JP5963624B2 - Composition and polymer - Google Patents

Description

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

  Episulfide compounds are used in a wide range of fields such as plastic raw materials, adhesives, drugs, insecticides, herbicides and the like.

  A plastic formed by polymerizing an episulfide compound has characteristics such as a high refractive index, a high Abbe number, a high heat resistance and a high strength. It is used as a material with performance.

  Since the episulfide compound has high polymerizability, it is used as an excellent quick-curing adhesive as compared with an epoxy compound that has been generally used as an adhesive.

  One method for polymerizing the episulfide compound includes a method using a polymerization catalyst, and several methods have been proposed so far.

  For example, Patent Document 1 proposes a method using a trivalent organic phosphorus compound, an amino group-containing organic compound, or a salt thereof. Patent Document 2 proposes a method using various onium salts as an energy ray-sensitive cationic polymerization initiator. Furthermore, in Non-Patent Document 1, a method using a zinc porphyrin complex, and in Non-Patent Document 2, a method using a salt of a thiol compound and 1,8-diazabicyclo [5.4.0] undec-7-ene, Non-Patent Document 3 proposes a method using a metal thiolate compound having zinc or cadmium as a central metal.

JP 2001-288177 A JP 2011-063776 A

Macromolecules 1990, 23, 3887-3892. Macromolecules 1999, 32, 4485-4487. J. et al. Chem. Soc. C 1969, 2087-2092.

  However, the trivalent organic phosphorus compound described in Patent Document 1 may react with an episulfide group to cause a desulfurization reaction, and a desired polymer may not be obtained. In addition, since the amino group-containing organic compound reacts with the episulfide group rapidly under normal temperature conditions where the composition with the episulfide compound can be most easily prepared, the stability as the composition may be low. Furthermore, side reactions may occur due to abrupt reaction with the episulfide group. Further, these salts contain a halogenated anion, which may cause a side reaction and inhibit a desired polymerization.

  The onium salt described in Patent Document 2 is a complex molecule designed to have a structure that absorbs specific energy rays, and a multi-step process is required to produce the molecule. It tends to be an expensive compound. Therefore, the composition of the onium salt and the episulfide compound inevitably tends to be expensive.

  The zinc porphyrin complex described in Non-Patent Document 1 has a low stability as a composition because a reaction with an episulfide group occurs abruptly under normal temperature conditions where a composition with an episulfide compound can be most easily prepared. There is. Furthermore, side reactions may occur due to abrupt reaction with the episulfide group. In addition, the method for synthesizing the porphyrin compound and its complex is complicated, and in order to produce it, a multi-step process is required, which tends to be an expensive compound. Therefore, the composition containing the zinc porphyrin complex inevitably tends to be expensive. Furthermore, the zinc porphyrin complex contains a zinc atom, and gives a relatively disadvantageous composition from the viewpoint of reducing the environmental load that has been attracting attention in recent years.

  The salt of thiol compound and 1,8-diazabicyclo [5.4.0] undec-7-ene described in Non-Patent Document 2 is useful because it is an inexpensive and easily prepared salt. It is a polymerization catalyst. However, this salt may have a low stability as a composition because a reaction with an episulfide group occurs abruptly under normal temperature conditions in which a composition with an episulfide compound can be most easily prepared. Furthermore, this salt may cause a side reaction due to a rapid reaction with the episulfide group.

  When the metal thiolate compound described in Non-Patent Document 3 has a low stability as a composition because a reaction with an episulfide group occurs abruptly at room temperature under which the composition with an episulfide compound can be most easily prepared. There is. Furthermore, this metal thiolate compound may cause a side reaction due to a rapid reaction with an episulfide group. In addition, a decomposition reaction may occur from a metal-sulfur bond present in the polymer, and the weather resistance of the polymer tends to decrease. In addition, the polymerization catalyst contains a metal, and gives a relatively unfavorable composition from the viewpoint of reducing the environmental load that has been attracting attention in recent years.

  Therefore, the present invention has been made in view of the above circumstances, and has a composition having excellent stability at room temperature, sufficiently high polymerizability, and few side reactions during polymerization, and the composition. It aims at providing the polymer obtained.

［式中、ａは、１以上の数を示し、Ｒ_１は、炭素数１〜３３の鎖状、分岐状若しくは環状の脂肪族炭化水素基又は置換若しくは無置換の芳香族炭化水素基を示す。］
［３］
前記ニトリル化合物の炭素数が、２〜３２である、項［１］又は［２］記載の組成物。
［４］
前記ニトリル化合物のニトリル基の数が、１〜８である、項［１］〜［３］のいずれか一項に記載の組成物。
［５］ 前記（Ａ）ニトリル化合物及び前記（Ｂ）三ハロゲン化ホウ素の少なくとも一部が錯体を形成している、項［１］〜［４］のいずれか一項に記載の組成物。
［６］
下記式（２）で表される、前記（Ａ）ニトリル化合物と前記（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］〜［５］のいずれか一項に記載の組成物。
指標α＝αｎ／αｂ （２）
αｎ：前記ニトリル化合物のニトリル基の物質量（ｍｏｌ）
αｂ：前記三ハロゲン化ホウ素の物質量（ｍｏｌ）
［７］
前記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］〜［６］のいずれか一項に記載の組成物。
［８］
前記エピスルフィド化合物が、３員環チオ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］〜［７］のいずれか一項に記載の組成物。
［９］
前記三ハロゲン化ホウ素の物質量（ｍｏｌ）と、前記エピスルフィド化合物に含まれるエピスルフィド基の物質量（ｍｏｌ）との比が、１：１０〜１：１０００００である、項［１］〜［８］のいずれか一項に記載の組成物。
［１０］
前記エピスルフィド化合物のエピスルフィド当量が、６５〜７００ｇ／ｍｏｌである、項［１］〜［９］のいずれか一項に記載の組成物。
［１１］
前記エピスルフィド化合物が、下記式（３）、（４）、（５）又は（６）で表される部分構造を有する、項［１］〜［１０］のいずれか一項に記載の組成物。

［式中、Ｒ_２０、Ｒ_２１、Ｒ_２２、Ｒ_２３、Ｒ_２４、Ｒ_２５、Ｒ_２６、Ｒ_２７、Ｒ_２８、Ｒ_２９、Ｒ_３０、Ｒ_３１、Ｒ_３２、Ｒ_３３及びＲ_３４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。］
［１２］
項［１］〜［１１］のいずれか一項に記載の組成物中の前記エピスルフィド化合物を重合して形成される、重合物。
［１３］
項［１］〜［１１］のいずれか一項に記載の組成物中の前記エピスルフィド化合物を加熱及び／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 composition containing (A) a nitrile compound, (B) boron trihalide, and (C) an episulfide compound.
[2]
The composition according to item [1], wherein the nitrile compound is a compound represented by the following formula (1).

[Wherein, a represents a number of 1 or more, and R ₁ represents a chain, branched or cyclic aliphatic hydrocarbon group having _{1 to} 33 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group. . ]
[3]
The composition according to item [1] or [2], wherein the nitrile compound has 2 to 32 carbon atoms.
[4]
The composition according to any one of Items [1] to [3], wherein the nitrile compound has 1 to 8 nitrile groups.
[5] The composition according to any one of items [1] to [4], wherein at least a part of the (A) nitrile compound and the (B) boron trihalide forms a complex.
[6]
Any one of Items [1] to [5], wherein an index α representing a ratio of the (A) nitrile compound and the (B) boron trihalide represented by the following formula (2) is 1-1000. The composition according to one item.
Index α = αn / αb (2)
αn: Substance amount of nitrile group of the nitrile compound (mol)
αb: amount of the boron trihalide (mol)
[7]
The composition according to any one of Items [1] to [6], wherein the boron trihalide is at least one selected from the group consisting of boron trifluoride, boron trichloride, and boron tribromide. object.
[8]
The composition according to any one of Items [1] to [7], wherein the episulfide compound is a compound having only a 3-membered ring thioether structure as a polymerizable functional group.
[9]
Items [1] to [8], wherein the ratio of the amount (mol) of boron trihalide to the amount (mol) of episulfide group contained in the episulfide compound is 1:10 to 1: 100000. The composition as described in any one of these.
[10]
The composition according to any one of Items [1] to [9], wherein an episulfide equivalent of the episulfide compound is 65 to 700 g / mol.
[11]
The composition according to any one of Items [1] to [10], wherein the episulfide compound has a partial structure represented by the following formula (3), (4), (5) or (6).

[Wherein R ₂₀ , R ₂₁ , R ₂₂ , R ₂₃ , R ₂₄ , R ₂₅ , R ₂₆ , R ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ , R ₃₁ , R ₃₂ , R ₃₃ and R ₃₄ 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. ]
[12]
A polymer formed by polymerizing the episulfide compound in the composition according to any one of items [1] to [11].
[13]
A method for producing a polymer, wherein the episulfide compound in the composition according to any one of items [1] to [11] is polymerized by heating and / or irradiation with energy rays.

  ADVANTAGE OF THE INVENTION According to this invention, while being excellent in stability at room temperature, it can provide the composition which has sufficiently high polymerizability, there are few side reactions at the time of superposition | polymerization, and the polymer obtained from this composition. .

  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 nitrile compound (hereinafter, sometimes referred to as “component (A)”), (B) boron trihalide (hereinafter, sometimes referred to as “component (B)”), (C) an episulfide compound (hereinafter sometimes referred to as “component (C)”). Hereinafter, the details of the components (A), (B) and (C) and other components contained in the composition will be described.

(Component (A): Nitrile compound)
Component (A) of this embodiment is a nitrile compound having one or more nitrile groups in the molecule. As the component (A), one kind of nitrile compound may be used alone, or a plurality of kinds of nitrile compounds may be used in combination.

  (A) When preparing a composition at room temperature, the nitrile compound tends to further suppress the polymerization of the (C) episulfide compound and improve the stability of the composition, and / or (C) episulfide Since it exists in the tendency which can suppress a side reaction more when superposing | polymerizing a compound, the compound represented by following formula (1) is preferable.

In the formula, a represents a number of 1 or more. R ₁ represents a chain, branched or cyclic aliphatic hydrocarbon group having _{1 to} 33 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group.

  (A) The carbon number of the nitrile compound tends to be able to suppress side reactions more when polymerizing the (C) episulfide compound, and / or when preparing the composition at room temperature, It is preferably 2 or more because polymerization can be further suppressed and the stability of the composition tends to be further improved. Since the vapor pressure tends to be higher and the handleability tends to be further improved, the carbon number is more preferably 3 or more. From the same viewpoint, the number of carbon atoms is more preferably 4 or more.

  (A) The number of carbon atoms of the nitrile compound is preferably 32 or less because it is easily available, the cost of the composition can be further suppressed, and it tends to be more economical. From the same viewpoint, the carbon number is preferably 20 or less. When preparing the composition, it is more preferable that the number of carbon atoms is 16 or less because the remaining of undissolved material can be further suppressed and a composition superior in uniformity can be obtained. From the same viewpoint, the number of carbon atoms is particularly preferably 12 or less.

  (A) The number of nitrile groups of the nitrile compound is such that when the composition is prepared at room temperature, the polymerization of the (C) episulfide compound can be further suppressed, and the stability of the composition tends to be further improved. The above is preferable. From the same viewpoint, the number of nitrile groups is more preferably 2 or more.

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

  (A) The structure of the nitrile compound may be a chain, a branched structure or a cyclic structure, but (B) the formation of a compound (complex) via a coordination bond with boron trihalide is easier. Therefore, it is preferably a chain or cyclic structure. (C) Since the (A) nitrile compound and (B) boron trihalide increase the solubility of the compound (complex) via a coordination bond and reduce the undissolved content in the episulfide compound, A) The structure of the nitrile compound is more preferably a chain structure.

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

(Monofunctional nitrile compound)
The monofunctional nitrile compound according to this embodiment is not particularly limited as long as it is a compound having one nitrile group. The monofunctional nitrile compound is represented by the following formula (7) when a is 1 in the above formula (1).

In the formula, R ₁ represents a chain, branched or cyclic aliphatic hydrocarbon group having _{1 to} 33 carbon atoms or a substituted or unsubstituted aromatic hydrocarbon group.

Specific examples of R ₁ include the following.

  Methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosanyl, heicosanyl, docosanyl, tricosanyl, tetracosanyl, pentacosanyl An aliphatic hydrocarbon group such as hexacosanyl, heptacosanyl, octacosanyl, nonacosanyl, triacontanyl, hentriacontanyl, dotriacontanil (these groups may be linear, branched or cyclic), and Substituted or unsubstituted aromatic hydrocarbon groups such as phenyl, naphthyl, anthracenyl and the like;

When the aromatic hydrocarbon group such as phenyl, naphthyl, anthracenyl has a substituent, examples of the substituent include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, Tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosanyl, heenicosanyl, docosanil, tricosanyl, tetracosanyl, pentacosanyl, hexacosanyl, heptacosanyl, octacosanyl, nonacosanyl, triacontanil, entriacontanyl, dotriacontanyl, etc. chain, branched or cyclic alkyl group, oR groups, OCOR groups, NR ₂ group, NHCOR group, CF ₃ group, CCl ₃ group, NO ₂ group, CN group, CHO group, COR group, _CO 2 R , SO ₂ R group, SO ₃ R group and the like. R represents an aliphatic hydrocarbon group or an aromatic hydrocarbon group.

  Among monofunctional nitrile 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) episulfide compound is further suppressed. At least one selected from the following group because the stability of the composition tends to be further improved and / or (C) when the episulfide compound is polymerized, the side reaction tends to be further suppressed. Are preferred.

  Acetonitrile, propionitrile, butyronitrile, pentanenitrile, hexanenitrile, heptanenitrile, octanenitrile, nonanenitrile, decanenitrile, undecanenitrile, dodecanenitrile, tridecanenitrile, tetradecanenitrile, pentadecanenitrile, hexadecanenitrile, heptadecanenitrile, octadecane Nitrile, Nonadecane nitrile, Icosan nitrile, Henicosan nitrile, Docosan nitrile, Tricosan nitrile, Tetracosan nitrile, Pentacosan nitrile, Hexacosan nitrile, Heptacosan nitrile, Octacosan nitrile, Nonacosonitrile , Hentriacontane nitrile, Dotriacontane nitrile, 2-cyanopropane, 2-cyanobutane, Anomethylpropane, cyanophenylpropane, cyanodiphenylpropane, cyanomethylbutane, cyanodimethylbutane, cyanophenylbutane, cyanodiphenylbutane, cyanomethylpentane, cyanodimethylpentane, cyanoethylpentane, cyanoethylmethylpentane, cyanophenylpentane, cyanodiphenylpentane , Cyanomethylhexane, cyanodimethylhexane, dianoethylhexane, cyanoethylmethylhexane, cyanophenylhexane, cyanodiphenylhexane, cyanomethylheptane, cyanodimethylheptane, cyanoethylheptane, cyanophenylheptane, cyanodiphenylheptane, cyanomethyloctane, cyano Dimethyloctane, cyanoethyloctane, cyanoethylmethyloctane, Anophenyloctane, cyanodiphenyloctane, cyanomethylnonane, cyanophenylnonane, cyanomethyldecane, cyanophenyldecane, cyanomethylundecane, cyanophenylundecane, cyanomethyldodecane, cyanophenyldodecane, cyanomethyltridecane, cyanomethyltetradecane, cyano Methylpentadecane, cyanomethylhexadecane, cyanomethylheptadecane, cyanomethyloctadecane;

  Cyclopropanecarbonitrile, cyclobutanecarbonitrile, cyclopentanecarbonitrile, cyclohexanecarbonitrile, cycloheptanecarbonitrile, cyclooctanecarbonitrile, cyclononanecarbonitrile, cycloundecanecarbonitrile, cyclododecanecarbonitrile, cyclotridecanecarbonitrile, cyclo Tetradecane carbonitrile, cyclopentadecane carbonitrile, cyclohexadecane carbonitrile, cycloheptadecane carbonitrile, cyclooctadecane carbonitrile, cyclononadecane carbonitrile, cycloicosane carbonitrile, cyclohenicosan carbonitrile, cyclodocosane carbonitrile, Cyclotricosancarbonitrile, cyclotetracosancarbonitrile, chic Pentacosancarbonitrile, cyclohexacosancarbonitrile, cycloheptacosancarbonitrile, cyclooctacosancarbonitrile, cyclononacosancarbonitrile, cyclotriacontanecarbonitrile, cyclohentriacotancarbonitrile, cyclodotriacontanecarbonitrile, methyl Cyclopropanecarbonitrile, dimethylcyclopropanecarbonitrile, phenylcyclopropanecarbonitrile, diphenylcyclopropanecarbonitrile, methylcyclobutanecarbonitrile, dimethylcyclobutanecarbonitrile, phenylcyclobutanecarbonitrile, diphenylcyclobutanecarbonitrile, methylcyclopentanecarbonitrile, dimethyl Cyclopentanecarbonitrile, phenylcyclopenta Carbonitrile, diphenylcyclopentanecarbonitrile, methylcyclohexanecarbonitrile, dimethylcyclohexanecarbonitrile, phenylcyclohexanecarbonitrile, diphenylcyclohexanecarbonitrile, methylcycloheptanecarbonitrile, dimethylcycloheptanecarbonitrile, phenylcycloheptanecarbonitrile, diphenylcycloheptane Carbonitrile;

