JPH0324504B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention exhibits excellent workability when pressing steel sheets (for example, hot-rolled pickled sheets, cold-rolled steel sheets, and galvanized steel sheets), has excellent rust prevention properties before and after pressing, and is further desorbed using a weak alkaline solution. The present invention relates to an energy beam-curable temporary coating composition for lubricating steel sheets that can be coated. Generally, steel sheets used for automobiles, light electrical products, and other metal processed products are treated with mineral oil-based rust inhibitors to prevent rust after being manufactured at a steel manufacturer and before being processed and painted at a processing company. is applied and shipped. Further, when press working a steel plate, press oil is generally applied in order to improve workability. However, since these anti-rust oils and press oils are non-drying, they make the steel surface sticky and are inconvenient to handle, and when pressing, the press oil scatters around the workplace, worsening the working environment. are doing. In addition, when pressing conditions are severe such as press working or deep drawing of high-strength steel plates, that is, when the surface pressure of the die is high, linear scratches or seizures (hereinafter referred to as die galling) may occur due to direct contact between the steel plate and the processing tool. ) is unavoidable and may lead to press cracks. In order to solve these problems, studies on lubricated steel plates with solid coatings are underway, and some of them have been implemented. The materials used for solid coatings include solid waxes such as paraffin waxes, naphthene waxes, higher carboxylic acid waxes, higher alcohol waxes, and higher amine waxes, and organic synthetic resins such as polyacrylic acid. can be mentioned. In addition, lubricants such as higher fatty acid salts, graphite, and molybdenum disulfide are mixed with these as necessary. However, these also have many problems when applied and dried by steel manufacturers. In other words, when coating steel materials, these materials are used after being dispersed or dissolved in a solvent, but if the solvent is an organic solvent, the working environment may deteriorate due to its volatilization, and the solvent treatment equipment may be affected. Installation,
Water is often used as a solvent due to problems such as fire hazard. However, even when water is used,
As described in No. 51-70175, when processing with continuous processing equipment at steel manufacturers, etc., the steel plate is preheated or hot air is blown after coating to speed up the evaporation of water. Even if these methods are used, for example, the steel plate is heated to 50℃ before coating, and then
When hot air at 80° C. is blown, the drying time is, for example, 10 to 15 seconds when the coating amount is 4 g/m ² .
Recent continuous processing equipment for steel plates is at least 100m/
If painting is carried out using continuous processing equipment with a processing speed of 100 m/min, it would take 17 to 15 seconds to ensure a drying time of 10 to 15 seconds.
Requires a line length of 25m. It is difficult in terms of equipment to process a steel plate over this length without coming into contact with feed rolls, pinch rolls, etc. In this regard, we focused on the fact that radically polymerizable compositions are cured in a very short time by irradiation with ionizing radiation or electromagnetic waves, especially ultraviolet rays,
The use of energy rays such as electron beams and ultraviolet rays for coating steel plates has become publicly known, including the above-mentioned Japanese Patent Application Laid-open No. 70175/1983. The present inventors have discovered that the above-mentioned energy ray irradiation cures the steel sheet, imparts lubricity superior to that of press oil required for solid lubricated steel sheets, has rust prevention properties, and is film-removable using a weak alkaline solution. The present invention was overcome by using a compound with a specific structure within a specific range, thereby completing the present invention. That is, the present invention () reacts 1 mole of a compound having one oxirane ring with 0.8 to 1.1 mole of an α,β-ethylenically unsaturated carboxylic acid having one carboxyl group, and then reacts a polybasic acid and/or its anhydride. α, obtained by reacting 0.5 to 1 mole of
100 parts by weight of a product (a) mainly consisting of a compound having one β-ethylenically unsaturated group and as necessary
A mixture containing up to 100 parts by weight of acrylic ester and/or methacrylic ester (b) having one α,β-ethylenically unsaturated group, with respect to 100 parts by weight of the mixture (b), () fluorine Resin powder lubricant 1-30 parts by weight and as required ()
