KR102357570B1 - New bis(hydroxyalkoxyphenyl)diphenylmethanes - Google Patents

Abstract

(식 중 R은 탄소원자 수 2~6의 알킬렌기를 나타내고, R₁은 페닐기이며, R₂는 각각 독립적으로 탄소원자 수 1~6의 알킬기, 탄소원자 수 1~6의 알콕시기 또는 할로겐원자를 나타내며, a는 1~3의 정수를 나타내고, b는 0 또는 1~3의 정수를 나타내며, 단 b가 2 이상인 경우 R₂는 동일해도 되고 상이해도 되며, 또한 1≤a＋b≤4이다.)로 나타내어지는 비스(히드록시알콕시페닐)디페닐메탄류이다.An object of the present invention is to provide a novel aromatic dihydroxyalkoxy compound that has high solubility, good operability with a low melting point, and can also be improved in properties such as optical properties and heat resistance.
As a means of solving the above problems, the present invention provides the following Chemical Formula 1
[Formula 1]

(wherein R represents an alkylene group having 2 to 6 carbon atoms, R ₁ is a phenyl group, and R ₂ is each independently an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom represents, a represents an integer of 1 to 3, b represents an integer of 0 or 1 to 3, with the proviso that when b is 2 or more, R ₂ may be the same or different, and 1≤a+b≤4.) bis(hydroxyalkoxyphenyl)diphenylmethanes represented by

Description

Novel bis(hydroxyalkoxyphenyl)diphenylmethanes {New bis(hydroxyalkoxyphenyl)diphenylmethanes}

The present invention relates to novel bis(hydroxyalkoxyphenyl)diphenylmethanes, and more particularly, to a dihydroxy compound having a diphenylmethane skeleton.

Such aromatic dihydroxy compounds are useful as raw materials for various chemical products, such as raw materials for aromatic polyester resins, polycarbonate resins, and acrylic derivatives, which are raw materials for high refractive resins.

In recent years, polynuclear aromatic polyvalent hydroxy compounds such as aromatic dihydroxy compounds have been used as raw materials for high-functional resins such as heat-resistant resins. Of these polynuclear aromatic polyvalent hydroxy compounds, aromatic dihydroxyalkoxy compounds having a diphenylmethane skeleton such as 1,1-bis[4-(2-hydroxyethoxy)phenyl]-1,1-diphenylmethane are poly It is used as a raw material for a monomer of an ester resin or an acrylic derivative which is a raw material for a high refractive resin (Patent Document 1, Patent Document 2, Patent Document 3).

However, 1,1-bis[4-(2-hydroxyethoxy)phenyl]-1,1-diphenylmethane has low solubility in solvents due to its high melting point and poor operability and processability. When used as a solvent, there are problems such as requiring a long time for dissolution or melting, or requiring more solvent or higher temperature.

Further, compounds such as 1,1-bis[4-(2-hydroxyethoxy)phenyl]-1-phenylethane have a low melting point and high solvent solubility, but the refractive index and glass transition temperature of the resulting resin are low (Patent Document) 4).

Accordingly, there is a demand for an aromatic dihydroxyalkoxy compound that has high solubility, good operability due to a low melting point, and can also improve properties such as optical properties and heat resistance.

US Patent No. 3796688 Publication Japanese Patent Laid-Open No. Hei02-111742 Japanese Patent Laid-Open No. 06-145320 Japanese Patent Laid-Open No. Hei 08-100053

Accordingly, an object of the present invention is to provide a novel aromatic dihydroxyalkoxy compound that has high solubility, good operability with a low melting point, and can also improve optical properties and properties such as heat resistance.

The present inventors have studied the above problems of aromatic dihydroxyalkoxy compounds having a tetraphenyl skeleton such as 1,1-bis[4-(2-hydroxyethoxy)phenyl]-1,1-diphenylmethane As a result of the study, in 1,1-bis[4-(2-hydroxyalkoxy)phenyl]-1,1-diphenylmethane, polynuclear aromatic dihydroxyalkoxy in which a phenyl group was further substituted with a phenyl group having a hydroxyalkoxy group The present invention was completed by discovering that the compound has excellent solubility in organic solvents due to its low melting point, and that the refractive index and glass transition temperature are also equal or excellent.

