Composition containing binaphthol-based compound

Abstract

To provide a composition containing a binaphthol-based compound, the composition having high expandability into toluene and low tendency to discolor during heating.SOLUTION: Provided is a composition that contains at least one additive selected from an alkylene glycol and its condensates, and a binaphthol-based compound represented by general formula (1), with 2 to 100 average added moles of alkylene oxide. The content of the additive is 100 to 5000 mass ppm relative to the total amount of the binaphthol-based compound represented by general formula (1).SELECTED DRAWING: None

Description

Technical Field

[0001] The present disclosure relates to a composition containing a binaphthol-based compound.

Background Art

[0002] In recent years, resin materials having a binaphthalene skeleton have attracted attention as optical system materials such as optical lenses and optical sheets because of their excellent optical properties and heat resistance.

[0003] Patent Document 1 discloses a polyacrylate resin into which a binaphthalene skeleton is introduced using a binaphthol-based compound. Patent Document 2 discloses an active energy ray curable resin composition containing a binaphthol-based compound. Patent Document 3 discloses a compound having a specific binaphthalene skeleton. Patent Document 4 discloses a method for producing a binaphthol-based compound in the presence of a specific compound.

[0004] In addition to polyacrylate resins, resin materials such as polyester resins, polyurethane resins, and epoxy resins have been studied, and a binaphthol-based compound is required as the above raw material monomer.

Prior Art Documents

Patent Documents

[0005]

Patent Document 1

Patent Document 2

Patent Document 3

Patent Document 4

Summary of the Invention

Problems to be Solved by the Invention

[0006] When synthesizing a target compound using a binaphthol-based compound as a raw material, generally, the binaphthol-based compound is dissolved in an organic solvent for the reaction. Examples of such an organic solvent include toluene, an aromatic hydrocarbon. When using toluene, there is a problem that it takes time for the binaphthol-based compound to dissolve in toluene (the developability is slow).

[0007] In addition, when a resin material is used as an optical material, the resin material is required to have a low hue so as not to adversely affect the optical properties. The inventors of the present invention examined the addition of various compounds to the binaphthol-based compound in order to improve the solubility of the binaphthol-based compound. As a result, it became clear from the examination by the inventors that such a composition containing such a compound and the binaphthol-based compound is colored when heated and causes the coloring of the resin material.

[0008] The present disclosure provides a composition containing a binaphthol-based compound, which has high developability in toluene and is less likely to be colored when heated.

Means for Solving the Problems

[0009] One aspect of the present disclosure relates to the following composition and a method for producing a resin. [1] At least one additive selected from alkylene glycol and its polycondensates, and a binaphthol-based compound represented by the following general formula (1) having an average addition mole number of alkylene oxide of 2 to 100, A composition containing a binaphthol-based compound, wherein the content of the additive is 100 to 5000 mass ppm based on the total amount of the binaphthol-based compound represented by the general formula (1).

Chemical Formula

[0010] According to the present disclosure, there is provided a composition containing a binaphthol-based compound, which has high developability in toluene and is less likely to be colored when heated. [Embodiments for Carrying Out the Invention]

[0011] Hereinafter, preferred embodiments of the present disclosure will be described in detail. However, the present invention is not limited to the following embodiments.

[0012] [Composition Containing Binaphthol-Based Compound] Hereinafter, a composition containing a binaphthol-based compound according to an embodiment will be described. The composition according to this embodiment contains at least one additive selected from alkylene glycols and their polycondensates (hereinafter also simply referred to as "additive"), and a binaphthol-based compound represented by the following general formula (1) with an average addition mole number of alkylene oxide of 2 to 100 (hereinafter also referred to as "Compound 1"). The content of the additive is 100 to 5000 mass ppm based on the total amount of Compound 1. The composition according to this embodiment contains the additive, and further, since the content is within the above numerical range, it has high developability in toluene and is less likely to be colored when heated.

