JP3102150B2 - Low viscosity epoxy resin composition - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a novel epoxy resin composition containing alkylene carbonate and a specific chlorine-containing compound and having good low-temperature storage stability.

[0002]

2. Description of the Related Art Epoxy resins have excellent mechanical properties,
Paints, electrical materials,
Widely used in the fields of composites and adhesives. However, since the viscosity of the epoxy resin at room temperature is as high as several thousand centipoise to 10,000 thousand centipoise in a liquid state, it is often diluted to a desired viscosity using an appropriate diluent when used. As the diluent, there is a non-reactive diluent which reacts when the epoxy resin is cured with the curing agent and does not react with the reactive diluent incorporated in the cured composition, but the non-reactive diluent remains in the cured product. Therefore, there is a problem that physical properties are deteriorated or voids are generated at the time of heat curing, and the use is limited to applications such as paints. On the other hand, reactive diluents do not have such a problem and are widely used for applications requiring excellent cured physical properties.

[0003]

However, recently, the most widely used butyl glycidyl ether, which is one of the reactive diluents, has been found to have a mutagenic effect, and the hygiene problem has been highlighted. Has occurred. Therefore, neopentyl glycol, 1,6 hexanediol, glycidyl ether of a long-chain alcohol, and the like have been proposed as reactive diluents replacing butyl glycidyl ether. In order to achieve this, a larger amount of the resin must be added to the epoxy resin, and as a result, there is a new problem that the physical properties of the cured product are adversely affected.

An alkylene carbonate represented by propylene carbonate is known as a reactive diluent having excellent diluting effect and low toxicity, but a mixture with a liquid epoxy resin precipitates crystals when stored in a cold place. Due to the drawback of easy storage, there was a problem in the storage stability in winter, and it was not practically used until now. That is, low toxicity,
There has been no epoxy resin composition that withstands storage at low temperatures, has an appropriate pot life after compounding with a curing agent, and exhibits excellent curing properties.Therefore, such epoxy resin compositions have been sought in the art. -ing An object of the present invention is to provide an epoxy resin composition satisfying the above-mentioned needs.

[0005]

Means for Solving the Problems The inventors have conducted intensive studies to achieve the above object, and as a result, have reached the present invention. That is, the present invention provides an epoxy resin (a) having an epoxy equivalent of more than 97, an alkylene 1,2 carbonate (b), one or more chlorine compounds (c) selected from the following (formula 1), In an epoxy resin composition comprising one or two or more polyol compounds (d) selected from (Formula 2), based on 100 parts by weight of (a),
(B) is 1 to 80 parts by weight, and the total weight of chlorine atoms in (c) is 50 to 50,000 pp with respect to the total weight of (a) + (b).
m and the total number of moles of diol groups in (d) is 15 meq / kg to 200 with respect to the total weight of (a) + (b).
(d) in an amount of meq / kg.

[0006]

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[0007]

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[0008]

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[0009]

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Examples of the epoxy resin include bisphenol A, bisphenol F, bisphenol AD, bisphenol S, tetramethylbisphenol A, tetramethylbisphenol F, and tetramethylbisphenol A.
D, epoxy resins obtained by the reaction of dihydric phenols such as tetramethylbisphenol S, biphenol, dihydroxynaphthalene, hydroquinone and resorcinol with epichlorohydrin; trihydric phenols such as trisphenolmethane and benzenetriol and epichlorohydrin Epoxy resin obtained by the reaction of phosphorus,
Examples include epoxy resins obtained by the reaction of polyphenols such as phenol novolak resins and cresol novolak resins with epichlorohydrin.

Of these, epoxy resins obtained by the reaction of dihydric phenols with epichlorohydrin are preferred, and the epoxy equivalent is particularly preferably from 100 to 40.
It is an epoxy resin having a relatively low polymerization degree of 0 g / eq. Such an epoxy resin has an epoxy equivalent of 1
There is 70 to 200 g / eq of bisphenol A type epoxy resin.

