Kumar Anil (Pittsburgh PA) Knowles David B. (Pittsburgh PA) Van Gemert Barry (Pittsburgh PA)
출원인 / 주소
Transitions Optical, Inc. (Pinellas Park FL 02)
인용정보
피인용 횟수 :
48인용 특허 :
22
초록▼
Described are novel reversible photochromic 2H-naphtho[1,2-b]pyran compounds, examples of which are compounds fused on the naphtho-portion of the naphthopyran ring with an indeno group or certain heterocyclic substituents. Certain substituents are also present at the 2 and 5 positions and sometimes
Described are novel reversible photochromic 2H-naphtho[1,2-b]pyran compounds, examples of which are compounds fused on the naphtho-portion of the naphthopyran ring with an indeno group or certain heterocyclic substituents. Certain substituents are also present at the 2 and 5 positions and sometimes at the 6 position of the naphthopyran ring. Also described are organic host materials that contain or that are coated with such compounds. Articles such as ophthalmic lenses or other plastic transparencies that incorporate the novel naphthopyran compounds or combinations thereof with complementary photochromic compounds, e.g., spiro(indoline) type compounds, are also described.
대표청구항▼
A naphthopyran compound represented by the following graphic formulae: [Figure] or [Figure] wherein, (a) A is selected from the group consisting of: (i) an unsubstituted, mono-substituted or di-substituted heterocyclic ring selected from the group consisting of benzothieno, benzofurano and indolo, t
A naphthopyran compound represented by the following graphic formulae: [Figure] or [Figure] wherein, (a) A is selected from the group consisting of: (i) an unsubstituted, mono-substituted or di-substituted heterocyclic ring selected from the group consisting of benzothieno, benzofurano and indolo, the 2,3 or 3,2 positions of said heterocyclic ring being fused to the i, j or k side of said naphthopyran; and (ii) an unsubstituted, mono-substituted or di-substituted indeno group fused to the i, j or k side of said naphthopyran; each of said heterocyclic ring and indeno group substituents being C1-C6 alkyl, C5-C7 cycloalkyl, C1-C6 alkoxy, chloro, fluoro, a benzo or mono-substituted benzo group fused to the benzo portion of the benzothieno, benzofurano, indeno or indolo moiety, said benzo substitutent being C1-C6 alkyl, C5-C7 cycloalkyl, C1-C6 alkyl mono-substituted (C5-C7)cycloalkyl, C1-C6 alkoxy, chloro or fluoro; (b) R1 is selected from the group consisting of: (i) －C(O)W, W being －OR4 or －N(R5)R6, wherein R4 is hydrogen, allyl, C1-C6 alkyl, phenyl, mono-substituted phenyl, phenyl(C1-C3)alkyl, mono-substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy(C2-C4)alkyl, C1-C6 chloroalkyl or C1-C6 fluoroalkyl; R5 and R6 are each selected from the group consisting of hydrogen, C1-C6 alkyl, C5-C7 cycloalkyl, unsubstituted, mono-substituted and di-substituted phenyl, or R5 and R6 together with the nitrogen atom form an unsubstituted, mono-substituted or di-substituted heterocyclic ring selected from the group consisting of 1-indolinyl, morpholino, piperidino, 1-pyrrolidyl, 1-imidazolidyl, 2-imidazolin-1-yl, pyrazolidyl, pyrazolinyl and 1-piperazinyl; and (ii) －C(R11)2X, wherein X is －CN, chloro, fluoro, hydroxy, benzoyloxy, C1-C6 alkoxy, C2-C6 acyloxy, amino, C1-C6 mono-alkylamino, C1-C6 dialkylamino, morpholino, piperidino, 1-indolinyl, pyrrolidyl, or trimethylsilyloxy, R11 is hydrogen, C1-C6 alkyl, phenyl or naphthyl, and each of said phenyl and heterocyclic ring substituents in this part (b) being C1-C6 alkyl or C1-C6 alkoxy; (c) R2 is hydrogen, C1-C6 alkyl, the mono-, di- or tri-substituted aryl groups phenyl or naphthyl, said aryl substituents being C1-C6 alkyl, C1-C6 alkoxy, chloro or fluoro; or (d) R1 and R2 together form the heterocyclic