Patents Assigned to Maruzen Petrochemical Co., Ltd.
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Patent number: 9216948Abstract: A method for producing a copolymer for semiconductor lithography containing less metal impurities, and a method for purifying a polymerization initiator for production of the copolymer, are provided. The method for purifying a polymerization initiator to be used for production of a polymer includes a filtering step wherein a solution of a polymerization initiator dissolved in an organic solvent is allowed to pass through a filter having a nominal pore size of not more than 1.0 ?m, to reduce the sodium content of the polymerization initiator solution to not more than 300 ppb with respect to the weight of the polymerization initiator. Further, the method for producing a copolymer for semiconductor lithography includes a polymerization step wherein the polymer for semiconductor lithography is synthesized by a radical polymerization reaction in the presence of a polymerization initiator purified by the above purification method.Type: GrantFiled: April 20, 2012Date of Patent: December 22, 2015Assignee: Maruzen Petrochemical Co., Ltd.Inventor: Youji Suzuki
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Patent number: 9023982Abstract: A method is provided for purifying a resin for photolithography wherein, from an insufficiently purified resin (also referred to as “crude resin”), low molecular weight impurities such as an unreacted monomer and a polymerization initiator, which cause a development defect of a resist pattern or deterioration of the storage stability of the resin for photolithography can be removed more effectively. The method for purifying a resin for photolithography includes an operation (a) wherein a slurry in which a resin is dispersed in a solution containing a good solvent and a poor solvent is stirred, and then an operation (b) wherein, to said slurry, a poor solvent is added to lower the ratio of the good solvent to the poor solvent, and then, the resin is separated from the solution.Type: GrantFiled: November 5, 2013Date of Patent: May 5, 2015Assignee: Maruzen Petrochemical Co., Ltd.Inventor: Tomo Oikawa
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Publication number: 20150005467Abstract: [Object] To provide a method of producing a homopolymer or random copolymer of hydroxyl group-containing vinyl ether simply and conveniently as well as efficiently. [Means for solving problem] A method of producing a homopolymer or random copolymer of hydroxyl group-containing vinyl ether according to the present invention comprises the step of polymerizing a monomer component comprising at least one hydroxyl group-containing vinyl ether using an oil-soluble radical polymerization initiator in the absence or presence of a solvent.Type: ApplicationFiled: February 4, 2013Publication date: January 1, 2015Applicant: Maruzen Petrochemical Co., Ltd.Inventors: Shinji Sugihara, Tomohiro Masukawa
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Patent number: 8859180Abstract: [Task to Be Achieved] To provide a chemically amplified type positive copolymer for semiconductor lithography, which has eliminated the problems of prior art, has a high development contrast, and has excellent resolution in fine-pattern formation; a composition for semiconductor lithography which contains the copolymer; and a process for producing the copolymer. [Means for Achievement] The copolymer for semiconductor lithography according to the present invention is a copolymer which has at least (A) a repeating unit having a structure which has an alkali-soluble group protected by an acid-labile, dissolution-suppressing group, (B) a repeating group having a lactone structure and (C) a repeating group having an alcoholic hydroxyl group and which is characterized by having an acid value of 0.01 mmol/g or less as determined by dissolving the copolymer in a solvent and subjecting the solution to neutralization titration with a solution of an alkali metal hydroxide using Bromothymol Blue as an indicator.Type: GrantFiled: October 19, 2007Date of Patent: October 14, 2014Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Tomo Oikawa, Takayoshi Okada, Masaaki Kudo, Takanori Yamagishi
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Publication number: 20140287219Abstract: An optical element material which is obtained by curing a resin composition for photoimprinting containing a photocurable monomer (A) of the formula (1) and a photocurable monomer (B) of the formula (2) in a weight ratio of from 30/70 to 87/13, and containing a photopolymerization initiator (C) in a content of from 0.01 to 30 parts by weight per 100 parts by weight of the total weight of the monomer (A) and the monomer (B), and which has a shrinkage on curing of at most 4.5%, and a method for producing it: wherein R1 is —CH?CH2, —CH2CH2—O—CH?CH2, —CH2—C(CH3)?CH2 or a glycidyl group; R2 and R3 are each independently hydrogen or a C1-4 alkyl group; R4 and R5 are each independently —O—CH?CH2, —O—CH2CH2—O—CH?CH2, —O—CO—CH?CH2, —O—CO—C(CH3)?CH2, —O—CH2CH2—O—CO—CH?CH2, —O—CH2CH2—O—CO—C(CH3)?CH2 or a glycidyl ether group; and R6 and R7 are each independently hydrogen or a C1-4 alkyl group.Type: ApplicationFiled: September 25, 2012Publication date: September 25, 2014Applicant: MARUZEN PETROCHEMICAL CO., LTD.Inventors: Yoshihisa Hayashida, Takuro Satsuka, Teruyo Ikeda