Alkylene 1,2 carbonates are cyclic carbonates containing one 1,2 carbonate group, with preferred alkylene chains containing 2 to 10 carbon atoms, the alkylene chains being straight or branched. You may. For example, ethylene carbonate, propylene carbonate, 1,2-butylene carbonate, 2,3-butylene carbonate, 1,2-hexylene carbonate, and 1,2-heptylene carbonate,
Particularly preferred alkylene carbonates are ethylene carbonate and propylene carbonate.

The amount of the alkylene carbonate used in the composition is an amount sufficient to make the viscosity of the epoxy resin easy to use according to the conditions of use and that does not substantially adversely affect the physical properties of the cured product. is there. Generally, in order to reduce the viscosity by adding an alkylene carbonate, at least 1 part by weight of the alkylene carbonate is required based on 100 parts by weight of the epoxy resin. On the other hand, if the addition amount is more than a certain amount, the crosslink density becomes low and the cured physical properties are lowered.
80 parts by weight with respect to 0 parts by weight. In coating applications, the viscosity after dilution is generally desirably about 1000 cps at room temperature, so that about 10 to 50 parts by weight, especially 10 to 30 parts by weight of alkylene carbonate is desirable per 100 parts by weight of the resin.

The chlorine compound is a derivative of a polyhydric phenol compound represented by the following (formula 1), wherein R represents an alkyl group or a hydrogen atom. Among them, those in which R is a methyl group or a hydrogen atom are preferred for the purpose of reducing the viscosity of the epoxy resin. Y represents a glycidyl group; X represents a 1-chloro-2-hydroxypropyl group. A group of compounds in which both X and Y are 1-chloro-2-hydroxypropyl groups are also included. Needless to say, the use of both a compound group in which X and Y are different and the same compound group is included, and the ratio of the two is not limited. n represents an integer of the number of repetitions, and among them, n = 0, 1, and 2 are preferable, and n = 0 is particularly preferable from the viewpoint of decreasing the viscosity of the epoxy resin composition.

As a specific example, for example, 2,2- (4 '
-Glycidyloxyphenyl) (4 "-(2" -hydroxy-3 ""-chloropropyloxy) phenyl) propane, 1,1- (4'-glycidyloxyphenyl)
(4 "-(2" -hydroxy-3 ""-chloropropyl) oxyphenyl) ethane, (4 "-glycidyloxyphenyl) (4"-(2 "-hydroxy-3""-
Chloropropyloxy) phenyl) methane, 2,2-
(3 ', 5'-dibromo-4'-glycidyloxyphenyl) (3 ", 5" -dibromophenyl-4 "-
(2 "-hydroxy-3" -chloropropyloxy) propane, 2,2-bis (4 '-(2 "-hydroxy-3" -chloropropyloxy) phenyl) propane, 1,1-bis (4 '-(2 "-hydroxy-3"-
Chloropropyloxy) phenyl) ethane,

Bis (4 '-(2 "-hydroxy-3"-)
Chloropropyloxy) phenyl) methane, 2,2-bis (3 ', 5'-dibromo-4'-(2 "-hydroxy-3" -chloropropyloxy) phenyl) propane,
1,4-di (2'-hydroxy-3'-chloropropyloxy) benzene, 1,3-di (2'-hydroxy-
3'-chloropropyloxy) benzene, 1,2-di (2'-hydroxy-3'-chloropropyloxy) benzene, 1-glycidyloxy-2- (2'-hydroxy-3'-chloropropyloxy) benzene 1-glycidyloxy-3- (2'-hydroxy-3'-chloropropyloxy) benzene, 1-glycidyloxy-4
-(2'-hydroxy-3'-chloropropyloxy)
Benzene, 1,3,5-tri (2'-hydroxy-3 '
-Chloropropyloxy) benzene,

