JPH0967383A - New thiabendazole fluorosilane derivative, its production and surface treating agent using the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce a new thiabendazole fluorosilane derivative useful as a surface treating agent for a metal, a high molecular and an inorganic materials, etc., especially a treating agent, etc., for copper foils used in copper- clad laminates for printed circuits by reacting a thiabendazole fluorine derivative with isocyanatosilanes. SOLUTION: This new thiabendazole fluorosilane derivative of formula I [R<1> is a group of formula II [R<3> is F or trifluoromethyl; (n) is an integer of 1-15}; R<2> is a group of formula III [R<4> and R<5> are each a 1-4C alkyl; (m) is an integer of 0-34]. The derivative is useful as a surface treating agent in order to carry out rust preventing, lubricating, water and oil repellent and antimicrobial treatments, etc., of surfaces of a metal, a polymeric and an inorganic materials, etc., especially a treating agent, etc., for copper foils used in copper clad laminates, etc., for printed circuits. The compound is obtained by reacting a thiabendazole fluorine derivative of formula IV with an isocyanatosilane compound of formula V.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a surface treatment agent for rust prevention, lubrication, water repellency, oil repellency, antibacterial property, etc. of metal, polymer material, inorganic material, etc. The present invention relates to a novel benzimidazole fluorosilane derivative suitable as a treatment agent for copper foil used for laminated plates and the like, a method for producing the same, and uses thereof.

[0002]

2. Description of the Related Art A copper clad laminate for printed circuits is formed by laminating a paper foil resin impregnated base material or a glass-epoxy resin impregnated base material on a copper foil by heating and pressing, and etching this. A board for electronic equipment is made by forming a circuit network and mounting an element such as a semiconductor device on the circuit network.
In these processes, adhesion with the base material, heating, immersion in acid or alkaline solution, application of resist ink, soldering, etc. are performed, so that the copper foil has adhesiveness, heat resistance, moisture resistance, chemical resistance, etc. Performance is required. Furthermore, it is also required that the copper foil does not undergo oxidative discoloration during storage. In order to meet these requirements, a copper layer has a brass layer forming treatment (JP-B-51-35711).
No. 54-6701), chromate treatment, coating of zinc-chromium group mixture consisting of zinc or zinc oxide and chromium oxide (Japanese Patent Publication No. 58-7077), and silane cups. A method of applying a ring agent to improve the adhesiveness between the copper foil and the resin substrate has also been proposed (Japanese Patent Publication No. 2-19994, JP-A-63-18).
3178, and JP-A-2-26097).

[0003]

However, since the printed circuit has been densified recently, the characteristics required for the copper foil such as the printed circuit used have become more severe.
In view of the present situation, the present invention forms a film with excellent adhesiveness on the surface of various metals such as copper, organic materials such as polymer materials, and inorganic materials such as ceramics, and remarkably repels the surface. It is an object to provide a novel compound effective as an excellent surface treatment agent capable of imparting water-based property, oil repellency, lubricity, anticorrosive property and antibacterial property, and to provide a surface treatment agent using the same. It is a thing.

[0004]

As a result of intensive studies, the present inventors have found that the above-mentioned problems can be solved by a specific group of thiabendazole derivatives containing fluorine, and have completed the present invention. That is, the present invention provides (i) a novel thiabendazole fluorosilane derivative represented by the following general formula (1).

[0005]

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[In the formula, R ¹ represents a group represented by the following general formula (2), R ³ in the following general formula (2) represents a fluorine or trifluoromethyl group, and n is an integer of 1 to 15] Is. Further, in the formula, R ² represents a group represented by the following general formula (3), and R ⁴ and R ⁵ in the following general formula (3) have 1 to 4 carbon atoms.
Is an alkyl group, and m is an integer of 0 to 3. ]

[0007]

[Chemical 6]

(Ii) The method for producing a thiabendazole fluorine silane derivative described in (i) above, wherein a thiabendazole fluorine derivative represented by the following general formula (4) is reacted with an isocyanate silane compound represented by the following general formula (5).

[0009]

[Chemical 7]

(In the formula, R ₁ represents a group represented by the following general formula (2), R ₃ in the following general formula (2) represents a fluorine or trifluoromethyl group, and n represents an integer of 1 to 15). It is.)

