Composition for adjusting refractive index, refractive index adjusting agent, and resin composition

Abstract

To provide a new composition for adjusting a refractive index, which can be suitably used for adjusting the refractive index of various materials, especially resin materials. The present invention also provides a refractive index-adjusting agent containing the refractive index-adjusting composition and a resin composition containing the refractive index-adjusting agent.SOLUTION: The composition for adjusting the refractive index is a composition used for adjusting the refractive index and contains a sucrose naphthoate compound. The refractive index adjusting composition of the present invention contains a trehalose naphthoate compound.SELECTED DRAWING: None

Description

[Technical Field]

[0001] The present invention relates to a refractive index adjusting composition, a refractive index adjuster, and a resin composition used to adjust the refractive index. [Background technology]

[0002] Resin materials and inorganic materials can be molded into various shapes, and the molded products are widely used in various fields. These molded products may contain various additives to improve their properties, and depending on the properties of the additives, the functions of the molded products can be improved or new functions can be imparted to the molded products (e.g., Patent Document 1).

[0003] When the molded body is, for example, a resin film, various refractive index adjusters are used as additives to improve its optical performance. For example, if the purpose is to increase the refractive index, inorganic particles having a high refractive index can be added to the molded body as a refractive index adjuster. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Application Laid-Open No. 2011-207798 Summary of the Invention [Problem to be solved by the invention]

[0005] The present invention aims to provide a novel refractive index adjusting composition that can be suitably used to adjust the refractive index of various materials, particularly resin materials. The present invention also aims to provide a refractive index adjuster containing the refractive index adjusting composition and a resin composition containing the refractive index adjuster. [Means for solving the problem]

[0006] As a result of extensive research into achieving the above-mentioned object, the present inventors have found that the above-mentioned object can be achieved by using a sucrose naphthoate compound or a trehalose naphthoate compound as an essential ingredient, and have thus completed the present invention.

[0007] That is, the present invention includes, for example, the subject matter described in the following sections. Item 1 A composition used for adjusting the refractive index, A refractive index adjusting composition containing a sucrose naphthoate compound. Section 2 A composition used for adjusting the refractive index, A refractive index adjusting composition containing a trehalose naphthoate compound. Section 3 Item 3. The refractive index adjusting composition according to item 1 or 2, which is used to adjust the refractive index of a resin. Section 4 Item 3. A refractive index adjuster comprising the refractive index adjusting composition according to Item 1 or 2. Section 5 Item 4. A resin composition comprising the refractive index adjusting composition according to item 3 and a resin. [Effects of the Invention]

[0008] The refractive index adjusting composition of the present invention can be suitably used to adjust the refractive index of various materials. DETAILED DESCRIPTION OF THE INVENTION

[0009]

[0023] In the present specification, the terms "contain" and "comprise" include the concepts of "contain," "comprise," "consist essentially of," and "consist only of."

[0010] The refractive index-adjusting composition of the present invention is a composition used for adjusting the refractive index. In one embodiment, the refractive index-adjusting composition of the present invention contains a sucrose naphthoate compound. That is, one embodiment of the present invention is a refractive index-adjusting composition containing at least a sucrose naphthoate compound.

[0011] In another embodiment, the refractive index-adjusting composition of the present invention contains a trehalose naphthoate compound. That is, another embodiment of the present invention is a refractive index-adjusting composition containing at least a trehalose naphthoate compound.

[0012] In summary, the present invention encompasses a refractive index adjusting composition containing a sucrose naphthoate compound and a refractive index adjusting composition containing a trehalose naphthoate compound.

[0013] The refractive index adjusting composition of the present invention can be suitably used in any embodiment to adjust the refractive index of various materials. In particular, since the refractive index adjusting composition of the present invention has a high refractive index, when added as an additive to various materials, the refractive index of the materials can be increased. Therefore, the refractive index adjusting composition of the present invention is useful as a refractive index adjuster.

[0014] Furthermore, since the refractive index adjusting composition of the present invention has a low Abbe number, it can be added as an additive to various materials to lower the Abbe number of the material. Therefore, by using the refractive index adjusting composition of the present invention, a resin with a low Abbe number can be obtained, and for example, by combining it with a resin with a high Abbe number and using it as a lens material, chromatic aberration correction becomes easier.

