US-12624149-B2 - Polythiol composition and optical composition comprising same

US12624149B2US 12624149 B2US12624149 B2US 12624149B2US-12624149-B2

Abstract

A polythiol composition according to exemplary embodiments includes at least two different polythiol-based compounds, wherein a peak area (%) of the polythiol compound represented by C8H18S6, which is measured through a high performance liquid chromatographic (HPLC) analysis graph obtained at a wavelength of 230 nm, ranges from 0.90% to 1.30%. By controlling the sub-polythiol compound, an optical product having excellent transmittance and optical properties can be manufactured.

Inventors

Jae Young Pai
Jeong Moo Kim
Hyuk Hee HAN
Jung Hwan MYUNG
Kyeong Hwan You

Assignees

SK PUCORE CO., LTD.

Dates

Publication Date: 20260512
Application Date: 20210907
Priority Date: 20200910

Claims (12)

1 . A polythiol composition, comprising at least two different polythiol-based compounds, wherein a peak area (%) of a polythiol compound represented by C 8 H 18 S 6 , which is measured through a high performance liquid chromatographic (HPLC) analysis graph obtained at a wavelength of 230 nm, ranges from 0.90% to 1.30%.
2 . The polythiol composition according to claim 1 , wherein the polythiol compound represented by C 8 H 18 S 6 has a structure represented by Formula 2 below:
3 . The polythiol composition according to claim 2 , wherein the polythiol-based compound includes a sub-polythiol compound represented by Formula 2 above, and a main polythiol compound having a higher molecular weight than that of the sub-polythiol compound.
4 . The polythiol composition according to claim 3 , wherein the main polythiol compound includes a tetrafunctional polythiol compound having a larger number of carbon atoms than that of the sub-polythiol compound.
5 . The polythiol composition according to claim 3 , wherein the main polythiol compound includes at least one selected from tetrafunctional polythiol compounds represented by Formulae 1-1 to 1-3 below:
6 . The polythiol composition according to claim 5 , wherein a Reaction rate Control Index defined by Equation 1 below ranges from 0.006 to 0.017: Reaction rate Control Index= A/B [Equation 1] (in Equation 1, A represents a peak area (%) of the polythiol compound represented by C 8 H 18 S 6 , which is measured through the HPLC analysis graph, and B represents a peak area (%) of the polythiol compound represented by each of Formulae 1-1 to 1-3, which is measured through the HPLC analysis graph).
7 . The polythiol composition according to claim 5 , wherein the peak area of each of the polythiol compounds represented by Formulae 1-1 to 1-3, which is measured through the HPL analysis graph, ranges from 78.6% to 85%.
8 . A method for preparing a polythiol composition, the method comprising: introducing a metal sulfide to a preliminary polyol compound to generate a polyol intermediate; adding a sub-polythiol compound formation promoter to the polyol intermediate; and converting the polyol intermediate into a polythiol-based compound through thiolation, and wherein the polythiol composition includes at least two different polythiol-based compounds, and wherein a peak area (%) of a polythiol compound represented by C 8 H 18 S 6 in the polythiol composition, which is measured through a high performance liquid chromatographic (HPLC) analysis graph obtained at a wavelength of 230 nm, ranges from 0.90% to 1.30%.
9 . The method according to claim 8 , wherein the preliminary polyol compound is synthesized by a reaction of 2-mercaptoethanol and epihalohydrin, wherein, in the step of adding the sub-polythiol compound formation promoter to the polyol intermediate, the promoter is added in a predetermined equivalent range to 2-mercaptoethanol so as to satisfy the range of a peak area (%) of the polythiol compound.
10 . The method according to claim 8 , wherein the sub-polythiol compound formation promoter includes glycidol.
11 . An optical composition, comprising: a polythiol composition which comprises at least two different polythiol-based compounds, wherein a peak area (%) of a polythiol compound represented by C 8 H 18 S 6 , which is measured through a high performance liquid chromatographic (HPLC) analysis graph obtained at a wavelength of 230 nm, ranges from 0.90% to 1.30%; and an isocyanate-based compound.
12 . An optical product, comprising a polythiourethane resin prepared from the optical composition according to claim 11 .

