Patents Assigned to San-Apro Ltd.
  • Publication number: 20240027901
    Abstract: Provided are: a photoacid generator that effectively generates acid even when a substance such as a colorant which attenuates or blocks radiated light is present at a high concentration, the film thickness thereof is large, and a light source is visible light to infrared light, particularly infrared light having low energy; and a highly curable photosensitive composition using the photoacid generator. The present invention is a photoacid generator that is a metal complex having, as a ligand, a ring structure formed by bonding five-membered ring aromatic heterocyclic compounds directly or by ?-conjugation, wherein a central metal has one or two axial ligands, and the axial ligand has an onium salt structure.
    Type: Application
    Filed: October 28, 2021
    Publication date: January 25, 2024
    Applicant: SAN-APRO LTD.
    Inventors: Atsushi Shiraishi, Futaba Kawakami
  • Publication number: 20230100642
    Abstract: Provided are: a new sulfonium salt highly photosensitive to active energy ray, in particular, i-line or h-line; and a new photoacid generator which is highly photosensitive to i-line or h-line, and comprises a sulfonium salt that is highly soluble in a solvent and a cationically polymerizable compound such as an epoxy compound, and has excellent storage stability in the formulation. The present invention pertains to a sulfonium salt represented by general formula (1), and a photoacid generator comprising said sulfonium salt.
    Type: Application
    Filed: January 4, 2021
    Publication date: March 30, 2023
    Applicant: SAN-APRO LTD.
    Inventors: Takuto Nakao, Yuji Nakamura
  • Publication number: 20220315530
    Abstract: Provided is an onium salt functioning as a photoacid generator. The photoacid generator can provide a chemically amplifiable photoresist composition when it is combined with a resin component whose solubility in alkali is increased by the action of an acid generated by active energy ray irradiation such as Light or electron beam irradiation. The present invention relates to an onium salt represented by the formula (1), containing an anion structure with a proportion of a facial isomer in a total of the facial isomer and a meridional isomer being 15.0% by weight or lower.
    Type: Application
    Filed: May 7, 2021
    Publication date: October 6, 2022
    Applicant: SAN-APRO LTD.
    Inventors: Yoshihiko AKAZAWA, Tomohito KIZU, Ryosuke TAKAHASHI, Yuji NAKAMURA, Hideki KIMURA
  • Patent number: 11370751
    Abstract: The sulfonium salt does not contain a toxic metal and exhibits higher cationic polymerization performance and crosslinking performance than a tetrakis(pentafluorophenyl)borate salt. The heat- or photo-acid generator contains the sulfonium salt. The sulfonium salt is formed of a sulfonium cation selected from a group represented by general formulas (1), (9), (10) and (11) described below and a gallate anion represented by formula (a). The heat- or photo-acid generator contains the sulfonium salt. The heat- or energy ray-curable composition contains the acid generator and a cationically polymerizable compound. A cured product can be obtained by curing the same.
    Type: Grant
    Filed: July 6, 2017
    Date of Patent: June 28, 2022
    Assignee: SAN APRO LTD.
    Inventors: Noriya Fukunaga, Yusaku Takashima
  • Publication number: 20220089562
    Abstract: Provided are a novel sulfonium salt having high photosensitivity to g-rays or h-rays; a novel photoacid generator containing a sulfonium salt that has high photosensitivity to g-rays or h-rays, has high solubility in solvents and cationically polymerizable compounds such as epoxy compounds, and has an excellent storage stability in compositions containing the cationically polymerizable compounds; and the like. The present invention relates to a sulfonium salt represented by the formula (1), a photoacid generator containing the sulfonium salt, and the like.
    Type: Application
    Filed: December 16, 2019
    Publication date: March 24, 2022
    Applicant: SAN-APRO LTD.
    Inventor: Takuto NAKAO
  • Publication number: 20210147352
    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: Application
    Filed: April 9, 2019
    Publication date: May 20, 2021
    Applicant: SAN-APRO LTD.
    Inventors: Takuto Nakao, Yusaku Takashima
  • Patent number: 10683266
    Abstract: A sulfonium salt is formed of a sulfonium cation selected from a group indicated by general formulas (1), (2), and (3) and a gallate anion represented by formula (a). A photoacid generator is characterized in that said sulfonium salt is contained therein. An energy-ray curable composition contains the acid generator and a cationic polymerizable compound. A cured product is formed by curing these substances.
    Type: Grant
    Filed: June 12, 2017
    Date of Patent: June 16, 2020
    Assignee: SAN APRO LTD.
    Inventors: Noriya Fukunaga, Yusaku Takashima
  • Publication number: 20190300476
    Abstract: A sulfonium salt is formed of a sulfonium cation selected from a group indicated by general formulas (1), (2), and (3) and a gallate anion represented by formula (a). A photoacid generator is characterized in that said sulfonium salt is contained therein. An energy-ray curable composition contains the acid generator and a cationic polymerizable compound. A cured product is formed by curing these substances.
