JPH051052A - Epoxy resin and its production - Google Patents

Abstract

PURPOSE:To provide a new epoxy resin having low softening point and excellent melt-flowability, heat-resistance, mechanical properties and moisture-resistance and utilizable in a variety of fields such as casting, lamination, paint and semiconductorsealing. CONSTITUTION:The objective epoxy resin is produced by reacting a low- molecular weight phenylphenol aralkyl resin of formula I [(n) is integer of 0-10; the content of the n=0 component in the resin is >=40% (GPC-Area %)] with an epihalohydrin in the presence of a halogenated hydrogen acceptor (preferably alkali metal hydroxide) at 40-120 deg.C. The resin of formula I has an average molecular weight of 400-1,500 and is produced by reacting 1mol of an aralkyl halide or aralkyl alcohol derivative of formula II (R is halogen, OH or <=4C alkoxy) (e.g. alpha,alpha'-dimethoxy-p-xylene) with >=3mol of phenylphenol in the presence of an acid catalyst and recovering the unreacted phenylphenol from the reaction mixture.

Description

Detailed Description of the Invention

[0001]

The present invention relates to a novel epoxy resin,
And a manufacturing method thereof. The epoxy resin of the present invention has a low softening point, is excellent in melt fluidity, and is also excellent in heat resistance, mechanical properties and moisture resistance, for casting, for lamination,
It is a resin that can be used in a wide range of fields such as paints and semiconductor sealants.

[0002]

2. Description of the Related Art Epoxy resins are used in a wide variety of fields such as matrix resins for composite materials and adhesives. A typical conventional epoxy resin is 2,2-bis (4-
Hydroxyphenyl) propane, bisphenols such as 4,4'-dihydroxydiphenylsulfone and 4,4'-diaminodiphenylmethane, obtained by reacting aromatic diamines such as 3,3'-diaminodiphenylsulfone with epihalohydrin, There are various types such as those obtained by reacting a phenol novolac resin or a cresol novolac resin with epihalohydrin, and each is used in various applications as described above in combination with an appropriate curing agent. However, these typical epoxy resins
It is hard to say that it can sufficiently meet the required performance in the advanced technology field. For example, those with a sulfone structure introduced into the skeleton, or those with a higher crosslink density due to the diamine structure show high heat resistance, but on the other hand, the water absorption rate becomes high, resulting in sacrificing moisture resistance and then heat resistance. Is improving. On the other hand, an epoxy resin using a phenol novolac resin has good moisture resistance, but heat resistance is still required to be improved.

Thus, conventional epoxy resins are still unsatisfactory in overall performance. In recent years, as a solution to this problem, Japanese Patent Publication No. 47-13782 proposes an epoxy resin obtained from a phenol aralkyl resin using a phenol as a raw material. This is an aralkyl halide or aralkyl alcohol derivative 1
A phenol aralkyl resin obtained by reacting 1.3 to 3.0 moles, substantially 1.5 to 1.9 moles, of phenols with respect to moles is reacted with epihalohydrin. It has been found that the cured compositions using these epoxy resins are superior in heat resistance, mechanical strength, moisture resistance, oxidation resistance and the like to those using the epoxy resin obtained from the phenol novolac resin.

[0004]

However, in recent years, the performance required for the matrix resin for composite materials is required to be greatly improved, especially in terms of moisture resistance. Moreover, in these matrix resins for composite materials, it is desired that the softening point of the raw material resin is low in terms of workability, and the softening point is preferably 100 ° C. or lower, and further, if it is liquid at room temperature. Ideal. This makes it possible to reduce or omit unnecessary work such as excessive heating and melting and the use of a solvent during kneading of raw material resins and various compounding agents. As a method of improving the moisture resistance in response to such demands for improvement in performance and work, it is conceivable to use a phenol aralkyl resin as a raw material having a large molecular weight as a phenol component. This is a concept that the hydrophobicity is increased by reducing the functional group density per unit molecule, and examples of such a phenol compound include phenylphenols.

However, when a resin is produced from phenylphenol as a raw material by the method disclosed in Japanese Patent Publication No. 47-13782, the amount of phenylphenol is limited to 1.3 to 3 mol per 1 mol of aralkyl halide or aralkyl alcohol derivative. The composition of the resulting phenylphenol aralkyl resin has a composition of 40 units in which n of the repeating unit in the general formula (I) is 0.
% (GPC Area%) or less, and the softening point of the epoxy resin obtained from the phenylphenol aralkyl resin in this composition range is 100 ° C. or more, so it was found that no improvement in workability was achieved.

