JP2014136766A - Composition and polymer - Google Patents

Abstract

PROBLEM TO BE SOLVED: To provide a composition having stability at room temperature and also having sufficiently high polymerizable properties, and a polymer obtained from the composition and having little coloration.SOLUTION: This invention relates to a composition that contains (A) a carbonate compound, (B) a boron trihalide, and (C) an epoxy compound, in which at least part of (A) the carbonate compound and (B) the boron trihalide forms a complex.

Description

  The present invention relates to a composition containing an epoxy compound and a polymer obtained from the composition.

  Epoxy compounds are used in a wide range of fields such as plastic raw material compounds, adhesives, paints, and electronic materials. Plastics formed by polymerizing epoxy compounds are used in a wide range of applications because of their excellent balance of strength, toughness, chemical resistance, electrical properties, and the like.

  In order to polymerize an epoxy compound, a polymerization catalyst capable of forming a bond by opening an epoxy group and a polymerizable compound capable of forming a bond by reacting with an epoxy group are used under desired conditions ( For example, heating, energy beam irradiation, etc.) are generally used. For this reason, from the viewpoint of handleability, it is desired that the epoxy compound and the polymerization catalyst and / or the polymerizable compound are mixed to form a single solution, which is excellent in stability at room temperature. That is, it is desired that the liquid is one liquid, has excellent stability at room temperature, and can be polymerized under desired conditions.

  As a method for achieving the above, a specific polymerization catalyst has been proposed. For example, Patent Documents 1 to 7 propose a method using a specific sulfonium salt as a polymerization catalyst.

JP-A-3-047164 Japanese Patent Laid-Open No. 4-001177 JP 2007-091702 A JP 2007-210983 A Japanese Unexamined Patent Publication No. 63-222002 JP 2010-241733 A JP 2012-046752 A

  However, in a composition comprising an epoxy compound and a conventionally known sulfonium salt, the epoxy compound may polymerize even at room temperature. Therefore, after making 1 liquid, it is desired to be more stable at room temperature. Further, although sulfonium hexafluoroantimonate type compounds are widely used as polymerization catalysts, it has been shown that non-antimony compound polymerization catalysts are desired from the viewpoint of toxicity of antimony compounds.

  Furthermore, a composition comprising an epoxy compound and a conventionally known sulfonium salt is polymerized, and the resulting polymer may be colored. Therefore, a polymerization catalyst that can obtain a polymer with less coloring is desired.

  Therefore, the present invention has been made in view of the above circumstances, and has a composition having excellent stability at room temperature and sufficiently high polymerizability, and a polymer with less coloration obtained from the composition. The purpose is to provide.

［式中、ａは、１以上の数を示し、Ｒ_１及びＲ_２は、炭素数１〜３３の鎖状、分岐状若しくは環状の脂肪族炭化水素基又は置換若しくは無置換の芳香族炭化水素基を示し、Ｒ_１及びＲ_２は、互いに連結されていてもよく、ａが２以上の場合、複数存在するＲ_２は同一でも異なっていてもよく、Ｒ_２同士が連結されていてもよい。］
［３］
（Ａ）カーボネート化合物の炭素数が、３〜２５である、項［１］又は［２］記載の組成物。
［４］
（Ａ）カーボネート化合物のカーボネート基の数が、１〜４である、項［１］〜［３］のいずれか一項に記載の組成物。
［５］
下記式（２）で表される（Ａ）カーボネート化合物と（Ｂ）三ハロゲン化ホウ素との比率を表す指標αが１〜１０００である、項［１］〜［４］のいずれか一項に記載の組成物。
指標α＝αｃ／αｂ （２）
αｃ：（Ａ）カーボネート化合物のカーボネート基の物質量（ｍｏｌ）
αｂ：（Ｂ）三ハロゲン化ホウ素の物質量（ｍｏｌ）
［６］
（Ｂ）三ハロゲン化ホウ素が、三フッ化ホウ素、三塩化ホウ素、及び三臭化ホウ素からなる群より選ばれる少なくとも１種である、項［１］〜［５］のいずれか一項に記載の組成物。
［７］
（Ｃ）エポキシ化合物が、３員環エーテル構造のみを重合性官能基として有する化合物である、項［１］〜［６］のいずれか一項に記載の組成物。
［８］
（Ｂ）三ハロゲン化ホウ素の物質量（ｍｏｌ）と、（Ｃ）エポキシ化合物に含まれるエポキシ基の物質量（ｍｏｌ）との比が、１：１０〜１：１０００００である、項［１］〜［７］のいずれか一項に記載の組成物。
［９］
（Ｃ）エポキシ化合物のエポキシ当量が、５５〜６００ｇ／ｍｏｌである、項［１］〜［８］のいずれか一項に記載の組成物。
［１０］
（Ｃ）エポキシ化合物が、下記式（３）、（４）、（５）又は（６）で表される部分構造を有する、項［１］〜［９］のいずれか一項に記載の組成物。

［式中、Ｒ_１０、Ｒ_１１、Ｒ_１２、Ｒ_１３、Ｒ_１４、Ｒ_１５、Ｒ_１６、Ｒ_１７、Ｒ_１８、Ｒ_１９、Ｒ_２０、Ｒ_２１、Ｒ_２２、Ｒ_２３及びＲ_２４はそれぞれ独立に、水素原子又は炭素数１〜２０の鎖状、分岐状若しくは環状の脂肪族炭化水素基又は置換若しくは無置換の芳香族炭化水素基を示す。］
［１１］
項［１］〜［１０］のいずれか一項に記載の組成物中の（Ｃ）エポキシ化合物を重合して形成される、重合物。
［１２］
項［１］〜［１０］のいずれか一項に記載の組成物中の（Ｃ）エポキシ化合物を加熱及び／又はエネルギー線照射により重合する、重合物を製造する方法。 The present invention relates to the following.
[1]
(A) a carbonate compound, (B) a boron trihalide, and (C) an epoxy compound, and (A) the carbonate compound and (B) at least a part of the boron trihalide form a complex. The composition.
[2]
(A) The composition according to item [1], wherein the carbonate compound is a compound represented by the following formula (1).

[Wherein, a represents a number of 1 or more, and R ₁ and R ₂ represent a chain, branched or cyclic aliphatic hydrocarbon group having 1 to 33 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon. R ₁ and R ₂ may be connected to each other, and when a is 2 or more, a plurality of R ₂ may be the same or different, and R ₂ may be connected to each other. . ]
[3]
(A) The composition according to item [1] or [2], wherein the carbonate compound has 3 to 25 carbon atoms.
[4]
(A) The composition according to any one of Items [1] to [3], wherein the number of carbonate groups of the carbonate compound is 1 to 4.
[5]
In any one of Items [1] to [4], an index α representing a ratio of (A) the carbonate compound represented by the following formula (2) and (B) boron trihalide is 1-1000. The composition as described.
Index α = αc / αb (2)
αc: (A) amount of carbonate group of carbonate compound (mol)
αb: (B) Boron trihalide substance amount (mol)
[6]
(B) The item [1] to [5], wherein the boron trihalide is at least one selected from the group consisting of boron trifluoride, boron trichloride, and boron tribromide. Composition.
[7]
(C) The composition according to any one of Items [1] to [6], wherein the epoxy compound is a compound having only a three-membered cyclic ether structure as a polymerizable functional group.
[8]
Item [1] The ratio of the substance amount (mol) of (B) boron trihalide to the substance amount (mol) of epoxy group contained in (C) the epoxy compound is 1:10 to 1: 100000. -The composition as described in any one of [7].
[9]
(C) The composition according to any one of Items [1] to [8], wherein the epoxy equivalent of the epoxy compound is 55 to 600 g / mol.
[10]
(C) The composition according to any one of items [1] to [9], wherein the epoxy compound has a partial structure represented by the following formula (3), (4), (5) or (6): object.

[Wherein R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ , R ₂₀ , R ₂₁ , R ₂₂ , R ₂₃ and R ₂₄ are each Independently, it represents a hydrogen atom, a chain, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group. ]
[11]
A polymer formed by polymerizing the epoxy compound (C) in the composition according to any one of items [1] to [10].
[12]
A method for producing a polymer, wherein the (C) epoxy compound in the composition according to any one of items [1] to [10] is polymerized by heating and / or energy beam irradiation.

  ADVANTAGE OF THE INVENTION According to this invention, while being excellent in stability at room temperature, the composition which has sufficiently high polymerizability, and the polymer with little coloring obtained from this composition can be provided.

  Hereinafter, a mode for carrying out the present invention (hereinafter referred to as “the present embodiment”) will be described in detail. However, the present invention is not limited to the following embodiment, and can be implemented with various modifications within the scope of the gist.

[Composition]
The composition according to this embodiment includes (A) a carbonate compound (hereinafter, sometimes referred to as “component (A)”), (B) boron trihalide (hereinafter, sometimes referred to as “component (B)”), (C) an epoxy compound (hereinafter referred to as “component (C)” in some cases). Hereinafter, the details of components (A), (B), (C) and other components contained in the composition will be described.

(Component (A): carbonate compound)
The component (A) of this embodiment is a carbonate compound containing one or more carbonate groups in the molecule. As the component (A), one type of carbonate compound may be used alone, or a plurality of types of carbonate compounds may be used in combination.

  (A) When the carbonate compound is prepared at room temperature, (C) the polymerization of the epoxy compound can be further suppressed, and the stability of the composition tends to be further improved, and / or (C) the epoxy. A compound represented by the following formula (1) is preferable since the transparency of the polymer obtained after polymerization of the compound tends to be further enhanced.

In the formula, a represents a number of 1 or more, and R ₁ and R ₂ represent a chain, branched or cyclic aliphatic hydrocarbon group having 1 to 33 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group. Show. R ₁ and R ₂ may be linked to each other. When a is 2 or more, a plurality of R ₂ may be the same or different. R ₂ may be linked together.

  (A) Carbon number of the carbonate compound tends to increase the transparency of the resulting polymer after polymerizing the epoxy compound (C) and / or when preparing the composition at room temperature ( C) Since the polymerization of the epoxy compound can be further suppressed and the stability of the composition tends to be further improved, it is preferably 3 or more. Since the vapor pressure tends to be higher and the handleability tends to be improved, the number of carbon atoms is more preferably 4 or more. From the same viewpoint, the number of carbon atoms is more preferably 5 or more.

  (A) The number of carbon atoms of the carbonate compound is preferably 25 or less because it can be easily obtained, the cost of the composition can be further suppressed, and it tends to be more economical. From the same viewpoint, the carbon number is preferably 17 or less. When preparing the composition, it is more preferable that the number of carbon atoms is 15 or less because the remaining of the undissolved material can be further suppressed and a composition excellent in uniformity can be obtained. From the same viewpoint, the number of carbon atoms is particularly preferably 13 or less.

  (A) The number of carbonate groups of the carbonate compound is such that when the composition is prepared at room temperature, (C) the polymerization of the epoxy compound can be further suppressed, and the stability of the composition tends to be further improved. It is above, and it is more preferable that it is 2 or more.

  (A) The number of carbonate groups of the carbonate compound is preferably 4 or less because it is easily available, the cost of the composition can be further suppressed, and it tends to be more economical. When preparing the composition, it is more preferable that the number of carbonate groups is 2 or less, because the residual undissolved material can be suppressed and a composition having excellent uniformity can be obtained.

  (A) The carbonate compound may have a chain, branched or cyclic structure, but (B) the formation of a compound (complex) via a boron trihalide and a coordination bond becomes easier. Therefore, it is preferably a chain or cyclic structure.

  (C) Since the (A) carbonate compound and (B) boron trihalide increase the solubility of the compound (complex) via the coordination bond and the undissolved content may be reduced with respect to the epoxy compound, The structure of the A) carbonate compound is more preferably a chain structure.

  Volatile content when a polymer and a cured product obtained by polymerizing a composition containing (A) a carbonate compound, (B) a boron trihalide, and (C) an epoxy compound are kept at a high temperature for a long period of time. Is reduced, and there is a tendency to suppress the generation of voids during molding by melt processing, or the contamination or corrosion of metal members in the vicinity of the polymer or cured product. More preferably, it is a ring structure.

  Specific examples of (A) carbonate compounds include aliphatic monofunctional carbonate compounds, aromatic monofunctional carbonate compounds, and polyfunctional carbonate compounds. These may be used alone or in combination.

(Aliphatic monofunctional carbonate compound)
The aliphatic monofunctional carbonate compound according to the present embodiment is not particularly limited as long as it has one carbonate group and only an aliphatic hydrocarbon group. Examples of the aliphatic monofunctional carbonate compound include a compound in which a is 1 and R ₁ and R ₂ are an aliphatic hydrocarbon group in the above formula (1).

When R ₁ and R ₂ are not linked, specific examples of R ₁ and R ₂ include the following.

  Methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henocosyl, docosyl, tricosyl, tetracosyl, pentacosyl, Aliphatic hydrocarbon groups such as hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, hentriacontyl, dotriacontyl (these groups may be linear, branched or cyclic).

In the case where R ₁ and R ₂ are linked, specific examples of R ₁ and R ₂ include the following.

  Methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, icosanylene, hexanilene, cosanylene, cosanylene, cosanylene, cosanylene, cosanylene, cosanylene, cosanylene Aliphatic hydrocarbon groups such as hexacosanylene, heptacosanylene, octacosanylene, nonacosanylene, triacontanilene, hentriacontanilene, dotriacontanilene (these groups may be linear, branched or cyclic).

  Among aliphatic monofunctional carbonate compounds, it is easy to obtain, the cost as a composition can be further suppressed, and there is a tendency to be more economical. When preparing a composition at room temperature, (C) polymerization of an epoxy compound is performed. Since it tends to be further suppressed, the stability of the composition tends to be further improved, and / or the transparency of the polymer obtained after polymerizing the epoxy compound (C) tends to be further improved, At least one compound selected from the group is preferred.

  Dimethyl carbonate, diethyl carbonate, di-n-propyl carbonate, diisopropyl carbonate, dicyclopropyl carbonate, di-n-butyl carbonate, diisobutyl carbonate, di-sec-butyl carbonate, di-tert-butyl carbonate, dicyclobutyl carbonate, Dipentyl carbonate, dicyclopentyl carbonate, dihexyl carbonate, dicyclohexyl carbonate, diheptyl carbonate, dioctyl carbonate, dicyclooctyl carbonate, dinonyl carbonate, didecyl carbonate, dicyclodecyl carbonate, diundecyl carbonate, didodecyl carbonate, ditridecyl carbonate, Ditetradecyl carbonate, dipentadecyl carbonate , Dihexadecyl carbonate, diheptadecyl carbonate, dioctadecyl carbonate, dinonadecyl carbonate, diicosyl carbonate, dihenicosyl carbonate, didocosyl carbonate, ditricosyl carbonate, ditetracosyl carbonate, dipentacosyl Carbonate, dihexacosyl carbonate, diheptacosyl carbonate, dioctacosyl carbonate, dinonacosyl carbonate, ditriacontyl carbonate, methyl ethyl carbonate, methyl n-propyl carbonate, methyl isopropyl carbonate, methyl cyclopropyl carbonate, methyl n-butyl carbonate, methyl isobutyl carbonate, methyl sec-butyl carbonate, methyl tert-butyl carbonate, Tylcyclobutyl carbonate, methyl pentyl carbonate, methyl cyclopentyl carbonate, methyl hexyl carbonate, methyl cyclohexyl carbonate, methyl heptyl carbonate, methyl octyl carbonate, methyl cyclooctyl carbonate, methyl nonyl carbonate, methyl decyl carbonate, methyl undecyl carbonate, methyl dodecyl carbonate , Methyl tridecyl carbonate, methyl tetradecyl carbonate, methyl pentadecyl carbonate, methyl hexadecyl carbonate, methyl heptadecyl carbonate, methyl octadecyl carbonate, methyl nonadecyl carbonate, methyl icosyl carbonate, methyl heicosyl carbonate, methyl docosyl carbonate , Mechi Rutricosyl carbonate, methyl tetracosyl carbonate, methyl pentacosyl carbonate, methyl hexacosyl carbonate, methyl heptacosyl carbonate, methyl octacosyl carbonate, methyl nonacosyl carbonate, methyl triacontyl carbonate;

Ethyl n-propyl carbonate, ethyl isopropyl carbonate, ethyl cyclopropyl carbonate, ethyl n-butyl carbonate, ethyl isobutyl carbonate, ethyl sec-butyl carbonate, ethyl tert-butyl carbonate, ethyl cyclobutyl carbonate, ethyl pentyl carbonate, ethyl cyclopentyl carbonate, Ethyl hexyl carbonate, ethyl cyclohexyl carbonate, ethyl heptyl carbonate, ethyl octyl carbonate, ethyl cyclooctyl carbonate, ethyl nonyl carbonate, ethyl decyl carbonate, ethyl undecyl carbonate, ethyl dodecyl carbonate, ethyl tridecyl carbonate, ethyl tetradecyl carbonate, ethyl pentade Silka Bonate, ethyl hexadecyl carbonate, ethyl heptadecyl carbonate, ethyl octadecyl carbonate, ethyl nonadecyl carbonate, ethyl icosyl carbonate, ethyl heicosyl carbonate, ethyl docosyl carbonate, ethyl tricosyl carbonate, ethyl tetracosyl carbonate, ethyl pen Tacosyl carbonate, ethyl hexacosyl carbonate, ethyl heptacosyl carbonate, ethyl octacosyl carbonate, ethyl nonacosyl carbonate, ethyl triacontyl carbonate, propyl cyclopropyl carbonate, propyl butyl carbonate, propyl cyclobutyl carbonate, propyl pentyl carbonate , Propylcyclopentyl carbonate, propylhexyl carbo Propyl propyl carbonate, propyl heptyl carbonate, propyl octyl carbonate, propyl cyclooctyl carbonate, propyl nonyl carbonate, propyl decyl carbonate, propyl undecyl carbonate, propyl dodecyl carbonate, propyl tridecyl carbonate, propyl tetradecyl carbonate, propyl pentadecyl Carbonate, propyl hexadecyl carbonate, propyl heptadecyl carbonate, propyl octadecyl carbonate, propyl nonadecyl carbonate, propyl icosyl carbonate, propyl henocosyl carbonate, propyl docosyl carbonate, propyl tricosyl carbonate, propyl tetracosyl carbonate, propyl pen octopus Sil carbonate, propyl hexacosyl carbonate, propyl heptacosyl carbonate, propyl octacosyl carbonate, propyl nonacosyl carbonate, propyl triacontyl carbonate;

  Cyclopropyl butyl carbonate, cyclopropyl cyclobutyl carbonate, cyclopropyl pentyl carbonate, cyclopropyl cyclopentyl carbonate, cyclopropyl hexyl carbonate, cyclopropyl cyclohexyl carbonate, cyclopropyl heptyl carbonate, cyclopropyl octyl carbonate, cyclopropyl cyclooctyl carbonate, cyclopropyl nonyl Carbonate, cyclopropyldecyl carbonate, cyclopropylundecyl carbonate, cyclopropyl dodecyl carbonate, cyclopropyl tridecyl carbonate, cyclopropyl tetradecyl carbonate, cyclopropyl pentadecyl carbonate, cyclopropyl hexadecyl carbonate, cyclopropyl heptade Carbonate, cyclopropyl octadecyl carbonate, cyclopropyl nonadecyl carbonate, cyclopropyl icosyl carbonate, cyclopropyl hecosyl carbonate, cyclopropyl docosyl carbonate, cyclopropyl tricosyl carbonate, cyclopropyl tetracosyl carbonate, cyclopropyl pentaco Sil carbonate, cyclopropyl hexacosyl carbonate, cyclopropyl heptacosyl carbonate, cyclopropyl octacosyl carbonate, cyclopropyl nonacosyl carbonate, cyclopropyl triacontyl carbonate, butyl cyclobutyl carbonate, butyl pentyl carbonate, butyl cyclopentyl carbonate, Butyl hexyl carbonate, butyl cyclohexyl Carbonate, butyl heptyl carbonate, butyl octyl carbonate, butyl cyclooctyl carbonate, butyl nonyl carbonate, butyl decyl carbonate, butyl undecyl carbonate, butyl dodecyl carbonate, butyl tridecyl carbonate, butyl tetradecyl carbonate, butyl pentadecyl carbonate, butyl hexadecyl Carbonate, butyl heptadecyl carbonate, butyl octadecyl carbonate, butyl nonadecyl carbonate, butyl icosyl carbonate, butyl heicosyl carbonate, butyl docosyl carbonate, butyl tricosyl carbonate, butyl tetracosyl carbonate, butyl pentacosyl carbonate, butyl Hexacosyl carbonate, butyl heptacosyl Carbonate, butyl octacosyl carbonate, butyl nonacosyl carbonate, butyl triacontyl carbonate;

  Pentylcyclopentyl carbonate, pentyl hexyl carbonate, pentyl cyclohexyl carbonate, pentyl heptyl carbonate, pentyl octyl carbonate, pentyl cyclooctyl carbonate, pentyl nonyl carbonate, pentyl decyl carbonate, pentyl cyclodecyl carbonate, pentyl undecyl carbonate, pentyl decyl carbonate, pentyl tridecyl Carbonate, pentyltetradecyl carbonate, pentyl pentadecyl carbonate, pentyl hexadecyl carbonate, pentyl heptadecyl carbonate, pentyl octadecyl carbonate, pentyl nonadecyl carbonate, pentyl icosyl carbonate, pentyl hencosyl carbonate, pentyl docosyl carbonate Bonate, pentyl tricosyl carbonate, pentyl tetracosyl carbonate, pentyl pentacosyl carbonate, pentyl hexacosyl carbonate, pentyl heptacosyl carbonate, pentyl octacosyl carbonate, pentyl nonacosyl carbonate, pentyl triacontyl carbonate, cyclopentyl hexyl Carbonate, cyclopentyl cyclohexyl carbonate, cyclopentyl heptyl carbonate, cyclopentyl octyl carbonate, cyclopentyl cyclooctyl carbonate, cyclopentyl nonyl carbonate, cyclopentyl decyl carbonate, cyclopentyl cyclodecyl carbonate, cyclopentyl undecyl carbonate, cyclopentyl dodecyl carbonate, cyclopentyl Lutridecyl carbonate, cyclopentyl tetradecyl carbonate, cyclopentyl pentadecyl carbonate, cyclopentyl hexadecyl carbonate, cyclopentyl heptadecyl carbonate, cyclopentyl octadecyl carbonate, cyclopentyl nonadecyl carbonate, cyclopentyl icosyl carbonate, cyclopentyl hencosyl carbonate, cyclopentyl docosyl carbonate, cyclopentyl Tricosyl carbonate, cyclopentyl tetracosyl carbonate, cyclopentyl pentacosyl carbonate, cyclopentyl hexacosyl carbonate, cyclopentyl heptacosyl carbonate, cyclopentyl octacosyl carbonate, cyclopentyl nonacosyl carbonate, cyclopentyl Triacontyl carbonate;

  Hexyl cyclohexyl carbonate, hexyl heptyl carbonate, hexyl octyl carbonate, hexyl cyclooctyl carbonate, hexyl nonyl carbonate, hexyl decyl carbonate, hexyl cyclodecyl carbonate, hexyl undecyl carbonate, hexyl decyl carbonate, hexyl tridecyl carbonate, hexyl tetradecyl carbonate, hexyl Pentadecyl carbonate, hexyl hexadecyl carbonate, hexyl heptadecyl carbonate, hexyl octadecyl carbonate, hexyl nonadecyl carbonate, hexylicosyl carbonate, hexyl henicosyl carbonate, hexyl docosyl carbonate, hexyl tricosyl carbonate, hexyl tetracosyl carbonate Bonate, hexyl pentacosyl carbonate, hexyl hexacosyl carbonate, hexyl heptacosyl carbonate, hexyl octacosyl carbonate, hexyl nonacosyl carbonate, hexyl triacontyl carbonate, cyclohexyl heptyl carbonate, cyclohexyl octyl carbonate, cyclohexyl cyclooctyl carbonate, Cyclohexyl nonyl carbonate, cyclohexyl decyl carbonate, cyclohexyl undecyl carbonate, cyclohexyl dodecyl carbonate, cyclohexyl tridecyl carbonate, cyclohexyl tetradecyl carbonate, cyclohexyl pentadecyl carbonate, cyclohexyl hexadecyl carbonate, cyclohexyl heptadecyl carbonate , Cyclohexyl octadecyl carbonate, cyclohexyl nonadecyl carbonate, cyclohexyl luicosyl carbonate, cyclohexyl heicosyl carbonate, cyclohexyl docosyl carbonate, cyclohexyl tricosyl carbonate, cyclohexyl tetracosyl carbonate, cyclohexyl pentacosyl carbonate, cyclohexyl hexacosyl carbonate, cyclohexyl Heptacosyl carbonate, cyclohexyl octacosyl carbonate, cyclohexyl nonacosyl carbonate, cyclohexyl triacontyl carbonate;

  Heptyl octyl carbonate, heptyl cyclooctyl carbonate, heptyl nonyl carbonate, heptyl decyl carbonate, heptyl undecyl carbonate, heptyl dodecyl carbonate, heptyl tridecyl carbonate, heptyl tetradecyl carbonate, heptyl pentadecyl carbonate, heptyl hexadecyl carbonate, heptyl heptadecyl carbonate , Heptyl octadecyl carbonate, octyl cyclooctyl carbonate, octyl nonyl carbonate, octyl decyl carbonate, octyl undecyl carbonate, octyl dodecyl carbonate, octyl tridecyl carbonate, octyl tetradecyl carbonate, octyl pentadecyl carbonate, octyl hexadecyl carbonate Octyl heptadecyl carbonate, octyl octadecyl carbonate, cyclooctyl nonyl carbonate, cyclooctyl decyl carbonate, cyclooctyl undecyl carbonate, cyclooctyl decyl carbonate, cyclooctyl tridecyl carbonate, cyclooctyl tetradecyl carbonate, cyclooctyl pentadecyl carbonate , Cyclooctyl hexadecyl carbonate, cyclooctyl heptadecyl carbonate, cyclooctyl octadecyl carbonate, nonyl decyl carbonate, nonyl undecyl carbonate, nonyl dodecyl carbonate, nonyl tridecyl carbonate, nonyl tetradecyl carbonate, nonyl pentadecyl carbonate, nonyl hexadecyl carbonate , Nylheptadecyl carbonate, nonyl octadecyl carbonate, decyl undecyl carbonate, decyl dodecyl carbonate, decyl tridecyl carbonate, decyl tetradecyl carbonate, decyl pentadecyl carbonate, decyl hexadecyl carbonate, decyl heptadecyl carbonate, decyl octadecyl carbonate, undecyl dodecyl Carbonate, undecyl tridecyl carbonate, undecyl tetradecyl carbonate, undecyl pentadecyl carbonate, undecyl hexadecyl carbonate, undecyl heptadecyl carbonate, undecyl octadecyl carbonate, dodecyl tridecyl carbonate, dodecyl tetradecyl carbonate, dodecyl pentadecyl carbonate Carbonate, dodecylhe Xadecyl carbonate, dodecyl heptadecyl carbonate, dodecyl octadecyl carbonate, tridecyl tetradecyl carbonate, tridecyl pentadecyl carbonate, tridecyl hexadecyl carbonate, tridecyl heptadecyl carbonate, tridecyl octadecyl carbonate, tetradecyl pentadecyl carbonate, tetradecyl Hexadecyl carbonate, tetradecyl heptadecyl carbonate, tetradecyl octadecyl carbonate, pentadecyl hexadecyl carbonate, pentadecyl heptadecyl carbonate, pentadecyl octadecyl carbonate, hexadecyl heptadecyl carbonate, hexadecyl octadecyl carbonate, heptadecyl octadecyl carbonate;

  Ethylene carbonate, propylene carbonate, 1,2-butylene carbonate, 2,3-butylene carbonate, 1,2-pentylene carbonate, 2,3-pentylene carbonate, 1,2-hexylene carbonate, 2,3-hexylene Carbonate, 3,4-hexylene carbonate, 1,2-heptylene carbonate, 2,3-heptylene carbonate, 3,4-heptylene carbonate, 1,2-octylene carbonate, 2,3-octylene Len carbonate, 3,4-octylene carbonate, 4,5-octylene carbonate, nonylene carbonate, decylene carbonate, undecylene carbonate, dodecylene carbonate, tridecylene carbonate, tetradecylene carbonate, pentadecylene carbonate, Xadecylene carbonate, heptadecylene carbonate, octadecylene carbonate, nonadecylene carbonate, icosanylene carbonate, heicosanylene carbonate, docosanylene carbonate, tricosanylene carbonate, tetracosanylene carbonate, pentacosanylene carbonate, Hexacosanylene carbonate, heptacosanylene carbonate, octacosanylene carbonate, nonacosanylene carbonate, triacontanilene carbonate, tetramethylene carbonate, pentamethylene carbonate, hexamethylene carbonate, heptamethylene carbonate, octamethylene carbonate, nonamethylene carbonate, deca Methylene carbonate, undecamethylene carbonate, dodecamethylene -Bonate, tridecamethylene carbonate, tetradecamethylene carbonate, pentadecamethylene carbonate, hexadecamethylene carbonate, heptacamethylene carbonate, octadecamethylene carbonate, nonadecamethylene carbonate, icosamethylene carbonate, heicosamethylene carbonate, docosamethylene Carbonate, tricosa methylene carbonate, tetracosa methylene carbonate, pentacosa methylene carbonate, hexacosa methylene carbonate, heptacosa methylene carbonate, octacosa methylene carbonate, nonacosamethylene carbonate, triacontamethylene carbonate;

  1,3-dioxolan-2-one, methyl-1,3-dioxolan-2-one, ethyl-1,3-dioxolan-2-one, propyl-1,3-dioxolan-2-one, cyclopropyl-1 , 3-dioxolan-2-one, butyl-1,3-dioxolan-2-one, cyclobutyl-1,3-dioxolan-2-one, pentyl-1,3-dioxolan-2-one, cyclopentyl-1,3 -Dioxolan-2-one, hexyl-1,3-dioxolan-2-one, cyclohexyl-1,3-dioxolan-2-one, heptyl-1,3-dioxolan-2-one, octyl-1,3-dioxolane 2-one, nonyl-1,3-dioxolan-2-one, decyl-1,3-dioxolan-2-one, undecyl-1,3-dioxolane- -One, dodecyl-1,3-dioxolan-2-one, phenyl-1,3-dioxolan-2-one, naphthyl-1,3-dioxolan-2-one, anthracenyl-1,3-dioxolan-2-one , Dimethyl-1,3-dioxolan-2-one, diethyl-1,3-dioxolan-2-one, dipropyl-1,3-dioxolan-2-one, dicyclopropyl-1,3-dioxolan-2-one Dibutyl-1,3-dioxolan-2-one, dicyclobutyl-1,3-dioxolan-2-one, dipentyl-1,3-dioxolan-2-one, dicyclopentyl-1,3-dioxolan-2-one, Dihexyl-1,3-dioxolan-2-one, dicyclohexyl-1,3-dioxolan-2-one, diheptyl-1,3-dioxy Lan-2-one, dioctyl-1,3-dioxolan-2-one, dinonyl-1,3-dioxolan-2-one, didecyl-1,3-dioxolan-2-one, diundecyl-1,3-dioxolane- 2-one, didodecyl-1,3-dioxolan-2-one, diphenyl-1,3-dioxolan-2-one, dinaphthyl-1,3-dioxolan-2-one, dianthracenyl-1,3-dioxolane-2- on;

  Methylethyl-1,3-dioxolan-2-one, methylpropyl-1,3-dioxolan-2-one, methylbutyl-1,3-dioxolan-2-one, methylpentyl-1,3-dioxolan-2-one Methylhexyl-1,3-dioxolan-2-one, methylcyclohexyl-1,3-dioxolan-2-one, methylheptyl-1,3-dioxolan-2-one, methyloctyl-1,3-dioxolane-2 -One, ethylpropyl-1,3-dioxolan-2-one, ethylbutyl-1,3-dioxolan-2-one, ethylpentyl-1,3-dioxolan-2-one, ethylhexyl-1,3-dioxolane-2 -One, ethylcyclohexyl-1,3-dioxolan-2-one, ethylheptyl-1,3-dioxolane 2-one, ethyloctyl-1,3-dioxolan-2-one, propylbutyl-1,3-dioxolan-2-one, propylpentyl-1,3-dioxolan-2-one, propylhexyl-1,3- Dioxolan-2-one, propylcyclohexyl-1,3-dioxolan-2-one, propylheptyl-1,3-dioxolan-2-one, propyloctyl-1,3-dioxolan-2-one, butylpentyl-1, 3-dioxolan-2-one, butylhexyl-1,3-dioxolan-2-one, butylcyclohexyl-1,3-dioxolan-2-one, butylheptyl-1,3-dioxolan-2-one, butyloctyl- 1,3-dioxolan-2-one, pentylhexyl-1,3-dioxolan-2-one, pliers Cyclohexyl-1,3-dioxolan-2-one, pentylheptyl-1,3-dioxolan-2-one, pentyloctyl-1,3-dioxolan-2-one, hexylcyclohexyl-1,3-dioxolan-2-one Hexylheptyl-1,3-dioxolan-2-one, hexyloctyl-1,3-dioxolan-2-one, cyclohexylheptyl-1,3-dioxolan-2-one, cyclohexyloctyl-1,3-dioxolane-2 -One, 4- (methoxymethyl) -1,3-dioxolan-2-one, methyl 2-({[2- (methoxycarbonyl) phenoxy] carbonyl} oxy) benzoate.

  More preferably, the aliphatic monofunctional carbonate compound is at least one compound selected from the following group.