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Patent number: 8759462Abstract: A method for producing a resist copolymer having a weight-average molecular weight of not less than 3000 and not more than 6000, in which copolymer the contents of an oligomer having a molecular weight of not more than 1000 and a byproduct derived from a polymerization initiator are small, is provided. The method for producing a resist copolymer comprises the step of continuously supplying a solution containing a monomer and a solution containing a polymerization initiator to a heated solvent to carry out a radical polymerization, wherein the variation range of the concentration of the polymerization initiator in polymerization solution is within ±25% of the median value between the maximum concentration and the minimum concentration during specific time; and the variation range of the concentration of unreacted monomer in the polymerization solution is within ±35% of the median value between the maximum concentration and the minimum concentration during specific time.Type: GrantFiled: November 13, 2012Date of Patent: June 24, 2014Assignee: Maruzen Petrochemical Co., Ltd.Inventor: Tomo Oikawa
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Patent number: 8721950Abstract: A resin for thermal imprint include a cyclic-olefin-based thermoplastic resin that contains at least one of skeletons represented by the following chemical equation 1 or the following chemical equation 2 in a main chain. The glass transition temperature Tg (° C.) and the value ([M]) of MFR at 260° C. satisfy the following equation 1, and [M]>10. The thermal imprint characteristics (transferability, mold release characteristic, and the like) are superior and the productivity (throughput) is improved. Tg(° C.Type: GrantFiled: November 1, 2012Date of Patent: May 13, 2014Assignees: Scivax Corporation, Maruzen Petrochemical Co., Ltd.Inventors: Takemori Toshifumi, Yoshiaki Takaya, Takahito Mita, Tetsuya Iizuka, Yuji Hashima, Takahisa Kusuura, Mitsuru Fujii, Takuji Taguchi, Anupam Mitra
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Patent number: 8709698Abstract: A radical polymerization initiator represented by the following formula (G) in the formula (G), R71 and R72 are each a hydrocarbon group of 3 to 6 carbon atoms which may contain nitrogen atom; R73 and R74 are each a hydrogen atom or an acid-dissociating, dissolution-suppressing group; and at least one of R73 and R74 is an acid-dissociating, dissolution-suppressing group represented by the following formula (R78); and wherein R77 is a hydrocarbon group of 1 to 26 carbon atoms which may contain hetero atoms.Type: GrantFiled: September 12, 2011Date of Patent: April 29, 2014Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Minoru Iijima, Takanori Yamagishi
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Publication number: 20140058028Abstract: Provided are a metal nanoparticle composite which exhibits excellent stability over time and retention stability and is useful as a raw material for a metal nanoparticle-dispersed film, a method for producing the composite, a metal nanoparticle dispersion liquid, a composition for forming a metal nanoparticle-dispersed film, and a metal nanoparticle-dispersed film. Disclosed is a metal nanoparticle composite comprising (A) a star-shaped polymer having a central core and arms bonded to the central core, the arms comprising a repeating unit represented by the following formula (1) and a repeating unit represented by the following formula (2); and (B) metal nanoparticles supported thereon: wherein in the formula (1), R1 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; and in the formula (2), R2 represents a methyl group or an ethyl group; and k represents an integer from 1 to 10.Type: ApplicationFiled: January 25, 2012Publication date: February 27, 2014Applicant: Maruzen Petrochemical Co., LTD.Inventors: Norihiro Yoshida, Takao Nishiura
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Publication number: 20140015162Abstract: A mold for imprinting has a mold pattern for transferring a pattern to a processing object. A base layer having a predetermined base pattern is formed by imprinting on a thermoplastic resin, a thermosetting resin, a photo-curable resin, or the like, and a mold layer is formed in such a way that the mode pattern is shapened along a surface of the base pattern by a surface preparation technique, such as CVD, PVD, or plating.Type: ApplicationFiled: September 17, 2013Publication date: January 16, 2014Applicant: MARUZEN PETROCHEMICAL CO., LTD.Inventors: Takahisa Kusuura, Anupam Mitra, Yoshiaki Takaya, Takuro Satsuka
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Patent number: 8597769Abstract: There are provided an etching mask which has a superior thermal imprinting characteristic and also a good anti-etching characteristic, a base material with the etching mask, a microfabricated product to which those etching mask and base material are applied, and a production method of the microfabricated product. The etching mask formed of a thermoplastic resin containing at least one kind of skeleton expressed by a chemical formula (1) or a chemical formula (2) in a main chain wherein R1, R2, R3, R4, R5, R6, R7, R8 in the formulae (1), (2) can be different or same one another, each of which is a hydrogen atom, a deuterium atom, a hydrocarbon group having a carbon number of 1 to 15, a halogen atom, or a substituent group containing a hetero atom like oxygen or sulfur, and may form a ring structure one another and wherein m and n are integers equal to or greater than 0.Type: GrantFiled: November 13, 2008Date of Patent: December 3, 2013Assignee: Maruzen Petrochemical Co. Ltd.Inventors: Yoshiaki Takaya, Takuro Satsuka, Yoshihisa Hayashida, Takahisa Kusuura, Anupam Mitra