An object of the present invention is to provide, as a matrix resin for composite materials, an epoxy resin which has improved heat resistance, oxidation resistance and mechanical performance, and has improved workability and low softening point. To develop.

[0007]

Means for Solving the Problems The inventors of the present invention have made extensive studies to solve the above problems, and as a result, have completed the present invention. That is, the present invention provides a low molecular weight phenylphenol aralkyl resin represented by the general formula (I)

[0008]

[Chemical 4] (Wherein, n represents an integer of 0 to 10 and contains 40% or more of n = 0) and an epihalohydrin in the presence of a hydrogen halide acceptor, an epoxy resin and a general formula (II) Aralkyl halide or aralkyl alcohol derivative represented by the formula

[0009]

[Chemical 5] (Wherein R represents a halogen atom, a hydroxyl group, or a lower alkoxy group having 4 or less carbon atoms) in the presence of an acid catalyst,
After reacting 3 times or more moles of phenylphenol, unreacted phenylphenol is recovered to obtain a low molecular weight phenylphenol aralkyl resin represented by the general formula (I), which is further reacted with a hydrogen halide acceptor. The present invention relates to a method for producing an epoxy resin by reacting epihalohydrin in the presence thereof.

The low molecular weight phenylphenol aralkyl resin used in the present invention is represented by the general formula (I), the number of repeating units n is in the range of 0 to 10, and n is 0.
It is a resin containing 40% (GPC Area%) or more of the above component, an average molecular weight of 400 to 1500, and a liquid or a softening point of 85 ° C. or less according to the ring and ball method of JIS K-2548. In the present invention, the content of n = 0 is represented by Area% analyzed by high performance liquid chromatography (GPC). As a result of studies by the present inventors, the present invention has revealed that a phenylphenol aralkyl resin represented by the general formula (I), which is a raw material of an epoxy resin, contains 40% (%) of a component in which the repeating unit n is 0. It is based on the finding that the softening point of the epoxy resin obtained from the phenylphenol aralkyl resin occupying more than GPC Area%) is 100 ° C. or lower.

The epoxy resin obtained from the phenylphenol aralkyl resin by the method of the present invention is a cured product which exhibits excellent performances in heat resistance, moisture resistance, mechanical strength and the like when combined with a general curing agent for epoxy resin. give. For example, when comparing an epoxy resin obtained from a phenylphenol aralkyl resin and an epoxy resin obtained from a phenol aralkyl resin with respect to a cured product obtained by using a phenol novolac resin as a curing agent, respectively, compared to the latter cured product, In the cured product, its Tg (glass transition temperature) rises by 30 to 60 ° C and the water absorption rate (D-2 / 100, boiling at 100 ° C for 2 hours)
Decreases from 1/2 to 3/4. Therefore, the epoxy resin obtained from the phenylphenol aralkyl resin is
Both the high heat resistance and the high humidity resistance are fully satisfied. Furthermore, since the epoxy resin of the present invention is oily at room temperature or has a low softening point, workability in compounding, coating, impregnation and the like is very good. It is a feature.

Next, the method for obtaining the low molecular weight phenylphenol aralkyl resin represented by the general formula (I) will be specifically described. The aralkyl halide or aralkyl alcohol derivative used in the present invention is represented by the general formula (II), wherein R is preferably chlorine, bromine, iodine, fluorine, a hydroxyl group, or a lower alkoxy group having 4 or less carbon atoms. The reaction is slow with an alkoxy group having 4 or more carbon atoms. Further, even when the carbon number is 4, that is, the butoxy group, the reaction tends to be slow with the tert-butoxy group. Therefore, suitable for use in the present invention are α, α′-dichloro-p-xylene, α, α′-
Dibromo-p-xylene, α, α′-diiodo-p-xylene, α, α′-dihydroxy-p-xylene, α,
α'-dimethoxy-p-xylene, α, α'-diethoxy-p-xylene, α, α'-di-n-propoxy-p
-Xylene, α, α'-diisopropoxy-p-xylene, α, α'-di-n-butoxy-p-xylene, α,
α'-di-sec-butoxy-p-xylene, α, α'-
Diisobutoxy-p-xylene and the like can be mentioned.

