US 12,077,636 B2
Highly soluble tris-(2,3-epoxypropyl)-isocyanurate and method for producing same
Motohiko Hidaka, Tokyo (JP); Takashi Oda, Funabashi (JP); Nobuyuki Kakiuchi, Funabashi (JP); and Hiroki Yamaguchi, Funabashi (JP)
Assigned to NISSAN CHEMICAL CORPORATION, Tokyo (JP)
Filed by NISSAN CHEMICAL CORPORATION, Tokyo (JP)
Filed on May 3, 2023, as Appl. No. 18/142,625.
Application 18/142,625 is a division of application No. 16/402,305, filed on May 3, 2019.
Application 16/402,305 is a division of application No. 14/759,486, abandoned, previously published as PCT/JP2014/050063, filed on Jan. 7, 2014.
Claims priority of application No. 2013-003377 (JP), filed on Jan. 11, 2013.
Prior Publication US 2023/0287179 A1, Sep. 14, 2023
Int. Cl. C08G 73/06 (2006.01); C07D 405/14 (2006.01); C08G 59/32 (2006.01); C08G 59/42 (2006.01); C08G 59/68 (2006.01); C09D 179/04 (2006.01); C09J 179/04 (2006.01)
CPC C08G 73/0644 (2013.01) [C07D 405/14 (2013.01); C08G 59/3245 (2013.01); C08G 59/4215 (2013.01); C08G 59/688 (2013.01); C09D 179/04 (2013.01); C09J 179/04 (2013.01); Y10T 428/2982 (2015.01)] 7 Claims
 
1. A method comprising
producing an α-type tris-(2,3-epoxypropyl)-isocyanurate crystal comprising β-type tris-(2,3-epoxypropyl)-isocyanurate in the crystal in a ratio of 2% by mass to 15% by mass and the crystal having a particle diameter of 1 μm to 500 μm, the method comprising:
generating tris-(2,3-epoxypropyl)-isocyanurate as an epichlorohydrin adduct of cyanuric acid by reacting 1 mol of cyanuric acid with 5 mol to 180 mol of epichlorohydrin and subsequently carrying out dehydrochlorination;
forming a tris-(2,3-epoxypropyl)-isocyanurate solution from the generated tris-(2,3-epoxypropyl)-isocyanurate and a solvent that includes one or more of methyl ethyl ketone, acetone, acetonitrile, ethyl acetate, or epichlorohydrin;
separating undissolved β-type tris-(2,3-epoxypropyl)-isocyanurate from the tris-(2,3-epoxypropyl)-isocyanurate solution as a solid to obtain a crystal with an increased content ratio of α-type tris-(2,3-epoxypropyl)-isocyanurate; and
extracting β-type tris-(2,3-epoxypropyl)-isocyanurate contained in the crystal or the tris-(2,3-epoxypropyl)-isocyanurate solution with an additional solvent to obtain a crystal with a further increased content ratio of α-type tris-(2,3-epoxypropyl)-isocyanurate, wherein the additional solvent is one or more of methyl ethyl ketone, acetone, methanol, ethanol, water, or isopropanol.