JP2014136780A - 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 ketone compound, (B) a boron trihalide, and (C) an epoxy compound, in wich at least part of (A) the ketone 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、ｃ、ｄ及びｆは、それぞれ独立に１以上の数を示し、ｂ及びｅは、それぞれ独立に２以上の数を示し、
Ｒ_１及びＲ_２は、それぞれ独立に、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し、Ｒ_３は、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、Ｒ_２、及びＲ_３は、互いに連結されていてもよく、
Ｒ_４及びＲ_５は、それぞれ独立に、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し、Ｒ_５同士は、同一でも異なっていてもよく、Ｒ_４、Ｒ_５及びＲ_５同士は、互いに連結されていてもよく、
Ｒ_６、Ｒ_７及びＲ_８は、それぞれ独立に、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し、Ｒ_６及びＲ_８同士は、同一でも異なっていてもよく、Ｒ_６、Ｒ_７又はＲ_８とＲ_６又はＲ_８とは、互いに連結されていてもよい。］
［３］
（Ａ）ケトン化合物の炭素数が、３〜３１である、項［１］又は［２］に記載の組成物。
［４］
（Ａ）ケトン化合物のケトン基の数が、１〜８である、項［１］〜［３］のいずれか一項に記載の組成物。
［５］
下記式（４）で表される（Ａ）ケトン化合物と（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＝αｋ／αｂ （４）
αｋ：（Ａ）ケトン化合物のケトン基の物質量（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（５）、（６）、（７）又は（８）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。］
［１０］
項［１］〜［９］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。
［１１］
項［１］〜［９］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 ketone compound, (B) a boron trihalide, and (C) an epoxy compound, and (A) the ketone 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 ketone compound is a compound represented by the following formula (1), (2) or (3).

[Wherein, a, c, d and f each independently represents a number of 1 or more; b and e each independently represents a number of 2 or more;
R ₁ and R ₂ each independently represent a chain, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group, and R ₃ represents a hydrogen atom Or a linear, branched or cyclic aliphatic or substituted or unsubstituted aromatic hydrocarbon group having 1 to 20 carbon atoms, wherein R ₁ , R ₂ , and R ₃ may be linked to each other;
R ₄ and R ₅ each independently represent a chain, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group, and R ₅ are the same However, they may be different, and R ₄ , R ₅ and R ₅ may be linked to each other,
R _6, R ₇ and R ₈ are each independently a number of 1 to 20 chain carbons, straight, branched or cyclic aliphatic hydrocarbon group or a substituted or unsubstituted aromatic hydrocarbon group, R ₆ and R ₈ may be the same or different, and R ₆ , R ₇ or R ₈ and R ₆ or R ₈ may be linked to each other. ]
[3]
(A) The composition according to item [1] or [2], wherein the ketone compound has 3 to 31 carbon atoms.
[4]
(A) The composition according to any one of Items [1] to [3], wherein the number of ketone groups of the ketone compound is 1 to 8.
[5]
In any one of Items [1] to [4], an index α representing a ratio of (A) a ketone compound represented by the following formula (4) and (B) boron trihalide is 1-1000. The composition as described.
Index α = αk / αb (4)
αk: (A) Amount of substance of the ketone group of the ketone 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 (5), (6), (7) or (8): 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. ]
[10]
Item 15. A polymer formed by polymerizing the epoxy compound (C) in the composition according to any one of items [1] to [9].
[11]
A method for producing a polymer, wherein the (C) epoxy compound in the composition according to any one of items [1] to [9] 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 ketone 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): Ketone compound)
Component (A) of the present embodiment is a ketone compound containing one or more ketone groups in the molecule. As the component (A), one type of ketone compound may be used alone, or a plurality of types of ketone compounds may be used in combination.

  The (A) ketone compound can further suppress the polymerization of the (C) epoxy compound and the stability of the composition tends to be further improved, and / or (C) a polymer obtained after polymerizing the epoxy compound The compound represented by the following formula (1), (2), or (3) is preferable because the transparency of the glass tends to be further improved.

In the formula, a, c, d and f each independently represent a number of 1 or more, and b and e each independently represent a number of 2 or more. R ₁ and R ₂ each independently represent a chain, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group. R ₃ represents hydrogen, a linear, branched or cyclic aliphatic group having 1 to 20 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group. R ₁ , R ₂ , and R ₃ may be linked to each other.
R ₄ and R ₅ each independently represent a chain, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group. R ₅ may be the same or different. R ₄ , R ₅ and R ₅ may be linked to each other. R ₆ , R ₇ and R ₈ each independently represent a chain, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group. R ₆ and R ₈ may be the same or different. R ₆ , R ₇ or R ₈ and R ₆ or R ₈ may be linked to each other.

In the above formula (1), when a is 2, R ₂ is a chain, branched or cyclic aliphatic hydrocarbon group having 2 to 20 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group. Preferably there is.

The above formula (2) shows a case where a is 2 or more and R ₂ does not exist in the above formula (1).

In Formula (1), when a is 1, R ₁ is CH ₃ , R ₂ is CH ₂ , and R ₃ is H, acetone is obtained. In Formula (1), when a is 2, R ₁ is CH ₃ , R ₂ is CH ₂ CH ₂ , and R ₃ is H, 2,5-heptanedione is obtained. Furthermore, in Formula (1), when a is 3, R ₁ is CH ₃ , R ₂ is CH ₂ , and R ₃ is H, 2,4,6-heptanetrione is obtained.

In the formula (2), when b is 2, c is 1, R ₄ is CH ₃ , and R ₅ is CH ₃ , 2,3-butanedione is obtained.

  (A) The carbon number of the ketone 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. The number of carbon atoms is more preferably 4 or more because the vapor pressure tends to be high and the handleability tends to be improved. From the same viewpoint, the carbon number is more preferably 6 or more.

  (A) The number of carbon atoms of the ketone compound is preferably 31 or less because it can be easily obtained, the cost of the composition can be further suppressed, and the economy tends to be excellent. From the same viewpoint, the carbon number is preferably 20 or less. When preparing the composition, it is more preferable that the number of carbon atoms is 14 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 12 or less.

  (A) The number of ketone groups of the ketone 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 preferable that it is 2 or more.

  (A) The number of ketone groups of the ketone compound is preferably 8 or less because it is easy to obtain, can reduce the cost of the composition, and tends to be economical. From the same viewpoint, the number of ketone groups is more preferably 6 or less. When preparing the composition, it is more preferable that the number of ketone groups is 4 or less because the remaining of undissolved material can be suppressed and a composition having excellent uniformity can be obtained. From the same viewpoint, the number of ketone groups is particularly preferably 3 or less.

  Specific examples of (A) ketone compounds include monofunctional ketone compounds, bifunctional ketone compounds, polyfunctional ketone compounds, and polyketone compounds. These may be used alone or in combination.

(Monofunctional ketone compound)
The monofunctional ketone compound according to this embodiment is not particularly limited as long as it is a compound having one ketone group.

  Among monofunctional ketone compounds, it is easy to obtain, can reduce the cost as a composition, tends to be more economical, and when preparing a composition at room temperature, further suppresses polymerization of the epoxy compound (C) 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.

  Acetone, 2-butanone, methylbutanone, dimethylbutanone, 2-pentanone, 3-pentanone, methylpentanone, dimethylpentanone, 2-hexanone, 3-hexanone, methylhexanone, ethylhexanone, dimethylhexanone, propylhexanone, isopropylhexanone Ethylmethylhexanone, ethyldimethylhexanone, 2-heptanone, 3-heptanone, 4-heptanone, methylheptanone, ethylheptanone, dimethylheptanone, propylheptanone, isopropylheptanone, ethylmethylheptanone, 2-octanone, 3-octanone, 4-octanone, methyloctanone, ethyloctanone, dimethyloctanone, 2-nonanone, 3-nonanone, 4-nonanone, 5-nonanone, methylnonanone, 2-deca 3-decanone, 4-decanone, 5-decanone, 2-undecanone, 3-undecanone, 4-undecanone, 5-undecanone, 6-undecanone, 2-dodecanone, 3-dodecanone, 4-dodecanone, 5-dodecanone, 6-dodecanone, 2-tridecanone, 3-tridecanone, 4-tridecanone, 5-tridecanone, 6-tridecanone, 7-tridecanone, diethyltridecanone, 2-tetradecanone, 3-tetradecanone, 4-tetradecanone, 5-tetradecanone, 6- Tetradecanone, 7-tetradecanone, 1- [1,1′-biphenyl] -4-yl-2-cyclohexaneethanone, 1- (4′-methyl [1,1′-biphenyl] -4-yl) -1- Octadecanone;

Acetophenone, methylacetophenone, ethylacetophenone, propiophenone, methylpropiophenone, ethylpropiophenone, butyrophenone, methylbutyrophenone, ethylbutyrophenone, isobutyrophenone, methylisobutyrophenone, ethylisobutyrophenone, tert-butylphenylketone, tert-butyl -Methyl phenyl ketone, tert-butyl-ethyl phenyl ketone, sec-butyl phenyl ketone, sec-butyl-methyl phenyl ketone, sec-butyl-ethyl phenyl ketone, valerophenone, methyl valerophenone, ethyl valerophenone, isopentyl phenyl ketone, Isopentyl (methylphenyl) ketone, isopentyl (ethylphenyl) ketone, neopentyl phenyl ketone Neopentyl (methylphenyl) ketone, neopentyl (ethylphenyl) ketone, hexanophenone, methylhexanophenone, ethylhexanophenone, heptanophenone, methylheptanophenone, ethylheptanophenone, octanophenone, methyloctanophenone , Ethyloctanophenone, nonanophenone, methylnonanophenone, ethylnonanophenone, decanophenone, methyldecanophenone, ethyldecanophenone, undecaffeone, methylundecanophenone, ethylundecanophenone, dodecanophenone, methyldodecanophenone Ethyl dodecanophenone;

Acetonaphthone, methyl acetonaphthone, propiononaphthone, methyl propionnaphthone, tert-butyl naphthyl ketone, tert-butyl- (methyl naphthyl) ketone, sec-butyl naphthyl ketone, sec-butyl- (methyl naphthyl) ketone, isobutyronaphthone , Methyl isobutyronaphthone, butyronaphthone, methyl butyronaphthone, valero naphthone, methyl valero naphthone, isopentyl naphthyl ketone, isopentyl (methyl naphthyl) ketone, neopentyl naphthyl ketone, neopentyl (methyl naphthyl) ketone, hexanonaphthone, methyl hexanonaphth Tons, heptanonaphthon, methylheptanonaphthon, octanonaphthon, methyloctanonaphthon, nonanonaphthon, methylnonanonaphthon, decanonahnaphthone, methy Decanonaphthone, undecanaphton, methylundecanonaphthone, dodecananaphthone, methyldodecanonaphthone, naphthylphenylketone, acetylphenanthrene, acetylanthracene, acetylpyrene, benzo [a] fluorenone, 4H-cyclopenta [def] phenanthren-4-one, 5- Acetyl-1,2-dihydroacenaphthylene, 3,3,5,5,8,8-pentamethyloctahydro-2 (1H) -naphthalenone;

