Patents Assigned to San-Apro Limited
  • Patent number: 11926581
    Abstract: 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: Grant
    Filed: April 9, 2019
    Date of Patent: March 12, 2024
    Assignee: SAN-APRO LIMITED
    Inventors: Takuto Nakao, Yusaku Takashima
  • Patent number: 10450266
    Abstract: 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: Grant
    Filed: October 13, 2015
    Date of Patent: October 22, 2019
    Assignee: SAN-APRO LIMITED
    Inventors: Masaaki Oka, Yuji Nakamura
  • Publication number: 20170233336
    Abstract: 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: Application
    Filed: October 13, 2015
    Publication date: August 17, 2017
    Applicant: SAN-APRO LIMITED
    Inventors: Masaaki Oka, Yuji Nakamura
  • Patent number: 9045398
    Abstract: 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: Grant
    Filed: May 29, 2014
    Date of Patent: June 2, 2015
    Assignees: 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
  • Patent number: 8329771
    Abstract: 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: Grant
    Filed: March 18, 2009
    Date of Patent: December 11, 2012
    Assignee: San-Apro Limited
    Inventors: Atsushi Shiraishi, Hideki Kimura
  • Patent number: 8278030
    Abstract: 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: Grant
    Filed: April 27, 2009
    Date of Patent: October 2, 2012
    Assignee: San-Apro Limited
    Inventors: Issei Suzuki, Hideki Kimura
  • Publication number: 20110039205
    Abstract: 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: Application
    Filed: April 27, 2009
    Publication date: February 17, 2011
    Applicant: SAN-APRO LIMITED
    Inventors: Issei Suzuki, Hideki Kimura
  • Publication number: 20110028585
    Abstract: 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: Application
    Filed: March 18, 2009
    Publication date: February 3, 2011
    Applicant: SAN-APRO LIMITED
    Inventors: Atsushi Shiraishi, Hideki Kimura
  • Patent number: 7709598
    Abstract: 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: Grant
    Filed: May 27, 2005
    Date of Patent: May 4, 2010
    Assignee: San-Apro Limited
    Inventors: Hideki Kimura, Jiro Yamamoto, Shinji Yamashita, Mitsuo Kurumaya, Takaaki Sonoda
  • Patent number: 7709548
    Abstract: 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: Grant
    Filed: December 17, 2007
    Date of Patent: May 4, 2010
    Assignee: San-Apro Limited
    Inventors: Masashi Date, Hideki Kimura, Shinji Yamashita, Jiro Yamamoto
  • Patent number: 7060858
    Abstract: 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: Grant
    Filed: December 17, 2001
    Date of Patent: June 13, 2006
    Assignee: San-Apro Limited
    Inventors: Masashi Date, Hideki Kimura, Jiro Yamamoto
  • Patent number: 6027777
    Abstract: 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: Grant
    Filed: October 10, 1996
    Date of Patent: February 22, 2000
    Assignees: Alcare Co. Ltd., SAN-APRO Limited
    Inventors: Hiroyuki Hirano, Wataru Okuyama, Nobuyasu Nakasugi, Shozo Oonishi
  • Patent number: 5665056
    Abstract: 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: Grant
    Filed: November 9, 1994
    Date of Patent: September 9, 1997
    Assignees: Alcare Co., Ltd., San-Apro Limited
    Inventors: Nobuyasu Nakasugi, Takayuki Sekine
  • Patent number: 5527266
    Abstract: 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: Grant
    Filed: June 6, 1994
    Date of Patent: June 18, 1996
    Assignee: San-Apro Limited
    Inventors: Kouzou Hiraishi, Nobuyasu Nakasugi
  • Patent number: 5064957
    Abstract: 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: Grant
    Filed: March 13, 1990
    Date of Patent: November 12, 1991
    Assignee: San-Apro Limited
    Inventor: Nobuyasu Nakasugi
  • Patent number: 5055581
    Abstract: 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: Grant
    Filed: May 2, 1990
    Date of Patent: October 8, 1991
    Assignee: San-Apro Limited
    Inventors: Keiichi Nakatani, Nobuyasu Nakasugi
  • Patent number: 5011935
    Abstract: 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: Grant
    Filed: June 27, 1989
    Date of Patent: April 30, 1991
    Assignee: San-Apro Limited
    Inventors: Keiichi Nakatani, Nobuyasu Nakasugi