  Dimethyl carbonate, diethyl carbonate, di-n-propyl carbonate, diisopropyl carbonate, di-n-butyl carbonate, diisobutyl carbonate, di-sec-butyl carbonate, di-tert-butyl carbonate, dipentyl carbonate, dihexyl carbonate, dicyclohexyl carbonate, di Heptyl carbonate, dioctyl carbonate, dinonyl carbonate, didecyl carbonate, diundecyl carbonate, didodecyl carbonate, methyl ethyl carbonate, methyl n-propyl carbonate, methyl isopropyl carbonate, methyl n-butyl carbonate, methyl isobutyl carbonate, methyl sec-butyl Carbonate, methyl tert-butyl carbonate, methyl Pentyl carbonate, methyl hexyl carbonate, methyl cyclohexyl carbonate, methyl heptyl carbonate, methyl octyl carbonate, methyl nonyl carbonate, methyl decyl carbonate, ethyl n-propyl carbonate, ethyl isopropyl carbonate, ethyl n-butyl carbonate, ethyl isobutyl carbonate, ethyl sec- Butyl carbonate, ethyl tert-butyl carbonate, ethyl pentyl carbonate, ethyl hexyl carbonate, ethyl cyclohexyl carbonate, ethyl heptyl carbonate, ethyl octyl carbonate, ethyl nonyl carbonate, ethyl decyl carbonate;

  Propyl butyl carbonate, propyl pentyl carbonate, propyl hexyl carbonate, propyl cyclohexyl carbonate, propyl heptyl carbonate, propyl octyl carbonate, propyl nonyl carbonate, propyl decyl carbonate, butyl pentyl carbonate, butyl hexyl carbonate, butyl cyclohexyl carbonate, butyl heptyl carbonate, butyl octyl Carbonate, butyl nonyl carbonate, butyl decyl carbonate, pentyl hexyl carbonate, pentyl cyclohexyl carbonate, pentyl heptyl carbonate, pentyl octyl carbonate, pentyl nonyl carbonate, pentyl decyl carbonate, hexyl cyclohexyl carbonate, hexyl hexyl Tyl carbonate, hexyl octyl carbonate, hexyl nonyl carbonate, hexyl decyl carbonate, cyclohexyl heptyl carbonate, cyclohexyl octyl carbonate, cyclohexyl nonyl carbonate, cyclohexyl decyl carbonate, heptyl octyl carbonate, heptyl nonyl carbonate, heptyl decyl carbonate, octyl nonyl carbonate, octyl decyl carbonate , Nonyl decyl carbonate;

  Ethylene carbonate, propylene carbonate, 1,2-butylene carbonate, 2,3-butylene carbonate, 1,2-pentylene carbonate, 1,2-hexylene carbonate, 2,3-hexylene carbonate, 3,4-hexylene Carbonate, 1,2-heptylene carbonate, 1,2-octylene carbonate, nonylene carbonate, decylene carbonate, tetramethylene carbonate, pentamethylene carbonate, hexamethylene carbonate, 1,3-dioxolan-2-one, methyl -1,3-dioxolan-2-one, ethyl-1,3-dioxolan-2-one, propyl-1,3-dioxolan-2-one, butyl-1,3-dioxolan-2-one, pentyl-1 , 3-Dioxolan-2-one, hex 1,3-dioxolan-2-one, cyclohexyl-1,3-dioxolan-2-one, heptyl-1,3-dioxolan-2-one, octyl-1,3-dioxolan-2-one, nonyl- 1,3-dioxolan-2-one, decyl-1,3-dioxolan-2-one, phenyl-1,3-dioxolan-2-one, dimethyl-1,3-dioxolan-2-one, diethyl-1, 3-dioxolan-2-one, dipropyl-1,3-dioxolan-2-one, dibutyl-1,3-dioxolan-2-one, dipentyl-1,3-dioxolan-2-one, dihexyl-1,3- Dioxolan-2-one, dicyclohexyl-1,3-dioxolan-2-one, diheptyl-1,3-dioxolan-2-one, dioctyl-1,3-di Kisoran-2-one, dinonyl 1,3-dioxolan-2-one, didecyl-1,3-dioxolan-2-one, diphenyl-1,3-dioxolan-2-one;

  Methylethyl-1,3-dioxolan-2-one, methylpropyl-1,3-dioxolan-2-one, methylbutyl-1,3-dioxolan-2-one, methylpentyl-1,3-dioxolan-2-one Methylhexyl-1,3-dioxolan-2-one, methylcyclohexyl-1,3-dioxolan-2-one, ethylpropyl-1,3-dioxolan-2-one, ethylbutyl-1,3-dioxolan-2-one ON, ethylpentyl-1,3-dioxolan-2-one, ethylhexyl-1,3-dioxolan-2-one, ethylcyclohexyl-1,3-dioxolan-2-one, propylbutyl-1,3-dioxolane-2 -One, propylpentyl-1,3-dioxolan-2-one, propylhexyl-1,3-dioxo 2-one, propylcyclohexyl-1,3-dioxolan-2-one, butylpentyl-1,3-dioxolan-2-one, butylhexyl-1,3-dioxolan-2-one, butylcyclohexyl-1, 3-dioxolan-2-one, pentylhexyl-1,3-dioxolan-2-one, pentylcyclohexyl-1,3-dioxolan-2-one, hexylcyclohexyl-1,3-dioxolan-2-one.

  More preferably, the aliphatic monofunctional carbonate compound is at least one compound selected from the following group.

  Diethyl carbonate, di-n-propyl carbonate, diisopropyl carbonate, di-n-butyl carbonate, diisobutyl carbonate, di-sec-butyl carbonate, di-tert-butyl carbonate, ethylene carbonate, propylene carbonate, 1,2-butylene carbonate, 1,3-dioxolan-2-one.

(Aromatic monofunctional carbonate compound)
The aromatic monofunctional carbonate compound according to the present embodiment is not particularly limited as long as it has one carbonate group and one or more aromatic hydrocarbon groups. Examples of the aromatic monofunctional carbonate compound include a compound in which a is 1 and R ₁ and / or R ₂ is an aromatic hydrocarbon group in the above formula (1).

When R ₁ and R ₂ are not linked, specific examples of aromatic hydrocarbon groups R ₁ and / or R ₂ include substituted or unsubstituted phenyl, naphthyl, anthracenyl and the like.

When these aromatic hydrocarbon groups have a substituent, examples of the substituent include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl , Hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, heicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, hentriacontyl, dotriacontyl, etc., linear, branched or cyclic alkyl groups, OR Group, OCOR group, NR ₂ group, NHCOR group, CF ₃ group, CCl ₃ group, NO ₂ group, CN group, CHO group, COR group, CO ₂ R group, SO ₂ R group, SO ₃ R group, etc. It is done. R represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group.

When R ₁ and R ₂ are linked, specific examples of R ₁ and / or R ₂ that are aromatic hydrocarbon groups include substituted or unsubstituted phenylene, naphthylene, anthracenylene, and the like.

When these aromatic hydrocarbon groups have a substituent, examples of the substituent include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl , Hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, heicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, hentriacontyl, dotriacontyl, etc., linear, branched or cyclic alkyl groups, OR Group, OCOR group, NR ₂ group, NHCOR group, CF ₃ group, CCl ₃ group, NO ₂ group, CN group, CHO group, COR group, CO ₂ R group, SO ₂ R group, SO ₃ R group, etc. It is done. R represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group.

When R ₁ and R ₂ are not linked and R ₁ or R ₂ is an aliphatic hydrocarbon group, the following can be mentioned as specific examples of the aliphatic hydrocarbon group.

  Methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henocosyl, docosyl, tricosyl, tetracosyl, pentacosyl, Aliphatic hydrocarbon groups such as hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, hentriacontyl, dotriacontyl (these groups may be linear, branched or cyclic).

In the case where R ₁ and R ₂ are linked and R ₁ or R ₂ is an aliphatic hydrocarbon group, specific examples of the aliphatic hydrocarbon group include the following.

  Methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, icosanylene, hexanilene, cosanylene, cosanylene, cosanylene, cosanylene, cosanylene, cosanylene, cosanylene Aliphatic hydrocarbon groups such as hexacosanylene, heptacosanylene, octacosanylene, nonacosanylene, triacontanilene, hentriacontanilene, dotriacontanilene (these groups may be linear, branched or cyclic).

  Among the aromatic monofunctional carbonate compounds, it is easy to obtain, the cost of the composition can be further suppressed, and it tends to be more economical. When preparing the composition at room temperature, (C) polymerization of the epoxy compound is performed. Since it tends to be further suppressed, the stability of the composition tends to be further improved, and / or the transparency of the polymer obtained after polymerizing the epoxy compound (C) tends to be further improved, At least one compound selected from the group is preferred.

  Diphenyl carbonate, bis (methylphenyl) carbonate, bis (ethylphenyl) carbonate, bis (propylphenyl) carbonate, bis (butylphenyl) carbonate, bis (methoxyphenyl) carbonate, bis (dimethylaminophenyl) carbonate, bis (fluorophenyl) ) Carbonate, bis (trifluoromethylphenyl) carbonate, bis (acetylphenyl) carbonate, bis (dimethylphenyl) carbonate, bis (diethylphenyl) carbonate, bis (dipropylphenyl) carbonate, bis (dibutylphenyl) carbonate, bis ( Dimethoxyphenyl) carbonate, bis [di (dimethylamino) phenyl] carbonate, bis (difluorophenyl) carbonate, bis [ (Trifluoromethyl) phenyl] carbonate, bis (diacetylphenyl) carbonate, bis (trimethylphenyl) carbonate, bis (triethylphenyl) carbonate, bis (tripropylphenyl) carbonate, bis (tributylphenyl) carbonate, bis (trimethoxyphenyl) ) Carbonate, bis [tri (dimethylamino) phenyl] carbonate, bis (trifluorophenyl) carbonate, bis [tri (trifluoromethyl) phenyl] carbonate, bis (triacetylphenyl) carbonate, dibenzyl carbonate, dinaphthyl carbonate, Bis (methylnaphthyl) carbonate, dianthracenyl carbonate, (methylphenyl) phenyl carbonate, (ethylphenyl) phenyl carbonate Bonate, (propylphenyl) phenyl carbonate, (butylphenyl) phenyl carbonate, benzylphenyl carbonate, naphthylphenyl carbonate, (anthracenylphenyl carbonate, (ethylphenyl) methylphenyl carbonate, (propylphenyl) methylphenyl carbonate, (butylphenyl) ) Methylphenyl carbonate, (methylphenyl) benzyl carbonate, (methylphenyl) naphthyl carbonate, (methylnaphthyl) methylphenyl carbonate, (methylphenyl) anthracenyl carbonate;

  (Propylphenyl) ethylphenyl carbonate, (butylphenyl) ethylphenyl carbonate, (ethylphenyl) benzyl carbonate, (ethylphenyl) naphthyl carbonate, (ethylphenyl) anthracenyl carbonate, (butylphenyl) propylphenyl carbonate, (propylphenyl) ) Benzyl carbonate, (propylphenyl) naphthyl carbonate, (propylphenyl) anthracenyl carbonate, (butylphenyl) benzyl carbonate, (butylphenyl) naphthyl carbonate, (butylphenyl) anthracenyl carbonate, benzylnaphthyl carbonate, benzylanthracene Nyl carbonate, naphthyl anthracenyl carbonate, methyl phenyl carbonate, ethyl phen Carbonate, n-propylphenyl carbonate, isopropylphenyl carbonate, cyclopropylphenyl carbonate, n-butylphenyl carbonate, isobutylphenyl carbonate, sec-butylphenyl carbonate, tert-butylphenyl carbonate, cyclobutylphenyl carbonate, pentylphenyl carbonate, cyclopentyl Phenyl carbonate, hexyl phenyl carbonate, cyclohexyl phenyl carbonate, heptyl phenyl carbonate, cycloheptyl phenyl carbonate, octyl phenyl carbonate, cyclooctyl phenyl carbonate, nonyl phenyl carbonate, decyl phenyl carbonate, undecyl phenyl carbonate, dodecyl phenyl car Nate, tridecyl phenyl carbonate, tetradecyl phenyl carbonate, pentadecyl phenyl carbonate, hexadecyl phenyl carbonate, heptadecyl phenyl carbonate, octadecyl phenyl carbonate, nonadecyl phenyl carbonate, icosyl phenyl carbonate, heicosyl phenyl carbonate, docosyl phenyl Carbonate, tricosyl phenyl carbonate, tetracosyl phenyl carbonate, pentacosyl phenyl carbonate, hexacosyl phenyl carbonate, heptacosyl phenyl carbonate, octacosyl phenyl carbonate, nonacosyl phenyl carbonate, triacontyl phenyl carbonate;

  (Methylphenyl) methyl carbonate, (methylphenyl) ethyl carbonate, (methylphenyl) n-propyl carbonate, (methylphenyl) isopropyl carbonate, (methylphenyl) cyclopropyl carbonate, (methylphenyl) n-butyl carbonate, (methylphenyl) ) Isobutyl carbonate, (methylphenyl) sec-butyl carbonate, (methylphenyl) tert-butyl carbonate, (methylphenyl) cyclobutyl carbonate, (methylphenyl) pentyl carbonate, (methylphenyl) cyclopentyl carbonate, (methylphenyl) hexyl carbonate , (Methylphenyl) cyclohexyl carbonate, (methylphenyl) heptyl carbonate, (methylphenyl) octane Carbonate, (methylphenyl) nonyl carbonate, (methylphenyl) cyclononyl carbonate, (methylphenyl) decyl carbonate, (methylphenyl) undecyl carbonate, (methylphenyl) dodecyl carbonate, (ethylphenyl) methyl carbonate, (ethylphenyl) ) Ethyl carbonate, (ethylphenyl) n-propyl carbonate, (ethylphenyl) isopropyl carbonate, (ethylphenyl) cyclopropyl carbonate, (ethylphenyl) n-butyl carbonate, (ethylphenyl) isobutyl carbonate, (ethylphenyl) sec- Butyl carbonate, (ethyl phenyl) tert-butyl carbonate, (ethyl phenyl) cyclobutyl carbonate, (ethyl phenyl ) Pentyl carbonate, (ethylphenyl) cyclopentyl carbonate, (ethylphenyl) hexyl carbonate, (ethylphenyl) cyclohexyl carbonate, (ethylphenyl) heptyl carbonate, (ethylphenyl) octyl carbonate, (ethylphenyl) nonyl carbonate, (ethylphenyl) Decyl carbonate, (ethylphenyl) undecyl carbonate, (ethylphenyl) dodecyl carbonate, (propylphenyl) methyl carbonate, (propylphenyl) ethyl carbonate, (propylphenyl) n-propyl carbonate, (propylphenyl) isopropyl carbonate, (propyl Phenyl) cyclopropyl carbonate, (propylphenyl) n-butyl carbonate, Ruphenyl) isobutyl carbonate, (propylphenyl) sec-butyl carbonate, (propylphenyl) tert-butyl carbonate, (propylphenyl) cyclobutyl carbonate, (propylphenyl) pentyl carbonate, (propylphenyl) cyclopentyl carbonate, (propylphenyl) hexyl Carbonate, (propylphenyl) cyclohexyl carbonate, (propylphenyl) heptyl carbonate, (propylphenyl) octyl carbonate, (propylphenyl) nonyl carbonate, (propylphenyl) decyl carbonate, (propylphenyl) undecyl carbonate, (propylphenyl) dodecyl Carbonate;

  (Butylphenyl) methyl carbonate, (butylphenyl) ethyl carbonate, (butylphenyl) n-propyl carbonate, (butylphenyl) isopropyl carbonate, (butylphenyl) cyclopropyl carbonate, (butylphenyl) n-butyl carbonate, (butylphenyl) ) Isobutyl carbonate, (butylphenyl) sec-butyl carbonate, (butylphenyl) tert-butyl carbonate, (butylphenyl) cyclobutyl carbonate, (butylphenyl) pentyl carbonate, (butylphenyl) cyclopentyl carbonate, (butylphenyl) hexyl carbonate , (Butylphenyl) cyclohexyl carbonate, (butylphenyl) heptyl carbonate, (butylphenyl) oct Carbonate, (butylphenyl) nonyl carbonate, (butylphenyl) decyl carbonate, (butylphenyl) undecyl carbonate, (butylphenyl) dodecyl carbonate, (methoxyphenyl) methyl carbonate, (methoxyphenyl) ethyl carbonate, (methoxyphenyl) Propyl carbonate, (methoxyphenyl) cyclopropyl carbonate, (methoxyphenyl) butyl carbonate, (methoxyphenyl) cyclobutyl carbonate, (methoxyphenyl) pentyl carbonate, (methoxyphenyl) cyclopentyl carbonate, (methoxyphenyl) hexyl carbonate, (methoxyphenyl) ) Cyclohexyl carbonate, (methoxyphenyl) heptyl carbonate, (methoxyphenyl) Nyl) octyl carbonate, (methoxyphenyl) nonyl carbonate, (methoxyphenyl) decyl carbonate, (methoxyphenyl) undecyl carbonate, (methoxyphenyl) dodecyl carbonate, (dimethylaminophenyl) methyl carbonate, (dimethylaminophenyl) ethyl carbonate, (Dimethylaminophenyl) propyl carbonate, (dimethylaminophenyl) cyclopropyl carbonate, (dimethylaminophenyl) butyl carbonate, (dimethylaminophenyl) cyclobutyl carbonate, (dimethylaminophenyl) pentyl carbonate, (dimethylaminophenyl) cyclopentyl carbonate, (Dimethylaminophenyl) hexyl carbonate, (Dimethylaminophenyl) cycl Rohexyl carbonate, (dimethylaminophenyl) heptyl carbonate, (dimethylaminophenyl) octyl carbonate, (dimethylaminophenyl) nonyl carbonate, (dimethylaminophenyl) decyl carbonate, (dimethylaminophenyl) undecyl carbonate, (dimethylaminophenyl) Dodecyl carbonate;

  (Fluorophenyl) methyl carbonate, (fluorophenyl) ethyl carbonate, (fluorophenyl) propyl carbonate, (fluorophenyl) cyclopropyl carbonate, (fluorophenyl) butyl carbonate, (fluorophenyl) cyclobutyl carbonate, (fluorophenyl) pentyl carbonate (Fluorophenyl) cyclopentyl carbonate, (fluorophenyl) hexyl carbonate, (fluorophenyl) cyclohexyl carbonate, (fluorophenyl) heptyl carbonate, (fluorophenyl) octyl carbonate, (fluorophenyl) nonyl carbonate, (fluorophenyl) decyl carbonate, (Fluorophenyl) undecyl carbonate, (Fluorophenyl) do Sil carbonate, (trifluoromethylphenyl) methyl carbonate, (trifluoromethylphenyl) ethyl carbonate, (trifluoromethylphenyl) propyl carbonate, (trifluoromethylphenyl) cyclopropyl carbonate, (trifluoromethylphenyl) butyl carbonate, ( (Trifluoromethylphenyl) cyclobutyl carbonate, (trifluoromethylphenyl) pentyl carbonate, (trifluoromethylphenyl) cyclopentyl carbonate, (trifluoromethylphenyl) hexyl carbonate, (trifluoromethylphenyl) cyclohexyl carbonate, (trifluoromethylphenyl) ) Heptyl carbonate, (trifluoromethylphenyl) octyl carbonate, (tri Fluoromethylphenyl) nonyl carbonate, (trifluoromethylphenyl) decyl carbonate, (trifluoromethylphenyl) undecyl carbonate, (trifluoromethylphenyl) dodecyl carbonate, (acetylphenyl) methyl carbonate, (acetylphenyl) ethyl carbonate, (Acetylphenyl) propyl carbonate, (acetylphenyl) cyclopropyl carbonate, (acetylphenyl) butyl carbonate, (acetylphenyl) cyclobutyl carbonate, (acetylphenyl) pentyl carbonate, (acetylphenyl) cyclopentyl carbonate, (acetylphenyl) hexyl carbonate , (Acetylphenyl) cyclohexyl carbonate, (acetylphenyl) heptyl car Bonate, (acetylphenyl) octyl carbonate, (acetylphenyl) nonyl carbonate, (acetylphenyl) decyl carbonate, (acetylphenyl) undecyl carbonate, (acetylphenyl) dodecyl carbonate;

  (Dimethylphenyl) methyl carbonate, (dimethylphenyl) ethyl carbonate, (dimethylphenyl) propyl carbonate, (dimethylphenyl) cyclopropyl carbonate, (dimethylphenyl) butyl carbonate, (dimethylphenyl) cyclobutyl carbonate, (dimethylphenyl) pentyl carbonate (Dimethylphenyl) cyclopentyl carbonate, (dimethylphenyl) hexyl carbonate, (dimethylphenyl) cyclohexyl carbonate, (dimethylphenyl) heptyl carbonate, (dimethylphenyl) octyl carbonate, (dimethylphenyl) nonyl carbonate, (dimethylphenyl) decyl carbonate, (Dimethylphenyl) undecyl carbonate, (dimethylphenyl) do Sil carbonate, (diethyl phenyl) methyl carbonate, (diethyl phenyl) ethyl carbonate, (diethyl phenyl) propyl carbonate, (diethyl phenyl) cyclopropyl carbonate, (diethyl phenyl) butyl carbonate, (diethyl phenyl) cyclobutyl carbonate, (diethyl phenyl) ) Pentyl carbonate, (diethylphenyl) cyclopentyl carbonate, (diethylphenyl) hexyl carbonate, (diethylphenyl) cyclohexyl carbonate, (diethylphenyl) heptyl carbonate, (diethylphenyl) octyl carbonate, (diethylphenyl) nonyl carbonate, (diethylphenyl) Decyl carbonate, (diethylphenyl) undecyl carbonate, ( Ethylphenyl) dodecyl carbonate, (dipropylphenyl) methyl carbonate, (dipropylphenyl) ethyl carbonate, (dipropylphenyl) propyl carbonate, (dipropylphenyl) cyclopropyl carbonate, (dipropylphenyl) butyl carbonate, (dipropyl) Phenyl) cyclobutyl carbonate, (dipropylphenyl) pentyl carbonate, (dipropylphenyl) cyclopentyl carbonate, (dipropylphenyl) hexyl carbonate, (dipropylphenyl) cyclohexyl carbonate, (dipropylphenyl) heptyl carbonate, (dipropylphenyl) ) Octyl carbonate, (dipropylphenyl) nonyl carbonate, (dipropylphenyl) decyl carbonate, (Dipropylphenyl) undecyl carbonate, (dipropylphenyl) dodecyl carbonate;

  (Dibutylphenyl) methyl carbonate, (dibutylphenyl) ethyl carbonate, (dibutylphenyl) propyl carbonate, (dibutylphenyl) cyclopropyl carbonate, (dibutylphenyl) butyl carbonate, (dibutylphenyl) cyclobutyl carbonate, (dibutylphenyl) pentyl carbonate (Dibutylphenyl) cyclopentyl carbonate, (dibutylphenyl) hexyl carbonate, (dibutylphenyl) cyclohexyl carbonate, (dibutylphenyl) heptyl carbonate, (dibutylphenyl) octyl carbonate, (dibutylphenyl) nonyl carbonate, (dibutylphenyl) decyl carbonate, (Dibutylphenyl) undecyl carbonate, (dibutylphenyl) do Sil carbonate, (trimethylphenyl) methyl carbonate, (trimethylphenyl) ethyl carbonate, (trimethylphenyl) propyl carbonate, (trimethylphenyl) cyclopropyl carbonate, (trimethylphenyl) butyl carbonate, (trimethylphenyl) cyclobutyl carbonate, (trimethylphenyl) ) Pentyl carbonate, (trimethylphenyl) cyclopentyl carbonate, (trimethylphenyl) hexyl carbonate, (trimethylphenyl) cyclohexyl carbonate, (trimethylphenyl) heptyl carbonate, (trimethylphenyl) octyl carbonate, (trimethylphenyl) nonyl carbonate, (trimethylphenyl) Decyl carbonate, (trimethyl pheny ) Undecyl carbonate, (trimethylphenyl) dodecyl carbonate, (triethylphenyl) methyl carbonate, (triethylphenyl) ethyl carbonate, (triethylphenyl) propyl carbonate, (triethylphenyl) cyclopropyl carbonate, (triethylphenyl) butyl carbonate, (triethyl) Phenyl) cyclobutyl carbonate, (triethylphenyl) pentyl carbonate, (triethylphenyl) cyclopentyl carbonate, (triethylphenyl) hexyl carbonate, (triethylphenyl) cyclohexyl carbonate, (triethylphenyl) heptyl carbonate, (triethylphenyl) octyl carbonate, (triethyl) Phenyl) nonyl carbonate, (triethyl) Ruphenyl) decyl carbonate, (triethylphenyl) undecyl carbonate, (triethylphenyl) dodecyl carbonate;

  (Tripropylphenyl) methyl carbonate, (tripropylphenyl) ethyl carbonate, (tripropylphenyl) propyl carbonate, (tripropylphenyl) cyclopropyl carbonate, (tripropylphenyl) butyl carbonate, (tripropylphenyl) cyclobutyl carbonate, (Tripropylphenyl) pentyl carbonate, (tripropylphenyl) cyclopentyl carbonate, (tripropylphenyl) hexyl carbonate, (tripropylphenyl) cyclohexyl carbonate, (tripropylphenyl) heptyl carbonate, (tripropylphenyl) octyl carbonate, (tri Propylphenyl) nonyl carbonate, (tripropylphenyl) decyl carbonate, (tripro Ruphenyl) undecyl carbonate, (tripropylphenyl) dodecyl carbonate, (tributylphenyl) methyl carbonate, (tributylphenyl) ethyl carbonate, (tributylphenyl) propyl carbonate, (tributylphenyl) cyclopropyl carbonate, (tributylphenyl) butyl carbonate, (Tributylphenyl) cyclobutyl carbonate, (tributylphenyl) pentyl carbonate, (tributylphenyl) cyclopentyl carbonate, (tributylphenyl) hexyl carbonate, (tributylphenyl) cyclohexyl carbonate, (tributylphenyl) heptyl carbonate, (tributylphenyl) octyl carbonate, (Tributylphenyl) nonyl carbonate , (Tributylphenyl) decyl carbonate, (tributylphenyl) undecyl carbonate, (tributylphenyl) dodecyl carbonate, benzyl methyl carbonate, benzyl ethyl carbonate, benzyl n-propyl carbonate, benzyl isopropyl carbonate, benzyl cyclopropyl carbonate, benzyl n-butyl Carbonate, benzyl isobutyl carbonate, benzyl sec-butyl carbonate, benzyl tert-butyl carbonate, benzyl cyclobutyl carbonate, benzyl pentyl carbonate, benzyl cyclopentyl carbonate, benzyl hexyl carbonate, benzyl cyclohexyl carbonate, benzyl heptyl carbonate, benzyl octyl carbonate, benzyl Nonyl carbonate, benzyl decyl carbonate, benzyl undecyl carbonate, benzyl dodecyl carbonate;

  Naphthyl methyl carbonate, naphthyl ethyl carbonate, naphthyl propyl carbonate, naphthyl cyclopropyl carbonate, naphthyl butyl carbonate, naphthyl cyclobutyl carbonate, naphthyl pentyl carbonate, naphthyl cyclopentyl carbonate, naphthyl hexyl carbonate, naphthyl cyclohexyl carbonate, naphthyl heptyl carbonate, naphthyl octyl carbonate, Naphthyl nonyl carbonate, naphthyl decyl carbonate, naphthyl undecyl carbonate, naphthyl dodecyl carbonate, anthracenyl methyl carbonate, anthracenyl ethyl carbonate, anthracenyl propyl carbonate, anthracenyl cyclopropyl carbonate, anthracenyl butyl carbonate , Anthracenyl cyclobutyl carbonate, anthracenyl pentyl carbonate, anthracenyl cyclopentyl carbonate, anthracenyl hexyl carbonate, anthracenyl cyclohexyl carbonate, anthracenyl heptyl carbonate, anthracenyl octyl carbonate, anthracenyl nonyl carbonate Anthracenyl decyl carbonate, anthracenyl undecyl carbonate, anthracenyl dodecyl carbonate.

  More preferably, the aromatic monofunctional carbonate compound is at least one compound selected from the following group.

  Diphenyl carbonate, bis (methylphenyl) carbonate, bis (methoxyphenyl) carbonate, bis (dimethylaminophenyl) carbonate, bis (fluorophenyl) carbonate, bis (trifluoromethylphenyl) carbonate, bis (acetylphenyl) carbonate, bis ( Dimethylphenyl) carbonate, bis (trimethylphenyl) carbonate, dibenzyl carbonate, (methylphenyl) phenyl carbonate, benzylphenyl carbonate, naphthylphenyl carbonate, (methylphenyl) benzyl carbonate;

  Benzyl naphthyl carbonate, methyl phenyl carbonate, ethyl phenyl carbonate, n-propyl phenyl carbonate, isopropyl phenyl carbonate, n-butyl phenyl carbonate, isobutyl phenyl carbonate, sec-butyl phenyl carbonate, tert-butyl phenyl carbonate, pentyl phenyl carbonate, hexyl phenyl Carbonate, cyclohexyl phenyl carbonate, heptyl phenyl carbonate, octyl phenyl carbonate, nonyl phenyl carbonate, decyl phenyl carbonate, undecyl phenyl carbonate, dodecyl phenyl carbonate;

  (Methylphenyl) methyl carbonate, (methylphenyl) ethyl carbonate, (methylphenyl) n-propyl carbonate, (methylphenyl) isopropyl carbonate, (methylphenyl) n-butyl carbonate, (methylphenyl) isobutyl carbonate, (methylphenyl) sec-butyl carbonate, (methylphenyl) tert-butyl carbonate, (methylphenyl) pentyl carbonate, (methylphenyl) hexyl carbonate, (methylphenyl) cyclohexyl carbonate, (methylphenyl) heptyl carbonate, (methylphenyl) octyl carbonate, ( Methoxyphenyl) methyl carbonate, (methoxyphenyl) ethyl carbonate, (methoxyphenyl) propyl carbonate , (Methoxyphenyl) butyl carbonate, (methoxyphenyl) pentyl carbonate, (methoxyphenyl) hexyl carbonate, (methoxyphenyl) cyclohexyl carbonate, (methoxyphenyl) heptyl carbonate, (methoxyphenyl) octyl carbonate, (dimethylaminophenyl) methyl carbonate (Dimethylaminophenyl) ethyl carbonate, (dimethylaminophenyl) propyl carbonate, (dimethylaminophenyl) butyl carbonate, (dimethylaminophenyl) pentyl carbonate, (dimethylaminophenyl) hexyl carbonate, (dimethylaminophenyl) cyclohexyl carbonate, ( Dimethylaminophenyl) heptyl carbonate, (dimethylaminopheny ) Octyl carbonate;

  (Fluorophenyl) methyl carbonate, (fluorophenyl) ethyl carbonate, (fluorophenyl) propyl carbonate, (fluorophenyl) butyl carbonate, (fluorophenyl) pentyl carbonate, (fluorophenyl) hexyl carbonate, (fluorophenyl) cyclohexyl carbonate, ( (Fluorophenyl) heptyl carbonate, (fluorophenyl) octyl carbonate, (trifluoromethylphenyl) methyl carbonate, (trifluoromethylphenyl) ethyl carbonate, (trifluoromethylphenyl) propyl carbonate, (trifluoromethylphenyl) butyl carbonate, ( (Trifluoromethylphenyl) pentyl carbonate, (trifluoromethylphenyl) hexane Carbonate, (trifluoromethylphenyl) cyclohexyl carbonate, (trifluoromethylphenyl) heptyl carbonate, (trifluoromethylphenyl) octyl carbonate, (acetylphenyl) methyl carbonate, (acetylphenyl) ethyl carbonate, (acetylphenyl) propyl carbonate , (Acetylphenyl) butyl carbonate, (acetylphenyl) pentyl carbonate, (acetylphenyl) hexyl carbonate, (acetylphenyl) cyclohexyl carbonate, (acetylphenyl) heptyl carbonate, (acetylphenyl) octyl carbonate;

  (Dimethylphenyl) methyl carbonate, (dimethylphenyl) ethyl carbonate, (dimethylphenyl) propyl carbonate, (dimethylphenyl) butyl carbonate, (dimethylphenyl) pentyl carbonate, (dimethylphenyl) hexyl carbonate, (dimethylphenyl) cyclohexyl carbonate, ( (Dimethylphenyl) heptyl carbonate, (dimethylphenyl) octyl carbonate, (trimethylphenyl) methyl carbonate, (trimethylphenyl) ethyl carbonate, (trimethylphenyl) propyl carbonate, (trimethylphenyl) butyl carbonate, (trimethylphenyl) pentyl carbonate, (trimethyl) Phenyl) hexyl carbonate, (trimethylphenyl) cyclohexane Sil carbonate, (trimethylphenyl) heptyl carbonate, (trimethylphenyl) octyl carbonate, benzyl methyl carbonate, benzyl ethyl carbonate, benzyl n-propyl carbonate, benzyl isopropyl carbonate, benzyl n-butyl carbonate, benzyl isobutyl carbonate, benzyl sec-butyl carbonate Benzyl tert-butyl carbonate, benzyl pentyl carbonate, benzyl hexyl carbonate, benzyl cyclohexyl carbonate, benzyl heptyl carbonate, benzyl octyl carbonate.

  More preferably, the aromatic monofunctional carbonate compound is at least one compound selected from the following group.

  Diphenyl carbonate, bis (methylphenyl) carbonate, bis (methoxyphenyl) carbonate, bis (dimethylaminophenyl) carbonate, bis (fluorophenyl) carbonate, bis (trifluoromethylphenyl) carbonate, bis (acetylphenyl) carbonate, bis ( Dimethylphenyl) carbonate, bis (trimethylphenyl) carbonate, dibenzyl carbonate, benzylphenyl carbonate, methylphenyl carbonate, ethylphenyl carbonate, n-propylphenyl carbonate, isopropylphenyl carbonate, n-butylphenyl carbonate, isobutylphenyl carbonate, sec- Butyl phenyl carbonate, tert-butyl phenyl carbonate.

(Polyfunctional carbonate compound)
The polyfunctional carbonate compound according to this embodiment is not particularly limited as long as it has two or more carbonate groups. Examples of the polyfunctional carbonate compound include compounds in which a is 2 or more in the above formula (1).

Specific examples of R ₁ include the following.

  Methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, icosanylene, hexanilene, cosanylene, cosanylene, cosanylene, cosanylene, cosanylene, cosanylene, cosanylene An aliphatic hydrocarbon group such as hexacosanylene, heptacosanylene, octacosanylene, nonacosanylene, triacontanilene, hentriacontanilene, dotriacontanilene (these groups may be linear, branched or cyclic), and Substituted or unsubstituted aromatic hydrocarbon groups such as phenylene, naphthylene, and anthracenylene;

When the aromatic hydrocarbon group such as phenylene, naphthylene, anthracenylene or the like has a substituent, examples of the substituent include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, Linear, branched or tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triaconyl, hentriacontyl, dotriacontyl cyclic alkyl group, OR groups, OCOR groups, NR ₂ group, NHCOR group, CF ₃ group, CCl ₃ group, NO ₂ group, CN group, CHO group, COR group, CO ₂ R group, SO ₂ R group, S ₃ R group and the like. R represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group.

In the case where R ₁ and R ₂ are not linked, specific examples of R ₂ include the following.

  Methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henocosyl, docosyl, tricosyl, tetracosyl, pentacosyl, Hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, hentriacontyl, dotriacontyl and other aliphatic hydrocarbon groups (these groups may be linear, branched or cyclic), and substituted or unsubstituted phenyl , Aromatic hydrocarbon groups such as naphthyl and anthracenyl.

When the aromatic hydrocarbon group such as phenyl, naphthyl, anthracenyl has a substituent, examples of the substituent include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, Linear, branched or tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triaconyl, hentriacontyl, dotriacontyl Cyclic alkyl group, OR group, OCOR group, NR ₂ group, NHCOR group, CF ₃ group, CCl ₃ group, NO ₂ group, CN group, CHO group, COR group, CO ₂ R group, SO ₂ R group, SO ₃ R Groups and the like. R represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group.

When R ₁ and R ₂ are linked, or when R ₂ is linked, if R ₂ is specifically exemplified, the following may be mentioned.

  Methylene, ethylene, propylene, butylene, pentylene, hexylene, heptylene, octylene, nonylene, decylene, undecylene, dodecylene, tridecylene, tetradecylene, pentadecylene, hexadecylene, heptadecylene, octadecylene, nonadecylene, icosyl, heicosyl, docotetrasil Hexacosyl, heptacosyl, octacosyl, nonacosyl, triacontyl, hentriacontyl, dotriacontyl and other aliphatic hydrocarbon groups (these groups may be linear, branched or cyclic), and substituted or unsubstituted phenylene , Aromatic hydrocarbon groups such as naphthylene and anthracenylene.