  Methylcyclooctanecarbonitrile, dimethylcyclooctanecarbonitrile, phenylcyclooctanecarbonitrile, diphenylcyclooctanecarbonitrile, methylcyclononanecarbonitrile, phenylcyclononanecarbonitrile, methylcyclodecanecarbonitrile, phenylcyclodecanecarbonitrile, methylcyclo Undecane carbonitrile, phenylcycloundecane carbonitrile, methylcyclododecane carbonitrile, phenylcyclododecane carbonitrile, methylcyclotridecane carbonitrile, methylcyclotetradecane carbonitrile, methylcyclopentadecane carbonitrile, methylcyclohexadecane carbonitrile, methylcyclohepta Decanecarbonitrile, methylcyclooctadecane Rubonitrile, benzonitrile, methylbenzonitrile, ethylbenzonitrile, propylbenzonitrile, butylbenzonitrile, methoxybenzonitrile, dimethylaminobenzonitrile, fluorobenzonitrile, trifluoromethylbenzonitrile, acetylbenzonitrile, dimethylbenzonitrile, Diethylbenzonitrile, dipropylbenzonitrile, dibutylbenzonitrile, dimethoxybenzonitrile, bis (dimethylamino) benzonitrile, difluorobenzonitrile, bis (trifluoromethyl) benzonitrile, diacetylbenzonitrile, trimethylbenzonitrile, triethylbenzonitrile, Tripropylbenzonitrile, tributylbenzonitrile, trimethoxybenzonitrile, tris (dimethylamine Roh) benzonitrile, trifluoroacetic benzonitrile, tris (trifluoromethyl) Bensonitoriru, triacetyl benzonitrile;

  Naphthonitrile, Methylnaphthonitrile, Ethylnaphthonitrile, Propylnaphthonitrile, Butylnaphthonitrile, Dimethylnaphthonitrile, Diethylnaphthonitrile, Diproylnaphthonitrile, Dibutylnaphthonitrile, Trimethylnaphthonitrile, Triethylnaphthonitrile, Tripropylnaphthonitrile, Tributyl Naphthonitrile, Anthracenecarbonitrile, Methylanthracenecarbonitrile, Ethylanthracenecarbonitrile, Propylanthracenecarbonitrile, Butylanthracenecarbonitrile, Dimethylanthracenecarbonitrile, Diethylanthracenecarbonitrile, Dipropylanthracenecarbonitrile, Dibutylanthracenecarbonitrile, Trimethylanthracene Carbonitrile, trie Luanthracenecarbonitrile, tripropylanthracenecarbonitrile, tributylanthracenecarbonitrile, phenanthrenecarbonitrile, methylphenanthrenecarbonitrile, ethylphenanthrenecarbonitrile, propylphenanthrenecarbonitrile, butylphenanthrenecarbonitrile, dimethylphenanthrenecarbonitrile, diethylphenanthrenecarbonitrile, Dipropylphenanthrenecarbonitrile, dibutylphenanthrenecarbonitrile, trimethylphenanthrenecarbonitrile, triethylphenanthrenecarbonitrile, tripropylphenanthrenecarbonitrile, tributylphenanthrenecarbonitrile, bicyclo [2.2.1] heptane-carbonitrile, bicyclo [2.2 2] octane - carbonitrile, spiro [2.5] octane - carbonitrile, adamantane carbonitrile.

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

  Acetonitrile, propionitrile, butyronitrile, pentanenitrile, hexanenitrile, heptanenitrile, octanenitrile, nonanenitrile, decanenitrile, undecanenitrile, dodecanenitrile, tridecanenitrile, tetradecanenitrile, pentadecanenitrile, hexadecanenitrile, heptadecanenitrile, octadecane Nitrile, nonadecane nitrile, 2-cyanopropane, 2-cyanobutane, cyanomethylpropane, cyanophenylpropane, cyanodiphenylpropane, cyanomethylbutane, cyanodimethylbutane, cyanophenylbutane, cyanodiphenylbutane, cyanomethylpentane, cyanomethylhexane , Cyanomethyl heptane, cyanomethyl octane, cyclopropanecarbonitrile, cyclobut Carbonitrile, cyclopentanecarbonitrile, cyclohexanecarbonitrile, cycloheptanecarbonitrile, cyclooctanecarbonitrile, cyclononanecarbonitrile, cycloundecanecarbonitrile, cyclododecanecarbonitrile, methylcyclopropanecarbonitrile, dimethylcyclopropanecarbonitrile, Phenylcyclopropanecarbonitrile, diphenylcyclopropanecarbonitrile, methylcyclobutanecarbonitrile, dimethylcyclobutanecarbonitrile, phenylcyclobutanecarbonitrile, diphenylcyclobutanecarbonitrile;

  Methylcyclopentanecarbonitrile, dimethylcyclopentanecarbonitrile, phenylcyclopentanecarbonitrile, diphenylpentanecarbonitrile, methylcyclohexanecarbonitrile, dimethylcyclohexanecarbonitrile, phenylcyclohexanecarbonitrile, diphenylcyclohexanecarbonitrile, methylcycloheptanecarbonitrile, phenyl Cycloheptanecarbonitrile, methylcyclooctanecarbonitrile, phenylcyclooctanecarbonitrile, methylcyclononanecarbonitrile, methylcyclodecanecarbonitrile, methylcycloundecanecarbonitrile, methylcyclododecanecarbonitrile, benzonitrile, methylbenzonitrile, ethylbenzo Nitrile, propyl benzonite Le, butyl benzonitrile, naphthonitrile, methyl naphthoxazole nitrile, ethyl naphthaldehyde nitrile, propyl naphthaldehyde nitrile, butyl naphthaldehyde nitrile.

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

  Propionitrile, butyronitrile, pentanenitrile, hexanenitrile, heptanenitrile, octanenitrile, nonanenitrile, decanenitrile, undecanenitrile, dodecanenitrile, 2-cyanopropane, 2-cyanobutane, cyclopropanecarbonitrile, cyclobutanecarbonitrile, cyclopentane Carbonitrile, cyclohexanecarbonitrile, benzonitrile.

(Bifunctional nitrile compound)
The bifunctional nitrile compound according to this embodiment is not particularly limited as long as it is a compound having two nitrile groups. Specific examples of the bifunctional nitrile compound include compounds in which a is 2 in the above formula (1).

  Among the bifunctional nitrile 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) episulfide compound is further suppressed. At least one selected from the following group because the stability of the composition tends to be further improved and / or (C) when the episulfide compound is polymerized, the side reaction tends to be further suppressed. Are preferred.

  Dicyanomethane, methyldicyanomethane, dimethyldicyanomethane, ethyldicyanomethane, diethyldicyanomethane, ethylmethyldicyanomethane, propyldicyanomethane, butyldicyanomethane, phenyldicyanomethane, diphenyldicyanomethane, methylphenyldicyanomethane, ethylphenyldicyanomethane, Dicyanoethane, methyldicyanoethane, dimethyldicyanoethane, trimethyldicyanoethane, tetramethyldicyanoethane, ethyldicyanoethane, diethyldicyanoethane, propyldicyanoethane, butyldicyanoethane, phenyldicyanoethane, diphenyldicyanoethane, methylphenyldicyanoethane, ethyl Phenyldicyanoethane, dicyanopropane, methyldicyanopropane, dimethyldicia Propane, trimethyldicyanopropane, tetramethyldicyanopropane, ethyldicyanopropane, diethyldicyanopropane, propyldicyanopropane, butyldicyanopropane, phenyldicyanopropane, diphenyldicyanopropane, methylphenyldicyanopropane, ethylphenyldicyanopropane, dicyanobutane, methyldicyano Butane, dimethyldicyanobutane, trimethyldicyanobutane, tetramethyldicyanobutane, ethyldicyanobutane, propyldicyanobutane, butyldicyanobutane, phenyldicyanobutane, diphenyldicyanobutane, dicyanopentane, methyldicyanopentane, dimethyldicyanopentane, trimethyldicyanopentane, Tetramethyldicyanopentane, ethyldicyanopentane , Propyldicyanopentane, butyldicyanopentane, phenyldicyanopentane, diphenyldicyanopentane, dicyanohexane, methyldicyanohexane, dimethyldicyanohexane, trimethyldicyanohexane, tetramethyldicyanohexane, ethyldicyanohexane, propyldicyanohexane, butyldicyanohexane, Phenyldicyanohexane, diphenyldicyanohexane;

  Dicyanoheptane, methyldicyanoheptane, dimethyldicyanoheptane, trimethyldicyanoheptane, tetramethyldicyanoheptane, ethyldicyanoheptane, propyldicyanoheptane, butyldicyanoheptane, phenyldicyanoheptane, diphenyldicyanoheptane, dicyanooctane, methyldicyanooctane, dimethyldicyanooctane , Trimethyldicyanooctane, tetramethyldicyanooctane, ethyldicyanooctane, propyldicyanooctane, butyldicyanooctane, phenyldicyanooctane, diphenyldicyanooctane, dicyanononane, methyldicyanononane, dimethyldicyanononane, ethyldicyanononane, phenyldicyanononane, dicyanodecane , Methyldicyanodecane, dimethyldisi Nodecane, ethyldicyanodecane, phenyldicyanodecane, dicyanoundecane, methyldicyanoundecane, dimethyldicyanoundecane, ethyldicyanoundecane, phenyldicyanoundecane, dicyanododecane, methyldicyanododecane, dimethyldicyanododecane, ethyldicyanododecane, phenyldicyanododecane, dicyanotri Decane, dicyanotetradecane, dicyanopentadecane, dicyanohexadecane, dicyanoheptadecane, dicyanooctadecane, dicyanononadecane, dicyanoicosane, dicyanohenicosan, dicyanodocosane, dicyanotricosane, dicyanotetracosane, dicyanopentacosane, dicyanohexacosane , Dicyanoheptacosane, dicyanooctacosane, dicyanononacosane, disi Notoriakontan, dicyano hentriacontane, dicyano de Tria near end;

  Cyclopropanedicarbonitrile, methylcyclopropanedicarbonitrile, dimethylcyclopropanedicarbonitrile, ethylcyclopropanedicarbonitrile, propylcyclopropanedicarbonitrile, butylcyclopropanedicarbonitrile, phenylcyclopropanedicarbonitrile, diphenylcyclo Propane dicarbonitrile, cyclobutanedicarbonitrile, methylcyclobutanedicarbonitrile, dimethylcyclobutanedicarbonitrile, trimethylcyclobutanedicarbonitrile, tetramethylcyclobutanedicarbonitrile, ethylcyclobutanedicarbonitrile, propylcyclobutanedicarbonitrile, butylcyclobutanedi Carbonitrile, phenylcyclobutanedicarbonitrile, diphenylcyclobutane Rubonitrile, cyclopentanedicarbonitrile, methylcyclopentanedicarbonitrile, dimethylcyclopentanedicarbonitrile, trimethylcyclopentanedicarbonitrile, tetramethylcyclopentanedicarbonitrile, ethylcyclopentanedicarbonitrile, propylcyclopentanedicarbonitrile , Butylcyclopentanedicarbonitrile, phenylcyclopentanedicarbonitrile, diphenylcyclopentanedicarbonitrile, cyclohexanedicarbonitrile, methylcyclohexanedicarbonitrile, dimethylcyclohexanedicarbonitrile, trimethylcyclohexanedicarbonitrile, tetramethylcyclohexanedicarbonitrile Nitrile, ethylcyclohexanedicarbonitrile, propylcyclohexanedi Rubonitrile, butylcyclohexanedicarbonitrile, phenylcyclohexanedicarbonitrile, diphenylcyclohexanedicarbonitrile, cycloheptanedicarbonitrile, methylcycloheptanedicarbonitrile, dimethylcycloheptanedicarbonitrile, ethylcycloheptanedicarbonitrile, phenylcycloheptane Dicarbonitrile, diphenylcycloheptanedicarbonitrile, cyclooctanedicarbonitrile, methylcyclooctanedicarbonitrile, dimethylcyclooctanedicarbonitrile, ethylcyclooctanedicarbonitrile, phenylcyclooctanedicarbonitrile, diphenylcyclooctanedicarb Nitrile;

  Cyclononanedicarbonitrile, methylcyclononanedicarbonitrile, phenylcyclononanedicarbonitrile, cyclodecanedicarbonitrile, methylcyclodecanedicarbonitrile, phenylcyclodecanedicarbonitrile, cycloundecanedicarbonitrile, methylcycloundecandi Carbonitrile, phenylcycloundecane dicarbonitrile, cyclododecanedicarbonitrile, methylcyclododecanedicarbonitrile, phenylcyclododecanedicarbonitrile, cyclotridecanedicarbonitrile, cyclotetradecanedicarbonitrile, cyclopentadecanedicarbonitrile, cyclo Hexadecane dicarbonitrile, cycloheptadecane dicarbonitrile, cyclooctadecane dicarbonitrile, cyclononadecane Carbonitrile, cycloicosane dicarbonitrile, cyclohenicosane dicarbonitrile, cyclodocosane dicarbonitrile, cyclotricosane dicarbonitrile, cyclotetracosane dicarbonitrile, cyclopentacosane dicarbonitrile, cyclohexacosane dicarbonitrile, cycloheptacosandicarbonitrile , Cyclooctacosandicarbonitrile, cyclononacosandicarbonitrile, cyclotriacontanedicarbonitrile, cyclohentriacondanedicarbonitrile, cyclodotriacontanedicarbonitrile;

  Cyclopropane diacetonitrile, cyclobutane diacetonitrile, cyclpentane diacetonitrile, cyclohexane diacetonitrile, cycloheptane diacetonitrile, cyclooctane diacetonitrile, cyclononane diacetonitrile, cyclodecane diacetonitrile, cycloundecane diacetonitrile, cyclododecane diacetonitrile, dicyanobenzene , Methyldicyanobenzene, ethyldicyanobenzene, propyldicyanobenzene, butyldicyanobenzene, methoxydicyanobenzene, dimethylaminodicyanobenzene, fluorodicyanobenzene, trifluoromethyldicyanobenzene, acetyldicyanobenzene, dimethyldicyanobenzene, diethyldicyanobenzene, dipropyl Dicyanobenzene, dibutyl Cyanobenzene, dimethoxydicyanobenzene, bis (dimethylamino) dicyanobenzene, difluorodicyanobenzene, bis (trifluoromethyl) dicyanobenzene, diacetyldicyanobenzene, trimethyldicyanobenzene, triethyldicyanobenzene, tripropyldicyanobenzene, tributyldicyanobenzene, tri Methoxydisinoanobenzene, tris (dimethylamino) dicyanobenzene, trifluorodicyanobenzene, tris (trifluoromethyl) dicyanobenzene, triacetyldicyanobenzene, dicyanonaphthalene, methyldicyanonaphthalene, ethyldicyanonaphthalene, propyldicyanonaphthalene, butyldicyano Naphthalene, methoxydicyanonaphthalene, dimethylaminodicyanonaphthalene Fluorodicyanonaphthalene, trifluoromethyldicyanonaphthalene, acetyldicyanonaphthalene, dicyanoanthracene, dicyanophenanthrene, bicyclo [2.2.1] heptane-dicarbonitrile, bicyclo [2.2.2] octane-dicarbonitrile, spiro [ 2.5] Octane-dicarbonitrile, adamantane dicarbonitrile.

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

  Dicyanomethane, dicyanoethane, dicyanobutane, dicyanopropane, dicyanopentane, dicyanohexane, dicyanoheptane, dicyanooctane, dicyanononane, dicyanodecane, dicyanoundecane, dicyanododecane, cyclopropanedicarbonitrile, cyclobutanedicarbonitrile, cyclopentanedicarbo Nitrile, cyclohexanedicarbonitrile, cycloheptanedicarbonitrile, cyclooctanedicarbonitrile, cyclononanedicarbonitrile, cyclodecanedicarbonitrile, cycloundecanedicarbonitrile, cyclododecanedicarbonitrile, cyclopropanediacetonitrile, cyclobutanedi Acetonitrile, cyclpentanediacetonitrile, cyclohexanediacetonitrile, cycloheptanedi Acetonitrile, octane dicarboxylic acetonitrile, dicyanobenzene, methyl dicyanobenzene, ethyl dicyanobenzene, propyl dicyanobenzene, butyl dicyanobenzene, dicyanonaphthalene.

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

  Dicyanoethane, dicyanopropane, dicyanobutane, dicyanopentane, dicyanohexane, dicyanoheptane, dicyanooctane, dicyanononane, dicyanodecane, cyclopropanedicarbonitrile, cyclobutanedicarbonitrile, cyclopentanedicarbonitrile, cyclohexanedicarbonitrile, cyclopropane Diacetonitrile, cyclohexane diacetonitrile, dicyanobenzene.

(Polyfunctional nitrile compound)
The polyfunctional nitrile compound according to this embodiment is not particularly limited as long as it is a compound having three or more nitrile groups. Specific examples of the polyfunctional nitrile compound include compounds in which a is 3 or more in the above formula (1).

  Among polyfunctional nitrile compounds, it is easy to obtain, can reduce the cost as a composition, tends to be more economical, and suppresses polymerization of (C) episulfide compound when preparing a composition at room temperature. At least one selected from the following group because the stability of the composition tends to be further improved and / or (C) when the episulfide compound is polymerized, the side reaction tends to be further suppressed. Are preferred.

