US-12624154-B2 - Xylylenediisocyanate composition and optical polymerizable composition comprising same

US12624154B2US 12624154 B2US12624154 B2US 12624154B2US-12624154-B2

Abstract

A xylylene diisocyanate (XDI) composition according to exemplary embodiments includes xylylene diisocyanate and an acidity regulator having a boiling point of 110° C. or higher, and the composition has an acidity of greater than 100 ppm and 1,000 ppm or less based on a total weight of the xylylene diisocyanate (XDI). An optical lens having a high transmittance and improved optical uniformity can be manufactured by controlling a polymerization reaction rate through acidity adjustment.

Inventors

Jae Young Pai
Jung Hwan MYUNG
Kyeong Hwan You
Hyuk Hee HAN
Jeong Moo Kim
Eui Jun Choi
Jung Hwan Shin

Assignees

SK PUCORE CO., LTD.

Dates

Publication Date: 20260512
Application Date: 20210902
Priority Date: 20200903

Claims (8)

1 . A xylylene diisocyanate composition, comprising: xylylene diisocyanate (XDI); and an acidity regulator, wherein the xylylene diisocyanate composition has an acidity of greater than 100 ppm and 1,000 ppm or less based on a total weight of the xylylene diisocyanate (XDI), wherein a chlorine content of the xylylene diisocyanate composition is less than 100 ppm, wherein the chlorine content of the xylylene diisocyanate composition is measured using a sample combustion apparatus and ion chromatography, and wherein the acidity regulator comprises at least one compound selected from the group consisting of: an inorganic acid compound including halogen acids, sulfuric acid and phosphoric acid; an organic acid compound including trifluoroacetic acid (TFA) and fatty acid; a solid acid including clay, cation exchange resin, acid-impregnated silica gel, acid-impregnated alumina and vanadium oxide; a cyclic amine compound; and a tertiary amine compound, and wherein an acidity variation before and after 3 months storage of the xylylene diisocyanate composition in a dark room at 25° C. is 40 ppm or less.
2 . The xylylene diisocyanate composition according to claim 1 , wherein the chlorine content in the xylylene diisocyanate composition is 10 ppm to 95 ppm.
3 . The xylylene diisocyanate composition according to claim 1 , wherein a transmittance to a light at 380 nm wavelength after 3 months storage in a dark room at 25° C. is 99% or more.
4 . The xylylene diisocyanate composition according to claim 1 , wherein an addition amount of the acidity regulator ranges from 300 ppm to 4,000 ppm.
5 . A polymerizable composition for an optical material, comprising: a xylylene diisocyanate composition according to claim 1 ; a polythiol-based compounds; and an additive.
6 . The polymerizable composition for an optical material according to claim 5 , wherein the additive includes at least one selected from the group consisting of a release agent, a reaction catalyst, a thermal stabilizer, an ultraviolet absorber, and a bluing agent.
7 . A method for preparation of a xylylene diisocyanate composition, the method comprising: synthesizing xylylene diisocyanate from xylenediamine to form a preliminary composition including xylylene diisocyanate; adjusting an acidity of the preliminary composition to a range of greater than 100 ppm to 1,000 ppm based on a total weight of the xylylene diisocyanate by using an acidity regulator, wherein the xylylene diisocyanate composition is prepared to have a chlorine content of less than 100 ppm by changing a distillation temperature of the xylylene diisocyanate composition in the synthesizing, and wherein the chlorine content of the xylylene diisocyanate composition is measured using a sample combustion apparatus and ion chromatography, wherein the acidity regulator comprises at least one compound selected from the group consisting of: an inorganic acid compound including halogen acids, sulfuric acid and phosphoric acid; an organic acid compound including trifluoroacetic acid (TFA) and fatty acid; a solid acid including clay, cation exchange resin, acid-impregnated silica gel, acid-impregnated alumina and vanadium oxide; a cyclic amine compound; and a tertiary amine compound, and wherein an acidity variation before and after 3 months storage of the xylylene diisocyanate composition in a dark room at 25° C. is 40 ppm or less.
8 . The method according to claim 7 , wherein, in the step of adjusting the acidity of the preliminary composition, the acidity regulator which is an acidic acidity regulator is added if the acidity of the preliminary composition is 100 ppm or less, while the acidity regulator which is a basic acidity regulator is added if the acidity of the preliminary composition exceeds 1,000 ppm.