When the aromatic hydrocarbon group such as phenylene, naphthylene, anthracenylene or the like has a substituent, examples of the substituent include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, Linear, branched or tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, henicosyl, docosyl, tricosyl, tetracosyl, pentacosyl, hexacosyl, heptacosyl, octacosyl, nonacosyl, triaconyl, hentriacontyl, dotriacontyl cyclic alkyl group, OR groups, OCOR groups, NR ₂ group, NHCOR group, CF ₃ group, CCl ₃ group, NO ₂ group, CN group, CHO group, COR group, CO ₂ R group, SO ₂ R group, S ₃ R group and the like. R represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group.

  Among the polyfunctional carbonate compounds, it is easy to obtain, the cost of the composition can be further suppressed, and it tends to be more economical. When preparing the composition at room temperature, the polymerization of the (C) epoxy compound is further suppressed. From the following group, the stability of the composition tends to be further improved and / or (C) the polymer obtained tends to be more transparent after polymerizing the epoxy compound. At least one compound selected is preferred.

  Ethylene glycol bis (methyl carbonate), ethylene glycol bis (ethyl carbonate), ethylene glycol bis (n-propyl carbonate), ethylene glycol bis (isopropyl carbonate), ethylene glycol bis (n-butyl carbonate), ethylene glycol bis (isobutyl carbonate) ), Ethylene glycol bis (sec-butyl carbonate), ethylene glycol bis (tert-butyl carbonate), ethylene glycol bis (cyclobutyl carbonate), ethylene glycol bis (pentyl carbonate), ethylene glycol bis (cyclopentyl carbonate), ethylene glycol bis (Hexyl carbonate), ethylene glycol bis (cyclohexyl carbonate), ethyl Glycol bis (heptyl carbonate), ethylene glycol bis (cycloheptyl carbonate), ethylene glycol bis (octyl carbonate), ethylene glycol bis (cyclooctyl carbonate), ethylene glycol bis (nonyl carbonate), ethylene glycol bis (decyl carbonate), Ethylene glycol bis (undecyl carbonate), ethylene glycol bis (dodecyl carbonate), ethylene glycol bis (tridecyl carbonate), ethylene glycol bis (tetradecyl carbonate), ethylene glycol bis (pentadecyl carbonate), ethylene glycol bis (hexadecyl) Carbonate), ethylene glycol bis (heptadecyl carbonate), ethylene glycol (Octadecyl carbonate), ethylene glycol bis (nonadecyl carbonate), ethylene glycol bis (icosyl carbonate), ethylene glycol bis (henicosyl carbonate), ethylene glycol bis (docosyl carbonate), ethylene glycol bis (tricosyl carbonate) ), Ethylene glycol bis (tetracosyl carbonate), ethylene glycol bis (pentacosyl carbonate), ethylene glycol bis (hexacosyl carbonate), ethylene glycol bis (heptacosyl carbonate), ethylene glycol bis (octacosyl carbonate) ), Ethylene glycol bis (nonacosyl carbonate), ethylene glycol bis (triacontyl carbonate);

  Ethylene glycol bis (phenyl carbonate), ethylene glycol bis [(methylphenyl) carbonate], ethylene glycol bis [(ethylphenyl) carbonate], ethylene glycol bis [(propylphenyl) carbonate], ethylene glycol bis [(butylphenyl) carbonate ], Ethylene glycol bis [(methoxyphenyl) carbonate], ethylene glycol bis [(dimethylaminophenyl) carbonate], ethylene glycol bis [(fluorophenyl) carbonate], ethylene glycol bis [(trifluoromethylphenyl) carbonate], ethylene Glycol bis [(acetylphenyl) carbonate], ethylene glycol bis [(dimethylphenyl) carbonate], ethylene Recall bis [(diethylphenyl) carbonate], ethylene glycol bis [(dipropylphenyl) carbonate], ethylene glycol bis [(dibutylphenyl) carbonate], ethylene glycol bis [(trimethylphenyl) carbonate], ethylene glycol bis [(triethyl Phenyl) carbonate], ethylene glycol bis [(tripropylphenyl) carbonate], ethylene glycol bis [(tributylphenyl) carbonate], ethylene glycol bis (benzyl carbonate), ethylene glycol bis (naphthyl carbonate), ethylene glycol bis [(methyl Naphthyl carbonate], ethylene glycol bis (anthracenyl carbonate);

  Propylene glycol bis (methyl carbonate), propylene glycol bis (ethyl carbonate), propylene glycol bis (n-propyl carbonate), propylene glycol bis (isopropyl carbonate), propylene glycol bis (n-butyl carbonate), propylene glycol bis (isobutyl carbonate) ), Propylene glycol bis (sec-butyl carbonate), propylene glycol bis (tert-butyl carbonate), propylene glycol bis (cyclobutyl carbonate), propylene glycol bis (pentyl carbonate), propylene glycol bis (cyclopentyl carbonate), propylene glycol bis (Hexyl carbonate), propylene glycol bis (cyclohexane Sil carbonate), propylene glycol bis (heptyl carbonate), propylene glycol bis (cycloheptyl carbonate), propylene glycol bis (octyl carbonate), propylene glycol bis (nonyl carbonate), propylene glycol bis (decyl carbonate), propylene glycol bis (un) Decyl carbonate), propylene glycol bis (dodecyl carbonate), propylene glycol bis (tridecyl carbonate), propylene glycol bis (tetradecyl carbonate), propylene glycol bis (pentadecyl carbonate), propylene glycol bis (hexadecyl carbonate), propylene glycol Bis (heptadecyl carbonate), propylene glycol vinyl (Octadecyl carbonate), propylene glycol bis (nonadecyl carbonate), propylene glycol bis (icosyl carbonate), propylene glycol bis (henicosyl carbonate), propylene glycol bis (docosyl carbonate), propylene glycol bis (tricosyl carbonate) , Propylene glycol bis (tetracosyl carbonate), propylene glycol bis (pentacosyl carbonate), propylene glycol bis (hexacosyl carbonate), propylene glycol bis (heptacosyl carbonate), propylene glycol bis (octacosyl carbonate) , Propylene glycol bis (nonacosyl carbonate), propylene glycol bis (triacontyl carbonate);

  Propylene glycol bis (phenyl carbonate), propylene glycol bis [(methylphenyl) carbonate], propylene glycol bis [(ethylphenyl) carbonate], propylene glycol bis [(propylphenyl) carbonate], propylene glycol bis [(butylphenyl) carbonate ], Propylene glycol bis [(methoxyphenyl) carbonate], propylene glycol bis [(dimethylaminophenyl) carbonate], propylene glycol bis [(fluorophenyl) carbonate], propylene glycol bis [(trifluorophenyl) carbonate], propylene glycol Bis [(acetylphenyl) carbonate], propylene glycol bis [(dimethylphenyl) carbonate , Propylene glycol bis [(diethylphenyl) carbonate], propylene glycol bis [(dipropylphenyl) carbonate], propylene glycol bis [(dibutylphenyl) carbonate], propylene glycol bis [(trimethylphenyl) carbonate], propylene glycol Bis [(triethylphenyl) carbonate], propylene glycol bis [(tripropylphenyl) carbonate], propylene glycol bis [(tributylphenyl) carbonate], propylene glycol bis (benzyl carbonate), propylene glycol bis (naphthyl carbonate), propylene glycol Bis [(methylnaphthyl) carbonate], propylene glycol bis (anthracenyl carbonate) ;

  1,3-propanediol bis (methyl carbonate), 1,3-propanediol bis (ethyl carbonate), 1,3-propanediol bis (n-propyl carbonate), 1,3-propanediol bis (isopropyl carbonate), 1,3-propanediol bis (n-butyl carbonate), 1,3-propanediol bis (isobutyl carbonate), 1,3-propanediol bis (sec-butyl carbonate), 1,3-propanediol bis (tert- Butyl carbonate), 1,3-propanediol bis (cyclobutyl carbonate), 1,3-propanediol bis (pentyl carbonate), 1,3-propanediol bis (cyclopentyl carbonate), 1,3-propanediol bis (hexylca) Bonate), 1,3-propanediol bis (cyclohexyl carbonate), 1,3-propanediol bis (heptyl carbonate), 1,3-propanediol bis (cycloheptyl carbonate), 1,3-propanediol bis (octyl carbonate) ), 1,3-propanediol bis (cyclooctyl carbonate), 1,3-propanediol bis (nonyl carbonate), 1,3-propanediol bis (decyl carbonate), 1,3-propanediol bis (undecyl carbonate) ), 1,3-propanediol bis (dodecyl carbonate), 1,3-propanediol bis (tridecyl carbonate), 1,3-propanediol bis (tetradecyl carbonate), 1,3-propanediol bis (penta Silcarbonate), 1,3-propanediol bis (hexadecyl carbonate), 1,3-propanediol bis (heptadecyl carbonate), 1,3-propanediol bis (octadecyl carbonate), 1,3-propanediol bis ( Nonadecyl carbonate), 1,3-propanediol bis (icosyl carbonate), 1,3-propanediol bis (henicosyl carbonate), 1,3-propanediol bis (docosyl carbonate), 1,3-propane Diol bis (tricosyl carbonate), 1,3-propanediol bis (tetracosyl carbonate), 1,3-propanediol bis (pentacosyl carbonate), 1,3-propanediol bis (hexacosyl carbonate), 1,3-propanedio Bis (heptacosyl carbonate), 1,3-propanediol bis (octacosyl carbonate), 1,3-propanediol bis (nonacosyl carbonate), 1,3-propanediol bis (triacontyl carbonate);

  1,3-propanediol bis (phenyl carbonate), 1,3-propanediol bis [(methylphenyl) carbonate], 1,3-propanediol bis [(ethylphenyl) carbonate], 1,3-propanediol bis [ (Propylphenyl) carbonate], 1,3-propanediol bis [(butylphenyl) carbonate], 1,3-propanediol bis [(dimethylphenyl) carbonate], 1,3-propanediol bis [(diethylphenyl) carbonate ], 1,3-propanediol bis [(dipropylphenyl) carbonate], 1,3-propanediol bis [(dibutylphenyl) carbonate], 1,3-propanediol bis [(trimethylphenyl) carbonate], 1, 3-propanediol Rubis [(triethylphenyl) carbonate], 1,3-propanediol bis [(tripropylphenyl) carbonate], 1,3-propanediol bis [(tributylphenyl) carbonate], 1,3-propanediol bis (benzyl carbonate) ), 1,3-propanediol bis (naphthyl carbonate), 1,3-propanediol bis [(methyl naphthyl) carbonate], 1,3-propanediol bis (anthracenyl carbonate);

  Butylene glycol bis (methyl carbonate), butylene glycol bis (ethyl carbonate), butylene glycol bis (propyl carbonate), butylene glycol bis (butyl carbonate), butylene glycol bis (cyclobutyl carbonate), butylene glycol bis (pentyl carbonate), butylene Glycol bis (cyclopentyl carbonate), butylene glycol bis (hexyl carbonate), butylene glycol bis (cyclohexyl carbonate), butylene glycol bis (heptyl carbonate), butylene glycol bis (octyl carbonate), butylene glycol bis (nonyl carbonate), butylene glycol bis (Decyl carbonate), butylene glycol bis (undecyl carbonate) Bonate), butylene glycol bis (dodecyl carbonate), butylene glycol bis (phenyl carbonate), butylene glycol bis [(methylphenyl) carbonate], butylene glycol bis [(dimethylphenyl) carbonate], butylene glycol bis [(trimethylphenyl) carbonate ], Butylene glycol bis (benzyl carbonate), pentylene glycol bis (methyl carbonate), pentylene glycol bis (ethyl carbonate), pentylene glycol bis (propyl carbonate), pentylene glycol bis (butyl carbonate), pentylene glycol bis (Cyclobutyl carbonate), pentylene glycol bis (pentyl carbonate), pentylene glycol bis (siku Pentyl carbonate), pentylene glycol bis (hexyl carbonate), pentylene glycol bis (cyclohexyl carbonate), pentylene glycol bis (heptyl carbonate), pentylene glycol bis (octyl carbonate), pentylene glycol bis (nonyl carbonate), pent Lenglycol bis (decyl carbonate), pentylene glycol bis (phenyl carbonate), pentylene glycol bis [(methylphenyl) carbonate], pentylene glycol bis [(dimethylphenyl) carbonate], pentylene glycol bis [(trimethylphenyl) Carbonate], pentylene glycol bis (benzyl carbonate);

  Hexylene glycol bis (methyl carbonate), hexylene glycol bis (ethyl carbonate), hexylene glycol bis (propyl carbonate), hexylene glycol bis (butyl carbonate), hexylene glycol bis (cyclobutyl carbonate), hexylene glycol bis (Pentyl carbonate), hexylene glycol bis (cyclopentyl carbonate), hexylene glycol bis (hexyl carbonate), hexylene glycol bis (cyclohexyl carbonate), hexylene glycol bis (heptyl carbonate), hexylene glycol bis (octyl carbonate), Hexylene glycol bis (nonyl carbonate), hexylene glycol bis (decyl carbonate), hexylene Recall bis (phenyl carbonate), hexylene glycol bis [(methylphenyl) carbonate], hexylene glycol bis [(dimethylphenyl) carbonate], hexylene glycol bis [(trimethylphenyl) carbonate], hexylene glycol bis (benzyl carbonate) );

  Cyclohexanediol bis (methyl carbonate), cyclohexanediol bis (ethyl carbonate), cyclohexanediol bis (n-propyl carbonate), cyclohexanediol bis (isopropyl carbonate), cyclohexanediol bis (n-butyl carbonate), cyclohexanediol bis (isobutyl carbonate) ), Cyclohexanediol bis (sec-butyl carbonate), cyclohexanediol bis (tert-butyl carbonate), cyclohexanediol bis (cyclobutylcarbonate), cyclohexanediol bis (pentylcarbonate), cyclohexanediol bis (cyclopentylcarbonate), cyclohexanediol bis (Hexyl carbonate), cyclohex Diol bis (cyclohexyl carbonate), cyclohexane diol bis (heptyl carbonate), cyclohexane diol bis (octyl carbonate), cyclohexane diol bis (nonyl carbonate), cyclohexane diol bis (decyl carbonate), cyclohexane diol bis (undecyl carbonate), cyclohexane diol bis (Dodecyl carbonate), cyclohexanediol bis (tridecyl carbonate), cyclohexanediol bis (tetradecyl carbonate), cyclohexanediol bis (pentadecyl carbonate), cyclohexanediol bis (hexadecyl carbonate), cyclohexanediol bis (heptadecyl carbonate), Cyclohexanediol bis (o Tadecyl carbonate), cyclohexanediol bis (phenyl carbonate), cyclohexanediol bis [(methylphenyl) carbonate], cyclohexanediol bis [(dimethylphenyl) carbonate], cyclohexanediol bis [(trimethylphenyl) carbonate], cyclohexanediol bis ( Benzyl carbonate);

  Heptylene glycol bis (methyl carbonate), heptylene glycol bis (ethyl carbonate), heptylene glycol bis (propyl carbonate), heptylene glycol bis (butyl carbonate), heptylene glycol bis (pentyl carbonate), Heptylene glycol bis (hexyl carbonate), heptylene glycol bis (cyclohexyl carbonate), heptylene glycol bis (heptyl carbonate), heptylene glycol bis (octyl carbonate), heptylene glycol bis (phenyl carbonate), Heptylene glycol bis (benzyl carbonate), octylene glycol bis (methyl carbonate), octylene glycol bis (ethyl carbonate), octylene glycol (Propyl carbonate) octylene glycol bis (butyl carbonate), octylene glycol bis (pentyl carbonate), octylene glycol bis (hexyl carbonate), octylene glycol bis (cyclohexyl carbonate), octylene glycol bis (heptyl carbonate), Octylene glycol bis (octyl carbonate), octylene glycol bis (phenyl carbonate), octylene glycol bis (benzyl carbonate), erythritol biscarbonate;

  Propane triol tris (methyl carbonate), propane triol tris (ethyl carbonate), propane triol tris (propyl carbonate), propane triol tris (butyl carbonate), propane triol tris (cyclobutyl carbonate), propane triol tris (pentyl carbonate), propane Triol tris (cyclopentyl carbonate), propane triol tris (hexyl carbonate), propane triol tris (cyclohexyl carbonate), propane triol tris (heptyl carbonate), propane triol tris (cycloheptyl carbonate), propane triol tris (octyl carbonate), propane triol Tris (cyclooctyl carbonate) ), Propane triol tris (nonyl carbonate), propane triol tris (decyl carbonate), propane triol tris (undecyl carbonate), propane triol tris (dodecyl carbonate), propane triol tris (tridecyl carbonate), propane triol tris (tetradecyl) Carbonate), propane triol tris (pentadecyl carbonate), propane triol tris (hexadecyl carbonate), propane triol tris (heptadecyl carbonate), propane triol tris (octadecyl carbonate), propane triol tris (phenyl carbonate), propane triol tris [ (Methylphenyl) carbonate], propanetriol tris [ Ruphenyl) carbonate], propanetriol tris [(propylphenyl) carbonate], propanetrioltris [(butylphenyl) carbonate], propanetrioltris [(dimethylphenyl) carbonate], propanetrioltris [(diethylphenyl) carbonate], propane Triol tris [(dipropylphenyl) carbonate], propane triol tris [(dibutylphenyl) carbonate], propane triol tris [(trimethylphenyl) carbonate], propane triol tris [(triethylphenyl) carbonate], propane triol tris [(tri Propylphenyl) carbonate], propanetriol tris [(tributylphenyl) carbonate], propane Triol tris (benzyl carbonate), propane triol tris (naphthyl carbonate), propane triol tris [(methyl naphthyl) carbonate], propane triol tris (anthracenyl carbonate);

  Butanetriol tris (methyl carbonate), butanetriol tris (ethyl carbonate), butanetriol tris (propyl carbonate), butanetriol tris (butyl carbonate), butanetriol tris (pentyl carbonate), butanetriol tris (hexyl carbonate), butanetriol Tris (cyclohexyl carbonate), butanetriol tris (heptyl carbonate), butanetriol tris (octyl carbonate), butanetriol tris (nonyl carbonate), butanetriol tris (decyl carbonate), butanetriol tris (phenyl carbonate), butanetriol tris ( Benzyl carbonate), pentanetriol tris (methyl carbonate) Pentanetriol tris (ethyl carbonate), pentanetriol tris (propyl carbonate), pentanetriol tris (butyl carbonate), pentanetriol tris (pentyl carbonate), pentanetriol tris (hexyl carbonate), pentanetriol tris (cyclohexyl carbonate), pentanetriol Tris (heptyl carbonate), pentane triol tris (octyl carbonate), pentane triol tris (nonyl carbonate), pentane triol tris (decyl carbonate), pentane triol tris (phenyl carbonate), pentane triol tris (benzyl carbonate), hexane triol tris ( Methyl carbonate), hexanetriol Lith (ethyl carbonate), hexane triol tris (propyl carbonate), hexane triol tris (butyl carbonate), hexane triol tris (pentyl carbonate), hexane triol tris (hexyl carbonate), hexane triol tris (cyclohexyl carbonate), hexane triol tris ( Heptyl carbonate), hexane triol tris (octyl carbonate), hexane triol tris (phenyl carbonate), hexane triol tris (benzyl carbonate);

  Cyclohexane triol tris (methyl carbonate), cyclohexane triol tris (ethyl carbonate), cyclohexane triol tris (propyl carbonate), cyclohexane triol tris (butyl carbonate), cyclohexane triol tris (cyclobutyl carbonate), cyclohexane triol tris (pentyl carbonate), cyclohexane Triol tris (cyclopentyl carbonate), cyclohexane triol tris (hexyl carbonate), cyclohexane triol tris (cyclohexyl carbonate), cyclohexane triol tris (heptyl carbonate), cyclohexane triol tris (cycloheptyl carbonate), cyclohexane triol tris (o Chill carbonate), cyclohexane triol tris (nonyl carbonate), cyclohexane triol tris (decyl carbonate), cyclohexane triol tris (undecyl carbonate), cyclohexane triol tris (dodecyl carbonate), cyclohexane triol tris (tridecyl carbonate), cyclohexane triol tris ( Tetradecyl carbonate), cyclohexane triol tris (pentadecyl carbonate), cyclohexane triol tris (hexadecyl carbonate), cyclohexane triol tris (heptadecyl carbonate), cyclohexane triol tris (octadecyl carbonate), cyclohexane triol tris (phenyl carbonate), cyclohex Santriol tris [(methylphenyl) carbonate], cyclohexanetrioltris [(ethylphenyl) carbonate], cyclohexanetrioltris [(propylphenyl) carbonate], cyclohexanetrioltris [(butylphenyl) carbonate], cyclohexanetrioltris [(dimethyl Phenyl) carbonate], cyclohexanetriol tris [(diethylphenyl) carbonate], cyclohexanetrioltris [(dipropylphenyl) carbonate], cyclohexanetrioltris [(dibutylphenyl) carbonate], cyclohexanetrioltris [(trimethylphenyl) carbonate], Cyclohexanetrioltris [(triethylphenyl) carbonate ], Cyclohexane triol tris [(tripropylphenyl) carbonate], cyclohexane triol tris [(tributylphenyl) carbonate], cyclohexane triol tris (benzyl carbonate), cyclohexane triol tris (naphthyl carbonate), cyclohexane triol tris [(methyl naphthyl) carbonate ], Cyclohexanetriol tris (anthracenyl carbonate).

  More preferably, the polyfunctional carbonate compound is at least one compound selected from the following group.

  Ethylene glycol bis (methyl carbonate), ethylene glycol bis (ethyl carbonate), ethylene glycol bis (n-propyl carbonate), ethylene glycol bis (isopropyl carbonate), ethylene glycol bis (n-butyl carbonate), ethylene glycol bis (isobutyl carbonate) ), Ethylene glycol bis (sec-butyl carbonate), ethylene glycol bis (tert-butyl carbonate), ethylene glycol bis (pentyl carbonate), ethylene glycol bis (hexyl carbonate), ethylene glycol bis (cyclohexyl carbonate), ethylene glycol bis ( Phenyl carbonate), ethylene glycol bis (benzyl carbonate), propylene glycol Bis (methyl carbonate), propylene glycol bis (ethyl carbonate), propylene glycol bis (n-propyl carbonate), propylene glycol bis (isopropyl carbonate), propylene glycol bis (n-butyl carbonate), propylene glycol bis (isobutyl carbonate), Propylene glycol bis (sec-butyl carbonate), propylene glycol bis (tert-butyl carbonate), propylene glycol bis (pentyl carbonate), propylene glycol bis (hexyl carbonate), propylene glycol bis (cyclohexyl carbonate), propylene glycol bis (phenyl carbonate) ), Propylene glycol bis (benzyl carbonate), 1 3-propanediol bis (methyl carbonate), 1,3-propanediol bis (ethyl carbonate), 1,3-propanediol bis (n-propyl carbonate), 1,3-propanediol bis (isopropyl carbonate), 1, 3-propanediol bis (n-butyl carbonate), 1,3-propanediol bis (isobutyl carbonate), 1,3-propanediol bis (sec-butyl carbonate), 1,3-propanediol bis (tert-butyl carbonate) ), 1,3-propanediol bis (phenyl carbonate);

  Butylene glycol bis (methyl carbonate), butylene glycol bis (ethyl carbonate), butylene glycol bis (phenyl carbonate), pentylene glycol bis (methyl carbonate), pentylene glycol bis (ethyl carbonate), pentylene glycol bis (phenyl carbonate) Hexylene glycol bis (methyl carbonate), hexylene glycol bis (ethyl carbonate), hexylene glycol bis (phenyl carbonate), cyclohexanediol bis (methyl carbonate), cyclohexanediol bis (ethyl carbonate), cyclohexanediol bis (n- Propyl carbonate), cyclohexanediol bis (isopropyl carbonate), cyclohexanediol (N-butyl carbonate), cyclohexanediol bis (isobutyl carbonate), cyclohexanediol bis (sec-butyl carbonate), cyclohexanediol bis (tert-butyl carbonate), cyclohexanediol bis (pentyl carbonate), cyclohexanediol bis (hexyl carbonate) ), Cyclohexanediol bis (cyclohexyl carbonate), cyclohexanediol bis (phenyl carbonate), cyclohexanediol bis (benzyl carbonate), erythritol biscarbonate;

  Propane triol tris (methyl carbonate), propane triol tris (ethyl carbonate), propane triol tris (propyl carbonate), propane triol tris (butyl carbonate), propane triol tris (pentyl carbonate), propane triol tris (hexyl carbonate), propane triol Tris (cyclohexyl carbonate), propane triol, propane triol tris (phenyl carbonate), propane triol tris (benzyl carbonate), butane triol tris (methyl carbonate), butane triol tris (ethyl carbonate), butane triol tris (phenyl carbonate), pentane Triol tris (methyl carbonate), pentane Riol Tris (ethyl carbonate), pentane triol tris (phenyl carbonate), hexane triol tris (methyl carbonate), hexane triol tris (ethyl carbonate), hexane triol tris (phenyl carbonate), cyclohexane triol tris (methyl carbonate), cyclohexane triol tris (Ethyl carbonate), cyclohexane triol tris (propyl carbonate), cyclohexane triol tris (butyl carbonate), cyclohexane triol tris (pentyl carbonate), cyclohexane triol tris (hexyl carbonate), cyclohexane triol tris (cyclohexyl carbonate), cyclohexane triol tris (pheny Carbonate), cyclohexane triol tris [(methylphenyl) carbonate], cyclohexanetriol tris [(dimethylphenyl) carbonate], cyclohexanetriol tris [(trimethylphenyl) carbonate], cyclohexanetriol tris (benzyl carbonate).

  More preferably, the polyfunctional carbonate compound is at least one compound selected from the following group.

  Ethylene glycol bis (methyl carbonate), ethylene glycol bis (ethyl carbonate), propylene glycol bis (methyl carbonate), propylene glycol bis (ethyl carbonate), cyclohexanediol bis (methyl carbonate), cyclohexanediol bis (ethyl carbonate), erythritol bis Carbonate, propane triol tris (methyl carbonate), propane triol tris (ethyl carbonate), cyclohexane triol tris (methyl carbonate), cyclohexane triol tris (ethyl carbonate).

(Component (B): boron trihalide)
The (B) boron trihalide of this embodiment is a compound composed of 3 halogen atoms and 1 boron atom.

  (B) Specific examples of boron trihalide include boron trifluoride, boron trichloride, boron tribromide, and boron triiodide. These may be used alone or in combination of two or more.

  (B) Boron trifluoride is preferably boron trifluoride, boron trichloride and boron tribromide because Lewis acidity tends to decrease and handleability tends to improve. (A) Bonding power of carbonate compound and (B) boron trihalide is improved, and when it is used as a composition, polymerization of (C) epoxy compound can be further suppressed, and the stability of the composition tends to be further improved. For this reason, boron trifluoride and boron trichloride are more preferable. From the same viewpoint, boron trifluoride is more preferable.

  When (A) a carbonate compound and (B) boron trihalide form a compound (complex) via a coordination bond, when preparing a composition at room temperature, (C) epoxy The polymerization of the compound can be further suppressed, and the stability of the composition tends to be further improved. To preferred. From the same viewpoint, it is more preferable that all of (B) boron trihalide contained in the composition form (A) a compound (complex) via a coordination bond with the carbonate compound.

(Component (C): Epoxy compound)
Component (C) of the present embodiment is a compound having at least one three-membered ether structure as a polymerizable functional group. As the component (C), one type of epoxy compound may be used alone, or a plurality of types of epoxy compounds may be used in combination.

  The polymerizable functional group refers to a substituent capable of providing a bond between monomers when forming a polymer in which monomers are linked via a bond.

  The component (C) may have only a three-membered ring ether structure as a polymerizable functional group, or may have a polymerizable functional group generally used together with the three-membered ring ether structure.

  Although it does not specifically limit as a polymerizable functional group generally used, For example, cyclic ether structure, cyclic thioether structure, lactone structure, cyclic carbonate structure and its sulfur-containing analog structure, cyclic acetal structure and its sulfur-containing analog structure, cyclic It can be selected from amine structures, cyclic imino ether structures, lactam structures, cyclic thiourea structures, cyclic phosphinate structures, cyclic phosphonite structures, cyclic phosphite structures, vinyl structures, allyl structures, (meth) acrylic structures, and cycloalkane structures.

  Epoxy compounds having a three-membered ring ether structure and a commonly used polymerizable functional group as the polymerizable functional group may have polymerizable functional groups with different polymerization conditions. Therefore, the epoxy compound is polymerized at least one polymerizable functional group to form a semipolymer, and after processing such as molding the semipolymer, further polymerize to make a complete polymer, It can be used as an effective means for an application that requires a process for obtaining desired physical properties.

  (C) As an epoxy compound, it has only a three-membered ring ether structure as a polymerizable functional group, or has a three-membered ring ether structure as a polymerizable functional group, and also has a lactone structure, a cyclic carbonate structure, and a sulfur-containing analog structure thereof At least one selected from the group consisting of a cyclic acetal structure and its sulfur-containing analog structure, a cyclic amine structure, a cyclic imino ether structure, a lactam structure, a cyclic thiourea structure, a cyclic phosphinate structure, a cyclic phosphonite structure, and a cyclic phosphite structure It is preferable to have a structure as a polymerizable functional group.

  Among these, since the residual of the polymerizable functional group tends to be suppressed, it has only a three-membered ring ether structure as a polymerizable functional group, or has a three-membered ring ether structure as a polymerizable functional group, and 4-membered ring, 6-membered ring, 7-membered lactone structure, 5-membered ring, 6-membered cyclic carbonate structure and its sulfur-containing analogue structure, 5-membered cyclic acetal structure and its sulfur-containing analogue structure, 3-membered ring, 4-membered Cyclic amine structure, 5-membered ring, 6-membered cyclic imino ether structure, 4-membered ring, 7-membered ring, 8-membered lactam structure, 5-membered ring, 6-membered cyclic thiourea structure, cyclic phosphinate structure, cyclic phosphonite structure, A compound having at least one structure selected from the group consisting of cyclic phosphite structures as a polymerizable functional group is more preferable. Furthermore, since it is easier to control the polymerizability, it tends to be able to suppress the remaining of the polymerizable functional group, does not require a multi-step polymerization process, can suppress the cost as a polymer, and is excellent in economic efficiency. Due to the tendency, a compound having only a three-membered cyclic ether structure as a polymerizable functional group is particularly preferred.

  The epoxy equivalent (WPE, g / mol) of component (C) is preferably 55 or more because the vapor pressure of the epoxy compound in the standard state is high and the handling tends to be easy. It is more preferable that the epoxy equivalent is 70 or more because the transparency of the resulting polymer tends to be further improved after polymerization. From the same viewpoint, the epoxy equivalent is more preferably 85 or more.

  The epoxy equivalent (WPE, g / mol) of the component (C) is preferably 600 or less because it tends to suppress residual epoxy groups when the composition is polymerized. Since the heat resistance of the cured product formed from the epoxy compound tends to improve, the epoxy equivalent is more preferably 500 or less. From the same viewpoint, the epoxy equivalent is more preferably 450 or less.

  The component (C) is not particularly limited as long as it is a compound having a three-membered cyclic ether structure as a polymerizable functional group, but it is easily available, the cost of the composition is suppressed, and the economy tends to be excellent. It preferably has a partial structure represented by the following formula (3), (4), (5) or (6). Moreover, since it exists in the tendency for the stability as a composition to improve more, it is more preferable to have a partial structure represented by following formula (3) or (4). From the viewpoint of transparency, it is more preferable to have a partial structure represented by the formula (3) since the transparency of the polymer obtained after polymerization of the composition tends to be further enhanced. From the viewpoint of heat resistance, it is more preferable to have a partial structure represented by the formula (4) because the heat resistance of a cured product formed from an epoxy compound tends to be further improved.

In the formula, R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ , R ₂₀ , R ₂₁ , R ₂₂ , R ₂₃ and R ₂₄ are each independent. Are a hydrogen atom, a chain, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group.

  Specific examples of the component (C) include monofunctional epoxy compounds, polyfunctional epoxy compounds that are glycidyl etherified products of polyphenol compounds, alicyclic epoxy compounds, and polyfunctional epoxy compounds that are glycidyl etherified products of various novolak compounds. , Aromatic epoxy compound nuclear hydrides, heterocyclic epoxy compounds, glycidyl ester epoxy compounds, glycidyl amine epoxy compounds, epoxy compounds obtained by glycidylation of halogenated phenols, polyfunctional aliphatic epoxy compounds, Examples thereof include a silicone compound having an epoxy group and a heteropolymerizable functional group-containing epoxy compound. These may be used alone or in combination.

(Monofunctional epoxy compound)
The monofunctional epoxy compound is not particularly limited as long as it is a compound having one three-membered cyclic ether structure. Specifically, ethylene oxide, propylene oxide, 1-butene oxide, 2-butene oxide, butadiene oxide, Butadiene diepoxide, cyclobutene oxide, 1,3-cyclobutadiene diepoxide, 1-pentene oxide, 2-pentene oxide, 1,3-pentadiene diepoxide, 1,4-pentadiene diepoxide, 2-methyl-2-butene Oxide, 2-methyl-3-butene oxide, cyclopentene oxide, 1,3-cyclopentadiene diepoxide, 1-methyl-cyclobutene oxide, 3-methyl-1-cyclobutene oxide, 1-hexene oxide, 2-hexene oxide , 3-hexene oxide 1,3-hexadiene diepoxide, 1,4-hexadiene diepoxide, 1,5-hexadiene diepoxide, 1,3,5-hexatriene epoxide, cyclohexene oxide, 1,3-cyclohexadiene diepoxide, 1,3 , 5-cyclohexatriene epoxide, 1-methyl-cyclopentene oxide, 3-methyl-cyclopentene oxide, 1-methyl-1,3-cyclopentadiene diepoxide, 2-methyl-1,3-cyclopentadiene diepoxide, 5- Methyl-1,3-cyclopentadiene diepoxide, 3,4-dimethyl-cyclobutene oxide, 2,3-dimethyl-cyclobutene oxide, 1,2-dimethyl-cyclobutene oxide, 1,2-dimethyl-1,3 -Cyclobutadiene diepoxide, 2, -Dimethyl-1,3-cyclobutadiene diepoxide, 3,3-dimethyl-1,2-epoxybutane, 1-heptene oxide, 2-heptene oxide, 3-heptene oxide, 1,3-heptadiene diene Epoxide, 1,4-heptadiene diepoxide, 1,5-heptadiene diepoxide, 1,5-heptadiene diepoxide, 1,6-heptadiene diepoxide, 1,3,5-heptatriene epoxide, 1 , 3,6-heptatriene epoxide, 1,4,6-heptatriene epoxide, cycloheptene oxide, 1-methyl-cyclohexene oxide, 3-methyl-cyclohexene oxide, 4-methyl-cyclohexene oxide, 1-methyl -1,3-cyclohexadiene diepoxide, 1-methyl-1,4-hexadi Enddiepoxide, 1-methyl-1,3,5-hexatrient epoxide, 1,2-epoxy-5-hexene, 1,2-epoxy-4-vinylcyclohexene, 2-norbornene oxide, 7-methyl-2- Norbornene oxide, 7,7-dimethyl-2-norbornene oxide, 2-methyl-2-norbornene oxide, 2,3-dimethyl-2-norbornene oxide, 2,7-dimethyl-2-norbornene oxide, 2,7,7 -Trimethyl-2-norbornene oxide, 2,3-epoxy-bicyclo [2.2.2] octane, 2,3-epoxy-2-methyl-bicyclo [2.2.2] octane, 2,3-epoxy- 2,3-dimethyl-bicyclo [2.2.2] octane, 2,3-epoxy-2,5-dimethyl-bicyclo [2.2. ] Octane, 2,3-epoxy-2,6-dimethyl-bicyclo [2.2.2] octane, 2,3-epoxy-2,3,5-trimethyl-bicyclo [2.2.2] octane, , 3-epoxy-2,5,6-trimethyl-bicyclo [2.2.2] octane, 2,3-epoxy-2,3,5,6-tetramethyl-bicyclo [2.2.2] octane, Dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, stilbene oxide, phenylglycidyl ether, 3- (2,2,3,3-tetrafluoropropoxy) -1,2-epoxypropane, pinene oxide , Isoprene monooxide, 1,2-epoxyethylbenzene, naphthyl glycidyl ether, 3- (2-biphenyloxy) -1,2-epoxy Cypropane, allyl glycidyl ether, 1,1-diphenyl-ethylene oxide, glycidyl (meth) acrylate, glycidyl butyrate, iodomethyloxirane, 4- (2,3-epoxypropyl) morpholine, glycidyl methyl ether, 2-phenyl-propylene Oxide, 2,3-epoxypropyl-furfuryl ether, 2,3,4,5,6-pentafluorostyrene oxide, ethyl-3-phenylglycidate, limonene oxide, epoxysuccinic acid, 3-glycidoxypropyltri Methoxysilane, (3-glycidoxypropyl) pentamethyldisiloxane, 3-glycidoxypropyl (methyl) dimethoxysilane, 3-glycidoxypropyl (methyl) diethoxysilane, 3-glycidoxypropyl (methyl) Dibutoxysilane, 2- (3,4-epoxycyclohexyl) ethyl (methyl) dimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyl (phenyl) diethoxysilane, 2,3-epoxypropyl (methyl) dimethoxysilane 2,3-epoxypropyl (phenyl) dimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-thioglycidoxypropyltriethoxysilane, 3-glycidoxypropyltributoxysilane, 2- (3,4 -Epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltriethoxysilane, 2,3-epoxypropyltrimethoxysilane and 2,3-epoxypropyltriethoxysilane.

