Composition and application thereof

Abstract

Provided is a tricyclodecanedimethanol composition which contains tricyclodecanedimethanol. The backscatter intensity T1 of the tricyclodecanedimethanol composition at an angle of 173°, which is measured at a temperature of 25°C using a dynamic light scattering measurement method, satisfies the formula: (T2 ÷ 0.8) ≤ T1 ≤ (T2× 5.0) wherein T2 represents the backscatter intensity of a standard sample (an aqueous suspension containing 0.002 vol% of a latex having a D50 value of 300 nm). Also provided is an application using the tricyclodecanedimethanol composition.

Description

Compositions and their applications

[0001] The present invention relates to a tricyclodecane dimethanol composition, an ultraviolet-curable composition, a polymer composition, a method for producing a tricyclodecane dimethanol composition, a method for storing a tricyclodecane dimethanol composition, and a method for producing an organic material.

[0002] In the fields of molding materials, electronic materials, and display device components, materials with alicyclic molecular structures are used due to their transparency, heat resistance, and low water absorption. Tricyclodecane dimethanol (hereinafter abbreviated as "TCDDM") is a dihydric alcohol with an alicyclic structure. TCDDM is produced by hydroformylating dicyclopentadiene with carbon monoxide and hydrogen in the presence of a catalyst to produce an aldehyde, which is then reduced by hydrogen (see Patent Documents 1, 2, Non-Patent Documents 1, and 2). TCDDM has been used as a synthetic raw material for molding materials such as polyesters and polycarbonates. Polymers containing TCDDM as a component are known to exhibit excellent performance in terms of hardness, transparency, heat resistance, and low water absorption due to their alicyclic structure, and are used in fields such as molding materials, electronic materials, and display device components. Furthermore, derivatives of TCDDM, such as diacrylate derivatives, dimethacrylate derivatives, and urethane acrylates, synthesized using TCDDM as a raw material, are used as ultraviolet-curable compositions. Cured products using such ultraviolet-curable compositions exhibit high surface hardness, high glass transition temperatures, excellent thermal decomposition resistance, and excellent development resistance, and are therefore attracting attention as electronic materials and display device components, such as hard coats, antifouling coats, and resists. Under these circumstances, Patent Document 3 discloses a tricyclodecane dimethanol composition, as well as an ultraviolet-curable composition and a polymer composition using the same.

[0003] Patent Document 3 describes that one component (a chiral compound whose one enantiomer is represented by formula (A)) among the isomers of a tricyclodecane dimethanol composition (TCDDM composition) has an extremely highly crystalline structure, and that by producing the composition so that the ratio of this component is equal to or greater than a predetermined value, it is possible to adjust the crystallinity of the TCDDM composition and obtain a TCDDM composition that is less likely to become stringy and has excellent handleability.

[0004] JP 2020-132624 A JP 2021-520401 A International Publication No. 2023 / 176641

[0005] Hitachi Chemical Technical Report, No. 51 (2008-7), pp. 7-12; Applied Catalyst, Vol. 19, pp. 259-273 (1985)

[0006] The TCDDM composition described in Patent Document 3 is a material that is less prone to stringiness and has excellent handleability. On the other hand, from the perspective of shelf life, a TCDDM composition that does not increase in viscosity during storage may be required. Furthermore, when considering formulation operations, a TCDDM composition with appropriate fluidity may be required. If the viscosity of a TCDDM composition increases, it may become difficult to pump the TCDDM composition or a raw material mixture containing the TCDDM composition (hereinafter referred to as the "TCDDM composition, etc.") using a gear pump or other device. Furthermore, heating to improve the fluidity of the TCDDM composition, etc., can cause deterioration of the TCDDM composition, etc. Furthermore, the use of TCDDM in the production of organic materials such as polymers and ultraviolet-curable compositions has been investigated. However, the inventors' investigations have revealed that the TCDDM composition can become cloudy or its fluidity can decrease depending on storage conditions, and that its viscosity can increase significantly, significantly reducing its handleability, depending on its thermal history and handling conditions.

[0007] The present invention aims to solve these problems and to provide a TCDDM composition that has excellent storage stability and fluidity, as well as an ultraviolet-curable composition and a polymer composition that use the TCDDM composition. Another object of the present invention is to suppress the clouding or loss of fluidity of the TCDDM composition. More specifically, the present invention aims to provide a TCDDM composition that is stored in a container, or a method for producing a TCDDM composition that suppresses clouding or loss of fluidity in a method for storing a TCDDM composition. Another object of the present invention is to provide a method for producing an organic material that suppresses an increase in viscosity of the TCDDM composition during storage and that enables efficient production of an organic material using the TCDDM composition as a raw material.

[0008] Under these circumstances, the inventors have conducted research and found that the 173° backscattering intensity T １ It has been found that adjusting the temperature to within a predetermined range can improve the storage stability and fluidity of the TCDDM composition. It has also been found that storing the TCDDM composition in a container while maintaining the temperature above 45°C can suppress clouding or a decrease in fluidity of the TCDDM composition. Furthermore, it has been found that organic materials can be efficiently produced by heating the TCDDM composition to 45°C or higher but lower than 120°C, and then feeding it into a processing machine for producing organic materials and processing it while maintaining the temperature at 45°C to but lower than 120°C.

[0009] That is, the present invention provides the following.

[0010] [1] A tricyclodecane dimethanol composition containing tricyclodecane dimethanol, wherein the 173° backscattering intensity T １ is the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷8.0≦T １ ≦T ２× 5.0. [2] The 173° backscattering intensity T １ But, T ２ ÷5.0≦T １ ≦T ２ The tricyclodecane dimethanol composition according to [1], wherein one enantiomer of the tricyclodecane dimethanol contains a chiral compound represented by formula (A), and the content of the chiral compound represented by formula (A) is 25 to 54 mass% relative to 100 mass% of the total mass of the tricyclodecane dimethanol. [4] The tricyclodecane dimethanol composition according to any one of [1] to [3], wherein the tricyclodecane dimethanol contains a chiral compound whose one enantiomer is represented by formula (A), and the content of the chiral compound represented by formula (A) is 33 to 38 mass% relative to 100 mass% of the total mass of the tricyclodecane dimethanol. [5] The tricyclodecane dimethanol composition according to any one of [1] to [4], wherein the tricyclodecane dimethanol contains a chiral compound whose one enantiomer is represented by formula (B), and the content of the chiral compound represented by formula (B) is 1.6 to 4.8 mass% relative to 100 mass% of the total mass of the tricyclodecane dimethanol. [6] The tricyclodecane dimethanol composition according to any one of [1] to [5], wherein the tricyclodecane dimethanol comprises a chiral compound whose one enantiomer is represented by formula (A) and a chiral compound whose other enantiomer is represented by formula (B), the content of the chiral compound represented by formula (A) is 33 to 38% by mass relative to 100% by mass of the total mass of the tricyclodecane dimethanol, and the content of the chiral compound represented by formula (B) is 1.6 to 4.8% by mass relative to 100% by mass of the total mass of the tricyclodecane dimethanol. [7] The tricyclodecane dimethanol composition according to any one of [1] to [6], wherein the tricyclodecane dimethanol content is 70% by mass or more, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition. [8] The tricyclodecane dimethanol composition according to any one of [1] to [7], which is substantially free of a fragrance carrier. [9] An ultraviolet-curable composition derived from the tricyclodecane dimethanol composition according to any one of [1] to [8].

[10] The ultraviolet-curable composition according to [9], which is used for at least one of a hard coat material, an antifouling coat material, a resist material, an inkjet ink, and a material for a 3D printer.

[11] A polymer composition derived from the tricyclodecane dimethanol composition according to any one of [1] to [8].

[12] The polymer composition according to

[11] , which is at least one resin selected from the group consisting of a polyester resin, an epoxy resin, an acrylate resin, a polycarbonate resin, and a polyurethane resin.

[13] A method for producing a tricyclodecane dimethanol composition stored in a container, the method comprising storing a tricyclodecane dimethanol composition (A0) containing tricyclodecane dimethanol obtained by distillation and purification in a container while maintaining the temperature at not less than 45°C, wherein the tricyclodecane dimethanol contains a chiral compound whose one enantiomer is represented by formula (A).

[14] The method for producing a tricyclodecane dimethanol composition according to

[13] , wherein the content of the tricyclodecane dimethanol is 70% by mass or more, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A0).

[15] The method for producing a tricyclodecane dimethanol composition according to

[13] or

[14] , wherein the tricyclodecane dimethanol composition is substantially free of a fragrance carrier.

[16] The method for producing a tricyclodecane dimethanol composition according to any one of

[13] to

[15] , wherein the container is a transport container.

[17] The method for producing a tricyclodecane dimethanol composition according to any one of

[13] to

[16] , wherein the content of the chiral compound of which one enantiomer is represented by formula (A) is 25% by mass or more and 54% by mass or less, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A0).

[18] The method for producing a tricyclodecane dimethanol composition according to any one of

[13] to

[17] , wherein the tricyclodecane dimethanol composition (A0) contains a chiral compound, one enantiomer of which is represented by formula (B).

[19] The method for producing a tricyclodecane dimethanol composition according to

[18] , wherein the content of the chiral compound of which one enantiomer is represented by formula (B) is 1.6% by mass or more and 4.8% by mass or less, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A0).

[20] The method for producing a tricyclodecane dimethanol composition according to

[18] , wherein the content of the chiral compound of which one enantiomer is represented by formula (B) is 1.6% by mass or more and 4.8% by mass or less, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A0). １ is the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷500≦T １ ≦T ２

[21] The method for producing the tricyclodecane dimethanol composition according to any one of

[13] to

[19] , wherein the 173° backscattering intensity T １ But, T ２ ÷8.0≦T １ ≦T ２

[22] The method for producing a tricyclodecane dimethanol composition according to

[20] , wherein the 173° backscattering intensity T １ is the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷8.0≦T １ ≦T ２ × 5.0.

[23] The method for producing the tricyclodecane dimethanol composition according to any one of

[13] to

[22] , wherein the tricyclodecane dimethanol composition stored in the container is heated while stored in the container and then directly fed from the container to a processing machine.

[24] The method for producing the tricyclodecane dimethanol composition according to

[23] , wherein the processing machine is a reactor and / or a blender.

[25] A method for storing a tricyclodecane dimethanol composition (A0) containing tricyclodecane dimethanol obtained by distillation and purification in a container while maintaining the temperature at not below 45°C, wherein the tricyclodecane dimethanol contains a chiral compound of which one enantiomer is represented by formula (A).

[26] The method for storing the tricyclodecane dimethanol composition according to

[25] , wherein the content of the tricyclodecane dimethanol is 70% by mass or more, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A0).

[27] The method for storing the tricyclodecane dimethanol composition according to

[25] or

[26] , wherein the tricyclodecane dimethanol composition is substantially free of a fragrance carrier.

[28] The method for storing the tricyclodecane dimethanol composition according to any one of

[25] to

[27] , wherein the content of the chiral compound of which one enantiomer is represented by formula (A) is 25% by mass or more and 54% by mass or less, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A0).

[29] The method for storing the tricyclodecane dimethanol composition according to any one of

[25] to

[28] , wherein the tricyclodecane dimethanol composition (A0) contains a chiral compound of which one enantiomer is represented by formula (B).

[30] The method for storing a tricyclodecane dimethanol composition according to

[29] , wherein the content of the chiral compound whose one enantiomer is represented by formula (B) is 1.6% by mass or more and 4.8% by mass or less, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A0).

[31] The method for storing a tricyclodecane dimethanol composition according to any one of

[25] to

[30] , wherein the tricyclodecane dimethanol composition stored in the container is heated while stored in the container, and then directly fed from the container into a processing machine.

[32] The method for storing a tricyclodecane dimethanol composition according to

[31] , wherein the processing machine is a reactor and / or a blender.

[33] A method for producing an organic material (excluding fragrance materials) comprising: heating part or all of a tricyclodecane dimethanol composition (A1) that contains tricyclodecane dimethanol and that is stored in a container and at a temperature of less than 45°C to 45°C or higher but lower than 120°C; and feeding the heated tricyclodecane dimethanol composition (A2) into a processing machine while maintaining the temperature at 45°C or higher but lower than 120°C; wherein the tricyclodecane dimethanol contains a chiral compound whose one enantiomer is represented by formula (A).

[34] The method for producing an organic material according to

[33] , wherein the content of tricyclodecane dimethanol in the organic material is 70% by mass or more relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A1).

[35] The method for producing an organic material according to

[33] or

[34] , wherein the tricyclodecane dimethanol composition (A1) is heated while stored in the container.

[36] The method for producing an organic material according to any one of

[33] to

[35] , wherein the tricyclodecane dimethanol composition (A1) is heated while stored in the container, and then directly introduced from the container into the processing machine.

[37] The method for producing an organic material according to

[33] to

[35] , wherein the 173° backscattering intensity T １ is the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷500≦T １ ≦T ２

[38] The method for producing an organic material according to any one of

[33] to

[36] , wherein the 173° backscattering intensity T of the tricyclodecane dimethanol composition (A2) measured at a temperature of 25°C using a dynamic light scattering measurement method is １ is the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷8.0≦T １ ≦T ２

[39] The method for producing an organic material according to any one of

[33] to

[37] , wherein the 173° backscattering intensity T １ But, T ２ ÷4.0≦T １ ≦T ２

[40] The method for producing an organic material according to any one of

[33] to

[39] , wherein the content of the chiral compound of which one enantiomer is represented by formula (A) in the tricyclodecane dimethanol composition (A1) is 25% by mass or more and 54% by mass or less, relative to the total mass of the tricyclodecane dimethanol composition (A1) (100% by mass).

[41] The method for producing an organic material according to any one of

[33] to

[40] , wherein the content of the chiral compound of which one enantiomer is represented by formula (A) in the tricyclodecane dimethanol composition (A1) is 33% by mass or more and 38% by mass or less, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A1).

[42] The method for producing an organic material according to any one of

[33] to

[41] , wherein the tricyclodecane dimethanol contains a chiral compound of which one enantiomer is represented by formula (B), and the content of the chiral compound of which one enantiomer is represented by formula (B) in the tricyclodecane dimethanol composition (A1) is 1.6% by mass or more and 48% by mass or less, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A1).

[43] The method for producing an organic material according to any one of

[33] to

[42] , wherein the processing machine is a reactor and / or a compounder.

[44] The method for producing an organic material according to any one of

[33] to

[43] , wherein the organic material is at least one polymer selected from the group consisting of polyester-based resins, epoxy-based resins, acrylate-based resins, polycarbonate-based resins, and polyurethane-based resins, or an ultraviolet-curable composition.

[45] The method for producing an organic material according to any one of

[33] to

[44] , wherein the tricyclodecane dimethanol composition (A1) is stored in the container in an environment of -5°C or higher and lower than 45°C for 24 hours or more before the heating.

[46] The method for producing an organic material according to any one of

[33] to

[45] , comprising storing the tricyclodecane dimethanol composition (A0) obtained by distillation and purification in the container while maintaining the temperature at not lower than 45°C.

[47] The method for producing an organic material according to any one of

[33] to

[46] , wherein the tricyclodecane dimethanol composition (A1) is heated while stored in the container and then directly charged from the container into the processing machine; the content of the compound represented by formula (A) in the tricyclodecane dimethanol (A1) is 25% by mass or more and 54% by mass or less, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A1); the processing machine is a reactor and / or a compounder; and the organic material is at least one polymer selected from the group consisting of polyester-based resins, epoxy-based resins, acrylate-based resins, polycarbonate-based resins, and polyurethane-based resins, or an ultraviolet-curable composition.

[48] ​​The method for producing an organic material according to any one of

[33] to

[47] , wherein the tricyclodecane dimethanol composition (A0) obtained by distillation and purification is stored in the container while maintaining the temperature at not less than 45°C, and the tricyclodecane dimethanol composition (A1) is left in an environment of not less than -5°C and less than 45°C while stored in the container for not less than 24 hours before the heating.

[49] The method for producing an organic material according to any one of

[33] to

[48] , wherein, after the tricyclodecane dimethanol composition (A0) has been stored in the container, no stirring is performed on the tricyclodecane dimethanol composition (A2) until it is directly charged into the processing machine.

[50] The method for producing an organic material according to any one of

[33] to

[49] , wherein, after the tricyclodecane dimethanol composition (A0) has been stored in the container, no heating is performed on the tricyclodecane dimethanol composition (A1) until it is heated to 45°C or higher and lower than 120°C.

[0011] The present invention provides a TCDDM composition that exhibits excellent storage stability and fluidity, as well as an ultraviolet-curable composition and a polymer composition that use the TCDDM composition. Furthermore, the present invention makes it possible to suppress clouding or a decrease in fluidity of the TCDDM composition during storage. More specifically, the present invention makes it possible to provide a TCDDM composition that is stored in a container and a method for storing the TCDDM composition, and in which clouding or a decrease in fluidity is suppressed. Furthermore, the present invention makes it possible to provide a method for producing an organic material that efficiently produces an organic material using the TCDDM composition as a raw material while suppressing an increase in viscosity of the TCDDM composition during storage. As a result, good workability when handling the TCDDM composition can be maintained, and the production efficiency of organic materials can be improved.

[0012] FIG. 1 shows a gas chromatogram of the TCDDM composition obtained in Example 1-1. It is a process schematic diagram showing the method for producing a TCDDM composition stored in a container of the present invention, as well as the subsequent steps of transporting, storing, and processing the TCDDM composition stored in the container. It is a process schematic diagram showing the method for producing a TCDDM composition stored in a container of the present invention, as well as the subsequent steps of processing the TCDDM composition stored in the container. It is a gas chromatogram of the TCDDM composition obtained in Example 2-1. FIG. 5 is a process schematic diagram showing each step of an example of the method for producing an organic material of the present invention. FIG. 6 shows a gas chromatogram of the TCDDM composition obtained in Example 3-1.

[0013] Hereinafter, an embodiment of the present invention (hereinafter simply referred to as "the present embodiment") will be described in detail. Note that the present embodiment is an example for explaining the present invention, and the present invention is not limited to only this embodiment.

[0014] In this specification, the word "to" is used to mean that the numerical values ​​before and after it are included as the upper and lower limits. "A to B" means that the range is A or more and B or less. In addition, any combination of the upper and lower limit values ​​of the numerical values ​​in this specification is an example of this embodiment.

[0015] In this specification, unless otherwise specified, "including A or B" means "including A," "including B," or "including A and B."

[0016] In this specification, "mass %" indicates the content ratio of a specific component contained in a total amount of 100 mass %. Furthermore, "mass %" and "weight %" have the same meaning.

[0017] As used herein, "optional" or "optionally" means that the subsequently described circumstance may or may not occur, and thus the description includes both the occurrence and non-occurrence of the circumstance.

[0018] In this specification, various physical properties and characteristic values ​​are those at 23° C. unless otherwise specified.

[0019] In this specification, the term "process" does not only refer to an independent process, but also includes processes that cannot be clearly distinguished from other processes as long as the process achieves its intended effect. If the measurement methods, etc. described in the standards shown in this specification change from year to year, they will be based on the standards in effect as of January 1, 2024, unless otherwise specified. If the measurement methods, etc. described in the standards shown in this specification have been abolished as of January 1, 2024, they will be based on the standards in effect at the time of abolition.

[0020] Hereinafter, the embodiments of the present invention will be described in detail. However, the explanation of the constituent elements described below is an example of an embodiment of the present invention, and the present invention is not limited to these contents.

[0021] The first embodiment of the present invention will now be described in detail.

[0022] <Tricyclodecane dimethanol composition> The tricyclodecane dimethanol composition (TCDDM composition) of this embodiment is a TCDDM composition containing tricyclodecane dimethanol, and has a 173° backscattering intensity T １ is the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷8.0≦T １ ≦T ２ × 5.0. By using such a composition, a TCDDM composition having excellent storage stability and excellent fluidity can be obtained. １ is an index showing the fluidity and storage stability of the TCDDM composition. １ The lower limit of T ２ By setting the value to ÷8.0 or more, the 173° backscattering intensity T １ tends to be relatively high, and microcrystals are generated in the TCDDM composition, which has a moderate fluidity and tends to be excellent in handling during blending operations, etc. １ The upper limit of ２ × 5.0 or less, the 173° backscattering intensity T １ The amount of TCDDM crystallites in the TCDDM composition is relatively low, the viscosity is less likely to increase during storage, and the storage stability tends to be good.

[0023] The backscattering intensity T １ can be achieved by adjusting the number of heating and stirring times of TCDMM, storage conditions, etc. For example, the backscattering intensity T １ T ２x 5.0 or less can be achieved by reducing the number of heating and cooling cycles after producing the TCDDM raw material, by reducing the number of times the TCDDM is stirred or transferred to a different container while heated, and by minimizing storage at temperatures between 45°C and 55°C. １ T ２ A ratio of ÷8.0 or more can be achieved by performing stirring with heating once, increasing the proportion of chiral compound A in TCDDM, or the like.

[0024] (First embodiment of the method for producing a TCDDM composition) A specific embodiment (first embodiment) of the method for producing a TCDDM composition of the present embodiment includes, for example, a method in which a TCDDM composition (A0) obtained by distillation purification and containing a chiral compound of which one enantiomer is represented by formula (A) is stored in a container while maintaining the temperature at not below 45°C, thereby obtaining the TCDDM composition as the TCDDM composition stored in the container.

[0025] In the first embodiment described above, the lower limit of the temperature until storage in the container is not particularly limited, but is preferably 45°C or higher, more preferably 50°C or higher, even more preferably 60°C or higher, still more preferably above 60°C, even more preferably 70°C or higher, even more preferably above 70°C, and particularly preferably 75°C or higher. On the other hand, the upper limit of the temperature until storage in the container is not particularly limited, but is preferably 110°C or lower, more preferably 100°C or lower, even more preferably 95°C or lower, even more preferably 90°C or lower, even more preferably less than 90°C, and even more preferably 85°C or lower. The above upper and lower limits can be combined arbitrarily. For example, the temperature at which the TCDDM composition (A0) obtained by distillation and purification is stored in a container is preferably 45°C or higher and 110°C or lower, more preferably 50°C or higher and 100°C or lower, even more preferably 60°C or higher and 95°C or lower, still more preferably higher than 60°C and 90°C or lower, still more preferably 70°C or higher and lower than 90°C, and even more preferably higher than 70°C and 85°C or lower.

[0026] In the first embodiment described above, the time for which the TCDDM composition (A0) obtained by distillation and purification is kept at a temperature not lower than 45°C is not particularly limited, but is preferably at least 1 hour, more preferably more than 1 hour, even more preferably at least 5 hours, still more preferably at least 15 hours, even more preferably at least 30 hours, and even more preferably at least 45 hours. Meanwhile, the upper limit of the temperature until storage in the container described above is not particularly limited, but is preferably at most 130 hours, more preferably at most 110 hours, even more preferably at most 90 hours, still more preferably at most 70 hours, even more preferably at most 60 hours, and even more preferably at most 50 hours. The above upper and lower limits can be combined in any manner. For example, the time for which the TCDDM composition (A0) obtained by distillation and purification is kept at a temperature not lower than 45°C is preferably from 1 hour to 130 hours, more preferably from more than 1 hour to 110 hours, even more preferably from 5 hours to 90 hours, still more preferably from 15 hours to 70 hours, even more preferably from 30 hours to 60 hours, and even more preferably from 45 hours to 50 hours.

[0027] In the first embodiment described above, the content ratio of the chiral compound having one enantiomer represented by formula (A) and the chiral compound having one enantiomer represented by formula (B) contained in TCDDM composition (A0) is synonymous with the content ratio of the chiral compound having one enantiomer represented by formula (A) and the chiral compound having one enantiomer represented by formula (B) contained in the TCDDM composition of this embodiment.

[0028] (Second embodiment of the method for producing a TCDDM composition) Alternatively, another embodiment (second embodiment) of the method for producing the TCDDM composition of this embodiment includes a method in which part or all of a TCDDM composition (A1) stored in a container and held at a temperature below 45°C, the TCDDM composition containing a chiral compound of which one enantiomer is represented by formula (A), is heated to 45°C or higher but lower than 120°C, and the heated TCDDM composition (A2) is charged into a processing machine while maintained at a temperature of 45°C or higher but lower than 120°C, to obtain a TCDDM composition stored in the processing machine. The lower limit of the temperature until storage in the container is not particularly limited, but is preferably 45°C or higher, more preferably 50°C or higher, even more preferably 60°C or higher, still more preferably above 60°C, even more preferably 70°C or higher, still more preferably above 70°C, and particularly preferably 75°C or higher. On the other hand, the upper limit of the temperature before storage in the above-mentioned container is not particularly limited, but is preferably 110°C or lower, more preferably 100°C or lower, even more preferably 95°C or lower, still more preferably 90°C or lower, even more preferably less than 90°C, and even more preferably 85°C or lower. The above upper and lower limits can be combined arbitrarily. For example, the temperature before storage in the above-mentioned container is preferably 45°C or higher and 110°C or lower, more preferably 50°C or higher and 100°C or lower, even more preferably 60°C or higher and 95°C or lower, even more preferably higher than 60°C and 90°C or lower, even more preferably 70°C or higher and lower than 90°C, and even more preferably higher than 70°C and 85°C or lower.

[0029] In the second embodiment described above, the total time during which the temperature of the TCDDM composition is in the range of 45°C or higher but lower than 120°C is not particularly limited, but is preferably 1 hour or longer, more preferably more than 1 hour, even more preferably 5 hours or longer, even more preferably 15 hours or longer, still more preferably 30 hours or longer, and even more preferably 45 hours or longer. Meanwhile, the upper limit of the temperature until storage in the container described above is not particularly limited, but is preferably 130 hours or shorter, more preferably 110 hours or shorter, even more preferably 90 hours or shorter, even more preferably 70 hours or shorter, still more preferably 60 hours or shorter, and even more preferably 50 hours or shorter. The above upper and lower limits can be arbitrarily combined. For example, the total time during which the temperature of the TCDDM composition is in the range of 45°C or higher but lower than 120°C is preferably 1 hour or longer but lower than 130 hours, more preferably more than 1 hour but lower than 110 hours, even more preferably 5 hours or longer but lower than 90 hours, still more preferably 15 hours or longer but lower than 70 hours, still more preferably 30 hours or longer but lower than 60 hours, and even more preferably 45 hours or longer but lower than 50 hours.

[0030] In the second embodiment described above, the content ratio of the chiral compound having one enantiomer represented by formula (A) and the chiral compound having one enantiomer represented by formula (B) contained in TCDDM composition (A0) is synonymous with the content ratio of the chiral compound having one enantiomer represented by formula (A) and the chiral compound having one enantiomer represented by formula (B) contained in the TCDDM composition of this embodiment.

[0031] In the TCDDM composition of this embodiment, the backscattering intensity T １ The lower limit of T ２ ÷8.0 or more, and T ２ ÷7.0 or more, and T ２ It is more preferable that T ２ It is more preferable that T is 5.0 or more. ２ It is more preferable that T is 4.8 or more. ２ It is more preferable that T is 4.0 or more. ２ It is even more preferable that T ２It is particularly preferable that T ２ In the TCDDM composition of the embodiment, the backscattering intensity T １ The upper limit of T ２ × 5.0 or less, and T ２ × 4.0 or less, and T ２ x 3.0 or less is more preferable, and T ２ More preferably, T ２ It is more preferable that T ２ × 1.0 or less is more preferable, and T ２ It is even more preferable that T ２ It is particularly preferable that T ２ It is most preferable that the backscattering intensity T is 1.6 or less. By making the backscattering intensity T equal to or greater than the lower limit, the TCDDM composition has a suitable fluidity, which tends to improve handling during blending operations and the like. Furthermore, by making the backscattering intensity T equal to or less than the upper limit, the viscosity of the TCDDM composition is less likely to increase during storage, which tends to improve storage stability. The above upper and lower limits can be combined arbitrarily. For example, in the TCDDM composition of the present invention, １ Is T ２ ÷8.0≦T １ ≦T ２ × 5.0, and T ２ ÷7.0≦T １ ≦T ２ × 4.0 or more is preferable, and T ２ ÷6.0≦T １ ≦T ２ x 3.0 or more is more preferable, and T ２ ÷5.0≦T １ ≦T ２ x 2.0 is more preferable, and T ２ ÷4.8≦T １ ≦T ２ × 1.5 is more preferable, and T ２ ÷4.0≦T １ ≦T ２ x 1.0 is more preferable, and T ２ ÷3.0≦T １ ≦T ２÷1.4 is even more preferred, and T ２ ÷2.5≦T １ ≦T ２ ÷1.5 is particularly preferred, and T ２ ÷2.0≦T １ ≦T ２ ÷1.6 is most preferred.