1,2,4-tri (2'-hydroxy-
3'-chloropropyloxy) benzene, 1-glycidyloxy-3,5-di (2'-hydroxy-3'-chloropropyloxy) benzene, 1-glycidyloxy-
2,4-di (2'-hydroxy-3'-chloropropyloxy) benzene, 1,3-diglycidyloxy-5
(2'-hydroxy-3'-chloropropyloxy) benzene, 1,3-diglycidyloxy-4- (2'-hydroxy-3'-chloropropyloxy) benzene, tri (4- (2'-hydroxy-) 3'-chloropropyloxy) phenyl) methane, tri (3- (2'-hydroxy-3'-chloropropyloxy) phenyl) methane,
Tri (2- (2'-hydroxy-3'-chloropropyloxy) phenyl) methane, di (4- (2 "-hydroxy-3" -chloropropyloxy) phenyl) (4'-
Glycidyloxyphenyl) methane,

Di (4'-glycidyloxyphenyl)
(4 "-(2" -hydroxy-3 ""-chloropropyloxy) phenyl) methane, di (2-glycidyloxyphenyl) (2 '-(2 "-hydroxy-3" -chloropropyloxy) phenyl) Methane, di (2- (2 "
-Hydroxy-3 "-chloropropyloxy) phenyl) (2'-glycidyloxyphenyl) methane, di (4 '-(2" -hydroxy-3 "-chloropropyloxy) phenyl) (2'-glycidyloxyphenyl)
Methane, di (2 '-(2 "-hydroxy-3"'-chloropropyloxy) phenyl) (4 "-glycidyloxyphenyl) methane, bis (2 '-(2" -hydroxy-3 "-chloropropyl) Oxy) -3'-methylphenyl) methane,

Bis (3'-methyl-4 '-(2 "-hydroxy-3" -chloropropyloxy) phenyl) methane, (2'-(2 "-hydroxy-3" -chloropropyloxy) -3 ' -Methylphenyl) (3 "-methyl-
4 "-(2" -hydroxy-3 ""-chloropropyloxy) -phenyl) methane, (2'-glycidyloxy-3'-methylphenyl) (2 "-(2" -hydroxy-3 "") -Chloropropyloxy) -3 "-methylphenyl) methane, (3'-methyl-4'-glycidyloxyphenyl) (3" -methyl-4 "-(2" -hydroxy-3 ""-chloropropyloxy ) -Phenyl) methane, among which 2,2- (4'-glycidyloxyphenyl) (4 "-(2""-hydroxy-
3 "'-chloropropyloxy) phenyl) propane,
(4'-glycidyloxyphenyl) (4 "-(2"-
Hydroxy-3 ″ -chloropropyloxy) phenyl)
Methane, 2,2-bis (4 '-(2 "-hydroxy-
3 "-chloropropyloxy) phenyl) propane is particularly preferred.

[0020]

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[0021]

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The chlorine compound represented by the formula (1) is added so that the weight of the chlorine atom is at least 50 ppm based on the total weight of the epoxy resin and the alkylene carbonate. If the amount is less than 50 ppm, there is a problem that crystals derived from the epoxy resin are precipitated when the mixture is stored at a low temperature. On the other hand, if it exceeds 50,000 ppm, the cured physical properties are adversely affected. Therefore preferably 100pp
m to 5000 ppm, particularly preferably 200 ppm to 1 ppm.
It is desirable to add 2,000 ppm.

The polyol compound is a derivative of a polyhydric phenol compound represented by the following (formula 2), wherein R represents an alkyl group or a hydrogen atom. Among them, those in which R is a methyl group or a hydrogen atom are preferred for the purpose of reducing the viscosity of the epoxy resin. X is a glycidyl group, Y is 1,2
-Represents a dihydroxypropyl group. A group of compounds in which both X and Y are 1,2-dihydroxypropyl groups are also included. Needless to say, the use of both a compound group in which X and Y are different and the same compound group is included, and the ratio of the two is not limited. n represents an integer of the number of repetitions, and among them, n = 0, 1, and 2 are preferable, and n = 0 is particularly preferable from the viewpoint of decreasing the viscosity of the epoxy resin composition.

