JP2001510820A - Novel N-alkyl-hydroxybenzylamines, their preparation, their use, and compositions containing the compounds - Google Patents

Abstract

(57) Abstract: The present invention provides a compound represented by the formula (I): Wherein R ₁ and R ₂ may be the same or different and provided that R ₁ and R ₂ do not simultaneously represent a hydrogen atom, a hydrogen atom or a monohydroxylated or polyhydroxylated reduction has been showing a _C 1 -C ₈ alkyl group; Q represents an -OH or -NH ₂ group; Z is a hydrogen atom or the following group (a) (Wherein R ₁ and R ₂ are the same as defined above), provided that Y ₁ and Y ₂ do not simultaneously represent a hydrogen atom, and Y ₁ and Y ₂ represent a hydrogen atom or an —OH group. It relates to a novel N-alkyl-hydroxybenzylamine.

Description

DETAILED DESCRIPTION OF THE INVENTION

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TECHNICAL FIELD OF THE INVENTION

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[Prior art]

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Problems to be Solved by the Invention and Means for Solving the Problems

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BEST MODE FOR CARRYING OUT THE INVENTION

The present invention provides a compound of formula (I): Wherein R ₁ and R ₂ may be the same or different, provided that R ₁ and R ₂ do not simultaneously represent a hydrogen atom or a hydrogen atom or monohydroxylated or polyhydroxylated shows the reduction has been _C 1 -C ₈ alkyl group; Q represents an -OH or -NH ₂ group; Z is a hydrogen atom or the following group (In the formula, _{R 1} and _{R 2} are the same as defined above), with the proviso that _{Y 1} and _{Y 2} do not show a hydrogen atom at the same time, _{Y 1} and _{Y 2} represents a hydrogen atom or an -OH group on the It relates to a novel N-alkyl-hydroxybenzylamine.

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【Example】

Example 1 The following formula: Of N-methyl-N- (1-deoxy-glucitol) 3,4-dihydroxyphenylmethylamine and N-methyl-N- (1-deoxy-glucitol) 2,3-dihydroxyphenylmethylamine

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Example 2 The following formula: Of 2,4 bis (N-methyl-N- (1-deoxy-glucitol) amino-methyl) -6-hydroxyphenol corresponding to

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Example 3 The following formula: 2,4 bis (N-methyl-N- (1-deoxy-glucitol) amino-methyl) -6-amino-phenol and 3,5 bis (N-methyl-
Preparation of N- (1-deoxy-glucitol) amino-methyl) -2-amino-phenol

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Example 4 The following formula: Of N-methyl-N- (1-deoxy-glucitol) 2,3,4-tri-hydroxyphenylmethylamine corresponding to

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Example 5 The following formula: N-methyl-N- (2-hydroxyethyl) 3,4-dihydroxyphenylmethylamine and N-methyl-N- (2-hydroxyethyl) 2
Of 2,3-dihydroxyphenylmethylamine

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[Procedure amendment]

[Submission date] March 23, 2000 (2000.3.23)

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] Full text

[Correction method] Change

[Correction contents]

Novel N-alkyl-hydroxybenzylamines, their preparation, their use, and compositions containing the compounds

[Claims]

Embedded image Wherein R ₁ and R ₂ may be the same or different, provided that R ₁ and R ₂ do not simultaneously represent a hydrogen atom. shows the reduction has been C ₁ -C ₈ alkyl group; Q represents an -OH or -NH ₂ group; Z is a hydrogen atom or the following group:

Embedded image (Wherein R ₁ and R ₂ are the same as defined above), provided that Y ₁ and Y ₂ do not simultaneously represent a hydrogen atom, and Y ₁ and Y ₂ represent a hydrogen atom or an —OH group. New N-alkyl-hydroxybenzylamines.