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Publication number: 20130288021Abstract: A resin composition for photoimprinting, a cured product of the resin composition which is excellent in etching and heat resistance, and a pattern forming process using the resin composition are provided. The resin composition contains photocurable monomer (A) containing at least one carbazole compound of formula (I): a photocurable monomer (B) containing at least one compound of the following formulae (II), (III), and (IV): and a photopolymerization initiator (C). The weight ratio of the photocurable monomer (A) to the photocurable monomer (B) is from 30/70 to 87/13.Type: ApplicationFiled: December 2, 2011Publication date: October 31, 2013Applicant: Maruzen Petrochemical Co., Ltd.Inventors: Yoshihisa Hayashida, Takuro Satsuka, Teruyo Ikeda, Norio Futaesaku, Toshifumi Takemori
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Patent number: 8492483Abstract: To provide a novel ABA-type triblock copolymer of vinyl ether series, comprising polyvinyl ether and an oxystyrene-series unit, and a process of producing the ABA-type copolymer at a series of steps. The invention relates to a novel ABA-type triblock copolymer comprising Segment A comprising an oxystyrene-series repeat unit (a) and Segment B comprising a vinyl ether-series repeat unit (b), in which the Segment A and the Segment B are bonded together with a single bond, and to a simple process of producing the same. The triblock copolymer can be produced at a series of steps in a simple manner, comprising living cationic polymerization of a vinyl ether-series monomer such as ethyl vinyl ether in the presence of a bifunctional initiator and a Lewis acid, and subsequently adding an oxystyrene-series monomer such as p-hydroxystyrene for living cationic polymerization.Type: GrantFiled: June 19, 2008Date of Patent: July 23, 2013Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Norihiro Yoshida, Hijiri Aoki, Takahito Mita, Ami Yamaguchi, Kazuhiko Haba, Goro Sawada
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Patent number: 8455596Abstract: The present invention provides a method for production of a copolymer for photoresists in which the bias of the monomer composition ration is small. This method for production is a method for production of a copolymer for photoresists, which copolymer containing at least two types of repeating units, the method having a supplying step of supplying a monomer solution and a solution containing a polymerization initiator into a polymerization reaction system, wherein the range of fluctuation of the monomer composition ratio of unreacted monomers is within the range between minus 15% and plus 15% or the standard deviation of the monomer composition ratio of unreacted monomers is within 2 in the polymerization reaction system during the period from the start of the polymerization reaction to the end of supplying of the monomer solution.Type: GrantFiled: February 9, 2010Date of Patent: June 4, 2013Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Tomo Oikawa, Eiichi Ikawa
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Publication number: 20130131405Abstract: A liquid molding resin component for a reaction injection molding process includes a liquid resin reaction monomer including metathesis polymerizable cycloolefin and a plurality of nonswelling mica. The plurality of nonswelling mica have an average particle size in a range of about 35 micro m to about 500 micro m and have a bulk density in a range of about 0.10 g/ml to about 0.27 g/ml. Further, a liquid resin component system for a reaction injection molding process includes a plurality of liquid resin components, at least one of which includes a catalyst, at least one of which includes an activator, and at least one of which includes a plurality of nonswelling mica having an average particle size in a range of about 35 micro m to about 500 micro m and having a bulk density in a range of about 0.10 g/ml to 0.27 g/ml.Type: ApplicationFiled: November 18, 2011Publication date: May 23, 2013Applicants: METTON AMERICA, INC., MARUZEN PETROCHEMICAL CO., LTD.Inventors: HIROMITSU BABA, TAKESHI KATO, HIROYUKI MINAMI, MASANORI ABE, YUSUKE YOKOO, BEAU JEREMY WEST
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Publication number: 20130123446Abstract: A method for producing a resist copolymer having a weight-average molecular weight of not less than 3000 and not more than 6000, in which copolymer the contents of an oligomer having a molecular weight of not more than 1000 and a byproduct derived from a polymerization initiator are small, is provided. The method for producing a resist copolymer comprises the step of continuously supplying a solution containing a monomer and a solution containing a polymerization initiator to a heated solvent to carry out a radical polymerization, wherein the variation range of the concentration of the polymerization initiator in polymerization solution is within ±25% of the median value between the maximum concentration and the minimum concentration during specific time; and the variation range of the concentration of unreacted monomer in the polymerization solution is within ±35% of the median value between the maximum concentration and the minimum concentration during specific time.Type: ApplicationFiled: November 13, 2012Publication date: May 16, 2013Applicant: MARUZEN PETROCHEMICAL CO., LTD.Inventor: MARUZEN PETROCHEMICAL CO., LTD.