Specific examples include, for example, 2,2- (4 '
-Glycidyloxyphenyl) (4 "-(2"',
3 ""-dihydroxypropyloxy) phenyl) propane, 1,1- (4'-glycidyloxyphenyl)
(4 "-(2"",3""-dihydroxypropyloxy) phenyl) ethane, (4" -glycidyloxyphenyl) (4 "-(2"",3""-dihydroxypropyloxy) phenyl) methane, 2,2- (3 ', 5'-
Dibromo-4'-glycidyloxyphenyl) (3 ",
5 "-dibromo-4"-(2 "", 3 ""-dihydroxypropyloxy) phenyl) propane, 2,2-bis (4 '-(2 ", 3" -dihydroxypropyloxy)
Phenyl) propane, 1,1-bis (4 ′-(2 ″,
3 "-dihydroxypropyloxy) phenyl) ethane, bis (4 '-(2", 3 "-dihydroxypropyloxy) phenyl) methane, 2,2-bis (3', 5 '
-Dibromo- (2 ", 3" -dihydroxypropyloxy) phenyl) propane,

1,4-di (2 ', 3'-dihydroxypropyloxy) benzene, 1,3-di (2', 3'-dihydroxypropyloxy) benzene, 1,2-di (2 ', 3' -Dihydroxypropyloxy) benzene, 1-glycidyloxy-2- (2 ', 3'-dihydroxypropyloxy) benzene, 1-glycidyloxy-3- (2', 3'-dihydroxypropyloxy)
Benzene, 1-glycidyloxy-4- (2 ', 3'-
Dihydroxypropyloxy) benzene, 1,3,5-
Tri (2 ', 3'-dihydroxypropyloxy) benzene, 1,2,4-tri (2', 3'-dihydroxypropyloxy) benzene, 1-glycidyloxy-3,
5-di (2 ', 3'-dihydroxypropyloxy) benzene, 1-glycidyloxy-2,4-di (2',
3'-dihydroxypropyloxy) benzene, 1,3
-Diglycidyloxy-5- (2 ', 3'-dihydroxypropyloxy) benzene, 1,3-diglycidyloxy-4- (2', 3'-dihydroxypropyloxy) benzene,

Tri (4 '-(2 ", 3" -dihydroxypropyloxy) phenyl) methane, tri (3'-
(2 ", 3" -dihydroxypropyloxy) phenyl) methane, tri (2 '-(2 ", 3" -dihydroxypropyloxy) phenyl) methane, di (4'-
(2 "", 3 ""-dihydroxypropyloxy) phenyl) (4 "-glycidyloxyphenyl) methane, di (4'-glycidyloxyphenyl) (4"-
(2 "", 3 ""-dihydroxypropyloxy) phenyl) methane, di (2'-glycidyloxyphenyl)
(2 "-(2"",3""-dihydroxypropyloxy) phenyl) methane, di (2"-(2 "", 3 ""-
Dihydroxypropyloxy) phenyl) (2 "-glycidyloxyphenyl) methane, di (2'-glycidyloxyphenyl) (4"-(2 "", 3 ""-dihydroxypropyloxy) phenyl) methane, (2'-
(2 "", 3 ""-dihydroxypropyloxy) phenyl) (2 "-(2"",3""-dihydroxypropyloxy) phenyl) (4""-glycidyloxyphenyl)methane;

