Organosilicon compound, surface treatment agent, and resin additive

Abstract

An organosilicon compound represented by formula (1) has excellent heat resistance and excellent adhesiveness to a metal surface, and can impart corrosion resistance to the metal surface. (In the formula, each of R1 independently represents a hydrogen atom, a C1-10 alkyl group, or a C6-10 aryl group; each of R2 independently represents a C1-10 alkyl group or a C1-10 aryl group; X represents a monovalent group having a nitrogen-containing heterocycle; m is an integer of 6-10; and n is an integer of 1-3.)

Description

Organosilicon compounds, surface treatment agents and resin additives

[0001] The present invention relates to an organosilicon compound, a surface treatment agent, and a resin additive.

[0002] BACKGROUND ART For the purpose of preventing metal rust, development of chromium-free (non-chromate) metal surface treatment agents has been promoted as an alternative to chromium-based surface treatment agents such as toxic chromate and chromate phosphate.

[0003] Patent Documents 1 and 2 propose the use of imidazole ring-containing organosilicon compounds and benzotriazole ring-containing organosilicon compounds as surface treatment agents for metals and the like, but the corrosion resistance, adhesion, etc., of these compounds are insufficient.

[0004] Furthermore, Patent Document 3 discloses a metal surface treatment agent containing a silane coupling agent having a benzotriazole ring and a urea bond. The benzotriazole ring and the urea bond form a coordinate bond to form a sparingly soluble complex, thereby exhibiting rust prevention properties, and the hydrolyzable silyl group provides excellent processing adhesion. However, there is room for improvement in heat resistance, corrosion resistance, and adhesiveness.

[0005] JP 2000-297093 A JP 6-279463 A JP 2016-79130 A

[0006] The present invention has been made in view of the above circumstances, and an object of the present invention is to provide an organosilicon compound that has excellent heat resistance and adhesion to metal surfaces and can impart corrosion resistance to metal surfaces, as well as a surface treatment agent and a resin additive that contain this organosilicon compound.

[0007] As a result of extensive research to achieve the above object, the present inventors have discovered that a specific organosilicon compound has excellent heat resistance and adhesion to metal surfaces and can impart corrosion resistance to metal surfaces, thereby completing the present invention.

[0008] That is, the present invention provides: 1. an organosilicon compound represented by the following formula (1): (In the formula, R 1each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms; R 2 each independently represents an alkyl group having 1 to 10 carbon atoms or an aryl group having 1 to 10 carbon atoms, X represents a monovalent group having a nitrogen-containing heterocycle, m is an integer of 6 to 10, and n is an integer of 1 to 3. 2. An organosilicon compound of 1, wherein X is a group selected from the following formulas (2) to (6): (In the formula, R 3 each independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 10 carbon atoms, and the wavy line portion represents a bond to an adjacent atom.) 3. The organosilicon compound of 1 wherein m is 8; 4. A surface treatment agent containing any of the organosilicon compounds of 1 to 3; 5. A resin additive containing any of the organosilicon compounds of 1 to 3; 6. An article surface-treated with any of the organosilicon compounds of 1 to 3.

[0009] The organosilicon compound of the present invention has a structure in which a nitrogen-containing heterocycle is bonded to a silicon atom via a long-chain alkylene, and therefore exhibits good rust-preventing performance due to the formation of coordinate bonds on the metal surface and hydrophobization, and also has excellent adhesiveness and heat resistance.The organosilicon compound of the present invention, which has such characteristics, does not contain chromium and can therefore be suitably used as a surface treatment agent for various materials, such as a surface treatment agent for metals, or as a resin additive.

[0010] The present invention will be described in detail below. [Organosilicon Compound] The organosilicon compound of the present invention is represented by the following formula (1).

[0011]

[0012] In formula (1), R 1 R each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms. 1The alkyl group having 1 to 10 carbon atoms, preferably 1 to 8 carbon atoms, and more preferably 1 to 6 carbon atoms may be linear, branched, or cyclic, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, n-hexyl, and cyclohexyl groups. Specific examples of the aryl group having 6 to 10 carbon atoms, preferably 6 to 8 carbon atoms, include phenyl and tolyl groups. Among these, R 1 is preferably a hydrogen atom, a methyl group, or an ethyl group, and more preferably a hydrogen atom.