[0032] As a more specific embodiment of the TCDDM composition of this embodiment, for example, １ The lower limit of the backscattering intensity T is preferably 1055 or more, more preferably 1100 or more, even more preferably 1500 or more, and particularly preferably 1800 or more. １ The upper limit of is preferably 10,550 or less, more preferably 8,000 or less, even more preferably 7,000 or less, particularly preferably 5,000 or less, and most preferably 3,500 or less. By setting it at or above the lower limit, the TCDDM composition has appropriate fluidity, which tends to make it easier to handle during blending operations and the like. Furthermore, by setting it at or below the upper limit, the viscosity of the TCDDM composition is less likely to increase during storage, which tends to improve storage stability. The above upper and lower limits can be combined in any way. For example, in the TCDDM composition of the present invention, １ , 1055≦T １ ≦10550 is preferred, and 1100≦T １ ≦8000 is more preferable, and 1500≦T １ ≦7000 is more preferable, and 1800≦T １ ≦5000 is particularly preferred, and 1800≦T １ ≦3500 is particularly preferred.

[0033] The TCDDM composition of this embodiment preferably contains a chiral compound having one enantiomer represented by formula (A) (sometimes referred to herein as "chiral compound A") and / or a chiral compound having one enantiomer represented by formula (B) (sometimes referred to herein as "chiral compound B"), and more preferably contains both chiral A compound and chiral B compound. That is, when the content of chiral compound A is high, microcrystals are formed in the TCDDM composition, and the TCDDM composition tends to have appropriate fluidity and be easy to handle in blending operations, etc., whereas when the content of chiral compound B is high, the proportion of chiral compound A becomes relatively low, which reduces the amount of TCDDM microcrystals in the TCDDM composition and makes it less likely to increase in viscosity during storage, tending to improve storage stability.

[0034] In the TCDDM composition of this embodiment, the lower limit of the content of chiral compound A is not particularly limited, but is preferably 25% by mass or more, more preferably 28% by mass or more, even more preferably 30% by mass or more, even more preferably 33% by mass or more, particularly preferably 34% by mass or more, even more preferably 35% by mass or more, and especially more preferably 36% by mass or more, relative to the total mass of the TCDDM (100% by mass). The upper limit of the content of chiral compound A is not particularly limited, but is preferably 54% by mass or less, more preferably 50% by mass or less, even more preferably 45% by mass or less, even more preferably 43% by mass or less, even more preferably 41% by mass or less, even more preferably 40% by mass or less, and especially more preferably 39% by mass or less. By ensuring that the content is equal to or greater than the lower limit, the TCDDM composition has appropriate fluidity and tends to be excellent in handling, such as during blending operations. Furthermore, by keeping the content at or below the above upper limit, the formation of TCDDM microcrystals in the TCDDM composition is suppressed, the viscosity is less likely to increase during storage, and storage stability tends to be improved. The above upper and lower limits can be combined arbitrarily. For example, in the TCDDM composition of the present invention, the content of the chiral compound A is not particularly limited, but is preferably 25% by mass or more and 54% by mass or less, more preferably 28% by mass or more and 50% by mass or less, even more preferably 30% by mass or more and 45% by mass or less, even more preferably 33% by mass or more and 43% by mass or less, even more preferably 34% by mass or more and 41% by mass or less, even more preferably 35% by mass or more and 40% by mass or less, and particularly preferably 36% by mass or more and 39% by mass or less, relative to the total mass of the TCDDM (100% by mass).

[0035] In the TCDDM composition of this embodiment, the lower limit of the content of chiral compound B is not particularly limited, but is preferably 1.6% by mass or more, more preferably 1.8% by mass or more, even more preferably 2.0% by mass or more, even more preferably 2.1% by mass or more, even more preferably 2.2% by mass or more, and even more preferably 2.3% by mass or more, relative to 100% by mass of the total mass of the TCDDM. The upper limit of the content of chiral compound B is not particularly limited, but is preferably 4.8% by mass or less, more preferably 4.6% by mass or less, even more preferably 4.4% by mass or less, even more preferably 4.3% by mass or less, even more preferably 4.2% by mass or less, even more preferably 4.0% by mass or less, and is preferably 3.8% by mass or less, 3.5% by mass or less, 3.2% by mass or less, 3.0% by mass or less, 2.8% by mass or less, and 2.7% by mass or less, in this order. By setting the content at or above the lower limit, the formation of TCDDM microcrystals in the TCDDM composition is suppressed, the viscosity is less likely to increase during storage, and storage stability tends to be improved. Furthermore, by setting the content at or below the upper limit, the TCDDM composition has appropriate fluidity, which tends to improve handling during blending and other operations. The upper and lower limits can be combined arbitrarily. For example, in the TCDDM composition of the present invention, the content of chiral compound B is not particularly limited, but is preferably 1.6% by mass to 4.8% by mass, more preferably 1.8% by mass to 4.6% by mass, even more preferably 2.0% by mass to 4.4% by mass, still more preferably 2.1% by mass to 4.3% by mass, even more preferably 2.2% by mass to 4.2% by mass, and even more preferably 2.3% by mass to 4.0% by mass, relative to 100% by mass of the total mass of the TCDDM.

[0036] In the TCDDM composition of the present invention, the lower limit of the tricyclodecane dimethanol content is not particularly limited, but from the viewpoint of ease of handling of the composition, it is preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, still more preferably 95% by mass or more, or even 97% by mass or more, or 99% by mass or more, relative to 100% by mass of the total TCDDM composition. On the other hand, the upper limit of the total content is not particularly limited, and a higher value is preferable, and it may be 100% by mass, relative to the total mass of the TCDDM composition.

[0037] The TCDDM composition of the present invention may contain compounds other than TCDDM, provided that the effects of the present invention are not impaired. The "compounds other than TCDDM" are not particularly limited, and examples include compounds having an aldehyde group that are reaction intermediates during TCDDM synthesis, compounds having a carbonyl group derived from compounds containing the aldehyde group, diols containing 12 carbon atoms that are mixed in during the manufacturing process, and known additives that are blended as needed. The content of the compounds other than TCDDM in the TCDDM composition of the present invention is not particularly limited as long as the effects of the present invention are not impaired. Typically, the content can be 0.01% by mass or more and 3% by mass or less, based on the total mass of the TCDDM composition (100% by mass). Alternatively, the composition may contain no compounds other than TCDDM (0% by mass).

[0038] In the TCDDM composition of the present invention, the lower limit of the total content of chiral compound A, chiral compound B, and chiral compound C is not particularly limited, but from the viewpoint of ease of handling the composition, it is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more, relative to 100% by mass of the total mass of the TCDDM composition. On the other hand, the upper limit of the total content is not particularly limited, and a higher value is preferable, and it may be 100% by mass, relative to the total mass of the TCDDM composition.

[0039] The TCDDM composition of the present invention is preferably substantially free of a flavor carrier. When the TCDDM composition of the present invention is substantially free of a flavor carrier, the resulting TCDDM composition tends to have better storage stability and flowability. "Substantially free of a flavor carrier" means that a flavor carrier is not intentionally added, and specifically means that the content of the flavor carrier in the tricyclodecane dimethanol composition is 5% by mass or less, preferably 1% by mass or less, more preferably 0.1% by mass or less, and even more preferably 0.01% by mass or less, relative to the total mass of the tricyclodecane dimethanol composition.

[0040] <Production Method of TCDDM Composition> The production method of the TCDDM composition of this embodiment includes the steps of hydroformylating dicyclopentadiene to obtain tricyclodecane dicarbaldehydes, reducing the tricyclodecane dicarbaldehyde to obtain a crude reaction solution containing tricyclodecane dimethanol, and purifying the crude reaction solution by distillation to obtain a tricyclodecane dimethanol composition. During this process, isomers are generated in the step of introducing formyl groups by hydroformylation, and a mixture of tricyclodecane dicarbaldehydes is obtained, which serve as precursors to chiral compound A, chiral compound B, and chiral compound C, respectively. A subsequent hydrogenation step yields chiral compound A, chiral compound B, chiral compound C, etc., respectively.

[0041] The method for controlling the ratios of chiral compound A, chiral compound B, and chiral compound C in this embodiment is not particularly limited, and may be controlled by adjusting the reaction conditions for hydroformylation, by isomerization using a method such as heating, or by purifying the produced TCDDM composition by distillation to adjust the ratios.

[0042] <Hydroformylation Reaction of Dicyclopentadiene> There are no particular limitations on the method for hydroformylating dicyclopentadiene, and the hydroformylation can be carried out according to a conventional method. For example, according to the method described in JP-A-2001-10999, dicyclopentadiene can be hydroformylated using hydrogen and carbon monoxide in a hydroformylation reaction solvent comprising a hydrocarbon compound, in the presence of a catalyst comprising a rhodium compound and an organophosphorus compound, to produce tricyclodecane dicarbaldehyde. The rhodium compound used in this hydroformylation step can be any precursor, regardless of its form, as long as it forms a complex with the organophosphorus compound and exhibits hydroformylation activity in the presence of hydrogen and carbon monoxide. That is, Rh(acac)(CO) ２ , Rh ２ O ３ , Rh ４ (CO) １２ , Rh ６ (CO) １６ , Rh(NO ３ ) ３ Alternatively, a catalyst precursor such as the above may be introduced into the reaction mixture together with an organophosphorus compound to form a catalytically active rhodium metal hydride carbonyl phosphorus complex in the reaction vessel, or a rhodium metal hydride carbonyl phosphorus complex catalyst may be prepared in advance and then introduced into the reaction vessel.

[0043] In a preferred embodiment of this invention, Rh(acac)(CO) ２ is used as a rhodium precursor, reacted with an organophosphorus compound in the presence of a solvent, and then introduced into a reactor together with an excess of free organophosphorus compound to form a catalytically active rhodium-organophosphorus complex catalyst. Organophosphorus compounds that form catalysts for the hydroformylation reaction with rhodium compounds include phosphites and phosphines.

[0044] Among these, the phosphite is preferably a phosphite represented by the general formula P(-OR １ ) (-OR ２ ) (-OR ３ ) (wherein, R １ , R ２ and R ３R represents an optionally substituted aryl group or an optionally substituted alkyl group. １ , R ２ and R ３ Specific examples of the alkyl group include aryl groups such as phenyl and naphthyl which may be substituted with a methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, methoxy group, etc.; aliphatic alkyl groups such as methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, etc.; alicyclic alkyl groups such as cyclopentyl and cyclohexyl which may be substituted with a lower alkyl group such as a methyl group, ethyl group, isopropyl group, n-butyl group, t-butyl group, etc.

[0045] Specific examples of suitable phosphites include, but are not limited to, tris(2-t-butylphenyl)phosphite, tris(3-methyl-6-t-butylphenyl)phosphite, tris(3-methoxy-6-t-butylphenyl)phosphite, tris(2,4-di-t-butylphenyl)phosphite, di(2-t-butylphenyl)(t-butyl)phosphite, etc. These phosphites may be used alone or in combination of two or more.

[0046] As the phosphine, alkylphosphines with large steric hindrance are particularly effective in the hydroformylation reaction of dicyclopentadiene. Representative examples include, but are not limited to, tricyclopropylphosphine, tricyclobutylphosphine, tricyclopentylphosphine, tricyclohexylphosphine, tricycloheptylphosphine, and tricyclooctylphosphine. These phosphines may be used alone or in combination of two or more.

[0047] The amount of the organophosphorus compound used in the hydroformylation reaction solution is in the range of 1 to 400 moles, preferably 3 to 200 moles, relative to the amount of rhodium metal, so that tricyclodecane dicarbaldehyde can be obtained at a sufficient hydroformylation reaction rate.

[0048] The hydroformylation reaction of dicyclopentadiene can be carried out without using a solvent, but is more preferably carried out using an organic solvent that is inert to the reaction.

[0049] After the hydroformylation reaction is completed, the reaction product solution containing tricyclodecane dicarbaldehyde is contacted with an alcohol to extract tricyclodecane dicarbaldehyde into an extraction solvent layer comprising alcohol, while leaving the catalyst components in the dihydroformylation reaction solvent layer, and then layer separation is carried out. Therefore, the hydroformylation reaction solvent is preferably one that separates from the alcohol. Examples of such solvents include aromatic hydrocarbon compounds, aliphatic hydrocarbon compounds, and alicyclic hydrocarbon compounds.

[0050] Suitable examples of aromatic hydrocarbon compounds that can be used include benzene, methylbenzenes such as toluene, xylene, mesitylene, and pseudocumene, ethylbenzenes such as ethylbenzene, diethylbenzene, and triethylbenzene, propylbenzenes such as isopropylbenzene, 1,3-diisopropylbenzene, and 1,4-diisopropylbenzene, and various other alkylbenzenes.

[0051] Examples of aliphatic hydrocarbon compounds include pentane, hexane, heptane, octane, isooctane, dodecane, and decane, but are not limited to these, as long as they are liquid at standard temperature and pressure.

[0052] As the alicyclic hydrocarbon compound, cyclohexane, cyclooctane, cyclododecane, decalin, methylcyclohexane, etc. are preferably used.

[0053] These solvents may be used alone or in combination of two or more. From the viewpoint of reaction efficiency, it is preferable to use the solvent so that the concentration of dicyclopentadiene in the reaction liquid is about 10 to 95% by mass, particularly about 30 to 90% by mass.

[0054] The amount of rhodium catalyst used is usually 10 to 5000 mass ppm, more preferably 50 to 2000 mass ppm, of rhodium metal relative to the raw material dicyclopentadiene. If rhodium is used at 50 ppm or more, it becomes necessary to recover the catalyst.

[0055] The temperature and pressure for the hydroformylation reaction of dicyclopentadiene are usually 40 to 160°C, preferably 80 to 140°C, and usually 1 to 15 MPa. If the temperature is lower than 40°C, the hydroformylation reaction rate is slow, and if it is higher than 160°C, side reactions from dicyclopentadiene and the hydroformylation reaction product in the reaction liquid proceed, resulting in a lower aldehyde yield. If the pressure is lower than 1 MPa, the hydroformylation reaction rate is slow, and if it is higher than 15 MPa, a high-pressure reaction apparatus will be used, resulting in higher equipment costs.

[0056] The molar ratio of hydrogen to carbon monoxide in the hydrogen / carbon monoxide mixed gas used in the reaction can be selected from the range of 0.2 to 5.0 as the introduced gas composition (hydrogen / carbon monoxide). If the hydrogen / carbon monoxide mixed gas is outside this range, the reaction activity or aldehyde selectivity of the hydroformylation reaction will decrease.

[0057] The hydroformylation reaction is carried out using a continuous feed method in which the starting material, dicyclopentadiene, is fed alone or as a mixed solution of dicyclopentadiene and a solvent to a reactor containing a rhodium-organophosphorus complex catalyst, a solvent, and a hydrogen / carbon monoxide mixed gas. This method reduces the production of cyclopentadiene, which inhibits the hydroformylation reaction due to thermal decomposition of dicyclopentadiene in the reactor, and maintains a good reaction rate and yield. To maintain the fluidity of dicyclopentadiene, it is preferable to dilute it with the aforementioned solvent and feed it to the reactor at a temperature at which it does not depolymerize and produce cyclopentadiene.

[0058] <Extraction of Tricyclodecane Dicarbaldehyde> After completion of the hydroformylation reaction, the reaction product liquid is contacted with an alcohol either as is or after being diluted with the hydrocarbon compound used as the hydroformylation reaction solvent in the reaction or with another hydrocarbon compound, to extract the product tricyclodecane dicarbaldehyde into the alcohol while leaving the catalyst components in the hydroformylation reaction solvent layer, followed by layer separation.

[0059] Examples of alcohols include primary alcohols having 1 to 3 carbon atoms and polyhydric alcohols having 2 to 6 carbon atoms. Primary alcohols include methanol, ethanol, and propanol. Examples of polyhydric alcohols having 2 to 6 carbon atoms include ethylene glycol, 1,3-propanediol, 1,2-propanediol, 1,4-butanediol, 1,2-butanediol, 1,3-butanediol, 2,3-butanediol, isomers of pentanediol, neopentyl glycol, hexanediol, glycerin, pentaerythritol, and trimethylolpropane. Among these, methanol, ethylene glycol, propanediol, and butanediol are preferred because they have relatively low boiling points, are inexpensive, and are easy to handle as liquids. These extraction solvents may be used alone or in combination of two or more. Extraction may be performed in the presence of water in the alcohol. The addition of water facilitates the distribution of aldehydes and catalyst components to each layer.

[0060] The reaction solvent and extraction solvent used in the hydroformylation reaction preferably have different densities to achieve effective layer separation. One suitable example of a combination of a hydroformylation reaction solvent containing tricyclodecane dicarbaldehyde and an extraction solvent is a combination of methylcyclohexane as the reaction solvent and ethylene glycol as the extraction solvent, or a combination of methylcyclohexane as the reaction solvent and methanol as the extraction solvent, and water.

[0061] The distribution of tricyclodecanedicarbaldehyde between the hydroformylation reaction solvent and the extraction solvent is equilibrium. In contrast, the catalyst components, rhodium and organophosphorus compounds, are present essentially exclusively in the hydroformylation reaction solvent, with concentrations in the extraction solvent below analytical limits. The volume ratio of the extraction solvent to the reaction product solution used is determined by the solubility of tricyclodecanedicarbaldehyde in the extraction solvent and the amount of tricyclodecanedicarbaldehyde to be extracted. For example, if the tricyclodecanedicarbaldehyde to be separated exhibits high solubility in the extraction solvent and is present at low concentrations in the reaction product solution, practical extraction of tricyclodecanedicarbaldehyde is possible using a low volume ratio (extraction solvent / reaction product solution) of extraction solvent. The higher the product concentration, the higher the volume ratio (extraction solvent / reaction product solution) required to extract tricyclodecanedicarbaldehyde from the reaction product solution. When tricyclodecane dicarbaldehyde exhibits relatively low solubility in the extraction solution, the volume ratio (extraction solvent / reaction product liquid) can vary within a range of 10:1 to 1:10. Furthermore, in order to increase the amount of tricyclodecane dicarbaldehyde extracted using a small amount of extraction solvent, it is effective to use separate extraction solvents and perform the extraction operation several times. Furthermore, in the final stage of the extraction operation, a hydroformylation reaction solvent such as methylcyclohexane may be added in an amount of approximately 5 to 20 mass% relative to the reaction product liquid. Addition of the hydroformylation reaction solvent can improve the catalyst removal rate. The temperature at which the extraction operation is performed is not particularly limited, but it is practical to perform the operation at or below the hydroformylation reaction temperature. After the reaction, the extraction solvent may be added to the hydroformylation reactor to perform the extraction operation, or the hydroformylation reaction product liquid may be withdrawn from the hydroformylation reactor and the extraction operation may be performed in an extraction tank. Alternatively, the extraction solvent may be added directly to the hydroformylation reactor to perform the extraction operation, and the catalyst components may be retained in the hydroformylation reactor to perform the subsequent hydroformylation reaction. When the hydroformylation reaction product liquid is withdrawn and the operation is carried out in an extraction tank, the reaction solvent layer of the hydrocarbon compound containing the catalyst is returned to the hydroformylation reactor and used again in the reaction. This process can be carried out as either a batch process or a continuous process.The above-described extraction procedure can yield a tricyclodecanedicarbaldehyde-containing solution containing 10 to 90% by mass of tricyclodecanedicarbaldehyde and 10 to 90% by mass of extraction solvent. When a reaction solvent is added, a tricyclodecanedicarbaldehyde-containing solution containing 5 to 90% by mass of tricyclodecanedicarbaldehyde, 5 to 90% by mass of extraction solvent, and 5 to 90% by mass of reaction solvent can be obtained. The alcohol in the extraction solvent reacts with a portion of the hydroformylation product, tricyclodecanedicarbaldehyde, to produce an acetal compound in which tricyclodecanedicarbaldehyde is acetalized. The content of the acetal compound in tricyclodecanedicarbaldehyde is typically about 0.1 to 50% by mass, and preferably about 1 to 25% by mass.

[0062] <Hydrogenation Reduction Reaction> The extract containing tricyclodecane dicarbaldehyde (tricyclodecane dicarbaldehyde-containing solution) obtained by the above extraction procedure is then subjected to hydrogenation reduction in the presence of a hydrogenation catalyst, preferably a ruthenium (Ru) catalyst, to produce TCDDM according to the following reaction formula (V). By carrying out this hydrogenation reduction reaction in the presence of water and a Ru catalyst, the acetal compound is rapidly converted to tricyclodecane dicarbaldehyde during the hydrogenation reaction of tricyclodecane dicarbaldehyde, and the tricyclodecane dicarbaldehyde converted from the acetal compound is hydrogenated, thereby making it possible to produce TCDDM in a high yield, which is preferable.

[0063] The amount of water present in the hydrogenation reduction reaction is preferably equal to or greater than the amount of the acetal compound in the hydrogenation reduction reaction solution, and is an amount that does not cause phase separation of the reaction solution. The water content of the entire reaction solution is preferably 2% by mass or more, preferably 2 to 30% by mass, more preferably 5 to 25% by mass, and particularly preferably 10 to 20% by mass. When the water content is within the above range, phase separation between the water and the reaction solvent does not occur, and the above-mentioned effects achieved by the presence of water in the hydrogenation reaction system can be effectively obtained. This water addition may be carried out in an extraction step in which the catalyst component and tricyclodecane dicarbaldehyde are separated from the hydroformylation reaction product solution, or water may be added to the reaction system immediately before the hydrogenation reduction reaction.

[0064] The reaction can be carried out in a batchwise manner by loading the catalyst as a slurry into a stirred reactor and separating the catalyst from the product liquid by settling and filtering after the reaction, or by a trickle reaction in which a molded catalyst is loaded into a tubular reactor and the product liquid and hydrogen gas are passed over the catalyst. The amount of catalyst used is not particularly limited as long as it allows the production of TCDDM with industrially advantageous productivity. The reaction temperature and pressure for the hydroreduction reaction are typically 40 to 200°C, preferably 70 to 150°C, and the reaction pressure is typically 15 MPa or less. Temperatures below 40°C slow the hydroreduction reaction rate, while temperatures above 200°C cause side reactions of the target TCDDM, resulting in a reduced TCDDM yield. Pressures above 15 MPa require the use of a high-pressure reactor, which increases the equipment costs.

[0065] <Removal of Residual Metals> The crude reaction solution obtained by the above hydrogenation reduction reaction operation contains metal elements derived from the hydrogenation catalyst as eluted components. By removing the metal elements from the crude reaction solution prior to distillation purification, it is possible to suppress thermal decomposition of TCDDM caused by the metal elements in the distillation purification step. There are no particular limitations on the method for removing metal elements from the crude reaction solution to reduce their content, and examples include activated carbon treatment, cation exchange resin, and silica gel adsorption. Activated carbon treatment is preferred because of its removal efficiency and the ability to reuse the adsorbent.

[0066] The activated carbon treatment method may be a batch process in which activated carbon is added to the crude reaction solution and stirred, followed by solid-liquid separation of the activated carbon by filtration or the like, or a continuous process in which the crude reaction solution is passed through an activated carbon-packed column. In the case of batch treatment, the amount of activated carbon added to the crude reaction solution is determined appropriately depending on the metal element adsorption capacity of the activated carbon, the metal element content in the crude reaction solution, and the like. Generally, activated carbon is preferably added to the crude reaction solution to a concentration of approximately 0.01 to 10 mass% and stirred. In the case of continuous treatment, the treatment flow rate is not particularly limited, but it is sufficient to treat at a length of space velocity (LHSV) of 1 to 10. Such activated carbon treatment may be performed multiple times. That is, the activated carbon-treated solution obtained by treating the crude reaction solution with activated carbon may be treated with activated carbon again. In this case, the type and amount of activated carbon used, treatment conditions, etc., used in the first activated carbon treatment and the second activated carbon treatment may be different from each other.

[0067] The lower the metal element content of the crude reaction liquid to be subjected to the next step of distillation purification, the more preferable it is from the viewpoint of suppressing thermal decomposition of TCDDM. The metal element content of the crude reaction liquid to be subjected to distillation purification is preferably 10 ppm by mass or less, particularly 5 ppm by mass or less, and particularly 1 ppm by mass or less. The pH of the crude reaction liquid to be subjected to distillation purification is preferably within the range of 6 to 8. A lower limit of pH of 6 or more is preferred because it suppresses the by-production of low-boiling compounds thought to be due to dehydration of TCDDM and high-boiling compounds thought to be due to dimerization such as etherification. An upper limit of pH of 8 or less is preferred because it makes the distillation purification equipment less susceptible to alkali corrosion.

[0068] Usually, the pH of the reaction product liquid obtained by the hydrogenation reduction reaction is 6 to 8, and even if this is subjected to treatment for removing the hydrogenation catalyst and treatment for removing metal elements, the pH remains almost unchanged. However, there are cases where the pH falls outside the range of 6 to 8 due to acid or alkali components eluted from the hydrogenation catalyst. In such cases, it is preferable to adjust the pH to 6 to 8 by adding a pH adjuster such as an acid or alkali as appropriate.

[0069] <Distillation> The crude reaction liquid with the reduced metal element content is then subjected to distillation purification. This distillation purification is preferably carried out using a distillation column having 10 to 30 theoretical plates and a column bottom temperature in the range of 150 to 250°C.

[0070] If the distillation column used for distillation purification has 10 or more theoretical plates, it is easy to separate the impurities from the product, and if it has 30 or fewer plates, the pressure difference between the top and bottom of the column is small, resulting in a low column bottom temperature, thereby reducing the heat load on the equipment. A more preferred number of theoretical plates is 15 to 30. If the column bottom temperature is 150°C or higher, it is possible to volatilize TCDDM, and if it is 250°C or lower, it is possible to suppress the by-production of high-boiling impurities due to dimerization of TCDDM. A more preferred column bottom temperature is 160 to 230°C.

[0071] There are no particular limitations on other conditions for the distillation column in distillation purification, but distillation is usually carried out at a pressure of 0.1 to 100 kPa and a reflux ratio of about 1 to 30. In particular, by controlling the reflux ratio and the amount of distillate, it becomes possible to adjust the abundance ratios of chiral compound A, chiral compound B, and chiral compound C in the resulting TCDDM composition. These conditions may be changed as desired depending on the equipment performance, vessel efficiency, recovery amount, etc. of the distillation column, and are not particularly limited as long as a TCDDM composition having the composition specified in this embodiment is obtained.

[0072] The bottom liquid of the distillation column obtained by such distillation purification may be further subjected to simple distillation at 0.1 to 10 kPa and 140 to 250° C. By such distillation purification, a TCDDM composition having a TCDDM purity of 98% or more can usually be obtained in high yield.

[0073] <UV-Curable Composition> The UV-curable composition of this embodiment is derived from the TCDDM composition of this embodiment. More specifically, the UV-curable composition of this embodiment is synthesized using the TCDDM composition of this embodiment as a raw material. Even more specifically, the UV-curable composition of this embodiment is synthesized using tricyclodecane dimethanol contained in the TCDDM composition of this embodiment as a raw material. The UV-curable composition can be produced by any conventional method without any particular limitations. In general, it is desirable to use the tricyclodecane dimethanol contained in the TCDDM composition as a raw material to produce a di(meth)acrylic acid ester derivative, a urethane acrylate, or other derivative. Both of the two hydroxy groups of the tricyclodecane dimethanol contained in the TCDDM composition may be used in the reaction, or one of the hydroxy groups may be reacted, leaving the other hydroxy group. In this case, the remaining hydroxy group may be converted to a functional group suitable for the intended use using an organic synthetic method. Specific methods for producing a di(meth)acrylic acid ester derivative from TCDDM using a TCDDM composition as a raw material include a method of reacting TCDDM with (meth)acrylic acid, a method of subjecting TCDDM to a transesterification reaction with a (meth)acrylic acid ester, and a method of reacting TCDDM with a halide of (meth)acrylic acid, such as (meth)acrylic acid chloride.