Embedded image Wherein R ₁ and R ₂ have the meanings given above, in the presence of a formol of an amine of the formula

Embedded image (Wherein Q, Y ₁ and Y ₂ have the above-mentioned meanings), which is characterized by performing Mannich condensation on the phenolic reducing agent

Embedded image Where m is 1 or 2 and monosubstituted and therefore Z represents H or disubstituted and thus Z is a group

Embedded image The method for preparing N-alkyl-hydroxybenzylamine according to claim 1, wherein the chemical equivalent of formaldehyde is represented by the following formula:

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention is directed to a novel N-alkyl-hydroxybenzylamine.

Also, a process for the production of these novel N-alkyl-hydroxybenzylamines, their use in metal surface treatments to prevent corrosion and to improve the adhesion of paints subsequently, and as active ingredients The purpose of the present invention is to provide a composition containing

[0003]

2. Description of the Related Art As measures for preventing corrosion of metal surfaces, there are already: polymers having a polyvinylphenol structure (EP-0911166 data); condensation polymers of the above-mentioned polyvinylphenols with formalin-phenol resin, tannin and lignin. (Documents of EP-0319017B1) ・ Substituted polyvinylphenols (Documents of US Pat. No. 4,978,399) ・ Substituted polyorthomethylenephenols (Documents of WO95 / 28449) ・ Substituted polyorthomethylenebisphenols (WO95 / 28509, WO97)
/ 04144 and WO97 / 04145 documents) Monomer molecules having substituted mono- and bisaminophenol nuclei (each EP
-0276072B1 and EP-0517356B1)).

[0004]

The problem to be solved by the present invention is to obtain, after treatment, a surface which simultaneously exhibits excellent flatness properties from the viewpoint of resistance to corrosion and adhesion of a paint applied thereto. Known polymer and monomer structures are not entirely satisfactory.

Accordingly, the present invention aims, inter alia, to correct the disadvantages of the prior art and to provide N-alkyl-hydroxybenzylamines which are more effective than known polymer and monomeric substances.

[0006] The applicant's company has developed a novel N-alkyl-
Successful development of hydroxybenzylamine.

[0007]

BEST MODE FOR CARRYING OUT THE INVENTION The present invention provides a compound of the formula (I):

Embedded image Wherein R ₁ and R ₂ may be the same or different, provided that R ₁ and R ₂ do not simultaneously represent a hydrogen atom. shows the reduction has been C ₁ -C ₈ alkyl group; Q represents an -OH or -NH ₂ group; Z is a hydrogen atom or the following group:

Embedded image (Wherein R ₁ and R ₂ are the same as defined above), provided that Y ₁ and Y ₂ do not simultaneously represent a hydrogen atom, and Y ₁ and Y ₂ represent a hydrogen atom or an —OH group. It relates to a novel N-alkyl-hydroxybenzylamine.

The molecules of the formula (I) exhibit a very strong affinity for metal surfaces; this affinity is due to their chelating ability; these molecules promote the adhesion of coatings as well as protective coatings. Forming a coating network on the metal surface such as that, and on which is an important function, they prevent any corrosion due to oxidation of the support.

In other words, the invention therefore also aims at the use of N-alkyl-hydroxybenzylamines of the formula (I) in the treatment of metal surfaces, which prevents corrosion and at the same time improves the adhesion of the paint. Is what you do.

[0010] Due to their internal structure in the form of orthophenol, these molecules are both chelating and iron reducing agents; thus, they support metal oxides,
In particular, it limits the oxidation of Fe (O) to Fe (II) and Fe (III). Thus, they are an advantageous alternative to known polymer structures which always exhibit undesired disadvantages.

In addition, these molecules do not degrade the metal support by chemical attack; thus, they protect the intact state of fragments that have undergone a treated surface.

Finally and above all, they can replace the currently used chromium phosphorylation treatments.

The process for the preparation of the compounds of formula (I) according to the present invention has the formula:

Embedded image Wherein R ₁ and R ₂ have the meanings given above, in the presence of a formol of an amine of the formula

Embedded image (Wherein Q, Y ₁ and Y ₂ have the above-mentioned meanings), which is characterized by performing Mannich condensation on the phenolic reducing agent

Embedded image Where m is 1 or 2 and monosubstituted and therefore Z represents H or disubstituted and thus Z is a group

Embedded image Represents the stoichiometric equivalent of formaldehyde). Starting materials of formulas (II) and (III) are commercially available or can be easily obtained by synthetic methods according to techniques well known to those skilled in the art.

