JPH0239505B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to N-glycidyl substituted amide compounds. More specifically, it relates to an N,N-2-substituted amide compound in which the amide group is substituted with at least one glycidyl group. The compounds of the present invention have the general formula (R ₁ is an aliphatic hydrocarbon group, an aromatic hydrocarbon group,
It is an alicyclic hydrocarbon group, and X is hydrogen, a glycidoxy group, or an N,N-diglycidylamino group. p
is an integer of 0 or 1, and q is an integer of 1 to 4. R ₂ is an alkyl group, an alkenyl group, an arylalkyl group, or an arylalkenyl group, r is an integer of 1 or 2, and s is an integer of 1 to 4. However, when X is hydrogen, p is 1, q
is 0 or 1, and when s is 1, r is 1 or 2, while when s is 2 to 4, r is 2. When X is a glycidoxy group, p is 1 and r is 2
It is. When X is an N,N-diglycidylamino group, p is 0 or 1, q is 1 or 2, s is 1 or 2, and r is 2. ) It is an N-glycidyl-substituted amide compound represented by the following, and is a new compound that has not been described in any literature. The N-glycidyl-substituted amide compound represented by the above general formula includes N-monoglycidyl-substituted aliphatic saturated and unsaturated monoamide compounds and N,N-
Diglycidyl substituted compounds, N-monoglycidyl substitution of aromatic and alicyclic monoamide compounds and N,
N-diglycidyl substituted compounds, N,N,N′,N′-tetraglycidyl substituted compounds of aliphatic saturated and unsaturated diamide compounds as polyamide compounds;
N, N, N' of aromatic and alicyclic diamide compounds,
N'-tetraglycidyl-substituted compounds, aromatic triamide compounds with N, N, N', N', N'', N''-hexaglycidyl-substituted compounds, aromatic tetraamide compounds with N, N, N', N', N ″、N″、N、N―
These include octaglycidyl-substituted compounds. Furthermore,
N,N of aliphatic saturated and unsaturated monoamide compounds
- One of the glycidoxy groups in diglycidyl-substituted compounds
-substituted compounds, N,N-diglycidyl substituted compounds of aromatic monoamide compounds with one to four glycidoxy groups substituted, and N,N,N',N'-tetraglycidyl substituted compounds of aromatic diamide compounds This includes compounds in which one or two glycidoxy groups are substituted. In addition, N,N-diglycidyl substituted compounds of aliphatic saturated, aromatic and alicyclic monoamide compounds are substituted with one or two N,N-diglycidylamino groups, and aliphatic saturated and aromatic diamide compounds. Also included are compounds in which N,N,N',N'-tetraglycidyl-substituted compounds are substituted with one or two N,N-diglycidylamino groups. As the most efficient method for producing the compound of the present invention, the method for producing an N-substituted amide compound provided above can be employed. That is, an amide compound and a halogen-substituted compound are reacted in an aprotic solvent in the presence of a strong basic substance to form an N-
This is a method for producing substituted amide compounds. In that method, when epichlorohydrin or dihalopropanol is used as the halogen-substituted compound, a glycidyl group-substituted N-substituted amide compound is produced. In addition, along with epihalohydrin or dihalopropanol as halogen-substituted compounds, alkyl halides, alkenyl halides,
By selectively reacting one type of aryl halide, it is possible to produce an N,N-substituted amide compound into which a glycidyl group and a residue corresponding to the halogen-substituted compound are introduced. It can also be produced by the following method, although the yield of the desired product is lower than in the previous method. Namely, there is a method in which a strong basic substance and an amide compound are reacted in advance in an aprotic solvent, and then a halogen-substituted compound is introduced to produce an N-substituted amide compound. React using transfer reaction to form N-