[0074] The reaction conditions for each of the above production methods are as follows. When a di(meth)acrylic acid ester derivative is produced using (meth)acrylic acid or a (meth)acrylic acid ester, the reaction can be promoted by using a catalyst and continuously removing the produced water or lower alcohol from the system. Examples of the catalyst include known esterification catalysts such as sulfuric acid, paratoluenesulfonic acid, boron trifluoride, and organotin compounds, and any catalyst can be selected and used. The amount of catalyst used is preferably 10 to 100,000 ppm relative to the total mass of the reaction substrates, from the viewpoints of reducing the load on the production equipment and reducing catalyst costs. When a di(meth)acrylic acid ester derivative is produced using a halide of (meth)acrylic acid, the reaction is preferably carried out in the presence of a basic compound, and the reaction can also be promoted using a catalyst. Examples of the basic compound include known basic compounds such as tertiary amines such as triethylamine and N-ethyldiisopropylamine, phosphates such as potassium phosphate and sodium phosphate, carbonates such as potassium carbonate and sodium carbonate, hydroxides such as potassium hydroxide and sodium hydroxide, and any of these can be selected and used. From the viewpoints of reducing the load on the production equipment and reducing raw material costs, the amount of the basic compound used is preferably 1.0 to 6.0 equivalents per equivalent of the halide of acrylic acid or methacrylic acid.

[0075] The catalyst may be any catalyst known for use in the esterification reaction of acid chlorides, such as pyridines such as N,N-dimethyl-4-aminopyridine, imidazoles such as N-methylimidazole, and tertiary amines such as triethylenediamine. The amount of catalyst used is preferably 10 to 100,000 ppm relative to the total mass of the reaction substrates, from the viewpoints of reducing the load on the production equipment and reducing catalyst costs.

[0076] In each of the above production methods, it is preferable to add a polymerization inhibitor to prevent thermal polymerization of (meth)acrylic acid, a (meth)acrylic acid ester, or a halide of (meth)acrylic acid.

[0077] Examples of the polymerization inhibitor include hydroquinone, paramethoxyphenol, 2,4-dimethyl-6-t-butylphenol, 3-hydroxythiophenol, α-nitroso-β-naphthol, parabenzoquinone, 2,5-dihydroxyparabenzoquinone, copper salts, phenothiazine, paraphenylenediamine, phenyl-β-naphthylamine, etc. The amount of the polymerization inhibitor used is preferably 10 to 100,000 ppm relative to the total mass of the reaction substrates, from the viewpoints of catalytic activity and reducing the influence on side reactions.

[0078] In each of the above production methods, the reaction temperature is preferably −20° C. or higher, more preferably 0° C. or higher, and is preferably 120° C. or higher, more preferably 100° C. or lower, from the viewpoint of shortening the reaction time and preventing polymerization. The reaction time is preferably 1 hour or longer, and preferably 20 hours or shorter.

[0079] A solvent can also be used in the reaction in each of the above production methods. The solvent is not particularly limited as long as it does not adversely affect the reaction, and examples include aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, and mesitylene; aliphatic hydrocarbons such as pentane, hexane, heptane, octane, nonane, decane, cyclohexane, and cyclooctane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, carbon tetrachloride, chlorobenzene, and trifluoromethylbenzene; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, anisole, tetrahydrofuran, and dioxane; ketones such as methyl ethyl ketone, diethyl ketone, and methyl isobutyl ketone; esters such as ethyl acetate and isopropyl acetate; nitriles such as acetonitrile; acyclic or cyclic amides such as dimethylformamide and N-methylpyrrolidinone; and acyclic or cyclic sulfoxides or sulfones such as dimethyl sulfoxide. These solvents may be used alone or in combination of two or more.

[0080] The structure of the urethane acrylate made from the TCDDM composition is not particularly limited as long as it is an acrylic acid or methacrylic acid ester derivative containing a urethane bond.

[0081] A preferred method for producing a urethane acrylate from TCDDM using a TCDDM composition as a raw material is to react the TCDDM composition, a polyisocyanate compound, and a monohydroxyacrylate compound in the presence of a catalyst. Furthermore, a polyol compound other than the TCDDM composition may be added to adjust the performance of the cured product. From the viewpoint of the hardness and heat resistance of the cured product, the content of the TCDDM composition relative to the total mass of the reaction substrate as a urethane acrylate raw material is preferably 10% by mass or more, more preferably 20% by mass or more, and even more preferably 30% by mass or more. Meanwhile, the upper limit of this content is not particularly limited, and a higher content is preferable.

[0082] Examples of the polyisocyanate compound include paraphenylene diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 2,2'-diphenylmethane diisocyanate, 2,4-diphenylmethane diisocyanate, 4,4'-diphenylmethane diisocyanate, diphenylether-4,4'-diisocyanate, o-xylylene diisocyanate, m-xylylene diisocyanate, p-xylylene diisocyanate, norbornenemethane diisocyanate, and hydrogenated versions thereof, pentamethylene diisocyanate, hexamethylene diisocyanate, dicyclohexylmethane diisocyanate, 1,4-cyclohexane diisocyanate, and isophorone diisocyanate. These compounds may be used in the form of nurates, adducts, or biurets, or as dimers or trimers. These compounds may be used alone or in combination of two or more.

[0083] In the monohydroxyacrylate compound, the structural moiety that bonds the hydroxy group and the acryloyloxy group is preferably composed of three or more carbon atoms. Examples of such compounds include acrylate compounds of aliphatic polyols having 3 or more carbon atoms, such as hydroxypropyl acrylate, trimethylolpropane diacrylate, pentaerythritol triacrylate, ditrimethylolpropane triacrylate, and dipentaerythritol pentaacrylate; (poly)oxyalkylene modified compounds in which a (poly)oxyalkylene chain such as a (poly)oxyethylene chain, a (poly)oxypropylene chain, or a (poly)oxytetramethylene chain has been introduced into the molecular structure of the acrylate compound; lactone modified compounds in which a (poly)lactone structure has been introduced into the molecular structure of the acrylate compound; isocyanuric acid diacrylate; (poly)oxyalkylene modified compounds in which a (poly)oxyalkylene chain such as a (poly)oxyethylene chain, a (poly)oxypropylene chain, or a (poly)oxytetramethylene chain has been introduced into the molecular structure of isocyanuric acid diacrylate; and lactone modified compounds in which a (poly)lactone structure has been introduced into the molecular structure of isocyanuric acid diacrylate. Further, methacrylate compounds in which the acrylate of the above-mentioned compound group is replaced with methacrylate may also be used. These may be used alone or in combination of two or more kinds.Examples of polyol compounds other than the TCDDM composition include linear diols such as ethylene glycol, 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, and 1,6-hexanediol; branched diols such as 2-methyl-1,3-propanediol, 2,2-dimethyl-1,3-propanediol, 1,4-dimethylolhexane, 2-ethyl-1,3-hexanediol, 2,2,4-trimethyl-1,3-pentanediol, and dimer diol; diethylene glycol; propylene glycol; Examples of the polyol compounds include diols having an ether group such as 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, 1,4-dihydroxyethylcyclohexane, and other diols having an alicyclic structure, xylylene glycol, 1,4-dihydroxyethylbenzene, 4,4'-methylenebis(hydroxyethylbenzene), and other diols having an aromatic group, glycerin, trimethylolpropane, pentaerythritol, and other polyols, polyether polyols, polyester polyols, polycarbonate polyols, etc. These polyol compounds may be used alone or in combination of two or more.

[0084] Examples of the catalyst include organic tin compounds such as dibutyltin dilaurate, trimethyltin hydroxide, and tetra-n-butyltin; organic bismuth compounds such as dibutylbismuth dilaurate and dioctylbismuth dilaurate; metal salts such as zinc octoate, tin octoate, cobalt naphthenate, stannous chloride, and stannic chloride; and amine catalysts such as triethylamine, benzyldiethylamine, 1,4-diazabicyclo[2,2,2]octane, 1,8-diazabicyclo[5,4,0]undecene, N,N,N',N'-tetramethyl-1,3-butanediamine, and N-ethylmorpholine.

[0085] It is preferable to add a polymerization inhibitor to prevent thermal polymerization of the monohydroxyacrylate compound, etc. The polymerization inhibitor is not particularly limited as long as it does not inhibit the reaction, and examples thereof include hydroquinone, paramethoxyphenol, 2,4-dimethyl-6-t-butylphenol, 3-hydroxythiophenol, α-nitroso-β-naphthol, parabenzoquinone, 2,5-dihydroxyparabenzoquinone, copper salts, phenothiazine, paraphenylenediamine, and phenyl-β-naphthylamine. The amount of polymerization inhibitor used is preferably 10 to 100,000 ppm relative to the total mass of the reaction substrates, from the viewpoints of catalytic activity and reducing the influence on side reactions.

[0086] In the above production method, the reaction temperature is preferably 30° C. or higher, more preferably 40° C. or higher, and is preferably 120° C. or lower, more preferably 100° C. or lower, from the viewpoint of shortening the reaction time and preventing polymerization. The reaction time is preferably 1 hour or longer, and preferably 10 hours or shorter.

[0087] A solvent can also be used in the reaction in each of the above production methods. The solvent is not particularly limited as long as it does not adversely affect the reaction, and examples include aromatic hydrocarbons such as benzene, toluene, xylene, ethylbenzene, and mesitylene; aliphatic hydrocarbons such as heptane, octane, nonane, decane, cyclohexane, and cyclooctane; halogenated hydrocarbons such as dichloromethane, chloroform, 1,2-dichloroethane, carbon tetrachloride, chlorobenzene, and trifluoromethylbenzene; ethers such as diisopropyl ether, dibutyl ether, anisole, tetrahydrofuran, and dioxane; ketones such as methyl ethyl ketone, diethyl ketone, and methyl isobutyl ketone; esters such as ethyl acetate and isopropyl acetate; nitriles such as acetonitrile; acyclic or cyclic amides such as dimethylformamide and N-methylpyrrolidinone; and acyclic or cyclic sulfoxides or sulfones such as dimethyl sulfoxide. These solvents may be used alone or in combination of two or more.

[0088] The ultraviolet-curable composition of this embodiment is synthesized using the TCDDM composition of this embodiment as a raw material, and therefore can be controlled to a high viscosity without impairing the performance originally required of an ultraviolet-curable composition, and has excellent coating stability. Therefore, the ultraviolet-curable composition of this embodiment can be suitably used for hard coating materials, antifouling coating materials, resist materials, inkjet inks, 3D printer materials, and the like.

[0089] In applications such as resists, a method is used in which the ultraviolet-curable composition is applied to a substrate by screen printing, flexible printing, or the like, and then cured. From the viewpoints of being able to apply the composition thinly and uniformly, being able to apply it thickly, and being able to print fine patterns on the substrate with high precision, the ultraviolet-curable composition is required to have high viscosity.

[0090] In applications such as hard coatings, antifouling coatings, and inkjet printing, the ultraviolet-curable composition is applied to a substrate by a coater method, a spray method, or a dispenser method, and then cured. From the viewpoint of accurately discharging a fixed amount of the ultraviolet-curable composition, the ultraviolet-curable composition is required to have a high viscosity.

[0091] The ultraviolet-curable composition of the present embodiment can be suitably used for applications such as hard coating materials, antifouling coating materials, resist materials, inkjet inks, and materials for 3D printers.

[0092] <Polymer Composition> The polymer composition of this embodiment is a polymer composition derived from the TCDDM composition of this embodiment, or a polymer composition derived from the ultraviolet-curable composition of this embodiment.

[0093] More specifically, the polymer composition of this embodiment is a polymer composition obtained by polymerizing the TCDDM composition of this embodiment or a composition containing the TCDDM composition, and includes a polymer containing structural units derived from tricyclodecane dimethanol in the TCDDM composition. The polymer composition of this embodiment is also a composition containing a polymer obtained by polymerizing the ultraviolet-curable composition of this embodiment. One embodiment of the polymer composition of this embodiment may be the polymer composition itself, or may be a polymer composition obtained by adding or removing an appropriate amount of a solvent such as water or an organic solvent to adjust the solids concentration, or may be a polymer composition obtained by removing the solvent and drying to obtain a solid. Furthermore, the polymer composition may be a polymer composition obtained by purifying a composition containing a polymer obtained by polymerization and appropriately removing impurities. If necessary, the polymer composition may further include appropriate additives, such as storage stabilizers (e.g., ultraviolet absorbers and antioxidants), colorants, antistatic agents, lubricants, fillers, flame retardants, and foaming agents, within limits that do not affect the performance of the polymer obtained by polymerization.

[0094] That is, the polymer composition of this embodiment may contain a polymer obtained by polymerizing the TCDDM composition of this embodiment or the UV-curable composition of this embodiment, and is not particularly limited in terms of its form, component composition, etc. Another embodiment of the polymer composition specifically includes at least one resin selected from the group consisting of polyester-based resins, epoxy-based resins, acrylate-based resins, polycarbonate-based resins, and polyurethane-based resins. In this embodiment, the polyester-based resin is a resin primarily composed of a polyethylene-based polymer such as polyethylene terephthalate (PET). The polyethylene-based polymer is not particularly limited, and refers to, for example, a polymer containing structural units derived from a polyol primarily containing glycol and structural units derived from a terephthalic acid compound, and also containing structural units derived from tricyclodecane dimethanol in the TCDDM composition of this embodiment.

[0095] In this embodiment, the epoxy resin is a resin containing an epoxy polymer as a main component. The epoxy polymer is not particularly limited, and examples thereof include a polymer containing structural units derived from a bisphenol compound and structural units derived from epichlorohydrin, and also containing structural units derived from tricyclodecane dimethanol in the TCDDM composition of this embodiment.

[0096] In this embodiment, the acrylate resin is a resin containing an acrylate polymer as a main component. The acrylate polymer is not particularly limited, and examples thereof include a polymer containing a structural unit derived from (meth)acrylic acid or a structural unit derived from a (meth)acrylic acid derivative, and containing a structural unit derived from tricyclodecane dimethanol in the TCDDM composition of this embodiment.

[0097] In this embodiment, the polycarbonate-based resin refers to a resin primarily composed of a polycarbonate-based polymer. The polycarbonate-based polymer is not particularly limited, and examples thereof include polymers containing structural units derived from bisphenol compounds, structural units derived from phosgene (carbonyl chloride), or structural units derived from diphenyl carbonate, and containing structural units derived from tricyclodecane dimethanol in the TCDDM composition of this embodiment. In this embodiment, the polyurethane-based resin refers to a resin primarily composed of a polyurethane-based polymer. The polyurethane-based polymer is not particularly limited, and examples thereof include polymers containing structural units derived from a glycol-based polyol and structural units derived from a bifunctional isocyanate, and containing structural units derived from tricyclodecane dimethanol in the TCDDM composition of this embodiment.

[0098] The second embodiment of the present invention will now be described in detail.

[0099] [Method for producing a TCDDM composition stored in a container] The method for producing a tricyclodecane dimethanol composition stored in a container of the present invention comprises storing a tricyclodecane dimethanol composition (A0) containing tricyclodecane dimethanol obtained by distillation purification (hereinafter sometimes referred to as "TCDDM composition (A0)") in a container while maintaining the temperature at not less than 45°C, wherein the tricyclodecane dimethanol contains a chiral compound one enantiomer of which is represented by formula (A) (hereinafter sometimes referred to as "chiral compound A"). Hereinafter, tricyclodecane dimethanol will also be referred to as "TCDDM". The above-described configuration effectively prevents the TCDDM composition from becoming cloudy during storage. Furthermore, it effectively prevents a decrease in the fluidity of the TCDDM composition. For convenience, the TCDDM composition stored in a container will be referred to herein as TCDDM composition (A1) stored in a container. Furthermore, the TCDDM composition stored in a container (A1) immediately before being introduced into a processing machine after transportation and / or storage may be referred to herein as TCDDM composition (A2).

[0100] Depending on its thermal history and handling conditions, a TCDDM composition may become cloudy during storage or its fluidity may decrease, making it difficult to handle. Under these circumstances, the inventors conducted detailed studies and found that repeated heating and cooling can cause the TCDDM composition to become cloudy and its fluidity to decrease. Specifically, chiral compounds in which one enantiomer is represented by formula (A) tend to crystallize and are prone to forming microcrystals upon cooling. The formation of microcrystals of TCDDM, such as chiral compound A, can cause the TCDDM composition to become cloudy and its fluidity to decrease. As a result, the TCDDM composition becomes difficult to handle. In this invention, the term "microcrystals" refers to minute particles with an average particle size of submicrons or less that are composed of TCDDM, such as chiral compound A, and that exhibit a microscopic structure as detected by the dynamic light scattering method described below.

[0101] [TCDDM composition (A0)] Next, tricyclodecane dimethanol composition (A0) (TCDDM composition (A0)) containing a chiral compound of which one enantiomer is represented by formula (A) will be described. TCDDM composition (A0) of the present invention is a composition obtained by distillation purification and containing a chiral compound of which one enantiomer is represented by the following formula (A) (chiral compound A):

[0102] The TCDDM composition (A0) of the present invention may contain, in addition to chiral compound A, tricyclodecane dimethanol, one enantiomer of which is represented by the following formula (B) (sometimes referred to herein as "chiral compound B"). That is, the more chiral compound A is contained, the more TCDDM microcrystals are produced in the TCDDM composition (A0), and the TCDDM composition (A0) tends to have appropriate fluidity and be excellent in handling during blending operations, etc. Furthermore, the more chiral compound B is contained, the relatively lower the proportion of chiral compound A is, and the more TCDDM microcrystals in the TCDDM composition (A0) are reduced or the increase in TCDDM microcrystals is suppressed, which makes it less likely for the viscosity to increase during storage and tends to improve storage stability.

[0103]

[0104] Furthermore, the TCDDM composition (A0) of the present invention may contain, in addition to chiral compound A and chiral compound B, and / or chiricyclodecane dimethanol, one enantiomer of which is represented by formula (C) (sometimes referred to herein as "chiral compound C"). That is, the greater the amount of chiral compound C, the relatively lower the proportion of chiral compound A, which reduces the amount of TCDDM microcrystals in the TCDDM composition (A0) or suppresses the increase of TCDDM microcrystals, making it less likely for the viscosity to increase during storage and tending to improve storage stability.

[0105]

[0106] (Content of chiral compound A) In the TCDDM composition (A0) of the present invention, there is no particular lower limit to the content of chiral compound A. However, from the viewpoint of excellent handling in blending operations and the like, because microcrystals are formed in the TCDDM composition (A0) and appropriate fluidity can be ensured, the content is preferably 25% by mass or more, more preferably 28% by mass or more, even more preferably 30% by mass or more, still more preferably 32% by mass or more, even more preferably 33% by mass or more, still more preferably 34% by mass or more, particularly more preferably 35% by mass or more, and most particularly more preferably 36% by mass or more, relative to the total mass of the TCDDM composition (A0) (100% by mass). Furthermore, the upper limit of the content of chiral compound A is not particularly limited, but from the viewpoints of suppressing the formation of TCDDM microcrystals in the TCDDM composition (A0), suppressing an increase in viscosity during storage, and improving storage stability, it is preferably 54% by mass or less, more preferably 50% by mass or less, even more preferably 45% by mass or less, still more preferably 43% by mass or less, even more preferably 41% by mass or less, still more preferably 40% by mass or less, particularly more preferably 39% by mass or less, and even more particularly more preferably 38.5% by mass or less. The above upper and lower limits can be combined as desired. For example, in TCDDM composition (A0), the content of chiral compound A is not particularly limited, but is preferably 25% by mass or more and 54% by mass or less, more preferably 28% by mass or more and 50% by mass or less, even more preferably 30% by mass or more and 45% by mass or less, even more preferably 32% by mass or more and 43% by mass or less, even more preferably 33% by mass or more and 41% by mass or less, even more preferably 34% by mass or more and 40% by mass or less, particularly more preferably 35% by mass or more and 39% by mass or less, and even particularly more preferably 36% by mass or more and 38.5% by mass or less, relative to the total mass of TCDDM composition (A0) (100% by mass). Note that, although Example 2-1 described below was carried out under conditions outside the preferred range of the content, the effects of the present invention can be obtained at a content within the above preferred range.

[0107] (Content of chiral compound B) In the TCDDM composition (A0) of the present invention, there is no particular lower limit to the content of chiral compound B. From the viewpoints of suppressing the formation of TCDDM microcrystals in the TCDDM composition (A0), suppressing an increase in viscosity during storage, and improving storage stability, the content of chiral compound B is preferably 1.6% by mass or more, more preferably 1.8% by mass or more, even more preferably 2.0% by mass or more, still more preferably 2.1% by mass or more, even more preferably 2.2% by mass or more, and even more preferably 2.3% by mass or more, relative to the total mass of TCDDM composition (A0) (100% by mass). Furthermore, although there is no particular upper limit to the content of chiral compound B in TCDDM composition (A0), from the viewpoint of producing TCDDM microcrystals in TCDDM composition (A0) and ensuring appropriate fluidity, thereby providing superior handling in blending operations and the like, the content is preferably 4.8% by mass or less, more preferably 4.6% by mass or less, even more preferably 4.4% by mass or less, still more preferably 4.3% by mass or less, even more preferably 4.2% by mass or less, still more preferably 4.0% by mass or less, and further preferably 3.8% by mass or less, 3.5% by mass or less, 3.2% by mass or less, 3.0% by mass or less, 2.8% by mass or less, and 2.7% by mass or less, relative to the total mass (100% by mass) of TCDDM composition (A0). The above upper and lower limits can be combined in any order. For example, in TCDDM composition (A0), the content of chiral compound B is not particularly limited, but is preferably 1.6% by mass to 4.8% by mass, more preferably 1.8% by mass to 4.6% by mass, even more preferably 2.0% by mass to 4.4% by mass, still more preferably 2.1% by mass to 4.3% by mass, even more preferably 2.2% by mass to 4.2% by mass, and even more preferably 2.3% by mass to 4.0% by mass, relative to 100% by mass of the total mass of TCDDM composition (A0). Note that, in Example 2-1 described below, the experiment was carried out under conditions outside the preferred range of the content, but the effects of the present invention can be obtained at a content within the preferred range.

[0108] (Content of chiral compound C) In the TCDDM composition (A0) of the present invention, there is no particular lower limit to the content of chiral compound C. However, from the viewpoints of suppressing the formation of TCDDM microcrystals in the TCDDM composition (A0), suppressing an increase in viscosity during storage, and improving storage stability, the content is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 18% by mass or more, still more preferably 20% by mass or more, even more preferably 22% by mass or more, and even more preferably 25% by mass or more, relative to the total mass of the TCDDM composition (A0) (100% by mass). Furthermore, although there are no particular limitations on the upper limit of the content of chiral compound C in TCDDM composition (A0), from the viewpoint of producing TCDDM microcrystals in TCDDM composition (A0) and ensuring appropriate fluidity, and therefore superior handling in blending operations and the like, the content is preferably 45% by mass or less, more preferably 40% by mass or less, even more preferably 38% by mass or less, still more preferably 35% by mass or less, even more preferably 33% by mass or less, and even more preferably 30% by mass or less, relative to the total mass of TCDDM composition (A0) (100% by mass). The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A0), the content of chiral compound C is not particularly limited, but is preferably 10% by mass to 45% by mass, more preferably 15% by mass to 40% by mass, even more preferably 18% by mass to 38% by mass, even more preferably 20% by mass to 35% by mass, even more preferably 22% by mass to 33% by mass, and even more preferably 25% by mass to 30% by mass, relative to the total mass of TCDDM composition (A0) (100% by mass). Note that, in Example 2-1 described below, the experiment was carried out under conditions outside the preferred range of the content, but the effects of the present invention can be obtained at a content within the preferred range.

[0109] (TCDDM Content in TCDDM Composition) In TCDDM composition (A0), there is no particular lower limit to the total TCDDM content, but from the viewpoint of ease of handling the composition, it is preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, still more preferably 95% by mass or more, even more preferably 97% by mass or more, and still more preferably 99% by mass or more, relative to 100% by mass of the total mass of TCDDM composition (A0). On the other hand, there is no particular upper limit to the total TCDDM content in TCDDM composition (A0), and a higher value is preferable, and it may even be 100% by mass, relative to the total mass of TCDDM composition (A0).

[0110] The TCDDM composition (A0) of the present invention may contain compounds other than TCDDM as long as the effects of the present invention are not impaired. The "compounds other than TCDDM" are not particularly limited, and examples include compounds having an aldehyde group that are reaction intermediates during TCDDM synthesis, compounds having a carbonyl group derived from compounds containing the aldehyde group, diols containing 12 carbon atoms that are mixed in during the manufacturing process, and known additives that are blended as needed. The content of the compounds other than TCDDM in the TCDDM composition (A0) of the present invention is not particularly limited as long as the effects of the present invention are not impaired. Typically, the content can be 0.01% by mass or more and 2% by mass or less, based on the total mass of the TCDDM composition (A0) (100% by mass). Alternatively, the composition may contain no compounds other than TCDDM (0% by mass).

[0111] (Total Content of Chiral Compounds A to C) In TCDDM composition (A0), the lower limit of the total content of chiral compound A, chiral compound B, and chiral compound C is not particularly limited, but from the viewpoint of handleability of the composition, it is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more, relative to 100% by mass of the total mass of TCDDM composition (A0). On the other hand, the upper limit of this total content is not particularly limited, and a higher value is preferable, and it may be 100% by mass, relative to the total mass of TCDDM composition (A0).

[0112] It is preferable that TCDDM composition (A0) is substantially free of a flavor carrier. When TCDDM composition (A0) is substantially free of a flavor carrier, the resulting TCDDM composition tends to be more inhibited from becoming cloudy or losing fluidity. The phrase "substantially free of a flavor carrier" means that a flavor carrier is not intentionally added, and specifically means that the content of the flavor carrier in TCDDM composition (A0) is 5% by mass or less, preferably 1% by mass or less, more preferably 0.1% by mass or less, and even more preferably 0.01% by mass or less, relative to the total mass of TCDDM composition (A0).

[0113] Hereinafter, a method for producing a tricyclodecane dimethanol (TCDDM) composition stored in a container according to the present invention, and a method for processing the TCDDM composition (A1) stored in the container will be described with reference to FIGS. 2 and 3.

[0114] (1) and (2) shown in Figures 2 and 3 are schematic process diagrams illustrating an example of a method for producing TCDDM composition (A1) stored in container 3 according to the present invention. (3) shown in Figure 2 illustrates an example of a subsequent transport and / or storage process for TCDDM composition (A1) obtained by the production method of the present invention and stored in a container. (4) shown in Figures 2 and 3 illustrate examples of subsequent processing steps for the TCDDM composition after (3) shown in Figure 2 and the TCDDM composition (A1) obtained in (2) shown in Figure 2, respectively. Hereinafter, (1) to (4) shown in Figure 2 will be referred to as steps (1) to (4), respectively.

[0115] Step (1) is specifically a production step for TCDDM composition (A0) in which TCDDM composition purified by distillation is stored in storage tank 2 and treated as TCDDM composition (A0). Step (2) is specifically a step of storing TCDDM composition (A0) in container 3 to obtain TCDDM composition (A1) stored in container 3. Step (3) is specifically a step including at least one of a transport step and a storage step for TCDDM composition (A1) stored in the container. Step (4) is specifically a step of introducing part or all of TCDDM composition (A1) after step (3) into processing machine (X) in FIG. 2 , and a step of introducing part or all of TCDDM composition (A1) obtained in step (2) into processing machine (X) in FIG. 3 . After step (4), TCDDM composition (A2) or TCDDM composition (A1) supplied to processing machine (X) is processed in processing machine (X).

[0116] In the method for producing the TCDDM composition stored in a container of the present invention (hereinafter referred to as the "method for producing the TCDDM composition of the present invention" or simply the "production method of the present invention"), steps (3) and (4) are not essential. Needless to say, not all of steps (1) to (4) are essential in the method for producing the TCDDM composition of the present invention. Each of the above steps will be described in detail below.

