US-20260125495-A1 - CURABLE COMPOSITION, CURED BODY, OPTICAL ARTICLE, LENS AND EYE GLASSES

Abstract

The present invention provides a curable composition which contains a first bismuth compound that comprises bismuth and at least one of an acryloyl group and a methacryloyl group, and a first polymerizable compound that comprises at least one polymerizable group selected from the group consisting of an acryloyl group, a methacryloyl group, a vinyl group and an allyl group, while having a boiling point of 90° C. or more at 1 atmosphere, wherein the content of a nitrile compound having a nitrile group is less than 10% by mass. The present invention also provides: a cured body of this curable composition; an optical article and a lens, each of which comprises this cured body; and eye glasses which comprise this lens.

Inventors

• Hayato MARUMOTO
• Takayoshi Kawasaki
• Takao Noguchi
• Yasutomo Shimizu

Assignees

• TOKUYAMA CORPORATION

Dates

Publication Date

20260507

Application Date

20230926

Priority Date

20221005

Claims (15)

1. 1 . A curable composition comprising: a first bismuth compound comprising bismuth and at least one of an acryloyl group or a methacryloyl group; and a first polymerizable compound having at least one polymerizable group selected from the group consisting of an acryloyl group, a methacryloyl group, a vinyl group, and an allyl group, and having a boiling point at 1 atm of 90° C. or higher, wherein a content of a nitrile compound having a nitrile group in the curable composition is less than 10 mass %.
2. 2 . The curable composition according to claim 1 , wherein a content of the first bismuth compound is 20 mass % or more and 90 mass % or less.
3. 3 . The curable composition according to claim 1 , wherein a content of the first polymerizable compound is 10 mass % or more and 80 mass % or less.
4. 4 . The curable composition according to claim 1 , wherein the first polymerizable compound comprises a monofunctional polymerizable compound having the polymerizable group in a number of one.
5. 5 . The curable composition according to claim 4 , wherein the monofunctional polymerizable compound has a boiling point of 100° C. or higher and 300° C. or lower.
6. 6 . The curable composition according to claim 4 , wherein the monofunctional polymerizable compound comprises a monofunctional (meth)acrylate represented by the following Formula (I): wherein, R 1 is a hydroxy group, a linear or branched alkyl group having 1 or more and 10 or less carbon atoms, a linear or branched alkoxy group having 1 or more and 10 or less carbon atoms, a cycloalkyl group having 4 or more and 10 or less carbon atoms, a heterocycloalkyl group having 3 or more and 10 or less carbon atoms and 1 or more and 3 or less hetero atoms, an aryl group having 4 or more and 10 or less carbon atoms, or a heteroaryl group having 3 or more and 10 or less carbon atoms and 1 or more and 3 or less hetero atoms, R 2 is a linear or branched alkylene group having 1 or more and 10 or less carbon atoms or an alkylene oxide group having 1 or more and 10 or less carbon atoms, R 3 is a hydrogen atom or a methyl group, and a is 0 or 1.
7. 7 . The curable composition according to claim 4 , wherein the monofunctional polymerizable compound comprises at least one (meth)acrylate selected from the group consisting of methoxyethyl acrylate, ethoxyethyl acrylate, methoxyethyl methacrylate, ethoxyethyl methacrylate, tetrahydrofurfuryl acrylate, and tetrahydrofurfuryl methacrylate.
8. 8 . The curable composition according to claim 1 , wherein the first polymerizable compound comprises a polyfunctional polymerizable compound having the polymerizable group in a number of two or more.
9. 9 . The curable composition according to claim 8 , wherein the polyfunctional polymerizable compound has a number average molecular weight of 90 or more and 2,000 or less, as determined by gel permeation chromatography analysis.
10. 10 . The curable composition according to claim 8 , wherein the polyfunctional polymerizable compound comprises a bifunctional (meth)acrylate represented by the following Formula (II): wherein, R 4 is a linear or branched alkylene group having 1 or more and 10 or less carbon atoms or a linear or branched alkylene oxide group having 1 or more and 10 or less carbon atoms, R 5 and R 6 each independently represent a hydrogen atom or a methyl group, and n is a number of 1 or more and 50 or less.
11. 11 . The curable composition according to claim 8 , wherein the polyfunctional polymerizable compound comprises a bifunctional (meth)acrylate selected from the group consisting of polyethylene glycol dimethacrylate, polyethylene glycol diacrylate, polypropylene glycol dimethacrylate, polypropylene glycol diacrylate, polytetramethylene glycol dimethacrylate, and polytetramethylene glycol diacrylate.
12. 12 . A cured product of the curable composition according to claim 1 .
13. 13 . An optical article comprising the cured product according to claim 12 .
14. 14 . A lens comprising the cured product according to claim 12 .
15. 15 . Eyeglasses comprising the lens according to claim 14 .