[0013] [Chemical formula] [In formula (1), R 11 and R 12 each independently represent a halogen atom or a monovalent hydrocarbon group having 1 to 22 carbon atoms, R 13 and R 14 each independently represent a hydrogen atom, a methyl group, or an ethyl group, Y 11 and Y 12 each independently represent a single bond or an oxygen atom, o1 and p1 each independently represent an integer of 0 to 4, and m and n each independently represent an integer of 0 or more. When o1 is an integer of 2 or more, a plurality of R 11 may be the same or different from each other, and a plurality of Y 11 may be the same or different from each other. When p1 is an integer of 2 or more, a plurality of R 12 may be the same or different from each other, and a plurality of Y 12 may be the same or different from each other. When m is an integer of 2 or more, a plurality of R 14 may be the same or different from each other. When n is an integer of 2 or more, a plurality of R 13 may be the same or different from each other. ]

[0014] Such a composition can be used, for example, in the synthesis of a resin having a binaphthalene skeleton. Examples of such resins include polyacrylate resins, polyester resins, polyurethane resins, and epoxy resins. Resins having a binaphthalene skeleton can be used as optical system materials.

[0015] (Compound 1) Hereinafter, Compound 1 will be described.

[0016] R 11 and R 12 When at least one of them is a halogen atom, the halogen atom may be fluorine, chlorine, bromine, or iodine. From the viewpoint of developability in a solvent, the halogen atom is preferably chlorine, bromine, or iodine, and more preferably bromine or iodine.

[0017] R 11 and R 12 When at least one of them is a monovalent hydrocarbon group having 1 to 22 carbon atoms, the hydrocarbon group may be an aliphatic hydrocarbon group (chain aliphatic hydrocarbon group), an alicyclic hydrocarbon group (cyclic aliphatic hydrocarbon group), or an aromatic hydrocarbon group.

[0018] The aliphatic hydrocarbon group may be either saturated or unsaturated, and may be either linear or branched. Examples of the aliphatic hydrocarbon group include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, t-butyl group, isobutyl group, amyl group, isoamyl group, hexyl group, heptyl group, 2-ethylhexyl group, octyl group, isooctyl group, nonyl group, isononyl group, decyl group, isodecyl group, undecyl group, lauryl group, tridecyl group, tetradecyl group, stearyl group, octadecyl group, behenyl group, and dodecyl group. From the viewpoint of solubility, the number of carbon atoms of the aliphatic hydrocarbon group is preferably 1 to 12, more preferably 1 to 6, and still more preferably 1 to 3.

[0019] The alicyclic hydrocarbon group may be either saturated or unsaturated. Examples of the alicyclic hydrocarbon group include a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and the like. When the alicyclic hydrocarbon group has two or more cyclic structures, examples of such an alicyclic hydrocarbon group include a decahydronaphthyl group, an adamantyl group, a norbornyl group, and the like.

[0020] Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a tolyl group, a xylyl group, a naphthyl group; aralkyl groups such as a benzyl group, a phenethyl group, a naphthylmethyl group, and the like. From the viewpoint of developability in a solvent, the number of carbon atoms of the aromatic hydrocarbon group is preferably 6 to 12, more preferably 6 to 10.

[0021] R 13 and R 14 are preferably a hydrogen atom or a methyl group, more preferably a hydrogen atom. Thereby, since the addition reaction of the alkylene oxide is fast, the binaphthol-based compound represented by the general formula (1) can be efficiently obtained.

[0022] Y 11 and Y 12 are preferably a single bond.

[0023] From the viewpoint of developability in a solvent, o1 and p1 are preferably 0 to 3, more preferably 0 to 2, still more preferably 0 to 1.

[0024] The average number of moles of alkylene oxide added is preferably 3 or more, more preferably 6 or more, still more preferably 8 or more. Thereby, the composition tends to be more excellent in developability in a solvent. The total value is preferably 70 or less, more preferably 50 or less, still more preferably 20 or less. Thereby, the composition tends to further suppress coloring during heating.

[0025] The total value of m and n may be 1 or more, 2 or more, 3 or more, 6 or more, or 8 or more. The total value may be 100 or less, 70 or less, 50 or less, or 20 or less.

[0026] m and n may each be 1 or more, 2 or more, 3 or more, or 4 or more. m and n may each be 50 or less, 35 or less, 25 or less, or 10 or less.

[0027] Compound 1 is an optically active compound because it has an asymmetric axis. Compound 1 may be a racemate, a chiral form, or a mixture thereof. When it is a mixture, the ratio (optical purity) of the racemate to the chiral form is not particularly limited.

[0028] Specific examples of Compound 1 include the reaction product of 1,1'-bi-2-naphthol and ethylene oxide, the reaction product of 1,1'-bi-2-naphthol and propylene oxide, and the reaction product of 6,6'-diphenyl-1,1'-bi-2-naphthol and ethylene oxide.