The present invention relates to an energy beam-curable alkaline film-removable temporary coating composition for steel plate lubrication treatment, characterized in that it contains 0.5 to 10 parts by weight of a sensitizer. Examples of the compound having one oxirane ring (hereinafter referred to as compound A) for obtaining the product (a) used in the present invention include monoglycidyl ether, monoglycidyl ester, and alicyclic monoepoxide. Examples of the monoglycidyl ethers include butyl glycidyl ether, 2-ethylhexyl glycidyl ether, 2-methyloctyl glycidyl ether, lauryl glycidyl ether, phenyl glycidyl ether, cresyl glycidyl ether, nonyl phenyl glycidyl ether, and phenyl (2-methyl glycidyl ether). ) ether, 2,4-
dibromophenyl glycidyl ether, 2,4,
Examples include 6-tribromophenyl glycidyl ether. The monoglycidyl esters mentioned above include n-hexanoic acid glycidyl ester, 2-ethylhexanoic acid glycidyl ester, isononanoic acid glycidyl ester, benzoic acid glycidyl ester, phenyl acetic acid glycidyl ester, Cardiula E (manufactured by Ciel Chemical Co., Ltd., versatate glycidyl ester, epoxy equivalent weight 240-250), etc. Examples of the alicyclic monoepoxides include cyclohexene oxide, cyclopentene oxide, bicycloheptene oxide, dipentene monoxide, 2-pinene oxide, octylene oxide,
Examples include styrene oxide. These compounds A can be used alone or in combination of two or more. In the composition of the present invention,
Particularly when importance is placed on rust prevention and hardenability, it is desirable to use aromatic monoglycidyl ether such as phenylglycidyl ether as compound A. Further, the α,β-ethylenically unsaturated carboxylic acid having one carboxyl group (hereinafter referred to as compound B) for obtaining the product (a) includes acrylic acid, methacrylic acid, crotonic acid, cinnamic acid, Examples include monoalkyl itaconic acid esters (e.g. methyl ester, ethyl ester, n-propyl ester, isopropyl ester).
A species or a mixture of two or more kinds may be used. From the viewpoint of curability of the composition of the present invention, it is preferable to use acrylic acid. In addition, the polybasic acid and its anhydride (hereinafter referred to as compound C) for obtaining product (a) are as follows:
Phthalic acid, isophthalic acid, tetrahydrophthalic acid, methyltetrahydrophthalic acid, hexahydrophthalic acid, methylhexahydrophthalic acid, hymic acid, methyl hymic acid, trimellitic acid,
Pyromellitic acid, succinic acid, adipic acid, phthalic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, hexahydrophthalic anhydride, methylhexahydrophthalic anhydride, hymic anhydride, methyl hymic anhydride, trimellitic anhydride, anhydride Examples include pyromellitic acid and succinic anhydride, and these may be used alone or in combination of two or more. From the viewpoint of curability and rust prevention properties of the composition of the present invention, phthalic acid, tetrahydrophthalic acid,
It is desirable to use cyclic polybasic acids such as methyltetrahydrophthalic acid, hexahydrophthalic acid, methylhexahydrophthalic acid, hymic acid, methylhymic acid, trimellitic acid, pyromellitic acid, and their anhydrides. The product (a) used in the present invention is obtained by first reacting compound A and compound B, and adding compound C to the reaction product.
It can be obtained by reacting. The reaction between compound A and compound B can be carried out without a catalyst, but it is desirable to carry out the reaction at the lowest possible temperature and in the shortest possible time to avoid thermal polymerization of the α,β-ethylenically unsaturated group. , for which the use of catalysts is advantageous. Examples of the catalyst include tertiary amines such as N,N-dimethylaniline, triethylamine, benzyldimethylamine, and N,N-dimethylaminoethyl methacrylate;
Ammonium salts such as trimethylbenzylammonium chloride give good results. Additionally, in order to prevent thermal polymerization of α,β-ethylenically unsaturated groups during the reaction, common thermal polymerization inhibitors (e.g., hydroquinone, t-butylhydroquinone, hydroquinone monomethyl ether, catechol, t-
It is desirable to use phenols such as butylcatechol and quinones such as benzoquinone and diphenylbenzoquinone in an amount of 0.01 to 0.5% by weight based on the total amount of compound A and compound B. The reaction may be carried out at a temperature of 100-130°C for 1-15 hours. If it is difficult to carry out the reaction without a solvent, the reaction may be carried out using an agent having no carboxyl group or hydroxyl group (for example, toluene, xylene, butyl acetate) as a solvent. The reaction product obtained in this way is not isolated, but is added with compound C and reacted at a temperature of 100 to 130°C to produce the desired product (a).