Description

TECHNICAL FIELD The present invention relates to a curable composition, a cured product, an optical article, a lens, and eyeglasses. BACKGROUND ART X-rays irradiated directly and stray X-rays irradiated indirectly by reflection or diffusion affect a crystalline lens of an eyeball of a human body, and may induce cataract. In order to solve this problem, an optical article such as a lens capable of shielding these X-rays and transmitting visible light is desired. Lead glass is known as an optical material for forming the optical article. The lead glass has high X-ray shielding performance, but has a high specific gravity. Therefore, X-ray shielding goggles provided with a lens containing lead glass have a large mass and may be difficult to be commonly used. As another optical material, a lead acrylate is also known. The lead acrylate has lower X-ray shielding performance than lead glass, but is lightweight. Therefore, the lead acrylate is used in optical articles for shielding stray X-rays. However, lead is an environmentally harmful substance, and an optical material not using lead is desired. As an alternative element of lead, for example, many metal elements such as bismuth, barium, antimony, tin, and tungsten are exemplified as candidates. Among these, bismuth is an element that is harmless to the human body such as being used as a gastrointestinal drug for years, has high X-ray shielding performance, and is suitable for lead substitution. A cured product of a curable composition containing a bismuth compound in which a phosphoric acid ester having a (meth)acryloyl group is bonded to bismuth, and a radically polymerizable monomer has high transparency and lightweight, and is suitable as an optical material (see Patent Documents 1 and 2). In order to enhance the mechanical properties of the cured product, it has been studied to add a nitrile compound to the curable composition. CITATION LIST Patent Document Patent Document 1: PCT International Publication No. WO2022/014591Patent Document 2: PCT International Publication No. WO2019/177084 DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention An object of the present invention is to provide a curable composition with reduced odor, a cured product with reduced odor, and an optical article, a lens, and eyeglasses containing the cured product. Means for Solving the Problems Specific means for solving the above problems include the following embodiments. <1> A curable composition containing: a first bismuth compound containing bismuth and at least one of an acryloyl group or a methacryloyl group; anda first polymerizable compound having at least one polymerizable group selected from the group consisting of an acryloyl group, a methacryloyl group, a vinyl group, and an allyl group, and having a boiling point at 1 atm of 90° C. or higher,in which a content of a nitrile compound having a nitrile group in the curable composition is less than 10 mass %. <2> The curable composition as described in <1>, in which a content of the first bismuth compound is 20 mass % or more and 90 mass % or less. <3> The curable composition as described in <1> or <2>, in which a content of the first polymerizable compound is 10 mass % or more and 80 mass % or less. <4> The curable composition as described in any one of <1> to <3>, in which the first polymerizable compound contains a monofunctional polymerizable compound having the polymerizable group in a number of one. <5> The curable composition as described in <4>, in which the monofunctional polymerizable compound has a boiling point of 100° C. or higher and 300° C. or lower. <6> The curable composition as described in aspect <4> or aspect <5>, in which the monofunctional polymerizable compound contains a monofunctional (meth)acrylate represented by the following Formula (I): wherein,R1 is a hydroxy group, a linear or branched alkyl group having 1 or more and 10 or less carbon atoms, a linear or branched alkoxy group having 1 or more and 10 or less carbon atoms, a cycloalkyl group having 4 or more and 10 or less carbon atoms, a heterocycloalkyl group having 3 or more and 10 or less carbon atoms and 1 or more and 3 or less hetero atoms, an aryl group having 4 or more and 10 or less carbon atoms, or a heteroaryl group having 3 or more and 10 or less carbon atoms and 1 or more and 3 or less hetero atoms,R2 is a linear or branched alkylene group having 1 or more and 10 or less carbon atoms or an alkylene oxide group having 1 or more and 10 or less carbon atoms,R3 is a hydrogen atom or a methyl group, anda is 0 or 1. <7> The curable composition as described in any one of <4> to <6>, in which the monofunctional polymerizable compound contains at least one (meth)acrylate selected from the group consisting of methoxyethyl acrylate, ethoxyethyl acrylate, methoxyethyl methacrylate, ethoxyethyl methacrylate, tetrahydrofurfuryl acrylate, and tetrahydrofurfuryl methacrylate. <8> The curable composition as described in any one of <1>