Rustproofing agent composition

Abstract

A rustproofing agent composition according to the present invention has favorable storage stability and comprises an aqueous solution of organic silicon compounds that includes (i), (ii), or both. (i) An organic silicon compound represented by formula (1) and an organic silicon compound represented by formula (2). (ii) A co-condensate of an organic silicon compound represented by formula (1) and an organic silicon compound represented by formula (2). (In the formulas, the R1's each independently represent a hydrogen atom, a C1–10 alkyl group, or a C6–10 aryl group, the R2's each independently represent a C1–10 alkyl group or a C6–10 aryl group, X represents a monovalent group that includes a nitrogen-containing heterocycle, the m's are each independently an integer from 1 to 20, inclusive, the n's are each independently an integer from 1 to 3, inclusive, p is an integer from 1 to 10, inclusive, and q is an integer from 0 to 5, inclusive.)

Description

Rust prevention treatment composition

[0001] The present invention relates to a rust prevention treatment composition, and more specifically to a rust prevention treatment composition comprising an aqueous solution of a specific organosilicon compound.

[0002] In recent years, water-based rust inhibitors have been in demand due to the safety of metalworking processes. For example, Patent Document 1 proposes a water-soluble rust inhibitor consisting of a composition containing an alkyl carboxylate and an aromatic carboxylate. However, the rust inhibitor of Patent Document 1 has a problem in that it does not provide sufficient long-term rust prevention in severe corrosive environments. Furthermore, Patent Document 2 proposes a metal surface treatment agent using an alkoxysilane having an imidazole ring, but the aqueous solution of the silane compound has poor storage stability, so an organic solvent such as alcohol must be used.

[0003] JP-A-2009-7497 JP-A-5-39295

[0004] The present invention has been made in view of the above circumstances, and has as its object to provide a rust preventative treatment composition which comprises an aqueous solution of an organosilicon compound and which has good storage stability.

[0005] As a result of extensive research conducted by the present inventors to achieve the above object, they discovered that an aqueous solution composition containing a cohydrolyzate of a specific organosilicon compound has excellent storage stability, and thus completed the present invention.

[0006] That is, the present invention provides: 1. A rust preventive treatment composition comprising an aqueous solution containing the following (i), (ii), or both: (i) an organosilicon compound represented by the following formula (1) and an organosilicon compound represented by the following formula (2); and (ii) a co-condensate of the organosilicon compound represented by the following formula (1) and the organosilicon compound represented by the following formula (2). (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 2each independently represents an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms, X represents a monovalent group having a nitrogen-containing heterocycle, each m is independently an integer of 1 to 20, each n is independently an integer of 1 to 3, p is an integer of 1 to 10, and q is an integer of 0 to 5. 2. The rust preventive treatment composition of 1, wherein X is a group selected from the following formulas (3) to (7): (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 a wavy line represents a bond to an adjacent atom.) 3. A rust preventive treatment composition according to 1, in which the alcohol content is 0.3 mass% or less based on the total amount of the composition; 4. An article treated with the rust preventive treatment composition according to any one of 1 to 3.

[0007] The rust preventive treatment composition of the present invention has excellent storage stability and can suppress gelation and the occurrence of precipitates. Furthermore, by treating an article such as a metal with the rust preventive treatment composition of the present invention, rust prevention properties can be imparted to the article.

[0008] The present invention will be specifically described below. The rust preventive treatment composition of the present invention comprises an aqueous solution containing the following (i), (ii), or both: (i) an organosilicon compound represented by the following formula (1) (hereinafter referred to as compound (1)) and an organosilicon compound represented by the following formula (2) (hereinafter referred to as compound (2)); (ii) a co-condensate of compound (1) and compound (2);

[0009]

[0010] In formula (1) and formula (2), 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.

[0011] In formula (1) and formula (2), 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 more preferred.

[0012] 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.

[0013] 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.

[0014] 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.

[0015] 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.

[0016] That is, the above X is preferably a group selected from the following formulas (3) to (7).

[0017] (In the formula, the wavy lines represent bonds to adjacent atoms.)

[0018] 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.

[0019] Specific examples of X are shown below, but are not limited to these.

[0020] (In the formula, the wavy lines represent bonds to adjacent atoms.)

[0021] In formula (1) and formula (2), m represents an integer of 1 to 20, but from the viewpoint of aqueous solution stability and rust-preventing performance, an integer of 3 to 12 is preferred, and an integer of 3 to 5 is more preferred. If m exceeds 20, the heterocyclic ring content per unit mass decreases, which may result in a decrease in rust-preventing performance and a decrease in water-solubility stability. n represents an integer of 1 to 3, but from the viewpoint of adhesiveness, 2 or 3 is preferred.

