Polymerizable composition for optical material, optical material obtained from polymerizable composition, and manufacturing method of optical material

Patent metadata

Field	Value
Publication number	US-2016272784-A1
Application number	US-201414777783-A
Country	US
Kind code	A1
Filing date	Mar 26, 2014
Priority date	Mar 26, 2013
Publication date	Sep 22, 2016
Grant date	—

Abstract

The polymerizable composition for an optical material of the present invention contains (A) at least one kind of isocyanate having two or more isocyanato groups, which contains aromatic isocyanate, (B) at least one kind of alcohol having two or more hydroxyl groups, (C) an acidic phosphoric acid ester represented by the following Formula (1), and (D) a benzotriazole-based compound, in which a ratio of secondary hydroxyl groups to the total molar number of primary and secondary hydroxyl groups contained in the alcohol (B) is equal to or greater than 50%, and the benzotriazole-based compound (D) is contained in an amount of 1 part by weight to 11 parts by weight with respect to a total of 100 parts by weight of the isocyanate (A) and the alcohol (B).

First claim

1 . A polymerizable composition for an optical material, comprising:
(A) at least one kind of isocyanate having two or more isocyanato groups, which contains aromatic isocyanate; (B) at least one kind of alcohol having two or more hydroxyl groups; (C) an acidic phosphoric acid ester represented by the following Formula (1); and (D) a benzotriazole-based compound, wherein a ratio of secondary hydroxyl groups to the total molar number of primary and secondary hydroxyl groups contained in the alcohol (B) is equal to or greater than 50%, and the benzotriazole-based compound (D) is contained in an amount of 1 part by weight to 11 parts by weight with respect to a total of 100 parts by weight of the isocyanate (A) and the alcohol (B),

wherein, in the formula, m represents an integer of 1 or 2, n represents an integer of 0 to 18, R 1 represents an alkyl group having 1 to 20 carbon atoms, and each of R 2 and R 3 independently represents a hydrogen atom, a methyl group, or an ethyl group.

2 . The polymerizable composition for an optical material according to claim 1 ,
wherein the alcohol (B) contains at least one kind of compounds selected from among glycerol, digylcerol, trimethylolpropane, pentaerythritol, di(trimethylolpropane), an ethylene oxide adduct of glycerol, an ethylene oxide adduct of trimethylolpropane, an ethylene oxide adduct of pentaerythritol, a propylene oxide adduct of glycerol, a propylene oxide adduct of trimethylolpropane, and a propylene oxide adduct of pentaerythritol.

3 . The polymerizable composition for an optical material according to claim 1 ,
wherein the alcohol (B) contains at least one kind of compounds selected from among a propylene oxide adduct of glycerol, a propylene oxide adduct of trimethylolpropane, and a propylene oxide adduct of pentaerythritol.

4 . The polymerizable composition for an optical material according to claim 1 ,
wherein the aromatic isocyanate is 2,4-tolylene diisocyanate or a mixture of 2,4-tolylene diisocyanate and 2,6-tolylene diisocyanate.

5 . The polymerizable composition for an optical material according to claim 1 ,
wherein a molar ratio of the isocyanato groups of the isocyanate (A) to the hydroxyl groups of the alcohol (B) is 0.8 to 1.2.

6 . The polymerizable composition for an optical material according to claim 1 ,
wherein the acidic phosphoric acid ester (C) is contained in an amount of 0.1 parts by weight to 3 parts by weight with respect to the total of 100 parts by weight of the isocyanate (A) and the alcohol (B).

7 . The polymerizable composition for an optical material according to claim 1 , further comprising a hindered amine-based compound,
wherein the hindered amine-based compound is contained in an amount of 0.1 parts by weight to 2 parts by weight with respect to the total of 100 parts by weight of the isocyanate (A) and the alcohol (B).

8 . The polymerizable composition for an optical material according to claim 1 ,
wherein the benzotriazole-based compound (D) is contained in an amount of 2.1 parts by weight to 10 parts by weight with respect to the total of 100 parts by mass of the isocyanate (A) and the alcohol (B).

9 . The polymerizable composition for an optical material according to claim 1 , further comprising (E) a phenol-based compound;
wherein the phenol-based compound (E) is contained in an amount of 0.5 parts by weight to 5 parts by weight with respect to the total of 100 parts by weight of the isocyanate (A) and the alcohol (B).