That is, the present invention

Formula 1

(wherein R represents an alkylene group having 2 to 6 carbon atoms, R ₁ is a phenyl group, and R ₂ is each independently an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom represents, a represents an integer of 1 to 3, b represents an integer of 0 or 1 to 3, with the proviso that when b is 2 or more, R ₂ may be the same or different, and 1≤a+b≤4.)

bis(hydroxyalkoxyphenyl)diphenylmethanes represented by

The bis(hydroxyalkoxyphenyl)diphenylmethanes of the present invention are aromatic dialcohols of polynuclear aromatic hydrocarbons having a diphenylmethane skeleton and a structure in which a phenyl group is also substituted with a phenyl group substituted with a hydroxyalkoxy group.

With such a structure, the aromatic dialcohol of the present invention has a low melting point and excellent solubility compared to conventional, for example, bis{4-(2-hydroxyethoxy)phenyl}diphenylmethane, operability can be improved. For example, when it is industrially used in a large amount, melting or dissolution time can be shortened. Further, even at a lower temperature, the same dissolution time can be obtained, or when the solvent used is the same, it is possible to reduce the amount of the solvent used.

In addition, conventional compounds such as 1,1-bis[4-(2-hydroxyethoxy)phenyl]-1-phenylethane have a low melting point and high solvent solubility, and the refractive index and glass transition temperature of the resulting resin is low, the compound of the present invention has a low melting point, but the refractive index and glass transition temperature do not change, but rather improve, so it is expected that the refractive index and heat resistance of the obtained resin are also improved.

The bis(hydroxyalkoxyphenyl)diphenylmethanes of the present invention are represented by the above formula (1).

_{In Formula 1, the substitution position of R 1} which is a phenyl group substituted with a phenyl group substituted with a hydroxyalkoxy group in the formula is preferably an ortho position of the hydroxyalkoxy group. In addition, the phenyl group substituted with a phenyl group substituted with a hydroxyalkoxy group may be substituted with an alkyl group having 1 to 3 carbon atoms or an alkoxyl group 1 to 2 within the range that does not impair the effects of the present invention, but heat resistance and refractive index It is preferable that it is not substituted from the viewpoint of. Moreover, a represents the integer of 1-3, Preferably it is 1 or 2, More preferably, it is 1.

In the formula, R ₂ each independently represents an alkyl group having 1 to 6 carbon atoms, an alkoxy group having 1 to 6 carbon atoms, or a halogen atom.

The alkyl group having 1 to 6 carbon atoms is preferably a linear or branched chain alkyl group having 1 to 4 carbon atoms or a cyclic alkyl group having 5 to 6 carbon atoms, specifically, for example, a methyl group, an ethyl group, A propyl group, an isopropyl group, n-butyl group, a p-butyl group, a cyclopentyl group, a cyclohexyl group, etc. are mentioned.

The alkoxy group having 1 to 6 carbon atoms is preferably a linear or branched alkoxy group having 1 to 4 carbon atoms or a cyclic alkoxy group having 5 to 6 carbon atoms, specifically, for example, an ethoxy group , a propoxy group, a p-butoxy group, a cyclohexyloxy group, and the like.

Specific examples of the halogen atom include a chlorine atom, a bromine atom, and an iodine atom.

As such R _{2 , an} alkyl group is preferable, and a methyl group is more preferable.

The substitution position of R ₂ is preferably the ortho position of the hydroxyalkoxy group when the number of substitutions b is 1.

Moreover, b represents 0 or the integer of 1-3, 0, 1 or 2 are preferable, and 0 or 1 is more preferable from a viewpoint of heat resistance and refractive index. When b is 2 or more, R ₂ may be the same or different, and is in the range of 1≤a+b≤4.

In the formula (1), in the formula, R represents an alkylene group having 2 to 6 carbon atoms.

The alkylene group is preferably a linear or branched alkylene group, more preferably an alkylene group having 2 to 4 carbon atoms, and particularly preferably an alkylene group having 2 or 3 carbon atoms. Therefore, specific examples of R include a 1,2-ethylenediyl group, a 1,2-propanediyl group, a 1,3-propanediyl group, a pentamethylene group, and a hexamethylene group.

