Van Gemert Barry (Murrysville PA) Kumar Anil (Pittsburgh PA)
출원인 / 주소
Transitions Optical, Inc. (Pinellas Park FL 02)
인용정보
피인용 횟수 :
33인용 특허 :
12
초록▼
Described are novel reversible photochromic 3H-naphtho[2,1-b]pyran compounds, examples of which are substituted with an oxy-bearing substituent at the number 8 carbon atom and with either an alkyl group at the number 7 carbon atom or with a carbonyl bearing substituent at the number 9 carbon atom an
Described are novel reversible photochromic 3H-naphtho[2,1-b]pyran compounds, examples of which are substituted with an oxy-bearing substituent at the number 8 carbon atom and with either an alkyl group at the number 7 carbon atom or with a carbonyl bearing substituent at the number 9 carbon atom and certain substituents at the 3-position of the pyran ring, e.g., 3,3-spirofluoren-9-ylidene 8-methoxy-9-carbomethoxy-3H-naphtho[2,1-b]pyran. 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 formula: [Figure] wherein: (a) R1 is hydrogen or a C1-C6 alkyl; R2 is hydrogen or the group, －C(O)W, W being －OR4 or －N(R5)R6, wherein R4 is hydrogen, allyl, C1-C6 alkyl, phenyl, C1-C6 monoalkyl substituted phenyl, C1-C6 monoalkoxy substit
A naphthopyran compound represented by the following graphic formula: [Figure] wherein: (a) R1 is hydrogen or a C1-C6 alkyl; R2 is hydrogen or the group, －C(O)W, W being －OR4 or －N(R5)R6, wherein R4 is hydrogen, allyl, C1-C6 alkyl, phenyl, C1-C6 monoalkyl substituted phenyl, C1-C6 monoalkoxy substituted phenyl, phenyl(C1-C3)alkyl, C1-C6 monoalkyl substituted phenyl(C1-C3)alkyl, C1-C6 monoalkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl, C1-C6 monofluoroalkyl, or C1-C6 monochloroalkyl, and wherein R5 and R6 each are selected from the group consisting of hydrogen, C1-C6 alkyl, C5-C7 cycloalkyl, phenyl and mono- or di-substituted phenyl, or R5 and R6 together with the attached nitrogen atom form a mono- or di-substituted or unsubstituted heterocyclic ring selected from the group consisting of indolinyl, morpholino, piperidino, 1-pyrrolidyl, 1-pyrrolinyl, 1-imidazolidyl, 2-imidazolin-1-yl, 2-pyrazolidyl and 1-piperazinyl, said phenyl and heterocyclic ring substituents being selected from C1-C6 alkyl and C1-C6 alkoxy; R3 is hydrogen, C1-C6 alkyl, phenyl(C1-C3)alkyl, C1-C6 monoalkyl substituted phenyl(C1-C3)alkyl, C1-C6 monoalkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C1-C4)alkyl, C5-C7 cycloalkyl, C1-C4 monoalkyl substituted C5-C7 cycloalkyl, C1-C6 monofluoroalkyl, C1-C6 monobromoalkyl, C1-C6 monochloroalkyl, allyl or the group, －C(O)X, wherein X is C1-C6 alkyl, phenyl, C1-C6 mono- or C1-C6 di-alkyl substituted phenyl, C1-C6 mono- or C1-C6 di-alkoxy substituted phenyl, C1-C6 alkoxy, phenoxy, C1-C6 mono- or C1-C6 di-alkyl substituted phenoxy, C1-C6 mono- or C1-C6 di-alkoxy substituted phenoxy, C1-C6 alkylamino, phenylamino, C1-C6 mono- or C1-C6 di-alkyl substituted phenylamino, or C1-C6 mono- or C1-C6 di-alkoxy substituted phenylamino, provided that one of R1 and R2 is hydrogen; and (b) B is selected from the group consisting of the unsubstituted, mono-, di- and tri-substituted aryl groups, phenyl and naphthyl; and (c) B′is selected from the group consisting of: (i) the unsubstituted, mono- and di-substituted aromatic heterocyclic groups dibenzothienyl, dibenzofuranyl, and carbazolyl, said aryl and aromatic heterocyclic substituents described in (b) and (c) being selected from the group consisting of hydroxy, amino, mono(C1-C6)alkylamino, di(C1-C6)alkylamino, morpholino, piperidino, 1-indolinyl, pyrrolidyl, 1-imidazolidyl, 2- imidazolin-1-yl, 2-pyrazolidyl, pyrazolinyl, 1-piperazinyl, C1-C6 alkyl, C1-C6 fluoroalkyl, C1-C6 chloroalkyl, C1-C6 alkoxy, mono(C1-C6)alkoxy(C1-C4)alkyl, acryloxy, methacryloxy, chloro and fluoro; (ii) the groups represented by the following graphic formulae: [Figure] [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 R13 is C1-C6 alkyl, C1-C6 alkoxy, hydroxy, chloro or fluoro, R14 and R15 are each hydrogen or C1-C6 alkyl, and m is the integer 0, 1 or 2; (iii) C1-C6 alkyl, C1-C6 fluoroalkyl, C1-C6 chloroalkyl, C1-C6 alkoxy(C1-C4)alkyl, C3-C6 cycloalkyl, mono(C1-C6)alkoxy(C3-C6)cycloalkyl, mono(C1-C6)alkyl(C3-C6) cycloalkyl, fluoro(C3-C6)cycloalkyl and chloro(C3-C6) cycloalkyl; and (iv) 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 (d) 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, provided that B and B′do not form spiro-tricyclic adamantylidene, each of said fluoren-9-ylidene substituents being selected from the group consisting of C1-C4 alkyl, C1-C4 alkoxy, fluoro and chloro.
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