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US 5,707,557 AGranted
Photochromic 3H-naphthopyrans
AssigneeOptische Werke G. Rodenstock
InventorsManfred Melzig, Herbert Zinner
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Abstract
Photochromic compounds with a 3H-naphthopyran structure having at least one pyrene moiety in the 3-position, a method for preparing such compounds, and the use of such compounds for producing photochromic articles from an organic synthetic material.
Claims11
A photochromic compound with a 3H-naphthopyran structure having at least one pyrene moiety in position 3, and corresponding to one of the following structures:
- ##STR5## wherein:
- B represents alkyl, alkenyl, vinyl, a carbo- or heterocyclic ring system with one to three rings and 5 to 13 ring atoms and one or two hetero atoms selected from the group N, O and S, in which one or more hydrogen atoms can be replaced with X independently of one another;
- X representing hydroxy, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, phenoxy, C.sub.4 -C.sub.7 -cycloalkyl, halogen or NRR' wherein R and R' independently of one another represent hydrogen or C.sub.1 -C.sub.6 -alkyl, or together form a C.sub.4 -C.sub.7 -cycloalkyl moiety or a 5-7-member heterocyclic ring;
- R.sub.2 and R.sub.4 through R.sub.7 independently represent hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.4 -C.sub.7 -cycloalkyl, halogen or NR"R'" wherein R" and R'" independently of one another represent hydrogen or C.sub.1 -C.sub.6 -alkyl, or together form a C.sub.4 -C.sub.7 -cycloalkyl moiety or a 5-7-member heterocyclic ring, C.sub.1 -C.sub.6 -carboxy(C.sub.1 -C.sub.6)alkyl, --O--(C.sub.1 -C.sub.6)carboxy-(C.sub.1 -C.sub.6)alkyl, cyano, C.sub.1 -C.sub.6 -acyl, C.sub.1 -C.sub.6 -acyloxy, substituted or unsubstituted arylacyloxy, substituted or unsubstituted aryloxy, substituted or unsubstituted aryl, or a 5-6-member substituted or unsubstituted heterocycle, wherein the substituent or substituents of the arylacyloxy, aryloxy or aryl moiety or of the 5-6-member heterocycle are independently selected from C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, C.sub.4 -C.sub.7 -cycloalkyl, halogen and cyano;
- and
- R.sub.3 represents hydrogen, C.sub.1 -C.sub.6 -alkyl, C.sub.5 -C.sub.7 -cycloalkyl, C.sub.1 -C.sub.6 -carboxy(C.sub.1 -C.sub.6)alkyl, --O--(C.sub.1 -C.sub.6)carboxy-(C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 -acyl, C.sub.1 -C.sub.6 -acyloxy, cyano, or halogen.
3 more elements
A method of preparing a photochromic compound comprising the steps of:
- 1) a) reacting a pyrene with an acid chloride corresponding to the formula ##STR6## to form a ketone, wherein B represents alkyl, alkenyl, vinyl, a carbocyclic or heterocyclic ring system with one to three rings and 5 to 13 ring atoms and one or two hetero atoms selected from the group N, O and S, wherein one or more hydrogen atoms can be replaced by X independently of one another, X representing hydroxy, C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, phenoxy, C.sub.4 -C.sub.7 -cycloalkyl, halogen or NRR' wherein R and R' independently represent H or C.sub.1 -C.sub.6 -alkyl, or together form a C.sub.4 -C.sub.7 -cycloalkyl group or a 5-7-member heterocyclic ring;
- or
- b) reacting a pyrenecarboxylic acid to form a pyrenecarboxylic acid chloride, and reacting the pyrenecarboxylic acid chloride with a moiety B, which has at least one aromatic ring, to form a ketone;
- or
- c) reacting a pyrenecarboxylic acid to form a pyrenecarboxylic acid chloride and reacting the pyrenecarboxylic acid chloride with a moiety B, which has at least one p-hydroxyl aromatic group, to form a p-hydroxyketone;
- 2) reacting the ketone obtained in step 1) a), b) or c) with a metal acetylide to form an alkinol, and
- 3) reacting the alkinol obtained in step 2) with a 1-naphthol or a 2-naphthol.
4 more elements
Dependencies are inferred from the claim text.