Mitsubishi Gas Chemical Company, Inc.

Mitsubishi Gas Chemical, Inc.

Kikuo Furukawa

Hiroshi Horikoshi

Hiroyasu Tanaka

Yoshio Nishimura

Shoichi Hayakawa

Minoru Kakuda

Eiji Koshiishi

Kousuke Namiki

Hiroyuki Tanagi

Takehiko Isobe

Yoshihisa Arai

Sawako Fuse

Takashi Aoki

Toshiaki Yamada

Kouhei Takemura

Hitoshi Okazaki

Yousuke Imagawa

Takashi Onozawa

Hiroshi Kurata

Kazuki Kariyazono

Toshiharu Yamashita

Mitsuharu Suzuki

A composition for a high refractive index, low dispersion resin for a close-contact double layer-type composite diffractive optical element that is highly photocurable and provides a high productivity, and a close-contact double layer-type composite diffractive optical element using such composition are provided. A composition for a high refractive index, low dispersion resin for a close-contact double layer-type composite diffractive optical element includes a thiol compound represented by general formula (1) or an oligomer synthesized by use of a thiol compound represented by general formula (1) (A component); and an ene compound including two or more polymerizable unsaturated bonds (B component). (In the formula, p represents an integer of 2 to 5; Xand Zindependently represent a hydrogen atom or a mercaptomethyl group; a ratio of sulfur atoms in a molecule is 40 to 80% by mass; and the number of thiol groups is 3 or larger.).

Composition for high refractive index low dispersion resins for composite diffractive optical elements, and composite diffractive optical element using the same

The purpose of the present invention is to appropriately control the rate of polymerization of a composition in which a thiol compound and an isocyanate compound are added to an episulfide compound and thereby provide an optical material which has high transparency. This composition for use as optical material comprises (a) an episulfide compound, (b) an isocyanate compound, (c) a thiol compound, and (d) a benzyl halide compound represented by formula (1): wherein: X is a halogen; L is selected from the group consisting of a hydrogen atom, a methyl group, a halogen, a mercaptomethyl group, and an isocyanate methyl group; and n is 1 or 2.

Composition for use as optical material

According to the present invention, it is possible to provide a photocurable composition which comprises a cyclic compound (a) represented by formula (1), an episulfide compound (b), and a photopolymerization initiator (c). In a preferred embodiment, the proportion of the cyclic compound (a) in the photocurable composition is 5-80 mass %, the proportion of the episulfide compound (b) is 20-95 mass %, and the proportion of the photopolymerization initiator (c) is 0.1-10 parts by mass per 100 parts by mass of the sum of the cyclic compound (a) and the episulfide compound (b). In the formula, C represents a carbon atom, X represents S, Se, or Te, and a to f are integers of 0-3, provided that 8&#x2265;(a+c+e)&#x2265;1, 8&#x2265;(b+d+f)&#x2265;2, and (b+d+f)&#x2265;(a+c+e). 

Photocurable composition and optical material

The present invention can provide a method for producing a cured product of an episulfide-based resin, the method having: (A) a step for obtaining a composition for a resin by mixing compound (a), compound (b) and a polymerization catalyst; (B) a step for pouring the composition for a resin into a mold; and (C) a step in which, by increasing the temperature of a heating medium, the composition for a resin is polymerized in the heating medium that contains a liquid having a thermal conductivity of 0.2 W/m&#xb7;K or higher, or in a shower of the heating medium. The maximum temperature of the heating medium in step (C) is 55 to 110&#xb0; C. wherein m represents an integer from 0 to 4 and n represents an integer from 0 to 2

Method for producing cured product of episulfide-based resin

Provided are a novel alicyclic ester compound and a method for producing a compound of general formula (1) at a high yield from a compound of general formula (2) and a compound of general formula (3). An adamantane compound expressed by general formula (2) and a hydroxyalkyl (meth)acrylate ester compound expressed by general formula (3) are reacted with each other by use of a dehydration condensation agent as a catalyst to obtain an alicyclic ester compound expressed by general formula (1).

(Meth)acrylic acid ester compound and production method therefor

Provided are a resist and a compound for the resist improving the sensitivity, the resolution and the line edge roughness (LER) in a good balance without spoiling basic properties of a chemical amplification resist such as pattern shape, dry etching resistance, heat resistance and the like. Provided are a method for producing an alicyclic ester compound expressed by general formula (1), an alicyclic ester compound expressed by general formula (1), a (meth)acrylic copolymer obtained by polymerization of the alicyclic ester compound, and a photosensitive resin composition containing the (meth)acrylic copolymer. A method for producing an alicyclic ester compound expressed by general formula (1) includes reacting an adamantane compound expressed by general formula (2) with hydroxyalkylamine expressed by general formula (3) to produce an adamantaneamide compound expressed by general formula (4), and then reacting the adamantaneamide compound expressed by general formula (4) with (meth)acrylic acid.

