Patents by Inventor Kiyoharu Tsutsumi
Kiyoharu Tsutsumi has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).
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Patent number: 11479637Abstract: Provided is a sheet-like prepreg that has both a low coefficient of linear thermal expansion and high flexibility and offers excellent anti-warpage performance and cracking resistance. The sheet-like prepreg according to the present invention includes a curable composition and a sheet-like porous support impregnated with the curable composition. The sheet-like porous support is made from a material having a coefficient of linear thermal expansion of 10 ppm/K or less. The sheet-like prepreg gives a cured product having a glass transition temperature of ?60° C. to 100° C. The curable composition includes one or more curable compounds (A) and at least one of a curing agent (B) and a curing catalyst (C). The curable compounds (A) include an epoxide having a weight per epoxy equivalent of 140 to 3000 g/eq in an amount of 50 weight percent or more of the totality of the curable compounds (A).Type: GrantFiled: October 3, 2017Date of Patent: October 25, 2022Assignee: DAICEL CORPORATIONInventors: Hiroto Miyake, Kiyoharu Tsutsumi, Ryosuke Ieki
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Patent number: 10711162Abstract: Provided are: an adhesive that offers high adhesiveness to bond and secure an adherend even in a high-temperature environment, as long as securing is necessary. The adherend can be removed without failure and without adhesive residue once securing becomes unnecessary; and a method for processing an adherend using the adhesive. The adhesive according to the present invention contains a multivalent vinyl ether compound (A) and at least one of a compound (B) and a compound (C). The compound (B) is represented by Formula (b). The compound (C) includes two or more constitutional units each represented by Formula (c).Type: GrantFiled: October 6, 2014Date of Patent: July 14, 2020Assignee: DAICEL CORPORATIONInventors: Yousuke Ito, Hiroki Tanaka, Kiyoharu Tsutsumi
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Publication number: 20200055979Abstract: Provided is a sheet-like prepreg that has both a low coefficient of linear thermal expansion and high flexibility and offers excellent anti-warpage performance and cracking resistance. The sheet-like prepreg according to the present invention includes a curable composition and a sheet-like porous support impregnated with the curable composition. The sheet-like porous support is made from a material having a coefficient of linear thermal expansion of 10 ppm/K or less. The sheet-like prepreg gives a cured product having a glass transition temperature of ?60° C. to 100° C. The curable composition includes one or more curable compounds (A) and at least one of a curing agent (B) and a curing catalyst (C). The curable compounds (A) include an epoxide having a weight per epoxy equivalent of 140 to 3000 g/eq in an amount of 50 weight percent or more of the totality of the curable compounds (A).Type: ApplicationFiled: October 3, 2017Publication date: February 20, 2020Applicant: DAICEL CORPORATIONInventors: Hiroto MIYAKE, Kiyoharu TSUTSUMI, Ryosuke IEKI
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Publication number: 20190329457Abstract: Provided is a resin composition capable of forming an imprint replica mold that enables easy removal of a residual layer and enables formation of high-accuracy patterns. The resin composition for replica mold formation includes (A) a thermoplastic or thermosetting resin, and (B) a compound. The resin (A) has a transmittance of light of 50% or more at one or more wavelengths from 200 to 450 nm. The compound (B) is capable of absorbing or scattering light at the wavelength(s). The compound (B) is present in a proportion of 0.5 to 50 parts by weight per 100 parts by weight of the resin (A). The resin (A) is preferably selected from olefinic resins and silicone resins.Type: ApplicationFiled: November 16, 2017Publication date: October 31, 2019Applicant: DAICEL CORPORATIONInventors: Hiroto MIYAKE, Kiyoharu TSUTSUMI
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Patent number: 10047257Abstract: Provided is an adhesive composition for multilayer semiconductors. The adhesive composition gives, when applied and dried by heating, an adhesive layer that has approximately no adhesiveness at a temperature lower than 50° C., but, when heated at such a temperature as to less cause damage to semiconductor chips, offers adhesiveness and is rapidly cured thereafter. This adhesive composition for multilayer semiconductors includes a polymerizable compound (A), at least one of a cationic-polymerization initiator (B1) and an anionic-polymerization initiator (B2), and a solvent (C). The polymerizable compound (A) contains 80% by weight or more of an epoxide having a softening point or melting point of 50° C. or higher. The cationic-polymerization initiator (B1) gives a composition having a thermal curing time of 3.5 minutes or longer at 130° C.Type: GrantFiled: September 25, 2014Date of Patent: August 14, 2018Assignee: DAICEL CORPORATIONInventors: Hiroki Tanaka, Katsuhiro Nakaguchi, Kiyoharu Tsutsumi, Yousuke Ito, Naoko Tsuji
