JP2005213382A - Hydroxyaromatic compound and method for producing the same - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a hydroxyaromatic compound suitably usable as a raw material for thermosetting resins requiring high heat resistance and high modulus, and to provide a method for producing the hydroxyaromatic compound. <P>SOLUTION: The hydroxyaromatic compound has a structure of general formula(1)( wherein, R<SP>1</SP>and R<SP>2</SP>are H, methyl, trifluoromethyl, adamantyl or phenyl; n is an integer of 1-10,000; m is 1 or 2; p is an integer of 1-5; and all of the hydrogen atoms except those of the hydroxy groups may be substituted with at least one substituent selected from a 1-20C aliphatic group, fluorine atom, trifluoromethyl, trifluoroethyl, pentafluoroethyl, phenyl and pentafluorophenyl groups ). <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention relates to a hydroxyaromatic compound and a method for producing the same.

Hydroxy aromatic compounds typified by phenolic resins are excellent in heat resistance, mechanical strength and moisture resistance when used in applications such as raw materials for epoxy resins, curing agents for epoxy resins, and resins for molding materials. It is widely used in various fields such as automobile parts. However, the present condition is that the material which satisfy | fills all the requirements in the advanced field | areas where further severe heat resistance and elastic modulus are requested | required especially especially the electronic material field | area has not been obtained yet.
As an improvement measure, studies have been made to stiffen the main chain by introducing a condensed ring into the phenol resin structure. For example, a technique relating to a resin in which a naphthalene structure is introduced into a phenol resin is disclosed (for example, , See Patent Document 1). However, the molecular weight of the resin into which the condensed ring is introduced is low, and the effects of improving heat resistance and elastic modulus due to the introduction of the condensed ring are not sufficiently exhibited.
Japanese Patent Laid-Open No. 6-211954

  The problem to be solved is to provide a hydroxy aromatic compound that can be suitably used as a raw material for a thermosetting resin that requires high heat resistance and high elastic modulus, and a method for producing the same.

（式中のＲ¹およびＲ²は、それぞれ独立して、水素原子、フッ素原子または有機基を示し、互いに同一であっても異なっていてもよい。式中のｎは、１以上、１００００以下の整数を示す。式中のｍは、１または２である。式中のｐは、１以上、５以下の整数である。また、式中のヒドロキシ基の水素原子を除く全ての水素原子は、フッ素原子または有機基で置換されていても良い。）
２．一般式（２）で表される化合物と、アルデヒド化合物とを縮合反応させることを特徴とする、一般式（１）で表されるヒドロキシ芳香族化合物の製造法。

（式中のｍは、１または２である。式中のｐは、１以上、５以下の整数である。また、式中のヒドロキシ基の水素原子を除く全ての水素原子は、フッ素原子または有機基で置換されていても良い。）
３．前記反応は、８０℃以上、２００℃以下の温度領域で行うものである、第２項に記載の一般式（１）で表されるヒドロキシ芳香族化合物の製造法。
４．前記反応は、酸触媒を用いるものである、第２項または第３項に記載の一般式（１）で表されるヒドロキシ芳香族化合物の製造法。 Such an object is achieved by the present invention described in the following items 1 to 4.
1. A hydroxyaromatic compound having a structure represented by the general formula (1).

(In the formula, R ¹ and R ² each independently represent a hydrogen atom, a fluorine atom or an organic group, and may be the same or different. N in the formula is 1 or more and 10,000 or less. M in the formula is 1 or 2. p in the formula is an integer of 1 or more and 5 or less, and all the hydrogen atoms excluding the hydrogen atom of the hydroxy group in the formula are And may be substituted with a fluorine atom or an organic group.)
2. A method for producing a hydroxy aromatic compound represented by the general formula (1), wherein the compound represented by the general formula (2) is subjected to a condensation reaction with an aldehyde compound.