[0029] Compound 1 may be used alone or in combination of two or more.

[0030] The content of Compound 1 may be 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, or 95% by mass or more based on the total amount of the composition.

[0031] (Additive) The additive will be described below.

[0032] Examples of the alkylene glycol include ethylene glycol, propylene glycol, and butylene glycol.

[0033] The polycondensate of alkylene glycol is obtained by the addition polymerization of alkylene oxide. Examples of such alkylene oxides include ethylene oxide, propylene oxide, and butylene oxide. The polycondensate of alkylene glycol may be one in which a single type of alkylene oxide is added alone, or may be one in which two or more types of alkylene oxides are co-added. In the case of co-addition, it may be block addition or random addition.

[0034] The number average molecular weight of the polycondensate of alkylene glycol is not particularly limited, but is preferably 200 or more and 10,000 or less. This makes it easier to handle. The number average molecular weight is more preferably 4000 or less, still more preferably 2500 or less, and particularly preferably 1000 or less. Thereby, the composition tends to be more excellent in developability in a solvent. The number average molecular weight of the polycondensate of alkylene glycol is measured according to JIS K1557-1:2007 Part 1 Method for Determining Hydroxyl Value.

[0035] The additive(s) may be used alone or in combination of two or more.

[0036] The content of the additive is preferably 500 mass ppm or more, more preferably 1000 mass ppm or more, based on the total amount of Compound 1. Thereby, the developability in a solvent tends to be further improved. The content of the additive is preferably 4000 mass ppm or less, more preferably 3000 mass ppm or less, based on the total amount of Compound 1. Thereby, coloring is more likely to be suppressed even when the composition is heated under acidic conditions.

[0037] [Production of Compound 1] Compound 1 can be obtained, for example, by mixing a compound (2) represented by the following general formula (2) (hereinafter also referred to as "Compound 2") and a reaction solvent in a predetermined reaction vessel and performing an addition reaction step of adding at least one of ethylene oxide, propylene oxide, and butylene oxide.

[0038] [Chemical formula] [In formula (2), R 21 and R 22 each independently represents a halogen atom or a monovalent hydrocarbon group having 1 to 22 carbon atoms, and Y 21 and Y 22 each independently represents a single bond or an oxygen atom, and o2 and p2 each represent an integer of 0 to 4. When o2 is an integer of 2 or more, a plurality of R 21 may be the same or different from each other, and a plurality of Y 21 may be the same or different from each other. When p2 is an integer of 2 or more, a plurality of R 22 may be the same or different from each other, and a plurality of Y 22 may be the same or different from each other.]

[0039] The reaction solvent is not particularly limited, but an organic solvent immiscible with water is preferably used. Examples of the reaction solvent include aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; aliphatic hydrocarbons such as pentane, hexane, and heptane; and alicyclic hydrocarbons such as cyclopentane, cyclohexane, cycloheptane, and cyclooctane. These may be used alone or in combination of two or more.

[0040] The addition amount of the solvent can be 100 to 1000 parts by mass with respect to 100 parts by mass of the charged amount of Compound 2. From the viewpoint of compatibility, 150 parts by mass or more is preferable, and from the viewpoint of economy, 500 parts by mass or less is preferable.

[0041] The reaction temperature is not particularly limited, but from the viewpoint of reactivity, it is preferably 90 to 150 °C, and more preferably 100 to 140 °C.

[0042] The reaction time in the addition reaction step is not particularly limited, but from the viewpoint of productivity, it is preferably 2 to 12 hours, more preferably 4 to 10 hours.

[0043] The pressure conditions in the addition reaction step are not particularly limited. For example, it may be atmospheric pressure or under pressure. When under pressure, from the viewpoint of safety, it is preferably 1.00 MPa·G or less, more preferably 0.50 MPa·G or less. The addition reaction step can be carried out under an inert gas atmosphere such as nitrogen or argon.

[0044] In the addition reaction step, a catalyst may coexist.

[0045] The catalyst is not particularly limited. For example, sodium hydroxide, potassium hydroxide, lithium hydroxide, rubidium hydroxide, and cesium hydroxide can be mentioned. These can be used alone or in combination of two or more.

[0046] The addition amount of the catalyst can be 0.01 to 1.0 part by mass based on 100 parts by mass of the charged amount of Compound 2.