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Publication number: 20160264822Abstract: Provided are: an adhesive that offers high adhesiveness to bond and secure an adherend even in a high-temperature environment, as long as securing is necessary. The adherend can be removed without failure and without adhesive residue once securing becomes unnecessary; and a method for processing an adherend using the adhesive. The adhesive according to the present invention contains a multivalent vinyl ether compound (A) and at least one of a compound (B) and a compound (C). The compound (B) is represented by Formula (b). The compound (C) includes two or more constitutional units each represented by Formula (c).Type: ApplicationFiled: October 6, 2014Publication date: September 15, 2016Applicant: DAICEL CORPORATIONInventors: Yousuke ITO, Hiroki TANAKA, Kiyoharu TSUTSUMI
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Publication number: 20160215183Abstract: Provided is an adhesive composition for multilayer semiconductors. The adhesive composition gives, when applied and dried by heating, an adhesive layer that has approximately no adhesiveness at a temperature lower than 50° C., but, when heated at such a temperature as to less cause damage to semiconductor chips, offers adhesiveness and is rapidly cured thereafter. This adhesive composition for multilayer semiconductors includes a polymerizable compound (A), at least one of a cationic-polymerization initiator (B1) and an anionic-polymerization initiator (B2), and a solvent (C). The polymerizable compound (A) contains 80% by weight or more of an epoxide having a softening point or melting point of 50° C. or higher. The cationic-polymerization initiator (B1) gives a composition having a thermal curing time of 3.5 minutes or longer at 130° C.Type: ApplicationFiled: September 25, 2014Publication date: July 28, 2016Applicant: DAICEL CORPORATIONInventors: Hiroki TANAKA, Katsuhiro NAKAGUCHI, Kiyoharu TSUTSUMI, Yousuke ITO, Naoko TSUJI
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Patent number: 8981040Abstract: Provided is a cationically polymerizable resin which is rapidly cured upon irradiation with light and forms a cured product excellent in flexibility and thermal stability. The cationically polymerizable resin is obtained through radical polymerization of an oxetane-ring-containing (meth)acryloyl compound represented by following Formula (1) alone or in combination with another radically polymerizable compound. In the formula, R1 represents hydrogen atom or methyl group; R2 represents hydrogen atom or an alkyl group; and “A” represents a linear or branched chain alkylene group having 2 to 20 carbon atoms.Type: GrantFiled: January 24, 2011Date of Patent: March 17, 2015Assignee: Daicel CorporationInventors: Naoko Araki, Yoshinori Funaki, Kiyoharu Tsutsumi, Tomoaki Mahiko
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Patent number: 8975349Abstract: Disclosed is a cationically polymerizable resin composition which includes an oxetane-ring-containing vinyl ether compound (A) and/or an alicyclic-epoxy-containing vinyl ether compound (B); and an oligomer or polymer (C) having a molecular weight of 500 or more, being liquid at 0° C., and containing at least one of structures represented by following Formulae (1a) to (1f), wherein Rx represents hydrogen atom or methyl group; R1 to R3 each independently represent a hydrocarbon group having 1 to 5 carbon atoms; “a” is an integer of from 0 to 5; and “b” is 1 or 2. This cationically polymerizable resin composition has a low viscosity, is easy to work, cures extremely rapidly upon irradiation with light, and can give a cured object excellent in flexibility, thermal stability, and bendability after heat treatment.Type: GrantFiled: May 20, 2010Date of Patent: March 10, 2015Assignee: Daicel CorporationInventors: Yoshinori Funaki, Kiyoharu Tsutsumi, Tomoaki Mahiko, Naoko Araki
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Patent number: 8735462Abstract: Provided is a radical-polymerizable resin capable of giving a cured material which is satisfactorily flexible, can relax stress upon usage as an adhesive, and does not cause disadvantages such as separation at the adhesive interface or breakage of an adherend, which stress occurs between the adhesive and the adherend upon heating or cooling and is caused by difference in coefficient of thermal expansion between them. The radical-polymerizable resin is obtained through cationic polymerization of a compound represented by any of following Formulae (1a) and (1b) and a compound represented by any of following Formulae (2a), (2b), (2c), (2d), (2e), and (2f). The radical-polymerizable resin is liquid at 0 ° C. and has a weight-average molecular weight of 500 or more. Symbols in the formulae are as defined in the description.Type: GrantFiled: March 28, 2011Date of Patent: May 27, 2014Assignee: Daicel CorporationInventors: Tomoaki Mahiko, Yoshinori Funaki, Kiyoharu Tsutsumi, Naoko Araki