A method for producing substituted amide compounds or using fluoride ions as a dehydrohalogenation catalyst,
Examples include methods for producing N-substituted amide compounds. The present invention will be explained in more detail below. The compounds of the present invention include N-glycidyl-substituted monoamide compounds, N-glycidyl-substituted compounds of polyamide compounds higher than diamide compounds, N-glycidyl-substituted glycidyl ether compounds of hydroxyl-substituted monoamide compounds, and N-glycidyl-substituted hydroxyl-substituted diamide compounds. It is classified into glycidyl-substituted glycidyl ether compounds, amino-group-substituted monoamide compounds (N-glycidyl-substituted compounds), amino-group-substituted diamide compounds (N-glycidyl-substituted compounds), and the like. N-glycidyl-substituted amide compounds of monoamide compounds include monoglycidyl-substituted compounds represented by general formula (1) and diglycidyl-substituted compounds represented by general formula (2). In the above formula, R ₁ is an alkyl group, an alkenyl group, an aryl group, or an alicyclic group. The alkyl group has the general formula
It is represented by C _o H _2o+1 -, where n is an integer from 0 to 20. The alkenyl group is represented by the general formula C _o H _2o-1 -, where n is an integer from 2 to 20. The aryl group is a substituent containing an aromatic group, and also includes an arylalkyl group and an arylalkenyl group. As the aromatic ring, a benzene ring, a naphthalene ring, an anthracene ring, etc. can be used. An alicyclic group is a substituent containing an alicyclic structure. Furthermore, those in which one or more halogen atoms are introduced into the hydrocarbon moiety of the above-mentioned substituent are also covered. On the other hand, R ₂ in general formula (1) is an alkyl group, alkenyl group, arylalkyl group or arylalkenyl group, and the alkyl group has the general formula C _o H _2o+1 -
where n is an integer from 1 to 20. The alkenyl group is represented by the general formula C _o H _2o-1 -, where n is an integer and is 2.
-20. As the aromatic ring, a benzene ring, a naphthalene ring, an anthracene ring, etc. can be used. Among polyvalent amide compounds, N-glycidyl-substituted amide compounds of diamide compounds are represented by general formula (3). R ₁ is an alkylene group, an alkenylene group, an arylene group, or an alicyclic group. The alkylene group is represented by the general formula -C _o H _2o -, where n is an integer and is 0-20. The alkenylene group is represented by the general formula -C _o H _2o-2 -, where n is an integer and is 2-20. The arylene group is a substituent containing an aromatic ring, and also includes an arylalkyl group and an arylalkenyl group. As the aromatic ring, a benzene ring, a naphthalene ring, an anthracene ring, etc. can be used. An alicyclic group is a structure containing an alicyclic structure. Those in which one or more halogen atoms are introduced into the hydrocarbon moiety of the above substituents are also covered.
The N-glycidyl-substituted amide compound of the triamide compound is represented by the general formula (4). R ₁ is an aromatic ring or an alicyclic group, and examples of the aromatic ring include a benzene ring, a naphthalene ring, and an anthracene ring. In addition, those in which one or more aromatic rings and one or more halogen atoms are substituted are also covered.
The N-glycidyl-substituted amide compound of the tetraamide compound is represented by the general formula (5). R ₁ is an aromatic ring or an alicyclic group, and examples of the aromatic ring include a benzene ring, a naphthalene ring, and an anthracene ring. In addition, aromatic rings in which one or more halogen atoms are substituted are also covered.