Cyclopropanone, methylcyclopropanone, dimethylcyclopropanone, trimethylcyclopropanone, tetramethylcyclopropanone, ethylcyclopropanone, diethylcyclopropanone, triethylcyclopropanone, tetraethylcyclopropanone, phenylcyclopropanone, Diphenylcyclopropanone, triphenylcyclopropanone, tetraphenylcyclopropanone, ethylmethylcyclopropanone, diethylmethylcyclopropanone, tetraethylcyclopropanone, diethyldimethylcyclopropanone, cyclobutanone, methylcyclobutanone, ethylcyclobutanone, phenylcyclobutanone , Dimethylcyclobutanone, trimethylcyclobutanone, tetramethylcyclobutanone, pentamethylcyclobutanone, Oxamethylcyclobutanone, diethylcyclobutanone, triethylcyclobutanone, triethylcyclobutanone, tetraethylcyclobutanone, pentaethylcyclobutanone, hexaethylcyclobutanone, diphenylcyclobutanone, triphenylcyclobutanone, tetraphenylcyclobutanone, pentaphenylcyclobutanone, hexaphenylcyclobutanone, cyclopentanone, methylcyclopentanone Non, ethylcyclopentanone, phenylcyclopentanone, dimethylcyclopentanone, trimethylcyclopentanone, tetramethylcyclopentanone, pentamethylcyclopentanone, hexamethylcyclopentanone, heptamethylcyclopentanone, diethylcyclopentanone , Triethylcyclopentanone, tetraethylsilane Lopentanone, pentaethylcyclopentanone, hexaethylcyclopentanone, heptaethylcyclopentanone, octaethylcyclopentanone, diphenylcyclopentanone, triphenylcyclopentanone, tetraphenylcyclopentanone, pentaphenylcyclopentanone, hexa Phenylcyclopentanone, heptaphenylcyclopentanone, octaphenylcyclopentanone;

Cyclohexanone, methylcyclohexanone, dimethylcyclohexanone, trimethylcyclohexanone, tetramethylcyclohexanone, pentamethylcyclohexanone, hexamethylcyclohexanone, heptamethylcyclohexanone, octamethylcyclohexanone, nonamethylcyclohexanone, decamethylcyclohexanone, ethylcyclohexanone, diethylcyclohexanone, triethylcyclohexanone, tetraethylcyclohexanone , Pentaethylcyclohexanone, hexaethylcyclohexanone, heptaethylcyclohexanone, octaethylcyclohexanone, nonaethylcyclohexanone, decaethylcyclohexanone, phenylcyclohexanone, diphenylcyclohexanone, triphenylcyclohexano , Tetraphenylcyclohexanone, pentaphenylcyclohexanone, hexaphenylcyclohexanone, heptaphenylcyclohexanone, octaphenylcyclohexanone, nonaphenylcyclohexanone, decaphenylcyclohexanone, cycloheptanone, propylcyclohexanone, butylcyclohexanone, pentylcyclohexanone, hexylcyclohexanone, methylcycloheptanone, Dimethylcycloheptanone, ethylcycloheptanone, diethylcycloheptanone, phenylcycloheptanone, diphenylcycloheptanone, cyclooctanone, methylcyclooctanone, dimethylcyclooctanone, ethylcyclooctanone, diethylcyclooctanone, phenyl Cyclooctanone, diphenylcyclooctano , Cyclononanone, methylcyclononanone, dimethylcyclononanone, ethylcyclononanone, diethylcyclononanone, phenylcyclononanone, diphenylcyclononanone, cyclodecanone, methylcyclodecanone, dimethylcyclodecanone, ethylcyclodecanone, Diethylcyclodecanone, phenylcyclodecanone, diphenylcyclodecanone, cycloundecanone, cyclododecanone, cyclotridecanone, cyclotetradecanone, decalon, adamantanone, adamantyl methyl ketone, norbornanone, bicyclo [2.2.2 ] Octane-1-one.

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

  Acetone, 2-butanone, methylbutanone, dimethylbutanone, 2-pentanone, 3-pentanone, methylpentanone, 2-hexanone, 3-hexanone, 2-heptanone, 3-heptanone, 4-heptanone, 2-octanone, 3- Octanone, 4-octanone, 2-nonanone, 3-nonanone, 4-nonanone, 5-nonanone, 2-decanone, 3-decanone, 4-decanone, 5-decanone, 2-undecanone, 3-undecanone, 4-undecanone, 5-undecanone, 6-undecanone, 2-dodecanone, 3-dodecanone, 4-dodecanone, 5-dodecanone, 6-dodecanone, 2-tridecanone, 3-tridecanone, 4-tridecanone, 5-tridecanone, 6-tridecanone, 7- Tridecanone, diethyl tridecanone, 2-tetradecanone 3-tetradecanone, 4-tetradecanone, 5-tetradecanone, 6-tetradecanone, 7-tetradecanone, 1- [1,1′-biphenyl] -4-yl-2-cyclohexaneethanone, 1- (4′-methyl [1] , 1′-biphenyl] -4-yl) -1-octadecanone, acetophenone, propiophenone, butyrophenone, isobutyrophenone, tert-butylphenylketone, valerophenone, isopentylphenylketone, neopentylphenylketone, hexanophenone, hepta Nophenone, octanophenone, nonanophenone, decanophenone, undecaffeone, dodecanophenone;

Acetonaphthone, propionnaphthone, tert-butyl naphthyl ketone, sec-butyl naphthyl ketone, isobutyronaphthone, butyronaphthone, valeronaphthone, isopentyl naphthyl ketone, neopentyl naphthyl ketone, hexanonaphthone, heptanonaphthone, octanonaphthone, acetylphenanthrene, acetylphenanthrene Benzo [a] fluorenone, 4H-cyclopenta [def] phenanthrene-4-one, 5-acetyl-1,2-dihydroacenaphthylene, 3,3,5,5,8,8-pentamethyloctahydro-2 (1H) -Naphthalenone, cyclopropanone, cyclobutanone, cyclopentanone, cyclohexanone, cycloheptanone, butylcyclohexanone, cyclooctanone, cyclo Nanon, cyclodecanone, cycloalkyl undecanoic, cyclododecanone, cycloalkyl tridecafluoro non, cycloalkyl tetradecanol non, decalone, adamantanone, adamantyl methyl ketone, norbornanone, bicyclo [2.2.2] octane-1-one.

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

  Dimethylbutanone, methylpentanone, 2-hexanone, 3-hexanone, 3-heptanone, 2-octanone, 3-octanone, 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2-undecanone, 6-undecanone 2-dodecanone, 5-dodecanone, 2-tridecanone, 7-tridecanone, diethyltridecanone, acetophenone, propiophenone, butyrophenone, isobutyrophenone, tert-butylphenylketone, valerophenone, isopentylphenylketone, neopentylphenylketone, Hexanophenone, heptanophenone, octanophenone, nonanophenone, decanophenone, undecaffeone, dodecanophenone, acetonaphthone, naphthylphenylketone, acetylphenanthrene, cyclohexane Sanon, butyl cyclohexanone, cyclooctanone, cyclononanone, cyclodecanone, cyclododecanone, bicyclo [2.2.2] octane-1-one.

(Bifunctional ketone compound)
The bifunctional ketone compound according to this embodiment is not particularly limited as long as it has two ketone groups and the ketone groups are not adjacent to each other.

  Among the bifunctional ketone 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.

  2,4-pentanedione, methyl-2,4-pentanedione, dimethyl-2,4-pentanedione, ethyl-2,4-pentanedione, diethyl-2,4-pentanedione, ethylmethyl-2,4- Pentanedione, 2,4-hexanedione, methyl-2,4-hexanedione, dimethyl-2,4-hexanedione, ethyl-2,4-hexanedione, diethyl-2,4-hexanedione, ethylmethyl-2 , 4-hexanedione, ethyldimethyl-2,4-hexanedione, diethylmethyl-2,4-hexanedione, diethyldimethyl-2,4-hexanedione, 2,5-hexanedione, methyl-2,5-hexane Dione, ethyl-2,5-hexanedione, dimethyl-2,5-hexanedione, ethylmethyl-2,5-hexanedio , Diethyl-2,5-hexanedione, trimethyl-2,5-hexanedione, ethyldimethyl-2,5-hexanedione, diethylmethyl-2,5-hexanedione, triethyl-2,5-hexanedione, tetramethyl -2,5-hexanedione, ethyltrimethyl-2,5-hexanedione, diethyldimethyl-2,5-hexanedione, triethylmethyl-2,5-hexanedione, tetraethyl-2,5-hexanedione, 2,4 -Heptanedione, 2,5-heptanedione, 2,6-heptanedione, 3,5-heptanedione, dimethyl-2,4-heptanedione, ethylmethyl-2,4-heptanedione, diethyl-2,4- Heptanedione, dimethyl-2,5-heptanedione, ethylmethyl-2,5-heptanedione, Ethyl-2,5-heptanedione, methyl-3,5-heptanedione, ethyl-3,5-heptanedione, dimethyl-3,5-heptanedione, ethylmethyl-3,5-heptanedione, diethyl-3, 5-heptanedione, 2,4-octanedione, methyl-2,4-octanedione, ethyl-2,4-octanedione, dimethyl-2,4-octanedione, ethylmethyl-2,4-octanedione, diethyl -2,4-octanedione;

2,5-octanedione, methyl-2,5-octanedione, dimethyl-2,5-octanedione, ethylmethyl-2,5-octanedione, diethyl-2,5-octanedione, 2,6-octanedione Methyl-2,6-octanedione, ethyl-2,6-octanedione, dimethyl-2,6-octanedione, ethylmethyl-2,6-octanedione, diethyl-2,6-octanedione, 2,7 -Octanedione, methyl-2,7-octanedione, ethyl-2,7-octanedione, dimethyl-2,7-octanedione, ethylmethyl-2,7-octanedione, diethyl-2,7-octanedione, 3,5-octanedione, methyl-3,5-octanedione, ethyl-3,5-octanedione, dimethyl-3,5-octanedione , Ethylmethyl-3,5-octanedione, diethyl-3,5-octanedione, 3,6-octanedione, methyl-3,6-octanedione, ethyl-3,6-octanedione, dimethyl-3, 6-octanedione, ethylmethyl-3,6-octanedione, diethyl-3,6-octanedione, 2,4-nonanedione, 2,5-nonanedione, 2,6-nonanedione, 2,7-nonanedione, 2, 8-nonanedione, 3,5-nonanedione, 3,6-nonanedione, 3,7-nonanedione, 3,8-nonanedione, 4,6-nonanedione, 4,7-nonanedione, 2,4-decanedione, 2,5- Decandione, 2,6-decanedione, 2,7-decanedione, 2,8-decanedione, 2,9-decanedione, 3,5-decanedione 3,6-decanedione, 3,7-decanedione, 3,8-decanedione, 4,6-decanedione, 4,7-decanedione, 2,4-undecanedione, 2,5-undecanedione, 2,6-undecanedione 2,7-undecanedione, 2,8-undecanedione, 2,9-undecanedione, 2,10-undecanedione, 3,5-undecanedione, 3,6-undecanedione, 3,7-undecanedione, 3,8-undecanedione, 3,9-undecanedione, 4,6-undecanedione, 4,7-undecanedione, 4,8-undecanedione, 5,7-undecanedione, 1,3-cyclobutanedione, methyl -1,3-cyclobutanedione, dimethyl-1,3-cyclobutanedione, trimethyl-1,3-cyclobutanedio , Tetramethylcyclobutanedione, ethylmethyl-1,3-cyclobutanedione, diethylmethyl-1,3-cyclobutanedione, triethylmethyl-1,3-cyclobutanedione, ethyl-1,3-cyclobutanedione, diethyl-1, 3-cyclobutanedione, triethyl-1,3-cyclobutanedione, tetraethyl-1,3-cyclobutanedione;