  Propanetricarbonitrile, methylpropanetricarbonitrile, dimethylpropanetricarbonitrile, trimethylpropanetricarbonitrile, ethylpropanetricarbonitrile, propylpropanetricarbonitrile, butylpropanetricarbonitrile, phenylpropanetricarbonitrile, diphenylpropanetri Carbonitrile, cyclopropanetricarbonitrile, methylcyclopropanetricarbonitrile, dimethylcyclopropanetricarbonitrile, trimethylcyclopropanetricarbonitrile, ethylcyclopropanetricarbonitrile, propylcyclopropanetricarbonitrile, butylcyclopropanetricarbonitrile , Phenylcyclopropanetricarbonitrile, diphenylcyclopropanetri Rubonitrile, butanetricarbonitrile, methylbutanetricarbonitrile, dimethylbutanetricarbonitrile, trimethylbutanetricarbonitrile, tetramethylbutanetricarbonitrile, ethylbutanetricarbonitrile, propylbutanetricarbonitrile, butylbutanetricarbonitrile, Phenylbutanetricarbonitrile, diphenylbutanetricarbonitrile, cyclobutanetricarbonitrile, methylcyclobutanetricarbonitrile, dimethylcyclobutanetricarbonitrile, trimethylcyclobutanetricarbonitrile, tetramethylcyclobutanetricarbonitrile, ethylcyclobutanetricarbonitrile, propylcyclobutane Tricarbonitrile, butylcyclobutane tricarbonitrile, Lucyclobutanetricarbonitrile, diphenylcyclobutanetricarbonitrile, pentanetricarbonitrile, methylpentanetricarbonitrile, dimethylpentanetricarbonitrile, trimethylpentanetricarbonitrile, tetramethylpentanetricarbonitrile, ethylpentanetricarbonitrile, propylpentane Tricarbonitrile, butylpentanetricarbonitrile, phenylpentanetricarbonitrile, diphenylpentanetricarbonitrile;

  Cyclopentanetricarbonitrile, methylcyclopentanetricarbonitrile, dimethylpentanetricarbonitrile, trimethylpentanetricarbonitrile, tetramethylpentanetricarbonitrile, ethylpentanetricarbonitrile, propylpentanetricarbonitrile, butylpentanetricarbonitrile, Phenylpentanetricarbonitrile, diphenylpentanetricarbonitrile, hexanetricarbonitrile, methylhexanetricarbonitrile, dimethylhexanetricarbonitrile, trimethylhexanetricarbonitrile, tetramethylhexanetricarbonitrile, ethylhexanetricarbonitrile, propylhexane Tricarbonitrile, butyl hexane tricarbonitrile, phenyl hexane tri Rubonitrile, diphenylhexanetricarbonitrile, cyclohexanetricarbonitrile, methylcyclohexanetricarbonitrile, dimethylcyclohexanetricarbonitrile, trimethylcyclohexanetricarbonitrile, tetramethylcyclohexanetricarbonitrile, ethylcyclohexanetricarbonitrile, propylcyclohexanetricarbonitrile, Butylcyclohexanetricarbonitrile, phenylcyclohexanetricarbonitrile, diphenylcyclohexanetricarbonitrile, heptanetricarbonitrile, methylheptanetricarbonitrile, dimethylheptanetricarbonitrile, phenylheptanetricarbonitrile, cycloheptanetricarbonitrile, methylcycloheptane Tricarbo Tolyl, dimethyl cycloheptane tri-carbonitrile;

  Octanetricarbonitrile, methyloctanetricarbonitrile, dimethyloctanetricarbonitrile, phenyloctanetricarbonitrile, cyclooctanetricarbonitrile, methylcyclooctanetricarbonitrile, dimethylcyclooctanetricarbonitrile, phenylcyclooctanetricarbonitrile, Nonanetricarbonitrile, cyclononanetricarbonitrile, decanetricarbonitrile, cyclodecanetricarbonitrile, undecanetricarbonitrile, cycloundecanetricarbonitrile, dodecanetricarbonitrile, cyclododecanetricarbonitrile, tridecanetricarbonitrile, tetradecane Tricarbonitrile, pentadecane tricarbonitrile, hexadecane tricarbonitrile, hep De country carbonitrile, octadecenyl country carbonitrile;

  Tricyanobenzene, methyltricyanobenzene, ethyltricyanobenzene, propyltricyanobenzene, butyltricyanobenzene, methoxytricyanobenzene, dimethylaminotricyanobenzene, fluorotricyanobenzene, trifluoromethyltricyanobenzene, acetyltricyano Benzene, dimethyltricyanobenzene, diethyltricyanobenzene, dipropyltricyanobenzene, dibutyltricyanobenzene, dimethoxytricyanobenzene, bis (dimethylamino) tricyanobenzene, difluorotricyanobenzene, bis (trifluoromethyl) tricyano Benzene, diacetyltricyanobenzene, trimethyltricyanobenzene, triethyltricyanobenzene, tripropyltricyanobenzene, Ributyltricyanobenzene, trimethoxytricyanobenzene, tris (dimethylamino) tricyanobenzene, trifluorotricyanobenzene, tris (trifluoromethyl) tricyanobenzene, triacetyltricyanobenzene, tricyanonaphthalene, methyltricyano Naphthalene, ethyltricyanonaphthalene, propyltricyanonaphthalene, butyltricyanonaphthalene, methoxytricyanonaphthalene, dimethylaminotricyanonaphthalene, fluorotricyanonaphthalene, trifluoromethyltricyanonaphthalene, acetyltricyanonaphthalene, dimethyltricyanonaphthalene, Diethyltricyanonaphthalene, dipropyltricyanonaphthalene, dibutyltricyanonaphthalene, dimethoxytricyanonaphth Len, bis (dimethylamino) tricyanonaphthalene, difluorotricyanonaphthalene, bis (trifluoromethyl) tricyanonaphthalene, diacetyltricyanonaphthalene, trimethyltricyanonaphthalene, triethyltricyanonaphthalene, tripropyltricyanonaphthalene, tributyltricyano Naphthalene, trimethoxytricyanonaphthalene, tris (dimethylamino) tricyanonaphthalene, trifluorotricyanonaphthalene, tris (trifluoromethyl) tricyanonaphthalene, triacetyltricyanonaphthalene;

  Tricyanoanthracene, methyltricyanoanthracene, ethyltricyanoanthracene, propyltricyanoanthracene, butyltricyanoanthracene, methoxytricyanoanthracene, dimethylaminotricyanoanthracene, fluorotricyanoanthracene, trifluoromethyltricyanoanthracene, acetyltricyano Anthracene, dimethyltricyanoanthracene, diethyltricyanoanthracene, dipropyltricyanoanthracene, dibutyltricyanoanthracene, dimethoxytricyanoanthracene, bis (dimethylamino) tricyanoanthracene, difluorotricyanoanthracene, bis (trifluoromethyl) tricyano Anthracene, diacetyltricyanoanthracene, trimethyltrisi Noanthracene, triethyltricyanoanthracene, tripropyltricyanoanthracene, tributyltricyanoanthracene, trimethoxytricyanoanthracene, tris (dimethylamino) tricyanoanthracene, trifluorotricyanoanthracene, tris (trifluoromethyl) tricyanoanthracene, Triacetyltricyanoanthracene, tricyanophenanthrene, methyltricyanophenanthrene, ethyltricyanophenanthrene, propyltricyanophenanthrene, butyltricyanophenanthrene, methoxytricyanophenanthrene, dimethylaminotricyanophenanthrene, fluorotricyanophenanthrene, trifluoromethyltricia Nophenanthrene, acetyltricyanophenant , Dimethyltricyanophenanthrene, diethyltricyanophenanthrene, dipropyltricyanophenanthrene, dibutyltricyanophenanthrene, dimethoxytricyanophenanthrene, bis (dimethylamino) tricyanophenanthrene, difluorotricyanophenanthrene, bis (trifluoromethyl) tricyano Phenanthrene, diacetyltricyanophenanthrene, trimethyltricyanophenanthrene, triethyltricyanophenanthrene, tripropyltricyanophenanthrene, tributyltricyanophenanthrene, trimethoxytricyanophenanthrene, tris (dimethylamino) tricyanophenanthrene, trifluorotricyanophenanthrene, tris (Trifluoromethyl) tricyanophena Trenth, triacetyltricyanophenanthrene;

  Propanetetracarbonitrile, methylpropanetetracarbonitrile, dimethylpropanetetracarbonitrile, ethylpropanetetracarbonitrile, propylpropanetetracarbonitrile, butylpropanetetracarbonitrile, phenylpropanetetracarbonitrile, diphenylpropanetetracarbonitrile, cyclopropanetetra Carbonitrile, methylcyclopropanetetracarbonitrile, dimethylcyclopropanetetracarbonitrile, ethylcyclopropanetetracarbonitrile, propylcyclopropanetetracarbonitrile, butylcyclopropanetetracarbonitrile, methylethylcyclopropanetetracarbonitrile, methylpropylcyclopropane Tetracarbonitrile, methylbutylcyclopropane Tracarbonitrile, ethylpropylcyclopropanetetracarbonitrile, ethylbutylcyclopropanetetracarbonitrile, propylbutylcyclopropanetetracarbonitrile, phenylcyclopropanetetracarbonitrile, diphenylcyclopropanetetracarbonitrile, butanetetracarbonitrile, methylbutanetetra Carbonitrile, dimethylbutanetetracarbonitrile, trimethylbutanetetracarbonitrile, tetramethylbutanetetracarbonitrile, ethylbutanetetracarbonitrile, propylbutanetetracarbonitrile, butylbutanetetracarbonitrile, phenylbutanetetracarbonitrile, diphenylbutanetetracarbonitrile Nitrile, cyclobutanetetracarbonitrile, methylcyclobutane Tracarbonitrile, dimethylcyclobutanetetracarbonitrile, trimethylcyclobutanetetracarbonitrile, tetramethylcyclobutanetetracarbonitrile, ethylcyclobutanetetracarbonitrile, propylcyclobutanetetracarbonitrile, butylcyclobutanetetracarbonitrile, phenylcyclobutanetetracarbonitrile, diphenylcyclobutanetetra Carbonitrile;

  Pentanetetracarbonitrile, methylpentanetetracarbonitrile, dimethylpentanetetracarbonitrile, trimethylpentanetetracarbonitrile, tetramethylpentanetetracarbonitrile, ethylpentanetetracarbonitrile, propylpentanetetracarbonitrile, butylpentanetetracarbonitrile, phenylpentane Tetracarbonitrile, diphenylpentanetetracarbonitrile, cyclopentanetetracarbonitrile, methylcyclopentanetetracarbonitrile, dimethylcyclopentanetetracarbonitrile, trimethylcyclopentanetetracarbonitrile, tetramethylcyclopentanetetracarbonitrile, ethylcyclopentanetetracarbonitrile Nitrile, propylcyclopentanetetracarbo Tolyl, butylcyclopentanetetracarbonitrile, phenylcyclopentanetetracarbonitrile, diphenylcyclopentanetetracarbonitrile, hexanetetracarbonitrile, methylhexanetetracarbonitrile, dimethylhexanetetracarbonitrile, trimethylhexanetetracarbonitrile, tetramethylhexanetetra Carbonitrile, ethylhexanetetracarbonitrile, propylhexanetetracarbonitrile, butylhexanetetracarbonitrile, phenylhexanetetracarbonitrile, diphenylhexanetetracarbonitrile, cyclohexanetetracarbonitrile, methylcyclohexanetetracarbonitrile, dimethylcyclohexanetetracarbonitrile, Trimethylcyclohexaneteto Carbonitrile, tetramethylcyclohexane tetracarbonitrile, ethylcyclohexane tetracarbonitrile, propyl cyclohexane tetracarbonitrile, butylcyclohexane tetracarbonitrile, phenylcyclohexane tetracarbonitrile, diphenylcyclohexane tetracarbonitrile;

  Heptanetetracarbonitrile, methylheptanetetracarbonitrile, dimethylheptanetetracarbonitrile, phenylheptanetetracarbonitrile, cycloheptanetetracarbonitrile, methylcycloheptanetetracarbonitrile, dimethylcycloheptanetetracarbonitrile, phenylcycloheptanetetracarbonitrile, Octanetetracarbonitrile, methyloctanetetracarbonitrile, dimethyloctanetetracarbonitrile, phenyloctanetetracarbonitrile, cyclooctanetetracarbonyl, methylcyclooctanetetracarbonitrile, dimethylcyclooctanetetracarbonitrile, phenylcyclooctanetetracarbonitrile, nonane Tetracarbonitrile, cyclononanetetracarboni Ril, decanetetracarbonitrile, cyclodecanetetracarbonitrile, undecanetetracarbonitrile, cycloundecanetetracarbonitrile, dodecanetetracarbonitrile, cyclododecanetetracarbonitrile, tridecanetetracarbonitrile, tetradecanetetracarbonitrile, pentadecanetetracarbonitrile , Hexadecanetetracarbonitrile, heptadecanetetracarbonitrile, octadecanetetracarbonitrile;

  Tetracyanobenzene, methyltetracyanobenzene, ethyltetracyanobenzene, propyltetracyanobenzene, butyltetracyanobenzene, methoxytetracyanobenzene, dimethylaminotetracyanobenzene, fluorotetracyanobenzene, trifluoromethyltetracyanobenzene, acetyltetracyano Benzene, dimethyltetracyanobenzene, diethyltetracyanobenzene, dipropyltetracyanobenzene, dibutyltetracyanobenzene, dimethoxytetracyanobenzene, bis (dimethylamino) tetracyanobenzene, difluorotetracyanobenzene, bis (trifluoromethyl) tetracyano Benzene, diacetyltetracyanobenzene, tetracyanonaphthalene, methyltetracyanonaphthalene, Tyltetracyanonaphthalene, propyltetracyanonaphthalene, butyltetracyanonaphthalene, methoxytetracyanonaphthalene, dimethylaminotetracyanonaphthalene, fluorotetracyanonaphthalene, trifluoromethyltetracyanonaphthalene, acetyltetracyanonaphthalene, dimethyltetracyanonaphthalene, diethyltetra Cyanonaphthalene, dipropyltetracyanonaphthalene, dibutyltetracyanonaphthalene, dimethoxytetracyanonaphthalene, bis (dimethylamino) tetracyanonaphthalene, difluorotetracyanonaphthalene, bis (trifluoromethyl) tetracyanonaphthalene, diacetyltetracyanonaphthalene, trimethyltetra Cyanonaphthalene, triethyltetracyanonaphthalene, Propyltetramethylcyclopentadienyl cyanonaphthalene, tributyl tetra cyano-naphthalene, tri methoxytetrahydropyran cyanonaphthalene, tris (dimethylamino) tetra-cyano-naphthalene, trifluoroacetic tetracyanoethylene naphthalene, tris (trifluoromethyl) tetracyanoethylene naphthalene, triacetyl tetracyanoethylene naphthalene;

  Tetracyanoanthracene, methyltetracyanoanthracene, ethyltetracyanoanthracene, propyltetracyanoanthracene, butyltetracyanoanthracene, methoxytetracyanoanthracene, dimethylaminotetracyanoanthracene, fluorotetracyanoanthracene, trifluoromethyltetracyanoanthracene, acetyltetracyano Anthracene, dimethyltetracyanoanthracene, diethyltetracyanoanthracene, dipropyltetracyanoanthracene, dibutyltetracyanoanthracene, dimethoxytetracyanoanthracene, bis (dimethylamino) tetracyanoanthracene, difluorotetracyanoanthracene, bis (trifluoromethyl) tetracyano Anthracene, diacetylteto Cyanoanthracene, trimethyltetracyanoanthracene, triethyltetracyanoanthracene, tripropyltetracyanoanthracene, tributyltetracyanoanthracene, trimethoxytetracyanoanthracene, tris (dimethylamino) tetracyanoanthracene, trifluorotetracyanoanthracene, tris (trifluoromethyl ) Tetracyanoanthracene, triacetyltetracyanoanthracene, tetracyanophenanthrene, methyltetracyanophenanthrene, ethyltetracyanophenanthrene, propyltetracyanophenanthrene, butyltetracyanophenanthrene, methoxytetracyanophenanthrene, dimethylaminotetracyanophenanthrene, fluorotetracyanophenanthrene , Trifluoromethyltetracyanophenanthrene, acetyltetracyanophenanthrene, dimethyltetracyanophenanthrene, diethyltetracyanophenanthrene, dipropyltetracyanophenanthrene, dibutyltetracyanophenanthrene, dimethoxytetracyanophenanthrene, bis (dimethylamino) tetracyanophenanthrene, difluorotetracyano Phenanthrene, bis (trifluoromethyl) tetracyanophenanthrene, diacetyltetracyanophenanthrene, trimethyltetracyanophenanthrene, triethyltetracyanophenanthrene, tripropyltetracyanophenanthrene, tributyltetracyanophenanthrene, trimethoxytetracyanophenanthrene, tris (dimethylamino) teto Lacyanophenanthrene, trifluorotetracyanophenanthrene, tris (trifluoromethyl) tetracyanophenanthrene, triacetyltetracyanophenanthrene;

  Propanepentacarbonitrile, methylpropanepentacarbonitrile, dimethylpropanepentacarbonitrile, phenylpropanepentacarbonitrile, cyclopropanepentacarbonitrile, butanepentacarbonitrile, methylbutanepentacarbonitrile, dimethylbutanepentacarbonitrile, phenylbutanepentacarbone Nitrile, cyclobutanepentacarbonitrile, methylcyclobutanepentacarbonitrile, dimethylcyclobutanepentacarbonitrile, phenylcyclobutanepentacarbonitrile, pentanepentacarbonitrile, methylpentanepentacarbonitrile, dimethylpentanepentacarbonitrile, phenylpentanepentacarbonitrile, cyclopentane Pentacarbonitrile, methylcyclopenta Pentacarbonitrile, dimethylcyclopentanepentacarbonitrile, phenylcyclopentanepentacarbonitrile, hexanepentacarbonitrile, methylhexanepentacarbonitrile, dimethylhexanepentacarbonitrile, phenylhexanepentacarbonitrile, cyclohexanepentacarbonitrile, methylcyclohexanepentacarbone Nitrile, dimethylcyclohexanepentacarbonitrile, phenylcyclohexanepentacarbonitrile, heptanepentacarbonitrile, cycloheptanepentacarbonitrile, octanepentacarbonitrile, cyclooctanepentacarbonitrile, nonanepentacarbonitrile, cyclononanepentacarbonitrile, decanepentacarbonitrile Nitrile, cyclodecanpentacarbo Tolyl, undecane pentacarbonitrile, cycloundecane pentacarbonitrile, dodecane pentacarbonitrile, cyclododecane pentacarbonitrile, tridecane pentacarbonitrile, tetradecane pentacarbonitrile, pentadecane pentacarbonitrile, hexadecane pentacarbonitrile, heptadecane pentacarbonitrile , Octadecane pentacarbonitrile, pentacyanobenzene, pentacyanonaphthalene, pentacyanoanthracene, pentacyanophenanthrene;

  Propanehexacarbonitrile, cyclopropanehexacarbonitrile, butanehexacarbonitrile, cyclobutanehexacarbonitrile, pentanehexacarbonitrile, cyclopentanehexacarbonitrile, hexanehexacarbonitrile, cyclohexanehexacarbonitrile, heptanehexacarbonitrile, cycloheptanehexa Carbonitrile, octanehexacarbonitrile, cyclooctanehexacarbonitrile, nonanehexacarbonitrile, cyclononanehexacarbonitrile, decanehexacarbonitrile, cyclodecanehexacarbonitrile, undecanehexacarbonitrile, cycloundecanehexacarbonitrile, dodecanehexacarbonitrile Nitrile, cyclododecane hexacarbonitrile, tridecane hex Carbonitrile, tetradecane hexa-carbonitrile, peta decane hexa-carbonitrile, hexadecane hexa-carbonitrile, heptadecane hexa-carbonitrile, octadecane hexa-carbonitrile, hexacyano benzene, hexacyano naphthalene, hexacyano anthracene down, hexacyano phenanthrene.

