JPH11189565A - Molecular compound containing phenol derivative as component compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject molecular compound manifesting excellent properties in a technological field such as selectively separating a useful material, making a material nonvolatile and making the material sustained release by using a phenol derivative having sulfonyl group or carbonyl group at the o- position of the hydroxy group as a component compound. SOLUTION: The objective molecular compound is obtained by using a phenol derivative of the formula (R1 and R5 are each H, a halogen, a 1-4C alkyl or the likes; R2 and R4 are each H, a 1-4C alkoxy, OH or the like, with the proviso that when one of R1 , R3 and R5 is a 1-4C alkoxy, R2 and R4 are each H, a halogen, OH or the like; R3 is H, a halogen, a 2-4C alkenyl or the like) as a component compound. The molecular compound is the compound in which two or more kinds of component compounds which can exist alone and stably are bonded to each other with a comparatively weak interaction without a covalent bond, such as a hydrogen bond and a van der Waals attraction and includes a hydrate, a solvate, an adduct, a clathrate compound and the like.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a novel molecular compound, and more particularly to a molecular compound comprising a phenol derivative having a specific structure as a component compound and a method for producing the same.

[0002]

2. Description of the Related Art A molecular compound is a compound in which two or more kinds of compounds are bonded by a relatively weak interaction other than a covalent bond represented by a hydrogen bond, van der Waals force, or the like. In recent years, since it has the property of dissociating into each component compound, selective separation of useful substances,
Applications in technical fields such as chemical stabilization, non-volatilization, sustained release, and powdering are expected.

An example of a specific molecular compound is an clathrate compound. For example, Japanese Patent Application Laid-Open No. 61-53201 discloses 1,1,6,6-tetraphenyl-2,4-hexadiyne-1,6. -Diol or 1,1-di (2,4-dimethylphenyl) -2-propyn-1-ol, JP-A-62-2701 discloses that 1,1'-bis-2-naphthol and 5 Inclusion compounds with -chloro-2-methyl-4-isothiazolin-3-one and the like are described. JP-A-3-279373 discloses an inclusion compound of a bisphenol compound and an isothiazolone compound. Further, Japanese Unexamined Patent Application Publication No.
No. 6 discloses an inclusion compound of tetrakisphenols with various organic compounds.

[0004]

However, in the prior art, a molecular compound having satisfactory performance in selective separation, chemical stabilization, non-volatization, sustained release, powdering, etc. has not yet been found. .

An object of the present invention is to provide a phenol derivative having a specific structure, which exhibits excellent performance in technical fields such as selective separation of useful substances, chemical stabilization, non-volatization, sustained release, and powdering, as a component compound. To provide a novel molecular compound.

[0006]

Means for Solving the Problems The inventors of the present invention have conducted intensive studies to achieve the above object, and as a result, a phenol derivative having a sulfonyl group or a carbonyl group at the ortho position of a hydroxyl group has effectively formed a molecular compound to be useful. The inventors have found that they show extremely excellent performance in the technical fields such as selective separation of substances, chemical stabilization, non-volatilization, sustained release, and powderization, and have completed the present invention.

That is, the present invention relates to a compound represented by the general formula (I):

Embedded image [Wherein, R ₁ and R ₅ may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group, C2
-C4 alkenyl group, C1-C4 alkoxy group, hydroxyl group, or

Embedded image (Y and Z are a C1 to C8 alkyl group, a C2 to C8 alkenyl group, a C1 to C6 alkoxy group, a hydroxyl group, an amino group which may have a substituent, and a cycloalkyl which may have a substituent. A phenyl group which may have a substituent or an aralkyl group which may have a substituent), and R ₂ and R ₄ may be the same or different, and represent a hydrogen atom , A halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, or a hydroxyl group, provided that any one of R ₁ , R ₃ or R ₅ is a C1-C4 alkoxy group. Or in the case of a hydroxyl group, a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group, or

Embedded image Wherein Y and Z are the same as defined above,
R ₃ is a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group, a general formula (II), a general formula (III)

Embedded image Ｘwhere X is

Embedded image (W represents any one of 0, 1, and 2, u represents 0 or 1, and q represents any of 0 to 4, R ₁₄ and R ₁₅ may be the same or different, and represent a hydrogen atom, Halogen atom, C
C1-C4 alkyl group, C2-C4 alkenyl group, C
1 to C4 represents an alkoxy group, a hydroxyl group, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent, wherein R ₁₆ is a hydrogen atom, a C1 to C4 alkyl group,
A 2-C4 alkenyl group, a C1-C4 alkoxy group,
A hydroxyl group, a phenyl group which may have a substituent or an aralkyl group which may have a substituent), and R ₆ , R ₉ ,
R ₁₀ may be the same or different from each other, and may be a hydrogen atom, a halogen atom, a C1 to C4 alkyl group,
4, an alkenyl group, a C1-C4 alkoxy group, a hydroxyl group, or

Embedded image Wherein Y and Z are the same as defined above,
R ₇ , R ₈ , R ₁₁ , and R ₁₃ may be the same or different from each other, and include a hydrogen atom, a halogen atom, a C1 to C4 alkyl group, a C2 to C4 alkenyl group, a C1 to C4 alkoxy group, or Represents a hydroxyl group, provided that when R ₁₂ is a C1 to C4 alkoxy group or a hydroxyl group, R ₁₁ is a hydrogen atom, a halogen atom, a C1 to C4 alkyl group, a C2 to C4 alkenyl group, a C1 to C4 alkoxy group, Hydroxyl group, or

Embedded image Wherein Y and Z are the same as defined above,
R ₁₂ is a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group, or

Embedded image (Wherein Y and Z are the same as described above), or

Embedded image Wherein Y and Z are the same as defined above,
When R ₃ is the general formula (II), R ₁ , R ₅ , R ₆ ,
One of R ₉

Embedded image (Wherein Y and Z are the same as described above);
_{When 3} is the general formula (III), at least one of R ₁ , R ₅ and R ₁₀ is

Embedded image (Wherein Y and Z are the same as described above);
_{When 3} is other than the general formula (II) or (III), _one of R ₁ and R ₅ is

Embedded image (Wherein Y and Z are the same as described above). ]
And a molecular compound comprising a phenol derivative represented by the following formula:

Further, the present invention provides a molecular compound comprising a phenol derivative represented by the general formula (I) as a component compound, wherein the molecular compound is an inclusion compound, and a molecular compound represented by the general formula (I). Phenol derivatives and antibacterial agents, antifungal agents, insecticides, pest repellents, fragrances, deodorants / deodorants, antifouling agents, curing for paints / resins / adhesives that react with the phenol derivatives to form molecular compounds And a curing accelerator, a natural essential oil, an antioxidant, a vulcanization accelerator or an organic solvent, which relates to a component compound and a molecular compound, and further comprises a phenol derivative represented by the general formula (I): The present invention relates to a method for producing the above molecular compound, which comprises reacting a component compound which reacts to form a molecular compound.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION The molecular compound in the present invention is
A compound in which two or more component compounds of a compound that can exist stably alone are bound by a relatively weak interaction other than a covalent bond represented by a hydrogen bond, van der Waals force, etc. Compounds, adducts,
Inclusion compounds and the like are included.

In the general formula (I), R ₁ and R ₅ may be the same or different and include a hydrogen atom, a halogen atom,
C1-C4 alkyl group, C2-C4 alkenyl group, C
1 to C4 alkoxy group, hydroxyl group, or

Embedded image (Y and Z are a C1 to C8 alkyl group, a C2 to C8 alkenyl group, a C1 to C6 alkoxy group, a hydroxyl group, an amino group which may have a substituent, and a cycloalkyl which may have a substituent. A phenyl group which may have a substituent or an aralkyl group which may have a substituent). Specific examples of R ₁ and R ₅ include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, and an iso-butyl group. , Sec-butyl group, tert
-Butyl group, vinyl group, allyl group, isopropenyl group,
1-propenyl group, 2-butenyl group, 3-butenyl group,
1,3-butanedienyl group, methoxy group, ethoxy group,
n-propoxy group, iso-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, te
rt-butoxy group and the like.

As Y and Z, a C1 to C6 alkyl group, a C2 to C6 alkenyl group, a C1 to C4 alkyl group, a C2 to C4 alkenyl group or a C1 to C4
4 alkoxy group, hydroxyl group, or cyclohexyl group which may have a halogen atom, C1-C4 alkyl group, C2-C4 alkenyl group, or C1-
A C4 alkoxy group, a hydroxyl group or a cyclopentyl group which may have a halogen atom, a C1 to C4 alkyl group, a C2 to C4 alkenyl group or C1.
To C4 alkoxy group or phenyl group optionally having a halogen atom, C1 to C4 alkyl group or C2
A benzyl group which may have a alkenyl group or a C1 to C4 alkoxy group or a hydroxyl group or a halogen atom, a C1 to C4 alkyl group or a C2 to C4
Alkenyl group or C1 to C4 alkoxy group or hydroxyl group or phenethyl group which may have a halogen atom, C1 to C4 alkyl group or C2 to C4
An alkenyl group or a C1-C4 alkoxy group or a hydroxyl group or an α-methylbenzyl group optionally having a halogen atom, or a C1-C4 alkyl group or a C2-C4 alkenyl group or a C1-C4 alkoxy group or a hydroxyl group Or a naphthyl group which may have a halogen atom is preferable, for example, methyl group, ethyl group, n-propyl group, iso-propyl group, n-butyl group, iso-butyl group, sec-butyl group, tert-
Butyl group, n-pentyl group, iso-pentyl group, se
c-pentyl group, neo-pentyl group, tert-pentyl group, n-hexyl group, iso-hexyl group, sec
-Hexyl group, n-heptyl group, iso-heptyl group,
sec-heptyl group, n-octyl group, iso-octyl group, sec-octyl group, vinyl group, allyl group, 1-
Propenyl group, iso-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1,3-butanedienyl group, 1-pentenyl group, 2-pentenyl group, 3
-Pentenyl, 4-pentenyl, hexynyl, hexidinyl, heptynyl, heptidinyl, octynyl, octidinyl, cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethyl Cyclohexyl group, tetramethylcyclohexyl group, pentamethylcyclohexyl group, hexamethylcyclohexyl group, cycloheptyl group, methylcycloheptyl group, phenyl group, o- or m- or p
-Tolyl group, 2,3- or 2,4- or 2,5- or 2,6- or or 3,4- or 3,5- or 4,6-xylyl group, o- or m- or p- Cumenyl, mesityl, benzyl, o- or m- or p-toluylmethyl, 2,3- or 2,4- or 2,5- or 2,6- or 3,4- or 3,5- Or 4,5-xylylmethyl group, mesitylmethyl group, o- or m- or p-cumenylmethyl group, phenethyl group, α-methylbenzyl group, 1-
Specific examples include a naphthyl group, a 2-naphthyl group, a methoxy group, an ethoxy group, and a dimethylamino group. In the following text, unless otherwise specified, R ₂ ,
Y and Z in R ₃ , R _{4 and the} like mean the same as described above.