[0047] The production method of Compound 1 may include a depressurization step of removing the solvent and unreacted alkylene oxide after the addition reaction step.

[0048] The temperature conditions in the depressurization step are not particularly limited, but from the viewpoint of efficiency, it is preferably 100 to 160 °C, more preferably 100 to 140 °C.

[0049] The pressure conditions in the depressurization step are not particularly limited, but from the viewpoint of efficiency, it is preferably -0.08 MPa·G or less, more preferably -0.09 MPa or less.

[0050] When a catalyst coexists in the addition reaction step, the method for producing Compound 1 may include a decatalyzation step of removing the catalyst. The catalyst may be removed, for example, by the following method. That is, the product and the adsorbent are mixed to obtain a mixture. The mixture is stirred while being heated. Thereby, the catalyst is adsorbed to the adsorbent. The catalyst is removed by filtering the adsorbent.

[0051] The temperature at which the mixture is heated is not particularly limited, but is preferably 60 to 100°C from the viewpoint of efficiency. The time for stirring the mixture while heating is not particularly limited, but is preferably 30 to 90 minutes from the viewpoint of efficiency.

[0052] [Production of polycondensate of alkylene glycol] As the polycondensate of alkylene glycol, those synthesized by polycondensation reaction of alkylene oxide can be used.

[0053] The polycondensation reaction can be carried out by performing a reaction of adding at least one of ethylene oxide, propylene oxide, and butylene oxide in a reaction vessel (addition reaction step).

[0054] Examples of the reaction vessel include an autoclave.

[0055] The reaction of adding at least one of ethylene oxide, propylene oxide, and butylene oxide can be carried out by adding at least one alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide, and butylene oxide to at least one selected from the group consisting of ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,2-butanediol, and water.

[0056] The addition amount (charged amount) of the alkylene oxide is not particularly limited, but from the viewpoint of handling, it is preferably 200 mol or less, more preferably 4 to 100 mol, relative to 1.00 mol of one or more charged amounts selected from the group consisting of ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,2-butanediol, and water.

[0057] The reaction temperature in the addition reaction step is not particularly limited, but from the viewpoint of reactivity, it is preferably 90 to 150°C, more preferably 100 to 140°C.

[0058] The reaction time in the addition reaction step is not particularly limited, but from the viewpoint of productivity, it is preferably 2 to 12 hours, more preferably 4 to 10 hours.

[0059] The pressure conditions in the addition reaction step are not particularly limited, and for example, it may be atmospheric pressure or under pressure. When under pressure, from the viewpoint of safety, it is preferably 1.00 MPa or less, more preferably 0.50 MPa or less.

[0060] The addition reaction step can be carried out under an inert gas atmosphere such as under nitrogen or under argon.

[0061] In the addition reaction step, a catalyst and a solvent (other solvents) may coexist.

[0062] The catalyst is not particularly limited, and examples thereof include sodium hydroxide, potassium hydroxide, lithium hydroxide, rubidium hydroxide, and cesium hydroxide. These can be used alone or in combination of two or more.

[0063] The addition amount of the catalyst can be 0.01 to 1.0 part by mass with respect to 100 parts by mass of one or more charged amounts selected from the group consisting of ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,2-butanediol, and water.

[0064] Other solvents are not particularly limited. For example, aromatic hydrocarbons such as benzene, toluene, xylene, mesitylene, chlorobenzene, and dichlorobenzene; aliphatic hydrocarbons such as pentane, hexane, and heptane; alicyclic hydrocarbons such as cyclopentane, cyclohexane, cycloheptane, and cyclooctane, etc. These may be used alone or in combination of two or more.

[0065] In addition, commercially available polycondensates of alkylene glycols can also be used. Commercially available products include polyethylene glycol 400 (FUJIFILM Wako Pure Chemical Corporation), polyethylene glycol 2000 (FUJIFILM Wako Pure Chemical Corporation), polyethylene glycol 4000 (FUJIFILM Wako Pure Chemical Corporation), polypropylene glycol 400 (FUJIFILM Wako Pure Chemical Corporation), etc.

Examples

[0066] Hereinafter, the present disclosure will be described in more detail by way of examples. However, the present invention is not limited by these examples in any way.