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

  Propanetricarbonitrile, cyclopropanetricarbonitrile, butanetricarbonitrile, cyclobutanetricarbonitrile, pentanetricarbonitrile, cyclopentanetricarbonitrile, hexanetricarbonitrile, cyclohexanetricarbonitrile, heptanetricarbonitrile, cycloheptanetri Carbonitrile, octanetricarbonitrile, cyclooctanetricarbonitrile, nonanetricarbonitrile, decanetricarbonitrile, undecanetricarbonitrile, dodecanetricarbonitrile, tricyanobenzene, tricyanonaphthalene, tricyanoanthracene, propanetetracarbonitrile , Cyclopropanetetracarbonitrile, butanetetracarbonitrile, cyclobutanetetracarbonite , Pentanetetracarbonitrile, cyclopentanetetracarbonitrile, hexanetetracarbonitrile, cyclohexanetetracarbonitrile, heptanetetracarbonitrile, cycloheptanetetracarbonitrile, octanetetracarbonitrile, cyclooctanetetracarbonyl, nonanetetracarbonitrile, decane Tetracarbonitrile, undecanetetracarbonitrile, dodecanetetracarbonitrile, tetracyanobenzene, tetracyanonaphthalene, tetracyanoanthracene, tetracyanophenanthrene;

  Propanepentacarbonitrile, cyclopropanepentacarbonitrile, butanepentacarbonitrile, cyclobutanepentacarbonitrile, pentanepentacarbonitrile, cyclopentanepentacarbonitrile, hexanepentacarbonitrile, cyclohexanepentacarbonitrile, heptanepentacarbonitrile, cycloheptanepenta Carbonitrile, octanepentacarbonitrile, cyclooctanepentacarbonitrile, nonanepentacarbonitrile, decanepentacarbonitrile, undecanepentacarbonitrile, dodecanepentacarbonitrile, propanehexacarbonitrile, cyclopropanehexacarbonitrile, butanehexacarbonitrile , Cyclobutane hexacarbonitrile, pentane hexacarbonitri , Cyclopentane hexa-carbonitrile, hexane hexa-carbonitrile, cyclohexanehexacarboxylic carbonitrile, heptane hex carbonitrile, octane hexa-carbonitrile, hexacyano benzene.

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

  Propanetricarbonitrile, butanetricarbonitrile, pentanetricarbonitrile, hexanetricarbonitrile, cyclohexanetricarbonitrile, tricyanobenzene, propanetetracarbonitrile, cyclopropanetetracarbonitrile, butanetetracarbonitrile, pentanetetracarbonitrile, Hexanetetracarbonitrile, cyclohexanetetracarbonitrile, tetracyanobenzene, pentanepentacarbonitrile, cyclopentanepentacarbonitrile, hexanepentacarbonitrile, cyclohexanepentacarbonitrile, pentanehexacarbonitrile, cyclopentanehexacarbonitrile, hexanehexacarbonitrile , Cyclohexanehexacarbonitrile.

(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. When (A) the binding force between the nitrile compound and (B) boron trihalide is improved and the composition is used, the polymerization of the (C) episulfide 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 nitrile compound and (B) boron trihalide form a compound (complex) via a coordination bond, the preparation of the composition at room temperature (C) episulfide It is preferable because the polymerization of the compound can be further suppressed, the stability of the composition tends to be further improved, and / or when the (C) episulfide compound is polymerized, the side reaction tends to be further suppressed. From the same viewpoint, it is more preferable that all of (B) boron trihalide contained in the composition form a compound (complex) via a coordination bond with (A) nitrile compound.

(Component (C): Episulfide compound)
Component (C) of this embodiment is a compound having at least one three-membered ring thioether structure as a polymerizable functional group. As the component (C), one type of episulfide compound may be used alone, or a plurality of types of episulfide 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.

  Component (C) may have only a three-membered ring thioether structure as a polymerizable functional group, or may have a commonly used polymerizable functional group together with the three-membered ring thioether structure.

  Although it does not specifically limit as a polymerizable functional group generally used, For example, a cyclic thioether structure, a lactone structure, a cyclic carbonate structure and its sulfur-containing analog structure, a cyclic acetal structure and its sulfur-containing analog structure, a cyclic amine structure, cyclic It can be selected from an 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.

  An episulfide compound having a three-membered thioether structure as a polymerizable functional group and a commonly used polymerizable functional group may have polymerizable functional groups with different polymerization conditions. Therefore, the episulfide compound is obtained by polymerizing at least one polymerizable functional group, forming a semipolymer, and performing a process such as molding the semipolymer, and then polymerizing it to obtain 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 episulfide compound, it has only a 3-membered ring thioether structure as a polymerizable functional group, or has a 3-membered ring thioether 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 thioether structure as a polymerizable functional group, or has a three-membered ring thioether 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 thioether structure as a polymerizable functional group is particularly preferable.

  The episulfide equivalent (WPT, g / mol) of the component (C) is preferably 65 or more because the vapor pressure in the standard state of the episulfide compound is high and the handling tends to be easy. The episulfide equivalent is more preferably 85 or more because it tends to suppress side reactions during polymerization. From the same viewpoint, the episulfide equivalent is more preferably 100 or more.

The episulfide equivalent (WPT, g / mol) of the component (C) is preferably 700 or less because it tends to suppress residual episulfide groups when the composition is polymerized. The episulfide equivalent is more preferably 600 or less because the heat resistance of the cured product formed from the episulfide compound tends to be improved. From the same viewpoint, the episulfide equivalent is more preferably 500 or less.

  The component (C) is not particularly limited as long as it is a compound having a three-membered ring thioether structure as a polymerizable functional group, but it is easily available, the cost of the composition is suppressed, and the economy tends to be excellent. It preferably has a partial structure represented by the following formula (3), (4), (5) or (6). Moreover, since it exists in the tendency for the stability as a composition to improve more, it is more preferable to have a partial structure represented by following formula (3) or (4). Furthermore, since it exists in the tendency which can suppress a side reaction more when superposing | polymerizing a composition, it is especially preferable to have a partial structure represented by Formula (3).

In the formula, R ₂₀ , R ₂₁ , R ₂₂ , R ₂₃ , R ₂₄ , R ₂₅ , R ₂₆ , R ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ , R ₃₁ , R ₃₂ , R ₃₃ and R ₃₄ 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 episulfide compounds, polyfunctional episulfide compounds that are thioglycidyl etherified products of polyphenol compounds, alicyclic episulfide compounds, and polyfunctional compounds that are thioglycidyl etherified products of various novolak compounds. Episulfide compounds, aromatic hydrides of aromatic episulfide compounds, heterocyclic episulfide compounds, thioglycidyl ester episulfide compounds, thioglycidylamine episulfide compounds, and episulfide compounds obtained by thioglycidylation of halogenated phenols (including sulfur) Examples include functional aliphatic episulfide compounds, silicone compounds having an episulfide group in the molecule, and heteropolymerizable functional group-containing episulfide compounds. These may be used alone or in combination.

(Monofunctional episulfide compound)
The monofunctional episulfide compound is not particularly limited as long as it is a compound having one three-membered ring thioether structure. Specifically, ethylene sulfide, propylene sulfide, 1-butene sulfide, 2-butene sulfide, butadiene sulfide , Butadiene dithioepoxide, cyclobutene sulfide, 1,3-cyclobutadiene dithioepoxide, 1-pentene sulfide, 2-pentene sulfide, 1,3-pentadiene dithioepoxide, 1,4-pentadiene dithioepoxide, 2-methyl-2- Butene sulfide, 2-methyl-3-butene sulfide, cyclopentene sulfide, 1,3-cyclopentadiene dithioepoxide, 1-methyl-cyclobutene sulfide, 3-methyl-1-cyclobutene sulfide, 1-hex Sulfide, 2-hexene sulfide, 3-hexene sulfide, 1,3-hexadiene dithioepoxide, 1,4-hexadiene dithioepoxide, 1,5-hexadiene dithioepoxide, 1,3,5-hexatrienethioepoxide, cyclohexene sulfide 1,3-cyclohexadiene dithioepoxide, 1,3,5-cyclohexatrienethioepoxide, 1-methyl-cyclopentene sulfide, 3-methyl-cyclopentene sulfide, 1-methyl-1,3-cyclopentadiene dithioepoxide, 2 -Methyl-1,3-cyclopentadiene dithioepoxide, 5-methyl-1,3-cyclopentadiene dithioepoxide, 3,4-dimethyl-cyclobutene sulfide, 2,3-dimethyl-cyclobutenesulfur 1,2-dimethyl-cyclobutene sulfide, 1,2-dimethyl-1,3-cyclobutadiene dithioepoxide, 2,3-dimethyl-1,3-cyclobutadiene dithioepoxide, 3,3-dimethyl-1 , 2-thioepoxybutane, 1-heptene sulfide, 2-heptene sulfide, 3-heptene sulfide, 1,3-heptadiene dithioepoxide, 1,4-heptadiene dithioepoxide, 1,5-heptadiene dithio Epoxide, 1,5-heptadiene dithioepoxide, 1,6-heptadiene dithioepoxide, 1,3,5-heptatrientiothiopoxide, 1,3,6-heptatrienethioepoxide, 1,4,6-heptatrient Lithioepoxide, cycloheptene sulfide, 1-methyl-cyclohexene Sulfide, 3-methyl-cyclohexene sulfide, 4-methyl-cyclohexene sulfide, 1-methyl-1,3-cyclohexadiene dithioepoxide, 1-methyl-1,4-hexadiene dithioepoxide, 1-methyl-1,3,5 -Hexatrienethioepoxide, 1,2-thioepoxy-5-hexene, 1,2-thioepoxy-4-vinylcyclohexene, 2-norbornene sulfide, 7-methyl-2-norbornene sulfide, 7,7-dimethyl-2-norbornene Sulfide, 2-methyl-2-norbornene sulfide, 2,3-dimethyl-2-norbornene sulfide, 2,7-dimethyl-2-norbornene sulfide, 2,7,7-trimethyl-2-norbornene sulfide, 2,3- Thioepoxy-bicyclo [ 2.2] octane, 2,3-thioepoxy-2-methyl-bicyclo [2.2.2] octane, 2,3-thioepoxy-2,3-dimethyl-bicyclo [2.2.2] octane, 2 , 3-thioepoxy-2,5-dimethyl-bicyclo [2.2.2] octane, 2,3-thioepoxy-2,6-dimethyl-bicyclo [2.2.2] octane, 2,3-thioepoxy-2 , 3,5-trimethyl-bicyclo [2.2.2] octane, 2,3-thioepoxy-2,5,6-trimethyl-bicyclo [2.2.2] octane, 2,3-thioepoxy-2,3 , 5,6-tetramethyl-bicyclo [2.2.2] octane, dioctyl thioepoxyhexahydrophthalate, di-2-ethylhexyl thioepoxyhexahydrophthalate, stibene sulfide, Nylthioglycidyl ether, 3- (2,2,3,3-tetrafluoropropoxy) -1,2-thioepoxypropane, pinene sulfide, isoprene monosulfide, 1,2-thioepoxyethylbenzene, naphthylthioglycidyl ether, 3 -(2-biphenyloxy) -1,2-thioepoxypropane, allyl thioglycidyl ether, 1,1-diphenyl-ethylene sulfide, thioglycidyl (meth) acrylate, thioglycidyl butyrate, iodomethyl thiirane, 4- (2, 3-thioepoxypropyl) morpholine, thioglycidyl methyl ether, 2-phenyl-propylene sulfide, 2,3-thioepoxypropyl-furfuryl ether, 2,3,4,5,6-pentafluorostyrene sulfide, ethyl-3 -F Phenylthioglycidate, limonene sulfide, thioepoxysuccinic acid, 3-thioglycidoxypropyltrimethoxysilane, (3-thioglycidoxypropyl) pentamethyldisiloxane, 3-thioglycidoxypropyl (methyl) dimethoxy Silane, 3-thioglycidoxypropyl (methyl) diethoxysilane, 3-thioglycidoxypropyl (methyl) dibutoxysilane, 2- (3,4-thioepoxycyclohexyl) ethyl (methyl) dimethoxysilane, 2- (3,4-thioepoxycyclohexyl) ethyl (phenyl) diethoxysilane, 2,3-thioepoxypropyl (methyl) dimethoxysilane, 2,3-thioepoxypropyl (phenyl) dimethoxysilane, 3-thioglycidoxypropyl Trimethoxysilane, 3-thio Lysidoxypropyltriethoxysilane, 3-thioglycidoxypropyltributoxysilane, 2- (3,4-thioepoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-thioepoxycyclohexyl) ethyltriethoxysilane, It may be selected from 2,3-thioepoxypropyltrimethoxysilane and 2,3-thioepoxypropyltriethoxysilane.

  Among them, the vapor pressure in the standard state is high, the handling is easy, the stability as the composition tends to be further improved, and the side reaction during polymerization tends to be further suppressed, so that it is monofunctional. The episulfide compound is preferably at least one compound selected from the following group.

  Ethylene sulfide, propylene sulfide, 1-butene sulfide, 2-butene sulfide, butadiene sulfide, butadiene dithioepoxide, cyclobutene sulfide, 1,3-cyclobutadiene dithioepoxide, 1-pentene sulfide, 2-pentene sulfide, 1,3- Pentadiene dithioepoxide, 1,4-pentadiene dithioepoxide, 2-methyl-2-butene sulfide, 2-methyl-3-butene sulfide, cyclopentene sulfide, 1,3-cyclopentadiene dithioepoxide, 1-methyl-cyclobutene sulfide, 3-methyl-1-cyclobutene sulfide, 1-hexene sulfide, 2-hexene sulfide, 3-hexene sulfide, 1,3-hexadiene dithioepoxide, 1,4-hexadi Dithioepoxide, 1,5-hexadiene dithioepoxide, 1,3,5-hexatrienethioepoxide, cyclohexene sulfide, 1,3-cyclohexadiene dithioepoxide, 1,3,5-cyclohexatrienethioepoxide, 1-methyl -Cyclopentene sulfide, 3-methyl-cyclopentene sulfide, 1-methyl-1,3-cyclopentadiene dithioepoxide, 2-methyl-1,3-cyclopentadiene dithioepoxide, 5-methyl-1,3-cyclopentadiene dithioepoxide, 3,4-dimethyl-cyclobutene sulfide, 2,3-dimethyl-cyclobutene sulfide, 1,2-dimethyl-cyclobutene sulfide, 1,2-dimethyl-1,3-cyclobutadiene dithioepoxide, 2,3- Methyl-1,3-cyclobutadienedithioepoxide, 3,3-dimethyl-1,2-thioepoxybutane, 1-heptene sulfide, 2-heptene sulfide, 3-heptene sulfide, 1,3-heptadiene dithio Epoxide, 1,4-heptadiene dithioepoxide, 1,5-heptadiene dithioepoxide, 1,5-heptadiene dithioepoxide, 1,6-heptadiene dithioepoxide, 1,3,5-heptatriene thioepoxide, 1 , 3,6-heptatrienethioepoxide, 1,4,6-heptatrienethioepoxide, cycloheptene sulfide, 1-methyl-cyclohexene sulfide, 3-methyl-cyclohexene sulfide, 4-methyl-cyclohexene sulfide, 1-methyl -1,3-cyclohex Sadiene dithioepoxide, 1-methyl-1,4-hexadiene dithioepoxide, 1-methyl-1,3,5-hexatrienethioepoxide, 1,2-thioepoxy-5-hexene, 1,2-thioepoxy-4- Vinylcyclohexene, dioctyl thioepoxyhexahydrophthalate, di-2-ethylhexyl thioepoxyhexahydrophthalate, stibene sulfide, phenylthioglycidyl ether, 3- (2,2,3,3-tetrafluoropropoxy) -1, 2-thioepoxypropane, pinene sulfide, isoprene monosulfide, 1,2-thioepoxyethylbenzene, naphthylthioglycidyl ether, 3- (2-biphenyloxy) -1,2-thioepoxypropane, allylthioglycidyl ether, 1,1 -Giffeni Ethylene sulfide oxide, thioglycidyl (meth) acrylate, thioglycidyl butyrate, iodomethyl thiirane, 4- (2,3-thioepoxypropyl) morpholine, thioglycidyl methyl ether, 2-phenyl-propylene sulfide, 2,3 -Thioepoxypropyl-furfuryl ether, 2,3,4,5,6-pentafluorostyrene sulfide, ethyl-3-phenylthioglycidate, limonene sulfide, thioepoxysuccinic acid, 3-thioglycidoxypropyltrimethoxy Silane, (3-thioglycidoxypropyl) pentamethyldisiloxane, 3-thioglycidoxypropyl (methyl) dimethoxysilane, 3-thioglycidoxypropyl (methyl) diethoxysilane, 3-thioglycidoxypropyl ( Til) dibutoxysilane, 2- (3,4-thioepoxycyclohexyl) ethyl (methyl) dimethoxysilane, 2- (3,4-thioepoxycyclohexyl) ethyl (phenyl) diethoxysilane, 2,3-thioepoxypropyl (Methyl) dimethoxysilane, 2,3-thioepoxypropyl (phenyl) dimethoxysilane, 3-thioglycidoxypropyltrimethoxysilane, 3-thioglycidoxypropyltriethoxysilane, 3-thioglycidoxypropyltributoxy Silane, 2- (3,4-thioepoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-thioepoxycyclohexyl) ethyltriethoxysilane, 2,3-thioepoxypropyltrimethoxysilane and 2,3-thio Epoxypropyltriethoxysila N.