In the general formula (I), R ₂ and R ₄ may be the same or different and include a hydrogen atom, a halogen atom,
C1-C4 alkyl group, C2-C4 alkenyl group, C
Represents an alkoxy group of 1 to C4 or a hydroxyl group, provided that R
_{When any of 1} , R ₃ or R ₅ is a C1 to C4 alkoxy group or a hydroxyl group, a hydrogen atom, a halogen atom,
A C4 alkyl group, a C2-C4 alkenyl group, a C1
A C4 alkoxy group, a hydroxyl group, or

Embedded image And represents, for example, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, n-
Propyl group, iso-propyl group, n-butyl group, is
o-butyl group, sec-butyl group, tert-butyl group, vinyl group, allyl group, isopropenyl group, 1-propenyl group, 2-butenyl group, 3-butenyl group, 1,3-
Butanedienyl group, methoxy group, ethoxy group, n-propoxy group, iso-propoxy group, n-butoxy group, i
Specific examples include a so-butoxy group, a sec-butoxy group, and a tert-butoxy group.

In the general formula (I), R ₃ is a hydrogen atom, a halogen atom, a C1 to C4 alkyl group, a C2 to C4
4 alkenyl group, C1-C4 alkoxy group, hydroxyl group, general formula (II), general formula (III), or

Embedded image Represents a group selected from Specific examples include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, tert
-Butyl group, vinyl group, allyl group, isopropenyl group,
1-propenyl group, 2-butenyl group, 3-butenyl group,
1,3-butanedienyl group, methoxy group, ethoxy group,
n-propoxy group, iso-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, te
rt-butoxy group and the like.

In the general formulas (II) and (III), X is

Embedded image (W represents any one of 0, 1, and 2, u represents 0 or 1, and q represents any of 0 to 4, R ₁₄ and R ₁₅ may be the same or different, and represent a hydrogen atom, Halogen atom, C
C1-C4 alkyl group, C2-C4 alkenyl group, C
1 to C4 represents an alkoxy group, a hydroxyl group, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent, wherein R ₁₆ is a hydrogen atom, a C1 to C4 alkyl group,
A 2-C4 alkenyl group, a C1-C4 alkoxy group,
A hydroxyl group, a phenyl group which may have a substituent or an aralkyl group which may have a substituent). Specifically, a 1,1-dimethylmethylene group, 1-methyl-t-
Butyl-methylene group, 1-methyl-1-phenyl-methylene group, 1-methyl-1-hydroxymethylene group, N-
Examples include a methylimino group, an N-methoxyimino group, an N-allylimino group, a 1,1-cyclohexylene group, and a 1,1-cyclopentylene group. Formulas (II) and (II
In I), R ₆ , R ₉ and R ₁₀ may be the same or different from each other and represent a hydrogen atom, a halogen atom, C1 to C4.
Alkyl group, C2-C4 alkenyl group, C1-C4
An alkoxy group, a hydroxyl group, or

Embedded image Represents a group selected from And, specifically, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, tert
-Butyl group, vinyl group, allyl group, isopropenyl group,
1-propenyl group, 2-butenyl group, 3-butenyl group,
1,3-butanedienyl group, methoxy group, ethoxy group,
n-propoxy group, iso-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, te
An rt-butoxy group and the like can be exemplified.

R ₇ , R ₈ , R ₁₁ and R ₁₃ may be the same or different from each other and include a hydrogen atom, a halogen atom,
A C4 alkyl group, a C2-C4 alkenyl group, a C1
Represents a C4 alkoxy group or a hydroxyl group. However, R ₁₂ is C1
R ₁₁ is a hydrogen atom, a halogen atom, a C 1 -C 4 alkyl group, a C 2 -C 4
4 alkenyl groups, C1 to C4 alkoxy groups, hydroxyl groups, or

Embedded image Represents a group selected from Specific examples include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, tert
-Butyl group, vinyl group, allyl group, isopropenyl group,
1-propenyl group, 2-butenyl group, 3-butenyl group,
1,3-butanedienyl group, methoxy group, ethoxy group,
n-propoxy group, iso-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, te
rt-butoxy group and the like. R ₁₂ is a hydrogen atom,
A halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group, or

Embedded image Represents a group selected from Specific examples include a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, an iso-butyl group, a sec-butyl group, tert
-Butyl group, vinyl group, allyl group, isopropenyl group,
1-propenyl group, 2-butenyl group, 3-butenyl group,
1,3-butanedienyl group, methoxy group, ethoxy group,
n-propoxy group, iso-propoxy group, n-butoxy group, iso-butoxy group, sec-butoxy group, te
rt-butoxy group and the like.

The phenol derivative used in the present invention is not particularly limited as long as it is a compound represented by the general formula (I) having at least one sulfonyl group or carbonyl group at the ortho position of the hydroxyl group. Table 1 (Tables 1001 to 1087) shows specific examples of the compounds represented by
Table 2 (Tables 1088 to 1158), Table 3 (Table 115)
9 to Table 1266).

[0017]

[Table 1001]

[0018]

[Table 1002]

[0019]

[Table 1003]

[0020]

[Table 1004]

[0021]

[Table 1005]

[0022]

[Table 1006]

[0023]

[Table 1007]

[0024]

[Table 1008]

[0025]

[Table 1009]

[0026]

[Table 1010]

[0027]

[Table 1011]

[0028]

[Table 1012]

[0029]

[Table 1013]

[0030]

[Table 1014]

[0031]

[Table 1015]

[0032]

[Table 1016]

[0033]

[Table 1017]

[0034]

[Table 1018]

[0035]

[Table 1019]

[0036]

[Table 1020]

[0037]

[Table 1021]

[0038]

[Table 1022]

[0039]

[Table 1023]

[0040]

[Table 1024]

[0041]

[Table 1025]

[0042]

[Table 1026]

[0043]

[Table 1027]

[0044]

[Table 1028]

[0045]

[Table 1029]

[0046]

[Table 1030]

[0047]

[Table 1031]

[0048]

[Table 1032]

[0049]

[Table 1033]

[0050]

[Table 1034]

[0051]

[Table 1035]

[0052]

[Table 1036]

[0053]

[Table 1037]

[0054]

[Table 1038]

[0055]

[Table 1039]

[0056]

[Table 1040]

[0057]

[Table 1041]

[0058]

[Table 1042]

[0059]

[Table 1043]

[0060]

[Table 1044]

[0061]

[Table 1045]

[0062]

[Table 1046]

[0063]

[Table 1047]

[0064]

[Table 1048]

[0065]

[Table 1049]

[0066]

[Table 1050]

[0067]

[Table 1051]

[0068]

[Table 1052]

[0069]

[Table 1053]

[0070]

[Table 1054]

[0071]

[Table 1055]

[0072]

[Table 1056]

[0073]

[Table 1057]

[0074]

[Table 1058]

[0075]

[Table 1059]

[0076]

[Table 1060]

[0077]

[Table 1061]

[0078]

[Table 1062]

[0079]

[Table 1063]

[0080]

[Table 1064]

[0081]

[Table 1065]

[0082]

[Table 1066]

[0083]

[Table 1067]

[0084]

[Table 1068]

[0085]

[Table 1069]

[0086]

[Table 1070]

[0087]

[Table 1071]

[0088]

[Table 1072]

[0089]

[Table 1073]

[0090]

[Table 1074]

[0091]

[Table 1075]

[0092]

[Table 1076]

[0093]

[Table 1077]

[0094]

[Table 1078]

[0095]

[Table 1079]

[0096]

[Table 1080]

[0097]

[Table 1081]

[0098]

[Table 1082]

[0099]

[Table 1083]

[0100]

[Table 1084]

[0101]

[Table 1085]

[0102]

[Table 1086]

[0103]

[Table 1087]

[0104]

[Table 1088]

[0105]

[Table 1089]

[0106]

[Table 1090]

[0107]

[Table 1091]

[0108]

[Table 1092]

[0109]

[Table 1093]

[0110]

[Table 1094]

[0111]

[Table 1095]

[0112]

[Table 1096]

[0113]

[Table 1097]

[0114]

[Table 1098]

[0115]

[Table 1099]

[0116]

[Table 1100]

[0117]

[Table 1101]

[0118]

[Table 1102]

[0119]

[Table 1103]

[0120]

[Table 1104]

[0121]

[Table 1105]

[0122]

[Table 1106]

[0123]

[Table 1107]

[0124]

[Table 1108]

[0125]

[Table 1109]

[0126]

[Table 1110]

[0127]

[Table 1111]

[0128]

[Table 1112]

[0129]

[Table 1113]

[0130]

[Table 1114]

[0131]

[Table 1115]

[0132]

[Table 1116]

[0133]

[Table 1117]

[0134]