Bis (2 '-(2 ", 3" -dihydroxypropyloxy) -3'-methylphenyl) methane, bis (3'-methyl-4'-(2 ", 3" -dihydroxypropyloxy) phenyl ) Methane, (2 ′-(2 ″,
3 "-dihydroxypropyloxy) -3'-methylphenyl) (3" -methyl-4 "-(2", 3 ""-dihydroxypropyloxy) phenyl) methane, (2 '
-Glycidyloxy-3'-methylphenyl) (2 "-
(2 ", 3""-dihydroxypropyloxy)-
3 "-methylphenyl) methane, (3'-methyl-4 '
-Glycidyloxyphenyl) (3 "-methyl-4"-
(2 "", 3 ""-dihydroxypropyloxy) -phenyl) methane, among which 2,2- (4 "-glycidyloxyphenyl) (4"-(2 "", 3 ""-).
Dihydroxypropyloxy) phenyl) propane,
(4′-glycidyloxyphenyl) (4 ″-
(2 "", 3 ""-dihydroxypropyloxy) phenyl) methane and 2,2-bis (4 "-(2", 3 "-dihydroxypropyloxy) phenyl) propane are particularly preferred.

[0028]

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[0029]

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The polyol compound represented by the formula (2) is added so that the equivalent of the diol group is at least 16 meq / kg or more based on the total weight of the epoxy resin and the alkylene carbonate. If it is less than 16 meq / kg, there is a problem that when the mixture is stored at a low temperature, crystals derived from the epoxy resin are precipitated. On the other hand, if it exceeds 200 meq / kg, the cured physical properties are adversely affected. Therefore, preferably 30 to 120 meq / kg, particularly preferably 40 to 100 meq / kg.
It is desirable to add q / kg. The epoxy resin composition formulated as described above has an appropriate viscosity for use, and withstands storage at low temperatures.

The epoxy resin compounded as described above can be cured using any known curing agent. That is, polyamine type, acid anhydride type, Lewis acid type,
The curing agent can be arbitrarily selected from Lewis bases and the like according to the purpose of use. Specific examples of the polyamine-based curing agent include ethylenediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, diethylaminopropylamine, metaphenylenediamine,
Examples include metaxylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, isophoronediamine, dicyandiamide, adipic dihydrazide, and polyamide polyamine.

Specific examples of the acid anhydride-based curing agent include phthalic anhydride, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, methyltetrahydrophthalic anhydride,
Examples include methyl hexahydrophthalic anhydride, methyl nadic anhydride, dodecyl succinic anhydride, chlorendic anhydride, pyromellitic anhydride, trimellitic anhydride and the like. As a Lewis acid system, boron trifluoride monoethylamine complex, as a Lewis base system, 2-ethyl-4-methylimidazole, 2,4,6-tris (dimethylmethylamino)
Phenol and the like.

The amount of the curing agent used for curing is appropriately determined according to the final use, but the amount of the amine hydrogen in the range of 0.5 to 2.0 relative to the epoxy group and the carbonate group contained in the epoxy resin composition. Alternatively, an amount of a curing agent that becomes an acid anhydride group is used. Filler before curing, if necessary
Pigments, dyes and plasticizers may be added. Curing conditions vary depending on the type of curing agent used and the purpose of use, but curing can be performed at a temperature from room temperature to 200 ° C.

[0034]

The present invention will be further described with reference to the following examples.

Example 1 Bisphenol A diglycidyl ether type liquid epoxy resin (epoxy equivalent: 189, viscosity: 138 at 25 ° C.)
00cps) 850g to propylene carbonate 150g
And 2,2- (4'-glycidyloxyphenyl) (4 "
5.2 g of-(2 "-hydroxy-3"'-chloropropyloxy) phenyl) propane and 2,2- (4'-glycidyloxyphenyl) (4 "-(2"",3""-
Dihydroxypropyloxy) phenyl) propane 1
4.6 g was added, and the mixture was sufficiently stirred at room temperature to obtain an epoxy resin composition. Properties of the epoxy resin composition were evaluated as shown in Table 1. Further, triethylenetetramine was added as a curing agent to 169 g of the epoxy resin composition.
Evaluation of the curing behavior using 4.3 g, that is, the equivalent of the sum of the number of moles of the epoxy group and the propylene carbonate of the composition,
The cured physical properties were evaluated.