(ie, a product mainly consisting of a compound having one α,β-ethylenically unsaturated group) is obtained. When an acid anhydride of a polybasic acid is used as compound C, if the reaction is delayed or the reaction system has a problem with thermal stability, add the above catalyst or thermal polymerization inhibitor to start the reaction. Just move on. Furthermore, when the reaction system has a high viscosity and is difficult to stir, the above-mentioned solvents may be used. When using a polybasic acid as compound C,
Conventional esterification methods may be employed. That is, the reaction may be allowed to proceed by using an acid catalyst such as para-toluenesulfonic acid and removing water produced as the reaction proceeds from the system by azeotropy with the solvent. When the product (a) thus obtained is synthesized using a solvent, the solvent is distilled off under reduced pressure. If necessary, the solvent may be distilled off under reduced pressure after adding the acrylic ester and/or methacrylic ester (b) which is a component of the composition of the present invention. Since compound A does not have a polymerizable double bond,
Not cured by active energy rays. Therefore, it is necessary to react with compound B as efficiently as possible. Further, since Compound B is highly acidic, it is desirable to leave it as little as possible from the viewpoint of rust prevention. Based on these facts, compound A and compound B
The molar ratio used is 1:0.8-1.1, preferably 1:0.9
A range of ~1.0 is desirable. Compound C is preferably used in an amount of 0.5 to 1.0 mol per mol of compound A. If it is less than 0.5 mol, the amount of carboxyl groups introduced into the curable component will decrease, resulting in poor film removal, while if it exceeds 1.0 mol, an excessive amount of compound C will remain, reducing the rust prevention properties. The acrylic ester and methacrylic ester (b) having one α,β-ethylenically unsaturated group used in the present invention may be those conventionally used in the field, such as methyl (meth)
Acrylate (indicates both methyl acrylate and methyl methacrylate; the same applies hereinafter), ethyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate,
Hexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, cyclohexyl (meth)acrylate, benzyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, 2-methoxyethyl (meth)acrylate ) acrylate,
Examples include cellosolve (meth)acrylate, 2-butoxyethyl (meth)acrylate, carbitol (meth)acrylate, dipropylene glycol monomethyl ether monoacrylate, triethylene glycol monomethyl ether monoacrylate, and tetrahydrofurfuryl (meth)acrylate. These may be used alone or in combination of two or more. The compound (b) is used as necessary for the purpose of adjusting the viscosity when coating the composition of the present invention, and 100 parts (parts by weight,
It is desirable to mix in an amount of up to 100 parts. Mixing in an excessive amount will result in a decrease in the curability of the composition of the present invention. Examples of lubricants include organic and inorganic lubricants. The former organic lubricants include fatty acids (e.g. oleic acid, linoleic acid, palmitic acid,
stearic acid, etc.), metal soaps (for example, by reacting organic acids such as lauric acid, stearic acid, ricinoleic acid, rosin, and naphthenic acid with metals such as aluminum, barium, calcium, iron, magnesium, lead, tin, and zinc). fatty acid soaps (e.g. those obtained by reacting the above fatty acids with sodium, potassium, ammonia), paraffin hydrocarbons (e.g. paraffin wax, beeswax, vegetable wax, chlorinated paraffin, etc.), high grade Alcohols (e.g. lauryl alcohol, stearyl alcohol, palmityl alcohol, etc.), fatty acid amides (e.g. those obtained from the above fatty acids and amines), fluororesin powder, polyethylene wax,
Examples include polyethylene powder, polypropylene powder and derivatives thereof. Examples of the latter inorganic lubricant include graphite, molybdenum disulfide, boron nitride, and the like. These can be used alone or in combination of two or more. However, in the present invention, in order to impart good press workability without impairing the curability and adhesion of the target composition, it is necessary to use the above-mentioned fluororesin powder, especially tetrafluoroethylene resin powder. preferable. Commercially available tetrafluoroethylene resins include "Hostaflon TF9202", "Hostaflon TF9205" (manufactured by Hoechst Japan Co., Ltd.), "Rublon L-2", "Hostaflon L-2", and "Hostaflon TF9205" (manufactured by Hoechst Japan).