[0011]

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(In the formula, R ⁴ and R ⁵ represent an alkyl group having 1 to 4 carbon atoms, and m is an integer of 0 to 3.) (iii) In the general formula (1) described in (i) above. The gist of the present invention is a surface treatment agent comprising at least one of the represented thiabendazole fluorosilane derivatives as an active ingredient. In the general formula (2), n is an integer of 1 to 15, preferably 5 to 12, and particularly preferably 7 to 9. Water repellency when n is 0,
If it does not exhibit oil repellency and n exceeds 15, the solubility in a solvent decreases. Particularly preferable examples of the novel thiabendazole fluorine derivative represented by the general formula (1) of the present invention are shown below.

[0013]

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[0014]

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The thiabendazole fluorine silane derivative represented by the general formula (1) of the present invention comprises 40 to 10 of the thiabendazole fluorine derivative represented by the general formula (4) and the isocyanate silane compound represented by the general formula (5).
It can be easily produced by reacting at 0 ° C.

[0016]

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(Each symbol is the same as the above) The general formula (4)
Examples of the compound represented by

[0018]

[Chemical 12]

And the like are preferred. In the isocyanate silane compound represented by the general formula (5), R ⁴ and R ⁵
Represents an alkyl group having 1 to 4 carbon atoms, that is, methyl, ethyl, n-propyl, i-propyl, n-butyl, isobutyl, t-butyl. Particularly preferred as the isocyanate silane compound,

[0020]

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[0021] The reaction between the thiabendazole fluorine derivative represented by the general formula (4) and the isocyanate silane compound is performed by using ethyl acetate or the like as a reaction solvent, and 1 to 2 mol of the isocyanate silane is used per 1 mol of the thiabendazole fluorine derivative of the general formula (4). It is preferred to react the compounds. The reaction time is about 30 minutes to 100 hours. It is preferable to use a catalyst for this reaction so that the reaction can be accelerated. Examples of such a catalyst include dibutyltin dilaurate and the like. In addition, the thiabendazole fluorine derivative represented by the general formula (4) is a compound represented by the following general formula (6) as disclosed in the specification filed by the present inventors on the same date as the present application (reference number: KD070616A6). ) And a 1,2-epoxypropane compound represented by
It can be easily produced by reacting at ˜150 ° C.

[0022]

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(In the formula, R ¹ is the same as above) Examples of the 1,2-epoxypropane compound represented by the general formula (6) include 3-perfluorooctyl-1,2-epoxypropane and 3-perfluoro. Nonyl-1,2-epoxypropane, 3-perfluorodecyl-1,2-epoxypropane, 3- (perfluoro-8-methylnonyl)-
1,2-epoxypropane, 3- (perfluoro-9-
Methyldecyl) -1,2-epoxypropane, 3- (perfluoro-10-methylundecyl) -1,2-epoxypropane and the like are preferable. The reaction between the thiabendazole and the 1,2-epoxypropane compound is carried out by adding 0.1-1.0 mol of the 1,2-epoxypropane compound to benzimidazole using dimethylformamide, dimethylacetamide or the like as a reaction solvent. The reaction time is about 1 to 100 hours, and the reaction temperature is about 100 to 150 ° C.

The thiabendazole fluorosilane derivative of the present invention is suitable as a surface treatment agent for metals. The film of the thiabendazole fluorosilane derivative of the present invention formed on a metal surface exhibits remarkable Teflon-grade water repellency and oil repellency as described below, and can significantly improve the rust preventive property of the metal surface. it can. In addition, the surface treatment agent of the present invention is not limited to a metal surface, and even when it is applied to various base materials such as ceramics, polymer materials and other organic materials and inorganic materials, the base material similarly has water repellency and repellent properties. It is possible to impart oiliness, lubricity and antibacterial properties. Further, by adding it to a synthetic resin such as an epoxy resin, water repellency, oil repellency, lubricity and antibacterial property can be imparted to the resin as well.
The case where the surface treating agent of the present invention is used as a metal surface treating agent will be further described, and the target metal is not particularly limited. For example, it is effective as a surface treatment agent for copper, aluminum, iron and alloys thereof. However, it is more preferable to use it as a surface treatment agent for copper and copper alloys, and particularly to sufficiently exhibit the effect of the present invention when used as a surface treatment agent for copper foil used in a copper clad laminate for printed circuits. can do. The copper foil includes a copper foil whose surface is roughened, a copper foil which is subjected to a brass layer formation treatment, a chromate treatment, a zinc-chromium group mixture coating treatment, and the like.