(In the formula, m is 1 or 2. p in the formula is an integer of 1 or more and 5 or less. In addition, all the hydrogen atoms except the hydrogen atom of the hydroxy group in the formula are fluorine atoms or (It may be substituted with an organic group.)
3. The method for producing a hydroxy aromatic compound represented by the general formula (1) according to Item 2, wherein the reaction is performed in a temperature range of 80 ° C or higher and 200 ° C or lower.
4). The said reaction uses an acid catalyst, The manufacturing method of the hydroxy aromatic compound represented by General formula (1) of the 2nd term | claim or the 3rd term | claim.

  According to the present invention, a hydroxy aromatic compound having excellent heat resistance and elastic modulus can be provided.

  The hydroxy aromatic compound of the present invention is represented by the general formula (1), and has a rigid fluorene structure in the main chain, and therefore has excellent heat resistance and elastic modulus, high heat resistance and high resistance. It can be suitably used as a thermosetting resin that requires an elastic modulus.

In the present invention, R ¹ and R ² in the general formula (1) each independently represent a hydrogen atom, a fluorine atom or an organic group, and may be the same or different from each other. Examples of the organic group include alkyl groups having 1 to 20 carbon atoms such as a methyl group, an ethyl group, a propyl group, and a butyl group: carbon numbers such as a methoxy group, an ethoxy group, a propyloxy group, and a butoxy group. Is an alkoxy group having a carbon number of 1 or more and 20 or less, such as a vinyl group, a propenyl group and a butenyl group, and an alkenyl group having a carbon number of 20 or less, an ethynyl group, a propynyl group and a butynyl group having 1 or more carbon atoms, 20 or less alkynyl groups: cyclopentyl group, cyclohexyl group, adamantyl group, alicyclic aliphatic group such as diamantyl group and biadamantyl group: aromatic group such as phenyl group, naphthyl group, phenoxy group and naphthoxy group: However, it is not limited to these. Moreover, the hydrogen atom in the organic group may be substituted with a fluorine atom.

  In the present invention, n in the general formula (1) represents an integer of 1 or more and 10,000 or less. Further, m in the general formula (1) represents 1 or 2, and p in the general formula (1) represents an integer of 1 or more and 5 or less.