  Among them, the vapor pressure in the standard state is high, the handling is easy, the stability as a composition tends to be further improved, and the transparency of the resulting polymer after the polymerization tends to be further improved. Therefore, the monofunctional epoxy compound is preferably at least one compound selected from the following group.

  Ethylene oxide, propylene oxide, 1-butene oxide, 2-butene oxide, butadiene oxide, butadiene diepoxide, cyclobutene oxide, 1,3-cyclobutadiene diepoxide, 1-pentene oxide, 2-pentene oxide, 1,3-pentadiene Diepoxide, 1,4-pentadiene diepoxide, 2-methyl-2-butene oxide, 2-methyl-3-butene oxide, cyclopentene oxide, 1,3-cyclopentadiene diepoxide, 1-methyl-cyclobutene oxide, 3 -Methyl-1-cyclobutene oxide, 1-hexene oxide, 2-hexene oxide, 3-hexene oxide, 1,3-hexadiene diepoxide, 1,4-hexadiene diepoxide, 1,5-hexadiene diepoxide, 1, , 5-hexatriene epoxide, cyclohexene oxide, 1,3-cyclohexadiene diepoxide, 1,3,5-cyclohexatriene epoxide, 1-methyl-cyclopentene oxide, 3-methyl-cyclopentene oxide, 1-methyl-1 , 3-cyclopentadiene diepoxide, 2-methyl-1,3-cyclopentadiene diepoxide, 5-methyl-1,3-cyclopentadiene diepoxide, 3,4-dimethyl-cyclobutene oxide, 2,3-dimethyl- Cyclobutene oxide, 1,2-dimethyl-cyclobutene oxide, 1,2-dimethyl-1,3-cyclobutadiene diepoxide, 2,3-dimethyl-1,3-cyclobutadiene diepoxide, 3,3-dimethyl- 1,2-epoxybutane, 1-hepteno Side, 2-heptene oxide, 3-heptene oxide, 1,3-heptadiene diepoxide, 1,4-heptadiene diepoxide, 1,5-heptadiene diepoxide, 1,5-heptadiene diepoxide, 1,6-heptadiene diepoxide, 1,3,5-heptatrient epoxide, 1,3,6-heptatrient epoxide, 1,4,6-heptatrient epoxide, cycloheptene oxide, 1-methyl -Cyclohexene oxide, 3-methyl-cyclohexene oxide, 4-methyl-cyclohexene oxide, 1-methyl-1,3-cyclohexadiene diepoxide, 1-methyl-1,4-hexadiene diepoxide, 1-methyl-1,3 , 5-hexatrient epoxide, 1,2-epoxy-5-hexene, 1, 2-epoxy-4-vinylcyclohexene, dioctyl epoxyhexahydrophthalate, di-2-ethylhexyl epoxyhexahydrophthalate, stilbene oxide, phenylglycidyl ether, 3- (2,2,3,3-tetrafluoropropoxy)- 1,2-epoxypropane, pinene oxide, isoprene monooxide, 1,2-epoxyethylbenzene, naphthyl glycidyl ether, 3- (2-biphenyloxy) -1,2-epoxypropane, allyl glycidyl ether, 1,1-diphenyl- Ethylene oxide, glycidyl (meth) acrylate, glycidyl butyrate, iodomethyloxirane, 4- (2,3-epoxypropyl) morpholine, glycidyl methyl ether, 2-phenyl-propylene oxide, 2,3- Poxypropyl-furfuryl ether, 2,3,4,5,6-pentafluorostyrene oxide, ethyl-3-phenylglycidate, limonene oxide, epoxysuccinic acid, 3-glycidoxypropyltrimethoxysilane, (3- Glycidoxypropyl) pentamethyldisiloxane, 3-glycidoxypropyl (methyl) dimethoxysilane, 3-glycidoxypropyl (methyl) diethoxysilane, 3-glycidoxypropyl (methyl) dibutoxysilane, 2- (3,4-epoxycyclohexyl) ethyl (methyl) dimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyl (phenyl) diethoxysilane, 2,3-epoxypropyl (methyl) dimethoxysilane, 2,3-epoxy Propyl (phenyl) dimethoxysilane 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropyltributoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3 4-Epoxycyclohexyl) ethyltriethoxysilane, 2,3-epoxypropyltrimethoxysilane and 2,3-epoxypropyltriethoxysilane.

  More preferably, the monofunctional epoxy compound is at least one compound selected from the following group.

  Propylene oxide, 1-butene oxide, 2-butene oxide, butadiene oxide, butadiene diepoxide, 1-pentene oxide, 2-pentene oxide, 1,3-pentadiene diepoxide, 1,4-pentadiene diepoxide, 2-methyl- 2-butene oxide, 2-methyl-3-butene oxide, cyclopentene oxide, 1-methyl-cyclobutene oxide, 3-methyl-1-cyclobutene oxide, 1-hexene oxide, 2-hexene oxide, 3-hexene oxide, 1,3-hexadiene diepoxide, 1,4-hexadiene diepoxide, 1,5-hexadiene diepoxide, 1,3,5-hexatriene epoxide, cyclohexene oxide, 1,3-cyclohexadiene diepoxide, 1-methyl -Siku Pentene oxide, 3-methyl-cyclopentene oxide, 2-heptene oxide, 3-heptene oxide, 1,3-heptadiene diepoxide, 1,4-heptadiene diepoxide, 1,5-heptadiene diepoxide, 1 , 5-heptadiene diepoxide, 1,6-heptadiene diepoxide, 1-methyl-cyclohexene oxide, 3-methyl-cyclohexene oxide, 4-methyl-cyclohexene oxide, 1,2-epoxy-5-hexene, 1, 2-epoxy-4-vinylcyclohexene, stilbene oxide, phenylglycidyl ether, 3- (2,2,3,3-tetrafluoropropoxy) -1,2-epoxypropane, pinene oxide, isoprene monooxide, 1,2- Epoxyethylbenzene, naphthylglycid Ether, 3- (2-biphenyloxy) -1,2-epoxypropane, allyl glycidyl ether, 1,1-diphenyl-ethylene oxide, glycidyl (meth) acrylate, glycidyl butyrate, iodomethyloxirane, 4- (2,3- Epoxypropyl) morpholine, glycidyl methyl ether, 2-phenyl-propylene oxide, 2,3-epoxypropyl-furfuryl ether, 2,3,4,5,6-pentafluorostyrene oxide, ethyl-3-phenylglycidate, Limonene oxide, epoxysuccinic acid, 3-glycidoxypropyltrimethoxysilane, (3-glycidoxypropyl) pentamethyldisiloxane, 3-glycidoxypropyl (methyl) dimethoxysilane, 3-glycidoxypropyl ( Methyl) Diethoxysilane, 3-glycidoxypropyl (methyl) dibutoxysilane, 2- (3,4-epoxycyclohexyl) ethyl (methyl) dimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyl (phenyl) diethoxy Silane, 2,3-epoxypropyl (methyl) dimethoxysilane, 2,3-epoxypropyl (phenyl) dimethoxysilane, 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycid Xylpropyltributoxysilane, 2- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-epoxycyclohexyl) ethyltriethoxysilane, 2,3-epoxypropyltrimethoxysilane, and 2,3 -Epoxypropyltriethoxy Run.

(Polyfunctional epoxy compound)
The polyfunctional epoxy compound which is a glycidyl etherified product of a polyphenol compound is not particularly limited, and specifically, bisphenol A, bisphenol F, bisphenol S, 4,4′-biphenol, tetramethylbisphenol A, dimethyl bisphenol A, tetramethylbisphenol F, dimethylbisphenol F, tetramethylbisphenol S, dimethylbisphenol S, tetramethyl-4,4′-biphenol, dimethyl-4,4′-biphenol, 1- (4-hydroxyphenyl) -2- [4- (1,1-bis- (4-hydroxyphenyl) ethyl) phenyl] propane, 2,2′-methylene-bis (4-methyl-6-tert-butylphenol), 4,4′-butylidene-bis (3-Methyl-6-tert-butylphenol ), Trishydroxyphenylmethane, resorcinol, hydroquinone, 2,6-di (t-butyl) hydroquinone, pyrogallol, phenols having a diisopropylidene skeleton, fluorene skeletons such as 1,1-di (4-hydroxyphenyl) fluorene And glycidyl etherified products of polyphenol compounds such as phenolized polybutadiene.

  Among these, a polyfunctional epoxy compound which is a glycidyl etherified product of a phenol having a bisphenol A skeleton or a bisphenol F skeleton is preferable because the production is easy, the cost of the composition is suppressed, and the economy is excellent.

  Typical examples of polyfunctional epoxy compounds that are glycidyl etherified products of phenols having a bisphenol skeleton are shown below.

式中、ｎは１以上の数を示す。

In the formula, n represents a number of 1 or more.

(Alicyclic epoxy compound)
The alicyclic epoxy compound is not particularly limited as long as it is an epoxy compound having an alicyclic epoxy structure. For example, the alicyclic epoxy compound is selected from epoxy compounds having a cyclohexene oxide group, a tricyclodecene oxide group, a cyclopentene oxide group, or the like. Can be.

  Specific examples of the alicyclic epoxy compound include 3,4-epoxycyclohexenylmethyl-3 ′, 4′-opepoxycyclohexene carboxylate, 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexanecarboxylate, 3 , 4-epoxycyclohexyloctyl-3,4-epoxycyclohexanecarboxylate, 2- (3,4-epoxycyclohexyl-5,5-spiro-3,4-epoxy) cyclohexane-meta-dioxane, bis (3,4- Epoxycyclohexylmethyl) adipate, vinylcyclohexene dioxide, bis (3,4-epoxy-6-methylcyclohexylmethyl) adipate, 3,4-epoxy-6-methylcyclohexyl-3,4-epoxy-6-methylcyclohexanecarboxylate , Methylene bis (3,4-epoxycyclohexane), dicyclopentadiene diepoxide, ethylene glycol di (3,4-epoxycyclohexylmethyl) ether, ethylene bis (3,4-epoxycyclohexanecarboxylate), and 1,2, 8,9-diepoxy limonene. Other polyfunctional alicyclic epoxy compounds include 1,2-epoxy-4- (2-oxiranyl) cyclohexene or 1,2-thioepoxy-4- (2,2-bis (hydroxymethyl) -1-butanol. 2-oxiranyl) cyclohexene adduct and the like.

  Typical examples of the alicyclic epoxy compound are shown below.

(Polyfunctional epoxy compound that is glycidyl etherified product of novolak compound)
The polyfunctional epoxy compound that is a glycidyl etherified product of a novolak compound is not particularly limited, and examples thereof include phenol, cresols, ethylphenols, butylphenols, octylphenols, bisphenol A, bisphenol F, bisphenol S, and naphthol. Glycidyl of various novolak compounds such as novolak compounds made from various phenols such as phenols, xylylene skeleton-containing phenol novolak compounds, dicyclopentadiene skeleton-containing phenol novolac compounds, biphenyl skeleton-containing phenol novolak compounds, and fluorene skeleton-containing phenol novolak compounds It can be selected from etherified compounds.

  Among these, a glycidyl etherified product of a novolak compound using phenol or cresol as a raw material is preferable because it is easy to produce, the cost of the composition is suppressed, and the cost is excellent.

  The typical example of the polyfunctional epoxy compound which is a glycidyl etherification product of a novolak compound is shown below.

式中、ｎは１以上の数を示す。

In the formula, n represents a number of 1 or more.

(Nuclear hydride of aromatic epoxy compound)
The nuclear hydride of the aromatic epoxy compound is not particularly limited. For example, a thioglycidyl etherified product of a phenol compound (bisphenol A, bisphenol F, bisphenol S, 4,4′-biphenol, etc.) or various phenols ( Phenol, cresols, ethylphenols, butylphenols, octylphenols, bisphenol A, bisphenol F, bisphenol S, naphthols, etc.) and hydrogenated glycidyl ethers of novolak compounds Can be chosen from.

(Heterocyclic epoxy compounds)
The heterocyclic epoxy compound is not particularly limited, and may be selected from, for example, a heterocyclic epoxy compound having a heterocyclic ring such as an isocyanuric ring and a hydantoin ring.

(Glycidyl ester epoxy compound)
The glycidyl ester epoxy compound is not particularly limited, and may be selected from epoxy compounds derived from carboxylic acid compounds such as hexahydrophthalic acid diglycidyl ester and tetrahydrophthalic acid diglycidyl ester.

(Glycidylamine epoxy compound)
The glycidylamine-based epoxy compound is not particularly limited, and is selected from, for example, epoxy compounds obtained by glycidylating amines such as aniline, toluidine, p-phenylenediamine, m-phenylenediamine, diaminodiphenylmethane derivatives and diaminomethylbenzene derivatives. Can be.

(Epoxy compound obtained by glycidylation of halogenated phenols)
Epoxy compounds obtained by glycidylation of halogenated phenols are not particularly limited. For example, brominated bisphenol A, brominated bisphenol F, brominated bisphenol S, brominated phenol novolac, brominated cresol novolac, chlorinated bisphenol. S and epoxy compounds obtained by glycidyl etherification of halogenated phenols such as chlorinated bisphenol A can be selected.

(Polyfunctional aliphatic epoxy compound)
The polyfunctional aliphatic epoxy compound is not particularly limited, and specifically includes 1,1-bisepoxymethane, 1-epoxy-1- (2,3-epoxypropyl) methane, 1,1- Bis (2,3-epoxypropyl) methane, 1-epoxy-1- (2,3-epoxypropyl) ethane, 1,2-bis (2,3-epoxypropyl) ethane, 1-epoxy-3- (2 , 3-epoxypropyl) butane, 1,3-bis (2,3-epoxypropyl) propane, 1-epoxy-4- (2,3-epoxypropyl) pentane, 1,4-bis (2,3-epoxy) Propyl) butane, 1-epoxy-5- (2,3-epoxypropyl) hexane, 1-epoxy-2- (γ-epoxybutylthio) ethane, 1-epoxy-2- [2- (γ-epoxybutyl) Thio) ethylthio] ethane, tetrakis (2,3-epoxypropyl) methane, 1,1,1-tris (2,3-epoxypropyl) propane, 1,1,3-tris (2,3-epoxypropyl)- 2-thiapropane, 1,2,4,5-bis (2,3-epoxypropyl) -3-thiapentane, 1,3 or 1,4-bisepoxycyclohexane, 1,3 or 1,4-bis (2, 3-epoxypropyl) cyclohexane, 2,5-bisepoxy-1,4-dithiane, 2,5-bis (2,3-epoxypropyl) -1,4-dithiane, 4-epoxy-1,2-cyclohexene oxide 2,2-bis [4-epoxycyclohexyl] propane, 2,2-bis [4- (2,3-epoxypropyl) cyclohexyl] propane, bis [4-epoxy Chlohexyl] methane, bis [4- (2,3-epoxypropyl) cyclohexyl] methane, bis [4- (2,3-epoxypropyl) cyclohexyl] sulfide, bis [4-epoxycyclohexyl] sulfide, bis (2,3 -Epoxypropyl) ether, bis [(2,3-epoxypropyl) oxy] methane, 1,2-bis [(2,3-epoxypropyl) oxy] ethane, 1,3-bis [(2,3-epoxy) Propyl) oxy] propane, 1,2-bis [(2,3-epoxypropyl) oxy] propane, 1-[(2,3-epoxypropyl) oxy] -2-[(2,3-epoxypropyl) oxy Methyl] propane, 1,4-bis [(2,3-epoxypropyl) oxy] butane, 1,3-bis [(2,3-epoxypropylene ) Oxy] butane, 1-[(2,3-epoxypropyl) oxy] -3-[(2,3-epoxypropyl) oxymethyl] butane, 1,5-bis [(2,3-epoxypropyl) oxy ] Pentane, 1-[(2,3-epoxypropyl) oxy] -4-[(2,3-epoxypropyl) oxymethyl] pentane, 1,6-bis [(2,3-epoxypropyl) oxy] hexane , 1-[(2,3-epoxypropyl) oxy] -5-[(2,3-epoxypropyl) oxymethyl] hexane, 1-[(2,3-epoxypropyl) oxy] -2-{[2 -(2,3-epoxypropyl) oxyethyl) oxy] ethane, 1-[(2,3-epoxypropyl) oxy) -2-{[2- (2- (2,3-epoxypropyl) oxyethyl) oxye L] oxy} ethane, tetrakis [(2,3-epoxypropyl) oxymethyl] methane, 1,1,1-tris [(2,3-epoxypropyl) oxymethyl) propane, 1,5-bis [(2 , 3-epoxypropyl) oxy] -2-[(2,3-epoxypropyl) oxymethyl] -3-thiapentane, 1,5-bis [(2,3-epoxypropyl) oxy] -2,4-bis [(2,3-epoxypropyl) oxymethyl] -3-thiapentane;

  1-[(2,3-epoxypropyl) oxy] -2,2-bis [(2,3-epoxypropyl) oxymethyl] -4-thiahexane, 1,5,6-tris [(2,3-epoxy Propyl) oxy] -4-[(2,3-epoxypropyl) oxymethyl] -3-thiahexane, 1,8-bis [(2,3-epoxypropyl) oxy] -4-[(2,3-epoxy Propyl) oxymethyl] -3,6-dithiaoctane, 1,8-bis [(2,3-epoxypropyl) oxy] -4,5-bis [(2,3-epoxypropyl) oxymethyl] -3,6 Dithiaoctane, 1,8-bis [(2,3-epoxypropyl) oxy] -4,4-bis [(2,3-epoxypropyl) oxymethyl] -3,6-dithiaoctane, 1,8-bis [ (2,3-D Xylpropyl) oxy] -2,4,5-tris [(2,3-epoxypropyl) oxymethyl] -3,6-dithiaoctane, 1,8-bis [(2,3-epoxypropyl) oxy] -2, 5-bis [(2,3-epoxypropyl) oxymethyl] -3,6-dithiaoctane, 1,9-bis [(2,3-epoxypropyl) oxy] -5-[(2,3-epoxypropyl) Oxymethyl] -5-{[2- (2,3-epoxypropyl) oxyethyl] oxymethyl} -3,7-dithianonane, 1,10-bis [(2,3-epoxypropyl) oxy] -5,6 -Bis {[2- (2,3-epoxypropyl) oxyethyl] oxy} -3,6,9-trithiadecane, 1,11-bis [(2,3-epoxypropyl) oxy] -4,8-bis [ (2,3-epoxy Propyl) oxymethyl] -3,6,9-trithiaundecane, 1,11-bis [(2,3-epoxypropyl) oxy] -5,7-bis [(2,3-epoxypropyl) oxymethyl] -3,6,9-trithiaundecane, 1,11-bis [(2,3-epoxypropyl) oxy] -5,7-{[2- (2,3-epoxypropyl) oxyethyl] oxymethyl}- 3,6,9-trithiaundecane, 1,11-bis [(2,3-epoxypropyl) oxy] -4,7-bis [(2,3-epoxypropyl) oxymethyl] -3,6,9 -Trithiaundecane, 1,3 or 1,4-bis [(2,3-epoxypropyl) oxy] cyclohexane, 1,3 or 1,4-bis [(2,3-epoxypropyl) oxymethyl] cyclohexane, Screw {4-[(2,3-D Poxypropyl) oxy] cyclohexyl} methane, 2,2-bis {4-[(2,3-epoxypropyl) oxy] cyclohexyl} propane, bis {4-[(2,3-epoxypropyl) oxy] cyclohexyl} sulfide 2,5-bis [(2,3-epoxypropyl) oxymethyl] -1,4-dithiane, 2,5-bis [(2,3-epoxypropyl) oxyethyloxymethyl] -1,4-dithiane Bis (2,3-epoxypropyl) sulfide, bis (2,3-epoxypropyl) disulfide, bis (2,3-epoxypropyl) trisulfide, bis [(2,3-epoxypropyl) thio] methane, bis [(2,3-epoxypropyl) dithio] methane, bis [(2,3-epoxypropyl) dithio] ethane, bis [(2,3-epoxypropyl) dithio Ethyl] sulfide, bis [(2,3-epoxypropyl) dithioethyl] disulfide, 1,2-bis [(2,3-epoxypropyl) thio] ethane, 1,3-bis [(2,3-epoxypropyl) Thio] propane, 1,2-bis [(2,3-epoxypropyl) thio] propane, 1-[(2,3-epoxypropyl) thio] -2-[(2,3-epoxypropyl) thiomethyl] propane 1,4-bis [(2,3-epoxypropyl) thio] butane, 1,3-bis [(2,3-epoxypropyl) thio] butane, 1-[(2,3-epoxypropyl) thio] -3-[(2,3-epoxypropyl) thiomethyl] butane, 1,5-bis [(2,3-epoxypropyl) thio] pentane, 1-[(2,3-epoxypropyl) thio] -4- [(2,3-epoxypropyl) thiome Til] pentane, 1,6-bis [(2,3-epoxypropyl) thio] hexane, 1-[(2,3-epoxypropyl) thio] -5-[(2,3-epoxypropyl) thiomethyl] hexane , 1-[(2,3-epoxypropyl) thio] -2-{[2- (2,3-epoxypropyl) thioethyl] thio} ethane, 1-[(2,3-epoxypropyl) thio] -2 -{[2- (2- (2,3-epoxypropyl) thioethyl) thioethyl] thio} ethane, tetrakis [(2,3-epoxypropyl) thiomethyl] methane, tetrakis [(2,3-epoxypropyl) dithiomethyl] Methane, 1,1,1-tris [(2,3-epoxypropyl) thiomethyl] propane, 1,2,3-tris [(2,3-epoxypropyl) dithio] propane, 1,5-bis [(2 , 3-epoxy Propyl) thio] -2-[(2,3-epoxypropyl) thiomethyl] -3-thiapentane, 1,5-bis [(2,3-epoxypropyl) thio] -2,4-bis [(2,3 -Epoxypropyl) thiomethyl] -3-thiapentane;

  1,6-bis [(2,3-epoxypropyl) dithiomethyl] -2-[(2,3-epoxypropyl) dithioethylthio] -4-thiahexane, 1-[(2,3-epoxypropyl) thio] -2,2-bis [(2,3-epoxypropyl) thiomethyl] -4-thiahexane, 1,5,6-tris [(2,3-epoxypropyl) thio] -4-[(2,3-epoxy Propyl) thiomethyl] -3-thiahexane, 1,8-bis [(2,3-epoxypropyl) thio] -4-[(2,3-epoxypropyl) thiomethyl] -3,6-dithiaoctane, 1,8- Bis [(2,3-epoxypropyl) thio] -4,5-bis [(2,3-epoxypropyl) thiomethyl] -3,6-dithiaoctane, 1,8-bis [(2,3-epoxypropyl) Thio] -4,4-bis [(2,3-et Xylpropyl) thiomethyl] -3,6-dithiaoctane, 1,8-bis [(2,3-epoxypropyl) thio] -2,4,5-tris [(2,3-epoxypropyl) thiomethyl] -3,6 Dithiaoctane, 1,8-bis [(2,3-epoxypropyl) thio] -2,5-bis [(2,3-epoxypropyl) thiomethyl] -3,6-dithiaoctane, 1,9-bis [( 2,3-epoxypropyl) thio] -5-[(2,3-epoxypropyl) thiomethyl] -5-{[2- (2,3-epoxypropyl) thioethyl] thiomethyl} -3,7-dithianonane, 1 , 10-bis [(2,3-epoxypropyl) thio] -5,6-bis {[2- (2,3-epoxypropyl) thioethyl] thio} -3,6,9-trithiadecane, 1,11- Bis [(2,3-epoxypropy ) Thio] -4,8-bis [(2,3-epoxypropyl) thiomethyl] -3,6,9-trithiaundecane, 1,11-bis [(2,3-epoxypropyl) thio] -5, 7-bis [(2,3-epoxypropyl) thiomethyl] -3,6,9-trithiaundecane, 1,11-bis [(2,3-epoxypropyl) thio] -5,7-{[2- (2,3-epoxypropyl) thioethyl] thiomethyl} -3,6,9-trithiaundecane, 1,11-bis [(2,3-epoxypropyl) thio] -4,7-bis [(2,3 -Epoxypropyl) thiomethyl] -3,6,9-trithiaundecane, tetra {2-[(2,3-epoxypropyl) thio] acetylmethyl} methane, 1,1,1-tri {2-[(2 , 3-epoxypropyl) thio] acetylmethyl} propane, tetra { -[(2,3-epoxypropyl) thiomethyl] acetylmethyl} methane, 1,1,1-tri {2-[(2,3-epoxypropyl) thiomethyl] acetylmethyl} propane, 1,3 or 1,4 -Bis [(2,3-epoxypropyl) thio] cyclohexane, 1,3 or 1,4-bis [(2,3-epoxypropyl) thiomethyl] cyclohexane, 2,5-bis [(2,3-epoxypropyl) ) Thiomethyl] -1,4-dithiane, 2,5-bis [(2,3-epoxypropyl) dithiomethyl] -1,4-dithiane, 2,5-bis [(2,3-epoxypropyl) thioethylthio Methyl] -1,4-dithiane, bis {4-[(2,3-epoxypropyl) thio] cyclohexyl} methane, 2,2-bis {4-[(2,3-epoxypropyl) thio] cyclohexyl} propane Bis {4-[(2,3-epoxypropyl) thio] cyclohexyl} sulfide, 2,2-bis {4-[(2,3-epoxypropyl) thio] cyclohexyl} propane, bis {4-[(2, 3-epoxypropyl) thio] cyclohexyl} sulfide.

  Among the above, since it is easy to produce, the cost as a composition can be suppressed, and it is excellent in economic efficiency. Therefore, the polyfunctional aliphatic epoxy compound is at least one compound selected from the following group. It is preferable.

  Bis [(2,3-epoxypropyl) oxy] methane, 1,2-bis [(2,3-epoxypropyl) oxy] ethane, 1,3-bis [(2,3-epoxypropyl) oxy] propane, 1,2-bis [(2,3-epoxypropyl) oxy] propane, 1-[(2,3-epoxypropyl) oxy] -2-[(2,3-epoxypropyl) methyl] propane, 1,4 -Bis [(2,3-epoxypropyl) oxy] butane, 1,3-bis [(2,3-epoxypropyl) oxy] butane, 1-[(2,3-epoxypropyl) oxy] -3- [ (2,3-epoxypropyl) methyl] butane, 1,6-bis [(2,3-epoxypropyl) oxy] hexane, 1-[(2,3-epoxypropyl) oxy] -5-[(2, 3-epoxypropyl) oxymethyl] hexane, 1- [ 2,3-epoxypropyl) oxy] -2-{[2- (2,3-epoxypropyl) oxyethyl] oxy} ethane, 1-[(2,3-epoxypropyl) oxy] -2-{[2- (2- (2,3-epoxypropyl) oxyethyl) oxyethyl] oxy} ethane, tetrakis [(2,3-epoxypropyl) oxymethyl] methane, 1,1,1-tris [(2,3-epoxypropyl) Oxymethyl] propane, 1-[(2,3-epoxypropyl) oxy] -2,2-bis [(2,3-epoxypropyl) oxymethyl] -4-thiahexane, 1,5,6-tris [( 2,3-epoxypropyl) oxy] -4-[(2,3-epoxypropyl) oxymethyl] -3-thiahexane;

  1,8-bis [(2,3-epoxypropyl) oxy] -4-[(2,3-epoxypropyl) oxymethyl] -3,6-dithiaoctane, 1,8-bis [(2,3-epoxy Propyl) oxy] -4,5-bis [(2,3-epoxypropyl) oxymethyl] -3,6-dithiaoctane, 1,8-bis [(2,3-epoxypropyl) oxy] -4,4- Bis [(2,3-epoxypropyl) oxymethyl] -3,6-dithiaoctane, 1,8-bis [(2,3-epoxypropyl) oxy] -2,4,5-tris [(2,3- Epoxypropyl) oxymethyl] -3,6-dithiaoctane, 1,8-bis [(2,3-epoxypropyl) oxy] -2,5-bis [(2,3-epoxypropyl) oxymethyl] -3, 6-dithiaoctane, 1,3 or 1,4-bis [ 2,3-epoxypropyl) oxy] cyclohexane, 1,3 or 1,4-bis [(2,3-epoxypropyl) oxymethyl] cyclohexane, bis {4-[(2,3-epoxypropyl) oxy] cyclohexyl } Methane, 2,2-bis {4-[(2,3-epoxypropyl) oxy] cyclohexyl} propane, bis {4-[(2,3-epoxypropyl) oxy] cyclohexyl} sulfide, 2,5-bis [(2,3-epoxypropyl) oxymethyl] -1,4-dithiane, 2,5-bis [(2,3-epoxypropyl) oxyethyloxymethyl] -1,4-dithiane, bis (2,3 -Epoxypropyl) sulfide, bis (2,3-epoxypropyl) disulfide, bis [(2,3-epoxypropyl) thio] methane, bis [(2,3-epoxypro L) dithio] methane, bis [(2,3-epoxypropyl) dithio] ethane, bis [(2,3-epoxypropyl) dithioethyl] sulfide, bis [(2,3-epoxypropyl) dithioethyl] disulfide, 1, 2-bis [(2,3-epoxypropyl) thio] ethane, 1,3-bis [(2,3-epoxypropyl) thio] propane, 1,2-bis [(2,3-epoxypropyl) thio] propane;

  1-[(2,3-epoxypropyl) thio] -2-[(2,3-epoxypropyl) thiomethyl] propane, 1,4-bis [(2,3-epoxypropyl) thio] butane, 1,3 -Bis [(2,3-epoxypropyl) thio] butane, 1-[(2,3-epoxypropyl) thio] -3-[(2,3-epoxypropyl) thiomethyl] butane, 1,6-bis [ (2,3-epoxypropyl) thio] hexane, 1-[(2,3-epoxypropyl) thio] -5-[(2,3-epoxypropyl) thiomethyl] hexane, 1-[(2,3-epoxy Propyl) thio] -2-{[2- (2,3-epoxypropyl) thioethyl] thio} ethane, 1-[(2,3-epoxypropyl) thio] -2-{[2- (2- (2 , 3-epoxypropyl) thioethyl) thioethyl] thio} ethane, te Lakis [(2,3-epoxypropyl) thiomethyl] methane, tetrakis [(2,3-epoxypropyl) dithiomethyl] methane, 1,1,1-tris [(2,3-epoxypropyl) thiomethyl] propane, 1, 2,3-tris [(2,3-epoxypropyl) dithio] propane, 1,6-bis [(2,3-epoxypropyl) dithiomethyl] -2-[(2,3-epoxypropyl) dithioethylthio] -4-thiahexane, 1-[(2,3-epoxypropyl) thio] -2,2-bis [(2,3-epoxypropyl) thiomethyl] -4-thiahexane, 1,5,6-tris [(2 , 3-epoxypropyl) thio] -4-[(2,3-epoxypropyl) thiomethyl] -3-thiahexane;

  1,8-bis [(2,3-epoxypropyl) thio] -4-[(2,3-epoxypropyl) thiomethyl] -3,6-dithiaoctane, 1,8-bis [(2,3-epoxypropyl) ) Thio] -4,5-bis [(2,3-epoxypropyl) thiomethyl] -3,6-dithiaoctane, 1,8-bis [(2,3-epoxypropyl) thio] -4,4-bis [ (2,3-epoxypropyl) thiomethyl] -3,6-dithiaoctane, 1,8-bis [(2,3-epoxypropyl) thio] -2,4,5-tris [(2,3-epoxypropyl) Thiomethyl] -3,6-dithiaoctane, 1,8-bis [(2,3-epoxypropyl) thio] -2,5-bis [(2,3-epoxypropyl) thiomethyl] -3,6-dithiaoctane, tetra {2-[(2,3-epoxypropyl) thio] Cetylmethyl} methane, 1,1,1-tri {2-[(2,3-epoxypropyl) thio] acetylmethyl} propane, tetra {2-[(2,3-epoxypropyl) thiomethyl] acetylmethyl} methane, 1,1,1-tri {2-[(2,3-epoxypropyl) thiomethyl] acetylmethyl} propane, 1,3 or 1,4-bis [(2,3-epoxypropyl) thio] cyclohexane, 1, 3 or 1,4-bis [(2,3-epoxypropyl) thiomethyl] cyclohexane, 2,5-bis [(2,3-epoxypropyl) thiomethyl] -1,4-dithiane, 2,5-bis [( 2,3-epoxypropyl) dithiomethyl] -1,4-dithiane, 2,5-bis [(2,3-epoxypropyl) thioethylthiomethyl] -1,4-dithiane, bis {4-[(2, 3-epoxyp Pyr) thio] cyclohexyl} methane, 2,2-bis {4-[(2,3-epoxypropyl) thio] cyclohexyl} propane, bis {4-[(2,3-epoxypropyl) thio] cyclohexyl} sulfide, 2,2-bis {4-[(2,3-epoxypropyl) thio] cyclohexyl} propane, bis {4-[(2,3-epoxypropyl) thio] cyclohexyl} sulfide.

