JPH0597944A - Resin composition, solder resist resin composition and their cured product - Google Patents

Abstract

PURPOSE:To provide a resin composition containing an epoxy (meth)acrylate produced by reacting a specific epoxy resin with (meth)acrylic acid, capable of being diluted or developed, and giving cured products having excellent soldering heat resistance, chemical resistance and electrically insulating property. CONSTITUTION:The objective resin composition contains an epoxy (meth)acrylate which is the reaction product of (A) an epoxy resin of formula I [R1, R2 are H, 1-4C alkyl; n is an integer of >=1; M is H, a group of formula II (when n is >=2, at least one of M is a group of formula II)] with (B) a (meth)acrylic acid.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a resin composition useful as a solder resist resin composition for printed wiring boards and a cured product thereof.

[0002]

2. Description of the Related Art In recent years, UV curable resin compositions have been widely used in various fields for reasons such as resource saving, energy saving, workability improvement and productivity improvement. In the field of printed wiring board processing, various inks such as solder resist inks and marking inks have been shifting from conventional thermosetting resin compositions to ultraviolet curable resin compositions for the same reason. Among them, the solder resist ink quickly moved to an ultraviolet curable resin composition.

[0003]

Although a screen printing method has been widely used as a method for forming a resist pattern on a printed wiring board, when such a screen printing method is used, in many cases, bleeding, bleeding, or bleeding during printing, or Causes a phenomenon such as sagging, which makes it impossible to cope with the recent increase in the density of printed wiring boards. To solve these problems, dry film type photoresists and liquid developable resist inks have been proposed and used, but in the case of dry film type photoresists, bubbles are generated during thermocompression bonding. It is easy to use, there is concern about heat resistance and adhesion, and it is expensive. On the other hand, currently available liquid resists are
There are those that use organic solvents as developing solutions and those that develop with dilute aqueous alkali solutions, but those that use organic solvents are not only risk of ignition, air pollution, but also expensive solvents and curing. There are also problems with solvent resistance and acid resistance of the product.
Further, regarding a liquid resist that can be developed with a dilute alkaline aqueous solution, an organic solvent is used as a diluent for the resist, and there is a risk of ignition in the case of spray coating.
Further, since development is performed with a dilute aqueous alkali solution, sodium ions and the like may remain in the resist coating film, which is a problem.

[0004]

Means for Solving the Problems As a result of intensive studies for solving the above-mentioned problems, the present inventors have found that water can be used as a diluent for a resin composition, and that it can be developed with water and cured. The film has excellent adhesion, solder heat resistance, chemical resistance, gold plating resistance, etc., and has succeeded in providing a resin composition and a cured product thereof which are particularly useful as a solder resist resin composition.

That is, the present invention uses the formula (1)

[0006]

[Chemical 5] (In the formula, R ₁ and R ₂ are each independently hydrogen or an alkyl group having 1 to 4 carbon atoms, n is an integer of 1 or more, M is hydrogen or

[0008]

[Chemical 6]

[0009] However, when n is 1, M is always

[0010]

[Chemical 7]

When n is 2 or more, at least one M is

[0012]

[Chemical 8]

[0013] ) A resin composition containing an epoxy (meth) acrylate which is a reaction product of an epoxy resin represented by (4) and (meth) acrylic acid, particularly a solder resist resin composition, and 2 a cured product of the resin composition described in 1 above. ..

The epoxy (meth) acrylate used in the present invention includes an epoxy resin represented by the formula (1) and (meth)
It can be obtained by reacting acrylic acid.
The epoxy resin represented by the formula (1) is a compound represented by the formula (2).

[0015]

[Chemical 9]

It can be obtained by reacting an alcoholic hydroxyl group of the formula (wherein R ₁ , R ₂ and n have the same meanings as in formula (1)) with epichlorohydrin. The compound represented by the formula (2) is a hydantoin compound represented by the formula (3).

[0017]

[Chemical 10]

(In the formula, R ₁ and R ₂ have the same meanings as in formula (1).) For example, hydantoin, 5,5-dimethylhydantoin, 5,5-diethylhydantoin,
5-ethyl-5-methylhydantoin, 5,5-dipropylhydantoin and the like and compounds represented by the formula (4)

[0019]

[Chemical 11]

(Wherein R ₁ and R ₂ have the same meanings as in formula (1)), and 1 mol of the hydantoin compound represented by formula (3) is represented by formula (4). Compound
It can be obtained by reacting at a ratio of 2 to 2 mol, preferably at 130 to 160 ° C. for usually 5 to 10 hours.

