Patents Assigned to San-Apro Limited
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Patent number: 11926581Abstract: The sulfonium salt has high photosensitivity to i-rays and high compatibility with cationically polymerizable compounds such as epoxy compounds, and is excellent storage stability in formulations containing such compounds. The sulfonium salt is represented by general formula (1). In formula (1), R represents an alkyl group or an aryl group; substituents, R1 to R5, each independently represent an alkyl group, a hydroxy group, an alkoxy group, an aryl group, an aryloxy group, a hydroxy(poly)alkyleneoxy group, or a halogen atom; R6 to R9 each independently represent an alkyl group, an aryl group, or a hydrogen atom; m1 to m5 each represent the number of occurrences of each of R1 to R5, m1 and m4 represent an integer of 0 to 3, m2 and m5 represent an integer of 0 to 4, m3 represents an integer of 0 to 5, and X? represents a monovalent polyatomic anion.Type: GrantFiled: April 9, 2019Date of Patent: March 12, 2024Assignee: SAN-APRO LIMITEDInventors: Takuto Nakao, Yusaku Takashima
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Patent number: 10450266Abstract: Provided are: a non-ionic photoacid generator containing a sulfonate compound having a high photosensitivity to i lines, exhibiting excellent heat-resistance stability, and exhibiting excellent solubility in a hydrophobic material; and a resin composition for photolithography containing the same. The present invention is a sulfonate compound characterized by being represented by general formula (1). [In formula (1), R1 represents an aryl group having 6 to 18 carbon atoms or a heterocyclic hydrocarbon group having 4 to 20 carbon atoms. R2 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an alkynyl group having 2 to 18 carbon atoms, or an aryl group having 6 to 18 carbon atoms. R3 represents a hydrocarbon group having 1 to 18 carbon atoms (in which some or all hydrogen atoms may be substituted with fluorine).Type: GrantFiled: October 13, 2015Date of Patent: October 22, 2019Assignee: SAN-APRO LIMITEDInventors: Masaaki Oka, Yuji Nakamura
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Publication number: 20170233336Abstract: Provided are: a non-ionic photoacid generator containing a sulfonate compound having a high photosensitivity to i lines, exhibiting excellent heat-resistance stability, and exhibiting excellent solubility in a hydrophobic material; and a resin composition for photolithography containing the same. The present invention is a sulfonate compound characterized by being represented by general formula (1). [In formula (1), R1 represents an aryl group having 6 to 18 carbon atoms or a heterocyclic hydrocarbon group having 4 to 20 carbon atoms. R2 represents a hydrogen atom, an alkyl group having 1 to 18 carbon atoms, an alkenyl group having 2 to 18 carbon atoms, an alkynyl group having 2 to 18 carbon atoms, or an aryl group having 6 to 18 carbon atoms. R3 represents a hydrocarbon group having 1 to 18 carbon atoms (in which some or all hydrogen atoms may be substituted with fluorine).Type: ApplicationFiled: October 13, 2015Publication date: August 17, 2017Applicant: SAN-APRO LIMITEDInventors: Masaaki Oka, Yuji Nakamura
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Patent number: 9045398Abstract: Provided is a novel sulfonium salt that has high solubility in a solvent and has high light sensitivity to, especially, light having a wavelength not longer than deep-UV (254 nm) and a novel photo-acid generator comprising the sulfonium salt. The invention relates to a sulfonium salt represented by the following general formula (1) and a novel photo-acid generator comprising the sulfonium salt. wherein R1 represents an electron withdrawing group; R2 and R3 each independently represent an alkyl group having 1 to 5 carbon atoms, an alkoxy group, an acyl group, a halogenated alkyl group, a halogen atom, a hydroxyl group, a cyano group, or a nitro group; p and q each independently represent an integer of 0 to 5; and X?represents a monovalent counter anion.Type: GrantFiled: May 29, 2014Date of Patent: June 2, 2015Assignees: SAN-APRO LIMITED, TOKYO OHKA KOGYA CO. LTD.Inventors: Issei Suzuki, Takuya Ikeda, Yusaku Takashima, Takeshi Furuta, Yoshitaka Komuro, Yoshiyuki Utsumi, Takaaki Kaiho, Toshiaki Hato
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Patent number: 8329771Abstract: The object of the present invention is to provide a photobase generator capable of efficiently generating amines (tertiary amines and amidine) high in catalytic activity by sensing light with a wavelength of from 350 to 500 nm (especially, from 400 to 500 nm). The present invention is a photobase generator characterized in being represented by general formula (1) or (2). Y+ is a quaternary ammonio group of general formula (3) to (5), and X? is a counter anion selected from among a borate anion, a phenolate anion, and a carboxylate anion.Type: GrantFiled: March 18, 2009Date of Patent: December 11, 2012Assignee: San-Apro LimitedInventors: Atsushi Shiraishi, Hideki Kimura