  In the present invention, examples of the hydroxy aromatic compound having the structure represented by the general formula (1) include poly (9- (2-hydroxyphenyl) fluorenediylmethylene) and poly (9- (3-hydroxyphenyl) full Orangeylmethylene), poly (9- (4-hydroxyphenyl) fluorenediylmethylene), poly (9- (2,3-dihydroxyphenyl) fluorangeylmethylene), poly (9- (2,4-dihydroxyphenyl) ) Fluorangeylmethylene), poly (9- (2,5-dihydroxyphenyl) fluorangeylmethylene), poly (9- (2,6-dihydroxyphenyl) fluorangeylmethylene), poly (9- (3 4-dihydroxyphenyl) fluorenediylmethylene), poly (9- (3,5-dihydroxyphenyl) Luoylylmethylene), poly (9- (2,3,4-trihydroxyphenyl) fluorenediylmethylene), poly (9- (2,3,5-trihydroxyphenyl) fluorangeylmethylene), poly ( 9- (2,3,6-trihydroxyphenyl) fluorenediylmethylene), poly (9- (2,4,5-trihydroxyphenyl) fluorenediylmethylene), poly (9- (2,4,6 -Trihydroxyphenyl) fluorenediylmethylene), poly (9- (2,3,4,5-tetrahydroxyphenyl) fluorenediylmethylene), poly (9- (2,3,4,6-tetrahydroxyphenyl) ) Fluorangeylmethylene), poly (9- (2,3,4,5,6-pentahydroxyphenyl) fluorangeylmethylene), poly (9 9-bis (2-hydroxyphenyl) fluorenediylmethylene), poly (9,9-bis (3-hydroxyphenyl) fluorenediylmethylene), poly (9,9-bis (4-hydroxyphenyl) fluorenediylyl Methylene), poly (9,9-bis (2-hydroxymethyl) fluorenediyl-methylmethylene), poly (9,9-bis (3-hydroxymethyl) fluorenediyl-methylmethylene), poly (9,9 -Bis (4-hydroxymethyl) fluorenediyl-methylmethylene), poly (9,9-bis (2-hydroxymethyl) fluorenediyl- (1-adamantyl) methylene), poly (9,9-bis (3 -Hydroxymethyl) fluorangeyl- (1-adamantyl) methylene), poly (9,9-bis (4-hydroxymethyl) Fluorenediyl- (1-adamantyl) methylene), poly (9,9-bis (2-hydroxyphenyl) fluorenediyl-phenylmethylene), poly (9,9-bis (3-hydroxyphenyl) fluorenediyl- Phenylmethylene), poly (9,9-bis (4-hydroxyphenyl) fluorenediyl-phenylmethylene), poly (9,9-bis (2-hydroxyphenyl) fluorenediyl- (1-adamantyl) methylene), Poly (9,9-bis (3-hydroxyphenyl) fluorenediyl- (1-adamantyl) methylene), poly (9,9-bis (4-hydroxyphenyl) fluorenediyl- (1-adamantyl) methylene), Poly (9,9-bis (2,3-dihydroxyphenyl) fluorenediylmethylene), poly (9, -Bis (2,4-dihydroxyphenyl) fluorenediylmethylene), poly (9,9-bis (2,5-dihydroxyphenyl) fluorenediylmethylene), poly (9,9-bis (2,6-dihydroxy) Phenyl) fluorenediylmethylene), poly (9,9-bis (3,4-dihydroxyphenyl) fluorenediylmethylene), poly (9,9-bis (3,5-dihydroxyphenyl) fluorangeylmethylene), Poly (9,9-bis (2,3,4-trihydroxyphenyl) fluorenediylmethylene), poly (9,9-bis (2,3,5-trihydroxyphenyl) fluorenediylmethylene), poly ( 9,9-bis (2,3,6-trihydroxyphenyl) fluorenediylmethylene), poly (9,9-bis (2,4,5-toe) Hydroxyphenyl) fluorangeylmethylene), poly (9,9-bis (2,4,6-trihydroxyphenyl) fluorenediylmethylene), poly (9,9-bis (2,3,4,5-tetra) Hydroxyphenyl) fluorangeylmethylene), poly (9,9-bis (2,3,4,6-tetrahydroxyphenyl) fluorenediylmethylene), poly (9,9-bis (2,3,4,5) , 6-pentahydroxyphenyl) fluorenediylmethylene), and the like, but is not limited thereto. Moreover, all the hydrogen atoms except the hydrogen atom of the hydroxy group in these structures may be substituted with at least one group selected from a fluorine atom or an organic group. Examples of the organic group include alkyl groups such as methyl group, ethyl group, propyl group and butyl group: alkoxy groups such as methoxy group, ethoxy group, propyloxy group and butoxy group: vinyl group, propenyl group and butenyl. Alkenyl groups such as ethynyl groups, alkynyl groups such as ethynyl groups, propynyl groups and butynyl groups: cycloaliphatic aliphatic groups such as cyclopentyl groups, cyclohexyl groups, adamantyl groups, diamantyl groups and biadamantyl groups: phenyl groups, naphthyl groups Groups, aromatic groups such as phenoxy group and naphthoxy group, and the like, but are not limited thereto. Moreover, the hydrogen atom in the organic group may be substituted with a fluorine atom.

The hydroxy aromatic compound represented by the general formula (1) of the present invention can be synthesized, for example, as follows.
First, the compound represented by the general formula (2) is dissolved or suspended in a suitable solvent. A hydroxyaromatic compound having a structure represented by the general formula (1) can be synthesized by adding an aldehyde compound and a catalyst and reacting by heating. As a method for isolating the hydroxyaromatic compound having the structure represented by the general formula (1) from the reaction solution, the reaction solution is cooled and the precipitated solid is separated from the solvent, and the solvent is distilled from the reaction solution under reduced pressure. The method of leaving is mentioned.