In the surface treatment agent of the present invention, at least one of the above thiabendazole fluorosilane derivatives is diluted with an alcohol such as methanol or ethanol or a solvent such as ethyl acetate to a concentration of 0.001 to 20% by weight. It is convenient and preferable to apply the method by dipping a metal in the liquid. If less than 0.001% by weight, the desired water repellency
Oil repellency and the like cannot be obtained, and when it exceeds 20% by weight, the effect is almost saturated, which is not preferable from an economical point of view. The thiabendazole fluorosilane derivative may be used alone, or may be mixed with another rust preventive agent, a coupling agent, or the like.

[0026]

BEST MODE FOR CARRYING OUT THE INVENTION

Example 1 Synthesis of thiabendazole fluorine derivative (thiabendazole and 3-perfluorodecyl-1,2
-Synthesis of a compound represented by the following formula (4-1) from the reaction with epoxypropane)

[0027]

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Thiabendazole 60.9 g (0.3 mo
1) is heated and dissolved in 600 ml of dimethylformamide, and 1
Heated to 45 ° C. From the dropping funnel, 3-perfluorodecyl-1,2-epoxypropane 34.56g
(0.06 mol) dissolved in 160 ml of heated dimethylformamide was added over 30 minutes. After the dropping was completed, the reaction was continued for another 100 hours. The reaction mixture became a dark brown solution. Then, the mixture was cooled to room temperature, and the precipitate was filtered with a glass filter and washed with hot dimethylformamide several times for purification. The obtained purified product was dried at 85 ° C. in a vacuum dryer. Yield 15.08g
(Yield 32.3%), and the thiabendazole fluorine derivative represented by the above formula (4-1) was obtained as a white powder. [For the identification data of this compound, see No .: KD070616A6) Example 1].

Thiabendazole Fluorosilane derivative (1
-1) (represented by the following formula (1-1) from the reaction of the thiabendazole fluorine derivative represented by the following formula (4-1) and 3-isocyanatopropyltriethoxysilane represented by the following formula (5-1) Synthesis of compounds

[0030]

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3.23 g (4.16 × 10 ^-3 mo) of the thiabendazole fluorine derivative represented by the above formula (4-1)
l) and 2.04 g (8.32 ×) of 3-isocyanatepropyltriethoxysilane represented by the above formula (5-1).
10 ⁻³ mol) was dissolved in 200 ml of ethyl acetate. Several drops of dibutyltin dilaurate as a reaction catalyst were added to this solution, and the reaction was carried out at a reaction temperature of 70 ° C. for 4 hours. Completion of the reaction was confirmed by high performance liquid chromatography when the peak of the thiabendazole fluorine derivative as a reaction raw material was not detected, and a thiabendazole fluorine silane derivative of the above formula (1-1) was obtained. The FT-
IR is shown. As shown in FIG. 1, the following signals were observed. νCH: 2820 to 3015 (cm ⁻¹ ) νC = O: 1660 to 1770 νCF: 1100 to 1300 νSiOC: 1020 to 1100 Example 2 Electrolytic copper foil (4.5 × 4.5 cm, thickness 70 μm) was mixed with acetone to 5 μm. It was ultrasonically cleaned for 1 minute, then washed with water, and immersed in a 3% aqueous solution of sulfuric acid for 1 minute for pickling. Then, it was washed with water and acetone in that order and dried with a dryer. Using a solution of the reaction mixture containing the thiabendazole fluorosilane derivative of the present invention obtained in Example 1 on the glossy surface of this electrolytic copper foil, 5
It was spin-coated at 00 RPM. After that, it is dried at 100 ° C. for 30 minutes and its surface wettability is measured by CA manufactured by Kyowa Interface Science.
It was evaluated by a -D type contact angle measuring device. Table 1 shows the evaluation results.