ring A, as defined in part(a)(i), provided that the 2,3 or 3,2 positions of said heterocyclic ring are fused to the f side of said naphthopyran, and provided further there is only one heterocyclic ring A fused to the naphthopyran; (e) each R3 is chloro, fluoro, C1-C6 alkyl, C1-C6 alkoxy, phenyl, naphthyl, phenoxy, naphthoxy or the group, －N(R5)R6, as defined in (b)(i) , and n is selected from the integers 0, 1 or 2, provided that group A, as defined in (a), is present, or each R3 is chloro, fluoro, phenoxy, naphthoxy or the group, －N(R5)R6, and n is selected from the integers 1, 2 or 3, provided that group A is absent; and (f) B and B′are each selected from the group consisting of: (i) the unsubstituted, mono-, di- and tri-substituted aryl groups phenyl and naphthyl; (ii) the unsubstituted, mono- and di-substituted heterocyclic aromatic groups pyridyl, furanyl, benzofuran-2-yl, benzofuran-3-yl, thienyl, benzothien-2-yl, benzothien-3-yl, dibenzothienyl, dibenzofuranyl, and carbazolyl, said aryl and heterocyclic substituents described in (i) and (ii) being selected from the group consisting of hydroxy, amino, C1-C6 monoalkylamino, C1-C6 dialkylamino, morpholino, piperidino, 1-indolinyl, pyrrolidyl, 1-imidazolidyl, 2-imidazolin-1-yl, 2-pyrazolidyl, pyrazolinyl, 1-piperazinyl, C1-C6 alkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy, mono(C1-C6)alkoxy(C1-C4)alkyl, acryloxy, methacryloxy, fluoro and chloro; (iii) the groups represented by the following graphic formulae: [Figure] wherein D is carbon or oxygen and E is oxygen or substituted nitrogen, provided that when E is substituted nitrogen, D is carbon, said nitrogen substituent being selected from the group consisting of hydrogen, C1-C6 alkyl, and C2-C6 acyl; each R8 is C1-C6 alkyl, C1-C6 alkoxy, hydroxy, chloro or fluoro; R9 and R10 are each hydrogen or C1-C6 alkyl; and m is the integer 0, 1 or 2; (iv) C1-C6 alkyl, C1-C6 chloroalkyl, C1-C6 fluoroalkyl, C1-C6 alkoxy(C1-C4)alkyl, C3-C6 cycloalkyl, mono(C1-C6)alkoxy(C3 -C6) cycloalkyl, mono(C1-C6)alkyl(C3-C6) cycloalkyl, chloro(C3-C6)cycloalkyl and fluoro(C3-C6)cycloalkyl; and (v) the group represented by the following graphic formula: [Figure] wherein U is hydrogen or C1-C4 alkyl, and V is selected from the unsubstituted, mono- and di-substituted members of the group consisting of naphthyl, phenyl, furanyl and thienyl, wherein the substituents for each member of said group are C1-C4 alkyl, C1-C4 alkoxy, fluoro or chloro; or (vi) B and B′taken together form fluoren-9-ylidene, mono- or di-substituted fluoren-9-ylidene or a member selected from the group consisting of saturated C3-C12 spiro-monocyclic hydrocarbon rings, saturated C7-C12 spiro-bicyclic hydrocarbon rings, and saturated C7-C12 spiro-tricyclic hydrocarbon rings, said fluoren-9-ylidene substituents being selected from the group consisting of C1-C4 alkyl, C1-C4 alkoxy, fluoro and chloro. A photochromic article comprising a polymeric organic host material and a photochromic amount of a naphthopyran compound of claim 1.
Hovey Richard J. (Sturbridge MA) Chu Nori Y. C. (Southbridge MA) Piusz Peter G. (Brimfield MA) Fuchsman Charles H. (Bemidji MN), Photochromic compounds.
Hovey Richard J. (Sturbridge MA) Chu Nori Y. C. (Southbridge MA) Piusz Peter G. (Longmeadow MA) Fuchsman Charles H. (Bemidji MN), Photochromic compounds.
Heller Harry G. (Llandaff GB7) Oliver Stephen N. (Felixstowe GB2) Whittall John (Caerphilly MI GB7) Tomlinson Ian (Midland MI), Photochromic spiropyran compounds.
Heller Harry G. (Cardiff GB7) Oliver Stephen N. (Felixstowe GB2) Whittall John (Caerphilly GB7) Brettle Jack (Towcester GB2) Trundle Clive (Towcester GB2) Baskerville Martin W. (Towcester GB2), Photoreactive lenses with adamantane spiro compounds.