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Patent number: 8278030Abstract: An object of the present invention is to provide a sulfonium salt that has sufficient photosensitivity by active energy rays, such as visible light, ultraviolet rays, electron beams, and X-rays. The present invention is a sulfonium salt represented by formula (1). It is noted that R1 is a group represented by formula (2); R2 and R3 each represent an aryl group having 6 to 30 carbon atoms, a heterocyclic hydrocarbon group having 4 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, or an alkynyl group having 2 to 30 carbon atoms; X? represents a monovalent polyatomic anion; R4 to R6 each represent an alkyl group, or the like; k represents an integer of 0 to 4; m represents an integer of 0 to 3; n represents an integer of 0 to 4; and A represents a group represented by —S—, —O—, —SO—, —SO2—, or —CO—.Type: GrantFiled: April 27, 2009Date of Patent: October 2, 2012Assignee: San-Apro LimitedInventors: Issei Suzuki, Hideki Kimura
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Publication number: 20110039205Abstract: An object of the present invention is to provide a sulfonium salt that has sufficient photosensitivity by active energy rays, such as visible light, ultraviolet rays, electron beams, and X-rays. The present invention is a sulfonium salt represented by formula (1). It is noted that R1 is a group represented by formula (2); R2 and R3 each represent an aryl group having 6 to 30 carbon atoms, a heterocyclic hydrocarbon group having 4 to 30 carbon atoms, an alkyl group having 1 to 30 carbon atoms, an alkenyl group having 2 to 30 carbon atoms, or an alkynyl group having 2 to 30 carbon atoms; X? represents a monovalent polyatomic anion; R4 to R6 each represent an alkyl group, or the like; k represents an integer of 0 to 4; m represents an integer of 0 to 3; n represents an integer of 0 to 4; and A represents a group represented by —S—, —O—, —SO—, —SO2—, or —CO—.Type: ApplicationFiled: April 27, 2009Publication date: February 17, 2011Applicant: SAN-APRO LIMITEDInventors: Issei Suzuki, Hideki Kimura
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Publication number: 20110028585Abstract: The object of the present invention is to provide a photobase generator capable of efficiently generating amines (tertiary amines and amidine) high in catalytic activity by sensing light with a wavelength of from 350 to 500 nm (especially, from 400 to 500 nm). The present invention is a photobase generator characterized in being represented by general formula (1) or (2). Y+ is a quaternary ammonio group of general formula (3) to (5), and X? is a counter anion selected from among a borate anion, a phenolate anion, and a carboxylate anion.Type: ApplicationFiled: March 18, 2009Publication date: February 3, 2011Applicant: SAN-APRO LIMITEDInventors: Atsushi Shiraishi, Hideki Kimura
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Patent number: 7709598Abstract: To obtain a polymerization initiator (acid generating agent) having excellent power for initiation of cationic polymerization without containing arsenic or antimony. Provided is a specific onium salt or transition metal complex salt of a fluorinated alkyl fluorophosphoric acid.Type: GrantFiled: May 27, 2005Date of Patent: May 4, 2010Assignee: San-Apro LimitedInventors: Hideki Kimura, Jiro Yamamoto, Shinji Yamashita, Mitsuo Kurumaya, Takaaki Sonoda
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Patent number: 7709548Abstract: A monosulfonium salt in which very little unreacted raw material remains, which has a purity of at least 96%, and which has one sulfonio group in its molecule is manufactured without a refining step. After (a) an aryl compound, (b) a sulfoxide compound, (c) a dehydrating agent, and (d) a BF4, PF6, AsF6, or SbF6 salt of an alkali metal or an alkaline earth metal are introduced into a reaction system, (e) an inorganic acid is added, so that the aryl compound (a) and the sulfoxide compound (b) are subjected to dehydration condensation.Type: GrantFiled: December 17, 2007Date of Patent: May 4, 2010Assignee: San-Apro LimitedInventors: Masashi Date, Hideki Kimura, Shinji Yamashita, Jiro Yamamoto
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Patent number: 7060858Abstract: It is an object of the invention to provide a method which makes it possible to manufacture the desired sulfonium salts directly without using a metathesis process and without using acids in large excess amounts. An aryl compound (A) in which a hydrogen atom is bonded to at least one of the carbon atoms of the aryl group, and a sulfoxide compound (B) which can be expressed by the formula: R1 SO R2 (where R1 and R2 indicate hydrocarbon groups or heterocyclic groups which may be substituted, and which may be the same or different) are reacted in the presence of a strong acid (C) which can be expressed by the formula: HMXmYn (where M indicates an element of group IIIa or group Va of the periodic table, X indicates a halogen atom, Y indicates a hydroxyl group, m and n are integers which are such that m+n=4 and n=0 to 3 in cases where M is an element of group IIIa, and m and n are integers which are such that m+n=6 and n=0 to 2 in cases where M is an element of group Va).Type: GrantFiled: December 17, 2001Date of Patent: June 13, 2006Assignee: San-Apro LimitedInventors: Masashi Date, Hideki Kimura, Jiro Yamamoto