The phenylphenol used in the reaction of the present invention is o-phenylphenol, m-phenylphenol or p-phenylphenol. In the reaction of the present invention, phenylphenol is added in an amount of 3.0 to 20 mol, preferably 3.0 to 10 m, per 1 mol of the aralkyl halide or aralkyl alcohol derivative represented by the general formula (II).
In the range of ol, heating is performed in the presence of an acid catalyst. Examples of the acid catalyst used in the method of the present invention include inorganic or organic acids, for example, mineral acids such as hydrochloric acid, sulfuric acid and phosphoric acid, organic sulfonic acids such as methanesulfonic acid and p-toluenesulfonic acid,
Furthermore, Friedel-Crafts type catalysts such as zinc chloride, aluminum chloride, stannic chloride, ferric chloride, sulfuric acid esters such as dimethylsulfate and diethylsulfate, super strong acids such as trifluoromethanesulfonic acid and boron trifluoride. Can be used alone or in combination. The amount of the catalyst used is about 0.0001 to 10% by weight, preferably about 0.001 to 1% by weight, based on the total weight of the phenylphenol, aralkyl halide or aralkyl alcohol derivative.

The reaction may be carried out by a method in which the raw materials are charged all at once and reacted, or a method in which an aralkyl halide or an aralkyl alcohol derivative is added to a mixture of phenylphenol and a catalyst and the reaction is sequentially carried out. Method is selected. As the reaction proceeds, hydrogen halide, water, alcohol or the like produced is trapped and removed outside the system. The reaction temperature is preferably 110 ° C or higher, and at 110 ° C or lower, the reaction becomes extremely slow. Further, in order to make the reaction time as short as possible, the reaction temperature is preferably in the range of 130 to 250 ° C, and further 130 to 1 ° C.
A range of 80 ° C is more desirable. The reaction time is about 1 to 30 hours.

After completion of the reaction, unreacted phenylphenol is removed by any means such as vacuum distillation to obtain a phenylphenol aralkyl resin. As a method of epoxidizing the phenylphenol aralkyl resin thus obtained, a known method can be applied. That is, the obtained phenylphenol aralkyl resin is reacted with epihalohydrin, preferably epichlorohydrin, usually in the temperature range of 40 to 120 ° C. in the presence of a hydrogen halide acceptor. The amount of epihalohydrin used in the reaction depends on the purpose of use of the epoxy resin, but is usually 2.0 to 30 times equivalent to the hydroxyl group in the phenylphenol aralkyl resin, preferably 10 considering the economical efficiency.
It is not more than double equivalent. Particularly suitable as the hydrogen halide acceptor of the present invention are alkali metal hydroxides such as potassium hydroxide and sodium hydroxide. The hydrogen halide acceptor is preferably added dropwise as an aqueous solution into the heated mixture of the phenylphenol aralkyl resin and epihalohydrin. The amount of the hydrogen halide acceptor used is 1.0 to 1.5 times the equivalent of the hydroxyl groups in the resin. After the reaction, excess acceptor substance and by-produced salt are removed from the reaction product by means such as vacuum distillation and washing with water.

The epoxy resin produced by the method of the present invention can be cured with a conventional curing agent. Typical examples of hardeners are the customary hardeners for epoxy resins, such as bis (4-aminophenyl) methane,
Aniline / formaldehyde resin, bis (4-aminophenyl) sulfone, propane-1,3-diamine, hexamethylenediamine, diethylenetriamine, triethylenetetramine, 2,2,4-trimethylhexane-1,6-diamine, m-xylyl Diamine, bis (4-aminocyclohexyl) methane, 2,2-bis (4-aminocyclohexyl) propane and 3-aminomethyl-3,5,5-trimethylcyclohexylamine (isophoronediamine)
Aliphatic, cycloaliphatic, aromatic and heterocyclic amines such as; polyaminoamides such as those obtained from aliphatic polyamines and dimerized or trimerized fatty acids; resorcinol, hydroquinone, 2,2-bis (4-hydroxyphenyl) ) Polyphenols such as propane and phenol / aldehyde resins; polythiols such as those marketed as "Thiochols"; eg phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, hexachloroendomethylenetetrahydrophthalic anhydride, Pyromellitic dianhydride, 3,4,3 ′, 4′-benzophenonetetracarboxylic dianhydride, the acid of the anhydride, and polycarboxylic acid such as isophthalic acid and terephthalic acid and its anhydride. When the curing agent is a polycarboxylic acid or an anhydride thereof, 0.4 to 1.1 equivalents of a carboxyl group or an anhydride group is usually used with respect to 1 equivalent of epoxy groups. When the curing agent is polyphenol, 0.75 to 1.25 phenolic hydroxyl groups are used per equivalent of epoxy groups.

