Photochromic composition
AssigneeTokuyama Corporation
InventorsTakashi Kobayakawa, Satoshi Imura, Kazumasa Itonaga, Kazuhiko Kuramoto
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AssigneeTokuyama Corporation
InventorsTakashi Kobayakawa, Satoshi Imura, Kazumasa Itonaga, Kazuhiko Kuramoto
Estimating the term…
A photochromic composition comprising (A) 100 parts by weight of a compound having at least one epoxy group in the molecule and (B) 0.0001 to 10,000 parts by weight of a photochromic compound. The compound (A) is represented by the following general formula ##STR1## wherein A is a residue of an n-valent alcoholic hydroxyl-containing compound, a residue of an n-valent phenolic-hydroxyl-containing compound, or a residue of an n-valent carboxylic acid, R.sup.1 is a hydrogen atom or a methyl group, and n is an integer of 1 to 4. Examples of the (A) compound include alcoholic hydroxyl-containing compounds such as monohydric, dihydric or trihydric alcohols, reaction products of phenolic hydroxyl-containing compounds such as phenol or hydroquinone with epichlorohydrin, or reaction products of carboxylic acids such as benzoic acid, or terephthalic acid with epichlorohydrin. Examples of the (B) photochromic compound include fulgide compounds, spirooxazine compounds and chromene compounds. A polymer obtained by polymerizing the above photochromic composition of the invention by a radical polymerization method has a good durability of photochromic properties, and also possesses a dark color-forming density, a fast color fading speed, is transparent, and has a high surface hardness. Thus, especially, the polymer is suitable for use as a photochromic lens.
A photochromic composition composed of (A) 100 parts by weight of a compound having at least one radical-polymerizable group and at least one epoxy group in the molecule and having the following general formula ##STR29## wherein each of R.sup.1 and R.sup.4 is a hydrogen atom or a methyl group and R.sup.2 and R.sup.3 represent an alkylene group having 1 to 4 carbon atoms which may be substituted by hydroxyl groups, or a group of ##STR30## wherein m and n are 0 or 1, and (B) 0.001 to 10,000 parts by weight of a photochromic compound.
A photochromic composition comprising (A) 100 parts by weight of an epoxy compound having an epoxy group represented by general formula (I) and (B) 0.0001 to 10,000 parts by weight of a fulgide compound represented by general formula (II), ##STR42## wherein each of R.sup.1 and R.sup.4 is a hydrogen atom or a methyl group and R.sup.2 and R.sup.3 represent the same or different alkylene groups having 1 to 4 carbon atoms which may be substituted by hydroxyl group, or a group of ##STR43## wherein m and n are 0 or 1, ##STR44## wherein ##STR45## is a divalent aromatic hydrocarbon group containing a benzene group and fused rings of 2 or 3 benzene rings or containing a divalent unsaturated heterocyclic group having 5- to 7-membered rings containing 1 to 2 oxygen atoms, nitrogen atoms or sulfur atoms as ring-constituted atoms, or fused rings of said ring and a benzene ring, each of which may contain a member selected from halogen atoms, alkyl groups having 1 to 4 carbon atoms, alkoxy groups having 1 to 4 carbon atoms, aryl groups having 6 to 10 carbon atoms, alkoxyaryl groups having 7 to 14 carbon atoms, such as aryl groups having 6 to 10 carbon atoms substituted by alkoxy groups having 1 to 4 carbon atoms, amino group, nitro group, and cyano group, R.sub.1 is an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a monovalent heterocyclic group having a 5- to 7-membered ring containing 1 to 2 oxygen atoms, nitrogen atoms or sulfur atoms as ring-constituted atoms or fused rings of the multi-membered ring and a benzene ring, ##STR46## is a norbornylidene group or an adamantylidene group, X is an oxygen atom, a group >N--R.sub.2, a group >N--A.sub.1 --B.sub.1 --(A.sub.2).sub.m --(B.sub.2).sub.n --R.sub.3, a group >N--A.sub.3 --A.sub.4 or a group >N--A.sub.3 --A.sub.4 in which R.sub.2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms, A.sub.1, A.sub.2, or A.sub.3 are the same or different and each represents an alkylene group having 1 to 4 carbon atoms or an alkylidene group having 2 to 4 carbon atoms, a cyclohexylene group or a dimethyl-cyclohexane-diyl group, B.sub.1 and B.sub.2 are the same or different and each may represent ##STR47## m and n are independently 0 or 1, and when m is 0, n is 0, R.sub.3 is an alkyl group having 1 to 4 carbon atoms, a naphthyl group or a naphthylalkyl group having 11 to 14 carbon atoms, A.sub.4 is a naphthyl group, and R.sub.4 is a halogen atom, a cyano group or a nitro group.