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

  Propylene sulfide, 1-butene sulfide, 2-butene sulfide, butadiene sulfide, butadiene dithioepoxide, 1-pentene sulfide, 2-pentene sulfide, 1,3-pentadiene dithioepoxide, 1,4-pentadiene dithioepoxide, 2-methyl- 2-butene sulfide, 2-methyl-3-butene sulfide, cyclopentene sulfide, 1-methyl-cyclobutene sulfide, 3-methyl-1-cyclobutene sulfide, 1-hexene sulfide, 2-hexene sulfide, 3-hexene sulfide, 1,3-hexadiene dithioepoxide, 1,4-hexadiene dithioepoxide, 1,5-hexadiene dithioepoxide, 1,3,5-hexatrienethioepoxide, cyclohexene sulfide 1,3-cyclohexadiene dithioepoxide, 1-methyl-cyclopentene sulfide, 3-methyl-cyclopentene sulfide, 2-heptene sulfide, 3-heptene sulfide, 1,3-heptadiene dithioepoxide, 1,4-heptadiene Dithioepoxide, 1,5-heptadiene dithioepoxide, 1,5-heptadiene dithioepoxide, 1,6-heptadiene dithioepoxide, 1-methyl-cyclohexene sulfide, 3-methyl-cyclohexene sulfide, 4-methyl-cyclohexene sulfide 1,2-thioepoxy-5-hexene, 1,2-thioepoxy-4-vinylcyclohexene, stibene sulfide, phenylthioglycidyl ether, 3- (2,2,3,3-tetrafluoropropoxy) -1,2 Thioepoxypropane, pinene sulfide, isoprene monosulfide, 1,2-thioepoxyethylbenzene, naphthylthioglycidyl ether, 3- (2-biphenyloxy) -1,2-thioepoxypropane, allylthioglycidyl ether, 1,1-diphenyl Ethylene sulfide, thioglycidyl (meth) acrylate, thioglycidyl butyrate, iodomethyl thiirane, 4- (2,3-thioepoxypropyl) morpholine, thioglycidyl methyl ether, 2-phenyl-propylene sulfide, 2,3- Thioepoxypropyl-furfuryl ether, 2,3,4,5,6-pentafluorostyrene sulfide, ethyl-3-phenylthioglycidate, limonene sulfide, thioepoxysuccinic acid, 3-thioglycidoxy Cypropyltrimethoxysilane, (3-thioglycidoxypropyl) pentamethyldisiloxane, 3-thioglycidoxypropyl (methyl) dimethoxysilane, 3-thioglycidoxypropyl (methyl) diethoxysilane, 3-thio Oglycidoxypropyl (methyl) dibutoxysilane, 2- (3,4-thioepoxycyclohexyl) ethyl (methyl) dimethoxysilane, 2- (3,4-thioepoxycyclohexyl) ethyl (phenyl) diethoxysilane, 2, 3-thioepoxypropyl (methyl) dimethoxysilane, 2,3-thioepoxypropyl (phenyl) dimethoxysilane, 3-thioglycidoxypropyltrimethoxysilane, 3-thioglycidoxypropyltriethoxysilane, 3-thioglycol Sidoxypropyl tributoxysilane 2- (3,4-thioepoxycyclohexyl) ethyltrimethoxysilane, 2- (3,4-thioepoxycyclohexyl) ethyltriethoxysilane, 2,3-thioepoxypropyltrimethoxysilane, and 2,3-thioepoxy Propyltriethoxysilane.

(Multifunctional episulfide compound)
The polyfunctional episulfide compound which is a thioglycidyl 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, tetramethyl bisphenol F, dimethyl bisphenol F, tetramethyl bisphenol S, dimethyl bisphenol S, tetramethyl-4,4′-biphenol, dimethyl-4,4′-biphenylphenol, 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- -Butylphenol), trishydroxyphenylmethane, resorcinol, hydroquinone, 2,6-di (t-butyl) hydroquinone, pyrogallol, phenols having a diisopropylidene skeleton, 1,1-di (4-hydroxyphenyl) fluorene, etc. It can be selected from phenols having a fluorene skeleton and thioglycidyl etherified products of polyphenol compounds such as phenolized polybutadiene.

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

  Typical examples of polyfunctional episulfide compounds which are thioglycidyl etherification 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 episulfide compounds)
The alicyclic episulfide compound is not particularly limited as long as it is an episulfide compound having an alicyclic episulfide structure, and is selected from, for example, episulfide compounds having a cyclohexene sulfide group, a tricyclodecene sulfide group, a cyclopentene sulfide group, or the like. Can be.

  Specific examples of the alicyclic episulfide compound include 3,4-thioepoxycyclohexenylmethyl-3 ′, 4′-thioepoxycyclohexenecarboxylate, 3,4-thioepoxycyclohexylmethyl-3,4-thioepoxycyclohexanecarboxyl. Rate, 3,4-thioepoxycyclohexyloctyl-3,4-thioepoxycyclohexanecarboxylate, 2- (3,4-thioepoxycyclohexyl-5,5-spiro-3,4-thioepoxy) cyclohexane-meta-dioxane, Bis (3,4-thioepoxycyclohexylmethyl) adipate, vinylcyclohexene disulfide, bis (3,4-thioepoxy-6-methylcyclohexylmethyl) adipate, 3,4-thioepoxy-6-methylcyclohexyl-3, -Thioepoxy-6-methylcyclohexanecarboxylate, methylenebis (3,4-thioepoxycyclohexane), dicyclopentadiene dithioepoxide, ethylene glycol di (3,4-thioepoxycyclohexylmethyl) ether, ethylenebis (3,4-thio) Epoxycyclohexanecarboxylate), and 1,2,8,9-dithioepoxylimonene. Other polyfunctional alicyclic episulfide compounds include 1,2-epoxy-4- (2-thiylyl) cyclohexene or 1,2-thioepoxy-4- (2,2-bis (hydroxymethyl) -1-butanol. 2-thiylyl) cyclohexene adduct and the like.

  Typical examples of the alicyclic episulfide compound are shown below.

(Polyfunctional episulfide compound which is a thioglycidyl etherified product of novolak compound)
The polyfunctional episulfide compound which is a thioglycidyl 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 Various novolak compounds such as novolak compounds made from various phenols such as naphthols, xylylene skeleton-containing phenol novolak compounds, dicyclopentadiene skeleton-containing phenol novolak compounds, biphenyl skeleton-containing phenol novolak compounds, and fluorene skeleton-containing phenol novolak compounds. It may be selected from thioglycidyl etherified compounds.

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

  Typical examples of polyfunctional episulfide compounds which are thioglycidyl etherification products of novolak compounds 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.

(Nuclear hydride of aromatic episulfide compound)
The nuclear hydride of the aromatic episulfide 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 the hydrogen of thioglycidyl etherified products of novolak compounds May be selected from the compounds.

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

(Thioglycidyl ester episulfide compound)
The thioglycidyl ester-based episulfide compound is not particularly limited, and may be selected from episulfide compounds derived from carboxylic acid compounds such as hexahydrophthalic acid diglycidyl ester and tetrahydrophthalic acid diglycidyl ester.

(Thioglycidylamine episulfide compound)
The thioglycidylamine-based episulfide compound is not particularly limited. For example, an episulfide compound obtained by thioglycidylating an amine such as aniline, toluidine, p-phenylenediamine, m-phenylenediamine, diaminodiphenylmethane derivative and diaminomethylbenzene derivative. Can be chosen from.

(Episulfide compounds obtained by thioglycidylation of halogenated phenols)
Episulfide compounds obtained by thioglycidylating halogenated phenols are not particularly limited, and examples thereof include brominated bisphenol A, brominated bisphenol F, brominated bisphenol S, brominated phenol novolak, brominated cresol novolak, and chlorinated. It can be selected from episulfide compounds obtained by thioglycidyl etherification of halogenated phenols such as bisphenol S and chlorinated bisphenol A.

((Sulfur-containing) polyfunctional aliphatic episulfide compound)
The (sulfur-containing) polyfunctional aliphatic episulfide compound is not particularly limited, and specifically, 1,1-bis (epithioethyl) methane, 1- (epithioethyl) -1- (β-epithiopropyl) ) Methane, 1,1-bis (β-epithiopropyl) methane, 1- (epithioethyl) -1- (β-epithiopropyl) ethane, 1,2-bis (β-epithiopropylethane), 1- ( Epithioethyl) -3- (β-epithiopropyl) butane, 1,3-bis (β-epithiopropyl) propane, 1- (epithioethyl) -4- (β-epithiopropyl) pentane, 1,4-bis (Β-epithiopropyl) butane, 1- (epithioethyl) -5- (β-epithiopropyl) hexane, 1- (epithioethyl) -2- (γ-epithiobutylthio) ethane, 1 (Epithioethyl) -2- [2- (γ-epithiobutylthio) ethylthio] ethane, tetrakis (β-epithiopropyl) methane, 1,1,1-tris (β-epithiopropyl) propane, 1,3 -Bis (β-epithiopropyl) -1- (β-epithiopropyl) -2-thiapropane, 1,5-bis (β-epithiopropyl) -2,4-bis (β-epithiopropyl)- 3-thiapentane, 1,3 or 1,4-bis (epithioethyl) cyclohexane, 1,3 or 1,4-bis (β-epithiopropyl) cyclohexane, 2,5-bis (epithioethyl) -1,4-dithiane 2,5-bis (β-epithiopropyl) -1,4-dithiane, 4-epithioethyl-1,2-cyclohexene sulfide, 2,2-bis [4- (epithioethyl) cycl Cyclohexyl] propane, 2,2-bis [4- (β-epithiopropyl) cyclohexyl] propane, bis [4- (epithioethyl) cyclohexyl] methane, bis [4- (β-epithiopropyl) cyclohexyl] methane, bis [4- (β-epithiopropyl) cyclohexyl] sulfide, bis [4- (epithioethyl) cyclohexyl] sulfide, bis (β-epithiopropyl) ether, bis (β-epithiopropyloxy) methane, 1,2- Bis (β-epithiopropyloxy) ethane, 1,3-bis (β-epithiopropyloxy) propane, 1,2-bis (β-epithiopropyloxy) propane, 1- (β-epithiopropyloxy) ) -2- (β-epithiopropyloxymethyl) propane, 1,4-bis (β-epithiopropyloxy) Xyl) butane, 1,3-bis (β-epithiopropyloxy) butane, 1- (β-epithiopropyloxy) -3- (β-epithiopropyloxymethyl) butane, 1,5-bis (β -Epithiopropyloxy) pentane, 1- (β-epithiopropyloxy) -4- (β-epithiopropyloxymethyl) pentane, 1,6-bis (β-epithiopropyloxy) hexane, 1- ( β-epithiopropyloxy) -5- (β-epithiopropyloxymethyl) hexane, 1- (β-epithiopropyloxy) -2-[(2-β-epithiopropyloxyethyl) oxy] ethane, 1- (β-epithiopropyloxy) -2-{[2- (2-β-epithiopropyloxyethyl) oxyethyl] oxy} ethane, tetrakis (β-epithiopropyloxy) Cymethyl) methane, 1,1,1-tris (β-epithiopropyloxymethyl) propane, 1,5-bis (β-epithiopropyloxy) -2- (β-epithiopropyloxymethyl) -3- Thiapentane, 1,5-bis (β-epithiopropyloxy) -2,4-bis (β-epithiopropyloxymethyl) -3-thiapentane;

  1- (β-epithiopropyloxy) -2,2-bis (β-epithiopropyloxymethyl) -4-thiahexane, 1,5,6-tris (β-epithiopropyloxy) -4- (β -Epithiopropyloxymethyl) -3-thiahexane, 1,8-bis (β-epithiopropyloxy) -4- (β-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis ( β-epithiopropyloxy) -4,5-bis (β-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyloxy) -4,4-bis (β -Epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyloxy) -2,4,5-tris (β-epithiopropyloxymethyl) -3,6-dithia Kutan, 1,8-bis (β-epithiopropyloxy) -2,5-bis (β-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,9-bis (β-epithiopropyloxy) -5- (β-epithiopropyloxymethyl) -5-[(2-β-epithiopropyloxyethyl) oxymethyl] -3,7-dithianonane, 1,10-bis (β-epithiopropyloxy) -5,6-bis [(2-β-epithiopropyloxyethyl) oxy] -3,6,9-trithiadecane, 1,11-bis (β-epithiopropyloxy) -4,8-bis (β -Epithiopropyloxymethyl) -3,6,9-trithiaundecane, 1,11-bis (β-epithiopropyloxy) -5,7-bis (β-epithiopropyloxymethyl) -3,6 , 9-to Thiaundecane, 1,11-bis (β-epithiopropyloxy) -5,7-[(2-β-epithiopropyloxyethyl) oxymethyl] -3,6,9-trithiaundecane, 1,11 -Bis (β-epithiopropyloxy) -4,7-bis (β-epithiopropyloxymethyl) -3,6,9-trithiaundecane, 1,3 or 1,4-bis (β-epithio) Propyloxy) cyclohexane, 1,3 or 1,4-bis (β-epithiopropyloxymethyl) cyclohexane, bis [4- (β-epithiopropyloxy) cyclohexyl] methane, 2,2-bis [4- ( β-epithiopropyloxy) cyclohexyl] propane, bis [4- (β-epithiopropyloxy) cyclohexyl] sulfide, 2,5-bis (β-epithiopropiyl) Ruoxymethyl) -1,4-dithiane, 2,5-bis (β-epithiopropyloxyethyloxymethyl) -1,4-dithiane, bis (β-epithiopropyl) sulfide, bis (β-epithiopropyl) Disulfide, bis (β-epithiopropyl) trisulfide, bis (β-epithiopropylthio) methane, bis (β-epithiopropyldithio) methane, bis (β-epithiopropyldithio) ethane, bis (β- Epithiopropyldithioethyl) sulfide, bis (β-epithiopropyldithioethyl) disulfide, 1,2-bis (β-epithiopropylthio) ethane, 1,3-bis (β-epithiopropylthio) propane, 1,2-bis (β-epithiopropylthio) propane, 1- (β-epithiopropylthio) -2- (β-epithiopro Pyrthiomethyl) propane, 1,4-bis (β-epithiopropylthio) butane, 1,3-bis (β-epithiopropylthio) butane, 1- (β-epithiopropylthio) -3- (β- Epithiopropylthiomethyl) butane, 1,5-bis (β-epithiopropylthio) pentane, 1- (β-epithiopropylthio) -4- (β-epithiopropylthiomethyl) pentane, 1,6 -Bis (β-epithiopropylthio) hexane, 1- (β-epithiopropylthio) -5- (β-epithiopropylthiomethyl) hexane, 1- (β-epithiopropylthio) -2- [ (2-β-epithiopropylthioethyl) thio] ethane, 1- (β-epithiopropylthio) -2-{[2- (2-β-epithiopropylthioethyl) thioethyl] thio} ethanetetrakis (Β-epithiopropylthiomethyl) methane, tetrakis (β-epithiopropyldithiomethyl) methane, 1,1,1-tris (β-epithiopropylthiomethyl) propane, 1,2,3-tris (β -Epithiopropyldithio) propane, 1,5-bis (β-epithiopropylthio) -2- (β-epithiopropylthiomethyl) -3-thiapentane, 1,5-bis (β-epithiopropylthio) ) -2,4-bis (β-epithiopropylthiomethyl) -3-thiapentane;

  1,6-bis (β-epithiopropyldithiomethyl) -2- (β-epithiopropyldithioethylthio) -4-thiahexane, 1- (β-epithiopropylthio) -2,2-bis (β -Epithiopropylthiomethyl) -4-thiahexane, 1,5,6-tris (β-epithiopropylthio) -4- (β-epithiopropylthiomethyl) -3-thiahexane, 1,8-bis ( β-epithiopropylthio) -4- (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylthio) -4,5-bis (β-epithio Propylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylthio) -4,4-bis (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8- Screw (β-E Thiopropylthio) -2,4,5-tris (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylthio) -2,5-bis (β- Epithiopropylthiomethyl) -3,6-dithiaoctane, 1,9-bis (β-epithiopropylthio) -5- (β-epithiopropylthiomethyl) -5-[(2-β-epithiopropyl) Thioethyl) thiomethyl] -3,7-dithianonane, 1,10-bis (β-epithiopropylthio) -5,6-bis [(2-β-epithiopropylthioethyl) thio] -3,6, 9-trithiadecane, 1,11-bis (β-epithiopropylthio) -4,8-bis (β-epithiopropylthiomethyl) -3,6,9-trithiaundecane, 1,11-bis (β -Epithiopropylthio) 5,7-bis (β-epithiopropylthiomethyl) -3,6,9-trithiaundecane, 1,11-bis (β-epithiopropylthio) -5,7-[(2-β-epi Thiopropylthioethyl) thiomethyl] -3,6,9-trithiaundecane, 1,11-bis (β-epithiopropylthio) -4,7-bis (β-epithiopropylthiomethyl) -3,6 , 9-trithiaundecane, tetra [2- (β-epithiopropylthio) acetylmethyl] methane, 1,1,1-tri [2- (β-epithiopropylthio) acetylmethyl] propane, tetra [2 -(Β-epithiopropylthiomethyl) acetylmethyl] methane, 1,1,1-tri [2- (β-epithiopropylthiomethyl) acetylmethyl] propane, 1,3 or 1,4-bis (β -Epithio (Lopylthio) cyclohexane, 1,3 or 1,4-bis (β-epithiopropylthiomethyl) cyclohexane, 2,5-bis (β-epithiopropylthiomethyl) -1,4-dithiane, 2,5-bis (Β-epithiopropyldithiomethyl) -1,4-dithiane, 2,5-bis (β-epithiopropylthioethylthiomethyl) -1,4-dithiane, bis [4- (β-epithiopropylthiol) ) Cyclohexyl] methane, 2,2-bis [4- (β-epithiopropylthio) cyclohexyl] propane, bis [4- (β-epithiopropylthio) cyclohexyl] sulfide, 2,2-bis [4- ( β-epithiopropylthio) cyclohexyl] propane, bis [4- (β-epithiopropylthio) cyclohexyl] sulfide may be selected.