[0022] p is an integer of 1 to 10, and from the viewpoint of water solubility stability, is preferably 2 or 3, and more preferably 2. q is an integer of 0 to 5, and from the viewpoint of water solubility stability, is preferably 0 or 1.

[0023] The compound (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.

[0024] Specific examples of compound (A) include chloromethyltrimethoxysilane, chloromethyltriethoxysilane, 3-chloropropyltrimethoxysilane, 3-chloropropyltriethoxysilane, 4-chlorobutyltrimethoxysilane, 4-chlorobutyltriethoxysilane, 4-bromobutyltrimethoxysilane, 4-bromobutyltriethoxysilane, 6-chlorohexyltrimethoxysilane, 6-chlorohexyltriethoxysilane, 6-bromohexyltrimethoxysilane, 6-bromohexyltriethoxysilane, 8-chlorooctyltrimethoxysilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyldimethoxymethylsilane, 8-chlorooctyldiethoxymethylsilane, 8-bromooctyltrimethoxysilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyldimethoxymethylsilane, 8-chlorooctyldiethoxymethylsilane, 8-bromooctyltriethoxysilane, 8-chloro ...triethoxymethylsilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyltriethoxymethylsilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyltriethoxymethylsilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyltriethoxymethylsilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyltriethoxymethylsilane, 8-chlorooctyltriethoxymethylsilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyltriethoxymethyl butyltrimethoxysilane, 8-bromooctyltriethoxysilane, 8-bromooctyldimethoxymethylsilane, 8-bromooctyldiethoxymethylsilane, 10-chlorodecyltrimethoxysilane, 10-chlorodecyltriethoxysilane, 10-bromodecyltrimethoxysilane, 10-bromodecyltriethoxysilane, 11-chloroundecyltrimethoxysilane, 11-chloroundecyltriethoxysilane, 11-bromoundecyltrimethoxysilane, 11-bromoundecyltriethoxysilane, 12-chlorododecyltrimethoxysilane, 12-chlorododecyltriethoxysilane, 12-bromododecyltrimethoxysilane, 12-bromododecyltriethoxysilane, etc. These may be used alone or in combination of two or more. Among these, 3-chloropropyltrimethoxysilane, 3-chloropropyltriethoxysilane, 4-chlorobutyltrimethoxysilane, 4-chlorobutyltriethoxysilane, 6-chlorohexyltrimethoxysilane, 6-chlorohexyltriethoxysilane, 8-chlorooctyltrimethoxysilane, 8-chlorooctyltriethoxysilane, 8-chlorooctyldimethoxymethylsilane, 8-chlorooctyldiethoxymethylsilane, 11-chloroundecyltrimethoxysilane, and 11-chloroundecyltriethoxysilane are preferred, and 3-chloropropyltrimethoxysilane and 3-chloropropyltriethoxysilane are more preferred.

[0025] 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.

[0026] 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.

[0027] 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.

[0028] Specific examples of the compound (2) include 3-aminopropyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3-aminopropylmethyldimethoxysilane, 3-aminopropylmethyldiethoxysilane, 3-(2-aminoethylamino)propyltrimethoxysilane, 3-(2-aminoethylamino)propyltriethoxysilane, 3-(2-aminoethylamino)propylmethyldimethoxysilane, 3-(2-aminoethylamino)propylmethyldiethoxysilane, 3-[2-(2-aminoethylamino)ethylamino]propyltrimethoxysilane, 3-[2-(2-aminoethylamino)ethylamino]propyltriethoxysilane, 3-[2-(2-aminoethylamino)ethylamino]propylmethyldimethoxysilane, 3-[2-(2-aminoethylamino)ethylamino]propylmethyldiethoxysilane, etc. These may be used alone or in combination of two or more.

[0029] In the composition of the present invention, the ratio of the compound (1) to the compound (2) is not particularly limited. However, from the viewpoints of storage stability and productivity, the ratio of the compound (2) to 1 mole of the compound (1) is preferably 0.1 to 100 moles, more preferably 0.5 to 20 moles, and even more preferably 1 to 10 moles.

[0030] The composition of the present invention can be prepared by mixing the compound (1) and the compound (2) in an air atmosphere or an inert gas atmosphere such as nitrogen, or by diluting the compound (1) and the compound (2) in water and, if necessary, an alcohol in an air atmosphere or an inert gas atmosphere such as nitrogen, to form a Si—OR compound represented by the formula (1) and the formula (2). 1 In this case, R 1 The compound can be obtained by hydrolyzing a part or all of the groups represented by an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms into silanol groups (Si—OH groups). Water may be added continuously during the hydrolysis reaction or before the reaction is started.

[0031] The temperature for the hydrolysis reaction is preferably 50 to 110° C., more preferably 60 to 105° C. The reaction time is preferably 1 to 30 hours, more preferably 5 to 25 hours.