    Type: Application
    Filed: June 12, 2017
    Publication date: October 3, 2019
    Applicant: SAN-APRO LTD.
    Inventors: Noriya Fukunaga, Yusaku Takashima
  • Publication number: 20190284134
    Abstract: The sulfonium salt does not contain a toxic metal and exhibits higher cationic polymerization performance and crosslinking performance than a tetrakis(pentafluorophenyl)borate salt. The heat- or photo-acid generator contains the sulfonium salt. The sulfonium salt is formed of a sulfonium cation selected from a group represented by general formulas (1), (9), (10) and (11) described below and a gallate anion represented by formula (a). The heat- or photo-acid generator contains the sulfonium salt. The heat- or energy ray-curable composition contains the acid generator and a cationically polymerizable compound. A cured product can be obtained by curing the same.
    Type: Application
    Filed: July 6, 2017
    Publication date: September 19, 2019
    Applicant: SAN APRO LTD.
    Inventors: Noriya Fukunaga, Yusaku Takashima
  • Publication number: 20180373145
    Abstract: The purpose of the present invention is to provide a photosensitive composition having excellent curability even when a colorant or other substance for attenuating or blocking radiated light is present at a high concentration, the film thickness thereof is large, and the light source is visible-to-infrared light, particularly infrared light having low energy. The present invention is a photosensitive composition characterized by containing as essential components (A) an onium salt represented by general formula (1), (B) a sensitizer, and (C) a radical polymerizable compound. (In formula (1), Rf each independently represents a C1-8 alkyl group, a C2-8 alkenyl group, or a C6-10 aryl group, 80% or more of hydrogen atoms bonded to the carbon atoms of each group being substituted with fluorine atoms, n represents an integer of 1 to 5, and A+ represents a monovalent onium cation.
    Type: Application
    Filed: December 20, 2016
    Publication date: December 27, 2018
    Applicant: SAN-APRO LTD.
    Inventor: Atsushi Shiraishi
  • Publication number: 20180329297
    Abstract: The heat- or energy ray-curable composition for members contains an onium gallate salt having a specific structure. The invention is a heat- or energy ray-curable composition comprising a cationic polymerizable compound and an acid generator containing an onium gallate salt represented by general formula (1). In formula (1), R1-R4 are each independently an alkyl group having 1 to 18 carbon atoms or Ar; however, at least one is Ar; Ar is an aryl group having 6 to 14 carbon atoms (not including the number of carbon atoms in the following substituents); some of the hydrogen atoms in the aryl group may be substituted by alkyl groups having 1 to 18 carbon atoms or the like; E represents an element of valence n of group 15 to group 17 (IUPAC notation); n is an integer of 1-3; and R5 is an organic group bonded to E.
    Type: Application
    Filed: August 5, 2016
    Publication date: November 15, 2018
    Applicants: SAN-APRO LTD., SAN-APRO LTD.
    Inventors: Noriya Fukunaga, Yusaku Takashima, Takuya Ikeda, Hideo Seike
  • Patent number: 9933701
    Abstract: Provided are a photobase generator having higher sensitivity to light than do conventional photobase generators, and a photosensitive resin composition containing the photobase generator. The present invention is a photobase generator characterized in containing a salt represented by general formula (1). (In formula (1), R1-R4 are mutually independent groups represented by general formula (2), C1-18 alkyl groups, or Ar, with at least one being a group represented by general formula (2); in formula (2), (D) is a divalent group bonded on at least one side to elemental boron, and Ar1 is the same as the aforementioned Ar; and Q+ is a monovalent onium cation.
    Type: Grant
    Filed: November 17, 2014
    Date of Patent: April 3, 2018
    Assignee: SAN APRO LTD.
    Inventors: Takuya Ikeda, Atsushi Shiraishi
  • Publication number: 20160368879
    Abstract: Provided is a non-ionic photoacid generator (A) expressed by general formula (1). R1 and R2 each independently represents an alkyl group having 1-18 carbons or a fluoroalkyl group having 1-18 carbons, an alkenyl group having 2-18 carbons, an alkynyl group having 2-18 carbons, an aryl group having 6-18 carbons, a silyl group, or the like; m and n respectively represent the number of R1s and R2s, each number being an integer from 0 to 3, and the total number (m+n) of R1s and R2s being an integer from 1 to 6. The m number of R1s and the n number of R2s may each be the same or different. R3 represents a hydrocarbon having 1-18 carbons wherein one part or all of the hydrogen may be substituted by fluorine.
    Type: Application
    Filed: July 3, 2014
    Publication date: December 22, 2016
    Applicant: SAN-APRO LTD.