1,3-cyclopentanedione, methyl-1,3-cyclopentanedione, ethyl-1,3-cyclopentanedione, dimethyl-1,3-cyclopentanedione, ethyl-2-methyl-1,3-cyclo Pentanedione, ethylmethyl-1,3-cyclopentanedione, diethyl-1,3-cyclopentanedione, trimethyl-1,3-cyclopentanedione, tetramethyl-1,3-cyclopentanedione, pentamethyl-1,3 -Cyclopentanedione, hexamethyl-1,3-cyclopentanedione, triethyl-1,3-cyclopentanedione, tetraethyl-1,3-cyclopentanedione, pentaethyl-1,3-cyclopentanedione, hexaethyl-1,3 -Cyclopentanedione, 1,3-cyclohexanedione, methyl- 1,3-cyclohexanedione, ethyl-1,3-cyclohexanedione, dimethyl-1,3-cyclohexanedione, ethylmethyl-1,3-cyclohexanedione, diethyl-1,3-cyclohexanedione, trimethyl-1,3- Cyclohexanedione, tetramethyl-1,3-cyclohexanedione, pentamethyl-1,3-cyclohexanedione, hexamethyl-1,3-cyclohexanedione, heptamethyl-1,3-cyclohexanedione, octamethyl-1,3-cyclohexanedione, triethyl -1,3-cyclohexanedione, tetraethyl-1,3-cyclohexanedione, pentaethyl-1,3-cyclohexanedione, hexaethyl-1,3-cyclohexanedione, heptaethyl-1,3-cyclohexanedione , Octaethyl-1,3-cyclohexanedione, 1,4-cyclohexanedione, methyl-1,4-cyclohexanedione, ethyl-1,4-cyclohexanedione, dimethyl-1,4-cyclohexanedione, ethylmethyl-1 , 4-cyclohexanedione, diethyl-1,4-cyclohexanedione, trimethyl-1,4-cyclohexanedione, tetramethyl-1,4-cyclohexanedione, pentamethyl-1,4-cyclohexanedione, hexamethyl-1,4- Cyclohexanedione, heptamethyl-1,4-cyclohexanedione, octamethyl-1,4-cyclohexanedione, triethyl-1,4-cyclohexanedione, tetraethyl-1,4-cyclohexanedione, pentaethyl-1,4-cyclohexanedione ON, hexaethyl-1,4-cyclohexanedione, heptaethyl-1,4-cyclohexanedione, octaethyl-1,4-cyclohexanedione;

1,3-cycloheptanedione, methyl-1,3-cycloheptanedione, ethyl-1,3-cycloheptanedione, dimethyl-1,3-cycloheptanedione, ethyl-2-methyl-1,3-cycloheptane Dione, ethylmethyl-1,3-cycloheptanedione, diethyl-1,3-cycloheptanedione, 1,4-cycloheptanedione, methyl-1,4-cycloheptanedione, ethyl-1,4-cycloheptanedione Dimethyl-1,4-cycloheptanedione, ethylmethyl-1,4-cycloheptanedione, diethyl-1,4-cycloheptanedione, 1,3-cyclooctanedione, methyl-1,3-cyclooctanedione, Ethyl-1,3-cyclooctanedione, dimethyl-1,3-cyclooctanedione, ethylmethyl -1,3-cyclooctanedione, diethyl-1,3-cyclooctanedione, 1,4-cyclooctanedione, methyl-1,4-cyclooctanedione, ethyl-1,4-cyclooctanedione, dimethyl-1 , 4-cyclooctanedione, ethylmethyl-1,4-cyclooctanedione, diethyl-1,4-cyclooctanedione, 1,5-cyclooctanedione, methyl-1,5-cyclooctanedione, ethyl-1, 5-cyclooctanedione, dimethyl-1,5-cyclooctanedione, ethylmethyl-1,5-cyclooctanedione, diethyl-1,5-cyclooctanedione, 1,3-cyclononanedione, methyl-1,3 -Cyclononanedione, ethyl-1,3-cyclononanedione, 1,4-cyclononanedione, methyl -1,4-cyclononanedione, ethyl-1,4-cyclononanedione, 1,5-cyclononanedione, methyl-1,5-cyclononanedione, ethyl-1,5-cyclononanedione, 1,3 -Cyclodecanedione, methyl-1,3-cyclodecanedione, ethyl-1,3-cyclodecanedione, 1,4-cyclodecanedione, methyl-1,4-cyclodecanedione, ethyl-1,4-cyclo Decanedione, 1,5-cyclodecanedione, methyl-1,5-cyclodecanedione, 1,6-cyclodecanedione, methyl-1,6-cyclodecanedione, ethyl-1,6-cyclodecanedione;

1,3-cycloundecanedione, 1,4-cycloundecanedione, 1,5-cycloundecanedione, 1,6-cycloundecanedione, 1,3-cyclododecanedione, 1,4-cyclododecanedione, 1, 5-cyclododecanedione, 1,6-cyclododecanedione, 1,7-cyclododecanedione, 1,3-cyclotridecanedione, 1,4-cyclotridecanedione, 1,5-cyclotridecanedione, 1 , 6-cyclotridecanedione, 1,7-cyclotridecanedione, 1,3-cyclotetradecanedione, 1,4-cyclotetradecanedione, 1,5-cyclotetradecanedione, 1,6-cyclotetradecanedione, , 7-cyclotetradecanedione, 1,8-cyclotetradecanedione, 1- [4- (4-propio Rubenzyl) phenyl-1-propanone, 2-benzoylcyclohexanone, 3-benzoylcyclohexanone, 4-benzoylcyclohexanone, bicyclo [2.2.1] heptane-2,5-dione, bicyclo [2.2.1] heptane-2 , 6-dione, bicyclo [2.2.1] heptane-2,7-dione, bicyclo [2.2.2] octane-2,5-dione, bicyclo [2.2.2] octane-2,6 -Dione, octahydro-1,3-naphthalenedione, octahydro-1,4-naphthalenedione, octahydro-1,5-naphthalenedione, octahydro-1,6-naphthalenedione, octahydro-1,7-naphthalenedione, octahydro- 1,8-naphthalenedione, 2-acetylcyclopropanone, 2-acetyl-cyclo Ntanon, 3-acetyl - cyclopentanone, 2-acetyl cyclohexanone, 3-acetyl cyclohexanone, 4-acetyl cyclohexanone, diphenyl-1,6-hexanedione.

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

  2,4-pentanedione, methyl-2,4-pentanedione, 2,4-hexanedione, 2,5-hexanedione, 2,4-heptanedione, 2,5-heptanedione, 2,6-heptanedione 3,5-heptanedione, 2,4-octanedione, 2,5-octanedione, 2,6-octanedione, 2,7-octanedione, 3,5-octanedione, 3,6-octanedione, 2,4-nonanedione, 2,5-nonanedione, 2,6-nonanedione, 2,7-nonanedione, 2,8-nonanedione, 3,5-nonanedione, 3,6-nonanedione, 3,7-nonanedione, 3, 8-nonanedione, 4,6-nonanedione, 4,7-nonanedione, 2,4-decanedione, 2,5-decanedione, 2,6-decanedione, 2,7-decane ON, 2,8-decanedione, 2,9-decanedione, 3,5-decanedione, 3,6-decanedione, 3,7-decanedione, 3,8-decanedione, 4,6-decanedione, 4,7-decanedione, 2,4-undecanedione, 2,5-undecanedione, 2,6-undecanedione, 2,7-undecanedione, 2,8-undecanedione, 2,9-undecanedione, 2,10-undecanedione, 3 , 5-Undecanedione, 3,6-Undecanedione, 3,7-Undecanedione, 3,8-Undecanedione, 3,9-Undecanedione, 4,6-Undecanedione, 4,7-Undecanedione, 4, 8-undecanedione, 5,7-undecanedione, 1,3-cyclobutanedione, tetramethylcyclobutanedione, 1, -Cyclopentanedione, 1,3-cyclohexanedione, 1,4-cyclohexanedione, 1,3-cycloheptanedione, 1,4-cycloheptanedione, 1,3-cyclooctanedione, 1,4-cyclooctanedione 1,5-cyclooctanedione, 1,3-cyclononanedione, 1,4-cyclononanedione, 1,5-cyclononanedione, 1,6-cyclodecanedione, 1,3-cycloundecanedione, , 4-cycloundecanedione, 1,5-cycloundecanedione, 1,6-cycloundecanedione, 1,3-cyclododecanedione, 1,4-cyclododecanedione, 1,5-cyclododecanedione, 1,6 -Cyclododecanedione, 1,7-cyclododecanedione, 1- [4- (4-propionylbenzyl) fe Nyl-1-propanone, 2-benzoylcyclohexanone, 3-benzoylcyclohexanone, 4-benzoylcyclohexanone, bicyclo [2.2.1] heptane-2,5-dione, bicyclo [2.2.1] heptane-2,6 -Dione, bicyclo [2.2.1] heptane-2,7-dione, octahydro-1,3-naphthalenedione, octahydro-1,4-naphthalenedione, octahydro-1,5-naphthalenedione, octahydro-1, 6-naphthalenedione, octahydro-1,7-naphthalenedione, octahydro-1,8-naphthalenedione, 2-acetyl-cyclopentanone, 2-acetylcyclohexanone, diphenyl-1,6-hexanedione.

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

  2,5-hexanedione, 3,9-undecanedione, 1,4-cyclohexanedione, 1,4-cyclooctanedione, bicyclo [2.2.1] heptane-2,5-dione, octahydro-1,4 Naphthalene dione, octahydro-1,5-naphthalene dione, diphenyl-1,6-hexanedione.

(Polyfunctional ketone compound)
The polyfunctional ketone compound according to this embodiment is not particularly limited as long as it has three or more ketone groups and the ketone groups are not adjacent to each other.

  Among the polyfunctional ketone 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.

  2,4,6-heptanetrione, 2,4,6-octanetrione, 2,5,7-octanetrione, 1,5-diphenyl-1,3,5-pentanetrione, 1,6-diphenyl-1, 3,5-hexanetrione, 1,3,6-hexanetrione, 1,6-diphenyl-1,3,6-hexanetrione, 1,7-diphenyl-1,3,5-heptanetrione, 1,7- Diphenyl-1,3,6-heptanetrione, 1,7-diphenyl-1,4,6-heptanetrione, 1,7-diphenyl-2,4,6-heptanetrione, 1,7-diphenyl-1,3 , 5,7-heptanetetraone, 1,8-diphenyl-1,3,5-octanetrione, 1,3,6-octanetrione, 1,8-diphenyl-1,3,6-octanetrione, 1, 3,7 Kutantrione, 1,8-diphenyl-1,3,7-octanetrione, 1,3,8-octanetrione, 1,8-diphenyl-1,3,8-octanetrione, 1,8-diphenyl-1,4 , 6-octanetrione, 1,4,7-octanetrione, 1,8-diphenyl-1,4,7-octanetrione, 1,4,8-octanetrione, 1,8-diphenyl-1,4,8 -Octanetrione, 1,8-diphenyl-1,5,7-octanetrione, 1,5,8-octanetrione, 1,8-diphenyl-1,5,8-octanetrione, 1,8-diphenyl-1 , 6,8-octanetrione, 1,8-diphenyl-2,4,6-octanetrione, 2,4,7-octanetrione, 1,8-diphenyl-2,4,7-octanetrione 1,8-diphenyl-1,3,4,7-octanetetraone, 1,8-diphenyl-1,3,4,8-octanetetraone, 1,8-diphenyl-1,3,5,7- Octanetetraone, 1,8-diphenyl-1,3,5,8-octanetetraone, 1,8-diphenyl-1,4,6,8-octanetetraone;

1,5-dinaphthyl-1,3,5-pentanetrione, 1,6-dinaphthyl-1,3,5-hexanetrione, 1,6-dinaphthyl-1,3,6-hexanetrione, 1,7-dinaphthyl -1,3,5-heptanetrione, 1,7-dinaphthyl-1,3,6-heptanetrione, 1,7-dinaphthyl-1,3,7-heptanetrione, 1,7-dinaphthyl-1,4 6-heptanetrione, 1,7-dinaphthyl-1,4,7-heptanetrione, 1,7-dinaphthyl-1,5,7-heptanetrione, 1,7-dinaphthyl-2,4,6-heptanetrione, 1,7-dinaphthyl-1,3,5,7-heptanetetraone, 1,8-dinaphthyl-1,3,5-octanetrione, 1,8-dinaphthyl-1,3,6-octanetrione, 1, 8-ji Futyl-1,3,7 octanetrione, 1,8-dinaphthyl-1,3,8-octanetrione, 1,8-dinaphthyl-1,4,6-octanetrione, 1,8-dinaphthyl-1,4 7-octanetrione, 1,8-dinaphthyl-1,4,8-octanetrione, 1,8-dinaphthyl-1,5,7-octanetrione, 1,8-dinaphthyl-1,5,8-octanetrione, 1,8-dinaphthyl-1,6,8-octanetrione, 1,8-dinaphthyl-2,4,6-octanetrione, 1,8-dinaphthyl-2,4,7-octanetrione, 1,8-dinaphthyl -1,3,5,7-octanetetraone, 1,8-dinaphthyl-1,3,5,8-octanetetraone, 1,8-dinaphthyl-1,4,6,8-octanetetraone, , 8-ji Fuchiru-2,4,5,7-octane tetra one;