Next, the amount of epichlorohydrin used is preferably 1 equivalent or more with respect to 1 equivalent of the alcoholic hydroxyl group in the formula (2). However, hydroxyl group 1
If the amount exceeds 15 times the equivalent weight, the effect of increasing the weight is almost lost and the volumetric efficiency is deteriorated, which is not preferable. It is preferable to use a quaternary ammonium salt such as tetramethylammonium chloride or benzyltrimethylammonium chloride as a catalyst when the compound represented by the formula (2) is reacted with epichlorohydrin. The amount used is preferably 0.3 to 50 g per 1 equivalent of the alcoholic hydroxyl group in the formula (2).

During the reaction, alkali metal hydroxide (eg,
It is preferable to use caustic soda, caustic potash, lithium hydroxide, calcium hydroxide, etc.). The amount of the alkali metal hydroxide used is preferably approximately equivalent to 1 equivalent of the epoxidized alcoholic hydroxyl group of the compound represented by the formula (2). The alkali metal hydroxide may be solid or aqueous solution. When using an aqueous solution, during the reaction,
The reaction can be carried out while distilling the water in the reaction system out of the reaction system under normal pressure or reduced pressure.

The reaction temperature is preferably 30 to 100 ° C.,
If the reaction temperature is lower than 30 ° C, the reaction becomes slow and a long-time reaction is required. When the reaction temperature exceeds 100 ° C., many side reactions occur, which is not preferable. After completion of the reaction, excess epichlorohydrin may be distilled off under reduced pressure, and then the produced resin may be dissolved in an organic solvent to carry out a dehydrohalogenation reaction with an alkali metal hydroxide. As the organic solvent, ityl isobutyl ketone, toluene, xylene and the like can be used, but methyl isobutyl ketone is preferably used.

The epoxy (meth) acrylate used in the present invention is about 0.3 to 1.5 of (meth) acrylic acid based on 1 equivalent of the epoxy group of the epoxy resin represented by the formula (1).
The reaction is carried out in an equivalent amount, particularly preferably in a ratio of about 0.5 to 1.0 equivalent, and as a diluent during the reaction, methyl ethyl ketone, ethyl cellosolve, ethyl cellosolve acetate, butyl cellosolve, diethylene glycol monomethyl ether, diethylene glycol dimethyl ether, diethylene glycol, which is soluble in water, is used as a diluent. It is preferable to use solvents such as propylene glycol monomethyl ether, dipropylene glycol monoethyl ether, isopropanol and n-propanol. It is preferable to use a catalyst (eg, triethylamine, benzyldimethylamine, methyltriethylammonium chloride, triphenylstibine, triphenylphosphine, etc.) to accelerate the reaction, and the amount of the catalyst to be used is based on the reaction raw material mixture. 0.1
It is preferably used in the range of 10 to 10 weight. In order to prevent the polymerization during the reaction, it is preferable to use a polymerization inhibitor (for example, metoquinone, hydroquinone, phenothiazine, etc.), and the amount thereof is relative to the reaction raw material mixture.
It is preferably used in the range of 0.01 to 1% by weight. The reaction temperature is preferably 60 to 150 ° C., and the reaction time is usually 5
~ 60 hours.

The amount of epoxy (meth) acrylate contained in the resin composition of the present invention (hereinafter simply referred to as composition) is
It is preferably 5 to 90% by weight, and particularly preferably 10 to 80% by weight in the composition.

The composition of the present invention further comprises diethylene glycol di (meth) acrylate, triethylene glycol di (meth) acrylate, triethylene glycol diglycidyl ether di (meth) acrylate, pentaerythritol tri (meth) acrylate, Trishydroxyethyl isocyanurate di (meth) acrylate, reactive monomers such as dipentaerythritol penta and hexaacrylate, phenol novolac type epoxy resin, cresol novolac type epoxy resin, bisphenol type epoxy resin, tris (2,3-epoxy) (Propyl) isocyanurate, epoxy compounds such as hydantoin epoxy resin, phenol novolac type epoxy resin and cresol novolac type epoxy resin (meta)
Acrylic acid reactants or compounds obtained by reacting these reactants with an acid anhydride can be contained. The amount of these used is the above-mentioned epoxy (meth) acrylate 1
0 to 100 parts by weight is preferable with respect to 00 parts by weight. When the epoxy compound is used, an epoxy resin curing agent (for example, dicyandiamide and its derivative, imidazole compound, triazine compound, urea compound, etc.)
Can be used alone or in combination of two or more. When an epoxy resin curing agent is used, the amount used is preferably 0.5 to 50 parts by weight with respect to 100 parts by weight of the epoxy compound.