(Silicone compound having an epoxy group in the molecule)
The silicone compound which has an epoxy group in a molecule | numerator is not specifically limited, For example, it may be chosen from the compound represented by following formula (7).
(R ₄₀ R ₄₁ R ₄₂ SiO _1/2 ) _a (R ₄₃ R ₄₄ SiO _2/2 ) _b (R ₄₅ SiO _3/2 ) _c (SiO _4/2 ) _d (7)

In the formula (7), a, b, c and d are numerical values satisfying a + b + c + d = 1.0, and 0 ≦ a / (a + b + c + d) ≦ 1, 0 ≦ b / (a + b + c + d) ≦ 1, 0 ≦ c / (A + b + c + d) ≦ 1 and 0 ≦ d / (a + b + c + d) <1. At least one of R ₄₀ to R ₄₅ represents a group containing an epoxy group, other _R 40 _{to R 45} represents a linear or branched hydrocarbon group or the hydrocarbon having 1 to 8 carbon atoms The group represents a fluorinated group. These may be the same as or different from each other.

(Hexogenous polymerizable functional group-containing epoxy compound)
The heteropolymerizable functional group-containing epoxy compound is not particularly limited, and may be selected from, for example, compounds represented by the following formula (8).

In the above formula (8), R _{50 to} R ₅₂ represent a substituted or unsubstituted chain, branched, or cyclic aliphatic or aromatic hydrocarbon group that may be thiated. m, n, o and p each independently represent a number of 1 or more. X represents an epoxy group. When Y represents a single type of polymerizable functional group, a cyclic ether structure, a cyclic thioether structure, a lactone structure, a cyclic carbonate structure, and a sulfur-containing analog structure thereof, a cyclic acetal structure, and a sulfur-containing analog structure thereof, a cyclic amine structure , A structure selected from a cyclic imino ether structure, a lactam structure, a cyclic thiourea structure, a cyclic phosphinate structure, a cyclic phosphonite structure, a cyclic phosphite structure, a vinyl structure, an allyl structure, a (meth) acrylic structure, and a cycloalkane structure. When a plurality of types of polymerizable functional groups are shown, at least two types of structures selected from the above group are shown.

The mixing ratio of (A) carbonate compound and (B) boron trihalide can be represented by an index α calculated by the following formula (2).
Index α = αc / αb (2)
αc: (A) amount of carbonate group of carbonate compound (mol)
αb: (B) Boron trihalide substance amount (mol)

  The index α indicates that all of (B) boron trihalide contained in the composition forms a compound (complex) via a coordination bond with (A) a carbonate compound, and the composition is prepared at room temperature. At this time, since the polymerization of the epoxy compound (C) can be further suppressed and the stability of the composition tends to be further improved, it is preferably 1 or more. From the same viewpoint, the index α is more preferably 1.5 or more.

  In the case where (A) the carbonate compound and (B) boron trihalide have a possibility that the compound through the coordination bond may be altered, the index α should be 2 or more in order to increase the stability of the compound. Is preferred.

  The index α is preferably 1000 or less because the residual α of the epoxy group contained in the (C) epoxy compound tends to be further suppressed when the composition is polymerized. From the same viewpoint, the index α is more preferably 500 or less. When the step of polymerizing the composition and removing the (A) carbonate compound contained in the resulting polymer is required, the cost required for the step can be further suppressed, and the economy tends to be superior. The index α is more preferably 100 or less.

  The index α is preferably 10 or less because (C) the epoxy compound tends to be more transparent after polymerization of the epoxy compound. From the same viewpoint, the index α is more preferably 5 or less.

  (B) Regarding the mixing ratio of boron trihalide and (C) epoxy compound, (B) the amount of boron trihalide (mol), and (C) the amount of epoxy group contained in the epoxy compound (mol) The ratio is preferably 1:10 to 1: 100000.

  (B) When the substance amount (mol) of boron trihalide is 1, (C) The substance amount (mol) of the epoxy group contained in the epoxy compound is 10 or more. In doing so, (C) the polymerization of the epoxy compound can be further suppressed, and the stability of the composition tends to be further improved, which is preferable. (B) When the substance amount (mol) of boron trihalide is 1, (C) the substance amount (mol) of the epoxy group contained in the epoxy compound is 20 or more. After that, it is more preferable because the transparency of the resulting polymer tends to be further improved. From the same viewpoint, when the substance amount (mol) of (B) boron trihalide is 1, it is more preferable that the substance amount (mol) of the epoxy group contained in the (C) epoxy compound is 50 or more. .

  (B) When the substance amount (mol) of boron trihalide is set to 1, (A) the carbonate compound that the substance amount (mol) of the epoxy group contained in the epoxy compound is 50 or more; Depending on the combination of (B) boron trihalide and (C) epoxy compound, the transparency of the obtained transparent polymer may be maintained over a long period of time, which may be preferable. From the same viewpoint, when the substance amount (mol) of (B) boron trihalide is 1, (C) the substance amount (mol) of the epoxy group contained in the epoxy compound is more preferably 100 or more. More preferably, it is 200 or more.

  (B) When the substance amount (mol) of boron trihalide is 1, (C) the substance amount (mol) of the epoxy group contained in the epoxy compound is 100000 or less, when polymerizing the composition, (C) Since there exists a tendency which can suppress the residual of the epoxy group contained in an epoxy compound more, it is preferable. (B) When the substance amount (mol) of boron trihalide is set to 1, the substance amount (mol) of the epoxy group contained in the (C) epoxy compound is 20000 or less, and (C) the epoxy compound is polymerized. After that, the transparency of the resulting polymer tends to be further improved, which is more preferable. From the same viewpoint, when the amount (mol) of (B) is 1, it is more preferable that the amount (mol) of the epoxy group contained in (C) the epoxy compound is 10,000 or less.

The mixing ratio of (B) boron trihalide and (C) epoxy compound can also be represented by the following formula (9).
Index β = αb / αep × 100 (9)
αb: (B) Boron trihalide substance amount (mol)
αep: (C) the amount of epoxy group contained in the epoxy compound (mol)

When the ratio of (B) the amount of boron trihalide (mol) to (C) the amount of epoxy group contained in the epoxy compound (mol) is 1:10, the index β = 10.
(B) When the ratio of the substance amount (mol) of boron trihalide and the substance amount (mol) of the epoxy group contained in (C) the epoxy compound is 1:20, the index β = 5.
When the ratio of the amount of (B) boron trihalide (mol) to the amount of (C) epoxy group contained in the epoxy compound is 1:50, the index β = 2.
When the ratio of (B) the amount of boron trihalide (mol) to (C) the amount of epoxy group contained in the epoxy compound (mol) is 1: 100, the index β = 1.
(B) When the ratio of the substance amount (mol) of boron trihalide and the substance amount (mol) of the epoxy group contained in (C) the epoxy compound is 1: 200, the index β = 0.5. .
(B) When the ratio of the substance amount (mol) of boron trihalide and the substance amount (mol) of the epoxy group contained in (C) the epoxy compound is 1: 100000, the index β = 0.001. .
(B) When the ratio of the substance amount (mol) of boron trihalide and the substance amount (mol) of the epoxy group contained in (C) the epoxy compound is 1: 20000, the index β = 0.005. .
(B) When the ratio of the substance amount (mol) of boron trihalide and the substance amount (mol) of the epoxy group contained in the epoxy compound (C) is 1: 10000, the index β = 0.01. .

  The method for preparing the composition is not particularly limited as long as it is a generally used method, but (A) a carbonate compound, (B) a boron trihalide and (C) an epoxy compound are simultaneously added, A method of adding two components arbitrarily selected from A) carbonate compound, (B) boron trihalide and (C) epoxy compound and then adding to the remaining components or adding the remaining components. . Among these, since the composition can be stably prepared and the stability as the composition tends to be excellent, after preparing a mixture containing (A) a carbonate compound and (B) boron trihalide, A method of adding (C) an epoxy compound or (C) adding an epoxy compound is preferable.

  A method for preparing a mixture containing (A) a carbonate compound and (B) boron trihalide is not particularly limited as long as it is a generally used method, but (A) a carbonate compound and (B) three Examples thereof include a method of directly reacting with a boron halide, a method of reacting (A) a carbonate compound with (B) a compound containing boron trihalide, and the like. Among these, the method of reacting (A) a carbonate compound and (B) a compound containing boron trihalide improves the handleability of the compound containing (B) boron trihalide, and It is more preferable because preparation tends to be easy.

  The temperature for preparing the mixture containing (A) the carbonate compound and (B) boron trihalide is not particularly limited, and is performed at a general usable temperature, but is preferably −80 to 100 ° C. . The temperature at which the mixture is prepared need not be constant, and may be changed midway.

  Since the time required for forming a coordination bond between (A) the carbonate compound and (B) boron trihalide tends to be shortened, the temperature for preparing the mixture is preferably −80 ° C. or higher. From the same viewpoint, the temperature for preparing the mixture is more preferably −60 ° C. or higher.

  Depending on the selection of the raw material, the raw material is solidified, and if there is a possibility that formation of a compound via a coordination bond consisting of (A) a carbonate compound and (B) boron trihalide may be hindered, solidification is suppressed. Therefore, it is preferable that the temperature for preparing the mixture is equal to or higher than the freezing point of the raw material.

  When the compound via a coordination bond comprising (A) a carbonate compound and (B) boron trihalide is unstable, the temperature at which the mixture is prepared is preferably 100 ° C. or lower. From the same viewpoint, the temperature for preparing the mixture is more preferably 80 ° C. or lower.

  Depending on the choice of raw materials, if the raw materials are volatilized and the mixing ratio of (A) carbonate compound and (B) may deviate from the desired ratio, the temperature at which the mixture is prepared should be adjusted to suppress volatilization. It is preferable to make it below the boiling point. It is also an effective means to suppress the volatilization of the raw material by setting the pressure for preparing the mixture to a desired pressure equal to or higher than atmospheric pressure.

  The atmosphere for preparing the mixture containing (A) a carbonate compound and (B) boron trihalide is not particularly limited as long as it is a commonly used atmosphere, but is usually an air atmosphere, a nitrogen atmosphere, and argon. An atmosphere or the like is used. Among these, (B) a nitrogen atmosphere and an argon atmosphere are preferable because boron trihalide tends to be handled stably. Moreover, since it exists in the tendency which is excellent in economical efficiency, nitrogen atmosphere is still more preferable.

  The pressure for preparing the mixture containing (A) the carbonate compound and (B) boron trihalide is not particularly limited, and the reaction is usually performed under atmospheric pressure. However, when the vapor pressure of the (A) carbonate compound in the standard state is low and the (A) carbonate compound may volatilize during the reaction, it is an effective means to pressurize at atmospheric pressure or higher. It is.

  When preparing a mixture containing (A) a carbonate compound and (B) boron trihalide, if (A) the carbonate compound is a solid, use a compound capable of dissolving (A) the carbonate compound. Thus, since a uniform mixture can be easily obtained, it may be an effective means.

  (A) Although the compound which can melt | dissolve a carbonate compound will not be specifically limited if it is generally used, As a specific example, n-pentane, n-hexane, isohexane, n-heptane, n-octane, Saturated hydrocarbon compounds such as isooctane, n-nonane, n-decane, cyclopentane, cyclohexane, cycloheptane and cyclooctane, and aromatic carbonization such as benzene, toluene, xylene, ethylbenzene, diethylbenzene, isopropylbenzene, naphthalene, tetralin and biphenyl Hydrogen compound, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichloroethane, tetrachloroethane, pentachloroethane, hexachloroethane, dichloroethylene, trichloroethylene, tetrachloroethylene, dichloropropane, Halogenated hydrocarbon compounds such as lichloropropane, isopropyl chloride, butyl chloride, hexyl chloride, chlorobenzene, dichlorobenzene, trichlorobenzene, chlorotoluene and chloronaphthalene, methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, hexanol , Alcohols such as heptanol, octanol, nonanol, decanol, undecanol, dodecanol, cyclohexanol and benzyl alcohol, acetone, methylacetone, ethylmethylketone, methylpropylketone, methylbutylketone, methylisobutylketone, methylhexylketone, diethylketone , Ethyl butyl ketone, dipropyl ketone, diisobutyl ketone and cyclohexanone Ethyl acetate, propyl acetate, butyl acetate, isobutyl acetate, pentyl acetate, hexyl acetate, octyl acetate, cyclohexyl acetate, methyl propionate, ethyl propionate, butyl propionate, methyl benzoate, ethyl benzoate, benzoate And esters such as propyl acid, butyl benzoate and benzyl benzoate. These compounds may be used alone or in combination.

  Among these, since (B) it is highly stable with respect to boron trihalide and tends to prepare a mixture stably, n-pentane, n-hexane, isohexane, n-heptane, n-octane, Saturated hydrocarbon compounds such as isooctane, n-nonane, n-decane, cyclopentane, cyclohexane, cycloheptane and cyclooctane, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichloroethane, tetrachloroethane, pentachloroethane, hexachloroethane, Dichloroethylene, trichlorethylene, tetrachloroethylene, dichloropropane, trichloropropane, isopropyl chloride, butyl chloride, hexyl chloride, chlorobenzene, dichlorobenzene, trichlorobenzene, chlorotoluene and chloronaphthalene Halogenated hydrocarbon compounds are preferred.

  When preparing a mixture containing (A) a carbonate compound and (B) boron trihalide, (A) a compound capable of dissolving the carbonate compound and (B) a compound containing boron trihalide are used. In addition, a mixture other than the desired compound may be contained in the mixture. In such a case, by performing distillation, a desired compound can be obtained as a distillate or as a distillation residue. The distillation temperature and distillation pressure are appropriately set depending on the boiling point of the compound separated by distillation.

  The distillation temperature is preferably 100 ° C. or lower, more preferably 80 ° C. or lower, and further preferably 60 ° C. or lower. By setting the distillation temperature to 100 ° C. or lower, decomposition of the compound via a coordination bond composed of (A) a carbonate compound and (B) boron trihalide may be suppressed. From the same viewpoint, 80 ° C. or lower is more preferable, and 60 ° C. or lower is more preferable. The distillation temperature does not need to be constant and may be changed in the middle.

  The distillation pressure is appropriately set depending on the distillation temperature, but when the distillation temperature exceeds 100 ° C., it is preferable that the pressure be lower than the atmospheric pressure. The distillation pressure need not be constant, and may be changed in the middle.

  The temperature for preparing the composition containing (A) a carbonate compound, (B) boron trihalide, and (C) an epoxy compound is not particularly limited, and is performed at a general usable temperature. It is preferable that it is 80-80 degreeC. The temperature at which the composition is prepared need not be constant, and may be changed midway.

  (A) When preparing a composition containing a carbonate compound, (B) boron trihalide, and (C) an epoxy compound, if there is a possibility that the raw material solidifies, the solidification of the raw material is suppressed, or Since the uniform composition tends to be obtained more easily by reducing the viscosity of the raw material, the temperature at which the composition is prepared is preferably −80 ° C. or higher. From the same viewpoint, the temperature for preparing the composition is more preferably −40 ° C. or higher. Since the necessity of using a large-sized cooling facility decreases and the cost for producing the composition tends to be suppressed, the temperature at which the composition is prepared is more preferably −20 ° C. or higher. From the same viewpoint, it is particularly preferably 0 ° C. or higher.

  When preparing a composition containing (A) a carbonate compound, (B) a boron trihalide, and (C) an epoxy compound, the polymerization of the (C) epoxy compound can be further suppressed, and a uniform composition can be made easier. Since there is a tendency to be obtained, the temperature for preparing the composition is preferably 60 ° C. or less. From the same viewpoint, the temperature for preparing the composition is more preferably 50 ° C. or lower. (C) Since the polymerization of the epoxy compound can be further suppressed and the stability of the composition tends to be further improved, the temperature at which the composition is prepared is more preferably 45 ° C. or lower. From the same viewpoint, the temperature is particularly preferably 40 ° C. or lower.

  The atmosphere for preparing the composition containing (A) a carbonate compound, (B) a boron trihalide, and (C) an epoxy compound is not particularly limited as long as it is a commonly used atmosphere. An atmosphere, a nitrogen atmosphere, an argon atmosphere, or the like is used. Among these, since the stability of (B) boron trihalide contained in the composition tends to be improved, a nitrogen atmosphere and an argon atmosphere are preferable. Moreover, since it exists in the tendency which is excellent in economical efficiency, nitrogen atmosphere is still more preferable.

  The pressure for preparing the composition containing (A) a carbonate compound, (B) boron trihalide, and (C) an epoxy compound is not particularly limited, and the preparation is usually performed under atmospheric pressure. However, when the vapor pressure in the standard state of the compound contained in the composition is low and there is a possibility of volatilization, it is an effective means to pressurize at atmospheric pressure or higher.

  When preparing a composition containing (A) a carbonate compound, (B) boron trihalide, and (C) an epoxy compound, the contained compound has a solid, or (A) the carbonate compound and (B ) When the mixture containing boron trihalide is a solid, a uniform composition can be easily obtained by using a soluble compound, which may be an effective means.

  The soluble compound as used herein refers to a solid compound and a mixture containing (A) a carbonate compound and (B) boron trihalide which is a solid compound. Means a compound capable of dissolving

  The soluble compound is not particularly limited as long as it is generally used. Specific examples include n-pentane, n-hexane, isohexane, n-heptane, n-octane, isooctane, n-nonane, n -Saturated hydrocarbon compounds such as decane, cyclopentane, cyclohexane, cycloheptane and cyclooctane, aromatic hydrocarbon compounds such as benzene, toluene, xylene, ethylbenzene, diethylbenzene, isopropylbenzene, naphthalene, tetralin and biphenyl, methylene chloride, chloroform , Carbon tetrachloride, ethylene chloride, trichloroethane, tetrachloroethane, pentachloroethane, hexachloroethane, dichloroethylene, trichloroethylene, tetrachloroethylene, dichloropropane, trichloropropane, isopropyl chloride , Halogenated hydrocarbon compounds such as butyl chloride, hexyl chloride, chlorobenzene, dichlorobenzene, trichlorobenzene, chlorotoluene and chloronaphthalene, methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, hexanol, heptanol, octanol , Alcohols such as nonanol, decanol, undecanol, dodecanol, cyclohexanol and benzyl alcohol, acetone, methyl acetone, ethyl methyl ketone, methyl propyl ketone, methyl butyl ketone, methyl isobutyl ketone, methyl hexyl ketone, diethyl ketone, ethyl butyl ketone , Ketones such as dipropyl ketone and diisobutyl ketone, cyclohexanone, and ethyl acetate, acetic acid Lopyl, butyl acetate, isobutyl acetate, pentyl acetate, hexyl acetate, octyl acetate, cyclohexyl acetate, methyl propionate, ethyl propionate, butyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, butyl benzoate and benzoic acid Examples include esters such as benzyl. The said compound may be used individually or may be used in combination of multiple.

  Among these, (B) it is highly stable with respect to boron trihalide, and a composition containing (A) a carbonate compound, (B) boron trihalide, and (C) an epoxy compound can be stably prepared. Because of the tendency, saturated hydrocarbon compounds such as n-pentane, n-hexane, isohexane, n-heptane, n-octane, isooctane, n-nonane, n-decane, cyclopentane, cyclohexane, cycloheptane, and cyclooctane , Methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichloroethane, tetrachloroethane, pentachloroethane, hexachloroethane, dichloroethylene, trichloroethylene, tetrachloroethylene, dichloropropane, trichloropropane, isopropyl chloride, butyl chloride, hexyl chloride, chloro Benzene, dichlorobenzene, trichlorobenzene, halogenated hydrocarbon compounds such as chlorotoluene and chloronaphthalene are preferred.

  In preparing a composition containing (A) a carbonate compound, (B) boron trihalide, and (C) an epoxy compound, by using a soluble compound, a composition other than the desired compound is contained in the composition. May be. In such a case, a method of removing the soluble compound by distillation under reduced pressure may be an effective means.

  The vacuum distillation temperature can further suppress the polymerization of the (C) epoxy compound, and the stability of the composition containing the (A) carbonate compound, (B) boron trihalide, and (C) epoxy compound is further improved. Since it exists in the tendency, it is preferable that it is 60 degrees C or less. From the same viewpoint, it is more preferably 50 ° C. or less, and further preferably 40 ° C. or less. The vacuum distillation pressure is appropriately set depending on the vacuum distillation temperature. The vacuum distillation temperature and the vacuum distillation pressure need not be constant, and may be changed midway.

  A method for obtaining a polymer from a composition containing (A) a carbonate compound, (B) boron trihalide, and (C) an epoxy compound is not particularly limited as long as it is a general method, but the composition is heated. A method of proceeding the polymerization by carrying out and / or a method of proceeding the polymerization by irradiation with energy rays is preferably used. Among these, the method of allowing the polymerization to proceed by heating is a more preferable method because it can be easily used in various situations and tends to be excellent in versatility. Moreover, when the epoxy compound contained in the composition has two or more polymerizable functional groups, a cured product can be obtained by the same method.

  Although it does not specifically limit as superposition | polymerization temperature at the time of polymerizing by heating and obtaining a polymer, It is preferable that it is -80-200 degreeC. The polymerization temperature does not need to be constant and may be changed in the middle.

  (C) The polymerization temperature is preferably 200 ° C. or lower because there is a tendency that the possibility of a complicated side reaction can be further reduced by the polymerization heat generated when the epoxy compound is polymerized. From the same viewpoint, the polymerization temperature is more preferably 180 ° C. or lower. (C) After polymerizing the epoxy compound, the transparency of the resulting polymer tends to be further improved, and therefore 160 ° C. or lower is more preferable. From the same viewpoint, the polymerization temperature is particularly preferably 150 ° C. or lower.

  (C) Polymerization of the epoxy compound is hindered by coagulation of the compound (A), (B), (C) present in the composition, a compound or the like via a coordination bond composed of the components (A) and (B) In the case where there is a possibility that the polymerization will occur, the polymerization temperature is preferably -80 ° C or higher. The polymerization temperature is more preferably −40 ° C. or higher because the necessity of using a large cooling facility tends to decrease and the cost for producing the polymer can be suppressed. From the same viewpoint, it is more preferably 0 ° C. or higher. The polymerization temperature is preferably 40 ° C. or higher because the mobility of the polymerization terminal of the polymer is further increased and the polymerization time of the (C) epoxy compound tends to be further shortened. From the same viewpoint, the polymerization temperature is more preferably 50 ° C. or higher, and further preferably 60 ° C. or higher.

  The polymerization atmosphere for proceeding polymerization by heating to obtain a polymer is not particularly limited as long as it is a commonly used atmosphere, but usually an air atmosphere, a nitrogen atmosphere, an argon atmosphere, or the like is used. Among these, a nitrogen atmosphere and an argon atmosphere are preferable because a desired bond tends to be formed during polymerization. Moreover, since it exists in the tendency which is excellent in economical efficiency, nitrogen atmosphere is still more preferable.

  There is no particular limitation on the polymerization pressure when the polymerization is carried out by heating to obtain a polymer, and the reaction is usually carried out under atmospheric pressure. However, when a compound having a low vapor pressure in the standard state and having a possibility of volatilization is used as a component contained in the composition, it is an effective means to pressurize at atmospheric pressure or higher.

  When the composition containing (A) a carbonate compound, (B) boron trihalide, and (C) an epoxy compound is highly viscous or solid, the composition is reduced in viscosity by a non-reactive compound, Obtaining a polymer having a desired shape is an effective means.

  The non-reactive compound is not particularly limited as long as it is generally used, but specific examples include n-pentane, n-hexane, isohexane, n-heptane, n-octane, isooctane, and n-nonane. , Saturated hydrocarbon compounds such as n-decane, cyclopentane, cyclohexane, cycloheptane and cyclooctane, aromatic hydrocarbon compounds such as benzene, toluene, xylene, ethylbenzene, diethylbenzene, isopropylbenzene, naphthalene, tetralin and biphenyl, methylene chloride , Chloroform, carbon tetrachloride, ethylene chloride, trichloroethane, tetrachloroethane, pentachloroethane, hexachloroethane, dichloroethylene, trichloroethylene, tetrachloroethylene, dichloropropane, trichloropropane, salt Halogenated hydrocarbon compounds such as isopropyl, butyl chloride, hexyl chloride, chlorobenzene, dichlorobenzene, trichlorobenzene, chlorotoluene and chloronaphthalene, acetone, methyl acetone, ethyl methyl ketone, methyl propyl ketone, methyl butyl ketone, methyl isobutyl ketone, Ketones such as methyl hexyl ketone, diethyl ketone, ethyl butyl ketone, dipropyl ketone and diisobutyl ketone, cyclohexanone, and ethyl acetate, propyl acetate, butyl acetate, isobutyl acetate, pentyl acetate, hexyl acetate, octyl acetate, cyclohexyl acetate, Methyl propionate, ethyl propionate, butyl propionate, methyl benzoate, ethyl benzoate, propyl benzoate, butyl benzoate and benzyl benzoate Esters and the like. The said compound may be used individually or may be used in combination of multiple.

  Among these, since (B) it is highly stable with respect to boron trihalide and tends to be able to stably prepare the composition, n-pentane, n-hexane, isohexane, n-heptane, n-octane , Isooctane, n-nonane, n-decane, cyclopentane, cyclohexane, cycloheptane, cyclooctane and other saturated hydrocarbon compounds, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichloroethane, tetrachloroethane, pentachloroethane, hexachloroethane , Dichloroethylene, trichloroethylene, tetrachloroethylene, dichloropropane, trichloropropane, isopropyl chloride, butyl chloride, hexyl chloride, chlorobenzene, dichlorobenzene, trichlorobenzene, chlorotoluene and chloronaphthalene Halogenated hydrocarbon compounds are preferred.

  When obtaining a polymer by proceeding with polymerization by heating, in order to accelerate the polymerization reaction or as an epoxy compound (C) contained in the composition, in addition to the three-membered ether structure, a three-membered ether structure When using a compound having other polymerizable functional group other than the above, the following compounds (1) to (11) are used as thermal polymerization accelerators for the purpose of easily proceeding the polymerization of the other polymerizable functional group. Adding it may be an effective means.

(1) Ethylamine, n-propylamine, sec-propylamine, n-butylamine, sec-butylamine, i-butylamine, tert-butylamine, pentylamine, hexylamine, heptylamine, octylamine, decylamine, laurylamine, mistyri Ruamine, 1,2-dimethylhexylamine, 3-pentylamine, 2-ethylhexylamine, allylamine, aminoethanol, 1-aminopropanol, 2-aminopropanol, aminobutanol, aminopentanol, aminohexanol, 3-ethoxypropylamine 3-propoxypropylamine, 3-isopropoxypropylamine, 3-butoxypropylamine, 3-isobutoxypropylamine, 3- (2-ethylhexyloxy) propylamine Emissions, amino cyclopentane, diaminocyclohexane, amino norbornene, aminomethyl cyclohexane, aminobenzene, benzylamine, phenethylamine, primary amines such as α- phenylethylamine, naphthylamine and furfurylamine;

  Ethylenediamine, 1,2-diaminopropane, 1,3-diaminopropane, 1,2-diaminobutane, 1,3-diaminobutane, 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diaminohexane 1,7-diaminoheptane, 1,8-diaminooctane, dimethylaminopropylamine, diethylaminopropylamine, bis- (3-aminopropyl) ether, 1,2-bis- (3-aminopropoxy) ethane, 1, 3-bis- (3-aminopropoxy) -2,2′-dimethylpropane, aminoethylethanolamine, 1,2-bisaminocyclohexane, 1,3-bisaminocyclohexane, 1,4-bisaminocyclohexane, 1, 3-bisaminomethylcyclohexane, 1,4-bisaminomethylcyclohexa 1,3-bisaminoethylcyclohexane, 1,4-bisaminoethylcyclohexane, 1,3-bisaminopropylcyclohexane, 1,4-bisaminopropylcyclohexane, hydrogenated 4,4′-diaminodiphenylmethane, 2-amino Piperidine, 4-aminopiperidine, 2-aminomethylpiperidine, 4-aminomethylpiperidine, 2-aminoethylpiperidine, 4-aminoethylpiperidine, N-aminoethylpiperidine, N-aminopropylpiperidine, N-aminoethylmorpholine, N -Aminopropylmorpholine, isophoronediamine, menthanediamine, 1,4-bisaminopropylpiperazine, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, 2,4-tolylenediamine, 2,6-triene Diamine, 2,4-toluenediamine, m-aminobenzylamine, 4-chloro-o-phenylenediamine, tetrachloro-p-xylylenediamine, 4-methoxy-6-methyl-m-phenylenediamine, m-xylylenediamine Amine, p-xylylenediamine, 1,5-naphthalenediamine, 2,6-naphthalenediamine, benzidine, 4,4′-bis (o-toluidine), dianisidine, 4,4′-diaminodiphenylmethane, 2,2- (4,4′-diaminodiphenyl) propane, 4,4′-diaminodiphenyl ether, 4,4′-thiodianiline, 4,4′-diaminodiphenylsulfone, 4,4′-diaminoditolylsulfone, methylenebis (o-chloro) Aniline), 3,9-bis (3-aminopropyl) -2,4,8,10- Tetraoxaspiro [5.5] undecane, diethylenetriamine, iminobispropylamine, methyliminobispropylamine, bis (hexamethylene) triamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine, N-aminoethylpiperazine, N Primary amines such as aminopropylpiperazine, 1,4-bis (aminoethylpiperazine), 1,4-bis (aminopropylpiperazine) and 2,6-diaminopyridine, bis (3,4-diaminophenyl) sulfone;

  Diethylamine, dipropylamine, di-n-butylamine, di-sec-butylamine, diisobutylamine, di-n-pentylamine, di-3-pentylamine, dihexylamine, dioctylamine, di (2-ethylhexyl) amine, methyl Hexylamine, diallylamine, pyrrolidine, piperidine, 2-picoline, 3-picoline, 4-picoline, 2,4-lupetidine, 2,6-lupetidine, 3,5-lupetidine, diphenylamine, N-methylaniline, N-ethylaniline , Secondary amines such as dibenzylamine, methylbenzylamine, dinaphthylamine, pyrrole, indoline, indole and morpholine;

  N, N′-dimethylethylenediamine, N, N′-dimethyl-1,2-diaminopropane, N, N′-dimethyl-1,3-diaminopropane, N, N′-dimethyl-1,2-diaminobutane, N, N′-dimethyl-1,3-diaminobutane, N, N′-dimethyl-1,4-diaminobutane, N, N′-dimethyl-1,5-diaminopentane, N, N′-dimethyl-1 , 6-Diaminohexane, N, N′-dimethyl-1,7-diaminoheptane, N, N′-diethylethylenediamine, N, N′-diethyl-1,2-diaminopropane, N, N′-diethyl-1 , 3-diaminopropane, N, N′-diethyl-1,2-diaminobutane, N, N′-diethyl-1,3-diaminobutane, N, N′-diethyl-1,4-diaminobutane, N, N ' Diethyl-1,6-diaminohexane, piperazine, 2-methylpiperazine, 2,5-dimethylpiperazine, 2,6-dimethylpiperazine, homopiperazine, 1,1-di- (4-piperidyl) methane, 1,2- Secondary polyamines such as di- (4-piperidyl) ethane, 1,3-di- (4-piperidyl) propane, 1,4-di- (4-piperidyl) butane and tetramethylguanidine;

  Trimethylamine, triethylamine, tri-n-propylamine, tri-iso-propylamine, tri-1,2-dimethylpropylamine, tri-3-methoxypropylamine, tri-n-butylamine, tri-iso-butylamine, tri- sec-butylamine, tri-pentylamine, tri-3-pentylamine, tri-n-hexylamine, tri-n-octylamine, tri-2-ethylhexylamine, tri-dodecylamine, tri-laurylamine, dicyclohexylethylamine, Cyclohexyldiethylamine, tri-cyclohexylamine, N, N-dimethylhexylamine, N-methyldihexylamine, N, N-dimethylcyclohexylamine, N-methyldicyclohexylamine, N, N-diethylethanol Min, N, N-dimethylethanolamine, N-ethyldiethanolamine, triethanolamine, tribenzylamine, N, N-dimethylbenzylamine, diethylbenzylamine, triphenylamine, N, N-dimethylamino-p-cresol, N, N-dimethylaminomethylphenol, 2- (N, N-dimethylaminomethyl) phenol, N, N-dimethylaniline, N, N-diethylaniline, pyridine, quinoline, N-methylmorpholine, N-methylpiperidine and Tertiary amines such as 2- (2-dimethylaminoethoxy) -4-methyl-1,3,2-dioxabornane;

  Tetramethylethylenediamine, pyrazine, N, N′-dimethylpiperazine, N, N′-bis ((2-hydroxy) propyl) piperazine, hexamethylenetetramine, N, N, N ′, N′-tetramethyl-1,3 -Butaneamine, 2-dimethylamino-2-hydroxypropane, diethylaminoethanol, N, N, N-tris (3-dimethylaminopropyl) amine, 2,4,6-tris (N, N-dimethylaminomethyl) phenol and Tertiary polyamines such as heptamethylisobiguanide;

  Imidazole, N-methylimidazole, 2-methylimidazole, 4-methylimidazole, N-ethylimidazole, 2-ethylimidazole, 4-ethylimidazole, N-butylimidazole, 2-butylimidazole, N-undecylimidazole, 2- Undecylimidazole, N-phenylimidazole, 2-phenylimidazole, N-benzylimidazole, 2-benzylimidazole, 1-benzyl-2-methylimidazole, N- (2′-cyanoethyl) -2-methylimidazole, N- ( Of 2'-cyanoethyl) -2-undecylimidazole, N- (2'-cyanoethyl) -2-phenylimidazole, 3,3-bis- (2-ethyl-4-methylimidazolyl) methane, alkylimidazole and isocyanuric acid With Various imidazoles such as condensates of mono and alkyl imidazole with formaldehyde;

  1,8-diazabicyclo [5.4.0] undecene-7,1,5-diazabicyclo [4.3.0] nonene-5,6-dibutylamino-1,8-diazabicyclo [5.4.0] undecene Amidines such as -7.

(2) A complex of the amine of (1) with borane and boron trifluoride.

(3) Trimethylphosphine, triethylphosphine, tri-iso-propylphosphine, tri-n-butylphosphine, tri-n-hexylphosphine, tri-n-octylphosphine, tricyclohexylphosphine, triphenylphosphine, tribenzylphosphine, tris (2-methylphenyl) phosphine, tris (3-methylphenyl) phosphine, tris (4-methylphenyl) phosphine, tris (diethylamino) phosphine, tris (4-methylphenyl) phosphine, dimethylphenylphosphine, diethylphenylphosphine, dicyclohexyl Phosphines such as phenylphosphine, ethyldiphenylphosphine, diphenylcyclohexylphosphine and chlorodiphenylphosphine.