[0015] (sucrose naphthoate compound) Sucrose naphthoate compounds are compounds formed by, for example, esterification of sucrose and naphthalenecarboxylic acid. Therefore, sucrose naphthoate compounds have a structure in which a hydroxyl group in a sucrose molecule is replaced with a naphthoate moiety, i.e., an Np-COO- moiety (Np represents a naphthyl group). In this case, the naphthyl group (Np) may be a 1-naphthyl group or a 2-naphthyl group.

[0016] The sucrose naphthoate compound may have the naphthoate moiety introduced into some or all of the multiple hydroxyl groups (up to eight) derived from the sucrose molecule. That is, the sucrose naphthoate compound may exist as a monoester, diester, triester, etc. The sucrose naphthoate compound contained in the refractive index-adjusting composition of the present invention may be any of these esters, or may contain one or more esters. The degree of esterification of the sucrose naphthoate compound is also not particularly limited. For example, the degree of esterification of the sucrose naphthoate compound is 1 or more, preferably 1.1 or more, and may also be 6 or more, or 7 or more. The degree of esterification of the sucrose naphthoate compound is particularly preferably 7 to 8.

[0017] The method for producing the sucrose naphthoate compound is not particularly limited, and for example, a wide variety of known production methods can be employed. For example, the sucrose naphthoate compound can be synthesized by the reaction of sucrose with naphthalenecarboxylic acid. Alternatively, the sucrose naphthoate compound can be synthesized by the transesterification reaction of sucrose with a naphthalenecarboxylic acid ester. Specific examples of the naphthalenecarboxylic acid include 1-naphthalenecarboxylic acid and 2-naphthalenecarboxylic acid. Examples of the naphthalenecarboxylic acid ester include alkyl esters of 1-naphthalenecarboxylic acid and alkyl esters of 2-naphthalenecarboxylic acid. The alkyl group in these alkyl ester moieties is, for example, an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, such as a methyl group.

[0018] Sucrose naphthoate compounds can also be synthesized by reacting sucrose with naphthoyl chloride, specifically 1-naphthoyl chloride or 2-naphthoyl chloride.

[0019] The sucrose used in the method for producing a sucrose naphthoate compound may be synthesized by a known method, or may be commercially available. The sucrose may be unreacted sucrose recovered during the production of a sucrose fatty acid ester (so-called "recovered sugar").

[0020] The sucrose naphthoate compound can also be obtained from commercial sources.

[0021] The sucrose naphthoate compound contained in the refractive index adjusting composition of the present invention may be one type or two or more types.

[0022] (Trehalose naphthoate compound) Trehalose naphthoate compounds are compounds formed, for example, by esterification of trehalose and naphthalenecarboxylic acid. Thus, trehalose naphthoate compounds have a structure in which the hydroxyl group in a trehalose molecule is replaced with a naphthoate moiety, i.e., an Np-COO- moiety (Np represents a naphthyl group). In this case, the naphthyl group (Np) may be either a 1-naphthyl group or a 2-naphthyl group.

[0023] The trehalose naphthoate compound may have naphthoate moieties introduced into some or all of the multiple hydroxyl groups (up to eight) derived from the trehalose molecule. In other words, the trehalose naphthoate compound may exist as a monoester, diester, triester, etc. The trehalose naphthoate compound contained in the refractive index-adjusting composition of the present invention may be any of these esters, or may contain one or more esters. The degree of esterification of the trehalose naphthoate compound is also not particularly limited. For example, the degree of esterification of the trehalose naphthoate compound is 1 or more, preferably 1.1 or more, and may also be 6 or more, or 7 or more. The degree of esterification of the trehalose naphthoate compound is particularly preferably 7 to 8.

[0024] The method for producing the trehalose naphthoate compound is not particularly limited, and for example, a wide variety of known production methods can be employed. For example, the trehalose naphthoate compound can be synthesized by the reaction of trehalose with naphthalenecarboxylic acid. Alternatively, the trehalose naphthoate compound can be synthesized by the transesterification reaction of trehalose with a naphthalenecarboxylic acid ester. Specific examples of the naphthalenecarboxylic acid include 1-naphthalenecarboxylic acid and 2-naphthalenecarboxylic acid. Examples of the naphthalenecarboxylic acid ester include alkyl esters of 1-naphthalenecarboxylic acid and alkyl esters of 2-naphthalenecarboxylic acid. The alkyl group in these alkyl ester moieties is, for example, an alkyl group having 1 to 10 carbon atoms, preferably an alkyl group having 1 to 4 carbon atoms, such as a methyl group.