The above condensation reaction can be carried out in the presence of an inert organic solvent.

Inert organic solvents include aliphatic volatile oils of the group comprising hexane, heptane, octane, nonane and dodecane, chlorinated derivatives of the group comprising dichloromethane, 1,2-dichloroethane, chloroform, trichloroethylene and tetrachloroethylene, diethyl And dialkyl ethers, polyalkoxyalkanes, polyalkoxy alcohols and alcohols in the group comprising dipropyl ether and dibutyl ether, the preferred solvents being benzene, toluene and xylene.

[0016] The amount of solvent used in the reaction is not critical.

Preferably, the reaction is carried out in the presence of a solvent which forms a heteroazeotrope with water when refluxed with the azeotrope; and the water formed by the reaction is gradually removed from the reaction medium as it is formed. It is. This technology makes it possible to obtain high productivity and high conversion rates.

The reaction is carried out at a temperature of 50 to 200 ° C., preferably 50 to 150 ° C., more preferably 50 to 100 ° C.

It can be carried out at atmospheric pressure, such as under the natural vapor pressure of formaldehyde; however, it is preferably carried out at atmospheric pressure with reflux of formaldehyde.

The molar amount of formaldehyde used relative to the amine of the formula (II) can vary in a ratio of from 0.1 to 5, preferably from 0.5 to 2.5 mol of formaldehyde / formula (II) A) moles of amine, more preferably from 1 to 2 mol / mol of formaldehyde are used.

The molar amount of the phenol of the formula (III) used for the amine of the formula (II) is
It can vary in a ratio of 0.1 to 2; preferably, phenol 0.4
An amount of phenol of from .1 to 1.5 mol / amine mol, more preferably from 0.5 to 1 mol / mol, is used.

The reaction can be carried out in the absence or presence of a catalyst; preferably an aliphatic tertiary amine such as trimethylamine, methyldiethylamine or triethylamine, a tertiary amine such as dimethylaniline, diethylaniline. Aniline,
Or operating in the presence of a basic catalyst which can be selected from cyclic amines such as pyridine or even imidazole; it is also possible to use alkaline bases such as soda, potassium or lime.

The amount of catalyst used for the amine of the formula (II) is from 0.1 to 5 mol% of catalyst per mol of amine.

The reaction conditions are maintained for a time necessary and sufficient to obtain an amine conversion of greater than 95%.

Due to their particularly advantageous properties, the N-alkyl-hydroxybenzylamines according to the invention can be used in the form of compositions which provide protection against corrosion in a manner which does not rely on chromium treatment.

[0026] The corrosion-inhibiting composition according to the invention can therefore be prepared as a solution or in the form of a dispersion in water or, optionally, in a solvent in which the surfactants, wetting agents and dispersants required for formulating the active ingredients are present. Characterized in that it comprises an effective amount of at least one N-alkyl-hydroxybenzylamine of the formula (I).

The term “effective amount” refers to the active substance necessary and sufficient to confer protection of the treated piece against corrosion for at least 100 hours, according to a series of saline spray tests as defined in ISO standard 9227. Means quantity.

In practice, the compositions according to the invention contain from 0.01 to 400 g, preferably from 0.2 to 100 g, of active ingredient per liter.

The composition according to the invention can be marketed in the form of a concentrate.

The active substance content of the concentrate is the maximum solubility in the solvent used.

If the solvent is water, its content can reach 50% by weight, ie 500 g / liter of solvent or water.

In use, the concentrate is diluted with the required amount of solvent or water.

Water is a preferred solvent for the composition according to the invention, but is not limited to aliphatic volatile oils, aromatic solvents such as benzene, toluene, xylene and alkylnaphthalene, halogenated solvents, alcohols, ethers, Polyethers, ketones and mixtures of these solvents can also be used.