[0013] R 2 each independently represents an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, and the alkyl group having 1 to 10 carbon atoms and the aryl group having 6 to 10 carbon atoms are each represented by R 1 Among these, a methyl group is preferred.

[0014] X represents a monovalent group having a nitrogen-containing heterocycle, which may be a heteroaromatic ring or a partially or fully saturated heterocycle, and may have either a monocyclic structure or a polycyclic structure (including a spirocyclic structure). The nitrogen-containing heterocycle may further contain an oxygen atom and / or a sulfur atom in the ring. Specific examples of the nitrogen-containing heteroaromatic ring include pyrrole, maleimide, imidazole, pyrazole, pyrazolone, triazole, tetrazole, pyridine, pyridone, pyrazine, pyrimidine, pyridazine, triazine, tetrazine, azepine, diazepine, oxazole, isoxazole, thiazole, thiazolinone, isothiazole, isothiazolinone, furazan, oxadiazole, oxazine, oxadiazine, oxazepine, oxadiazepine, thiadiazole, thiazine, thiazepine, thiadiazepine, indole, isoindole, indolizine, indazole, pyrindine, quinoline, isoquinoline, quinolizine, purine, phthalazine, pteridine, naphthyridine, quinoxaline, quinazoline, cinnoline, benzoxazole, benzothiazole, benzimidazole, benzofurazan, benzothiadiazole, and benzotriazole rings.

[0015] Specific examples of partially or fully saturated nitrogen-containing heterocycles include pyrroline, pyrrolidone, pyrrolidine, pyrrolizidine, succinimide, imidazoline, imidazolidine, imidazolidone, triazoline, triazolidine, tetrazoline, tetrazolidine, pyrazoline, pyrazolidine, pyrazolidone, dihydropyridine, tetrahydropyridine, piperidine, piperidone, dihydropyrazine, tetrahydropyrazine, piperazine, dihydropyrimidine, tetrahydropyrimidine, perhydropyrimidine, dihydropyridazine, tetrahydropyridazine, and paclitaxel. -hydropyridazine, triazinane, triazinanetrione (isocyanuric acid), dihydroazepine, tetrahydroazepine, perhydroazepine, dihydrodiazepine, tetrahydrodiazepine, perhydrodiazepine, dihydrooxazole, tetrahydrooxazole (oxazolidine), dihydroisoxazole, tetrahydroisoxazole (isoxazolidine), dihydrothiazole (thiazoline), tetrahydrothiazole (thiazolidine), thiazolidinone, dihydroisothiazole (isothiazoline), tetrahydroisothiazoline dihydrooxazepine, tetrahydrooxazepine, perhydrooxazepine, dihydrooxadiazepine, tetrahydrooxadiazepine, perhydrooxadiazepine, dihydrooxadiazepine, dihydrothiadiazole, tetrahydrothiadiazole (thiadiazolidine), dihydrothiazolidine Azine, tetrahydrothiazine, dihydrothiadiazine, tetrahydrothiazepine, tetrahydrothiazepine, perhydrothiazepine, dihydrothiadiazepine, tetrahydrothiadiazepine, perhydrothiadiazepine, morpholine, thiomorpholine, indoline, isoindoline, dihydroindazole, perhydroindazole, dihydroquinoline, tetrahydroquinoline, perhydroquinoline, dihydroisoquinoline, tetrahydroisoquinoline, perhydroisoquinoline, dihydrophthalazine, tetrahydrophthalazine,Examples of such an alkyl group include perhydrophthalazine, dihydronaphthyridine, tetrahydronaphthyridine, perhydronaphthyridine, dihydroquinoxaline, tetrahydroquinoxaline, perhydroquinoxaline, dihydroquinazoline, tetrahydroquinazoline, perhydroquinazoline, dihydrocinnoline, tetrahydrocinnoline, perhydrocinnoline, dihydrobenzoxazine, dihydrobenzothiazine, pyrazinomorpholine, dihydrobenzoxazole, perhydrobenzoxazole, dihydrobenzothiazole, perhydrobenzothiazole, dihydrobenzimidazole, and a perhydrobenzimidazole ring.