[0032] The alcohol component R 1 OH (R 1 is an alkyl group having 1 to 10 carbon atoms or an aryl group having 6 to 10 carbon atoms.) and the alcohol component added together with water as needed during the hydrolysis reaction are preferably removed by a separation method such as distillation. Distillation is preferably carried out simultaneously with the hydrolysis reaction.

[0033] The total amount of the compound (1) and the compound (2) contained in the composition of the present invention is not particularly limited, but from the viewpoints of storage stability and productivity, it is preferably 0.1 to 50 mass % and more preferably 10 to 40 mass % based on the total amount of the aqueous solution composition. In addition, a part or all of the compound (1) and the compound (2) may form a co-condensation product by intermolecular condensation between silanol groups.

[0034] From the viewpoint of safety, the amount of alcohol contained in the composition of the present invention is preferably 0.3% by mass or less, more preferably 0.1% by mass or less, based on the total amount of the composition. The amount of alcohol in the composition can be confirmed by gas chromatography (GC) analysis, and it is even more preferable that the amount of alcohol in the composition of the present invention is not detected by GC analysis (below the detection limit).

[0035] The composition of the present invention can impart rust prevention properties to various materials, articles, etc. by applying it to these materials, articles, etc. Specific examples of the materials and articles include various articles made of various metallic materials such as iron, stainless steel, aluminum, nickel, zinc, and copper.

[0036] The present invention will be described in more detail below with reference to synthesis examples, examples, and comparative examples, but the present invention is not limited to these examples. Note that Me represents a methyl group. [Gas chromatography (hereinafter referred to as GC) analysis conditions] GC apparatus: 6890N manufactured by Agilent Technologies Detector: Flame ionization detector (FID) Column: HP-5 J-413 (length 30 m x inner diameter 0.32 mm, film thickness 0.25 μm) Column temperature: 50°C → 10°C / min → 300°C (held for 10 minutes) Inlet temperature: 250°C Detector temperature: 300°C Carrier gas: He Carrier gas flow rate: 1.0 mL / min

[0037] [1] Synthesis of Organosilicon Compound [Synthesis Example 1] 102.12 g (1.5 mol) of imidazole and 400 g of dimethylformamide were placed in a 1 L separable flask equipped with a stirrer, reflux condenser, dropping funnel, and thermometer. 81.03 g (1.5 mol) of sodium methoxide was added while stirring at 10°C, and the mixture was heated to 120°C. 298.08 g (1.5 mol) of 3-chloropropyltrimethoxysilane was added dropwise thereto, and the mixture was stirred at 120°C for 3 hours. The reaction was then terminated by confirming by GC that the peak of the raw material imidazole had completely disappeared. Distillation was then performed to obtain organosilicon compound 1, a pale yellow liquid represented by the following formula (8):

[0038]

[0039] Synthesis Example 2: 177.21 g (1.5 mol) of benzimidazole and 400 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. 298.08 g (1.5 mol) of 3-chloropropyltrimethoxysilane was added dropwise thereto, and the mixture was stirred at 120°C for 3 hours. The reaction was then terminated by confirming by GC that the peak of the starting imidazole had completely disappeared. Distillation was then carried out to obtain organosilicon compound 2, a pale yellow liquid represented by the following formula (9):

[0040]

[0041] [2] Production of Rust Prevention Treatment Composition [Example 1-1] 50 g of the organosilicon compound 1 obtained in Synthesis Example 1, 70 g of 3-aminopropyltrimethoxysilane (KBM-903, manufactured by Shin-Etsu Chemical Co., Ltd.; the same applies hereinafter), and 120 g of ion-exchanged water were added to a nitrogen-purged 500 mL pressure reaction vessel, and the mixture was distilled with stirring until the internal temperature reached 100°C to remove the produced methanol. Thereafter, ion-exchanged water was added to a concentration of 30% by mass, thereby obtaining a rust prevention treatment composition. The resulting composition had a transparent appearance, and no methanol was detected in GC analysis.

[0042] Example 1-2: 80 g of organosilicon compound 1 obtained in Synthesis Example 1, 50 g of 3-aminopropyltrimethoxysilane, and 130 g of ion-exchanged water were added to a nitrogen-purged 500 mL pressure reaction vessel, and the mixture was distilled with stirring until the internal temperature reached 100°C to remove the produced methanol. Thereafter, ion-exchanged water was added to a concentration of 30% by mass, yielding a rust prevention treatment composition. The resulting composition was transparent in appearance, and no methanol was detected in GC analysis.