[0025] Trehalose naphthoate can also be synthesized by reacting trehalose with naphthoyl chloride, specifically 1-naphthoyl chloride or 2-naphthoyl chloride.

[0026] Trehalose used in the method for producing a trehalose naphthoate compound may be synthesized by a known method, or trehalose may be obtained from commercial products.

[0027] The trehalose naphthoate compound can also be obtained as a commercial product.

[0028] The refractive index adjusting composition of the present invention may contain one or more types of trehalose naphthoate compounds.

[0029] (Refractive index adjusting composition) The refractive index-adjusting composition of the present invention contains a sucrose naphthoate compound and / or a trehalose naphthoate compound, i.e., the refractive index-adjusting composition of the present invention may contain both a sucrose naphthoate compound and a trehalose naphthoate compound.

[0030] The refractive index-adjusting composition of the present invention may contain other components in addition to the sucrose naphthoate compound and the trehalose naphthoate compound, as long as the effects of the present invention are not impaired. Examples of other components include pH adjusters, light stabilizers, antioxidants, preservatives, surfactants, fillers such as inorganic particles, flame retardants, pigments, colorants, mildew inhibitors, lubricants, etc. One or more of these additives may be contained in the refractive index-adjusting composition of the present invention.

[0031] The refractive index adjusting composition of the present invention may be either solid or liquid. When the refractive index adjusting composition of the present invention is solid, its shape is not particularly limited, and examples thereof include powder, granules, flakes, lumps, pellets, etc. When the refractive index adjusting composition of the present invention is liquid, it may be, for example, a solution or a dispersion such as a slurry. The liquid refractive index adjusting composition can be formed, for example, using a solvent.

[0032] The type of solvent is not particularly limited, and an appropriate solvent can be selected depending on the purpose. For example, a solvent can be selected depending on the purpose of dissolving or dispersing the sucrose naphthoate compound and the trehalose naphthoate compound. The solvent may be water or various organic solvents. When the refractive index-adjusting composition of the present invention contains a solvent, the content thereof is not particularly limited.

[0033] When the refractive index adjusting composition of the present invention is in a solid state, the composition may be dissolved or dispersed in a solvent when used or stored.

[0034] When the refractive index-adjusting composition of the present invention contains a sucrose naphthoate compound, the content ratio of the sucrose naphthoate compound is not particularly limited. For example, the content ratio of the sucrose naphthoate compound can be 50% by mass or more, preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, and particularly preferably 95% by mass or more, based on the total amount of the refractive index-adjusting composition of the present invention excluding the solvent. The refractive index-adjusting composition of the present invention may consist solely of the sucrose naphthoate compound.

[0035] When the refractive index-adjusting composition of the present invention contains a trehalose naphthoate compound, the content of the trehalose naphthoate compound is not particularly limited. For example, the content of the trehalose naphthoate compound can be 50% by mass or more, preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, and particularly preferably 95% by mass or more, based on the total mass of the refractive index-adjusting composition of the present invention excluding the solvent. The refractive index-adjusting composition of the present invention may consist solely of the trehalose naphthoate compound.

[0036] The method for preparing the refractive index adjusting composition of the present invention is not particularly limited, and the composition can be obtained by mixing a predetermined amount of a sucrose naphthoate compound or a trehalose naphthoate compound with other components that are blended as necessary. The mixing method is not particularly limited, and any known mixing means can be widely used.

[0037] The refractive index-adjusting composition of the present invention contains a sucrose naphthoate compound and / or a trehalose naphthoate compound, and therefore can have a high refractive index. For example, the refractive index of the sucrose naphthoate compound and / or the trehalose naphthoate compound is both 1.66, which is higher than that of other sucrose fatty acid ester compounds or trehalose fatty acid ester compounds. Therefore, the refractive index-adjusting composition of the present invention can be suitably used as an additive for materials for adjusting the refractive index, particularly for various materials requiring a high refractive index.

[0038] The refractive index-adjusting composition of the present invention has a smaller Abbe number than other sucrose fatty acid ester compounds and trehalose fatty acid ester compounds. Taking advantage of this small Abbe number, the composition can be suitably used in applications where a low Abbe number is required.

[0039] Therefore, the refractive index adjusting composition of the present invention is particularly suitable as a refractive index adjuster. The refractive index adjuster may consist of only the refractive index adjusting composition of the present invention, or may be combined with other additives. The refractive index adjuster can adjust the refractive index of various materials by containing the refractive index adjusting composition of the present invention.