The N-glycidyl-substituted glycidyl ether compound of the hydroxyl-substituted monoamide compound is represented by the general formula (6). n is an integer of 1 to 4, and when n=1, R ₁ is an alkylene group, alkenylene group, or arylene group. When n = 2 to 4, R ₁ represents an aromatic ring,
A benzene ring, a naphthalene ring, an anthracene ring, etc. are applicable. The alkylene group is represented by the general formula -C _o H _2o -,
n=an integer from 1 to 20. The alkenylene group is represented by the general formula -C _o H _2o-2 -, where n is an integer from 2 to 20. The arylene group is a substituent containing an aromatic ring, and examples of the aromatic ring include a benzene ring, a naphthalene ring, and an anthracene ring. In addition, those in which the hydrocarbon moiety of the above substituent is substituted with one or more halogen atoms are also covered. The N-glycidyl-substituted glycidyl ether compound of the hydroxyl-substituted diamide compound is represented by the general formula (7). n is an integer of 1 or 2, and R ₁ represents an aromatic ring such as a benzene ring, a naphthalene ring, an anthracene ring, etc. In addition, those in which the hydrocarbon moiety of the above substituent is substituted with one or more halogen atoms are also covered. The N-glycidyl-substituted amide compound of the amino group-substituted monoamide compound is represented by the general formula (8). n is an integer of 1 and 2, and R ₁ is an alkylene group, an arylene group, or an alicyclic group. The alkylene group is represented by the general formula -C _o H _2o -, where n is an integer from 1 to 20. The arylene group is a substituent containing an aromatic ring, and also includes an arylalkyl group. A benzene ring, a naphthalene ring, an anthracene ring, etc. can be used as the aromatic ring. An alicyclic group is a substituent containing an alicyclic structure. In addition, those in which the hydrocarbon moiety of the above substituent is substituted with one or more halogen atoms are also covered. The N-glycidyl-substituted amide compound of the amino group-substituted diamide compound is represented by the general formula (9). n is an integer of 1 or 2, and R ₁ is an aromatic ring, and examples of the aromatic ring include a benzene ring, a naphthalene ring, and an anthracene ring. In addition, aromatic rings in which one or more halogen atoms are substituted are also covered. Representative examples of the compounds of the present invention are illustrated below. Examples of N-glycidyl-substituted amide compounds of monoamide compounds include N-methyl-N-glycidyl acetamide, N-ethyl-N-glycidylformamide,
N-butyl-N-glycidylpropioamide, N
-Methyl-N-glycidylsteramide, N-decyl-N-glycidyl lauramide, N-stearyl-N-glycidylpropioamide, N-allyl-
N-glycidylacetamide, N-methallyl-N
-Glycidylpropioamide, N-butenyl-N
-Glycidylformamide, N-hexenyl-N
-Glycidylsteramide, N-benzyl-N-glycidylformamide, N-fetinel-N-glycidylacetamide, N-phenylpropyl-
N-glycidylpropioamide, N-cinnamyl-N-glycidyl lauramide, N-methyl-N-
Glycidyl acrylamide, N-methyl-N-glycidylmethacrylamide, N-ethyl-N-glycidylcrotonamide, N-butyl-N-glycidyl acrylamide, N-methyl-N-glycidyldecenamide, N-decyl-N- Glycidylbutenamide, N-stearyl-N-glycidylcrotonamide, N-allyl-N-glycidyl acrylamide, N-allyl-N-glycidylmethacrylamide, N-methallyl-N-glycidylcrotonamide, N-butenyl- N-glycidyl methacrylamide, N-hexenyl-N-glycidyldecenamide, N-benzyl-N-glycidyl acrylamide, N-phenethyl-N-glycidyl acrylamide, N-phenethyl-N-glycidylcrotoamide, N-phenylpropyl -N-glycidylmethacrylamide, N-cinnamyl-N-glycidyldecenamide, N-methyl-N-glycidylbenzamide, N-ethyl-N-glycidyltolylamide, N-butyl-N-glycidylphenylacetamide, N- Methyl-N-glycidylcinnamamide, N-decyl-N-glycidylnaphthalenecarboxamide, N-stearyl-N-glycidylanthracenecarboxamide, N-allyl-N-