The composition of the present invention may further contain water as a diluent in any amount.

As a method for curing the composition of the present invention to obtain a cured product, there are curing methods by electron beam, ultraviolet ray and heat, but it is preferable to cure by ultraviolet ray and, if necessary, heat. A photopolymerization initiator is used in the case of curing with ultraviolet rays. As the photopolymerization initiator, any known photopolymerization initiator can be used, but one having good storage stability after blending is desirable. Examples of such a photopolymerization initiator include, for example, benzoin, benzyl, benzoisomethyl ether, benzoin isopropyl ether, acetophenone, 2,2-dimethoxy-2-phenylacetophenone, 2,2-diethoxy-2-phenylacetophenone, 1,1-dicucloacetophenone, 1-hydroxycyclohexyl phenyl ketone, 2-methyl-1
-[4- (methylthio) phenyl] -2-morpholinopropan-1-one, N, N-dimethylaminoacetophenone, 2-methylanthraquinone, 2-ethylanthraquinone, 2-tert-butylanthraquinone, 1-chloroanthraquinone, 2-amyl anthraquinone, 2-
Aminoanthraquinone, 2,4-dimethylthioxanthone, 2,4-diethylthioxanthone, 2,4-diisopropylthioxanthone, acetophenone dimethyl ketal, benzophenone, methylbenzophenone, 4,4
Examples include ′ -dichlorobenzophenone, 4,4′-bisdiethylaminobenzophenone, Michler's ketone, and the like. These may be used alone or in combination of two or more. Furthermore, such a photopolymerization initiator is
N, N-dimethylaminobenzoic acid ethyl ester, N,
The known photosensitizers such as N-dimethylaminobenzoic acid isoamyl ester, triethanolamine and triethylamine can be used alone or in combination of two or more kinds. A preferred combination is 2,4-diethylthioxanthone or 2-isopropylthioxanthone and N, N-.
Combination with dimethylaminobenzoic acid ethyl ester, 2
-Methyl-1- [4- (methylthio) phenyl] -2-
A combination of morpholinopropan-1-one (Irgacure 907, manufactured by Ciba-Geigy) and 2,4-diethylthioxanthone or 2-isopropylthioxanthone is used. The proportion of the photopolymerization initiator used is preferably 0 to 50 parts by weight, and particularly preferably 4 to 35 parts by weight, per 100 parts by weight of the epoxy (meth) acrylate. When curing with heat, the heating temperature is preferably 120 to 170 ° C., and the heating time is preferably 30 minutes to 2 hours.

The composition of the present invention further comprises inorganic fillers such as talc, silica, alumina, barium sulfate, magnesium oxide and the like, and cyanine green as a color pigment,
Cyanine blue or the like can be added. In addition,
As required, hexamethoxymelamine, melamine resins such as hexabutoxymelamine, thixotropic agents such as Aerosil, silicone, fluoropolymers, leveling agents such as acrylic copolymers, defoaming agents, ultraviolet rays, absorbers,
An antioxidant, a polymerization inhibitor, etc. can also be added.

The composition of the present invention can be obtained by blending the blending components preferably in the above proportions and uniformly mixing them with a roll mill or the like. When the composition of the present invention is used as a solder resist resin composition, it is cured as follows to obtain a cured product. That is, a screen printing method, a spray method, a roll coating method, an electrostatic coating method, a printed wiring board,
10 to 100μ by the method such as curtain flow coating
The resin composition of the present invention is applied in a thickness of m
After being dried at 80 ° C., the negative film is brought into direct contact with the coating film, followed by irradiation with ultraviolet rays, and the unirradiated portion of the coating film is dissolved and removed with water, and then at 120 to 170 ° C. for 30 minutes to 1 minute.
A cured film is obtained by heat curing for a time.

The composition of the present invention is particularly useful as a solder resist resin composition, and is also useful as an insulating paint, a printing ink, a coating agent and the like. The resin composition containing the epoxy (meth) acrylate of the present invention is excellent in terms of developability and hardness of a cured product, solder heat resistance, acid resistance, alkali resistance, solvent resistance, insulation resistance and the like.