  Examples of the solvent include water, methanol, ethanol, propanol, butanol, cyclohexanol, tetrahydrofuran, benzene, toluene, and xylene, but are not limited thereto. Preferably, a water-insoluble solvent having a boiling point higher than that of water and a specific gravity of less than 1 such as butanol or toluene may be used. By using these, water generated during the reaction can be efficiently removed by the fractionating tube, and the reaction can be promoted. The amount of the solvent used is 1 to 30 times, preferably 1 to 10 times the weight of the compound represented by the general formula (2).

  Examples of the aldehyde compound include, but are not limited to, formaldehyde, benzaldehyde, acetaldehyde, adamantyl aldehyde, and the like, and those that generate formalin and formaldehyde under reaction conditions can also be used. In addition, the amount of the aldehyde compound used is 0.1 equivalent times or more and 2 equivalent times or less, preferably 0.5 equivalent times or more, with respect to the compound represented by the general formula (2). 0.5 equivalent times or less, more preferably 0.8 equivalent times or more and 1.2 equivalent times or less.

  The catalyst is preferably an acid catalyst, and specific examples include acetic acid, chloroacetic acid, dichloroacetic acid, trichloroacetic acid, formic acid, phosphoric acid, oxalic acid, sulfuric acid, nitric acid, and hydrochloric acid, but are not limited thereto. Absent. Sulfuric acid or hydrochloric acid is preferable. The amount of the catalyst used is 0.001 equivalent times or more and 1 equivalent time or less, preferably 0.001 equivalent times or more, and 0.001 equivalent time or more, relative to the compound represented by the general formula (2). 5 equivalent times or less, more preferably 0.001 equivalent times or more and 0.01 equivalent times or less. As a method for charging the catalyst, it may be charged as it is, or after being diluted to a suitable concentration with a solvent such as water.

  In the said reaction, as reaction temperature, 80 to 200 degreeC is preferable, More preferably, it is 100 to 150 degreeC. By making it react within the said range, the water produced | generated during reaction can be efficiently removed with a fractionating pipe, and it becomes possible to promote reaction. Moreover, in the said reaction, as reaction time, 1 hour or more and 7 days or less are preferable, More preferably, it is 1 hour or more and 5 hours or less.