In addition, in the hydroxyalkoxy group represented by -OR-OH in the formula, the bonding position of the hydroxyl group bonded to the alkylene group R is not bonded to the carbon atom constituting the alkylene group R directly bonded to the ether group (referred to as the 1-position carbon atom). does not That is, it is bonded to the carbon atom at the 2nd and 6th positions of the alkylene group R.

When the number of carbon atoms in R is 3 or more, it is preferable to couple to the 2nd or 3rd position of the alkylene group R, more preferably the 2nd position. Therefore, as a preferable hydroxyalkoxy group, specifically, for example, a 2-hydroxyethoxy group, a 2-hydroxypropoxy group, a 2-hydroxy-1-methylethoxy group, a 3-hydroxypropoxy group, etc. are used. can be heard

Accordingly, preferred bis(hydroxyalkoxyphenyl)diphenylmethanes in the bis(hydroxyalkoxyphenyl)diphenylmethanes of the present invention represented by Formula 1 are bis(hydroxyethoxyphenyl)diphenylmethanes, It is represented by the following formula (2).

( _{Wherein, R 1} , R ₂ , a and b are the same as those of Formula 1, and R ₃ each independently represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms, provided that each hydroxyethoxy group The total number of carbon atoms of _{R 3 to be substituted is 4 or less.)}

In the formula (2), _{the alkyl group of R 3} includes, for example, a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an isobutyl group. Among them, R ₃ is preferably a hydrogen atom or a methyl group.

In addition, as a preferable combination of _{R 3} substituted with each hydroxyethoxy group, when _{two R 3} are bonded to the same carbon atom, it is preferable that at least one of the _{two R 3 is a hydrogen atom, and R 3} is It is more preferable that all are hydrogen atoms.

Therefore, as preferable bis(hydroxyalkoxyphenyl)diphenylmethanes, specifically, for example, 1,1-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]-1,1-diphenylmethane ,

1,1-bis[4-(2-hydroxypropoxy)-3-phenylphenyl]-1,1-diphenylmethane, 1,1-bis[4-(2-hydroxy-1-methylethoxy) )-3-phenylphenyl]-1,1-diphenylmethane, 1,1-bis[4-(3-hydroxypropoxy)-3-phenylphenyl]-1,1-diphenylmethane, 1,1 -bis[4-(2-hydroxyethoxy)-3,5-diphenylphenyl]-1,1-diphenylmethane, 1,1-bis[4-(2-hydroxyethoxy)-3- Methyl-5-phenylphenyl]-1,1-diphenylmethane, 1,1-bis[4-(2-hydroxyethoxy)-2-methyl-5-phenylphenyl]-1,1-diphenylmethane and the like.

The method for producing the bis(hydroxyalkoxyphenyl)diphenylmethanes, preferably bis(hydroxyethoxyphenyl)diphenylmethanes, represented by the above formula (1) of the present invention is not particularly limited, and a known method is used. It is possible to manufacture

For example, bisphenols of the following formula (3) and alkylene carbonates of the following formula (4) or alkylene oxides of the following formula (5) corresponding to the bis(hydroxyalkoxyphenyl)diphenylmethanes represented by the formula (1) of the present invention and a method of producing the bisphenol by using the above-mentioned bisphenol and a halogenated alcohol represented by the following formula (6) in the presence of an alkali such as potassium carbonate in a polar solvent such as dimethylformamide.

Among these production methods, the method using alkylene carbonates or alkylene oxides is a method for producing bis(hydroxyethoxyphenyl)diphenylmethanes of Formula 2, which is a preferred embodiment of the present invention, mainly from the viewpoint of economy. desirable.

( _{Wherein, R 1} , R ₂ , a or b is the same as that of Formula 1.)

(wherein R ₃ is the same as that of Formula 2)

(Wherein, R ₃ is the same as that of Formula 2).

(Wherein, R is the same as that of Formula 1, X represents a halogen atom, provided that X is not substituted with a carbon atom substituted with a hydroxyl group.)

With respect to the method for producing the bis(hydroxyalkoxyphenyl)diphenylmethanes of the present invention, as an example, the method using the above-described alkylene carbonates will be described in further detail.

When the reaction is shown as a reaction scheme, for example, the reaction of 1,1-bis(4-hydroxy-3-phenylphenyl)-1,1-diphenylmethane and ethylene carbonate is represented by the following reaction scheme (1).

