Photochromic compounds

Patent metadata

Field	Value
Publication number	US-10501446-B2
Application number	US-201816007067-A
Country	US
Kind code	B2
Filing date	Jun 13, 2018
Priority date	Jul 1, 2003
Publication date	Dec 10, 2019
Grant date	Dec 10, 2019

Abstract

A photochromic compound is provided, which may be a pyran, an oxazine, or a fulgide. The photochromic compound has at least one substituent Q attached thereto, each Q independently being —N3, —CN, —COOR′, —CCR′, —C(R′)C(R′)R′, —OCOR′, —OCOOR′, —SR′, —OSO2R′″, and/or —CON(R′)R′, wherein each R′ is hydrogen, an unsubstituted or substituted alkyl group having from 1 to 18 carbon atoms; an unsubstituted or substituted aryl group, an unsubstituted or substituted alkene or alkyne group having from 2 to 18 carbon atoms, wherein the substituents are halo or hydroxyl and R″′ is —CF3 or a perfluorinated alkyl group having from 2 to 18 carbon atoms The number, locations and nature of the constituents Q are dependent upon the structure of the photochromic compound.

First claim

We claim:

1. A photochromic material represented by the following graphic formula:

wherein:
(A) substituent Q comprises —N 3 , —CN, —COOR′, —CCR′, —C(R′)C(R′)R′, —OCOR′, —OCOOR′, —SR′, —OSO 2 R″′, and/or —CONHR′, wherein R′ independently comprises hydrogen, an unsubstituted or substituted alkyl group having from 1 to 18 carbon atoms, an unsubstituted or substituted aryl group, an unsubstituted or substituted alkene or alkyne group having from 2 to 18 carbon atoms, wherein said substituents are chosen from halo and hydroxyl and R″′ comprises —CF 3 or a perfluorinated alkyl group having from 2 to 18 carbon atoms;
(B) i is an integer chosen from 0 to the total number of available positions and each R is independently chosen for each occurrence from:
(a) a group represented by B described hereinafter;
(b) —C(O)X 24 , wherein X 24 is chosen from a lengthening agent L, hydroxy, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, phenyl that is unsubstituted or mono-substituted with C 1 -C 18 alkyl or C 1 -C 18 alkoxy, amino that is unsubstituted, mono- or di-substituted with at least one of C 1 -C 18 alkyl, phenyl, benzyl, and naphthyl;
(c) —OX 7 and —N(X 7 ) 2 ; wherein X 7 is chosen from:
(i) a lengthening agent L, hydrogen, C 1 -C 18 alkyl, C 1 -C 18 acyl, phenyl(C 1 -C 18 )alkyl, mono(C 1 -C 18 )alkyl substituted phenyl(C 1 -C 18 )alkyl, mono(C 1 -C 18 )alkoxy substituted phenyl(C 1 -C 18 )alkyl; C 1 -C 18 alkoxy(C 1 -C 18 )alkyl; C 3 -C 10 cycloalkyl; mono(C 1 -C 18 )alkyl substituted C 3 -C 10 cycloalkyl, C 1 -C 18 haloalkyl, allyl, benzoyl, mono-subsituted benzoyl, naphthoyl or mono-substituted naphthoyl, wherein each of said benzoyl and naphthoyl substituents are independently chosen from C 1 -C 18 alkyl, and C 1 -C 18 alkoxy;
(ii) —CH(X 8 )X 9 , wherein X 8 is chosen from a lengthening agent L, hydrogen or C 1 -C 18 alkyl; and X 9 is chosen from a lengthening agent L, —CN, —CF 3 , or —COOX 10 , wherein X 10 is chosen from a lengthening agent L, hydrogen or C 1 -C 18 alkyl;
(iii) —C(O)X 6 , wherein X 6 is chosen from at least one of: a lengthening agent L, hydrogen, C 1 -C 18 alkoxy, phenoxy that is unsubstituted, mono- or di- substituted with C 1 -C 18 alkyl or C 1 -C 18 alkoxy, an aryl group that is unsubstituted, mono- or di-substituted with C 1 -C 18 alkyl or C 1 -C 18 alkoxy, an amino group that is unsubstituted, mono- or di-substituted with C 1 -C 18 alkyl, and a phenylamino group that is unsubstituted, mono- or di-substituted with C 1 -C 18 alkyl or C 1 -C 18 alkoxy;or
(iv) tri(C 1 -C 18 )alkylsilyl, tri(C 1 -C 18 )alkylsilyloxy, tri(C 1 -C 18 )alkoxysilyl, tri(C 1 -C 18 )alkoxysilyloxy, di(C 1 -C 18 )alkyl(C 1 -C 18 alkoxy)silyl, di(C 1 -C 18 )alkyl(C 1 -C 18 alkoxy)silyloxy, di(C 1 -C 18 )alkoxy(C 1 -C 18 alkyl)silyl or di(C 1 -C 18 )alkoxy(C 1 -C 18 alkyl)silyloxy;

(d) —SX 11 ; wherein X 11 is chosen from a lengthening agent L, hydrogen, C 1 -C 18 alkyl, C 1 -C 18 haloalkyl, an aryl group that is unsubstituted, or mono- or di- substituted with C 1 -C 18 alkyl, C 1 -C 18 alkoxy, or halogen;
(e) a nitrogen containing ring represented by Formula i:

wherein
(i) n is an integer chosen from 0, 1, 2, and 3, and each U is independently chosen for each occurrence from —CH 2 —, —CH(X 12 )—, —C(X 12 ) 2 —, —CH(X 13 )—, —C(X 13 ) 2 —, and —C(X 12 )(X 13 )—, wherein X 12 is chosen from a lengthening agent L and C 1 -C 12 alkyl, and X 13 is chosen from a lengthening agent L, phenyl and naphthyl, and
(ii) U′ is chosen from U, —O—, —S—, —S(O)—, —NH—, —N(X 12 )— or —N(X 13 )—, and m is an integer chosen from 1, 2, and 3;