[Table 1118]

[0135]

[Table 1119]

[0136]

[Table 1120]

[0137]

[Table 1121]

[0138]

[Table 1122]

[0139]

[Table 1123]

[0140]

[Table 1124]

[0141]

[Table 1125]

[0142]

[Table 1126]

[0143]

[Table 1127]

[0144]

[Table 1128]

[0145]

[Table 1129]

[0146]

[Table 1130]

[0147]

[Table 1131]

[0148]

[Table 1132]

[0149]

[Table 1133]

[0150]

[Table 1134]

[0151]

[Table 1135]

[0152]

[Table 1136]

[0153]

[Table 1137]

[0154]

[Table 1138]

[0155]

[Table 1139]

[0156]

[Table 1140]

[0157]

[Table 1141]

[0158]

[Table 1142]

[0159]

[Table 1143]

[0160]

[Table 1144]

[0161]

[Table 1145]

[0162]

[Table 1146]

[0163]

[Table 1147]

[0164]

[Table 1148]

[0165]

[Table 1149]

[0166]

[Table 1150]

[0167]

[Table 1151]

[0168]

[Table 1152]

[0169]

[Table 1153]

[0170]

[Table 1154]

[0171]

[Table 1155]

[0172]

[Table 1156]

[0173]

[Table 1157]

[0174]

[Table 1158]

[0175]

[Table 1159]

[0176]

[Table 1160]

[0177]

[Table 1161]

[0178]

[Table 1162]

[0179]

[Table 1163]

[0180]

[Table 1164]

[0181]

[Table 1165]

[0182]

[Table 1166]

[0183]

[Table 1167]

[0184]

[Table 1168]

[0185]

[Table 1169]

[0186]

[Table 1170]

[0187]

[Table 1171]

[0188]

[Table 1172]

[0189]

[Table 1173]

[0190]

[Table 1174]

[0191]

[Table 1175]

[0192]

[Table 1176]

[0193]

[Table 1177]

[0194]

[Table 1178]

[0195]

[Table 1179]

[0196]

[Table 1180]

[0197]

[Table 1181]

[0198]

[Table 1182]

[0199]

[Table 1183]

[0200]

[Table 1184]

[0201]

[Table 1185]

[0202]

[Table 1186]

[0203]

[Table 1187]

[0204]

[Table 1188]

[0205]

[Table 1189]

[0206]

[Table 1190]

[0207]

[Table 1191]

[0208]

[Table 1192]

[0209]

[Table 1193]

[0210]

[Table 1194]

[0211]

[Table 1195]

[0212]

[Table 1196]

[0213]

[Table 1197]

[0214]

[Table 1198]

[0215]

[Table 1199]

[0216]

[Table 1200]

[0219]

[Table 1201]

[0218]

[Table 1202]

[0219]

[Table 1203]

[0220]

[Table 1204]

[0221]

[Table 1205]

[0222]

[Table 1206]

[0223]

[Table 1207]

[0224]

[Table 1208]

[0225]

[Table 1209]

[0226]

[Table 1210]

[0227]

[Table 1211]

[0228]

[Table 1212]

[0229]

[Table 1213]

[0230]

[Table 1214]

[0231]

[Table 1215]

[0232]

[Table 1216]

[0233]

[Table 1217]

[0234]

[Table 1218]

[0235]

[Table 1219]

[0236]

[Table 1220]

[0237]

[Table 1221]

[0238]

[Table 1222]

[0239]

[Table 1223]

[0240]

[Table 1224]

[0241]

[Table 1225]

[0242]

[Table 1226]

[0243]

[Table 1227]

[0244]

[Table 1228]

[0245]

[Table 1229]

[0246]

[Table 1230]

[0247]

[Table 1231]

[0248]

[Table 1232]

[0249]

[Table 1233]

[0250]

[Table 1234]

[0251]

[Table 1235]

[0252]

[Table 1236]

[0253]

[Table 1237]

[0254]

[Table 1238]

[0255]

[Table 1239]

[0256]

[Table 1240]

[0257]

[Table 1241]

[0258]

[Table 1242]

[0259]

[Table 1243]

[0260]

[Table 1244]

[0261]

[Table 1245]

[0262]

[Table 1246]

[0263]

[Table 1247]

[0264]

[Table 1248]

[0265]

[Table 1249]

[0266]

[Table 1250]

[0267]

[Table 1251]

[0268]

[Table 1252]

[0269]

[Table 1253]

[0270]

[Table 1254]

[0271]

[Table 1255]

[0272]

[Table 1256]

[0273]

[Table 1257]

[0274]

[Table 1258]

[0275]

[Table 1259]

[0276]

[Table 1260]

[0277]

[Table 1261]

[0278]

[Table 1262]

[0279]

[Table 1263]

[0280]

[Table 1264]

[0281]

[Table 1265]

[0282]

[Table 1266]

Among the phenol derivatives represented by the general formula (I), from the viewpoints of ease of synthesis and performances such as selective separation of useful substances, chemical stabilization, non-volatization, sustained release, and powdering, In particular, compound numbers 1 to 64 and 77 to 8 described in Table 1
6, 123-138, 209-230, 295-31
0, 381-396, 467-482, 553-56
8, 639-654, 695-740, 811-82
6, 861-924, 937-942, 983-99
8, 1069 to 1090, 1155 to 1170, 124
1-1256, 1327-1342, 1413-142
8, 1499-1514, 1585-1600, 163
1-1634 and 1671-1686 are preferable. More preferably, 37 to 48, 77 to 82, and 123 shown in Table 1.
~ 134, 209 ~ 220, 295 ~ 306, 381 ~
392, 467-478, 553-564, 639-6
50, 695-736, 811-822, 897-90
8, 983-994, 1069-1080, 1155
1166, 1241-1252, 1327-1338,
1413-1424, 1499-1510, 1585
1596, 1671 to 1682, especially 37 to 39, 41 to 43, 45 to 47, 209 to 2
11, 213 to 215, 295 to 297, 299 to 30
1, 381-383, 385-387, 389-39
1, 467-469, 471-473, 553-55
5,555-559,695-697,699-70
1, 811 to 813, 815 to 817, 897 to 89
9, 901-903, 905-907, 1069-10
71, 1073 to 1075, 1155 to 1157, 11
59-1161, 1241-1243, 1245-12
47, 1327-1329, 1331-1333, 14
13-1415, 1417-1419, 1585-15
87, 1589-1591, 1671-1673, 16
75-1677 is particularly preferred.

In particular, Compound No. 172 shown in Table 2
1-1790, 1836-1850, 1906-192
0, 1976-1990, 2046-2060, 211
6-2130, 2188-2200, 2256-227
0, 2326 to 2345, 2396 to 2410, 242
1-2490, 2536-2550, 2606-262
0, 2676-2692, 2746-2760, 281
6-2830, 2886-2900, 2956-297
0, 3026 to 3040 and 3096 to 3110 are preferred. More preferably, 1766 to 1780 described in Table 2,
1909, 1910, 1914, 1915, 1919,
1920, 1979, 1980, 1984, 1985,
2049, 2050, 2054, 2055, 2059,
2060, 2119, 2120, 2124, 2125,
2189, 2190, 2194, 2195, 2329,
2330, 2334, 2335, 2399, 2400,
2404, 2405, 2466-2480, 2609,
2610, 2614, 2615, 2679, 2680,
2684, 2865, 2749, 2750, 2754,
2755, 2819, 2820, 2824, 2825,
2889, 2890, 2894, 2895, 3029,
3030, 3034, 3035, 3099, 3100,
3104 and 3105.

Compound No. 3870 described in Table 3
-4297, 4404-4618, 4833-5260
Are preferred. Among them, compound numbers 3870 to 4190 and 4512 to 4618 described in Table 3 are particularly preferable. More preferably, 3870-3883, 3977-3
990, 4084-4097 and 4084-4097.

The phenol derivative represented by the general formula (I) is, for example, a dihydroxydiphenylsulfone derivative,
Dihydroxydiphenyl ether derivative, dihydroxydiphenylthioether derivative, dihydroxydiphenylketone derivative, 2,2-bis (hydroxyphenyl)
Propane derivatives, substituted phenols and the like, alkylsulfonyl chloride, alkenylsulfonyl chloride, phenylsulfonyl chloride, alkylcarbonyl chloride,
It can be produced by a Friedel-Crafts reaction with alkenylcarbonyl chloride, phenylcarbonyl chloride and the like in the presence of a Lewis acid such as iron chloride, aluminum chloride and zinc chloride.

The phenol derivative of the present invention is usually a crystalline solid, but may be amorphous or oily. In some cases, the phenol derivative represented by the general formula (I) belongs to the present invention irrespective of the form, although the polymorph may take a crystalline polymorph.

