Patents by Inventor Yusuke Nagae

Yusuke Nagae 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).

  • Patent number: 11970432
    Abstract: The present invention provides a process for preparing 2-methyl-N-(2?-methylbutyl)butanamide of the following formula (1): the process comprising: subjecting an ?-arylethyl-2-methylbutylamine compound of the following general formula (2): wherein Ar represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, to N-2-methylbutyrylation to form an N-?-arylethyl-2-methyl-N-(2?-methylbutyl)butanamide compound of the following general formula (3): wherein Ar is as defined above, and removing the ?-arylethyl group of the resulting compound (3) to form 2-methyl-N-(2?-methylbutyl)butanamide (1).
    Type: Grant
    Filed: February 28, 2023
    Date of Patent: April 30, 2024
    Assignee: SHIN-ETSU CHEMICAL CO., LTD.
    Inventors: Takeshi Kinsho, Yusuke Nagae, Shogo Tsukaguchi, Yasuhiko Kutsuwada, Tatsuya Hojo, Takeru Watanabe
  • Patent number: 11958801
    Abstract: A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M1 represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, wherein Z1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3).
    Type: Grant
    Filed: January 13, 2023
    Date of Patent: April 16, 2024
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Akihiro Baba, Takeshi Kinsho, Yusuke Nagae
  • Patent number: 11921078
    Abstract: A sensor element includes an element body and a porous protective layer arranged to cover a part of a surface of the element body. The protective layer includes an inlet protective layer arranged to cover a gas inlet formed in the surface of the element body, and at least a part of a face included in the surface of the element body, the face on which the gas inlet is opens, and an arithmetic average roughness Rap of an inner peripheral surface of an internal space of the inlet protective layer satisfies at least one of conditions below: the arithmetic average roughness Rap is 8 ?m or more, and the arithmetic average roughness Rap is higher than an arithmetic average roughness Rac of a bonding surface of the protective layer, the bonding surface at which the protective layer is bonded to the element body.
    Type: Grant
    Filed: August 25, 2021
    Date of Patent: March 5, 2024
    Assignee: NGK INSULATORS, LTD.
    Inventors: Tomoki Nagae, Yoshimasa Kondo, Yusuke Ogiso, Katsunao Uenishi, Atsushi Watanabe, Ayato Koizumi
  • Publication number: 20240067595
    Abstract: Provided is a 3-acyloxymethyl-3-butenal acetal compound of General Formula (10): wherein R1 and R2, which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, and X1 is an acyloxy group having 1 to 6 carbon atoms.
    Type: Application
    Filed: September 21, 2023
    Publication date: February 29, 2024
    Inventors: Takeshi Kinsho, Akihiro Baba, Yusuke Nagae, Tomohiro Watanabe
  • Patent number: 11897842
    Abstract: A method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (1), the method including the step of coupling a nucleophilic reagent of General Formula (8): wherein M is a cationic moiety, with an acetal compound of General Formula (9): wherein R1 and R2, which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, and X is a leaving group, to obtain the 7-methyl-3-methylene-7-octenal acetal compound.
    Type: Grant
    Filed: June 6, 2022
    Date of Patent: February 13, 2024
    Inventors: Takeshi Kinsho, Akihiro Baba, Yusuke Nagae, Tomohiro Watanabe
  • Publication number: 20240025837
    Abstract: A method for producing 7-methyl-3-methylene-7-octenal of Formula (2) is provided and includes a step of hydrolyzing a 7-methyl-3-methylene-7-octenal acetal compound of General Formula (1): wherein R1 and R2, which may be the same or different, are each analkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms to obtain the 7-methyl-3-methylene-7-octenal (2).