Scheme (1)

In this method, the raw material bisphenols represented by the formula (3) are preferably, for example, 1,1-bis(4-hydroxy-3-phenylphenyl)-1,1-diphenylmethane, 1,1-bis (5-methyl-4-hydroxy-3-phenylphenyl)-1,1-diphenylmethane, 1,1-bis(2-methyl-4-hydroxy-5-phenylphenyl)-1,1-di phenylmethane, 1,1-bis(4-hydroxy-3,5-diphenylphenyl)-1,1-diphenylmethane, 1,1-bis(4-hydroxy-2-phenylphenyl)-1, 1-diphenylmethane etc. are mentioned.

In addition, examples of the alkylene carbonate represented by the formula (4) include ethylene carbonate, propylene carbonate, 1,2-butylene carbonate, and the like.

In addition, the usage-amount of alkylene carbonate is the range of about 2-10 mol normally with respect to 1 mol of bisphenols, Preferably it is the range of about 3-5 mol.

The reaction is usually carried out in the presence of a base catalyst.

Examples of the base catalyst include alkali catalysts such as sodium hydroxide, potassium hydroxide, sodium carbonate and potassium carbonate, and quaternary ammonium halides such as tetrabutylammonium bromide, tetraethylammonium chloride and tetramethylammonium chloride.

The amount of the catalyst is usually in the range of 0.005 to 0.5 moles, preferably 0.01 to 0.3 moles, per 1 mole of the bisphenols.

The reaction temperature is usually in the range of 100 to 150°C, preferably in the range of 120 to 130°C.

A solvent is usually used for the reaction. Examples of the solvent include aromatic hydrocarbon solvents such as toluene and xylene, ketone solvents such as acetone and methyl isobutyl ketone, ether solvents such as tetrahydrofuran, dioxane, and 1,2-diethoxyethane, 1-butanol, 2-butanol , aliphatic alcohol solvents such as ethylene glycol, and non-protic polar solvents such as dimethylformamide and dimethyl sulfoxide. As for the quantity of a solvent, 50-300 weight part is preferable with respect to 100 weight part of bisphenols, for example, 100-200 weight part is more preferable.

For the reaction, for example, reaction raw materials, catalyst, solvent, etc. may be put into a reaction vessel at once and heated to the reaction temperature, or a mixture of bisphenols, solvent, and catalyst may be heated to a predetermined temperature to add alkylene carbonates thereto. You can drop it.

After completion of the reaction, the target product can be taken out as a crude product or a high-purity product from the reaction mixture by a known purification method.

For example, after completion of the reaction, water is added to the reaction mixture to decompose excess alkylene carbonate. When an alkali catalyst is used, an acid may be added to neutralize it. Next, after adding a solvent for separating water as needed, the oil layer is washed with water to remove the catalyst or neutralized salt.

After that, the oil layer is cooled or the oil layer is concentrated, dissolved by adding a solvent, cooled, crystallized, and filtered to obtain the target product. Recrystallization makes it possible to obtain a higher purity target.

In addition, the bisphenols of the raw material represented by the above formula (3) can be purified using a known method. For example, it can be obtained by a method in which the phenylphenols represented by the formula (7) corresponding to the above bisphenols and the dichlorodiphenylmethanes represented by the formula (8) are reacted under heating. When the above reaction is shown as a reaction scheme, for example, a reaction to obtain 1,1-bis(4-hydroxy-3-phenylphenyl)-1,1-diphenylmethane by reaction of 2-phenylphenols with dichlorodiphenylmethane is represented by the following reaction formula (2).

Scheme (2)

( _{Wherein, R 1} , R ₂ , a and b are the same as those of Formula 1. However, R ₁ is not substituted at the para position of the hydroxyl group, and when b is 1 or more, R ₂ is not substituted at the para position of the hydroxyl group. not.)

In the above reaction, the molar ratio of dichlorodiphenylmethanes to phenylphenols is usually in the range of 2 to 10 moles, preferably 2.5 to 5 moles, of phenyl-substituted phenols relative to 1 mole of dichlorodiphenylmethanes.

A catalyst does not need to be used normally.

Usually, for example, a method of reacting in a temperature range of 20 to 80 ° C., preferably in a range of 40 to 70 ° C., and then raising the temperature in a range of 100 ° C. to 150 ° C., preferably in a range of 120 to 130 ° C. desirable.