  Among these, since the production is easy, the cost as a composition can be suppressed and the economy is excellent. Therefore, the (sulfur-containing) polyfunctional aliphatic episulfide compound is at least one selected from the following group: It is preferable that it is a compound of these.

  Bis (β-epithiopropyloxy) methane, 1,2-bis (β-epithiopropyloxy) ethane, 1,3-bis (β-epithiopropyloxy) propane, 1,2-bis (β-epi Thiopropyloxy) propane, 1- (β-epithiopropyloxy) -2- (β-epithiopropyloxymethyl) propane, 1,4-bis (β-epithiopropyloxy) butane, 1,3-bis (Β-epithiopropyloxy) butane, 1- (β-epithiopropyloxy) -3- (β-epithiopropyloxymethyl) butane, 1,6-bis (β-epithiopropyloxy) hexane, 1 -(Β-epithiopropyloxy) -5- (β-epithiopropyloxymethyl) hexane, 1- (β-epithiopropyloxy) -2-[(2-β-epithiopropyloxy) Ethyl) oxy] ethane, 1- (β-epithiopropyloxy) -2-{[2- (2-β-epithiopropyloxyethyl) oxyethyl] oxy} ethane, tetrakis (β-epithiopropyloxymethyl) Methane, 1,1,1-tris (β-epithiopropyloxymethyl) propane, 1- (β-epithiopropyloxy) -2,2-bis (β-epithiopropyloxymethyl) -4-thiahexane, 1,5,6-tris (β-epithiopropyloxy) -4- (β-epithiopropyloxymethyl) -3-thiahexane;

  1,8-bis (β-epithiopropyloxy) -4- (β-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyloxy) -4,5- Bis (β-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyloxy) -4,4-bis (β-epithiopropyloxymethyl) -3,6- Dithiaoctane, 1,8-bis (β-epithiopropyloxy) -2,4,5-tris (β-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyl) Oxy) -2,5-bis (β-epithiopropyloxymethyl) -3,6-dithiaoctane, 1,3 or 1,4-bis (β-epithiopropyloxy) cyclohexane, 1,3 or 1, 4-bis (β-epithiopropyloxymethyl) cyclohexane, bis [4- (β-epithiopropyloxy) cyclohexyl] methane, 2,2-bis [4- (β-epithiopropyloxy) cyclohexyl] propane, Bis [4- (β-epithiopropyloxy) cyclohexyl] sulfide, 2,5-bis (β-epithiopropyloxymethyl) -1,4-dithiane, 2,5-bis (β-epithiopropyloxyethyl) Oxymethyl) -1,4-dithiane, bis (β-epithiopropyl) sulfide, bis (β-epithiopropyl) disulfide, bis (β-epithiopropylthio) methane, bis (β-epithiopropyldithio) Methane, bis (β-epithiopropyldithio) ethane, bis (β-epithiopropyldithioethyl) sulfide, bi (Β-epithiopropyldithioethyl) disulfide, 1,2-bis (β-epithiopropylthio) ethane, 1,3-bis (β-epithiopropylthio) propane, 1,2-bis (β-epi Thiopropylthio) propane;

  1- (β-epithiopropylthio) -2- (β-epithiopropylthiomethyl) propane, 1,4-bis (β-epithiopropylthio) butane, 1,3-bis (β-epithiopropyl) Thio) butane, 1- (β-epithiopropylthio) -3- (β-epithiopropylthiomethyl) butane, 1,6-bis (β-epithiopropylthio) hexane, 1- (β-epithio) Propylthio) -5- (β-epithiopropylthiomethyl) hexane, 1- (β-epithiopropylthio) -2-[(2-β-epithiopropylthioethyl) thio] ethane, 1- (β -Epithiopropylthio) -2-{[2- (2-β-epithiopropylthioethyl) thioethyl] thio} ethanetetrakis (β-epithiopropylthiomethyl) methane, tetrakis (β-epithiopropyldi) Omethyl) methane, 1,1,1-tris (β-epithiopropylthiomethyl) propane, 1,2,3-tris (β-epithiopropyldithio) propane, 1,6-bis (β-epithiopropyl) Dithiomethyl) -2- (β-epithiopropyldithioethylthio) -4-thiahexane, 1- (β-epithiopropylthio) -2,2-bis (β-epithiopropylthiomethyl) -4-thiahexane 1,5,6-tris (β-epithiopropylthio) -4- (β-epithiopropylthiomethyl) -3-thiahexane;

  1,8-bis (β-epithiopropylthio) -4- (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylthio) -4,5- Bis (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropylthio) -4,4-bis (β-epithiopropylthiomethyl) -3,6- Dithiaoctane, 1,8-bis (β-epithiopropylthio) -2,4,5-tris (β-epithiopropylthiomethyl) -3,6-dithiaoctane, 1,8-bis (β-epithiopropyl) Thio) -2,5-bis (β-epithiopropylthiomethyl) -3,6-dithiaoctane, tetra [2- (β-epithiopropylthio) acetylmethyl] methane, 1,1,1-tri [2 -(Β-epithiopropy Thio) acetylmethyl] propane, tetra [2- (β-epithiopropylthiomethyl) acetylmethyl] methane, 1,1,1-tri [2- (β-epithiopropylthiomethyl) acetylmethyl] propane, 1 , 3 or 1,4-bis (β-epithiopropylthio) cyclohexane, 1,3 or 1,4-bis (β-epithiopropylthiomethyl) cyclohexane, 2,5-bis (β-epithiopropylthio) Methyl) -1,4-dithiane, 2,5-bis (β-epithiopropyldithiomethyl) -1,4-dithiane, 2,5-bis (β-epithiopropylthioethylthiomethyl) -1,4 -Dithiane, bis [4- (β-epithiopropylthio) cyclohexyl] methane, 2,2-bis [4- (β-epithiopropylthio) cyclohexyl] propane, [4- (β-epithiopropylthio) cyclohexyl] sulfide, 2,2-bis [4- (β-epithiopropylthio) cyclohexyl] propane, bis [4- (β-epithiopropylthio) cyclohexyl] Sulfide.

(Silicone compound having an episulfide group in the molecule)
The silicone compound having an episulfide group in the molecule is not particularly limited, and may be selected from, for example, compounds represented by the following formula (8).
(R ₇₀ R ₇₁ R ₇₂ SiO _1/2 ) _a (R ₇₃ R ₇₄ SiO _2/2 ) _b (R ₇₅ SiO _3/2 ) _c (SiO _4/2 ) _d (8)

In the formula (8), 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 ₇₀ to R ₇₅ represents a group containing an episulfide group, other _R 70 _{to R 75} 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.

(Disulfide functional group-containing episulfide compound)
The heteropolymerizable functional group-containing episulfide compound is not particularly limited, and may be selected from, for example, compounds represented by the following formula (9).

In the above formula (9), R _{80 to} R ₈₂ 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 episulfide group. When Y represents a single type of polymerizable functional group, 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, and a cyclic imino ether A structure selected from a 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) nitrile compound and (B) boron trihalide can be represented by an index α calculated by the following formula (2).
Index α = αn / αb (2)
αn: (A) Amount of substance of nitrile group of nitrile 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 coordinate bond with (A) a nitrile compound, and the composition is prepared at room temperature. At this time, since the polymerization of the (C) episulfide compound 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.

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

  The index α is preferably 1000 or less because it tends to suppress the remaining of the episulfide group contained in the (C) episulfide compound when the composition is polymerized. When the process of polymerizing the composition and removing the (A) nitrile 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 500 or less. From the same viewpoint, the index α is more preferably 100 or less.

  The index α is 10 or less, a polymer and a cured product obtained by polymerizing a composition containing (A) a nitrile compound, (B) boron trihalide, and (C) an episulfide compound, Volatility when holding at high temperature for a long period of time is further reduced, and there is a tendency to suppress the generation of voids during molding by melt processing, or contamination or corrosion of metal parts near the polymer or cured product To preferred. From the same viewpoint, the index α is more preferably 5 or less.

  (B) Regarding the mixing ratio of boron trihalide and (C) episulfide compound, (B) the amount of boron trihalide (mol) and (C) the amount of episulfide group contained in the episulfide 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 episulfide group contained in the episulfide compound is 10 or more, and the composition is prepared at room temperature. In this case, the polymerization of the (C) episulfide compound can be further suppressed, and the stability of the composition tends to be further improved, which is preferable. (B) When the substance quantity (mol) of boron trihalide is 1, (C) the substance quantity (mol) of the episulfide group contained in the episulfide compound is 20 or more, and (C) the episulfide compound is polymerized. In doing so, it is more preferable because side reactions tend to be more suppressed. 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 episulfide group contained in the (C) episulfide compound is 50 or more. .

  (B) When the substance amount (mol) of boron trihalide is 1, (C) the substance amount (mol) of the episulfide group contained in the episulfide compound is 50 or more, (A) the nitrile compound, Depending on the combination of (B) boron trihalide and (C) episulfide 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, it is more preferable that the substance amount (mol) of the episulfide group contained in (C) the episulfide compound is 100 or more. More preferably, it is 200 or more.

  (B) When the substance amount (mol) of boron trihalide is set to 1, (C) the substance amount (mol) of the episulfide group contained in the episulfide compound is 100000 or less when polymerizing the composition. (C) Since it exists in the tendency which can suppress the residue of the episulfide group contained in an episulfide compound more, it is preferable. (B) When the substance amount (mol) of boron trihalide is 1, the substance amount (mol) of episulfide group contained in (C) episulfide compound is 20000 or less, and (C) episulfide compound is polymerized. This is more preferable because it tends to suppress side reactions more. From the same viewpoint, when the amount (mol) of (B) is 1, it is more preferable that the amount (mol) of the episulfide group contained in the (C) episulfide compound is 10,000 or less.

The mixing ratio of (B) boron trihalide and (C) episulfide compound can also be represented by the following formula (10).
Index β = αb / αt × 100 (10)
αb: (B) Boron trihalide substance amount (mol)
αt: Substance content (mol) of episulfide group contained in (C) episulfide compound

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

  The method of preparing the composition is not particularly limited as long as it is a commonly used method, but (A) a nitrile compound, (B) a boron trihalide and (C) a method of simultaneously adding an episulfide compound, A method in which two components selected arbitrarily among A) nitrile compound, (B) boron trihalide and (C) episulfide 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 nitrile compound and (B) boron trihalide, The method of adding to (C) episulfide compound or adding (C) episulfide compound is preferable.

  A method for preparing a mixture containing (A) a nitrile compound and (B) boron trihalide is not particularly limited as long as it is a generally used method, but (A) a nitrile compound and (B) three Examples thereof include a method in which boron halide is directly reacted, a method in which (A) a nitrile compound is reacted with (B) a compound containing boron trihalide, and the like. Among these, the method of reacting (A) a nitrile 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) a nitrile 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) a nitrile 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 the formation of a compound via a coordination bond consisting of (A) a nitrile compound and (B) boron trihalide may be prevented, 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 nitrile compound and (B) boron trihalide is unstable, the temperature for preparing the mixture is preferably set to 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) nitrile compound and (B) may deviate from the desired ratio, the temperature at which the mixture is prepared should be adjusted to suppress volatilization. It is preferable to make it below the boiling point. It is also an effective means to suppress the volatilization of the raw material by setting the pressure for preparing the mixture to a desired pressure equal to or higher than atmospheric pressure.

  The atmosphere for preparing the mixture containing (A) a nitrile 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) a nitrile 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) nitrile compound in the standard state is low and the (A) nitrile 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 nitrile compound and (B) boron trihalide, if (A) the nitrile compound is a solid, use a compound capable of dissolving (A) the nitrile compound. Thus, since a uniform mixture can be easily obtained, it may be an effective means.

  (A) Although the compound which can melt | dissolve a nitrile compound will not be specifically limited if it is generally used, As a specific example, n-pentane, n-hexane, isohexane, n-heptane, n-octane, Saturated hydrocarbon compounds such as isooctane, n-nonane, n-decane, cyclopentane, cyclohexane, cycloheptane and cyclooctane, 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, tri Halogenated hydrocarbon compounds such as chloropropane, 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 , 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 And 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 nitrile compound and (B) boron trihalide, (A) a compound capable of dissolving the nitrile compound or (B) a compound containing boron trihalide is 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 nitrile 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 nitrile compound, (B) boron trihalide, and (C) an episulfide compound is not particularly limited, and is performed at a general usable temperature. It is preferable that it is 80-100 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 nitrile compound, (B) boron trihalide, and (C) an episulfide compound, if there is a possibility that the raw material solidifies, the solidification of the raw material is suppressed, or Since the uniform composition tends to be obtained more easily by reducing the viscosity of the raw material, the temperature at which the composition is prepared is preferably −80 ° C. or higher. From the same viewpoint, the temperature for preparing the composition is more preferably −40 ° C. or higher. The temperature for preparing the composition is more preferably −20 ° C. or more because the necessity of using a large cooling facility tends to decrease and the cost for producing the composition tends to be suppressed. From the same viewpoint, it is particularly preferably 0 ° C. or higher.

  When preparing a composition containing (A) a nitrile compound, (B) boron trihalide, and (C) an episulfide compound, polymerization of the (C) episulfide 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 100 ° C. or less. From the same viewpoint, the temperature for preparing the composition is more preferably 80 ° C. or lower. (C) Since the polymerization of the episulfide 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 nitrile compound, (B) boron trihalide, and (C) an episulfide 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 nitrile compound, (B) boron trihalide, and (C) an episulfide 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 nitrile compound, (B) boron trihalide, and (C) an episulfide compound, if the contained compound has a solid, or (A) the nitrile 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 nitrile compound and (B) boron trihalide, which are 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) boron trihalide is highly stable, and a composition containing (A) a nitrile compound, (B) boron trihalide, and (C) an episulfide 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, Robenzen, dichlorobenzene, trichlorobenzene, halogenated hydrocarbon compounds such as chlorotoluene and chloronaphthalene are preferred.

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

  The vacuum distillation temperature can further suppress the polymerization of the (C) episulfide compound, and the stability of the composition containing the (A) nitrile compound, (B) boron trihalide, and (C) episulfide compound is further improved. Since it exists in the tendency, it is preferable that it is 40 degrees C or less. From the same viewpoint, it is more preferably 35 ° C. or lower, and further preferably 25 ° 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 nitrile compound, (B) boron trihalide, and (C) an episulfide 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 episulfide 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 superposing | polymerizing by heating and obtaining a polymer, It is preferable that it is -80-160 degreeC. The polymerization temperature does not need to be constant and may be changed in the middle.

  (C) The polymerization temperature is preferably 160 ° C. or lower because there is a tendency that the possibility of coloring the resulting polymerized product can be reduced by the polymerization heat generated when the episulfide compound is polymerized. (C) When superposing | polymerizing an episulfide compound, since it exists in the tendency which can suppress a side reaction more, 140 degrees C or less is more preferable. From the same viewpoint, the polymerization temperature is more preferably 120 ° C. or less, and particularly preferably 100 ° C. or less.

  (C) Polymerization of the episulfide 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. Since there is a tendency that the polymerization time of the (C) episulfide compound can be further shortened by further increasing the mobility of the polymerization terminal of the polymer, the polymerization temperature is preferably 40 ° C. or higher. From the same viewpoint, the polymerization temperature is more preferably 50 ° C. or higher, and further preferably 60 ° C. or higher.

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

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

  When the composition containing (A) a nitrile compound, (B) boron trihalide, and (C) an episulfide 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.