[0016] Specific examples of spiro-bonded bicyclic nitrogen-containing heterocycles and bridged bicyclic nitrogen-containing heterocycles include azaspiro[4.4]nonane, oxazaspiro[4.4]nonane, azaspiro[4.5]decane, oxazaspiro[4.5]decane, azabicyclo[2.2.1]heptane, azabicyclo[3.1.1]heptane, azabicyclo[3.2.1]octane, azabicyclo[2.2.2]octane, and azabicyclo[2.2.2]octane rings.

[0017] Among these, nitrogen-containing heteroaromatic rings containing neither oxygen nor sulfur atoms are preferred, and imidazole, benzimidazole, triazole (1,2,3-triazole or 1,2,4-triazole), and benzotriazole rings are more preferred.

[0018] That is, the above X is preferably a group selected from the following formulas (2) to (6).

[0019] (In the formula, the wavy lines represent bonds to adjacent atoms.)

[0020] In the formula, R 3 R each independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 10 carbon atoms. 3The alkyl group having 1 to 12 carbon atoms may be linear, branched, or cyclic, and specific examples thereof include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl, n-pentyl, n-hexyl, cyclohexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, etc. Specific examples of the aryl group having 6 to 10 carbon atoms include phenyl, tolyl, xylyl, etc.

[0021] Specific examples of X are shown below, but are not limited to these.

[0022] (In the formula, the wavy lines represent bonds to adjacent atoms.)

[0023] m represents an integer of 6 to 10, preferably an integer of 8 to 10, and more preferably 8. If m is less than 6, heat resistance and rust prevention properties may be insufficient, and if m exceeds 10, the content of heterocycles per unit mass may decrease, resulting in decreased rust prevention properties and adhesiveness. n represents an integer of 1 to 3, preferably 2 or 3 from the viewpoint of adhesiveness.

[0024] The organosilicon compound represented by the above formula (1) can be obtained, for example, by reacting (A) an organosilicon compound containing a halogenated alkyl group (hereinafter referred to as compound (A)) with (B) a nitrogen-containing heterocyclic compound (hereinafter referred to as compound (B)) in air or in an inert gas atmosphere such as nitrogen.

[0025] Specific examples of compound (A) include 6-chlorohexyltrimethoxysilane, 6-chlorohexyltriethoxysilane, 6-bromohexyltrimethoxysilane, 6-bromohexyltriethoxysilane, 8-chlorooctyltrimethoxysilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyldimethoxymethylsilane, 8-chlorooctyldiethoxymethylsilane, 8-bromooctyltrimethoxysilane, 8-bromooctyltriethoxysilane, 8-bromooctyldimethoxymethylsilane, 8-bromooctyldiethoxymethylsilane, 10-chlorodecyltrimethoxysilane, 10-chlorodecyltriethoxysilane, 10-bromodecyltrimethoxysilane, 10-bromodecyltriethoxysilane, etc. These may be used alone or in combination of two or more.

[0026] Among these, 8-chlorooctyltrimethoxysilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyldimethoxymethylsilane, 8-chlorooctyldiethoxymethylsilane, 10-chlorodecyltrimethoxysilane, and 10-chlorodecyltriethoxysilane are preferred, and 8-chlorooctyltrimethoxysilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyldimethoxymethylsilane, and 8-chlorooctyldiethoxymethylsilane are more preferred.

[0027] Specific examples of compound (B) include imidazole, 1-methylimidazole, 2-methylimidazole, 4-methylimidazole, 4(5)-ethylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, 2-isopropylimidazole, 2-propylimidazole, 2-butylimidazole, 4-phenylimidazole, 2-phenylimidazole, 2-undecylimidazole, 4-methyl-2-phenylimidazole, 1,2,4-triazole, 1,2,3-triazole, 5,6-dimethylbenzimidazole, 2-ethyl-1H-benzimidazole, 2-methylbenzimidazole, 5-methylbenzimidazole, 2-nonylbenzimidazole, 2-phenylbenzimidazole, benzimidazole, benzotriazole, 5,6-dimethylazimidobenzene, and 5-methylbenzotriazole. These may be used alone or in combination of two or more. Among these, imidazole and benzimidazole are preferred.