Examples 2 to 5, Comparative Examples 1 and 2, 2,2- (4'-glycidyloxyphenyl) to be added
An epoxy resin composition was prepared in the same manner as in Example 1 except that the amount of (4 "-(2""-hydroxy-3""-chloropropyloxy) phenyl) propane was changed to the amount shown in Table 1. Then, evaluation was performed in the same manner as in Example 1.

Example 6 Bisphenol A diglycidyl ether type liquid epoxy resin (epoxy equivalent: 189, viscosity: 138 at 25 ° C.)
00cps) 230 g of propylene carbonate in 770 g
And 2,2- (4'-glycidyloxyphenyl) (4 "
-(2 "-hydroxy-3"'-chloropropyloxy) phenyl) propane (5.2 g) and 2,2- (4'-
Glycidyloxyphenyl) (4 "-(2"",3""
-Dihydroxypropyloxy) phenyl) propane 1
5.0 g was added, and the mixture was sufficiently stirred at room temperature to obtain an epoxy resin composition. The evaluation was performed in the same manner as in Example 1.

Example 7 Bisphenol A diglycidyl ether type liquid epoxy resin (epoxy equivalent: 189, viscosity: 138 at 25 ° C.)
(00 cps) 909 g of propylene carbonate (91 g) and 2,2- (4'-glycidyloxyphenyl) (4 "-
5.2 g of (2 ""-hydroxy-3 ""-chloropropyloxy) phenyl) propane and 2,2- (4 "-glycidyloxyphenyl) (4"-(2 "", 3 ""-)
Dihydroxypropyloxy) phenyl) propane 1
4.3 g was added and stirred well at room temperature to obtain an epoxy resin composition. The evaluation was performed in the same manner as in Example 1.

Comparative Example 3 Bisphenol A diglycidyl ether type liquid epoxy resin (epoxy equivalent: 189, viscosity: 138 at 25 ° C.)
00cps) 450g of propylene carbonate in 550g
And 2,2- (4'-glycidyloxyphenyl) (4 "
5.2 g of-(2 "-hydroxy-3"'-chloropropyloxy) phenyl) propane and 2,2- (4'-glycidyloxyphenyl) (4 "-(2"",3""-
Dihydroxypropyloxy) phenyl) propane 1
5.9 g was added, and the mixture was sufficiently stirred at room temperature to obtain an epoxy resin composition. The evaluation was performed in the same manner as in Example 1.

Comparative Example 4 Bisphenol A diglycidyl ether type liquid epoxy resin (epoxy equivalent: 189, viscosity: 138 at 25 ° C.)
00 cps) to 1000 g of 2,2- (4'-glycidyloxyphenyl) (4 "-(2" -hydroxy-3 "").
-Chloropropyloxy) phenyl) propane 5.1 g
And 2,2- (4'-glycidyloxyphenyl) (4 "
13.9 g of-(2 "", 3 ""-dihydroxypropyloxy) phenyl) propane was added, and the mixture was stirred well at room temperature to obtain an epoxy resin composition. The evaluation was performed in the same manner as in Example 1.

Comparative Example 5 Bisphenol A diglycidyl ether type liquid epoxy resin (epoxy equivalent: 189, viscosity: 138 at 25 ° C.)
00cps) 850g to propylene carbonate 150g
And 2,2- (4'-glycidyloxyphenyl) (4 "
-(2 "-hydroxy-3"'-chloropropyloxy) phenyl) propane (5.1 g) was added, and the mixture was stirred well at room temperature to obtain an epoxy resin composition. Properties of the epoxy resin composition were evaluated as shown in Table 1. Further, evaluation of curing behavior and evaluation of cured physical properties were performed using triethylenetetramine as a curing agent in an amount of 24.3 g per 168 g of the epoxy resin composition, that is, the equivalent of the sum of the number of moles of propylene carbonate and the epoxy group of the composition.