The solvent is not particularly required if the raw material can be mixed in a liquid phase, but is preferably used if the raw material cannot be mixed for reasons such as when the raw material is a solid at the reaction temperature. The solvent used is not particularly limited as long as it does not inhibit the reaction. For example, aromatic hydrocarbon solvents such as toluene and xylene, saturated hydrocarbon solvents such as n-heptane and cyclohexane, and ether solvents such as dioxane and tetrahydrofuran and the like.

For the reaction, for example, reaction raw materials may be put in a batch to react, or dichlorodiphenylmethane may be added dropwise to react after adding phenylphenols under low temperature, and then the temperature may be raised to further react.

After completion of the reaction, from the reaction mixture, it is possible to obtain the desired product as a crude product or purified product by a known purification method.

Example

Next, the present invention will be described more specifically with reference to Examples.

(Reference Example 1) (Synthesis of raw material bisphenol)

306.2 g of 99.0% pure 2-phenylphenol and 183.6 g of xylene were placed in a 1 liter four-necked flask equipped with a stirring device, and the temperature was raised to 60° C. to dissolve. 141.6 g of dichlorodiphenylmethane was added dropwise to the solution at 60°C while stirring over 4.5 hours. After completion of the dropwise addition, the reaction solution was heated to 120°C and stirred at 120°C to 135°C for 30 hours.

After completion of the reaction, the reaction mixture was cooled to 30° C., neutralized by adding 16% sodium hydroxide aqueous solution to the reaction mixture, and the precipitated crystals were separated by filtration. The obtained crystals were dried at 60 DEG C under reduced pressure to obtain 97.5 g of yellow powdery crystals with a purity of 74.7% (by high-performance liquid chromatography analysis).

To 47.5 g of 97.5 g of the obtained crystals, 190.0 g of methyl isobutyl ketone was added, stirred at 110°C in a slurry state for 4 hours, cooled to room temperature, the crystals were filtered off and dried. 160.0 g of methyl isobutyl ketone was added to the crystal, followed by the same operation to obtain 35.8 g of a crystal having a purity of 96.7% by high performance liquid chromatography analysis.

Further, 769.8 g of methyl ethyl ketone was added to 16.0 g of the obtained crystal 35.8 g, and the temperature was raised to 81° C. to dissolve. Distilled water was added to the solution, stirred, and the water washing operation of separating and removing the aqueous layer was performed 4 times. The washed oil layer was concentrated to 78.9 g, cooled and crystallized.

After cooling to room temperature, the precipitated crystals are filtered off, dried, and 1,1-bis(3-phenyl-4-hydroxyphenyl)-1,1-diphenylmethane having a purity of 99.0% by high performance liquid chromatography analysis. 12.9 g were obtained.

Melting point: 290.8 ° C (differential scanning calorimetry)

Molecular weight: 503 (M-H) ^- (liquid chromatography mass spectrometry)

¹ H-NMR measurement result

(400 MHz, solvent; DMSO-d6, internal standard: tetramethylsilane)

(Example 1)

A 200 ml four-neck flask equipped with a stirring device was purged with nitrogen, and thereto, 1,1-bis(4-hydroxy-3-phenylphenyl)diphenylmethane 14.5 g of 96.7% purity, 7.6 g ethylene carbonate, and hydroxide Potassium 0.3 g, tetrabutylammonium bromide 0.3 g, n-butanol 72.5 g were added, and the temperature was raised to 115°C, followed by stirring at a temperature of 115°C to 120°C for 44 hours.

On the way, 0.7 g of ethylene carbonate was added after 33 hours, 0.7 g after 38 hours, and 1.4 g after 40 hours. To this reaction solution was added 36.2 g of distilled water, stirred at 95°C for 6 hours, and then neutralized by adding acetic acid at 70°C. After separating the water layer, 36.2 g of distilled water was added to the oil layer, washed with water, and the oil layer was washed with water again in the same operation and the temperature was raised to 85° C. under reduced pressure to distill off the solvent from the oil layer.

17.6 g of a white solid as a distillation residue was redissolved in 26.4 g of methyl isobutyl ketone, and 53.0 g of methanol was added to the solution for crystallization.