  In the present invention, the compound represented by the general formula (2) includes 9- (2-hydroxyphenyl) fluorene, 9- (3-hydroxyphenyl) fluorene, 9- (4-hydroxyphenyl) fluorene, 9- ( 2,3-dihydroxyphenyl) fluorene, 9- (2,4-dihydroxyphenyl) fluorene, 9- (2,5-dihydroxyphenyl) fluorene, 9- (2,6-dihydroxyphenyl) fluorene, 9- (3 4-dihydroxyphenyl) fluorene, 9- (3,5-dihydroxyphenyl) fluorene, 9- (2,3,4-trihydroxyphenyl) fluorene, 9- (2,3,5-trihydroxyphenyl) fluorene, 9 -(2,3,6-trihydroxyphenyl) fluorene, 9- (2,4,5-trihydroxyphenyl) L) fluorene, 9- (2,4,6-trihydroxyphenyl) fluorene, 9- (2,3,4,5-tetrahydroxyphenyl) fluorene, 9- (2,3,4,6-tetrahydroxyphenyl) ) Fluorene, 9- (2,3,4,5,6-pentahydroxyphenyl) fluorene, 9,9-bis (2-hydroxyphenyl) fluorene, 9,9-bis (3-hydroxyphenyl) fluorene, 9-bis (4-hydroxyphenyl) fluorene, 9,9-bis (2,3-dihydroxyphenyl) fluorene, 9,9-bis (2,4-dihydroxyphenyl) fluorene, 9,9-bis (2,5 -Dihydroxyphenyl) fluorene, 9,9-bis (2,6-dihydroxyphenyl) fluorene, 9,9-bis (3,4-dihydroxyphenyl) Nyl) fluorene, 9,9-bis (3,5-dihydroxyphenyl) fluorene, 9,9-bis (2,3,4-trihydroxyphenyl) fluorene, 9,9-bis (2,3,5-tri) Hydroxyphenyl) fluorene, 9,9-bis (2,3,6-trihydroxyphenyl) fluorene, 9,9-bis (2,4,5-trihydroxyphenyl) fluorene, 9,9-bis (2,4 , 6-trihydroxyphenyl) fluorene, 9,9-bis (2,3,4,5-tetrahydroxyphenyl) fluorene, 9,9-bis (2,3,4,6-tetrahydroxyphenyl) fluorene, 9 , 9-bis (2,3,4,5,6-pentahydroxyphenyl) fluorene, and the like, but is not limited thereto. Moreover, all the hydrogen atoms except the hydrogen atom of the hydroxy group in these structures may be substituted with a fluorine atom or an organic group. Examples of the organic group include alkyl groups such as methyl group, ethyl group, propyl group and butyl group: alkoxy groups such as methoxy group, ethoxy group, propyloxy group and butoxy group: vinyl group, propenyl group and butenyl. Alkenyl groups such as ethynyl groups, alkynyl groups such as ethynyl groups, propynyl groups and butynyl groups: cycloaliphatic aliphatic groups such as cyclopentyl groups, cyclohexyl groups, adamantyl groups, diamantyl groups and biadamantyl groups: phenyl groups, naphthyl groups Group, aromatic group such as phenoxy group and naphthoxy group, and the like, but is not limited thereto. Moreover, the hydrogen atom in the organic group may be substituted with a fluorine atom.

  Examples are given below to illustrate the present invention, but the present invention is not limited thereby.

The obtained compound was subjected to ¹ H-NMR spectrum measurement, infrared spectroscopic analysis, molecular weight measurement, thermogravimetric analysis, and elastic modulus measurement for property evaluation. Each measurement condition was as follows.
[Test method]
(1) Nuclear magnetic resonance spectrum analysis ( ¹ H-NMR): Measured at a resonance frequency of 400 MHz using a JNM-GSX400 type manufactured by JEOL. As a measurement solvent, deuterated dimethyl sulfoxide DMSO-d ₆ was used.
(2) Infrared spectroscopic analysis (IR): Measured by the KBr tablet method using Shimadzu FT-IR8900 type.
(3) Elemental analysis: Carbon and hydrogen were measured using a Model 2400 manufactured by PERKIN ELMER.
(4) Molecular weight: The weight average molecular weight Mw and the number average molecular weight Mn were calculated by polystyrene conversion using a high performance liquid chromatograph SD-8022 manufactured by Tosoh Corporation.
(5) Thermogravimetric analysis: Using a TG / DTA6200 model manufactured by Seiko Instruments Inc., the amount of thermogravimetric decrease was measured under a temperature increase rate of + 5 ° C./min under a dry nitrogen stream of 200 mL / min. .
(6) Elastic modulus: Using an ENT-1100 manufactured by Elionix Co., Ltd., the elastic modulus of a film having a thickness of 30 μm prepared from the obtained compound was measured in an atmosphere at a temperature of 22 ° C. and a humidity of 50%. The coating was prepared by applying a coating varnish composed of a sample for measurement and cyclohexanone on a silicon substrate to obtain a uniform film thickness by spin coating, and then heating and drying at 100 ° C. for 10 minutes.

