| US 7,556,750 B2 | ||
| Photochromic materials with reactive substituents | ||
| Wenjing Xiao, Murrysville, Pa. (US); and Barry Van Gemert, Pitcairn, Pa. (US) | ||
| Assigned to Transitions Optical, Inc., Pihellas Park, Fla. (US) | ||
| Filed on Apr. 08, 2005, as Appl. No. 11/102,280. | ||
| Prior Publication US 2006/0226400 A1, Oct. 12, 2006 | ||
| Int. Cl. G02B 5/23 (2006.01); G03C 1/00 (2006.01) | ||
| U.S. Cl. 252—586 [204/157.69; 359/4; 365/119; 430/332] | 30 Claims |
| 1. A photochromic material comprising:
a photochromic naphthopyran; and
at least one reactive substituent bonded to the photochromic naphthopyran, wherein each reactive substituent is independently
represented by one of:
-A-D-E-G-J;
-G-E-G-J;
-D-E-G-J;
-A-D-J;
-D-G-J; and
-D-J; wherein:
(i) each -A- is independently —C(═O)—, —OC(═O)—, —NHC(═O)—, or —CH2—;
(ii) each -D- is independently:
(a) a diamine residue or a derivative thereof, said diamine residue being an aliphatic diamine residue, a cyclo aliphatic
diamine residue, a diazacycloalkane residue, an azacyclo aliphatic amine residue, a diazacrown ether residue, or an aromatic
diamine residue, wherein a first amine nitrogen of said diamine residue forms a bond with -A- or the photochromic naphthopyran,
and a second amine nitrogen of said diamine residue forms a bond with -E-, -G-, or -J; or
(b) an amino alcohol residue or a derivative thereof, said amino alcohol residue being an aliphatic amino alcohol residue,
a cyclo aliphatic amino alcohol residue, an azacyclo aliphatic alcohol residue, a diazacyclo aliphatic alcohol residue, or
an aromatic amino alcohol residue, wherein an amine nitrogen of said amino alcohol residue forms a bond with -A- or the photochromic
naphthopyran, and an alcohol oxygen of said amino alcohol residue forms a bond with -E-, -G-, or -J; or said amine nitrogen
of said amino alcohol residue forms a bond with -E-, -G-, or -J, and said alcohol oxygen of said amino alcohol residue forms
a bond with -A- or the photochromic naphthopyran;
(iii) each -E- is independently a dicarboxylic acid residue or a derivative thereof, said dicarboxylic acid residue being
an aliphatic dicarboxylic acid residue, cycloaliphatic dicarboxylic acid residue, or an aromatic dicarboxylic acid residue,
wherein a first carbonyl group of said dicarboxylic acid residue forms a bond with -G- or -D-, and a second carbonyl group
of said dicarboxylic acid residue forms a bond with -G-;
(iv) each -G- is independently:
(a) —[(OC2H4)x(OC3H6)y(OC4H8)z]—O—, wherein x, y, and z, are each independently a number between 0 and 50, and the sum of x, y, and z ranges from 1 to 50;
or
(b) a polyol residue or a derivative thereof, said polyol residue being an aliphatic polyol residue, a cyclo aliphatic polyol
residue, and an aromatic polyol residue, wherein a first polyol oxygen of said polyol residue forms a bond with -E-, -D-,
or the photochromic naphthopyran, and a second polyol oxygen of said polyol residue forms a bond with -E- or -J; and
(v) each -J is independently a group comprising a reactive moiety or residue thereof; or -J is hydrogen, provided that if
-J is hydrogen, -J is bonded to an oxygen of group -D- or -G-, forming a reactive moiety.
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