(4) Tetramethylammonium chloride, tetramethylammonium bromide, tetramethylammonium acetate, tetraethylammonium chloride, tetraethylammonium bromide, tetraethylammonium acetate, tetra-n-butylammonium fluoride, tetra-n-butylammonium chloride, tetra-n -Butylammonium bromide, tetra-n-butylammonium iodide, tetra-n-butylammonium acetate, tetra-n-butylammonium borohydride, tetra-n-butylammonium hexafluorophosphite, tetra-n-butylammonium hydrogensal Fight, tetra-n-butylammonium tetrafluoroborate, tetra-n-butyl Ruammonium tetraphenylborate, tetra-n-butylammonium paratoluenesulfonate, tetra-n-hexylammonium chloride, tetra-n-hexylammonium bromide, tetra-n-hexylammonium acetate, tetra-n-octylammonium chloride, Tetra-n-octylammonium bromide, tetra-n-octylammonium acetate, trimethyl-n-octylammonium chloride, trimethylbenzylammonium chloride, trimethylbenzylammonium bromide, triethyl-n-octylammonium chloride, triethylbenzylammonium chloride, triethylbenzylammonium Bromide, tri-n-butyl-n-octylammoni Muchloride, tri-n-butylbenzylammonium fluoride, tri-n-butylbenzylammonium chloride, tri-n-butylbenzylammonium bromide, tri-n-butylbenzylammonium iodide, methyltriphenylammonium chloride, methyltriphenylammonium Bromide, ethyltriphenylammonium chloride, ethyltriphenylammonium bromide, n-butyltriphenylammonium chloride, n-butyltriphenylammonium bromide, 1-methylpyridinium bromide, 1-ethylpyridinium bromide, 1-n-butylpyridinium bromide, 1-n-hexylpyridinium bromide, 1-n-octylpyridinium bromide, 1-n-dode Silpyridinium bromide, 1-n-phenylpyridinium bromide, 1-methylpicolinium bromide, 1-ethylpicolinium bromide, 1-n-butylpicolinium bromide, 1-n-hexylpicolinium bromide, 1-n-octylpicoly Quaternary ammonium salts such as nium bromide, 1-n-dodecylpicolinium bromide and 1-n-phenylpicolinium bromide.

(5) Tetramethylphosphonium chloride, tetramethylphosphonium bromide, tetraethylphosphonium chloride, tetraethylphosphonium bromide, tetra-n-butylphosphonium chloride, tetra-n-butylphosphonium bromide, tetra-n-butylphosphonium iodide, tetra-n- Hexylphosphonium bromide, tetra-n-octylphosphonium bromide, methyltriphenylphosphonium bromide, methyltriphenylphosphonium iodide, ethyltriphenylphosphonium bromide, ethyltriphenylphosphonium iodide, n-butyltriphenylphosphonium bromide, n-butyltri Phenylphosphonium iodide, n-hexyltriphenylphosphonium bromide De, n- octyl triphenylphosphonium bromide, tetraphenylphosphonium bromide, tetrakis hydroxymethyl phosphonium chloride, tetrakis hydroxymethyl phosphonium bromide, tetrakis hydroxyethyl phosphonium chloride and phosphonium salts such as tetrakis hydroxybutyl phosphonium chloride.

(6) Trimethylsulfonium bromide, triethylsulfonium bromide, tri-n-butylsulfonium chloride, tri-n-butylsulfonium bromide, tri-n-butylsulfonium iodide, tri-n-butylsulfonium tetrafluoroborate, tri-n- Sulfonium salts such as hexylsulfonium bromide, tri-n-octylsulfonium bromide, triphenylsulfonium chloride, triphenylsulfonium bromide and triphenylsulfonium iodide.

(7) Iodonium salts such as diphenyliodonium chloride, diphenyliodonium bromide, and diphenyliodonium iodide.

(8) Mineral acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, carbonic acid and half esters thereof.

(9) Lewis acid typified by boron trifluoride and boron trifluoride etherate.

(10) Organic acids and their half esters.

(11) Silicic acid and tetrafluoroboric acid.

  These compounds may be used alone or in combination.

  Polymerization by irradiation with energy rays is a method for producing a polymer by irradiating energy rays (ultraviolet rays, near ultraviolet rays, visible light, light such as near infrared rays and infrared rays, and electron beams). The type of energy beam is not particularly limited, but is preferably light, more preferably ultraviolet light.

  The source of energy rays is not particularly limited. For example, a low pressure mercury lamp, a medium pressure mercury lamp, a high pressure mercury lamp, an ultrahigh pressure mercury lamp, a UV lamp, a xenon lamp, a carbon arc lamp, a metal halide lamp, a fluorescent lamp, a tungsten lamp, Various light sources such as an argon ion laser, helium cadmium laser, helium neon laser, krypton ion laser, various semiconductor lasers, YAG laser, excimer laser, light emitting diode, CRT light source, plasma light source, and electron beam irradiator can be used.

  When polymerizing by energy ray irradiation, in order to accelerate the polymerization, it may be an effective means to add the following compound as a photopolymerization accelerator.

  Benzoins and benzoin alkyl ethers (benzoin, benzyl, benzoin methyl ether and benzoin isopropyl ether), acetophenones (acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1, 1-dichloroacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1- (4- (methylthio) phenyl) -2-morpholino-propan-1-one and N, N-dimethylaminoacetophenone), anthraquinones ( 2-methylanthraquinone, 2-ethylanthraquinone, 2-tert-butylanthraquinone, 1-chloroanthraquinone, 2-amylanthraquinone and 2-aminoanthraquinone), thioxane (2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, 2,4-diisopropylthioxanthone, etc.), ketals (acetophenone dimethyl ketal, benzyldimethyl ketal, etc.), benzophenones (benzophenone, methyl) Benzophenone, 4,4′-dichlorobenzophenone and 4,4′-bisdiethylaminobenzophenone, etc.), xanthones, benzoates (such as ethyl 4-dimethylaminobenzoate and 2- (dimethylamino) ethylbenzoate), amines ( Triethylamine, triethanolamine, etc.), iodonium salt compounds, sulfonium salt compounds, ammonium salt compounds, phosphonium salt compounds, arsonium salt compounds, stibonium salt compounds, Kisoniumu salt compound, a selenonium salt compound, and, stannonium salt compound. These may be used alone or in combination.

  The composition containing (A) a carbonate compound, (B) boron trihalide, and (C) an epoxy compound may further contain (D) a chain transfer agent. (D) By using a chain transfer agent, the resulting polymer and cured product have a reduced volatile content when held for a long time at high temperature, and void formation occurs during molding by melt processing, or the polymer or It tends to be possible to further suppress contamination or corrosion of the metal member in the vicinity of the cured product.

  (D) The chain transfer agent is not particularly limited as long as it is generally used, but it may be at least one compound selected from the group consisting of cyclic ester compounds, cyclic siloxane compounds, and hydroxyl group-containing compounds. preferable. These may be used alone or in combination. (C) Since the transparency of the resulting polymer may be reduced depending on the selection of the epoxy compound, (D) the chain transfer agent is at least one selected from the group consisting of cyclic ester compounds and hydroxyl group-containing compounds. More preferably, it is a seed compound. (C) Since the polymerization time of the epoxy compound tends to be shortened, (D) the chain transfer agent is more preferably a hydroxyl group-containing compound.

(Cyclic ester compound)
The cyclic ester compound is not particularly limited as long as it has an ester group in the cyclic structure. Specifically, ethano-2-lactone, propano-2-lactone, propano-3-lactone, butano- 2-lactone, butano-3-lactone, butano-4-lactone, 3-methyl-butano-4-lactone, pentano-2-lactone, pentano-3-lactone, pentano-4-lactone, pentano-5-lactone, 4-methyl-pentano-4-lactone, hexano-2-lactone, hexano-3-lactone, hexano-4-lactone, hexano-5-lactone, hexano-6-lactone, heptano-2-lactone, heptano-3- Lactone, heptano-4-lactone, heptano-5-lactone, heptano-6-lactone, heptano-7-lac , Octano-2-lactone, octano-3-lactone, octano-4-lactone, octano-5-lactone, octano-6-lactone, octano-7-lactone, octano-8-lactone, nonano-2-lactone, Nonano-3-lactone, Nonano-4-lactone, Nonano-5-lactone, Nonano-6-lactone, Nonano-7-lactone, Nonano-8-lactone, Nonano-9-lactone, Decano-2-lactone, Decano- 3-lactone, decano-4-lactone, decano-5-lactone, decano-6-lactone, decano-7-lactone, decano-8-lactone, decano-9-lactone, decano-10-lactone;

  Undecano-2-lactone, Undecano-3-lactone, Undecano-4-lactone, Undecano-5-lactone, Undecano-6-lactone, Undecano-7-lactone, Undecano-8-lactone, Undecano-9-lactone, Undecano- 10-lactone, undecano-11-lactone, dodecano-2-lactone, dodecano-3-lactone, dodecano-4-lactone, dodecano-5-lactone, dodecano-6-lactone, dodecano-7-lactone, dodecano-8- Lactone, dodecano-9-lactone, dodecano-10-lactone, dodecano-11-lactone, dodecano-12-lactone, tridecano-2-lactone, tridecano-3-lactone, tridecano-4-lactone, tridecano-5-lactone, Tridecano-6-lactone, Decano-7-lactone, tridecano-8-lactone, tridecano-9-lactone, tridecano-10-lactone, tridecano-11-lactone, tridecano-12-lactone, tridecano-13-lactone, tetradecano-2-lactone, tetradecano- 3-lactone, tetradecano-4-lactone, tetradecano-5-lactone, tetradecano-6-lactone, tetradecano-7-lactone, tetradecano-8-lactone, tetradecano-9-lactone, tetradecano-10-lactone, tetradecano-11 Lactone, tetradecano-12-lactone, tetradecano-13-lactone, tetradecano-14-lactone;

Pentadecano-2-lactone, pentadecano-3-lactone, pentadecano-4-lactone, pentadecano-5-lactone, pentadecano-6-lactone, pentadecano-7-lactone, pentadecano-8-lactone, pentadecano-9-lactone, pentadecano- 10-lactone, pentadecano-11-lactone, pentadecano-12-lactone, pentadecano-13-lactone, pentadecano-14-lactone, pentadecano-15-lactone, hexadecano-2-lactone, hexadecano-3-lactone, hexadecano-4- Lactone, hexadecano-5-lactone, hexadecano-6-lactone, hexadecano-7-lactone, hexadecano-8-lactone, hexadecano-9-lactone, hexadecano-10-lactone, hexade Roh-11-lactone, Hekisadekano-12-lactone, Hekisadekano-13-lactone, Hekisadekano-14-lactone, Hekisadekano-15-lactone, Hekisadekano-16-lactone, it can be chosen from.

  Among them, (D) the chain transfer agent remains in the polymer or cured product and / or (C) the increase in the polymerization time of the epoxy compound tends to be suppressed. The compound is preferably at least one compound selected from the following group.

  Butano-4-lactone, pentano-4-lactone, pentano-5-lactone, hexano-4-lactone, hexano-6-lactone, heptano-4-lactone, heptano-7-lactone, octano-4-lactone, octano- 8-lactone, decano-10-lactone, dodecano-12-lactone, tetradecano-14-lactone, hexadecano-16-lactone.

  More preferably, it is at least one compound selected from the following group.

  Butano-4-lactone, pentano-4-lactone, hexano-4-lactone.

(Cyclic siloxane compound)
The cyclic siloxane compound is not particularly limited as long as the cyclic structure is a compound formed by a siloxane bond. Specifically, the cyclic siloxane compound is at least one compound that can be selected from the following group.

  Trimethylcyclotrisiloxane, triethylcyclotrisiloxane, tripropylcyclotrisiloxane, tributylcyclotrisiloxane, tripentylcyclotrisiloxane, trihexylcyclotrisiloxane, triheptylcyclotrisiloxane, trioctylcyclotrisiloxane, trinonylcyclotrisiloxane , Tridecylcyclotrisiloxane, triphenylcyclotrisiloxane, hexamethylcyclotrisiloxane, hexaethylcyclotrisiloxane, hexapropylcyclotrisiloxane, hexabutylcyclotrisiloxane, hexapentylcyclotrisiloxane, hexahexylcyclotrisiloxane, hexaheptyl Cyclotrisiloxane, hexaoctylcyclotrisiloxane, hexanonylcycloto Siloxane, hexadecyl cyclotrisiloxane, hexaphenylcyclotrisiloxane, trimethyl triphenyl cyclotrisiloxane;

  Tetramethylcyclotetrasiloxane, tetraethylcyclotetrasiloxane, tetrapropylcyclotetrasiloxane, tetrabutylcyclotetrasiloxane, tetrapentylcyclotetrasiloxane, tetrahexylcyclotetrasiloxane, tetraheptylcyclotetrasiloxane, tetraoctylcyclotetrasiloxane, tetranonylcyclo Tetrasiloxane, tetradecylcyclotetrasiloxane, tetraphenylcyclotetrasiloxane, octamethylcyclotetrasiloxane, octaethylcyclotetrasiloxane, octapropylcyclotetrasiloxane, octabutylcyclotetrasiloxane, octapentylcyclotetrasiloxane, octahexylcyclotetrasiloxane , Octaheptylcyclotetrasiloxane Oct octyl cyclotetrasiloxane, octa nonyl cyclotetrasiloxane, octadecyl cyclotetrasiloxane, octaphenylcyclotetrasiloxane, tetramethyl tetraphenyl cyclotetrasiloxane;

  Pentamethylcyclopentasiloxane, pentaethylcyclopentasiloxane, pentapropylcyclopentasiloxane, pentabutylcyclopentasiloxane, pentapentylcyclopentasiloxane, pentahexylcyclopentasiloxane, pentaheptylcyclopentasiloxane, pentaoctylcyclopentasiloxane, pentanonyl Cyclopentasiloxane, pentadecylcyclopentasiloxane, pentaphenylcyclopentasiloxane, decamethylcyclopentasiloxane, decaethylcyclopentasiloxane, decapropylcyclopentasiloxane, decabutylcyclopentasiloxane, decapentylcyclopentasiloxane, decahexylcyclopenta Siloxane, decaheptylcyclopentasiloxane, decaoctyl Black pentasiloxane, decanonyl cyclopentasiloxane, decamethylcyclopentasiloxane decyl cyclopentasiloxane, decamethylcyclopentasiloxane phenyl cyclopentasiloxane, pentamethyl pentaphenyl cyclopentasiloxane.

  Among these, (D) the chain transfer agent remains in the polymer or cured product and / or (C) the increase in the polymerization time of the epoxy compound tends to be suppressed, so that the cyclic siloxane. The compound is preferably at least one compound selected from the following group.

  Hexamethylcyclotrisiloxane, hexaethylcyclotrisiloxane, hexapropylcyclotrisiloxane, hexabutylcyclotrisiloxane, hexapentylcyclotrisiloxane, hexahexylcyclotrisiloxane, trimethyltriphenylcyclotrisiloxane, octamethylcyclotetrasiloxane, octa Ethylcyclotetrasiloxane, Octapropylcyclotetrasiloxane, Octabutylcyclotetrasiloxane, Octapentylcyclotetrasiloxane, Octahexylcyclotetrasiloxane, Tetramethyltetraphenylcyclotetrasiloxane, Decamethylcyclopentasiloxane, Decaethylcyclopentasiloxane, Deca Propylcyclopentasiloxane, decabutylcyclopentasiloxane, Pentyl cyclopentasiloxane, decamethylcyclopentasiloxane hexyl cyclopentasiloxane, pentamethyl pentaphenyl cyclopentasiloxane.

More preferably, it is at least one compound selected from the following group.
Hexamethylcyclotrisiloxane, octamethylcyclotetrasiloxane, decamethylcyclopentasiloxane.

(Hydroxyl-containing compound)
The hydroxyl group-containing compound is not particularly limited as long as it is a compound having a hydroxyl group in the structure. Specifically, it is at least one compound that can be selected from the following group.

  Methanol, ethanol, 1-propanol, 2-propanol, cyclopropanol, methylcyclopropanol, dimethylcyclopropanol, ethylcyclopropanol, propylcyclopropanol, butylcyclopropanol, 1-butanol, 2-butanol, tert-butanol, cyclobutanol, Methylcyclobutanol, dimethylcyclobutanol, ethylcyclobutanol, propylcyclobutanol, butylcyclobutanol, 1-pentanol, 2-pentanol, 3-pentanol, cyclopentanol, methylcyclopentanol, dimethylcyclopentanol, ethyl Cyclopentanol, propylcyclopentanol, butylcyclopentanol, methyl-1-butanol, methyl-2-butanol, Methyl-1-butanol, dimethyl-2-butanol, ethyl-1-butanol, ethyl-2-butanol, 1-hexanol, 2-hexanol, 3-hexanol, cyclohexanol, methylcyclohexanol, dimethylcyclohexanol, ethylcyclohexanol , Propylcyclohexanol, butylcyclohexanol;

  Methyl-1-pentanol, methyl-2-pentanol, methyl-3-pentanol, dimethyl-1-pentanol, dimethyl-2-pentanol, dimethyl-3-pentanol, ethyl-1-pentanol, ethyl 2-pentanol, ethyl-3-pentanol, 1-heptanol, 2-heptanol, 3-heptanol, cycloheptanol, methylcycloheptanol, dimethylcycloheptanol, ethylcycloheptanol, methyl-1-hexanol, Methyl-2-hexanol, methyl-3-hexanol, dimethyl-1-hexanol, dimethyl-2-hexanol, ethyl-1-hexanol, ethyl-2-hexanol, ethyl-3-hexanol, 1-octanol, 2-octanol, 3-octanol, 4-o Pentanol, cyclo octanol, methyl cyclo octanol, dimethyl cyclooctanol, ethyl cyclo octanol, nonanol, cycloalkyl nonanol, decanol, cycloalkyl, octadecanol, undecanol, dodecanol, tridecanol, tetradecanol, pentadecanol, hexadecanol;

  Ethylene glycol, 1,2-propanediol, 1,3-propanediol, methylpropanediol, dimethylpropanediol, cyclopropanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, methylbutanediol, dimethylbutanediol, cyclobutanediol, methylcyclobutanediol, dimethylcyclobutanediol, ethylcyclobutanediol, propylcyclobutanediol, butylcyclobutanediol, 1,2-pentanediol, 1,3-pentane Diol, 1,4-pentanediol, 1,5-pentanediol, methylpentanediol, dimethylpentanediol, cyclopentanediol, methylcyclopentanediol, dimethyl Lucyclopentanediol, ethylcyclopentanediol, propylcyclopentanediol, butylcyclopentanediol, 1,2-hexanediol, 1,3-hexanediol, 1,4-hexanediol, 1,5-hexanediol, 1, 6-hexanediol, methylhexanediol, dimethylhexanediol, cyclohexanediol, methylcyclohexanediol, dimethylcyclohexanediol, ethylcyclohexanediol, propylcyclohexanediol, butylcyclohexanediol;

  1,2-heptanediol, 1,3-heptanediol, 1,4-heptanediol, 1,5-heptanediol, 1,6-heptanediol, 1,7-heptanediol, cycloheptanediol, methylcycloheptanediol Dimethylcycloheptanediol, 1,2-octanediol, 1,3-octanediol, 1,4-octanediol, 1,5-octanediol, 1,6-octanediol, 1,7-octanediol, 1, 8-octanediol, cyclooctanediol, methylcyclooctanediol, dimethylcyclooctanediol, nonanediol, cyclononanediol, decanediol, cyclodecanediol, undecanediol, dodecanediol, tridecanediol, tetradecanediol, Printer-decanediol, hexadecane diol;

  Glycerol, erythritol, xylitol, mannitol, boremitol, glucose, sucrose, diethylene glycol, triethylene glycol, tetraethylene glycol, pentaethylene glycol, hexaethylene glycol, octaethylene glycol, dodecaethylene glycol, methylal, PEG200, PEG300, PEG400, PEG600, PEG1000, PEG1500, PEG1540, PEG4000, PEG6000, polycarbonate diol;

  Polyester-8-hydroxy-1-acetylene bis-MPA dendron generation 3 (product name, manufactured by Aldrich), Polyester-16-hydroxy-1-acetylene bis-MPA dendron generation 4 (product name, manufactured by Aldrich), polyester- 32-hydroxy-1-acetylene bis-MPA dendron generation 5 (product name, manufactured by Aldrich), polyester-8-hydroxy-1-carboxyl bis-MPA dendron generation 3 (product name, manufactured by Aldrich), polyester-16 Hydroxy-1-carboxyl bis-MPA dendron generation 4 (product name, manufactured by Aldrich), polyester-32-hydroxy-1-carboxyl Su-MPA Dendron Generation 5 (product name, manufactured by Aldrich), Hyperbranched bis-MPA polyester-16-hydroxyl, Generation 2 (product name, manufactured by Aldrich), Hyperbranched bis-MPA polyester-32-hydroxyl, Generation 3 (product name, manufactured by Aldrich).

  Among these, (D) the chain transfer agent remains in the polymer or cured product, and / or (C) the increase in polymerization time of the epoxy compound tends to be suppressed. The compound is preferably at least one compound selected from the following group.

  Methanol, ethanol, 1-propanol, 2-propanol, 1-butanol, 2-butanol, 1-pentanol, 2-pentanol, 3-pentanol, cyclopentanol, 1-hexanol, 2-hexanol, 3-hexanol , Cyclohexanol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, , 2-pentanediol, 1,3-pentanediol, 1,4-pentanediol, 1,5-pentanediol, cyclopentanediol, 1,2-hexanediol, 1,3-hexanediol, 1,4-hexane Diol, 1,5-hexanediol, 1,6-hexanediol, Cyclohexane diol, glycerol, methylal.

  More preferably, it is at least one compound selected from the following group.

  2-propanol, 2-butanol, 2-pentanol, 3-pentanol, cyclopentanol, 2-hexanol, 3-hexanol, cyclohexanol, ethylene glycol, 1,2-propanediol, 1,3-propanediol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, 2,3-butanediol, methylal.

  (D) The mixing ratio of the chain transfer agent and the (C) epoxy compound is such that (D) the amount (mol) of the chain transfer agent and the amount (mol) of the epoxy group contained in the (C) epoxy compound. The ratio is preferably 1:10 to 1: 10000.

  (D) When the amount (mol) of the chain transfer agent is 1, (C) the amount of the epoxy group contained in the epoxy compound (mol) is 10 or more. Residue in the product or cured product is suppressed, and there is a tendency that the volatile content when the polymer and the cured product obtained by polymerizing the epoxy compound (C) are kept at a high temperature for a long time is further reduced. ,preferable. (D) When the substance amount (mol) of the chain transfer agent is 1, (C) the substance amount (mol) of the epoxy group contained in the epoxy compound is 20 or more. This is more preferable because the mechanical strength of the cured product tends to be improved. From the same viewpoint, when the amount (mol) of the (D) chain transfer agent is 1, it is more preferable that the amount (mol) of the epoxy group contained in the (C) epoxy compound is 50 or more.

  (D) When the substance amount (mol) of the chain transfer agent is 1, (C) the epoxy compound is polymerized because the substance amount (mol) of the epoxy group contained in the epoxy compound is 10,000 or less. The polymer and the cured product obtained in this manner are preferable because the volatile content when kept for a long time at a high temperature tends to be further reduced. From the same viewpoint, when the amount (mol) of the chain transfer agent (D) is 1, the amount (mol) of the epoxy group contained in the epoxy compound (C) is more preferably 2000 or less, and Preferably it is 1000 or less. A composition containing (A) a carbonate compound, (B) boron trihalide, and (C) an epoxy compound is further added with (D) a chain transfer agent, and the resulting polymer and cured product are heated under high temperature. The reason why the volatile component tends to be reduced when held for a long time is not clear, but (D) the chain transfer agent may suppress the depolymerization of the polymer and the cured product.

The mixing ratio of the (D) chain transfer agent and the (C) epoxy compound can also be represented by the following formula (10).
Index γ = αd / αep × 100 (10)
αd: (D) amount of chain transfer agent (mol)
αep: (C) the amount of epoxy group contained in the epoxy compound (mol)

(D) When the ratio of the amount (mol) of the chain transfer agent to the amount (mol) of the epoxy group contained in the epoxy compound (C) is 1:10, the index γ = 10.
(D) When the ratio of the amount (mol) of the chain transfer agent to the amount (mol) of the epoxy group contained in the epoxy compound (C) is 1:20, the index γ = 5.
(D) When the ratio of the amount (mol) of the chain transfer agent to the amount (mol) of the epoxy group contained in the epoxy compound (C) is 1:50, the index γ = 2.
(D) When the ratio of the amount (mol) of the chain transfer agent to the amount (mol) of the epoxy group contained in the epoxy compound (C) is 1: 10000, the index γ = 0.01. .
(D) When the ratio of the amount (mol) of the chain transfer agent to the amount (mol) of the epoxy group contained in the epoxy compound (C) is 1: 2000, the index γ = 0.05. .
(D) When the ratio of the amount (mol) of the chain transfer agent to the amount (mol) of the epoxy group contained in the epoxy compound (C) is 1: 1000, the index γ = 0.1. .

  As a method for preparing a composition containing (A) a carbonate compound, (B) boron trihalide, (C) an epoxy compound, and (D) a chain transfer agent, any method that is generally used can be used. Without limitation, (A) carbonate compound, (B) boron trihalide, (C) epoxy compound, (D) a method of adding a chain transfer agent, (A) carbonate compound, (B) boron trihalide, (C) The method of adding at least 2 component arbitrarily selected among the epoxy compound and (D) chain transfer agent, adding to the remaining component, and / or adding the remaining component is mentioned. Among these, since the composition can be stably prepared and the stability as the composition tends to be excellent, after preparing a mixture containing (A) a carbonate compound and (B) boron trihalide, A method of adding the remaining component (C) to the epoxy compound and (D) the chain transfer agent and / or adding the remaining component is preferable.

  Polymers and cured products obtained by polymerizing the composition are various organic resins, inorganic fillers, colorants, leveling agents, lubricants, surfactants, silicone compounds, reactive diluents, A reactive diluent, an antioxidant, a light stabilizer and the like can be appropriately contained. In addition, generally used as additives for plastics (plasticizers, flame retardants, stabilizers, antistatic agents, impact resistance enhancers, foaming agents, antibacterial / antifungal agents, conductive fillers, antifogging agents, crosslinking agents, etc.) The substance to be obtained may be blended with the polymer or the cured product.

  The organic resin is not particularly limited, and examples thereof include an acrylic resin, a polyester resin, and a polyimide resin.

  Examples of the inorganic filler include silicas (fused crushed silica, crystal crushed silica, spherical silica, fumed silica, colloidal silica, precipitated silica, etc.), silicon carbide, silicon nitride, boron nitride, calcium carbonate, magnesium carbonate, Barium sulfate, calcium sulfate, mica, talc, clay, aluminum oxide, magnesium oxide, zirconium oxide, titanium oxide, aluminum hydroxide, magnesium hydroxide, calcium silicate, aluminum silicate, lithium aluminum silicate, zirconium silicate, barium titanate, glass Examples include fibers, carbon fibers, and molybdenum disulfide. Among these, silicas, calcium carbonate, aluminum oxide, zirconium oxide, titanium oxide, aluminum hydroxide, calcium silicate, and barium titanate are preferable, and silica is more preferable in view of physical properties of the cured product. These inorganic fillers may be used alone or in combination.

  The colorant is not particularly limited as long as it is a substance used for the purpose of coloring. The pigment may be selected from inorganic pigments such as titanium oxide, lead sulfate, chrome yellow, zinc yellow, chrome vermilion, valve shell, cobalt violet, bitumen, ultramarine, carbon black, chrome green, chrome oxide and cobalt green. These colorants may be used alone or in combination.

  A leveling agent is not specifically limited, For example, the oligomer of molecular weight 4000-12000 formed from acrylates, such as ethyl acrylate, butyl acrylate, and 2-ethylhexyl acrylate, epoxidized soybean fatty acid, epoxidized abiethyl alcohol, hydrogenated castor oil As well as titanium coupling agents. These leveling agents may be used alone or in combination.

  The lubricant is not particularly limited, and hydrocarbon lubricants such as paraffin wax, micro wax and polyethylene wax, higher fatty acid lubricants such as lauric acid, myristic acid, palmitic acid, stearic acid, arachidic acid and behenic acid, stearylamide, Higher fatty acid amide type lubricants such as palmitylamide, oleylamide, methylenebisstearamide and ethylenebisstearamide, hydrogenated castor oil, butyl stearate, ethylene glycol monostearate and pentaerythritol (mono-, di-, tri- , Or higher fatty acid ester lubricants such as tetra-stearate, alcohol lubricants such as cetyl alcohol, stearyl alcohol, polyethylene glycol and polyglycerol, lauric acid, myristic acid, palmitic acid, stearin , Metal soaps such as magnesium, calcium, cadmium, barium, zinc and lead such as arachidic acid, behenic acid, ricinoleic acid and naphthenic acid, and natural waxes such as carnauba wax, candelilla wax, beeswax and montan wax. obtain. These lubricants may be used alone or in combination.

  A surfactant refers to an amphiphilic substance having a hydrophobic group having no affinity for a solvent in a molecule and a philic group (usually a hydrophilic group) having an affinity for a solvent. The kind of surfactant is not specifically limited, For example, a silicon-type surfactant, a fluorine-type surfactant, etc. are mentioned. Surfactants may be used alone or in combination.

  The silicone compound is not particularly limited, and examples thereof include silicone resins, silicone condensates, silicone partial condensates, silicone oils, silane coupling agents, silicone oils, and polysiloxanes. The silicone compound may be modified by introducing an organic group at both ends, one end, or side chains. The method for modifying the silicone compound is not particularly limited. For example, amino modification, epoxy modification, alicyclic epoxy modification, carbinol modification, methacryl modification, polyether modification, mercapto modification, carboxyl modification, phenol modification, silanol modification, Examples include polyether modification, polyether methoxy modification, and diol modification.

  The reactive diluent is not particularly limited. For example, alkyl glycidyl ether, monoglycidyl ether of alkylphenol, neopentyl glycol diglycidyl ether, 1,6-hexanediol diglycidyl ether, alkanoic acid glycidyl ester, ethylene glycol diglycidyl ether And propylene glycol diglycidyl ether.

  The non-reactive diluent is not particularly limited, and may be selected from high boiling solvents such as benzyl alcohol, butyl diglycol and propylene glycol monomethyl ether.

  The antioxidant is not particularly limited, and can be selected from, for example, phenolic antioxidants, phosphorus antioxidants, sulfur antioxidants, and amine antioxidants. These may be used alone or in combination. Specific examples of the antioxidant include the following (1) to (4).

(1) Phenol antioxidants: For example, the following alkylphenols, hydroquinones, thioalkyl or thioaryls, bisphenols, benzyl compounds, triazines, β- (3,5-di-tert-butyl-4-hydroxy Phenyl) propionic acid and monohydric or polyhydric alcohol ester, β- (5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid and monohydric or polyhydric alcohol ester, β- (3 , 5-dicyclohexyl-4-hydroxyphenyl) propionic acid and monohydric or polyhydric alcohol ester, 3,5-di-tert-butyl-4-hydroxyphenylacetic acid and monohydric or polyhydric alcohol ester, β -(3,5-Di-tert-butyl-4-hydroxyphenyl) propionic acid amide And vitamins.

(1-1) Alkylphenols: 2,6-di-tert-butyl-4-methylphenol, 2-tert-butyl-4,6-dimethylphenol, 2,6-di-tert-butyl-4-ethylphenol 2,6-di-tert-butyl-4-n-butylphenol, 2,6-di-tert-butyl-4-isobutylphenol, 2,6-dicyclopentyl-4-methylphenol, 2- (α-methyl) Cyclohexyl) -4,6-dimethylphenol, 2,6-dioctadecyl-4-methylphenol, 2,4,6-tricyclohexylphenol, 2,6-di-tert-butyl-4-methoxymethylphenol, linear Nonylphenols having a branched or branched side chain (for example, 2,6-di-nonyl-4-methylphenol), 2,4- Methyl-6- (1′-methylundec-1′-yl) phenol, 2,4-dimethyl-6- (1′-methylheptadec-1′-yl) phenol, 2,4-dimethyl-6- (1 '-Methyltridec-1'-yl) phenol and mixtures thereof, 4-hydroxylaurylanilide, 4-hydroxystearanilide, and octyl N- (3,5-di-tert-butyl-4-hydroxyphenyl) carbamate.

(1-2) Hydroquinones: 2,6-di-tert-butyl-4-methoxyphenol, 2,5-di-tert-butylhydroquinone, 2,5-di-tert-amylhydroquinone, 2,6-diphenyl -4-octadecyloxyphenol, 2,6-di-tert-butylhydroquinone, 2,5-di-tert-butyl-4-hydroxyanisole, 3,5-di-tert-butyl-4-hydroxyanisole, 3, 5-di-tert-butyl-4-hydroxyphenyl stearate and bis (3,5-di-tert-butyl-4-hydroxyphenyl) adipate.

(1-3) Thioalkyl or thioaryls: 2,4-dioctylthiomethyl-6-tert-butylphenol, 2,4-dioctylthiomethyl-6-methylphenol, 2,4-dioctylthiomethyl-6-ethylphenol, 2,6-di-dodecylthiomethyl-4-nonylphenol, 2,2'-thiobis (6-tert-butyl-4-methylphenol), 2,2'-thiobis (4-octylphenol), 4,4'- Thiobis (6-tert-butyl-3-methylphenol), 4,4'-thiobis (6-tert-butyl-2-methylphenol), 4,4'-thiobis (3,6-di-sec-amylphenol) ) And 4,4′-bis (2,6-dimethyl-4-hydroxyphenyl) disulfide.

(1-4) Bisphenols: 2,2′-methylenebis (6-tert-butyl-4-methylphenol), 2,2′-methylenebis (6-tert-butyl-4-ethylphenol), 2,2 ′ -Methylenebis [4-methyl-6- (α-methylcyclohexyl) phenol], 2,2'-methylenebis (4-methyl-6-cyclohexylphenol), 2,2'-methylenebis (6-nonyl-4-methylphenol) ), 2,2′-methylenebis (4,6-di-tert-butylphenol), 2,2′-ethylidenebis (4,6-di-tert-butylphenol), 2,2′-ethylidenebis (6-tert) -Butyl-4-isobutylphenol), 2,2′-methylenebis [6- (α-methylbenzyl) -4-nonylphenol], 2, 2′-methylenebis [6- (α, α-dimethylbenzyl) -4-nonylphenol], 4,4′-methylenebis (2,6-di-tert-butylphenol), 4,4′-methylenebis (6-tert- Butyl-2-methylphenol), 1,1-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 2,6-bis (3-tert-butyl-5-methyl-2-hydroxy) Benzyl) -4-methylphenol, 1,1,3-tris (5-tert-butyl-4-hydroxy-2-methylphenyl) butane, 1,1-bis (5-tert-butyl-4-hydroxy-2) -Methylphenyl) -3-n-dodecyl mercaptobutane, ethylene glycol bis [3,3-bis (3'-tert-butyl-4'-hydroxypheny L) butyrate], bis (3-tert-butyl-4-hydroxy-5-methyl-phenyl) dicyclopentadiene, bis [2- (3′-tert-butyl-2′-hydroxy-5′-methylbenzyl) -6-tert-butyl-4-methylphenyl] terephthalate, 1,1-bis (3,5-dimethyl-2-hydroxyphenyl) butane, 2,2-bis (3,5-di-tert-butyl-4 -Hydroxyphenyl) propane, 2,2-bis (5-tert-butyl-4-hydroxy-2-methylphenyl) -4-n-dodecylmercaptobutane and 1,1,5,5-tetra (5-tert- (Butyl-4-hydroxy-2-methylphenyl) pentane.