[0067] [Adjustment of Composition] <Example 1> 100.0 g of 1,1'-bi-2-naphthol (Fuji Film Wako Pure Chemical Industries, Ltd., 0.35 mol), 0.2 g of potassium hydroxide, and 200.0 g of toluene were charged into a 1 L autoclave equipped with a Dean-Stark apparatus. Subsequently, the inside of the autoclave was heated to 115°C, and the system was refluxed to remove the moisture inside the system until no more moisture distilled out. Thereafter, the inside of the autoclave was sealed and purged with nitrogen. The inside of the autoclave was heated to 120°C, and 154.0 g (3.5 mol) of ethylene oxide was intermittently introduced into the autoclave so that the pressure inside the autoclave did not exceed 0.5 MPa·G. Thereafter, an alkylene oxide addition reaction was allowed to proceed under reaction conditions of a reaction temperature of 120°C and a reaction time of 6 hours to obtain a product. After completion of the reaction, a depressurization treatment was carried out at 120°C and -0.09 MPa·G for 2 hours to remove the solvent and unreacted ethylene oxide from the product. After the product was cooled to 80°C, 2.5 g of Kyoward 600S (Kyowa Chemical Industry Co., Ltd., trade name) was added, and stirring was carried out at 80°C for 1 hour to perform a de-catalysis treatment. The product was filtered to remove Kyoward 600S. 0.01 g (100 ppm by mass) of polyethylene glycol 400 (Fuji Film Wako Pure Chemical Industries, Ltd., number average molecular weight: 360 - 440) was added to 100 g of the product (a compound in which an average of 9.9 moles of ethylene oxide was added to 1,1'-bi-2-naphthol) and mixed to obtain a composition.

[0068] <Example 2> A composition was obtained in the same manner as in Example 1, except that the addition amount of polyethylene glycol 400 was changed from 0.01 g to 0.05 g (500 ppm by mass).

[0069] <Example 3> A composition was obtained in the same manner as in Example 1, except that the addition amount of polyethylene glycol 400 was changed from 0.01 g to 0.10 g (1000 ppm by mass).

[0070] <Example 4> A composition was obtained in the same manner as in Example 1, except that the addition amount of polyethylene glycol 400 was changed from 0.01 g to 0.20 g (2000 ppm by mass).

[0071] <Example 5> A composition was obtained in the same manner as in Example 1, except that the amount of polyethylene glycol 400 added was changed from 0.01 g to 0.30 g (3000 mass ppm).

[0072] <Example 6> A composition was obtained in the same manner as in Example 1, except that the amount of polyethylene glycol 400 added was changed from 0.01 g to 0.30 g (3000 mass ppm).

[0073] <Example 7> A composition was obtained in the same manner as in Example 1, except that the amount of polyethylene glycol 400 added was changed from 0.01 g to 0.50 g (5000 mass ppm).

[0074] <Example 8> A composition was obtained in the same manner as in Example 1, except that the amount of ethylene oxide introduced was changed from 154.0 g to 46.2 g (1.05 mol) and the amount of polyethylene glycol 400 added was changed from 0.01 g to 0.20 g (2000 mass ppm). The product was a compound in which an average of 2.8 moles of ethylene oxide was added to 1,1'-bi-2-naphthol.

[0075] <Example 9> A composition was obtained in the same manner as in Example 1, except that the amount of ethylene oxide introduced was changed from 154.0 g to 616.7 g (14.0 mol) and the amount of polyethylene glycol 400 added was changed from 0.01 g to 0.20 g (2000 mass ppm). The product was a compound in which an average of 39.9 moles of ethylene oxide was added to 1,1'-bi-2-naphthol.

[0076] <Example 10> The composition was obtained in the same manner as in Example 1, except that the 2 L autoclave was changed to include a Dean-Stark apparatus, the introduced amount of ethylene oxide was changed from 154.0 g to 1233.4 g (28.0 mol), and the added amount of polyethylene glycol 400 was changed from 0.01 g to 0.20 g (2000 mass ppm). The product was a compound in which an average of 79.9 moles of ethylene oxide was added to 1,1'-bi-2-naphthol.

[0077] <Example 11> A composition was obtained in the same manner as in Example 1, except that 0.20 g (2000 mass ppm) of polyethylene glycol 4000 (Fuji Film Wako Pure Chemical Corporation, number average molecular weight: 2700 - 3300) was used instead of 0.01 g of polyethylene glycol 400.

[0078] <Example 12> A composition was obtained in the same manner as in Example 11, except that polypropylene glycol 400 (Fuji Film Wako Pure Chemical Corporation, number average molecular weight: 400) was used instead of polyethylene glycol 4000.