As mentioned above, formulations that are exclusively aqueous are preferred.

The pH of the composition according to the invention is between 1 and 12, preferably between 4 and 9, more preferably between 5 and 8.

To adjust this pH, use is made of an organic or inorganic acid, preferably a combination of acids, one organic and the other inorganic; the precise adjustment of the pH of the composition requires the addition of a small amount of an inorganic or organic base. The addition is performed.

Organic acids that can be used include acetic acid, tartaric acid, oxalic acid, citric acid, adipic acid, acrylic acid and methacrylic acid, succinic acid, and maleic acid, malonic acid, glutamic acid, aspartic acid, gluconic acid, lactic acid, gallic The group includes polycarboxylic acids including acids, iminodiacetic acid, salicylic acid, sulfosalicylic acid, and glycolic acid.

Examples of the inorganic acid include hydrochloric acid, sulfuric acid, phosphorous acid, nitric acid, sulfamic acid and phosphoric acid.

The “organic acid / inorganic acid” combination components and the pH are chosen so as to obtain optimal properties with respect to protection against corrosion.

The base used to precisely adjust the pH is preferably diethylamine,
Alkylamines of the group including isopropylamine, ethylenediamine, diethylenetriamine, triethylenetetramine, hexamethylenetetramine, amines having a functional group OH of the group including hydroxylamine, mono- and polyethanolamine, isopropanolamine, morpholine, ammonium carbonate, ammonia , Soda and potash.

It is possible to adjust the pH using one or more of these compounds in a total of 0.1 to 100 g / l, preferably 0.5 to 30 g / l.

The composition according to the invention may comprise other corrosion inhibitors, adhesion promoters, dispersants, wetting agents, emulsifiers, thickeners, defoamers, plasticizers, anti-gelling agents, antifungals, antibacterials. , Soluble and insoluble resins, organic polymers, pigments, colorants and inorganic fillers and any other compounds known to those skilled in the art.

Other corrosion inhibitors that can be used include zinc phosphate, alkaline earth sulphonate, used at a concentration of 0.05 to 2%.

[0044] Adhesion promoters that can be used include silanes, organotitanic acids, and zircoaluminate complexes commercially available under the name MANCHEM ™.

Examples of resins that can be used include acrylic resins, vinyl chloride acrylic copolymers, and phenolic resins modified by Mannich reaction.

Fillers and pigments that can be used include silica, silicate, and silicoaluminate.

The composition according to the invention comprises: a step of defatting the surface of the pieces to be treated by any composition or technique known to a person skilled in the art; a step of rinsing the pieces to be treated; 15 to 60 ° C., preferably At a temperature of 15 to 40 ° C., immersing the pieces in the composition, sprinkling the composition on the surface of the piece to be treated or applying with a brush or ink roll, treating with the composition according to the invention; It can be used within the context of a process comprising successively rinsing with hot or cold water, drying at a temperature of 40 to 160 ° C.

The liquid or powder coating can then be applied by any coating application technique known to those skilled in the art.

If the composition is applied by dipping, the dipping time must be sufficient to obtain a uniform deposition of the active substance, which is generally less than 15 minutes, often between 30 and 180 seconds The deposition thus obtained is between 0.5 and 15 g /
This corresponds to a coating weight on the order of m ² or 0.1 to 15 g / m ² of active substance on the treated surface.

[0050]

EXAMPLES Example 1 The following formula:

Embedded image Of the isomers N-methyl-N- (1-deoxy-glucitol) 3,4-dihydroxyphenylmethylamine and N-methyl-N- (1-deoxy-glucitol) 2,3-dihydroxyphenylmethylamine corresponding to Preparation In a 500 ml reactor equipped with a stirrer, thermometer, reflux condenser, "Dean Stark" (technical term referring to a distillation controller capable of extracting reaction water) and an injection ampoule, 70 g of toluene, n- 60 g of butanol, 11 g of pyrocatechol (
110 mmol), 23.4 g (120 mmol) of N-methyl-glucamine and 0.8 g (10 mmol) of 50% soda.