  In order to accelerate the polymerization reaction when the polymerization is progressed by heating, or as the (C) episulfide compound contained in the composition, in addition to the 3-membered ring thioether structure, a 3-membered ring thioether 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-te Traoxaspiro [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, octylamine, 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- ( 2'-cyanoethyl) -2-undecylimidazole, N- (2'-cyanoethyl) -2-phenylimidazole, 3,3-bis- (2-ethyl-4-methylimidazolyl) methane, alkylimidazole and isocyanuric acid of Various imidazoles such as condensates of pressurized product and an 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-monoforino-propan-1-one and N, N-dimethylaminoacetophenone), anthraquinones ( 2-methylanthraquinone, 2-ethylanthraquinone, 2-tert-butylanthraquinone, 1-chloroanthraquinone, 2-amylanthraquinone and 2-aminoanthraquinone), thioxane (Such as 2,4-dimethylthiosantone, 2,4-diethylthioxanthone, 2-chlorothioxanthone, and 2,4-diisopropylthioxanthone), ketals (such as acetophenone dimethyl ketal and benzyl dimethyl ketal), benzophenones (benzophenone, Methylbenzophenone, 4,4′-dichlorobenzophenone and 4,4′-bisdiethylaminobenzophenone, etc.), xanthones, benzoates (ethyl 4-dimethylaminobenzoate and 2- (dimethylamino) ethylbenzoate, etc.), amines (Triethylamine, triethanolamine, etc.), iodonium salt compound, sulfonium salt compound, ammonium salt compound, phosphonium salt compound, arsonium salt compound, stibonium salt compound, o Soniumu salt compound, a selenonium salt compound, and, stannonium salt compound. These may be used alone or in combination.

  The composition containing (A) a nitrile compound, (B) boron trihalide, and (C) an episulfide 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 episulfide 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 episulfide compound tends to be shortened, the chain transfer agent (D) 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 the polymerization time of the episulfide 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 episulfide 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 the above, (D) the chain transfer agent remains in the polymer or cured product and / or (C) the increase in the polymerization time of the episulfide 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 the polymerization time of the episulfide compound tends to be suppressed, so that a hydroxyl group is contained. 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.

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

  (D) When the substance amount (mol) of the chain transfer agent is 1, the substance amount (mol) of the episulfide group contained in (C) the episulfide compound is 10 or more. Residue in the product or cured product is suppressed, and the volatile matter when the polymer and the cured product obtained by polymerizing the (C) episulfide compound are kept at a high temperature for a long time tends to be further reduced. ,preferable. (D) When the substance amount (mol) of the chain transfer agent is 1, the substance amount (mol) of the episulfide group contained in the (C) episulfide compound is 20 or more, so that it is formed from the (C) episulfide compound. 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 episulfide group contained in the (C) episulfide compound is 50 or more.

  (D) When the substance amount (mol) of the chain transfer agent is 1, the substance amount (mol) of the episulfide group contained in the (C) episulfide compound is 10,000 or less, so that the (C) episulfide compound is polymerized. 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 substance amount (mol) of the (D) chain transfer agent is 1, the substance amount (mol) of the episulfide group contained in the (C) episulfide compound is more preferably 2000 or less. Preferably it is 1000 or less. A composition containing (A) a nitrile compound, (B) boron trihalide, and (C) an episulfide 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) episulfide compound can also be expressed by the following formula (11).
Index γ = αd / αt × 100 (11)
αd: (D) amount of chain transfer agent (mol)
αt: Substance content (mol) of episulfide group contained in (C) episulfide compound

(D) When the ratio of the amount (mol) of the chain transfer agent to the amount (mol) of the episulfide group contained in the (C) episulfide compound 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 episulfide group contained in the (C) episulfide compound 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 episulfide group contained in the (C) episulfide compound 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 episulfide group contained in the (C) episulfide compound 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 episulfide group contained in the (C) episulfide compound 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 episulfide group contained in the (C) episulfide compound is 1: 1000, the index γ = 0.1. .

  As a method for preparing a composition containing (A) a nitrile compound, (B) boron trihalide, (C) an episulfide compound, and (D) a chain transfer agent, any method that is generally used can be used. Without limitation, (A) a nitrile compound, (B) boron trihalide, (C) an episulfide compound, (D) a method of simultaneously adding a chain transfer agent, (A) a nitrile compound, (B) boron trihalide, (C) Episulfide compounds and (D) Chain transfer agents may be mixed with at least two arbitrarily selected components, then added to the remaining components, and / or a method of adding the remaining components. Among these, since the composition can be stably prepared and the stability as the composition tends to be excellent, after preparing a mixture containing (A) a nitrile compound and (B) boron trihalide, A method of adding the remaining component (C) to the episulfide 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, hydrocarbon lubricants such as paraffin wax, microwax 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 type of the surfactant is not particularly limited, and examples thereof include a silicon surfactant and a fluorine surfactant. 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 of modifying the silicone compound is not particularly limited, and examples thereof include 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-hydroxylauranilide, 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) oximide, 3-thiaundecanol, 3-thiapentadecanol, trimethylhexanediol, trimethylolpropane, and 4-hydroxymethyl Esters with mono- or polyhydric alcohols selected from til-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 alcohol: 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, trimethylolethane, trimethylolpropane, 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 (12), 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（１２）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 (12), 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, motors, coils 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 cans, outer surface lacquer, extrusion tube coating, general anticorrosion coating, maintenance process, lacquer for woodworking products, electrodeposition primer for automobiles, 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, various metal products exterior and anticorrosion coating, pipe interior / exterior coating, electrical component insulation coating, etc. ), Composite materials (pipes and tanks for chemical plants, aircraft materials, automotive 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 materials) Thin 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-nitrile compound: ¹¹ B-NMR measurement>
¹¹ B-NMR measurement was performed according to the following procedure.
(1) 10 mg of trimethoxyborane (manufactured by Wako Pure Chemical Industries, Ltd.) was weighed into a sample bottle, chloroform-d (manufactured by Wako Pure Chemical Industries, Ltd.) was added, and the total amount was adjusted to 1 g.
(2) Weigh 10 mg of boron trihalide compound used to prepare the boron trihalide-nitrile compound in a sample bottle, add chloroform-d (manufactured by Wako Pure Chemical Industries, Ltd.), Adjusted to 1 g.
(3) In a sample bottle, 10 mg of the prepared boron trihalide-nitrile compound was weighed, and chloroform-d (manufactured by Wako Pure Chemical Industries, Ltd.) was added to adjust the total amount 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-nitrile compound.

<Calculation of episulfide equivalent (WPT): 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 adjust the total amount to 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: 200 times From the above measurement results, the episulfide equivalent was calculated according to the following procedure.
(3) The area value of the episulfide group-derived peak was calculated from the ¹ H-NMR chart.
Here, the peak derived from the episulfide group refers to a peak derived from one hydrogen on the hydrocarbon constituting the episulfide group. A peak not overlapping with a peak derived from hydrogen other than hydrogen derived from an episulfide group constituting the episulfide 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 (3) and (4) above were substituted into the following formula to determine the episulfide equivalent (g / mol).
Episulfide equivalent (g / mol) = (SAMG / EPIA) × (TBEM / TBEG) × (TBEA / 2)
EPIA: Area value of peak derived from episulfide group TBEA: Area value of peak derived from two hydrogens of TBE TBEG: Weight of TBE used in preparing solution for ¹ H-NMR measurement (g) 20 mg in the 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 episulfide group in the episulfide 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 value calculated in the above (3) and (4) was substituted into the following formula to obtain the episulfide equivalent (g / mol).
Episulfide equivalent (g / mol) = SAMG × (number of hydrogen constituting episulfide group-derived peak / EPIA) × (TBEM / TBEG) × (TBEA / 2)

<Calculation of mixing index α>
The mixing index α was calculated by the following formula (2).
Index α = αn / αb (2)
here,
αn: (A) Amount of substance of nitrile group of nitrile 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 (10).
Index β = αb / αt × 100 (10)
here,
αb: (B) Boron trihalide substance amount (mol)
αt: (C) The amount (mol) of the episulfide group contained in the episulfide compound, respectively.

<Calculation of episulfide 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 adjust the total amount to 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
Cumulative number: 200 times From the above measurement results, the episulfide group reaction rate was calculated by the following procedure.
(3) The area value of the episulfide group-derived peak was calculated from the ¹ H-NMR chart.
Here, the peak derived from the episulfide group refers to a peak derived from one hydrogen on the hydrocarbon constituting the episulfide group. A peak not overlapping with a peak derived from hydrogen other than hydrogen derived from an episulfide group constituting the episulfide 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 episulfide group reaction rate (%).
Episulfide group reaction rate (%) = 100−EPIA × (TBEG / TBEM) × (2 / TBEA) × (REAG / SAMG) × (WPT / EPIG) × 100
EPIA: Area value of peak derived from episulfide group TBEA: Area value of peak derived from two hydrogens of TBE EPIG: Weight of episulfide compound used in preparing composition (g)
WPT: episulfide equivalent (g / mol) of the episulfide 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 episulfide group in the episulfide 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 value calculated in the above (3) and (4) was substituted into the following formula to obtain the episulfide group reaction rate (%).
Episulfide group reaction rate (%) = 100− {EPIA / (number of hydrogen constituting episulfide group-derived peak)} × (TBEG / TBEM) × (2 / TBEA) × (REAG / SAMG) × (WPT / EPIG) × 100

<Calculation of episulfide 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 episulfide 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 episulfide group reaction rate was calculated according to the following procedure.
(4) The area value of the episulfide group-derived peak was calculated from the FT-IR chart.
Here, the peak derived from an episulfide group refers to a peak derived from vibration between atoms constituting the episulfide 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 episulfide group is appropriately selected.
(5) The area value calculated in (4) was substituted into the following formula to determine the episulfide group reaction rate (%).
Episulfide group reaction rate (%) = 100−RIRA / SIRA × 100
RIRA: Peak area derived from episulfide group in the FT-IR chart obtained as a result of measuring the sample SIRA: In the FT-IR chart obtained as a result of measuring the episulfide compound before polymerization used in preparing the sample , Peak area derived from episulfide groups.

<Calculation of vinyl group production rate: 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 adjust the total amount to 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
Integration number: 200 times From the above measurement results, the vinyl group production rate was calculated by the following procedure.
(3) The area value of the vinyl group-derived peak was calculated from the ¹ H-NMR chart.
Here, the peak derived from a vinyl group refers to a peak derived from one hydrogen on the hydrocarbon constituting the vinyl group. A hydrogen that constitutes a compound contained in the sample and that does not overlap with a peak derived from hydrogen other than hydrogen derived from a vinyl group 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 (3) and (4) above were substituted into the following formula to determine the episulfide equivalent (g / mol).
Vinyl group production rate (%) = VINA × (TBEG / TBEM) × (2 / TBEA) × (REAG / SAMG) × (WPT / EPIG) × 100
VINA: Area value of peak derived from vinyl group TBEA: Area value of peak derived from two hydrogens of TEB: Weight of episulfide compound used in preparing composition (g)
WPT: episulfide equivalent (g / mol) of the episulfide 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 vinyl group is observed as the same peak in the ¹ H-NMR measurement, calculation can be performed by changing the procedure of (5) as follows.
(5-2) The area values calculated in the above (3) and (4) were substituted into the following formula to determine the vinyl group production rate (%).
Vinyl group production rate (%) = {VINA / (number of hydrogen constituting vinyl group-derived peak)} × (TBEG / TBEM) × (2 / TBEA) × (REAG / SAMG) × (WPT / EPIG) × 100

<Stability evaluation A>
A part of the prepared composition was put in a thermostat set at 20 ° C. and held for 1 hour, and then the episulfide group reaction rate was calculated by the EA method.
The stability is judged as good (“A”) when the episulfide group reaction rate is 10% or less, judged as particularly good (“AA”) when it 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 episulfide group reaction rate was calculated by the EB method.
The stability is judged as good (“A”) when the episulfide group reaction rate is 10% or less, judged as particularly good (“AA”) when it is 5% or less, and poor (“ C ").

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

<Side reactivity evaluation A>
The vinyl group production rate of the prepared polymer was calculated.
The side reactivity is judged as good (“A”) when the vinyl group production rate is 5% or less, judged as particularly good (“AA”) when it is 2% or less, and otherwise poor ( "C").

<Side reactivity evaluation B>
In the side reactivity evaluation A, when the polymer was not completely dissolved in chloroform-d, the evaluation was carried out by the following method.
(1) The sample for evaluation was made into a powder sample with a freeze pulverizer.
(2) The powder sample of the above (1) was transferred to an NMR tube having a diameter of 4 mmφ, and solid ¹³ C-NMR was measured under the following conditions.
Fourier transform nuclear magnetic resonance apparatus: “ECA700 type” manufactured by JEOL Ltd.
Nuclide: ¹³ C
Integration number: 16,000 times Measurement method: CP / MAS method MAS: 10,000 Hz
(3) From the above measurement results, it was judged as particularly good (“AA”) when no vinyl group-derived peak was observed, and judged as poor (“C”) when observed.

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

The raw materials used in the production examples, examples and comparative examples are shown in the following (1) to (113).
(Epoxy compound)
(1) Epoxy compound B: ethylene oxide (manufactured by Aldrich, hereinafter referred to as “EO”)
Epoxy equivalent (WPE): 44 g / eq.
(2) Epoxy compound C: propylene oxide (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “PO”)
Epoxy equivalent (WPE): 58 g / eq.
(3) Epoxy compound D: 1,2-epoxybutane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “12EB”)
Epoxy equivalent (WPE): 72 g / eq.
(4) Epoxy compound E: 1,2-epoxypentane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “12EP”)
Epoxy equivalent (WPE): 86 g / eq.
(5) Epoxy compound F: 1,2-epoxyhexane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “12EH”)
Epoxy equivalent (WPE): 100 g / eq.
(6) Epoxy compound G: 1,2-epoxyheptane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “12EHP”)
Epoxy equivalent (WPE): 114 g / eq.
(7) Epoxy compound H: 1,2-epoxyoctane (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “12EO”)
Epoxy equivalent (WPE): 128 g / eq.
(8) Epoxy compound I: 1,2-epoxydecane (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “12ED”)
Epoxy equivalent (WPE): 156 g / eq.
(9) Epoxy compound J: 1,2-epoxydodecane (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “12EDD”)
Epoxy equivalent (WPE): 184 g / eq.
(10) Epoxy compound K: 1,2-epoxytetradecane (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “12ETD”)
Epoxy equivalent (WPE): 212 g / eq.
(11) Epoxy compound L: 1,2-epoxyhexadecane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “12EHD”)
Epoxy equivalent (WPE): 240 g / eq.
(12) Epoxy compound M: 1,2-epoxy octadecane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “12EOD”)
Epoxy equivalent (WPE): 268 g / eq.
(13) Epoxy compound N: 1,2-epoxy eicosane (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “12EEC”)
Epoxy equivalent (WPE): 297 g / eq.
(14) Epoxy compound A: phenylglycidyl ether (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “PGE”)
Epoxy equivalent (WPE): 150 g / eq.
(15) Epoxy compound O: bisphenol A type epoxy compound (hereinafter referred to as “Bis-A-1”)
・ Product name: Asahi Kasei Epoxy Co., Ltd.
Epoxy equivalent (WPE): 189 g / eq.
(16) Epoxy compound P: hydrogenated bisphenol A type epoxy compound (hereinafter referred to as “hydrogenated Bis-A”)
・ 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 “Bis-A-2”)
・ Product name: Asahi Kasei Epoxy Co., Ltd.
Epoxy equivalent (WPE): 480 g / eq.
(18) Epoxy compound R: bisphenol A type epoxy compound (hereinafter referred to as “Bis-A-3”)
・ Product name: Asahi Kasei Epoxy Co., Ltd.
Epoxy equivalent (WPE): 560 g / eq.
(19) Epoxy compound S: bisphenol A type epoxy compound (hereinafter referred to as “Bis-A-4”)
・ Product name: Asahi Kasei Epoxy Co., Ltd.
Epoxy equivalent (WPE): 650 g / eq.
(20) Epoxy compound T: cyclopentene oxide (manufactured by Aldrich, hereinafter referred to as “C5O”)
Epoxy equivalent (WPE): 84 g / eq.
(21) Epoxy compound U: cyclohexene oxide (manufactured by Aldrich, hereinafter referred to as “C6O”)
Epoxy equivalent (WPE): 98 g / eq.
(22) Epoxy compound V: cycloheptene oxide (manufactured by Aldrich, hereinafter referred to as “C7O”)
Epoxy equivalent (WPE): 112 g / eq.
(23) Epoxy compound W: cyclooctene oxide (manufactured by Aldrich, hereinafter referred to as “C8O”)
Epoxy equivalent (WPE): 126 g / eq.
(24) Epoxy compound X: cycloaliphatic epoxy compound (hereinafter referred to as “CEL”)
・ Product name: Daicel Chemical Industries, Ltd. “Celoxide 2021P”
Epoxy equivalent (WPE): 131 g / eq.
(25) Epoxy compound Y: bis (2,3-epoxypropyl) disulfide (hereinafter referred to as “BEDS”)
BEDS was synthesized according to the method described in JP-A-2002-194083.
Epoxy equivalent (WPE): 91 g / eq.
(26) Epoxy compound Z: 1,3-bis (3-glycidoxypropyl) -1,1,3,3-tetramethyldisiloxane (hereinafter referred to as “BGTD”)
・ Product name: Shin-Etsu Chemical Co., Ltd., “LS-7970”
Epoxy equivalent (WPE): 182 g / eq.
(27) Epoxy compound AA: bis [2- (3,4-epoxycyclohexyl) ethyl] tetramethyldisiloxane (hereinafter referred to as “BCTD”)
-Trade name: Gelest, Inc. , "SIB1092.0"
Epoxy equivalent (WPE): 192 g / eq.
(28) Epoxy compound AB: 1,3,5,7-tetra- (3-glycidoxypropyl) tetramethylcyclotetrasiloxane (hereinafter referred to as “TGCS”)
Euro. Polym. J. et al. 2010, 46, 1545. TGCS was synthesized according to the method described.
Epoxy equivalent (WPE): 174 g / eq.
(29) Epoxy compound AC: 1,3,5,7-tetra- [2- (3,4-epoxycyclohexylethyl)] tetramethylcyclotetrasiloxane (hereinafter referred to as “TCCS”)
TCCS was synthesized according to the method described in JP-A 2000-103859.
Epoxy equivalent (WPE): 184 g / eq.
(30) Epoxy compound AD: butadiene monooxide (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “BDMO”)
Epoxy equivalent (WPE): 70 g / eq.
(31) Epoxy compound AE: 1,2-epoxy-5-hexene (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “EPHE”)
Epoxy equivalent (WPE): 98 g / eq.
(32) Epoxy compound AF: Allyl glycidyl ether (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “AGE”)
Epoxy equivalent (WPE): 114 g / eq.
(33) Epoxy compound AG: 1,2-epoxy-4-vinylcyclohexane (manufactured by Aldrich, hereinafter referred to as “EVCH”)
Epoxy equivalent (WPE): 124 g / eq.
(34) Epoxy compound AH: Glycidyl methacrylate (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “GLMT”)
Epoxy equivalent: 142 g / eq.