5" (manufactured by Daikin Industries, Ltd.). The above lubricant () is blended in an amount of 1 to 30 parts per 100 parts of the mixture () of the above-mentioned product (a) and acrylic ester and/or methacrylic ester (b) blended as necessary. do. If the amount is less than the specified amount, the lubricating effect of the composition of the present invention will be poor, while if it is in excess, the strength of the cured coating will decrease, causing problems such as coating pieces adhering to the die during press processing. will occur. The sensitizer used in the present invention may be incorporated when the composition of the present invention is cured by ultraviolet rays, as is conventionally known, and does not necessarily need to be incorporated in the case of electron beam curing. Specific examples thereof may also be known in the art. For example, benzoin,
Benzoin methyl ether, benzoin ethyl ether, benzoin isopropyl ether, benzoin n-butyl ether, benzoin butyl ether, benzophenone, 2-chlorothioxanthone, 2-methylthioxanthone, 2-isopropylthioxanthone, 4,4'-dimethylbenzoin, benzyl dimethyl ketal, 1 , 1,1-trichloroacetophenone, 2-hydroxy-2-
Methyl-1-phenylpropan-1-one, 1-
(4-isopropylphenyl)-2-hydroxy-
Examples include 2-methylpropan-1-one.
These can be used alone or in combination of two or more. This sensitizer () is blended in an amount of 0.5 to 10 parts per 100 parts of the above mixture (). If the amount is less than the specified amount, the curing of the composition of the present invention will be slow during UV curing, while if it is in excess, the curability will not improve, which is economically disadvantageous. The composition of the present invention includes the above-mentioned components () to ().
In addition, if necessary, materials used in normal paint compositions such as antifoaming agents, anti-sagging agents, surface conditioners, rust preventives, plasticizers, colorants, and solvents may be added to provide rust prevention and film removal properties. It may be blended within a range that does not have an adverse effect on. The composition of the present invention can be obtained by mixing the above-mentioned components using a conventional dispersing machine (for example, a ball mill, three-roll mill, sand mill, high-speed mixer, etc.). Next, conventionally known techniques may be employed to coat steel materials with the composition of the present invention. That is, the coating can be carried out using conventional methods such as roll coater, spray, curtain flow coater, etc. However, in order to coat a high viscosity material such as the composition of the present invention at a low coating amount of ² to 5 g/m2, It is desirable to use a hot roll coater. The composition applied to the steel material may then be cured using ultraviolet rays or electron beams in accordance with conventional methods. As a UV source, the wavelength is 200 ~
A normal high-pressure mercury lamp that generates 450 mμ of ultraviolet light,
Ultra-high pressure mercury lamps, metal halide lamps, etc. can be used. In the electron beam irradiation process, an electron beam accelerator that generates an electron beam with an energy of 10 KeV to 3 MeV can be used. The lubricated steel sheet thus obtained is coated with a solid film that is excellent in rust prevention, press workability, and removability with a weak alkaline solution. Next, the present invention will be specifically explained with reference to Reference Examples, Examples, and Comparative Examples. In addition, in these examples, parts mean parts by weight. Reference Example 1 150 parts (1 mol) of phenyl glycidyl ether and 1.1 parts of N,N-dimethylaminoethyl methacrylate were placed in a flask equipped with a stirrer, and the temperature was raised to 110°C. Thereafter, while maintaining the same temperature and stirring, a mixture of 72 parts (1 mole) of acrylic acid and 0.2 part of hydroquinone monomethyl ether was added dropwise over about 1 hour. Thereafter, the mixture was reacted at the same temperature for 5 hours with stirring. After the reaction product was allowed to cool to room temperature, 41.6 parts of toluene, 0.8 parts of N,N-dimethylaminoethyl methacrylate, 0.2 parts of hydroquinone monomethyl ether, and 152 parts (1 mol) of tetrahydrophthalic anhydride were added thereto, and the mixture was stirred. The reaction was carried out at 115°C for 3 hours to obtain a solution of reaction product (a). The acid value of this reaction product solution was 144. The general formula of the reaction product (a) is as follows. After that, the reaction product solution was left to cool to 50°C,