1,3,5-cyclohexanetrione, methyl-1,3,5-cyclohexanetrione, ethyl-1,3,5-cyclohexanetrione, dimethyl-1,3,5-cyclohexanetrione, ethylmethyl-1,3 5-cyclohexanetrione, diethyl-1,3,5-cyclohexanetrione, trimethyl-1,3,5-cyclohexanetrione, tetramethyl-1,3,5-cyclohexanetrione, pentamethyl-1,3,5-cyclohexanetrione, Hexamethyl-1,3,5-cyclohexanetrione, 1,3,5-cycloheptanetrione, methyl-1,3,5-cycloheptanetrione, ethyl-1,3,5-cycloheptanetrione, 1,3,5 -Cyclooctanetrione, methyl-1,3,5-cyclooctanetrione , Ethyl-1,3,5-cyclooctanetrione, 1,3,6-cyclooctanetrione, methyl-1,3,6-cyclooctanetrione, ethyl-1,3,6-cyclooctanetrione, acetyl-2 , 4-pentanedione, diacetyl-2,4-pentanedione, acetyl-2,4-hexanedione, diacetyl-2,4-hexanedione, acetyl-2,5-hexanedione, diacetyl-2,5-hexanedione , Triacetyl-2,5-hexanedione, tetraacetyl-2,5-hexanedione;

Acetyl-2,4-heptanedione, diacetyl-2,4-heptanedione, acetyl-2,5-heptanedione, diacetyl-2,5-heptanedione, triacetyl-2,5-heptanedione, tetraacetyl-2 , 5-heptanedione, acetyl-2,6-heptanedione, diacetyl-2,6-heptanedione, triacetyl-2,6-heptanedione, tetraacetyl-2,6-heptanedione, pentaacetyl-2,6 -Heptanedione, hexaacetyl-2,6-heptanedione, acetyl-3,5-heptanedione, diacetyl-3,5-heptanedione, acetyl-2,4-octanedione, diacetyl-2,4-octanedione, Acetyl-2,5-octanedione, diacetyl-2,5-octanedione, triaceti -2,5-octanedione, tetraacetyl-2,5-octanedione, acetyl-2,6-octanedione, diacetyl-2,6-octanedione, triacetyl-2,6-octanedione, tetraacetyl-2 , 6-octanedione, pentaacetyl-2,6-octanedione, 2,6-octanedione, acetyl-2,7-octanedione, diacetyl-2,7-octanedione, triacetyl-2,7-octanedione Tetraacetyl-2,7-octanedione, pentaacetyl-2,7-octanedione, hexaacetyl-2,7-octanedione, heptaacetyl-2,7-octanedione, acetyl-3,5-octanedione, Diacetyl-3,5-octanedione, triacetyl-3,6-octanedione, tetraacetate -3,6-octanedione, diacetylcyclopropanone, triacetylcyclopropanone, tetraacetylcyclopropanone, acetyl-1,3-cyclobutanedione, diacetyl-1,3-cyclobutanedione, triacetyl-2,4 -Cyclobutanedione, tetraacetyl-1,3-cyclobutanedione;

Diacetylcyclopentanone, triacetylcyclopentanone, tetraacetylcyclopentanone, pentaacetylcyclopentanone, hexaacetylcyclopentanone, heptaacetylcyclopentanone, octaacetylcyclopentanone, acetyl-1,3-cyclopentanedione , Diacetyl-1,3-cyclopentanedione, triacetyl-1,3-cyclopentanedione, tetraacetyl-1,3-cyclopentanedione, pentaacetyl-1,3-cyclopentanedione, hexaacetyl-1,3 -Cyclopentanedione, diacetyl-cyclohexanone, triacetylcyclohexanone, tetraacetylcyclohexanone, pentaacetylcyclohexanone, hexaacetylcyclohexanone, heptaacetylcyclohexanone , Octaacetylcyclohexanone, dibenzoylcyclohexanone, acetyl-1,3-cyclohexanedione, diacetyl-1,3-cyclohexanedione, triacetyl-1,3-cyclohexanedione, tetraacetyl-1,3-cyclohexanedione, pentaacetyl- 1,3-cyclohexanedione, hexaacetyl-1,3-cyclohexanedione, acetyl-1,4-cyclohexanedione, diacetyl-1,4-cyclohexanedione, triacetyl-1,4-cyclohexanedione, tetraacetyl-1, 4-cyclohexanedione, pentaacetyl-1,4-cyclohexanedione, hexaacetyl-1,4-cyclohexanedione, acetyl-1,3,5-cyclohexanetrione, diacetyl-1,3,5-cycl Hexanetrione, triacetyl-1,3,5-cyclohexanetrione, tetraacetyl-1,3,5-cyclohexanetrione, pentaacetyl-1,3,5-cyclohexanetrione, hexaacetyl-1,3,5-cyclohexanetrione .

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

  2,4,6-heptanetrione, 2,4,6-octanetrione, 1,5-diphenyl-1,3,5-pentanetrione, 1,6-diphenyl-1,3,5-hexanetrione, 1, 3,6-hexanetrione, 1,6-diphenyl-1,3,6-hexanetrione, 1,7-diphenyl-1,3,5,7-heptanetetraone, 1,5-dinaphthyl-1,3 5-pentanetrione, 1,6-dinaphthyl-1,3,5-hexanetrione, 1,6-dinaphthyl-1,3,6-hexanetrione, 1,7-dinaphthyl-1,3,5,7-heptane Tetraone, 1,3,5-cyclohexanetrione, methyl-1,3,5-cyclohexanetrione, ethyl-1,3,5-cyclohexanetrione, dimethyl-1,3,5-cyclohexanetrione ON, ethylmethyl-1,3,5-cyclohexanetrione, diethyl-1,3,5-cyclohexanetrione, trimethyl-1,3,5-cyclohexanetrione, tetramethyl-1,3,5-cyclohexanetrione, pentamethyl- 1,3,5-cyclohexanetrione, hexamethyl-1,3,5-cyclohexanetrione, 1,3,5-cycloheptanetrione, 1,3,5-cyclooctanetrione, 1,3,6-cyclooctanetrione, Acetyl-2,4-pentanedione, diacetyl-2,4-pentanedione, acetyl-2,4-hexanedione, diacetyl-2,4-hexanedione, acetyl-2,5-hexanedione, diacetyl-2,5 -Hexanedione, triacetyl-2,5-hexanedione, tetraacetate 2,5-hexanedione, diacetyl-cyclohexanone, triacetylcyclohexanone, tetraacetylcyclohexanone, dibenzoylcyclohexanone, acetyl-1,3-cyclohexanedione, diacetyl-1,3-cyclohexanedione, acetyl-1,4-cyclohexane Dione, diacetyl-1,4-cyclohexanedione, acetyl-1,3,5-cyclohexanetrione, diacetyl-1,3,5-cyclohexanetrione.

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

  2,4,6-heptanetrione, 1,5-diphenyl-1,3,5-pentanetrione, 1,7-diphenyl-1,3,5,7-heptanetetraone, 1,3,5-cyclohexanetrione , Methyl-1,3,5-cyclohexanetrione, dimethyl-1,3,5-cyclohexanetrione, trimethyl-1,3,5-cyclohexanetrione, tetramethyl-1,3,5-cyclohexanetrione, pentamethyl-1 , 3,5-cyclohexanetrione, hexamethyl-1,3,5-cyclohexanetrione, acetyl-2,4-pentanedione, diacetyl-2,4-pentanedione, acetyl-2,5-hexanedione, diacetyl-2, 5-hexanedione, diacetyl-cyclohexanone, dibenzoylcyclohexanone, acetyl 1,3-cyclohexanedione, acetyl-1,4-cyclohexanedione, acetyl-1,3,5-cyclohexane trione.

(Polyketone compound)
The polyketone compound according to the present embodiment is not particularly limited as long as it is a compound having two or more ketone groups and having a structure in which the ketone groups are adjacent to each other (structure directly bonded).

  Among the polyketone compounds, it becomes easy to obtain, the cost as a composition can be further suppressed, and it tends to be more economical, and when preparing the composition at room temperature, the polymerization of (C) the epoxy compound can be further suppressed. It is selected from the following group because the stability of the composition tends to be further improved and / or (C) the transparency of the resulting polymer tends to be further improved after polymerizing the epoxy compound. At least one compound is preferred.

  2,3-butanedione, 2,3-pentanedione, 2,3-hexanedione, methyl-2,3-hexanedione, ethyl-2,3-hexanedione, dimethyl-2,3-hexanedione, 3,4 -Hexanedione, 2,3-heptanedione, 3,4-heptanedione, methyl-2,3-heptanedione, ethyl-2,3-heptanedione, dimethyl-2,3-heptanedione, ethylmethyl-2, 3-heptanedione, diethyl-2,3-heptanedione, methyl-3,4-heptanedione, dimethyl-3,4-heptanedione, ethylmethyl-3,4-heptanedione, ethyl-3,4-heptanedione , Diethyl-3,4-heptanedione, 2,3-octanedione, methyl-2,3-octanedione, ethyl-2,3-octanedione Dimethyl-2,3-octanedione, ethylmethyl-2,3-octanedione, diethyl-2,3-octanedione, 3,4-octanedione, methyl-3,4-octanedione, ethyl-3,4- Octanedione, dimethyl-3,4-octanedione, ethylmethyl-3,4-octanedione, diethyl-3,4-octanedione, 4,5-octanedione, methyl-4,5-octanedione, ethyl- 4,5-octanedione, dimethyl-4,5-octanedione, ethylmethyl-4,5-octanedione, diethyl-4,5-octanedione, 2,3-nonanedione, 3,4-nonanedione, 4,5 -Nonanedione, 2,3-decanedione, 3,4-decanedione, 4,5-decanedione, 5,6-decanedione;

1,2-cyclobutanedione, methyl-1,2-cyclobutanedione, dimethyl-1,2-cyclobutanedione, trimethyl-1,2-cyclobutanedione, tetramethyl-1,2-cyclobutanedione, ethyl-1,2- Cyclobutanedione, diethyl-1,2-cyclobutanedione, triethyl-1,2-cyclobutanedione, tetraethyl-1,2-cyclobutanedione, ethylmethyl-1,2-cyclobutanedione, diethylmethyl-1,2-cyclobutanedione, Triethylmethyl-1,2-cyclobutanedione, 1,2-cyclopentanedione, methyl-1,2-cyclopentanedione, ethyl-1,2-cyclopentanedione, dimethyl-1,2-cyclopentanedione, ethylmethyl -1,2-cyclopentanedione, die 1,2-cyclopentanedione, trimethyl-1,2-cyclopentanedione, diethylmethyl-1,2-cyclopentanedione, triethyl-1,2-cyclopentanedione, tetramethyl-1,2-cyclopentane Dione, pentamethyl-1,2-cyclopentanedione, hexamethyl-1,2-cyclopentanedione, tetraethyl-1,2-cyclopentanedione, pentaethyl-1,2-cyclopentanedione, hexaethyl-1,2-cyclopentane Dione, 1,2-cyclohexanedione, methyl-1,2-cyclohexanedione, ethyl-1,2-cyclohexanedione, dimethyl-1,2-cyclohexanedione, ethylmethyl-1,2-cyclohexanedione, diethyl-1, 2-cyclohexanedione, trime 1,2-cyclohexanedione, tetramethyl-1,2-cyclohexanedione, pentamethyl-1,2-cyclohexanedione, hexamethyl-1,2-cyclohexanedione, heptamethyl-1,2-cyclohexanedione, octamethyl-1, 2-cyclohexanedione, triethyl-1,2-cyclohexanedione, tetraethyl-1,2-cyclohexanedione, pentaethyl-1,2-cyclohexanedione, hexaethyl-1,2-cyclohexanedione, heptaethyl-1,2-cyclohexanedione, Octaethyl-1,2-cyclohexanedione;

