KR-102961239-B1 - Xyllylene diisocyanate composition and optically polymerizable composition containing the same

Abstract

The xylylene diisocyanate (XDI) composition according to exemplary embodiments comprises xylylene diisocyanate and an acidity regulator with a boiling point of 110°C or higher, and has an acidity of more than 100 ppm and less than or equal to 1,000 ppm based on the total weight of xylylene diisocyanate (XDI). By controlling the acidity, the polymerization reaction rate can be controlled so that an optical lens having high transmittance and improved optical uniformity can be manufactured.

Inventors

• 배재영
• 명정환
• 류경환
• 한혁희
• 김정무
• 최의준
• 신정환

Assignees

• 주식회사 온빛

Dates

Publication Date

20260507

Application Date

20210902

Priority Date

20200903

Claims (15)

1. As a xylylene diisocyanate composition, It comprises xylylene diisocyanate (XDI) and an acidity regulator with a boiling point of 110°C or higher, and The above acidity regulator includes one or more of acetic acid and benzoic acid, and The above xylylene diisocyanate composition has an acidity of more than 100 ppm and less than or equal to 1,000 ppm based on the total weight of xylylene diisocyanate (XDI), A xylylene diisocyanate composition having a chlorine content of less than 100 ppm.
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3. A xylylene diisocyanate composition according to claim 1, wherein the chlorine content in the xylylene diisocyanate composition is 10 ppm to 95 ppm.
4. A xylylene diisocyanate composition according to claim 1, wherein the change in acidity before and after storage in a dark room at 25°C for 3 months is 40 ppm or less.
5. A xylylene diisocyanate composition according to claim 1, wherein the transmittance to 380 nm wavelength light is 99% or higher after storage in a dark room at 25°C for 3 months.
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10. A xylylene diisocyanate composition according to claim 1, wherein the amount of the acidity regulator added is 300 ppm to 4,000 ppm.
11. Xylylene diisocyanate composition according to claim 1; Polythiol-based compounds; and Optically polymerizable composition containing additives.
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13. An optically polymerizable composition according to claim 11, wherein the additive comprises at least one selected from the group consisting of a release agent, a reaction catalyst, a heat stabilizer, a UV absorber, and a blueing agent.
14. As a method for preparing a xylylene diisocyanate composition, A step of synthesizing xylylene diisocyanate from xylylene diamine to form a pre-composition containing xylylene diisocyanate; and The method includes the step of adjusting the acidity of the above pre-composition to a range of more than 100 ppm and 1,000 ppm using an acidity regulator with a boiling point of 110°C or higher, and The above acidity regulator includes one or more of acetic acid and benzoic acid, and A method for preparing a xylylene diisocyanate composition, wherein the xylylene diisocyanate composition is prepared such that the chlorine content in the xylylene diisocyanate composition is less than 100 ppm.
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Description

Xyllylene diisocyanate composition and optically polymerizable composition containing the same The present invention relates to a xylylene diisocyanate composition and an optically polymerizable composition containing the same. More specifically, the invention relates to a xylylene diisocyanate composition prepared through the reaction of an amine salt and an optically polymerizable composition containing the same. Diisocyanate compounds are widely used, for example, as raw materials for the manufacture of polyurethane-based resins. For instance, diisocyanate compounds are used to manufacture optical lenses that utilize polyurethane-based resins, and the physical properties of the diisocyanate compounds as raw materials can directly affect the optical properties of the optical lenses, such as transparency and refractive index. For example, a polythiourethane-based resin produced by reacting a polythiol compound and a diisocyanate compound can be used as a base material for the optical lens. Among the above 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 optical lenses can be prepared by preparing a composition containing XDI and mixing it with a composition containing a polythiol compound. The physical properties of the XDI composition and the synthesis process need to be designed considering the stability of XDI and appropriate reactivity with the polythiol compound. For example, Korean Patent Publication No. 2012-0076329 discloses a urethane-based optical material manufactured using an isocyanate compound. However, it does not consider the physical properties of the isocyanate composition itself. Hereinafter, embodiments of the present application will be described in detail. However, as the present invention is susceptible to various modifications and may take various forms, specific embodiments are illustrated in the drawings and described in detail in the text. Nevertheless, this is not intended to limit the present invention to the specific disclosed forms, and it should be understood that it includes all modifications, equivalents, and substitutions that fall within the spirit and scope of the present invention. Unless otherwise defined, all terms used herein, including technical or scientific terms, have the same meaning as generally understood by those skilled in the art to which the present invention pertains. Terms such as those defined in commonly used dictionaries should be interpreted as having a meaning consistent with their meaning in the context of the relevant technology, and should not be interpreted in an ideal or overly formal sense unless explicitly defined in this application. According to one aspect of the present application, a composition comprising xylylene diisocyanate (XDI) (hereinafter abbreviated as XDI composition) is provided. According to exemplary embodiments, the XDI composition comprises XDI and may have an acidity of more than 100 ppm and less than or equal to 1,000 ppm based on the total weight of XDI. The term "acidity" as used in this application may be a value representing the amount of acidic component released by reacting with alcohol at room temperature, for example, converted to HCl and expressed as a ratio to the total weight of XDI. The XDI included in the above XDI composition may react with a polythiol-based compound, such as a trifunctional thiol compound and/or a tetrafunctional thiol compound, to obtain a polythiourethane resin. According to exemplary examples, the acidity of the XDI composition may be controlled as a factor affecting the stability of XDI and its reactivity with the polythiol-based compound. For example, if the acidity of the XDI composition increases excessively, the polymerization reactivity with polythiol-based compounds may be excessively reduced. Consequently, the process yield of the polythiourethane resin for manufacturing optical lenses may decrease. Furthermore, a cloudy phenomenon may occur during the casting process for lens molding. If the acidity of the XDI composition is reduced excessively, the polymerization reactivity with the polythiol-based compound may increase excessively. Consequently, instead of the desired polythiourethane resin, other by-products in the form of, for example, oligomers or polymers may increase, which may result in lens magma. Additionally, the self-reactivity of XDI may increase, leading to cloudiness during long-term storage. Consequently, as described below, the transmittance of the undiluted composition may decrease when stored in a dark room for three months at room temperature (25°C). Furthermore, due to self-reaction during long-term storage, the desired target acidity may fluctuate, making it impossible to achieve acidity control. Considering the aspects described above, according to exemplary embodiments, the acidity of the XDI composition