[0028] The reaction may be carried out in a solvent as needed, as long as the reaction is not inhibited. Examples of the solvent include aliphatic hydrocarbon solvents such as pentane, hexane, heptane, and decane; ether solvents such as tetrahydrofuran and 1,4-dioxane; amide solvents such as formamide, dimethylformamide, and N-methylpyrrolidone; and aromatic hydrocarbon solvents such as benzene, toluene, and xylene.

[0029] The above reaction is an exothermic reaction, and side reactions may occur if the temperature becomes too high. Therefore, the reaction temperature during production is preferably 20 to 150°C, more preferably 30 to 130°C, and even more preferably 40 to 110°C. The reaction time for the above reaction is not particularly limited as long as it allows temperature control of the above-mentioned exothermic reaction and is a time that allows the exothermic reaction to be completed, but is preferably 10 minutes to 24 hours, and more preferably 1 to 10 hours.

[0030] [Surface Treatment Agent] The surface treatment agent of the present invention contains an organosilicon compound represented by the above formula (1) and is particularly suitable for use as a metal surface treatment agent. From the viewpoint of stability, the organosilicon compound represented by the above formula (1) is contained in a concentration of preferably 0.001 to 20% by mass, and more preferably 0.005 to 10% by mass, of the surface treatment agent of the present invention.

[0031] The surface treatment agent of the present invention may further contain an organosilicon compound other than the organosilicon compound represented by the above formula (1). Examples of the other organosilicon compounds include amino group-containing organosilicon compounds, epoxy group-containing organosilicon compounds, and isocyanuric acid structure-containing organosilicon compounds. Among these, amino group-containing organosilicon compounds are preferred.

[0032] The amino group-containing organosilicon compound may be a compound having at least one amino group selected from the group consisting of a primary amino group, a secondary amino group, and a tertiary amino group, and an alkoxysilyl group. Specific examples thereof include 3-aminopropyltrimethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldiethoxysilane, 8-aminooctyltrimethoxysilane, 8-aminooctyldimethoxysilane, 8-aminooctyltriethoxysilane, 8-aminooctylmethyldiethoxysilane, N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, N-(β-aminoethyl)-γ-aminopropyltrimethoxysilane, N-(β-aminoethyl)-γ-aminopropyltriethoxy ... Examples thereof include N-(β-aminoethyl)-γ-aminopropylmethyldimethoxysilane, N-(β-aminoethyl)-γ-aminopropyltriethoxysilane, N-(β-aminoethyl)-γ-aminopropylmethyldiethoxysilane, N-(β-aminoethyl)-γ-aminooctyltrimethoxysilane, N-(β-aminoethyl)-γ-aminooctylmethyldimethoxysilane, N-(β-aminoethyl)-γ-aminooctyltriethoxysilane, N-(β-aminoethyl)-γ-aminopropylmethyldiethoxysilane, N-phenyl-3-aminopropyltrimethoxysilane, and N-phenyl-3-aminopropylmethyldimethoxysilane.

[0033] Specific examples of epoxy group-containing organosilicon compounds include 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropylmethyldimethoxysilane, 3-glycidoxypropyltriethoxysilane, 3-glycidoxypropylmethyldiethoxysilane, 2-(3,4-epoxycyclohexyl)ethyltrimethoxysilane, etc. Specific examples of isocyanuric acid structure-containing organosilicon compounds include tris(trimethoxysilylpropyl)isocyanurate.

[0034] When other organosilicon compounds are used, the ratio of the organosilicon compound represented by the above formula (1) to the other organosilicon compounds is not particularly limited, but from the viewpoints of storage stability and productivity, the amount of the other organosilicon compound relative to 1 mole of the organosilicon compound represented by the above formula (1) is preferably 0.1 to 100 moles, more preferably 0.5 to 20 moles, and even more preferably 1 to 10 moles.

[0035] The surface treatment agent of the present invention may further contain water, an organic solvent, or both as a solvent. From the viewpoint of the stability of the composition, it is preferable to use water adjusted to an acidic state. Examples of acids used to adjust the acidic state include organic acids such as formic acid, acetic acid, and citric acid; and inorganic acids such as hydrochloric acid. When an acid is used, the amount added is preferably 0.001 to 0.5 mass %, more preferably 0.01 to 0.2 mass %, of the total surface treatment agent. When an acid is used, water adjusted to an acidic state by mixing the acid and water in advance may be used, or the acid may be added to a surface treatment agent containing water to adjust the acidic state.