[0117] (Step (1)) Step (1) shown in Figure 2 is a production step for the starting material TCDDM composition (A0). The production of TCDDM composition (A0) can be carried out by a known method. The TCDDM composition (A0) of the present invention can be obtained, for example, through a step of hydroformylating dicyclopentadiene to obtain tricyclodecane dicarbaldehyde, a step of reducing the tricyclodecane dicarbaldehyde to obtain a crude reaction solution containing tricyclodecane dimethanol (TCDDM), and a step of purifying the crude reaction solution by distillation. For details of these steps, please refer to paragraphs

[0046] to

[0017] of WO 2023 / 176641, the contents of which are incorporated herein by reference. As a specific embodiment, in Figures 2 and 3, there is shown a method in which the crude reaction solution is purified by distillation using a distillation purification column 1, and the purified TCDDM composition is recovered in a storage tank 2 to obtain TCDDM composition (A0).

[0118] (Step (2)) Step (2) shown in Figures 2 and 3 includes transferring and storing the TCDDM composition (A0) obtained in step (1) in container 3 while maintaining the temperature above 45°C, thereby obtaining TCDDM composition (A1) containing chiral compound A, which is stored in a container. Ideally, the TCDDM composition (A0) is used immediately after distillation. For example, it is desirable to feed the TCDDM composition (A0) immediately after distillation into processing machine (X). However, from a commercial and economical perspective, TCDDM composition (A0) is usually stored in container 3 in step (2), as shown in Figure 2, to obtain TCDDM composition (A1). The obtained TCDDM composition (A1) is transported or stored in the state stored in container 3 in step (3), which will be described later, and then fed into processing machine (X). Furthermore, the TCDDM composition (A1) stored in container 3 may be stored in a warehouse or the like before or after transportation. Alternatively, as shown in Figure 3, TCDDM composition (A0) is stored in container 3 in step (2) to obtain TCDDM composition (A1). The obtained TCDDM composition (A1) may be charged into processing machine (X) without going through step (3). For reasons that will be described later, TCDDM composition (A1) obtained by the TCDDM composition production method of the present invention is suitable for charging the TCDDM composition (A1) stored in a container described above into a processing machine after storage and transportation, or for charging it directly into a processing machine.

[0119] (Temperature until TCDDM composition (A0) is stored in container) In the method for producing a TCDDM composition of the present invention, the TCDDM composition (A0) obtained by distillation and purification is stored in container 3 while maintaining a temperature not lower than 45°C. By storing the distillation-purified TCDDM composition (A0) in container 3 while maintaining a temperature not lower than 45°C in this manner, clouding of the TCDDM composition (A0) can be effectively prevented. This is presumably because the suppression of the formation of microcrystals in the TCDDM composition (A0) and the suppression of an increase in viscosity can be used to maintain good storage stability of the TCDDM composition (A0). As a result, it becomes possible to more efficiently produce organic materials using the TCDDM composition. Details of the organic material of the present invention will be described later.

[0120] In the method for producing a TCDDM composition of the present invention, it is necessary to maintain the temperature of the TCDDM composition (A0) obtained by distillation and purification at not less than 45°C until it is transferred from the storage tank 2 to the container 3 for storage. The lower limit of the temperature until storage is not particularly limited, but is preferably 45°C or higher, more preferably 50°C or higher, even more preferably 60°C or higher, still more preferably 65°C or higher, still more preferably 70°C or higher, even more preferably above 70°C, and particularly preferably 75°C or higher. On the other hand, the upper limit of the temperature until storage is not particularly limited, but is preferably 110°C or lower, more preferably 100°C or lower, even more preferably 95°C or lower, still more preferably 90°C or lower, still more preferably below 90°C, and even more preferably 85°C or lower. The above upper and lower limits can be combined in any manner. For example, the temperature from the storage tank 2 until storage in the container 3 is preferably 45°C or higher and 110°C or lower, more preferably 50°C or higher and 100°C or lower, even more preferably 60°C or higher and 95°C or lower, even more preferably higher than 60°C and 90°C or lower, even more preferably 70°C or higher and lower than 90°C, and even more preferably higher than 70°C and 85°C or lower.

[0121] The time for which the TCDDM composition (A0) obtained by distillation and purification is kept at a temperature not lower than 45°C is not particularly limited, but is preferably at least 1 hour, more preferably more than 1 hour, even more preferably at least 5 hours, still more preferably at least 15 hours, even more preferably at least 30 hours, and even more preferably at least 45 hours. Meanwhile, the upper limit of the temperature until storage in the aforementioned container is not particularly limited, but is preferably at most 130 hours, more preferably at most 110 hours, even more preferably at most 90 hours, still more preferably at most 70 hours, even more preferably at most 60 hours, and even more preferably at most 50 hours. The above upper and lower limits can be combined arbitrarily. For example, the time for which the TCDDM composition (A0) obtained by distillation and purification is kept at a temperature not lower than 45°C is preferably from 1 hour to 130 hours, more preferably from more than 1 hour to 110 hours, even more preferably from 5 hours to 90 hours, still more preferably from 15 hours to 70 hours, even more preferably from 30 hours to 60 hours, and even more preferably from 45 hours to 50 hours.

[0122] The temperature of the TCDDM composition from storage tank 2 to storage in vessel 3 may fluctuate within a range not below 45° C. Specifically, the temperature change from distillation purification 1 to storage in vessel 3 is preferably within ±30° C., more preferably within ±20° C., even more preferably within ±15° C., even more preferably within ±10° C., and still more preferably within ±5° C.

[0123] As described above, the distillation-purified TCDDM composition (A0) can be temporarily stored in storage tank 2 located between distillation purification column 1 and vessel 3, and then transferred to vessel 3 for storage while maintaining a temperature above 45°C. Alternatively, the distillation-purified TCDDM composition (A0) can be stored in vessel 3 directly from distillation purification column 1 without passing through storage tank 2. Storing directly from distillation purification column 1 to vessel 3 means that no intermediate operations such as heating or stirring are performed during transfer from distillation purification column 1 to vessel 3; more specifically, it means that TCDDM composition (A0) is supplied from distillation purification column 1 to vessel 3 and stored therein in a single transfer step.

[0124] The container 3 is preferably a transport container. The transport container is used to store the TCDDM composition (A0) obtained by distillation and purification and to transport it to the market. Specific examples of the transport container include metal containers such as drums, gallon cans, and 18-liter cans; plastic containers such as plastic drums, polyethylene tanks, and plastic cans; and glass containers such as gallon bottles. From the viewpoints of transportation cost and ease of handling, drums are preferred.

[0125] (Step (3)) Step (3) in Figure 2 can include at least one of the following steps: transporting TCDDM composition (A1) obtained by the production method of the present invention and stored in container 3; storing TCDDM composition (A1) stored in container 3; storing TCDDM composition (A1) after the transport; or transporting TCDDM composition (A1) after the storage. Specific embodiments include a case in which a manufacturer of the TCDDM composition stores TCDDM composition (A1) stored in container 3; a case in which a transporter of TCDDM composition (A1) stored in container 3 transports or stores TCDDM composition (A1) stored in container 3; or a case in which a customer of TCDDM composition (A1) stored in container 3 stores TCDDM composition (A1) stored in container 3. The TCDDM composition obtained after TCDDM composition (A1) undergoes step (3) is referred to as TCDDM composition (A2).

[0126] (Temperature of TCDDM composition (A1) stored in container) The method for producing a TCDDM composition of the present invention is suitable when the TCDDM composition (A1) obtained by the method is stored in container 3 and placed in an environment of −5° C. or higher and lower than 45° C. for 24 hours or more before being fed into processing machine (X) in step (4) described below. In this specification, the term "placed" includes not only storage in a warehouse, but also movement of TCDDM composition (A1) stored in a container in a state where it is not subjected to excessive vibration, such as during transportation.

[0127] When TCDDM composition (A1) is stored in container 3 in an environment of −5°C or higher but lower than 45°C for 24 hours or longer, the lower limit of the temperature of the storage environment is not particularly limited, but from the viewpoint of suppressing the formation of microcrystals in TCDDM composition (A1) and thereby further improving the effect of suppressing an increase in viscosity, it is preferably −5°C or higher, more preferably 0°C or higher, even more preferably 5°C or higher, even more preferably 10°C or higher, and even more preferably 15°C or higher. On the other hand, the upper limit of the temperature of the storage environment is not particularly limited, but from the viewpoint of further improving the effect of suppressing deterioration of TCDDM composition (A1) due to thermal decomposition or alteration, it is preferably less than 45°C, more preferably 43°C or lower, even more preferably 40°C or lower, even more preferably 35°C or lower, and even more preferably 30°C or lower. The above upper and lower limits can be combined as desired. For example, when TCDDM composition (A1) is stored in container 3 and placed in an environment of −5° C. or higher and lower than 45° C. for 24 hours or longer, the temperature of the storage environment is preferably −5° C. or higher and lower than 45° C., more preferably 0° C. or higher and 43° C. or lower, even more preferably 5° C. or higher and 40° C. or lower, still more preferably 10° C. or higher and 35° C. or lower, and even more preferably 15° C. or higher and 30° C. or lower.

[0128] The temperature of the storage environment may fluctuate within a range of −5° C. or higher and lower than 45° C. Specifically, the temperature change of the storage environment is preferably within ±20° C., more preferably within ±15° C.

[0129] In the case where the product is stored in a container and placed in an environment of -5°C or higher and lower than 45°C for 24 hours or longer, the period of time for which the product is placed is usually 24 hours or longer and up to 3 years.

[0130] (Step (4)) Step (4) shown in Figures 2 and 3 is a step in which TCDDM composition (A1) obtained in step (2) and stored in container 3 or TCDDM composition (A2) obtained in step (3) is charged into processing machine (X). Typically, TCDDM composition (A1) obtained in step (2) and stored in container 3 is subjected to step (3) to obtain TCDDM composition (A2), and then step (4) is carried out. In this specification, "processing the TCDDM composition" refers to, for example, converting the TCDDM composition into another compound by chemical reaction in a reactor described below, or mixing the TCDDM composition with another substance in a blender described below.

[0131] (Heating Temperature of TCDDM Composition (A1) Before Charging into Processing Machine) Step (4) shown in FIG. 2 or FIG. 3 is a step of charging a part or all of TCDDM composition (A1) or TCDDM composition (A2) into processing machine (X).

[0132] The processing machine (X) is not particularly limited as long as it is a device for processing TCDDM composition (A1) or TCDDM composition (A2). For example, it may be a machine for converting the TCDDM composition into a desired shape or properties, or for converting TCDDM into another compound. Specific examples include known reactors and known compounders.

[0133] TCDDM composition (A1) or TCDDM composition (A2) can be charged into processing machine (X) in a state where it is heated or maintained at a temperature of 45°C or higher and lower than 120°C. By charging TCDDM composition (A1) or TCDDM composition (A2) in a state where it is heated or maintained at a temperature of 45°C or higher and lower than 120°C in whole or in part into processing machine (X), it is possible to suppress the formation of microcrystals in the TCDDM composition and to suppress an increase in viscosity. Alternatively, the TCDDM composition is less likely to become cloudy, allowing subsequent processing to be carried out more efficiently.

[0134] (Heating or warming temperature of TCDDM composition (A1) and TCDDM composition (A2)) There is no particular lower limit to the heating or warming temperature of TCDDM composition (A1) or TCDDM composition (A2). From the viewpoints of suppressing the formation of microcrystals in the TCDDM composition before it is fed into a processing machine, suppressing an increase in viscosity, and maintaining good handleability of the TCDDM composition when it is fed into a processing machine, the lower limit is 45°C or higher, preferably 50°C or higher, more preferably 52°C or higher, even more preferably 54°C or higher, even more preferably 56°C or higher, and even more preferably 58°C or higher. On the other hand, the upper limit of the heating temperature or heat-retention temperature is not particularly limited, but from the viewpoints of suppressing deterioration due to thermal decomposition or alteration of the TCDDM composition and suppressing increases in utility costs such as steam and electricity, it is preferably less than 120°C, preferably 100°C or less, more preferably 80°C or less, even more preferably 75°C or less, still more preferably 70°C or less, and even more preferably 65°C or less. The above upper and lower limits can be arbitrarily combined. For example, the heating temperature or heat-retention temperature of TCDDM composition (A1) or TCDDM composition (A2) is 45°C or higher and lower than 120°C, preferably 50°C or higher and 100°C or lower, more preferably 52°C or higher and 80°C or lower, even more preferably 54°C or higher and 75°C or lower, still more preferably 56°C or higher and 70°C or lower, and even more preferably 58°C or higher and 65°C or lower.

[0135] The heating temperature or the temperature for keeping warm may fluctuate within a range of 45° C. or higher and lower than 120° C. Specifically, the temperature change in the temperature environment is preferably within ±20° C., more preferably within ±15° C., even more preferably within ±10° C., and even more preferably within ±5° C.

[0136] Examples of a method for heating or keeping all or part of TCDDM composition (A1) or TCDDM composition (A2) at a temperature of 45°C or higher but lower than 120°C include a method in which TCDDM composition (A1) or TCDDM composition (A2) is heated or kept warm while stored in container 3. By not transferring TCDDM composition (A1) or TCDDM composition (A2) from container 3 to another container or the like before heating, the generation of microcrystals of chiral compound A in the TCDDM composition can be more effectively suppressed. Alternatively, as another method for heating or keeping warm, for example, TCDDM composition (A1) or TCDDM composition (A2) can be heated in a pipe or the like that supplies it to processing machine (X).

[0137] (Temperature During Feeding of TCDDM Composition (A1) or TCDDM Composition (A2) into Processor (X)) TCDDM composition (A1) or TCDDM composition (A2) is preferably fed into processor (X) while heated or maintained at a temperature of 45° C. or higher and lower than 120° C. There is no particular lower limit to the temperature of TCDDM composition (A1) or TCDDM composition (A2) during feeding into processor (X) after heating or maintaining the temperature, but from the viewpoints of suppressing the formation of microcrystals in the TCDDM composition during feeding into the processor and suppressing an increase in viscosity, and maintaining good handleability of the TCDDM composition, a temperature of 50° C. or higher is preferred, more preferably 52° C. or higher, even more preferably 54° C. or higher, even more preferably 56° C. or higher, and even more preferably 58° C. or higher. On the other hand, the upper limit of the temperature is not particularly limited, but from the viewpoints of suppressing deterioration due to thermal decomposition or alteration of the TCDDM composition and suppressing increases in utility costs such as steam and electricity, it is preferably 100°C or lower, more preferably 80°C or lower, even more preferably 75°C or lower, still more preferably 70°C or lower, and even more preferably 65°C or lower. The above upper and lower limits can be arbitrarily combined. For example, the temperature of TCDDM composition (A1) or TCDDM composition (A2) during the period from heating to being fed into processing machine (X) is preferably 50°C or higher and 100°C or lower, more preferably 52°C or higher and 80°C or lower, even more preferably 54°C or higher and 75°C or lower, still more preferably 56°C or higher and 70°C or lower, and even more preferably 58°C or higher and 65°C or lower.

[0138] The temperature of TCDDM composition (A1) or TCDDM composition (A2) after heating and before being fed into the processing machine may fluctuate within a range of 45° C. or higher and lower than 120° C. Specifically, the temperature change after heating and before being fed into the processing machine is preferably within ±20° C., more preferably within ±15° C., even more preferably within ±10° C., and even more preferably within ±5° C.

[0139] The heated TCDDM composition (A1) or TCDDM composition (A2) may be charged partially or entirely into the processing machine (X). The charging of a portion of TCDDM composition (A1) or TCDDM composition (A2) into the processing machine (X) also includes the case where TCDDM composition (A1) or TCDDM composition (A2) is charged sequentially into the processing machine (X). Furthermore, after charging a portion of TCDDM composition (A1) or TCDDM composition (A2) into the processing machine (X), the container 3 containing the remaining TCDDM composition (A1) or TCDDM composition (A2) may be temporarily stored, and then the remaining TCDDM composition (A1) or TCDDM composition (A2) may be charged into the processing machine (X) again to produce the organic material. The processing machine into which the remaining TCDDM composition (A1) or TCDDM composition (A2) is charged may be the same as or different from the previous processing machine. Furthermore, when a portion of TCDDM composition (A1) or TCDDM composition (A2) is loaded into a processing machine and then container 3 containing the remaining TCDDM composition (A2) is temporarily stored, container 3 containing the remaining TCDDM composition (A2) can also be stored while maintaining a temperature of 45°C or higher and lower than 120°C.

[0140] In the method for producing a TCDDM composition of the present invention, in step (3), TCDDM composition (A1) can be heated while stored in container 3, and the TCDDM composition (A2) obtained by heating can then be directly charged from container 3 to processing machine (X). That is, in the production method of the present invention, TCDDM composition (A1) stored in container 3 is heated while stored in container 3 in step (3) to form TCDDM composition (A2), and TCDDM composition (A2) is then directly charged from container 3 to processing machine (X) in step (4).

[0141] In this specification, the term "directly adding" refers to transferring the contents of the container 3 into the processing machine (X) in a single step of "transferring" without any intermediate operations such as heating or stirring during the transfer from the container 3 to the processing machine (X). Needless to say, this also includes cases where the "transferring" step is performed via a connecting pipe between the container 3 and the processing machine (X). By eliminating the transfer step, the generation of microcrystals in the TCDDM composition (A2) can be effectively suppressed.

[0142] It is preferable that the TCDDM composition (A1) stored in the container 3 in the step (2) is not heated until it is heated to 45° C. or higher and lower than 120° C. in the step (4) and then supplied to the processing machine (X). The above-described configuration enables more efficient production of organic materials.

[0143] (Method for producing an organic material) The TCDDM composition (A1) or TCDDM composition (A2) stored in container 3 is preferably used for producing an organic material. A preferred embodiment of the method for producing an organic material using the TCDDM composition stored in container 3 is shown below.

[0144] (First embodiment of method for producing organic material) A preferred first embodiment of the method for producing an organic material comprises, in step (4), heating part or all of TCDDM composition (A1) or TCDDM composition (A2) stored in container 3 to 45°C or higher and lower than 120°C while maintaining TCDDM composition (A0) obtained by distillation purification so that the temperature does not fall below 45°C, and then charging the heated TCDDM composition (A2) into processing machine (X) while maintaining it within the temperature range. In step (4), TCDDM composition (A1) or (A2) is heated while stored in container 3, and the resulting TCDDM composition (A1) or (A2) is directly charged from container 3 into processing machine (X). In the first embodiment, the content of chiral compound A in TCDDM composition (A1) is preferably 25% by mass or higher and 54% by mass or lower, based on the total mass of TCDDM composition (A1), 100% by mass.

[0145] Furthermore, the organic material is preferably at least one polymer selected from the group consisting of polyester-based resins, epoxy-based resins, acrylate-based resins, polycarbonate-based resins, and polyurethane-based resins, or an ultraviolet-curable composition.

[0146] (Second embodiment of the method for producing an organic material) A second preferred embodiment of the method for producing an organic material is the first embodiment, further comprising storing the TCDDM composition (A1) in a container 3 in an environment of −5° C. or higher and lower than 45° C. for 24 hours or longer before heating.

[0147] (Third embodiment of the method for producing an organic material) A preferred third embodiment of the method for producing an organic material is such that, in the first embodiment and / or the second embodiment, no stirring is performed after the TCDDM composition (A0) has been stored in container 3 until the TCDDM composition (A2) is directly charged into the processing machine (X).

[0148] (Fourth embodiment of the method for producing an organic material) A preferred fourth embodiment of the method for producing an organic material is a method for producing a TCDDM composition stored in container 3 in any of the first to third embodiments, in which, after TCDDM composition (A0) has been stored in container 3, no heating is carried out until TCDDM composition (A1) is heated to a temperature of 45°C or higher but lower than 120°C.

[0149] [TCDDM composition (A1)] Next, tricyclodecane dimethanol composition (A1) (TCDDM composition (A1)) containing a chiral compound of which one enantiomer is represented by formula (A) will be described. TCDDM composition (A1) in the present invention is the TCDDM composition after undergoing the above-mentioned step (2), and is a composition stored in container 3, containing a chiral compound of which one enantiomer is represented by the following formula (A) (chiral compound A):

[0150]

[0151] TCDDM composition (A1) in the present invention can be obtained by storing the above-mentioned starting material TCDDM composition (A0) in vessel 3 while maintaining its temperature above 45°C. Specifically, the TCDDM composition (A1) can also be obtained by distilling and purifying a crude reaction liquid obtained through a step of hydroformylating dicyclopentadiene to obtain tricyclodecane dicarbaldehyde and a step of obtaining a crude reaction liquid containing tricyclodecane dimethanol by reduction of the tricyclodecane dicarbaldehyde, and then directly storing the crude reaction liquid in vessel 3 while maintaining its temperature above 45°C.

[0152] The TCDDM composition (A1) of the present invention may contain, in addition to chiral compound A, tricyclodecane dimethanol, one enantiomer of which is represented by the following formula (B) (sometimes referred to herein as "chiral compound B"). That is, the more chiral compound A is contained, the more microcrystals are produced in the TCDDM composition (A1), and the more suitable the fluidity and the easier it tends to be to handle in blending operations and the like. The more chiral compound B is contained, the relatively lower the proportion of chiral compound A is, and the fewer TCDDM microcrystals there are in the TCDDM composition (A1) or the more inhibited the increase in TCDDM microcrystals is, so that the viscosity is less likely to increase during storage and the storage stability tends to be better.

[0153]

[0154] Furthermore, the TCDDM composition (A1) of the present invention may contain, in addition to chiral compound A and chiral compound B, and / or chiricyclodecane dimethanol, one enantiomer of which is represented by formula (C) (sometimes referred to herein as "chiral compound C") In other words, the more chiral compound C is contained, the more the TCDDM microcrystals in the TCDDM composition (A1) are reduced or the increase of TCDDM microcrystals is suppressed, and the viscosity is less likely to increase during storage, tending to improve storage stability.

[0155]

[0156] In addition, chiral compound A, chiral compound B, and chiral compound C in TCDDM composition (A1) can be treated as synonymous with chiral compound A, chiral compound B, and chiral compound B in TCDDM composition (A0), respectively.

[0157] (Content of chiral compound A) In the TCDDM composition (A1) of the present invention, there is no particular lower limit to the content of chiral compound A. However, from the viewpoint of excellent handling in blending operations and the like, since microcrystals are formed in the TCDDM composition (A1) and appropriate fluidity can be ensured, the content is preferably 25% by mass or more, more preferably 28% by mass or more, even more preferably 30% by mass or more, still more preferably 32% by mass or more, even more preferably 33% by mass or more, still more preferably 34% by mass or more, particularly more preferably 35% by mass or more, and most particularly more preferably 36% by mass or more, relative to the total mass of TCDDM composition (A1) (100% by mass). Furthermore, the upper limit of the content of chiral compound A is not particularly limited, but from the viewpoints of suppressing the formation of TCDDM microcrystals in TCDDM composition (A1), suppressing an increase in viscosity during storage, and improving storage stability, it is preferably 54% by mass or less, more preferably 50% by mass or less, even more preferably 45% by mass or less, still more preferably 43% by mass or less, even more preferably 41% by mass or less, still more preferably 40% by mass or less, particularly more preferably 39% by mass or less, and even particularly more preferably 38.5% by mass or less, relative to the total mass of TCDDM composition (A1) (100% by mass). The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A1), the content of chiral compound A is preferably 25% by mass to 54% by mass, more preferably 28% by mass to 50% by mass, even more preferably 30% by mass to 45% by mass, even more preferably 32% by mass to 43% by mass, even more preferably 33% by mass to 41% by mass, still more preferably 34% by mass to 40% by mass, particularly preferably 35% by mass to 39% by mass, and even particularly preferably 36% by mass to 38.5% by mass. While Example 2-1 described below was carried out under conditions outside the preferred range of the content, the effects of the present invention can be achieved at a content within the preferred range.

[0158] (Content of chiral compound B) In the TCDDM composition (A1) of the present invention, there is no particular lower limit to the content of chiral compound B. From the viewpoints of suppressing the formation of TCDDM microcrystals in the TCDDM composition (A1), suppressing an increase in viscosity during storage, and improving storage stability, the content of chiral compound B is preferably 1.6% by mass or more, more preferably 1.8% by mass or more, even more preferably 2.0% by mass or more, still more preferably 2.1% by mass or more, even more preferably 2.2% by mass or more, and even more preferably 2.3% by mass or more, relative to the total mass (100% by mass) of the TCDDM composition (A1). Although there is no particular upper limit to the content of chiral compound B in TCDDM composition (A1), from the viewpoint of forming microcrystals in TCDDM composition (A1) and ensuring appropriate fluidity, thereby providing better handling in blending operations and the like, the content is preferably 4.8% by mass or less, more preferably 4.6% by mass or less, even more preferably 4.4% by mass or less, still more preferably 4.3% by mass or less, even more preferably 4.2% by mass or less, still more preferably 4.0% by mass or less, and further preferably 3.8% by mass or less, 3.5% by mass or less, 3.2% by mass or less, 3.0% by mass or less, 2.8% by mass or less, and 2.7% by mass or less, relative to the total mass (100% by mass) of TCDDM composition (A1). The above upper and lower limits can be combined in any order. For example, in TCDDM composition (A1), the content of chiral compound B is preferably 1.6% by mass to 4.8% by mass, more preferably 1.8% by mass to 4.6% by mass, even more preferably 2.0% by mass to 4.4% by mass, still more preferably 2.1% by mass to 4.3% by mass, even more preferably 2.2% by mass to 4.2% by mass, and even more preferably 2.3% by mass to 4.0% by mass, relative to the total mass of TCDDM composition (A1) (100% by mass). Note that, although Example 2-1 described below was carried out under conditions outside the preferred range of the content, the effects of the present invention can be obtained at a content within the preferred range.

[0159] (Content of chiral compound C) In the TCDDM composition (A1) of the present invention, there is no particular lower limit to the content of chiral compound C. However, from the viewpoints of suppressing the formation of TCDDM microcrystals in the TCDDM composition (A1), suppressing an increase in viscosity during storage, and improving storage stability, the content is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 18% by mass or more, still more preferably 20% by mass or more, even more preferably 22% by mass or more, and even more preferably 25% by mass or more, relative to the total mass of the TCDDM composition (A1) (100% by mass). Furthermore, although there is no particular upper limit to the content of chiral compound C in TCDDM composition (A1), from the viewpoint of producing microcrystals in TCDDM composition (A1) and ensuring appropriate fluidity, thereby providing superior handling in blending operations and the like, the content is preferably 45% by mass or less, more preferably 40% by mass or less, even more preferably 38% by mass or less, still more preferably 35% by mass or less, even more preferably 33% by mass or less, and even more preferably 30% by mass or less, relative to the total mass of TCDDM composition (A1) (100% by mass). The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A1), the content of chiral compound C is preferably 10% by mass to 45% by mass, more preferably 15% by mass to 40% by mass, even more preferably 18% by mass to 38% by mass, even more preferably 20% by mass to 35% by mass, still more preferably 22% by mass to 33% by mass, and even more preferably 25% by mass to 30% by mass, relative to the total mass of TCDDM composition (A1) (100% by mass). While Example 2-1, described below, was carried out under conditions outside the preferred range of the content, the effects of the present invention can be achieved at a content within the preferred range.

[0160] (TCDDM Content) In TCDDM composition (A1), there is no particular lower limit to the total TCDDM content, but from the viewpoint of ease of handling the composition, it is preferably 80% by mass or more, more preferably 90% by mass or more, even more preferably 95% by mass or more, even more preferably 97% by mass or more, and even more preferably 99% by mass or more, based on 100% by mass of the total mass of TCDDM composition (A1). On the other hand, there is no particular upper limit to the total TCDDM content in TCDDM composition (A1), and a higher value is preferable, and it may even be 100% by mass, based on the total mass of TCDDM composition (A1).

[0161] (Total Content of Chiral Compounds A to C) In TCDDM composition (A1), the lower limit of the total content of chiral compound A, chiral compound B, and chiral compound C is not particularly limited, but from the viewpoint of ease of handling of the composition, it is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more, relative to 100% by mass of the total mass of TCDDM composition (A1). On the other hand, the upper limit of this total content is not particularly limited, and a higher value is preferable, and it may be 100% by mass, relative to the total mass of TCDDM composition (A1).

[0162] (Backscattering intensity T of TCDDM composition (A1) １ ) 173° backscatter intensity T １ is an index showing the fluidity and storage stability of a TCDDM composition.

