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 :
22인용 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 the group, －C(O)W, W being －OR4 or －N(R5)R6, wherein R4 is hydrogen, allyl, C1-C6 alkyl, phenyl, mono(C1-C6)alkyl substituted phenyl, mono(C1-C6)alkoxy substituted phenyl, phenyl(C1-C3)alkyl, mono(C1-C6
A naphthopyran compound represented by the following graphic formula: [Figure] wherein, (a) R1 is the group, －C(O)W, W being －OR4 or －N(R5)R6, wherein R4 is hydrogen, allyl, C1-C6 alkyl, phenyl, mono(C1-C6)alkyl substituted phenyl, mono(C1-C6)alkoxy substituted phenyl, phenyl(C1-C3)alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(C1-C3)alkyl, C1-C6 alkoxy(C2-C4)alkyl, or C1-C6 haloalkyl; R5 and R6 are each selected from the group consisting of hydrogen, C1-C6 alkyl, C5-C7 cycloalkyl, phenyl and mono- or di-substituted phenyl, said phenyl substituents being selected from C1-C6 alkyl and C1-C6 alkoxy, and said halo substituent being chloro or fluoro; (b) R2 and each R3 are hydrogen, C1-C6 alkyl, C3-C7 cycloalkyl, substituted or unsubstituted phenyl, the group －OR7, wherein R7 is hydrogen, C1-C6 alkyl, phenyl(C1-C3)-alkyl, mono(C1-C6)alkyl substituted phenyl(C1-C3)alkyl, mono(C1-C6)alkoxy substituted phenyl(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(R8)X, wherein X is －CN, －CF3, halogen, or －C(O)W and R8 is hydrogen or C1-C6 alkyl, or R7 is the group, －C(O)Y, wherein Y is hydrogen, C1-C6 alkyl, C1-C6 alkoxy, the substituted or unsubstituted aryl groups phenyl or naphthyl, phenoxy, C1-C6 mono- or di-alkyl substituted phenoxy, C1-C6 mono- or di-alkoxy substituted phenoxy, each of said phenyl and naphthyl substituents being selected from C1-C6 alkyl or C1-C6 alkoxy, said halogen or halo substituents being chloro or fluoro, and n is selected from the integers 0, 1, 2 or 3; and (c) B is selected from the group consisting of unsubstituted, mono-, di- and tri-substituted aryl groups phenyl and naphthyl, said aryl substituents being selected from the group consisting of C1-C6 alkyl, C1-C6 alkoxy, halogen, amino, C1-C6 monoalkylamino, C1-C6 dialkylamino, morpholino, piperidino, indolinyl, 1-imidazolidyl, 2-imidazolin-1-yl, 2-pyrazolidyl, pyrazolinyl, 1-piperazinyl and pyrrolidyl, said halogen being chloro or fluoro; (d) B′is selected from the group consisting of: (i) mono-substituted aryl groups phenyl and naphthyl, said aryl substituents being selected from the group consisting of amino, C1-C6 monoalkylamino, C1-C6 dialkylamino, morpholino, piperidino, indolinyl, 1-imidazolidyl, 2-imidazolin-1-yl, 2-pyrazolidyl, pyrazolinyl, 1-piperazinyl and pyrrolidyl; (ii) 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, each of said substituent of said group being C1-C4 alkyl, C1-C4 alkoxy, fluoro, or chloro; and (iii) the group represented by the following graphic formula: [Figure] wherein M is CH2, O, S, N-R14, wherein R14 is selected from the group consisting of hydrogen, C1-C6 alkyl, C5-C7 cycloalkyl, phenyl, mono-substituted, and di-substituted phenyl, said phenyl substituents being selected from C1-C6 alkyl, C1-C6 alkoxy, chloro and fluoro; R9 is C1-C6 alkyl, C1-C6 alkoxy, chloro or fluoro and a is selected from the integers 0, 1, 2 and 3; (e) 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 hydrocarbons, saturated C7-C12 spiro-bicyclic hydrocarbons and saturated C7-C12 spiro-tricyclic hydrocarbons, provided that said bicyclic and tricyclic hydrocarbons include members other than adamantylidene, bornylidene and norbornylidene, said fluoren-9-ylidene substituents being selected from the group consisting of C1-C4 alkyl, C1-C4 alkoxy, fluoro and chloro; or (f) B and B′are each selected from the groups as defined in (d) (ii) and (d) (iii). A photochromic article comprising a polymeric organic host material and a photochromic amount of a naphthopyran compound of claim 1.
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