10 . A manufacturing method of a polyurethane-molded product, comprising:
a step of obtaining the polymerizable composition for an optical material according to claim 1 by mixing the alcohol (B), the acidic phosphoric acid ester (C), and the benzotriazole-based compound (D) together and then mixing the resultant with at least one kind of the isocyanate (A), which contains aromatic isocyanate and has two or more isocyanato groups, at a temperature of equal to or less than 30° C.; a step of casting the polymerizable composition into a casting mold; and a step of polymerizing the polymerizable composition by starting the polymerization of the composition at a temperature of equal to or less than 30° C.

11 . The manufacturing method of a polyurethane-molded product according to claim 10 ,
wherein the step of obtaining the polymerizable composition for an optical material includes a step of obtaining the polymerizable composition for an optical material according to claim 9 by mixing the alcohol (B), the acidic phosphoric acid ester (C), the benzotriazole-based compound (D), and the phenol-based compound (E) together and then mixing the resultant with at least one kind of the isocyanate (A), which contains aromatic isocyanate and has two or more isocyanato groups, at a temperature of equal to or less than 30° C.

12 . A manufacturing method of a plastic polarizing lens, comprising:
a step of obtaining the polymerizable composition for an optical material according to claim 1 by mixing the alcohol (B), the acidic phosphoric acid ester (C), and the benzotriazole-based compound (D) together and then mixing the resultant with at least one kind of the isocyanate (A), which contains aromatic isocyanate and has two or more isocyanato groups, at a temperature of equal to or less than 30° C.; a step of fixing a polarizing film in a casting mold for lens casting in a state in which at least one surface of the polarizing film is separated from the mold; a step of injecting the polymerizable composition into a space between the polarizing film and the mold; and a step of laminating a layer comprised of polyurethane resin over at least one surface of the polarizing film by polymerizing and curing the polymerizable composition by starting the polymerization of the composition at a temperature of equal to or less than 30° C.

13 . The manufacturing method of a plastic polarizing lens according to claim 12 ,
wherein the step of obtaining the polymerizable composition for an optical material includes a step of obtaining the polymerizable composition for an optical material according to claim 9 by mixing the alcohol (B), the acidic phosphoric acid ester (C), the benzotriazole-based compound (D), and the phenol-based compound (E) together and then mixing the resultant with at least one kind of the isocyanate (A), which contains aromatic isocyanate and has two or more isocyanato groups, at a temperature of equal to or less than 30° C.

14 . A manufacturing method of a polyurethane-molded product, comprising:
a step (i) of obtaining a prepolymer by adding the alcohol (B) to the isocyanate (A) such that a ratio of the hydroxyl groups to the isocyanato groups of the isocyanate (A) falls into a range of 10 mol % to 20 mol % and reacting the isocyanate (A) with the alcohol (B) in the presence of the acidic phosphoric acid ester (C), the benzotriazole-based compound (D), and the hindered amine-based compound, a step (ii) of obtaining the polymerizable composition for an optical material described in claim 1 by further adding the alcohol (B) to the prepolymer and mixing the alcohol (B) and the prepolymer together at a temperature of equal to or less than 30° C.; and a step (iii) of polymerizing the prepolymer and the alcohol (B) contained in the polymerizable composition.

15 . The manufacturing method according to claim 14 ,
wherein the step (i) includes a step of obtaining a prepolymer by adding the alcohol (B) to the isocyanate (A) such that the ratio of the hydroxyl groups t

Assignees

• Mitsui Chemicals Inc

Inventors

• Ito Shinsuke
• Kawato Nobuo
• Suesugi Kouji
• Kuma Shigetoshi
• Ogawa Tatsuya
• Hashimoto Toshiya
• Tanaka Mamoru

Classifications

• C08G18/48

  Polyethers · CPC title

• C08L75/04

  Polyurethanes · CPC title

• C08K5/29

  Compounds containing {one or more} carbon-to-nitrogen double bonds · CPC title

• B29D11/00009

  Production of simple or compound lenses · CPC title

• C08G18/7621 Primary

  being toluene diisocyanate including isomer mixtures · CPC title