    Type: Application
    Filed: September 22, 2023
    Publication date: January 25, 2024
    Inventors: Takeshi Kinsho, Akihiro Baba, Yusuke Nagae, Tomohiro Watanabe
  • Publication number: 20230391710
    Abstract: The present invention provides a novel compound, (4Z,6E)-4,6-undecadienyl trimethylacetate (1). The present invention further provides a process for preparing (4Z,6E)-4,6-undecadienyl trimethylacetate (1), the process comprising subjecting a 4-halobutyl trimethylacetate compound (2) wherein X1 represents a halogen atom, to a phosphonium salt formation reaction with a phosphine compound of the following general formula (3) wherein Ar represents, independently of each other, an aryl group, to obtain a [4-(trimethylacetyloxy)butyl]triarylphosphonium halide compound (4) wherein Y represents a halogen atom, and Ar is as defined above, subjecting the [4-(trimethylacetyloxy)butyl]triarylphosphonium halide compound (4) to a deprotonation reaction in the presence of a base to obtain a reaction product mixture, and subjecting the reaction product mixture to a Wittig reaction with (2E)-2-heptenal (5) to obtain (4Z,6E)-4,6-undecadienyl trimethylacetate (1).
    Type: Application
    Filed: June 1, 2023
    Publication date: December 7, 2023
    Inventors: Yuki Miyake, Takeru Watanabe, Yusuke Nagae
  • Patent number: 11807602
    Abstract: The present invention relates to a process for preparing a 3-isopropenyl-6-heptenal compound of the following formula (2): wherein R1 represents a hydrogen atom or a methyl group, the process comprising: subjecting a 3-isopropenyl-6-heptenoate ester compound of the following formula (1): wherein R1 is as defined above, and R2 represents a monovalent hydrocarbon group having 1 to 10 carbon atoms, to a reduction reaction with a reducing agent to form the 3-isopropenyl-6-heptenal compound (2).
    Type: Grant
    Filed: December 7, 2021
    Date of Patent: November 7, 2023
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Akihiro Baba, Takeshi Kinsho, Naoki Ishibashi, Yusuke Nagae
  • Publication number: 20230312454
    Abstract: The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH2CH2CH=CHCH2CH2OCH2OCH2R1 (1), R1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH3(CH2)3CH=CH(CH2)8CH=CHCH2CH2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).
    Type: Application
    Filed: April 19, 2023
    Publication date: October 5, 2023
    Inventors: Yuki Miyake, Takeshi Kinsho, Yusuke Nagae
  • Patent number: 11746078
    Abstract: The present invention relates to a process for preparing a (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (S,R)-(2), wherein R1 represents a monovalent hydrocarbon group having 1 to 6 carbon atoms, and a bold wedged bond represents the absolute configuration, and a (1R,2S)-(2-acetoxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (R,S)-(3), wherein R1 is as defined above, a hashed wedged bond represents the absolute configuration, and Ac represents an acetyl group, the process comprising: subjecting a (1RS,2SR)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound of the following general formula (RS,SR)-(2), wherein R1 is as defined above, and a hashed unwedged bond represents a relative configuration, to a kinetic resolution reaction with a lipase in the presence of vinyl acetate to obtain the (1S,2R)-(2-hydroxy-3,5,5-trimethyl-3-cyclopentenyl)methyl carboxylate compound ((S,R)-(2)
    Type: Grant
    Filed: January 21, 2022
    Date of Patent: September 5, 2023
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomohiro Watanabe, Takeshi Kinsho, Takeru Watanabe, Miyoshi Yamashita, Yusuke Nagae
  • Publication number: 20230202968
    Abstract: The present invention provides a process for preparing 2-methyl-N-(2?-methylbutyl)butanamide of the following formula (1): the process comprising: subjecting an ?-arylethyl-2-methylbutylamine compound of the following general formula (2): wherein Ar represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, to N-2-methylbutyrylation to form an N-?-arylethyl-2-methyl-N-(2?-methylbutyl)butanamide compound of the following general formula (3): wherein Ar is as defined above, and removing the ?-arylethyl group of the resulting compound (3) to form 2-methyl-N-(2?-methylbutyl)butanamide (1).
