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US 6,203,729 B1Granted
[Pyrrole]naphthopyranes, their preparation, and compositions and (co)polymer matrices containing them
AssigneeCorning Incorporated
InventorOlivier Breyne
Life of this patent
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Abstract
Disclosed are naphthopyran-type compounds having a pyrrole group annelated in position 5.6, as well as compositions and particularly (co)polymer matrices containing them. These compounds, compositions, and matrices have photochromic properties. These [pyrrole]naphthopyran compounds have the general formula: Articles containing these photochromic compounds, such as ophthalmic and/or solar glasses, lenses, glazing, devices, and the like, are also disclosed.
Claims32
A compound having the following formula (I):
- in which:
- R1 and R2, which are identical or different, independently represent:
- a hydrogen,
- a linear or branched alkyl group which comprises 1 to 12 carbon atoms,
- a cycloalkyl group which comprises 3 to 12 carbon atoms,
- an aryl or heteroaryl group which comprises in its basic structure 6 to 24 carbon atoms or 4 to 24 carbon atoms respectively and at least one heteroatom selected from sulphur, oxygen, and nitrogen;
- said basic structure being optionally substituted with at least one substituent selected from:
- a halogen,
- a hydroxy group,
- a linear or branched alkyl group comprising 1 to 12 carbon atoms,
- a linear or branched alkoxy group comprising 1 to 12 carbon atoms,
- a haloalkyl or haloalkoxy group corresponding to the (C1-C12) alkyl or alkoxy groups above respectively which are substituted with at least one halogen atom,
- a linear or branched alkenyl group comprising 2 to 12 carbon atoms,
- an -NH2 group,
- an -NHR group, R representing a linear or branched alkyl group comprising 1 to 6 carbon atoms,
- a
- group in which R′ and R″ are identical or different and independently represent a linear or branched alkyl group comprising 1 to 6 carbon atoms, or R′ and R″, together with the nitrogen atom to which they are bound, represent a 5- or 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulphur, and nitrogen, said nitrogen being optionally substituted with an R′″ group which is a linear or branched alkyl group comprising 1 to 6 carbon atoms, and
- a methacryloyl group or an acryloyl group, or
- an aralkyl or heteroaralkyl group, the alkyl part of which is linear or branched and comprises 1 to 4 carbon atoms, and the aryl part of which has the same definition as that given above for the aryl and heteroaryl group, or
- said two substituents, R1 and R2, together form an adamantyl, norbornyl, fluorenylidene, di(C1-C6)alkylanthracenylidene, or spiro(C5-C6)cyclo-alkylanthracenylidene group;
- said group being optionally substituted with at least one [of the substituents listed above for R1, R2 :
- an aryl or heteroaryl group] substituent selected from the group consisting of:
- a halogen,
- a hydroxy group,
- a linear or branched alkyl group comprising 1 to 12 carbon atoms,
- a linear or branched alkoxy group comprising 1 to 12 carbon atoms,
- a haloalkyl or haloalkoxy group corresponding to the (C1-Cl2) alkyl or alkoxy groups above respectively which are substituted with at least one halogen atom,
- a linear or branched alkenyl group comprising 2 to 12 carbon atoms,
- an —NH2 group,
- an —NHR group, R representing a linear or branched alkyl group comprising 1 to 6 carbon atoms,
- a
- group in which R′ and R″ are identical or different and independently represent a linear or branched alkyl group comprising 1 to 6 carbon atoms, or R′ and R″, together with the nitrogen atom to which they are bound, represent a 5- or 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulphur, and nitrogen, said nitrogen being optionally substituted with an R′″ group which is a linear or branched alkyl group comprising 1 to 6 carbon atoms, and
- a methacryloyl group or an acryloyl group;
- R3 represents:
- a methyl group,
- a CR5R6OR7 group in which:
- R5 and R6 are identical or different and represent, independently, hydrogen or a linear or branched alkyl group which comprises 1 to 6 carbon atoms, and
- R7 represents:
- hydrogen,
- a linear or branched alkyl group which comprises 1 to 6 carbon atoms,
- an aralkyl group, wherein the alkyl group comprises 1 to 3 carbon atoms and the aryl group is selected from a phenyl or naphthyl group optionally substituted with at least one substituent selected from the group consisting of:
- a halogen,
- a hydroxy group,
- a linear or branched alkyl group comprising 1 to 12 carbon atoms,
- a linear or branched alkoxy group comprising 1 to 12 carbon atoms,
- a haloalkyl or haloalkoxy group corresponding to the (C1-C12) alkyl or alkoxy groups above respectively which are substituted with at least one halogen atom,
- a linear or branched alkenyl group comprising 2 to 12 carbon atoms,
- an —NH2 group,
- an —NHR group, R representing a linear or branched alkyl group comprising 1 to 6 carbon atoms,
- a
- group in which R′ and R″ are identical or different and independently represent a linear or branched alkyl group comprising 1 to 6 carbon atoms, or R′ and R″, together with the nitrogen atom to which they are bound, represent a 5- or 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulphur, and nitrogen, said nitrogen being optionally substituted with an R′″ group which is a linear or branched alkyl group comprising 1 to 6 carbon atoms, and
- a methacryloyl group or an acryloyl group,
- a CH2CN group,
- a CH2COOR8 group in which R8 represents a hydrogen or a linear or branched alkyl group which comprises 1 to 6 carbon atoms, or