[0043] [Example 1-3] 30 g of organosilicon compound 1 obtained in Synthesis Example 1, 90 g of 3-aminopropyltrimethoxysilane, and 120 g of ion-exchanged water were added to a nitrogen-purged 500 mL pressure reaction vessel, and the resulting methanol was removed by distillation with stirring until the internal temperature reached 100°C. Thereafter, ion-exchanged water was added to a concentration of 30% by mass, yielding a rust prevention treatment composition. The resulting composition was transparent in appearance, and no methanol was detected in GC analysis.

[0044] [Examples 1-4] 50 g of organosilicon compound 2 obtained in Synthesis Example 2, 70 g of 3-aminopropyltrimethoxysilane, and 120 g of ion-exchanged water were added to a nitrogen-purged 500 mL pressure reaction vessel, and the mixture was distilled with stirring until the internal temperature reached 100°C to remove the produced methanol. Thereafter, ion-exchanged water was added to a concentration of 30% by mass, yielding a rust prevention treatment composition. The resulting composition was transparent in appearance, and no methanol was detected in GC analysis.

[0045] [Examples 1-5] 50 g of organosilicon compound 1 obtained in Synthesis Example 1, 70 g of 3-(2-aminoethylamino)propyltrimethoxysilane (KBM-603, manufactured by Shin-Etsu Chemical Co., Ltd.), and 120 g of ion-exchanged water were added to a nitrogen-purged 500 mL pressure reaction vessel, and the mixture was distilled with stirring until the internal temperature reached 100°C to remove the produced methanol. Thereafter, ion-exchanged water was added to a concentration of 30% by mass, yielding a rust prevention treatment composition. The resulting composition was transparent in appearance, and no methanol was detected in GC analysis.

[0046] [Comparative Example 1-1] 10 g of organosilicon compound 1 obtained in Synthesis Example 1 and 150 g of ion-exchanged water were added to a nitrogen-purged 500 mL pressure reaction vessel, and the mixture was distilled with stirring until the internal temperature reached 100°C to remove the produced methanol. Thereafter, ion-exchanged water was added to a concentration of 5 mass%, yielding a rust prevention treatment composition. The resulting composition had a transparent appearance, and no methanol was detected in GC analysis.

[0047] Comparative Example 1-2 100 g of organosilicon compound 1 obtained in Synthesis Example 1 and 200 g of ion-exchanged water were placed in a nitrogen-purged 500 mL pressure reaction vessel, and the resulting methanol was distilled off while stirring until the internal temperature reached 100°C, causing the system to gel.

[0048] <Evaluation of Storage Stability> The rust preventive treatment compositions obtained in Examples 1-1 to 1-5 and Comparative Example 1-1 above were stored at 50°C under sealed conditions for a predetermined period (1 week, 1 month, 3 months) and then visually observed for appearance to evaluate stability. A transparent solution with no observed precipitate was rated as ◯, and a non-existent precipitate was rated as ×. The results are shown in Table 1.

[0049]

[0050] As shown in Table 1, it is clear that the rust preventive treatment compositions of Examples 1-1 to 1-5 have superior storage stability compared to that of Comparative Example 1-1.

[0051] [2] Production of Treated Articles [Examples 2-1 to 2-5, Comparative Example 2-1] A commercially available copper plate (manufactured by KDS Corporation; 70 × 150 × 1 mm) was pretreated by immersing it in a 30 mass % HSO aqueous solution for 30 seconds and then drying. Ion-exchanged water was added to the rust preventive treatment agent compositions obtained in Examples 1-1 to 1-5 and Comparative Example 1-1 above to prepare a 5 mass % aqueous solution, and the pretreated copper plate was immersed in this for 5 minutes and then dried at 25°C for 60 minutes to obtain a test plate.

[0052] <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. The results are shown in Table 2. 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

[0053]

[0054] As shown in Table 2, the treated copper plates of Examples 2-1 to 2-5 are superior in rust prevention (corrosion resistance) compared to that of Comparative Example 2-1.

Claims

1. A rust preventative treatment composition comprising an aqueous solution containing the following (i), (ii), or both: (i) an organosilicon compound represented by the following formula (1) and an organosilicon compound represented by the following formula (2); (ii) a co-condensate of the organosilicon compound represented by the following formula (1) and the organosilicon compound represented by the following formula (2). (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 6 to 10 carbon atoms, X represents a monovalent group having a nitrogen-containing heterocycle, each m is independently an integer of 1 to 20, each n is independently an integer of 1 to 3, p is an integer of 1 to 10, and q is an integer of 0 to 5.

2. The rust preventative treatment composition according to claim 1, wherein X is a group selected from the following formulas (3) to (7): (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 rust preventive treatment composition according to claim 1, wherein the alcohol content is 0.3 mass % or less based on the total composition.

4. An article treated with the rust preventive treatment composition according to any one of claims 1 to 3.

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