In the present invention, the substance forming a molecular compound with the phenol derivative represented by the general formula (I) is not particularly limited as long as it can form a molecular compound with such a derivative. Specific examples include water, methanol, ethanol, isopropanol, n-butanol,
n-octanol, 2-ethylhexanol, allyl alcohol, propargyl alcohol, 1,2-butanediol, 1,3-butanediol, 1,4-butanediol, cyclohexanediol, 2-bromo-2-nitropropane-1, 3-diol, 2,2-dibromo-2
Alcohols such as -nitroethanol, 4-chlorophenyl-3-iodopropargyl formal, formaldehyde, acetaldehyde, n-butyraldehyde, aldehydes such as propionaldehyde, benzaldehyde, phthalaldehyde, α-bromocinnamaldehyde, phenylacetaldehyde, acetone, Methyl ethyl ketone, diethyl ketone, dibutyl ketone, methyl isobutyl ketone, cyclohexanone, acetylacetone,
Ketones such as 2-bromo-4'-hydroxyacetophenone, acetonitrile, acrylonitrile, n-butyronitrile, malononitrile, phenylacetonitrile,
Benzonitrile, cyanopyridine, 2,2-dibromomethylglutarnitrile, 2,3,5,6-tetrachloroisophthalonitrile, 5-chloro-2,4,6-trifluoroisophthalonitrile, 1,2-dibromo −2,4
-Nitriles such as dicyanobutane, diethyl ether,
Dibutyl ether, tetrahydrofuran, dioxane,
Ethers such as tetrahydropyran, dioxolan and trioxane, methyl acetate, ethyl acetate, butyl acetate, n
Esters such as heptyl acetate, bis-1,4-bromoacetoxy-2-butene, sulfonamides such as benzenesulfonamide, N-methylformamide;
N, N-dimethylformamide, dicyandiamide, dibromonitrilepropionamide, 2,2-dibromo-
3-nitrilopropionamide, N, N-diethyl-m
Amides such as toluamide, halogenated hydrocarbons such as dichloromethane, chloroform, dichloroethylene and tetrachloroethylene, lactams such as ε-caprolactam, lactones such as ε-caprolactone, oxiranes such as arylglycidyl ether, morpholines, phenol, Cresol, resorcinol, p-chloro-m
-Phenols such as cresol, formic acid, acetic acid, propionic acid, oxalic acid, citric acid, adipic acid, tartaric acid, carboxylic acids such as benzoic acid, phthalic acid, salicylic acid and thiocarboxylic acids, sulfamic acids, thiocarbamic acids, thiosemicarbazides Urea such as urea, phenylurea, diphenylurea, thiourea, phenylthiourea, diphenylthiourea, N, N-dimethyldichlorophenylurea, thioureas, isothioureas, sulfonylureas, thiophenol, allyl mercaptan, n- Thiols such as butyl mercaptan and benzyl mercaptan,
Sulfides such as benzyl sulfide and butyl methyl sulfide; disulfides such as dibutyl disulfide, dibenzyl disulfide and tetramethylthiuram disulfide; sulphoxides such as dimethyl sulphoxide, dibutyl sulphoxide and dibenzyl sulphoxide; dimethyl sulfone, phenyl sulphone and phenyl- ( 2-cyano-2-chlorovinyl) sulfone, hexabromodimethyl sulfone, diiodomethyl paratolylsulfone and other sulfones, thiocyanic acid and isothiocyanic acid such as methyl thiocyanate and methyl isothiocyanate, glycine, alanine, leucine, lysine,
Amino acids such as methionine and glutamine, amide and urethane compounds, acid anhydrides, aromatic hydrocarbons such as benzene, toluene, xylene, alkanes, alkenes, alkynes, butyl isocyanate, cyclohexyl isocyanate, phenyl isocyanate, etc. Isocyanates, thiocyanates and isothiocyanates such as methylenebisthiocyanate and methylenebisisothiocyanate, nitro compounds such as tris (hydroxymethyl) nitromethane, ammonia, methylamine,
Ethylamine, propylamine, butylamine, pentylamine, hexylamine, allylamine, hydroxylamine, ethanolamine, benzylamine, ethylenediamine, 1,2-propanediamine, 1,3-propanediamine, 1,4-butanediamine, 1,5 -Pentanediamine, 1,6-hexanediamine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, dipropylenediamine, N, N-dimethylethylenediamine, N, N'-dimethylethylenediamine, N, N-dimethyl-1,3 -Propanediamine, N
-Ethyl-1,3-propanediamine, trimethylhexamethylenediamine, alkyl-t-monoamine, menthanediamine, isophoronediamine, guanidine, N-
Acyclic aliphatic amines such as (2-hydroxypropyl) aminomethanol, cyclohexylamine, cyclohexanediamine, bis (4-aminocyclohexyl) methane, pyrrolidines, azetidines, piperidines, piperazine, N-aminoethylpiperazine; Piperazines such as N, N'-dimethylpiperazine; cycloaliphatic amines such as pyrrolines; aniline; N-methylaniline;
N-dimethylaniline, o-phenylenediamine, m-
Phenylenediamine, p-phenylenediamine, diaminodiphenylmethane, diaminodiphenylsulfone, m
-Modified polyamines such as aromatic amines such as killed diamines, polyamines added with epoxy compounds, polyamines added with Michael, polyamines added with Mannich, polyamines added with thiourea, polyamines blocked with ketones, imidazole, 2-
Methylimidazole, 2-ethylimidazole, 2-isopropylimidazole, 2-n-propylimidazole, 2-ethyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 2-undecyl-1H-
Imidazole, 2-heptadecyl-1H-imidazole, 2-phenyl-1H-imidazole, 4-methyl-
2-phenyl-1H-imidazole, 1-benzyl-2
-Imidazoles such as methylimidazole, pyrrole,
Pyridine, picoline, pyrazine, pyridazine, pyrimidine, pyrazole, triazole, benzotriazole,
Triazine, tetrazole, purine, indole, quinoline, isoquinoline, carbazole, imidazoline, pyrroline, oxazole, piperine, pyrimidine, pyridazine, benzimidazole, indazole, quinazoline, quinoxaline, phthalimide, adenine, cytosine, guanine, uracil, 2-methoxycarbonylbenz Imidazole, 2,3,5,6-tetrachloro-4-
Methanesulfonylpyridine, 2,2-dithio-bis-
(Pyridine-1-oxide), N-methylpyrrolidone, methyl 2-benzimidazolecarbamate, 2-
Sodium pyridinethiol-1-oxide, hexahydro-1,3,5-tris (2-hydroxyethyl)-
s-triazine, hexahydro-1,3,5-triethyl-s-triazine, 2-methylthio-4-t-butylamino-6-cyclopropylamino-s-triazine,
N- (fluorodichloromethylthio) phthalimide, 1
-Bromo-3-chloro-5,5-dimethylhydantoin, 2-methoxycarbonylbenzimidazole, 2,
Nitrogen-containing heterocyclic compounds such as 4,6-trichlorophenylmaleimide, furan, furfuryl alcohol, tetrahydrofurfuryl alcohol, furfurylamine, pyran,
Oxygen-containing heterocyclic compounds such as coumarin, benzofuran, xanthene and benzodioxane, oxazole, isoxazole, benzoxazole, benzisoxazole,
5-methyloxazolidine, 4- (2-nitrobutyl)
Nitrogen- and oxygen-containing heterocyclic compounds such as morpholine and 4,4 ′-(2-ethyl-2-nitrotrimethylene) dimorpholine, thiophene, 3,3,4,4-tetrahydrothiophene-1,1-dioxide, , 5-dichloro-1,
Sulfur-containing heterocycles such as 2-dithiolan-3-one, 5-chloro-4-phenyl-1,2-dithiolan-3-one, 3,3,4,4-tetrachlorotetrahydrothiophen-1,1-dioxide Compound, thiazole, benzothiazole, 5-chloro-2-methyl-4-isothiazoline-
3-one, 2-methyl-4-isothiazolin-3-one, 4,5-dichloro-3-n-octylisothiazolin-3-one, 2-octyl-4-isothiazoline-3
-One, 1,2-benzisothiazolin-3-one, 2
Nitrogen-containing and sulfur heterocyclic compounds such as thiocyanomethylbenzothiazole, 2- (4-thiazolyl) benzimidazole and 2-thiocyanomethylbenzothiazole; steroids such as cholesterol; alkaloids such as brucine, quinine and theophylline; Natural essential oils such as cineole, hinokitiol, menthol, terpineol, borneol, nopol, citral, citronellol, citronellal, geraniol, menthone, eugenol, linalool, dimethyloctanol, synthetic flavors such as quince, jasmine and lemon, ascorbic acid, nicotinic acid And related compounds such as vitamins and nicotinamide.

The molecular compound of the present invention is obtained by directly mixing the phenol derivative represented by the general formula (I) with the above-mentioned substance forming a molecular compound with the derivative, or by mixing in a solvent. Can be obtained by In the case of a substance having a low boiling point or a substance having a high vapor pressure, a target molecular compound can be obtained by allowing the phenol derivative of the present invention to act on the vapor of these substances. Further, first, a molecular compound of the phenol derivative of the present invention and a certain substance is formed, and the molecular compound is reacted with another substance by the above-mentioned method to obtain a target molecular compound.

The fact that the substance obtained by these methods is indeed a molecular compound can be confirmed by thermal analysis (TG and DTA),
It can be confirmed by infrared absorption spectrum (IR), X-ray diffraction pattern, solid-state NMR spectrum, and the like. The composition of the molecular compound can be confirmed by thermal analysis, ¹ H NMR spectrum, high performance liquid chromatography (HPLC), elemental analysis and the like.

In the molecular compound of the present invention, the ratio of each component compound constituting the molecular compound may be changed depending on the production conditions. Further, by reacting two or more kinds of substances with the phenol derivative of the present invention, a molecular compound consisting of three or more components can be obtained.

The molecular compound of the present invention is useful for selective separation of useful substances, chemical stabilization, non-volatilization, pulverization, etc., and for the purpose of stably producing a molecular compound having a constant composition. It is preferably crystalline, and more preferably a crystalline inclusion compound. At this time, even the same molecular compound may take a polymorph. Crystallinity can be confirmed mainly by examining the X-ray diffraction pattern. The presence of polymorphs was determined by thermal analysis, X-ray diffraction pattern,
It can be confirmed by solid state NMR and the like. Here, an clathrate is a compound in which a three-dimensional structure formed by bonding atoms or molecules has pores of an appropriate size, in which other atoms or molecules have non-covalent interactions. Indicates a substance that has entered at a constant composition ratio.

The form of use of the molecular compound of the present invention is not particularly limited, and for example, two or more kinds of molecular compounds each composed of different component compounds can be used in combination. The molecular compound of the present invention can be used in combination with other substances as long as the intended function is not impaired.
An excipient or the like may be added to the molecular compound of the present invention to form granules or tablets for use. Further, they can be used by adding them to resins, paints, and their raw materials and raw material compositions. The molecular compound of the present invention can be used as it is as a raw material for organic synthesis, or the molecular compound can be used as a specific reaction field.