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Publication number: 20130056906Abstract: A resin for thermal imprint include a cyclic-olefin-based thermoplastic resin that contains at least one of skeletons represented by the following chemical equation 1 or the following chemical equation 2 in a main chain. The glass transition temperature Tg (° C.) and the value ([M]) of MFR at 260° C. satisfy the following equation 1, and [M]>10. The thermal imprint characteristics (transferability, mold release characteristic, and the like) are superior and the productivity (throughput) is improved. Tg(° C.Type: ApplicationFiled: November 1, 2012Publication date: March 7, 2013Applicants: MARUZEN PETROCHEMICAL CO., LTD., SCIVAX CORPORATIONInventors: SCIVAX CORPORATION, MARUZEN PETROCHEMICAL CO., LTD.
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Method for producing a copolymer solution with a uniform concentration for semiconductor lithography
Patent number: 8377625Abstract: A method of producing a copolymer solution for semiconductor lithography having a copolymer and a solvent for coating film formation, which copolymer contains at least one repeating unit selected from the group consisting of: a repeating unit (A) having a hydroxyl group; a repeating unit (B) having a structure in which a hydroxyl group is protected by a group which suppresses dissolution into an alkaline developer and which dissociates in the action of an acid; a repeating unit (C) having a lactone structure; and a repeating unit (D) having a cyclic ether structure, the difference in the copolymer concentration among a plurality of containers which were filled with copolymer solution from the same manufacturing lot is not more than a certain range, or the method includes a certain production step.Type: GrantFiled: October 28, 2009Date of Patent: February 19, 2013Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Takanori Yamagishi, Ichiro Kato, Akiko Tanaka, Miyako Asano -
Patent number: 8324332Abstract: A resin for thermal imprint including a cyclic-olefin-based thermoplastic resin that contains at least one of skeletons represented by the following chemical equation 1 or the following chemical equation 2 in a main chain. The glass transition temperature Tg (° C.) and the value ([M]) of MFR at 260° C. satisfy the following equation 1, and [M]>10. The thermal imprint characteristics (transferability, mold release characteristic, and the like) are superior and the productivity (throughput) is improved. Tg (° C.Type: GrantFiled: August 25, 2006Date of Patent: December 4, 2012Assignees: Scivax Corporation, Maruzen Petrochemical Co., Ltd.Inventors: Takemori Toshifumi, Yoshiaki Takaya, Takahito Mita, Tetsuya Iizuka, Yuji Hashima, Takahisa Kusuura, Mitsuru Fujii, Takuji Taguchi, Anupam Mitra
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Publication number: 20120271020Abstract: A method for producing a copolymer for semiconductor lithography containing less metal impurities, and a method for purifying a polymerization initiator for production of the copolymer, are provided. The method for purifying a polymerization initiator to be used for production of a polymer includes a filtering step wherein a solution of a polymerization initiator dissolved in an organic solvent is allowed to pass through a filter having a nominal pore size of not more than 1.0 ?m, to reduce the sodium content of the polymerization initiator solution to not more than 300 ppb with respect to the weight of the polymerization initiator. Further, the method for producing a copolymer for semiconductor lithography includes a polymerization step wherein the polymer for semiconductor lithography is synthesized by a radical polymerization reaction in the presence of a polymerization initiator purified by the above purification method.Type: ApplicationFiled: April 20, 2012Publication date: October 25, 2012Applicant: Maruzen Petrochemical Co., Ltd.Inventor: Youji SUZUKI