A photochromic composition comprising (A) 100 parts by weight of an epoxy compound having an epoxy group represented by general formula (I) and (B) 0.0001 to 10,000 parts by weight of a fulgide compound represented by general formula (II), and (C) 0.001 to 10 parts by weight, per 100 parts by weight of the epoxy compound (A), of a radical-polymerization initiator, ##STR51## wherein each of R.sup.1 and R.sup.4 is a hydrogen atom or a methyl group and R.sup.2 and R.sup.3 represent the same or different alkylene groups having 1 to 4 carbon atoms which may be substituted by hydroxyl group, or a group of ##STR52## wherein m and n are 0 or 1, ##STR53## wherein ##STR54## is a divalent aromatic hydrocarbon group containing a benzene group and fused rings of 2 or 3 benzene rings or containing a divalent unsaturated heterocyclic group having 5- to 7-membered rings containing 1 to 2 oxygen atoms, nitrogen atoms or sulfur atoms as ring-constituted atoms, or fused rings of said ring and a benzene ring, each of which may contain a member selected from halogen atoms, alkyl groups having 1 to 4 carbon atoms alkoxy groups having 1 to 4 carbon atoms, aryl groups having 6 to 10 carbon atoms, alkoxyaryl groups having 7 to 14 carbon atoms, such as aryl groups having 6 to 10 carbon atoms substituted by alkoxy groups having 1 to 4 carbon atoms, amino group, nitro group, and cyano group, R.sub.1 is an alkyl group having 1 to 4 carbon atoms, an aryl group having 6 to 10 carbon atoms, and a monovalent heterocyclic group having a 5- to 7-membered ring containing 1 to 2 oxygen atoms, nitrogen atoms or sulfur atoms as ring-constituted atoms or fused rings of the multi-membered ring and a benzene ring, ##STR55## is a norbornylidene group or an adamantylidene group, X is an oxygen atom, a group >N--R.sub.2, a group >N--A.sub.1 --B.sub.1 --(A.sub.2).sub.m --(B.sub.2).sub.n --R.sub.3, a group >N--A.sub.3 --A.sub.4 or a group >N--A.sub.3 --A.sub.4 in which R.sub.2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms, A.sub.1, A.sub.2, or A.sub.3 are the same or different and each represents an alkylene group having 1 to 4 carbon atoms or an alkylidene group having 2 to 4 carbon atoms, a cyclohexylene group or a dimethyl-cyclohexane-diyl group, B.sub.1 and B.sub.2 are the same or different and each may represent ##STR56## m and n are independently 0 or 1, and when m is 0, n is 0, R.sub.3 is an alkyl group having 1 to 4 carbon atoms, a naphthyl group or a naphthylalkyl group having 11 to 14 carbon atoms, A.sub.4 is a naphthyl group, and R.sub.4 is a halogen atom, a cyano group or a nitro group.
A photochromic composition composed of (A) 100 parts by weight of a compound having at least one radical-polymerizable group and at lest one epoxy group in the molecular and having the following general formula ##STR57## wherein each of R.sup.1 and R.sup.4 is a hydrogen atom of a methyl group and R.sup.2 amd R.sup.3 represent an alkylene group having 1 to 4 carbon atoms which may be substituted by hydroxyl groups, or a group of ##STR58## wherein m and n are 0 or 1, (B) 0.001 to 10,000 parts by weight of a photochromic compound being composed of a combination of (1) a photochromic compound having the following formula ##STR59## wherein ##STR60## is a divalent aromatic hydrocarbon group or a divalent unsaturated heterocyclic group each of which may be substituted by a halogen atom, an ethyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms or an aryl group having 6 to 10 carbon atoms, R.sup.1 is an alkyl group, an aryl group, or a monovalent heterocyclic group, ##STR61## is a norbornylidene group or an adamantylidene group, X is an oxygen atom, a group >N--R.sub.2, a group >N--A.sub.1 --B.sub.1 --(A.sub.2).sub.m --(B.sub.2).sub.n --R.sub.3, a group >N--A.sub.3 --A.sub.4 or a group >N--A.sub.3 --R.sub.4 in which R.sub.2 is a hydrogen atom, an alkyl group or an aryl group, A.sub.1, A.sub.2, or A.sub.3 are the same or different and each represents an alkylene group or an alkylidene group, a cycloalkylene group or an alkylcycloalkane-diyl group, B.sub.1 and B.sub.2 are the same or different and each may represent ##STR62## m and n are independently 0 or 1, and when m is 0, n is 0, R.sub.3 is an alkyl group a naphthyl group or a naphthylalkyl group, A.sub.4 is a naphthyl group, and R.sub.4 is a halogen atom, a cyano group or a nitro group and (2) a photochromic compound having the following formula ##STR63## wherein R.sub.1 and R.sub.2 are both hydrogen atoms, R.sub.3 and R.sub.4 are the same or different alkyl groups having 1 to 4 carbon atoms, or together may form a cicyclo (3,3,1)9-nonylidene group or a norbornylidene group, and ##STR64## is an aromatic hydrocarbon group which may be substituted by an alkyl group having 1 to 20 carbon atoms or an alkoxy group having 1 to 20 carbon atoms.
Dependencies are inferred from the claim text.