The temperature of the mixture is brought to 70 ° C. and then 36% formaldehyde for 15 minutes.
5 g (150 mmol) are introduced.

The whole is refluxed for one hour and then 9.5 g of water (ie a theoretical amount of 90
%) Is azeotropically distilled.

Introduce 100 g of distilled water from the injection ampoule and then clarify at 80 ° C. for 15 minutes.

The aqueous phase is stripped to remove traces of residual solvent (technical term referring to the removal of traces of solvent by distillation).

Thus, two monosubstituted isomers corresponding to a 94% yield: N-methyl-N- (1-deoxy-glucitol) -3,4-dihydroxyphenylmethylamine, N-methyl- 116 g of a 29% solution of a dry extract, a research substance composed of N- (1-deoxy-glucitol) -2,3-dihydroxyphenylmethylamine, are obtained.

The separation was not attempted because both molecules are effective.

This solution of the active substance can be used directly for formulating corrosion inhibitor compositions.

Example 2 The following formula:

Embedded image Preparation of 2,4-bis (N-methyl-N- (1-deoxy-glucitol) amino-methyl) -6-hydroxyphenol corresponding to Agitator, thermometer, reflux condenser, "Dean Stark" and injection ampoule In a equipped 500 ml reactor, toluene 50 g, n-butanol 50 g, pyrocatechol 5.5 g (50 mmol), N-methyl-glucamine 21.5 g (11
0 mmol) and 0.4 g (5 mmol) of 50% soda.

The temperature of the mixture is brought to 70 ° C. and then 36% formaldehyde for 15 minutes
7 g (140 mmol) are introduced.

The whole is refluxed for 1 hour and then, in the course of 2 hours, 10.2 g of water (ie 1 to theoretical amount)
(00%) is azeotropically distilled.

Introduce 100 g of distilled water from the injection ampoule and then clarify at 70 ° C. for 15 minutes.

The aqueous phase stripped to remove traces of residual solvent is collected.

In this way, 96 g of a 28% solution of the dry extract, a research substance, corresponding to a yield of 95%, are obtained.

The solution of the active substance can be used directly for formulating corrosion inhibitor compositions.

Example 3 The following formula:

Embedded image 2,4 bis (N-methyl-N- (1-deoxy-glucitol) amino-methyl) -6-amino-phenol and 3,5 bis (N-methyl-N- (1-deoxy) Preparation of -Glucitol) amino-methyl) -2-amino-phenol In a 500 ml reactor equipped with stirrer, thermometer, reflux condenser, "Dean Stark" and injection ampoule, 50 g of toluene, 70 g of n-butanol, 5.5 g (50 mmol) of aminophenol, 21.5 g of N-methyl-glucamine
(110 mmol) and 0.4 g (5 mmol) of 50% soda.

The temperature of the mixture is brought to 70 ° C. and then 36% formaldehyde in 15 minutes
7 g (140 mmol) are introduced.

The whole is refluxed for one hour and then 9.4 g of water (ie a theoretical amount of 98
%) Is azeotropically distilled.

100 g of distilled water are introduced from the injection ampoule and then clarified at 80 ° C. for 15 minutes.

The aqueous phase stripped to remove traces of residual solvent is collected.

Thus, 27% of the dry extract, a research substance, corresponding to a yield of 100%
101 g of solution are obtained.

The solution of the active substance can be used directly for formulating corrosion inhibitor compositions.

Example 4 The following formula:

Embedded image Preparation of N-Methyl-N- (1-deoxy-glucitol) 2,3,4-tri-hydroxyphenylmethylamine Corresponding to Equipped with Stirrer, Thermometer, Reflux Cooler, "Dean Stark" and Injection Ampoule In a 1 liter reactor, 100 g of toluene, 200 g of n-butanol, 25.5 g (200 mmol) of pyrogallol, 46.8 g of N-methyl-glucamine
(240 mmol) and 1.6 g (20 mmol) of 50% soda.

The temperature of the mixture is brought to 70 ° C. and then 36% formaldehyde 25.
0 g (300 mmol) are introduced.

