JPH0717955A - Benzotriazole derivative - Google Patents

Abstract

PURPOSE:To obtain the novel compound derivative consisting of a specific benzotriazole derivative containing 1,2,4-triazole group and t-amino group in the molecule and extremely useful as a rust-proofing agent for copper. CONSTITUTION:This benzotriazole derivative expressed by the formula IV and useful as a rust-proofing agent for copper can be produced by charging a 1-H benzotriazole expressed by the formula I (R1 is H or CH3), 1,2,4-triazole expressed by the formula II and a primary amine expressed by the formula III (R2 is alkyl, hydroxyalkyl or cycloalkyl) (e.g. 2-ethylhexylamine) in a reactor, adding methanol and formaldehyde to the mixture, reacting at 50-60 deg.C for 4hr and distilling out methanol under a slightly reduced pressure.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to novel benzotriazole derivatives. The benzotriazole derivative according to the present invention is useful as an anticorrosive agent for copper.

[0002]

BACKGROUND OF THE INVENTION The present inventors have previously found and proposed that a specific benzotriazole derivative is useful as an anticorrosive agent for metals (JP-A-2-117668, JP-A-2-117683 and JP-A-2-117683). Kaihei 2-207077).
As a result of subsequent studies, the present inventors have found that a benzotriazole derivative having a unique structure different from that of the above derivative is extremely useful as a rust preventive for copper, and have completed the present invention. .

[0003]

The present invention therefore seeks to provide new benzotriazole derivatives which are particularly useful as rust inhibitors for copper.

[0004]

In order to solve the above problems, the present invention provides a novel benzotriazole derivative represented by the following general formula.

[0005]

[Chemical 2]

[In the formula, R ₁ represents H or —CH ₃ ,
R ₂ represents alkyl, hydroxyalkyl or cycloalkyl. In the benzotriazole derivative of the present invention, alkyl and hydroxyalkyl as R ₂ are preferably those having 1 to 18 carbon atoms, and cycloalkyl is one having 5 to 8 carbon atoms. Is preferred.

In producing the benzotriazole derivative of the present invention, for example, a benzotriazole represented by the following general formula (1), a primary amine represented by the general formula (2) and a general formula (3) are represented. 1,2,4-triazole with formalin in a suitable solvent
The reaction is carried out by stirring at 40 to 70 ° C. under normal pressure for 3 to 4 hours. However, the temperature and time are not limited to the above. Paraform may be used instead of formalin. After completion of the reaction, the solvent is removed under reduced pressure to obtain the desired product. As a solvent,
Although not particularly limited, polar solvents such as alcohol and acetone are preferably used.

[0008]

[Chemical 3]

[0009]

[Chemical 4]

[0010]

[Chemical 5]

In the above formulas (1) and (2), R ₁
And R ₂ have the same meaning as defined above.

[0012]

EXAMPLES The present invention will be further described below with reference to examples. Example 1 In a 500 ml four-necked flask equipped with a stirrer, a thermometer and a reflux condenser, 200 g of methanol, 40.0 g of 1-H benzotriazole (0.336 M) and 23.2 g of 1,2,4-triazole ( 0.336M), 4-ethylhexylamine 43.5g (0.337M) and formalin 20.2g (0.673M) were charged, and 50-60 ° C.
The reaction is continued for 4 hours. Then, the methanol is distilled off under a light reduced pressure to obtain 113 g of a yellow viscous compound of the following formula. The yield was 99%.

[0013]

[Chemical 6]

The results of elemental analysis of this compound are shown below. Element name Measured value (%) Calculated value (%) Carbon 63.6 63.34 Nitrogen 28.2 28.74 Hydrogen 7.1 7.1 7.92 Each element was in good agreement with the calculated value.

Example 2 In a 500 ml four-necked flask equipped with a stirrer, a thermometer and a reflux condenser, 200 g of methanol, 44.7 g of tolyltriazole (0.336 M) and 23.2 g of 1,2,4-triazole ( 0.336M), 4-ethylhexylamine 43.5g (0.337M) and formalin 2
Charge 0.2 g (0.673 M) and continue the reaction at 50-60 ° C. for 4 hours. Then, methanol was distilled off under a light reduced pressure to obtain a pale yellow viscous compound 1 of the following formula.
18 g are obtained. The yield was 99%.

[0016]

[Chemical 7]

The results of elemental analysis of this compound are shown below. Element name Measured value (%) Calculated value (%) Carbon 64.9 64.23 Nitrogen 27.1 27.60 Hydrogen 7.9 8.17 Each element was in good agreement with the calculated value.