Chan,You Ping; Breyne,Olivier, Benzo-, naphtho-and phenanthrochromene substituted by carbamated or ureated phenyls, preparation thereof and compositions and articles containing them.
Broekhuis, Michael D.; Byker, Harlan J.; Millett, Frederick A., Enhanced thermochromic window which incorporates a film with multiple layers of alternating refractive index.
Chan You-Ping,FRX ; Jean Patrick,FRX, Naphthopyrans and phenanthropyrans annelated in C5-C6 with a bicycle group and compositions and (co) polymer matrices containing them.
You-Ping Chan FR; Patrick Jean FR, Naphthopyrans and phenanthropyrans annelated in C5-C6 with a bicyclic group, and compositions and (co) polymer matrices containing them.
Breyne, Olivier; Chan, You-Ping; Patrick, Jean, Naphthopyrans annelated in C5-C6 with a dihydrobenzo-cycloheptatriene-type carbocycle and compositions and matrices containing them.
Breyne, Olivier; Chan, You-Ping; Jean, Patrick, Naphthopyrans annelated in C5-C6 with an indene- or dihydronaphthalene-type carbocycle, and compositions and (co)polymer matrices containing them.
Olivier Breyne FR; You-Ping Chan FR; Patrick Jean FR, Naphthopyrans having a perfluoroalkyl substituent in position 5, preparation and compositions and matrices containing them.
Breyne, Olivier; Chan, You-Ping; Jean, Patrick, Naphthopyrans with a heterocycle in the 5, 6-position, preparation, and (co)polymer compositions and matrices containing them.
Lu, Yunyi; Xiao, Wenjing; Walters, Robert W.; Wang, Feng; Haley, M. Frank; Lewis, Jason R.; Chopra, Anu; Kim, Beon-Kyu; Yu, Huayun, Photochromic compounds having at least two photochromic moieties.
Chopra, Anu; Deng, Jun; Kim, Beon-Kyu; Knowles, David B.; Molock, Frank; Montes, Victor A.; Straight, Stephen D.; Xiao, Wenjing; Yu, Huayun, Photochromic materials having extended pi-conjugated systems and compositions and articles including the same.
Chopra, Anu; Deng, Jun; Kim, Beon-Kyu; Knowles, David B.; Molock, Jr., Frank F.; Montes, Victor A.; Straight, Stephen D.; Xiao, Wenjing; Yu, Huayun, Photochromic materials having extended pi-conjugated systems and compositions and articles including the same.
Chopra, Anu; Deng, Jun; Kim, Beon-Kyu; Knowles, David B.; Molock, Jr., Frank F.; Montes, Victor A.; Straight, Stephen D.; Xiao, Wenjing; Yu, Huayun, Photochromic materials having extended pi-conjugated systems and compositions and articles including the same.
Chopra, Anu; Deng, Jun; Kim, Beon-Kyu; Knowles, David B.; Molock, Jr., Frank F.; Montes, Victor A.; Straight, Stephen D.; Xiao, Wenjing; Yu, Huayun, Photochromic materials having extended pi-conjugated systems and compositions and articles including the same.
Chopra, Anu; Deng, Jun; Kim, Beon-Kyu; Knowles, David B.; Molock, Jr., Frank F.; Montes, Victor A.; Straight, Stephen D.; Xiao, Wenjing; Yu, Huayun, Photochromic materials having extended pi-conjugated systems and compositions and articles including the same.
Bancroft, Kevin E.; Chopra, Anu; Dai, Xiao-Man; Kim, Beon-Kyu; Knowles, David B.; Lewis, Jason R.; Montes, Victor A.; Straight, Stephen D.; Tomasulo, Massimiliano; Van Gemert, Barry; Walters, Robert W.; Xiao, Wenjing; Yu, Huayun; Zezinka, Elizabeth A., Photochromic materials that include indeno-fused naphthopyrans.
Florent Frederic Henri,FRX ; Henry David,FRX ; Vachet Andre Jean,FRX ; Vial Jacques Jean,FRX, Temperature stable and sunlight protected photochromic articles.
Florent Frederic Henri,FRX ; Henry David,FRX ; Vachet Andre Jean,FRX ; Vial Jacques Jean,FRX, Temperature stable and sunlight protected photochromic articles.
Frederic Henri Florent FR; David Henry FR; Andre Jean Vachet FR; Jacques Jean Vial FR, Temperature stable and sunlight protected photochromic articles.
※ AI-Helper는 부적절한 답변을 할 수 있습니다.