Glycidylbenzamide, N-methallyl-N-glycidyltolylamide, N-butenyl-N-glycidylphenylacetamide, N-hexenyl-
N-glycidylallylbenzamide, N-benzyl-N-glycidylbenzamide, N-phenethyl-N-glycidyltolylamide, N-benzyl-N-glycidylcinnamamide, N-phenylpropyl-N-glycidylphenylacetamide,
N-Methyl-N-glycidylcyclohexanecarboxamide, N-ethyl-N-glycidylcyclohexylacetamide, N-butyl-N-glycidylcyclohexanecarboxamide, N-decyl-N-glycidylcyclohexylpropioamide, N-allyl-N-glycidylcyclohexane Carboxamide, N-methallyl-N-glycidylcyclohexylacetamide, N-benzyl-N
-Glycidylcyclohexanecarboxamide, N
-phenethyl-N-glycidylcyclohexylacetamide and the like. In addition, in N,N-diglycidyl substituted compounds,
For example, N,N-diglycidylformamide, N,
N-diglycidyl acetamide, N,N-diglycidylpropioamide, N,N-diglycidylbutyramide, N,N-diglycidylbutyramide,
N,N-diglycidylchloroacetamide, N,
N-diglycidylchloropropioamide, N,N
-Diglycidyl dichloroamide, N,N-diglycidyl acrylamide, N,N-diglycidyl methacrylamide, N,N-diglycidyl crotonamide, N,N-diglycidyl vinylacetamide, N,N-diglycidyl decena Mid, N, N-
Diglycidyl nonadecenamide, N,N-diglycidyl chloracrylamide, N,N-diglycidylbenzamide, N,N-diglycidylnaphthalenecarboxamide, N,N-diglycidylanthracenecarboxamide, N,N-diglycidyltolylamide , N,N-diglycidylphenylacetamide, N,N-diglycidyl phenylpropioamide, N,N-diglycidyl phenyl decanamide, N,N-diglycidyl phenyl acrylamide, N,N-di Glycidylbenzylacrylamide, N,N-diglycidylcinnamamide, N,
N-diglycidylallylbenzamide, N,N-
Diglycidylchlorobenzamide, N,N-diglycidyldichlorobenzamide, N,N-diglycidylchlorobromobenzamide, N,N-diglycidylcyclobutanecarboxamide, N,N-
diglycidyl cyclopentane carboxamide,
N,N-diglycidylcyclohexanecarboxamide, N,N-diglycidylcyclopentanecarboxamide, N,N-diglycidylcyclohexylacetamide, N,N-diglycidylcyclohexylpropioamide, N,N-diglycidylcyclohexenecarboxamide, N, N-diglycidylcyclohexadienecarboxamide, N,N
- Examples include diglycidylcyclopentylphenylacetamide. In addition, N-glycidyl-substituted amide compounds of polyvalent amide compounds include, for example, N,N,N',N'-tetraglycidyl oxamide, N,N,N',N'-
Tetraglycidyl malonamide, N, N, N',
N'-tetraglycidyl succinamide, N, N,
N′,N′-tetraglycidylglutaramide, N,
N,N′,N′-tetraglycidyl adipamide, N,
N,N',N'-tetraglycidylpiperamide, N,
N,N',N'-tetraglycidyl suberamide, N,
N,N′,N′-tetraglycidyl azeramide, N,
N,N',N'-tetraglycidyl sebaamide, N,
N,N',N'-tetraglycidyl octadecanedicarboxamide, N,N,N',N'-tetraglycidyl fumaramide, N,N,N',N'-tetraglycidyl maleamide, N,N,N' , N'-tetraglycidylcitraconamide, N, N, N', N'-
Tetraglycidyl mesaconamide, N, N, N',
N′-tetraglycidyldecenedicarboxamide,
N,N,N',N'-tetraglycidyl octadecenedicarboxamide, N,N,N',N'-tetraglycidyl phthalamide, N,N,N',N'-tetraglycidyl isophthalamide, N, N, N′,
N'-tetraglycidyl terephthalamide, N,N,
N',N'-tetraglycidylnaphthalene dicarboxamide, N,N,N',N'-tetraglycidyl anthracenedicarboxamide, N,N,N',
N'-tetraglycidylcarbamoylphenylacetamide, N,N,N',N'-tetraglycidylphenylcitraconamide, N,N,N',N'-
Tetraglycidyl diphenamide, N, N, N′,
N′-tetraglycidylchloroisophthalamide,
N,N,N',N'-tetraglycidylbromoisophthalamide, N,N,N',N'-tetraglycidylcyclobutanedicarboxamide, N,N,N',
N'-tetraglycidylcyclopentanedicarboxamide, N,N,N',N'-tetraglycidylcyclohexanedicarboxamide, N,N,N',
N'-tetraglycidylcycloheptanecarboxamide, N,N,N',N'-tetraglycidylcyclohexenedicarboxamide, N,N,N',