For example, in the present invention, the above-mentioned general formula (I)
A phenol derivative represented by
Chloro-2-methyl-4-isothiazolin-3-one,
Isothiazolone fungicides such as 2-methyl-4-isothiazolin-3-one, antibacterial and insecticide insect repellents such as hinokitiol and 1,8-cineole, fragrances such as rosemary, antifouling agents such as isothiazolone compounds, and anhydrous. Catalysts such as curing agents for epoxy resins such as phthalic acid, tetrahydrophthalic anhydride and 2-ethyl-4-methylimidazole and curing accelerators for epoxy resins such as 1,8-diazabicyclo (4,5,0) undecene-7 Or an inclusion compound in which an organic solvent such as toluene, xylene, or pyridine is used as a guest, in addition to the action inherent to the guest compound, sustained release, reduction of skin irritation, chemical stabilization, non-volatization, powderization, Fungicides, antibacterial agents, insecticides / insect repellents, fragrances, antifouling agents, curing agents for epoxy resins, etc. that have new functions such as selective separation of useful substances The catalyst is extremely useful as an organic solvent.

[0295]

Next, the present invention will be described in more detail by way of examples, which should not be construed as limiting the present invention.

Example 1 26 g (50 mmol) of 3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone (compound No. 38 shown in Table 1, melting point 245 ° C.) was dispersed in 500 ml of ethyl acetate. Suspended. Caisson WT (Rohm & Haas) 220m
l [5-chloro-2-methyl-4-isothiazoline-3
-One 22 g (150 mmol), 8.4 g of 2-methyl-4-isothiazolin-3-one, and the balance including magnesium chloride, magnesium nitrate, and water].
The mixture was heated and stirred for 10 minutes. After standing at room temperature for 24 hours, the ethyl acetate layer was taken out, and the ethyl acetate was evaporated and concentrated under reduced pressure.
The precipitated crystals were collected by filtration. Thereafter, the crystals were dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours.
3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone and 5-chloro-2-methyl-
A molecular compound having a composition ratio with 4-isothiazolin-3-one of 1: 2 (molar ratio) was obtained. The identity of the molecular compound of this composition was confirmed by thermal analysis (TG / DTA), ¹ HNMR and X-ray diffraction pattern. The X-ray diffraction pattern confirmed that the present molecular compound was clearly crystalline. This molecular compound is 5-chloro-2-methyl-4-
Isothiazolin-3-one at about 140 ° C to 160 ° C
In the range of Thermal analysis of this molecular compound (TG / DT
A) Chart, ¹ H NMR spectrum (using deuterated chloroform solvent) and X-ray diffraction pattern are shown in FIGS. 1, 2 and 3.
Respectively. Thus, the molecular compound of the present invention
The active ingredient 5-chloro-2-methyl-4-isothiazolin-3-one of Caisson WT, which is a liquid, irritating and highly degradable fungicide, was powdered and provided with thermal stabilization.

Example 2 26 g of 3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone, Caisson WT2
20 ml and 900 ml of methanol were added and dissolved by heating and stirring. Thereafter, methanol was gradually evaporated under reduced pressure at room temperature, and the precipitated crystals were collected by filtration. The crystals were dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours to give 3,3'-bis (phenylsulfonyl) -4,4 '.
-Dihydroxydiphenyl sulfone and 5-chloro-2-
A molecular compound having a composition ratio of 1: 2 (molar ratio) with methyl-4-isothiazolin-3-one was obtained. Thermal analysis (TG / DTA), ¹
Confirmed by 1 H NMR and X-ray diffraction pattern. The X-ray diffraction pattern confirmed that the present molecular compound was clearly crystalline.

In the same manner, when methanol was rapidly evaporated and concentrated under reduced pressure at room temperature to precipitate crystals, 3,3'-bis (phenylsulfonyl) -4,4 '
-Dihydroxydiphenyl sulfone and 5-chloro-2-
A molecular compound having a composition ratio of 1: 1 (molar ratio) with methyl-4-isothiazolin-3-one was obtained. Thermal analysis (TG / DTA), ¹
Confirmed by 1 H NMR and X-ray diffraction pattern. The X-ray diffraction pattern confirmed that the present molecular compound was clearly crystalline.

As described above, the molecular compound of the present invention is obtained by powdering the active ingredient 5-chloro-2-methyl-4-isothiazolin-3-one of Caisson WT, which is a liquid, irritating and highly degradable fungicide. , And thermal stabilization.

Example 3 3,3'-Bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone 26 was added to 220 ml of an industrial disinfectant, Caisson WT (manufactured by Rohm & Haas).
g was added and stirred at room temperature in a suspended state for 10 minutes. After standing at room temperature for 24 hours, the solid was collected by filtration, dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours, and
Compositional ratio of bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone to 5-chloro-2-methyl-4-isothiazolin-3-one 1: 1 (molar ratio)
Was obtained. The identity of the molecular compound of this composition was confirmed by thermal analysis (TG / DTA), ¹ HNMR and X-ray diffraction pattern. The X-ray diffraction pattern confirmed that the present molecular compound was clearly crystalline. This molecular compound released 5-chloro-2-methyl-4-isothiazolin-3-one in the range of about 120 ° C to 205 ° C. Thus, the molecular compound of the present invention is a liquid, irritating and highly degradable fungicide, Caisson WT.
Of the active ingredient 5-chloro-2-methyl-4-isothiazolin-3-one in powder form and provided thermal stabilization.

Comparative Example 1 In Examples 1 to 3, instead of 3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone, the same moles of 4,4'-dihydroxydiphenylsulfone and bis (4-hydroxyphenyl) ether, bis (4-hydroxyphenyl) thioether,
Examples 1 to 3 except that bis (4-hydroxyphenyl) methane, 2,2-bis (4-hydroxyphenyl) propane, bis (4-hydroxyphenyl) ketone or 2,4'-dihydroxydiphenylsulfone was used. The same operation was performed. However, in each case, a molecular compound with 5-chloro-2-methyl-4-isothiazolin-3-one was not produced.

Example 4 26 g (50 mmol) of 3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone
And 17 g of 2-ethyl-4-methylimidazole (150
mmol) was added to 400 ml of ethyl acetate and dissolved by heating. Thereafter, the mixture was allowed to stand at room temperature for 24 hours, and the precipitated crystals were collected by filtration, dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours, and 3,3'-bis (phenylsulfonyl)-
A molecular compound having a composition ratio of 4,4'-dihydroxydiphenylsulfone and 2-ethyl-4-methylimidazole of 1: 2 (molar ratio) was obtained. The identity of the molecular compound of this composition was confirmed by thermal analysis (TG / DTA), ¹ HNMR and X-ray diffraction pattern. The X-ray diffraction pattern confirmed that the present molecular compound was crystalline. 2
-Ethyl-4-methylimidazole has a melting point of 47 ° C., whereas the molecular compound has a melting point of 199 ° C.
2-Ethyl-4-methylimidazole was released from around 195 ° C. The ¹ H NMR spectrum (using dimethyl sulfoxide-d ₆ solvent) and the X-ray diffraction pattern of the present molecular compound are shown in FIGS. 4 and 5, respectively. Thus, the molecular compound of the present invention is a compound having a low melting point, 2-ethyl-4-.
Crystallization of methylimidazole, and control of melting and volatilization were enabled.

Next, the composition of the above 3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone and 2-ethyl-4-methylimidazole acting as a curing agent and a curing accelerator for an epoxy resin. Ratio 1:
The curing characteristics of the epoxy resin were examined using a molecular compound consisting of 2 (molar ratio) as an inclusion catalyst. As the epoxy monomer, UVR-6410, a general-purpose monomer manufactured by Union Carbide, was used.
The above-mentioned clathrate catalyst was added to 0.4 g as a pure component of a curing agent (2-ethyl-4-methylimidazole) per 0 g, and the mixture was thoroughly stirred for 5 minutes in a 50 ml Teflon beaker. A part thereof was used as a DSC (differential scanning calorimeter) measurement sample. FIG. 6 shows the DSC measurement results. As can be seen from FIG. 6, when the inclusion catalyst of 2-ethyl-4-methylimidazole using 3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone as a host was used at 114 ° C. Curing began and at 135 ° C. the curing reaction reached the top. on the other hand,
The reaction was carried out in the same manner as described above except that 2-ethyl-4-methylimidazole was used as a curing agent instead of using the inclusion catalyst. The curing started at 79 ° C., and the curing reaction reached the top at 114 ° C. . From these facts, by using 2-ethyl-4-methylimidazole as the inclusion catalyst, the curing start temperature is increased, and the temperature difference from the start of curing to the top of the curing reaction is small, and the heat sensitivity is low. Was confirmed to rise.

Example 5 20 g (38 mmol) of 3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone
And 12 g (150 mmol) of pyridine were dissolved in 100 ml of methanol at room temperature. After standing at 0 ° C. for 24 hours, the precipitated crystals were collected by filtration, dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours, and 3,3′-bis (phenylsulfonyl) -4,4′-dihydroxydiphenylsulfone. A molecular compound having a composition ratio of pyridine and pyridine of 1: 2 (molar ratio) was obtained. The identity of the molecular compound of this composition was confirmed by thermal analysis (TG / DTA), ¹ HNMR and X-ray diffraction pattern. The X-ray diffraction pattern confirmed that the present molecular compound was crystalline. This molecular compound released pyridine in the range of about 90 ° C to 200 ° C. ¹ H NMR spectrum (using dimethyl sulfoxide-d ₆ solvent) and thermal analysis (TG / DT) of this molecular compound
A) The charts are shown in FIGS. 7 and 8, respectively. Thus, the molecular compound of the present invention powdered pyridine, which is a liquid at room temperature, and enabled control of volatilization.