(1-5) benzyl compounds: 3,5,3 ′, 5′-tetra-tert-butyl-4,4′-dihydroxydibenzyl ether, octadecyl-4-hydroxy-3,5-dimethylbenzyl mercaptoacetate Tridecyl-4-hydroxy-3,5-di-tert-butylbenzylmercaptoacetate, tris (3,5-di-tert-butyl-4-hydroxybenzyl) amine, bis (4-tert-butyl-3- Hydroxy-2,6-dimethylbenzyl) dithioterephthalate, bis (3,5-di-tert-butyl-4-hydroxybenzyl) sulfide, isooctyl-3,5-di-tert-butyl-4-hydroxybenzyl mercaptoacetate Tart, dioctadecyl-2,2-bis (3,5-di-tert-butyl-2- Loxybenzyl) malonate, di-octadecyl-2- (3-tert-butyl-4-hydroxy-5-methylbenzyl) malonate, di-dodecylmercaptoethyl-2,2-bis (3,5-di-tert-butyl) -4-hydroxybenzyl) malonate, bis [4- (1,1,3,3-tetramethylbutyl) phenyl] -2,2-bis (3,5-di-tert-butyl-4-hydroxybenzyl) malonate 1,3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) -2,4,6-trimethylbenzene, 1,4-bis (3,5-di-tert-butyl- 4-hydroxybenzyl) -2,3,5,6-tetramethylbenzene and 2,4,6-tris (3,5-di-tert-butyl-4-hydroxybenzyl) Phenol.

(1-6) Triazines: 2,4-bis (octylmercapto) -6- (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octylmercapto -4,6-bis (3,5-di-tert-butyl-4-hydroxyanilino) -1,3,5-triazine, 2-octyl mercapto-4,6-bis (3,5-di-tert -Butyl-4-hydroxyphenoxy) -1,3,5-triazine, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenoxy) -1,2,3-triazine, , 3,5-tris (3,5-di-tert-butyl-4-hydroxybenzyl) isocyanurate, 1,3,5-tris (4-tert-butyl-3-hydroxy-2,6-dimethylbenzyl) ) Iso Anurat, 2,4,6-tris (3,5-di-tert-butyl-4-hydroxyphenylethyl) -1,3,5-triazine, 1,3,5-tris (3,5-di-tert -Butyl-4-hydroxyphenylpropionyl) -hexahydro-1,3,5-triazine and 1,3,5-tris (3,5-dicyclohexyl-4-hydroxybenzyl) isocyanurate.

(1-7) Esters of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid and mono- or polyhydric alcohols: β- (3,5-di-tert-butyl-4 -Hydroxyphenyl) propionic acid and methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl Glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N′-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethyl Hexanediol, Trimethylo Propane esters of mono- or polyhydric alcohols selected from, and 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane.

(1-8) Esters of β- (5-tert-butyl-4-hydroxy-3-methylphenyl) propionic acid and mono- or polyhydric alcohols: β- (5-tert-butyl-4-hydroxy-3 -Methylphenyl) propionic acid and methanol, ethanol, n-octanol, i-octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl Glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris (hydroxyethyl) isocyanurate, N, N′-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethyl Hexanediol, tri Tyrolpropane, 4-hydroxymethyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane, and 3,9-bis {2- [3- (3-tert-butyl-4 -Hydroxy-5-methylphenyl) propionyloxy] -1,1-dimethylethyl} -2,4,8,10-tetraoxaspiro [5.5] undecane or an ester with a monohydric or polyhydric alcohol .

(1-9) β- (3,5-dicyclohexyl-4-hydroxyphenyl) propionic acid and a monovalent or polyhydric alcohol ester: β- (3,5-dicyclohexyl-4-hydroxyphenyl) propionic acid; Methanol, ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, Tris (hydroxyethyl) isocyanurate, N, N′-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, and 4-hydroxy Esters with mono- or polyhydric alcohols selected from methyl-1-phospha-2,6,7-trioxabicyclo [2.2.2] octane and the like.

(1-10) 3,5-di-tert-butyl-4-hydroxyphenylacetic acid and monohydric or polyhydric alcohol ester: 3,5-di-tert-butyl-4-hydroxyphenylacetic acid, methanol, Ethanol, octanol, octadecanol, 1,6-hexanediol, 1,9-nonanediol, ethylene glycol, 1,2-propanediol, neopentyl glycol, thiodiethylene glycol, diethylene glycol, triethylene glycol, pentaerythritol, tris ( Hydroxyethyl) isocyanurate, N, N′-bis (hydroxyethyl) oxamide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, and 4-hydroxymethyl-1-phospha 2,6,7 ester of a monohydric or polyhydric alcohol selected from the trio key rust [2.2.2] octane.

(1-11) Amide of β- (3,5-di-tert-butyl-4-hydroxyphenyl) propionic acid: N, N′-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) ) Hexamethylenediamide, N, N′-bis (3,5-di-tert-butyl-4-hydroxyphenylpropionyl) trimethylenediamide, N, N′-bis (3,5-di-tert-butyl-4) -Hydroxyphenylpropionyl) hydrazide and N, N'-bis {2- [3- (3,5-di-tert-butyl-4-hydroxyphenyl) propionyloxy] ethyl} oxamide.

(1-12) Vitamins: α-tocopherol, β-tocopherol, γ-tocopherol, δ-tocopherol and mixtures thereof, tocotrienol, and ascorbic acid.

(2) Phosphorous antioxidants: The following phosphonates, phosphites and oxaphosphaphenanthrenes.

(2-1) Phosphonates: dimethyl-2,5-di-tert-butyl-4-hydroxybenzylphosphonate, diethyl-3,5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-3 , 5-di-tert-butyl-4-hydroxybenzylphosphonate, dioctadecyl-5-tert-butyl-4-hydroxy-3-methylbenzylphosphonate, tetrakis (2,4-di-tert-butylphenyl)- Calcium salt of monoethyl ester of 4,4′-biphenylene diphosphonate and 3,5-di-tert-butyl-4-hydroxybenzylphosphonic acid.

(2-2) Phosphites: trioctyl phosphite, trilauryl phosphite, tridecyl phosphite, octyl diphenyl phosphite, tris (2,4-di-tert-butylphenyl) phosphite, triphenyl phosphite , Tris (butoxyethyl) phosphite, tris (nonylphenyl) phosphite, distearyl pentaerythritol diphosphite, tetra (tridecyl) -1,1,3-tris (2-methyl-5-tert-butyl-4- Hydroxyphenyl) butanediphosphite, tetra (C12-C15 mixed alkyl) -4,4'-isopropylidenediphenyldiphosphite, tetra (tridecyl) -4,4'-butylidenebis (3-methyl-6-tert-butylphenol ) Diphosphite, G (3,5-di-tert-butyl-4-hydroxyphenyl) phosphite, tris (mono, dimixed nonylphenyl) phosphite, hydrogenated-4,4′-isopropylidenediphenol polyphosphite, bis ( Octylphenyl) -bis [4,4′-butylidenebis (3-methyl-6-tert-butylphenol)]-1,6-hexanediol diphosphite, phenyl-4,4′-isopropylidenediphenol-pentaerythritol di Phosphite, bis (2,4-di-tert-butylphenyl) pentaerythritol diphosphite, bis (2,6-di-tert-butyl-4-methylphenyl) pentaerythritol diphosphite, tris [4,4 '-Isopropylidenebis (2-tert-butylphenol)] Sulphite, phenyl diisodecyl phosphite, di (nonylphenyl) pentaerythritol diphosphite, tris (1,3-di-stearoyloxyisopropyl) phosphite, and 4,4'-isopropylidenebis (2-tert-butylphenol)- Di (nonylphenyl) phosphite.

(2-3) Oxaphosphaphenanthrenes: 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 8-chloro-9,10-dihydro-9-oxa-10 Phosphaphenanthrene-10-oxide and 8-t-butyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide.

(3) Sulfur-based antioxidants: dialkylthiopropionates such as the following, esters of octylthiopropionic acid and polyhydric alcohol, esters of laurylthiopropionic acid and polyhydric alcohol, and stearyl thiopropionic acid and polyhydric acid Esters with alcohol.

(3-1) Dialkylthiopropionates: dilauryl thiodipropionate, dimyristyl thiodipropionate, and distearyl thiodipropionate.

(3-2) Esters of octylthiopropionic acid and polyhydric alcohols: octylthiopropionic acid and a polyhydric alcohol selected from glycerin, trimethylolethane, trimethylolpropane, pentaerythritol, trishydroxyethyl isocyanurate, and the like ester.

(3-3) Esters of lauryl thiopropionic acid and polyhydric alcohols: Esters of lauryl thiopropionic acid and glycerin, trimethylol ethane, trimethylol propane, pentaerythritol, and trishydroxyethyl isocyanurate.

(3-4) An ester of stearyl thiopropionic acid and a polyhydric alcohol: stearyl thiopropionic acid and a polyhydric alcohol selected from glycerin, trimethylolethane, trimethylolpropane, pentaerythritol, trishydroxyethyl isocyanurate, and the like ester.

(4) Amine-based antioxidants: N, N′-di-isopropyl-p-phenylenediamine, N, N′-di-sec-butyl-p-phenylenediamine, N, N′-bis (1,4- Dimethylpentyl) -p-phenylenediamine, N, N′-bis (1-ethyl-3-methylpentyl) -p-phenylenediamine, N, N′-bis (1-methylheptyl) -p-phenylenediamine, N , N′-dicyclohexyl-p-phenylenediamine, N, N′-diphenyl-p-phenylenediamine, N, N′-bis (2-naphthyl) -p-phenylenediamine, N-isopropyl-N′-phenyl-p -Phenylenediamine, N- (1,3-dimethylbutyl) -N'-phenyl-p-phenylenediamine, N- (1-methylheptyl) -N'-phenyl-p Phenylenediamine, N-cyclohexyl-N′-phenyl-p-phenylenediamine, 4- (p-toluenesulfamoyl) diphenylamine, N, N′-dimethyl-N, N′-di-sec-butyl-p-phenylene Diamine, diphenylamine, N-allyldiphenylamine, 4-isopropoxydiphenylamine, N-phenyl-1-naphthylamine, N- (4-tert-octylphenyl) -1-naphthylamine, N-phenyl-2-naphthylamine, octylated diphenylamine ( For example, p, p′-di-tert-octyldiphenylamine), 4-n-butylaminophenol, 4-butyrylaminophenol, 4-nonanoylaminophenol, 4-dodecanoylaminophenol, 4-octadecanoylamino Feno Bis (4-methoxyphenyl) -amine, 2,6-di-tert-butyl-4-dimethylaminomethylphenol, 2,4′-diaminodiphenylmethane, 4,4′-diaminodiphenylmethane, N, N, N ', N'-tetramethyl-4,4'-diaminodiphenylmethane, 1,2-bis [(2-methylphenyl) amino] ethane, 1,2-bis (phenylamino) propane, (o-tolyl) biguanide, Bis [4- (1 ′, 3′-dimethylbutyl) phenyl] amine, tert-octylated N-phenyl-1-naphthylamine, mono- and di-alkylated tert-butyl- / tert-octyldiphenylamine mixtures, mono Mixtures of-and di-alkylated nonyldiphenylamine, mono- and di-alkylated dodecyldiphenyl Mixtures of amines, mixtures of mono- and di-alkylated isopropyl / isohexyl diphenylamine, mixtures of mono- and di-alkylated tert-butyldiphenylamine, 2,3-dihydro-3,3-dimethyl-4H-1,4 -Benzothiazine, phenothiazine, mixtures of mono- and di-alkylated tert-butyl / tert-octylphenothiazines, mixtures of mono- and di-alkylated tert-octylphenothiazines, N-allylphenothiazine, N, N, N ' , N′-tetraphenyl-1,4-diaminobut-2-ene, N, N-bis (2,2,6,6-tetramethylpiperidi-4-yl) hexamethylenediamine, bis (2,2, 6,6-tetramethylpiperidi-4-yl) sebacate, 2,2,6,6-tetramethyl Piperidin-4-one, and, 2,2,6,6-tetramethyl-4-ol.

  The light stabilizer is not particularly limited, but may be selected from ultraviolet absorbers such as triazole, benzophenone, ester, acrylate, nickel, triazine, and oxamide, and hindered amine light stabilizers. . These may be used alone or in combination. Specific examples of the light stabilizer include the following (1) to (8).

(1) Triazoles: 2- (2′-hydroxy-5 ′-(1,1,3,3-tetramethylbutyl) phenyl) benzotriazole, 2- (2′-hydroxy-4′-octyloxyphenyl) Benzotriazole, 2- [3′-tert-butyl-2′-hydroxy-5 ′-(2-octyloxycarbonylethyl) phenyl] -5-chlorobenzotriazole, 2- {3′-tert-butyl-5 ′ -[2- (2-Ethylhexyloxy) carbonylethyl] -2'-hydroxyphenyl} -5-chlorobenzotriazole, 2- [3'-tert-butyl-2'-hydroxy-5 '-(2-methoxycarbonyl) Ethyl) phenyl] -5-chlorobenzotriazole, 2- [3′-tert-butyl-2′-hydroxy-5 ′-(2-methyl) Xoxycarbonylethyl) phenyl] benzotriazole, 2- [3′-tert-butyl-2′-hydroxy-5 ′-(2-octyloxycarbonylethyl) phenyl] benzotriazole, 2- {3′-tert-butyl- 5 ′-[2- (2-ethylhexyloxy) carbonylethyl] -2′-hydroxyphenyl} benzotriazole, 2- (3′-dodecyl-2′-hydroxy-5′-methylphenyl) benzotriazole, 2- [ 3′-tert-butyl-2′-hydroxy-5 ′-(2-isooctyloxycarbonylethyl) phenyl] benzotriazole, 2,2′-methylenebis [4- (1,1,3,3-tetramethylbutyl) ) -6-benzotriazol-2-ylphenol], 2- [3′-tert-butyl-5] Transesterification product of-(2-methoxycarbonylethyl) -2'-hydroxyphenyl] -2H-benzotriazole and polyethylene glycol 300, a triazole compound represented by the following formula (11), and 2- [2'- Hydroxy-3 ′-(α, α-dimethylbenzyl) -5 ′-(1,1,3,3-tetramethylbutyl) phenyl] benzotriazole; 2- [2′-hydroxy-3 ′-(1,1 , 3,3-tetramethylbutyl) -5 ′-(α, α-dimethylbenzyl) phenyl] benzotriazole.

上記式（１１）中、Ｒは、３’−ｔｅｒｔ−ブチル−４’−ヒドロキシ−５’−２Ｈ−ベンゾトリアゾール−２−イルフェニルである。

In the above formula (11), R is 3′-tert-butyl-4′-hydroxy-5′-2H-benzotriazol-2-ylphenyl.

(2) Benzophenone series: 4-decyloxy, 4-benzyloxy, 4,2 ', 4'-trihydroxy and 2'-hydroxy-4,4'-dimethoxy derivatives.

(3) Esters: 4-tert-butylphenyl salicylate, phenyl salicylate, octylphenyl salicylate, dibenzoylresorcinol, bis (4-tert-butylbenzoyl) resorcinol, benzoylresorcinol, 2,4-di-tert-butyl Phenyl 3,5-di-tert-butyl-4-hydroxybenzoate, hexadecyl-3,5-di-tert-butyl-4-hydroxybenzoate, octadecyl-3,5-di-tert-butyl-4-hydroxy Benzoate and 2-methyl-4,6-di-tert-butylphenyl 3,5-di-tert-butyl-4-hydroxybenzoate.

(4) Acrylate system: ethyl-α-cyano-β, β-diphenyl acrylate, isooctyl-α-cyano-β, β-diphenyl acrylate, methyl-α-carbomethoxycinnamate, methyl-α-cyano-β -Methyl-p-methoxycinnamate, butyl-α-cyano-β-methyl-p-methoxycinnamate, methyl-α-carbomethoxy-p-methoxycinnamate and N- (β-carbomethoxy-β-cyanovinyl) -2-Methylindoline.

(5) Nickel-based: 1: 1 or 1: 2 complexes with or without additional ligands such as n-butylamine, triethanolamine and N-cyclohexyldiethanolamine (eg, 2,2′-thiobis [4 -(1,1,3,3-tetramethylbutyl) phenol] nickel complex), nickel dibutyldithiocarbamate, 4-hydroxy-3,5-di-tert-butylbenzyl phosphate monoalkyl ester (for example, Methyl salts or ethyl esters), nickel complexes of ketoximes (eg, nickel complexes of 2-hydroxy-4-methylphenylundecyl ketoxime), and 1-phenyl-4 with or without additional ligands -Nickel complex of lauroyl-5-hydroxypyrazole.

(6) Triazine series: 2,4,6-tris (2-hydroxy-4-octyloxyphenyl) -1,3,5-triazine, 2- (2,4-dihydroxyphenyl) -4,6-bis ( 2,4-dimethylphenyl) -1,3,5-triazine, 2,4-bis (2-hydroxy-4-propyloxyphenyl) -6- (2,4-dimethylphenyl) -1,3,5- Triazine, 2- (2-hydroxy-4-octyloxyphenyl) -4,6-bis (4-methylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-dodecyloxyphenyl)- 4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-tridecyloxyphenyl) -4,6-bis (2,4-dimethylphenyl) -1,3, -Triazine, 2- [2-hydroxy-4- (2-hydroxy-3-butyloxypropoxy) phenyl] -4,6-bis (2,4-dimethyl) -1,3,5-triazine, 2- [ 2-hydroxy-4- (2-hydroxy-3-octyloxypropyloxy) phenyl] -4,6-bis (2,4-dimethyl) -1,3,5-triazine, 2- [2-hydroxy-4 -(2-hydroxy-3-dodecyloxypropoxy) phenyl] -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine, 2- (2-hydroxy-4-methoxyphenyl)- 4,6-diphenyl-1,3,5-triazine, 2,4,6-tris [2-hydroxy-4- (3-butoxy-2-hydroxypropoxy) phenyl] -1,3,5-triazine, -(2-hydroxyphenyl) -4- (4-methoxyphenyl) -6-phenyl-1,3,5-triazine and 2- {2-hydroxy-4- [3- (2-ethylhexyl-1-oxy) -2-hydroxypropyloxy] phenyl} -4,6-bis (2,4-dimethylphenyl) -1,3,5-triazine.

(7) Oxamide series: 4,4′-dioctyloxyoxanilide, 2,2′-diethoxyoxanilide, 2,2′-dioctyloxy-5,5′-di-tert-butoxanilide, 2,2 '-Didodecyloxy-5,5'-di-tert-butoxanilide, 2-ethoxy-2'-ethyloxanilide, N, N'-bis (3-dimethylaminopropyl) oxamide, 2-ethoxy-5 tert-butyl-2'-ethoxanilide and mixtures thereof with 2-ethoxy-2'-ethyl-5,4'-di-tert-butoxanilide, mixtures of o- and p-methoxy-disubstituted oxanilides, and o- And a mixture of p-ethoxy-disubstituted oxanilide.

(8) Hindered amine series: bis (2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (2,2,6,6-tetramethyl-4-piperidyl) succinate, bis (1,2, 2,6,6-pentamethyl-4-piperidyl) sebacate, bis (1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate, bis (1,2,2,6,6- Pentamethyl-4-piperidyl) n-butyl-3,5-di-tert-butyl-4-hydroxybenzylmalonate, 1- (2-hydroxyethyl) -2,2,6,6-tetramethyl-4-hydroxy Condensate of piperidine and succinic acid, N, N′-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-tert-octylamino-2, Linear or cyclic condensates with dichloro-1,3,5-triazine, tris (2,2,6,6-tetramethyl-4-piperidyl) nitrilotriacetate, tetrakis (2,2,6,6) -Tetramethyl-4-piperidyl) -1,2,3,4-butanetetracarboxylate, 1,1 '-(1,2-ethanediyl) -bis (3,3,5,5-tetramethylpiperazinone ), 4-benzoyl-2,2,6,6-tetramethylpiperidine, 4-stearyloxy-2,2,6,6-tetramethylpiperidine, bis (1,2,2,6,6-pentamethylpiperidyl) ) -2-n-butyl-2- (2-hydroxy-3,5-di-tert-butylbenzyl) malonate, 3-n-octyl-7,7,9,9-tetramethyl-1,3,8 -Triazaspiro [4 5] Decane-2,4-dione, bis (1-octyloxy-2,2,6,6-tetramethylpiperidyl) sebacate, bis (1-octyloxy-2,2,6,6-tetramethylpiperidyl) Succinate, N, N′-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-morpholino-2,6-dichloro-1,3,5-triazine linear Cyclic condensates;

  2-Chloro-4,6-bis (4-n-butylamino-2,2,6,6-tetramethylpiperidyl) -1,3,5-triazine and 1,2-bis (3-aminopropylamino) Condensate with ethane, 2-chloro-4,6-di- (4-n-butylamino-1,2,2,6,6-pentamethylpiperidyl) -1,3,5-triazine and 1,2 A condensate with bis (3-aminopropylamino) ethane, 8-acetyl-3-dodecyl-7,7,9,9-tetramethyl-1,3,8-triazaspiro [4.5] decane-2, 4-dione, 3-dodecyl-1- (2,2,6,6-tetramethyl-4-piperidyl) pyrrolidine-2,5-dione, 3-dodecyl-1- (1,2,2,6,6) -Pentamethyl-4-piperidyl) pyrrolidine-2,5-dione, 5- (2 Ethylhexanoyl) -oxymethyl-3,3,5-trimethyl-2-morpholinone, 1- (2-hydroxy-2-methylpropyl) -4-octadecanoyloxy-2,2,6,6-tetramethylpiperidine 1,3,5-tris (N-cyclohexyl-N- (2,2,6,6-tetramethylpiperazin-3-one-4-yl) amino) -s-triazine, 1,3,5-tris [N-cyclohexyl-N- (1,2,2,6,6-pentamethylpiperazin-3-one-4-yl) amino] -s-triazine, 2,4-bis [(1-cyclohexyloxy-2 , 2,6,6-piperidin-4-yl) butylamino] -6-chloro-s-triazine and N, N′-bis (3-aminopropyl) ethylenediamine, 4-hexadecyl Oxy - and mixtures of 4-stearyloxy-2,2,6,6-tetramethylpiperidine;

  A condensate of N, N′-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine and 4-cyclohexylamino-2,6-dichloro-1,3,5-triazine, 1 , 2-bis (3-aminopropylamino) ethane with 2,4,6-trichloro-1,3,5-triazine and 4-butylamino-2,2,6,6-tetramethylpiperidine 1,6-hexanediamine and 2,4,6-trichloro-1,3,5-triazine, N, N-dibutylamine and 4-butylamino-2,2,6,6-tetramethylpiperidine N- (2,2,6,6-tetramethyl-4-piperidyl) -n-dodecylsuccinimide, N- (1,2,2,6,6-pentamethyl-4-piperidyl) -n -Dodecilsk Imide, 2-undecyl-7,7,9,9-tetramethyl-1-oxa-3,8-diaza-4-oxo-spiro [4.5] decane; 5- (2-ethylhexanoyl) oxymethyl -3,3,5-trimethyl-2-morpholinone, 7,7,9,9-tetramethyl-2-cycloundecyl-1-oxa-3,8-diaza-4-oxo-spiro [4.5] Reaction product of decane and epichlorohydrin, 1,1-bis (1,2,2,6,6-pentamethyl-4-piperidyloxycarbonyl) -2- (4-methoxyphenyl) ethene, N, N '-Bis-formyl-N, N'-bis (2,2,6,6-tetramethyl-4-piperidyl) hexamethylenediamine, 4-methoxymethylenemalonic acid and 1,2,2,6,6-pentamethyl -4-hydroxy Diesters with peridine, poly [methylpropyl-3-oxy-4- (2,2,6,6-tetramethyl-4-piperidyl)] siloxane, and maleic anhydride α-olefin copolymer and 2,2, Reaction product with 6,6-tetramethyl-4-aminopiperidine or 1,2,2,6,6-pentamethyl-4-aminopiperidine.

  The use of the composition and the polymer or cured product formed by polymerizing the composition is not particularly limited. For example, electronic materials (eg castings and circuits of insulators, AC transformers, switchgears, etc.) Units, various component packages, IC / LED / semiconductor peripheral materials [sealing materials, lens materials, substrate materials, die bond materials, chip coating materials, laminated plates, optical fibers, optical waveguides, optical filters, adhesives for electronic components , Coating materials, sealing materials, insulating materials, photoresists, encap materials, potting materials, light transmission layers and interlayer insulating layers of optical disks, light guide plates, antireflection films, etc.], rotating machines such as generators and motors, windings Wire impregnation, printed wiring board, laminated board, insulation board, medium-sized insulators, coils, connectors, terminals, various cases, electrical components, etc.), paint (corrosion-resistant paint, maintenance, Marine coating, corrosion-resistant lining, primer for automobiles and home appliances, beverage / beer can, outer surface lacquer, extrusion tube coating, general corrosion-resistant coating, maintenance coating, lacquer for woodwork products, automotive electrodeposition primer, other industrial electrodeposition coatings, Beverage / beer can inner surface lacquer, coil coating, drum / can inner surface coating, acid-resistant lining, wire enamel, insulation paint, automotive primer, exterior / corrosion coating for various metal products, pipe inner / outer surface coating, electrical component insulation coating, etc.) , Composite materials (Chemical plant pipes and tanks, aircraft materials, automobile parts, various sports equipment, carbon fiber composite materials, aramid fiber composite materials, etc.), civil engineering and building materials (floor materials, paving materials, membranes, anti-slip and thin Layer pavement, concrete splicing / uplifting, anchor embedded adhesion, precast concrete Bonding, tile adhesion, repairing cracks in concrete structures, grouting and leveling of pedestals, anti-corrosion and waterproofing of water and sewage facilities, anti-corrosion laminated lining of tanks, anti-corrosion coating of iron structures, mastic coating of building exterior walls, etc.), Adhesives (adhesives of the same or different materials such as metal, glass, ceramics, cement concrete, wood and plastic, adhesives for assembly of automobiles, railway vehicles, aircraft, etc., adhesives for manufacturing prefabricated composite panels, etc. Molds, two-component molds, sheet types, etc.), aircraft / automobile / plastic molding jigs (press molds, stretched dies, matched dies and other resin molds, vacuum molding / blow molding molds, master models, casting patterns, lamination Jigs, jigs for various inspections, etc.), modifiers and stabilizers (resin processing of fibers, stabilizers for polyvinyl chloride, synthetic rubber) And the like, rubber modifiers (vulcanizing agents, vulcanization accelerators, etc.) and the like.

  Examples of the lens material include a lens for an optical device, a lens for an automobile lamp, a spectacle lens, a pickup lens such as a CD / DVD, and a lens for a projector.

  The use of the LED encapsulant is not particularly limited, and is a display, an electric display panel, a traffic light, a display backlight (organic EL display, mobile phone, mobile PC, etc.), automotive interior / exterior illumination, illumination, It can be used in a wide range of fields such as lighting equipment and flashlights.

  Examples that specifically describe this embodiment will be described below. The present invention is not limited to the following examples as long as the gist thereof is not exceeded.

<Detection of complex contained in boron trihalide-carbonate compound: ¹¹ B-NMR measurement>
¹¹ B-NMR measurement was performed according to the following procedure.
(1) To a sample bottle, 10 mg of trimethoxyborane (manufactured by Wako Pure Chemical Industries, Ltd.) was weighed and chloroform-d (manufactured by Wako Pure Chemical Industries, Ltd.) was added to prepare a total amount of 1 g.
(2) Weigh 10 mg of boron trihalide compound used to prepare the boron trihalide-carbonate compound in a sample bottle, add chloroform-d (manufactured by Wako Pure Chemical Industries, Ltd.), Prepared to 1 g.
(3) In a sample bottle, 10 mg of the prepared boron trihalide-carbonate compound was weighed, and chloroform-d (manufactured by Wako Pure Chemical Industries, Ltd.) was added to prepare a total amount of 1 g.
(4) The solution of (2) was transferred to a special NMR tube (for example, “N-502B” manufactured by Nippon Seimitsu Chemical Co., Ltd.) that can be inserted into an NMR tube having a diameter of 5 mmφ.
(5) The solution of (1) was transferred to an NMR tube having a diameter of 5 mmφ, the special NMR tube of (4) was inserted, and ¹¹ B-NMR was measured under the following conditions.
Fourier transform nuclear magnetic resonance apparatus: “α-400” manufactured by JEOL Ltd.
Nuclide: ¹¹ B
Accumulation count: 1000 times (6) The solution of (3) above was transferred to a special NMR tube (for example, “N-502B” manufactured by Japan Seimitsu Chemical Co., Ltd.) that can be inserted into an NMR tube having a diameter of 5 mmφ.
(7) The solution of (1) was transferred to an NMR tube having a diameter of 5 mmφ, the special NMR tube of (6) was inserted, and ¹¹ B-NMR was measured in the same manner as in (5) above.
(8) In the measurement results obtained in the above (5) and (7), the peak of trimethoxyborane is 18 ppm, and the peak obtained in (7) is different from the peak obtained in (5). When detected, it was judged that a complex was formed in the prepared boron trihalide-carbonate compound.

<Epoxy equivalent (WPE)>
It was measured according to “JIS K7236: 2001 (How to determine epoxy equivalent of epoxy resin)”.

<Calculation of mixing index α>
The mixing index α was calculated by the following formula (2).
Index α = αc / αb (2)
here,
αc: (A) amount of carbonate group of carbonate compound (mol)
αb: (B) represents the amount (mol) of boron trihalide.

<Calculation of mixing index β>
The mixing index β was calculated by the following formula (9).
Index β = αb / αep × 100 (9)
here,
αb: (B) Boron trihalide substance amount (mol)
αep: (C) The amount (mol) of the epoxy group contained in the epoxy compound, respectively.

<Calculation of epoxy group reaction rate (hereinafter referred to as “EA method”): ¹ H-NMR measurement>
¹ H-NMR measurement was performed according to the following procedure.
(1) A 10 mg sample and 20 mg of an internal standard substance were weighed into a sample bottle, and chloroform-d (manufactured by Wako Pure Chemical Industries, Ltd.) was further added to prepare a total amount of 1 g.
Internal standard substance: 1,1,2,2-tetrabromoethane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “TBE”)
(2) The solution of (1) was transferred to an NMR tube having a diameter of 5 mmφ, and ¹ H-NMR was measured under the following conditions.
Fourier transform nuclear magnetic resonance apparatus: “α-400” manufactured by JEOL Ltd.
Nuclide: ¹ H
Accumulation count: 1000 times From the above measurement results, the epoxy group reaction rate was calculated by the following procedure.
(3) The area value of the peak derived from the epoxy group was calculated from the ¹ H-NMR chart.
Here, the peak derived from the epoxy group refers to a peak derived from one hydrogen on the hydrocarbon constituting the epoxy group. A peak that does not overlap with a peak derived from hydrogen other than hydrogen derived from an epoxy group constituting the epoxy compound is appropriately selected.
(4) The area value of the peak derived from the internal standard substance was calculated from the ¹ H-NMR chart.
(5) The area values calculated in the above (3) and (4) were substituted into the following formula to determine the epoxy group reaction rate (%).
Epoxy group reaction rate (%) = 100−EPOA × (TBEG / TBEM) × (2 / TBEA) × (REAG / SAMG) × (WPE / EPOG) × 100
EPOA: Area value of peak derived from epoxy group TBEA: Area value of peak derived from two hydrogens of TBE EPOG: Weight of epoxy compound used in preparing composition (g)
WPE: Epoxy equivalent (g / mol) of the epoxy compound used in preparing the composition
REAG: Weight of composition (g)
TBEG: Weight (g) of TBE used in preparing a solution for ¹ H-NMR measurement (20 mg in this example)
TBEM: Molecular weight of TBE SAMG: The weight (g) of the sample used in preparing the solution for ¹ H-NMR measurement (10 mg in this example)
When the hydrogen on the hydrocarbon constituting the epoxy group in the epoxy compound contained in the sample is observed as the same peak in the ¹ H-NMR measurement, the procedure of (5) is changed as follows. This makes it possible to calculate.
(5-2) The area values calculated in (3) and (4) above were substituted into the following formula to determine the epoxy group reaction rate (%).
Epoxy group reaction rate (%) = 100− {EPOA / (number of hydrogen constituting the epoxy group-derived peak)} × (TBEG / TBEM) × (2 / TBEA) × (REAG / SAMG) × (WPE / EPOG) x 100

<Calculation of epoxy group reaction rate (hereinafter referred to as “EB method”): FT-IR measurement>
In the EA method, when the sample does not dissolve in chloroform-d, the epoxy group reaction rate is calculated by the EB method.
The FT-IR measurement was performed according to the following procedure.
(1) In an agate mortar, 2 mg of a sample and 100 mg of potassium bromide (Aldrich, IR grade) were weighed and ground with an agate pestle until uniform.
(2) The sample (1) (50 mg) was molded into a disk shape using a tablet molding machine.
(3) The molded product of (2) was placed in a tablet sample holder, and FT-IR measurement was performed under the following conditions.
Fourier transform infrared spectrometer: “Nicolet 6700” manufactured by Thermo Fisher Scientific
Resolution: 4cm ^-1
Measurement method: Permeation method integration number: 128 times From the above measurement results, the epoxy group reaction rate was calculated according to the following procedure.
(4) The area value of the peak derived from the epoxy group was calculated from the FT-IR chart.
Here, the peak derived from an epoxy group refers to a peak derived from vibration between atoms constituting the epoxy group. In the compound contained in the sample, a peak that does not overlap with a peak derived from vibration between atoms other than a peak derived from an epoxy group is appropriately selected.
(5) The area value calculated in (4) was substituted into the following formula to determine the epoxy group reaction rate (%).
Epoxy group reaction rate (%) = 100−RIRA / SIRA × 100
RIRA: In the FT-IR chart obtained as a result of measuring the sample, the peak area derived from the epoxy group SIRA: In the FT-IR chart obtained as a result of measuring the epoxy compound before polymerization used for preparing the sample , Peak area derived from epoxy group.

<Stability evaluation A>
A part of the prepared composition was put into a thermostat set at 20 ° C. and held for 24 hours, and then the epoxy group reaction rate was calculated by the EA method.
Stability is determined to be good (“A”) when the epoxy group reaction rate is 10% or less, particularly good (“AA”) when the epoxy group reaction rate is 5% or less, and poor (“ C ").

<Stability evaluation B>
In the stability evaluation A, when the composition was not completely dissolved in chloroform-d, the epoxy group reaction rate was calculated by the EB method.
Stability is determined to be good (“A”) when the epoxy group reaction rate is 10% or less, particularly good (“AA”) when the epoxy group reaction rate is 5% or less, and poor (“ C ").

<Polymerization evaluation A>
The epoxy group reaction rate of the obtained polymer was calculated by the EA method.
Polymerizability is judged to be good (“A”) when the epoxy group reaction rate is 90% or more, particularly good (“AA”) when it is 95% or more, and poor (“ C ").