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Publication number: 20130035465Abstract: Provided is a radically polymerizable resin which has a low viscosity, has excellent workability, and is rapidly cured upon application of heat and/or light to form a cured product having excellent flexibility and thermal stability. The radically polymerizable resin composition is obtained by cationic polymerization of an oxetane-ring-containing (meth)acrylic ester compound represented by following Formula (1) alone or in combination with another cationically polymerizable compound. In Formula (1), R1 represents hydrogen atom or methyl group; R2 represents hydrogen atom or an alkyl group; and “A” represents a linear or branched chain alkylene group having 4 to 20 carbon atoms.Type: ApplicationFiled: April 8, 2011Publication date: February 7, 2013Applicant: DAICEL CORPORATIONInventors: Naoko Araki, Yoshinori Funaki, Kiyoharu Tsutsumi, Tomoaki Mahiko
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Publication number: 20130030078Abstract: Provided is a radical-polymerizable resin capable of giving a cured material which is satisfactorily flexible, can relax stress upon usage as an adhesive, and does not cause disadvantages such as separation at the adhesive interface or breakage of an adherend, which stress occurs between the adhesive and the adherend upon heating or cooling and is caused by difference in coefficient of thermal expansion between them. The radical-polymerizable resin is obtained through cationic polymerization of a compound represented by any of following Formulae (1a) and (1b) and a compound represented by any of following Formulae (2a), (2b), (2c), (2d), (2e), and (2f). The radical-polymerizable resin is liquid at 0° C. and has a weight-average molecular weight of 500 or more. Symbols in the formulae are as defined in the description.Type: ApplicationFiled: March 28, 2011Publication date: January 31, 2013Applicant: DAICEL CORPORATIONInventors: Tomoaki Mahiko, Yoshinori Funaki, Kiyoharu Tsutsumi, Naoko Araki
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Publication number: 20120309930Abstract: Provided is a cationically polymerizable resin which is rapidly cured upon irradiation with light and forms a cured product excellent in flexibility and thermal stability. The cationically polymerizable resin is obtained through radical polymerization of an oxetane-ring-containing (meth)acryloyl compound represented by following Formula (1) alone or in combination with another radically polymerizable compound. In the formula, R1 represents hydrogen atom or methyl group; R2 represents hydrogen atom or an alkyl group; and “A” represents a linear or branched chain alkylene group having 2 to 20 carbon atoms.Type: ApplicationFiled: January 24, 2011Publication date: December 6, 2012Inventors: Naoko Araki, Yoshinori Funaki, Kiyoharu Tsutsumi, Tomoaki Mahiko
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Patent number: 8236971Abstract: A polycyclic ester containing a cyano group and a lactone skeleton, represented by following Formula (1): wherein Ra represents, for example, a hydrogen atom or an alkyl group having one to six carbon atoms which may have a halogen atom; R1s each represent, for example, a halogen atom or an alkyl or haloalkyl group having one to six carbon atoms; “m” is the number of R1s; “n” is the number of cyano groups; and CH2?C(Ra)COO— group may have either of an endo conformation and an exo conformation. Accordingly, there is provided a novel polycyclic ester containing a cyano group and a lactone skeleton which is useful typically as a monomeric component for highly functional polymers. A polymer, for example, derived from this compound is highly soluble in an organic solvent while remaining stable typically to chemicals and exhibits improved hydrolyzability and/or improved solubility in water after hydrolysis.Type: GrantFiled: October 8, 2010Date of Patent: August 7, 2012Assignee: Daicel Chemical Industries, Ltd.Inventors: Keizo Inoue, Takahiro Iwahama, Masamichi Nishimura, Kiyoharu Tsutsumi
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Publication number: 20120077946Abstract: Disclosed is a cationically polymerizable resin composition which includes an oxetane-ring-containing vinyl ether compound (A) and/or an alicyclic-epoxy-containing vinyl ether compound (B); and an oligomer or polymer (C) having a molecular weight of 500 or more, being liquid at 0° C., and containing at least one of structures represented by following Formulae (1a) to (1f), wherein Rx represents hydrogen atom or methyl group; R1 to R3 each independently represent a hydrocarbon group having 1 to 5 carbon atoms; “a” is an integer of from 0 to 5; and “b” is 1 or 2. This cationically polymerizable resin composition has a low viscosity, is easy to work, cures extremely rapidly upon irradiation with light, and can give a cured object excellent in flexibility, thermal stability, and bendability after heat treatment.Type: ApplicationFiled: May 20, 2010Publication date: March 29, 2012Inventors: Yoshinori Funaki, Kiyoharu Tsutsumi, Tomoaki Mahiko, Naoko Araki