Comparative Example 6 Bisphenol A diglycidyl ether type liquid epoxy resin (epoxy equivalent: 189, viscosity: 138 at 25 ° C.)
00cps) 850g to propylene carbonate 150g
And 2,2- (4'-glycidyloxyphenyl) (4 "
5.7 g of-(2 "-hydroxy-3""-chloropropyloxy) phenyl) propane and 2,2- (4'-glycidyloxyphenyl) (4"-(2 "", 3 ""-)
Dihydroxypropyloxy) phenyl) propane 11
7 g was added, and the mixture was sufficiently stirred at room temperature to obtain an epoxy resin composition. Properties of the epoxy resin composition were evaluated as shown in Table 1. Further, triethylenetetramine is added as a curing agent to 178 g of the epoxy resin composition.
Using 3 g, that is, the equivalent of the sum of the number of moles of the epoxy group and the propylene carbonate of the composition, the curing behavior and the cured physical properties were evaluated.

Reference Example 1 2,2- (4'-glycidyloxyphenyl) (4 "-
Synthesis of (2 "-hydroxy-3""-chloropropyloxy) phenyl) propane 340 g of bisphenol A diglycidyl ether was placed in a 1 L four-necked flask equipped with a stirrer, a condenser, a thermometer, and a gas inlet tube. Hydrogen chloride gas was bubbled while heating to 60 ° C. and stirring. The reaction mixture was analyzed for epoxy equivalent, and the reaction was terminated when the initial value became twice the initial value. The reaction mixture was separated by preparative GPC to obtain the title compound.

Reference Example 2 2,2- (4'-glycidyloxyphenyl) (4 "-
Synthesis of (2 "", 3 ""-dihydroxypropyloxy) phenyl) propane Bisphenol A diglycidyl ether 3 was placed in a 1 L four-necked flask equipped with a stirrer, condenser, and thermometer.
40 g and 60 g of acetic acid were added, heated to 90 ° C., and stirred for 2 hours. The reaction mixture was analyzed for epoxy equivalent, and the reaction was terminated when the initial value was twice the initial value. Excess acetic acid was removed by washing with water, followed by fractionation by preparative GPC to obtain the title compound.

[0045]

[Table 1]

[0046]

[Table 2]

[0047]

[Table 3]

[0048]

[Table 4]

[0049]

According to the present invention, a specific chlorine compound and a specific diol compound are present in a mixture of an epoxy resin and an alkylene carbonate, so that the mixture has a viscosity suitable for casting and coating, has low toxicity, and An epoxy resin composition having good low-temperature preservability can be obtained. This composition has an appropriate gel time and has good physical properties after curing.

──────────────────────────────────────────────────続 き Continuation of front page (56) References JP-A-3-258853 (JP, A) JP-A-4-88050 (JP, A) JP-A-55-25474 (JP, A) JP-A-61-1985 211354 (JP, A) (58) Fields investigated (Int. Cl. ⁷ , DB name) C08L 63/00-63/10 C08K 5/10 C08K 5/13 C08G 59/40

Claims (1)

(57) [Claims] 1. An epoxy resin (a) having an epoxy equivalent of more than 97 and an alkylene 1,2 carbonate (b)
And an epoxy resin composition comprising one or more chlorine compounds (c) selected from the following (Formula 1) and one or two or more polyol compounds (d) selected from the following (Formula 2) In the product, (b) is 1 to 80 parts by weight with respect to 100 parts by weight of (a), and the total weight of chlorine atoms in (c) is 50 to 50 parts with respect to the total weight of (a) + (b). 5000
(C) in an amount of 0 ppm, and the total number of moles of the diol group in (d) is 15 meq / kg to 2 to the total weight of (a) + (b).
(D) in an amount of 00 meq / kg. Embedded image Embedded image Embedded image Embedded image