Kumar Anil (Pittsburgh PA) Knowles David B. (Apollo PA) Van Gemert Barry (Murrysville PA)
출원인 / 주소
Transitions Optical, Inc. (Pinellas Park FL 02)
인용정보
피인용 횟수 :
109인용 특허 :
18
초록▼
Described are novel reversible photochromic 2H-naphtho[1,2-b]pyran compounds, examples of which are compounds having certain substituents at the number 5 carbon atom of the naphtho-portion of the naphthopyran and at the 2-position of the pyran ring. Certain substituents may also be present at the nu
Described are novel reversible photochromic 2H-naphtho[1,2-b]pyran compounds, examples of which are compounds having certain substituents at the number 5 carbon atom of the naphtho-portion of the naphthopyran and at the 2-position of the pyran ring. Certain substituents may also be present at the number 6, 7, 8, 9 or 10 carbon atoms of the naphtho portion of the naphthopyran. 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 selected from the group consisting of, －SR7, －OR4, －CH(COOR7)2, －CH2COOR7, －N(R5)R6, －N(R7)C(O)R7, －C(R7)2OH, －CN, －CF3, halogen, C1-C6 alkyl, C3-C7 cycloalkyl, the mono-, di- and tri- substituted ary1
A naphthopyran compound represented by the following graphic formula: [Figure] wherein, (a) R1 is selected from the group consisting of, －SR7, －OR4, －CH(COOR7)2, －CH2COOR7, －N(R5)R6, －N(R7)C(O)R7, －C(R7)2OH, －CN, －CF3, halogen, C1-C6 alkyl, C3-C7 cycloalkyl, the mono-, di- and tri- substituted ary1 groups phenyl and naphthyl, unsubstituted and mono-substituted phenyl(C1-C3)alkyl, unsubstituted and mono-substituted naphthyl(C1-C3)alkyl, (C1-C6)alkoxy(C2-C4)alkyl, the unsubstituted, mono- and di-substituted heterocyclic aromatic groups pyridyl, pyrrolyl, indolyl, furanyl, benzofuranyl, thienyl and benzothienyl; wherein R7 is C1-C6 alkyl, or the mono-, di- or tri-substituted aryl groups phenyl and naphthyl, R4 is hydrogen, C1-C6 alky, the mono- or di-substituted aryl groups phenyl and naphthyl, unsubstituted or mono-substituted phenyl(C1-C3)alkyl, unsubstituted or mono-substituted naphthyl(C1-C3)alkyl, (C1-C6)alkoxy(C2-C4)alkyl, C3-C7 cycloalkyl, mono(C1-C4)alkyl substituted C3-C7 cycloalkyl, C1-C6 haloalkyl, allyl, the group, －CH(R14)X, wherein X is －CN, －CF3, halogen, or －C(O)W, W being －OR12, wherein R12 is hydrogen, allyl, C1-C6 alkyl, unsubstituted or mono-substituted phenyl, unsubstituted or mono-substituted phenyl (C1-C3)alkyl, (C1-C6)alkoxy(C2-C4)alkyl, or C1-C6 haloalkyl, and R14 is hydrogen or C1-C6 alkyl; or R4 is the group; －C(O)Y, wherein Y is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, unsubstituted, mono- or disubstituted phenyl, unsubstituted, mono- or di-substituted phenoxy, R5 and R6 are each selected from the group consisting of hydrogen, C1-C6 alkyl, C5-C7 cycloalkyl, phenyl, mono- or 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, each of the said phenyl, phenoxy and heterocyclic substituents being selected from the group consisting of hydroxy, amino, C1-C6 monoalkylamino, C1-C6 dialkylamino, piperidino, morpholino, pyrryl, indolinyl, pyrrolidyl, trimethylsilyloxy, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, mono(C1-C6)alkoxy(C1-C4)alkyl, acryloxy, methacryloxy and halogen, each of said halogen or (halo) groups being fluoro or chloro; (b) R2 is the group, －OR4, R4 being the same as defined in (a); (c) each R3 is selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halogen, unsubstituted and mono-substituted phenyl, unsubstituted and mono-substituted phenoxy, said phenyl and phenoxy substituents being selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy and halogen, each of said halogen groups being fluoro or chloro, and n is selected from the integers 0, 1, 2, and 3; (d) 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, benzofuranyl, thienyl, benzothienyl, dibenzothienyl, dibenzofuranyl, and carbazolyl, said phenyl, naphthyl and heterocyclic substituents being selected from the group consisting of hydroxy, amino, C1-C6 monoalkylamino, C1-C6 dialkylamino, piperidino, morpholino, 1-indolinyl, pyrrolidyl, 1-imidazolidyl, 2-imidazolin-1-yl, 2-pyrazolidyl, pyrazolinyl, 1-piperazinyl, C1-C6 alkyl, C1-C6 haloalkyl, C1-C6 alkoxy, mono(C1-C6)alkoxy(C1-C4)alkyl, acryloxy, methacryloxy and halogen, each of said halogen or (halo) groups being fluoro or 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 or halogen, said halogen being 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 haloalkyl, C1-C6 alkoxy(C1-C4) alkyl, C3-C6 cycloalkyl, mono (C1-C6) alkoxy (C3-C6) cycloalkyl, mono (C1-C6) alkyl (C3-C6) cycloalkyl and halo(C3-C6)cycloalkyl, said halo groups being fluoro or chloro; 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 group consisting of 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 an unsubstituted, 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.
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