Tokuyama Corporation

Tokuyama Soda Kabushiki Kaisha

Satoshi Imura

Takashi Tanaka

Takashi Kobayakawa

Yasuji Kida

Hironobu Nagoh

Kazuhiko Kuramoto

Kazumasa Itonaga

Kenji Tanaka

Toshihiro Nishitake

Junji Momoda

Tsuneyoshi Tanizawa

Shinsuke Tanaka

Seiji Okazaki

Kayo Iwamoto

Process for production of photochromic cured product

A photopolymerizable composition comprising:

Photopolymerizable composition and transparent cured product thereof

Photochromic curable composition

A fulgide or fulgimide compound having a cyclopropyl group as a substituent. The compound has excellent durability which changes reversibly in color from a colorless form to a colored form by the action of light containing ultraviolet rays such as sunlight or the light from a mercury lamp. There are also provided processes for its production, a composition comprising it, and its use.

Photochromic compound

Spiropyrone compounds represented by the general formula ##STR1## wherein ##STR2## is a substituted or an unsubstituted aromatic hydrocarbon group or a substituted or an unsubstituted unsaturated heterocyclic group, and ##STR3## is a substituted or an unsubstituted 2-bicyclo�3,3,1!9-nonenylidene group, that are starting materials of spiropyran compounds which change from a colorless state into a colored or a densely colored state upon irradiation with the light containing ultraviolet rays such as the sunlight or the light of a mercury lamp, the change being reversible, and a process for preparing the spiropyrone compounds. The process comprises reacting a compound represented by the general formula ##STR4## wherein ##STR5## is as defined above, with a compound of the general formula ##STR6## wherein ##STR7## is as defined above.

Process for preparing the spiropyrone compounds

A polymerizable composition comprising at least two di(meth)acrylate compounds of the specific general formula (I), e.g., dimethacrylate compounds of polyethylene glycol adduct of 2,2-bis(4-hydroxyphenyl)propane, wherein the content of di(meth)acrylate compound of the general formula (I) in which m+n is 2 to 3 is 30 to 80 mol % and the content of di(meth)acrylate compound of the general formula (I) in which m+n is 6 to 12 is 20 to 50 mol %, and organic glass formed of a polymer from the polymerizable composition, the polymerizable composition being suitable as a transparent resin, particularly as a raw material for an ophthalmic lens which is free of optical strain, has sufficient hardness and is excellent in impact resistance and light resistance.

Polymerizable composition and organic glass

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 (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.

Photochromic composition

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 compound represented by the following general formula (II): ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, represent a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, a phenyl group, a benzyl group, a phenethyl group, an alkylamine group having 1 to 4 carbon atoms, or a dialkylamino group having 2 to 8 carbon atoms, and ##STR2## represents a nobornylidene group or bicyclo [3,3,1]9-nonylidene group which may have a substituent, and ##STR3## represents a pyridine, quinoline, pyrrole or benzothiophene group which may have a substituent.

A photochromic compound of the present invention is a spiroxazine compound represented by the following formula: ##STR1## wherein R.sup.1 to R.sup.3 represent a monovalent organic group such as alkyl group, Y represents a fused heterocyclic aromatic hydrocarbon group or an unsaturated heterocyclic group if R.sup.1 and R.sup.2 are both methyl groups, and represents an aromatic hydrocarbon group or unsaturated heterocyclic group if R.sup.1 and R.sup.2 are other than the above mentioned. This compound shows an excellent photochromic characteristics even at high temperatures not less than ambient temperature.

Photochromic compound, composition and use thereof

A photochromic compound represented by the following general formula [I] ##STR1## wherein ##STR2## represents a divalent aromatic hydrocarbon group or a divalent heterocyclic group each of which may have a substituent,

Photochromic compound, process for production thereof, use thereof and

Disclosed is a compound represented by the following general formula(I): ##STR1## wherein R.sub.1 and R.sub.2, which may be the same or different, represent a hydrogen atom, an alkyl group, an aryl group, an aralkyl group or a substituted amino group, R.sub.3 and R.sub.4, which may be the same or different, represent an alkyl group, or R.sub.3 and R.sub.4 together form a nobornylidene group or bicyclo (3, 3, 1) 9-nonylidene group which may have a substituent, and ##STR2## represents a divalent aromatic hydrocarbon group or divalent unsaturated heterocyclic group which may have a substituent, with the proviso that when R.sub.3 and R.sub.4 represent an alkyl group, ##STR3## represents a bicyclic aromatic fused ring which is substituted with at least one substituent selected form the group consisting of a halgoen atom, an alkyl group, an alkoxy group, --R.sub.5 --S--R.sub.6 and ##STR4## (in which R.sub.5 represents an alkylene group or --O--R.sub.8).sub.n (in which R.sub.8 represents an alkylene group and n is a positive integer), R.sub.6 and R.sub.7, which may be the same or different, represent an alkyl group, and X represents --N&lt;, --P&lt;, ##STR5## at least one of the substituents being an alkyl group having 6 to 20 carbon atoms, an alkoxy group having 6 to 20 carbon atoms, --R.sub.5 --S--R.sub.6 or ##STR6## a composition comprising this compound, and a photochromic lens composed of this composition.

A compound represented by the following general formula [I] ##STR1## wherein ##STR2## represents a norbornylidene group or an adamantylidene group each of which may have a substituent, and

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Tokuyama, Japan

Satoshi Imura