- a COR, group in which Rg represents a linear or branched alkyl group which comprises 1 to 6 carbon atoms, a cycloalkyl or bicycloalkyl group which comprises 3 to 12 carbon atoms, a phenyl or naphthyl group optionally substituted with at least one substituent selected from the group consisting of:
- a halogen,
- a hydroxy group,
- a linear or branched alkyl group comprising 1 to 12 carbon atoms,
- a linear or branched alkoxy group comprising 1 to 12 carbon atoms,
- a haloalkyl or haloalkoxy group corresponding to the (C1-C12) alkyl or alkoxy groups above respectively which are substituted with at least one halogen atom,
- a linear or branched alkenyl group comprising 2 to 12 carbon atoms,
- an —NH2 group,
- an —NHR group, R representing a linear or branched alkyl group comprising 1 to 6 carbon atoms,
- a
- group in which R′ and R″ are identical or different and independently represent a linear or branched alkyl group comprising 1 to 6 carbon atoms, or R′ and R″, together with the nitrogen atom to which they are bound, represent a 5- or 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulphur, and nitrogen, said nitrogen being optionally substituted with an R′″ group which is a linear or branched alkyl group comprising 1 to 6 carbon atoms, and
- a methacryloyl group or an acryloyl group, or
- a —COR10, —COOR10, or CONHR10 group, wherein R10 represents a linear or branched alkyl group comprising 1 to 6 carbon atoms, or a cycloalkyl group comprising 3 to 6 carbon atoms, or a linear or branched alkenyl group which comprises 2 to 12 carbon atoms, or a phenyl or benzyl group which is optionally substituted with at least one substituent selected from the group consisting of:
- a halogen,
- a hydroxy group,
- a linear or branched alkyl group comprising 1 to 12 carbon atoms,
- a linear or branched alkoxy group comprising 1 to 12 carbon atoms,
- a haloalkyl or haloalkoxy group corresponding to the (C1-C12) alkyl or alkoxy groups above respectively which are substituted with at least one halogen atom,
- a linear or branched alkenyl group comprising 2 to 12 carbon atoms,
- an —NH2 group,
- an —NHR group, R representing a linear or branched alkyl group comprising 1 to 6 carbon atoms,
- a
- group in which R′ and R″ are identical or different and independently represent a linear or branched alkyl group comprising 1 to 6 carbon atoms, or R′ and R″, together with the nitrogen atom to which they are bound, represent a 5- or 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulphur, and nitrogen, said nitrogen being optionally substituted with an R′″ group which is a linear or branched alkyl group comprising 1 to 6 carbon atoms, and
- a methacryloyl group or an acryloyl group;
- and
- R4 represents:
- hydrogen,
- a linear or branched alkyl group which comprises 1 to 12 carbon,
- a cycloalkyl group which comprises 3 to 12 carbon atoms,
- a linear or branched alkenyl group which comprises 2 to 12 carbon atoms,
- a phenyl or benzyl group which is optionally substituted with at least one substituent selected from the group consisting of:
- a halogen,
- a hydroxy group,
- a linear or branched alkyl group comprising 1 to 12 carbon atoms,
- a linear or branched alkoxy group comprising 1 to 12 carbon atoms,
- a haloalkyl or haloalkoxy group corresponding to the (C1-C12) alkyl or alkoxy groups above respectively which are substituted with at least one halogen atom,
- a linear or branched alkenyl group comprising 2 to 12 carbon atoms,
- an —NH2 group,
- an —NHR group, R representing a linear or branched alkyl group comprising 1 to 6 carbon atoms,
- a
- group in which R′ and R″ are identical or different and independently represent a linear or branched alkyl group comprising 1 to 6 carbon atoms, or R′ and R″, together with the nitrogen atom to which they are bound, represent a 5- or 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulphur, and nitrogen, said nitrogen being optionally substituted with an R′″ group which is a linear or branched alkyl group comprising 1 to 6 carbon atoms, and
- a methacryloyl group or an acryloyl group,
- a —COR10, —COOR10, or CONHR10 group, wherein R10 represents a linear or branched alkyl group comprising 1 to 6 carbon atoms, or a cycloalkyl group comprising 3 to 6 carbon atoms, or a linear or branched alkenyl group which comprises 2 to 12 carbon atoms, or a phenyl or benzyl group which is optionally substituted with at least one substituent selected from the group consisting of:
- a halogen,
- a hydroxy group,
- a linear or branched alkyl group comprising 1 to 12 carbon atoms,
- a linear or branched alkoxy group comprising 1 to 12 carbon atoms,
- a haloalkyl or haloalkoxy group corresponding to the (C1-C12) alkyl or alkoxy groups above respectively which are substituted with at least one halogen atom,
- a linear or branched alkenyl group comprising 2 to 12 carbon atoms,
- an —NH2 group,
- an —NHR group, R representing a linear or branched alkyl group comprising 1 to 6 carbon atoms,
- a
- group in which R′ and R″ are identical or different and independently represent a linear or branched alkyl group comprising 1 to 6 carbon atoms, or R′ and R″, together with the nitrogen atom to which they are bound, represent a 5- or 7-membered ring which can comprise at least one other heteroatom selected from oxygen, sulphur, and nitrogen, said nitrogen being optionally substituted with an R′″ group which is a linear or branched alkyl group comprising 1 to 6 carbon atoms, and
- a methacryloyl group or an acryloyl group, or
- a methacryloyl group or an acryloyl group.
106 more elements
Dependencies are inferred from the claim text.