US 12,275,813 B2
Polymerizable composition for optical materials and application of same
Nigel Ribeiro, Omuta (JP); Hongbo Wang, Singapore (SG); and Yixi Lin, Singapore (SG)
Assigned to MITSUI CHEMICALS, INC., Tokyo (JP)
Appl. No. 16/771,788
Filed by MITSUI CHEMICALS, INC., Tokyo (JP)
PCT Filed Dec. 14, 2018, PCT No. PCT/JP2018/046196
§ 371(c)(1), (2) Date Jun. 11, 2020,
PCT Pub. No. WO2019/117305, PCT Pub. Date Jun. 20, 2019.
Claims priority of application No. 10201710468Q (SG), filed on Dec. 15, 2017.
Prior Publication US 2021/0017327 A1, Jan. 21, 2021
This patent is subject to a terminal disclaimer.
Int. Cl. C08G 18/66 (2006.01); C08G 18/38 (2006.01); C08G 18/42 (2006.01); C08G 18/76 (2006.01); C08K 5/1545 (2006.01); G02B 1/04 (2006.01)
CPC C08G 18/6633 (2013.01) [C08G 18/3876 (2013.01); C08G 18/4277 (2013.01); C08G 18/7642 (2013.01); C08K 5/1545 (2013.01); G02B 1/041 (2013.01)] 19 Claims
OG exemplary drawing
 
1. A polymerizable composition for a plastic lens, comprising:
a polyester polyol (a) having a weight average molecular weight of more than 4,000 g/mol and 10,000 g/mol or less;
a photochromic compound (b); and
a polymerization reactive compound (c), other than the polyester polyol (a),
wherein the polymerization reactive compound (c) consisting of a combination of a polyiso(thio)cyanate compound and a polythiol compound having two or more mercapto groups,
wherein the polyester polyol (a) is at least one selected from a polycaprolactone diol represented by the following General Formula (1) and a polycaprolactone polyol represented by the following General Formula (2),

OG Complex Work Unit Chemistry
wherein, in General Formula (1), R represents the diol, and n represents a unit number of the caprolactone monomer, and each unit number is an integer of 2 to 88,

OG Complex Work Unit Chemistry
wherein, in general formula (2), Q represents the polyol with 3 or more primary hydroxyl groups, and n represents a unit number of the caprolactone monomer, and each unit number is an integer of 2 to 58,
wherein the polythiol compound having two or more mercapto groups consists of one or more compounds selected from methanedithiol, 1,2-ethanedithiol, 1,2,3-propanetrithiol, 1,2-cyclohexanedithiol, bis(2-mercaptoethyl) ether, tetrakis(mercaptomethyl) methane, diethylene glycol bis(2-mercaptoacetate), diethylene glycol bis(3-mercaptopropionate), ethylene glycol bis(2-mercaptoacetate), ethylene glycol bis(3-mercaptopropionate), trimethylolpropane tris(2-mercaptoacetate), trimethylolpropane tris(3-mercaptopropionate), trimethylolethane tris(2-mercaptoacetate), trimethylolethane tris(3-mercaptopropionate), pentaerythritol tetrakis(2-mercaptoacetate), pentaerythritol tetrakis(3-mercaptopropionate), bis(mercaptomethyl) sulfide, bis(mercaptomethyl)disulfide, bis(mercaptoethyl) sulfide, bis(mercaptoethyl)disulfide, bis(mercaptopropyl) sulfide, bis(mercaptomethylthio) methane, bis(2-mercaptoethylthio) methane, bis(3-mercaptopropylthio) methane, 1,2-bis(mercaptomethylthio) ethane, 1,2-bis(2-mercaptoethylthio) ethane, 1,2-bis(3-mercaptopropylthio) ethane, 1,2,3-tris(mercaptomethylthio) propane, 1,2,3-tris(2-mercaptoethylthio) propane, 1,2,3-tris(3-mercaptopropylthio) propane, 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, tetrakis(mercaptomethylthiomethyl) methane, tetrakis(2-mercaptoethylthiomethyl) methane, tetrakis(3-mercaptopropylthiomethyl) methane, bis(2,3-mercaptopropyl) sulfide, 2,5-dimercaptomethyl-1,4-dithiane, 2,5-dimercapto-1,4-dithiane, 2,5-dimercaptomethyl-2,5-dimethyl-1,4-dithiane, and esters of these thioglycolic acid and mercaptopropionic acid, hydroxymethyl sulfide bis(2-mercaptoacetate), hydroxymethyl sulfide bis(3-mercaptopropionate), hydroxyethyl sulfide bis(2-mercaptoacetate), hydroxyethyl sulfide bis(3-mercaptopropionate), hydroxymethyl disulfide bis(2-mercaptoacetate), hydroxymethyl disulfide bis(3-mercaptopropionate), hydroxyethyl disulfide bis(2-mercaptoacetate), hydroxyethyl disulfide bis(3-mercaptopropionate), 2-mercaptoethyl ether bis(2-mercaptoacetate), 2-mercaptoethyl ether bis(3-mercaptopropionate), thiodiglycolic acid bis(2-mercaptoethylester), thiodipropionic acid bis(2-mercaptoethylester), dithiodiglycolic acid bis(2-mercaptoethyl ester), dithiodipropionic acid bis(2-mercaptoethylester), 1,1,3,3-tetrakis(mercaptomethylthio) propane, 1,1,2,2-tetrakis(mercaptomethylthio) ethane, 4,6-bis(mercaptomethylthio)-1,3-dithiane, tris(mercaptomethylthio) methane, and tris(mercaptoethylthio) methane, 1,2-dimercaptobenzene, 1,3-dimercaptobenzene, 1,4-dimercaptobenzene, 1,2-bis(mercaptomethyl)benzene, 1,3-bis(mercaptomethyl)benzene, 1,4-bis(mercaptomethyl)benzene, 1,2-bis(mercaptoethyl)benzene, 1,3-bis(mercaptoethyl)benzene, 1,4-bis(mercaptoethyl)benzene, 1,3,5-trimercaptobenzene, 1,3,5-tris(mercaptomethyl) benzene, 1,3,5-tris(mercaptomethyleneoxy) benzene, 1,3,5-tris(mercaptoethyleneoxy) benzene, 2,5-toluenedithiol, 3,4-toluenedithiol, 1,5-naphthalenedithiol, and 2,6-naphthalenedithiol, 3,4-thiophene dithiol, bismuthiol, 4,6-bis(mercaptomethylthio)-1,3-dithiane, and 2-(2,2-bis(mercaptomethylthio) ethyl)-1,3-dithietane.