[0036] The organic solvent is not particularly limited, but examples thereof include methanol, ethanol, isopropanol, n-butanol, diacetone alcohol, ethylene glycol, ethyl cellosolve, butyl cellosolve, propylene glycol monomethyl ether, propylene glycol monomethyl ether acetate, N,N-dimethylformamide, dimethylacetamide, N-methyl-2-pyrrolidone, methyl ethyl ketone, and methyl isobutyl ketone, and these may be used alone or in combination of two or more.

[0037] [Resin Additives] The organosilicon compound represented by formula (1) can be added to various resins either alone or as a composition containing the organosilicon compound and the solvent described above to impart adhesion and rust prevention to metal surfaces. Examples of resins include silicone resin, vinyl chloride resin, acrylic resin, phenolic resin, epoxy resin, polycarbonate resin, and polybutylene terephthalate resin. The amount of the organosilicon compound represented by formula (1) is preferably 0.001 to 20% by mass, more preferably 0.005 to 10% by mass, based on the resin.

[0038] EXAMPLES The present invention will be explained in more detail below by showing examples and comparative examples, but the present invention is not limited to these examples.

[0039] [1] Synthesis of Organosilicon Compound [Example 1-1] 102.12 g (1.5 mol) of imidazole and 500 g of dimethylformamide were placed in a 1 L separable flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer, and 81.03 g (1.5 mol) of sodium methoxide was added while stirring at 10 ° C., and the mixture was heated to 120 ° C. 403.28 g (1.5 mol) of 8-chlorooctyltrimethoxysilane was added dropwise thereto, and the mixture was stirred at 120 ° C. for 3 hours. Thereafter, the reaction was terminated by confirming that the peak of the raw material imidazole had completely disappeared by gas chromatography (GC). Thereafter, distillation was performed to obtain a pale yellow liquid organosilicon compound represented by the following formula (7):

[0040]

[0041] Example 1-2 The same procedure as in Example 1-1 was carried out, except that the imidazole in Example 1-1 was changed to 333.57 g (1.5 mol) of 2-undecylimidazole, to obtain a pale yellow liquid organosilicon compound represented by the following formula (8).

[0042]

[0043] Example 1-3 The same procedure as in Example 1-1 was carried out, except that the imidazole in Example 1-1 was changed to 103.61 g (1.5 mol) of 1,2,4-triazole, to obtain a pale yellow liquid organosilicon compound represented by the following formula (9).

[0044]

[0045] Example 1-4 The same procedure as in Example 1-1 was carried out, except that the imidazole in Example 1-1 was changed to 177.21 g (1.5 mol) of benzimidazole, to obtain a colorless, transparent liquid organosilicon compound represented by the following formula (10).

[0046]

[0047] Example 1-5 The same procedure as in Example 1-1 was carried out, except that the imidazole in Example 1-1 was changed to 178.70 g (1.5 mol) of benzotriazole, to obtain a pale yellow liquid organosilicon compound represented by the following formula (11).

[0048]

[0049] Comparative Example 1-1 The same procedure as in Example 1-1 was carried out, except that 8-chlorooctyltrimethoxysilane was replaced with 298.08 g (1.5 mol) of 3-chloropropyltrimethoxysilane, to obtain a pale yellow liquid organosilicon compound represented by the following formula (12).

[0050]

[0051] Comparative Example 1-2 The same procedure as in Example 1-1 was carried out, except that the imidazole in Example 1-1 was changed to 177.21 g (1.5 mol) of benzimidazole and the 8-chlorooctyltrimethoxysilane was changed to 298.08 g (1.5 mol) of 3-chloropropyltrimethoxysilane, to obtain a pale yellow liquid organosilicon compound represented by the following formula (13).

[0052]

[0053] [2] Production of Surface Treatment Agents [Examples 2-1 to 2-5, Comparative Examples 2-1 and 2-2] To a mixed solvent of 89.5 g of propylene glycol monomethyl ether and 9.5 g of a 0.1% by mass aqueous acetic acid solution was added 1 g of each of the organosilicon compounds (7) to (13) obtained in Examples 1-1 to 1-5 and Comparative Examples 1-1 and 1-2, and the mixture was stirred at room temperature for 60 minutes to obtain surface treatment agents.