    Type: Application
    Filed: February 28, 2023
    Publication date: June 29, 2023
    Inventors: Takeshi Kinsho, Yusuke Nagae, Shogo Tsukaguchi, Yasuhiko Kutsuwada, Tatsuya Hojo, Takeru Watanabe
  • Patent number: 11661394
    Abstract: The present invention relates to a 6-hydroxy-3-hexenyl alkoxymethyl ether compound of the following general formula (1): HOCH2CH2CH?CHCH2CH2OCH2OCH2R? (1), R1 representing a hydrogen atom, an n-alkyl group having 1 to 9 carbon atoms, or a phenyl group; and also relates to a process for preparing a 3,13-octadecadien-1-ol compound of the following formula (6): CH3(CH2)3CH?CH(CH2)8CH?CHCH2CH2OH (6) from the 6-hydroxy-3-hexenyl alkoxymethyl ether compound (1).
    Type: Grant
    Filed: September 30, 2021
    Date of Patent: May 30, 2023
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Yuki Miyake, Takeshi Kinsho, Yusuke Nagae
  • Publication number: 20230148099
    Abstract: A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M1 represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, wherein Z1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3).
    Type: Application
    Filed: January 13, 2023
    Publication date: May 11, 2023
    Inventors: Akihiro Baba, Takeshi Kinsho, Yusuke Nagae
  • Patent number: 11629119
    Abstract: The present invention provides a process for preparing 2-methyl-N-(2?-methylbutyl) butanamide of the following formula (1):the process comprising: subjecting an ?-arylethyl-2-methylbutylamine compound of the following general formula (2): wherein Ar represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, to N-2-methylbutyrylation to form an N-?-arylethyl-2-methyl-N-(2?-methylbutyl)butanamide compound of the following general formula (3): wherein Ar is as defined above, and removing the ?-arylethyl group of the resulting compound (3) to form 2-methyl-N-(2? -methylbutyl)butanamide (1).
    Type: Grant
    Filed: May 24, 2022
    Date of Patent: April 18, 2023
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takeshi Kinsho, Yusuke Nagae, Shogo Tsukaguchi, Yasuhiko Kutsuwada, Tatsuya Hojo, Takeru Watanabe
  • Patent number: 11591282
    Abstract: A process for process for preparing 6-isopropenyl-3-methyl-9-decenyl acetate of the following formula (3), wherein Ac represents an acetyl group, the process comprising steps of: preparing a nucleophilic reagent, 5-isopropenyl-2-methyl-8-nonenyl compound, of the following general formula (1): wherein M1 represents Li, MgZ1, ZnZ1, Cu, CuZ1, or CuLiZ1, wherein Z1 represents a halogen atom or a 5-isopropenyl-2-methyl-8-nonenyl group, from a 5-isopropenyl-2-methyl-8-nonenyl halide compound of the following general formula (4): wherein X1 represents a halogen atom; subjecting the nucleophilic reagent (1), 5-isopropenyl-2-methyl-8-nonenyl compound, to an addition reaction with at least one electrophilic reagent selected from the group consisting of formaldehyde, paraformaldehyde, and 1,3,5-trioxane, followed by a hydrolysis reaction to form 6-isopropenyl-3-methyl-9-decenol of the following formula (2); and acetylating 6-isopropenyl-3-methyl-9-decenol (2) to form 6-isopropenyl-3-methyl-9-decenyl acetate (3).
    Type: Grant
    Filed: April 20, 2021
    Date of Patent: February 28, 2023
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Akihiro Baba, Takeshi Kinsho, Yusuke Nagae
  • Publication number: 20220411363
    Abstract: The present invention provides a process for preparing 2-methyl-N-(2?-methylbutyl)butanamide of the following formula (1):the process comprising: subjecting an ?-arylethyl-2-methylbutylamine compound of the following general formula (2): wherein Ar represents a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, to N-2-methylbutyrylation to form an N-?-arylethyl-2-methyl-N-(2?-methylbutyl)butanamide compound of the following general formula (3): wherein Ar is as defined above, and removing the ?-arylethyl group of the resulting compound (3) to form 2-methyl-N-(2?-methylbutyl)butanamide (1).