<Polymerization evaluation B>
In the polymerization evaluation A, when the polymer was not completely dissolved in chloroform-d, the epoxy group reaction rate was calculated by the EB method.
Polymerizability is judged to be good (“A”) when the epoxy group reaction rate is 90% or more, particularly good (“AA”) when it is 95% or more, and poor (“ C ").

<Transparency evaluation>
Yellowness (YI) was measured according to the following procedure.
YI was determined according to “ASTM D1925-70 (1988): Test Method for Yellowness Index of Plastics”.
(1) A part of the prepared composition is put in a short optical path decomposition cell (manufactured by Sterna, open type 20 / O, 12.5 mm × 3.5 mm × 45 mm, optical path length 1 mm), and the polymerizable property of the composition Polymerization was performed at the same temperature and time as the conditions for the evaluation.
In addition, in polymerizability evaluation, about the thing which prepared the polymer in the sealed pressure bottle, the sample for evaluation was prepared in the following procedures.
(2-1) The polymer was taken out from the pressure bottle and dissolved in the same weight of dichloromethane (manufactured by Wako Pure Chemical Industries, Ltd.) to obtain a polymer solution.
The compound used for dissolving the polymer is not particularly limited as long as it can dissolve the polymer and can be removed in a later step.
(2-2) The obtained polymer solution was put into a short optical path decomposition cell (manufactured by Sterna, open type 20 / O, 12.5 mm × 3.5 mm × 45 mm, optical path length 1 mm).
(2-3) Vacuum dryer (Tokyo Rika Kikai Co., Ltd., VOS-451D, ULVAC Kiko Co., Ltd., small oil rotary vacuum pump GCD-201X was used for the vacuum pump) above (2- The cell obtained in 2) was placed and dried at room temperature, 13 Pa, for 24 hours.
In addition, the temperature and pressure at the time of drying are not particularly limited, and the conditions under which the volatiles contained in the polymer solution are not volatilized rapidly may be appropriately selected. In this example, the pressure was gradually reduced from normal pressure to finally 13 kPa.
(3) YI was measured with the following apparatus for the cell containing the polymer obtained in (1) or (2-3).
Spectral color meter: “SD5000” manufactured by Nippon Denshoku Industries Co., Ltd.
Transparency is judged as good (“A”) when YI is 10 or less, judged as particularly good (“AA”) when YI is 5 or less, and judged as poor (“C”) in other cases. did.

<Comprehensive judgment>
In all evaluations of stability evaluation, polymerization evaluation and transparency evaluation, when judged to be particularly good, and judged to be good in at least one evaluation, and judged to be particularly good or good in other evaluations When it was, it was set as a pass ("AA" or "A") as comprehensive judgment. All other cases were rejected ("C").

The raw materials used in Examples, Comparative Examples and Preparation Examples are shown in the following (1) to (93).
(Epoxy compound)
(1) Epoxy compound A: ethylene oxide (manufactured by Aldrich, hereinafter referred to as “EPO-1”)
Epoxy equivalent (WPE): 44 g / eq.
(2) Epoxy compound B: propylene oxide (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “EPO-2”)
Epoxy equivalent (WPE): 58 g / eq.
(3) Epoxy compound C: 1,2-epoxybutane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “EPO-3”)
Epoxy equivalent (WPE): 72 g / eq.
(4) Epoxy compound D: 1,2-epoxypentane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “EPO-4”)
Epoxy equivalent (WPE): 86 g / eq.
(5) Epoxy compound E: 1,2-epoxyhexane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “EPO-5”)
Epoxy equivalent (WPE): 100 g / eq.
(6) Epoxy compound F: 1,2-epoxyheptane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “EPO-6”)
Epoxy equivalent (WPE): 114 g / eq.
(7) Epoxy compound G: 1,2-epoxyoctane (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “EPO-7”)
Epoxy equivalent (WPE): 128 g / eq.
(8) Epoxy compound H: 1,2-epoxydecane (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “EPO-8”)
Epoxy equivalent (WPE): 156 g / eq.
(9) Epoxy compound I: 1,2-epoxydodecane (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “EPO-9”)
Epoxy equivalent (WPE): 184 g / eq.
(10) Epoxy compound J: 1,2-epoxytetradecane (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “EPO-10”)
Epoxy equivalent (WPE): 212 g / eq.
(11) Epoxy compound K: 1,2-epoxyhexadecane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “EPO-11”)
Epoxy equivalent (WPE): 240 g / eq.
(12) Epoxy compound L: 1,2-epoxy octadecane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “EPO-12”)
Epoxy equivalent (WPE): 268 g / eq.
(13) Epoxy compound M: 1,2-epoxy eicosane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “EPO-13”)
Epoxy equivalent (WPE): 297 g / eq.
(14) Epoxy compound N: phenylglycidyl ether (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “EPO-14”)
Epoxy equivalent (WPE): 150 g / eq.
(15) Epoxy compound O: bisphenol A type epoxy compound (hereinafter referred to as “EPO-15”)
・ Product name: “AER”, manufactured by Asahi Kasei Epoxy Corporation
Epoxy equivalent (WPE): 189 g / eq.
(16) Epoxy compound P: hydrogenated bisphenol A type epoxy compound (hereinafter referred to as “EPO-16”)
・ Product name: “YX8000”, manufactured by Japan Epoxy Resin Co., Ltd.
Epoxy equivalent (WPE): 205 g / eq.
(17) Epoxy compound Q: bisphenol A type epoxy compound (hereinafter referred to as “EPO-17”)
・ Product name: “AER”, manufactured by Asahi Kasei Epoxy Corporation
Epoxy equivalent (WPE): 450 g / eq.
(18) Epoxy compound R: bisphenol A type epoxy compound (hereinafter referred to as “EPO-18”)
・ Product name: “AER”, manufactured by Asahi Kasei Epoxy Corporation
Epoxy equivalent (WPE): 480 g / eq.
(19) Epoxy compound S: bisphenol A type epoxy compound (hereinafter referred to as “EPO-19”)
・ Product name: “AER”, manufactured by Asahi Kasei Epoxy Corporation
Epoxy equivalent (WPE): 560 g / eq.
(20) Epoxy compound T: bisphenol A type epoxy compound (hereinafter referred to as “EPO-20”)
・ Product name: “AER”, manufactured by Asahi Kasei Epoxy Corporation
Epoxy equivalent (WPE): 650 g / eq.
(21) Epoxy compound U: cyclopentene oxide (manufactured by Aldrich, hereinafter referred to as “EPO-21”)
Epoxy equivalent (WPE): 84 g / eq.
(22) Epoxy compound V: cyclohexene oxide (manufactured by Aldrich, hereinafter referred to as “EPO-22”)
Epoxy equivalent (WPE): 98 g / eq.
(23) Epoxy compound W: cycloheptene oxide (manufactured by Aldrich, hereinafter referred to as “EPO-23”)
Epoxy equivalent (WPE): 112 g / eq.
(24) Epoxy compound X: cyclooctene oxide (manufactured by Aldrich, hereinafter referred to as “EPO-24”)
Epoxy equivalent (WPE): 126 g / eq.
(25) Epoxy compound Y: alicyclic epoxy compound (hereinafter referred to as “EPO-25”)
・ Product name: Daicel Chemical Industries, Ltd. “Celoxide 2021P”
Epoxy equivalent (WPE): 131 g / eq.
(26) Epoxy compound Z: bis (2,3-epoxypropyl) disulfide (hereinafter referred to as “EPO-26”)
BEDS was synthesized according to the method described in JP-A-2002-194083.
Epoxy equivalent (WPE): 91 g / eq.
(27) Epoxy compound AA: 1,3-bis (3-glycidoxypropyl) -1,1,3,3-tetramethyldisiloxane (hereinafter referred to as “EPO-27”)
・ Product name: Shin-Etsu Chemical Co., Ltd., “LS-7970”
Epoxy equivalent (WPE): 182 g / eq.
(28) Epoxy compound AB: bis [2- (3,4-epoxycyclohexyl) ethyl] tetramethyldisiloxane (hereinafter referred to as “EPO-28”)
-Trade name: Gelest, Inc. , "SIB1092.0"
Epoxy equivalent (WPE): 192 g / eq.
(29) Epoxy compound AC: 1,3,5,7-tetra- (3-glycidoxypropyl) tetramethylcyclotetrasiloxane (hereinafter referred to as “EPO-29”)
Euro. Polym. J. et al. 2010, 46, 1545. TGCS was synthesized according to the method described.
Epoxy equivalent (WPE): 174 g / eq.
(30) Epoxy compound AD: 1,3,5,7-tetra- [2- (3,4-epoxycyclohexylethyl)] tetramethylcyclotetrasiloxane (hereinafter referred to as “EPO-30”)
TCCS was synthesized according to the method described in JP-A 2000-103859.
Epoxy equivalent (WPE): 184 g / eq.
(31) Epoxy compound AE: butadiene monoxide (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “EPO-31”)
Epoxy equivalent (WPE): 70 g / eq.
(32) Epoxy compound AF: 1,2-epoxy-5-hexene (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “EPO-32”)
Epoxy equivalent (WPE): 98 g / eq.
(33) Epoxy compound AG: allyl glycidyl ether (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “EPO-33”)
Epoxy equivalent (WPE): 114 g / eq.
(34) Epoxy compound AH: 1,2-epoxy-4-vinylcyclohexane (manufactured by Aldrich, hereinafter referred to as “EPO-34”)
Epoxy equivalent (WPE): 124 g / eq.
(35) Epoxy compound AI: Glycidyl methacrylate (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “EPO-35”)
Epoxy equivalent: 142 g / eq.

(Carbonate compound)
(36) Carbonate compound A: dimethyl carbonate (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBA”)
(37) Carbonate compound B: 1,3-dioxolan-2-one (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBB”. It is also expressed as ethylene carbonate as another name.)
(38) Carbonate compound C: ethyl methyl carbonate (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBC”)
(39) Carbonate compound D: 4-methyl-1,3-dioxolan-2-one (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBD”. It is also expressed as propylene carbonate.)
(40) Carbonate compound E: 1,3-dioxan-2-one (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBE”)
(41) Carbonate compound F: diethyl carbonate (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBF”)
(42) Carbonate compound G: 4-ethyl-1,3-dioxolan-2-one (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBG”. As an alias, it is also expressed as 1,2-butylene carbonate. )
(43) Carbonate compound H: 4- (methoxymethyl) -1,3-dioxolan-2-one (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBH”)
(44) Carbonate compound I: Dipropyl carbonate (manufactured by Aldrich, hereinafter referred to as “MCBI”)
(45) Carbonate compound J: 5,5-dimethyl-1,3-dioxan-2-one (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “MCBJ”)
(46) Carbonate compound K: 5,5-diethyl-1,3-dioxan-2-one (manufactured by Aldrich, hereinafter referred to as “MCBK”)
(47) Carbonate compound L: 3,5-dimethylphenylethyl carbonate (manufactured by Aldrich, hereinafter referred to as “MCBL”)
(48) Carbonate compound M: Diphenyl carbonate (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBM”)
(49) Carbonate compound N: benzyl phenyl carbonate (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBN”)
(50) Carbonate compound O: dibenzyl carbonate (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBO”)
(51) Carbonate compound P: bis (2-methoxyphenyl) carbonate (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBP”)
(52) Carbonate compound Q: methyl 2-({[2- (methoxycarbonyl) phenoxy] carbonyl} oxy) benzoate (manufactured by Aldrich, hereinafter referred to as “MCBQ”)
(53) Carbonate compound R: didodecyl carbonate (manufactured by Aldrich, hereinafter referred to as “MCBR”)
(54) Carbonate compound S: ethylene glycol bis (methyl carbonate) (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBS”)
(55) Carbonate compound T: erythritol bis (carbonate) (manufactured by Aldrich, hereinafter referred to as “MCBT”)
(56) Carbonate compound U: ethylene glycol bis (ethyl carbonate) (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MCBU”)

(Boron trihalide compound)
(57) Boron trihalide compound A: Boron trifluoride dimethyl ether complex (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “BF3DME”)
(58) Boron trihalide compound B: boron trifluoride diethyl ether complex (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “BF3DEE”)
(59) Boron trihalide compound C: Boron trifluoride dibutyl ether complex (manufactured by Aldrich, hereinafter referred to as “BF3DBE”)
(60) Boron trihalide compound D: Boron trifluoride tert-butyl methyl ether complex (manufactured by Aldrich, hereinafter referred to as “BF3TBME”)
(61) Boron trihalide compound E: Boron trifluoride tetrahydrofuran complex (manufactured by Aldrich, hereinafter referred to as “BF3THF”)
(62) Boron trihalide compound F: Boron trifluoride methyl sulfide complex (manufactured by Aldrich, hereinafter referred to as “BF3DMS”)
(63) Boron trihalide compound G: Boron trifluoride methanol complex (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “BF3MNOL”)
(64) Boron trihalide compound H: Boron trifluoride propanol complex (manufactured by Aldrich, hereinafter referred to as “BF3PNOL”)
(65) Boron trihalide compound I: Boron trifluoride acetic acid complex (manufactured by Aldrich, hereinafter referred to as “BF3ACOH”)
(66) Boron trihalide compound J: Boron trifluoride phenol complex (manufactured by Aldrich, hereinafter referred to as “BF3PHNOL”)
(67) Boron trihalide compound K: Boron trifluoride ethylamine complex (manufactured by Aldrich, hereinafter referred to as “BF3MEA”)
(68) Boron trihalide compound L: Boron trifluoride piperidine complex (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “BF3PPD”)
(69) Boron trihalide compound Q: Boron trichloride (1.0 mol / L dichloromethane solution) (manufactured by Aldrich, hereinafter referred to as “BCl 3 DCM”)
(70) Boron trihalide compound R: Boron tribromide (1.0 mol / L dichloromethane solution) (manufactured by Aldrich, hereinafter referred to as “BBr3DCM”)

(Thermal polymerization accelerator)
(71) Phosphonium salt compound: tetra-n-butylphosphonium bromide (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “TBPB”)
(72) Amine compound A: Tributylamine (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “TBA”)
(73) Amine compound B: N, N-dimethylcyclohexylamine (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “DMCHA”)
(74) Amine compound C: N, N-diethylethanolamine (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “DEENA”)
(75) Sulfonium salt compound A: trade name “SI-25” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S25”)
(76) Sulfonium salt compound B: trade name “SI-60” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S60”)
(77) Sulfonium salt compound C: trade name “SI-80” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S80”)
(78) Sulfonium salt compound D: Trade name “SI-100” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S100”)
(79) Sulfonium salt compound E: Trade name “SI-110” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S110”)
(80) Sulfonium salt compound F: Trade name “SI-150” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S150”)
(81) Sulfonium salt compound G: trade name “SI-180” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S180”)

(Additive compound)
(82) Additive Compound A: Dichloromethane (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “DCM”)
(83) Additive compound B: diethyl ether (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “DEE”)

(Chain transfer agent)
(84) Chain transfer agent A: 1-butanol (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “CTRA”)
(85) Chain transfer agent B: 2-butanol (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “CTRB”)
(86) Chain transfer agent C: ethylene glycol (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “CTRC”)
(87) Chain transfer agent D: 1,2-propanediol (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “CTRD”)
(88) Chain transfer agent E: 2,3-butanediol (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “CTRE”)
(89) Chain transfer agent F: butano-4-lactone (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “CTRF”)
(90) Chain transfer agent G: pentano-4-lactone (manufactured by Aldrich, hereinafter referred to as “CTRG”)
(91) Chain transfer agent H: 1,3-dioxan-2-one (manufactured by Aldrich, hereinafter referred to as “CTRH”)
(92) Chain transfer agent I: Hexamethylcyclotrisiloxane (manufactured by Shin-Etsu Chemical Co., Ltd., hereinafter referred to as “CTRI”)
(93) Chain transfer agent J: Octamethylcyclotetrasiloxane (manufactured by Shin-Etsu Chemical Co., Ltd., hereinafter referred to as “CTRJ”)

Example 1
<Preparation of boron trihalide-carbonate compound>
(1) Preparation: On the magnetic stirrer, a water bath equipped with a throwing-type cooling / heating unit was placed, and water and a stirrer were placed therein. The throw-in type cooling and heating unit was activated and the temperature of water was set to 20 ° C.
(2) A reaction vessel in a nitrogen atmosphere was placed in the water bath of (1) above, and each raw material was added to the reaction vessel according to the composition ratio in Table 1, and stirred for 1 hour.
(3) A vacuum distillation apparatus was attached to the reaction vessel, and the pressure was gradually reduced. Finally, the pressure was reduced to 2 kPa and maintained for 4 hours.
(4) Using the reaction solution obtained in (3) above, it was confirmed that a complex was formed by performing analysis by ¹¹ B-NMR.
The procedure of said (1)-(4) was performed and the boron trihalide carbonate compound (henceforth "BF3-MCBA") was prepared.

<Preparation and polymerization of composition>
(5) Preparations were made in the same procedure as (1) above.
(6) A reaction vessel having a nitrogen atmosphere was placed in the water bath of (5) above, and each raw material was added to the reaction vessel according to the composition ratio in Table 3 and stirred to prepare a composition.
(7) The composition prepared in the above (6) was polymerized according to the polymerization conditions shown in Table 5 to obtain a polymer.
In addition, as polymerization conditions, either of the following was used.
・ Polymerization condition A
(1) Hold at 60 ° C. for 1 hour (2) Temperature rise to 120 ° C. (temperature rise rate: 10 ° C./hr)
(3) Hold at 120 ° C. for 1 hour ・ Polymerization condition B
(1) Hold at 60 ° C. for 1 hour (2) Temperature rise to 120 ° C. (temperature rise rate: 10 ° C./hr)
(3) Hold at 120 ° C. for 1 hour (4) Temperature rise to 150 ° C. (temperature rise rate: 20 ° C./hr)
(5) Hold at 150 ° C. for 30 minutes

(Examples 2 to 70)
Except having set it as the composition ratio of Tables 1-6, and superposition | polymerization conditions, the composition was prepared by the method similar to Example 1, and the polymer was obtained.
In Examples 24 to 30, 43 to 46, and 53 to 57, samples for polymerization evaluation and transparency evaluation were prepared in sealed pressure-resistant bottles for evaluation.
The evaluation results of the compositions prepared in Examples 1 to 70 are shown in Tables 5 and 6.

(Comparative Examples 1 to 59)
According to the compositions of Tables 7 and 8, compositions of Comparative Examples 1 to 59 were prepared by the same method as in Example 1, and polymers were obtained according to the polymerization conditions of Tables 9 and 10. In Comparative Examples 25-31, 44-47, and 54-58, samples for polymerization evaluation were prepared in sealed pressure-resistant bottles for evaluation. Tables 9 and 10 show the evaluation results of the compositions prepared in Comparative Examples 1 to 59.

  As shown in Tables 1 to 10, the present embodiment contains (A) a carbonate compound, (B) a boron trihalide, and (C) an epoxy compound, and (A) a carbonate compound and (B ) It was confirmed that a composition in which at least a part of boron trihalide forms a complex is excellent in stability and polymerizability, and a highly transparent polymer can be obtained by polymerizing the composition. . On the other hand, a composition containing an ether compound having one ether group, a sulfide compound, an alcohol compound, an acidic compound, a nitrogen-containing compound, a boron trihalide, an epoxy compound, an epoxy According to a comparative example using a known thermal polymerization accelerator used when polymerizing a compound, none satisfying all of the evaluation of stability, polymerizability and transparency was confirmed.

(Example 71)
<Preparation of glass substrate coated with polymer>
(1) The polymer obtained in Example 67 was dissolved in the same weight of dichloromethane (manufactured by Wako Pure Chemical Industries, Ltd.) to obtain a polymer solution.
The compound used for dissolving the polymer is not particularly limited as long as it can dissolve the polymer and can be removed in a later step.
(2) A polymer solution of the above (1) is dropped on a square quartz glass plate (manufactured by GL Science Co., Ltd., size 10 mm × 10 mm, thickness 1 mm) that has been subjected to double-sided optical polishing. Coated to about 41 μm by company No. 18).
(3) Obtained in (2) above in a vacuum dryer (Tokyo Rika Kikai Co., Ltd., VOS-451D, ULVAC Kiko Co., Ltd., small oil rotary vacuum pump GCD-201X was used for the vacuum pump). The obtained quartz glass plate was put and dried at room temperature, 13 Pa, for 24 hours.
In addition, the temperature and pressure at the time of drying are not particularly limited, and the conditions under which the volatiles contained in the polymer solution are not volatilized rapidly may be appropriately selected. In the present example, the pressure was gradually reduced to finally 13 kPa.

<Evaluation for maintaining light transmittance of polymer on glass substrate>
(4) The total light transmittance of the polymer coated part on the quartz glass plate after drying was measured using a haze meter (NDH-5000W, manufactured by Nippon Denshoku Industries Co., Ltd.) (all obtained here) The light transmittance is referred to as “TLT0”.) In this example, the total light transmittance was 86%.
(5) The quartz glass plate after drying was placed in a thermo-hygrostat (manufactured by ESPEC Corporation, PSL-4J) set at a temperature of 25 ° C. and a humidity of 60% RH for 300 days and held.
(6) The total light transmittance of the polymer-coated part on the quartz glass plate obtained in (5) above was measured in the same manner as in (4) above (the total light transmittance obtained here was “ TLT300 ").
(7) When TLT300 is 80% or more, it is judged to be good (“A”), when it is 85% or more, it is judged to be particularly good (“AA”), and otherwise it is defective (“C”) It was judged. In this example, since TLT300 was 80%, it was judged to be good.
(8) The light transmission maintenance ratio (hereinafter referred to as “dTLT”) was calculated using the following formula.
dTLT (%) = TLT300 / TLT0 × 100
(9) When the light transmission maintenance ratio is 90% or more, it is judged as good (“A”), and when it is 95% or more, it is judged as particularly good (“AA”). ("C"). In this example, since the maintenance ratio of light transmittance was 93%, it was judged to be good.
(10) In the above evaluations (7) and (9), when judged to be particularly good at the same time, and judged to be good in at least one evaluation, and judged to be particularly good or good in other evaluations In some cases, it was determined to pass ("AA" or "A") as a comprehensive judgment. All other cases were rejected ("C").
In this example, TLT300 was 80% and good ("A"), dTLT was 93% and good ("A"), and both evaluations were good. It was judged as good (“A”).

(Examples 72 to 74)
A glass substrate coated with the polymer was evaluated in the same manner as in Example 71 except that the polymer obtained in the examples shown in Table 11 was used.

  As shown in Table 11, it contains (A) a carbonate compound, (B) a boron trihalide, and (C) an epoxy compound, and (A) a carbonate compound and (B) three according to this embodiment. It was confirmed that a polymer obtained by polymerizing a composition in which at least a part of boron halide forms a complex has little change in transparency even after long-term storage.

(Preparation Example 1)
<Preparation of boron trihalide-carbonate compound (BF3-MCBB-2)>
(1) Preparation: On the magnetic stirrer, a water bath equipped with a throwing-type cooling / heating unit was placed, and water and a stirrer were placed therein. The throw-in type cooling and heating unit was activated and the temperature of water was set to 20 ° C.
(2) A reaction vessel in a nitrogen atmosphere was placed in the water bath of (1) above, and each raw material was added to the reaction vessel according to the composition ratio in Table 12, and stirred for 1 hour.
(3) A vacuum distillation apparatus was attached to the reaction vessel, and the pressure was gradually reduced. Finally, the pressure was reduced to 2 kPa and maintained for 4 hours.
(4) Using the reaction solution obtained in (3) above, it was confirmed that a complex was formed by performing analysis by ¹¹ B-NMR.
The procedures (1) to (4) were performed to prepare a boron trihalide-carbonate compound (hereinafter referred to as “BF3-MCBB-2”).

(Preparation Examples 2-9)
A boron trihalide-carbonate compound was prepared in the same manner as in Preparation Example 1 except that the composition ratios in Table 12 were used.

(Example 75)
<Preparation and polymerization of composition>
(1) Preparation: On the magnetic stirrer, a water bath equipped with a throwing-type cooling / heating unit was placed, and water and a stirrer were placed therein. The throw-in type cooling and heating unit was activated and the temperature of water was set to 20 ° C.
(2) A reaction vessel in a nitrogen atmosphere was placed in the water bath of (1) above, and the composition was prepared by adding to the reaction vessel and stirring according to the composition ratio in Table 13.
(3) The composition prepared in the above (2) was polymerized according to the polymerization conditions shown in Table 15 to obtain a polymer.
In addition, as polymerization conditions, either of the following was used.
・ Polymerization condition C
(1) Hold at 60 ° C. for 1 hour (2) Temperature rise to 120 ° C. (temperature rise rate: 10 ° C./hr)
(3) Hold at 120 ° C. for 4 hours ・ Polymerization condition D
(1) Hold at 60 ° C. for 1 hour (2) Temperature rise to 120 ° C. (temperature rise rate: 10 ° C./hr)
(3) Hold at 120 ° C. for 4 hours (4) Temperature increase to 150 ° C. (temperature increase rate: 20 ° C./hr)
(5) Hold at 150 ° C. for 30 minutes

<Heat-resistant stability evaluation of polymer (hereinafter referred to as “RA method”): When the epoxy compound that is the base of the polymer has one epoxy group>
(4) Obtained in (3) above in a vacuum dryer (VOS-451D, manufactured by Tokyo Rika Kikai Co., Ltd., and a small oil rotary vacuum pump GCD-201X manufactured by ULVAC Kiko Co., Ltd. was used as the vacuum pump). The polymer obtained was put and dried at 50 ° C. and 13 Pa for 24 hours.
(5) The polymer obtained in the above (4) was transferred to a dry glass container, and the weight of the polymer was measured (hereinafter referred to as “RGWS”).
(6) After putting in a thermostat (Espec Corp., IPHH-202) and making it nitrogen atmosphere, the chamber internal temperature was 150 degreeC and hold | maintained for 2000 hours.
(7) The weight of the polymer obtained in the above (6) was measured (hereinafter referred to as “RGWF”).
(8) The weight change of the polymer (hereinafter referred to as “RGW”) was calculated by the following formula.
RGW (%) = 100−RGWF / RGWS × 100
(9) When RGW is 5% or less, it is judged as good (“A”), when RGW is 2% or less, it is judged as particularly good (“AA”), and otherwise it is defective (“C”) It was judged. In this example, since RGW was 1%, it was judged to be particularly good.

<Heat-resistant stability evaluation of polymer (hereinafter referred to as “RB method”): When the epoxy compound that is the base of the polymer has one epoxy group>
It was performed in the same manner as the RA method except that the temperature in the thermostatic chamber was 170 ° C.

<Heat-resistant stability evaluation of polymer (hereinafter referred to as “RC method”): When the epoxy compound that is the base of the polymer has two or more epoxy groups>
It was performed in the same manner as the RA method except that the temperature in the thermostatic chamber was 200 ° C.

<Heat-resistant stability evaluation of polymer (hereinafter referred to as “RD method”): When the epoxy compound that is the base of the polymer has two or more epoxy groups>
It was carried out in the same manner as the RA method except that the temperature in the thermostatic chamber was 220 ° C.

(Examples 76 to 139)
A polymer was obtained in the same manner as in Example 75 except that the composition ratios in Tables 13 and 14 and the polymerization conditions in Tables 15 and 16 were used. Tables 15 and 16 show the evaluation results of the polymers obtained in Examples 75 to 139.
In Examples 91 to 97 and 104 to 112, the polymer was prepared in a sealed pressure bottle.

  As shown in Tables 13-16, (A) the carbonate compound, (B) boron trihalide, and (C) epoxy according to this embodiment because the structure of the (A) carbonate compound is a cyclic structure. A polymer and a cured product obtained by polymerizing a composition containing a compound, wherein (A) a carbonate compound and (B) at least a part of boron trihalide form a complex, are kept for a long time at a high temperature. However, it was confirmed that there was little volatile matter and the stability at high temperature was high.

(Example 140)
<Preparation of boron trihalide-carbonate compound (BF3-MCBD-1)>
(1) Preparation: On the magnetic stirrer, a water bath equipped with a throwing-type cooling / heating unit was placed, and water and a stirrer were placed therein. The throw-in type cooling and heating unit was activated and the temperature of water was set to 20 ° C.
(2) A reaction vessel having a nitrogen atmosphere was placed in the water bath of (1) above, and 42% by mass of 4-methyl-1,3-dioxolan-2-one and 58% by mass of boron trifluoride diethyl ether complex were Added to the reaction vessel and stirred for 1 hour.
(3) A vacuum distillation apparatus was attached to the reaction vessel, and the pressure was gradually reduced. Finally, the pressure was reduced to 2 kPa and maintained for 4 hours.
(4) Using the product obtained in (3) above, it was confirmed that a complex was formed by performing an analysis by ¹¹ B-NMR.

<Preparation and polymerization of composition>
(5) Preparations were made in the same procedure as (1) above.
(6) A reaction vessel in a nitrogen atmosphere was placed in the water bath of (5) above, and was added to the reaction vessel according to the composition ratio in Table 17 and stirred to prepare a composition.
(7) A polymer was obtained by polymerizing the composition prepared in (6) above according to the polymerization conditions shown in Table 20.
The mixing index γ was calculated by the following formula (10).
Index γ = αd / αep × 100 (10)
here,
αd: (D) amount of chain transfer agent (mol)
αep: (C) The amount (mol) of the epoxy group contained in the epoxy compound, respectively.
(8) The epoxy group reaction rate of the polymer obtained in the above (7) was measured by the method shown in Table 20, and it was confirmed that the epoxy group in the original epoxy compound was polymerized.

(Examples 141-249)
Polymers were obtained by the same method as in Example 140 except that the composition ratios in Tables 17 to 19 and the polymerization conditions in Tables 20 to 22 were used. The evaluation results of the polymers obtained in Examples 140 to 249 are shown in Tables 20 to 22.
In Examples 162 to 168, 175 to 190, and 197 to 205, the polymer was prepared in a sealed pressure bottle.

  As shown in Tables 17-22, this embodiment contains (A) a carbonate compound, (B) a boron trihalide, (C) an epoxy compound, and (D) a chain transfer agent. A polymer and a cured product obtained by polymerizing a composition in which at least a part of a carbonate compound and (B) boron trihalide forms a complex have little volatile content even when kept at a high temperature for a long period of time. It was confirmed that the stability at high temperature was high.

  The composition of the present embodiment and a polymer or cured product obtained by polymerizing the composition are electronic materials (insulators, AC transformers, switchgear and other casting units, circuit units, various parts packages, ICs / LEDs)・ Semiconductor peripheral materials [sealing materials, lens materials, substrate materials, die bonding materials, chip coating materials, laminated plates, optical fibers, optical waveguides, optical filters, adhesives for electronic components, coating materials, sealing materials, insulating materials, Photoresists, encap materials, potting materials, optical transmission layers and interlayer insulation layers of optical disks, light guide plates, antireflection films, etc.], rotating coils of generators, motors, winding impregnations, printed wiring boards, laminates, Insulation boards, medium-sized insulators, coils, connectors, terminals, various cases, electrical parts, etc.), paint (corrosion-resistant paint, maintenance, ship painting, corrosion-resistant lining, automobile / house Product primer, beverage / beer can, outer surface lacquer, extrusion tube coating, general anticorrosion coating, maintenance coating, woodwork product lacquer, automotive electrodeposition primer, other industrial electrodeposition coating, beverage / beer can inner surface lacquer, coil coating , Drum / can inner surface coating, acid-resistant lining, wire enamel, insulation paint, automotive primer, beautiful and anticorrosion coating of various metal products, pipe interior / exterior coating, electrical parts insulation coating, etc.), composite materials (chemical plant pipes, etc.) Tanks, aircraft materials, automotive parts, various sports equipment, carbon fiber composite materials, aramid fiber composite materials, etc.), civil engineering and building materials (floor materials, pavement materials, membranes, anti-slip / thin layer pavements, concrete jointing / raising) , Anchor embedded adhesive, precast concrete joint, tile adhesive, concrete structure Repair of cracks in pedestals, grout and leveling of pedestals, anticorrosion and waterproofing of water and sewage facilities, anticorrosive laminated lining of tanks, anticorrosion of iron structures, mastic coating of exterior walls of buildings, etc., adhesives (metal, glass, ceramics) -Adhesives of the same or different materials such as cement concrete, wood, plastics, adhesives for assembly of automobiles, railway vehicles, aircraft, etc., adhesives for manufacturing prefabricated composite panels, etc .: One-part type, two-part type, sheet type ), Aircraft / automobile / plastic molding jigs (resin molds such as press dies, stretched dies, matched dies, vacuum molding / blow molding molds, master models, casting patterns, laminated jigs, various inspection jigs Etc.), modifiers / stabilizers (fiber resin processing, stabilizers for polyvinyl chloride, additives to synthetic rubber, etc.), rubber modifiers (vulcanizing agents, Industrial applicability as vulcanization accelerators).

Claims (12)

  (A) a carbonate compound, (B) a boron trihalide, and (C) an epoxy compound, and at least a part of the (A) carbonate compound and the (B) boron trihalide forms a complex. The composition. The composition of Claim 1 whose said (A) carbonate compound is a compound represented by following formula (1).

[Wherein, a represents a number of 1 or more, and R ₁ and R ₂ represent a chain, branched or cyclic aliphatic hydrocarbon group having 1 to 33 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group. R ₁ and R ₂ may be linked to each other. When a is 2 or more, a plurality of R ₂ may be the same or different, and R ₂ may be linked to each other. ]   The composition according to claim 1 or 2, wherein the (A) carbonate compound has 3 to 25 carbon atoms.   The composition according to any one of claims 1 to 3, wherein the number of carbonate groups of the (A) carbonate compound is 1 to 4. The index (alpha) showing the ratio of the said (A) carbonate compound and the said (B) boron trihalide represented by following formula (2) is 1-1000, It is any one of Claims 1-4. The composition as described.
Index α = αc / αb (2)
αc: Amount (mol) of carbonate group of the carbonate compound (A)
αb: (B) the amount of boron trihalide (mol)   The composition according to any one of claims 1 to 5, wherein the (B) boron trihalide is at least one selected from the group consisting of boron trifluoride, boron trichloride, and boron tribromide. .   The composition according to any one of claims 1 to 6, wherein the (C) epoxy compound is a compound having only a three-membered cyclic ether structure as a polymerizable functional group.   The ratio of the substance amount (mol) of the (B) boron trihalide and the substance amount (mol) of the epoxy group contained in the (C) epoxy compound is 1:10 to 1: 100,000. The composition as described in any one of 1-7.   The composition according to any one of claims 1 to 8, wherein the epoxy equivalent of the (C) epoxy compound is 55 to 600 g / mol. The composition according to any one of claims 1 to 9, wherein the (C) epoxy compound has a partial structure represented by the following formula (3), (4), (5) or (6).

[Wherein R ₁₀ , R ₁₁ , R ₁₂ , R ₁₃ , R ₁₄ , R ₁₅ , R ₁₆ , R ₁₇ , R ₁₈ , R ₁₉ , R ₂₀ , R ₂₁ , R ₂₂ , R ₂₃ and R ₂₄ are each Independently, it represents a hydrogen atom, a chain, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group. ]   The polymer formed by polymerizing the said (C) epoxy compound in the composition as described in any one of Claims 1-10.   The manufacturing method of the polymer which polymerizes the said (C) epoxy compound in the composition as described in any one of Claims 1-10 by heating and / or energy ray irradiation.