Method for producing novel ali cyclic ester compound, novel alicyclic ester compound, (meth)acrylic copolymer produced by polymerizing said compound, and photosensitive resin composition using said copolymer

The present invention provides a resist or a compound for use as a resist, which is highly sensitive and well-balanced without losing the fundamental physical properties required as a chemically amplified resist (e.g., resolution, line edge roughness (LER)). The present invention is directed to a (meth)acrylate compound represented by general formula (1) and a process for preparation thereof, as well as a (meth)acrylic copolymer obtainable by polymerization of the (meth)acrylate compound of general formula (1) and a photosensitive resin composition thereof: (wherein Rrepresents a hydrogen atom or a methyl group, Rrepresents a linear or branched alkyl group containing 2 to 4 carbon atoms, and each Rmay be the same or different and represents a group represented by the following formula (2) or (3), etc.) (provided that formulae (2) and (3) are as defined in the specification of the present application).

(Meth)acrylate compound, (meth)acrylic copolymer and photosensitive resin composition containing same

According to the present invention, a curable composition can be provided, said composition being characterized by comprising: (A) an episulfide compound; and (B) a photobase generator comprising an organoboron compound represented by general formula (1) below: (In general formula (1), R, R, R, Rand Rmay be the same as or different from one another and independently represent an alkyl group having 1 to 8 carbon atoms; and Ar, Arand Armay be the same as or different from one another and independently represent a group selected from the group consisting of a phenyl group, a naphthyl group, an anthracenyl group and a phenanthryl group, each of which may have a substituent selected from the group consisting of an alkyl group, an aryl group, an alkenyl group, a cycloalkyl group and a heterocyclic group.)

Curable composition

The present invention provides, as a chemically amplified resist, a well-balanced resist or compound which results in improved sensitivity, resolution and line edge roughness (LER) without impairing the fundamental physical properties required as a resist (e.g., pattern shape, dry etching resistance, heat resistance). A mixture of cycloaliphatic ester compounds represented by general formulae (1) to (3), and a process for preparation thereof, as well as a (meth)acrylic copolymer comprising the cycloaliphatic ester compounds of general formulae (1) to (3) and a photosensitive resin composition thereof are provided.

Alicyclic ester compound, and (meth)acrylic copolymer and photosensitive resin composition containing same

The present invention can provide a process for producing a hydroxy adamantane carboxylic acid compound represented by the above formula (2), which comprises (i) reacting an adamantane compound represented by the above formula (1) with carbon monoxide or with a carbon monoxide source in a proton acid solution prepared at a concentration of 90% by mass or more to thereby cause carboxylation of the OX group(s), and then (ii) adding an oxidizing agent to the reaction mixture to cause oxidation of the bridgehead C&#x2014;H bond to thereby generate a hydroxyl group.

Process for producing hydroxy adamantane carboxylic acid compounds

Provided according to the present invention are an adamantyl (meth)acrylate represented by formula (1), having a formazin standard turbidity of less than 1.7 NTU (Nephelometric Turbidity Unit) in methylethylketone or tetrahydrofuran, and also a (meth)acrylic copolymer comprising the adamantyl (meth)acrylate as a repeating unit: 

Adamantyl (meth)acrylic monomer and (meth)acrylic polymer containing the same as repeating unit

The present invention provides an efficient production method suitable to industrial-scale production not requiring column purification for adamantyl (meth)acrylates having an adamantine skeleton having utility in crosslinked resins, optical fibers, optical waveguides, optical disc substrates and other optical materials.

Method for producing adamantyl (meth)acrylates

The adamantane derivatives of the present invention which are represented by the general formula (1): wherein X is a hydrogen atom, alkyl, halogen-containing alkyl, halogen, or hydroxyl-, halogen-, nitrile- or ether-containing hydrocarbyl, and a plurality of X groups, if any, may be the same or different from each other; nis an integer of 1 to 14; Rto Rmay be the same or different from each other and are independently alkyl or halogen-containing alkyl; and Yand Ymay be the same or different from each other and are independently a hydrogen atom or a group represented by the general formula (2): wherein Rto Rmay be the same or different from each other and are independently a hydrogen atom, alkyl, halogen or halogen-containing alkyl, are excellent in optical properties, heat resistance and acid-dissociating property, and useful as crosslinking-type resins, optical materials such as optical fibers, light wave guides, optical disk substrates and photoresists as well as raw materials thereof, intermediate products of medicines or agricultural chemicals, and various other industrial products.

Adamantane derivatives and resin compositions using the same as raw material

In the present invention, an adamantyl acrylate compound is produced by a process comprising a first step and a second step without using acid halide. In the first step, a 2-adamantanone compound is reacted with a hydrocarbyl halide in the presence of lithium metal to form an adamantanolate intermediate that is then reacted with an acrylic ester compound in the second step to produce the aimed adamantyl acrylate compound.

Production method of adamantyl acrylate compounds

Adamantanediols are produced by the hydroxylation of adamantane compounds in a water/organic solvent two-phase system in the presence of a ruthenium compound and a hypochlorite. Throughout the hydroxylation, the hypochlorite concentration in the water phase is regulated within a narrow limited range, for example, by monitoring the pH of the reaction system. With such a control of the hypochlorite concentration, the adamantanediols are produced in a high selectivity and a high yield.

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Tokyo, Japan

Kikuo Furukawa