[0032]

[Table 1]

* Reference value N. L. Jarvis and W.D. A. Zisma
n; Encyclopedia of Chemica
l Technology vol. 9,707L. S.
Penn and E. R. Bowler; Surfa
ce and Interface Analysis, vo
l. 3, No. 4,161 (1981) Examples 3, 4, 5, 6 Stainless steel plate (Example 3), Steel plate (Example 4), Aluminum (Example 5) and Slide glass (Example 6)
Was ultrasonically cleaned with acetone for 5 minutes and then with water. These substrates were spin-coated at 500 RPM using the surface treatment agent solution containing the reaction mixture containing the thiabendazole fluorosilane derivative of the present invention obtained in Example 1. Then, it was dried at 100 ° C. for 30 minutes and its surface wettability was evaluated by a Kyowa Interface Science CA-D type contact angle measuring device. Table 2 shows the evaluation results.

[0034]

[Table 2]

Comparative Examples 1 to 6 Electrolytic copper foil used in Examples (after degreasing and pickling Comparative Example 1), carbon steel (Comparative Example 2), SUS304 (Comparative Example 3), aluminum (Comparative Example 4) The surface wettability was evaluated in the same manner as in Example except that the surface treatment agent of the present invention was not used using a slide glass (Comparative Example 5) and a Teflon plate (Comparative Example 6). The results are shown in Table 3.

[0036]

[Table 3]

By comparing Examples 2 to 6 with the above Comparative Example, it can be seen that the thiabendazole fluorosilane derivative of the present invention exhibits remarkable water repellency and oil repellency. Example 7 Electrolytic copper foil, carbon steel, SUS304, aluminum, and slide glass were spin-coated at 500 RPM using the surface treatment agent solution obtained from the reaction mixture containing the thiabendazole fluorosilane derivative of the present invention obtained in Example 1. . Then, it was dried at 100 ° C. for 30 minutes and immersed in boiling water for 1 hour, and the surface wettability was evaluated by a Kyowa Interface Science CA-D type contact angle measuring device. Table 4 shows the evaluation results.

[0038]

[Table 4]

Almost no decrease in water repellency was observed in any of the substrates, which shows that the surface-treated coating of the present invention has extremely high durability. Example 8 Synthesis of thiabendazole fluorine silane derivative (1-2) (from reaction of thiabendazole fluorine derivative represented by the following formula (4-2) with 3-isocyanatopropyltriethoxysilane represented by the following formula (5-1) Synthesis of compound represented by formula (1-2))

[0040]

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1.41 g (2.08 × 10 ^-3 mo) of the thiabendazole fluorine derivative represented by the above formula (4-2)
l) and 3-isocyanatopropyltriethoxysilane represented by the above formula (5-1) 4.08 g (16.64)
(× 10 ⁻³ mol) was dissolved in 100 ml of ethyl acetate.
Several drops of dibutyltin dilaurate were added to this solution as a reaction catalyst, and the reaction was carried out at a reaction time of 67 ° C. for 54 hours. Completion of the reaction was confirmed by high performance liquid chromatography when the peak of the thiabendazole fluorine derivative as a reaction raw material was not detected, and a thiabendazole fluorine silane derivative of the above formula (1-2) was obtained. The F in Figure 2
T-IR is shown. As shown in FIG. 2, the following signals were recognized. νCH: 2820 to 3015 (cm ⁻¹ ) νC = O: 1660 to 1770 νCF: 1100 to 1300 νSiOC: 1020 to 1100 Example 9 Electrodeposited copper foil (4.5 × 4.5 cm, thickness 70 μm) with acetone 5 It was ultrasonically cleaned for 1 minute, then washed with water, and immersed in a 3% aqueous solution of sulfuric acid for 1 minute for pickling. Then, it was washed with water and acetone in that order and dried with a dryer. Using a solution comprising the reaction mixture containing the thiabendazole fluorosilane derivative of the present invention obtained in Example 8 on the glossy surface of this electrolytic copper foil, 5
It was spin-coated at 00 RPM. After that, it is dried at 100 ° C. for 30 minutes and its surface wettability is measured by CA manufactured by Kyowa Interface Science.
It was evaluated by a -D type contact angle measuring device. Table 5 shows the evaluation results.

[0042]

[Table 5]

* Reference value N. L. Jarvis and W.D. A. Zisma
n; Encyclopedia of Chemica
l Technology vol. 9,707 L.S. S. Penn and E. R. Bowler; S
urface and Interface Analysis
sis, vol. 3, No. 4,161 (1981) Examples 10, 11, 12, 13 Stainless steel plate (Example 10), steel plate (Example 11), aluminum (Example 12) and slide glass (Example 13) were replaced with acetone. Ultrasonic cleaning for 5 minutes and then water washing. These substrates were spin-coated at 500 RPM using the surface treating agent solution consisting of the reaction mixture containing the thiabendazole fluorosilane derivative of the present invention obtained in Example 8. Then, it was dried at 100 ° C. for 30 minutes and its surface wettability was evaluated by a Kyowa Interface Science CA-D type contact angle measuring device. The evaluation results are shown in Table 6.