(Cheerizing agent)
(35) Thiaminating agent: Thiourea (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “TU”)

(Hydroxyl compound)
(36) Hydroxyl compound A: 1,2-propylene glycol (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “12PG”)
(37) Hydroxyl compound B: 1,3-propylene glycol (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “13PG”)
(38) Hydroxyl compound C: 1,2-butanediol (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “12BD”)
(39) Hydroxyl compound D: 1,3-butanediol (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “13BD”)

(Nitrile compound)
(40) Nitrile compound A: acetonitrile (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “MNCA”)
(41) Nitrile compound B: propionitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCB”)
(42) Nitrile compound C: butyronitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCC”)
(43) Nitrile compound D: pentanenitrile (manufactured by Aldrich, hereinafter referred to as “MNCD”)
(44) Nitrile compound E: Hexanenitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCE”)
(45) Nitrile compound F: heptanenitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCF”)
(46) Nitrile compound G: cyclohexanecarbonitrile (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “MNCG”)
(47) Nitrile compound H: benzonitrile (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “MNCH”)
(48) Nitrile Compound I: Octanenitrile (Wako Pure Chemical Industries, Ltd., hereinafter referred to as “MNCI”)
(49) Nitrile compound J: Nonanenitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCJ”)
(50) Nitrile compound K: decane nitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCK”)
(51) Nitrile compound L: undecane nitrile (manufactured by Aldrich, hereinafter referred to as “MNCL”)
(52) Nitrile compound M: dodecane nitrile (manufactured by Wako Pure Chemical Industries, Ltd., hereinafter referred to as “MNCM”)
(53) Nitrile compound N: tridecane nitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCN”)
(54) Nitrile compound O: Tetradecane nitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCO”. Also expressed as myristonitrile as another name)
(55) Nitrile compound P: pentadecane nitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCP”)
(56) Nitrile compound Q: heptadecane nitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCQ”)
(57) Nitrile compound R: Octadecane nitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCR”, also expressed as stearonitrile)
(58) Nitrile compound S: Nonadecane nitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCS”)
(59) Nitrile compound T: 2-phenyltetradecanenitrile (manufactured by Aldrich, hereinafter referred to as “MNCT”)
(60) Nitrile compound U: propanedinitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCU”. It is also expressed as dicyanomethane or malononitrile as another name)
(61) Nitrile compound V: butanedinitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCV”. It is also expressed as dicyanoethane or succinonitrile as another name)
(62) Nitrile Compound W: Pentanedinitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCW”. It is also expressed as dicyanopropane or glutaronitrile as another name)
(63) Nitrile compound X: dimethyldicyanomethane (manufactured by Aldrich, hereinafter referred to as “MNCX”. It is also expressed as dimethylmalononitrile as another name)
(64) Nitrile compound Y: Hexanedinitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCY”. It is also expressed as dicyanobutane or adiponitrile as another name)
(65) Nitrile compound Z: heptanedinitrile (Aldrich, hereinafter referred to as “MNCZ”, also referred to as dicyanopentane or pimelonitrile)
(66) Nitrile compound AA: Octanedinitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCAA”. It is also expressed as dicyanohexane or suberonitrile as another name)
(67) Nitrile compound AB: 1,4-cyclohexanedicarbonitrile (manufactured by Aldrich, hereinafter referred to as “MNCAB”)
(68) Nitrile compound AC: decandinitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCAC”. It is also expressed as dicyanooctane or sebacononitrile as another name)
(69) Nitrile compound AD: 2,3-diphenylbutanedinitrile (manufactured by Aldrich, hereinafter referred to as “MNCAD”. Also expressed as 2,3-diphenyldicyanoethane or 2,3-diphenylsuccinonitrile as another name) )
(70) Nitrile compound AE: 2,2,7,7-tetraphenyloctanedinitrile (manufactured by Aldrich, hereinafter referred to as “MNCAE”. As another name, 2,2,7,7-tetraphenyldicyanohexane or 2, (Also expressed as 2,7,7-tetraphenylsuberonitrile)
(71) Nitrile compound AF: 1,2,3-propanetricarbonitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCAF”)
(72) Nitrile compound AG: 1,3,5-pentanetricarbonitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCAG”)
(73) Nitrile compound AH: 1,3,5-cyclohexanetricarbonitrile (manufactured by Tokyo Chemical Industry Co., Ltd., hereinafter referred to as “MNCAH”)
(74) Nitrile compound AI: 1,1,3,3-propanetetracarbonitrile (manufactured by Aldrich, hereinafter referred to as “MNCAI”)
(75) Nitrile compound AJ: 3-methyl-3-propyl-1,1,2,2-cyclopropanetetracarbonitrile (manufactured by Aldrich, hereinafter referred to as “MNCAJ”)
(76) Nitrile compound AK: 1,1,3,3,5,5-hexacyanopentane (manufactured by Aldrich, hereinafter referred to as “MNCAK”)

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

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

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

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

(Production Example 1)
<Production of episulfide compound>
The episulfide compound was prepared according to the following procedure.
(1) Preparation: Place a water bath with a water-cooling heating unit containing water and a stirrer or an oil bath containing oil and a stirrer on a magnetic stirrer so that the temperature reaches a predetermined temperature. Set.
(2) Each raw material was placed in a flask containing a stirrer according to the composition ratio in Table 1 and mixed and stirred to obtain a uniform reaction solution in which the thiating agent was dissolved.
(3) The reaction was performed according to the reaction temperature and reaction time shown in Table 2.
(4) The reaction solution was allowed to stand until the temperature reached room temperature.
(5) Diethyl ether (Wako Pure Chemical Industries, Ltd.) and ultrapure water (Wako Pure Chemical Industries, Ltd.) and ultrapure water (Wako Pure Chemical Industries, Ltd.) were added to the reaction solution. The solution was allowed to stand until the layers were separated, and the diethyl ether layer was taken out.
(6) To the diethyl ether layer obtained in (5) above, saturated brine was added and mixed and stirred. Thereafter, stirring was stopped, and the mixture was allowed to stand until the diethyl ether layer and the saturated saline layer were separated, and only the diethyl ether layer was taken out.
(7) Anhydrous magnesium sulfate (Wako Pure Chemical Industries, Ltd.) was added to the diethyl ether layer obtained in (6) above, mixed and stirred, and the anhydrous magnesium sulfate was removed by filtration to obtain a diethyl ether layer.
(8) The low boiling point compound (including diethyl ether) contained in the diethyl ether layer obtained in (7) above was distilled off using a rotary evaporator to obtain a reaction product containing an episulfide compound.
(9) The reaction product obtained in (8) above was purified by the following method (A) or (B).
(A) The episulfide compound was purified by distillation with reference to the methods exemplified in the New Experimental Science Course (Maruzen Co., Ltd.) and the Chemical Experiment Manual (Gihodo Publishing Co., Ltd.).
(B) With reference to the method exemplified in the New Experimental Science Course (Maruzen Co., Ltd.) and the Chemical Experiment Manual (Gihodo Publishing Co., Ltd.), separation by column chromatography and distilling off the used developing solvent, The episulfide compound was purified.
In addition, as conditions for column chromatography, silica gel 60N (spherical, neutral) (manufactured by Kanto Chemical Co., Inc.) was used as a filler, and a mixed solvent in which the content of ethyl acetate was gradually increased from n-hexane as a developing solvent. Was used.
In this production example, purification was performed by the method (A).
(10) The WPT of the episulfide compound obtained in (9) above was calculated.

(Production Examples 2-34)
An episulfide compound was produced by the same method as in Production Example 1 except that the composition ratios in Table 1 and the reaction temperatures, reaction times, and purification methods in Table 2 were used.

Example 1
<Preparation of boron trihalide-nitrile 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 having 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 3, 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-nitrile compound (hereinafter referred to as “BF3-MNCA”).
<Preparation and polymerization of composition>
(5) Preparations were made in the same procedure as (1) above.
(6) A reaction vessel in a nitrogen atmosphere was placed in the water bath of (5) above, and each raw material was added to the reaction vessel according to the composition ratio in Table 6 and stirred to prepare a composition.
(7) The composition prepared in the above (6) was polymerized according to the polymerization conditions shown in Table 9 to obtain a polymer.

(Examples 2-89)
Except having set it as the composition ratio of Tables 3-11, and superposition | polymerization conditions, the composition was prepared by the method similar to Example 1, and the polymer was obtained.
In Examples 40 to 46, 58 to 61, and 68 to 72, samples for polymerization evaluation and side reactivity evaluation were prepared in a sealed pressure bottle for evaluation.
The evaluation results of the compositions prepared in Examples 1 to 89 are shown in Tables 9, 10, and 11.

(Comparative Examples 1-56)
According to the compositions of Tables 12 and 13, the compositions of Comparative Examples 1 to 56 were prepared in the same manner as in Example 1, and polymers were obtained according to the polymerization conditions of Tables 14 and 15. In Comparative Examples 23 to 29, 41 to 44, and 51 to 55, samples for polymerization evaluation and side reactivity evaluation were prepared in sealed pressure bottles for evaluation. The evaluation results of the compositions prepared in Comparative Examples 1 to 56 are shown in Tables 14 and 15.

  As shown in Tables 3 to 15, the composition containing (A) a nitrile compound, (B) boron trihalide, and (C) an episulfide compound according to this embodiment is stable and polymerizable. It was confirmed that the polymer was obtained by polymerizing the composition with little side reaction when polymerizing the composition. On the other hand, a composition containing one compound selected from an ether compound having one ether group, a sulfide compound, an alcohol compound, an acidic compound, and a nitrogen-containing compound, boron trihalide, and an episulfide compound; According to a comparative example using a known thermal polymerization accelerator used when polymerizing a compound, none satisfying all of the evaluations of stability, polymerizability and side reactivity were confirmed.

(Example 90)
<Preparation of glass substrate coated with polymer>
(1) The polymer obtained in Example 82 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.

<Transparency maintenance evaluation 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 88%.
(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 83%, it was judged to be good.
(8) The transparency maintenance ratio (hereinafter referred to as “dTLT”) was calculated using the following formula.
dTLT (%) = TLT300 / TLT0 × 100
(9) When the transparency maintenance ratio is 90% or more, it is judged as good (“A”), when it is 95% or more, it is judged as particularly good (“AA”). "C"). In this example, the transparency maintenance ratio was 94%, so it was judged 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 this case, it was determined to pass (("AA" or "A") as a comprehensive judgment. In all other cases, it was determined to be rejected ("C").
In this example, TLT300 was 83% and good ("A"), dTLT was 94% and good ("A"), and both evaluations were good. It was judged as good (“A”).

(Examples 91-94)
A glass substrate coated with the polymer was evaluated in the same manner as in Example 90 except that the polymer obtained in the examples shown in Table 16 was used.

  As shown in Table 16, a polymer obtained by polymerizing a composition containing (A) a nitrile compound, (B) boron trihalide, and (C) an episulfide compound according to this embodiment is It was confirmed that the change in transparency was small even after long-term storage.

(Example 95)
<Preparation of boron trihalide-nitrile compound (BF3-MNCV-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) Place the reaction vessel in a nitrogen atmosphere in the water bath of (1) above, add 15% by mass of butanedinitrile, 54% by mass of boron trifluoride diethyl ether complex, and 31% by mass of dichloromethane to the reaction vessel. Stir for 1 hour.
(3) A vacuum distillation apparatus was attached to the reaction vessel, and the pressure was gradually reduced. Finally, the pressure was reduced to 2 kPa and maintained for 4 hours.
(4) Using the product obtained in (3) above, it was confirmed that a complex was formed by performing an analysis by ¹¹ B-NMR.

<Preparation and polymerization of composition>
(5) Preparations were made in the same procedure as (1) above.
(6) A reaction vessel in a nitrogen atmosphere was placed in the water bath of (5) above, and was added to the reaction vessel according to the composition ratio in Table 17 and stirred to prepare a composition.
(7) The composition prepared in the above (6) was polymerized according to the polymerization conditions shown in Table 21 to obtain a polymer.
The mixing index γ was calculated by the following formula (11).
Index γ = αd / αt × 100 (11)
here,
αd: (D) amount of chain transfer agent (mol)
αt: (C) The amount (mol) of the episulfide group contained in the episulfide compound, respectively.
(8) The episulfide group reaction rate of the polymer obtained in the above (7) was measured by the method shown in Table 21, and it was confirmed that the episulfide group in the original episulfide compound was polymerized.

<Evaluation of heat resistance stability of polymer (hereinafter referred to as “RA method”): When the episulfide compound which is the base of the polymer has one episulfide group>
(9) Obtained in the above (7) in a vacuum dryer (VOS-451D, manufactured by Tokyo Rika Kikai Co., Ltd., and ULVAC Kiko Co., Ltd., small oil rotary vacuum pump GCD-201X was used as the vacuum pump). 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 chamber temperature was 180 ° C. and held for 1000 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.

<Evaluation of heat stability of polymer (hereinafter referred to as “RB method”): When the episulfide compound which is the base of the polymer has two or more episulfide groups>
It was performed in the same manner as the RA method except that the temperature in the thermostatic chamber was 250 ° C.

(Examples 96 to 247)
Polymers were obtained in the same manner as in Example 95 except that the composition ratios in Tables 17 to 20 and the polymerization conditions in Tables 21 to 24 were used. The evaluation results of the polymers obtained in Examples 95 to 247 are shown in Tables 21 to 24.
In Examples 125 to 131, 138 to 152, 159 to 173, and 180 to 187, the polymer was prepared in a sealed pressure bottle.

  As shown in Tables 17 to 24, the composition containing (A) a nitrile compound, (B) boron trihalide, (C) an episulfide compound, and (D) a chain transfer agent according to this embodiment. It was confirmed that the polymer and cured product obtained by polymerization had a low volatile content even when kept at a high temperature for a long period of time, and had a high stability at a high temperature.

  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 anti-corrosion coating, maintenance equipment, woodwork product lacquer, automotive electrodeposition primer, other industrial electrodeposition coatings, beverage / beer can inner surface lacquer, coil Coating, inner surface of drums and cans, acid-resistant lining, wire enamel, insulation paint, automotive primer, exterior and anticorrosion coating of various metal products, pipe interior and exterior coating, electrical parts insulation coating, etc.), composite materials (chemical plant pipes)・ Tanks, aircraft materials, automobile parts, various sporting goods, carbon fiber composite materials, aramid fiber composite materials, etc.), civil engineering and building materials (floor materials, paving materials, membranes, anti-slip / thin layer pavements, concrete joints, bulks Raising, anchor embedding, precast concrete bonding, tile bonding, 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 (10)

A composition containing (A) a nitrile compound, (B) boron trihalide, and (C) an episulfide compound ,
At least a part of the (A) nitrile compound and the (B) boron trihalide forms a complex,
The index α representing the ratio of the (A) nitrile compound and the (B) boron trihalide represented by the following formula (2) is 1-1000,
Index α = αn / αb (2)
αn: Substance amount of nitrile group of the nitrile compound (mol)
αb: amount of the boron trihalide (mol)
The composition whose ratio of the substance amount (mol) of the said boron trihalide and the substance amount (mol) of the episulfide group contained in the said episulfide compound is 1: 10-1: 100000 . The composition according to claim 1, wherein the nitrile compound is a compound represented by the following formula (1).

[Wherein, a represents a number of 1 or more, and R ₁ represents a chain, branched or cyclic aliphatic hydrocarbon group having _{1 to} 33 carbon atoms, or a substituted or unsubstituted aromatic hydrocarbon group. . ]   The composition according to claim 1 or 2, wherein the nitrile compound has 2 to 32 carbon atoms.   The composition according to claim 1, wherein the nitrile compound has 1 to 8 nitrile groups. The composition according to any one of claims 1 to 4 , wherein the 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 5 , wherein the episulfide compound is a compound having only a 3-membered ring thioether structure as a polymerizable functional group. The composition according to any one of claims 1 to 6 , wherein an episulfide equivalent of the episulfide compound is 65 to 700 g / mol. The composition according to any one of claims 1 to 7 , wherein the episulfide compound has a partial structure represented by the following formula (3), (4), (5) or (6).

[Wherein R ₂₀ , R ₂₁ , R ₂₂ , R ₂₃ , R ₂₄ , R ₂₅ , R ₂₆ , R ₂₇ , R ₂₈ , R ₂₉ , R ₃₀ , R ₃₁ , R ₃₂ , R ₃₃ and R ₃₄ 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. ] Polymerizing the episulfide compound in the composition according to any one of claims 1-8, a method of manufacturing a polymer. A method for producing a polymer, wherein the episulfide compound in the composition according to any one of claims 1 to 8 is polymerized by heating and / or energy beam irradiation.