Example 6 20 g of 3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone (38 mmol
l), 12 g (150 mmol) of pyridine, and 1,3
4.6 g of dimethyl-2-imidazolidinone (40 mm
ol) was dissolved by heating in 200 ml of ethyl acetate at room temperature.
After leaving at 0 ° C. for 24 hours, the precipitated crystals were collected by filtration, and dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours.
3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone, pyridine, and 1,3
-Composition ratio with dimethyl-2-imidazolidinone 1:
A molecular compound consisting of 1: 1 (molar ratio) was obtained. Thermal analysis (TG / DTA), ¹
Confirmed by 1 H NMR and X-ray diffraction pattern. The X-ray diffraction pattern confirmed that the present molecular compound was crystalline. The present molecular compound converts pyridine and 1,3-dimethyl-2-imidazolidinone to a temperature of about 118 ° C to 212 ° C.
Released in the ° C range. The ¹ H NMR spectrum (using dimethyl sulfoxide-d ₆ solvent) and the thermal analysis (TG / DTA) chart of the present molecular compound are shown in FIGS. 9 and 10, respectively.

As described above, the molecular compound of the present invention powdered pyridine and 1,3-dimethyl-2-imidazolidinone which are liquid at room temperature, and enabled control of volatilization of both.

Comparative Example 2 In Examples 5 and 6, instead of 3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone, the same moles of 4,4'-dihydroxydiphenylsulfone and bis (4-hydroxyphenyl) ether, bis (4-hydroxyphenyl) thioether, bis (4-hydroxyphenyl) methane, 2,2-
Bis (4-hydroxyphenyl) propane, bis (4-
Examples 5 and 6 except that (hydroxyphenyl) ketone or 2,4'-dihydroxydiphenylsulfone was used.
The same operation as described above was performed. However, in each case, a molecular compound with pyridine and 1,3-dimethyl-2-imidazolidinone was not produced.

Example 7 15 g (28 mmol) of 3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone
Was dissolved in 100 ml of tetrahydrofuran by heating, and then left at room temperature for 72 hours. The precipitated crystals were collected by filtration and dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours.
A molecular compound having a composition ratio of 3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone and tetrahydrofuran of 1: 4 (molar ratio) was obtained. Similarly, 1,4-dioxane and N, N-dimethylformamide were used instead of tetrahydrofuran, and 3,3'-bis (phenylsulfonyl) -4,4 ', respectively.
A molecular compound having a composition ratio of dihydroxydiphenyl sulfone and 1,4-dioxane of 1: 1 (molar ratio),
And 3,3'-bis (phenylsulfonyl) -4,4 '
A molecular compound having a composition ratio of -dihydroxydiphenyl sulfone and N, N-dimethylformamide of 1: 1.5 (molar ratio) was obtained. The fact that these are molecular compounds was confirmed by thermal analysis (TG / DTA), ¹ HNMR and X-ray diffraction pattern. The X-ray diffraction pattern confirmed that the present molecular compound was crystalline. As described above, the molecular compound of the present invention enables powdering of tetrahydrofuran, 1,4-dioxane and N, N-dimethylformamide which are liquid at room temperature.

Comparative Example 3 In Example 7, instead of 3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone, the same moles of 4,4'-dihydroxydiphenylsulfone and bis (4 -Hydroxyphenyl) ether, bis (4-hydroxyphenyl) thioether, bis (4-hydroxyphenyl) methane, 2,2-bis (4-hydroxyphenyl) propane, bis (4-hydroxyphenyl) ketone or 2,4 ′ The same operation as in Example 7 was performed except that -dihydroxydiphenyl sulfone was used. However, molecular compounds with tetrahydrofuran, 1,4-dioxane and N, N-dimethylformamide were not produced in any case.

Example 8 2,4-bis (phenylsulfonyl) phenol 20 g
Was heated and dissolved in 100 ml of a mixed solvent of 1,3-dimethyl-2-imidazolidinone and methanol 1: 1 (volume ratio), left at 5 ° C. for 24 hours, and the precipitated crystals were collected by filtration.
The mixture was dried under reduced pressure at room temperature for 5 hours using a rotary vacuum pump, and a molecule consisting of 2,4-bis (phenylsulfonyl) phenol and 1,3-dimethyl-2-imidazolidinone in a composition ratio of 1: 1 (molar ratio). The compound was obtained. next,
Pyridine was used in place of 1,3-dimethyl-2-imidazolidinone and methanol.
A molecular compound having a composition ratio of 4-bis (phenylsulfonyl) phenol and pyridine of 1: 1 (molar ratio) was obtained. Also, after heating and dissolving 20 g of 2,4-bis (phenylsulfonyl) phenol in 50 ml of N, N-dimethylformamide, the N, N-dimethylformamide was removed using a rotary evaporator, and the solid residue was heated to 80 ° C. The mixture was dried under reduced pressure using a rotary vacuum pump for 5 hours to obtain a molecular compound having a composition ratio of 2,4-bis (phenylsulfonyl) phenol and N, N-dimethylformamide of 1: 1 (molar ratio). Furthermore,
A similar operation was performed using dimethylsulfoxide instead of N, N-dimethylformamide to obtain a molecule having a composition ratio of 2,4-bis (phenylsulfonyl) phenol and dimethylsulfoxide of 1: 0.75 (molar ratio). The compound was obtained. It was confirmed by thermal analysis (TG / DTA), ¹ HNMR and X-ray diffraction pattern that each was a molecular compound having the above composition. The X-ray diffraction pattern confirmed that each molecular compound was clearly crystalline. Each molecular compound has 1,3-dimethyl-2-imidazolidinone in the range of about 130-230 ° C., pyridine in the range of about 90-210 ° C., and N, N-dimethylformamide in the range of about 95-185 ° C. In the range, dimethyl sulfoxide was released in the range of approximately 95 ° C to 220 ° C.

¹ H NMR spectrum of a molecular compound of 2,4-bis (phenylsulfonyl) phenol and 1,3-dimethyl-2-imidazolidinone, pyridine, N, N-dimethylformamide and dimethylsulfoxide (dimethylsulfoxide-d Figure ₆ solvent used), respectively 1
1, FIG. 12, FIG. 13 and FIG. 14, the thermal analysis (TG /
DTA) charts are shown in FIGS. 15, 16, 17 and 18, respectively. For comparison, 2,4-bis The ¹ HNMR spectrum of the (phenylsulfonyl) phenol (dimethylsulfoxide -d ₆ solvent used) 19
It was shown to.

As described above, the molecular compound of the present invention comprises 1,3-dimethyl-2-imidazolidinone, which is liquid at room temperature,
Pyridine, N, N-dimethylformamide and dimethylsulfoxide were powdered and allowed for volatilization control.

Example 9 20 g of 2,4,6-tris (phenylsulfonyl) phenol was suspended in 100 ml of acetone, heated at a reflux temperature for 10 minutes, left at 5 ° C. for 24 hours, and the precipitated crystals were collected by filtration. The mixture was dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours to obtain a molecular compound having a composition ratio of 2,4,6-tris (phenylsulfonyl) phenol and acetone of 1: 1 (molar ratio). In addition, instead of acetone, ethyl acetate, tetrahydrofuran or 1,4-dioxane was used, and the same operation was performed to obtain 2,4,6-
A molecular compound consisting of tris (phenylsulfonyl) phenol and ethyl acetate, tetrahydrofuran or 1,4-dioxane in a composition ratio of 1: 1 (molar ratio) was obtained. The fact that each is a molecular compound having the above composition is determined by thermal analysis (TG
/ DTA), ¹ HNMR and X-ray diffraction pattern. The X-ray diffraction pattern confirmed that each molecular compound was clearly crystalline. Each molecular compound has acetone in the range of about 90C to 132C, ethyl acetate in the range of about 70C to 81C, tetrahydrofuran in the range of about 85C to 188C, and dimethylsulfoxide in the range of about 92C to 136C. Released at

¹ HN of a molecular compound of 2,4,6-tris (phenylsulfonyl) phenol with acetone, ethyl acetate, tetrahydrofuran and 1,4-dioxane
The MR spectrum (using dimethyl sulfoxide-d ₆ solvent) is shown in FIGS. 20, 21, 22 and 23, respectively, and the thermal analysis (TG / DTA) chart is shown in FIG.
4, FIG. 25, FIG. 26 and FIG. Also, shown for comparison, 2,4,6-tris The ¹ HNMR spectrum of the (phenylsulfonyl) phenol (dimethylsulfoxide -d ₆ solvent used) Figure 28.

As described above, the molecular compound of the present invention powdered acetone, ethyl acetate, tetrahydrofuran and 1,4-dioxane, which were liquid at room temperature, and enabled control of volatilization.

Example 10 5.3 g of 3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone was added to methanol 1
The solution was added to 50 ml, and dissolved by heating and stirring. Here 2-
Octyl-4-isothiazolin-3-one (5.9 g) was added, and the mixture was heated and stirred for 10 minutes. After allowing to stand at room temperature for 24 hours, the precipitated crystals were collected by filtration. The crystals were dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours.
A molecular compound having a compositional ratio of -bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone and 2-octyl-4-isothiazolin-3-one of 1: 2 (molar ratio) was obtained. The identity of the molecular compound of this composition was confirmed by thermal analysis (TG / DTA), ¹ HNMR, and X-ray diffraction pattern. The X-ray diffraction pattern confirmed that the present molecular compound was clearly crystalline.

Further, 3,3'-bis (phenylsulfonyl) -4,4'-dihydroxydiphenylsulfone5.
3 g was added to 150 ml of ethyl acetate, and suspended by heating and stirring. Here, 2-octyl-4-isothiazoline-3
5.9 g of -ON was added, and the mixture was heated and stirred for 10 minutes. After allowing to stand at room temperature for 24 hours, the crystals were collected by filtration. The crystals were dried under reduced pressure at room temperature using a rotary vacuum pump for 5 hours to obtain the same molecular compound as described above. The melting point of the present molecular compound was 109 ° C. As described above, the molecular compound of the present invention is 2-octyl-4-isothiazoline-3, which is a bactericide which is liquid, irritating and highly decomposable at room temperature.
-One powdered and provided thermal stabilization.