    Inventors: Takuya IKEDA, Hideki KIMURA, Tomoyuki SHIBAGAKI, Masaaki OKA
  • Publication number: 20160299429
    Abstract: Provided are a photobase generator having higher sensitivity to light than do conventional photobase generators, and a photosensitive resin composition containing the photobase generator. The present invention is a photobase generator characterized in containing a salt represented by general formula (1). (In formula (1), R1-R4 are mutually independent groups represented by general formula (2), C1-18 alkyl groups, or Ar, with at least one being a group represented by general formula (2); in formula (2), (D) is a divalent group bonded on at least one side to elemental boron, and Ar1 is the same as the aforementioned Ar; and Q+ is a monovalent onium cation.
    Type: Application
    Filed: November 17, 2014
    Publication date: October 13, 2016
    Applicant: SAN APRO LTD.
    Inventors: Takuya Ikeda, Atsushi Shiraishi
  • Publication number: 20160009737
    Abstract: There is provided a photobase generator and a photosensitive resin composition containing the photobase generator. The photobase generator includes an ammonium salt represented by general formula (1). In formula (1), R1 to R4 independently represent an alkyl group having 1 to 18 carbon atoms or Ar, wherein at least one of R1 to R4 represents Ar; Ar represents an aryl group having 6 to 14 carbon atoms (excluding carbon atoms contained in a substituent as mentioned below), wherein some of hydrogen atoms in the aryl group may be independently substituted by an alkyl group having 1 to 18 carbon atoms or the like; Y+ represents an ammonio group represented by general formula (2) or (3); and E represents a hydrogen atom or a group represented by general formula (5).
    Type: Application
    Filed: February 26, 2014
    Publication date: January 14, 2016
    Applicant: SAN-APRO LTD.
    Inventors: Takuya Ikeda, Atsushi Shiraishi, Takeshi Furuta
  • Publication number: 20140357896
    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: Application
    Filed: May 29, 2014
    Publication date: December 4, 2014
    Applicants: SAN-APRO LTD., TOKYO OHKA KOGYO CO., LTD.
    Inventors: Issei Suzuki, Takuya Ikeda, Yusaku Takashima, Takeshi Furuta, Yoshitaka Komuro, Yoshiyuki Utsumi, Takaaki Kaiho, Toshiaki Hato
  • Patent number: 8617787
    Abstract: There is provided a sulfonium salt having high photosensitivity to the i-line. The invention relates to a sulfonium salt represented by formula (1) described below: [in formula (1), R1 to R6 each independently represent an alkyl group, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, an acyloxy group, an arylthio group, an alkylthio group, an aryl group, a heterocyclic hydrocarbon group, an aryloxy group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a hydroxy(poly)alkyleneoxy group, an optionally substituted amino group, a cyano group, a nitro group, or a halogen atom, m1 to m6 each represent the number of occurrences of each of R1 to R6, m1, m4, and m6 each represent an integer of 0 to 5, m2, m3, and m5 each represent an integer of 0 to 4, and X? represents a monovalent polyatomic anion].
    Type: Grant
    Filed: February 4, 2010
    Date of Patent: December 31, 2013
    Assignee: San-Apro, Ltd.
    Inventors: Issei Suzuki, Hideki Kimura
  • Patent number: 8338074
    Abstract: It is intended to provide the following resin composition for stereolithography which is superior in storage stability and aging stability during operation, shows no increase in viscosity upon prolonged storage, has a high light-curing sensitivity and, therefore, makes it possible to produce, upon photo irradiation, an object by stereolithography, which is superior in dimensional accuracy, fabricating accuracy, water resistance, moisture resistance and mechanical properties at a high fabricating speed and a high productivity.
    Type: Grant
    Filed: June 24, 2004
    Date of Patent: December 25, 2012
    Assignees: CMET Inc., San-Apro Ltd.
    Inventors: Takashi Ito, Tsuneo Hagiwara, Hideki Kimura, Masashi Date, Jiro Yamamoto
  • Publication number: 20110300482
    Abstract: There is provided a sulfonium salt having high photosensitivity to the i-line. The invention relates to a sulfonium salt represented by formula (1) described below: [in formula (1), R1 to R6 each independently represent an alkyl group, a hydroxy group, an alkoxy group, an alkylcarbonyl group, an arylcarbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, an arylthiocarbonyl group, an acyloxy group, an arylthio group, an alkylthio group, an aryl group, a heterocyclic hydrocarbon group, an aryloxy group, an alkylsulfinyl group, an arylsulfinyl group, an alkylsulfonyl group, an arylsulfonyl group, a hydroxy(poly) alkyleneoxy group, an optionally substituted amino group, a cyano group, a nitro group, or a halogen atom, m1 to m6 each represent the number of occurrences of each of R1 to R6, m1, m4, and m6 each represent an integer of 0 to 5, m2, m3, and m5 each represent an integer of 0 to 4, and X? represents a monovalent polyatomic anion].
    Type: Application
    Filed: February 4, 2010
    Publication date: December 8, 2011
    Applicant: SAN-APRO, LTD
    Inventors: Issei Suzuki, Hideki Kimura