N'-tetraglycidyl camphoramide, N,N,
N′, N′, N″, N″—Hexaglycidylbenzenetricarboxamide, N, N, N′, N′, N″, N″—
Hexaglycidyl naphthalene tricarboxamide, N, N, N′, N′, N″, N″-Hexaglycidyl naphthalene tricarboxamide, N, N, N′,
N′, N″, N″-hexaglycidylchlorobenzenetricarboxamide, N, N, N′, N′, N″,
N″-hexaglycidylcyclohexanetricarboxamide, N, N, N′, N′, N″, N″, N,
N-octaglycidyl pyromellituamide,
N,N,N′,N′,N″,N″,N,N-octaglycidylnaphthalenetetracarboxamide,
Examples include N, N, N', N', N'', N'', N, N-octaglycidylcycloheptane tetracarboxamide. On the other hand, N-glycidyl-substituted glycidyl ether compounds of hydroxyl-substituted monoamide compounds include, for example, N,N-diglycidylglycidoxypropioamide, N,N,-diglycidylglycidoxydiphenylacetamide, N,N-diglycidyl Glycidoxybutyramide, N,N-diglycidylglycidoxyheptanamide, N,N-diglycidylglycidoxydecanamide, N,N-diglycidylglycidoxycrotonamide, N,N-diglycidyl Glycidoxydimethylheptinamide, N,N-diglycidylglycidoxybenzamide, N,N-
Diglycidylglycidoxytolylamide, N,N
-Diglycidylglycidoxyphenylbenzamide, N,N-diglycidylglycidoxynaphthalenecarboxamide, N,N-diglycidyldiglycidoxybenzamide, N,N-diglycidyltriglycidoxybenzamide, N,N-diglycidyldiglycidoxybenzamide Examples include sidoxytolylamide. In N-glycidyl-substituted glycidyl ether compounds of hydroxyl-substituted diamide compounds, N, N, N′,
N′-tetraglycidylglycidoxyphthalamide,
N,N,N',N'-tetraglycidylglycidoxyisophthalamide, N,N,N',N'-tetraglycidylglycidoxyterephthalamide, N,N,
N',N'-tetraglycidyl diglycidoxyphthalamide, N,N,N',N'-tetraglycidyl diglycidoxyisophthalamide, N,N,N',
Examples include N'-tetraglycidyl diglycidoxyterephthalamide. N-glycidyl-substituted compounds of amino group-substituted monoamide compounds include N,N,N',N'-tetraglycidylglycinamide, N,N,N',N'-tetraglycidylalanineamide, N,N-diglycidylamino -N,N-diglycidylbutanamide, N,N,N',N'-tetraglycidyldiamino-N'',N''-diglycidylpropionamide,
N,N-diglycidylamino-N',N'-diglycidylbenzamide, N,N-diglycidylamino-N',N'-diglycidylchlorobenzamide,
N,N-diglycidylamino-N',N'-diglycidyltribromobenzamide, N,N,N',
N'-tetraglycidyldiamino-N'',N''-diglycidylbenzamide, N,N-diglycidylaminophenyl-N',N'-diglycidylacetamide, N,N-diglycidylaminophenyl-
N',N'-diglycidylpropionamide, N,N
-Diglycidylamino-N',N'-diglycidylnaphthalenecarboxamide, N,N-diglycidylamino-N',N'-cyclohexanecarboxamide, etc. N-glycidyl substituted compounds of amino group-substituted diamide compounds include N,N,N′,N′,N″,N″-hexaglycidyl aspartodiamide, N,N-diglycidylamino-,N′,N′, N″,N″-tetraglycidylglutaradiamide, N,N-diglycidylamino-N′,N′,N″,N″-tetraglycidyl phthalamide, N,N-diglycidylamino-
N′, N′, N″, N″-tetraglycidyl isophthalamide, N, N-diglycidylamino-N′, N′,
Examples include N″, N″-tetraglycidyl terephthalamide. Among the compounds exemplified above, N-glycidyl-substituted amide compounds of lower fatty acid amides can be isolated and purified relatively easily by operations such as distillation. However, other N-glycidyl-substituted amide compounds, especially N,N-diglycidyl compounds, have very low volatility and are difficult to isolate by distillation. On the other hand, the glycidyl group is a highly reactive substituent, and reacts with reactive compounds such as alkaline substances present in the reaction system, causing side reactions such as addition condensation and the opening of the epoxy ring. Therefore, the epoxy equivalent of the product will be higher than the theoretical value, and the degree of deviation will depend on the reactivity of the amide compound to be reacted. It is. The N-glycidyl-substituted