[0318]

Industrial Applicability The novel molecular compound of the present invention can be prepared by a simple operation and can impart functions such as chemical stabilization, non-volatilization, sustained release, and powdering of various substances. In addition, selective separation and recovery of specific substances can be performed. Further, the molecular compound of the present invention can be used in combination with various substances, and can also be used in various forms. Therefore, the present invention can be used in a very wide range of fields, and has great industrial significance.

[Brief description of the drawings]

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 shows 3,3′-bis (phenylsulfonyl) -4,4′-dihydroxydiphenylsulfone and 5-chloro-2-methyl-4-isothiazoline of Example 1 of the present invention.
It is a figure which shows the thermal-analysis (TG / DTA) chart of the molecular compound which has a composition ratio with 3-one 1: 2 (molar ratio).

FIG. 2 shows 3,3′-bis (phenylsulfonyl) -4,4′-dihydroxydiphenylsulfone and 5-chloro-2-methyl-4-isothiazoline of Example 1 of the present invention.
FIG. 3 is a view showing a ¹ HNMR spectrum (using a heavy chloroform solvent) of a molecular compound having a composition ratio with 3-one of 1: 2 (molar ratio).

FIG. 3 shows 3,3′-bis (phenylsulfonyl) -4,4′-dihydroxydiphenylsulfone and 5-chloro-2-methyl-4-isothiazoline of Example 1 of the present invention.
It is a figure which shows the X-ray-diffraction pattern of the molecular compound which has a composition ratio with 3-one 1: 2 (molar ratio).

FIG. 4: Composition ratio of 3,3′-bis (phenylsulfonyl) -4,4′-dihydroxydiphenylsulfone and 2-ethyl-4-methylimidazole of Example 4 of the present invention 1: 2 (molar ratio) ¹ H NMR spectrum (using dimethyl sulfoxide-d ₆ solvent) of a molecular compound consisting of

FIG. 5: Composition ratio of 3,3′-bis (phenylsulfonyl) -4,4′-dihydroxydiphenylsulfone and 2-ethyl-4-methylimidazole of Example 4 of the present invention 1: 2 (molar ratio) 3 is a view showing an X-ray diffraction pattern of a molecular compound consisting of

FIG. 6: Composition ratio of 3,3′-bis (phenylsulfonyl) -4,4′-dihydroxydiphenylsulfone and 2-ethyl-4-methylimidazole of Example 4 of the present invention 1: 2 (molar ratio) FIG. 4 is a view showing DSC measurement results showing the curing characteristics of an epoxy resin when an inclusion catalyst comprising:

FIG. 7 shows ¹ HNMR of a molecular compound having a composition ratio of 3,2′-bis (phenylsulfonyl) -4,4′-dihydroxydiphenylsulfone and pyridine of 1: 2 (molar ratio) according to Example 5 of the present invention. FIG. 3 is a view showing a spectrum (using a dimethyl sulfoxide-d ₆ solvent).

FIG. 8 is a thermal analysis of a molecular compound having a compositional ratio of 3,3′-bis (phenylsulfonyl) -4,4′-dihydroxydiphenylsulfone and pyridine of 1: 2 (molar ratio) according to Example 5 of the present invention. It is a figure showing a (TG / DTA) chart.

FIG. 9: Composition ratio 1 with 3,3′-bis (phenylsulfonyl) -4,4′-dihydroxydiphenylsulfone, pyridine and 1,3-dimethyl-2-imidazolidinone of Example 6 of the present invention FIG. 1 is a view showing a ¹ HNMR spectrum (using a dimethyl sulfoxide-d ₆ solvent) of a molecular compound consisting of 1: 1 (molar ratio).

FIG. 10: Composition ratio 1 with 3,3′-bis (phenylsulfonyl) -4,4′-dihydroxydiphenylsulfone, pyridine and 1,3-dimethyl-2-imidazolidinone of Example 6 of the present invention It is a figure which shows the thermal-analysis (TG / DTA) chart of the molecular compound which consists of 1: 1 (molar ratio).

FIG. 11 shows ^{one of the} molecular compounds having a composition ratio of 2,1-bis (phenylsulfonyl) phenol and 1,3-dimethyl-2-imidazolidinone of 1: 1 (molar ratio) in Example 8 of the present invention. shows a HNMR spectrum (dimethylsulfoxide -d ₆ solvent used).

FIG. 12: Composition ratio of 2,4-bis (phenylsulfonyl) phenol to pyridine of Example 8 of the present invention of 1: 1
FIG. 3 is a diagram showing a ¹ H NMR spectrum (using a dimethyl sulfoxide-d ₆ solvent) of a molecular compound consisting of (molar ratio).

FIG. 13 shows a molecular compound having a composition ratio of 2,4-bis (phenylsulfonyl) phenol and N, N-dimethylformamide of 1: 1 (molar ratio) according to Example 8 of the present invention.
FIG. 3 is a view showing a ¹ HNMR spectrum (using a dimethyl sulfoxide-d ₆ solvent).

2,4-bis (phenylsulfonyl) of Example 8 in FIG. 14 the present invention the composition ratio of phenol and dimethylsulfoxide 1: 0.75 molecular compound consisting of (molar ratio) ¹
Shows a HNMR spectrum (dimethylsulfoxide -d ₆ solvent used).

FIG. 15 is a graph showing heat of a molecular compound having a composition ratio of 1,4-bis (phenylsulfonyl) phenol and 1,3-dimethyl-2-imidazolidinone of 1: 1 (molar ratio) in Example 8 of the present invention. It is a figure showing an analysis (TG / DTA) chart.

FIG. 16: Composition ratio of 2,4-bis (phenylsulfonyl) phenol and pyridine of Example 8 of the present invention of 1: 1
Thermal analysis of molecular compounds consisting of (molar ratio) (TG / DT
A) is a diagram showing a chart.

FIG. 17 is a thermal analysis (TG / DTA) of a molecular compound consisting of 2,4-bis (phenylsulfonyl) phenol and N, N-dimethylformamide in a composition ratio of 1: 1 (molar ratio) in Example 8 of the present invention. FIG.

FIG. 18 is a thermal analysis (TG / DTA) chart of a molecular compound having a composition ratio of 2,4-bis (phenylsulfonyl) phenol and dimethylsulfoxide of 1: 0.75 (molar ratio) in Example 8 of the present invention. FIG.

FIG. 19 shows a ¹ H NMR spectrum of 2,4-bis (phenylsulfonyl) phenol (dimethyl sulfoxide-
d ₆ solvent used). FIG.

FIG. 20 shows a ¹ H NMR spectrum (dimethyl sulfoxide-d ₆ ) of a molecular compound having a composition ratio of 2,4,6-tris (phenylsulfonyl) phenol and acetone of 1: 1 (molar ratio) according to Example 9 of the present invention. FIG.

FIG. 21 shows a ¹ HNMR spectrum (dimethylsulfoxide-d) of a molecular compound having a composition ratio of 2,4,6-tris (phenylsulfonyl) phenol and ethyl acetate of 1: 1 (molar ratio) in Example 9 of the present invention. FIG. ₆ is a view showing ( ₆ solvents used).

FIG. 22 shows ¹ H of a molecular compound having a composition ratio of 2,4,6-tris (phenylsulfonyl) phenol and tetrahydrofuran of 1: 1 (molar ratio) in Example 9 of the present invention.
FIG. 3 is a view showing an NMR spectrum (using a dimethyl sulfoxide-d ₆ solvent).

FIG. 23 shows ¹ H of a molecular compound having a composition ratio of 2,4,6-tris (phenylsulfonyl) phenol and 1,4-dioxane of 1: 1 (molar ratio) according to Example 9 of the present invention.
FIG. 3 is a view showing an NMR spectrum (using a dimethyl sulfoxide-d ₆ solvent).

FIG. 24 is a thermal analysis (TG / TG) of a molecular compound having a composition ratio of 2,4,6-tris (phenylsulfonyl) phenol and acetone of 1: 1 (molar ratio) according to Example 9 of the present invention.
FIG. 4 is a diagram showing a DTA) chart.

FIG. 25 is a thermal analysis (TG) of a molecular compound having a composition ratio of 2,4,6-tris (phenylsulfonyl) phenol and ethyl acetate of 1: 1 (molar ratio) according to Example 9 of the present invention.
FIG. 3 is a diagram showing a (/ DTA) chart.

FIG. 26 is a thermal analysis (TG / DTA) chart of a molecular compound having a composition ratio of 2,4,6-tris (phenylsulfonyl) phenol and tetrahydrofuran of 1: 1 (molar ratio) in Example 9 of the present invention. FIG.

FIG. 27 is a thermal analysis (TG / TG) of a molecular compound having a composition ratio of 2,4,6-tris (phenylsulfonyl) phenol and 1,4-dioxane of 1: 1 (molar ratio) according to Example 9 of the present invention. FIG. 4 is a diagram showing a DTA) chart.

FIG. 28: 2,4,6-tris (phenylsulfonyl)
FIG. 3 is a view showing a ¹ HNMR spectrum of phenol (using a dimethyl sulfoxide-d ₆ solvent).

Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07C 317/24 C07C 317/24 323/22 323/22 323/65 323/65 C09K 3/00 110 C09K 3/00 110C 15/14 15 / 14 15/24 15/24 C11B 5/00 C11B 5/00 9/00 9/00 Z // A61K 7/32 A61K 7/32 7/46 301 7/46 301 (72) Inventor Hiroyuki Suzuki Chiba 12-54, Goi-Minamikaigan, Hara-shi Nippon Soda Functional Products Laboratory Co., Ltd.