Description

This application is a national stage application of PCT/KR2021/012122 filed on Sep. 7, 2021, which claims priority to Korean Patent Application No. 10-2020-0116308 filed on Sep. 10, 2020. The disclosure of each of the foregoing applications is incorporated herein by reference in its entirety. BACKGROUND 1. Field The present invention relates to a polythiol composition and an optical composition including the same. More particularly, the present inventions relates to a polythiol composition including polythiol-based compounds different from each other, and an optical composition including the same. 2. Description of the Related Art A polythiol compound is widely used, for example, as a raw material for manufacturing a polyurethane resin. For example, a polythiol compound is used to manufacture an optical lens using a polyurethane resin, and quality such as purity of the polythiol compound as a raw material may directly influence on the quality of the optical lens. For example, a polythiourethane-based compound prepared by reacting a polythiol compound and an isocyanate compound may be used as a base material of the optical lens. For example, Korean Patent Laid-Open Publication No. 10-1338568 discloses a method for synthesizing a polythiol compound by reacting a polyol compound with thiourea to prepare an isothiouronium salt, and then hydrolyzing it using aqueous ammonia. Depending on the number of functional groups, a chain length, etc. of the synthesized polythiol compound, optical properties such as a transparency, refractive index, etc. of the lens may be finely modified. Accordingly, in order to reliably implement an optical lens with desired optical properties, it may necessary to finely control the constitutional composition of a polythiol compound. SUMMARY An object according to exemplary embodiments is to provide a polythiol composition with improved reaction properties and optical properties, as well as a method for preparation thereof. An object according to exemplary embodiments is to provide an optical composition including a polythiol composition with improved reaction properties and optical properties. An object according to exemplary embodiments is to provide an optical product manufactured using the optical composition described above. A polythiol composition according to exemplary embodiments includes: at least two different polythiol-based compounds, wherein a peak area (%) of the polythiol compound represented by C8H18S6, which is measured through a high performance liquid chromatographic (HPLC) analysis graph obtained at a wavelength of 230 nm, may range from 0.90% to 1.30%. In some embodiments, the polythiol compound represented by C8H18S6, may have a structure of Formula 2 below: In some embodiments, the polythiol-based compound may include a sub-polythiol compound represented by Formula 2 above, and a main polythiol compound having a higher molecular weight than that of the sub-polythiol compound. In some embodiments, the main polythiol compound may include a tetrafunctional polythiol compound having a larger number of carbon atoms than that of the sub-polythiol compound. In some embodiments, the main polythiol compound may include at least one selected from tetrafunctional polythiol compounds represented by Formulae 1-1 to 1-3 below: In some embodiments, a Reaction rate Control Index defined by Equation 1 below may range from 0.006 to 0.017: Reaction rate Control Index: RCI=A/B [Equation 1] (in Equation 1, A represents a peak area (%) of the polythiol compound represented by C8H18S6, which is measured through the HPLC analysis graph, and B represents a peak area (%) of the polythiol compound represented by each of Formulae 1-1 to 1-3, which is measured through the HPLC analysis graph). In some embodiments, a peak area of each of the polythiol compounds represented by Formulae 1-1 to 1-3, which is measured through the HPLC analysis graph, may range from 78.6% to 85%. According to a method for preparing a polythiol composition in exemplary embodiments, a metal sulfide may be introduced into a preliminary polyol compound to generate a polyol intermediate. Subsequently, a sub-polythiol compound formation promoter may be added to the polyol intermediate. Then, the polyol intermediate may be converted into a polythiol-based compound through thiolation. In some embodiments, the polythiol composition may include at least two different polythiol-based compounds, wherein a peak area (%) of the polythiol compound represented by C8H18S6, which is measured through a high performance liquid chromatographic (HPLC) analysis graph obtained at a wavelength of 230 nm, may range from 0.90% to 1.30%. In some embodiments, the preliminary polyol compound may be synthesized by a reaction of 2-mercaptoethanol and epihalohydrin, wherein the polythiol compound formation promoter in the polyol intermediate may be added in a predetermined equivalent range to 2-mercaptoethanol so as to satisfy the range of a pea