Description

This application is a national stage application of PCT/KR2021/011838 filed on Sep. 2, 2021, which claims priority to Korean Patent Application No. 10-2020-0112405 filed on Sep. 3, 2020, in the Korean Intellectual Property Office (KIPO), the entire disclosure of which is incorporated by reference herein. CROSS-REFERENCE TO RELATED APPLICATION This application claims priority to Korean Patent Application No. 10-2020-0112405 filed on Sep. 3, 2020 in the Korean Intellectual Property Office (KIPO), the entire disclosure of which is incorporated by reference herein. BACKGROUND 1. Field The present invention relates to a xylylene diisocyanate composition and an optical polymerizable composition (“polymerizable composition for an optical material”) including the same. More specifically, the present invention relates to a xylylene diisocyanate composition prepared by a reaction of an amine salt, and a polymerizable composition for an optical material including the same. 2. Description of the Related Art A diisocyanate compound is widely used, for example, as a raw material for manufacturing a polyurethane resin. For example, a diisocyanate compound is used for manufacturing an optical lens using a polyurethane resin, and physical properties of the diisocyanate compound as a manufacturing raw material may directly affect optical properties such as transparency and refractive index of the optical lens. For example, a polythiourethane resin prepared by reacting a polythiol compound and a diisocyanate compound may be utilized as the base material of the optical lens. Among the diisocyanate compounds, xylylene diisocyanate (XDI) is widely used in consideration of chemical and optical properties such as reactivity and transparency. For example, a polymerizable composition for an optical lens may be prepared by preparing a composition including XDI and mixing it with a composition including a polythiol compound. In consideration of the stability of XDI and appropriate reactivity with the polythiol compound, it is necessary to design physical properties of the composition of XDI, the synthesis process and the like. For example, Korean Patent Laid-Open Publication No. 2012-0076329 discloses a urethane-based optical material prepared using an isocyanate compound. However, physical properties of the isocyanate composition itself are not considered. SUMMARY An object according to exemplary embodiments is to provide a xylylene diisocyanate composition having improved reaction stability and optical properties, and a method for preparation thereof. In addition, another object according to exemplary embodiments is to provide a polymerizable composition for an optical material which includes a xylylene diisocyanate composition having improved reaction stability and optical properties. Further, another object according to exemplary embodiments is to provide an optical product prepared from the polymerizable composition for an optical material. A xylylene diisocyanate composition according to exemplary embodiments includes: xylylene diisocyanate (XDI); and an acidity regulator having a boiling point of 110° C. or higher, wherein the xylylene diisocyanate composition has an acidity of greater than 100 ppm and 1,000 ppm or less based on a total weight of the xylylene diisocyanate (XDI). In some embodiments, a chlorine content in the composition may be less than 100 ppm. In some embodiments, the chlorine content in the composition may be 10 ppm to 95 ppm. In some embodiments, an acidity variation of the xylylene diisocyanate composition before and after 3 months storage in a dark room at 25° C. may be 40 ppm or less. In some embodiments, a transmittance of the xylylene diisocyanate composition to a light at 380 nm wavelength after 3 months storage in a dark room at 25° C. may be 99% or more. In some embodiments, the acidity regulator may include at least one inorganic acid compound selected from the group consisting of halogen acids, sulfuric acid, phosphoric acid, and phosphoric acid ester-based compounds. In some embodiments, the acidity regulator may include at least one organic acid compound selected from the group consisting of acetic acid, benzoic acid, trifluoroacetic acid (TFA), fatty acid, and aromatic carboxylic acid halide. In some embodiments, the acidity regulator may include at least one solid acid selected from the group consisting of clay, silica alumina, cation exchange resin, acid-impregnated silica gel, acid-impregnated alumina, aluminum oxide, and vanadium oxide. In some embodiments, the acidity regulator may include a cyclic amine compound or a tertiary amine compound. In some embodiments, an addition amount of the acidity regulator may range from 300 ppm to 4,000 ppm. A polymerizable composition for an optical material according to exemplary embodiments includes: a xylylene diisocyanate composition which includes xylylene diisocyanate (XDI) and an acidity regulator having a boiling point of 110° C. or higher, and h