1,2-cycloheptanedione, methyl-1,2-cycloheptanedione, ethyl-1,2-cycloheptanedione, dimethyl-1,2-cycloheptanedione, ethylmethyl-1-1,2-cycloheptanedione, Diethyl-1,2-cycloheptanedione, 1,2-cyclooctanedione, methyl-1,2-cyclooctanedione, ethyl-1,2-cyclooctanedione, dimethyl-1,2-cyclooctanedione, ethylmethyl -1,2-cyclooctanedione, diethyl-1,2-cyclooctanedione, 1,2-cyclononanedione, methyl-1,2-cyclononanedione, ethyl-1,2-cyclononanedione, 1,2 -Cyclodecanedione, methyl-1,2-cyclodecanedione, ethyl-1,2-cyclodecanedione, 1,2 -Cycloundecanedione, 1,2-cyclododecanedione, 1,2-cyclotridecanedione, 1,2-cyclotetradecanedione, bicyclo [2.2.1] heptane-2,3-dione, bicyclo [2. 2.2] octane-2,3-dione, octahydro-1,2-naphthalenedione, 2,3,4-pentanetrione, 2,3,4-hexanetrione, 2,3,5-hexanetrione, 2, 3,4,5-hexanetetraone, 2,3,4-heptanetrione, 2,3,5-heptanetrione, 2,3,6-heptanetrione, 2,4,5-heptanetrione, 2,5 6-heptanetrione, 3,4,5-heptanetrione, 2,3,4,5-heptanetetraone, 2,3,4,6-heptanetetraone, 2,3,4,5,6-heptanepe Taon, 2,3,4-octanetrione, 2,3,5-octanetrione, 2,3,6-octanetrione, 2,3,7-octanetrione, 2,4,5-octanetrione, 2,4 , 7-octanetrione, 2,5,6-octanetrione, 3,4,5-octanetrione, 3,4,6-octanetrione, 3,5,6-octanetrione;

Diphenyl-1,2,3-propanetrione, diphenyl-1,2,3-butanetrione, diphenyl-1,2,4-butanetrione, diphenyl-1,2,3,4-butanetetraone, diphenyl-1 , 2,3-pentanetrione, diphenyl-1,2,4-pentanetrione, diphenyl-1,2,5-pentanetrione, diphenyl-2,3,4-pentanetrione, diphenyl-1,2,3,4 -Pentanetetraone, diphenyl-1,2,3,5-pentanetetraone, diphenyl-1,2,3,4,5-pentanepentone, diphenyl-1,2,3-hexanetrione, diphenyl-1, 2,4-hexanetrione, diphenyl-1,2,5-hexanetrione, diphenyl-1,2,6-hexanetrione, diphenyl-1 3,4-hexanetrione, diphenyl-1,4,5-hexanetrione, diphenyl-2,3,4-hexanetrione, diphenyl-2,3,5-hexanetrione, diphenyl-1,2,3,4- Hexanetetraone, diphenyl-1,2,3,5-hexanetetraone, diphenyl-1,2,3,6-hexanetetraone, diphenyl-2,3,4,5-hexanetetraone;

Diphenyl-1,2,3,4,5-hexanepentaone, diphenyl-1,2,3,4,6-hexanepentaone, diphenyl-1,2,3,4,5,6-hexanehexaone, Diphenyl-1,2,3-heptanetrione, diphenyl-1,2,4-heptanetrione, diphenyl-1,2,5-heptanetrione, diphenyl-1,2,6-heptanetrione, diphenyl-1,3,3 4-heptanetrione, diphenyl-1,4,5-heptanetrione, diphenyl-1,5,6-heptanetrione, diphenyl-1,2,7-heptanetrione, diphenyl-2,3,4-heptanetrione,- Diphenyl-2,3,5-heptanetrione, diphenyl-2,3,6-heptanetrione, diphenyl-2,3,7-heptanetrione, Phenyl-2,4,5-heptanetrione, diphenyl-2,5,6-heptanetrione, diphenyl-3,4,5-heptanetrione, diphenyl-1,2,3,4-heptanetetraone, diphenyl-1 , 2,3,5-heptanetetraone, diphenyl-1,2,3,6-heptanetetraone, diphenyl-1,2,3,7-heptanetetraone, diphenyl-2,3,4,5-heptane Tetraone, diphenyl-2,3,4,6-heptanetetraone;

Diphenyl-1,2,3-octanetrione, diphenyl-1,2,4-octanetrione, diphenyl-1,2,5-octanetrione, diphenyl-1,2,6-octanetrione, diphenyl-1,2, 7-octanetrione, diphenyl-1,2,8-octanetrione, diphenyl-1,3,4-octanetrione, diphenyl-1,4,5-octanetrione, diphenyl-1,5,6-octanetrione, diphenyl -1,6,7-octanetrione, diphenyl-2,3,4-octanetrione, diphenyl-2,3,5-octanetrione, diphenyl-2,3,6-octanetrione, diphenyl-2,3,7 -Octanetrione, diphenyl-2,4,5-octanetrione, diphenyl-2,5,6-octanetrione Diphenyl-3,4,5-octanetrione, diphenyl-3,4,6-octanetrione, diphenyl-1,2,3,4-octanetetraone, diphenyl-1,2,3,5-octanetetraone ON, diphenyl-1,2,3,6-octanetetraone, diphenyl-1,2,3,7-octanetetraone, diphenyl-1,2,3,8-octanetetraone, diphenyl-1,3,3 4,5-octanetetraone, diphenyl-1,3,4,6-octanetetraone, diphenyl-1,3,5,6-octanetetraone, diphenyl-1,4,5,6-octanetetraone, Diphenyl-1,4,5,7-octanetetraone, diphenyl-1,4,5,8-octanetetraone, diphenyl-1,4,6,7-octanetetraone, Phenyl-1,5,6,7-octanetetraone, diphenyl-1,5,6,8-octanetetraone, diphenyl-2,3,4,5-octanetetraone, diphenyl-2,3,4, 6-octanetetraone, diphenyl-2,3,4,7-octanetetraone, diphenyl-2,4,5,6-octanetetraone, diphenyl-2,4,5,7-octanetetraone, diphenyl- 3,4,5,6-octanetetraone;

Dinaphthyl-1,2,3-propanetrione, dinaphthyl-1,2,3-butanetrione, dinaphthyl-1,2,4-butanetrione, dinaphthyl-1,2,3,4-butanetetraone, dinaphthyl-1 , 2,3-pentanetrione, dinaphthyl-1,2,4-pentanetrione, dinaphthyl-1,2,5-pentanetrione, dinaphthyl-1,3,4-pentanetrione, dinaphthyl-2,3,4-pentane Trione, dinaphthyl-1,2,3,4-pentanetetraone, dinaphthyl-1,2,3,5-pentanetetraone, dinaphthyl-1,2,3,4,5-pentanepentaone, dinaphthyl-1, 2,3-hexanetrione, dinaphthyl-1,2,4-hexanetrione, dinaphthyl-1,2,5-hexanetrione, dinaphthyl-1 2,6-hexanetrione, dinaphthyl-1,3,4-hexanetrione, dinaphthyl-1,4,5-hexanetrione, dinaphthyl-1,4,5-hexanetrione, dinaphthyl-2,3,4-hexanetrione , Dinaphthyl-2,3,5-hexanetrione, dinaphthyl-2,4,5-hexanetrione, dinaphthyl-1,2,3,4-hexanetetraone, dinaphthyl-1,2,3,5-hexanetrione , Dinaphthyl-1,2,3,6-hexanetetraone, dinaphthyl-2,3,4,5-hexanetetraone, dinaphthyl-1,2,3,4,5-hexanepentone, dinaphthyl-1,2 , 3,4,6-hexanepentaone, dinaphthyl-1,2,3,4,5,6-hexanehexaone;

Dinaphthyl-1,2,3-heptanetrione, dinaphthyl-1,2,4-heptanetrione, dinaphthyl-1,2,5-heptanetrione, dinaphthyl-1,2,6-heptanetrione, dinaphthyl-1,2, 7-heptanetrione, dinaphthyl-1,3,4-heptanetrione, dinaphthyl-1,4,5-heptanetrione, dinaphthyl-1,5,6-heptanetrione, dinaphthyl-2,3,4-heptanetrione , Dinaphthyl-2,3,5-heptanetrione, dinaphthyl-2,3,6-heptanetrione, dinaphthyl-2,3,7-heptanetrione, dinaphthyl-2,4,5-heptanetrione, dinaphthyl-3,4 , 5-heptanetrione, dinaphthyl-1,2,3,4-heptanetetraone, dinaphthyl-1,2,3,5- Butanetetraone, dinaphthyl-1,2,3,6-heptanetetraone, dinaphthyl-1,2,3,7-heptanetetraone, dinaphthyl-1,3,4,5-heptanetetraone, dinaphthyl-1, 3,4,6-heptanetetraone, dinaphthyl-1,3,4,7-heptanetetraone, dinaphthyl-1,3,5,6-heptanetetraone, dinaphthyl-1,4,5,6-heptanetetraone ON, dinaphthyl-2,4,5,6-heptanetetraone, dinaphthyl-2,3,4,5-heptanetetraone, dinaphthyl-2,3,4,6-heptanetetraone;

Dinaphthyl-1,2,3-octanetrione, dinaphthyl-1,2,4-octanetrione, dinaphthyl-1,2,5-octanetrione, dinaphthyl-1,2,6-octanetrione, dinaphthyl-1,2, 7-octanetrione, dinaphthyl-1,2,8-octanetrione, dinaphthyl-1,3,4-octanetrione, dinaphthyl-1,4,5-octanetrione, dinaphthyl-1,5,6-octanetrione, dinaphthyl -1,6,7-octanetrione, dinaphthyl-2,3,4-octanetrione, dinaphthyl-2,3,5-octanetrione, dinaphthyl-2,3,6-octanetrione, dinaphthyl-2,3,7 -Octanetrione, dinaphthyl-2,4,5-octanetrione, dinaphthyl-2,5,6-octanetrione , Dinaphthyl-3,4,5-octanetrione, dinaphthyl-3,4,6-octanetrione, dinaphthyl-1,2,3,4-octanetetraone, dinaphthyl-1,2,3,5-octanetetraone ON, dinaphthyl-1,2,3,6-octanetetraone, dinaphthyl-1,2,3,7-octanetetraone, dinaphthyl-1,2,3,8-octanetetraone, dinaphthyl-1,3, 4,5-octanetetraone, dinaphthyl-1,3,4,6-octanetetraone, dinaphthyl-1,3,4,7-octanetetraone, dinaphthyl-1,3,4,8-octanetetraone, Dinaphthyl-1,3,5,6-octanetetraone, dinaphthyl-1,4,5,6-octanetetraone, dinaphthyl-1,4,5,7-octanetetraone, Naphthyl-1,4,5,8-octanetetraone, dinaphthyl-1,4,6,7-octanetetraone, dinaphthyl-1,5,6,7-octanetetraone, dinaphthyl-1,5,6 8-octanetetraone, dinaphthyl-2,3,4,5-octanetetraone, dinaphthyl-2,3,4,6-octanetetraone, dinaphthyl-2,3,4,7-octanetetraone, dinaphthyl- 2,4,5,6-octanetetraone, dinaphthyl-3,4,5,6-octanetetraone;

