Triazine compounds and methods for producing the same

Abstract

Provided is a triazine compound represented by formula (1). [In the formula, each of R1-R3 is independently a hydrogen atom, an alkyl group, or a group represented by formula (2) or formula (3), and at least one thereof is a group represented by formula (3). (In the formulae: each R4 is independently a hydrogen atom or a C1-C7 alkyl group; R5 is a C1-C12 alkyl group; and n is an integer of 1-5.)]

Description

[Technical Field]

[0001] The present invention relates to triazine compounds and methods for producing the same. [Background technology]

[0002] Conventionally, triazine compounds having an unsaturated group at the terminal end are known to be represented by the following formula (A) (Patent Document 1). However, no triazine compounds having an unsaturated bond at the terminal end via a glycol-derived substituent are known. [ka] [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] International Publication No. 01 / 062821 [Overview of the Initiative] [Problems that the invention aims to solve]

[0004] This invention has been made in view of the above circumstances, and aims to provide a novel triazine compound having an unsaturated bond at its terminus. [Means for solving the problem]

[0005] The inventors, after diligent research to achieve the above objective, arrived at the following formula (4): [ka] [In the formula, R 11 ~R 13 Each of these is independently a hydrogen atom, an alkyl group, or a group represented by the following formula (2), but at least one of them is a group represented by the following formula (2). [ka] (In the formula, R 4 is each independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms. R 5 is an alkyl group having 1 to 12 carbon atoms. )] It has been found that a triazine compound represented by the following formula (5)

Chemical formula

[0006] That is, the present invention provides the following triazine compound and a method for producing the same. 1. A triazine compound represented by the following formula (1).

Chemical formula

Chemical formula

[0007] According to the present invention, a triazine compound having an unsaturated bond at its terminus can be produced. Such a triazine compound is expected to be used as an ultraviolet absorber. Furthermore, by reacting the unsaturated bond at the terminus and incorporating it into a polymer, a high molecular weight type ultraviolet absorber can be produced, which is expected to improve chemical resistance and heat resistance, making it particularly useful in the manufacture of semiconductor devices. [Modes for carrying out the invention]

[0008] The triazine compound having an unsaturated bond at its terminus in the present invention is represented by the following formula (1). [ka]

[0009] In formula (1), R 1 ~R 3 Each of these is independently a hydrogen atom, an alkyl group, a group represented by formula (2) below, or a group represented by formula (3) below, but at least one of them is a group represented by formula (3) below. [ka]

[0010] In equations (2) and (3), R 4 Each of these is independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms. 5 n is an alkyl group having 1 to 12 carbon atoms. n is an integer from 1 to 5.

[0011] R 1 ~R 3 Examples of alkyl groups represented by include C1 to C12 alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, and dodecyl group. The alkyl group is preferably a methyl group, ethyl group, or propyl group.

[0012] R4 Examples of alkyl groups having 1 to 7 carbon atoms represented by R include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, tert-butyl, pentyl, neopentyl, hexyl, and heptyl groups. Of these, R 4 A hydrogen atom or a methyl group is preferred as the element.

[0013] R 5 Examples of alkyl groups having 1 to 12 carbon atoms represented by R include methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, dodecyl group, etc. Of these, R 5 The preferred group is a methyl group, ethyl group, propyl group, or 2-ethylhexyl group.

[0014] In equation (3), n is an integer between 1 and 5, but is preferably an integer between 2 and 4, and more preferably 2 or 3.

[0015] R 1 ~R 3 Preferably, all of these are groups represented by formula (3).

[0016] Specific examples of compounds represented by formula (1) are listed below, but are not limited to these. [ka]

[0017] [ka]

[0018] [ka]

[0019] The compound represented by formula (1) is given by the following formula (4) [ka] [In the formula, R 11 ~R 13 Each of these is independently a hydrogen atom, an alkyl group, or a group represented by the following formula (2), but at least one of them is a group represented by the following formula (2). [ka] (In the formula, R 4 and R 5 (This is the same as above.) A triazine compound represented by the following formula (5) [ka] (In the formula, n is an integer between 1 and 5.) It is obtained by reacting an allyl ether compound represented by [formula].

[0020] R 11 ~R 13 Examples of alkyl groups represented by include C1 to C12 alkyl groups such as methyl group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, tert-butyl group, pentyl group, neopentyl group, hexyl group, heptyl group, octyl group, 2-ethylhexyl group, nonyl group, decyl group, and dodecyl group. The alkyl group is preferably a methyl group, ethyl group, or propyl group.

[0021] Specific examples of compounds represented by formula (4) are listed below, but are not limited to these. [ka]

[0022] [ka]

[0023] Specific examples of allyl ether compounds represented by formula (5) are listed below, but are not limited to these. [ka]

[0024] The amount of allyl ether compound represented by formula (5) used is preferably 20 to 100 moles, and more preferably 30 to 70 moles, per mole of the compound represented by formula (4).

[0025] In the above reaction, an allyl ether compound can be used as the reaction solvent by adding a large excess of it. However, other solvents may also be used as optional, in which case a solvent compatible with the compound represented by formula (4) and the allyl ether compound represented by formula (5) is preferred. Specific examples of such solvents include ethers such as diethyl ether, tetrahydrofuran, and dioxane; aromatic hydrocarbons such as benzene, toluene, and xylene; and halogenated hydrocarbons such as dichloroethane, chloroform, and chlorobenzene.

[0026] An acid catalyst may be used in the above reaction. Examples of the acid catalyst include nitric acid, hydrochloric acid, sulfuric acid, and fuming sulfuric acid. The amount of the acid catalyst used is preferably 0.1 to 1.0 equivalents, and more preferably 0.1 to 0.2 equivalents, per mole of the compound represented by formula (4).