[0032]

EXAMPLES The present invention will be described in more detail below with reference to examples. The parts in the synthetic examples and examples are parts by weight. Synthesis Example of Epoxy Resin Represented by Formula (1) Synthesis Example 1 2,4-Diglycidyl-5,5-dimethylhydantoin (epoxy equivalent 137) 548 parts, 5,5-dimethylhydantoin 128 parts, triethanolamine 2 parts Was added and the reaction product 67 was obtained by stirring at 140 ° C. for 5 hours.
6 parts (epoxy equivalent: 360, softening point: 76 ° C., average value of n in formula (2): 2.1) was added to epichlorohydrin 20.
After dissolving in 00 parts, 13 parts of tetramethylammonium chloride was added, and 98.5% Na was added at 70 ° C. with stirring.
104 parts of OH were added over 100 minutes. After the addition, the reaction was further performed at 70 ° C. for 3 hours. Then, most of the excess unreacted epichlorohydrin was distilled off under reduced pressure, the reaction product containing the by-product salt was dissolved in 1500 parts of methyl isobutyl ketone, the by-product salt was filtered and removed, and then methyl isobutyl ketone was distilled. Then, 722 parts of an epoxy resin (a) having an epoxy equivalent of 216 and a softening point of 65 ° C. was obtained. When the obtained epoxy resin (a) is calculated from the epoxy equivalent, about 1.8 of 2.1 alcoholic hydroxyl groups in the formula (2) are epoxidized.

Synthesis Example 2 822 parts of 2,4-diglycidyl-5,5-dimethylhydantoin (epoxy equivalent 137), 256 parts of 5,5-dimethylhydantoin and 3.5 parts of triethanolamine were added, and the mixture was added at 140 ° C. for 7 hours. Reaction product 1 obtained by stirring
After dissolving 078 parts (epoxy equivalent 577, softening point 90 ° C., average value of n in formula (2) is 4.3) in 4070 parts epichlorohydrin, 26 parts tetramethylammonium chloride are added, and the mixture is stirred at 70 ° C. At 98.
211 parts of 5% NaOH was added over 100 minutes. After the addition, the reaction was further performed at 70 ° C. for 3 hours. Then, most of the excess unreacted epichlorohydrin was distilled off under reduced pressure, and the reaction product containing a by-product salt was removed with methyl isobutyl ketone 2500.
Part, and the by-product salt was filtered off to remove it, and then methyl isobutyl ketone was distilled to obtain 1221 parts of an epoxy resin (b) having an epoxy equivalent of 239 and a softening point of 81 ° C. The epoxy resin (b) thus obtained was calculated from the epoxy equivalents to give about 3.1 of the 4.1 alcoholic hydroxyl groups in the formula (2).
Seven are epoxidized.

Synthesis Example 3 2,4-Diglycidyl-5,5-diethylhydantoin (epoxy equivalent 153), 612 parts, 5,5-diethylhydantoin 156 parts and 2.5 parts of triethanolamine were added, and the mixture was added at 5 ° C at 140 ° C. After dissolving 768 parts of a reaction product obtained by stirring for time (epoxy equivalent 410, softening point 73 ° C., average value of n in formula (2) is 2.1) in 2000 parts of epichlorohydrin, tetramethylammonium chloride Add 14 parts and stir at 70 ° C. for 9
104 parts 8.5% NaOH were added over 100 minutes.
After the addition, the reaction was further performed at 70 ° C. for 3 hours. Then, most of the excess unreacted epichlorohydrin was distilled off under reduced pressure,
The reaction product containing by-product salt was treated with methyl isobutyl ketone 16
It was dissolved in 00 parts and filtered to remove the by-product salt, and then methyl isobutyl ketone was distilled to obtain 833 parts of an epoxy resin (c) having an epoxy equivalent of 238 and a softening point of 64 ° C. In the obtained epoxy resin (c), when calculated from the epoxy equivalent, about 1.9 of 2.1 alcoholic hydroxyl groups in the formula (2) are epoxidized.

Synthetic Example of Epoxy (meth) acrylate Synthetic Example 4 216 parts of the epoxy resin (a) obtained in Synthetic Example 1, 68.5 parts of acrylic acid, 0.5 part of methquinone, 2.0 parts of triphenylphosphine and 122 parts of diethylene glycol monomethyl ether was charged, the temperature was raised to 95 ° C, the reaction was performed at 95 ° C, and the reaction solution was reacted for about 35 hours until the acid value (mgKOH / g) became 1.0 or less. The product A) was obtained. The viscosity of product A (25 ° C.) was 450 poise.