93.5 parts of 2-hydroxypropyl acrylate, which is an acrylic ester (b), was added and stirring was continued to form a uniform solution. Next, toluene was distilled off from this solution under reduced pressure to obtain a solution consisting of 80 parts of the reaction product (a) and 20 parts of the acrylic ester (b). Reference Example 2 150 parts (1 mol) of phenyl glycidyl ether and 1.1 parts of N,N-dimethylaminoethyl methacrylate were placed in a flask equipped with a stirrer, and the temperature was raised to 110°C. Thereafter, while maintaining the same temperature and stirring, a mixture of 72 parts (1 mole) of acrylic acid and 0.2 part of hydroquinone monomethyl ether was added dropwise over about 1 hour. Thereafter, the mixture was reacted at the same temperature for 5 hours with stirring. After the reaction product was allowed to cool to room temperature, 38.2 parts of toluene, 0.6 parts of N,N-dimethylaminoethyl methacrylate, 0.1 part of hydroquinone monomethyl ether, and 121.6 parts (0.8 mol) of tetrahydrophthalic anhydride were added thereto, and the mixture was stirred. 3 at 115℃
The reaction was carried out for a period of time to obtain a solution of the reaction product (a). The acid value of this reaction product solution was 115. The general formula of the reaction product (a) is as follows. After that, the reaction product solution was left to cool to 50°C,
86 parts of 2-hydroxypropyl acrylate, which is an acrylic ester (b), was added and stirring was continued to form a uniform solution. Next, toluene was distilled off from this solution under reduced pressure to obtain a solution consisting of 80 parts of the reaction product (a) and 20 parts of the acrylic ester (b). Reference Example 3 150 parts (1 mol) of phenyl glycidyl ether and 1.1 parts of N,N-dimethylaminoethyl methacrylate were placed in a flask equipped with a stirrer, and the temperature was raised to 110°C. Thereafter, while maintaining the same temperature and stirring, a mixture of 72 parts (1 mole) of acrylic acid and 0.2 part of hydroquinone monomethyl ether was added dropwise over about 1 hour. Thereafter, the mixture was reacted at the same temperature for 5 hours with stirring. After the reaction product was allowed to cool to room temperature, 41.1 parts of toluene, 0.7 parts of NN-dimethylaminoethyl methacrylate, 0.1 part of hydroquinone monomethyl ether, and 148 parts (1 mol) of phthalic anhydride were added thereto, and the mixture was heated at 115°C with stirring. Let it react for 3 hours,
A solution of reaction product (a) was obtained. The acid value of this reaction product solution was 150. The general formula of the reaction product (a) is as follows. After that, the reaction product solution was left to cool to 50°C,
92.5 parts of tetrahydrofurfuryl acrylate, which is an acrylic ester (b), was added, and stirring was continued to form a uniform solution. Next, Torun was distilled off from this solution under reduced pressure to obtain a solution consisting of 80 parts of the reaction product (a) and 20 parts of the acrylic ester (b). Reference Example 4 150 parts (1 mol) of phenyl glycidyl ether and 1.1 parts of N,N-dimethylaminoethyl methacrylate were placed in a flask equipped with a stirrer, and the temperature was raised to 110°C. Thereafter, while maintaining the same temperature and stirring, a mixture of 72 parts (1 mole) of acrylic acid and 0.2 part of hydroquinone monomethyl ether was added dropwise over about 1 hour. Thereafter, the mixture was reacted at the same temperature for 5 hours with stirring. After the reaction product was allowed to cool to room temperature, 35.8 parts of toluene, 0.5 parts of N,N-dimethylaminoethyl methacrylate, 0.1 part of hydroquinone monomethyl ether, and 100 parts (1 mol) of succinic anhydride were added thereto, and the mixture was stirred for 120 parts. React at ℃ for 3 hours,
A solution of reaction product (a) was obtained. The acid value of this reaction product solution was 170. The general formula of the reaction product (a) is as follows. After that, the reaction product solution was left to cool to 50°C,
80.5 parts of tetrahydrofurfuryl acrylate, which is an acrylic ester (b), was added and stirring was continued to form a uniform solution. Next, toluene was distilled off from this solution under reduced pressure to obtain a solution consisting of 80 parts of the reaction product (a) and 20 parts of the acrylic ester (b). Reference Example 5 Put 186 parts (1 mol) of 2-ethylhexyl glycidyl ether and 1.3 parts of N,N-dimethylaminoethyl methacrylate into a flask equipped with a stirrer, and add 110 parts of N,N-dimethylaminoethyl methacrylate.