1,2,3-cyclobutanetrione, 1,2,3-cyclopentanetrione, methyl-1,2,3-cyclopentanetrione, ethyl-1,2,3-cyclopentanetrione, dimethyl-1,2,3 -Cyclopentanetrione, ethylmethyl-1,2,3-cyclopentanetrione, diethyl-1,2,3-cyclopentanetrione, trimethyl-1,2,3-cyclopentanetrione, tetramethyl-1,2,3 -Cyclopentanetrione, triethyl-1,2,3-cyclopentanetrione, tetraethyl-1,2,3-cyclopentanetrione, 1,2,4-cyclopentanetrione, methyl-1,2,4-cyclopentanetrione Ethyl-1,2,4-cyclopentanetrione, dimethyl-1,2,4-cyclopentanetrione, Tilmethyl-1,2,4-cyclopentanetrione, diethyl-1,2,4-cyclopentanetrione, trimethyl-1,2,4-cyclopentanetrione, tetramethyl-1,2,4-cyclopentanetrione, Triethyl-1,2,4-cyclopentanetrione, tetraethyl-1,2,4-cyclopentanetrione, butyl-1,2,4-cyclopentanetrione, 1,2,3,4-cyclopentanetetraone, methyl -1,2,3,4-cyclopentanetetraone, ethyl-1,2,3,4-cyclopentanetetraone, dimethyl-1,2,3,4-cyclopentanetetraone, ethylmethyl-1, 2,3,4-cyclopentanetetraone, diethyl-1,2,3,4-cyclopentanetetraone;

1,2,3-cyclohexanetrione, methyl-1,2,3-cyclohexanetrione, ethyl-1,2,3-cyclohexanetrione, dimethyl-1,2,3-cyclohexanetrione, ethylmethyl-1,2,3 -Cyclohexanetrione, diethyl-1,2,3-cyclohexanetrione, trimethyl-1,2,3-cyclohexanetrione, triethyl-1,2,3-cyclohexanetrione, tetramethyl-1,2,3-cyclohexanetrione, pentamethyl -1,2,3-cyclohexanetrione, hexamethyl-1,2,3-cyclohexanetrione, tetraethyl-1,2,3-cyclohexanetrione, pentaethyl-1,2,3-cyclohexanetrione, hexaethyl-1,2,3 -Cyclohexanetrione, 1, , 4-cyclohexanetrione, methyl-1,2,4-cyclohexanetrione, ethyl-1, -1,4-cyclohexanetrione, dimethyl-1,2,4-cyclohexanetrione, ethylmethyl-1,2,4 -Cyclohexanetrione, diethyl-1,2,4-cyclohexanetrione, trimethyl-1,2,4-cyclohexanetrione, tetramethyl-1,2,4-cyclohexanetrione, pentamethyl-1,2,4-cyclohexanetrione, hexamethyl -1,2,4-cyclohexanetrione, triethyl-1,2,4-cyclohexanetrione, tetraethyl-1,2,4-cyclohexanetrione, pentaethyl-1,2,4-cyclohexanetrione, hexaethyl-1,2,4 -Cyclohexanetrione;

1,2,3,4-cyclohexanetetraone, 1,2,3,5-cyclohexanetetraone, 1,2,4,5-cyclohexanetetraone, 1,2,3-cycloheptanetrione, methyl-1, 2,3-cycloheptanetrione, ethyl-1,2,3-cycloheptanetrione, 1,2,4-cycloheptanetrione, methyl-1,2,4-cycloheptanetrione, ethyl-1,2,4- Cycloheptanetrione, 1,2,5-cycloheptanetrione, methyl-1,2,5-cycloheptanetrione, ethyl-1,2,5-cycloheptanetrione, 1,2,3-cyclooctanetrione, methyl- 1,2,3-cyclooctanetrione, ethyl-1,2,3-cyclooctanetrione, 1,2,4-cyclooctanetrione, methyl- , 2,4-cyclooctanetrione, ethyl-1,2,4-cyclooctanetrione, 1,2,5-cyclooctanetrione, methyl-1,2,5-cyclooctanetrione, ethyl-1,2 , 5-cyclooctanetrione, acetyl-1,2-cyclobutanedione, diacetyl-1,2-cyclobutanedione, acetyl-1,2-cyclopentanedione, diacetyl-1,2-cyclopentanedione, triacetyl-1, 2-cyclopentanedione, tetraacetyl-1,2-cyclopentanedione, pentaacetyl-1,2-cyclopentanedione, hexaacetyl-1,2-cyclopentanedione;

Acetyl-1,2,3-cyclopentanetrione, diacetyl-1,2,3-cyclopentanetrione, triacetyl-1,2,3-cyclopentanetrione, tetraacetyl-1,2,3-cyclopentanetrione, Acetyl-1,2,4-cyclopentanetrione, diacetyl-1,2,4-cyclopentanetrione, triacetyl-1,2,4-cyclopentanetrione, tetraacetyl-1,2,4-cyclopentanetrione, Acetyl-1,2-cyclohexanedione, diacetyl-1,2-cyclohexanedione, triacetyl-1,2-cyclohexanedione, tetraacetyl-1,2-cyclohexanedione, pentaacetyl-1,2-cyclohexanedione, hexaacetyl -1,2-cyclohexanedione, acetyl- , 2,3-cyclohexanetrione, diacetyl-1,2,3-cyclohexanetrione, triacetyl-1,2,3-cyclohexanetrione, tetraacetyl-1,2,3-cyclohexanetrione, pentaacetyl-1,2, 3-cyclohexanetrione, hexaacetyl-1,2,3-cyclohexanetrione, acetyl-1,2,4-cyclohexanetrione, diacetyl-1,2,4-cyclohexanetrione, triacetyl-1,2,4-cyclohexanetrione Tetraacetyl-1,2,4-cyclohexanetrione, pentaacetyl-1,2,4-cyclohexanetrione, hexaacetyl-1,2,4-cyclohexanetrione, acetyl-1,2-cyclohexanedione, 4,5- Pyrenees on, 5,6-cris Dione.

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

  2,3-butanedione, 2,3-pentanedione, 2,3-hexanedione, 3,4-hexanedione, 2,3-heptanedione, 3,4-heptanedione, 2,3-octanedione, 3, 4-octanedione, 4,5-octanedione, 2,3-nonanedione, 3,4-nonanedione, 4,5-nonanedione, 2,3-decanedione, 3,4-decanedione, 4,5-decanedione, 5, 6-decanedione, 1,2-cyclobutanedione, 1,2-cyclopentanedione, methyl-1,2-cyclopentanedione, dimethyl-1,2-cyclopentanedione, 1,2-cyclohexanedione, methyl-1, 2-cyclohexanedione, dimethyl-1,2-cyclohexanedione, 1,2-cycloheptanedione, 1,2-cyclooctanedi 1,2-cyclononanedione, 1,2-cyclodecanedione, 1,2-cycloundecanedione, 1,2-cyclododecanedione, bicyclo [2.2.1] heptane-2,3-dione, Bicyclo [2.2.2] octane-2,3-dione, octahydro-1,2-naphthalenedione, 2,3,4-pentanetrione, 2,3,4-hexanetrione, 2,3,5-hexane Trione, 2,3,4,5-hexanetetraone, 2,3,4-heptanetrione, 2,3,5-heptanetrione, 2,3,6-heptanetrione, 2,4,5-heptanetrione, 2,5,6-heptanetrione, 3,4,5-heptanetrione, 2,3,4,5-heptanetetraone, 2,3,4,6-heptanetetraone, 2,3,4,5 6-Heptane Ntaone, 2,3,4-octanetrione, 2,3,5-octanetrione, 2,3,6-octanetrione, 2,3,7-octanetrione, 2,4,5-octanetrione, 2,4 , 7-octanetrione, 2,5,6-octanetrione, 3,4,5-octanetrione, 3,4,6-octanetrione, 3,5,6-octanetrione;

Diphenyl-1,2,3-propanetrione, diphenyl-1,2,3-butanetrione, diphenyl-1,2,4-butanetrione, diphenyl-1,2,3,4-butanetetraone, diphenyl-1 , 2,3-pentanetrione, diphenyl-1,2,4-pentanetrione, diphenyl-1,2,5-pentanetrione, diphenyl-2,3,4-pentanetrione, diphenyl-1,2,3-hexane Trione, diphenyl-1,2,4-hexanetrione, diphenyl-1,2,5-hexanetrione, diphenyl-1,2,6-hexanetrione, diphenyl-1,3,4-hexanetrione, diphenyl-1, 4,5-hexanetrione, diphenyl-2,3,4-hexanetrione, diphenyl-2,3,5-hexanetrione 1,2,4-cyclopentanetrione, methyl-1,2,4-cyclopentanetrione, dimethyl-1,2,4-cyclopentanetrione, butyl-1,2,4-cyclopentanetrione, 1, 2,3-cyclohexanetrione, 1,2,4-cyclohexanetrione, 1,2,3,4-cyclohexanetetraone, 1,2,3,5-cyclohexanetetraone, 1,2,4,5-cyclohexanetetra ON, 1,2,3-cycloheptanetrione, 1,2,4-cycloheptanetrione, 1,2,5-cycloheptanetrione, 1,2,3-cyclooctanetrione, 1,2,4-cyclooctane Trione, 1,2,5-cyclooctanetrione, acetyl-1,2-cyclobutanedione, diacetyl-1,2-cyclobutanedione Acetyl-1,2-cyclopentanedione, diacetyl-1,2-cyclopentanedione, acetyl-1,2,3-cyclopentanetrione, diacetyl-1,2,3-cyclopentanetrione, acetyl-1,2, 4-cyclopentanetrione, diacetyl-1,2,4-cyclopentanetrione, acetyl-1,2-cyclohexanedione, diacetyl-1,2-cyclohexanedione, acetyl-1,2,3-cyclohexanetrione, diacetyl-1 , 2,3-cyclohexanetrione, acetyl-1,2,4-cyclohexanetrione, diacetyl-1,2,4-cyclohexanetrione, acetyl-1,2-cyclohexanedione, 4,5-pyrenedione, 5,6-chrysene Zeon.

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

  2,3-butanedione, 2,3-pentanedione, 2,3-hexanedione, 3,4-hexanedione, 2,3-heptanedione, 3,4-heptanedione, 2,3-octanedione, 1, 2-cyclobutanedione, 1,2-cyclopentanedione, methyl-1,2-cyclopentanedione, 1,2-cyclohexanedione, methyl-1,2-cyclohexanedione, 1,2-cyclooctanedione, 1,2 -Cyclodecanedione, 2,3,4-pentanetrione, diphenyl-1,2,3-propanetrione, diphenyl-1,2,4-pentanetrione, 1,2,4-cyclopentanetrione, methyl-1, 2,4-cyclopentanetrione, butyl-1,2,4-cyclopentanetrione, 1,2,3-cyclohexanetrione, ace Ru-1,2-cyclopentanedione, acetyl-1,2,4-cyclopentanetrione, acetyl-1,2-cyclohexanedione, acetyl-1,2,3-cyclohexanetrione, 4,5-pyrenedione, 5, 6-Chrysenedione.

(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) When the binding force between the ketone compound and (B) boron trihalide is improved and the composition is made into a composition, the polymerization of the (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 ketone 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 the (B) boron trihalide contained in the composition form a compound (complex) via a coordination bond with the (A) ketone 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 is preferable to have a partial structure represented by the following formula (5), (6), (7) or (8). Moreover, since it exists in the tendency which the stability as a composition improves more, it is more preferable to have the partial structure represented by following formula (5) or (6). From the viewpoint of transparency, it is more preferable to have a partial structure represented by the formula (5) 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 (6) because the heat resistance of the cured product formed from the 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 (9).
(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 (9)

In the formula (9), 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 (10).