Synthesis Example 5 239 parts of the epoxy resin (b) obtained in Synthesis Example 2, 68.5 parts of acrylic acid, 0.5 part of methoquinone, 2.0 parts of triphenylphosphine and 133 parts of diethylene glycol monomethyl ether were charged. The reaction was carried out at 0 ° C., and the reaction was carried out for about 35 hours until the acid value (mgKOH / g) of the reaction solution became 1.0 or less to obtain an epoxy acrylate (Product B). The viscosity of product B was 645 poise (25 ° C.).

Synthesis Example 6 238 parts of the epoxy resin (c) obtained in Synthesis Example 3, 68.5 parts of acrylic acid, 0.5 part of methoquinone, 2.0 parts of triphenylphosphine and 132 parts of diethylene glycol monomethyl ether were charged, The reaction was carried out at 95 ° C. until the acid value (mgKOH / g) of the reaction solution became 1.0 or less, and the reaction was carried out for about 35 hours to obtain an epoxy acrylate (product C). The viscosity of product C was 410 poise (25 ° C.).

Examples 1 to 4, Comparative Examples 1 and 2 A solder resist resin composition (ink) was blended according to the blending composition (numerical values are parts by weight) shown in Table 1 and kneaded with three rolls. This is applied to the entire surface of the copper through-hole printed wiring board by spray coating so that the film thickness after drying is 25 μm, the coating film is pre-dried at 80 ° C. for 20 minutes, and then the back surface is similarly coated. It was pre-dried at 30 ° C for 30 minutes. Next, a solder mask pattern film is brought into contact with the coating surface, and a metal halide lamp double-side simultaneous exposure apparatus (HMW680 manufactured by Oak Co., Ltd.) is used to obtain 500 mJ /
It was exposed with a light amount of cm ^{2, and} the unirradiated portion of the coating film was developed with water at a spray pressure of 2.5 kg / cm ² and a liquid temperature of 25 ° C. for 60 seconds to be dissolved and removed. The developability of the obtained product was evaluated as described below. Then, it is heated and cured at 150 ° C. for 60 minutes in a hot air drier, and the test piece having the obtained cured film is tested for hardness of cured film, solder heat resistance, acid resistance, alkali resistance, solvent resistance and insulation resistance. went.

The results are shown in Table 2. Test method and evaluation method (Developability) The developability was visually evaluated with a magnifying glass. ○ ・ ・ ・ ・ Fully developed △ △ ・ ・ ・ Slightly undeveloped area × ・ ・ ・ ・ Greatly undeveloped area (Cured film hardness) Hardened film hardness measured according to JISK5400 did. (Solder heat resistance) According to the test method of JISC6481,
The test piece was immersed in a solder bath at 260 ° C. for 10 seconds 10 times or 4 times to evaluate the change in appearance. (Post-flux resistance) Dipping was performed 10 times for 10 seconds to evaluate the change in appearance. ○ ・ ・ ・ ・ No change in appearance △ ・ ・ ・ ・ ・ ・ Discoloration of the cured film is observed × ・ ・ ・ ・ Floating, peeling, or solder dip in the cured film Note) Post-flux used: JS-64P (Yamaei) (Chemical Co., Ltd.) (Flux resistance for levelers) Dipped for 10 seconds 4 times,
The change in appearance was evaluated. ○ ・ ・ ・ ・ No change in appearance △ ・ ・ ・ ・ ・ ・ Discoloration of cured film is observed × ・ ・ ・ ・ Floating, peeling, and solder dip in cured film Note) Flux for leveler used: SSF-832
(Manufactured by Sanei Chemical Co., Ltd.)

(Acid resistance) The test piece was immersed in a 10 vol% sulfuric acid aqueous solution at 25 ° C. for 15 minutes, and the appearance of the cured film was visually observed. Regarding the adhesiveness, a peeling test using a cellophane tape was performed on the solder pattern portion to determine the peeled state of the resist. ○ ・ ・ ・ ・ No change in appearance and no peeling of the cured film △ ・ ・ ・ ・ No change in appearance, but slight peeling of the cured film × ・ ・ ・ ・ Floating of the cured film was observed. Peeling test showed large peeling (alkali resistance) A test piece was immersed in a 10 wt% sodium hydroxide aqueous solution at 25 ° C. for 15 minutes, and the same test as the acid resistance test was conducted for evaluation. (Solvent resistance) The test piece was immersed in dichloromethane at 25 ° C for 30 minutes, and the appearance change was observed. ○ ・ ・ ・ ・ No change in appearance × ・ ・ ・ ・ Swelling or permeation (insulation resistance) The initial insulation resistance was measured using a test piece, and the IPC-SM-840B test was performed. According to the method (IPC class III), moisture absorption after 7 days and insulation resistance after contact with electricity were measured.

