Photochromic compounds

Patent metadata

Field	Value
Publication number	US-10532997-B2
Application number	US-201816008157-A
Country	US
Kind code	B2
Filing date	Jun 14, 2018
Priority date	Jul 1, 2003
Publication date	Jan 14, 2020
Grant date	Jan 14, 2020

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 —N 3 , —CN, —COOR′, —CCR′, —C(R′)C(R′)R′, —OCOR′, —OCOOR′, —SR′, —OSO 2 R′″, 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 —CF 3 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 naphthol 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 Rm′″, and/or CON(R′)R′, wherein each 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; and
(B) each 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) hydrogen, C 1 -C 18 alkyl, C 2 -C 18 alkylidene, C 2 -C 18 alkylidyne, vinyl, C 3 -C 10 cycloalkyl, C 1 -C 18 haloalkyl, allyl, halogen, and benzyl that is unsubstituted or mono-substituted with at least one of C 1 -C 18 alkyl and C 1 -C 18 alkoxy;
(b) phenyl that is mono-substituted at the para position with at least one substituent chosen from: C 1 -C 18 alkoxy, linear or branched chain C 1 -C 20 alkylene, linear or branched chain C 1 -C 4 polyoxyalkylene, cyclic C 3 -C 20 alkylene, phenylene, naphthylene, C 1 -C 18 alkyl substituted phenylene, mono- or poly-urethane(C 1 -C 20 )alkylene, mono- or poly-ester(C 1 -C 20 )alkylene, mono- or poly-carbonate(C 1 -C 20 )alkylene, polysilanylene, polysiloxanylene and mixtures thereof wherein the at least one substituent is connected to an aryl group of a photochromic material;
(c) —CH(CN) 2 and —CH(COOX 1 ) 2 , wherein X 1 is chosen from at least one of a lengthening agent L, hydrogen, C 1 -C 18 alkyl that is unsubstituted or mono-substituted with phenyl, phenyl(C 1 -C 18 )alkyl that is mono-substituted with C 1 -C 18 alkyl, C 1 -C 18 haloalkyl, or C 1 -C 18 alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C 1 -C 18 alkyl, C 1 -C 18 haloalkyl, lengthening agent L and C 1 -C 18 alkoxy;
(d) —CH(X 2 )(X 3 ), wherein:
(i) X 2 is chosen from at least one of a lengthening agent L, hydrogen, C 1 -C 18 alkyl, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C 1 -C 18 alkyl and C 1 -C 18 alkoxy; and
(ii) X 3 is chosen from at least one of —COOX 1 , —COX 1 , —COX 4 , and —CH 2 OX 5 , wherein:
(A) X 4 is chosen from at least one of morpholino, piperidino, amino that is unsubstituted, mono- or di-substituted with C 1 -C 18 alkyl, and an unsubstituted, mono or di-substituted group chosen from phenylamino and diphenylamino, wherein each substituent is independently chosen from C 1 -C 18 alkyl or C 1 -C 18 alkoxy; and
(B) X 5 is chosen from a lengthening agent L, hydrogen, —C(O)X 2 , C 1 -C 18 alkyl that is unsubstituted or mono-substituted with (C 1 -C 18 )alkoxy or phenyl, phenyl(C 1 -C 18 )alkyl that is mono-substituted with (C 1 -C 18 )alkoxy, and an aryl group that is unsubstituted, mono- or di-substituted, wherein each aryl substituent is independently chosen from C 1 -C 18 alkyl and C 1 -C 18 alkoxy;

(e) an unsubstituted, mono-, di-, or tri-substituted aryl group; 9-julolidinyl; or an unsubstituted, mono- or di-substituted heteroaromatic group chosen from pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzofuranyl, dibenzothienyl, carbazoyl, benzopyridyl, indolinyl, and fluorenyl; wherein each aryl and heteroaromatic substituent is independently chosen for each occurrence from:
(i) a lengthening agent L;
(ii) —COOX 1 or —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;
(iii) aryl, haloaryl, C 3 -C 10 cycloalkylaryl, and an aryl group that is mono- or di-substituted with C 1 -C 18 alkyl or C 1 -C 18 alkoxy;
(iv) C 1 -C 18 alkyl, C 3 - C 10 cycloalkyl, C 3 -C 10 cycloalkyloxy(C 1 -C 18 )alkyl, aryl(C 1 -C 18 )alkyl, aryloxy(C 1 -C 18 )alkyl, mono- or di-(C 1 -C 18 )alkylaryl (C 1 -C 18 )alkyl, mono- or di-(C 1 -C 18 )alkoxyaryl(C 1 -C 18 )alkyl, C 1 -C 18 haloalkyl, and mono(C 1 -C 18 )alkoxy(C 1 -C 18 )alkyl;
(v) C 1 -C 18 alkoxy, C 3 -C 10 cycloalkoxy; cycloalkyloxy(C 1 -C 18 )alkoxy, aryl(C 1 -C 18 )alkoxy, aryloxy(C 1 -C 18 )alkoxy, mono- or di-(C 1 -C 18 )alkylaryl(C 1 -C 18 )alkoxy, and mono- or di-(C 1 -C 18 )alkoxyaryl(C 1 -C 18 )alkoxy;
(vi) aminocarbonyl, aminocarbonyl(C 1 -C 18 )alkylene, amino, mono- or di-(C 1 -C 18 )alkylamino, diarylamino, piperazino, N-(C 1 -C 18 )alkylpiperazino, N-arylpiperazino, aziridino, indolino, piperidino, morpholino, thiomorpholino, tetrahydroquinolino, tetrahydroisoquinolino, pyrrolidyl, hydroxy, acryloxy, methacryloxy, and halogen;
(vii) —OX 7 or —N(X 7 ) 2 , wherein X 7 is chosen from:
(A) 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;
(B) —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;
(C) —C(O)X 6 ; or
(D) 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;

(viii) 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;
(ix) a nitrogen containing ring represented by Formula i:

wherein
(A) 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 18 alkyl, and X 13 is chosen from a lengthening agent L, phenyl and naphthyl, and
(B) 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, and

(x) a 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

Assignees

• Transitions Optical Inc

Inventors

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

Classifications

• C09K2211/1088

  containing oxygen as the only heteroatom · CPC title

• G02B5/23

  Photochromic filters · CPC title

• C07D311/94

  condensed with rings other than six-membered or with ring systems containing such rings · CPC title

• C09K2211/1033

  with oxygen · CPC title

• Y10T428/31786

  Of polyester [e.g., alkyd, etc.] · CPC title