[0163] The 173° backscattering intensity T of the TCDDM composition (A1) measured at a temperature of 25°C using a dynamic light scattering measurement method １ The lower limit of the 173° backscattering intensity T １ The relative increase in the TCDDM composition (A1) resulted in the formation of microcrystals, and the TCDDM composition (A1) had a suitable fluidity, which made it easier to handle during blending operations, etc., and therefore the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷500 or more is preferable, and T ２÷250 or more is more preferable, and T ２ ÷200 or more is more preferable, and T ２ ÷100 or more is more preferable, and T ２ ÷50 or more is more preferable, and T ２ ÷10 or more is even more preferable, and T ２ On the other hand, the backscattering intensity T １ The upper limit of the 173° backscattering intensity T １ is relatively reduced, the amount of TCDDM microcrystals in the TCDDM composition (A1) is reduced or the increase in the amount of TCDDM microcrystals is suppressed, the viscosity is less likely to increase, and storage stability is improved. ２ × 5.0 or less is preferable, and T ２ × 2.0 or less is more preferable, and T ２ More preferably, ２ ÷2 or less is more preferable, and T ２ ÷3 or less is more preferable, and T ２ ÷4 or less is even more preferable, and T ２ The upper and lower limits can be arbitrarily combined. For example, in the TCDDM composition (A1), the backscattering intensity T １ Is T ２ ÷500≦T １ ≦T ２ is preferred, and T ２ ÷250≦T １ ≦T ２ ÷2 is more preferable, and T ２ ÷200≦T １ ≦T ２ ÷3 is more preferred, and T ２ ÷100≦T １ ≦T ２ ÷4 is more preferred, and T ２ ÷50≦T １ ≦T ２ ÷5 is even more preferable, and T ２ ÷8.0≦T １ ≦T ２ x 5.0 is even more preferable, and T ２ ÷8.0≦T １ ≦T ２× 2.0 is particularly preferred, and T ２ ÷8.0≦T １ ≦T ２ is most preferred.

[0164] As a more specific embodiment of the TCDDM composition (A1) of the present invention, for example, １ The lower limit of the backscattering intensity T is not particularly limited, but is preferably 10 or more, more preferably 50 or more, and even more preferably 100 or more, because the TCDDM composition (A1) has a suitable fluidity and tends to be superior in handling during preparation operations and the like. １ The upper limit of is not particularly limited, but is preferably 5,000 or less, more preferably 3,000 or less, and even more preferably 1,000 or less, since this tends to prevent the viscosity of TCDDM composition (A2) from increasing and improve storage stability and ease of handling in preparation operations, etc. The upper and lower limits can be arbitrarily combined. For example, in the TCDDM composition (A1), the 173° backscattering intensity T １ is preferably 10 or more and 5000 or less, more preferably 50 or more and 3000 or less, and even more preferably 100 or more and 1000 or less. １ is measured as described in the Examples below.

[0165] Backscatter intensity T １ There are no particular limitations on the method for keeping within the above range, but this can be achieved, for example, by storing TCDDM composition (A0) in container 3 while maintaining a temperature not lower than 45°C. More preferably, this can be achieved by suppressing heating after production of the TCDDM raw material (TCDDM composition (A0)), stirring the TCDDM in a heated state, transferring the TCDDM to another container, or the like.

[0166] [TCDDM composition (A2)] In the present invention, TCDDM composition (A2) refers to TCDDM composition (A1) after step (3). That is, TCDDM composition (A2) refers to the TCDDM composition (A1) stored in container 3 after transportation and / or storage. In step (4), TCDDM composition (A2) can be heated in part or in whole and introduced into a processing machine. In the present invention, TCDDM composition (A0) is stored in container 3 while being maintained at a temperature not lower than 45°C in step (2). Therefore, TCDDM composition (2) after transportation and storage of TCDDM composition (A1) can be easily processed when introduced into a processing machine.

[0167] In addition to chiral compound A, TCDDM composition (A2) of the present invention may contain chiral compound B represented by formula (B) and chiral compound C represented by formula (C). That is, the more chiral compound A present, the more microcrystals are formed in TCDDM composition (A2), and the more suitable the fluidity is, which tends to improve handling during blending and other operations. The more chiral compound B present, the lower the proportion of chiral compound A, which reduces the amount of TCDDM microcrystals in TCDDM composition (A1) or suppresses the increase in TCDDM microcrystals, which tends to reduce the viscosity increase during storage and improve storage stability. The more chiral compound C present, the lower the proportion of chiral compound A, which reduces the amount of TCDDM microcrystals in TCDDM composition (A1) or suppresses the increase in TCDDM microcrystals, which tends to reduce the viscosity increase during storage and improve storage stability.

[0168] In addition, chiral compound A, chiral compound B, and chiral compound C in TCDDM composition (A2) can be treated as synonyms for chiral compound A, chiral compound B, and chiral compound C in TCDDM composition (A1), respectively.

[0169] (Content of chiral compound A) In the TCDDM composition (A2) of the present invention, there is no particular lower limit on the content of chiral compound A. From the viewpoints of producing microcrystals in the TCDDM composition (A2), ensuring appropriate fluidity, and providing excellent handling in blending operations and the like, the content of chiral compound A is preferably 25% by mass or more, more preferably 28% by mass or more, even more preferably 30% by mass or more, still more preferably 32% by mass or more, even more preferably 33% by mass or more, still more preferably 34% by mass or more, particularly more preferably 35% by mass or more, and most particularly more preferably 36% by mass or more, relative to the total mass of the TCDDM composition (A2) (100% by mass). Furthermore, although there is no particular upper limit to the content of chiral compound A, from the viewpoints of suppressing the formation of TCDDM microcrystals in TCDDM composition (A2), suppressing an increase in viscosity during storage, and improving storage stability, the content is preferably 54% by mass or less, more preferably 50% by mass or less, even more preferably 45% by mass or less, still more preferably 43% by mass or less, even more preferably 41% by mass or less, still more preferably 40% by mass or less, particularly more preferably 39% by mass or less, and particularly more preferably 38.5% by mass or less, relative to the total mass of TCDDM composition (A2) (100% by mass). The above upper and lower limits can be combined as desired. For example, in TCDDM composition (A2), the content of chiral compound A is preferably 25% by mass to 54% by mass, more preferably 28% by mass to 50% by mass, even more preferably 30% by mass to 45% by mass, even more preferably 32% by mass to 43% by mass, even more preferably 33% by mass to 41% by mass, still more preferably 34% by mass to 40% by mass, particularly preferably 35% by mass to 39% by mass, and even particularly preferably 36% by mass to 38.5% by mass. While Example 2-1 below was carried out under conditions outside the preferred range of the content, the effects of the present invention can be achieved at a content within the preferred range.

[0170] (Content of chiral compound B) In the TCDDM composition (A2) of the present invention, there is no particular lower limit to the content of chiral compound B. From the viewpoints of suppressing the formation of TCDDM microcrystals in the TCDDM composition (A2), suppressing an increase in viscosity during storage, and improving storage stability, the content of chiral compound B is preferably 1.6% by mass or more, more preferably 1.8% by mass or more, even more preferably 2.0% by mass or more, still more preferably 2.1% by mass or more, even more preferably 2.2% by mass or more, and even more preferably 2.3% by mass or more, relative to the total mass of TCDDM composition (A2) (100% by mass). Although there is no particular upper limit to the content of chiral compound B in TCDDM composition (A2), from the viewpoint of forming microcrystals in TCDDM composition (A2), ensuring appropriate fluidity, and thereby improving handleability in blending operations, etc., the content is preferably 4.8% by mass or less, more preferably 4.6% by mass or less, even more preferably 4.4% by mass or less, still more preferably 4.3% by mass or less, even more preferably 4.2% by mass or less, still more preferably 4.0% by mass or less, and further preferably 3.8% by mass or less, 3.5% by mass or less, 3.2% by mass or less, 3.0% by mass or less, 2.8% by mass or less, and 2.7% by mass or less, relative to the total mass (100% by mass) of TCDDM composition (A2). The above upper and lower limits can be combined in any order. For example, in TCDDM composition (A2), the content of chiral compound B is preferably 1.6% by mass to 4.8% by mass, more preferably 1.8% by mass to 4.6% by mass, even more preferably 2.0% by mass to 4.4% by mass, still more preferably 2.1% by mass to 4.3% by mass, even more preferably 2.2% by mass to 4.2% by mass, and even more preferably 2.3% by mass to 4.0% by mass, relative to the total mass of TCDDM composition (A2) (100% by mass). While Example 2-1, described below, was carried out under conditions outside the preferred range of the content, the effects of the present invention can be achieved at a content within the preferred range.

[0171] (Content of chiral compound C) In the TCDDM composition (A2) of the present invention, there is no particular lower limit to the content of chiral compound C. From the viewpoints of suppressing the formation of TCDDM microcrystals in the TCDDM composition (A1), suppressing an increase in viscosity during storage, and improving storage stability, the content of chiral compound C is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 18% by mass or more, still more preferably 20% by mass or more, even more preferably 22% by mass or more, and even more preferably 25% by mass or more, relative to the total mass of the TCDDM composition (A2) (100% by mass). Furthermore, the upper limit of the content of chiral compound C in TCDDM composition (A2) is not particularly limited, but from the viewpoint of forming microcrystals in TCDDM composition (A1), ensuring appropriate fluidity, and thus providing better handling during blending operations, etc., the content is preferably 45% by mass or less, more preferably 40% by mass or less, even more preferably 38% by mass or less, even more preferably 35% by mass or less, even more preferably 33% by mass or less, and even more preferably 30% by mass or less, relative to the total mass of TCDDM composition (A2) (100% by mass). By setting the content at or above the lower limit, the amount of TCDDM microcrystals in TCDDM composition (A1) can be reduced. The above upper and lower limits can be combined in any desired manner. For example, in TCDDM composition (A1), the content of chiral compound B is preferably 10% by mass to 45% by mass, more preferably 15% by mass to 40% by mass, even more preferably 18% by mass to 38% by mass, even more preferably 20% by mass to 35% by mass, still more preferably 22% by mass to 33% by mass, and even more preferably 25% by mass to 30% by mass, relative to the total mass of TCDDM composition (A2) (100% by mass). While Example 2-1, described below, was carried out under conditions outside the preferred range of the content, the effects of the present invention can be achieved at a content within the preferred range.

[0172] (TCDDM Content) In TCDDM composition (A2), the lower limit of the TCDDM content is not particularly limited, but from the viewpoint of ease of handling of the composition, it is preferably 80% by mass or more, more preferably 90% by mass or more, even more preferably 95% by mass or more, still more preferably 97% by mass or more, and still more preferably 99% by mass or more, relative to 100% by mass of the total mass of TCDDM composition (A2). On the other hand, the upper limit of the total content is not particularly limited, and a higher value is preferable, and it may be 100% by mass, relative to the total mass of TCDDM composition (A2).

[0173] (Total Content of Chiral Compounds A to C) In TCDDM composition (A2), the lower limit of the total content of chiral compound A, chiral compound B, and chiral compound C is not particularly limited, but from the viewpoint of ease of handling of the composition, it is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more, relative to 100% by mass of the total mass of TCDDM composition (A2). On the other hand, the upper limit of this total content is not particularly limited, and a higher value is preferable, and it may be 100% by mass, relative to 100% by mass of the total mass of TCDDM composition (A2).

[0174] (Backscattering intensity T of TCDDM composition (A2) １ ) 173° backscatter intensity T １ is an index showing the fluidity and storage stability of a TCDDM composition.

[0175] The 173° backscattering intensity T of the TCDDM composition (A2) measured at a temperature of 25°C using a dynamic light scattering measurement method １ The lower limit of the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷100 or more is preferable, and T ２ ÷50 or less is more preferable, and T ２ ÷30 or more is more preferable, and T２ ÷10 or more is more preferable, and T ２ On the other hand, the backscattering intensity T １ The upper limit of T is not particularly limited, but it is preferable that the TCDDM composition (A2) has a reduced amount of TCDDM microcrystals or an increased amount of TCDDM microcrystals is suppressed, and the viscosity increase during processing is suppressed, resulting in good storage stability and ease of handling during preparation operations. ２ × 2.0 or less is preferable, and T ２ × 1.5 or less is more preferable, and T ２ More preferably, ２ ÷1.3 or less is particularly preferred, and T ２ The above upper and lower limits can be arbitrarily combined. For example, in the TCDDM composition (A2), the backscattering intensity T １ Is T ２ ÷100≦T １ ≦T ２ × 2.0 is preferred, and T ２ ÷50≦T １ ≦T ２ × 1.5 is more preferable, and T ２ ÷30≦T １ ≦T ２ is more preferred, and T ２ ÷10≦T １ ≦T ２ ÷1.3 is more preferred, and T ２ ÷7≦T １ ≦T ２ ÷1.5 is even more preferred.

[0176] As a more specific embodiment of the TCDDM composition (A2) of the present invention, for example, １ The lower limit of the backscattering intensity T is preferably 50 or more, more preferably 100 or more, and even more preferably 700 or more. １The upper limit of is not particularly limited, but is preferably 10,000 or less, more preferably 8,000 or less, and even more preferably 5,000 or less, from the viewpoint of preventing an increase in the viscosity of TCDDM composition (A2) and improving storage stability and ease of handling in preparation operations, etc. The upper and lower limits can be arbitrarily combined. For example, １ is preferably 50 to 10,000, more preferably 100 to 8,000, and even more preferably 700 to 5,000. １ is measured as described in the Examples below.

[0177] Backscatter intensity T １ The method for adjusting the temperature to within the above range is not particularly limited, but for example, it can be achieved by heating the TCCM composition (A1) stored in a container at a temperature below 45° C. to 45° C. or higher and lower than 120° C. More preferably, it can be achieved by carrying out the above-mentioned step (3) in FIG.

[0178] [Method for storing TCCDM composition] The method for storing a TCCDM composition of the present invention comprises storing a TCCDM composition (A0) containing tricyclodecane dimethanol obtained by distillation and purification in a container while maintaining the temperature at not less than 45°C, wherein the tricyclodecane dimethanol contains a chiral compound whose one enantiomer is represented by formula (A).

[0179] The details of the embodiment relating to the method for storing a TCDDM composition of the present invention are the same as those of the step of storing a tricyclodecane dimethanol composition (A0) containing a chiral compound of which one enantiomer is represented by formula (A) in a container while maintaining the temperature at not less than 45°C, as described above in [Method for producing a TCDDM composition stored in a container], and the preferred ranges are also the same.

[0180] In the method for storing a TCCDM composition of the present invention, the content of the chiral compound contained in the TCCDM composition, one of the enantiomers of which is represented by formula (A), is preferably 25% by mass or more and 54% by mass or less, relative to the total mass of the TCCDM composition (A0) (100% by mass).

[0181] In the method for storing a TCDDM composition, the details of the chiral compound of which one enantiomer is represented by formula (A) are the same as those described above in [Method for producing a TCDDM composition stored in a container], and the preferred range of the content of the chiral compound of formula (A) in the TCDDM composition is also the same.

[0182] In the method for preserving a TCCDM composition of the present invention, the TCCDM composition (A0) can contain tricyclodecane dimethanol, one enantiomer of which is represented by formula (B).

[0183] In the method for storing a TCCDM composition of the present invention, the content of the chiral compound contained in the TCCDM composition, one of the enantiomers of which is represented by formula (B), is preferably 1.6% by mass or more and 4.8% by mass or less, relative to the total mass of the TCCDM composition (A0) (100% by mass).

[0184] In the method for storing a TCDDM composition of the present invention, the details of the chiral compound of which one enantiomer is represented by formula (B) are the same as those described above in [Method for producing a TCDDM composition stored in a container], and the preferred range of the content of tricyclodecane dimethanol represented by formula (B) in the TCDDM composition is also the same.

[0185] In the method for preserving a TCCDM composition of the present invention, the TCCDM composition (A0) can contain tricyclodecane dimethanol, one enantiomer of which is represented by formula (C).

[0186] In the method for storing a TCCDM composition of the present invention, the content of tricyclodecane dimethanol, one of the enantiomers of which is represented by formula (C), contained in the TCCDM composition is preferably 10% by mass or more and 45% by mass or less, relative to the total mass of the TCCDM composition (A0) (100% by mass).

[0187] Details of the tricyclodecane dimethanol of which one enantiomer is represented by formula (C) in the method for storing a TCDDM composition of the present invention are the same as those described above in [Method for producing a TCDDM composition stored in a container], and the preferred range of the content of tricyclodecane dimethanol represented by formula (C) in the TCDDM composition is also the same.

[0188] In the method for preserving a TCCDM composition of the present invention, the tricyclodecane dimethanol composition stored in the container can be heated while stored in the container and then directly introduced from the container into a processing machine for use. In the method for preserving a TCCDM composition of the present invention, the processing machine can be a reactor and / or a compounder. Details of the processing machine used in the method for preserving a TCCDM composition are the same as those described above in "Method for producing a TCDDM composition stored in a container."

[0189] The details of the embodiment relating to the method for storing a TCDDM composition of the present invention are the same as those described above in [Method for producing a TCDDM composition stored in a container], and the preferred ranges are also the same.

[0190] [Organic Materials] The TCDDM composition (A1) and further the TCDDM composition (A2) are processed and used as various organic materials. The organic materials are not particularly limited in type, and can be used to produce known organic materials. The organic material is not particularly limited, but is preferably at least one polymer selected from the group consisting of polyester resins, epoxy resins, acrylate resins, polycarbonate resins, and polyurethane resins, or an ultraviolet-curable composition.

[0191] The polyester resin in the present invention is a resin mainly composed of a polyethylene polymer such as polyethylene terephthalate (PET). The polyethylene polymer is not particularly limited, and refers to, for example, a polymer containing structural units derived from a polyol mainly containing glycol and structural units derived from a terephthalic acid compound, and also containing structural units derived from tricyclodecane dimethanol in the TCDDM composition (A2).

[0192] The epoxy resin in the present invention is a resin containing an epoxy polymer as a main component. The epoxy polymer is not particularly limited, and examples thereof include a polymer containing structural units derived from a bisphenol compound and structural units derived from epichlorohydrin, and also containing structural units derived from tricyclodecane dimethanol in the TCDDM composition (A2).

[0193] The acrylate resin in the present invention is a resin containing an acrylate polymer as a main component. The acrylate polymer is not particularly limited, and examples thereof include a polymer containing a structural unit derived from (meth)acrylic acid or a structural unit derived from a (meth)acrylic acid derivative, and containing a structural unit derived from tricyclodecane dimethanol in the TCDDM composition (A2).

[0194] The polycarbonate resin in the present invention is a resin containing a polycarbonate polymer as a main component. The polycarbonate polymer is not particularly limited, and examples thereof include a polymer containing a structural unit derived from a bisphenol compound, a structural unit derived from phosgene (carbonyl chloride), or a structural unit derived from diphenyl carbonate, and containing a structural unit derived from tricyclodecane dimethanol in the TCDDM composition (A2).

[0195] The polyurethane resin in the present invention is a resin containing a polyurethane polymer as a main component. The polyurethane polymer is not particularly limited, and examples thereof include a polymer containing a structural unit derived from a polyol mainly containing a glycol and a structural unit derived from a bifunctional isocyanate, and also containing a structural unit derived from tricyclodecane dimethanol in the TCDDM composition (A2).

[0196] The UV-curable composition of the present invention is a UV-curable composition derived from TCDDM composition (A2). More specifically, the UV-curable composition is a UV-curable composition synthesized using TCDDM composition (A2) as a raw material. Even more specifically, the UV-curable composition is a UV-curable composition synthesized using tricyclodecane dimethanol contained in TCDDM composition (A2) as a raw material. The method for producing the UV-curable composition is not particularly limited and can be carried out according to a conventional method. In general, it is desirable to use tricyclodecane dimethanol in TCDDM composition (A2) as a raw material to produce a derivative such as a di(meth)acrylic acid ester derivative or a urethane acrylate. For details regarding the method for producing these derivatives, please refer to paragraphs

[0098] to

[0117] of WO 2023 / 176641, the contents of which are incorporated herein by reference.

[0197] The ultraviolet-curable composition can be suitably used for hard coating materials, antifouling coating materials, resist materials, inkjet inks, and materials for 3D printers.

[0198] The third embodiment of the present invention will now be described in detail.

[0199] [Method for Producing an Organic Material] The method for producing an organic material of the present invention includes heating a portion or all of a tricyclodecane dimethanol composition (A1) containing tricyclodecane dimethanol, which is stored in a container and has a temperature below 45°C, to 45°C or higher but lower than 120°C, and processing the heated tricyclodecane dimethanol composition (A2) in a processing machine while maintaining the temperature at 45°C to lower than 120°C, wherein the tricyclodecane dimethanol contains a chiral compound one enantiomer of which is represented by formula (A). However, it is preferable that the organic material is not a fragrance material. That is, it is preferable that the organic material in the method for producing an organic material of this embodiment does not include a fragrance material. The above configuration makes it possible to suppress an increase in viscosity of the TCDDM composition during storage, and to provide a method for producing an organic material that can efficiently produce an organic material using the TCDDM composition as a raw material.

[0200] Depending on its thermal history and handling conditions, the viscosity of a TCDDM composition may increase during storage, resulting in a decrease in fluidity and handleability. Under these circumstances, the inventors and others conducted detailed studies and found that repeated heating and cooling can increase the viscosity of a TCDDM composition, potentially hindering the efficient production of organic materials. Specifically, chiral compounds in which one enantiomer is represented by formula (A) (hereinafter sometimes referred to as "chiral compound A") are prone to crystallization and tend to form microcrystals upon cooling. The formation of microcrystals of TCDDM, such as chiral compound A, increases the viscosity of the TCDDM composition, reducing its fluidity and handleability. As a result, problems such as difficulty in feeding the composition into a processing machine for producing organic materials or the TCDDM composition itself becoming cloudy can occur, preventing the efficient production of organic materials. In this invention, the term "microcrystals" refers to tiny particles with an average particle size of submicrons or less that are composed of TCDDM, such as chiral compound A, and exhibit a microscopic structure as detected by the dynamic light scattering method described below.

[0201] In the method for producing an organic material of the present invention, a TCDDM composition (A1) containing chiral compound A that is stored in a container is heated to a temperature of less than 45°C, and then maintained at that temperature, thereby effectively suppressing the formation of microcrystals of TCDDM such as chiral compound A in the TCDDM composition, and by maintaining this state, an organic material can be produced efficiently.

[0202] The method for producing an organic material of the present invention will be described below with reference to FIG. 5. FIG. 5 is a process schematic diagram illustrating the steps of an example of the method for producing an organic material of the present invention. (1) to (5) represent the individual steps. Hereinafter, these steps will be referred to as steps (1) to (5). Specifically, step (1) is a process for producing the raw material TCDDM composition (A0). step (2) is a process for storing TCDDM composition (A0) in a container to obtain TCDDM composition (A1) containing chiral compound A, which is stored in the container at a temperature below 45°C. steps (3) and (4) are each independently a transportation step and / or a storage step. step (5) is a process for heating a part or all of TCDDM composition (A1) to a temperature of 45°C or higher but lower than 120°C, and then feeding the heated TCDDM composition (A2) into processing machine (X) while maintaining the temperature at 45°C or higher but lower than 120°C. Thereafter, TCDDM composition (A2) is processed in processing machine (X) to obtain an organic material. It goes without saying that not all of the steps (1) to (5) are essential in the method for producing an organic material of the present invention.

[0203] Each of the above steps will be described in detail below.

[0204] Step (1) in Figure 5 above is a production process for the starting material TCDDM composition (A0). The production of TCDDM composition (A0) can be carried out by a known method. The TCDDM composition (A0) of the present invention can be obtained, for example, through a process comprising hydroformylating dicyclopentadiene to obtain tricyclodecane dicarbaldehyde, reducing the tricyclodecane dicarbaldehyde to obtain a crude reaction solution containing tricyclodecane dimethanol, and purifying the crude reaction solution by distillation. For details of these processes, please refer to paragraphs 0046 to 0017 of WO 2023 / 176641, the contents of which are incorporated herein by reference.

[0205] FIG. 5 (2) shows a process for obtaining TCDDM composition (A1) containing chiral compound A, which is stored in a container at a temperature of less than 45° C. by storing TCDDM composition (A0) in a container. While it would be sufficient if the distillation-purified TCDDM composition (A0) could be directly introduced into a processing machine for producing an organic material, the distillation-purified TCDDM composition (A0) is typically stored in a container, transported, and then processed into an organic material. Furthermore, the TCDDM composition stored in a container may be stored in a warehouse or the like before and after transportation. The organic material production method of the present invention is suitable for such cases in which the TCDDM composition is stored and transported before being processed into an organic material.

[0206] (Temperature until TCDDM composition (A0) is stored in a container) In the method for producing an organic material of the present invention, it is preferable to store the TCDDM composition (A0) obtained by distillation purification in a container while maintaining the temperature above 45°C. By storing the distillation-purified TCDDM composition (A0) in a container while maintaining the temperature above 45°C, the formation of microcrystals in the TCDDM composition (A0) and an increase in viscosity are suppressed, thereby maintaining the storage stability of the TCDDM composition (A0). As a result, it is possible to produce organic materials more efficiently. The temperature from the distillation purification to storage in a storage container is preferably maintained above 45°C, and the lower limit of the temperature until storage is preferably 45°C or higher, more preferably 50°C or higher, even more preferably 60°C or higher, still more preferably above 60°C, even more preferably 70°C or higher, still more preferably above 70°C, and particularly preferably 75°C or higher. The upper limit of the temperature before storage is preferably 110°C or lower, more preferably 100°C or lower, even more preferably 95°C or lower, still more preferably 90°C or lower, even more preferably less than 90°C, and even more preferably 85°C or lower. The upper and lower limits of the temperature from the distillation purification (tank) to storage in the storage container can be arbitrarily combined. For example, the temperature before storage is preferably 45°C or higher and 110°C or lower, more preferably 50°C or higher and 100°C or lower, even more preferably 60°C or higher and 95°C or lower, even more preferably higher than 60°C and 90°C or lower, even more preferably 70°C or higher and lower than 90°C, and even more preferably higher than 70°C and 85°C or lower.

[0207] The time for which the TCDDM composition (A0) obtained by distillation and purification is kept so as not to fall below 45°C is preferably at least 1 hour, more preferably more than 1 hour, even more preferably at least 5 hours, even more preferably at least 15 hours, still more preferably at least 30 hours, and even more preferably at least 45 hours. Meanwhile, the upper limit of the temperature until storage in the aforementioned container is preferably 130 hours or less, more preferably 110 hours or less, even more preferably 90 hours or less, still more preferably 70 hours or less, even more preferably 60 hours or less, and even more preferably 50 hours or less. The above upper and lower limits can be arbitrarily combined. For example, the time for which the TCDDM composition (A0) obtained by distillation and purification is kept so as not to fall below 45°C is preferably at least 1 hour and not more than 130 hours, more preferably more than 1 hour and not more than 110 hours, even more preferably 5 hours or more and not more than 90 hours, even more preferably 15 hours or more and not more than 70 hours, still more preferably 30 hours or more and not more than 60 hours, and even more preferably 45 hours or more and not more than 50 hours.

[0208] The temperature from the distillation purification (tank) to storage in the storage container may fluctuate as long as it does not fall below 45° C. Specifically, the temperature change from the distillation purification to storage in the storage container is preferably within ±30° C., more preferably within ±20° C., even more preferably within ±15° C., still more preferably within ±10° C., and even more preferably within ±5° C.

[0209] The distillation-purified TCDDM composition (A0) can be stored in a container directly from the distillation purification column. "Storing in a container directly from the distillation purification column" means that no intermediate operations such as heating or stirring are performed during transfer from the distillation purification column to the container; more specifically, "transferring" the TCDDM composition (A0) from the distillation purification column to the container is performed in a single step. Alternatively, the distillation-purified TCDDM composition (A0) can be temporarily stored in a storage tank located between the distillation purification column and the container, heated or maintained at a temperature not lower than 45°C, and then transferred to the container for storage.

[0210] The container in which the TCDDM composition (A0) is stored is not particularly limited in type, and any container capable of storing TCDDM may be used. Therefore, the container includes not only drums, 18-liter cans, glass bottles, etc., but also transportation vehicles such as trailers. From the viewpoints of transportation cost and ease of handling, drums are preferred.

[0211] Steps (1) and (2) in Fig. 5 are not necessarily required. For example, a TCDDM composition (A1) containing chiral compound A stored in a container at a temperature of less than 45°C can be purchased from a manufacturer of raw materials for the TCDDM composition.