[Example 1]
(Synthesis of poly (9,9-bis (4-hydroxyphenyl) fluorenediylmethylene))
35 g (0.1 mol) of 9,9-bis (4-hydroxyphenyl) fluorene and 100 g of 1-butanol were stirred at 60 ° C. and dissolved. A 37% formaldehyde aqueous solution 8.1 g (0.1 mol) and 50% sulfuric acid 1 g (0.005 mol) were added thereto. The reaction solution was stirred at 100 ° C. for 1 hour and further at 140 ° C. for 2 hours while removing water using a Dean-Stark trap. Subsequently, the pressure inside the reactor was reduced to remove the solvent. The obtained solid was pulverized and washed with water to obtain 36 g of poly (9,9-bis (4-hydroxyphenyl) fluorenediylmethylene).
The various measured values regarding the obtained compound are shown below. These data indicate that the obtained compound is the target product. ¹ H-NMR spectrum is shown in FIG. 1, IR absorption spectrum is shown in FIG. 2, and the results of thermogravimetric analysis are shown in FIG.
¹ H-NMR (400 MHz, DMSO-d6, ppm): δ 3.1-4.0 (2H), δ 6.2-8.0 (14H), δ 8.8-9.8 (2H)
IR (KBr, / cm): 3506, 3061, 3017, 2930, 2872, 1609, 1508, 1447, 1329, 1175, 820
Elemental analysis: [theoretical value (converted to one unit)] C: 86.16%, H: 5.01%, O: 8.83%, [actual value] C: 83.56%, H: 5.49 %
Molecular weight: Mw = 12,500, Mn = 2970
Elastic modulus: 4.8 GPa

[Example 2]
(Synthesis of high molecular weight poly (9,9-bis (4-hydroxyphenyl) fluorenediylmethylene))
9,9-bis (4-hydroxyphenyl) fluorene (35 g, 0.1 mol) and toluene (100 g) were stirred at room temperature. A 37% formaldehyde aqueous solution 8.1 g (0.1 mol) and 50% sulfuric acid 1 g (0.005 mol) were added thereto. The reaction solution was stirred at 100 ° C. for 1 hour and further at 130 ° C. for 2 hours while removing water using a Dean-Stark trap. The reaction solution was cooled in a water bath and the solid was collected by filtration. After pulverizing the solid, the solid was stirred and washed in methanol. Further, by washing with water, 11 g of high molecular weight poly (9,9-bis (4-hydroxyphenyl) fluorenediylmethylene) was obtained.
The various measured values regarding the obtained compound are shown below. These data indicate that the obtained compound is the target product.
¹ H-NMR (400 MHz, DMSO-d6, ppm): δ3.0-4.1 (2H), δ5.8-8.0 (14H), δ8.7-9.4 (2H)
IR (KBr, / cm): 3489, 3061, 3017, 2934, 1607, 1506, 1447, 1329, 1175, 820
Elemental analysis: [theoretical value (converted to one unit)] C: 86.16%, H: 5.01%, O: 8.83%, [actual value] C: 84.04%, H: 5.11 %
Molecular weight: Mw = 53700, Mn = 26200
Elastic modulus: 4.9 GPa

[Example 3]
(Synthesis of poly (9,9-bis (4-hydroxyphenyl) fluorenediyl-phenylmethylene))
In Example 1, except that 8.1 g (0.1 mol) of 37% formaldehyde aqueous solution, 11 g (0.1 mol) of benzaldehyde, and 1 g (0.005 mol) of 50% sulfuric acid were changed to 0.5 g (0.005 mol) of sulfuric acid. In the same manner as in Example 1, 44 g of poly (9,9-bis (4-hydroxyphenyl) fluorenediyl-phenylmethylene) was obtained.
The various measured values regarding the obtained compound are shown below. These data indicate that the obtained compound is the target product.
¹ H-NMR (400 MHz, DMSO-d6, ppm): δ 5.3-7.9 (19H), δ 8.7-9.4 (2H)
IR (KBr, / cm): 3500, 3050, 3017, 2931, 1612, 1500
Elemental analysis: [theoretical value (converted to one unit)] C: 87.65%, H: 5.06%, O: 7.30%, [actual measurement value] C: 86.76%, H: 5.00 %
Molecular weight: Mw = 1600, Mn = 2580
Elastic modulus: 5.1 GPa

