Described are a series of novel benzospiropyran and naphthospiropyran compounds in which a norcamphor group (or its alkyl-substituted homologues) or a tricyclodecane group (or its alkyl-substituted derivatives) are appended at the 2-position of the benzospiropyran or naphthospiropyran ring. Also described are organic host materials that contain or that are coated with materials containing such compounds. Articles, such as ophthalmic or plano lenses, that incorporate the novel pyran compounds or combinations of the novel pyran compounds with other complementary photochromic compounds are described.
Spiropyrone compounds represented by the general formula ##STR1## wherein ##STR2## is a substituted or an unsubstituted aromatic hydrocarbon group or a substituted or an unsubstituted unsaturated heterocyclic group, and ##STR3## is a substituted or an unsubstituted 2-bicyclo[3,3,1]9-nonenylidene group, that are starting materials of spiropyran compounds which change from a colorless state into a colored or a densely colored state upon irradiation with the light containing ultraviolet rays such as the sunlight or the light of a mercury lamp, the change being reversible, and a process for preparing the spiropyrone compounds. The process comprises reacting a compound represented by the general formula ##STR4## wherein ##STR5## is as defined above, with a compound of the general formula ##STR6## wherein ##STR7## is as defined above.
The present invention teaches an ultraviolet active wristband. The ultraviolet active wristband is made of the same materials as any wristband already in the market. However, the present wristband has the intriguing propriety of changing color reversibly from clear to any visible color (violet, blue, red, orange, yellow . . . ) when exposed to an ultraviolet source. The wavelength interval of the ultraviolet source is [250 nm-400 nm]. Therefore, it is also sensitive to the spectrum of ultraviolet sunlight that is [290 nm-400 nm]. The active chemical is a photochromic substance such as spiropyrans, spiroxazines.
A naphthopyran compound of general formula (I) ##STR1## wherein R.sub.1 represents a group of the formula --NR.sub.2 R.sub.3 wherein each of R.sub.2 and R.sub.3, which may be the same or different, independently represents an alkyl group, or a carbocyclic or heterocyclic group, or R.sub.2 and R.sub.3 taken together with the nitrogen atom to which they are attached represent a heterocyclic ring having one or more hetero atoms and which may optionally carry at least one substituent selected from alkyl, aryl, or heteroaryl groups; each of R.sub.4 and R.sub.5, which may be the same or different, independently represents an alkyl, alkenyl, carbocyclic or heterocyclic group, or R.sub.4 and R.sub.5 taken together with the carbon atom to which they are attached form a carboxylcyclic ring or a heterocyclic ring; and R.sub.6 represents a hydrogen atom or a substituent selected from alkyl, alkoxy, aryl, aryloxy, heteroaryl, halogen, a group of formula R.sub.1 as defined above, azo, imino, amide, carboxylate, ester, cyano, trifluoromethyl or nitro, and in addition R.sub.6 may represent a carbocyclic or heterocyclic ring fused to ring A. The naphthopyran compounds of the invention are useful as photochromic materials in lenses, e.g. sunglasses, and photochromic transparencies for cars and aircraft. The invention also provides, as new intermediate compounds, amine-substituted chloro-naphthols and amine-substituted naphthols.
A spiro (indolino) oxazine compound of general formula (I) ##STR1## wherein R.sub.1 represents a group of the formula --NR.sub.2 R.sub.3 wherein each of R.sub.2 and R.sub.3, which may be the same or different, independently represents an alkyl group, or a carbocyclic group, preferably aryl, or a heterocyclic group, or R.sub.2 and R.sub.3 taken together with the nitrogen atom to which they are attached represent a heterocyclic ring having one or more heteroatoms and which may optionally carry at least one substituent selected from alkyl, aryl or heteroaryl groups; --X-- is selected from --O--, --S--, --Se--, --NH-- or --NR-- wherein R represents an alkyl group, and ring A is a carbocyclic or heterocyclic ring which can be optionally substituted with a group of formula R.sub.8 as defined above, or may optionally have a carbocyclic or heterocyclic ring fused thereto; and wherein R.sub.4 -R.sub.8 are as defined in the specification. The spiro (indolino) oxazine compounds of the invention are useful as photochromic materials.
The present invention has for subjects, novel benzopyran derivatives, substituted in position 2 with an adamantyl group as well as the compositions and (co)polymer matrices containing such derivatives. Said derivatives possess interesting photochromic properties.