amide compound of the present invention described above is representative of existing monoglycidyl ether compounds such as butyl glycidyl ether, allyl glycidyl ether, and phenyl glycidyl ether, monoglycidyl ester compounds such as glycidyl methacrylate, and bisphenol type epoxy resins. diglycidyl ether compounds such as diglycidyl phthalate, diglycidyl ester compounds such as diglycidyl phthalate, diglycidyl amine compounds such as N,N-diglycidylaniline, N,N-diglycidyltoluidine, and further N,N,N',N' - It corresponds to glycidyl-substituted compounds that are not N-glycidyl-substituted amides, such as tetraglycidyl diamine compounds such as tetraglycidyl xylylene diamine, N,N,N',N'-tetraglycidyldiaminodiphenylmethane, and these Reactive diluents, crosslinking agents, epoxidation reagents, and
It has a wide range of uses as a resin improver, epoxy resin, etc., as well as as a raw material for adhesives, paints, and as a binder for composite materials related to electronic materials. Next, the present invention will be further explained by examples. Example 1 Production of N,N-diglycidyl propionamide: Add 15 g of propionamide, 56 g of epichlorohydrin, and 20 g of sodium hydroxide to 150 ml of dimethyl sulfoxide (hereinafter abbreviated as DMSO) and heat at 40°C.
The mixture was allowed to react for 4 hours. After the reaction, insoluble materials were separated, 200 ml of benzene and 150 ml of distilled water were added, and the mixture was thoroughly stirred and then separated.The aqueous layer was extracted twice with 100 ml of benzene, and the benzene layer was collected and dried over magnesium sulfate. The benzene layer was distilled under reduced pressure, and a 114-116°C/3 mmHg fraction was collected to obtain 27 g (yield: 73%) of N,N-diglycidylpropionamide. The epoxy equivalent was measured by perchloric acid titration and found to be 94 g/eg. (Theoretical value 93/eg.). Examples 2 to 4 Reactions were carried out using the combinations of raw materials, strong basic substances, and solvents listed in Table 1 under the conditions listed in Table 1. In addition,
The reaction was carried out by adding 0.05 g of phenethiazine.
After the reaction, treatment was carried out in exactly the same manner as in Example 1, and the results shown in Table 2 were obtained.

【table】

【table】

[Table] Example 5 Production of N-n-butyl-N-glycidyl acrylamide: 14 g of acrylamide, 37 g of epichlorohydrin, 46 g of n-butyl chloride, 20 g of sodium hydroxide, and 0.05 g of phenothiazine were added to 150 ml of DMSO, and the mixture was heated at 40°C for 5 hours. The reaction was carried out. After the reaction, after separating the insoluble matter, the raw materials and solvent were distilled off, 100 ml of benzene and 50 ml of distilled water were added to the residual liquid, and after thorough stirring, the layers were separated, and the aqueous layer was extracted twice with 50 ml of benzene. The benzene layer was collected and dried with magnesium sulfate. Distill the benzene layer under reduced pressure to give 103 to 105
C/5 mmHg fraction was collected to obtain 22 g of N-n-butyl-N-glycidyl acrylamide (yield 59%). The epoxy equivalent was measured by perchloric acid titration and found to be 184 g/eg. (Theoretical value 183 g/eg.). Examples 6 to 10 Reactions were carried out using the combinations of raw materials, strong basic substances, and solvents listed in Table 3 under the conditions listed in Table 3. After the reaction, treatment was carried out in exactly the same manner as in Example 5, and Table 4
The results described were obtained.