[0040] The method for using the refractive index adjusting composition of the present invention is not particularly limited, and for example, it can be incorporated into various materials by an appropriate method. For example, the refractive index adjusting composition of the present invention (or the refractive index adjusting agent) can be incorporated into a material by adding the refractive index adjusting composition of the present invention (or the refractive index adjusting agent) at any stage in the production of the material. Alternatively, when molding a material into a molded product, the material and the refractive index adjusting composition of the present invention can be mixed to prepare a raw material, and the raw material can be molded to incorporate the refractive index adjusting composition of the present invention (or the refractive index adjusting agent) into the molded product. By these methods, the refractive index adjusting composition of the present invention can be incorporated into a material or its molded product, thereby adjusting the refractive index of the material.

[0041] When the refractive index adjusting composition of the present invention is added to various materials, the materials may be in a solid state or in a liquid state such as a solution.

[0042] The material is not particularly limited, and examples thereof include resins, glass, and other inorganic materials, preferably resins. That is, the refractive index adjusting composition of the present invention is preferably used to adjust the refractive index of a resin. In addition, the refractive index adjusting composition of the present invention can also be combined with a resin to form a resin composition. The resin composition may be a molded product or a raw material for obtaining a molded product.

[0043] The type of resin is not particularly limited, and examples thereof include known resins such as acrylic resin, styrene resin, hydrogenated polystyrene resin, polyester resin, polycarbonate resin, fluororesin, polyvinyl chloride, polyurethane resin, polyamide resin, and polyolefin resin.

[0044] The shape of the material to which the refractive index adjusting composition of the present invention is added is not particularly limited, and examples thereof include films, thin films, sheets, substrates, and various other molded products.

[0045] When the refractive index adjusting composition of the present invention is incorporated into a material (e.g., a resin), the content is not particularly limited. For example, when a refractive index adjusting composition containing a sucrose naphthoate compound is incorporated into a material, the sucrose naphthoate compound is preferably contained in an amount of 0.1% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more, particularly preferably 2% by mass or more, and preferably 30% by mass or less, more preferably 20% by mass or less, even more preferably 15% by mass or less, particularly preferably 10% by mass or less, based on the total amount of the material.

[0046] Furthermore, when a refractive index adjusting composition containing a trehalose naphthoate compound is incorporated into a material, the trehalose naphthoate compound is contained in an amount of preferably 0.1% by mass or more, more preferably 0.5% by mass or more, even more preferably 1% by mass or more, and particularly preferably 2% by mass or more, based on the total amount of the material, and preferably 30% by mass or less, more preferably 20% by mass or less, even more preferably 15% by mass or less, and particularly preferably 10% by mass or less.

[0047] In specifying the inventions included in the present disclosure, the components (properties, structures, functions, etc.) described in each embodiment of the present disclosure may be combined in any manner. In other words, the present disclosure includes all subject matter consisting of all combinations of the components that can be combined as described in this specification. [Example]

[0048] The present invention will be explained in more detail below with reference to examples, but the present invention is not limited to these examples.

[0049] (Production Example 1a; Sucrose 2-naphthoate) Sucrose 2-naphthoate was prepared by a known method. Specifically, 34.2 parts of sucrose and 70 parts of water were placed in a 1 L five-neck flask equipped with a stirrer, thermometer, cooling condenser, dropping funnel, and a pH electrode connected to a pH meter and dissolved. Then, 100 parts of cyclohexanone containing 75.0 parts of 2-naphthoyl chloride was gradually added while cooling to below 10°C in a water bath. Then, while maintaining the temperature below 20°C, 48.5 parts of 48% aqueous caustic soda solution was added via the dropping funnel at a rate that maintained the pH at 10-11. The water bath was removed, and the mixture was stirred at room temperature for 1 hour at 20-30°C to complete the reaction. After that, a small amount of sodium carbonate was added and the mixture was heated to convert the trace amounts of remaining 2-naphthoyl chloride to sodium benzoate. The mixture was then allowed to stand for approximately 30 minutes, after which the aqueous phase was separated and removed. 70 parts of water was added, and the temperature was raised to 40-50°C in a hot water bath. After stirring for 30 minutes, the mixture was allowed to stand for about 30 minutes to separate and remove the aqueous phase. After repeating the same procedure two more times (total number of water washes: 3), the temperature was raised to 120°C, and the solvent was distilled off under reduced pressure to obtain the title sucrose 2-naphthoate with an esterification degree of 7-8.