The temperature was raised to ℃. Thereafter, while maintaining the same temperature and stirring, a mixture of 72 parts (1 mole) of acrylic acid and 0.3 part of hydroquinone monomethyl ether was added dropwise over about 1 hour. Thereafter, the mixture was reacted at the same temperature for 5 hours with stirring. After the reaction product was allowed to cool to room temperature, 45.6 parts of toluene, 0.8 parts of N,N-dimethylaminoethyl methacrylate, 0.2 parts of hydroquinone monomethyl ether, and 152 parts (1 mol) of tetrahydrophthalic anhydride were added thereto, and the mixture was stirred. The reaction was carried out at 115°C for 6 hours to obtain a solution of the reaction product (a). The acid value of this reaction product solution was 136. The general formula of the reaction product (a) is as follows. After that, the reaction product solution was left to cool to 50°C,
102.5 parts of tetrahydrofurfuryl acrylate, which is an acrylic ester (b), was added, and stirring was continued to form a uniform solution. Next, toluene was distilled off from this solution under reduced pressure to obtain a solution consisting of 80 parts of the reaction product (a) and 20 parts of the acrylic ester (b). Reference Example 6 150 parts (1 mole) of phenyl glycidyl ether and 1.1 parts of N,N-dimethylaminoethyl methacrylate were placed in a flask equipped with a stirrer, and the temperature was raised to 110°C. Thereafter, while maintaining the same temperature and stirring, a mixture of 72 parts (1 mole) of acrylic acid and 0.2 part of hydroquinone monomethyl ether was added dropwise over about 1 hour. Thereafter, the reaction was continued at the same temperature for 5 hours with stirring. Reference Example 7 In a flask with a stirrer, 24 parts of toluene, 100 parts (1 mole) of succinic anhydride, 116 parts (1 mole) of 2-hydroxyethyl acrylate, 1.1 g of N,N-dimethylaminoethyl methacrylate, and 0.2 part of hydroquinone monomethyl ether. was added and reacted at 100°C for 5 hours. Thereafter, toluene was distilled off under reduced pressure to obtain a reaction product. Examples 1-5 Each component shown in Table 1 was mixed in the indicated amount and uniformly dispersed using a three-roll mill. In addition, fluororesin powder in the table: "Luburon L-2" manufactured by Daikin Industries, Ltd.

[Table] The obtained composition was applied to a 0.8 mm thick cold-rolled steel plate using a natural roll coater to a film thickness of 2 to 4 μm. Thereafter, the coated steel plate was passed under two ozone-type concentrating ultraviolet irradiation lamps with an input of 80 W/cm at a speed of 30 m/min to obtain a lubricated steel plate. A sample piece was cut from this steel plate and a performance investigation was conducted. The results are shown in Table 2. The details of the test method adopted are as follows. (1) Press workability: 50φ cylindrical deep drawing test, BHF = 0.5 tons, presence or absence of drawing through at each drawing ratio (O: drawing through,
X: Breakage) and maximum punch load measurement. (2) Film removal performance: Using 20g of "Fine Cleaner 4349" manufactured by Nippon Parkerizing Co., Ltd., the film removal rate was measured at each spray time at 60°C and a spray pressure of 1.0Kg/ ^cm2 . (3) Rust prevention: Wet and dry cycle test (1 cycle: 60℃,
Measurement of rusted area in each cycle (98% RH, 2 hours + 60℃ drying 2 hours). Comparative Examples 1-2 In the same manner as in Example 1, each component shown in Table 3 was mixed in the indicated amounts to obtain a composition. The composition was coated on a steel plate in the same manner as in Example 1 and subjected to performance investigation. The results are shown in Table 2.

【table】

[Table] Comparative Example 3 A cold-rolled steel plate coated with a commercially available press oil (“Press Oil #620” manufactured by Nippon Craft Oil Co., Ltd.) was subjected to a performance investigation in the same manner as in Example 1. The results are shown in Table 2.

【table】

Claims (1)

[Claims] 1 () 1 mol of a compound having one oxirane ring and 0.8 to 1.1 mol of an α,β-ethylenically unsaturated carboxylic acid having one carboxyl group are reacted, and then 0.5 to 1 mol of a polybasic acid and/or its anhydride is reacted.
A product mainly composed of a compound having one α,β-ethylenically unsaturated group obtained by reacting moles
(a) A mixture containing 100 parts by weight and, if necessary, up to 100 parts by weight of an acrylic ester and/or methacrylic ester (b) having one α,β-ethylenically unsaturated group; Energy for steel sheet lubrication treatment, characterized in that 1 to 30 parts by weight of () fluororesin powder lubricant and () 0.5 to 10 parts by weight of sensitizer are blended to 100 parts by weight. Line-curing alkaline-removable temporary coating composition.