In the above formula (10), 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) ketone compound and (B) boron trihalide can be represented by an index α calculated by the following formula (4).
Index α = αk / αb (4)
αk: (A) Amount of substance of the ketone group of the ketone 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) the ketone 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 ketone compound and (B) the boron trihalide compound may be altered through a coordinate bond, 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 process of polymerizing the composition and removing the (A) ketone compound contained in the resulting polymer is necessary, the cost required for the process 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 1, (C) the substance amount (mol) of the epoxy group contained in the epoxy compound is 50 or more, (A) the ketone compound, 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 (11).
Index β = αb / αep × 100 (11)
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 ketone compound, (B) a boron trihalide and (C) an epoxy compound are simultaneously added, A method in which two components selected arbitrarily among A) ketone compound, (B) boron trihalide and (C) epoxy compound are mixed and then added to the remaining components or the remaining components are added. . 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 ketone 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 ketone compound and (B) boron trihalide is not particularly limited as long as it is a generally used method, but (A) a ketone compound and (B) three Examples thereof include a method of directly reacting boron halide, a method of reacting (A) a ketone compound and (B) a compound containing boron trihalide, and the like. Among these, the method of reacting (A) a ketone 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 ketone 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 ketone 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 choice of 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 ketone 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 the coordination bond consisting of (A) a ketone 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) the ketone compound and (B) may deviate from the desired ratio, the temperature at which the mixture is prepared is controlled in order 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) the ketone 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 ketone 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) ketone compound in the standard state is low and the (A) ketone compound may volatilize during the reaction, it is an effective means to pressurize at or above atmospheric pressure. It is.

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

  (A) The compound capable of dissolving the ketone compound is not particularly limited as long as it is generally used. Specific examples thereof include 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 compounds, methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, trichloroethane, tetrachloroethane, pentachloroethane, hexachloroethane, dichloroethylene, trichloroethylene, tetrachloroethylene, dichloropropane, trike Halogenated hydrocarbon compounds such as propane, 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, methyl acetone, ethyl methyl ketone, methyl propyl ketone, methyl butyl ketone, methyl isobutyl ketone, methyl hexyl ketone, diethyl ketone, Ketones such as ethyl butyl ketone, dipropyl ketone, diisobutyl ketone and 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, Examples include esters such as 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 ketone compound and (B) boron trihalide, (A) a compound capable of dissolving the ketone 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 ketone 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 ketone 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.

  When preparing a composition containing (A) a ketone compound, (B) boron trihalide, and (C) an epoxy compound, if there is a possibility that the raw material may solidify, 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 ketone compound, (B) boron trihalide, and (C) an epoxy compound, polymerization of (C) the epoxy compound can be further suppressed, and a uniform composition can be more easily produced. Since there is a tendency to be obtained, the temperature for preparing the composition is preferably 80 ° C. or less. From the same viewpoint, the temperature for preparing the composition is more preferably 70 ° 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 60 ° 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 ketone 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 ketone 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 ketone compound, (B) boron trihalide, and (C) an epoxy compound, the contained compound has a solid, or (A) the ketone 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 ketone compound and (B) boron trihalide which is a solid. 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 ketone 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, chloroben Emissions, dichlorobenzene, trichlorobenzene, halogenated hydrocarbon compounds such as chlorotoluene and chloronaphthalene are preferred.

  When preparing a composition containing (A) a ketone 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 (C) the epoxy compound, and the stability of the composition containing (A) the ketone compound, (B) boron trihalide, and (C) the epoxy compound is further improved. Since it exists in the tendency, it is preferable that it is 80 degrees C or less. From the same viewpoint, it is more preferably 70 ° C. or lower, and further preferably 60 ° C. or lower. 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 ketone 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 60 ° C. or higher, and further preferably 80 ° 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 ketone 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 ketone 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 at least one compound selected from the group consisting of cyclic ester compounds, cyclic carbonate compounds, cyclic siloxane compounds, and hydroxyl group-containing compounds. It is preferable that 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 selected from the group consisting of cyclic ester compounds, cyclic carbonate compounds, and hydroxyl group-containing compounds. More preferably, it is at least one compound selected. (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 is a compound having an ester group in the cyclic structure. Specifically, it is at least one compound that can be selected from the following group.

  Etano-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-lactone, octano-2- Lactone, Octano-3-lactone, Octano-4-lactone, Octano-5-lactone, Oct No-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.

  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 ester 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 carbonate compound)
The cyclic carbonate compound is not particularly limited as long as it is a compound having a carbonate group in the cyclic structure. Specifically, it is at least one compound that can be selected from the following group.

  Ethylene carbonate, propylene carbonate, butylene carbonate, pentylene carbonate, hexylene carbonate, heptylene carbonate, octylene carbonate, nonylene carbonate, decylene carbonate, undecylene carbonate, dodecylene carbonate, tridecylene carbonate, tetradecylene carbonate , Pentadecylene carbonate, hexadecylene carbonate, propyl-1,3-dioxolan-2-one, butyl-1,3-dioxolan-2-one, pentyl-1,3-dioxolan-2-one, hexyl-1 , 3-dioxolan-2-one, cyclohexyl-1,3-dioxolan-2-one, 1,3-dioxan-2-one, methyl-1,3-dioxan-2-one, dimethyl-1,3 Dioxane-2-one, ethyl-1,3-dioxane-2-one, propyl-1,3-dioxane-2-one, butyl-1,3-dioxane-2-one, pentyl-1,3-dioxane- 2-one, hexyl-1,3-dioxane-2-one, cyclohexyl-1,3-dioxane-2-one.

  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.

  Ethylene carbonate, propylene carbonate, butylene carbonate, pentylene carbonate, hexylene carbonate, propyl-1,3-dioxolan-2-one, butyl-1,3-dioxolan-2-one, 1,3-dioxane-2-one , Dimethyl-1,3-dioxan-2-one, ethyl-1,3-dioxan-2-one, propyl-1,3-dioxan-2-one, butyl-1,3-dioxan-2-one.

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

  Ethylene carbonate, propylene carbonate, butylene carbonate, 1,3-dioxane-2-one, dimethyl-1,3-dioxane-2-one.

(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. The composition containing (A) a ketone 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 at 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 (D) chain transfer agent and (C) epoxy compound can also be represented by the following formula (12).
Index γ = αd / αep × 100 (12)
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 ketone 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) a ketone compound, (B) boron trihalide, (C) an epoxy compound, (D) a method of simultaneously adding a chain transfer agent, (A) a ketone 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 ketone 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 (13), 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（１３）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 (13), 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-ketone 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 in preparing the boron trihalide-ketone compound in a sample bottle, add chloroform-d (manufactured by Wako Pure Chemical Industries, Ltd.), Prepared to 1 g.
(3) To the sample bottle, 10 mg of the prepared boron trihalide-ketone compound was weighed, chloroform-d (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the total amount was adjusted to 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-ketone 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 (4).
Index α = αk / αb (4)
here,
αk: (A) Amount of substance of the ketone group of the ketone 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 (11).
Index β = αb / αep × 100 (11)
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 placed in a thermostat set at 30 ° 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").

About the raw material used by the Example and the comparative example, it shows to the following (1)-(119).
(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.

(Ketone compound)
(36) Ketone compound A: Acetone (manufactured by Aldrich, hereinafter referred to as “MKCA”)
(37) Ketone compound B: 2-butanone (manufactured by Aldrich, hereinafter referred to as “MKCB”)
(38) Ketone compound C: cyclobutanone (manufactured by Aldrich, hereinafter referred to as “MKCC”)
(39) Ketone compound D: 3-pentanone (manufactured by Aldrich, hereinafter referred to as “MKCD”)
(40) Ketone compound E: 3-methyl-2-butanone (manufactured by Aldrich, hereinafter referred to as “MKCE”)
(41) Ketone compound F: cyclopentanone (manufactured by Aldrich, hereinafter referred to as “MKCF”)
(42) Ketone compound G: 3-hexanone (manufactured by Aldrich, hereinafter referred to as “MKCG”)
(43) Ketone compound H: 3,3-dimethyl-2-butanone (manufactured by Aldrich, hereinafter referred to as “MKCH”)
(44) Ketone compound I: 3-methyl-2-pentanone (manufactured by Aldrich, hereinafter referred to as “MKCI”)
(45) Ketone compound J: cyclohexanone (manufactured by Aldrich, hereinafter referred to as “MKCJ”)
(46) Ketone compound K: 3-heptanone (manufactured by Aldrich, hereinafter referred to as “MKCK”)
(47) Ketone compound L: 3-octanone (manufactured by Aldrich, hereinafter referred to as “MKCL”)
(48) Ketone compound M: cyclooctanone (manufactured by Aldrich, hereinafter referred to as “MKCM”)
(49) Ketone compound N: 5-nonanone (manufactured by Aldrich, hereinafter referred to as “MKCN”)
(50) Ketone compound O: cyclononanone (manufactured by Aldrich, hereinafter referred to as “MKCO”)
(51) Ketone compound P: 2-decanone (manufactured by Aldrich, hereinafter referred to as “MKCP”)
(52) Ketone compound Q: cyclodecanone (manufactured by Aldrich, hereinafter referred to as “MKCQ”)
(53) Ketone compound R: 2-undecanone (manufactured by Aldrich, hereinafter referred to as “MKCR”)
(54) Ketone compound S: 3-dodecanone (manufactured by Aldrich, hereinafter referred to as “MKCS”)
(55) Ketone compound T: cyclododecanone (manufactured by Aldrich, hereinafter referred to as “MKCT”)
(56) Ketone compound U: 7-tridecanone (manufactured by Aldrich, hereinafter referred to as “MKCU”)
(57) Ketone compound V: 3-tetradecanone (manufactured by Aldrich, hereinafter referred to as “MKCV”)
(58) Ketone compound W: 1- [1,1′-biphenyl] -4-yl-2-cyclohexaneethanone (manufactured by Aldrich, hereinafter referred to as “MKCW”)
(59) Ketone compound X: 1- (4′-methyl [1,1′-biphenyl] -4-yl) -1-octadecanone (manufactured by Aldrich, hereinafter referred to as “MKCX”)
(60) Ketone compound Y: 2,3-butanedione (manufactured by Aldrich, hereinafter referred to as “MKCY”)
(61) Ketone compound Z: 2,3-pentanedione (manufactured by Aldrich, hereinafter referred to as “MKCZ”)
(62) Ketone compound AA: 2,4-pentanedione (manufactured by Aldrich, hereinafter referred to as “MKCAA”)
(63) Ketone compound AB: 2,3-hexanedione (manufactured by Aldrich, hereinafter referred to as “MKCAB”)
(64) Ketone compound AC: 2,5-hexanedione (manufactured by Aldrich, hereinafter referred to as “MKCAC”)
(65) Ketone compound AD: 1,2-cyclohexanedione (manufactured by Aldrich, hereinafter referred to as “MKCAD”)
(66) Ketone compound AE: 1,3-cyclohexanedione (manufactured by Aldrich, hereinafter referred to as “MKCAE”)
(67) Ketone compound AF: 1,4-cyclohexanedione (manufactured by Aldrich, hereinafter referred to as “MKCAF”)
(68) Ketone compound AG: 3-methyl-1,2-cyclopentanedione (manufactured by Aldrich, hereinafter referred to as “MKCAG”)
(69) Ketone compound AH: 2,3-heptanedione (manufactured by Aldrich, hereinafter referred to as “MKCAH”)
(70) Ketone compound AI: bicyclo [2.2.1] heptane-2,5-dione (manufactured by Alrich, hereinafter referred to as “MKKAI”)
(71) Ketone compound AJ: 1,4-cyclooctanedione (manufactured by Aldrich, hereinafter referred to as “MKCAJ”)
(72) Ketone compound AK: Octahydro-1,5-naphthalenedione (manufactured by Aldrich, hereinafter referred to as “MKCAK”)
(73) Ketone compound AL: 1,2-cyclodecanedione (manufactured by Aldrich, hereinafter referred to as “MKCAL”)
(74) Ketone compound AM: 3,9-undecanedione (Aldrich, hereinafter referred to as “MKCAM”)
(75) Ketone compound AN: 1,2-cyclododecanedione (manufactured by Aldrich, hereinafter referred to as “MKCAN”)
(76) Ketone compound AO: 1,6-diphenyl-1,6-hexanedione (manufactured by Aldrich, hereinafter referred to as “MKCAO”)
(77) Ketone compound AP: 2-acetyl-1,3-cyclopentanedione (manufactured by Aldrich, hereinafter referred to as “MKCAP”)
(78) Ketone compound AQ: 1,3-diphenyl-1,2,3-propanetrione (Aldrich, hereinafter referred to as “MKCAQ”)
(79) Ketone compound AR: 2,6-dibenzoylcyclohexanone (manufactured by Aldrich, hereinafter referred to as “MKCAR”)
(80) Ketone compound AS: 3,4-diacetyl-2,5-hexanedione (manufactured by Aldrich, hereinafter referred to as “MKCAS”)

