US 11,667,748 B2
Curable composition, curable paste material, curable sheet material, curable modeling material, curing method, and cured product
Noriya Hayashi, Tokyo (JP); Toshikatsu Sakakibara, Tokyo (JP); Yusuke Kobayashi, Tokyo (JP); and Tatsuya Kimura, Tokyo (JP)
Assigned to MITSUBISHI HEAVY INDUSTRIES, LTD., Tokyo (JP)
Appl. No. 16/636,673
Filed by MITSUBISHI HEAVY INDUSTRIES, LTD., Tokyo (JP)
PCT Filed Aug. 29, 2017, PCT No. PCT/JP2017/030905
§ 371(c)(1), (2) Date Feb. 5, 2020,
PCT Pub. No. WO2019/043778, PCT Pub. Date Mar. 7, 2019.
Prior Publication US 2020/0190251 A1, Jun. 18, 2020
Int. Cl. C08G 59/24 (2006.01); C08G 59/02 (2006.01); C08G 65/18 (2006.01); C08K 5/375 (2006.01); C08K 3/36 (2006.01); C08G 59/22 (2006.01); C08G 65/22 (2006.01); C08G 59/68 (2006.01); C08L 63/00 (2006.01)
CPC C08G 59/245 (2013.01) [C08G 59/022 (2013.01); C08G 65/18 (2013.01); C08K 5/375 (2013.01); C08K 3/36 (2013.01)] 20 Claims
 
1. A curable composition comprising:
a cationic polymerizable compound;
a thermal polymerization initiator; and
a storage stabilizer, and
a filler, wherein the cationic polymerizable compound includes
at least one glycidyl ether compound, at least one alicyclic epoxy compound, and at least one oxetane compound; or
at least one glycidyl ether compound, and at least one oxetane compound; or
at least one alicyclic epoxy compound, and at least one oxetane compound,
the oxetane compound includes 4,4′-bis[(3-ethyl-3-oxetanyl) methoxymethyl] biphenyl,
the thermal polymerization initiator is a compound capable of decomposing at a temperature of 65° C. or lower and generating a Lewis acid or a protonic acid,
the thermal polymerization initiator includes a sulfonium salt represented by the following Formula (I-1-1),

OG Complex Work Unit Chemistry
and a sulfonium salt represented by the following Formula (I-2),

OG Complex Work Unit Chemistry
wherein R1 represent a hydrogen atom, a methyl group, an acetyl group, or a methoxycarbonyl group, R2, and R3 each independently represents a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms, and R4 represents a hydrogen atom, a halogen atom, a nitro group, a methyl group, or a methoxy group, R5 represents an alkyl group having 1 to 4 carbon atoms, and X represents SbF6, PF6, AsF6, or BF4,
a content of the thermal polymerization initiator is 0.3 to 3 parts by mass with respect to 100 parts by mass of the cationic polymerizable compound,
the storage stabilizer is a compound that can capture the Lewis acid or the protonic acid generated by the decomposition of the thermal polymerization initiator,
the filler is at least one selected from the group consisting of glass, silica, ceramic, plastic, and metal,
a content of the filler is 50-80% by mass with respect to the total mass of the curable composition, and
chain curing is enabled by thermal energy generated by a polymerization reaction of the cationic polymerizable compound at a temperature of 65° C. or lower.