[0212] Steps (3) and (4) in Figure 5 are each independently a transporting step and / or a storage step. Specific examples of steps (3) and (4) in Figure 5 include a case in which a manufacturer of the TCDDM composition stores the TCDDM composition (A1) stored in a container, a case in which a transporter of the TCDDM composition (A1) transports or stores the TCDDM composition (A1) stored in a container, and a case in which a customer of the TCDDM composition (A1) stores the TCDDM composition (A1) stored in a container.

[0213] (Temperature of TCDDM composition (A1) stored in a container) The method for producing an organic material of the present invention is particularly suitable when TCDDM composition (A1) is stored in a container and placed in an environment of −5° C. or higher and lower than 45° C. for 24 hours or longer before heating in step (5) described below. Here, "placed" includes not only storage in a warehouse, but also movement of TCDDM composition (A1) stored in a container in a state where it is not subjected to excessive vibration, such as during transportation.

[0214] When the TCDDM composition is stored in a container in an environment of -5°C or higher but lower than 45°C for 24 hours or longer, the lower limit of the storage temperature is preferably -5°C or higher, more preferably 0°C or higher, even more preferably 5°C or higher, still more preferably 10°C or higher, and even more preferably 15°C or higher. The upper limit of the storage temperature is preferably less than 45°C, more preferably 43°C or lower, even more preferably 40°C or lower, still more preferably 35°C or lower, and even more preferably 30°C or lower. By setting the temperature at or above the lower limit, the formation of microcrystals in the TCDDM composition is suppressed, thereby further improving the effect of suppressing an increase in viscosity. By setting the temperature below or equal to or below the upper limit, the effect of suppressing deterioration of the TCDDM composition due to thermal decomposition or alteration is further improved. The upper and lower limits of the storage temperature can be combined in any manner. For example, the temperature combination of the storage environment is preferably −5° C. or higher and lower than 45° C., more preferably 0° C. or higher and 43° C. or lower, even more preferably 5° C. or higher and 40° C. or lower, even more preferably 10° C. or higher and 35° C. or lower, and even more preferably 15° C. or higher and 30° C. or lower.

[0215] The temperature of the storage environment may fluctuate within a range of −5° C. or higher and lower than 45° C. Specifically, the temperature change of the storage environment is preferably within ±20° C., more preferably within ±15° C.

[0216] In the case where the product is stored in a container and placed in an environment of -5°C or higher and lower than 45°C for 24 hours or longer, the period of time for which the product is placed is usually 24 hours or longer and up to 3 years.

[0217] Steps (3) and (4) in Fig. 5 are not necessarily required. For example, the TCDDM composition (A1) containing chiral compound A, which has been stored in a container and is kept at a temperature of less than 45°C, can be purchased and directly put into a processing machine for processing.

[0218] (Heating temperature of TCDDM composition (A1) before feeding into processing machine) Step (5) in Figure 5 above shows a process in which part or all of TCDDM composition (A1) is heated to 45°C or higher but lower than 120°C, and the heated TCDDM composition (A2) is fed into processing machine (X) while maintained at a temperature of 45°C or higher but lower than 120°C. By heating part or all of TCDDM composition (A1) to 45°C or higher but lower than 120°C, and feeding the heated TCDDM composition (A2) into processing machine (X) while maintaining a temperature of 45°C or higher but lower than 120°C in this way, it is possible to suppress the formation of microcrystals in the TCDDM composition and an increase in viscosity, and also to prevent the TCDDM composition from becoming cloudy, allowing for more efficient production of organic materials.

[0219] The lower limit of the heating temperature of the TCDDM composition (A1) is 45°C or higher, preferably 50°C or higher, more preferably 52°C or higher, even more preferably 54°C or higher, still more preferably 56°C or higher, and even more preferably 58°C or higher. The upper limit of the heating temperature is less than 120°C, preferably 100°C or lower, more preferably 80°C or lower, even more preferably 75°C or lower, still more preferably 70°C or lower, and even more preferably 65°C or lower. By setting the heating temperature at or above the lower limit, the formation of microcrystals in the TCDDM composition before loading into a processing machine can be suppressed, and an increase in viscosity can be suppressed, thereby maintaining good handleability of the TCDDM composition when loaded into a processing machine. By setting the heating temperature at or below the upper limit, the TCDDM composition can be prevented from decomposing or deteriorating due to thermal decomposition. Furthermore, an increase in utility costs such as steam and electricity can be suppressed. The upper and lower limits of the heating temperature can be combined in any combination. The upper and lower limits of the heating temperature can be combined in any combination. For example, the heating temperature is 45°C or higher and lower than 120°C, preferably 50°C or higher and 100°C or lower, more preferably 52°C or higher and 80°C or lower, even more preferably 54°C or higher and 75°C or lower, even more preferably 56°C or higher and 70°C or lower, and even more preferably 58°C or higher and 65°C or lower.

[0220] The heating temperature may fluctuate within a range of 45° C. or higher and lower than 120° C. Specifically, the temperature change in the temperature environment is preferably within ±20° C., more preferably within ±15° C., even more preferably within ±10° C., and even more preferably within ±5° C.

[0221] Heating of TCDDM composition (A1) is preferably carried out while the TCDDM composition (A1) is stored in a container. By not transferring the composition to another container, the generation of microcrystals of chiral compound A can be more effectively suppressed. However, in the method for producing an organic material of the present invention, it is not necessarily necessary to heat the TCDDM composition (A1) while it is stored in a container. For example, heating in a pipe connecting the TCDDM composition (A1) to a processing machine is also considered to be included in the heating of part or all of the TCDDM composition (A1) to a temperature of 45°C or higher but lower than 120°C.

[0222] (Heating Temperature During Feeding of TCDDM Composition (A1) into Processing Machine (X)) The heated TCDDM composition (A2) is fed into the processing machine while being maintained at a temperature of 45°C or higher but lower than 120°C. The lower limit of the temperature of TCDDM composition (A2) during feeding into the processing machine after heating is preferably 50°C or higher, more preferably 52°C or higher, even more preferably 54°C or higher, still more preferably 56°C or higher, and even more preferably 58°C or higher. The upper limit of the temperature of TCDDM composition (A2) during feeding into the processing machine after heating is preferably 100°C or lower, more preferably 80°C or lower, still more preferably 75°C or lower, still more preferably 70°C or lower, and even more preferably 65°C or lower. By ensuring that the temperature is equal to or higher than the lower limit, the formation of microcrystals in the TCDDM composition during feeding into the processing machine can be suppressed, and an increase in viscosity can be suppressed, thereby maintaining good handleability of the TCDDM composition. Furthermore, by keeping the temperature at or below the upper limit, deterioration due to thermal decomposition or alteration of the TCDDM composition can be suppressed. Furthermore, increases in utility costs such as steam and electricity can be suppressed. The upper and lower limits for the temperature of the TCDDM composition (A2) during the heating process and subsequent feeding into the processing machine can be arbitrarily combined. For example, the temperature is preferably 50°C or higher and 100°C or lower, more preferably 52°C or higher and 80°C or lower, even more preferably 54°C or higher and 75°C or lower, even more preferably 56°C or higher and 70°C or lower, and even more preferably 58°C or higher and 65°C or lower.

[0223] The temperature of the TCDDM composition (A2) during heating and subsequent feeding into the processing machine may fluctuate within a range of 45° C. or higher and lower than 120° C. Specifically, the temperature change during heating and subsequent feeding into the processing machine is preferably within ±20° C., more preferably within ±15° C., even more preferably within ±10° C., and even more preferably within ±5° C.

[0224] The heated TCDDM composition (A2) may be charged partially or entirely into the processing machine. The term "charging a portion of the TCDDM composition (A2)" also includes the case where the TCDDM composition (A2) is charged into the processing machine sequentially. Furthermore, after charging a portion of the TCDDM composition (A2) into the processing machine, the container containing the remaining TCDDM composition (A2) may be temporarily stored, and the TCDDM composition (A2) may then be charged into the processing machine again to produce the organic material. The processing machine into which the remaining TCDDM composition (A2) is charged may be the same as or different from the previous processing machine. Furthermore, when charging a portion of the TCDDM composition (A2) into the processing machine and then temporarily storing the container containing the remaining TCDDM composition (A2), it is preferable to store the container containing the remaining TCDDM composition (A2) at a temperature of 45°C or higher but lower than 120°C.

[0225] In the method for producing an organic material of the present invention, it is preferable to heat the TCDDM composition (A1) while it is stored in the container, and then directly charge the heated TCDDM composition (A2) from the container into the processing machine.

[0226] In this specification, "directly adding" means that the contents of the container are transferred into the processing machine in a single "transfer" step, without any intermediate operations such as heating or stirring. Therefore, it goes without saying that the "transfer" step also includes the case where the contents are transferred via a connecting pipe between the container and the processing machine. Eliminating the transfer step can effectively suppress the generation of microcrystals in the TCDDM composition (A2).

[0227] The processing machine is not particularly limited in type, provided that it is a device for processing the TCDDM composition (A2). The processing machine is not particularly limited as long as it is a machine for converting the TCDDM composition into a desired shape or properties, or for converting TCDDM into another compound, and examples thereof include a reactor and a compounder. Furthermore, "processing the TCDDM composition" refers, for example, to causing a chemical reaction in the reactor to convert the TCDDM composition into another compound, or to mixing the TCDDM composition with another substance in the compounder.

[0228] In the production method of the present invention, after TCDDM composition (A0) has been stored in a container, it is preferable not to heat TCDDM composition (A1) until it is heated to a temperature of 45° C. or higher but lower than 120° C. This configuration enables more efficient production of organic materials.

[0229] A preferred embodiment of the method for producing an organic material of the present invention will be described below. A first preferred embodiment of the method for producing an organic material of the present invention comprises heating part or all of TCDDM composition (A1) stored in a container at a temperature below 45°C to 45°C or higher but lower than 120°C, and then feeding the heated TCDDM composition (A2) into a processing machine while maintaining the temperature at 45°C or higher but lower than 120°C for processing, wherein the TCDDM composition (A1) is heated while still stored in the container and then directly fed from the container into the processing machine, wherein the content of chiral compound A in the TCDDM composition (A1) is 25% by mass or higher but lower than 54% by mass, based on 100% by mass of the total mass of the TCDDM composition (A1), the processing machine is a reactor and / or a compounder, and the organic material is at least one polymer selected from the group consisting of polyester resins, epoxy resins, acrylate resins, polycarbonate resins, and polyurethane resins, or an ultraviolet-curable composition.

[0230] A second preferred embodiment of the method for producing an organic material of the present invention is the method for producing an organic material of the first embodiment, further comprising storing TCDDM composition (A0) obtained by distillation and purification in a container while maintaining the temperature above 45°C, and TCDDM composition (A1) in the container has been placed in an environment of −5°C or higher and lower than 45°C for 24 hours or longer before heating.

[0231] A third preferred embodiment of the method for producing an organic material of the present invention is the method for producing an organic material of the first and / or second embodiments, in which no stirring is performed after the TCDDM composition (A0) is stored in a container until the TCDDM composition (A2) is directly charged into the processing machine.

[0232] A fourth preferred embodiment of the method for producing an organic material of the present invention is the method for producing an organic material of any one of the first to third embodiments, wherein, after TCDDM composition (A0) has been stored in a container, heating is not carried out until TCDDM composition (A1) is heated to a temperature of 45°C or higher but lower than 120°C.

[0233] [TCDDM composition (A1)] Next, tricyclodecane dimethanol composition (A1) (TCDDM composition (A1)) containing a chiral compound of which one enantiomer is represented by formula (A) will be described. TCDDM composition (A1) of the present invention is a composition containing a chiral compound of which one enantiomer is represented by formula (A) (chiral compound A), which is stored in a container and maintained at a temperature of less than 45°C:

[0234]

[0235] The TCDDM composition (A1) of the present invention can be obtained by storing the above-mentioned starting material TCDDM composition (A0) in a container while maintaining its temperature above 45° C. Specifically, the TCDDM composition (A1) can also be obtained by distilling and purifying a crude reaction solution obtained through a step of hydroformylating dicyclopentadiene to obtain tricyclodecane dicarbaldehyde and a step of obtaining a crude reaction solution containing tricyclodecane dimethanol by reduction of the tricyclodecane dicarbaldehyde, and then directly storing the crude reaction solution in a container while maintaining its temperature above 45° C.

[0236] (Backscattering intensity T of TCDDM composition (A1) １ In the TCDDM composition (A1) of the present invention, the 173° backscattering intensity T １ The lower limit of is not particularly limited, but is ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷500≦T １ ≦T ２ The above-mentioned constitution makes it possible to obtain a TCDDM composition (A1) having excellent storage stability and excellent flowability.

[0237] 173°backscatter intensity T １ is an index showing the fluidity and storage stability of a TCDDM composition.

[0238] The backscattering intensity T １ The lower limit of T ２ By setting the value to ÷ 500 or more, the 173° backscattering intensity T １ The backscattering intensity T １ The upper limit of T ２ By setting the following, the 173° backscattering intensity T １is relatively reduced, the amount of TCDDM microcrystals in the TCDDM composition (A1) is reduced or the increase in the amount of TCDDM microcrystals is suppressed, and an increase in viscosity during storage is suppressed, resulting in good storage stability.

[0239] Backscatter intensity T １ T ２ The method for achieving the above is not particularly limited, but can be achieved, for example, by storing a part or all of the TCDDM composition (A0) in a container while maintaining the temperature at a temperature of 45° C. or higher and lower than 120° C. so that the temperature does not fall below 45° C. On the other hand, the backscattering intensity T １ T ２ The method for achieving a ratio of ÷500 or more is not particularly limited, but can be achieved, for example, by suppressing heating of the TCDDM raw material (TCDDM composition (A0)) after production, stirring of the TCDDM in a heated state, or transferring of the TCDDM to another container.

[0240] In the TCDDM composition (A1) of the present invention, the backscattering intensity T １ The lower limit of T ２ ÷500 or more is preferable, and T ２ ÷250 or more is more preferable, and T ２ ÷200 or more is more preferable, and T ２ ÷100 or more is particularly preferred, and T ２ The backscattering intensity T １ The upper limit of T ２ The following is preferred: T ２ ÷2 or less is more preferable, and T ２ ÷3 or less is more preferable, and T ２ ÷4 or less is more preferable, and T ２ It is even more preferable that the backscattering intensity T is 5 or less. By making the backscattering intensity T equal to or greater than the lower limit, the TCDDM composition (A1) has a suitable fluidity, which makes it easier to handle during preparation operations and the like. Furthermore, by making the backscattering intensity T equal to or less than the upper limit, the viscosity of the TCDDM composition (A1) is less likely to increase during storage, resulting in good storage stability. The above upper and lower limits can be combined arbitrarily. For example, in the TCDDM composition (A1), １ Is T ２ ÷500≦T１ ≦T ２ is preferred, and T ２ ÷250≦T １ ≦T ２ ÷2 is more preferable, and T ２ ÷200≦T １ ≦T ２ ÷3 is more preferred, and T ２ ÷100≦T １ ≦T ２ ÷4 is more preferred, and T ２ ÷50≦T １ ≦T ２ ÷5 is even more preferable.

[0241] As a more specific embodiment of the TCDDM composition (A1) of the present invention, for example, １ The lower limit of the backscattering intensity T is preferably 10 or more, more preferably 50 or more, even more preferably 100 or more, even more preferably 200 or more, and still more preferably 400 or more. １ The upper limit of is preferably 5000 or less, more preferably 3000 or less, even more preferably 2000 or less, even more preferably 1000 or less, and even more preferably 900 or less. By setting it at or above the lower limit, TCDDM composition (A1) has appropriate fluidity, which makes it easier to handle during blending operations and the like. Furthermore, by setting it at or below the upper limit, the viscosity of TCDDM composition (A1) is less likely to increase during storage, resulting in good storage stability. The above upper and lower limits can be combined in any way. For example, in TCDDM composition (A1), １ , 10≦T １ ≦5000 is preferred, and 50≦T １ ≦3000 is more preferable, and 100≦T １ ≦2000 is more preferable, and 200≦T １ ≦1000 is more preferable, and 400≦T １ Even more preferably ≦900.

[0242] The TCDDM composition (A1) of the present invention may contain, in addition to chiral compound A, chiral compound A and / or chitricyclodecane dimethanol (sometimes referred to herein as "chiral compound B"), one enantiomer of which is represented by the following formula (B): In other words, the more chiral compound A is contained, the more microcrystals are produced in the TCDDM composition (A1), and the more suitable the fluidity and the easier it tends to be to handle in blending operations and the like; and the more chiral compound B is contained, the relatively lower the proportion of chiral compound A is, and the more TCDDM microcrystals in the TCDDM composition (A1) are reduced or the increase of TCDDM microcrystals is inhibited, which makes it less likely to increase in viscosity during storage and tends to improve storage stability.

[0243]

[0244] Furthermore, the TCDDM composition (A1) of the present invention may contain, in addition to chiral compound A and chiral compound B, and / or chiricyclodecane dimethanol, one enantiomer of which is represented by formula (C) (sometimes referred to herein as "chiral compound C") In other words, the more chiral compound C is contained, the more the TCDDM microcrystals in the TCDDM composition (A1) are reduced or the increase of TCDDM microcrystals is suppressed, and the viscosity is less likely to increase during storage, tending to improve storage stability.

[0245]

[0246] (Content of Chiral Compound A) In the TCDDM composition (A1) of the present invention, the lower limit of the content of chiral compound A is not particularly limited, but is preferably 25% by mass or more, more preferably 28% by mass or more, even more preferably 30% by mass or more, even more preferably 32% by mass or more, even more preferably 33% by mass or more, even more preferably 34% by mass or more, particularly more preferably 35% by mass or more, and particularly more preferably 36% by mass or more, relative to the total mass of the TCDDM composition (A1) (100% by mass). The upper limit of the content of chiral compound A is not particularly limited, but is preferably 54% by mass or less, more preferably 50% by mass or less, even more preferably 45% by mass or less, even more preferably 43% by mass or less, even more preferably 41% by mass or less, even more preferably 40% by mass or less, particularly more preferably 39% by mass or less, and particularly more preferably 38.5% by mass or less. By setting the content at or above the lower limit, microcrystals are generated in the TCDDM composition (A1), ensuring appropriate fluidity and excellent handling during blending operations, etc. By setting the content at or below the upper limit, the generation of TCDDM microcrystals in the TCDDM composition (A1) is suppressed, and an increase in viscosity during storage is suppressed, resulting in good storage stability. The above upper and lower limits can be combined in any desired manner. For example, in TCDDM composition (A1), the content of the chiral compound A is not particularly limited, but is preferably from 25 to 54 mass%, more preferably from 28 to 50 mass%, even more preferably from 30 to 45 mass%, even more preferably from 32 to 43 mass%, even more preferably from 33 to 41 mass%, even more preferably from 34 to 40 mass%, particularly preferably from 35 to 39 mass%, and even particularly preferably from 36 to 38.5 mass%, relative to the total mass of the TCDDM composition (A1) (100 mass%).

[0247] (Content of chiral compound B) In TCDDM composition (A1) of the present invention, the lower limit of the content of chiral compound B is not particularly limited, but is preferably 1.6 mass% or more, more preferably 1.8 mass% or more, even more preferably 2.0 mass% or more, still more preferably 2.1 mass% or more, even more preferably 2.2 mass% or more, and still more preferably 2.3 mass% or more, relative to 100 mass% total mass of TCDDM composition (A1). The upper limit of the content of chiral compound B in TCDDM composition (A1) is not particularly limited, but is preferably 4.8% by mass or less, more preferably 4.6% by mass or less, even more preferably 4.4% by mass or less, even more preferably 4.3% by mass or less, even more preferably 4.2% by mass or less, and even more preferably 4.0% by mass or less, in the order of 3.8% by mass or less, 3.5% by mass or less, 3.2% by mass or less, 3.0% by mass or less, 2.8% by mass or less, and 2.7% by mass or less, based on the total mass (100% by mass) of TCDDM composition (A1). By ensuring that the content is equal to or greater than the lower limit, the formation of TCDDM microcrystals in TCDDM composition (A1) is suppressed, and an increase in viscosity during storage is suppressed, resulting in improved storage stability. By ensuring that the content is equal to or less than the upper limit, microcrystals are formed in TCDDM composition (A1), ensuring appropriate fluidity and providing better handling during blending operations, etc. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A1), the content of chiral compound B is not particularly limited, but is preferably from 1.6 to 4.8 mass%, more preferably from 1.8 to 4.6 mass%, even more preferably from 2.0 to 4.4 mass%, still more preferably from 2.1 to 4.3 mass%, even more preferably from 2.2 to 4.2 mass%, and even more preferably from 2.3 to 4.0 mass%, relative to the total mass of TCDDM composition (A1) (100 mass%).

[0248] (Content of Chiral Compound C) In the TCDDM composition (A1) of the present invention, the lower limit of the content of chiral compound C is not particularly limited, but is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 18% by mass or more, still more preferably 20% by mass or more, even more preferably 22% by mass or more, and still more preferably 25% by mass or more, relative to 100% by mass of the total mass of the TCDDM composition (A1). The upper limit of the content of chiral compound C in the TCDDM composition (A1) is not particularly limited, but is preferably 45% by mass or less, more preferably 40% by mass or less, even more preferably 38% by mass or less, even more preferably 35% by mass or less, still more preferably 33% by mass or less, and still more preferably 30% by mass or less, relative to 100% by mass of the total mass of the TCDDM composition (A1). By setting the content at or above the lower limit, the formation of TCDDM microcrystals in the TCDDM composition (A1) is suppressed, and an increase in viscosity during storage is suppressed, resulting in improved storage stability. Furthermore, by setting the content at or below the upper limit, microcrystals are generated in the TCDDM composition (A1), ensuring appropriate fluidity and thus superior handling during blending operations. The upper and lower limits can be arbitrarily combined. For example, the content of the chiral compound C in the TCDDM composition (A1) is not particularly limited, but is preferably 10% by mass to 45% by mass, more preferably 15% by mass to 40% by mass, even more preferably 18% by mass to 38% by mass, even more preferably 20% by mass to 35% by mass, still more preferably 22% by mass to 33% by mass, and even more preferably 25% by mass to 30% by mass, relative to the total mass of the TCDDM composition (A1).

[0249] (TCDDM Content) In TCDDM composition (A1), there is no particular lower limit to the total TCDDM content, but from the viewpoint of ease of handling the composition, it is preferably 70% by mass or more, more preferably 80% by mass or more, even more preferably 90% by mass or more, still more preferably 95% by mass or more, even more preferably 97% by mass or more, and still more preferably 99% by mass or more, relative to 100% by mass of the total mass of TCDDM composition (A1). On the other hand, there is no particular upper limit to the total TCDDM content in TCDDM composition (A1), and a higher value is preferable, and it may even be 100% by mass, relative to the total mass of TCDDM composition (A1).

[0250] The TCDDM composition (A1) of the present invention may contain compounds other than TCDDM as long as the effects of the present invention are not impaired. The "compounds other than TCDDM" are not particularly limited, and examples include compounds having an aldehyde group that are reaction intermediates during the synthesis of TCDDM, compounds having a carbonyl group derived from compounds containing the aldehyde group, diols containing 12 carbon atoms that are mixed in during the manufacturing process, and known additives that are blended as needed. The content of the compounds other than TCDDM in the TCDDM composition (A1) of the present invention is not particularly limited as long as the effects of the present invention are not impaired. Typically, the content of the compounds other than TCDDM is 0.01% by mass or more and 2% by mass or less, based on the total mass of the TCDDM composition (A1) (100% by mass). Alternatively, the composition may contain no compounds other than TCDDM (0% by mass).

[0251] (Total Content of Chiral Compounds A to C) In TCDDM composition (A1), the lower limit of the total content of chiral compound A, chiral compound B, and chiral compound C is not particularly limited, but from the viewpoint of ease of handling of the composition, it is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more, relative to 100% by mass of the total mass of TCDDM composition (A1). On the other hand, the upper limit of this total content is not particularly limited, and a higher value is preferable, and it may be 100% by mass, relative to the total mass of TCDDM composition (A1).

[0252] [TCDDM composition (A2)] The TCDDM composition (A2) of the present invention is obtained by heating a part or all of the TCDDM composition (A1) to a temperature of 45°C or higher and lower than 120°C.

[0253] (Backscattering intensity T of TCDDM composition (A2) １ The TCDDM composition (A2) has a 173° backscattering intensity T １ is the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷8.0≦T １ ≦T ２ × 5.0. With the above-mentioned configuration, a TCDDM composition (A2) having excellent storage stability and excellent fluidity can be obtained. １ The lower limit of T ２ By making the backscattering intensity T / 8.0 or more, microcrystals are generated in the TCDDM composition (A1), and the composition has a suitable fluidity, making it less likely to exhibit spinnability and providing excellent handling during preparation operations, etc. １ The upper limit of ２ By making the ratio x 5.0 or less, the amount of TCDDM microcrystals in the TCDDM composition (A2) is reduced or the increase in the amount of TCDDM microcrystals is suppressed, thereby suppressing an increase in viscosity during processing and improving storage stability and ease of handling during blending operations, etc.

[0254] Backscatter intensity T １ The method for adjusting the temperature to fall within the above range is not particularly limited, but for example, this can be achieved by heating a part or all of the TCCM composition (A1) stored in a container at a temperature below 45° C. to 45° C. or higher and lower than 120° C. More preferably, this can be achieved by carrying out steps (2) to (4) in FIG. 5 described above.

[0255] In the TCDDM composition (A2), the backscattering intensity T １ The lower limit of T ２ ÷8.0 or more is preferable, and T ２ ÷4.0 or more is more preferable, and T２ ÷3.5 or less is more preferable, and T ２ ÷3.0 or more is more preferable, and T ２ ÷2.5 or more is more preferable, and T ２ Furthermore, in the TCDDM composition of the embodiment, the backscattering intensity T １ The upper limit of T ２ × 5.0 or less is preferable, and T ２ × 2.0 or less is more preferable, and T ２ x 1.5 or less is more preferable, and T ２ More preferably, ２ ÷1.3 or less is more preferable, and T ２ It is even more preferable that the backscattering intensity T is 1.5 or less. By making the backscattering intensity T equal to or greater than the lower limit, the TCDDM composition (A2) has appropriate fluidity, and is therefore less likely to exhibit spinnability, resulting in excellent handling during blending operations and the like. Furthermore, by making the backscattering intensity T equal to or less than the upper limit, the viscosity is less likely to increase, resulting in good storage stability and ease of handling during blending operations and the like. The above upper and lower limits can be combined arbitrarily. For example, in the TCDDM composition (A2), １ Is T ２ ÷8.0≦T １ ≦T ２ × 5.0 is preferable, and T ２ ÷4.0≦T １ ≦T ２ × 2.0 is more preferable, and T ２ ÷3.5≦T １ ≦T ２ × 1.5 is more preferable, and T ２ ÷3.0≦T １ ≦T ２ is more preferred, and T ２ ÷2.5≦T １ ≦T ２ ÷1.3 is even more preferable, and T ２ ÷2.0≦T １ ≦T ２ ÷1.5 is even more preferred.

[0256] In addition, in Example 3-1 (T ２ ÷1), the backscattering intensity T １However, in the present invention, the backscattering intensity T １ In this case, the effects of the present invention can be obtained.

[0257] As a more specific embodiment of the TCDDM composition (A2) of the present invention, for example, １ The lower limit of the backscattering intensity T is preferably 500 or more, more preferably 800 or more, even more preferably 1100 or more, even more preferably 1500 or more, and still more preferably 2000 or more. １ The upper limit of is preferably 10,000 or less, more preferably 8,000 or less, even more preferably 7,000 or less, even more preferably 6,000 or less, and even more preferably 5,000. By setting it to the lower limit or more, TCDDM composition (A2) has appropriate fluidity, and is therefore less likely to exhibit spinnability, resulting in better handling during blending operations and the like. Furthermore, by setting it to the upper limit or less, the viscosity of TCDDM composition (A2) is less likely to increase, resulting in better storage stability and easier handling during blending operations and the like. The above upper and lower limits can be combined in any way. For example, in TCDDM composition (A2), １ , 500≦T １ ≦10000 is preferred, and 800≦T １ ≦8000 is more preferable, and 1100≦T １ ≦7000 is more preferable, and 150≦T １ ≦6000 is more preferable, and 2000≦T １ Even more preferred is ≦5000.