[0079] <Example 13> A composition was obtained in the same manner as in Example 1, except that 203.5 g (3.5 mol) of propylene oxide was used instead of 154.0 g (3.5 mol) of ethylene oxide, and the added amount of polyethylene glycol 400 was changed from 0.01 g to 0.20 g (2000 mass ppm). The product was a compound in which an average of 9.8 moles of propylene oxide was added to 1,1'-bi-2-naphthol.

[0080] <Example 14> A composition was obtained in the same manner as in Example 13, except that polypropylene glycol 400 was used instead of polyethylene glycol 400.

[0081] <Example 15> A flask equipped with a stirrer, a cooler, and a thermometer was prepared. 100.00 g (0.226 mol) of 6,6'-dibromo-1,1'-bi-2-naphthol, 60.40 g (0.495 mol) of phenylboronic acid, 225 mL of 2M aqueous potassium carbonate solution, 600 mL of toluene, 600 mL of ethanol, 3.42 g of tri(o-tolyl)phosphine, and 0.51 g of palladium(II) acetate were charged into the flask and reacted at 80 °C for 15 hours. After completion of the reaction, the reaction solution was filtered to remove the catalyst and a filtrate was obtained. The filtrate was washed with 1M aqueous sodium hydroxide solution and then washed with distilled water until neutral. Thereafter, the filtrate was recrystallized with toluene to recover crystals. The crystals were vacuum dried at 90 °C for 7 hours. As a result, 112 g of white crystals of 6,6'-diphenyl-1,1'-bi-2-naphthol were obtained.

[0082] A composition was obtained in the same manner as in Example 1, except that 100 g of 6,6'-diphenyl-1,1'-bi-2-naphthol was used instead of 100 g of 1,1'-bi-2-naphthol, the introduced amount of ethylene oxide was changed from 154.0 g to 100.3 g, and the added amount of polyethylene glycol 400 was changed from 0.01 g to 0.20 g (2000 mass ppm). The product was a compound in which an average of 9.9 moles of ethylene oxide was added to 6,6'-diphenyl-1,1'-bi-2-naphthol.

[0083] <Example 16> A composition was obtained in the same manner as in Example 11, except that monoethylene glycol was used instead of polyethylene glycol 4000.

[0084] <Example 17> A composition was obtained in the same manner as in Example 11, except that polyethylene glycol 2000 (manufactured by Fujifilm Wako Pure Chemical Corporation, number average molecular weight: 1800 - 2200) was used instead of polyethylene glycol 4000.

[0085] <Comparative Example 1> A composition was obtained in the same manner as in Example 1, except that polyethylene glycol 400 was not added.

[0086] <Comparative Example 2> A composition was obtained in the same manner as in Example 1, except that the amount of polyethylene glycol 400 added was changed from 0.01 g to 0.60 g (6000 mass ppm).

[0087] <Comparative Example 3> A composition was obtained in the same manner as in Example 1, except that the amount of ethylene oxide introduced was changed from 154.0 g to 15.4 g (0.35 mol) and the amount of polyethylene glycol 400 added was changed from 0.01 g to 0.20 g (2000 mass ppm). The product was a compound in which an average of 0.8 mol of ethylene oxide was added to 1,1'-bi-2-naphthol.

[0088] <Comparative Example 4> The reaction was carried out in a 2 L autoclave equipped with a Dean-Stark apparatus. A composition was obtained in the same manner as in Example 1, except that the amount of ethylene oxide introduced was changed from 154.0 g to 1695.9 g (38.5 mol) and the amount of polyethylene glycol 400 added was changed from 0.01 g to 0.20 g (2000 mass ppm). The product was a compound in which an average of 110.0 mol of ethylene oxide was added to 1,1'-bi-2-naphthol.

[0089] [Measurement of the average number of moles of alkylene oxide added] The hydroxyl value of Compound 1 was measured in accordance with the method for determining the hydroxyl value (Part 1 of JIS K1557-1:2007). The measured hydroxyl value was substituted into the following formula (3). Thereby, the average number of moles of alkylene oxide added to Compound 1 was determined.