[0054] [3] Production of Treated Articles A commercially available copper plate (manufactured by KDS Corporation; 70 mm × 150 mm × 1 mm) was pretreated by immersing it in a 30% by mass HSO aqueous solution for 30 seconds and then drying. The pretreated copper plate was then immersed for 5 minutes in the surface treatment agents obtained in Examples 2-1 to 2-5 and Comparative Examples 2-1 and 2-2 above, and then dried at room temperature for 60 minutes to obtain a test plate. The heat resistance and corrosion resistance of the obtained test plate were evaluated according to the following evaluation methods. The results are shown in Table 1.

[0055] (1) Evaluation of heat resistance After heat treatment of the test plates in an oven at 150°C for 30 minutes, the appearance was visually evaluated as follows: ○: No discoloration ×: Discoloration (2) Evaluation of corrosion resistance The obtained test plates were subjected to a salt spray test based on JIS Z 2371:2015 for 50 hours and 100 hours, after which the corroded area was measured and the corrosion resistance was evaluated according to the following method: A: Corroded area is 0% B: Corroded area is more than 0% but less than 30% C: Corroded area is 30% or more but less than 50% D: Corroded area is 50% or more but less than 70% E: Corroded area is 70% or more

[0056]

[0057] As shown in Table 1, the test plates of Examples 2-1 to 2-5 are superior in heat resistance and rust prevention (corrosion resistance) to those of Comparative Examples 2-1 and 2-2.

[0058] [4] Production of Resin Compositions [Examples 3-1 to 3-5, Comparative Examples 3-1 and 3-2] Resin compositions were prepared by adding 0.5% by mass of each of the organosilicon compounds (7) to (13) obtained in Examples 1-1 to 1-5 and Comparative Examples 1-1 and 1-2 to a silicone resin (KR-251 manufactured by Shin-Etsu Chemical Co., Ltd.).

[0059] The adhesive properties of the resulting resin compositions were evaluated using the following method. The results are shown in Table 2. (3) Evaluation of Adhesion A commercially available copper plate (manufactured by KDS Corporation; 70 × 150 × 1 mm) was pretreated by immersing it in a 30% by mass H2SO4 aqueous solution for 30 seconds and then drying. The resin compositions obtained in Examples 3-1 to 3-5 and Comparative Examples 3-1 and 3-2 were applied to the pretreated copper plate using a bar coater 5 and dried at 25°C for 60 minutes to obtain test plates with coating films formed on the copper plate. The resulting test plates were immersed in boiling water at 100°C for 1 hour and then subjected to a 25-grid cross-cut test in accordance with JIS K5600-5-6:1999. The presence or absence of peeling of the coating film was evaluated using the following three-point scale: ⊚: No peeling was observed. ◯: Partial peeling was observed. ×: Complete peeling was observed.

[0060]

[0061] As shown in Table 2, it can be seen that the coating films made of the resin compositions of Examples 3-1 to 3-5 have superior adhesion compared to those of Comparative Examples 3-1 and 3-2.

Claims

1. An organosilicon compound represented by the following formula (1): (In the formula, R 1 each independently represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an aryl group having 6 to 10 carbon atoms; R 2 each independently represents an alkyl group having 1 to 10 carbon atoms or an aryl group having 1 to 10 carbon atoms, X represents a monovalent group having a nitrogen-containing heterocycle, m is an integer of 6 to 10, and n is an integer of 1 to 3.

2. The organosilicon compound according to claim 1, wherein X is a group selected from the following formulas (2) to (6): (In the formula, R 3 each independently represents a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or an aryl group having 6 to 10 carbon atoms, and the wavy line represents a bond to an adjacent atom.

3. The organosilicon compound according to claim 1, wherein m is 8.

4. A surface treatment agent containing the organosilicon compound according to any one of claims 1 to 3.

5. A resin additive containing the organosilicon compound according to any one of claims 1 to 3.

6. An article whose surface has been treated with the organosilicon compound according to any one of claims 1 to 3.

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