Photochromic dichroic naphtho-pyrans and optical articles containing them

1. A naphthopyran compound represented by the formulae (I) to (II)

wherein:

m 1 is an integer comprised from 0 to 5 inclusive;

m 2 is an integer comprised from 0 to 5 inclusive;

p is an integer comprised from 0 to 4 inclusive;

q is equal to 0

R 1 , R 2 and R 4 , identical or different, independently from each other, represent a group selected from halogen, H, —R a , aryl, —OH, —OR a , —SH, —SR a , —NH 2 , —NR a R a1 , —NR b R c , —NR a1 COR a , —NR a1 CO(aryl), —NR a1 aryl, —N-aryl 2 , —N(aryl)CO(aryl), —CO 2 R a , —CO 2 R a1 , —OC(O)—R d , and —X—(R e )—Y, and linear or branched (C 1 -C 18 ) perfluoroalkyl group, wherein:

R a represents a linear or branched (C 1 -C 18 ) alkyl group or linear or branched (C 1 -C 18 ) perfluoroalkyl group;

R a1 represents a group selected from hydrogen, linear or branched (C 1 -C 18 ) alkyl group, and linear or branched (C 1 -C 18 ) perfluoroalkyl group;

R b and R c ,

together and in combination with the nitrogen atom, represent a saturated 5 to 7 membered heterocyclic group which comprises optionally one additional heteroatom selected from O, N and S, and which may be optionally substituted by one or two group(s), identical or different, selected from halogen, —R a , —OH, —OR a , —NH 2 , and —NR a R a1 , wherein R a and R a1 are as defined hereinbefore,

or together and in combination with the nitrogen atom and the adjacent phenyl group form a heterocyclic group of formula (A), (B), (C) or (D) wherein t is an integer comprised from 0 to 2 inclusive, and R a and R a1 are as defined hereinbefore:

X represents a group selected from oxygen atom, —N(R a1 )—, sulphur atom, —S(O)— and —S(O 2 )— wherein R a1 is as defined hereinbefore;

Y represents a group selected from —OR a1 , —NR a1 R a2 , and —SR a1 wherein R a1 is as defined hereinbefore and R a2 represent a group selected from hydrogen and linear or branched (C 1 -C 18 ) alkyl group;

R e represents a linear or branched (C 1 -C 18 ) alkylene group, which may be optionally substituted by a group selected from halogen, hydroxyl, linear or branched (C 1 -C 6 ) alkoxy, and amino;

R d represents a group selected from linear or branched (C 1 -C 18 ) alkyl group, linear or branched (C 1 -C 18 ) perfluoroalkyl group, —(R e )—Y, and aryl group which is optionally substituted by 1 to 4 groups selected from halogen, —R a , —OH, —OR a , —SH, —SR a , —NH 2 , —NR a R a1 , —NR b R c , —CO—R a , —CO 2 R a1 wherein R a , R a1 , R b , R c , R d , R e and Y are as defined hereinbefore;

Z 1 represent a group selected from:

wherein:

R 3 represents a group selected from halogen, —R a , —OH, —OR a , —SH, —SR a , —NH 2 , and —NR a R a1 , each or R 3 being identical or different;

J is selected from O, S, NRa 1 , wherein R a1 is as defined hereinbefore;

n is an integer comprised from 0 to 6 inclusive;

Z 2 represents a group selected from H, halogen, —R a , —OH, —OR a , —SH, —SR a , —NH 2 , —NR a R a1 , —CO—R a , —CO 2 R a1 , and —O—Z—R 6 ,

wherein R a and R a1 are as defined hereinbefore;

R 6 represents a group selected from:

—R a which may be optionally substituted by a group selected from halogen, —OH, —OR a , —SH, —SR a , —NH 2 , —NR a R a1 , —CO—R a , and —CO 2 R a1 , wherein R a and R a1 are as defined hereinbefore;

cycloalkyl, heterocycloalkyl, aryl, heteroaryl, which may be optionally substituted by 1 to 4 groups selected from halogen, —OH, —OR a , —SH, —SR a , —NH 2 , —NR a R a1 , —CO—R a , —O—C(O)—R a and —CO 2 R a1 ,

Z represents a group selected from CO, CS, SO, SO 2 , CO 2 , C(O)S, CS 2 , C(O)NH, C(O)NR a , C(S)NH, C(S)NR a and C═NR a , wherein R a is as defined hereinbefore

Z 3 represents a group selected from hydrogen, —CO 2 R a1 , CHO, —CH 2 OH, —CH 2 OR a1 , —CR a R a1 OH, —R a1 , and linear or branched (C 2 -C 18 ) alkenyl;

with the provision that for compounds of formula (II) when Z 1 represents a group

then Z 3 is not a hydrogen.

2. The naphthopyran compound according to claim 1 , wherein Z 1 represent a group selected from:

3. The naphthopyran compound of claim 1 , selected from one of the following compounds:

Methyl 6-(4′-dodecyloxybiphenyl-4-yl)-2-phenyl-2-(4-pyrrolidinophenyl)-2H-naphtho[1,2-b]pyran-5-carboxylate;

Methyl 2-(4-diethylaminophenyl)-2-phenyl-6-(4′-pentylbiphenyl-4-yl)-2H-naphtho[1,2-b]pyran-5-carboxylate;

Methyl 6-(4′-pentylbiphenyl-4-yl)-2-phenyl-2-(4-pyrrolidinophenyl)-2H-naphtho[1,2-b]pyran-5-carboxylate;

6-[(4-Dibutylaminophenyl)ethynyl]-3-phenyl-3-(4-pyrrolidinophenyl)-3H-naphtho[2,1-b]pyran;

3-(2-Fluorophenyl)-6-(5-phenyl-2-thienyl)-3-(4-pyrrolidinophenyl)-3H-naphtho[2,1-b]pyran.