The epoxy resin produced by the method of the present invention can also be cured with a catalytic curing agent. Examples of the catalytic curing agent include known amines such as tertiary amines such as dimethylbenzylamine, imidazoles such as 2-undecylimidazole, and various metal compounds. The amount of catalytic curing agent used is 10% by weight of epoxy resin.
1 to 40 parts per 0 part is generally used.

[0018]

EXAMPLES Next, the present invention will be described in more detail with reference to examples, but the present invention is not limited thereto. Example 1 In a reactor equipped with a stirrer, a thermometer, a Dean-Stark azeotropic trap, and a condenser, α, α′-dimethoxy-p-xylene 249 g (1.5 mol), o-phenylphenol 1275 g (7.5 mol) And methanesulfonic acid 7.6 g (0.5
%) Was charged, and the reaction was carried out at 150 to 160 ° C. for 4 hours while stirring. The produced methanol was sequentially trapped and removed from the system. After completion of the reaction, unreacted o-phenylphenol was removed by vacuum distillation to obtain 482 g of o-phenylphenol aralkyl resin having the structure of general formula (I). The composition of the resin by high performance liquid chromatography is Area%, n = 0 is 61.8%, n = 1 is 17.9%, n =
2 was 8.5% and n ≧ 3 was 11.8%. The hydroxy equivalent weight of this resin was 253.2 g / eq, and the softening point (hereinafter the same) measured by the ring and ball method described in JIS K-2548 was 64 ° C. 450 g of this o-phenylphenol aralkyl resin and 822 g (8.9 mol) of epichlorohydrin were mixed, and a stirrer,
The reactor was equipped with a Dean Stark azeotropic distillation trap and a dropping funnel. While stirring this mixture, the temperature was raised to 115 to 119 ° C, 196 g of 40% sodium hydroxide aqueous solution was added dropwise at the same temperature for 4 hours, and distilled water was continuously separated and removed, and epichlorohydrin was added to the reactor. Returned to. After completion of the dropping, distilled water was removed to complete the reaction.
After this, excess epichlorohydrin was removed by vacuum distillation. Next, the reaction product was dissolved in 1500 g of toluene, sodium chloride and a slight excess of sodium hydroxide were filtered off, then washed twice with 500 g of water, and toluene was distilled off under reduced pressure to obtain a brown solid epoxy. 503 g of resin was obtained. This has an epoxy equivalent of 342 g / eq and a softening point of 47.
It was ℃.

Example 2 207.3 g (1.5 mol) of α, α'-dihydroxy-p-xylene and 2550 g of p-phenylphenol were placed in a reactor equipped with a stirrer, a thermometer, a Dean Stark azeotropic trap, and a condenser. (15 mol) and methanesulfonic acid 1.38 g (0.
05%) and stir at 150-160 ℃ for 4
The reaction was carried out over time. The generated water was sequentially trapped and removed to the outside of the system. After completion of the reaction, unreacted p-phenylphenol is removed by distillation under reduced pressure to have the structure of general formula (I)
453 g of p-phenylphenol aralkyl resin was obtained. The composition of the resin by high performance liquid chromatography is n = 0.
Is 83.6%, n = 1 is 9.4%, n = 2 is 4.1%, and n ≧ 3 is
It was 2.9%. The hydroxy equivalent weight of this resin is 248.6.
g / eq, and the softening point was 42 ° C. 400 g of this p-phenylphenol aralkyl resin and 744 g (8.0 mol) of epichlorohydrin were mixed and charged into a reaction vessel equipped with a stirrer, a Dean Stark azeotropic distillation trap and a dropping funnel. Stir this mixture while stirring 115-119
After the temperature was raised to 0 ° C., 197 g of 40% aqueous sodium hydroxide solution was added dropwise at the same temperature over 4 hours, the distilled water was continuously separated and removed, and epichlorohydrin was returned to the reactor. After completion of the dropping, distilled water was removed to complete the reaction. After this, excess epichlorohydrin was removed by vacuum distillation. The reaction product was dissolved in 1300 g of toluene, sodium chloride and a small excess of sodium hydroxide were filtered off, washed twice with 500 g of water, and toluene was distilled off under reduced pressure to obtain 451 g of a yellow oily epoxy resin. Obtained. The epoxy equivalent of this epoxy resin was 338 g / eq, and the viscosity measured by an E-type viscometer manufactured by Tokyo Keiki Co., Ltd. was 950 g / cm · sec (35 ° C.).