【table】

[Table] Example 11 Production of N,N-diglycidylbenzamide: Add 24 g of benzamide, 56 g of epichlorohydrin, and 20 g of sodium hydroxide to 150 ml of DMSO.
The reaction was carried out at ℃ for 2 hours. After the reaction, after separating the insoluble materials, the raw materials and solvent were distilled off, and 100 ml of benzene and 50 ml of distilled water were added to the remaining liquid.
After thorough stirring, the mixture was separated, and the aqueous layer was extracted twice with 50 ml of benzene. The benzene layer was collected and dried over magnesium sulfate. After benzene was distilled off, the remaining solvent and the like were further distilled off at 120°C/2 mmHg to obtain 42 g (yield 91%) of the desired N,N-diglycidylbenzamide. The epoxy equivalent was measured by perchloric acid titration and found to be 119 g/eg. (Theoretical value 117 g/eg.). Furthermore, when the refractive index of this material was measured at 25°C, it was 1.5410. Examples 12 to 24 Reactions were carried out using the combinations of raw materials, strong basic substances, and solvents listed in Table 5 under the conditions listed in Table 5. After the reaction, treatment was carried out in exactly the same manner as in Example 11, and Table 6
The results described were obtained.

【table】

【table】

[Table] Example 25 Production of N-methyl-N-glycidyl acrylamide: 150 ml of sulforane, 14 g of acrylamide, 0.05 g of phenothiazine, 37 g of epichlorohydrin,
20 g of sodium hydroxide was added, 15 g of methyl chloride was further blown into the mixture, and the reaction was carried out at 40° C. for 3 hours. After the reaction, insoluble materials were separated and the liquid was distilled under reduced pressure. The 57-59℃/2mmHg fraction was collected, and 18g of N-methyl-N-glycidyl-acrylamide (yield
63%). The epoxy equivalent was measured by perchloric acid titration and found to be 142 g/eg. (Theoretical value 141g/eg.)
was obtained. Examples 26 to 27 Reactions were carried out using the combinations of raw materials, strong basic substances, and solvents listed in Table 7 under the conditions listed in Table 7. After the reaction, treatment was carried out in exactly the same manner as in Example 26, and Table 8
The results described were obtained.

【table】

[Table] Example 28 Adhesion test: N,N-diglycidyl-p produced in Example 17
-Glycidoxy-benzamide was used to conduct an adhesion test on steel plates with the following formulation. ●Blend 100 parts of N,N-diglycidyl-p-glycidoxy-benzamide, 6 parts of dicyandiamide, and 2 parts of Erosyl were thoroughly kneaded using three rolls. Furthermore, 30 parts of alumina was uniformly dispersed therein and degassed under reduced pressure to obtain a blend. ● Creation of test piece Width 25m/m x length 100mm degreased with acetone
Apply the compound to a steel plate (JIS G3141) measuring m/m x 1.6 m/m thick from one end to 12.5 m/m, place another steel plate on top of it, and press it with a clip. A test piece was prepared by curing at 180°C for 60 minutes. ●Test When the tensile shear strength of the test piece was measured according to JIS K6850, a value of 190 Kg/cm ³ was obtained.

Claims (1)

[Claims] 1. General formula (R ₁ is an aliphatic hydrocarbon group, aromatic hydrocarbon group, or alicyclic hydrocarbon group, and X is hydrogen, a glycidoxy group, or an N,N-diglycidylamino group. p is an integer of 0 or 1. and q is 1~
It is an integer of 4. R ₂ is an alkyl group, an alkenyl group, an arylalkyl group, or an arylalkenyl group, r is an integer of 1 or 2, and s is an integer of 1 to 4. However, when X is hydrogen, p
is 0 or 1, q is 0 or 1, and when s is 1, r is 1 or 2, while when s is 2 to 4, r is 2. When X is a glycidoxy group, p is 1 and r is 2. When X is an N,N-diglycidylamino group, p is 1, q is 1 or 2,
s is 1 or 2, and r is 2. ) N-glycidyl substituted amide compound represented by: