FI116845B - Amine-based curing agent, curable resin composition containing said curing agent and corrosion-resistant coating composition containing said curing agent - Google Patents

Description

An amine-based hardener, a hardening agent comprising said hardener, and a corrosion resistant coating comprising said hardener, the baserat härdningsmedel, harbar hartskomposition innehällande ningsmedel och corrosionbeständig beläggningskomposition 5 nämnt härdningsmedel

The present invention relates to an amine based hardener which, as an epoxy resin hardener having good curing properties at this temperature and which is well compatible with the petroleum resin widely used in corrosion resistance, contained a resin composition and a corrosion resistant surface having good curing properties. a low-temperature, er-free, corrosion-resistant coating composition that can be used to coat interiors such as ballast tanks.

An amine-based hardener that can be used as an epoxy is known in the art. The resin containing the aforementioned hardener and epoxy resin is curing at room temperature, so that it can be widely used in a high corrosion resistant * * 'corrosion resistant mold for structures and the like. However, the resin composition of the aforementioned resin composition has poor performance, for example in winter:; at odorous temperatures to reveal the original properties of the epoxy resin.

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In order to improve the curing properties, methods (1) to (4) have been proposed in the art, which are (1) the use of a hardener k 25 captan based hardener, (3) an acrylate-containing hardener and (4) an epoxy-urethane curing system use.

· «« • · * ·. . . A disadvantage of the above-mentioned method (1) is that a known film having poor water and chemical resistance or which also has the disadvantage of odor development.

A disadvantage of the above-mentioned process (3) is that although the Michel addition reaction between α and amine may improve the cure properties of the subunit, nonetheless, the cured film ester linkages may result in a cured film having room potency properties.

The aforementioned process (4) is such that a hardener system consisting of a combination of epoxy resin epoxy-polyol and ίο is used as a hardener, which provides practical requirements for thinking at low temperatures. However, the above-mentioned hardener is associated with the disadvantages that the isocyanate may be expanded in magnitude, the long-term corrosion-resistant property is unstable; compatibility with the ma 15 resin used in the corrosion-resistant coating composition is poor, and the design of the high-stress corrosion coating composition is difficult.

A coating epoxy resin based coating composition has been used in the art; · / as a durable coating composition for ships and steel structures. Ed]. coating composition has good corrosion resistance, water] 20 cabbage resistance and other properties, but its disadvantage (['use is problematic for safety and health reasons, k (• · φ' · '' tar, and tar black color makes maintenance and control difficult p: after spreading it because it makes the enclosed space look like pj operating in this mode is dangerous.

There have been many suggestions in the art for a light coating composition vs · »that is used to coat a ship's interior, such as a ballast tank, using: **: petroleum-based resin. The Applicant has also proposed unsatisfactory curing properties of the corrosion bead 3 due to the use of a hardener based thereon, whereby the coating may not have good film properties.

The inventors of the present invention have carried out thorough research to solve the above problems and have found that the aj hardener can be made by modifying a specific thionic product with an epoxy resin having good cure temperature and compatibility with a widely used petroleum based cure The use of ίο amine based hardener makes it possible to obtain a tar-corrosion-resistant coating composition having good curing temperature and to form a light-colored coating film, which are related to sion resistance, water resistance, adhesion and the like, thereby achieving the present invention.

In a first embodiment of the present invention, a base hardener is prepared by reacting the product of a condensation reaction between (a) an amine, (b) phenaldehyde, (d) an epoxy, which epoxy resin comprises at least two epoxy groups * * the amine (a) being xylene diamine and aliphatic polyamine . . ·. The phenol (b) being at least one of bisphenol A, bisphenol F and cataract !!!; a mixture of a selected compound and an alkylphenol having an alkylphenol • * ... of 9 or more carbon atoms.

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In another embodiment of the present invention, there is provided a ke composition comprising (A) an epoxy resin and (B) an amine-based cosmopolymer prepared by reacting (a) xylene diamine and an aliphatic polyamine. ·: *. a product of at least one of the condensation reaction of at least one of bisphenol A, bisphenol F, and carbolic acid with an alkyl phenol having 9 or more carbon atoms in the alkyl chain and (c) an epoxy resin comprising at least two epoxy groups 4 and alkylphenol; having an alkyl chain of 9 or more carbon atoms and (c) a product of a condensation reaction of formaldehyde with an epoxy resin comprising at least two epoxy groups thereof, and which petroleum-based resin (C) is present in an amount of 20 to 150 parts by weight of 5 resin solids for.

The amine retainer used in the first embodiment of the present invention or the second and third embodiments of the present invention is an amine-based hardener (B) (which may be referred to hereinafter as the amine-based hardener of the present invention). the product of the formaldehyde cation reaction with (d) an epoxy resin which comprises two epoxy groups per molecule.

The amine (a) of the present invention is a polyamine blend of xylene diamine. Preferred examples of aliphatic polyamides include diethylenetriamine, triethylenetetramine and the like.

Mixing ratio of xylene diamine to aliphatic polyamine .v. 2: 1 to 1: 2 weight ratio. Higher amount of xylene than this ratio to a coating film with poor adhesion properties. Secondly: ^ the aliphatic polyamine leads to poor curing properties at 20 ° C and poor compatibility with petroleum based] ♦ ·. * L *; The phenol (b) of the present invention is 9 or more carbon atoms in the alkyl chain of at least one compound selected from the group consisting of bisphenol F and carbolic acid and alkylphenol. Alkyl ... alkyl chain having 9 or more carbon atoms. The use of such an alkyl less than 9 carbon atoms undesirably attenuates y * with the petroleum based resin. Examples of alkylphenyl include nonylphenol, dodecylphenol, cardanol and the like.

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The epoxy resins (d) used in the present invention are, for example, at least two epoxy groups per molecule, and the preferred epoxy equivalent is 150-600. Particularly preferred epoxy resin (d) type epoxy resin has water resistance and cold curing properties. The amine based hardener of the present invention may be obtained by a handicapped process wherein the above components (a), (b) are followed, followed by heating and dehydrolysis at 50-180 ° C. to obtain the product of the condensation reaction of component (d) and heated at 20-200 ° C to react the amino group present in this condensed tea with the epoxy group].

The molar mixtures of the aforementioned components (a), (b), (c) and (d) are such that 0.7-1.3 moles of component (b), 0.7-1.3 moles of component and component (d) 0.2-0.5 mol kt per mol of component (a) is used. When the amount of component (a) is greater than the ec 15 mole ratio, low curing properties will degrade, and unreacted products may separate from surface to surface. On the other hand, when the amount of component (a) is mentioned above: V: less, the curing properties may be impaired and the coatings may be left unreacted on component (b), whereby the water amine * * * «*: ·] can be used as an epoxy resin hardener, has good curing properties: at low temperature, and can shorten drying and:]: at normal temperature.

For example, in the second and third embodiments of the present invention, the Ki resin (A) is, for example, one having at least two epoxy resins (A) in the molecule and having an epoxy equivalent of 150-600, preferably 180 µm. The ratio of known epoxy to phenol-type epoxy resin, aliphatic epoxy resin, glycidyl 6 may preferably be such that the elution between the hydrogen equivalent present in component (B) and the epoxy equivalent of component (A) can be in the range 0.5-1.0.

In another embodiment of the present invention, the curable resin! Optionally comprising petroleum-based resin, other liquid mi-reactive or non-reactive diluent; pigments such as continued corrosion pigment, color pigment and the like; additives such as an organic solvent, a descending agent, a coloring agent, a wetting agent, a reaction agent, an adhesive, a dewatering agent and the like.

In a third embodiment of the present invention, the petroleum base may preferably be a petroleum resin solid at a standard having a softening point in the range of 50-150 ° C, preferably 80-100 ° C. such petroleum resins include aromatics based on the polymerization of C ^ ja fractions such as styrene derivatives obtained during heavy naphtha cracking, indene and asi me me5 ja C C C C C C C C C C C C C C C al C C C C C C C C C C C C C C C C C C, dienes, for example cyclopentadiene, 1,3-Penta <* 20, respectively, for partial cyclic polymerization; resins which are strong * «:] 'clubs aromatic petroleum resin for hydrogenation, alicyclopol resin prepared by cyclopentadiene polymerization, and resins.

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When the petroleum-based resin (C) has a softening point below 50 ° C, the water resistance of * · * 25 films may be reduced, and component (C) may be applied to the surface of the film, which may retain adhesive properties. ° C, the coating coefficient * * * * may increase, resulting in inferior workability j: *** · inferior physical properties of the film.

A 7-based aromatic-based petroleum resin for hydrogen compatibility with components (A) and (B).

When the number of hydroxyl groups in this hydroxyl group-containing medium is less than 0.5 mole per molecule, compatibility with the? 5 hardener may be impaired and adversely affect the performance of the coating. Water in excess of 1.5 moles may be impaired

In a third embodiment of the present invention, this corrosive ointment composition may contain petroleum-based resin (C) in an amount of from 20 to 150 parts by weight from 50 to 150 parts by weight per 10,100 parts by weight of cured resin. When the above amount is less than 1 part, satisfactory water resistance is not achieved. On the other hand, with more than 150 parts by weight, it is impossible for the brittle coating film s to achieve good physical properties and cure: at low temperatures have been greatly reduced.

In a third embodiment of the present invention, this corrosive ointment composition may optionally include a second liquid modifier; pigments such as extender pigment, corrosion tor, color pigment and the like; reactive diluent; coating: additives commonly used in V such as organic solvent, glass 20 jet, run-off agent, wetting agent, reaction, supra. . \ adhesive, dehydrating agent, and n

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»'* According to a third embodiment of the present invention, cor 9 ··v: the coating composition is a two-component coating composition; * · A; a basic amine-based hardener (B) containing epoxy resin (A) and petroleum-based resin (C), which is usually deposited on a shaft: T: a zinc-resistant coating film such as zinc primer.

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The above coating composition can be coated with known • · tplnm Initon 11m own cLiminnr ^ i-hil / coll o il so 8

Example 1

Manufacture of amine based hardener

A reactor equipped with a stirrer and a thermometer was charged with 68 xylene diamines, 52 g (0.5 moles) of diethylenetriamine, 114 g (0.5 moles of phenol A) and 110 g (0.5 moles) of nonylphenol, followed by Hueus, adding 81 g (one). mole) 37% formalin to carry out the reaction at 100 ° C and allow the reaction to proceed for 2 hours, and pc to obtain the product of the condensation reaction by adding 95 g (0.25 n Epon # 828 (trade name, epoxy resin, epoxy equivalent: 190, maj ίο Shell Epoxy Co., Ltd.) by reacting at 80 ° C for 2 hours with a solvent mixture of toluene: isopropanol = 1: 1 to give an amine base (B1) containing 60% of non-volatile substances Hardener solution λ 900 eps (measured at 25 ° At C, 60 rpm using a type B viscometer

Examples 2-4 and Comparative Examples 1-6 Example 1, except for Table 1 es, where applicable, the black ash from the corresponding amine-based hardeners (B-2) - (B-9) * was such that high viscosity rendered the cure Vale non-existent. In Table 1, the composition is given in molar ratio, (hi • ».! * (Note 2)).

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• 20 (Note 1) Epon # 1001: Epoxy Resin, Epoxy Equivalent: 47: ·: ··: Yuka Shell Epoxy Co., Ltd., Trade Name.

* * * * · * '* (Note 2) Epiclon # 520: Trade name, monoepoxy compound, mark] v: pon Ink and Chemicals, Inc.

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table 1

Examples Comparative example 1 2 | 3 | 4 1 [2 3 | 4

Amiim Bottom Hardener B-1 B-2 B-3 B-4 B-5 B-6 B-7 B-8

Composition: a. Metaxylenediamine 0.5 0.6 0.5 0.5 1.0 - 0.5 0.5 Diethylenetriamine 0.5 0.6 0.5 0.5 - 1.0 0.5 0.5 b. bisphenolA 0.5 0.5 0.6 0.5 0.5 0.5 - 0.5 Nonylphenol 0.5 0.5 0.6 0.5 0.5 0.5 1.0 0.5 c. formaldehyde 1.0 1.0 1.0 1.0 1.0 1.0 1.0 Ύβ d. Epon 828 0.25 0.25 0.25 0.25 0.25 0 ^ 25

Epon 1001 (note 1) 0.25

Epiclon 520 (Note 2) 0.2:

Concentration of non - volatile substances 60 60 60 60 60 60 60 60

Viscosity (cps / 25 ° C) 900 400 400 2000 600 1000 400 40C

Active hydrogen equivalent 150 122 165 198 187 124 149 102 lentil

Examples 5-8 and Comparative Examples 7-12V 5 Preparation of a curable resin composition • ♦

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| . One liter reactor was charged with 100 parts of Epon 828 and the resulting amine-based hardeners as shown in Table 2, followed by stirring and stirring each time to obtain a 1: 1 resin composition. Formulations Performed in Performance • ·· v 2 ίο Performance Tests The test results are shown in Table 2. In Table 3, the following meanings are given.

··· • ♦ · · · (Note 3) Versamin F20: Trade name, Mannich modified m-blade \ active hydrogen equivalent: 80, marketed by Henkel Japan Ltd., hi: 1 QinaiHen nifnicimc-1 ΠΠ OA ·, riΠΠΠ 10 after which the coating was dried at 5 ° C, 65% relative] for 1 hour, after which the appearance of the coating film was visually evaluated.

3: No changes; 2: turbidity developed; 1: separation.

5 (* 2) Curing Properties at Low Temperature: Immediately after mixing, each sample was coated on a polished mild steel sheet (0.8 x 70 x to obtain a dry film thickness of about 250 µm) followed by drying at 5 ° C. , 65% relative for 10 hours, after which the surface of the coating film was pressed with a finger and visually evaluated as follows.

3: Heavy finger pressing does not result in coating film slip; Finger pressing leads to coating film slipping; 1: Lightweight printing leads to slip of the coating film.

15 (* 3) Adhesion Properties: Immediately after mixing, each sample was plated on steel: Y: onto a sheet of steel (2 x 70 x 150 mm) so that a dry film of about 250 µm was obtained using a applicator, followed by a pin! . ·. at 5 ° C, 65% relative humidity for 7 days, Y *. 20 each plating test panels which were subjected to cross-cuts * * ... adhesion test by forming cross-cuts on the test panels with * · [/] applied cellophane tape, and the tape was visually scored for * * t '' * as follows: 3: good; 2: partially separated; 1: Separation occurs throughout the surface.

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Table 2 __Examples__Comparison _ 5 I 6 I 7 I 8 T | 8 I 9 ΊΊ

Epon 828___100 100 100 100 100 100 100 1

Ammonium based hardener (B-l) 100________ __ (B2) ___ 100_______ _ (B-3) ____ 100______ __ (B-4) _____ 100_____ __ (B-5) ______ 100____ __ (B-6) _______ 100 __ (BJ} ________ 100

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l (B-9) ________

Amine based hardener for comparison (Note 3) _________

Performance * Compatibility__3 3 3 3 3 3 _3__3 Cold Cure 3 3 3 3 3 2 _2__7 _ Adhesion Properties | 3 3 | 3 [3 | 3 | 3 | 3 \ 7

Example 9 s Preparation of a corrosion resistant coating composition. . One liter reactor was charged with 100 parts Epon 828, 70 parts • · · · *, 100 parts talc, 100 parts hydroxyl groups petroleum (4), 10 parts anti-spill agent (note 5) and 10 c; .i .: followed by mixing and stirring the dispersants 10 to form a dispersion which acts as a rial, to this base material] iT: part of an amine-based hardener (B1) just prior to coating; T; was stirred to obtain a corrosion resistant coating composition.

Examples 10-14 and Comparative Examples 13-21 * * i i · «:: Example 9 was repeated except for the compositions shown in Table 3, to obtain the corresponding anti-corrosive coating compositions 12 (Note 5) Disparlon A630-20XN: trade name, polyamide wax, mar! moto Chemicals Ltd.

(Note 6) Coronate L: Trade name, Isocyanate hardener, Toluene-d modified product, NCO content: 13%, marketed by Nippon Polyure 5 Co., Ltd.

performance test

For each of the above corrosion-resistant coating compositions, the following performance tests are performed. The results are shown in Table 4.

(* 4) Compatibility: 10 The above (* 1) was repeated except that the corrosion-resistant surfaces were used in place of the resin compositions used in (* 1).

(* 5) Curing properties at low temperature:

The above (* 2) was repeated except that the corrosion resistant surfaces were used in place of the resin compositions used in (* 2).

is (* 6) Flexibility: * · ♦ I · • * I *, Each corrosion-resistant coating composition was coated on a greased, polished, mild steel sheet (0.8 x 70 x 150 i * * * approximately 250 µm dry film thickness using the aeration method, after which the coating was dried at 20 ° C, 65 ° A for 20 days for 7 days, the respective coating test panels were bent to a 90 degree bending angle 2 so that the surface of the coating film remained outside; fractures of the mucosa are evaluated visually: T: 3: no fractures, 2: few fractures, m ··· 25

13 primer) so that the dry film thickness was about 25 µm, the primer was dried for 1 day, the self-spraying spray was applied to give the dry film thickness about 250 µm, followed by atmospheric drying at 20 ° C, 65% RH coating the test panels

Each coating test panel was immersed for 14 days in such an upol coating test panel coating layer exposed to hot (and the back side of the test panel contacting water at 20 ° C), after which the coating surface is visually evaluated.

3: nothing abnormal; 2: slight blistering and healing; and 1: marked blistering and rust formation.

(* 8) Seawater tolerance

The coating test panels obtained as described above (* 7) were immersed in water at 50 ° C for 3 months, after which the pin was visually evaluated as follows. 3: nothing common *; 2: slight blistering; and 1: marked blistering.

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The present invention provides an amine-based coke prepared by molding a specific Mannich-re epoxy resin having good cure properties at low 1 which is well compatible with the petroleum-based resin, a film with good corrosion resistance and good adhesion

The present invention provides a tar-free, moth coating composition which has good cure properties at low and no problem for health and safety aspects of an amine-based hardener made by molding a composite product of the Mannich reaction with an epoxy resin. with. According to the present invention, the corrosion wicking composition is capable of forming a coating film which is a color having good corrosion resistance properties, water resistant and adhesive.

The corrosion-resistant coating composition of the present invention uses a high-stress, corrosion-resistant coating! in ships and steel structures.

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Claims (10)

An amine-based hardener characterized in that it is prepared by a condensation reaction of an amine, (b) phenol, and (c) formaldehyde with an epoxy resin comprising at least 5 groups per molecule, said amine (a) being a mixture of xylene diamine and its polyamine , and wherein said phenol (b) has at least one carbon atom in the alkyl chain of at least one compound selected from the group consisting of bisphenol F and carbolic acid and the alkylphenylphenol, wherein the molar ratios of the components (a), (b), (c) and (d) ; For component (b), 0.7-1.3 moles are used, component (c) is used 0, component (d) is used 0.2-0.5 moles, respectively, for each component. 2. Aminbaserad härdare enligt patentkrav 1, kännetecknad av att blandmngsförhällandet av xylendiaminen och den alifatiska polyami tryckt som viktsförhällande. An amine-based hardener according to claim 1, having a mixing ratio z of 2: 1 to 1: 2 by weight ratio of tun: xylene diamine to aliphatic polyamine. 3. Aminbaserad hardare according to claim 1, characterized in that between the blandmngsförhällandet At least the ena ur Gruppen bestäe to A, bisphenol F and karbolsyra valda compound and alkylfenolen 2 which viktsförhällande. The amine-based hardener of claim 1, wherein at least one of bisphenol A, bisphenol F and carbolic acid and the phenol (b) have a mixing ratio of from 2: 1 to 1 na. 4. A curable resin composition, characterized in that it comprises (A) i: (B) an amine-based hardener prepared by subjecting (a) a mixture of (a) ks * ψ * *: · [and an aliphatic polyamine (b) a reaction product of at least one compound selected from bisphenol A: and a carboxylic acid and an alkylphenol having v: 9 or more carbon atoms and (c) formaldehyde to react with (d) an epoxy resin which is the molar ratios of components (a), (b), (c) and (d) of the epoxy group per molecule and wherein the curing agent is used; ·· · - ·· ·. 0.7-1.3 mole of component (b) is used, component (c) is used 4. Härdande gartssammansättning, kännetecknad av att den epoxiharts och (B) Amino-bases härdare, som är framställd genom at av en condylation reaction (a) en blandning av en xylendia 15 fisking polyamin, och (b) en blandning av ätminstone en föreningi. bestäende av bisphenol A, bisphenol F och en carbolysis och en alkylkedja har 9 eller flera kolatomer, och (c) formaldehyde react epoxy resin, mica epoxy resin omfattar ätminstone epoxyigrupper f där härdande hartssammansättning molförhäländena för; \ v 20 na (a), (b), (c) och (d) and the att attenuator 0.7-1.3 mol av 0.7-1.3 mol av component (c) och 0.2 -0.5 mol av component (d) rei: mol av component (a). 5. Härdande resinsammansättning enligt patentkrav 4, covers • epoxy resin (A) omfattar epoxy group per molecule V: 25 valences 150-600. 6. Härdande resartsammansättning enligt patentkrav 4, covers. * *. blandmngsförhällandet mellan component (A) and component (B) ä • tt. % 0 et al, av bisphenol A, bisphenol F och en carbolysis och en alkylphenol, stalk a eler flera collatomer, och (c) formaldehyde reagent (s) med epoxy resin, epoxy group per molecule, och vi Rade resins (C) 20-150 viktsdelar mot 100 viktsdelaj 5 ämne i det härdande resumset och i vilken ytbeläggningssammansätta landena för de använda componentema (a), (b), (c) och (d) and murkara der 0,7-1,3 mol av component (b), 0.7-1.3 mol av component (c) och component (d) respective mot en mol av component (a). The curable resin composition of claim 4, wherein the mixing ratio of component (A) to component (B) is from 0.5 to 1.0 equivalent of the active hydrogen equivalent present in component (B) and ke epoxy equivalent. A corrosion-resistant coating composition, characterized in that s epoxy resin, (B) amine-based hardener and (C) petroleum-based amine-based hardener (B) are prepared by subjecting (a) xylene to a mixture of at least one bisphenol A, a compound selected from carbolic acid and an alkylphenol having alkyl; 10 or more carbon atoms, the product of the cation between the mixture and (c) formaldehyde reacting with (d) an epoxy resin containing two epoxy groups per molecule and containing 20 wt. The proportions of (a), (b), 15 are such that 0.7-1.3 moles of component (b) are used, and 0.7-1.3 moles of component (d) are used of 0.2- (I create per mole of component (a). Corrosion resistant coating according to claim 7, characterized in that said epoxy resin (A) comprises at least two bile. 20 leeches and has an epoxy equivalent of 150-600. The corrosion-resistant coating according to claim 7, characterized in that the petroleum-based resin (C) comprises from 0.5 to 1.5 mol · * · · ...: groups per molecule, and its soft a corrosion resistant coating according to claim 7, characterized in that the mixing between component (A) and component (B) is such that the equivalent of active hydrogen present in component (B) is; • ·; the equivalent ratio of the epoxy equivalent of component (A) is 0.5-1.0 · Ning, och en alkylphenol, stalk alkyl and har 9 eller flera kolatomer, (hällandena av de i härdaren anna componentema (a), (b), ( c) oc att man använder 0.7-1.3 mol av component (b), 0.7-1.3 mol av cor 0.2-0.5 mol av component (d) respektive mot en mol av component ( 8. The corrosion resistance of the epoxy resin (A) omfattar of the epoxy molecules and epoxy equivalents 150-600. 9. The corrosive properties of the resin (C) innefattar 0.5 rxylgroup per molecule, and the temperature of the resin at 50-150 ° C. 10. The corrosive acid component (A) and the epoxy equivalent component (A) of 0.5-1.0 are used to adjust the att equivalents of the component (A) and the epoxy equivalent. • 9 • 99 9 9 9 9 9 99 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 9 999 9 9 9 9 9 9 9 • * · * · · • I · 999 9,999 9,9 9,999