(Boron trihalide compound)
(81) Boron trihalide compound A: Boron trifluoride dimethyl ether complex (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “BF3DME”)
(82) Boron trihalide compound B: Boron trifluoride diethyl ether complex (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “BF3DEE”)
(83) Boron trihalide compound C: Boron trifluoride dibutyl ether complex (manufactured by Aldrich, hereinafter referred to as “BF3DBE”)
(84) Boron trihalide compound D: Boron trifluoride tert-butyl methyl ether complex (manufactured by Aldrich, hereinafter referred to as “BF3TBME”)
(85) Boron trihalide compound E: boron trifluoride tetrahydrofuran complex (manufactured by Aldrich, hereinafter referred to as “BF3THF”)
(86) Boron trihalide compound F: boron trifluoride methyl sulfide complex (manufactured by Aldrich, hereinafter referred to as “BF3DMS”)
(87) Boron trihalide compound G: Boron trifluoride methanol complex (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “BF3MNOL”)
(88) Boron trihalide compound H: Boron trifluoride propanol complex (manufactured by Aldrich, hereinafter referred to as “BF3PNOL”)
(89) Boron trihalide compound I: boron trifluoride acetic acid complex (manufactured by Aldrich, hereinafter referred to as “BF3ACOH”)
(90) Boron trihalide compound J: Boron trifluoride phenol complex (manufactured by Aldrich, hereinafter referred to as “BF3PHNOL”)
(91) Boron trihalide compound K: Boron trifluoride ethylamine complex (manufactured by Aldrich, hereinafter referred to as “BF3MEA”)
(92) Boron trihalide compound L: Boron trifluoride piperidine complex (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “BF3PPD”)
(93) Boron trihalide compound Q: Boron trichloride (1.0 mol / L dichloromethane solution) (manufactured by Aldrich, hereinafter referred to as “BCl 3 DCM”)
(94) Boron trihalide compound R: Boron tribromide (1.0 mol / L dichloromethane solution) (manufactured by Aldrich, hereinafter referred to as “BBr3DCM”)

(Thermal polymerization accelerator)
(95) Phosphonium salt compound: tetra-n-butylphosphonium bromide (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “TBPB”)
(96) Amine compound A: Tributylamine (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “TBA”)
(97) Amine compound B: N, N-dimethylcyclohexylamine (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “DMCHA”)
(98) Amine compound C: N, N-diethylethanolamine (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “DEENA”)
(99) Sulfonium salt compound A: Trade name “SI-25” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S25”)
(100) Sulfonium salt compound B: trade name “SI-60” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S60”)
(101) Sulfonium salt compound C: trade name “SI-80” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S80”)
(102) Sulfonium salt compound D: trade name “SI-100” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S100”)
(103) Sulfonium salt compound E: trade name “SI-110” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S110”)
(104) Sulfonium salt compound F: Trade name “SI-150” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S150”)
(105) Sulfonium salt compound G: trade name “SI-180” (manufactured by Sanshin Chemical Industry Co., Ltd., hereinafter referred to as “S180”)

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

(Chain transfer agent)
(108) Chain transfer agent A: 1-butanol (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “CTRA”)
(109) Chain transfer agent B: 2-butanol (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “CTRB”)
(110) Chain transfer agent C: ethylene glycol (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “CTRC”)
(111) Chain transfer agent D: 1,2-propanediol (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “CTRD”)
(112) Chain transfer agent E: 2,3-butanediol (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “CTRE”)
(113) Chain transfer agent F: butano-4-lactone (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “CTRF”)
(114) Chain transfer agent G: Pentano-4-lactone (manufactured by Aldrich, hereinafter referred to as “CTRG”)
(115) Chain transfer agent H: ethylene carbonate (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “CTRH”)
(116) Chain transfer agent I: Propylene carbonate (manufactured by Aldrich, hereinafter referred to as “CTRI”)
(117) Chain transfer agent J: 1,3-dioxan-2-one (manufactured by Aldrich, hereinafter referred to as “CTRJ”)
(118) Chain transfer agent K: hexamethylcyclotrisiloxane (manufactured by Shin-Etsu Chemical Co., Ltd., hereinafter referred to as “CTRK”)
(119) Chain transfer agent L: Octamethylcyclotetrasiloxane (manufactured by Shin-Etsu Chemical Co., Ltd., hereinafter referred to as “CTRL”)

Example 1
<Preparation of boron trihalide-ketone 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 procedures (1) to (4) were performed to prepare a boron trihalide-ketone compound (hereinafter referred to as “BF3-MKCA”).

<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 80 ° C. for 1 hour (2) Temperature rise to 130 ° C. (temperature rise rate: 10 ° C./hr)
(3) Hold at 130 ° C. for 1 hour ・ Polymerization condition B
(1) Hold at 80 ° C. for 1 hour (2) Temperature rise to 130 ° C. (temperature rise rate: 10 ° C./hr)
(3) Hold at 130 ° 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 2-94)
Except having set it as the composition ratio of Tables 1-9, and superposition | polymerization conditions, the composition was prepared by the method similar to Example 1, and the polymer was obtained.
In Examples 48 to 54, 67 to 70, and 77 to 81, samples for polymerization evaluation and transparency evaluation were prepared in sealed pressure bottles for evaluation.
The evaluation results of the compositions prepared in Examples 1 to 94 are shown in Tables 7, 8, and 9.

(Comparative Examples 1 to 59)
According to the composition of Tables 10 and 11, the compositions of Comparative Examples 1 to 59 were prepared by the same method as in Example 1, and the polymer was obtained according to the polymerization conditions of Tables 12 and 13. In Comparative Examples 25-31, 44-47, and 54-58, samples for polymerization evaluation were prepared in sealed pressure-resistant bottles for evaluation. Tables 12 and 13 show the evaluation results of the compositions prepared in Comparative Examples 1 to 59.

  As shown in Tables 1 to 13, the present embodiment contains (A) a ketone compound, (B) boron trihalide, and (C) an epoxy compound, and (A) a ketone 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 95)
<Preparation of glass substrate coated with polymer>
(1) The polymer obtained in Example 91 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 96 to 98)
A glass substrate coated with the polymer was evaluated in the same manner as in Example 95 except that the polymer obtained in the examples shown in Table 14 was used.

  As shown in Table 14, this embodiment contains (A) a ketone compound, (B) boron trihalide, and (C) an epoxy compound, and (A) a ketone compound and (B) three. 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.

Example 99
<Preparation of boron trihalide-ketone compound (BF3-MKCJ-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 in a nitrogen atmosphere was placed in the water bath of (1) above, and 41% by mass of cyclohexanone and 59% 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 having 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 15 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 19.
The mixing index γ was calculated by the following formula (12).
Index γ = αd / αep × 100 (12)
here,
αd: (D) amount of chain transfer agent (mol)
αep: (C) The amount (mol) of the epoxy group contained in the epoxy compound, respectively.
Moreover, any of the following was used as polymerization conditions.
・ Polymerization condition C
(1) Hold at 80 ° C. for 1 hour (2) Temperature rise to 130 ° C. (temperature rise rate: 10 ° C./hr)
(3) Hold at 130 ° C. for 4 hours ・ Polymerization condition D
(1) Hold at 80 ° C. for 1 hour (2) Temperature rise to 130 ° C. (temperature rise rate: 10 ° C./hr)
(3) Hold at 130 ° C. for 4 hours (4) Temperature increase to 150 ° C. (temperature increase rate: 20 ° C./hr)
(5) Hold at 150 ° C. for 30 minutes (8) The epoxy group reaction rate of the polymer obtained in (7) above is measured by the method of Table 19, and the epoxy group in the original epoxy compound is polymerized. I confirmed.

<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>
(9) Obtained in (7) above in a vacuum dryer (VOS-451D, manufactured by Tokyo Rika Kikai Co., Ltd.) The polymer obtained was put and dried at 50 ° C. and 13 Pa for 24 hours.
(10) The polymer obtained in (9) above was transferred to a dry glass container, and the weight of the polymer was measured (hereinafter referred to as “RGWS”).
(11) A thermostat (IPHH-202, manufactured by Espec Corp.) was placed in a nitrogen atmosphere, and then the temperature in the chamber was set to 150 ° C. and held for 2000 hours.
(12) The weight of the polymer obtained in (11) above was measured (hereinafter referred to as “RGWF”).
(13) The change in the weight of the polymer (hereinafter referred to as “RGW”) was calculated by the following equation.
RGW (%) = 100−RGWF / RGWS × 100
(14) 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 100 to 257)
Polymers were obtained in the same manner as in Example 99 except that the composition ratios in Tables 15 to 18 and the polymerization conditions in Tables 19 to 22 were used. The evaluation result of the polymer obtained in Examples 99-257 is shown in Tables 19-22.
In Examples 129 to 135, 142 to 157, 164 to 179, and 186 to 194, the polymer was prepared in a sealed pressure bottle.

  As shown in Tables 15 to 22, this embodiment contains (A) a ketone compound, (B) 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 ketone compound and (B) boron trihalide form a complex have a low 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 ketone compound, (B) a boron trihalide, and (C) an epoxy compound, and at least a part of the (A) ketone compound and the (B) boron trihalide forms a complex. The composition. The composition according to claim 1, wherein the (A) ketone compound is a compound represented by the following formula (1), (2) or (3).

[Wherein, a, c, d and f each independently represents a number of 1 or more; b and e each independently represents a number of 2 or more;
R ₁ and R ₂ each independently represent a chain, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group, and R ₃ represents a hydrogen atom Or a linear, branched or cyclic aliphatic or substituted or unsubstituted aromatic hydrocarbon group having 1 to 20 carbon atoms, wherein R ₁ , R ₂ and R ₃ may be linked to each other;
R ₄ and R ₅ each independently represent a chain, branched or cyclic aliphatic hydrocarbon group having 1 to 20 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group, and R ₅ are the same However, they may be different, and R ₄ , R ₅ and R ₅ may be linked to each other,
R _6, R ₇ and R ₈ are each independently a number of 1 to 20 chain carbons, straight, branched or cyclic aliphatic hydrocarbon group or a substituted or unsubstituted aromatic hydrocarbon group, R ₆ and R ₈ may be the same or different, and R ₆ , R ₇ or R ₈ and R ₆ or R ₈ may be linked to each other. ]   The composition according to claim 1 or 2, wherein the (A) ketone compound has 3 to 31 carbon atoms.   The composition according to any one of claims 1 to 3, wherein the number of ketone groups of the (A) ketone compound is 1 to 8. The index α representing the ratio of the (A) ketone compound and the (B) boron trihalide represented by the following formula (4) is 1 to 1000, according to any one of claims 1 to 4. The composition as described.
Index α = αk / αb (4)
αk: Substance amount (mol) of the ketone group of the (A) ketone compound
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 (5), (6), (7) or (8).

[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.