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Patent number: 6027777Abstract: A forming material for the fabrication of appliances for fixing, supporting, correcting and holding human bodies, characterized by a main forming material body including a quantity of granulated materials each coated with a moisture-curable urethane prepolymer contained within a water-permeable material container, the main forming material body being hermetically enclosed in a moisture-impermeable material container, wherein the moisture-curable urethane prepolymer and the water-permeable material container are unreactive with each other and have a low adhesive strength with respect to each other to provide good long term preservability and ease of operability to allow modeling and conforming the main forming material body to a desired shape.Type: GrantFiled: October 10, 1996Date of Patent: February 22, 2000Assignees: Alcare Co. Ltd., SAN-APRO LimitedInventors: Hiroyuki Hirano, Wataru Okuyama, Nobuyasu Nakasugi, Shozo Oonishi
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Patent number: 5665056Abstract: A water-curable support bandage constitutes a flexible fabric coated with a water-curable polyurethane resin composition containing a polyurethane prepolymer consisting of a polyol and a polyisocyanate, a catalyst and a stabilizer, wherein the polyol contains a polyethylene glycol and a bisphenol system diol. The water-curable support bandage provides greater storage stability, working time adequate for application to a diseased or injured body part, adequate modeling time, and cures rapidly thereafter to achieve a weight bearing strength. In the polyol a polypropylene glycol can be substituted for the polyethylene glycol.Type: GrantFiled: November 9, 1994Date of Patent: September 9, 1997Assignees: Alcare Co., Ltd., San-Apro LimitedInventors: Nobuyasu Nakasugi, Takayuki Sekine
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Patent number: 5527266Abstract: Proposed is a moisture-curable polyurethane resin composition having good storage stability under a moisture-free condition without affecting the curability in the presence of moisture. The composition comprises (a) a polyurethane prepolymer as a reaction product of a polyol compound and a polyisocyanate compound, (b) a catalytic compound to promote curing of the composition and (c) a stabilizer which is trifluoromethane sulfonic acid in a limited amount. The improvement in the storage stability of the composition is particularly remarkable when trifluoromethane sulfonic acid is used in combination with a specific curing catalyst. The composition is useful in the preparation of a surgical casting tape by coating or impregnating a flexible substrate web such as a glass fiber cloth therewith.Type: GrantFiled: June 6, 1994Date of Patent: June 18, 1996Assignee: San-Apro LimitedInventors: Kouzou Hiraishi, Nobuyasu Nakasugi
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Patent number: 5064957Abstract: A novel morpholino-substituted tertiary amine compound is proposed which is tris[2-(4-morpholino)ethyl] amine or a derivative thereof by optionally substituting methyl and/or ethyl groups for a part or all of the hydrogen atoms at the 2- and 6-positions of the morpholine rings. The amine compound can be synthesized by heating tris[N,N-di(2-hydroxyethyl)aminoethyl] amine or a corresponding derivative thereof in a mixture with sulfuric acid. The amine compound is useful as a catalyst for the urethane-forming reaction between a polyisocyanate compound and a polyol compound without the problems of environmental pollution or unpleasant odor as in the use of methyl or ethyl morpholine for the same purpose.Type: GrantFiled: March 13, 1990Date of Patent: November 12, 1991Assignee: San-Apro LimitedInventor: Nobuyasu Nakasugi
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Patent number: 5055581Abstract: The invention provides a novel compound which is a bis(4-alkyl-substituted piperazinylalkyl) ether such as bis[2-(4-methylpiperazinyl)ethyl] ether and bis[2-(4-ethylpiperazinyl)ethyl] ether. The compound, which can be prepared by the dehydrochlorination reaction between a 1-alkyl-substituted piperazine and a bis(chloroalkyl) ether, is useful as a catalyst for the urethane-forming reaction between a polyisocyanate compound and a polyol compound to give an advantage that a sufficiently long mixing time is available to ensure full uniformity of the reaction mixture before substantial proceeding of the reaction.Type: GrantFiled: May 2, 1990Date of Patent: October 8, 1991Assignee: San-Apro LimitedInventors: Keiichi Nakatani, Nobuyasu Nakasugi
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Patent number: 5011935Abstract: A urethane catalyst which is an imidazole ether compound of the formula ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are independently hydrogen, methyl or ethyl and R.sub.4 is ethylene, n-propylene or isopropylene.The imidazole compounds provide for delayed initiation while maintaining an acceptable cure time in the production of polyurethane foam.Type: GrantFiled: June 27, 1989Date of Patent: April 30, 1991Assignee: San-Apro LimitedInventors: Keiichi Nakatani, Nobuyasu Nakasugi