[0027] In the above reaction, the reaction temperature is not particularly limited, but is usually 40 to 200°C, preferably 90 to 170°C, and the reaction time is about 2 to 30 hours, preferably 4 to 6 hours.

[0028] The triazine compound of the present invention can be obtained by washing the reaction product with water and then removing the solvent, etc. Specifically, it is preferable to remove the acid catalyst, etc., by washing with water after the reaction is complete, and then distill off any excess allyl ether compound, solvent, etc., under reduced pressure and heating to obtain the triazine compound of the present invention.

[0029] The triazine compound of the present invention can be used as an ultraviolet absorber and is also effective in the manufacture of semiconductor devices. [Examples]

[0030] The present invention will be specifically described below with reference to examples, but the present invention is not limited to the following examples. 1 H-NMR spectral analysis was performed using a Bruker 400MHz analyzer.

[0031] [Example 1] A 1 L separable flask equipped with a nitrogen gas inlet tube, thermometer, and Liebig condenser contains the following formula (6): [ka] 98 g (0.1 mol) of the compound represented by [formula] was added and dissolved in 378 g (3.7 mol) of allyl glycol, and 1.00 g (0.010 mol) of sulfuric acid was gradually added. The mixture was then heated to 160°C and reacted for 5 hours. After the reaction was complete, 500 g of toluene and 1000 g of pure water were added, and the mixture was separated into an organic layer and an aqueous layer. The allyl glycol and toluene in the organic layer were then removed by distillation under reduced pressure at 160°C to obtain 81 g of a reddish-brown, highly viscous liquid. 1 ¹H-NMR spectral analysis confirmed that the compound is a triazine compound with an unsaturated bond at its terminus, as shown in formula (7) below. 1 The results of the 1H-NMR are shown in Table 1. [ka]

[0032] [Table 1]

[0033] [ka]

[0034] [Example 2] A 1 L separable flask equipped with a nitrogen gas inlet tube, thermometer, and Liebig condenser contains the following formula (8): [ka] 75 g (0.1 mol) of the compound represented by [formula] was added and dissolved in 378 g (3.7 mol) of allyl glycol, and 1.00 g (0.010 mol) of sulfuric acid was gradually added. The mixture was then heated to 160°C and reacted for 5 hours. After the reaction was complete, 500 g of toluene and 1000 g of pure water were added, and the mixture was separated into an organic layer and an aqueous layer. The allyl glycol and toluene in the organic layer were then removed by distillation under reduced pressure at 160°C to obtain 82 g of a reddish-brown, highly viscous liquid. The resulting compound... 1 ¹H-NMR spectral analysis confirmed that the compound is a triazine compound with an unsaturated bond at the terminal end, as shown in formula (9) below. [ka]

[0035] [Example 3] A 1 L separable flask equipped with a nitrogen gas inlet tube, thermometer, and Liebig condenser contains the following formula (10): [ka] 66 g (0.1 mol) of the compound represented by [formula] was added and dissolved in 378 g (3.7 mol) of allyl glycol, and 1.00 g (0.010 mol) of sulfuric acid was gradually added. The mixture was then heated to 160°C and reacted for 5 hours. After the reaction was complete, 500 g of toluene and 1000 g of pure water were added, and the mixture was separated into an organic layer and an aqueous layer. The allyl glycol and toluene in the organic layer were then removed by distillation under reduced pressure at 160°C to obtain 72 g of a reddish-brown, highly viscous liquid. 1 ¹H-NMR spectral analysis confirmed that the compound is a triazine compound with an unsaturated bond at its terminus, as shown in formula (11) below. [ka]

Claims

1. A triazine compound represented by the following formula (1). 【Chemistry 1】 [In the formula, R 1 ~R 3 Each of these is independently a hydrogen atom, an alkyl group, a group represented by formula (2) below, or a group represented by formula (3) below, but at least one of them is a group represented by formula (3) below. 【Chemistry 2】 (In the formula, R 4 Each of these is independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms. 5 n is an alkyl group having 1 to 12 carbon atoms. n is an integer from 1 to 5.

2. R 4 The triazine compound according to claim 1, wherein each is independently a hydrogen atom or a methyl group.

3. R 5 The triazine compound according to claim 1, wherein the triazine compound is a methyl group, an ethyl group, a propyl group, or a 2-ethylhexyl group.

4. The triazine compound according to any one of claims 1 to 3, wherein n is 2 or 3.

5. A method for producing a triazine compound represented by the following formula (1), comprising the step of reacting a triazine compound represented by the following formula (4) with an allyl ether compound represented by the following formula (5). 【Transformation 3】 [In the formula, R 11 ~R 13 Each of these is independently a hydrogen atom, an alkyl group, or a group represented by the following formula (2), but at least one of them is a group represented by the following formula (2). 【Chemistry 4】 (wherein, R 4 is a hydrogen atom or an alkyl group having 1 to 7 carbon atoms. R 5 is an alkyl group having 1 to 12 carbon atoms.) ] 【Transformation 5】 (In the formula, n is an integer between 1 and 5.) 【Transformation 6】 [In the formula, R 1 ~R 3 Each of these is independently a hydrogen atom, an alkyl group, a group represented by formula (2) below, or a group represented by formula (3) below, but at least one of them is a group represented by formula (3) below. 【Transformation 7】 (In the formula, R 4 Each of these is independently a hydrogen atom or an alkyl group having 1 to 7 carbon atoms. 5 n is an alkyl group having 1 to 12 carbon atoms. n is an integer from 1 to 5.

Images