[0050] (Production Example 1b; Sucrose 1-naphthoate) The title sucrose 2-naphthoate having an esterification degree of 7 to 8 was obtained by the same procedure as in Production Example 1a, except that 2-naphthoyl chloride was changed to 1-naphthoyl chloride.

[0051] (Production Example 2: Trehalose 2-naphthoate) The title trehalose 2-naphthoate with an esterification degree of 7 to 8 was obtained by carrying out the same procedure as in Production Example 1a, except that sucrose was replaced with trehalose (manufactured by Nagasevita).

[0052] Example 1a The sucrose 2-naphthoate compound obtained in Production Example 1a was used as a refractive index adjusting composition.

[0053] Example 1b The sucrose 1-naphthoate compound obtained in Production Example 1b was used as a refractive index adjusting composition.

[0054] Example 2 The trehalose 2-naphthoate obtained in Production Example 2 was used as a refractive index adjusting composition.

[0055] (Comparative Example 1) Sucrose benzoate with an esterification degree of 7.3 was obtained as a refractive index adjusting composition.

[0056] (Comparative Example 2) Sucrose benzoate with an esterification degree of 6 was obtained as a refractive index adjusting composition.

[0057] (Comparative Example 3) Sucrose acetate was obtained as a refractive index adjusting composition.

[0058] Comparative Example 4 Trehalose benzoate was obtained as a refractive index adjusting composition.

[0059] (Comparative Example 5) Trehalose octaacetate was obtained as a refractive index adjusting composition.

[0060] (Evaluation method) [Refractive index measurement] The refractive index of the refractive index-adjusting composition obtained in each Example and Comparative Example at a wavelength of 589 nm was measured using a Metricon "Prism Coupler" refractive index measuring device. Specifically, the refractive index-adjusting composition (solid) obtained in each Example and Comparative Example was added to dichloromethane to a concentration of 10% by mass to prepare a solution, and this solution was applied to a PET film using a No. 44 bar coater, followed by drying in a 50°C dryer for 10 minutes to obtain a film of the refractive index-adjusting composition. This film was used as a sample for refractive index measurement, and the refractive index was measured.

[0061] (Evaluation results) Table 1 shows the results of measuring the refractive index at a wavelength of 589 nm for the refractive index adjusting compositions obtained in each of the Examples and Comparative Examples.

[0062] The results of Examples 1a, 1b, and 2 shown in Table 1 show that the refractive index-adjusting compositions containing a sucrose naphthoate compound or a trehalose naphthoate compound have a higher refractive index than other sucrose ester compounds or trehalose ester compounds.

[0063] It is also clear that the refractive index adjusting composition containing a sucrose naphthoate compound or a trehalose naphthoate compound has a low Abbe number.

[0064] Therefore, the refractive index adjusting composition of the present invention has a high refractive index and a small Abbe number, and therefore can be said to have the property of being able to increase the dispersion of white light.

[0065] [Table 1]

[0066] Tables 2 to 4 show the results of measuring the Abbe number when the refractive index adjusting compositions obtained in Example 1a, Example 2, and Comparative Examples 1 to 4 were added to resins (PMMA resin in Table 2, polystyrene resin in Table 3, and polycarbonate resin in Table 4) in an amount of 5 mass %. In this measurement, the refractive index adjusting composition was added to a toluene solution of the resin so that the amount was 5 mass % relative to the total amount of the resin, and a film was produced using this solution. In Tables 2 to 4, "blank" refers to the Abbe number result for a resin to which no refractive index adjusting composition was added.

[0067] From Table 2, it can be seen that the refractive index adjusting compositions obtained in the examples have low Abbe numbers, and therefore, when added to a resin, the Abbe number of the resin can be lowered. Therefore, by using the refractive index adjusting composition of the present invention, a resin with a low Abbe number can be obtained, and for example, by combining it with a resin with a high Abbe number and using it as a lens material, etc., chromatic aberration correction becomes easier.

[0068] [Table 2]

[0069] Table 3

[0070] Table 4

Claims

1. A composition used for adjusting the refractive index, A refractive index adjusting composition containing a sucrose naphthoate compound.

2. A composition used for adjusting the refractive index, A refractive index adjusting composition containing a trehalose naphthoate compound.

3. The refractive index adjusting composition according to claim 1 or 2, which is used to adjust the refractive index of a resin.

4. A refractive index adjuster comprising the refractive index adjusting composition according to claim 1 or 2.

5. A resin composition comprising the refractive index adjusting composition according to claim 3 and a resin.

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