[0090] Average number of moles of alkylene oxide added ={((56100×2) / hydroxyl value) - molecular weight of Compound 2} / molecular weight of alkylene oxide ··· Formula (3)

[0091] [Solubility test] In this test, the solubility of the compositions of each example and comparative example in toluene solvent was evaluated. Specifically, 20 g of toluene was weighed into a 100 mL beaker. A stir bar was placed in the beaker and the toluene was stirred at 30 °C and 100 rpm. Each composition was heated to 60 °C. 1 g of the composition was dropped into the beaker in which the toluene was being stirred, and the time from the end of dropping until the solution was uniformly dissolved was measured. The dissolution time was evaluated according to the following criteria. Those with an evaluation of "B" or higher were considered qualified. The results are shown in Tables 1 to 3.

[0092] (Criteria) A: Dissolution time is less than 600 seconds B: Dissolution time is 600 seconds or more and less than 900 seconds C: Dissolution time is 900 seconds or more

[0093] [Heat Coloration Test] In this test, the hue change of the compositions of each example and comparative example under high temperature and acidic catalyst was evaluated. Specifically, 45 g of each composition, 3.5 g of methanesulfonic acid, and 1.5 g of water were put into a 200 mL beaker and mixed uniformly to obtain a mixture. The mixture was heated at 105 °C for 3 hours in an open system, and the hue values before and after heating were measured. The measuring instrument and measuring method were as follows. The difference in hue values before and after the heating test was evaluated according to the following criteria. Those with an evaluation of "B" or higher were considered qualified. The results are shown in Tables 1 to 3. · Measuring instrument: Automatic Petroleum Product Color Tester OME - 2000 (manufactured by Nippon Denshoku Industries Co., Ltd.) · Measuring method: In accordance with "Petroleum Products - Color Test Method (JIS K0071 - 2:1998, Part 2 Gardner)", the Gardner value was measured.

[0094] (Criteria) A: Difference in hue value is less than 1.0 B: Difference in hue value is 1.0 or more and less than 3.0 C: Difference in hue value is 3.0 or more

[0095] [Comprehensive Evaluation] Those in which the determination of solubility or heat coloration was "B" or higher in both cases were considered qualified.

[0096]

Table 1

[0097]

Table 2

[0098]

Table 3

[0099] As shown in Tables 1 to 3, the compositions (Examples 1 to 17) in which the blending amount of the polyalkylene glycol with respect to the binaphthol-based compound is 100 mass ppm or more and 5000 mass ppm or less have good developability (solubility) in the solvent, and the color difference before and after the heating test is small, and coloring is suppressed.

[0100] On the other hand, the composition (Comparative Example 1) in which the blending amount of the polyalkylene glycol with respect to the binaphthol-based compound is less than 100 mass ppm has low developability (solubility) in the solvent, and the composition (Comparative Example 2) in which the blending amount is more than 5000 mass ppm has a large color difference before and after the heating test and is colored.

Claims

Claim 1 Comprising at least one additive selected from alkylene glycols and their polycondensates, and a binaphthol-based compound represented by the following general formula (1) in which the average number of moles of added alkylene oxide is 2 to 100, A composition containing a binaphthol-based compound, wherein the content of the additive is 100 to 5000 mass ppm based on the total amount of the binaphthol-based compound represented by the general formula (1). 【Chemical 1】 [In formula (1), R １１ and R １２ each independently represent a halogen atom or a monovalent hydrocarbon group having 1 to 22 carbon atoms, R １３ and R １４ each independently represent a hydrogen atom, a methyl group, or an ethyl group, Y １１ and Y １２ each independently represent a single bond or an oxygen atom, o1 and p1 each independently represent an integer of 0 to 4, and m and n each independently represent an integer of 0 or more. When o1 is an integer of 2 or more, a plurality of R １１ may be the same or different from each other, and a plurality of Y １１ may be the same or different from each other. When p1 is an integer of 2 or more, a plurality of Rs １２ may be the same or different from each other, and a plurality of Ys １２ may be the same or different from each other. When n is an integer of 2 or more, a plurality of Rs present １３ may be the same or different from each other. When m is an integer of 2 or more, a plurality of R's １４ may be the same or different from each other. ] Claim 2 The composition according to claim 1, which is for the synthesis of a resin having a binaphthalene skeleton for optical system materials. Claim 3 Containing the polycondensate of the alkylene glycol, The composition according to claim 1 or 2, wherein the number average molecular weight of the polycondensate of the alkylene glycol is 200 to 10000. Claim 4 The composition according to claim 1 or 2, containing the alkylene glycol.

Images