The whole is refluxed for one hour and then azeotropically distills 21 g of water in the course of 2 hours.

Introduce 250 g of distilled water from the injection ampoule and then clarify at 90 ° C. for 30 minutes.

The aqueous phase stripped to remove traces of residual solvent is collected.

In this way, 242 g of a 31% solution of the dried extract, a research substance, corresponding to a yield of 99%, are obtained.

The solution of the active substance can be used directly for formulating corrosion inhibitor compositions.

Example 5 The following formula:

Embedded image Preparation of the isomers N-methyl-N- (2-hydroxyethyl) 3,4-dihydroxyphenylmethylamine and N-methyl-N- (2-hydroxyethyl) 2,3-dihydroxyphenylmethylamine corresponding to In a 500 ml reactor equipped with thermometer, reflux condenser, "Dean Stark" and injection ampoule, 100 g of toluene, 100 g of n-butanol, 22 g (200 mmol) of pyrocatechol, 2- (methylamino) -ethanol 1
8 g (240 mmol) and 1.6 g (20 mmol) of 50% soda are charged.

The temperature of the mixture was brought to 70 ° C. and then 25 g of 36% formaldehyde in 15 minutes
(300 mmol).

The whole is refluxed for 1 hour and then 21.6 g of water are azeotropically distilled in the course of 2 hours.

Introduce 200 g of distilled water from the injection ampoule and then clarify at 80 ° C. for 30 minutes.

The aqueous phase stripped to remove traces of residual solvent is collected.

In this way, 146 g of a 18.5% solution of the dry extract, which is the research substance, is obtained.

The solution of the active substance can be used directly for formulating corrosion inhibitor compositions.

The following examples illustrate the effect of the N-alkyl-hydroxybenzylamines of the present invention on preventing corrosion of metal surfaces.

In this regard, the N-alkyl-hydroxybenzylamines of the invention and the prior art molecules according to Examples 1 to 3 are described in Table I with the indicated materials, times, temperatures and methods of operation. Used in the method.

The composition used is as follows: Composition A1 according to the invention: adipic acid 0.5 g / l phosphoric acid 0.4 g / l molecule of Example 1 1 g / l soda 0.15 g / l tri Ethylenetetramine is added to bring the pH to 6.0. Composition A2 according to the invention: Same as composition A1, except that the test compound is that of example 2. Composition A3 according to the invention: Same as composition A1 except that the test compound is that of example 3. Composition C1 according to the invention: The test compound is EP 0 319 017-A2 (US application no. 1286).
No. 73, claiming priority of application) and having the formula:

Embedded image Where X ₁ = H X ₂ =

Embedded image The same as the composition A1 except that it has

[0089]

[Table 1]

The RIDOLINE 417 CF and RIDOSOL 161 CF materials are degreasing compositions based on alkali derivatives and surfactants and marketed by the applicant's company.

The method is as follows: one is a 0.7 mm thick cold-rolled mild steel of ZESNFA 36.401 grade, the other is a 0.7 mm thick electrolytic zinc coated mild steel of NFA 36.260 grade EZ rating; Applies to test specimens of different types.

The test piece has a plate-like shape having a width of 10 cm and a length of 20 cm.

At the same time, as a comparative example, the same specimen was subjected to classical phosphorylation and a subsequent chrome rinse, but the specimen was subjected to an uncharacterized series of classical phosphorylation, the steps being: 1 v / v% DURIDINE F 775 CF + 0 at 50 ° C. for 150 seconds
. Degreasing with 1 v / v% RIDOSOL 162 CF Rinsing at room temperature for 60 seconds Rinning with 0.1 v / v% DEOXYLYTE 41 at room temperature for 40 seconds Rinsing with replacement water for 60 seconds at room temperature Dry for 300 seconds.

DURIDINE F 775 CF and RIDOSOL 162 CF, aqueous solutions based on phosphoric acid and surfactants, respectively, are commercially available from Applicants' company.