    Type: Application
    Filed: May 24, 2022
    Publication date: December 29, 2022
    Inventors: Takeshi Kinsho, Yusuke Nagae, Shogo Tsukaguchi, Yasuhiko Kutsuwada, Tatsuya Hojo, Takeru Watanabe
  • Publication number: 20220324783
    Abstract: The present invention provides a process for preparing a dimethylcyclobutane compound of the following general formula (1A), the process comprising reacting a dimethylcyclobutanone compound of the following general formula (2) with a phosphonic ester compound of the following general formula (3) to produce an unsaturated ester compound of the following general formula (4), having a dimethylcyclobutane ring, and subjecting the unsaturated ester compound (4), having a dimethylcyclobutane ring, to a reduction reaction to produce the dimethylcyclobutane compound (1A).
    Type: Application
    Filed: June 7, 2022
    Publication date: October 13, 2022
    Inventors: Naoki Ishibashi, Yusuke Nagae, Takeshi Kinsho
  • Publication number: 20220315513
    Abstract: The present invention relates to a process for preparing a (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound of the following general formula (3-Z): wherein Y represents a halogen atom, Ar represents, independently of each other, an aryl group, and R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 15 carbon atoms, or R1 and R2 may form together a divalent hydrocarbon group, R1-R2, having 2 to 10 carbon atoms, the process comprising: subjecting a (7Z)-11-halo-1,1-dialkoxy-7-undecene compound of the following general formula (1-Z): wherein X1 represents a halogen atom, and R1 and R2 are as defined above to a phosphonium salt formation reaction with a phosphine compound of the following general formula (2): wherein Ar is as defined above to form the (4Z)-11,11-dialkoxy-4-undecenyltriarylphosphonium halide compound (3-Z).
    Type: Application
    Filed: March 18, 2022
    Publication date: October 6, 2022
    Inventors: Yuki Miyake, Takeshi Kinsho, Yusuke Nagae
  • Publication number: 20220306565
    Abstract: There are provided methods of efficiently producing compounds that are, for example, sex pheromones of San Jose Scale. For example, there is provided a method for producing a 7-methyl-3-methylene-7-octenyl carboxylate compound (1), the method including the step of coupling a nucleophilic reagent expressed as a 3-methyl-3-butenyl M of General Formula (8): wherein M is a cationic moiety, with an acetal compound of General Formula (9): wherein R1 and R2, which may be the same or different, are each an alkyl group having 1 to 6 carbon atoms, or are bonded to each other to form a divalent alkylene group having 2 to 12 carbon atoms, and X is a leaving group, to obtain the 7-methyl-3-methylene-7-octenal acetal compound.
    Type: Application
    Filed: June 6, 2022
    Publication date: September 29, 2022
    Inventors: Takeshi Kinsho, Akihiro Baba, Yusuke Nagae, Tomohiro Watanabe
  • Publication number: 20220259136
    Abstract: The present invention provides a process for preparing a diester compound of the following general formula (1), having a dimethylcyclobutane ring, wherein R1 and R2 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, the process comprising reacting a dimethylcyclobutanone compound of the following general formula (2), wherein R1 is as defined above, with a phosphonic ester compound of the following general formula (3), wherein R2 and R3 represent, independently of each other, a monovalent hydrocarbon group having 1 to 10 carbon atoms, to produce the diester compound (1), having a dimethylcyclobutane ring.
    Type: Application
    Filed: May 5, 2022
    Publication date: August 18, 2022
    Inventors: Naoki Ishibashi, Yusuke Nagae, Takeshi Kinsho