Thereafter, the crystals obtained by cooling and filtration were washed with methanol, dried under reduced pressure at 65°C, and 1,1-bis[4-(2-hydroxyl) as a white powder having a purity of 97.8% (by high-performance liquid chromatography analysis). 13.8 g of oxy)-3-phenylphenyl]-1,1-diphenylmethane was obtained. The yield with respect to the raw material 1,1-bis(4-hydroxy-3-phenylphenyl)-1,1-diphenylmethane was 81.2 mol%.

Further, the same purification operation of dissolving in methyl isobutyl ketone, adding methanol, recrystallization, and filtration, was performed twice, and dried under reduced pressure at 125° C. to obtain a purity of 99.1% (by high-performance liquid chromatography analysis) white crystals of 1,1-bis [4-(2-hydroxyethoxy)-3-phenylphenyl]-1,1-diphenylmethane 10.7 g was obtained. The yield with respect to the raw material 1,1-bis(4-hydroxy-3-phenylphenyl)-1,1-diphenylmethane was 62.9 mol%.

Melting point: 160°C (by differential scanning calorimetry)

Molecular weight: 593 (M+H) ⁺ (liquid chromatography mass spectrometry)

¹ H-NMR measurement result (400 MHz, solvent; DMSO-d6, internal standard: tetramethylsilane)

(Comparison of physical properties measurement)

The glass transition temperature and the compound concentration in the saturated solution in the examples below were measured by the following method.

<Measuring method of glass transition temperature>

In a differential scanning calorimeter, after melting each compound, the glass transition point was measured by cooling and heating again. At this time, the measurement start temperature was set to 30°C, and the temperature increase rate was set to 10°C/min.

<Method for measuring compound concentration in saturated solution>

3 g of the solvent was put into a test tube, and the compound to be measured at the measurement temperature was added to make a saturated solution. The supernatant concentration of this saturated solution was measured with a calibration curve by liquid chromatography.

(Example 1 measurement of compound physical properties)

The glass transition temperature, melting point, and refractive index of 1,1-bis[4-(2-hydroxyethoxy)-3-phenylphenyl]-1,1-diphenylmethane of Example 1 were measured and summarized in Table 3 .

In addition, the concentration of the compound in the saturated solution was measured and summarized in Table 4.

(Comparative Example 1)

The glass transition temperature, melting point, and refractive index of 1,1-bis[4-(2-hydroxyethoxy)phenyl]-1,1-diphenylmethane (BisPDP-2EO) having a purity of 98.9% were measured and summarized in Table 3 did

In addition, the concentration of the compound in the saturated solution was measured and summarized in Table 4.

(Comparative Example 2)

The glass transition temperature, melting point, and refractive index of 1,1-bis[4-(2-hydroxyethoxy)phenyl]-1-phenylethane (BisPAP-2EO) having a purity of 98.9% were measured and summarized in Table 3.

In addition, the concentration of the compound in the saturated solution was measured and summarized in Table 4.

Purity: The detection peak by high-performance liquid chromatography is calculated as an area percentage

Melting Point: Differential Scanning Calorimetry

Refractive Index: Extrapolation

Purity: The detection peak by high-performance liquid chromatography is calculated as an area percentage

MIBK: methyl isobutyl ketone

According to the results of the above Examples and Comparative Examples, according to the compound of the present invention in which a phenyl group is further bonded to a phenyl group to which a hydroxyethoxy group is bonded, the melting point is lower than that of BisPDP-2EO to which a phenyl group is not further bonded, and also in a solvent. It can be understood that the solubility for

Considering this result, in addition to the phenyl group to which the hydroxyethoxy group is bonded, an alkyl group, an alkoxy group, or a halogen atom is bonded together with the phenyl group, or instead of the ethylene group to which the hydroxy group of the hydroxyethoxy group is bonded, it contains 3 to 6 carbon atoms. It can also be seen that even if an alkylene group is employed, it has the same properties with respect to a low melting point and solubility in a solvent.

In addition, BisPAP-2EO having a bis(hydroxyethoxyphenyl)phenylethane skeleton has a low melting point and is excellent in solvent solubility, but the compound of the present invention has significantly superior glass transition temperature and refractive index.

Claims (1)

Bis(hydroxyalkoxyphenyl)diphenylmethanes represented by the following formula (1).
[Formula 1]

(In the formula, R represents an alkylene group having 2 or 3 carbon atoms.)