[0258] In addition to chiral compound A, TCDDM composition (A2) of the present invention may contain chiral compound B represented by formula (B) and chiral compound C represented by formula (C). That is, the more chiral compound A is contained, the more microcrystals are formed in TCDDM composition (A2), and the more suitable the fluidity is, which tends to improve handling during blending operations, etc. The more chiral compound B is contained, the lower the proportion of chiral compound A becomes, which reduces the amount of TCDDM microcrystals in TCDDM composition (A1) or suppresses the increase of TCDDM microcrystals, which tends to reduce the viscosity increase during storage, and tends to improve storage stability. The more chiral compound C is contained, the lower the proportion of chiral compound A becomes, which reduces the amount of TCDDM microcrystals in TCDDM composition (A1) or suppresses the increase of TCDDM microcrystals, which tends to reduce the viscosity increase during storage, and tends to improve storage stability.

[0259]

[0260]

[0261] In addition, chiral compound A, chiral compound B, and chiral compound C in TCDDM composition (A2) can be treated as synonyms for chiral compound A, chiral compound B, and chiral compound C in TCDDM composition (A1), respectively.

[0262] (Content of Chiral Compound A) In the TCDDM composition (A2) of the present invention, the lower limit of the content of chiral compound A is, but is not particularly limited to, preferably 25% by mass or more, more preferably 28% by mass or more, even more preferably 30% by mass or more, even more preferably 32% by mass or more, even more preferably 33% by mass or more, even more preferably 34% by mass or more, particularly more preferably 35% by mass or more, and even particularly more preferably 36% by mass or more, relative to 100% by mass of the total mass of TCDDM composition (A2). The upper limit of the content of chiral compound A is, but is not particularly limited to, preferably 54% by mass or less, more preferably 50% by mass or less, even more preferably 45% by mass or less, even more preferably 43% by mass or less, even more preferably 41% by mass or less, even more preferably 40% by mass or less, particularly more preferably 39% by mass or less, and even particularly more preferably 38.5% by mass or less, relative to 100% by mass of the total mass of TCDDM composition (A2). By setting the content at or above the lower limit, microcrystals are generated in the TCDDM composition (A2), ensuring appropriate fluidity and excellent handling during blending operations, etc. By setting the content at or below the upper limit, the generation of TCDDM microcrystals in the TCDDM composition (A2) is suppressed, and an increase in viscosity during storage is suppressed, resulting in good storage stability. The above upper and lower limits can be combined in any desired manner. For example, in TCDDM composition (A2), the content of chiral compound A is not particularly limited, but is preferably from 25 to 54 mass%, more preferably from 28 to 50 mass%, even more preferably from 30 to 45 mass%, even more preferably from 32 to 43 mass%, even more preferably from 33 to 41 mass%, even more preferably from 34 to 40 mass%, particularly preferably from 35 to 39 mass%, and even particularly preferably from 36 to 38.5 mass%, relative to the total mass of TCDDM composition (A2) (100 mass%).

[0263] (Content of chiral compound B) In TCDDM composition (A2) of the present invention, the lower limit of the content of chiral compound B is not particularly limited, but is preferably 1.6 mass% or more, more preferably 1.8 mass% or more, even more preferably 2.0 mass% or more, still more preferably 2.1 mass% or more, even more preferably 2.2 mass% or more, and still more preferably 2.3 mass% or more, relative to the total mass of TCDDM composition (A2) (100 mass%). The upper limit of the content of chiral compound B in TCDDM composition (A2) is not particularly limited, but is preferably 4.8% by mass or less, more preferably 4.6% by mass or less, even more preferably 4.4% by mass or less, even more preferably 4.3% by mass or less, even more preferably 4.2% by mass or less, and even more preferably 4.0% by mass or less, in the order of 3.8% by mass or less, 3.5% by mass or less, 3.2% by mass or less, 3.0% by mass or less, 2.8% by mass or less, and 2.7% by mass or less, based on the total mass (100% by mass) of TCDDM composition (A2). By ensuring that the content is equal to or greater than the lower limit, the formation of TCDDM microcrystals in TCDDM composition (A2) is suppressed, and an increase in viscosity during storage is suppressed, resulting in improved storage stability. By ensuring that the content is equal to or less than the upper limit, microcrystals are formed in TCDDM composition (A2), ensuring appropriate fluidity, and thus reducing the need for handling during blending operations, etc. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A2), the content of chiral compound B is not particularly limited, but is preferably from 1.6 to 4.8 mass%, more preferably from 1.8 to 4.6 mass%, even more preferably from 2.0 to 4.4 mass%, still more preferably from 2.1 to 4.3 mass%, even more preferably from 2.2 to 4.2 mass%, and even more preferably from 2.3 to 4.0 mass%, relative to the total mass of TCDDM composition (A2) (100 mass%).

[0264] (Content of Chiral Compound C) In TCDDM composition (A2) of the present invention, the lower limit of the content of chiral compound C is not particularly limited, but is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 18% by mass or more, still more preferably 20% by mass or more, even more preferably 22% by mass or more, and still more preferably 25% by mass or more, relative to 100% by mass of the total mass of TCDDM composition (A2). The upper limit of the content of chiral compound C in TCDDM composition (A2) is not particularly limited, but is preferably 45% by mass or less, more preferably 40% by mass or less, even more preferably 38% by mass or less, even more preferably 35% by mass or less, still more preferably 33% by mass or less, and still more preferably 30% by mass or less, relative to 100% by mass of the total mass of TCDDM composition (A2). By setting the content at or above the lower limit, the formation of TCDDM microcrystals in TCDDM composition (A1) is suppressed, and an increase in viscosity during storage is suppressed, resulting in improved storage stability. Furthermore, by setting the content at or below the upper limit, microcrystals are generated in TCDDM composition (A1), ensuring appropriate fluidity and thus superior handling during blending operations. The upper and lower limits can be arbitrarily combined. For example, the content of chiral compound B in TCDDM composition (A1) is not particularly limited, but is preferably 10% by mass to 45% by mass, more preferably 15% by mass to 40% by mass, even more preferably 18% by mass to 38% by mass, even more preferably 20% by mass to 35% by mass, still more preferably 22% by mass to 33% by mass, and even more preferably 25% by mass to 30% by mass, relative to the total mass of TCDDM composition (A2) (100% by mass).

[0265] (TCDDM Content) In TCDDM composition (A2), the lower limit of the TCDDM content is not particularly limited, but from the viewpoint of ease of handling of the composition, it is preferably 80% by mass or more, more preferably 90% by mass or more, even more preferably 95% by mass or more, still more preferably 97% by mass or more, and still more preferably 99% by mass or more, relative to 100% by mass of the total mass of TCDDM composition (A2). On the other hand, the upper limit of the total content is not particularly limited, and a higher value is preferable, and it may be 100% by mass, relative to the total mass of TCDDM composition (A2).

[0266] (Total Content of Chiral Compounds A to C) In TCDDM composition (A2), there is no particular lower limit to the total content of chiral compound A, chiral compound B, and chiral compound C, but from the viewpoint of ease of handling the composition, it is preferably 80% by mass or more, more preferably 90% by mass or more, and even more preferably 95% by mass or more, relative to 100% by mass of the total mass of TCDDM composition (A2). On the other hand, there is no particular upper limit to the total content, and a higher value is preferable, and it may be 100% by mass, relative to 100% by mass of the total mass of TCDDM composition (A2).

[0267] [Organic Material] The organic material obtained by the organic material production method of the present invention is not particularly limited as long as it is an organic material obtained from the TCDDM composition (A2), and can be used to produce known organic materials. The organic material is not particularly limited, but is preferably at least one polymer selected from the group consisting of polyester-based resins, epoxy-based resins, acrylate-based resins, polycarbonate-based resins, and polyurethane-based resins, or an ultraviolet-curable composition. Examples of polyester-based resins, epoxy-based resins, acrylate-based resins, polycarbonate-based resins, polyurethane-based resins, and ultraviolet-curable compositions include those described in the "Second Embodiment" above.

[0268] The present invention will be explained in more detail below with reference to examples. The materials, amounts used, ratios, treatment contents, treatment procedures, etc. shown in the following examples can be changed as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. If the measuring instruments used in the examples are difficult to obtain due to discontinuation or the like, measurements can be made using other instruments with equivalent performance.

[0269] [Raw Materials] The compounds used in the Examples and Comparative Examples are as follows: DCPD: dicyclopentadiene (manufactured by the company) Rh(acac)(CO) ２ : acetylacetonatodicarbonylrhodium (manufactured by N.E. Chemcat Corporation) DBPO: tris(2,4-di-tert-butylphenyl)phosphite (manufactured by Tokyo Chemical Industry Co., Ltd.) Methylcyclohexane (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) Ruthenium-supported carbon (dry basis Ru content 5 mass%, water content 56 mass%) (trade name: Ru / C, manufactured by N.E. Chemcat Corporation) Nickel-chromium-supported diatomaceous earth catalyst (nickel-supported diatomaceous earth with a nickel support amount of 12% and a chromium support amount of 2%, produced in accordance with the description in Example 1 of JP 2005-279587 A) Powdered activated carbon (trade name: Tokusei Shirasagi, manufactured by Osaka Gas Chemicals Co., Ltd.)

[0270] [Measurement Methods] Evaluations in the examples and comparative examples were carried out by the following methods.

[0271] <Identification of Chiral Compounds A to C Contained in TCDDM Compositions> Chiral compounds A to C contained in the TCDDM compositions obtained in the Examples and Comparative Examples were determined by nuclear magnetic resonance spectroscopy according to the following procedure.

[0272] Samples of the TCDDM composition were dissolved in deuterated chloroform (CDCl ３ The sample solution was transferred to an NMR sample tube with an outer diameter of 5 mm. １ H-NMR, １３ C-NMR, DEPT, COSY, TOCSY, NOESY,１ H- １３ C HSQC, １ H- １３ C HMBC spectrum was measured. １ The H-NMR measurement conditions were a resonance frequency of 600 MHz, a flip angle of 45°, a data acquisition time of 3 s, a pulse repetition time of 10 s, an accumulation number of 16, and a measurement temperature of 25° C. The chemical shift reference was set at 0.00 ppm for the TMS signal. １３ The C-NMR measurement conditions were a resonance frequency of 151 MHz, a flip angle of 45°, a data acquisition time of 2 s, a pulse repetition time of 5 s, an accumulation count of 10,000, and a temperature of 25°C. The chemical shift reference was set to the TMS signal at 0.00 ppm. The structure was identified from the signal correlation.

[0273] <Measurement of Xa, Xb, Xc, and Xt> For the TCDDM compositions obtained in the Examples and Comparative Examples, the peak area Xa of chiral compound A, the peak area Xb of chiral compound B, the peak area Xc of chiral compound C, and the total peak area Xt of TCDDM were calculated using gas chromatography under the following gas chromatography analysis conditions. (Gas Chromatography Analysis Conditions) Measuring device: Gas chromatograph measuring device (product name: GC-2025, manufactured by Shimadzu Corporation) Carrier gas: Helium, linear velocity: 30 cm / sec Column: Capillary column (product name: DB-1, manufactured by Agilent Technologies, length 30 m × inner diameter 0.25 mm × film thickness 1.00 μm) Temperature (heating conditions): Heating from 160°C (no holding time) to 300°C (holding time 2 minutes) at a heating rate of 5°C / min Injection port temperature: 200°C Ion source temperature: 300°C Sample amount: 0.3 μL Split ratio: 1:30 Detector: Flame ionization detector (FID)

[0274] Gas chromatograms of the TCDDM compositions obtained in Examples 1-1, 2-1 and 3-1 are shown in FIGS. 1, 4 and 6, respectively.

[0275] In Figure 1, the peak labeled (1) between elution times 13.85 minutes and 14.05 minutes ("Peak 1") is the peak of chiral compound A in the TCDDM composition. In Figure 4, the peak labeled (1) between elution times 14.05 minutes and 14.35 minutes ("Peak 1") is the peak of chiral compound A in the TCDDM composition. In Figure 6, the peak labeled (1) between elution times 13.85 minutes and 14.05 minutes ("Peak 1") is the peak of chiral compound A in the TCDDM composition.

[0276] In Figure 1, the peak labeled (2) between elution times 13.65 and 13.85 minutes ("Peak 2") is the peak of chiral compound B in the TCDDM composition. In Figure 4, the peak labeled (2) between elution times 13.90 and 14.05 minutes ("Peak 2") is the peak of chiral compound B in the TCDDM composition. In Figure 6, the peak labeled (2) between elution times 13.75 and 13.85 minutes ("Peak 2") is the peak of chiral compound B in the TCDDM composition.

[0277] In Figure 1, the peak labeled (3) between elution times 13.65 and 13.85 minutes ("Peak 3") is the peak of chiral compound C in the TCDDM composition. In Figure 4, the peak labeled (3) between elution times 13.55 and 13.72 minutes ("Peak 3") is the peak of chiral compound C in the TCDDM composition. In Figure 6, the peak labeled (3) between elution times 13.35 and 13.55 minutes ("Peak 3") is the peak of chiral compound C in the TCDDM composition.

[0278] The peak preceding peak 3, which is derived from a compound in which the tricyclodecane skeleton is an exo form, the peak between peaks 2 and 3, and the peak following peak 1 were determined to be other TCDDM isomers.

[0279] The peak areas Xa, Xb, Xc, and Xt were determined according to the following procedure. For the gas chromatogram shown in FIG. 1 , the area between the baseline and the gas chromatogram curve in the elution time range of 13.00 to 14.4 minutes was designated Xt. For the gas chromatogram shown in FIG. 1 , the area between the baseline and the gas chromatogram curve in the elution time range of 13.85 to 14.05 minutes was designated Xa. For the gas chromatogram shown in FIG. 1 , the area between the baseline and the gas chromatogram curve in the elution time range of 13.65 to 13.85 minutes was designated Xb. For the gas chromatogram shown in FIG. 1 , the area between the baseline and the gas chromatogram curve in the elution time range of 13.65 to 13.85 minutes was designated Xc. For the gas chromatogram shown in FIG. 4 , the area between the baseline and the gas chromatogram curve in the elution time range of 13.20 to 14.5 minutes was designated Xt. For the gas chromatogram shown in FIG. 4, the area between the baseline and the gas chromatogram curve in the elution time range of 14.05 to 14.30 minutes was designated Xa. For the gas chromatogram shown in FIG. 4, the area between the baseline and the gas chromatogram curve in the elution time range of 13.90 to 14.05 minutes was designated Xb. For the gas chromatogram shown in FIG. 4, the area between the baseline and the gas chromatogram curve in the elution time range of 13.55 to 13.72 minutes was designated Xc. For the gas chromatogram shown in FIG. 6, the area between the baseline and the gas chromatogram curve in the elution time range of 13.00 to 14.4 minutes was designated Xt. For the gas chromatogram shown in FIG. 6, the area between the baseline and the gas chromatogram curve in the elution time range of 13.85 to 14.05 minutes was designated Xa. For the gas chromatogram shown in Figure 6, the area between the baseline and the gas chromatogram curve in the elution time range of 13.75 to 13.85 minutes was defined as Xb, and the area between the baseline and the gas chromatogram curve in the elution time range of 13.35 to 13.55 minutes was defined as Xc.For details of these measurement methods, please refer to the description in International Publication No. 2023 / 176641, the contents of which are incorporated herein by reference.

[0280] <Mass Analysis of TCDDM Composition> To confirm the formation of TCDDM for the TCDDM compositions obtained in the Examples and Comparative Examples, gas chromatography mass spectrometry was used to measure the m / z and fragment pattern by the following gas chromatography mass spectrometry. (Gas chromatography mass spectrometry conditions) Measurement device: Gas chromatograph (product name: GCMS-QP2010Ultra, manufactured by Shimadzu Corporation) Carrier gas: Helium, linear velocity: 40 cm / sec Column: BPX-5 (manufactured by Trajan Scientific and Medical, length 60 m × inner diameter 0.32 mm × film thickness 0.25 μm) Temperature (heating conditions): Heat from 160°C at 5°C / min to 300°C (hold time 2 min) Vaporizer temperature: 200°C Ion source temperature: 250°C MS interface temperature: 300°C Injection volume: 0.5 μL Split ratio: 1:30

[0281] <Backscatter intensity T １ Measurement of 173° backscattering intensity T for the TCDDM compositions obtained in the Examples and Comparative Examples was measured at a temperature of 25°C for the TCDDM compositions using a dynamic light scattering measurement method according to the following procedure. １ As a standard sample, D ５０ A 1% by volume aqueous suspension of spherical latex (product: standard particle size 3300A, Thermo Fisher Scientific Co., Ltd.) having a particle size of 300 nm was irradiated with ultrasonic waves in an ultrasonic bath for 3 minutes, and then diluted to 0.002% by volume with pure water filtered through a 0.2 μm filter. The backscattering intensity T ２ was measured.

[0282] A sample of the TCDDM composition placed in a glass reagent bottle was immersed in an oil bath set at 60° C., and the sample was heated while being stirred until the measurement temperature of the TCDDM composition reached 60° C. Next, stirring of the sample was stopped, and 1 mL of the TCDDM composition was sampled and placed in a measurement cell. The measurement cell was placed in a thermostatic bath attached to a dynamic light scattering measurement device, and while the measurement temperature of the TCDDM composition was maintained at 60° C., the backscattering intensity T １ The backscattering intensity T １ For Examples 1-1 to 1-6 and Comparative Examples 1-1 to 1-3, measurements were carried out immediately before immersion of the TCDDM composition samples in the oil bath (0 hour) and 96 hours, 175 hours, and 196 hours after immersion in the oil bath. For Examples 2-1, 3-1, and 3-2 and Comparative Examples 2-1, 3-1, and 3-2, measurements were carried out immediately before immersion of the TCDDM composition samples in the oil bath (0 hour) and 96 hours after immersion in the oil bath.

[0283] (Measurement conditions) Measuring device: dynamic light scattering measuring device (trade name: Zetasizer Nano ZS, manufactured by Malvern Panalytical) Detection method: 173° backscattering detection method (scattered light detector placed 173° behind the sample) Sample temperature: 60° C. Cell: glass

[0284] <Storage Stability> The TCDDM compositions obtained in Examples 1-1 to 1-6 and Comparative Examples 1-1 and 1-2 were evaluated for transparency and fluidity as indicators of storage stability. The evaluation methods were as follows. (Transparency) The appearance of the TCDDM compositions after storage for two months at room temperature (25°C) was visually observed and rated according to the following three-level rating criteria. The ratings were made by majority vote of five experts. (Rating Criteria) - The appearance was transparent. - The appearance was slightly cloudy. - The appearance was cloudy. (Fluidity) 10 mL of sample was placed in a 20 mL glass bottle (inner diameter 25 mm x total length 55 mm), the bottle was capped, and heated to 60°C. The time from when the glass bottle was horizontal to when the liquid level reached the lid (hereinafter referred to as "flow time") was measured.

[0285] <Handling Ease Test> Regarding the TCDDM compositions obtained in Examples 1-1 to 1-6 and Comparative Examples 1-1 and 1-2, handling ease, which is one indicator of storage stability, was evaluated by immersing the tip of a glass rod 10 mm into the TCDDM composition at room temperature (20°C) and then lifting it 10 cm, and evaluating the spinnability according to the following evaluation criteria. (Evaluation criteria) 1: No spinnability was observed. 2: Spinnability was observed, but the thread broke immediately. 3: Spinnability was observed, but the thread broke after a while. 4: Spinnability was observed, and the thread remained without breakage.

[0286] <Storage Condition> The TCDDM composition (A1) and the TCDDM composition (A2) obtained in Example 2-1 and Comparative Example 2-1 were evaluated for fluidity and transparency as indicators of storage condition. The evaluation method was as follows. (Fluidity) 10 mL of sample was placed in a 20 mL glass bottle (inner diameter 25 mm × total length 55 mm), and the glass bottle was capped and heated to 60°C. The glass bottle was then placed horizontally, and if the liquid level reached the lid within 5 minutes, it was deemed to have "fluidity." The evaluation was made by five experts, with the final evaluation being made by majority vote. (Transparency) The appearance of the TCDDM composition after storage for two months at room temperature (25°C) was visually observed and evaluated according to the following three-level evaluation criteria. The evaluation was made by five experts, with the evaluation being made by majority vote. (Evaluation Criteria) - The appearance was transparent. - The appearance was slightly transparent. - The appearance was cloudy.

[0287] <Determination of Suitability for Organic Material Production> The TCDDM compositions (A2) obtained in Examples 3-1 and 3-2 and Comparative Examples 3-1 and 3-2 were evaluated for fluidity and transparency as indicators for determining suitability for organic material production. The evaluation method was as follows. (Fluidity) 10 mL of sample was placed in a 20 mL glass bottle (inner diameter 25 mm × total length 55 mm), the bottle was capped, and heated to 60°C. If the liquid level reached the lid within 5 minutes of the glass bottle being placed horizontally, the composition was deemed to have "fluidity." The evaluation was conducted by five experts, with the final evaluation being made by majority vote. (Transparency) The appearance of the TCDDM compositions after storage at room temperature (25°C) for two months was visually observed and evaluated according to the following two-stage evaluation criteria. The evaluation was conducted by five experts, with the evaluation being made by majority vote. (Evaluation Criteria) - The appearance was transparent. - The appearance was cloudy.

[0288] [Example 1-1] [TCDDM Synthesis Example] <Hydroformylation Reaction> In a 500 mL autoclave reactor (vertical stirring type), Rh(acac)(CO) was added as a raw material compound for a hydroformylation reaction catalyst under a nitrogen atmosphere. ２ 14.5 mg of methylcyclohexane and 1090.8 mg of DBPO were weighed out, 89 g of methylcyclohexane as an organic solvent, and 113 g of DCPD as a raw material compound were charged, and the temperature of the reaction solution in the reactor was raised to 70 ° C. while stirring by up-and-down stirring. Next, a mixed gas of hydrogen and carbon monoxide (hydrogen:carbon monoxide = 1:1 (molar ratio)) was quickly injected through the gas inlet valve so that the pressure in the reactor was 3 MPaG, and the reaction was carried out for 1 hour while maintaining this pressure. Thereafter, the temperature of the reaction solution was raised to 100 ° C., and the reaction was carried out for an additional 5 hours. During the reaction, the amount of mixed gas consumed in the reaction was continuously introduced into the reactor while maintaining the pressure in the reactor at 3 MPaG. After completion of the reaction, the reaction solution in the reactor was cooled to room temperature, and the remaining gas in the reactor was depressurized to obtain 248 g of a hydroformylation reaction product solution. The amount of DCPD, a raw material compound, contained in the reaction solution before the reaction and the amount of tricyclodecane dicarbaldehyde, a product, in the reaction solution after the reaction were analyzed by gas chromatography to determine the yield of tricyclodecane dicarbaldehyde, which was 99%.

[0289] <Extraction Procedure> 76 g of methanol and 51 g of water were added to 248 g of the obtained hydroformylation reaction product liquid, and the mixture was stirred for 30 minutes under a nitrogen atmosphere. The mixture was then allowed to stand for 30 minutes, allowing it to separate into two phases, and an extraction procedure was then performed. 8.8 g of methylcyclohexane was added to the obtained lower phase (a1), and the mixture was stirred for 30 minutes. The mixture was then allowed to stand for 30 minutes, allowing it to separate into two phases, and an extraction procedure was then performed, yielding 288 g of lower phase (a2). The composition of the obtained lower phase (a2) was analyzed by gas chromatography, and was found to be 47% by mass of tricyclodecane dicarbaldehyde, 27% by mass of methanol, 14% by mass of water, 7% by mass of methylcyclohexane, and 5% by mass of other components.

[0290] <Hydrogenation reduction reaction> 50 g of the lower phase (a2) obtained by the above-mentioned extraction operation and 0.10 g of nickel-chromium-supported diatomaceous earth catalyst were charged into a 200 mL autoclave reactor, and the temperature of the reaction solution in the reactor was raised to 160 ° C. while stirring at 1200 rpm. Next, hydrogen gas was injected through the gas inlet valve so that the pressure in the reactor was 3 MPaG, and the reaction was carried out for 3 hours while maintaining this pressure and the temperature of the reaction solution. During the reaction, the amount of mixed gas consumed in the reaction was continuously introduced into the reactor so as to maintain the pressure in the reactor at 3 MPaG. After completion of the reaction, the reaction solution in the reactor was cooled to room temperature, the remaining gas in the reactor was depressurized, and the nickel-chromium-supported diatomaceous earth catalyst was separated by filtration using a filter with a pore size of 5 μm, yielding 44 g of a reaction product liquid. The amount of tricyclodecane dicarbaldehyde, a raw material compound, contained in the reaction solution before the reaction and the amount of TCDDM, a product in the reaction solution after the reaction, were analyzed by gas chromatography. The yield of TCDDM was 98%.

[0291] <Distillation Purification> 1,800 g of the reaction product liquid after the hydroreduction reaction was charged into a batch-type distillation column (3 L, four-neck flask) equivalent to five structured packing trays. 890 g of low-boiling components, primarily solvent, were distilled off at a minimum internal column pressure of 10 kPa and a maximum column bottom temperature of 100°C. Distillation was then continued at an internal column pressure of 0.3 kPa and a column bottom temperature of 120°C until 15 g of distillate was obtained from the top of the distillation column. The distillation column equivalent to five structured packing trays was then replaced with a glass pot distillation column, and simple distillation was carried out at a pressure of 0.3 kPa and a temperature of 165°C. The TCDDM composition was distilled from the top of the column, and the initial fraction and main fraction were recovered in this order. The amount of TCDDM composition recovered as the main fraction was 745 g. The resulting TCDDM composition was heated at 60°C for one day. The evaluation results of the resulting TCDDM composition are shown in Table 1.

[0292] Example 1-2 A hydroreduction reaction was carried out under the same conditions as in Example 1-1, except that the temperature of the reaction solution was changed from 160°C to 180°C, to obtain a reaction product solution. The yield of TCDDM in the reaction product solution was 99%. After distillation purification under the same conditions as in Example 1-1, the amount of TCDDM composition recovered as the main fraction was 725 g. A TCDDM composition was obtained under the same conditions as in Example 1-1, except that the heating temperature of the TCDDM composition after distillation was changed from 60°C to 50°C. The evaluation results of the obtained TCDDM composition are shown in Table 1.

[0293] Example 1-3 A TCDDM composition was obtained under the same conditions as in Example 1-1, except that the heating temperature of the TCDDM composition after distillation was changed from 60° C. to 50° C. The evaluation results of the obtained TCDDM composition are shown in Table 1.

[0294] Example 1-4 A hydroreduction reaction was carried out under the same conditions as in Example 1-1, except that a ruthenium-supported carbon catalyst was used instead of the nickel-chromium-supported diatomaceous earth catalyst, to obtain a reaction product liquid. The yield of TCDDM in the reaction product liquid was 98%. After distillation and purification under the same conditions as in Example 1-1, the amount of TCDDM composition recovered as the main fraction was 720 g. The evaluation results of the obtained TCDDM composition are shown in Table 1.

[0295] A TCDDM composition was obtained under the same conditions as in Example 1-1, except that the heating period of the TCDDM composition after distillation was changed from 1 day to 4 days. The evaluation results of the obtained TCDDM composition are shown in Table 1.

[0296] Example 1-6 In the distillation purification of Example 1-1, a distillation column equivalent to 20 plates of structured packing (a four-neck flask with a capacity of 3 L) was used instead of the batch distillation column equivalent to 5 plates of structured packing. Light-boiling components, mainly composed of the solvent, were distilled off from 1,800 g of the reaction product liquid after the hydrogenation reduction reaction, and the distillation was continued at an internal column pressure of 0.6 kPa and a column bottom temperature of 185°C until 119 g of distillate was obtained from the top of the distillation column. A TCDDM composition was obtained under the same conditions as in Example 1-1, except for the above. The yield of the TCDDM composition recovered as the main fraction after distillation purification was 601 g. The evaluation results of the obtained TCDDM composition are shown in Table 1.

[0297] Comparative Example 1-1 A TCDDM composition was obtained under the same conditions as in Example 1-1, except that the TCDDM composition was not heated after distillation. The evaluation results of the obtained TCDDM composition are shown in Table 2.