[0044]

[Table 6]

Example 14 An electrolytic copper foil (4.5 × 4.5 cm, thickness 70 μm) was ultrasonically cleaned with acetone for 5 minutes, then washed with water, and immersed in a 3% sulfuric acid aqueous solution for 1 minute for pickling. Then, it was washed with water and acetone in that order and dried with a dryer. A glossy surface of this electrolytic copper foil was spin coated at 500 RPM using a surface treating agent comprising a reaction mixture containing the thiabendazole fluorosilane derivative of the present invention obtained in Examples 1 and 8.
Drying was performed at 100 ° C. for 30 minutes. Moisture resistance is relative humidity 9
The sample was treated for 24 hours in a thermo-hygrostat at 5% and a temperature of 80 ° C., and the change in surface color tone before and after the test was visually evaluated. An untreated copper foil was used for comparison. The evaluation results are shown in Table 7.

[0046]

[Table 7]

Example 15 An electrolytic copper foil (4.5 × 4.5 cm, thickness 70 μm) was ultrasonically cleaned with acetone for 5 minutes, then washed with water, and immersed in a 3% sulfuric acid aqueous solution for 1 minute for pickling. Then, it was washed with water and acetone in that order and dried with a dryer. A glossy surface of this electrolytic copper foil was spin coated at 500 RPM using a surface treating agent comprising a reaction mixture containing the thiabendazole fluorosilane derivative of the present invention obtained in Examples 1 and 8.
Then, it was dried at 100 ° C. for 30 minutes, and its adhesion was evaluated by wiping the surface with a bencot manufactured by Asahi Chemical. The results using the contact angle of water as an index for evaluation are shown below.

[0048]

[Table 8]

Example 16 A stainless steel plate (5.5 × 5.5 cm, thickness 2 mm) was ultrasonically cleaned with acetone for 5 minutes, then with acetone and dried with a dryer. This stainless steel plate was spin-coated at 500 RPM using a surface treatment agent comprising a reaction mixture containing the thiabendazole fluorosilane derivative of the present invention obtained in Examples 1 and 8. Then 100
It was dried at 30 ° C. for 30 minutes, and its adhesion was evaluated by wiping the surface with Ascott's Bemcot. The contact angle of water was used as an index for evaluation. The results are shown in Table 9.

[0050]

[Table 9]

Example 17 A rolled copper plate (5.5 × 5.5 cm, thickness 2 mm) was degreased with acetone, and the surface was soft-etched with a hydrogen peroxide solution / sulfuric acid aqueous solution. Example 1 and Example 8 were applied to this rolled copper plate.
Using the surface treatment agent solution comprising the reaction mixture containing the thiabendazole fluorosilane derivative of the present invention obtained in 5
It was spin-coated at 00 RPM. Then, it was dried at 100 ° C. for 30 minutes, and its tribological characteristics were evaluated by a Bowden-Leben tester. The experimental conditions are shown below. Ball test piece: Steel ball for φ3.96 rolling bearing Sliding speed: 0.23 mm / s Stroke: 4.5 mm Vertical load: 400 g Temperature: Room temperature The evaluation results are shown in FIG. From FIG. 3, when the surface treating agent containing the thiabendazole fluorine silane derivative of the present invention is used, the initial friction coefficient is smaller than that of the untreated one, and the one represented by the derivative (1-2) is contained. It can be seen that, even when the reciprocating motion is 1000 times, there is almost no increase in the friction coefficient, and good lubricating durability is exhibited.

Example 18 The antibacterial properties of the thiabendazole fluorosilane derivative of the present invention obtained in Example 1 were evaluated as follows. (1) Test strain Trichoderma harzianum Cladosporium resinae Asperigillus terreus Penicillium funiculosum (2) Preparation of test bacterial solution PDA slant medium (DIFCO), 25
After subculturing 3 times at 7 ° C for 7 days each, sterilized physiological saline 1
0 ml was added and filtered. The obtained bacterial solution was treated with 10 ⁵ cf.
It was adjusted to u / ml and used for the test.

