "c" and "e" are numbers from 0 to 4 and 0 to 2 respectively.

6 more elements

An article comprising an organic host material containing a photochromic amount of a photochromic compound represented by the following graphic formula:

##STR11## wherein:
(a) R.sub.1 is selected from the group consisting of C.sub.1 -C.sub.8 alkyl, C.sub.2 -C.sub.5 alkenyl, phenyl, benzyl, 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;
(b) R.sub.2, R.sub.2 ', R.sub.3 and R.sub.3 ' are each selected from the group consisting of hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.4 alkoxyalkyl, phenyl, 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;
or R.sub.2 and R.sub.2 ' or R.sub.3 and R.sub.3 ' combine to form a C.sub.3 -C.sub.6 cycloalkyl;
(c) R.sub.4 and R.sub.5 are each selected from the group consisting of hydrogen, C.sub.1 -C.sub.5 alkyl, C.sub.1 -C.sub.5 alkoxy, phenyl, phenoxy, mono- and di-substituted phenoxy, nitro, cyano, C.sub.1 -C.sub.4 monohaloalkyl, C.sub.1 -C.sub.4 polyhaloalkyl, C.sub.1 -C.sub.4 alkylsulfonyl, trihaloacetyl, benzoyl, benzoyloxy, and C.sub.1 -C.sub.4 acyloxy, said phenoxy substituents being selected from electron donating and electron withdrawing groups;
(d) R.sub.6 is selected from the group consisting of hydrogen C.sub.1 -C.sub.5 alkoxy, C.sub.1 -C.sub.5 alkoxy-C.sub.1 -C.sub.5 alkoxy, phenoxy, benzyloxy, mono- and di-substituted phenoxy, halogen, C.sub.1 -C.sub.5 thioalkoxy, thiophenoxy, thiobenzyloxy, mono- and di-substituted phenyl and C.sub.1 -C.sub.6 dialkylamino, said phenoxy substituents being selected from electron donating and electron withdrawing groups, and said phenyl substituents being selected from C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.2 alkoxy and C.sub.1 -C.sub.2 dialkylamino groups;
(e) X is nitrogen or carbon;
and
(f) the letters "c" and "e" are numbers from 0 to 4 and 0 to 2 respectively.

6 more elements

Dependencies are inferred from the claim text.

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Abstract