Table 1 Actual Example Comparative Example 1 2 3 4 1 2 Product A 100 〃 B 100 50 〃 C 100 50 KAYARAD R-5027 * 1 116.7 〃 R-5089 * 2 116.7 〃 R-2059 * 3 20 20 20 20 20 20 TEPIC-S * 4 30 30 30 30 EPPN-201 * 5 10 KAYARAD DPHA * 6 10 10 10 5 10 10 Diethylene glycol mono 300 300 300 300 90 390 Methyl ether Irgacure 907 * 7 12 12 12 8 12 12 KAYACURE DETX * 8 3 3 3 2 3 3 Dicyandiamide 5 5 2 5 5 (Epoxy resin curing agent) Phthalocyanine green (pigment) 2 2 2 2 2 2 2 KS-603 (antifoaming agent) * 9 2 2 2 2 2 2 2 Hexamethoxymelamine 10 tar 60 60 50 40 60 60 Water 90 90 90 90 − −

Note) * 1 KAYARAD R-5027: Nippon Kayaku Co., Ltd.
Made of phenol novolac type epoxy acrylate and dibasic acid anhydride reaction product, butyl cellosolve acetate 4
Product containing 0% by weight, acid value 68.5 (mgKOH / g) * 2 KAYARAD R-5089: Nippon Kayaku Co., Ltd.
Made of bisphenol A type epoxy acrylate and dibasic acid anhydride reaction product, carbitol acetate 40% by weight
Contained products, acid value 63 (mgKOH / g) * 3 KAYARAD R-2058: Nippon Kayaku Co., Ltd.
Made of phenol novolac type epoxy acrylate, butyl cellosolve acetate 30% by weight. * 4 TEPIC-S: Nissan Chemical Co., Ltd., tris (2,3-epoxypropyl) isocyanurate, melting point 95-125 ° C. * 5 EPPN-201: Nippon Kayaku Co., Ltd., phenol novolac type epoxy resin, Softening point 65 ° C * 6 KAYARAD DPHA: manufactured by Nippon Kayaku Co., Ltd.
Dipentaerythritol, polyacrylate * 7 Irgacure 907: Ciba Geigy, photopolymerization initiator * 8 KAYACURE DETX: Nippon Kayaku Co., Ltd.
Photopolymerization initiator * 9 KS-603: Shin-Etsu Chemical Co., Ltd., antifoaming agent

Table 2 Actual Example Comparative Example 1 2 3 4 1 2 Image quality ○ ○ ○ ○ × × Hardened film hardness 8H 8H 8H 6H 8H 4H Solder heat resistance Post flux resistance ○ ○ ○ ○ ○ ○ Leveler flux resistance ○ ○ ○ ○ ○ ○ Table 2 (continued) Practical example Comparative example 1 2 3 4 1 2 Acid resistance ○ ○ ○ ○ ○ × Alkali resistance ○ ○ ○ ○ ○ ○ Solvent resistance ○ ○ ○ ○ △ △ Insulation resistance (Ω) Initial value (× 10 ¹³ ) 3.5 3.4 3.1 2.5 3.9 3.1 Value after test (× 10 ¹² ) 1.9 2.5 1.5 1.0 5.5 4.2

As is apparent from the table, the resin composition of the present invention can be diluted with water and can be developed with water. It is also found that the cured film has a large hardness and is excellent in heat resistance, acid resistance and alkali resistance.

[0045]

Industrial Applicability The resin composition of the present invention can be diluted with water, can be developed with water, and has resistance to a developing solution in the exposed area, and its cured product has adhesion, solder heat resistance and chemical resistance. sex,
It has excellent electrical insulation properties and is particularly suitable as a solder resist resin composition.

Claims (3)

[Claims] 1. A formula (1): (In the formula, R ₁ and R ₂ are each independently hydrogen or an alkyl group having 1 to 4 carbon atoms, n is an integer of 1 or more, M is hydrogen or [Chemical 3] And when n is 2 or more, at least one M is Is. A resin composition containing an epoxy (meth) acrylate, which is a reaction product of an epoxy resin represented by and (meth) acrylic acid. 2. A solder resist resin composition containing the epoxy (meth) acrylate according to claim 1. 3. A cured product of the resin composition according to claim 1 or 2.