(3) Medium used Sterile PG medium (Eiken E-MF08) was dispensed into 9 ml of sterile test tubes for use. (4) Antibacterial agent (thiabendazole fluorosilane derivative)
Concentration 100, 50, 25 (μg / ml) Note) A 0.2 wt% methanol solution was adjusted to a predetermined concentration using sterile water. (5) Antibacterial property test 1 ml of the drug test solution at each concentration step was placed in a test tube containing a PG medium, inoculated with 10 μl of the test bacteria, cultured at 25 ° C. for 14 days, and then judged by the growth of the bacteria. (6) Results Table 10 shows the results. The minimum inhibitory concentration (MIC) of the thiabendazole fluorosilane derivative is T. har
100 μg / ml against Zianum, C.I. r
For esinae, a slight growth inhibitory effect was observed at 100 μg / ml. It had no effect on the other two strains.

[0054]

[Table 10]

Example 19 Synthesis of thiabendazole fluorine silane derivative (1-3) [Thiabendazole fluorine derivative represented by the following formula (4-3) and 3-isocyanatepropyltriethoxysilane represented by the following formula (5-1) Of the compound represented by the following formula (1-3) from the reaction of

[0056]

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1.72 g (2.08 × 10 ^-3 mo) of the thiabendazole fluorine derivative represented by the above formula (4-3)
l) and 3-isocyanatopropyltriethoxysilane represented by the above formula (5-1) 1.02 g (4.16 ×)
10 ⁻³ mol) was dissolved in 100 ml of ethyl acetate. Several drops of dibutyltin dilaurate were added to this solution as a reaction catalyst, and the reaction was carried out at a reaction temperature of 67 ° C. for 30 hours. Completion of the reaction was confirmed by high performance liquid chromatography when the peak of the thiabendazole fluorine derivative as a reaction raw material was not detected, and a thiabendazole fluorine derivative of the above formula (1-3) was obtained. Figure 4 shows the FT-IR
Is shown. As shown in FIG. 4, the following signals were recognized. νCH: 2820 to 3010 (cm ⁻¹ ) νC = O: 1650 to 1780 νCF: 1100 to 1340 νSiOC: 1000 to 1100

[0058]

As described above, the novel thiabendazole fluorinated silane derivative of the present invention imparts remarkable water repellency, oil repellency and antibacterial property to the surface of metal etc.
Lubricity and antibacterial property can be improved.

[Brief description of drawings]

FIG. 1 is an FT-IR spectrum of a thiabendazole fluorosilane derivative of the present invention [formula (1-1)],

FIG. 2 is an FT-IR spectrum of a thiabendazole fluorosilane derivative of the present invention [formula (1-2)],

FIG. 3 Evaluation of lubricity of a surface treatment agent containing a thiabendazole fluorosilane derivative of the present invention,

FIG. 4 is an FT-IR spectrum of the thiabendazole fluorosilane derivative of the present invention [formula (1-3)].

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI Technical indication C10M 105/76 C10M 105/76 C23C 22/00 C23C 22/00 Z

Claims (3)

[Claims] 1. A novel thiabendazole fluorosilane derivative represented by the following general formula (1). Embedded image [In the formula, R ¹ represents a group represented by the following general formula (2), R ³ in the following general formula (2) represents a fluorine or trifluoromethyl group, and n is an integer of 1 to 15. Further, in the formula, R ² represents a group represented by the following general formula (3), R ⁴ and R ⁵ in the following general formula (3) represent an alkyl group having 1 to 4 carbon atoms, and m represents 0 to 3 Is an integer. ] [Chemical 2] 2. The thiabendazole fluorine silane derivative according to claim 1, wherein a thiabendazole fluorine derivative represented by the following general formula (4) is reacted with an isocyanate silane compound represented by the following general formula (5). Production method. Embedded image (In the formula, R ¹ represents a group represented by the following general formula (2), R ³ in the following general formula (2) represents a fluorine or trifluoromethyl group, and n is an integer of 1 to 15. ) [Chemical 4] (In the formula, R ⁴ and R ⁵ represent an alkyl group having 1 to 4 carbon atoms,
m is an integer of 0 to 3. ) 3. A surface treating agent comprising at least one of the thiabendazole fluorosilane derivative represented by the general formula (1) according to claim 1 as an active ingredient.