Example 3 In a reactor equipped with a stirrer, a thermometer, a Dean Stark azeotropic trap, and a condenser, α, α'-dimethoxy-p-xylene 249 g (1.5 mol) and o-phenylphenol 765 g ( 4.5 mol) and trifluoromethanesulfonic acid
Charge 0.01 g (0.001%) and stir 150-160 with stirring.
The reaction was carried out at ℃ for 4 hours. The generated water was sequentially trapped and removed to the outside of the system. After completion of the reaction, unreacted o-phenylphenol was removed by distillation under reduced pressure to obtain 452 g of o-phenylphenol aralkyl resin having the structure of general formula (I). The resin composition by high performance liquid chromatography was 43.7% for n = 0, 21.3% for n = 1, and 13.8 for n = 2.
%, And n ≧ 3 was 21.2%. The hydroxy equivalent weight of this resin was 261.2 g / eq, and the softening point was 88 ° C. 400 g of this o-phenylphenol aralkyl resin and 712.3 g (7.7 mol) of epichlorohydrin were mixed and charged into a reaction vessel equipped with a stirrer, a Dean Stark azeotropic distillation trap and a dropping funnel. While stirring the mixture, the temperature was raised to 115 to 119 ° C, and then 40% at the same temperature.
168 g of an aqueous sodium hydroxide solution was added dropwise over 4 hours. The distilled water was continuously separated and removed, and epichlorohydrin was returned to the reactor. After completion of the dropping, distilled water was removed to complete the reaction. After this, excess epichlorohydrin was removed by vacuum distillation. The reaction product was dissolved in 1300 g of toluene, sodium chloride and a small excess of sodium hydroxide were filtered off, washed twice with 500 g of water, and toluene was distilled off under reduced pressure to obtain a yellow oily epoxy resin.
g was obtained. The epoxy equivalent of this epoxy resin is 349 g / eq.
And the softening point was 67 ° C.

Comparative Example 1 In a reaction vessel equipped with a stirrer, a thermometer, and a Dane Stark azeotropic distillation trap, α, α'-dimethoxy-p-
166 g (1.0 mol) of xylene, 179 g (1.9 mol) of phenol and 1.5 g of paratoluenesulfonic acid were charged, and the mixed solution was stirred while maintaining the temperature at 130 ° C to 150 ° C. The methanol produced during the reaction was distilled off. After 3 hours, the generation of methanol disappeared and the condensation was completed. General formula (A)
280 g of a phenol aralkyl resin composition having the structure of (Chemical Formula 6) was obtained.

[0022]

[Chemical 6] The average molecular weight of the obtained resin was 2054, and the average repeating unit m was 10 when estimated from this average molecular weight. The softening point was 73.5 ° C. 240 g of this resin and 694 g (7.5 mol) of epichlorohydrin were mixed and charged into a reaction vessel equipped with a stirrer, a Dean Stark azeotropic distillation trap and a dropping funnel. Do not stir this mixture.
After the temperature was raised to ˜119 ° C., 165 g of 40% sodium hydroxide aqueous solution was added dropwise at the same temperature over 3 hours, distilled water was continuously separated and removed, and epichlorohydrin was returned to the reactor. After completion of the dropping, distilled water was removed to complete the reaction. After this, excess epichlorohydrin was removed by vacuum distillation. The reaction product was dissolved in 1500 g of toluene, and sodium chloride and a slight excess of sodium hydroxide were filtered off.
It was washed twice with 00 g of water, and toluene was distilled off under reduced pressure to obtain 275 g of a yellow solid epoxy resin. This had an epoxy equivalent of 274 g / eq and a softening point of 54 ° C.