Example 3 In a 500 ml four-necked flask equipped with a stirrer, a thermometer and a reflux condenser, 200 g of acetone, 40.0 g of 1-H benzotriazole (0.336 M) and 1,2,4-triazole 23 were added. .2g (0.336M), monoethanolamine 20.9g (0.337M) and paraform 2
Charge 0.2 g (0.673 M) and continue the reaction at 50-60 ° C. for 4 hours. Then, acetone was distilled off under a light reduced pressure to obtain a yellow viscous compound of the following formula: 92 g
To get The yield was 100%.

[0019]

[Chemical 8]

The results of elemental analysis of this compound are shown below. Element Name Measured value (%) Calculated value (%) Carbon 52.8 52.55 Nitrogen 35.1 35.77 Hydrogen 5.5 5.5 5.84 Oxygen 5.7 5.84 Calculated values for each element Well matched.

Example 4 In a 500 ml four-necked flask equipped with a stirrer, a thermometer and a reflux condenser, 200 g of acetone and 4 tolyltriazole were added.
0.0g (0.336M), 1,2,4-triazole 23.2g (0.336M), monoethanolamine 2
0.9g (0.337M) and paraform 20.20
g (0.673M) and charged at 50-60 ° C for 4
Continue to react for hours. Then, the acetone is distilled off under a light reduced pressure to obtain 96 g of a yellow viscous compound of the following formula. The yield was 99%.

[0022]

[Chemical 9]

The results of elemental analysis of this compound are shown below. Element name Measured value (%) Calculated value (%) Carbon 54.5 54.16 Nitrogen 33.8 34.03 Hydrogen 6.4 6.25 Oxygen 5.1 5.56 Well matched.

Example 5 In a 500 ml four-necked flask equipped with a stirrer, a thermometer and a reflux condenser, 200 g of methanol, 40.0 g of 1-H benzotriazole (0.336 M) and 1,2,4-triazole 23 were added. .2g (0.336M), cyclohexylamine 33.4g (0.337M) and formalin 2
Charge 0.2 g (0.673 M) and continue the reaction at 50-60 ° C. for 4 hours. Then, methanol was distilled off under a light reduced pressure to obtain a yellow viscous compound of the following formula 10
3 g are obtained. The yield was 99%.

[0025]

[Chemical 10]

The results of elemental analysis of this compound are shown below. Element name Measured value (%) Calculated value (%) Carbon 62.0 61.74 Nitrogen 31.2 31.51 Hydrogen 6.8 6.75 Each element was in good agreement with the calculated value.

Anticorrosion Test for Copper (1) JIS-K2513 An anticorrosion test was conducted on the above compounds by the corrosion test method for copper plates of petroleum products. Conditions: 100 ° C./3 hours Mixing: Base oil (Monsanto base oil) 98 parts Corrosion accelerator (DAILUBU S285) 2 parts (manufactured by Dainippon Ink and Chemicals, Inc.) Rust inhibitor: Compound of Examples 1, 2 and 5 0.1 part The obtained results are shown below.

Antirust Agent ASTM Copper Plate Corrosion Standard Blank 4b Compounds of Example 1 1a-1b Compounds of Example 1 1a-1b Compounds of Example 5 1a-1b Compounds of Examples 1, 2 and 5 All showed good rustproofing effect on copper.

(2) 0.1 g of the compound of Example 3 or 4 was dissolved in 200 ml of 5% saline, a copper wire was immersed in this solution, and the mixture was left in an incubator at 50 ° C. The results obtained are shown below. Anti-corrosive agent 1 hour, 2 days, 4 days later Blank ▲ ★★ Compound of Example 3 ◎ ◎ ○ Compound of Example 4 ◎ ◎ ○ ★: Surface changed to brown, green rust occurred and the solution It becomes opaque.

▲: The entire surface changes to light brown. ◯: Spot rust occurs on part of the surface. A: Almost no change is observed on the surface. Both the compound of Example 3 and the compound of 4 showed a good rust preventive effect on copper.

[0031]

INDUSTRIAL APPLICABILITY According to the present invention, a novel benzotriazole derivative which is extremely useful as an anticorrosive agent for copper is provided.

Claims (1)

[Claims] 1. A benzotriazole derivative represented by the following general formula. [Chemical 1] [In the formula, R ₁ represents H or —CH ₃ , and R ₂ represents alkyl, hydroxyalkyl or cycloalkyl. ]