[0298] A TCDDM composition was obtained under the same conditions as in Example 1-1, except that the heating time of the TCDDM composition after distillation was changed from 1 day to 8 days. The evaluation results of the obtained TCDDM composition are shown in Table 2.

[0299] A TCDDM composition was obtained under the same conditions as in Example 1-1, except that the conditions for heating the TCDDM composition after distillation were changed to 70°C for 1 hour. The evaluation results of the obtained TCDDM composition are shown in Table 2.

[0300] The TCDDM compositions obtained in Examples 1-1 to 1-6 and Comparative Examples 1-1 to 1-3 were subjected to gas chromatography mass spectrometry by the method described above to measure the m / z and fragment patterns. It was confirmed that peaks 1 to 3 in each case exhibited m / z and fragment patterns corresponding to TCDDM. Representative fragments observed are listed below. MS(EI): 178 ([M-18]+), 165, 147, 119, 105, 91, 81, 67

[0301]

[0302] In Tables 1 and 2 above, the amount of each TCDDM is expressed in mass %.

[0303] In the evaluation of storage stability, the lower the analytical value of the dynamic light scattering intensity, the lower the crystallinity and the higher the fluidity of the TCDDM composition, i.e., the better the storage stability of the TCDDM composition. As is clear from the above results, the TCDDM compositions of the present invention had excellent storage stability and appropriate fluidity (Examples 1-1 to 1-6). In contrast, the backscattering intensity T １ T ２ When the value was less than ÷8.0 (Comparative Example 1-1), the fluidity was poor. １ T ２ In Comparative Example 1-3, in which the heating conditions for the TCDDM composition after distillation were changed to 70°C for 1 hour, the backscattering intensity T １ T ２ It fell below ÷8.0.

[0304] [Example 2-1] [TCDDM Synthesis Example] <Hydroformylation Reaction> In a 500 mL autoclave reactor (vertical stirring type), Rh(acac)(CO) was added as a raw material compound for a hydroformylation reaction catalyst under a nitrogen atmosphere. ２13.2 mg of methylcyclohexane and 911.6 mg of DBPO were weighed out, and 72 g of methylcyclohexane as an organic solvent and 94 g of DCPD as a raw material compound were charged. Then, while stirring by up-and-down stirring, the temperature of the reaction solution in the reactor was raised to 70 ° C. Next, a mixed gas of hydrogen and carbon monoxide (hydrogen:carbon monoxide = 1:1 (molar ratio)) was quickly injected through the gas inlet valve so that the pressure in the reactor was 3 MPaG, and the reaction was carried out for 1 hour while maintaining this pressure. Thereafter, the temperature of the reaction solution was raised to 100 ° C., and the reaction was carried out for an additional 5 hours. During the reaction, the amount of mixed gas consumed in the reaction was continuously introduced into the reactor while maintaining the pressure in the reactor at 3 MPaG. After completion of the reaction, the reaction solution in the reactor was cooled to room temperature, and the remaining gas in the reactor was depressurized to obtain 185 g of a hydroformylation reaction product solution. The amount of DCPD, a raw material compound, contained in the reaction solution before the reaction and the amount of tricyclodecane dicarbaldehyde, a product, in the reaction solution after the reaction were analyzed by gas chromatography to determine the yield of tricyclodecane dicarbaldehyde, which was 99%.

[0305] <Extraction Procedure> 55 g of methanol and 37 g of water were added to 185 g of the obtained hydroformylation reaction product liquid, and the mixture was stirred for 30 minutes under a nitrogen atmosphere. The mixture was then allowed to stand for 30 minutes, allowing it to separate into two phases, and an extraction procedure was then performed. 6.7 g of methylcyclohexane was added to the obtained lower phase (a1), and the mixture was stirred for 30 minutes. The mixture was then allowed to stand for 30 minutes, allowing it to separate into two phases, and an extraction procedure was then performed, yielding 219 g of lower phase (a2). The composition of the obtained lower phase (a2) was analyzed by gas chromatography, and was found to be 47 mass% tricyclodecane dicarbaldehyde, 27 mass% methanol, 14 mass% water, 7 mass% methylcyclohexane, and 5 mass% other components.

[0306] <Hydrogenation reduction reaction> 50 g of the lower phase (a2) obtained by the above-mentioned extraction operation and 0.03 g of the ruthenium-supported carbon catalyst were charged into a 200 mL autoclave reactor, and the temperature of the reaction solution in the reactor was raised to 160°C while stirring at 1200 rpm. Next, hydrogen gas was injected through the gas inlet valve so that the pressure in the reactor became 3 MPaG, and the reaction was carried out for 3 hours while maintaining this pressure and the temperature of the reaction solution. During the reaction, the amount of mixed gas consumed in the reaction was continuously introduced into the reactor so as to maintain the pressure in the reactor at 3 MPaG. After completion of the reaction, the reaction solution in the reactor was cooled to room temperature, the remaining gas in the reactor was released, and the nickel-chromium-supported diatomaceous earth catalyst was separated by filtration using a filter with a pore size of 5 μm, yielding 44 g of a reaction product liquid. The amount of tricyclodecane dicarbaldehyde, a raw material compound, contained in the reaction solution before the reaction and the amount of TCDDM, a product in the reaction solution after the reaction, were analyzed by gas chromatography. The yield of TCDDM was 98%.

[0307] <Distillative Purification> 1,800 g of the reaction product liquid after the hydrogenation reduction reaction was charged into a batch distillation column (3 L, four-neck flask) equivalent to 20 plates of structured packing, and 890 g of low-boiling components mainly composed of the solvent were distilled off at a minimum internal column pressure of 1 kPa and a maximum column bottom temperature of 100°C. Distillation was then continued at an internal column pressure of 0.6 kPa and a column bottom temperature of 185°C until 120 g of distillate was obtained from the top of the distillation column. The distillation column equivalent to 5 plates of structured packing was then replaced with a glass single distillation column, and simple distillation was carried out at a pressure of 0.3 kPa and a temperature of 165°C, distilling TCDDM composition (A0) from the top of the column, with the initial fraction and the main fraction being recovered in this order. The amount of TCDDM composition (A0) recovered as the main fraction was 600 g. The resulting TCDDM composition (A0) was placed in a glass reagent bottle while maintaining the temperature above 45°C, specifically at 70-80°C, to obtain TCDDM composition (A1) stored in the container. The glass reagent bottle in this example corresponds to container 3 shown in Figures 2 and 3. A sample of TCDDM composition (A1) placed in the glass reagent bottle was immersed in an oil bath set at 60°C for 96 hours, and the sample was heated with stirring until the measured temperature of the TCDDM composition reached 60°C, resulting in TCDDM composition (A2). This operation corresponds to the operation in step (4) shown in Figures 2 and 3, in which the TCDDM composition is heated to a temperature in the range of 45°C or higher but lower than 120°C before being introduced into processing machine (X). Next, stirring of the sample was stopped, and 1 mL of the TCDDM composition (A2) was sampled and placed in a measurement cell. The measurement cell was placed in a thermostatic chamber equipped in a dynamic light scattering measurement device, and the backscattering intensity T １ Measurements were made and the state of preservation was visually observed.

[0308] Regarding the TCDDM composition (A1) and the TCDDM composition (A2), the results of mass spectrometry of the TCDDM composition, storage state, backscattering intensity T １ , and the backscattering intensity of the standard sample T ２ The results of the comparison are shown in Table 3.

[0309] Comparative Example 2-1 In Example 2-1, TCDDM composition (A0) recovered as the main fraction from the pot distillation column was cooled to a measurement temperature of 25°C, then placed in a glass reagent bottle to obtain TCDDM composition (B1), which was then stored in a container. A sample of TCDDM composition (B1) placed in the glass reagent bottle was immersed in an oil bath set at a temperature of 60°C for 96 hours, and the sample was heated with stirring until the measurement temperature of the TCDDM composition reached 60°C, resulting in TCDDM composition (B2). Next, the backscattering intensity T １ Measurements were made and the state of preservation was visually observed.

[0310] Regarding the TCDDM composition (B1) and the TCDDM composition (B2), the results of mass spectrometry of the TCDDM composition showed that the storage state and backscattering intensity T １ , and the backscattering intensity of the standard sample T ２ The results of the comparison are shown in Table 3.

[0311]

[0312] The TCDDM composition of Example 2-1 has excellent storage stability and a backscattering intensity T １ In other words, it was found that there were few microcrystals that cause cloudiness. In contrast, the TCDDM composition of Comparative Example 2-1 had poor storage conditions, lacked fluidity, and was difficult to load into the measurement cell. １ In other words, by storing the TCDDM composition obtained by distillation and purification in a container at a temperature not lower than 45°C, clouding was suppressed, and further, a decrease in fluidity was also suppressed.

[0313] [Example 3-1] [TCDDM Synthesis Example] <Hydroformylation Reaction> In a 500 mL autoclave reactor (vertical stirring type), Rh(acac)(CO) was added as a raw material compound for a hydroformylation catalyst under a nitrogen atmosphere. ２14.0 mg of methylcyclohexane and 1121.8 mg of DBPO were weighed out, 88 g of methylcyclohexane as an organic solvent, and 113 g of DCPD as a raw material compound were charged. Then, while stirring by up-and-down stirring, the temperature of the reaction solution in the reactor was raised to 70°C. Next, a mixed gas of hydrogen and carbon monoxide (hydrogen:carbon monoxide = 1:1 (molar ratio)) was quickly injected through the gas inlet valve so that the pressure in the reactor became 3 MPaG, and the reaction was carried out for 1 hour while maintaining this pressure. Thereafter, the temperature of the reaction solution was raised to 100°C, and the reaction was carried out for an additional 5 hours. During the reaction, the amount of mixed gas consumed in the reaction was continuously introduced into the reactor while maintaining the pressure in the reactor at 3 MPaG. After completion of the reaction, the reaction solution in the reactor was cooled to room temperature, and the remaining gas in the reactor was depressurized, yielding 248 g of a hydroformylation reaction product solution. The amount of DCPD, a raw material compound, contained in the reaction solution before the reaction and the amount of tricyclodecane dicarbaldehyde, a product, in the reaction solution after the reaction were analyzed by gas chromatography to determine the yield of tricyclodecane dicarbaldehyde, which was 99%.

[0314] <Extraction Procedure> 75 g of methanol and 49 g of water were added to 247 g of the obtained hydroformylation reaction product liquid, and the mixture was stirred for 30 minutes under a nitrogen atmosphere. The mixture was then allowed to stand for 30 minutes, allowing it to separate into two phases, and an extraction procedure was then carried out. 9.2 g of methylcyclohexane was added to the obtained lower phase (a1), and the mixture was stirred for 30 minutes. The mixture was then allowed to stand for 30 minutes, allowing it to separate into two phases, and an extraction procedure was then carried out, yielding 288 g of lower phase (a2). The composition of the obtained lower phase (a2) was analyzed by gas chromatography, and it was found to contain 47 mass% tricyclodecane dicarbaldehyde, 27 mass% methanol, 14 mass% water, 7 mass% methylcyclohexane, and 5 mass% other components.

[0315] <Hydrogenation Reduction Reaction> 50 g of the lower phase (a2) obtained by the above-mentioned extraction operation and 0.03 g of the ruthenium-supported carbon catalyst were charged into a 200 mL autoclave reactor, and the temperature of the reaction solution in the reactor was raised to 160°C while stirring at 1200 rpm. Next, hydrogen gas was injected through the gas inlet valve to a pressure of 3 MPaG inside the reactor, and the reaction was carried out for 3 hours while maintaining this pressure and the temperature of the reaction solution. During the reaction, the amount of mixed gas consumed in the reaction was continuously introduced into the reactor so as to maintain the pressure inside the reactor at 3 MPaG. After completion of the reaction, the reaction solution in the reactor was cooled to room temperature, the remaining gas in the reactor was released, and the ruthenium-supported carbon catalyst was separated by filtration using a filter with a pore size of 5 μm, yielding 44 g of reaction product solution. The amount of tricyclodecane dicarbaldehyde, a raw material compound, contained in the reaction solution before the reaction, and the amount of TCDDM, a product in the reaction solution after the reaction, were analyzed by gas chromatography. The yield of TCDDM was 98%.

[0316] <Distillation Purification> 1,800 g of the reaction product liquid after the hydrogenation reduction reaction was charged into a batch distillation column (3 L, four-neck flask) equivalent to five structured packing trays. 890 g of low-boiling components, primarily solvent, were distilled off at a minimum internal column pressure of 10 kPa and a maximum column bottom temperature of 100°C. Distillation was then continued at an internal column pressure of 0.3 kPa and a column bottom temperature of 120°C until 15 g of distillate was obtained from the top of the distillation column. The distillation column equivalent to five structured packing trays was then replaced with a glass single distillation column, and simple distillation was carried out at a pressure of 0.3 kPa and a temperature of 165°C, distilling TCDDM composition (A0) from the top of the column. The initial fraction and main fraction were recovered in this order. The amount of TCDDM composition (A0) recovered as the main fraction was 745 g. The obtained TCDDM composition (A0) was placed in a glass reagent bottle and maintained at a temperature below 45°C to obtain TCDDM composition (A1) stored in a container at a temperature below 45°C. The backscattering intensity T １ , the backscattering intensity of the standard sample T ２ The results of mass spectrometry of the TCDDM composition are shown in Table 4 for comparison with the above.

[0317] The obtained TCDDM composition (A1) was stored in a glass bottle, and the sample was heated at the temperature shown in Table 4 for 96 hours (4 days). After that, the backscattering intensity T １ , the backscattering intensity of the standard sample T ２ The results of mass spectrometry of the TCDDM composition are also shown in Table 4 for comparison with the above.

[0318] Example 3-2 A hydrogenation reduction reaction was carried out under the same conditions as in Example 3-1, except that 0.10 g of nickel-chromium-supported diatomaceous earth was used instead of 0.03 g of ruthenium-supported carbon as the catalyst, and the temperature of the reaction solution was changed from 160°C to 180°C. The reaction product solution was obtained under the same conditions as in Example 3-1, yielding a TCDDM yield of 99%. The reaction product solution was then purified by distillation under the same conditions as in Example 3-1, yielding a TCDDM composition (A1). The resulting TCDDM composition (A1) was heated under the same conditions as in Example 3-1 to obtain a TCDDM composition (A2), which was then evaluated. The evaluation results are shown in Table 4.

[0319] Comparative Example 3-1 In the distillation purification of Example 3-1, a distillation column equivalent to 20 plates of structured packing (a four-neck flask with a capacity of 3 L) was used instead of the batch distillation column equivalent to 5 plates of structured packing. Light-boiling components, primarily solvent, were distilled off from 1,800 g of the reaction product liquid after the hydrogenation reduction reaction. The distillation was continued at an internal pressure of 0.6 kPa and a bottom temperature of 185°C until 119 g of distillate was obtained from the top of the distillation column. A TCDDM composition was obtained under the same conditions as in Example 3-1, except for the above. The yield of the TCDDM composition recovered as the main fraction after distillation purification was 601 g. The resulting TCDDM composition (A1) was allowed to stand at room temperature (25°C) for 96 hours (4 days) without heating, and was evaluated as TCDDM composition (A2). The evaluation results are shown in Table 4.

[0320] Comparative Example 3-2 A sample of the TCDDM composition (A1) obtained in Example 3-1 and stored in a glass bottle was heated at 60°C for 24 hours, cooled to room temperature, allowed to stand at 60°C for another 24 hours, and then heated again at 60°C for 96 hours (4 days), and evaluated. The evaluation results are shown in Table 4.

[0321]

[0322] As is clear from the above results, the organic material could be appropriately produced by the organic material production method of the present invention (Examples 3-1 and 3-2). In contrast, when heating was not performed (Comparative Example 3-1), the raw material viscosity was high and production was not successful. On the other hand, when the raw material was heated to 60°C, cooled to room temperature (25°C), and then heated again to 60°C (Comparative Example 3-2), the raw material became cloudy and production was not successful.

[0323] Although the present invention has been described in detail with reference to specific embodiments, it will be apparent to those skilled in the art that various modifications can be made without departing from the spirit and scope of the invention.

[0324] 1: Distillation column 2: Storage tank 3: Container X: Processing machine

Claims

1. A tricyclodecane dimethanol composition containing tricyclodecane dimethanol, wherein the 173° backscattering intensity T １ is the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷8.0≦T １ ≦T ２ A tricyclodecane dimethanol composition satisfying the above condition of 5.

0.

2. The 173° backscatter intensity T １ But, T ２ ÷5.0≦T １ ≦T ２ 2. The tricyclodecane dimethanol composition according to claim 1, wherein the tricyclodecane dimethanol composition satisfies the following formula:

3. The tricyclodecane dimethanol composition according to claim 1, wherein the tricyclodecane dimethanol contains a chiral compound of which one enantiomer is represented by formula (A), and the content of the chiral compound represented by formula (A) is 25 to 54 mass% relative to 100 mass% of the total mass of the tricyclodecane dimethanol.

4. The tricyclodecane dimethanol composition according to claim 1, wherein the tricyclodecane dimethanol contains a chiral compound of which one enantiomer is represented by formula (A), and the content of the chiral compound represented by formula (A) is 33 to 38 mass% relative to 100 mass% of the total mass of the tricyclodecane dimethanol.

5. The tricyclodecane dimethanol composition according to claim 1, wherein the tricyclodecane dimethanol contains a chiral compound of which one enantiomer is represented by formula (B), and the content of the chiral compound represented by formula (B) is 1.6 to 4.8 mass% relative to 100 mass% of the total mass of the tricyclodecane dimethanol.

6. The tricyclodecane dimethanol composition according to claim 1, wherein the tricyclodecane dimethanol comprises a chiral compound of which one enantiomer is represented by formula (A) and a chiral compound of which the other enantiomer is represented by formula (B), the content of the chiral compound represented by formula (A) is 33 to 38 mass% relative to 100 mass% of the total mass of the tricyclodecane dimethanol, and the content of the chiral compound represented by formula (B) is 1.6 to 4.8 mass% relative to 100 mass% of the total mass of the tricyclodecane dimethanol.

7. The tricyclodecane dimethanol composition according to claim 1, wherein the content of said tricyclodecane dimethanol is 70 mass % or more relative to 100 mass % of the total mass of said tricyclodecane dimethanol composition.

8. The tricyclodecane dimethanol composition of claim 1, which is substantially free of a fragrance carrier.

9. An ultraviolet-curable composition derived from the tricyclodecane dimethanol composition according to any one of claims 1 to 8.

10. The ultraviolet-curable composition according to claim 9, which is used in at least one of a hard coat material, an antifouling coat material, a resist material, an inkjet ink, and a material for a 3D printer.

11. A polymer composition derived from the tricyclodecane dimethanol composition according to any one of claims 1 to 8.

12. The polymer composition according to claim 11, which is at least one resin selected from the group consisting of polyester resins, epoxy resins, acrylate resins, polycarbonate resins, and polyurethane resins.

13. A method for producing a tricyclodecane dimethanol composition stored in a container, comprising storing a tricyclodecane dimethanol composition (A0) containing tricyclodecane dimethanol obtained by distillation and purification in a container while maintaining the temperature at not less than 45°C, wherein the tricyclodecane dimethanol contains a chiral compound of which one enantiomer is represented by formula (A).

14. A method for producing a tricyclodecane dimethanol composition according to claim 13, wherein the content of the tricyclodecane dimethanol is 70 mass% or more relative to 100 mass% of the total mass of the tricyclodecane dimethanol composition (A0).

15. The method for producing a tricyclodecane dimethanol composition according to claim 13, wherein the tricyclodecane dimethanol composition is substantially free of a fragrance carrier.

16. The method for producing a tricyclodecane dimethanol composition according to claim 13, wherein the container is a shipping container.

17. The method for producing a tricyclodecane dimethanol composition according to claim 13, wherein the content of the chiral compound of which one enantiomer is represented by formula (A) is 25% by mass or more and 54% by mass or less, relative to the total mass of the tricyclodecane dimethanol composition (A0) (100% by mass).

18. The method for producing a tricyclodecane dimethanol composition according to claim 13, wherein the tricyclodecane dimethanol composition (A0) contains a chiral compound of which one enantiomer is represented by formula (B).

19. The method for producing a tricyclodecane dimethanol composition according to claim 18, wherein the content of the chiral compound of which one enantiomer is represented by formula (B) is 1.6% by mass or more and 4.8% by mass or less, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A0).

20. The 173° backscattering intensity T of the tricyclodecane dimethanol composition stored in the container was measured at 25°C using a dynamic light scattering measurement method. １ is the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷500≦T １ ≦T ２ The method for producing the tricyclodecane dimethanol composition according to claim 13, which satisfies the above formula:

21. The 173° backscatter intensity T １ But, T ２ ÷8.0≦T １ ≦T ２ The method for producing a tricyclodecane dimethanol composition according to claim 20, which satisfies the above formula:

22. The 173° backscattering intensity T of the tricyclodecane dimethanol composition stored in the container was measured at 25°C using a dynamic light scattering measurement method. １ is the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷8.0≦T １ ≦T ２ The method for producing a tricyclodecane dimethanol composition according to claim 13, wherein the ratio of the total weight of the tricyclodecane dimethanol composition to the total weight of the tricyclodecane dimethanol composition satisfies the above formula (1).

23. A method for producing a tricyclodecane dimethanol composition according to any one of claims 13 to 22, wherein the tricyclodecane dimethanol composition stored in the container is heated while stored in the container, and then directly fed from the container into a processing machine.

24. The method for producing a tricyclodecane dimethanol composition according to claim 23, wherein the processing equipment is a reactor and / or a compounder.

25. A method for storing a tricyclodecane dimethanol composition (A0) containing tricyclodecane dimethanol obtained by distillation and purification, comprising storing the tricyclodecane dimethanol composition (A0) in a container while maintaining the temperature at not less than 45°C, wherein the tricyclodecane dimethanol contains a chiral compound, one enantiomer of which is represented by formula (A).

26. A method for storing a tricyclodecane dimethanol composition according to claim 25, wherein the content of the tricyclodecane dimethanol is 70 mass% or more relative to 100 mass% of the total mass of the tricyclodecane dimethanol composition (A0).

27. A method for preserving a tricyclodecane dimethanol composition according to claim 25, wherein the tricyclodecane dimethanol composition is substantially free of a fragrance carrier.

28. A method for storing a tricyclodecane dimethanol composition according to claim 25, wherein the content of the chiral compound of which one enantiomer is represented by formula (A) is 25% by mass or more and 54% by mass or less, relative to the total mass of the tricyclodecane dimethanol composition (A0) (100% by mass).

29. A method for storing a tricyclodecane dimethanol composition according to claim 25, wherein the tricyclodecane dimethanol composition (A0) contains a chiral compound of which one enantiomer is represented by formula (B).

30. A method for storing a tricyclodecane dimethanol composition according to claim 29, wherein the content of the chiral compound of which one enantiomer is represented by formula (B) is 1.6% by mass or more and 4.8% by mass or less, relative to the total mass (100% by mass) of the tricyclodecane dimethanol composition (A0).

31. The method for storing a tricyclodecane dimethanol composition according to any one of claims 25 to 30, wherein the tricyclodecane dimethanol composition stored in the container is heated while stored in the container, and then directly fed from the container into a processing machine.

32. The method for preserving a tricyclodecane dimethanol composition according to claim 31, wherein the processing machine is a reactor and / or a compounder.

33. A method for producing an organic material (excluding fragrance materials) comprising: heating part or all of a tricyclodecane dimethanol composition (A1) containing tricyclodecane dimethanol, which is stored in a container and at a temperature below 45°C, to 45°C or higher but lower than 120°C; and processing the heated tricyclodecane dimethanol composition (A2) while maintaining the temperature at 45°C or higher but lower than 120°C; wherein the tricyclodecane dimethanol contains a chiral compound, one enantiomer of which is represented by formula (A).

34. A method for producing an organic material according to claim 33, wherein the content of tricyclodecane dimethanol in the organic material is 70 mass% or more relative to 100 mass% of the total mass of the tricyclodecane dimethanol composition (A1).

35. The method for producing an organic material according to claim 33, wherein the tricyclodecane dimethanol composition (A1) is heated while being stored in the container.

36. The method for producing an organic material according to claim 33, wherein the tricyclodecane dimethanol composition (A1) is heated while stored in the container, and then directly introduced from the container into the processing machine.

37. The 173° backscattering intensity T of the tricyclodecane dimethanol composition (A1) measured at 25°C using a dynamic light scattering measurement method. １ is the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷500≦T １ ≦T ２ The method for producing an organic material according to any one of claims 33 to 36, wherein 38. The 173° backscattering intensity T of the tricyclodecane dimethanol composition (A2) measured at 25°C using a dynamic light scattering measurement method. １ is the standard sample (D ５０ The backscattering intensity of a 0.002% by volume aqueous suspension of latex with a diameter of 300 nm was calculated as T ２ When this is done, T ２ ÷8.0≦T １ ≦T ２ The method for producing an organic material according to any one of claims 33 to 36, which satisfies x 5.

0.

39. The 173° backscatter intensity T １ But, T ２ ÷4.0≦T １ ≦T ２ 39. The method for producing an organic material according to claim 38, which satisfies the condition of x 2.

0.

40. A method for producing an organic material according to any one of claims 33 to 36, wherein the content of the chiral compound of which one enantiomer is represented by formula (A) in the tricyclodecane dimethanol composition (A1) is 25% by mass or more and 54% by mass or less, relative to the total mass of the tricyclodecane dimethanol composition (A1) (100% by mass).

41. The method for producing an organic material according to any one of claims 33 to 36, wherein the content of the chiral compound of which one enantiomer is represented by formula (A) in the tricyclodecane dimethanol composition (A1) is 33% by mass or more and 38% by mass or less, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A1).

42. The method for producing an organic material according to any one of claims 33 to 36, wherein the tricyclodecane dimethanol contains a chiral compound having one enantiomer represented by formula (B), and the content of the chiral compound having one enantiomer represented by formula (B) in the tricyclodecane dimethanol composition (A1) is 1.6% by mass or more and 48% by mass or less, relative to the total mass of the tricyclodecane dimethanol composition (A1) (100% by mass).

43. The method for producing an organic material according to any one of claims 33 to 36, wherein the processing machine is a reactor and / or a compounder.

44. A method for producing an organic material according to any one of claims 33 to 36, wherein the organic material is at least one polymer selected from the group consisting of polyester resins, epoxy resins, acrylate resins, polycarbonate resins, and polyurethane resins, or an ultraviolet-curable composition.

45. A method for producing an organic material according to any one of claims 33 to 36, wherein the tricyclodecane dimethanol composition (A1) is stored in the container in an environment of -5°C or higher and lower than 45°C for 24 hours or longer before being heated.

46. A method for producing an organic material according to any one of claims 33 to 36, comprising storing the tricyclodecane dimethanol composition (A0) obtained by distillation and purification in the container while maintaining the temperature at not less than 45°C.

47. The method for producing an organic material according to claim 33, wherein the tricyclodecane dimethanol composition (A1) is heated while stored in the container and then directly charged from the container into the processing machine, the content of the compound represented by formula (A) in the tricyclodecane dimethanol (A1) is 25% by mass or more and 54% by mass or less, relative to 100% by mass of the total mass of the tricyclodecane dimethanol composition (A1), the processing machine is a reactor and / or a mixer, and the organic material is at least one polymer selected from the group consisting of polyester-based resins, epoxy-based resins, acrylate-based resins, polycarbonate-based resins, and polyurethane-based resins, or an ultraviolet-curable composition.

48. The method for producing an organic material described in claim 47, wherein the tricyclodecane dimethanol composition (A0) obtained by distillation and purification is stored in the container while maintaining the temperature above 45°C, and the tricyclodecane dimethanol composition (A1) is left in an environment of -5°C or higher and lower than 45°C for 24 hours or more while stored in the container before heating.

49. The method for producing an organic material described in claim 47, wherein after the tricyclodecane dimethanol composition (A0) is stored in the container, the tricyclodecane dimethanol composition (A2) is not stirred before being directly charged into the processing machine.

50. The method for producing an organic material described in claim 47, wherein after the tricyclodecane dimethanol composition (A0) is stored in the container, heating is not performed until the tricyclodecane dimethanol composition (A1) is heated to a temperature of 45°C or higher but lower than 120°C.

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