Comparative Example 2 A reaction vessel equipped with a stirrer, a thermometer, and a Dean Stark azeotropic distillation trap was charged with α, α'-dimethoxy-p.
-Xylene 166g (1.0mol), o-phenylphenol 255
g (1.5 mol) and methanesulfonic acid 2.1 g (0.5%) were charged, and the reaction was carried out at 150 to 160 ° C. for 4 hours while stirring. The produced methanol was sequentially trapped and removed to the outside of the system. After completion of the reaction, unreacted o-phenylphenol is removed by distillation under reduced pressure to obtain a structure of general formula (I): 326
g of o-phenylphenol aralkyl resin was obtained. The composition of the resin by high performance liquid chromatography is n = 0
17.5%, n = 1 16.3%, n = 2 13.4%, n = 3 1
0.7%, and n ≧ 4 was 42.1%. The hydroxy equivalent weight of this resin was 283 g / eq, and the softening point was 110 ° C. 250 g of this o-phenylphenol aralkyl resin
And 409 g (4.4 mol) of epichlorohydrin were mixed and charged into a reaction vessel equipped with a stirrer, a thermometer, a Dean Stark azeotropic distillation trap and a dropping funnel. The temperature of this mixture was raised to 115 to 119 ° C with stirring, and then, at the same temperature, 4
97 g of 0% sodium hydroxide aqueous solution was added dropwise over 3 hours.
Azeotropic water was separated and removed outside the system, and epichlorohydrin was returned to the reactor. After completion of the dropping, distilled water was removed to complete the reaction. After this, excess epichlorohydrin was removed by vacuum distillation. The reaction product was dissolved in 1500 g of toluene, sodium chloride and a slight excess of sodium hydroxide were filtered off, and then washed with 500 g of water twice. Toluene was distilled off under reduced pressure to remove the brown solid epoxy resin 2
82 g was obtained. The epoxy equivalent of this product was 387 g / eq, and the softening point was 102 ° C.

Example of Use A curing agent was added to each of the epoxy resins obtained in Examples 1, 2 and 3 and Comparative Examples 1 and 2 and the epoxy resin (EOCN-102S, manufactured by Nippon Kayaku) derived from o-cresol novolac. As phenol novolac resin (BRG # 5
58: Showa High Polymer Co., Ltd. was blended under the conditions shown in Table 1 (Tables 1 and 2) and casted. The physical properties of the cured resin after processing were measured by the following methods. Boiled water absorption rate: Boiled 100 ° C, 2 hours bending test: JIS K-7203 Tensile test: JIS K-7113 The measurement results are shown in Table-1. In addition, Tg in the table indicates a glass transition temperature.

[0025]

[Table 1]

[0026]

[Table 2]

As is clear from Table 1, the cured products shown in Use Examples 1 to 3 obtained by using the epoxidized phenylphenol aralkyl resin of the present invention are obtained from the epoxidized o-cresol novolac resin. Compared with the cured product of Use Example 6, its heat resistance (Tg) was kept at a high level, but its moisture resistance (boiling water absorption) was a much lower value, showing a significant improvement. Furthermore, when compared with the cured product of Use Example 4 obtained from the epoxidized product of the phenol aralkyl resin, it exhibits a low water absorption rate which is even higher than the low water absorption rate which is the characteristic of the epoxidized product of the phenol aralkyl resin, and has a much higher heat resistance. It can be seen that it has the property. In addition, although the epoxidized phenylphenol aralkyl resin (Use Example 5) has a high level of physical properties, the molecular weight distribution of the phenylphenol aralkyl resin itself is higher than that of the phenylphenol aralkyl resin used according to the present invention. Because
The softening point of the obtained epoxide is 100 ° C. or higher,
For the reasons described above, the workability during use is significantly reduced, which is not preferable. That is, the epoxidized phenylphenol aralkyl resin obtained by the present invention is an epoxy resin which gives a cured product exhibiting high levels of both heat resistance and humidity resistance, and has good workability and excellent performance balance. .

[0028]

As described above in detail, since the epoxy resin of the present invention is a resin having a low softening point, it is a resin having excellent workability such as kneading and compounding.

Further, the cured composition has extremely good mechanical strength, heat resistance, and moisture resistance, and the epoxy resin of the present invention has various properties which have hitherto failed to satisfy the demands from the field of electronic materials. Since the performance can be greatly improved, its effect is extremely large.

Claims (2)

[Claims] 1. A low molecular weight phenylphenol aralkyl resin represented by the general formula (I) (chemical formula 1): An epoxy resin obtained by reacting (in the formula, n represents an integer of 0 to 10 and contains 40% or more of n = 0) with epihalohydrin in the presence of a hydrogen halide acceptor. 2. An aralkyl halide or aralkyl alcohol derivative represented by the general formula (II) (chemical formula 2): (Wherein R represents a halogen atom, a hydroxyl group, or a lower alkoxy group having 4 or less carbon atoms) in the presence of an acid catalyst.
After reacting more than twice the molar amount of phenylphenol, the unreacted phenylphenol is recovered to give a low molecular weight phenylphenol aralkyl resin represented by the general formula (I) (Chemical Formula 3). (Wherein n represents an integer of 0 to 10 and contains 40% or more of n = 0), and further, epihalohydrin is reacted in the presence of a hydrogen halide acceptor. Resin manufacturing method.