[Example 4]
(Synthesis of poly (9,9-bis (4-hydroxyphenyl) fluorenediyl- (1-adamantyl) methylene))
In Example 1, 8.1 g (0.1 mol) of a 37% formaldehyde aqueous solution, 16 g (0.1 mol) of 1-adamantyl aldehyde, 1 g (0.005 mol) of 50% sulfuric acid and 0.5 g (0.005 mol) of sulfuric acid Except that, 43 g of poly (9,9-bis (4-hydroxyphenyl) fluorenediyl- (1-adamantyl) phenylmethylene) was obtained in the same manner as in Example 1.
The various measured values regarding the obtained compound are shown below. These data indicate that the obtained compound is the target product.
¹ H-NMR (400 MHz, DMSO-d6, ppm): δ 0.7-2.2 (15H), δ 5.8-7.9 (14H), δ 8.7-9.4 (2H)
IR (KBr, / cm): 3500, 3050, 3017, 2931, 1612, 1500
Elemental analysis: [theoretical value (converted to one unit)] C: 87.06%, H: 6.49%, O: 6.44%, [actual value] C: 86.17%, H: 6.70 %
Molecular weight: Mw = 7080, Mn = 1300
Elastic modulus: 5.0 GPa

[Comparative Example 1]
Phenol 130 g (1.4 mol), 37% formaldehyde aqueous solution 92.4 g (1.1 mol), oxalic acid dihydrate 1 g (0.0079 mol), and water 13 mL were stirred at 100 ° C. for 1 hour. Further, 1 g (0.0079 mol) of oxalic acid dihydrate was added and heated at 100 ° C. for 1 hour, and then 400 mL of water was added to cool the reaction solution. The precipitated solid was dried at 120 ° C. under reduced pressure to obtain 140 g of a phenol resin.
The various measured values regarding the obtained compound are shown below. The results of thermogravimetric analysis are shown in FIG.
Molecular weight: Mw = 3100, Mn = 800
Elastic modulus: 2.4 GPa

  From the above, it is clear that the hydroxy aromatic compound having the structure represented by the general formula (1) of the present invention is superior in heat resistance and elastic modulus than the conventional phenol resin.

FIG. 1 is a diagram showing a ¹ H-NMR spectrum of the hydroxyaromatic compound obtained in Example 1 of the present invention. FIG. 2 is a diagram showing an IR absorption spectrum of the hydroxyaromatic compound obtained in Example 1 of the present invention. FIG. 3 is a diagram showing the results of thermogravimetric analysis of the hydroxyaromatic compound obtained in Example 1 of the present invention and the phenol resin obtained in Comparative Example 1.

Claims (4)

A hydroxyaromatic compound having a structure represented by the general formula (1).

(In the formula, R ¹ and R ² each independently represent a hydrogen atom, a fluorine atom or an organic group, and may be the same or different. N in the formula is 1 or more and 10,000 or less. M in the formula is 1 or 2. p in the formula is an integer of 1 or more and 5 or less, and all the hydrogen atoms except the hydrogen atom of the hydroxy group in the formula are And may be substituted with a fluorine atom or an organic group.) A method for producing a hydroxy aromatic compound represented by the general formula (1), wherein the compound represented by the general formula (2) is subjected to a condensation reaction with an aldehyde compound.

(In the formula, m is 1 or 2. p in the formula is an integer of 1 or more and 5 or less. In addition, all the hydrogen atoms except the hydrogen atom of the hydroxy group in the formula are fluorine atoms or (It may be substituted with an organic group.)   The method for producing a hydroxy aromatic compound represented by the general formula (1) according to claim 2, wherein the reaction is performed in a temperature range of 80 ° C or higher and 200 ° C or lower. The method for producing a hydroxy aromatic compound represented by the general formula (1) according to claim 2 or 3, wherein the reaction uses an acid catalyst.

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