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Publication number: 20110027717Abstract: A photoresist composition contains a polyol compound and a vinyl ether compound, which polyol compound having an aliphatic group and an aromatic group bound alternately, and which aromatic group has an aromatic ring and two or more hydroxyl groups on the aromatic ring. The polyol compound can be prepared, for example, through an acid-catalyzed reaction, such as a Friedel-Crafts reaction, between an aliphatic polyol and an aromatic polyol. The aliphatic polyol is preferably an alicyclic polyol, whereas the aromatic polyol is preferably hydroquinone. The photoresist composition gives a resist film showing excellent alkali solubility and high etching resistance and thereby gives a resist pattern with less LER and less pattern collapse.Type: ApplicationFiled: April 2, 2009Publication date: February 3, 2011Inventors: Kiyoharu Tsutsumi, Arimichi Okumura
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Publication number: 20110027725Abstract: A polyol compound for photoresists has at least one aliphatic group and at least one aromatic group bound to each other alternately, in which the aromatic group has at least one aromatic ring and two or more hydroxyl groups bound to the aromatic ring. The polyol compound for photoresists can be prepared through an acid-catalyzed reaction, such as a Friedel-Crafts reaction, between an aliphatic polyol and an aromatic polyol. The aliphatic polyol is preferably an alicyclic polyol. The aromatic polyol is preferably hydroquinone. By protecting phenolic hydroxyl group(s) thereof with a protecting group capable of leaving with an acid, the polyol compound for photoresists gives a compound for photoresists. A photoresist composition containing this compound can form a resist pattern which shows less line edge roughness (LER), excels in resolution and etching resistance, and is fine and sharp.Type: ApplicationFiled: April 2, 2009Publication date: February 3, 2011Inventors: Kiyoharu Tsutsumi, Yoshinori Funaki, Arimichi Okumura
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Publication number: 20110027726Abstract: A polymer compound for photoresists contains alkali-soluble groups being protected by protecting groups capable of leaving with an acid, and is thereby insoluble or sparingly soluble in an alkaline developer, in which part or all of the protecting groups are multifunctional protecting groups each protecting two or more alkali-soluble groups. The alkali-soluble groups may be phenolic hydroxyl groups. The polymer compound may correspond to a polyol compound having an aliphatic group and an aromatic group bound to each other alternately, the aromatic group having an aromatic ring and two or more hydroxyl groups bound to the aromatic ring, except with phenolic hydroxyl groups of the polyol compound being protected by protecting groups capable of leaving with an acid. The polymer compound for photoresists can give a resist film with less line edge roughness (LER), while exhibiting excellent workability and resolution.Type: ApplicationFiled: April 2, 2009Publication date: February 3, 2011Inventors: Kiyoharu Tsutsumi, Arimichi Okumura
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Publication number: 20110028743Abstract: A polycyclic ester containing a cyano group and a lactone skeleton, represented by following Formula (1): wherein Ra represents, for example, a hydrogen atom or an alkyl group having one to six carbon atoms which may have a halogen atom; R1s each represent, for example, a halogen atom or an alkyl or haloalkyl group having one to six carbon atoms; “m” is the number of R1s; “n” is the number of cyano groups; and CH2?C(Ra)COO— group may have either of an endo conformation and an exo conformation. Accordingly, there is provided a novel polycyclic ester containing a cyano group and a lactone skeleton which is useful typically as a monomeric component for highly functional polymers. A polymer, for example, derived from this compound is highly soluble in an organic solvent while remaining stable typically to chemicals and exhibits improved hydrolyzability and/or improved solubility in water after hydrolysis.Type: ApplicationFiled: October 8, 2010Publication date: February 3, 2011Inventors: Keizo Inoue, Takahiro Iwahama, Masamichi Nishimura, Kiyoharu Tsutsumi
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Patent number: 7834114Abstract: Disclosed is a polycyclic ester containing a cyano group and a lactone skeleton, represented by following Formula (1): wherein Ra represents, for example, a hydrogen atom or an alkyl group having one to six carbon atoms which may have a halogen atom; R1s each represent, for example, a halogen atom or an alkyl or haloalkyl group having one to six carbon atoms; “m” is the number of R1s; “n” is the number of cyano groups; and CH2?C(Ra)COO— group may have either of an endo conformation and an exo conformation. Accordingly, there is provided a novel polycyclic ester containing a cyano group and a lactone skeleton which is useful typically as a monomeric component for highly functional polymers. A polymer, for example, derived from this compound is highly soluble in an organic solvent while remaining stable typically to chemicals and exhibits improved hydrolyzability and/or improved solubility in water after hydrolysis.Type: GrantFiled: December 1, 2009Date of Patent: November 16, 2010Assignee: Daicel Chemical Industries, Ltd.Inventors: Keizo Inoue, Takahiro Iwahama, Masamichi Nishimura, Kiyoharu Tsutsumi