After the treatment according to Table I and the phosphorylation treatment, the treated surface is measured for corrosion resistance and the adhesion of the applied paint.

The corrosion resistance is measured by a salt spray test according to ISO Standard No. 9227.

As part of the test, the test specimen includes an inverted V-shaped wound.

After exposure to saline spray for 100 hours, the total thickness of the erosion in the wound and other areas is measured. The results are as follows: ・ Excellent and rated “++” when the corrosion is 0 to 4 mm, ・ Normal and rated “+” when the corrosion is more than 4 mm and up to 7 mm, ・ Evaluated as “−” when the corrosion was greater than 7 mm. Is considered.

[0099] The adhesiveness of the paint is measured by a checkerboard evaluation method according to NFT Standard No. 30.038.

The results are scored from 0 to 5. A score of 0 corresponds to excellent adhesion without any peeling, and a rating of 5 corresponds to complete peeling of the paint.

The results recorded are summarized in Table II.

[0102]

[Table 2]

From the tests in this table, the composition based on the molecules according to the invention gives on the one hand better results than the prior art molecules containing phenol molecules in their structure, on the other hand in all respects It is clearly recognized that the results are comparable to the classical phosphorylation method, without the disadvantages that require a post chromium rinse.

As it uses room temperature, it is simple to use and does not require rinsing after processing, it also answers the need for energy savings when compared to this latter technique. As described in claim 1 of the specification (translation) before the amendment,
In short, the present invention relates to a novel N-alkyl-hydroxybenzylamine represented by the formula (I), which is described in claim 3, claim 7, and paragraph [00]
02], the compound is used for corrosion prevention treatment of metal surfaces. It is believed that those skilled in the art will be able to fully understand the essential parts of the present invention from the description before amendment. However, in the description of the specification before amendment, there are some parts that are written in the original text, and this is a kind of mistranslation in the sense that it is not expressed in proper Japanese. Therefore, this specification was insufficient as a translation in including such mistranslation. Therefore, in order to make the specification consistent, and to make the translation faithful and appropriate to the original text,
The statement has been amended with this mistranslation correction. The amendment items and the amended points are the portions described in the original text in the specification before the amendment,
It seems obvious without having to point out one by one. In addition, while referring to the specification before the amendment,
Compared with the original, those skilled in the art will understand that the amended specification is an appropriately translated one and is within the scope of the matters described in the original. You.

──────────────────────────────────────────────────続 き Continuing on the front page (72) Inventor Jean-Jacques Gasse France, F-27600, Guyron Ryu, Jacques Prevert, 18 (72) Inventor, Michel Gimon France, F-95370, Montigny Les Colmeires Rue de la Frette 20 Bis (72) Inventor Joel Bonin France F-93200 Saint-Denis-Ru-Gaston-Durdan-17 (72) Inventor Stephane Gagnepang France-F-93400-Saint-Owen-Anpass-de-la-gender-merie-2F-term (reference) 4H006 AA01 AA03 AB80 AC21 AC52 BJ50 BN10 BN30 BU38 4K062 AA01 BB12 CA05 CA08 GA03

Claims (7)

[Claims] 1. Formula (I): Wherein R ₁ and R ₂ may be the same or different, provided that R ₁ and R ₂ do not simultaneously represent a hydrogen atom or a hydrogen atom or monohydroxylated or polyhydroxylated shows the reduction has been _C 1 -C ₈ alkyl group; Q represents an -OH or -NH ₂ group; Z is a hydrogen atom or the following group (In the formula, _{R 1} and _{R 2} are the same as defined above), with the proviso that _{Y 1} and _{Y 2} do not show a hydrogen atom at the same time, _{Y 1} and _{Y 2} represents a hydrogen atom or an -OH group on the New N-alkyl-hydroxybenzylamines. (2) (3) 4. The method according to claim 1, wherein the N-alkyl-hydroxybenzylamine is present in an amount of at least 0.1 per liter.
A composition according to claim 3, characterized in that it contains from 01 to 400 g, preferably from 0.2 to 100 g. (5) 6. 7.