(f) the group represented by Formula ii or iii;

wherein X 14 , X 15 , and X 16 are independently chosen for each occurrence from a lengthening agent L, hydrogen, C 1 -C 18 alkyl, phenyl or naphthyl, or X 14 and X 15 together form a ring of 5 to 8 carbon atoms; p is an integer chosen from 0, 1, or 2, and X 17 is independently chosen for each occurrence from a lengthening agent L, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, or halogen;
(g) immediately adjacent R groups together form a group represented by Formula vii, viii, or ix:

wherein
(i) W and W′ are independently chosen for each occurrence from —O—, —N(X 7 )—, —C(X 14 )—, and —C(X 17 )—;
(ii) X 14 , X 15 and X 17 , wherein X 14 , and X 15 are independently chosen for each occurrence from a lengthening agent L, hydrogen, C 1 -C 18 alkyl, phenyl or naphthyl, or X 14 and X 15 together form a ring of 5 to 8 carbon atoms; and X 17 is independently chosen for each occurrence from a lengthening agent L, C 1 -C 18 alkyl, C 1 -C 18 alkoxy, or halogen; and
(iii) q is an integer chosen from 0, 1, 2, 3, and 4; and

(h) a lengthening agent L represented by:
—[S 1 ] c -[Q 1 -[S 2 ] d ] d′ -[Q 2 -[S 3 ] e ] e′ -[Q 3 -[S 4 ] f ] f′ —S 5 —P

wherein:
(i) each Q 1 , Q 2 , and Q 3 is independently chosen for each occurrence from: a divalent group chosen from: an unsubstituted or a substituted aromatic group, an unsubstituted or a substituted alicyclic group, an unsubstituted or a substituted heterocyclic group, and mixtures thereof, wherein substituents are chosen from: a group represented by P, liquid crystal mesogens, halogen, poly(C 1 -C 18 alkoxy), C 1 -C 18 alkoxycarbonyl, C 1 -C 18 alkylcarbonyl, C 1 -C 18 alkoxycarbonyloxy, aryloxycarbonyloxy, perfluoro(C 1 -C 18 )alkoxy, perfluoro (C 1 -C 18 )alkoxycarbonyl, perfluoro(C 1 -C 18 )alkylcarbonyl, perfluoro(C 1 -C 18 )alkylamino, di-(perfluoro(C 1 -C 18 )alkyl)amino, perfluoro(C 1 -C 18 )alkylthio, C 1 -C 18 alkylthio, C 1 -C 18 acetyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkoxy, a straight-chain or branched C 1 -C 18 alkyl group that is mono-substituted with cyano, halo, or C 1 -C 18 alkoxy, or poly-substituted with halo, and a group comprising one of the following formulae: -M(T) (t-1) and -M(OT) (t-1) , wherein M is chosen from aluminum, antimony, tantalum, titanium, zirconium and silicon, T is chosen from organofunctional radicals, organofunctional hydrocarbon radicals, aliphatic hydrocarbon radicals and aromatic hydrocarbon radicals, and t is the valence of M;
(ii) c, d, e, and f are each independently chosen from an integer ranging from 0 to 20, inclusive; and each S 1 , S 2 , S 3 , S 4 , and S 5 is independently chosen for each occurrence from a spacer unit chosen from:
(1) —(CH 2 ) g —, —(CF 2 ) h —, —Si(CH 2 ) g —, —(Si[(CH 3 ) 2 ]O) h —, wherein g is independently chosen for each occurrence from 1 to 20; h is a whole number from 1 to 16 inclusive;
(2) —N(Z)—, —C(Z)═C(Z)—, —C(Z)═N—, —C(Z′)—C(Z′)— or a single bond, wherein Z is independently chosen for each occurrence from hydrogen, C 1 -C 18 alkyl, C 3 -C 10 cycloalkyl and aryl, and Z′ is independently chosen for each occurrence from C 1 -C 18 alkyl, C 3 -C 10 cycloalkyl and aryl; and
(3) —O—, —C(O)—, —C≡C—, —N═N—, —S—, —S(O)—, —S(O)(O)—, —(O)S(O)—, —(O)S(O)O—, —O(O)S(O)O—, or straight-chain or branched C 1 -C 24 alkylene residue, said C 1 -C 24 alkylene residue being unsubstituted, mono-substituted by cyano or halo, or poly-substituted by halo; provided that when two spacer units comprising heteroatoms are linked together the spacer units are linked so that heteroatoms are not directly linked to each other and when S 1 and S 5 are linked to PC and P, respectively, they are linked so that two heteroatoms are not directly linked to each other;

(iii) P is chose

Assignees

• Transitions Optical Inc

Inventors

• He Meng
• Dabideen Darrin R
• Kellar Ii Terry A
• Kumar Anil

Classifications

• G02B1/04

  made of organic materials, e.g. plastics (G02B1/08 takes precedence) · CPC title

• C09K2211/1029

  containing one nitrogen atom as the heteroatom · CPC title

• C07D311/92

  Naphthopyrans; Hydrogenated naphthopyrans · CPC title

• C07D405/10 Primary

  linked by a carbon chain containing aromatic rings · CPC title

• Y10T428/31663

  As siloxane, silicone or silane · CPC title