Claims (7)

[Claims] 1. A compound of the general formula (I) [Wherein, R ₁ and R ₅ may be the same or different and each represent a hydrogen atom, a halogen atom, a C1-C4 alkyl group, C2
To C4 alkenyl group, C1 to C4 alkoxy group, hydroxyl group, or (Y and Z are a C1 to C8 alkyl group, a C2 to C8 alkenyl group, a C1 to C6 alkoxy group, a hydroxyl group, an amino group which may have a substituent, and a cycloalkyl which may have a substituent. A phenyl group which may have a substituent or an aralkyl group which may have a substituent), and R ₂ and R ₄ may be the same or different, and represent a hydrogen atom ,
Represents a halogen atom, an alkyl group of C1 to C4, an alkenyl group of C2 to C4, an alkoxy group of C1 to C4, or a hydroxyl group, provided that any one of R ₁ , R ₃ or R ₅ is C ₁ to C
In the case of an alkoxy group or a hydroxyl group of 4, a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group, or Wherein Y and Z are the same as defined above, and R ₃ represents a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, or a hydroxyl group. , General formula (II), general formula (III) ＸIn the formula, X is (W represents any one of 0, 1, and 2, u represents 0 or 1, and q represents any of 0 to 4, R ₁₄ and R ₁₅ may be the same or different, and represent a hydrogen atom, Halogen atom, C
C1-C4 alkyl group, C2-C4 alkenyl group, C
1 to C4 represents an alkoxy group, a hydroxyl group, a phenyl group which may have a substituent, or an aralkyl group which may have a substituent, wherein R ₁₆ is a hydrogen atom, a C1 to C4 alkyl group,
A 2-C4 alkenyl group, a C1-C4 alkoxy group,
A hydroxyl group, a phenyl group which may have a substituent or an aralkyl group which may have a substituent), and R ₆ , R ₉ ,
R ₁₀ may be the same or different from each other, and may be a hydrogen atom, a halogen atom, a C1 to C4 alkyl group,
4 alkenyl group, C1 to C4 alkoxy group, hydroxyl group, or Wherein Y and Z are the same as defined above,
R ₇ , R ₈ , R ₁₁ , and R ₁₃ may be the same or different from each other, and include a hydrogen atom, a halogen atom, a C1 to C4 alkyl group, a C2 to C4 alkenyl group, a C1 to C4 alkoxy group, or Represents a hydroxyl group, provided that when R ₁₂ is a C1 to C4 alkoxy group or a hydroxyl group, R ₁₁ is a hydrogen atom, a halogen atom, a C1 to C4 alkyl group, a C2 to C4 alkenyl group, a C1 to C4 alkoxy group, Hydroxyl group, or Wherein Y and Z are the same as defined above,
R ₁₂ is a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group, or (Wherein Y and Z are as defined above), or｝ or Wherein Y and Z are the same as defined above,
When R ₃ is the general formula (II), R ₁ , R ₅ , R ₆ ,
One of R ₉ is (Wherein Y and Z are the same as defined above), and when R ₃ is the general formula (III), at least one of R ₁ , R ₅ and R ₁₀ is (Wherein Y and Z are the same as defined above), and when R ₃ is other than the general formula (II) or (III), _one of R ₁ and R ₅ is 12] (Wherein Y and Z are the same as described above). ]
The molecular compound which uses the phenol derivative represented by these as a component compound. 2. A compound of the general formula (IV) Wherein A is (W represents any one of 0, 1, and 2; u represents 0 or 1, respectively); and R ₁₈ , R ₁₉ , R ₂₁ , R
₂₄ may be the same or different from each other, represent a hydrogen atom, a halogen atom, C1 -C4 alkyl groups, or an alkenyl group of C2-C4, the R ₁₇ embedded image (Y and Z are a C1-C6 alkyl group, a C2-C6 alkenyl group, a C1-C4 alkyl group or a C2-
C4 alkenyl group or C1 to C4 alkoxy group or hydroxyl group or cyclohexyl group optionally having a halogen atom, C1 to C4 alkyl group or C2
-C4 alkenyl group or C1-C4 alkoxy group or hydroxyl group or cyclopentyl group which may have a halogen atom, C1-C4 alkyl group or C
A phenyl group which may have a 2-C4 alkenyl group or a C1-C4 alkoxy group or a halogen atom,
A C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group or a benzyl group optionally having a halogen atom, C1
C1 to C4 alkyl group or C2 to C4 alkenyl group or C1 to C4 alkoxy group or hydroxyl group or phenethyl group which may have a halogen atom;
Α-methylbenzyl group which may have a C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group or a halogen atom,
Or a C1 to C4 alkyl group or a C2 to C4 alkenyl group or a C1 to C4 alkoxy group or a hydroxyl group or a naphthyl group which may have a halogen atom), and R ₂₀ , R ₂₂ and R ₂₃ are each other Which may be the same or different, a hydrogen atom, a halogen atom, C1
A C4 alkyl group, a C2-C4 alkenyl group, a C1
Molecules that the phenol derivative represented by the representative] a C4 alkoxy group or R ₁₇ the same groups of the component compounds. 3. A compound of the general formula (V) Wherein B is (W represents 0, 1, or 2 and u represents 0 or 1, respectively), and R ₂₆ , R ₂₇ , R ₃₀ , and R
₃₂ may be the same or different from each other, and represent a hydrogen atom,
Halogen atom, C1-C4 alkyl group, or C2-C
4 represents an alkenyl group, and R ₂₅ , R ₂₈ , R ₂₉ and R ₃₁ are
May be the same or different, and each may be a hydrogen atom, a halogen atom, a C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, or (Y and Z are a C1-C6 alkyl group, a C2-C6 alkenyl group, a C1-C4 alkyl group or a C2-
C4 alkenyl group or C1 to C4 alkoxy group or hydroxyl group or cyclohexyl group optionally having a halogen atom, C1 to C4 alkyl group or C2
-C4 alkenyl group or C1-C4 alkoxy group or hydroxyl group or cyclopentyl group which may have a halogen atom, C1-C4 alkyl group or C
A phenyl group which may have a 2-C4 alkenyl group or a C1-C4 alkoxy group or a halogen atom,
A C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group or a benzyl group optionally having a halogen atom, C1
C1 to C4 alkyl group or C2 to C4 alkenyl group or C1 to C4 alkoxy group or hydroxyl group or phenethyl group which may have a halogen atom;
Α-methylbenzyl group which may have a C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group or a halogen atom,
Or a C1 to C4 alkyl group or a C2 to C4 alkenyl group or a C1 to C4 alkoxy group, a hydroxyl group or a naphthyl group which may have a halogen atom), and R ₂₅ , R ₂₈ , R ₂₉ At least one of them is (Y and Z are a C1-C6 alkyl group, a C2-C6 alkenyl group, a C1-C4 alkyl group or a C2-C6
4 alkenyl group or C1 to C4 alkoxy group or hydroxyl group or cyclohexyl group optionally having a halogen atom, C1 to C4 alkyl group or C2 to C4
C4 alkenyl group or C1 to C4 alkoxy group or hydroxyl group or cyclopentyl group optionally having a halogen atom, C1 to C4 alkyl group or C2
An alkenyl group of -C4 or an alkoxy group of C1-C4 or a phenyl group optionally having a halogen atom,
A C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group or a benzyl group which may have a halogen atom,
A C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group or a phenethyl group which may have a halogen atom;
Α-methylbenzyl group optionally having 4 alkyl groups or C2 to C4 alkenyl groups or C1 to C4 alkoxy groups or hydroxyl groups or halogen atoms, or C1 to C4 alkyl groups or C2 to C4 alkenyl groups or C1 to C4 alkoxy group, hydroxyl group or naphthyl group which may have a halogen atom).]. 4. A compound of the general formula (VI) Wherein R ₃₃ is (Y and Z are a C1-C6 alkyl group, a C2-C6 alkenyl group, a C1-C4 alkyl group or a C2-
C4 alkenyl group or C1 to C4 alkoxy group or hydroxyl group or cyclohexyl group optionally having a halogen atom, C1 to C4 alkyl group or C2
-C4 alkenyl group or C1-C4 alkoxy group or hydroxyl group or cyclopentyl group which may have a halogen atom, C1-C4 alkyl group or C
A phenyl group which may have a 2-C4 alkenyl group or a C1-C4 alkoxy group or a halogen atom,
A C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group or a benzyl group optionally having a halogen atom, C1
C1 to C4 alkyl group or C2 to C4 alkenyl group or C1 to C4 alkoxy group or hydroxyl group or phenethyl group which may have a halogen atom;
Α-methylbenzyl group which may have a C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group or a halogen atom,
Or a C1-C4 alkyl group, a C2-C4 alkenyl group, a C1-C4 alkoxy group, a hydroxyl group, or a naphthyl group which may have a halogen atom), and R ₃₄ , R ₃₅ , R ₃₆ , R ₃₇
May be the same or different from each other, and represent a hydrogen atom,
A C4 alkyl group, a C2-C4 alkenyl group, a C1
A C4 alkoxy group, a hydroxyl group, a halogen atom, or R ₃₃
Represents the same group as ] The molecular compound which uses the phenol derivative represented by these as a component compound. 5. The molecular compound according to claim 1, wherein the molecular compound is an inclusion compound. 6. A compound of the formula (I), (IV), (V) or (V
A phenol derivative represented by I), an antibacterial agent and an antifungal agent which react with the phenol derivative to form a molecular compound,
Pesticides, insect repellents, fragrances, deodorants / deodorants, antifouling agents, curing agents and curing accelerators for paints, resins, adhesives, natural essential oils,
The molecular compound according to any one of claims 1 to 5, wherein an antioxidant, a vulcanization accelerator or an organic solvent is used as a component compound. 7. Reacting a phenol derivative represented by the general formula (I), (IV), (V) or (VI) with a component compound which reacts with the phenol derivative to form a molecular compound. The method for producing a molecular compound according to any one of claims 1 to 6, characterized in that: