Compositions and their applications

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

[Technical Field]

[0001] This invention relates to a tricyclodecanedimethanol composition, an ultraviolet-curable composition, a polymer composition, a method for producing a tricyclodecanedimethanol composition, a method for storing a tricyclodecanedimethanol composition, and a method for producing an organic material. [Background technology]

[0002] In the fields of molding materials, electronic materials, and components for display devices, materials with alicyclic molecular structures are used from the viewpoint of transparency, heat resistance, and low water absorption. Tricyclodecanedimethanol (hereinafter abbreviated as "TCDDM") is a dihydric alcohol having an alicyclic structure. TCDDM is produced by a hydroformylation reaction in which dicyclopentadiene is reacted with carbon monoxide and hydrogen in the presence of a catalyst to obtain an aldehyde, which is then reduced by hydrogenation (Patent Document 1, Patent Document 2, Non-Patent Document 1, Non-Patent Document 2). TCDDM has been used as a raw material for the synthesis of molding materials such as polyester and polycarbonate. 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 components for display devices. Furthermore, derivatives of TCDDM, such as diacrylate ester derivatives, dimethacrylate ester derivatives, and urethane acrylates, which are synthesized using TCDDM as a raw material, are used as UV-curable compositions. Cured products using such UV-curable compositions exhibit high surface hardness, high glass transition temperature, excellent heat decomposition resistance, and superior development resistance, and are therefore attracting attention as components for electronic materials and display devices such as hard coats, antifouling coatings, and resists. Under these circumstances, Patent Document 3 discloses a tricyclodecanedimethanol composition, as well as an ultraviolet-curable composition and a polymer composition using the same.

[0003] Patent Document 3 describes that one component of the isomers of a tricyclodecanedimethanol composition (TCDDM composition) (one of the enantiomers being a chiral compound represented by formula (A)) has an extremely crystalline structure, and that by manufacturing the TCDDM composition so that the ratio of this component is above a predetermined value, the crystallinity of the TCDDM composition can be adjusted, resulting in a TCDDM composition that is less prone to stringing and has excellent handling properties. [ka] [Prior art documents] [Patent Documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2020-132624 [Patent Document 2] Japanese Patent Publication No. 2021-520401 [Patent Document 3] International Publication No. 2023 / 176641 [Non-patent literature]

[0005] [Non-Patent Document 1] Hitachi Chemical Technical Report, No. 51 (2008-7), pp. 7-12 [Non-Patent Document 2] Applied Catalyst,Vol.19,pp259-273(1985) [Overview of the project] [Problems that the invention aims to solve]

[0006] The TCDDM composition described in Patent Document 3 is a material that is less prone to stringing and has excellent handling properties. On the other hand, from the viewpoint of shelf life, there are cases where a TCDDM composition that does not increase in viscosity during storage is required. Furthermore, considering the compounding process, there are also cases where a TCDDM composition with appropriate fluidity is required. When the viscosity of the TCDDM composition increases, it becomes difficult to pump the TCDDM composition or the raw material mixture containing the TCDDM composition (hereinafter referred to as the "TCDDM composition etc.") with a gear pump or the like, or there are problems such as the TCDDM composition etc. deteriorating when heated to improve the fluidity of the TCDDM composition etc. Furthermore, studies have been conducted on using TCDDM in the production of organic materials such as polymers and ultraviolet curable compositions. However, as a result of the studies by the present inventors, it has been found that the TCDDM composition may become cloudy or its fluidity may decrease depending on the storage conditions, and its viscosity may increase significantly depending on its thermal history and handling conditions, resulting in a significant decrease in handling properties.

[0007] An object of the present invention is to solve such problems, and to provide a TCDDM composition having excellent storage stability and excellent fluidity, and an ultraviolet curable composition and a polymer composition using the TCDDM composition. Another object of the present invention is to suppress the clouding or decrease in fluidity of the TCDDM composition. More specifically, it is an object to provide a method for producing a TCDDM composition in which clouding or a decrease in fluidity is suppressed in a method for producing a TCDDM composition stored in a container or a method for storing a TCDDM composition. Furthermore, an object of the present invention is to provide a method for producing an organic material that suppresses an increase in viscosity during storage of the TCDDM composition and enables efficient production of an organic material using the TCDDM composition as a raw material.

Means for Solving the Problems

[0008] Under such circumstances, as a result of the inventors' study, it has been found that by adjusting the 173° backscattering intensity T1 of the TCDDM composition within a predetermined range, the storage stability and fluidity of the TCDDM composition can be improved. Also, it has been found that by storing the TCDDM composition in a container while keeping it at a temperature not lower than 45°C, clouding or a decrease in fluidity of the TCDDM composition can be suppressed. Furthermore, it has been found that by heating the TCDDM composition to a temperature of 45°C or higher and lower than 120°C and feeding it into a processing machine for producing an organic material for processing while maintaining the temperature within the range of 45°C to lower than 120°C, an organic material can be efficiently produced.

[0009] That is, the gist of the present invention is as follows.

[0010] [1] A tricyclodecane dimethanol composition containing tricyclodecane dimethanol, wherein the 173° backscattering intensity T1 measured at a temperature of 25°C using the dynamic light scattering measurement method of the tricyclodecane dimethanol composition satisfies T2÷8.0≦T1≦T2×5.0, where T2 is the backscattering intensity of a 0.002% by volume aqueous suspension of a latex having a standard sample (D 50 having a particle size of 300 nm), a tricyclodecane dimethanol composition. [2] The tricyclodecane dimethanol composition according to [1], wherein the 173° backscattering intensity T1 satisfies T2÷5.0≦T1≦T2×2.0. [3] The tricyclodecane dimethanol composition according to [1] or [2], wherein the tricyclodecane dimethanol contains a chiral compound in which one enantiomer is represented by the formula (A), and the content ratio of the chiral compound represented by the formula (A) is 25 to 54% by mass based on 100% by mass of the total mass of the tricyclodecane dimethanol. [Chemical formula] [4] The tricyclodecanedimethanol composition according to any one of [1] to [3], wherein one of the enantiomers of the tricyclodecanedimethanol is a chiral compound represented by formula (A), and the content of the chiral compound represented by formula (A) is 33 to 38% by mass with respect to 100% by mass of the total mass of the tricyclodecanedimethanol. [ka] [5] The tricyclodecanedimethanol composition according to any one of [1] to [4], wherein one of the enantiomers of the tricyclodecanedimethanol is a chiral compound represented by formula (B), and the content of the chiral compound represented by formula (B) is 1.6 to 4.8% by mass with respect to 100% by mass of the total mass of the tricyclodecanedimethanol. [ka] [6] The tricyclodecanedimethanol comprises a chiral compound in which one enantiomer is represented by formula (A), and a chiral compound in which the 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 tricyclodecanedimethanol. 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 tricyclodecanedimethanol. A tricyclodecanedimethanol composition according to any one of [1] to [5]. [ka] [ka] [7] The tricyclodecanedimethanol composition according to any one of [1] to [6], wherein the content of the tricyclodecanedimethanol is 70% by mass or more based on 100% by mass of the total mass of the tricyclodecanedimethanol composition. [8] A tricyclodecanedimethanol composition according to any one of [1] to [7], which is substantially free of a fragrance carrier. A UV-curable composition derived from the tricyclodecanedimethanol composition described in any one of [9][1] to [8].

[10] The ultraviolet-curable composition according to [9], used in at least one of hard coat materials, antifouling coat materials, resist materials, inkjet inks, and 3D printer materials. A polymer composition derived from any one of the tricyclodecanedimethanol compositions described in

[11] [1] to [8].

[12] The polymer composition according to

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

[13] The tricyclodecanedimethanol composition (A0) obtained by distillation purification, containing tricyclodecanedimethanol, is stored in a container while being kept at a temperature no lower than 45°C. The tricyclodecanedimethanol contains a chiral compound in which one of its enantiomers is represented by formula (A). A method for producing a tricyclodecanedimethanol composition stored in a container. [ka]

[14] The method for producing the tricyclodecanedimethanol composition according to

[13] , wherein the content of the tricyclodecanedimethanol is 70% by mass or more with respect to 100% by mass of the total mass of the tricyclodecanedimethanol composition (A0).

[15] A method for producing the tricyclodecanedimethanol composition according to

[13] or

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

[16] A method for producing a tricyclodecanedimethanol composition according to any one of

[13] to

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

[17] A method for producing a tricyclodecanedimethanol composition according to any one of

[13] to

[16] , wherein the content of the chiral compound represented by formula (A) as one of the enantiomers is 25% by mass or more and 54% by mass or less with respect to 100% by mass of the total mass of the tricyclodecanedimethanol composition (A0).

[18] A method for producing the tricyclodecanedimethanol composition according to any one of

[13] to

[17] , wherein the tricyclodecanedimethanol composition (A0) comprises a chiral compound represented by formula (B) as one of its enantiomers. [ka]

[19] The method for producing the tricyclodecanedimethanol composition according to

[18] , wherein the content of the chiral compound represented by formula (B) as one of the enantiomers is 1.6% by mass or more and 4.8% by mass or less with respect to 100% by mass of the total mass of the tricyclodecanedimethanol composition (A0).

[20] The 173° backscattering intensity T1 of the tricyclodecanedimethanol composition stored in the container was measured at a temperature of 25°C using a dynamic light scattering method, and was found to be equal to that of the standard sample (D 50 A method for producing a tricyclodecanedimethanol composition according to any one of

[13] to

[19] , wherein T2 is the backscattering intensity of a 0.002 volume% aqueous suspension of latex having a wavelength of 300 nm, and T2 satisfies T2 ÷ 500 ≤ T1 ≤ T2.

[21] A method for producing the tricyclodecanedimethanol composition according to

[20] , wherein the 173° backscattering intensity T1 satisfies T2÷8.0 ≤ T1 ≤ T2.

[22] The 173° backscattering intensity T1 of the tricyclodecanedimethanol composition stored in the container was measured at a temperature of 25°C using a dynamic light scattering method, and was found to be equal to that of the standard sample (D 50 A method for producing a tricyclodecanedimethanol composition according to any one of

[13] to

[21] , wherein the backscattering intensity of a 0.002 volume% aqueous suspension of latex having a wavelength of 300 nm is T2, and T2÷8.0≦T1≦T2×5.0.

[23] A method for producing a tricyclodecanedimethanol composition according to any one of

[13] to

[22] , wherein the tricyclodecanedimethanol composition stored in the container is heated while stored in the container and then directly introduced from the container into a processing machine.

[24] The method for producing a tricyclodecanedimethanol composition according to

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

[25] The tricyclodecanedimethanol composition (A0) obtained by distillation purification, containing tricyclodecanedimethanol, is stored in a container while being kept at a temperature no lower than 45°C. A method for preserving a tricyclodecanedimethanol composition, wherein one of the enantiomers of the tricyclodecanedimethanol is a chiral compound represented by formula (A). [ka]

[26] A method for preserving a tricyclodecanedimethanol composition according to

[25] , wherein the content of tricyclodecanedimethanol is 70% by mass or more with respect to 100% by mass of the total mass of the tricyclodecanedimethanol composition (A0).

[27] A method for preserving the tricyclodecanedimethanol composition according to

[25] or

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

[28] A method for preserving a tricyclodecanedimethanol composition according to any one of

[25] to

[27] , wherein the content of the chiral compound represented by formula (A) as one of the enantiomers is 25% by mass or more and 54% by mass or less with respect to 100% by mass of the total mass of the tricyclodecanedimethanol composition (A0).

[29] A method for storing a tricyclodecanedimethanol composition according to any one of

[25] to

[28] , wherein the tricyclodecanedimethanol composition (A0) contains a chiral compound represented by formula (B) as one of its enantiomers. [ka]

[30] The method for preserving the tricyclodecanedimethanol composition according to

[29] , wherein the content of the chiral compound represented by formula (B) as one of the enantiomers is 1.6% by mass or more and 4.8% by mass or less with respect to 100% by mass of the total mass of the tricyclodecanedimethanol composition (A0).

[31] A method for storing a tricyclodecanedimethanol composition according to any one of

[25] to

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

[32] The method for storing a tricyclodecanedimethanol composition according to

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

[33] A process that includes heating a portion or all of a tricyclodecanedimethanol composition (A1) containing tricyclodecanedimethanol, which is stored in a container and at a temperature below 45°C, to a temperature of 45°C or higher and below 120°C, and then putting the heated tricyclodecanedimethanol composition (A2) into a processing machine and processing it while maintaining the temperature of 45°C or higher and below 120°C. A method for producing an organic material (excluding fragrance materials), wherein the tricyclodecanedimethanol contains a chiral compound whose enantiomer is represented by formula (A). [ka]

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

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

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

[33] or

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

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

[33] to

[35] , wherein the tricyclodecanedimethanol composition (A1) is heated while it is stored in the container, and then directly transferred from the container to the processing machine.

[37] The 173° backscattering intensity T1 of the tricyclodecanedimethanol composition (A1), measured at a temperature of 25°C using a dynamic light scattering method, was found to be equal to that of the standard sample (D 50 A method for producing an organic material according to any one of

[33] to

[36] , wherein the backscattering intensity of a 0.002 volume% aqueous suspension of latex having a wavelength of 300 nm is T2, and T2 ÷ 500 ≤ T1 ≤ T2.

[38] The 173° backscattering intensity T1 of the tricyclodecanedimethanol composition (A2), measured at a temperature of 25°C using a dynamic light scattering method, was found to be equal to that of the standard sample (D 50 A method for producing an organic material according to any one of

[33] to

[37] , wherein when the backscattering intensity of a 0.002 volume% aqueous suspension of latex having a wavelength of 300 nm is T2, T2÷8.0≦T1≦T2×5.0.

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

[38] , wherein the 173° backscattering intensity T1 satisfies T2÷4.0 ≤ T1 ≤ T2×2.0.

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

[33] to

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

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

[33] to

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

[42] The tricyclodecanedimethanol contains a chiral compound whose enantiomer is represented by formula (B), A method for producing an organic material according to any one of

[33] to

[41] , wherein the content of the chiral compound represented by formula (B) as one of the enantiomers in the tricyclodecanedimethanol composition (A1) is 1.6% by mass or more and 48% by mass or less, based on 100% by mass of the total mass of the tricyclodecanedimethanol composition (A1). [ka]

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

[33] to

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

[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 resins, epoxy resins, acrylate resins, polycarbonate resins, and polyurethane resins, or an ultraviolet curable composition.

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

[33] to

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

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

[33] to

[45] , comprising storing the tricyclodecanedimethanol composition (A0) obtained by distillation purification in the container while keeping the temperature at any temperature below 45°C.

[47] After heating the tricyclodecanedimethanol composition (A1) while it is still stored in the container, it is directly transferred from the container to the processing machine. The content of the compound represented by formula (A) in the tricyclodecanedimethanol (A1) is 25% by mass or more and 54% by mass or less, based on 100% by mass of the total mass of the tricyclodecanedimethanol composition (A1). The processing machine is a reactor and / or a blender, A method for producing an organic material according to any one of

[33] to

[46] , 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.

[48] ​​The tricyclodecanedimethanol composition (A0) obtained by distillation purification is stored in the container while keeping the temperature no lower than 45°C. The method for producing an organic material according to any one of

[33] to

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

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

[33] to

[48] , wherein the tricyclodecanedimethanol composition (A0) is stored in the container and no stirring is performed between the time the tricyclodecanedimethanol composition (A2) is directly added to the processing machine.

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

[33] to

[49] , wherein after the tricyclodecanedimethanol composition (A0) is stored in the container, no heating is performed until the tricyclodecanedimethanol composition (A1) is heated to 45°C or higher and less than 120°C. [Effects of the Invention]

[0011] The present invention makes it possible to provide a TCDDM composition with excellent storage stability and fluidity, as well as an ultraviolet-curable composition and a polymer composition using the TCDDM composition. Furthermore, the present invention makes it possible to suppress turbidity or a decrease in fluidity when storing a TCDDM composition. More specifically, it is possible to provide a TCDDM composition in which turbidity or a decrease in fluidity is suppressed in a TCDDM composition stored in a container and in a method for storing a TCDDM composition. Furthermore, the present invention provides a method for producing organic materials that can efficiently generate organic materials using the TCDDM composition as a raw material while suppressing the 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. [Brief explanation of the drawing]

[0012] [Figure 1] Figure 1 shows the gas chromatogram of the TCDDM composition obtained in Example 1-1. [Figure 2] This diagram shows a method for producing a TCDDM composition stored in the container of the present invention, as well as a schematic diagram illustrating subsequent transport, storage, and processing methods for the TCDDM composition stored in the container. [Figure 3] This diagram shows a method for producing a TCDDM composition stored in the container of the present invention, as well as a schematic diagram illustrating subsequent processing steps for the TCDDM composition stored in the container. [Figure 4] The gas chromatogram of the TCDDM composition obtained in Example 2-1 is shown. [Figure 5] Figure 5 is a schematic diagram showing each step of an example of a method for producing an organic material according to the present invention. [Figure 6] Figure 6 shows the gas chromatogram of the TCDDM composition obtained in Example 3-1. [Modes for carrying out the invention]

[0013] The following describes in detail embodiments for carrying out the present invention (hereinafter simply referred to as "this embodiment"). Note that the following embodiment is illustrative for explaining the present invention, and the present invention is not limited to this embodiment.

[0014] In this specification, "~" is used to mean that the numbers before and after it are included as the lower and upper limits. "A~B" means that it is greater than or equal to A and less than or equal to B. Furthermore, the upper and lower limits of the numerical values ​​in this specification are given as examples of this embodiment, regardless of the combination of upper and lower limits.

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

[0016] In this specification, "mass%" indicates the percentage of a given component contained in 100% of the total amount. Furthermore, "mass%" and "weight%" are synonymous.

[0017] In this specification, “optional” or “optionally” means that the following situations may or may not occur, and therefore these descriptions include both cases in which the situations occur and cases in which they do not.

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

[0019] In this specification, the term "process" includes not only independent processes but also any process that cannot be clearly distinguished from other processes, as long as its intended function is achieved. If the measurement methods, etc., described in the standards shown in this specification differ from year to year, unless otherwise specified, the standards as of January 1, 2024 shall apply. If the measurement methods, etc., described in the standards shown in this specification have been discontinued as of January 1, 2024, the standards in effect at the time of discontinuation shall apply.

[0020] The embodiments of the present invention will be described in detail below, but the description of the constituent elements described below is merely one example of an embodiment of the present invention and is not limited to these.

[0021] The following describes in detail the first embodiment of the present invention.

[0022] <Tricyclodecanedimethanol composition> The tricyclodecanedimethanol composition (TCDDM composition) of this embodiment is a TCDDM composition containing tricyclodecanedimethanol, wherein the 173° backscattering intensity T1 measured at a temperature of 25°C using the dynamic light scattering measurement method for the tricyclodecanedimethanol composition is equal to that of a standard sample (D 50 The composition satisfies the condition T2÷8.0 ≤ T1 ≤ T2×5.0 when the backscattering intensity of a 0.002 volume% aqueous suspension of latex with a wavelength of 300 nm is T2. By adopting this configuration, a TCDDM composition with excellent storage stability and excellent fluidity can be obtained. The 173° backscattering intensity T1 is an indicator of the fluidity and storage stability of the TCDDM composition. Setting the lower limit of the backscattering intensity T1 to T2 ÷ 8.0 or higher tends to result in a relatively higher 173° backscattering intensity T1, leading to the formation of microcrystals in the TCDDM composition and resulting in moderate fluidity, which is advantageous during handling operations such as compounding. On the other hand, setting the upper limit of the backscattering intensity T1 to T2 × 5.0 or lower results in a relatively lower 173° backscattering intensity T1, reducing the amount of TCDDM microcrystals in the TCDDM composition, making it less likely for viscosity to increase during storage, and thus improving storage stability.

[0023] The backscatter intensity T1 described above can be achieved by adjusting the number of heating and stirring cycles of TCDDM, storage conditions, etc. For example, to make the backscatter intensity T1 T2 × 5.0 or less, this can be achieved by reducing the number of heating and cooling cycles after the production of the TCDDM raw materials, reducing the number of times the TCDDM is stirred or transferred to other containers while heated, and minimizing storage at temperatures between 45°C and 55°C. On the other hand, to make the backscatter intensity T1 T2 ÷ 8.0 or more, this can be achieved by performing heating and stirring once, and by increasing the proportion of chiral compound A in the TCDDM.

[0024] (First form of a method for producing a TCDDM composition) One specific embodiment (first form) of the method for producing the TCDDM composition of this embodiment is a method in which a TCDDM composition (A0) obtained by distillation purification, in which one enantiomer is a chiral compound represented by formula (A), is stored in a container while maintaining the temperature at no more than 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 before storage in the container described above is not particularly limited, but is preferably 45°C or higher, more preferably 50°C or higher, even more preferably 60°C or higher, even more preferably over 60°C, even more preferably 70°C or higher, even more preferably over 70°C, and particularly preferably 75°C or higher. On the other hand, the upper limit of the temperature before storage in the container described above 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 in any way. For example, the temperature at which the TCDDM composition (A0) obtained by distillation purification is stored in a container is preferably 45°C to 110°C, more preferably 50°C to 100°C, even more preferably 60°C to 95°C, even more preferably over 60°C and under 90°C, even more preferably 70°C to under 90°C, and even more preferably over 70°C and under 85°C.

[0026] In the first embodiment described above, the time for keeping the TCDDM composition (A0) obtained by distillation purification at a temperature not below 45°C is not particularly limited, but is preferably 1 hour or more, more preferably more than 1 hour, even more preferably 5 hours or more, even more preferably 15 hours or more, even more preferably 30 hours or more, and even more preferably 45 hours or more. On the other hand, the upper limit of the temperature until storage in the above-mentioned container is not particularly limited, but is preferably 130 hours or less, more preferably 110 hours or less, even more preferably 90 hours or less, even 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 combined arbitrarily. For example, the time for keeping the TCDDM composition (A0) obtained by distillation purification at a temperature not below 45°C is preferably 1 hour or more and 130 hours or less, more preferably more than 1 hour and 110 hours or less, even more preferably 5 hours or more and 90 hours or less, even more preferably 15 hours or more and 70 hours or less, even more preferably 30 hours or more and 60 hours or less, and even more preferably 45 hours or more and 50 hours or less.

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

[0028] (Second form of method for producing TCDDM composition) Alternatively, another embodiment (second form) for producing the TCDDM composition of this embodiment is a method in which, for example, part or all of a TCDDM composition (A1) containing a chiral compound represented by formula (A) as one enantiomer, which is stored in a container and at a temperature of less than 45°C, is heated to 45°C or higher and less than 120°C, and the heated TCDDM composition (A2) is put into a processing machine while maintaining a temperature of 45°C or higher and less than 120°C, thereby obtaining a TCDDM composition as a TCDDM composition stored in the processing machine. The lower limit of the temperature at which the product is stored in the container described above is not particularly limited, but is preferably 45°C or higher, more preferably 50°C or higher, even more preferably 60°C or higher, even more preferably over 60°C, even more preferably 70°C or higher, even more preferably over 70°C, and particularly preferably 75°C or higher. On the other hand, the upper limit of the temperature at which the product is stored in the container described above 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 below 90°C, and even more preferably 85°C or lower. The above upper and lower limits can be combined in any way. For example, the temperature at which the product is stored in the container described above is preferably 45°C to 110°C, more preferably 50°C to 100°C, even more preferably 60°C to 95°C, even more preferably over 60°C and 90°C, even more preferably 70°C to less than 90°C, and even more preferably over 70°C and 85°C.

[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 to less than 120°C is not particularly limited, but is preferably 1 hour or more, more preferably more than 1 hour, even more preferably 5 hours or more, even more preferably 15 hours or more, even more preferably 30 hours or more, and even more preferably 45 hours or more. On the other hand, the upper limit of the temperature until storage in the container described above is not particularly limited, but is preferably 130 hours or less, more preferably 110 hours or less, even more preferably 90 hours or less, even 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 combined in any way. For example, the total time during which the temperature of the TCDDM composition is in the range of 45°C to less than 120°C is preferably 1 hour to 130 hours, more preferably more than 1 hour and 110 hours, even more preferably 5 hours to 90 hours, even more preferably 15 hours to 70 hours, even more preferably 30 hours to 60 hours, and even more preferably 45 hours to 50 hours.

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

[0031] In the TCDDM composition of this embodiment, the lower limit of the backscattering intensity T1 is T2 ÷ 8.0 or more, preferably T2 ÷ 7.0 or more, more preferably T2 ÷ 6.0 or more, even more preferably T2 ÷ 5.0 or more, even more preferably T2 ÷ 4.8 or more, even more preferably T2 ÷ 4.0 or more, even more preferably T2 ÷ 3.0 or more, particularly preferably T2 ÷ 2.5 or more, and most preferably T2 ÷ 2.0 or more. Furthermore, in the TCDDM composition of this embodiment, the upper limit of the backscattering intensity T1 is T2 × 5.0 or less, preferably T2 × 4.0 or less, more preferably T2 × 3.0 or less, even more preferably T2 × 2.0 or less, even more preferably T2 × 1.5 or less, even more preferably T2 × 1.0 or less, even more preferably T2 ÷ 1.4 or less, particularly preferably T2 ÷ 1.5 or less, and most preferably T2 ÷ 1.6 or less. By setting the viscosity above the lower limit, the TCDDM composition tends to have appropriate fluidity, making it easier to handle during compounding and other operations. Conversely, by setting the viscosity below the upper limit, the viscosity of the TCDDM composition is less likely to increase during storage, resulting in better storage stability. The above upper and lower limits can be combined arbitrarily. For example, in the TCDDM composition of the present invention, the backscatter intensity T1 can be T2÷8.0≦T1≦T2×5.0, preferably T2÷7.0≦T1≦T2×4.0 or more, more preferably T2÷6.0≦T1≦T2×3.0 or more, even more preferably T2÷5.0≦T1≦T2×2.0, even more preferably T2÷4.8≦T1≦T2×1.5, even more preferably T2÷4.0≦T1≦T2×1.0, even more preferably T2÷3.0≦T1≦T2÷1.4, particularly preferably T2÷2.5≦T1≦T2÷1.5, and most preferably T2÷2.0≦T1≦T2÷1.6.

[0032] In a more specific embodiment of the TCDDM composition of this embodiment, for example, the lower limit of the backscatter intensity T1 is preferably 1055 or higher, more preferably 1100 or higher, even more preferably 1500 or higher, and particularly preferably 1800 or higher. Also, in the TCDDM composition, the upper limit of the backscatter intensity T1 is preferably 10550 or lower, more preferably 8000 or lower, even more preferably 7000 or lower, particularly preferably 5000 or lower, and most preferably 3500 or lower. Setting it above the lower limit tends to make the TCDDM composition more fluid, thus improving handling during compounding operations. Also, setting it below the upper limit tends to make the viscosity of the TCDDM composition less likely to increase when stored, resulting in better storage stability. The above upper and lower limits can be combined arbitrarily. For example, in the TCDDM composition of the present invention, the backscatter intensity T1 is preferably 1055 ≤ T1 ≤ 10550, more preferably 1100 ≤ T1 ≤ 8000, even more preferably 1500 ≤ T1 ≤ 7000, particularly preferably 1800 ≤ T1 ≤ 5000, and particularly preferably 1800 ≤ T1 ≤ 3500.

[0033] The TCDDM composition of this embodiment preferably contains a chiral compound whose enantiomer is represented by formula (A) (hereinafter referred to as "chiral compound A") and / or a chiral compound whose enantiomer is represented by formula (B) (hereinafter referred to as "chiral compound B"), and more preferably contains both chiral compound A and chiral compound B. In other words, when there is a high amount of chiral compound A, microcrystals form in the TCDDM composition, and it tends to have good handling properties such as moderate fluidity due to the high amount of chiral compound B. When there is a high amount of chiral compound B, the proportion of chiral compound A becomes relatively low, the amount of TCDDM microcrystals in the TCDDM composition decreases, the viscosity does not increase easily during storage, and the storage stability tends to be good. [ka] [ka]

[0034] In the TCDDM composition of this embodiment, the lower limit of the content of chiral compound A is not particularly limited, but it 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 even more preferably 36% by mass or more, based on 100% by mass of the total mass of TCDDM. Furthermore, the upper limit of the content of chiral compound A is not particularly limited, but it 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 even more preferably 39% by mass or less. By setting the content above the lower limit, the TCDDM composition tends to have appropriate fluidity, making it easier to handle during compounding operations and other processes. Furthermore, by keeping the value below the upper limit, the formation of microcrystals of TCDDM in the TCDDM composition is suppressed, which tends to reduce viscosity increases during storage and improve storage stability. 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 especially most preferably 36% by mass or more and 39% by mass or less.

[0035] In the TCDDM composition of this embodiment, the lower limit of the content of chiral compound B is not particularly limited, but it 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, based on 100% by mass of the total mass of TCDDM. Furthermore, the upper limit of the content of chiral compound B is not particularly limited, but it 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 even more 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 that order of preference. By setting the value above the lower limit, the formation of microcrystals of TCDDM in the TCDDM composition is suppressed, making it less likely for viscosity to increase during storage and resulting in better storage stability. Furthermore, by setting the value below the upper limit, the TCDDM composition has appropriate fluidity, which tends to make it easier to handle during compounding and other operations. 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 B is not particularly limited, but is preferably 1.6% by mass or more and 4.8% by mass or less, more preferably 1.8% by mass or more and 4.6% by mass or less, even more preferably 2.0% by mass or more and 4.4% by mass or less, even more preferably 2.1% by mass or more and 4.3% by mass or less, even more preferably 2.2% by mass or more and 4.2% by mass or less, and even more preferably 2.3% by mass or more and 4.0% by mass or less, based on 100% by mass of the total mass of the TCDDM.

[0036] In the TCDDM composition of the present invention, the lower limit of the content of tricyclodecanedimethanol is not particularly limited, but from the viewpoint 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, even more preferably 95% by mass or more, and may also be 97% by mass or more, or 99% by mass or more, based on 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 may be 100% by mass of the total mass of the TCDDM composition.

[0037] The TCDDM composition 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 include, for example, compounds having an aldehyde group that are reaction intermediates during TCDDM synthesis, compounds having a carbonyl group derived from the aldehyde group-containing compound, C12 diols that are introduced during the manufacturing process, and known additives that may be added as needed. In the TCDDM composition of the present invention, the content of compounds other than TCDDM is not particularly limited as long as it does not impair the effects of the present invention, and can usually be 0.01% by mass or more and 3% by mass or less based on 100% by mass of the total mass of the TCDDM composition. It is also possible to have a composition that does not contain any 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 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, based on 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 may be 100% by mass of the total mass of the TCDDM composition.

[0039] In the TCDDM composition of the present invention, it is preferable that it substantially does not contain a fragrance carrier. Since the TCDDM composition of the present invention substantially does not contain a fragrance carrier, the storage stability and fluidity of the obtained TCDDM composition tend to be more excellent. Note that "substantially does not contain a fragrance carrier" means that the fragrance carrier is not intentionally contained. Specifically, the content of the fragrance carrier contained 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 with respect to the total mass of the tricyclodecane dimethanol composition.

[0040] <Method for producing TCDDM composition> The method for producing the TCDDM composition of the present embodiment includes a step of hydroformylating dicyclopentadiene to obtain tricyclodecane dicarbaldehydes, a step of obtaining a crude reaction solution containing tricyclodecane dimethanol by a reduction reaction of the tricyclodecane dicarbaldehyde, and a step of distilling and purifying the crude reaction solution to obtain a tricyclodecane dimethanol composition. At this time, in the step of introducing a formyl group by hydroformylation, isomers are generated, so tricyclodecane dicarbaldehydes, which are precursors of each of chiral compound A, chiral compound B, and chiral compound C, are obtained as a mixture. Then, by the hydrogenation step, chiral compound A, chiral compound B, chiral compound C, etc. are obtained respectively.

[0041] The method for controlling the ratios of chiral compound A, chiral compound B, and chiral compound C in the present embodiment is not particularly limited, but it may be controlled by adjusting the reaction conditions of hydroformylation, it may be isomerized using a method such as heating, or the ratios may be adjusted by distilling and purifying the produced TCDDM composition.

[0042] <Hydroformylation reaction of dicyclopentadiene> The method for hydroformylating dicyclopentadiene is not particularly limited and can be carried out according to a conventional method. For example, according to the method described in JP-A-2001-10999, in a hydroformylation reaction solvent composed of a hydrocarbon compound, dicyclopentadiene can be hydroformylated to produce tricyclodecane dicarbaldehyde using hydrogen and carbon monoxide in the coexistence of a catalyst composed of a rhodium compound and an organic phosphorus compound. The rhodium compound used in this hydroformylation step forms a complex with the organic phosphorus compound and exhibits hydroformylation activity in the presence of hydrogen and carbon monoxide regardless of the form of its precursor. That is, Rh(acac)(CO)2, Rh2O3, Rh4(CO) 12 , Rh6(CO) 16 , Rh(NO3)3 and other catalyst precursor substances can be introduced into the reaction mixture together with the organic phosphorus compound, and a rhodium metal hydridocarbonyl phosphorus complex having catalytic activity can be formed in the reaction vessel, or a rhodium metal hydridocarbonyl phosphorus complex catalyst can be prepared in advance and introduced into the reaction vessel.

[0043] In a preferred specific example of this embodiment, Rh(acac)(CO)2 is used as a rhodium precursor substance and reacted with an organic phosphorus compound in the presence of a solvent, and then introduced into a reactor together with an excess of free organic phosphorus compound to obtain a rhodium-organic phosphorus complex catalyst having catalytic activity. Examples of the rhodium compound and the organic phosphorus compound that forms a catalyst for the hydroformylation reaction include phosphites and phosphines.

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

[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, and di(2-t-butylphenyl)(t-butyl) phosphite. These phosphites may be used individually or in combination of two or more.

[0046] Alkyl phosphines, which exhibit particularly high steric hindrance, are 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 individually or in combination of two or more.

[0047] The amount of organophosphorus compound used can be adjusted so that tricyclodecanedicarbadehyde can be obtained at a sufficient hydroformylation reaction rate if the organophosphorus compound is present in the hydroformylation reaction solution in an amount of 1 to 400 molar times, preferably 3 to 200 molar times, relative to the rhodium metal.

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

[0049] Furthermore, after the hydroformylation reaction is complete, the reaction product containing tricyclodecanedicarbaldehyde is brought into contact with alcohol, and while the catalyst component remains in the dihydroformylation reaction solvent layer, tricyclodecanedicarbaldehyde is extracted into an extraction solvent layer consisting of alcohol, and layer separation is performed. For this reason, 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 aromatic hydrocarbon compounds include benzene and toluene, methylbenzenes such as 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, but are not limited to, pentane, hexane, heptane, octane, isooctane, dodecane, and decane, as long as they are liquids at standard temperature and pressure.

[0052] Suitable alicyclic hydrocarbon compounds include cyclohexane, cyclooctane, cyclododecane, decalin, and methylcyclohexane.

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

[0054] The amount of rhodium catalyst used is typically 10 to 5000 ppm by mass, more preferably 50 to 2000 ppm by mass, relative to the dicyclopentadiene raw material. If rhodium is used at a concentration of 50 ppm or higher, catalyst recovery will be necessary.

[0055] The temperature and pressure for the hydroformylation reaction of dicyclopentadiene are typically 40 to 160°C, preferably 80 to 140°C, and 1 to 15 MPa. If the temperature is below 40°C, the hydroformylation reaction rate is slow, and if it is above 160°C, side reactions from dicyclopentadiene and the hydroformylation reaction product in the reaction solution proceed, reducing the yield of the aldehyde. If the pressure is below 1 MPa, the hydroformylation reaction rate is slow, and if it is above 15 MPa, high-pressure reactors are 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 a range of 0.2 to 5.0 as the input gas composition (hydrogen / carbon monoxide). If the hydrogen / carbon monoxide mixed gas falls outside this range, the reaction activity of the hydroformylation reaction or the aldehyde selectivity will decrease.

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

[0058] <Extraction of tricyclodecanedicarboxylic acid> After the hydroformylation reaction is complete, the reaction product is either left as is, or diluted with the hydrocarbon compound used in the reaction as the hydroformylation solvent or another hydrocarbon compound, and then brought into contact with alcohol. The catalyst component remains in the hydroformylation solvent layer, and the product, tricyclodecanedicarbadehyde, is extracted into the alcohol for layer separation.

[0059] Examples of alcohols include primary alcohols with 1 to 3 carbon atoms and polyhydric alcohols with 2 to 6 carbon atoms. Examples of primary alcohols include methanol, ethanol, and propanol. Examples of polyhydric alcohols with 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, pentanediol isomers, 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 individually or in combination of two or more. Extraction may also be carried out with water present in addition to the alcohol. The addition of water facilitates the distribution of aldehydes and catalyst components to each layer.

[0060] For the hydroformylation reaction, it is preferable that the reaction solvent and extraction solvent have different densities to achieve effective layer separation. One preferred example of a hydroformylation reaction solvent and extraction solvent combination containing tricyclodecanedicarbadehyde is the combination of methylcyclohexane as the reaction solvent and ethylene glycol as the extraction solvent, methylcyclohexane as the reaction solvent and methanol as the extraction solvent, and water.

[0061] The distribution of tricyclodecanedicarboxylic acid between the hydroformylation reaction solvent and the extraction solvent is in equilibrium. In contrast, the catalytic components rhodium and organophosphorus compounds are substantially present only in the hydroformylation reaction solvent, and are present in the extraction solvent only at levels below the analytical limit. The volume ratio of the extraction solvent to the reaction product solution used depends on the solubility of tricyclodecanedicarbadehyde in the extraction solvent and the amount of tricyclodecanedicarbadehyde to be extracted. For example, if the tricyclodecanedicarbadehyde to be separated has high solubility in the extraction solvent and is present at a low concentration in the reaction product solution, practical extraction of tricyclodecanedicarbadehyde is possible by using an extraction solvent with a low volume ratio (extraction solvent / reaction product solution). The higher the concentration of the product, the higher the volume ratio (extraction solvent / reaction product) required to extract tricyclodecanedicarbadehyde from the reaction product. If tricyclodecanedicarbadehyde exhibits relatively low solubility in the extraction solution, the volume ratio (extraction solvent / reaction product) can vary within the range of 10:1 to 1:10. Furthermore, to increase the amount of tricyclodecanedicarbadehyde extracted with a small amount of extraction solvent, it is effective to divide the extraction solvent and perform the extraction operation several times. In the final extraction stage, a hydroformylation reaction solvent such as methylcyclohexane may be added at a concentration of approximately 5-20% by mass relative to the reaction product. Adding the hydroformylation reaction solvent can improve the catalyst removal rate. There are no particular restrictions on the temperature at which the extraction operation is performed, but it is practical to carry it out at or below the hydroformylation reaction temperature. After the reaction in the hydroformylation reactor, the extraction solvent may be added and the extraction operation performed, or the hydroformylation reaction product may be withdrawn from the hydroformylation reactor and the operation performed in an extraction tank. Alternatively, the extraction solvent can be added directly to the hydroformylation reactor and the extraction operation performed, and the catalyst component can be retained in the hydroformylation reactor to carry out the next hydroformylation reaction. If the hydroformylation reaction product is withdrawn and the operation is performed in an extraction tank, the reaction solvent layer of the hydrocarbon compound containing the catalyst is returned to the hydroformylation reactor and used again for the reaction. This process can be carried out as a batch process or a continuous process. The extraction procedure described above yields a tricyclodecanedicarbaldehyde-containing solution with 10-90% by mass of tricyclodecanedicarbaldehyde and 10-90% by mass of the extraction solvent. When a reaction solvent is added, a tricyclodecanedicarbaldehyde-containing solution with 5-90% by mass of tricyclodecanedicarbaldehyde, 5-90% by mass of the extraction solvent, and 5-90% by mass of the 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 acetal compounds in tricyclodecanedicarbaldehyde is typically around 0.1 to 50% by mass, and more specifically, around 1 to 25% by mass.

[0062] <Hydrogenation-reduction reaction> The extract containing tricyclodecanedicarbadehyde obtained by the above extraction operation (tricyclodecanedicarbadehyde-containing solution) is then subjected to hydrogenation reduction in the presence of a hydrogenation catalyst, preferably a ruthenium (Ru) catalyst, to produce TCDDM as shown in the following reaction formula (V). This hydrogenation-reduction reaction is preferable because, when carried out in the presence of water and a Ru catalyst, the acetal compound is rapidly converted to tricyclodecanedicarbaldehyde during the hydrogenation reaction of tricyclodecanedicarbaldehyde, and TCDDM can be produced in high yield by hydrogenating the tricyclodecanedicarbaldehyde converted from the acetal compound.

[0063] In the hydrogenation-reduction reaction, the amount of water present is preferably equal to or greater than the amount of acetal compound in the hydrogenation-reduction reaction solution, and is such that the reaction solution does not undergo phase separation. The water content relative to the total reaction solution is preferably 2% by mass or more, preferably 2-30% by mass, more preferably 5-25% by mass, and particularly preferably 10-20% by mass. When the water content is within the above range, the water and reaction solvent do not undergo phase separation, and the aforementioned effects of having water in the hydrogenation reaction system can be effectively obtained. This water may be added in an extraction step to separate the catalyst component and tricyclodecanedicarbadehyde from the hydroformylation reaction product solution, or water may be added to the reaction system immediately before the hydrogenation-reduction reaction.

[0064] The reaction method involves charging the catalyst as a slurry into a stirred reactor, carrying out the reaction in a batch manner, and then separating the catalyst from the product by sedimentation filtration after the reaction. Alternatively, a molded catalyst is charged into a tubular reactor, and an irrigation reaction is carried out in which the product and hydrogen gas are flowed over the catalyst. The amount of catalyst used is not particularly limited as long as it allows for the production of TCDDM with industrially advantageous productivity. The reaction temperature and pressure for hydrogenation-reduction reactions are typically 40-200°C, preferably 70-150°C, and the reaction pressure is usually 15 MPa or less. If the temperature is below 40°C, the hydrogenation-reduction reaction rate is slow, and if it is above 200°C, side reactions from the target product TCDDM proceed, reducing the yield of TCDDM. If the pressure is above 15 MPa, high-pressure reactors are used, resulting in higher 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, the thermal decomposition of TCDDM caused by the metal elements in the distillation purification process can be suppressed. There are no particular limitations on the method for removing metal elements from the crude reaction solution and reducing their content, and examples include activated carbon treatment, cation exchange resin, and silica gel adsorption. Activated carbon treatment is preferred due to 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 it may be a continuous process in which the crude reaction solution is passed through an activated carbon-packed column. In batch processing, the amount of activated carbon added to the crude reaction solution is appropriately determined based on the metal element adsorption capacity of the activated carbon and the metal element content in the crude reaction solution. Generally, it is preferable to add activated carbon to the crude reaction solution at a concentration of approximately 0.01 to 10% by mass and then stir. For continuous processing, there are no particular restrictions on the processing flow rate, but it is sufficient to process at a spatial 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, the treatment conditions, etc. may be changed between the first and second activated carbon treatments.

[0067] The lower the metal element content of the crude reaction solution subjected to the next step of distillation purification, the better from the viewpoint of suppressing the thermal decomposition of TCDDM. The metal element content of the crude reaction solution subjected to distillation purification is preferably 10 ppm by mass or less, particularly 5 ppm by mass or less, and especially 1 ppm by mass or less. The pH of the crude reaction solution subjected to distillation purification is preferably in the range of 6 to 8. A lower pH of 6 or higher is preferable because it suppresses the by-product formation of low-boiling point compounds that are thought to be caused by the dehydration of TCDDM and by-product formation of high-boiling point compounds that are thought to be caused by dimerization such as etherification. An upper pH of 8 or lower is preferable because it makes the distillation purification equipment less susceptible to alkaline corrosion.

[0068] Normally, the pH of the reaction product obtained from a hydrogenation-reduction reaction is 6-8. Even if this is subjected to treatment to remove the hydrogenation catalyst or metal elements, the pH will remain largely unchanged. However, the pH may deviate from the 6-8 range due to acidic and alkaline components leached from the hydrogenation catalyst. In such cases, it is preferable to adjust the pH to 6-8 by adding an appropriate pH adjusting agent such as an acid or alkali.

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

[0070] If the number of theoretical stages in a distillation column used for distillation purification is 10 or more, impurities and the product can be easily separated. If it is 30 or less, the pressure difference between the top and bottom of the column is small, and the temperature at the bottom of the column is low, thus reducing the heat load on the equipment. A more preferable number of theoretical stages is 15 to 30. If the column bottom temperature is 150°C or higher, TCDDM can be volatilized, and if it is 250°C or lower, the dimerization of TCDDM can suppress the by-product formation of high-boiling impurities. A more preferable column bottom temperature is 160-230°C.

[0071] There are no particular restrictions on other conditions of the distillation column during distillation purification, but it is usually carried out at a pressure of 0.1 to 100 kPa and a reflux ratio of 1 to 30. In particular, by controlling the reflux ratio and distillation rate, it is possible to adjust the relative abundance of chiral compound A, chiral compound B, and chiral compound C in the obtained TCDDM composition. These conditions can be arbitrarily changed according to the equipment performance of the distillation column, the efficiency of the kettle, the amount recovered, etc., and there are no particular restrictions as long as a TCDDM composition with the composition specified in this embodiment can be obtained.

[0072] The bottom liquor 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. Such distillation purification typically yields a TCDDM composition with a TCDDM purity of 98% or higher in high yield.

[0073] <Ultraviolet curable composition> The UV-curable composition of this embodiment is a UV-curable composition derived from the TCDDM composition of this embodiment. More specifically, the UV-curable composition of this embodiment is a UV-curable composition synthesized using the TCDDM composition of this embodiment as a raw material. Even more specifically, the UV-curable composition of this embodiment is a UV-curable composition synthesized using tricyclodecanedimethanol contained in the TCDDM composition of this embodiment as a raw material. There are no particular restrictions on the method for producing the UV-curable composition, and it can be carried out according to conventional methods. Generally, it is desirable to use tricyclodecanedimethanol in the TCDDM composition as a raw material, and to use it as a derivative such as a di(meth)acrylic acid ester derivative or urethane acrylate. Both hydroxyl groups of tricyclodecanedimethanol contained in the TCDDM composition may be used in the reaction, or one of the hydroxyl groups may be reacted while the other remains. In this case, the remaining hydroxyl group may be converted to a functional group suitable for the application by organic synthesis methods. Methods for producing di(meth)acrylic acid ester derivatives from TCDDM using a TCDDM composition as a raw material include, specifically, a method of reacting TCDDM with (meth)acrylic acid, a method of transesterifying TCDDM with (meth)acrylic acid ester, and a method of reacting TCDDM with a (meth)acrylic acid halide such as (meth)acrylic acid chloride.

[0074] The reaction conditions and other factors in each of the above manufacturing methods are as follows: When producing di(meth)acrylic acid ester derivatives using (meth)acrylic acid or (meth)acrylic acid esters, the reaction can be accelerated by using a catalyst and continuously removing the resulting water or lower alcohol from the system. Examples of the catalysts include those known as esterification catalysts such as sulfuric acid, p-toluenesulfonic acid, boron trifluoride, and organotin compounds, which can be arbitrarily selected and used. The amount of catalyst used is preferably 10 to 100,000 ppm relative to the total mass of the reaction substrate, from the viewpoint of reducing the load on the manufacturing equipment and reducing catalyst costs. When producing di(meth)acrylic acid ester derivatives using (meth)acrylic acid halides, it is preferable to carry out the reaction in the presence of a basic compound, and a catalyst can also be used to accelerate the reaction. Examples of the basic compound include tertiary amines such as triethylamine and N-ethyldiisopropylamine, phosphates such as potassium phosphate and sodium phosphate, carbonates such as potassium carbonate and sodium carbonate, and hydroxides such as potassium hydroxide and sodium hydroxide, all of which are known basic compounds and can be arbitrarily selected and used. From the viewpoint of reducing the load on the manufacturing equipment and reducing raw material costs, it is preferable to use 1.0 to 6.0 equivalents of the basic compound per equivalent of acrylic acid or methacrylic acid halide.

[0075] Examples of the catalysts include pyridines such as N,N-dimethyl-4-aminopyridine, imidazoles such as N-methylimidazole, and tertiary amines such as triethylenediamine, all of which are known catalysts for the esterification reaction of acid chlorides, and can be arbitrarily selected and used from among these. The amount of catalyst used is preferably 10 to 100,000 ppm relative to the total mass of the reaction substrate, from the viewpoint of reducing the load on the manufacturing equipment and reducing catalyst costs.

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

[0077] Examples of polymerization inhibitors 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 substrate, from the viewpoint of reducing the impact on catalytic activity and side reactions.

[0078] In each of the above manufacturing methods, the reaction temperature is preferably -20°C or higher, more preferably 0°C or higher, more preferably 120°C, and 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 more, and more preferably 20 hours or less.

[0079] Solvents can also be used in the reactions described above for each manufacturing method. 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 urethane acrylate derived from the TCDDM composition is not particularly limited in structure, as long as it is an acrylic acid or methacrylic acid ester derivative containing a urethane bond.

[0081] A preferred method for producing 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, polyol compounds other than the TCDDM composition may be added to adjust the performance of the cured product. The proportion 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, from the viewpoint of the hardness and heat resistance of the cured product. On the other hand, there is no particular upper limit to the above proportion, and a higher proportion is preferable.

[0082] Examples of the polyisocyanate compounds include paraphenylenediisocyanate, 2,4-tolylenediisocyanate, 2,6-tolylenediisocyanate, 2,2'-diphenylmethanediisocyanate, 2,4-diphenylmethanediisocyanate, 4,4'-diphenylmethanediisocyanate, diphenyl ether-4,4'-diisocyanate, o-xylylenediisocyanate, m-xylylenediisocyanate, p-xylylenediisocyanate, norbornenemethanediisocyanate and their hydrides, pentamethylenediisocyanate, hexamethylenediisocyanate, dicyclohexylmethanediisocyanate, 1,4-cyclohexanediisocyanate, isophoronediisocyanate, and the like. These can be used as nurates, adducts, biuretes, dimers, or trimers. They may be used individually or in combination of two or more.

[0083] The monohydroxyacrylate compound is preferably such that the structural site bonding the hydroxyl group and the acryloyloxy group consists 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 obtained by introducing (poly)oxyalkylene chains such as (poly)oxyethylene chains, (poly)oxypropylene chains, and (poly)oxytetramethylene chains into the molecular structure of the acrylate compounds; lactone modified compounds obtained by introducing a (poly)lactone structure into the molecular structure of the acrylate compounds; isocyanuric acid diacrylate; (poly)oxyalkylene modified compounds obtained by introducing (poly)oxyalkylene chains such as (poly)oxyethylene chains, (poly)oxypropylene chains, and (poly)oxytetramethylene chains into the molecular structure of isocyanuric acid diacrylate; and lactone modified compounds obtained by introducing a (poly)lactone structure into the molecular structure of isocyanuric acid diacrylate. Furthermore, methacrylate compounds obtained by replacing the acrylate in the aforementioned group of compounds with methacrylate may also be used. These may be used individually or in combination of two or more. 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; and propylene glycol. Examples of polyols include diols having ether groups such as 1,4-cyclohexanediol, 1,4-cyclohexanedimethanol, and 1,4-dihydroxyethylcyclohexane; diols having alicyclic structures such as xylylene glycol, 1,4-dihydroxyethylbenzene, and 4,4'-methylenebis(hydroxyethylbenzene); polyols such as glycerin, trimethylolpropane, and pentaerythritol; polyether polyols; polyester polyols; and polycarbonate polyols. These polyol compounds may be used individually or in combination of two or more.

[0084] Examples of the catalysts include organotin compounds such as dibutyltin dilaurate, trimethyltin hydroxide, and tetra-n-butyltin; organobismuth compounds such as dibutylbismuth dilaurate and dioctylbismuth dilaurate; metal salts such as zinc octyolate, tin octyolate, cobalt naphthenate, stannous chloride, and stannous 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 monohydroxyacrylate compounds and the like. The polymerization inhibitor is not particularly limited as long as it does not inhibit the reaction, and examples 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 substrate, from the viewpoint of reducing the impact on catalytic activity and side reactions.

[0086] In the above manufacturing method, the reaction temperature is preferably 30°C or higher, more preferably 40°C or higher, preferably 120°C or lower, and 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 more, and preferably 10 hours or less.

[0087] Solvents can also be used in the reactions described above for each manufacturing method. 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] Since the UV-curable composition of this embodiment is synthesized using the TCDDM composition of this embodiment as a raw material, its viscosity can be controlled to a high level without impairing the performance inherently required of a UV-curable composition, and it exhibits excellent coating stability. For this reason, the UV-curable composition of this embodiment can be suitably used as a hard coat material, an antifouling coating material, a resist material, an inkjet ink, and a material for 3D printers.

[0089] For applications such as photoresists, a method is used in which the UV-curable composition is applied to a substrate using screen printing or flex printing and then cured. From the viewpoint of being able to apply it thinly and uniformly, to be able to apply it in thick layers, and to be able to print fine patterns on the substrate with high precision, the UV-curable composition is required to have high viscosity.

[0090] For applications such as hard coats and anti-fouling coatings, including inkjet printing, methods are used in which the UV-curable composition is applied to a substrate using a coater, spray, or dispenser and then cured. From the viewpoint of accurately and quantitatively dispensing the UV-curable composition, the UV-curable composition is required to have high viscosity.

[0091] The UV-curable composition of this embodiment can be suitably used in applications such as hard coat materials, antifouling coating materials, resist materials, inkjet inks, and 3D printer materials.

[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 is a composition containing a polymer that includes structural units derived from tricyclodecanedimethanol in the TCDDM composition. Furthermore, the polymer composition of this embodiment is 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 it may be obtained by adding or removing an appropriate amount of a solvent such as water or an organic solvent to adjust the solid content concentration, or it may be obtained by removing the solvent and drying to obtain a solid. Furthermore, it may be a polymer composition obtained by appropriately removing impurities and purifying a composition containing the polymer obtained by polymerization, or it may be obtained by adding appropriate additives, such as preservative stabilizers (such as ultraviolet absorbers and antioxidants), colorants, antistatic agents, lubricants, fillers, flame retardants, and foaming agents, as needed, to the extent that they do not affect the performance of the polymer obtained by polymerization.

[0094] In other words, the polymer composition of this embodiment may include 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 or component composition. Another embodiment of the polymer composition specifically includes at least one selected from the group consisting of polyester resins, epoxy resins, acrylate resins, polycarbonate resins, and polyurethane resins. In this embodiment, the polyester resin is a resin mainly composed of a polyethylene polymer such as polyethylene terephthalate (PET). The polyethylene polymer is not particularly limited, and for example, it refers to a polymer that contains structural units derived from a polyol mainly composed of glycol and structural units derived from a terephthalic acid compound, and also contains structural units derived from tricyclodecanedimethanol in the TCDDM composition of this embodiment.

[0095] In this embodiment, the epoxy resin is a resin mainly composed of an epoxy polymer. The epoxy polymer is not particularly limited, and examples include polymers that contain structural units derived from bisphenol compounds and structural units derived from epichlorohydrin, and also contain structural units derived from tricyclodecanedimethanol in the TCDDM composition of this embodiment.

[0096] In this embodiment, the acrylate resin is a resin mainly composed of an acrylate polymer. The acrylate polymer is not particularly limited, and examples include polymers that contain structural units derived from (meth)acrylic acid or structural units derived from (meth)acrylic acid derivatives, and also polymers that contain structural units derived from tricyclodecanedimethanol in the TCDDM composition of this embodiment.

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

[0098] The following describes in detail a second embodiment of the present invention.

[0099] [Method for producing TCDDM composition stored in a container] The present invention provides a method for producing a tricyclodecanedimethanol composition stored in a container, comprising storing a tricyclodecanedimethanol composition (A0) (hereinafter sometimes referred to as "TCDDM composition (A0)") obtained by distillation purification, in a container while maintaining the temperature at no more than 45°C, characterized in that the tricyclodecanedimethanol contains a chiral compound (hereinafter sometimes referred to as "chiral compound A") whose enantiomer is represented by formula (A). Hereafter, tricyclodecanedimethanol may also be referred to as "TCDDM". [ka] The above configuration effectively suppresses turbidity of the TCDDM composition during storage. Furthermore, it effectively suppresses the decrease in fluidity of the TCDDM composition. In this specification, for convenience, a TCDDM composition stored in a container will be referred to as TCDDM composition (A1) stored in a container. Furthermore, in this specification, the TCDDM composition (A1) stored in a container, immediately before being fed into the processing machine after transportation and / or storage, may be referred to as TCDDM composition (A2).

[0100] Depending on its thermal history and handling conditions, TCDDM compositions may become cloudy or lose fluidity during storage, resulting in reduced handling properties. Under these circumstances, detailed studies by the inventors revealed that repeated heating and cooling caused the TCDDM composition to become cloudy and its fluidity to decrease. Specifically, one of the enantiomers of the chiral compound represented by formula (A) is prone to crystallization and easily forms microcrystals when cooled. When microcrystals of TCDDM such as chiral compound A form, the TCDDM composition becomes cloudy and its fluidity decreases. 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, which consist of TCDDM such as chiral compound A and exhibit a microscopic structural structure as detected by the dynamic light scattering method described later.

[0101] [TCDDM composition (A0)] Next, we will describe a tricyclodecanedimethanol composition (A0) (TCDDM composition (A0)) containing a chiral compound in which one of the enantiomers is represented by formula (A). The TCDDM composition (A0) in the present invention is a composition containing a chiral compound (chiral compound A) whose enantiomer is represented by the following formula (A), obtained by distillation purification.

[0102] The TCDDM composition (A0) in the present invention may contain, in addition to chiral compound A, tricyclodecanedimethanol (hereinafter referred to as "chiral compound B") whose enantiomer is represented by the following formula (B). In other words, the higher the amount of chiral compound A, the more microcrystals of TCDDM are formed in the TCDDM composition (A0), resulting in moderate fluidity and thus a tendency to be superior during handling operations such as compounding. Conversely, the higher the amount of chiral compound B, 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 in TCDDM microcrystals, making it less likely for viscosity to increase during storage and resulting in good storage stability.

[0103] [ka]

[0104] Furthermore, the TCDDM composition (A0) in the present invention may contain, in addition to chiral compound A and chiral compound B, and / or a chiricyclodecanedimethanol (hereinafter referred to as "chiral compound C") whose enantiomer is represented by formula (C). In other words, the higher the amount of chiral compound C, the lower the proportion of chiral compound A becomes, which reduces the amount of TCDDM microcrystals in the TCDDM composition (A0) or suppresses the increase in TCDDM microcrystals, making it less likely for viscosity to increase during storage and resulting in good storage stability.

[0105] [ka]

[0106] (Percentage of chiral compound A content) In the TCDDM composition (A0) of the present invention, the lower limit of the content of chiral compound A is not particularly limited, but from the viewpoint of superior handling during compounding operations, such as the formation of microcrystals in the TCDDM composition (A0) and ensuring appropriate fluidity, it 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, especially more preferably 35% by mass or more, and even more especially more preferably 36% by mass or more, based on 100% by mass of the total mass of the TCDDM composition (A0). Furthermore, while there is no particular upper limit to the content of chiral compound A, from the viewpoint of suppressing the formation of microcrystals of TCDDM in the TCDDM composition (A0), suppressing the increase in viscosity during storage, and ensuring good 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, even more preferably 43% by mass or less, even more preferably 41% by mass or less, even more preferably 40% by mass or less, especially more preferably 39% by mass or less, and even more especially more preferably 38.5% by mass or less. The above upper and lower limits can be combined arbitrarily. For example, in the TCDDM composition (A0), the content of the chiral compound A is not particularly limited, but is preferably 25% to 54% by mass, more preferably 28% to 50% by mass, even more preferably 30% to 45% by mass, even more preferably 32% to 43% by mass, even more preferably 33% to 41% by mass, even more preferably 34% to 40% by mass, even more preferably 35% to 39% by mass, and even more preferably 36% to 38.5% by mass. Although Example 2-1, described below, is carried out under conditions outside the preferred range of content ratios, the effects of the present invention can be obtained at the above-mentioned preferred range of content ratios.

[0107] (Percentage of chiral compound B content) In the TCDDM composition (A0) of the present invention, the lower limit of the content of chiral compound B is not particularly limited, but from the viewpoint of suppressing the formation of microcrystals of TCDDM in the TCDDM composition (A0), suppressing the increase in viscosity during storage, and having good storage stability, it is preferable that the content is 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, based on 100% by mass of the total mass of the TCDDM composition (A0). Furthermore, while there is no particular upper limit to the content of chiral compound B in the TCDDM composition (A0), from the viewpoint of superior handling during compounding operations, etc., a content of 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 even more 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 is preferred in that order. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A0), the content of the chiral compound B is not particularly limited, but is preferably 1.6% by mass or more and 4.8% by mass or less, more preferably 1.8% by mass or more and 4.6% by mass or less, even more preferably 2.0% by mass or more and 4.4% by mass or less, even more preferably 2.1% by mass or more and 4.3% by mass or less, even more preferably 2.2% by mass or more and 4.2% by mass or less, and even more preferably 2.3% by mass or more and 4.0% by mass or less. Although Example 2-1, described below, is carried out under conditions outside the preferred range of content ratios, the effects of the present invention can be obtained at the above-mentioned preferred range of content ratios.

[0108] (Percentage of chiral compound C content) In the TCDDM composition (A0) of the present invention, the lower limit of the content of chiral compound C is not particularly limited, but from the viewpoint of suppressing the formation of microcrystals of TCDDM in the TCDDM composition (A0), suppressing the increase in viscosity during storage, and having good storage stability, it is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 18% by mass or more, even more preferably 20% by mass or more, even more preferably 22% by mass or more, and even more preferably 25% by mass or more, based on 100% by mass of the total mass of the TCDDM composition (A0). Furthermore, while there is no particular upper limit to the content of chiral compound C in the TCDDM composition (A0), it is preferable that the content is 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, based on 100% by mass of the total mass of the TCDDM composition (A0). The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A0), the content of the chiral compound C is not particularly limited, but is preferably 10% to 45% by mass, more preferably 15% to 40% by mass, even more preferably 18% to 38% by mass, even more preferably 20% to 35% by mass, even more preferably 22% to 33% by mass, and even more preferably 25% to 30% by mass, based on 100% by mass of the total mass of TCDDM composition (A0). Although Example 2-1, described below, is carried out under conditions outside the preferred range of content ratios, the effects of the present invention can be obtained at the above-mentioned preferred range of content ratios.

[0109] (Percentage of TCDDM content in the TCDDM composition) In the TCDDM composition (A0), there is no particular lower limit to the total amount of TCDDM contained, but from the viewpoint of handling the composition, it is preferable that it be 70% by mass or more, more preferably 80% by mass or more, even 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 the TCDDM composition (A0). On the other hand, the upper limit of the total amount of TCDDM contained in the TCDDM composition (A0) is not particularly limited, and a higher percentage is preferable, and may be 100% by mass relative to the total mass of the 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 include, for example, compounds having an aldehyde group that are reaction intermediates during TCDDM synthesis, compounds having a carbonyl group derived from the aldehyde group-containing compound, C12 diols that are introduced during the manufacturing process, and known additives that may be added as needed. In the TCDDM composition (A0) of the present invention, the content of compounds other than TCDDM is not particularly limited as long as it does not impair the effects of the present invention, and can usually be 0.01% by mass or more and 2% by mass or less based on 100% by mass of the total mass of the TCDDM composition (A0). It is also possible to have a composition that does not contain any compounds other than TCDDM (0% by mass).

[0111] (Total content of chiral compounds A-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 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, based on 100% by mass of the total mass of TCDDM composition (A0). On the other hand, the upper limit of the total content is not particularly limited, and a higher percentage is preferable, and may be 100% by mass relative to the total mass of the TCDDM composition (A0).

[0112] In TCDDM composition (A0), it is preferable that it is substantially free of fragrance carriers. When TCDDM composition (A0) is substantially free of fragrance carriers, the resulting TCDDM composition tends to be less cloudy or less fluid. "Substantially free of fragrance carriers" means intentionally omitting fragrance carriers, and specifically means that the amount of fragrance carriers contained 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, based on the total mass of TCDDM composition (A0).

[0113] The following describes a method for producing a tricyclodecanedimethanol (TCDDM) composition stored in the container of the present invention, and further, a method for processing the TCDDM composition (A1) stored in the container, with reference to Figures 2 and 3.

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

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

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

[0117] (Process (1)) Step (1) shown in Figure 2 is the manufacturing process for the raw material, TCDDM composition (A0). The TCDDM composition (A0) can be manufactured by known methods. The TCDDM composition (A0) in the present invention can be obtained, for example, by the steps of hydroformylation of dicyclopentadiene to obtain tricyclodecanedicarbaldehyde, reduction of the tricyclodecanedicarbaldehyde to obtain a crude reaction solution containing tricyclodecanedimethanol (TCDDM), and distillation purification of the crude reaction solution. Details thereof can be found in paragraphs 0046-0017 of International Publication No. 2023 / 176641, which are incorporated herein by reference. As a specific embodiment, Figures 2 and 3 show 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] (Process (2)) Step (2), shown in Figures 2 and 3, includes the step of transferring the TCDDM composition (A0) obtained in step (1) to container 3 and storing it while maintaining the temperature at 45°C or higher, thereby obtaining a TCDDM composition (A1) containing chiral compound A in a stored state in the container. Ideally, the TCDDM composition (A0) should be used immediately after distillation. For example, it is desirable to put the TCDDM composition (A0) immediately after distillation into the processing machine (X). However, from a commercial and economic standpoint, typically, as shown in Figure 2, the TCDDM composition (A0) is stored in container 3 in step (2) to obtain TCDDM composition (A1). The obtained TCDDM composition (A1) is then transported or stored in container 3 in step (3), which will be described later, and subsequently fed into the processing machine (X). Furthermore, the TCDDM composition (A1) stored in container 3 may be stored in a warehouse or the like before and after transport. Alternatively, as shown in Figure 3, the TCDDM composition (A0) is stored in container 3 in step (2) to obtain TCDDM composition (A1). The obtained TCDDM composition (A1) may be fed into the processing machine (X) without going through step (3). The TCDDM composition (A1) obtained using the method for producing the TCDDM composition of the present invention is suitable for cases where the TCDDM composition (A1) stored in a container is put into a processing machine after storage and transportation, or when it is put directly into a processing machine, for reasons described later.

[0119] (Temperature until TCDDM composition (A0) is stored in a container) In the method for producing the TCDDM composition of the present invention, the TCDDM composition (A0) obtained by distillation purification is stored in container 3 while maintaining a temperature no lower than 45°C. By storing the distilled and purified TCDDM composition (A0) in container 3 while maintaining a temperature no lower than 45°C, the clouding of the TCDDM composition (A0) can be effectively suppressed. This is presumed to be because the formation of microcrystals in the TCDDM composition (A0) is suppressed, and the increase in viscosity is suppressed, thereby maintaining good storage stability of the TCDDM composition (A0). As a result, it becomes possible to produce organic materials using the TCDDM composition more efficiently. Details of the organic materials in the present invention will be described later.

[0120] In the method for producing the TCDDM composition of the present invention, it is necessary to maintain the temperature of the TCDDM composition (A0) obtained by distillation purification from the storage tank 2 to the container 3 so that it does not fall below 45°C. 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, even more preferably 65°C or higher, even more preferably 70°C or higher, even more preferably over 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, 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 in any way. For example, the temperature from the storage tank 2 to the container 3 is preferably 45°C or more and 110°C or less, more preferably 50°C or more and 100°C or less, even more preferably 60°C or more and 95°C or less, even more preferably over 60°C and 90°C or less, even more preferably 70°C or more and less than 90°C, and even more preferably over 70°C and 85°C or less.

[0121] Furthermore, the time for keeping the TCDDM composition (A0) obtained by distillation purification at a temperature not below 45°C is not particularly limited, but is preferably 1 hour or more, more preferably more than 1 hour, even more preferably 5 hours or more, even more preferably 15 hours or more, even more preferably 30 hours or more, and even more preferably 45 hours or more. On the other hand, the upper limit of the temperature until storage in the above-mentioned container is not particularly limited, but is preferably 130 hours or less, more preferably 110 hours or less, even more preferably 90 hours or less, even 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 combined arbitrarily. For example, the time for keeping the TCDDM composition (A0) obtained by distillation purification at a temperature not below 45°C is preferably 1 hour or more and 130 hours or less, more preferably more than 1 hour and 110 hours or less, even more preferably 5 hours or more and 90 hours or less, even more preferably 15 hours or more and 70 hours or less, even more preferably 30 hours or more and 60 hours or less, and even more preferably 45 hours or more and 50 hours or less.

[0122] Furthermore, the temperature from the storage tank 2 to the container 3 where the TCDDM composition is stored may fluctuate within a range that does not fall below 45°C. Specifically, the temperature change from the distillation purification 1 to storage in the container 3 is preferably within ±30°C, more preferably within ±20°C, even more preferably within ±15°C, even more preferably within ±10°C, and even more preferably within ±5°C.

[0123] As described above, the distilled and purified TCDDM composition (A0) can be temporarily stored in a storage tank 2 located between the distillation column 1 and the container 3, and then transferred to the container 3 for storage while maintaining the temperature so that it does not fall below 45°C. Alternatively, the distilled and purified TCDDM composition (A0) can be stored directly in container 3 from the distillation column 1 without passing through storage tank 2. Storing directly in container 3 from the distillation column 1 means that no intermediate operations such as heating or stirring are involved when transferring from the distillation column 1 to container 3. More specifically, it means that the TCDDM composition (A0) is supplied and stored from the distillation column 1 to container 3 in a single transfer step.

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

[0125] (Step (3)) Step (3) in Figure 2 may include at least one of the following: transporting the TCDDM composition (A1) stored in container 3 obtained by the manufacturing method of the present invention; storing the TCDDM composition (A1) stored in container 3; storing the TCDDM composition (A1) after transport; or transporting the TCDDM composition (A1) after storage. Specific embodiments include a form in which a manufacturer of the TCDDM composition stores the TCDDM composition (A1) stored in container 3; a form in which a carrier transports or stores the TCDDM composition (A1) stored in container 3; and a form in which a customer of the TCDDM composition (A1) stored in container 3 stores the TCDDM composition (A1) stored in container 3. The TCDDM composition obtained after the TCDDM composition (A1) undergoes step (3) is called TCDDM composition (A2).

[0126] (Temperature of TCDDM composition (A1) stored in the container) The method for producing the TCDDM composition of the present invention is preferable when the TCDDM composition (A1) obtained by the above production method is stored in container 3 and left in an environment of -5°C or higher and less than 45°C for 24 hours or more before being put into the processing machine (X) in step (4) described later. In this specification, "placed" includes not only storage in a warehouse, but also moving TCDDM composition (A1) stored in a container in a manner that does not subject it to excessive vibration, such as during transportation.

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

[0128] The temperature of the storage environment may fluctuate within the range of -5°C to less than 45°C. Specifically, the temperature change of the storage environment is preferably within ±20°C, and more preferably within ±15°C.

[0129] In cases where the product is stored in a container and left in an environment between -5°C and 45°C for 24 hours or more, the number of days it is left in such an environment is typically between 24 hours and 3 years.

[0130] (Step (4)) Step (4) shown in Figures 2 and 3 above is the step of putting the TCDDM composition (A1) stored in the container 3 obtained in step (2) or the TCDDM composition (A2) obtained in step (3) into the processing machine (X). Normally, the TCDDM composition (A1) stored in container 3 obtained in step (2) is used to obtain TCDDM composition (A2) via step (3), after which step (4) is carried out. In this specification, "processing the TCDDM composition" means, for example, causing a chemical reaction in the TCDDM composition in a reactor described later to convert it into another compound, or mixing the TCDDM composition with other substances in a blender described later.

[0131] (Heating temperature of TCDDM composition (A1) before input into processing machine) Step (4), shown in Figure 2 or Figure 3, is the step of feeding part or all of the TCDDM composition (A1) or TCDDM composition (A2) into the processing machine (X).

[0132] The processing machine (X) is not particularly limited as long as it is an apparatus for processing TCDDM composition (A1) or TCDDM composition (A2). For example, this could be a machine for converting a TCDDM composition into a desired shape or properties, or for converting TCDDM into other compounds. Specifically, known reactors and known compounders are examples.

[0133] The TCDDM composition (A1) or TCDDM composition (A2) can be introduced into the processing machine (X) in part or in whole after being heated or kept at a temperature of 45°C or higher but less than 120°C. By introducing part or all of the TCDDM composition (A1) or TCDDM composition (A2) into a processing machine (X) while maintaining a temperature of 45°C to less than 120°C, the formation of microcrystals in the TCDDM composition and the increase in viscosity can be suppressed. Alternatively, the TCDDM composition may become less cloudy, allowing for more efficient subsequent processing.

[0134] (Heating or keeping temperature of TCDDM composition (A1) and TCDDM composition (A2)) The lower limit of the heating temperature or holding temperature of the TCDDM composition (A1) or TCDDM composition (A2) is not particularly limited, but from the viewpoint of suppressing the formation of microcrystals in the TCDDM composition before it is put into the processing machine, suppressing an increase in viscosity, and maintaining good handling of the TCDDM composition when it is put into the processing machine, it 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 the temperature for maintaining warmth is not particularly limited, but from the viewpoint of suppressing deterioration due to thermal decomposition or alteration of the TCDDM composition and suppressing an increase in utility costs such as steam and electricity, it is less than 120°C, preferably 100°C or less, more preferably 80°C or less, even more preferably 75°C or less, even more preferably 70°C or less, and even more preferably 65°C or less. The above upper and lower limits can be combined in any way. For example, the heating temperature or holding temperature of the TCDDM composition (A1) or TCDDM composition (A2) is 45°C or more and less than 120°C, preferably 50°C or more and 100°C or less, more preferably 52°C or more and 80°C or less, even more preferably 54°C or more and 75°C or less, even more preferably 56°C or more and 70°C or less, and even more preferably 58°C or more and 65°C or less.

[0135] The heating temperature or the temperature holding temperature may be raised or lowered within the range of 45°C to less than 120°C. Specifically, the temperature change of 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] A method for heating or maintaining a portion or all of a TCDDM composition (A1) or TCDDM composition (A2) at a temperature of 45°C or higher but less than 120°C is to heat or maintain the TCDDM composition (A1) or TCDDM composition (A2) while it is stored in container 3. By not transferring the TCDDM composition from container 3 to another container before heating, the formation of microcrystals of chiral compound A in the TCDDM composition can be suppressed more effectively. Alternatively, as another method of heating or maintaining temperature, the TCDDM composition (A1) or TCDDM composition (A2) may be heated in a pipe or the like that supplying it to the processing machine (X).

[0137] (Temperature during the process of loading TCDDM composition (A1) or TCDDM composition (A2) into the processing machine (X)) It is preferable to heat or maintain the TCDDM composition (A1) or TCDDM composition (A2) at a temperature of 45°C or higher and less than 120°C before introducing it into the processing machine (X). The lower limit of the temperature of the TCDDM composition (A1) or TCDDM composition (A2) between heating or keeping warm and being introduced into the processing machine (X) is not particularly limited, but from the viewpoint of suppressing the formation of microcrystals in the TCDDM composition during introduction into the processing machine, suppressing the increase in viscosity, and maintaining good handling of the TCDDM composition, it is 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 temperature is not particularly limited, but from the viewpoint of suppressing deterioration of the TCDDM composition due to thermal decomposition and alteration, and suppressing an increase 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, even more preferably 70°C or lower, and even more preferably 65°C or lower. The above upper and lower limits can be combined in any way. For example, the temperature of the TCDDM composition (A1) or TCDDM composition (A2) between heating and being fed into the processing machine (X) is preferably 50°C to 100°C, more preferably 52°C to 80°C, even more preferably 54°C to 75°C, even more preferably 56°C to 70°C, and even more preferably 58°C to 65°C.

[0138] Furthermore, the temperature of the TCDDM composition (A1) or TCDDM composition (A2) between heating and being fed into the processing machine may fluctuate within the range of 45°C to less than 120°C. Specifically, the temperature change between heating and 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 partially or entirely fed into the processing machine (X). Furthermore, partially feeding the TCDDM composition (A1) or TCDDM composition (A2) into the processing machine (X) includes the case where the TCDDM composition (A1) or TCDDM composition (A2) is fed into the processing machine (X) sequentially. Additionally, after partially feeding the 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 saved, and then the TCDDM composition (A1) or TCDDM composition (A2) may be fed back into the processing machine (X) to produce the organic material. The processing machine into which the remaining TCDDM composition (A1) or TCDDM composition (A2) is fed may be the same as the previous processing machine or a different machine. Furthermore, if, after loading a portion of the TCDDM composition (A1) or TCDDM composition (A2) into the processing machine, the container 3 containing the remaining TCDDM composition (A2) is to be stored, the storage of the container 3 containing the remaining TCDDM composition (A2) can also be carried out while maintaining a temperature of 45°C or higher and less than 120°C.

[0140] In the method for producing the TCDDM composition of the present invention, in step (3), the TCDDM composition (A1) is heated while stored in the container 3, and the heated TCDDM composition (A2) can then be directly fed from the container 3 into the processing machine (X). In other words, in the manufacturing method of the present invention, the TCDDM composition (A1) stored in container 3 is heated in step (3) while still stored in container 3 to become TCDDM composition (A2), and then in step (4), TCDDM composition (A2) is directly fed from container 3 into processing machine (X).

[0141] In this specification, "direct transfer" means that the contents of container 3 are transferred to the processing machine (X) in a single step of "transferring," without any intermediate operations such as heating or stirring. It goes without saying that this also includes cases where the contents are transferred via a connecting pipe between container 3 and the processing machine (X) during the "transferring" step. By reducing the transfer process, the formation of microcrystals in the TCDDM composition (A2) can be effectively suppressed.

[0142] Preferably, the TCDDM composition (A1) stored in container 3 in step (2) is not heated in step (4) until it is supplied to the processing machine (X) and heated to 45°C or higher but less than 120°C. This configuration makes it possible to produce organic materials more efficiently.

[0143] (Method of manufacturing organic materials) The TCDDM composition (A1) or TCDDM composition (A2) stored in container 3 is preferably used in the production of organic materials. The following describes a preferred embodiment of a method for producing an organic material using the TCDDM composition stored in container 3.

[0144] (First form of a method for manufacturing organic materials) A preferred first embodiment of the method for producing an organic material includes, in step (4), heating part or all of the TCDDM composition (A1) or TCDDM composition (A2) stored in container 3, while keeping the TCDDM composition (A0) obtained by distillation purification at a temperature not below 45°C, to a temperature of 45°C or higher and less than 120°C, and then feeding the heated TCDDM composition (A2) into a processing machine (X) for processing while keeping it within the temperature range. In step (4), the TCDDM composition (A1) or (A2) is heated while stored in container 3, and the resulting TCDDM composition (A1) or (A2) is directly fed from container 3 into the processing machine (X). In the first embodiment, the content of chiral compound A in the TCDDM composition (A1) is preferably 25% by mass or more and 54% by mass or less, based on 100% by mass of the total mass of the TCDDM composition (A1).

[0145] Furthermore, the organic material 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.

[0146] (Second form of method for manufacturing organic materials) A preferred second embodiment of the method for producing the organic material is that, in the first embodiment, the TCDDM composition (A1) is further stored in container 3 in an environment of -5°C or higher and below 45°C for 24 hours or more before heating.

[0147] (Third form of method for manufacturing organic materials) A preferred third embodiment of the method for producing the organic material is that, in the first and / or second embodiment, no stirring is performed between the time the TCDDM composition (A0) is stored in the container 3 and the time the TCDDM composition (A2) is directly put into the processing machine (X).

[0148] (Fourth form of method for manufacturing organic materials) A preferred fourth embodiment of the method for producing the organic material is a method for producing the TCDDM composition stored in the container 3, wherein, in any of the first to third embodiments, heating is not performed until the TCDDM composition (A1) is heated to 45°C or higher and less than 120°C after the TCDDM composition (A0) has been stored in the container 3.

[0149] [TCDDM composition (A1)] Next, we will describe a tricyclodecanedimethanol composition (A1) (TCDDM composition (A1)) containing a chiral compound in which one of the enantiomers is represented by formula (A). The TCDDM composition (A1) in the present invention is the TCDDM composition after going through step (2) above, and is stored in container 3, and is a composition containing a chiral compound (chiral compound A) in which one of the enantiomers is represented by the following formula (A).

[0150] [ka]

[0151] The TCDDM composition (A1) in the present invention is obtained by storing the above-mentioned raw material, TCDDM composition (A0), in a container 3 while maintaining the temperature at no more than 45°C. More specifically, it can also be obtained by hydroformyrating dicyclopentadiene to obtain tricyclodecanedicarbaldehyde, and then obtaining a crude reaction solution containing tricyclodecanedimethanol by the reduction reaction of the tricyclodecanedicarbaldehyde, and then purifying the crude reaction solution obtained through these steps by distillation and storing it directly in container 3 while maintaining a temperature no lower than 45°C.

[0152] The TCDDM composition (A1) in the present invention may contain, in addition to chiral compound A, tricyclodecanedimethanol (hereinafter referred to as "chiral compound B") whose enantiomer is represented by the following formula (B). In other words, the more chiral compound A there is, the more microcrystals are formed in the TCDDM composition (A1), resulting in moderate fluidity and thus superior handling during compounding operations. Conversely, the more chiral compound B there is, the relatively lower the proportion of chiral compound A, reducing the amount of TCDDM microcrystals in the TCDDM composition (A1) or suppressing the increase in TCDDM microcrystals, which tends to reduce viscosity during storage and improve storage stability.

[0153] [ka]

[0154] Furthermore, the TCDDM composition (A1) in the present invention may contain, in addition to chiral compound A and chiral compound B, and / or a chiricyclodecanedimethanol (hereinafter referred to as "chiral compound C") whose enantiomer is represented by formula (C). In other words, the higher the amount of chiral compound C, the less the amount of TCDDM microcrystals in the TCDDM composition (A1) decreases or the more the amount of TCDDM microcrystals increases, making it less likely for the viscosity to increase during storage and resulting in better storage stability.

[0155] [ka]

[0156] Furthermore, 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] (Percentage of chiral compound A content) In the TCDDM composition (A1) of the present invention, the lower limit of the content of chiral compound A is not particularly limited, but from the viewpoint of superior handling during compounding operations, such as the formation of microcrystals in the TCDDM composition (A1) and ensuring appropriate fluidity, it 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, especially more preferably 35% by mass or more, and even more especially more preferably 36% by mass or more, based on 100% by mass of the total mass of the TCDDM composition (A1). Furthermore, while there is no particular upper limit to the content of chiral compound A, from the viewpoint of suppressing the formation of microcrystals of TCDDM in the TCDDM composition (A1), suppressing the increase in viscosity during storage, and ensuring good storage stability, it is preferable that the content of chiral compound A be 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, especially more preferably 39% by mass or less, and even more especially more preferably 38.5% by mass or less, based on 100% by mass of the total mass of the TCDDM composition (A1). The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A1), the content of the chiral compound A is preferably 25% to 54% by mass, more preferably 28% to 50% by mass, even more preferably 30% to 45% by mass, even more preferably 32% to 43% by mass, even more preferably 33% to 41% by mass, even more preferably 34% to 40% by mass, even more preferably 35% to 39% by mass, and even more preferably 36% to 38.5% by mass. Although Example 2-1, described below, is carried out under conditions outside the preferred range of content ratios, the effects of the present invention can be obtained at the above-mentioned preferred range of content ratios.

[0158] (Percentage of chiral compound B content) In the TCDDM composition (A1) of the present invention, the lower limit of the content of chiral compound B is not particularly limited, but from the viewpoint of suppressing the formation of microcrystals of TCDDM in the TCDDM composition (A1), suppressing the increase in viscosity during storage, and having good storage stability, it is preferable that the content is 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, based on 100% by mass of the total mass of the TCDDM composition (A1). Furthermore, while there is no particular upper limit to the content of chiral compound B in the TCDDM composition (A1), from the viewpoint of superior handling during compounding operations, etc., since microcrystals are formed in the TCDDM composition (A1) and appropriate fluidity is ensured, it is preferable that the content is 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 even more 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 that order of preference. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A1), the content of the chiral compound B is preferably 1.6% by mass or more and 4.8% by mass or less, more preferably 1.8% by mass or more and 4.6% by mass or less, even more preferably 2.0% by mass or more and 4.4% by mass or less, even more preferably 2.1% by mass or more and 4.3% by mass or less, even more preferably 2.2% by mass or more and 4.2% by mass or less, and even more preferably 2.3% by mass or more and 4.0% by mass or less, based on 100% by mass of the total mass of TCDDM composition (A1). Although Example 2-1, described below, is carried out under conditions outside the preferred range of content ratios, the effects of the present invention can be obtained at the above-mentioned preferred range of content ratios.

[0159] (Percentage of chiral compound C content) In the TCDDM composition (A1) of the present invention, the lower limit of the content of chiral compound C is not particularly limited, but from the viewpoint of suppressing the formation of microcrystals of TCDDM in the TCDDM composition (A1), suppressing the increase in viscosity during storage, and having good storage stability, it is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 18% by mass or more, even more preferably 20% by mass or more, even more preferably 22% by mass or more, and even more preferably 25% by mass or more, based on 100% by mass of the total mass of the TCDDM composition (A1). Furthermore, while there is no particular upper limit to the content of chiral compound C in the TCDDM composition (A1), it is preferable that the content be 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, based on 100% by mass of the total mass of the TCDDM composition (A1). The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A1), the content of the chiral compound C is preferably 10% to 45% by mass, more preferably 15% to 40% by mass, even more preferably 18% to 38% by mass, even more preferably 20% to 35% by mass, even more preferably 22% to 33% by mass, and even more preferably 25% to 30% by mass, based on 100% by mass of the total mass of TCDDM composition (A1). Although Example 2-1, described below, is carried out under conditions outside the preferred range of content ratios, the effects of the present invention can be obtained at the above-mentioned preferred range of content ratios.

[0160] (TCDDM content) In TCDDM composition (A1), there is no particular lower limit to the total amount of TCDDM contained, but from the viewpoint of handling the composition, it is preferable that it be 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, the upper limit of the total amount of TCDDM contained in TCDDM composition (A1) is not particularly limited, and a higher percentage is preferable, and may be 100% by mass relative to the total mass of TCDDM composition (A1).

[0161] (Total content of chiral compounds A-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 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, based on 100% by mass of the total mass of TCDDM composition (A1). On the other hand, the upper limit of the total content is not particularly limited, and a higher value is preferable; it may be 100% by mass relative to the total mass of the TCDDM composition (A1).

[0162] (Backscattering intensity T1 of TCDDM composition (A1)) The 173° backscattering intensity T1 is an indicator of the fluidity and storage stability of the TCDDM composition.

[0163] The lower limit of the 173° backscatter intensity T1 measured at a temperature of 25°C using the dynamic light scattering measurement method for the TCDDM composition (A1) is not particularly limited, but the 173° backscatter intensity T1 increases relatively, microcrystals are formed in the TCDDM composition (A1), and the TCDDM composition (A1) has appropriate fluidity, and from the viewpoint of being superior during handling operations such as compounding, standard sample (D 50When the backscattering intensity of a 0.002 volume% aqueous suspension of latex with a wavelength of 300 nm is T2, T2÷500 or more is preferred, T2÷250 or more is more preferred, T2÷200 or more is even more preferred, T2÷100 or more is even more preferred, T2÷50 or more is even more preferred, T2÷10 or more is even more preferred, and T2÷8 or more is particularly preferred. On the other hand, the upper limit of the backscattering intensity T1 is not particularly limited, but from the viewpoint of reducing the relative 173° backscattering intensity T1 when the TCDDM composition (A1) is stored, reducing the amount of TCDDM microcrystals in the TCDDM composition (A1) or suppressing the increase of TCDDM microcrystals, making it less likely for viscosity to increase and improving storage stability, T2 × 5.0 or less is preferred, T2 × 2.0 or less is more preferred, T2 or less is even more preferred, T2 ÷ 2 or less is even more preferred, T2 ÷ 3 or less is even more preferred, T2 ÷ 4 or less is even more preferred, and T2 ÷ 5 or less is particularly preferred. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A1), the backscatter intensity T1 is preferably T2÷500≦T1≦T2, more preferably T2÷250≦T1≦T2÷2, even more preferably T2÷200≦T1≦T2÷3, even more preferably T2÷100≦T1≦T2÷4, even more preferably T2÷50≦T1≦T2÷5, even more preferably T2÷8.0≦T1≦T2×5.0, particularly preferably T2÷8.0≦T1≦T2×2.0, and most preferably T2÷8.0≦T1≦T2.

[0164] As a more specific embodiment of the TCDDM composition (A1) in the present invention, for example, the lower limit of the backscattering intensity T1 is not particularly limited, but since the TCDDM composition (A1) has appropriate fluidity, it tends to be better during handling operations such as compounding, so it is preferably 10 or more, more preferably 50 or more, and even more preferably 100 or more. On the one hand, the upper limit of the rear scattering intensity T1 is not particularly limited. However, since the viscosity of the TCDDM composition (A2) is less likely to increase and the handling properties such as storage stability and compounding operations tend to be better, it is preferably 5000 or less, more preferably 3000 or less, and even more preferably 1000 or less. The above upper and lower limit values can be arbitrarily combined. For example, in the TCDDM composition (A1), the 173° rear scattering intensity T1 measured at a temperature of 25°C using the dynamic light scattering measurement method of the composition 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. The rear scattering intensity T1 of the TCDDM composition (A1) is measured according to the description of the examples described later.

[0165] The method of setting the rear scattering intensity T1 within the above range is not particularly limited. For example, it can be achieved by storing the TCDDM composition (A0) in container 3 while keeping the temperature from falling below 45°C. More preferably, it can be achieved by suppressing heating after manufacturing the TCDDM raw material (TCDDM composition (A0)), stirring of TCDDM in a heated state, and transfer of containers, etc.

[0166] [TCDDM composition (A2)] The TCDDM composition (A2) in the present invention refers to the TCDDM composition (A1) after undergoing the above step (3). That is, the TCDDM composition (A2) refers to the TCDDM composition stored in the above container 3 after transportation and / or storage. In step (4), a part or all of the TCDDM composition (A2) can be heated and introduced into a processing machine. In the present invention, since the TCDDM composition (A0) is stored in container 3 while being kept from falling below 45°C in step (2), the TCDDM composition (2) after transporting and storing the TCDDM composition (A1) can be easily processed even when introduced into a processing machine.

[0167] In the TCDDM composition (A2) of the present invention, in addition to the chiral compound A, it may contain a chiral compound B represented by the above formula (B) and a chiral compound C represented by the above formula (C). That is, the more chiral compound A there is, the more microcrystals are formed in the TCDDM composition (A2), and since it has appropriate fluidity, it tends to be excellent during handling such as formulation operations. The more chiral compound B there is, the relatively lower the proportion of chiral compound A becomes, the microcrystals of TCDDM in the TCDDM composition (A1) decrease or the increase in the microcrystals of TCDDM is suppressed, and the viscosity is less likely to increase during storage, and the storage stability tends to be good. When there is a large amount of chiral compound C, the proportion of chiral compound A becomes relatively low, the microcrystals of TCDDM in the TCDDM composition (A1) decrease or the increase in the microcrystals of TCDDM is suppressed, and the viscosity is less likely to increase during storage, and the storage stability tends to be good.

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

[0169] (Content ratio of chiral compound A) In the TCDDM composition (A2) of the present invention, the lower limit of the content ratio of the chiral compound A is not particularly limited, but from the viewpoint of excellent handling during formulation operations and the like where microcrystals are formed in the TCDDM composition (A2) and appropriate fluidity can be ensured, based on 100% by mass of the total mass of the TCDDM composition (A2), 25% by mass or more is preferable, 28% by mass or more is more preferable, 30% by mass or more is further preferable, 32% by mass or more is still more preferable, 33% by mass or more is even more preferable, 34% by mass or more is still even more preferable, 35% by mass or more is particularly even more preferable, and 36% by mass or more is more particularly even more preferable. Furthermore, while there is no particular upper limit to the content of chiral compound A, from the viewpoint of suppressing the formation of microcrystals of TCDDM in the TCDDM composition (A2), suppressing the increase in viscosity during storage, and ensuring good storage stability, it is preferable that the content be 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, especially more preferably 39% by mass or less, and even more especially more preferably 38.5% by mass or less, based on 100% by mass of the total mass of the TCDDM composition (A2). The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A2), the content of the chiral compound A is preferably 25% to 54% by mass, more preferably 28% to 50% by mass, even more preferably 30% to 45% by mass, even more preferably 32% to 43% by mass, even more preferably 33% to 41% by mass, even more preferably 34% to 40% by mass, even more preferably 35% to 39% by mass, and even more preferably 36% to 38.5% by mass. Although Example 2-1, described below, is carried out under conditions outside the preferred range of content ratios, the effects of the present invention can be obtained at the above-mentioned preferred range of content ratios.

[0170] (Percentage of chiral compound B content) In the TCDDM composition (A2) of the present invention, the lower limit of the content of chiral compound B is not particularly limited, but from the viewpoint of suppressing the formation of microcrystals of TCDDM in the TCDDM composition (A2), suppressing the increase in viscosity during storage, and having good storage stability, it 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, based on 100% by mass of the total mass of the TCDDM composition (A2). Furthermore, while there is no particular upper limit to the content of chiral compound B in the TCDDM composition (A2), from the viewpoint of ensuring good handling during compounding operations, etc., by allowing microcrystals to form in the TCDDM composition (A2) and ensuring appropriate fluidity, it is preferable that the content be 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 even more 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 that order of preference. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A2), the content of the chiral compound B is preferably 1.6% by mass or more and 4.8% by mass or less, more preferably 1.8% by mass or more and 4.6% by mass or less, even more preferably 2.0% by mass or more and 4.4% by mass or less, even more preferably 2.1% by mass or more and 4.3% by mass or less, even more preferably 2.2% by mass or more and 4.2% by mass or less, and even more preferably 2.3% by mass or more and 4.0% by mass or less, based on 100% by mass of the total mass of TCDDM composition (A2). Although Example 2-1, described below, is carried out under conditions outside the preferred range of content ratios, the effects of the present invention can be obtained at the above-mentioned preferred range of content ratios.

[0171] (Percentage of chiral compound C content) In the TCDDM composition (A2) of the present invention, the lower limit of the content of chiral compound C is not particularly limited, but from the viewpoint of suppressing the formation of microcrystals of TCDDM in the TCDDM composition (A1), suppressing the increase in viscosity during storage, and having good storage stability, it is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 18% by mass or more, even more preferably 20% by mass or more, even more preferably 22% by mass or more, and even more preferably 25% by mass or more, based on 100% by mass of the total mass of the TCDDM composition (A2). Furthermore, while there is no particular upper limit to the content of chiral compound C in the TCDDM composition (A2), it is preferable that the content be 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, based on 100% by mass of the total mass of the TCDDM composition (A2). By setting the upper limit above the lower limit, the microcrystals of TCDDM in the TCDDM composition (A1) The upper and lower limits above can be arbitrarily combined. For example, in the TCDDM composition (A1), the content of the chiral compound B is preferably 10% to 45% by mass, more preferably 15% to 40% by mass, even more preferably 18% to 38% by mass, even more preferably 20% to 35% by mass, even more preferably 22% to 33% by mass, and even more preferably 25% to 30% by mass, based on 100% by mass of the total mass of the TCDDM composition (A2). Although Example 2-1, described below, is carried out under conditions outside the preferred range of content ratios, the effects of the present invention can be obtained at the above-mentioned preferred range of content ratios.

[0172] (TCDDM content) In the TCDDM composition (A2), there is no particular lower limit to the TCDDM content, but from the viewpoint of handling the composition, it is preferable that it be 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 the TCDDM composition (A2). On the other hand, the upper limit of the total content is not particularly limited, and a higher value is preferable; it may be 100% by mass relative to the total mass of the TCDDM composition (A2).

[0173] (Total content of chiral compounds A-C) In the 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 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, based on 100% by mass of the total mass of the 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, based on 100% by mass of the total mass of the TCDDM composition (A2).

[0174] (Backscattering intensity T1 of TCDDM composition (A2)) The 173° backscattering intensity T1 is an indicator of the fluidity and storage stability of the TCDDM composition.

[0175] The lower limit of the 173° backscatter intensity T1 measured at a temperature of 25°C using the dynamic light scattering measurement method for the TCDDM composition (A2) is not particularly limited, but because microcrystals are formed in the TCDDM composition (A1) and the TCDDM composition (A2) has appropriate fluidity, it is less likely to exhibit stringiness and is superior in handling operations such as compounding, the standard sample (D 50 When the backscattering intensity of a 0.002 volume% aqueous suspension of latex with a wavelength of 300 nm is T2, T2 ÷ 100 or more is preferred, T2 ÷ 50 or less is more preferred, T2 ÷ 30 or more is even more preferred, T2 ÷ 10 or more is even more preferred, and T2 ÷ 7 or more is even more preferred. On the other hand, the upper limit of the backscattering intensity T1 is not particularly limited, but from the viewpoint of reducing the amount of TCDDM microcrystals in the TCDDM composition (A2) or suppressing the increase in TCDDM microcrystals, suppressing the increase in viscosity during processing, and improving storage stability and handling in compounding operations, T2 × 2.0 or less is preferred, T2 × 1.5 or less is more preferred, T2 or less is even more preferred, T2 ÷ 1.3 or less is particularly preferred, and T2 ÷ 1.5 or less is most preferred. The above upper and lower limits can be combined arbitrarily. For example, in the TCDDM composition (A2), the backscatter intensity T1 is preferably T2÷100≦T1≦T2×2.0, more preferably T2÷50≦T1≦T2×1.5, even more preferably T2÷30≦T1≦T2, even more preferably T2÷10≦T1≦T2÷1.3, and even more preferably T2÷7≦T1≦T2÷1.5.

[0176] As a more specific embodiment of the TCDDM composition (A2) in the present invention, for example, the lower limit of the backscattering intensity T1 is preferably 50 or more, more preferably 100 or more, and even more preferably 700 or more. On the other hand, the upper limit of the backscattering intensity T1 is not particularly limited, but from the viewpoint of preventing the viscosity of the TCDDM composition (A2) from increasing and improving storage stability and handling during compounding operations, it is preferably 10,000 or less, more preferably 8,000 or less, and even more preferably 5,000 or less. The above upper and lower limits can be combined in any way. For example, the backscattering intensity T1 of the TCDDM composition (A2) is preferably 50 to 10000, more preferably 100 to 8000, and even more preferably 700 to 5000. The backscatter intensity T1 of the TCDDM composition (A2) is measured according to the example described below.

[0177] The method for setting the backscatter intensity T1 within the above range is not particularly limited, but can be achieved, for example, by heating the TCCM composition (A1), which is stored in a container and at a temperature below 45°C, to 45°C or higher and less than 120°C. More preferably, it can be achieved by performing step (3) in Figure 2 described above.

[0178] [Method for storing TCCDM composition] The method for storing the TCCDM composition of the present invention includes storing the TCCDM composition (A0) containing tricyclodecane dimethanol obtained by distillation purification in a container while keeping it at a temperature not lower than 45°C. The tricyclodecane dimethanol contains a chiral compound in which one enantiomer is represented by formula (A). This is the method for storing the TCCDM composition.

Chemical formula

[0179] Details of the embodiments regarding the method for storing the TCDDM composition of the present invention are synonymous with the step of storing the tricyclodecane dimethanol composition (A0) containing a chiral compound in which one enantiomer is represented by formula (A), as described in the above [Method for producing a TCDDM composition stored in a container], while keeping it at a temperature not lower than 45°C. The preferred ranges are also the same.

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

[0181] Details of the chiral compound in which one enantiomer is represented by formula (A) in the method for storing the TCDDM composition are synonymous with the matters described in the above [Method for producing a TCDDM composition stored in a container]. The preferred range of the content ratio of the chiral compound represented by formula (A) in the TCDDM composition is also the same.

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

Chemical formula

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

[0184] The details of the chiral compound represented by formula (B) as one of the enantiomers in the method for preserving the TCDDM composition of the present invention are the same as those described in the above-mentioned [Method for producing a TCDDM composition stored in a container], and the preferred range of the content of tricyclodecanedimethanol 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) may contain tricyclodecanedimethanol, in which one of the enantiomers is represented by formula (C). [ka]

[0186] In the method for preserving the TCCDM composition of the present invention, the content of tricyclodecanedimethanol, in which one of the enantiomers is represented by formula (C), is preferably 10% by mass or more and 45% by mass or less, based on 100% by mass of the total mass of the TCCDM composition (A0).

[0187] The details of the method for storing the TCDDM composition of the present invention, in which one of the enantiomers is tricyclodecanedimethanol represented by formula (C), are the same as those described in the above-mentioned [Method for producing a TCDDM composition stored in a container], and the preferred range of the content ratio of tricyclodecanedimethanol represented by formula (C) in the TCDDM composition is also the same.

[0188] In the method for storing the TCCDM composition of the present invention, the tricyclodecanedimethanol composition stored in the container can be heated while stored in the container and then directly dispensed from the container into a processing machine. In the method for preserving the TCCDM composition of the present invention, the processing equipment can be a reactor and / or a blender. The details of the processing machine in the method for storing the TCDDM composition are the same as those described in the above-mentioned [Method for producing TCDDM composition stored in a container].

[0189] Details of embodiments of the present invention regarding the method for storing the TCDDM composition are the same as the details of embodiments described above in [Method for producing a TCDDM composition stored in a container], and the preferred range is also the same.

[0190] [Organic materials] The TCDDM composition (A1), and furthermore, the TCDDM composition (A2), are processed and used as various organic materials. The type of organic material is not particularly specified and can be used in the manufacture of 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 this invention is a resin mainly composed of a polyethylene polymer such as polyethylene terephthalate (PET). The polyethylene polymer is not particularly limited, and for example, it is a polymer that contains structural units derived from a polyol mainly composed of glycol and structural units derived from a terephthalic acid compound, and also contains structural units derived from tricyclodecanedimethanol in the TCDDM composition (A2).

[0192] The epoxy resin in the present invention is a resin mainly composed of an epoxy polymer. The epoxy polymer is not particularly limited, and examples include polymers that contain structural units derived from bisphenol compounds and structural units derived from epichlorohydrin, and also contain structural units derived from tricyclodecanedimethanol in the TCDDM composition (A2).

[0193] The acrylate-based resin in the present invention is a resin mainly composed of an acrylate-based polymer. The acrylate-based polymer is not particularly limited, and examples include polymers that contain structural units derived from (meth)acrylic acid or structural units derived from (meth)acrylic acid derivatives, and also contain structural units derived from tricyclodecanedimethanol in the TCDDM composition (A2).

[0194] The polycarbonate resin in the present invention is a resin mainly composed of a polycarbonate polymer. The polycarbonate polymer is not particularly limited, and examples include polymers that contain structural units derived from bisphenol compounds, structural units derived from phosgene (carbonyl chloride), or structural units derived from diphenyl carbonate, and also polymers that contain structural units derived from tricyclodecanedimethanol in the TCDDM composition (A2).

[0195] The polyurethane resin in the present invention is a resin mainly composed of a polyurethane polymer. The polyurethane polymer is not particularly limited, and examples include polymers that include structural units derived from a glycol-based polyol and structural units derived from a bifunctional isocyanate, and also include structural units derived from tricyclodecanedimethanol in the TCDDM composition (A2).

[0196] The UV-curable composition in 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 tricyclodecanedimethanol 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 conventional methods. Generally, it is desirable to use tricyclodecanedimethanol in the TCDDM composition (A2) as a raw material and to use it as a derivative such as a di(meth)acrylic acid ester derivative or a urethane acrylate. Details regarding the production methods of these derivatives can be found in paragraphs 0098 to 0117 of International Publication No. 2023 / 176641, which are incorporated herein by reference.

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

[0198] The following describes in detail a third embodiment of the present invention.

[0199] [Methods for manufacturing organic materials] The present invention provides a method for producing an organic material, comprising heating part or all of a tricyclodecanedimethanol composition (A1), which is stored in a container and at a temperature below 45°C, to 45°C or higher and below 120°C, and then processing the heated tricyclodecanedimethanol composition (A2) by introducing it into a processing machine while maintaining the temperature between 45°C and below 120°C, wherein the tricyclodecanedimethanol contains a chiral compound in which one enantiomer 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 the organic material of this embodiment is not a fragrance material. [ka] The above configuration makes it possible to suppress the increase in viscosity of the TCDDM composition during storage and to provide a method for producing organic materials that can efficiently generate organic materials using the TCDDM composition as a raw material.

[0200] Depending on its thermal history and handling conditions, TCDDM compositions may experience increased viscosity, decreased fluidity, and reduced handling properties during storage. Under these circumstances, detailed studies by the inventors revealed that repeated heating and cooling can increase the viscosity of the TCDDM composition, making it difficult to efficiently manufacture organic materials. Specifically, one of the enantiomers of the chiral compound represented by formula (A) (hereinafter sometimes referred to as "chiral compound A") is prone to crystallization and easily forms microcrystals when cooled. When microcrystals of TCDDM such as chiral compound A form, the viscosity of the TCDDM composition increases, its fluidity decreases, and its handling becomes difficult. As a result, it may become difficult to feed the TCDDM composition into processing machines for manufacturing organic materials, or the TCDDM composition itself may become cloudy, making it difficult to efficiently manufacture organic materials. In this invention, the term "microcrystals" refers to minute particles with an average particle size of submicrons or less, which consist of TCDDM such as chiral compound A and exhibit a microscopic structural structure as detected by the dynamic light scattering method described later.

[0201] In the method for producing organic materials of the present invention, a TCDDM composition (A1) containing chiral compound A stored in a container at a temperature below 45°C is heated and then maintained at that temperature. This effectively suppresses the formation of microcrystals made of TCDDM such as chiral compound A in the TCDDM composition and maintains that state, thereby enabling the efficient production of organic materials.

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

[0203] The details of each of the above steps will be explained below.

[0204] Step (1) in Figure 5 above is the manufacturing process for the raw material, TCDDM composition (A0). The TCDDM composition (A0) can be manufactured by known methods. The TCDDM composition (A0) in the present invention can be obtained, for example, by the steps of hydroformylation of dicyclopentadiene to obtain tricyclodecanedicarbaldehyde, reduction of the tricyclodecanedicarbaldehyde to obtain a crude reaction solution containing tricyclodecanedimethanol, and distillation purification of the crude reaction solution. Details thereof can be found in paragraphs 0046-0017 of International Publication No. 2023 / 176641, which are incorporated herein by reference.

[0205] Figure 5(2) above shows the process of obtaining a TCDDM composition (A1) containing chiral compound A, which is stored in a container and at a temperature of less than 45°C, by storing the TCDDM composition (A0) in a container. Ideally, the distilled and purified TCDDM composition (A0) could be directly fed into a processing machine for manufacturing organic materials. However, typically, the distilled and purified TCDDM composition (A0) is stored in containers, transported, and then processed into organic materials. Furthermore, the TCDDM composition stored in containers may be kept in warehouses or similar places before and after transport. The method for manufacturing organic materials of the present invention is suitable for cases where the TCDDM composition is stored and transported before being processed into organic materials.

[0206] (Temperature until TCDDM composition (A0) is stored in a container) In the method for producing organic materials of the present invention, it is preferable to store the TCDDM composition (A0) obtained by distillation purification in a container while maintaining the temperature at no more than 45°C. By storing the distilled and purified TCDDM composition (A0) in a container while maintaining the temperature at no more than 45°C, the formation of microcrystals in the TCDDM composition (A0) and the increase in viscosity can be suppressed, thereby maintaining good storage stability of the TCDDM composition (A0). As a result, it becomes possible to produce organic materials more efficiently. It is preferable to maintain the temperature from the distillation and purification process to storage in a storage container at a temperature of 45°C or higher. 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, even more preferably over 60°C, even more preferably 70°C or higher, even more preferably over 70°C, and particularly preferably 75°C or higher. The upper limit of the temperature until storage 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 below 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 until storage is preferably 45°C to 110°C, more preferably 50°C to 100°C, even more preferably 60°C to 95°C, even more preferably over 60°C and 90°C or below, even more preferably 70°C to less than 90°C, and even more preferably over 70°C and 85°C or below.

[0207] Furthermore, the time for keeping the TCDDM composition (A0) obtained by distillation purification at a temperature not below 45°C is preferably 1 hour or more, more preferably more than 1 hour, even more preferably 5 hours or more, even more preferably 15 hours or more, even more preferably 30 hours or more, and even more preferably 45 hours or more. On the other hand, the upper limit of the temperature until storage in the above-mentioned container is preferably 130 hours or less, more preferably 110 hours or less, even more preferably 90 hours or less, even 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 combined arbitrarily. For example, the time for keeping the TCDDM composition (A0) obtained by distillation purification at a temperature not below 45°C is preferably 1 hour or more and 130 hours or less, more preferably more than 1 hour and 110 hours or less, even more preferably 5 hours or more and 90 hours or less, even more preferably 15 hours or more and 70 hours or less, even more preferably 30 hours or more and 60 hours or less, and even more preferably 45 hours or more and 50 hours or less.

[0208] Furthermore, the temperature from the distillation purification (tank) to storage in the storage container may fluctuate within a range that 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, even more preferably within ±10°C, and even more preferably within ±5°C.

[0209] The distilled and purified TCDDM composition (A0) described above can be stored in a container directly from the distillation column. Storing directly from the distillation column means that no intermediate operations such as heating or stirring are involved in the transfer from the distillation column to the container; more specifically, it means that the TCDDM composition (A0) is stored in a container in a single step of transfer. Alternatively, the distilled and purified TCDDM composition (A0) may be temporarily stored in a storage tank located between the distillation column and the container, heated or kept warm so that the temperature does not fall below 45°C, and then transferred to the container for storage.

[0210] The container in which the TCDDM composition (A0) is stored is not specifically defined in terms of type, and any container capable of storing TCDDM can be widely used. Therefore, the container includes drums, 18-liter cans, glass bottles, and transport vehicles such as trailers. From the viewpoint of transportation costs and ease of handling, drums are preferred.

[0211] Steps (1) and (2) in Figure 5 above are not necessarily required. For example, a TCDDM composition (A1) containing chiral compound A, which is stored in a container and at a temperature below 45°C, can be purchased from a TCDDM composition raw material manufacturer or the like.

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

[0213] (Temperature of TCDDM composition (A1) stored in the container) The method for producing the organic material of the present invention is particularly suitable when the TCDDM composition (A1) is stored in a container and left in an environment of -5°C or higher and below 45°C for 24 hours or more before heating in step (5) described later. In this context, "to be placed" includes not only storage in a warehouse, but also the movement of TCDDM composition (A1) stored in a container in a manner that avoids excessive vibration, such as during transportation.

[0214] When stored in a container and left in an environment of -5°C or higher but less than 45°C for 24 hours or more, the lower limit of the storage environment temperature 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. The upper limit of the storage environment temperature 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. By setting the value above the lower limit, the formation of microcrystals in the TCDDM composition is suppressed, thereby further improving the effect of suppressing viscosity increase. Furthermore, by setting the value below or below the upper limit, the effect of suppressing deterioration of the TCDDM composition due to thermal decomposition or alteration is further improved. Furthermore, the upper and lower limits of the storage environment temperature can be arbitrarily combined. For example, a preferred combination of storage environment temperatures is -5°C or higher and less 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 the range of -5°C to less than 45°C. Specifically, the temperature change of the storage environment is preferably within ±20°C, and more preferably within ±15°C.

[0216] In cases where the product is stored in a container and left in an environment between -5°C and 45°C for 24 hours or more, the number of days it is left in such an environment is typically between 24 hours and 3 years.

[0217] Steps (3) and (4) in Figure 5 above are not necessarily required. For example, a TCDDM composition (A1) containing chiral compound A, which is stored in a container and at a temperature below 45°C, can be purchased and processed directly into the processing machine.

[0218] (Heating temperature of TCDDM composition (A1) before input into processing machine) Step (5) in Figure 5 above shows the process of heating part or all of the TCDDM composition (A1) to 45°C or higher but less than 120°C, and then feeding the heated TCDDM composition (A2) into the processing machine (X) while maintaining the temperature between 45°C and lower but less than 120°C. By heating part or all of the TCDDM composition (A1) to 45°C or higher but less than 120°C, and then feeding the heated TCDDM composition (A2) into the processing machine (X) while maintaining the temperature between 45°C and lower but less than 120°C, the formation of microcrystals in the TCDDM composition can be suppressed, the increase in viscosity can be suppressed, the TCDDM composition is less likely to become cloudy, and organic materials can be manufactured more efficiently.

[0219] The lower limit of the heating temperature for 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, even 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, even more preferably 70°C or lower, and even more preferably 65°C or lower. By setting the value above the lower limit, the formation of microcrystals in the TCDDM composition before it is fed into the processing machine can be suppressed, and the increase in viscosity can be suppressed, thus maintaining good handling of the TCDDM composition when it is fed into the processing machine. Furthermore, by setting the value below the upper limit, deterioration of the TCDDM composition due to thermal decomposition and alteration can be suppressed. In addition, 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 way. Furthermore, the upper and lower limits of the heating temperature can be arbitrarily combined. For example, the heating temperature is 45°C or more and less than 120°C, preferably 50°C or more and 100°C or less, more preferably 52°C or more and 80°C or less, even more preferably 54°C or more and 75°C or less, even more preferably 56°C or more and 70°C or less, and even more preferably 58°C or more and 65°C or less.

[0220] The heating temperature may fluctuate within the range of 45°C to less than 120°C. Specifically, the temperature change of 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] It is preferable to heat the TCDDM composition (A1) while it is still stored in the container. By not transferring the composition to another container, the formation of microcrystals of chiral compound A can be more effectively suppressed. However, in the method for producing organic materials of the present invention, it is not necessarily required to heat the TCDDM composition (A1) while it is stored in a container. For example, heating the TCDDM composition (A1) in piping or the like connecting it to a processing machine is also included in heating part or all of the TCDDM composition (A1) to 45°C or higher and less than 120°C.

[0222] (Heating temperature during the process of loading the TCDDM composition (A1) into the processing machine (X)) The heated TCDDM composition (A2) is introduced into the processing machine while maintaining a temperature of 45°C or higher and less than 120°C. The lower limit of the temperature of the TCDDM composition (A2) after heating and before being fed into the processing machine is 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. The upper limit of the temperature of the TCDDM composition (A2) after heating and before being fed into the processing machine is preferably 100°C or lower, more preferably 80°C or lower, even more preferably 75°C or lower, even more preferably 70°C or lower, and even more preferably 65°C or lower. By setting the value above the lower limit, the formation of microcrystals in the TCDDM composition during processing can be suppressed, and the increase in viscosity can be suppressed, thus maintaining good handling properties of the TCDDM composition. Furthermore, by setting the value below the upper limit, deterioration of the TCDDM composition due to thermal decomposition and alteration can be suppressed. In addition, an increase in utility costs such as steam and electricity can be suppressed. The above upper and lower limits for the temperature of the TCDDM composition (A2) during the process of heating and then feeding it into the processing machine can be arbitrarily combined. For example, the temperature is preferably 50°C to 100°C, more preferably 52°C to 80°C, even more preferably 54°C to 75°C, even more preferably 56°C to 70°C, and even more preferably 58°C to 65°C.

[0223] The temperature of the TCDDM composition (A2) during the process of heating and then feeding it into the post-processing machine may fluctuate within the range of 45°C to less than 120°C. Specifically, the temperature change during the process of heating and then feeding it into the post-processing machine is preferably within ±20°C, more preferably within ±15°C, even more preferably within ±10°C, and most preferably within ±5°C.

[0224] The heated TCDDM composition (A2) may be partially or entirely fed into the processing machine. Furthermore, partially feeding the TCDDM composition (A2) into the processing machine includes the case where the TCDDM composition (A2) is fed into the machine sequentially. Additionally, after partially feeding the TCDDM composition (A2) into the processing machine, the container holding the remaining TCDDM composition (A2) may be saved, and then the remaining TCDDM composition (A2) may be fed into the processing machine again to produce the organic material. The processing machine into which the remaining TCDDM composition (A2) is fed may be the same as or different from the previous processing machine. Furthermore, if, after a portion of the TCDDM composition (A2) has been put into the processing machine, the container holding the remaining TCDDM composition (A2) is to be stored, it is preferable to maintain the temperature of the container holding the remaining TCDDM composition (A2) at 45°C or higher and less than 120°C.

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

[0226] In this specification, "direct transfer" means that the contents of the container are transferred into the processing machine in a single step, without any intermediate operations such as heating or stirring. Therefore, it goes without saying that this includes cases where the contents are transferred via connecting pipes between the container and the processing machine. By reducing the transfer process, the formation of microcrystals in the TCDDM composition (A2) can be effectively suppressed.

[0227] The processing machine is not limited to any particular type, as long as it is a device for processing the TCDDM composition (A2). The processing machine is not particularly limited to any machine that converts the TCDDM composition into a desired shape or properties, or converts TCDDM into other compounds, and examples include reactors and mixers. Furthermore, "processing the TCDDM composition" means, for example, causing a chemical reaction in the reactor to convert the TCDDM composition into another compound, or mixing the TCDDM composition with other substances in the mixer.

[0228] In the manufacturing method of the present invention, it is preferable not to heat the TCDDM composition (A1) until it is heated to 45°C or higher and less than 120°C after the TCDDM composition (A0) has been stored in a container. This configuration makes it possible to manufacture organic materials more efficiently.

[0229] The following describes preferred embodiments of the method for producing the organic material of the present invention. A preferred first embodiment of the method for producing an organic material of the present invention is a method for producing an organic material in which part or all of a TCDDM composition (A1) stored in a container and at a temperature below 45°C is heated to 45°C or higher and less than 120°C, and the heated TCDDM composition (A2) is put into a processing machine for processing while maintaining a temperature of 45°C or higher and less than 120°C, wherein the heating of the TCDDM composition (A1) is performed while it is stored in the container, and then it is put directly from the container into the processing machine, the content of chiral compound A in the TCDDM composition (A1) is 25% by mass or higher and 54% by mass or less based on 100% by mass of the total mass of the TCDDM composition (A1), the processing machine is a reactor and / or a blender, 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 preferred second embodiment of the method for producing organic materials of the present invention is a method for producing organic materials in which, in the first embodiment, the TCDDM composition (A0) obtained by distillation purification is stored in a container while being kept at a temperature no lower than 45°C, and the TCDDM composition (A1) is stored in a container and left in an environment of -5°C or higher and less than 45°C for 24 hours or more before heating.

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

[0232] A preferred fourth embodiment of the method for producing organic materials of the present invention is a method for producing organic materials in which, in any of the first to third embodiments, heating is not performed until the TCDDM composition (A1) is heated to 45°C or higher and less than 120°C after the TCDDM composition (A0) has been stored in a container.

[0233] [TCDDM composition (A1)] Next, we will describe a tricyclodecanedimethanol composition (A1) (TCDDM composition (A1)) containing a chiral compound in which one of the enantiomers is represented by formula (A). The TCDDM composition (A1) in the present invention is a composition containing a chiral compound (chiral compound A) in which one of the enantiomers is represented by the following formula (A), which is stored in a container and at a temperature of less than 45°C.

[0234] [ka]

[0235] The TCDDM composition (A1) in the present invention is obtained by storing the above-mentioned raw material, TCDDM composition (A0), in a container while keeping it at a temperature no lower than 45°C. More specifically, it can also be obtained by hydroformyrating dicyclopentadiene to obtain tricyclodecanedicarbaldehyde, and then obtaining a crude reaction solution containing tricyclodecanedimethanol by the reduction reaction of the tricyclodecanedicarbaldehyde, and then purifying the crude reaction solution obtained through these steps by distillation, and storing it directly in a container while maintaining a temperature no lower than 45°C.

[0236] (Backscattering intensity T1 of TCDDM composition (A1)) In the TCDDM composition (A1) of the present invention, the lower limit of the 173° backscatter intensity T1 measured at a temperature of 25°C using the dynamic light scattering measurement method of the composition is not particularly limited, but is less limited than that of a standard sample (D 50 When the backscattering intensity of a 0.002 volume% aqueous suspension of latex with a wavelength of 300 nm is T2, it is preferable that T2 ÷ 500 ≤ T1 ≤ T2. The above configuration yields a TCDDM composition (A1) that exhibits excellent storage stability and fluidity.

[0237] The 173° backscattering intensity T1 is an indicator of the fluidity and storage stability of the TCDDM composition.

[0238] By setting the lower limit of the backscattering intensity T1 to T2÷500 or more, the 173° backscattering intensity T1 relatively increases, causing microcrystals to form in the TCDDM composition (A1), ensuring appropriate fluidity, which is advantageous during handling operations such as compounding. On the other hand, by setting the upper limit of the backscattering intensity T1 to T2 or less, the 173° backscattering intensity T1 relatively decreases, reducing the amount of TCDDM microcrystals in the TCDDM composition (A1) or suppressing the increase of TCDDM microcrystals, suppressing the increase in viscosity during storage, and resulting in good storage stability.

[0239] The method for setting the backscatter intensity T1 to T2 or less is not particularly limited, but can be achieved, for example, by storing part or all of the TCDDM composition (A0) in a container while maintaining a temperature of, for example, 45°C to less than 120°C, so that the temperature does not fall below 45°C. On the other hand, the method for setting the backscatter intensity T1 to T2÷500 or more is not particularly limited, but can be achieved, for example, by suppressing heating after the manufacture of the TCDDM raw material (TCDDM composition (A0)), stirring of the TCDDM while it is heated, or transferring it to another container.

[0240] In the TCDDM composition (A1) of the present invention, the lower limit of the backscattering intensity T1 is preferably T2 ÷ 500 or more, more preferably T2 ÷ 250 or more, even more preferably T2 ÷ 200 or more, particularly preferably T2 ÷ 100 or more, and most preferably T2 ÷ 50 or more. Furthermore, the upper limit of the backscattering intensity T1 is preferably T2 or less, more preferably T2÷2 or less, even more preferably T2÷3 or less, even more preferably T2÷4 or less, and even more preferably T2÷5 or less. By setting the viscosity above the lower limit, the TCDDM composition (A1) has appropriate fluidity, making it easier to handle during compounding and other operations. Furthermore, by setting the viscosity below the upper limit, the viscosity of the TCDDM composition (A1) does not increase easily during storage, resulting in good storage stability. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A1), the backscatter intensity T1 is preferably T2÷500≦T1≦T2, more preferably T2÷250≦T1≦T2÷2, even more preferably T2÷200≦T1≦T2÷3, even more preferably T2÷100≦T1≦T2÷4, and even more preferably T2÷50≦T1≦T2÷5.

[0241] As a more specific embodiment of the TCDDM composition (A1) in the present invention, for example, the lower limit of the backscatter intensity T1 is preferably 10 or more, more preferably 50 or more, even more preferably 100 or more, even more preferably 200 or more, and even more preferably 400 or more. Also, in the TCDDM composition (A1), the upper limit of the backscatter intensity T1 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 the viscosity above the lower limit, the TCDDM composition (A1) has appropriate fluidity, making it easier to handle during compounding and other operations. Furthermore, by setting the viscosity below the upper limit, the viscosity of the TCDDM composition (A1) does not increase easily during storage, resulting in good storage stability. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A1), the backscatter intensity T1 is preferably 10 ≤ T1 ≤ 5000, more preferably 50 ≤ T1 ≤ 3000, even more preferably 100 ≤ T1 ≤ 2000, even more preferably 200 ≤ T1 ≤ 1000, and even more preferably 400 ≤ T1 ≤ 900.

[0242] The TCDDM composition (A1) in the present invention may contain, in addition to chiral compound A, and / or one of its enantiomers represented by formula (B) below, chiricyclodecanedimethanol (hereinafter referred to as "chiral compound B"). In other words, the more chiral compound A there is, the more microcrystals are formed in the TCDDM composition (A1), resulting in moderate fluidity and thus superior handling during compounding operations. Conversely, the more chiral compound B there is, the relatively lower the proportion of chiral compound A, reducing the amount of TCDDM microcrystals in the TCDDM composition (A1) or suppressing the increase in TCDDM microcrystals, which tends to reduce viscosity during storage and improve storage stability.

[0243] [ka]

[0244] Furthermore, the TCDDM composition (A1) in the present invention may contain, in addition to chiral compound A and chiral compound B, and / or a chiricyclodecanedimethanol (hereinafter referred to as "chiral compound C") whose enantiomer is represented by formula (C). In other words, the higher the amount of chiral compound C, the less the amount of TCDDM microcrystals in the TCDDM composition (A1) decreases or the more the amount of TCDDM microcrystals increases, making it less likely for the viscosity to increase during storage and resulting in better storage stability.

[0245] [ka]

[0246] (Percentage of chiral compound A content) 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, especially more preferably 35% by mass or more, and even more especially preferably 36% by mass or more, based on 100% by mass of the total mass of the TCDDM composition (A1). Furthermore, while there is no particular upper limit to the content of chiral compound A, it 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, especially more preferably 39% by mass or less, and even more especially more preferably 38.5% by mass or less. By setting the value above the lower limit, microcrystals are formed in the TCDDM composition (A1), ensuring adequate fluidity, which is advantageous during handling operations such as compounding. Conversely, by setting the value below the upper limit, the formation of microcrystals of TCDDM in the TCDDM composition (A1) is suppressed, preventing an increase in viscosity during storage and resulting in good storage stability. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A1), the content of the chiral compound A is not particularly limited, but is preferably 25% to 54% by mass, more preferably 28% to 50% by mass, even more preferably 30% to 45% by mass, even more preferably 32% to 43% by mass, even more preferably 33% to 41% by mass, even more preferably 34% to 40% by mass, even more preferably 35% to 39% by mass, and even more preferably 36% to 38.5% by mass.

[0247] (Percentage of chiral compound B content) In the TCDDM composition (A1) of the present invention, the lower limit of the content of chiral compound B is not particularly limited, but it 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, based on 100% by mass of the total mass of the TCDDM composition (A1). Furthermore, the upper limit of the content of chiral compound B in TCDDM composition (A1) is not particularly limited, but it 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 in that order, it is preferable to have 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. By setting the value above the lower limit, the formation of microcrystals of TCDDM in the TCDDM composition (A1) is suppressed, preventing an increase in viscosity during storage and resulting in good storage stability. Conversely, by setting the value below the upper limit, microcrystals are formed in the TCDDM composition (A1), ensuring appropriate fluidity, which is superior during handling operations such as compounding. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A1), the content of the chiral compound B is not particularly limited, but is preferably 1.6% by mass or more and 4.8% by mass or less, more preferably 1.8% by mass or more and 4.6% by mass or less, even more preferably 2.0% by mass or more and 4.4% by mass or less, even more preferably 2.1% by mass or more and 4.3% by mass or less, even more preferably 2.2% by mass or more and 4.2% by mass or less, and even more preferably 2.3% by mass or more and 4.0% by mass or less.

[0248] (Percentage of chiral compound C content) In the TCDDM composition (A1) of the present invention, the lower limit of the content of chiral compound C is not particularly limited, but it is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 18% by mass or more, even more preferably 20% by mass or more, even more preferably 22% by mass or more, and even more preferably 25% by mass or more, based on 100% by mass of the total mass of the TCDDM composition (A1). Furthermore, the upper limit of the content of chiral compound C in the TCDDM composition (A1) is not particularly limited, but it 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, based on 100% by mass of the total mass of the TCDDM composition (A1). By setting the value above the lower limit, the formation of microcrystals of TCDDM in the TCDDM composition (A1) is suppressed, preventing an increase in viscosity during storage and resulting in good storage stability. Conversely, by setting the value below the upper limit, microcrystals are formed in the TCDDM composition (A1), ensuring appropriate fluidity, which is superior during handling operations such as compounding. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A1), the content of the chiral compound C is not particularly limited, but is preferably 10% to 45% by mass, more preferably 15% to 40% by mass, even more preferably 18% to 38% by mass, even more preferably 20% to 35% by mass, even more preferably 22% to 33% by mass, and even more preferably 25% to 30% by mass, based on 100% by mass of the total mass of TCDDM composition (A1).

[0249] (TCDDM content) In TCDDM composition (A1), there is no particular lower limit to the total amount of TCDDM contained, but from the viewpoint of handling the composition, it is preferable that it be 70% by mass or more, more preferably 80% by mass or more, even 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, the upper limit of the total amount of TCDDM contained in TCDDM composition (A1) is not particularly limited, and a higher percentage is preferable, and may 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 include, for example, compounds having an aldehyde group that are reaction intermediates during TCDDM synthesis, compounds having a carbonyl group derived from the aldehyde group-containing compound, C12 diols that are introduced during the manufacturing process, and known additives that may be added as needed. In the TCDDM composition (A1) of the present invention, the content of compounds other than TCDDM is not particularly limited as long as it does not impair the effects of the present invention, and can usually be 0.01% by mass or more and 2% by mass or less based on 100% by mass of the total mass of the TCDDM composition (A1). It is also possible to have a composition that does not contain any compounds other than TCDDM (0% by mass).

[0251] (Total content of chiral compounds A-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 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, based on 100% by mass of the total mass of TCDDM composition (A1). On the other hand, the upper limit of the total content is not particularly limited, and a higher value is preferable; it may be 100% by mass relative to the total mass of the TCDDM composition (A1).

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

[0253] (Backscattering intensity T1 of TCDDM composition (A2)) The TCDDM composition (A2) was measured at a temperature of 25°C using a dynamic light scattering method, and its 173° backscatter intensity T1 was equal to that of the standard sample (D 50When the backscattering intensity of a 0.002 volume% aqueous suspension of latex with a wavelength of 300 nm is T2, it is preferable that T2 ÷ 8.0 ≤ T1 ≤ T2 × 5.0 is satisfied. The above configuration yields a TCDDM composition (A2) that exhibits excellent storage stability and fluidity. By setting the lower limit of the backscattering intensity T1 to T2 ÷ 8.0 or higher, microcrystals are formed in the TCDDM composition (A1), resulting in moderate fluidity, making it less prone to stringing and excellent handling during compounding operations. On the other hand, by setting the upper limit of the backscattering intensity T1 to T2 × 5.0 or lower, the amount of TCDDM microcrystals in the TCDDM composition (A2) is reduced or the increase in TCDDM microcrystals is suppressed, suppressing the increase in viscosity during processing, resulting in good storage stability and handling during compounding operations.

[0254] The method for setting the backscatter intensity T1 within the above range is not particularly limited, but can be achieved, for example, by heating part or all of the TCCM composition (A1), which is stored in a container and at a temperature below 45°C, to 45°C or higher and less than 120°C. More preferably, it can be achieved by performing steps (2) to (4) of Figure 5 described above.

[0255] In the TCDDM composition (A2), the lower limit of the backscattering intensity T1 is preferably T2÷8.0 or higher, more preferably T2÷4.0 or higher, even more preferably T2÷3.5 or lower, even more preferably T2÷3.0 or higher, even more preferably T2÷2.5 or higher, and even more preferably T2÷2.0 or higher. Furthermore, in the TCDDM composition of the embodiment, the upper limit of the backscattering intensity T1 is preferably T2×5.0 or lower, more preferably T2×2.0 or lower, even more preferably T2×1.5 or lower, even more preferably T2 or lower, even more preferably T2÷1.3 or lower, and even more preferably T2÷1.5 or lower. By setting the viscosity above the lower limit, the TCDDM composition (A2) has appropriate fluidity, making it less prone to stringing and easier to handle during compounding operations. Furthermore, by setting the viscosity below the upper limit, the viscosity does not increase easily, resulting in good storage stability and ease of handling during compounding operations. The above upper and lower limits can be combined in any way. For example, in the TCDDM composition (A2), the backscattering intensity T1 is preferably T2÷8.0≦T1≦T2×5.0, more preferably T2÷4.0≦T1≦T2×2.0, even more preferably T2÷3.5≦T1≦T2×1.5, even more preferably T2÷3.0≦T1≦T2, even more preferably T2÷2.5≦T1≦T2÷1.3, and even more preferably T2÷2.0≦T1≦T2÷1.5.

[0256] In Example 3-1 (T2÷1) described later, the experiment was conducted under conditions that fall outside the preferred range of backscatter intensity T1. However, in the present invention, the effects of the present invention can be obtained at the preferred range of backscatter intensity T1.

[0257] In a more specific embodiment of the TCDDM composition (A2) of the present invention, for example, the lower limit of the backscatter intensity T1 is preferably 500 or more, more preferably 800 or more, even more preferably 1100 or more, even more preferably 1500 or more, and even more preferably 2000 or more. Also, in the TCDDM composition (A2), the upper limit of the backscatter intensity T1 is preferably 10000 or less, more preferably 8000 or less, even more preferably 7000 or less, even more preferably 6000 or less, and even more preferably 5000. By setting the viscosity above the lower limit, the TCDDM composition (A2) has appropriate fluidity, making it less prone to stringing and easier to handle during compounding operations. Conversely, by setting the viscosity below the upper limit, the viscosity of the TCDDM composition (A2) does not increase easily, resulting in improved storage stability and ease of handling during compounding operations. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A2), the backscatter intensity T1 is preferably 500 ≤ T1 ≤ 10000, more preferably 800 ≤ T1 ≤ 8000, even more preferably 1100 ≤ T1 ≤ 7000, even more preferably 150 ≤ T1 ≤ 6000, and even more preferably 2000 ≤ T1 ≤ 5000.

[0258] The TCDDM composition (A2) in the present invention may contain, in addition to chiral compound A, chiral compound B represented by the following formula (B) and chiral compound C represented by the following formula (C). In other words, the more chiral compound A is present, the more microcrystals are formed in the TCDDM composition (A2), and the more fluid it tends to be, making it easier to handle during compounding and other operations. The higher the amount of chiral compound B, the lower the relative proportion of chiral compound A becomes, which tends to reduce the amount of TCDDM microcrystals in the TCDDM composition (A1) or suppress the increase in TCDDM microcrystals, making it less likely for viscosity to increase during storage and resulting in good storage stability. When there is a high amount of chiral compound C, the proportion of chiral compound A becomes relatively low, which reduces the amount of TCDDM microcrystals in the TCDDM composition (A1) or suppresses the increase in TCDDM microcrystals. This tends to reduce viscosity increase during storage and improve storage stability.

[0259] [ka]

[0260] [ka]

[0261] Furthermore, chiral compound A, chiral compound B, and chiral compound C in TCDDM composition (A2) can be treated as synonymous with chiral compound A, chiral compound B, and chiral compound B in TCDDM composition (A1), respectively.

[0262] (Percentage of chiral compound A content) In the TCDDM composition (A2) of the present invention, the lower limit of the content of chiral compound A is not particularly limited, but it 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, especially more preferably 35% by mass or more, and even more especially preferably 36% by mass or more, based on 100% by mass of the total mass of the TCDDM composition (A2). Furthermore, while there is no particular upper limit to the content of chiral compound A, it 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, even more preferably 39% by mass or less, and even more preferably 38.5% by mass or less. By setting the value above the lower limit, microcrystals are formed in the TCDDM composition (A2), ensuring appropriate fluidity and providing excellent handling during compounding operations. Conversely, by setting the value below the upper limit, the formation of microcrystals of TCDDM in the TCDDM composition (A2) is suppressed, preventing an increase in viscosity during storage and resulting in good storage stability. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A2), the content of the chiral compound A is not particularly limited, but is preferably 25% to 54% by mass, more preferably 28% to 50% by mass, even more preferably 30% to 45% by mass, even more preferably 32% to 43% by mass, even more preferably 33% to 41% by mass, even more preferably 34% to 40% by mass, even more preferably 35% to 39% by mass, and even more preferably 36% to 38.5% by mass.

[0263] (Percentage of chiral compound B content) In the TCDDM composition (A2) of the present invention, the lower limit of the content of chiral compound B is not particularly limited, but it 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, based on 100% by mass of the total mass of the TCDDM composition (A2). Furthermore, the upper limit of the content of chiral compound B in TCDDM composition (A2) is not particularly limited, but it 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 in that order, it is preferable to have 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. By setting the value above the lower limit, the formation of microcrystals of TCDDM in the TCDDM composition (A2) is suppressed, the increase in viscosity during storage is suppressed, and storage stability is improved. Furthermore, by setting the value below the upper limit, microcrystals are formed in the TCDDM composition (A2), ensuring appropriate fluidity, thus improving handling during compounding and other operations. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A2), the content of the chiral compound B is not particularly limited, but is preferably 1.6% by mass or more and 4.8% by mass or less, more preferably 1.8% by mass or more and 4.6% by mass or less, even more preferably 2.0% by mass or more and 4.4% by mass or less, even more preferably 2.1% by mass or more and 4.3% by mass or less, even more preferably 2.2% by mass or more and 4.2% by mass or less, and even more preferably 2.3% by mass or more and 4.0% by mass or less.

[0264] (Percentage of chiral compound C content) In the TCDDM composition (A2) of the present invention, the lower limit of the content of chiral compound C is not particularly limited, but it is preferably 10% by mass or more, more preferably 15% by mass or more, even more preferably 18% by mass or more, even more preferably 20% by mass or more, even more preferably 22% by mass or more, and even more preferably 25% by mass or more, based on 100% by mass of the total mass of the TCDDM composition (A2). Furthermore, the upper limit of the content of chiral compound C in the TCDDM composition (A2) is not particularly limited, but it 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, based on 100% by mass of the total mass of the TCDDM composition (A2). By setting the value above the lower limit, the formation of microcrystals of TCDDM in the TCDDM composition (A1) is suppressed, preventing an increase in viscosity during storage and resulting in good storage stability. Conversely, by setting the value below the upper limit, microcrystals are formed in the TCDDM composition (A1), ensuring appropriate fluidity, which is superior during handling operations such as compounding. The above upper and lower limits can be combined arbitrarily. For example, in TCDDM composition (A1), the content of the chiral compound B is not particularly limited, but is preferably 10% to 45% by mass, more preferably 15% to 40% by mass, even more preferably 18% to 38% by mass, even more preferably 20% to 35% by mass, even more preferably 22% to 33% by mass, and even more preferably 25% to 30% by mass, based on 100% by mass of the total mass of TCDDM composition (A2).

[0265] (TCDDM content) In the TCDDM composition (A2), there is no particular lower limit to the TCDDM content, but from the viewpoint of handling the composition, it is preferable that it be 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 the TCDDM composition (A2). On the other hand, the upper limit of the total content is not particularly limited, and a higher value is preferable; it may be 100% by mass relative to the total mass of the TCDDM composition (A2).

[0266] (Total content of chiral compounds A-C) In the 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 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, based on 100% by mass of the total mass of the 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, based on 100% by mass of the total mass of the TCDDM composition (A2).

[0267] [Organic materials] The organic material obtained by the method for producing organic materials of the present invention is not particularly limited as long as it is an organic material obtained from TCDDM composition (A2), and can be used in the production of 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. Examples of polyester resins, epoxy resins, acrylate resins, polycarbonate resins, polyurethane resins, and ultraviolet-curable compositions are those described in the "Second Embodiment" above. [Examples]

[0268] The present invention will be described in more detail below with reference to examples. The materials, amounts used, proportions, processing content, and processing procedures shown in the following examples can be modified as appropriate, as long as they do not depart from the spirit of the present invention. Therefore, the scope of the present invention is not limited to the specific examples shown below. When the measuring instruments and the like used in the examples are difficult to obtain due to obsolescence or the like, measurements can be made using other instruments having equivalent performance.

[0269] [Raw materials] The compounds used in the examples and comparative examples are as follows. · DCPD: Dicyclopentadiene (manufactured by the company itself) · Rh(acac)(CO)2: Rhodium acetylacetonate dicarbonyl (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 Corporation) · Ruthenium-supported carbon (dry basis Ru content 5% by mass, water content 56% by mass) (trade name: Ru / C, manufactured by N.E. Chemcat Corporation) · Nickel-chromium-supported diatomaceous earth catalyst (nickel-supported diatomaceous earth with a nickel loading of 12% and a chromium loading of 2% manufactured according to the description of Example 1 of JP-A-2005-279587) · Powdered activated carbon (trade name: Characteristic White Egret, manufactured by Osaka Gas Chemical Co., Ltd.)

[0270] [Measurement method] The evaluations in the examples and comparative examples were carried out by the following methods.

[0271] <Identification of chiral compounds A to C contained in the TCDDM composition> The chiral compounds A to C contained in the TCDDM compositions obtained in the examples and comparative examples were calculated by the following procedure using nuclear magnetic resonance spectroscopy.

[0272] A sample of the TCDDM composition was dissolved in deuterated chloroform (CDCl3, containing 0.03 v / v% TMS), and the sample solution was transferred to an NMR sample tube with an outer diameter of 5 mm. Using a nuclear magnetic resonance spectrometer (trade name: AVANCE NEO 600 type NMR, manufactured by Bruker), the 1 1H-NMR 13C-NMR, DEPT, COSY, TOCSY, NOESY, 1 H- 13 C HSQC, 1 H- 13 C HMBC spectra were measured. 1 The measurement conditions for 1H-NMR were as follows: resonance frequency 600 MHz, flip angle 45°, data acquisition time 3 s, pulse repetition time 10 s, number of integrations 16, and measurement temperature 25 °C. The reference for chemical shift was set such that the signal of TMS was 0.00 ppm. 13 The measurement conditions for 13C-NMR were as follows: resonance frequency 151 MHz, flip angle 45°, data acquisition time 2 s, pulse repetition time 5 s, number of integrations 10000, and temperature 25 °C. The reference for chemical shift was set such that the signal of TMS was 0.00 ppm. The structure was identified from the signal correlations.

[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 chromatogram measuring device (trade 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 (temperature rising condition): Rising from 160 °C (holding time none) at a temperature rising rate of 5 °C / min to 300 °C (holding time 2 min) Inlet temperature: 200 °C Ion source temperature: 300 °C Sample amount: 0.3 μL Split ratio: 1:30 Detector: Flame ionization detector (FID)

[0274] The gas chromatograms of the TCDDM compositions obtained in Examples 1-1, 2-1, and 3-1, described below, are shown in Figures 1, 4, and 6, respectively.

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

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

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

[0278] The peak before peak 3, which is derived from the compound with the exo tricyclodecane skeleton, the peak between peak 2 and peak 3, and the peak after peak 1 were identified as 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 Figure 1, Xt was defined as the area between the baseline and the gas chromatogram curve in the range of elution times from 13.00 to 14.4 minutes. For the gas chromatogram shown in Figure 1, Xa was defined as the area between the baseline and the gas chromatogram curve in the elution time range of 13.85 to 14.05 minutes. In the gas chromatogram shown in Figure 1, Xb is defined as the area between the baseline and the gas chromatogram curve in the range of elution times from 13.65 to 13.85 minutes. In the gas chromatogram shown in Figure 1, Xc was defined as the area between the baseline and the gas chromatogram curve in the range of elution times from 13.65 to 13.85 minutes. For the gas chromatogram shown in Figure 4, Xt was defined as the area between the baseline and the gas chromatogram curve in the elution time range of 13.20 to 14.5 minutes. In the gas chromatogram shown in Figure 4, Xa was defined as the area between the baseline and the gas chromatogram curve in the elution time range of 14.05 to 14.30 minutes. Regarding the gas chromatogram shown in FIG. 4, the area in the range of elution times from 13.90 to 14.05 minutes between the baseline and the gas chromatogram curve was defined as Xb. Regarding the gas chromatogram shown in FIG. 4, the area in the range of elution times from 13.55 to 13.72 minutes between the baseline and the gas chromatogram curve was defined as Xc. Regarding the gas chromatogram shown in FIG. 6, the area in the range of elution times from 13.00 to 14.4 minutes between the baseline and the gas chromatogram curve was defined as Xt. Regarding the gas chromatogram shown in FIG. 6, the area in the range of elution times from 13.85 to 14.05 minutes between the baseline and the gas chromatogram curve was defined as Xa. Regarding the gas chromatogram shown in FIG. 6, the area in the range of elution times from 13.75 to 13.85 minutes between the baseline and the gas chromatogram curve was defined as Xb. Regarding the gas chromatogram shown in FIG. 6, the area in the range of elution times from 13.35 to 13.55 minutes between the baseline and the gas chromatogram curve was defined as Xc. Details of these measurement methods can be referred to the description in International Publication No. 2023 / 176641, and this content is incorporated herein.

[0280] <Mass spectrometry of the TCDDM composition> For the TCDDM compositions obtained in the examples and comparative examples, in order to confirm the formation of TCDDM, gas chromatography mass spectrometry was used to measure m / z and the fragmentation pattern by the following gas chromatography mass spectrometry. (Gas chromatography mass spectrometry conditions) Measuring device: Gas chromatogram measuring device (trade 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 a rate of 5°C / min to 300°C (holding time 2 minutes) Evaporation chamber temperature: 200℃ Ion source temperature: 250℃ MS interface temperature: 300℃ Injection volume: 0.5μL Split ratio: 1:30

[0281] <Measurement of backscatter intensity T1> For the TCDDM compositions obtained in the examples and comparative examples, the 173° backscatter intensity T1 was measured using dynamic light scattering measurement, at a temperature of 25°C, according to the following procedure. Also, as a standard sample, D 50 A 1 / vol% aqueous suspension of spherical latex with a particle size of 300 nm (product name: particle size standard particles 3300A, Thermo Fisher Scientific Co., Ltd.) was irradiated with ultrasound for 3 minutes in an ultrasonic bath, and then diluted to 0.002 vol% using pure water filtered through a 0.2 μm filter. The backscatter intensity T2 of this diluted solution was then measured.

[0282] A sample of the TCDDM composition, placed in a glass reagent bottle, was immersed in an oil bath set to 60°C. 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, 1 mL of the TCDDM composition was sampled and placed in a measurement cell. The measurement cell was then placed in a constant temperature bath attached to a dynamic light scattering analyzer, and while maintaining the measurement temperature of the TCDDM composition at 60°C, the backscatter intensity T1 was measured and the fluidity was visually observed under the following measurement conditions. The backscatter intensity T1 was measured for Examples 1-1 to 1-6 and Comparative Examples 1-1 to 1-3 immediately before immersion of the TCDDM composition sample in the oil bath (0 hours) and 96 hours, 175 hours, and 196 hours after immersion in the oil bath. Example 3 For steps -1 and 3-2, the tests were conducted immediately before immersing the TCDDM composition sample in the oil bath (0 hours) and 96 hours after immersion in the oil bath.

[0283] (Measurement conditions) Measurement device: Dynamic light scattering measurement device (product name: Zetasizer Nano ZS, manufactured by Malvern Panalytical) Detection method: 173° backscatter detection method (a scatter light detector is 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 their transparency and fluidity as indicators of storage stability. The evaluation method is as follows. (Transparency) The appearance of the TCDDM composition was visually observed after being stored at room temperature (25°C) for two months and judged according to the following three-stage criteria. The judgment was made by five experts and decided by majority vote. (Judgment criteria) • The exterior was transparent. • The exterior was slightly cloudy. • The exterior was cloudy white. (Flowability) A 10 mL sample was placed in a 20 mL glass bottle (25 mm inner diameter x 55 mm total length), the bottle was sealed, and heated to 60°C. Then, the time it took for the liquid level to reach the lid after the glass bottle was placed horizontally (hereinafter referred to as "flow time") was measured.

[0285] <Handling Test> For the TCDDM compositions obtained in Examples 1-1 to 1-6 and Comparative Examples 1-1 and 1-2, the handling properties, which are one of the indicators of storage stability, were evaluated by immersing the tip of a glass rod 10 mm into the TCDDM composition at room temperature (20°C) and pulling it up 10 cm, according to the following criteria. (Judgment criteria) 1: It did not exhibit towing properties. 2: It showed some pulling ability, but the thread broke immediately. 3: It exhibited a tendency to pull on the thread, and then broke after a while. 4: It exhibited string-pulling properties and remained intact without breaking.

[0286] <Condition> Example 2 - 1 The fluidity and transparency of the obtained TCDDM compositions (A1) and (A2) were evaluated as indicators of their storage condition. The evaluation method is as follows. (Fluidity) A 10 mL sample was placed in a 20 mL glass bottle (25 mm inner diameter x 55 mm total length), the bottle was sealed, and heated to 60°C. If the liquid level reached the lid within 5 minutes when the bottle was held horizontally, it was considered "fluid." The evaluation was conducted by five experts, and the final decision was made by majority vote. (Transparency) The appearance of the TCDDM composition was visually observed after being stored at room temperature (25°C) for two months and judged according to the following three-stage criteria. The judgment was made by five experts and decided by majority vote. (Judgment criteria) • The exterior was transparent. • The exterior was somewhat transparent. • The exterior was cloudy white.

[0287] <Determination of suitability for the manufacture of organic materials> The TCDDM compositions (A2) obtained in Examples 3-1, 3-2 and Comparative Examples 3-1, 3-2 were evaluated for their fluidity and transparency as indicators for determining their suitability for the manufacture of organic materials. The evaluation method is as follows. (Fluidity) A 10 mL sample was placed in a 20 mL glass bottle (25 mm inner diameter x 55 mm total length), the bottle was sealed, and heated to 60°C. If the liquid level reached the lid within 5 minutes when the bottle was held horizontally, it was considered "fluid." The evaluation was conducted by five experts, and the final decision was made by majority vote. (Transparency) The appearance of the TCDDM composition was visually observed after being stored at room temperature (25°C) for two months and judged according to the following two-stage criteria. The judgment was made by five experts and decided by majority vote. (Judgment criteria) • The exterior was transparent. • The exterior was cloudy white.

[0288] [Example 1-1] [Example of TCDDM synthesis] <Hydroformylation reaction> In a 500 mL autoclave reactor (up and down stirring type), under a nitrogen atmosphere, 214.5 mg of Rh(acac)(CO) and 0.8 mg of DBPO109 were weighed out as the starting compounds for the hydroformylation reaction catalyst. 89 g of methylcyclohexane was added as the organic solvent, and 113 g of DCPD was added as another starting compound. The reaction mixture in the reactor was then heated to 70°C while stirring from both ends. Next, a mixture of hydrogen and carbon monoxide (hydrogen:carbon monoxide = 1:1 molar ratio) was rapidly introduced into the reactor through a gas inlet valve to maintain a pressure of 3 MPaG. The reaction was allowed to proceed for 1 hour while maintaining this pressure. After that, the temperature of the reaction mixture was raised to 100°C, and the reaction was allowed to proceed for another 5 hours. During the reaction, the amount of mixed gas consumed in the reaction was continuously introduced into the reactor while maintaining a pressure of 3 MPaG. After the reaction was complete, the reaction mixture in the reactor was cooled to room temperature, and the remaining gas in the reactor was released to obtain 248 g of hydroformylation reaction product. The amount of DCPD, the starting compound, in the reaction mixture before the reaction and the amount of tricyclodecanedicarbaldehyde produced in the reaction product after the reaction were analyzed by gas chromatography to determine the yield of tricyclodecanedicarbaldehyde. The yield was 99%.

[0289] <Extraction operation> To 248 g of the obtained hydroformylation reaction product, 76 g of methanol and 51 g of water were added, and the mixture was stirred under a nitrogen atmosphere for 30 minutes. After standing for 30 minutes, the mixture was separated into two phases and extracted. 8.8 g of methylcyclohexane was added to the obtained lower phase (a1), and the mixture was stirred for 30 minutes. After standing for 30 minutes, the mixture was separated into two phases and extracted to obtain 288 g of the lower phase (a2). Analysis of the composition of the obtained lower phase (a2) by gas chromatography revealed that it consisted of 47% by mass of tricyclodecanedicarboxylase, 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> In a 200 mL autoclave reactor, 50 g of the lower phase (a2) obtained by the extraction procedure described above and 0.10 g of nickel-chromium supported diatomaceous earth catalyst were charged. The reaction mixture was then heated to 160 °C while stirring at 1200 rpm. Next, hydrogen gas was introduced through a gas inlet valve to maintain a pressure of 3 MPaG in the reactor. The reaction was then carried out for 3 hours while maintaining this pressure and the temperature of the reaction mixture. During the reaction, the amount of mixed gas consumed in the reaction was continuously introduced into the reactor to maintain a pressure of 3 MPaG. After the reaction was complete, the reaction mixture 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 5 μm pore size filter to obtain 44 g of reaction product. The amount of the starting compound tricyclodecanedicarbaldehyde in the reaction mixture before the reaction and the amount of TCDDM produced in the reaction product after the reaction were analyzed by gas chromatography. The yield of TCDDM was 98%.

[0291] <Distillation and purification> 1800 g of the reaction product after the hydrogenation-reduction reaction was charged into a batch-type distillation column (a 3 L four-necked flask) equivalent to five stages of ordered packing. At a minimum column pressure of 10 kPa and a maximum column bottom temperature of 100 °C, 890 g of light-boiling components, mainly solvents, were removed by distillation. Then, the column pressure was reduced to 0.3 kPa and the column bottom temperature to 120 °C, and distillation was carried out until 15 g of distillate was obtained from the top of the distillation column. Next, the distillation column equivalent to the five-stage ordered packing was replaced with a glass monodistillation column, and the TCDDM composition was distilled from the top of the column by simple distillation at a pressure of 0.3 kPa and a temperature of 165°C, and recovered in the order of initial distillation and then main distillation. The amount of TCDDM composition recovered as the main distillation was 745 g. The obtained TCDDM composition was heated at 60°C for one day. The evaluation results of the obtained TCDDM composition are shown in Table 1.

[0292] [Examples 1-2] In the hydrogenation-reduction reaction of Example 1-1, the 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 the reaction product. The yield of TCDDM in the reaction product was 99%. After distillation and purification under the same conditions as in Example 1-1, the amount of TCDDM composition recovered as the final distillate was 725 g. The TCDDM composition was obtained under the same conditions as in Example 1-1, except that the heating temperature of the distilled TCDDM composition was changed from 60°C to 50°C. The evaluation results of the obtained TCDDM composition are shown in Table 1.

[0293] [Examples 1-3] In Example 1-1, 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] [Examples 1-4] In the hydrogenation-reduction reaction of Example 1-1, a ruthenium-supported carbon catalyst was used instead of the nickel-chromium-supported diatomaceous earth catalyst, but the hydrogenation-reduction reaction was carried out under the same conditions as in Example 1-1 to obtain the reaction product. The yield of TCDDM in the reaction product was 98%. After distillation and purification under the same conditions as in Example 1-1, the amount of TCDDM composition recovered as the final distillate was 720 g. The evaluation results of the obtained TCDDM composition are shown in Table 1.

[0295] [Examples 1-5] In Example 1-1, 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] [Examples 1-6] In the distillation purification of Example 1-1, instead of a batch-type distillation column equivalent to 5 stages of ordered packing, a distillation column equivalent to 20 stages of ordered packing (a 3L four-necked flask) was used. After removing the light-boiling components, mainly solvents, from 1800g of the reaction product after the hydrogenation-reduction reaction, distillation was carried out at a column pressure of 0.6kPa and a column bottom temperature of 185°C until 119g of distillate was obtained from the top of the distillation column. Except as described above, the TCDDM composition was obtained under the same conditions as in Example 1-1. The amount of TCDDM composition recovered as the main distillate by distillation purification was 601 g. The evaluation results of the obtained TCDDM composition are shown in Table 1.

[0297] [Comparative Example 1-1] In Example 1-1, the 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] [Comparative Example 1-2] In Example 1-1, 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] [Comparative Examples 1-3] In Example 1-1, a TCDDM composition was obtained under the same conditions as in Example 1-1, except that the heating conditions for 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 using the method described above, and the m / z and fragment patterns were measured. It was confirmed that in all cases, peaks 1 to 3 showed m / z and fragment patterns corresponding to TCDDM. The following are some representative fragments that have been observed. MS(EI):178([M-18]+), 165, 147, 119, 105, 91, 81, 67

[0301] [Table 1] [Table 2]

[0302] In Tables 1 and 2 above, the unit of each TCDDM quantity is mass %.

[0303] In evaluating storage stability, a lower analytical value of dynamic light scattering intensity indicates lower crystallinity and higher fluidity of the TCDDM composition, i.e., good storage stability of the TCDDM composition. As is clear from the above results, the TCDDM composition of the present invention exhibited excellent storage stability and moderate fluidity (Examples 1-1 to 1-6). In contrast, when the backscattering intensity T1 of the TCDDM composition was less than T2÷8.0 (Comparative Example 1-1), the fluidity was poor. Also, when the backscattering intensity T1 of the TCDDM composition exceeded T2×2 (Comparative Example 1-2), the storage stability was poor. Furthermore, in Comparative Example 1-3, where the heating conditions for the TCDDM composition after distillation were changed to 70°C for 1 hour, the backscattering intensity T1 of the TCDDM composition was less than T2÷8.0.

[0304] [Example 2-1] [Example of TCDDM synthesis] <Hydroformylation reaction> In a 500 mL autoclave reactor (up and down stirring type), under a nitrogen atmosphere, 213.2 mg of Rh(acac)(CO) and 911.6 mg of DBPO were weighed out as the starting compounds for the hydroformylation reaction catalyst. 72 g of methylcyclohexane was added as the organic solvent, and 94 g of DCPD was added as another starting compound. The reaction mixture in the reactor was then heated to 70°C while stirring from both ends. Next, a mixture of hydrogen and carbon monoxide (hydrogen:carbon monoxide = 1:1 molar ratio) was rapidly introduced into the reactor through a gas inlet valve to maintain a pressure of 3 MPaG. The reaction was allowed to proceed for 1 hour while maintaining this pressure. After that, the reaction mixture was heated to 100°C and allowed to proceed for another 5 hours. During the reaction, the amount of mixed gas consumed in the reaction was continuously introduced into the reactor while maintaining a pressure of 3 MPaG. After the reaction was complete, the reaction mixture in the reactor was cooled to room temperature, and the remaining gas in the reactor was released to obtain 185 g of hydroformylation reaction product. The amount of DCPD, the starting compound, in the reaction mixture before the reaction and the amount of tricyclodecanedicarbaldehyde produced in the reaction product after the reaction were analyzed by gas chromatography to determine the yield of tricyclodecanedicarbaldehyde. The yield was 99%.

[0305] <Extraction operation> To 185 g of the obtained hydroformylation reaction product, 55 g of methanol and 37 g of water were added, and the mixture was stirred under a nitrogen atmosphere for 30 minutes. After standing for 30 minutes, the mixture was separated into two phases and extracted. 6.7 g of methylcyclohexane was added to the obtained lower phase (a1), and the mixture was stirred for 30 minutes. After standing for 30 minutes, the mixture was separated into two phases and extracted to obtain 219 g of the lower phase (a2). Analysis of the composition of the obtained lower phase (a2) by gas chromatography revealed that it consisted of 47% by mass of tricyclodecanedicarboxylase, 27% by mass of methanol, 14% by mass of water, 7% by mass of methylcyclohexane, and 5% by mass of other components.

[0306] <Hydrogenation-reduction reaction> In a 200 mL autoclave reactor, 50 g of the lower phase (a2) obtained by the extraction procedure described above and 0.03 g of ruthenium-supported carbon catalyst were charged. The reaction mixture was then heated to 160 °C while stirring at 1200 rpm. Next, hydrogen gas was introduced through a gas inlet valve to maintain a pressure of 3 MPaG in the reactor. The reaction was then carried out for 3 hours while maintaining this pressure and the temperature of the reaction mixture. During the reaction, the amount of mixed gas consumed in the reaction was continuously introduced into the reactor to maintain a pressure of 3 MPaG. After the reaction was complete, the reaction mixture 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 5 μm pore size filter to obtain 44 g of reaction product. The amount of the starting compound tricyclodecanedicarbaldehyde in the reaction mixture before the reaction and the amount of TCDDM produced in the reaction product after the reaction were analyzed by gas chromatography. The yield of TCDDM was 98%.

[0307] <Distillation and purification> 1800 g of the reaction product after the hydrogenation-reduction reaction was charged into a batch-type distillation column (a 3 L four-necked flask) equivalent to 20 stages of ordered packing. At a minimum column pressure of 1 kPa and a maximum column bottom temperature of 100 °C, 890 g of light-boiling components, mainly solvents, were removed by distillation. Then, the column pressure was reduced to 0.6 kPa and the column bottom temperature to 185 °C, and distillation was carried out until 120 g of distillate was obtained from the top of the distillation column. Next, the distillation column equivalent to the five-stage ordered packing column was replaced with a glass single-stage distillation column, and the TCDDM composition (A0) was distilled from the top of the column by simple distillation at a pressure of 0.3 kPa and a temperature of 165°C, and recovered in the order of initial distillation and then main distillation. The amount of TCDDM composition (A0) recovered as the main distillation was 600 g. The obtained 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 a container. In this experimental example, the glass reagent bottle corresponds to container 3 shown in Figures 2 and 3. A sample of TCDDM composition (A1) in a glass reagent bottle was immersed in an oil bath set to 60°C for 96 hours. The sample was then heated while stirring until the measurement temperature of the TCDDM composition reached 60°C, which was then prepared as 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 between 45°C and 120°C before being fed into the processing machine (X). Next, stirring of the sample was stopped, 1 mL of TCDDM composition (A2) was sampled and placed in a measurement cell, and the measurement cell was placed in a constant temperature bath attached to the dynamic light scattering measurement device. While maintaining the measurement temperature of the TCDDM composition at 60°C, the backscatter intensity T1 was measured and the storage condition was visually observed.

[0308] Table 3 shows the results of mass spectrometry of TCDDM compositions (A1) and (A2), as well as the storage conditions, backscatter intensity T1, and a comparison with the backscatter intensity T2 of a standard sample.

[0311] [Table 3]

[0312] The TCDDM composition of Example 2-1 exhibited excellent storage properties and a low backscattering intensity T1. In other words, it was found to contain few microcrystals that cause turbidity. 。 In other words, by storing the TCDDM composition obtained by distillation purification in a container at a temperature not below 45°C, turbidity was suppressed, and furthermore, a decrease in fluidity was also suppressed.

[0313] [Example 3-1] [Example of TCDDM synthesis] <Hydroformylation reaction> In a 500 mL autoclave reactor (up and down stirring type), under a nitrogen atmosphere, 214.0 mg of Rh(acac)(CO) and 1121.8 mg of DBPO were weighed out as the starting compounds for the hydroformylation reaction catalyst. 88 g of methylcyclohexane was added as the organic solvent, and 113 g of DCPD was added as another starting compound. The reaction mixture in the reactor was then heated to 70°C while stirring from both ends. Next, a mixture of hydrogen and carbon monoxide (hydrogen:carbon monoxide = 1:1 molar ratio) was rapidly introduced into the reactor through a gas inlet valve to maintain a pressure of 3 MPaG. The reaction was allowed to proceed for 1 hour while maintaining this pressure. After that, the reaction mixture was heated to 100°C and allowed to proceed for another 5 hours. During the reaction, the amount of mixed gas consumed in the reaction was continuously introduced into the reactor while maintaining a pressure of 3 MPaG. After the reaction was complete, the reaction mixture in the reactor was cooled to room temperature, and the remaining gas in the reactor was released to obtain 248 g of hydroformylation reaction product. The amount of DCPD, the starting compound, in the reaction mixture before the reaction and the amount of tricyclodecanedicarbaldehyde produced in the reaction product after the reaction were analyzed by gas chromatography to determine the yield of tricyclodecanedicarbaldehyde. The yield was 99%.

[0314] <Extraction operation> To 247 g of the obtained hydroformylation reaction product, 75 g of methanol and 49 g of water were added, and the mixture was stirred under a nitrogen atmosphere for 30 minutes. After standing for 30 minutes, the mixture was separated into two phases and extracted. 9.2 g of methylcyclohexane was added to the obtained lower phase (a1), and the mixture was stirred for 30 minutes. After standing for 30 minutes, the mixture was separated into two phases and extracted to obtain 288 g of the lower phase (a2). Analysis of the composition of the obtained lower phase (a2) by gas chromatography revealed that it consisted of 47% by mass of tricyclodecanedicarboxylase, 27% by mass of methanol, 14% by mass of water, 7% by mass of methylcyclohexane, and 5% by mass of other components.

[0315] <Hydrogenation-reduction reaction> In a 200 mL autoclave reactor, 50 g of the lower phase (a2) obtained by the extraction procedure described above and 0.03 g of ruthenium-supported carbon catalyst were charged. The reaction mixture was then heated to 160 °C while stirring at 1200 rpm. Next, hydrogen gas was introduced through a gas inlet valve to maintain a pressure of 3 MPaG in the reactor. The reaction was then carried out for 3 hours while maintaining this pressure and the temperature of the reaction mixture. During the reaction, the amount of mixed gas consumed in the reaction was continuously introduced into the reactor to maintain a pressure of 3 MPaG. After the reaction was complete, the reaction mixture 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 5 μm pore filter to obtain 44 g of reaction product. The amount of the starting compound tricyclodecanedicarbaldehyde in the reaction mixture before the reaction and the amount of TCDDM produced in the reaction product after the reaction were analyzed by gas chromatography. The yield of TCDDM was 98%.

[0316] <Distillation and purification> 1800 g of the reaction product after the hydrogenation-reduction reaction was charged into a batch-type distillation column (a 3 L four-necked flask) equivalent to five stages of ordered packing. At a minimum column pressure of 10 kPa and a maximum column bottom temperature of 100 °C, 890 g of light-boiling components, mainly solvents, were removed by distillation. Then, the column pressure was reduced to 0.3 kPa and the column bottom temperature to 120 °C, and distillation was carried out until 15 g of distillate was obtained from the top of the distillation column. Next, the distillation column equivalent to the five-stage ordered packing column was replaced with a glass single-distillation column, and the TCDDM composition (A0) was distilled from the top of the column by simple distillation at a pressure of 0.3 kPa and a temperature of 165°C, and recovered in the order of initial distillation and then main distillation. The amount of TCDDM composition (A0) recovered as the main distillation was 745 g. The obtained TCDDM composition (A0) was placed in a glass reagent bottle and kept at a temperature below 45°C, and TCDDM composition (A1) was obtained, which was stored in a container and kept at a temperature below 45°C. Table 4 shows the backscatter intensity T1 of the obtained TCDDM composition (A1), a comparison with the backscatter intensity T2 of the standard sample, and the results of mass spectrometry of the TCDDM composition.

[0317] Table 4 also shows the backscatter intensity T1 of TCDDM composition (A2) after heating the obtained TCDDM composition (A1) in a glass bottle for 96 hours (4 days) at the temperatures shown in Table 4, a comparison with the backscatter intensity T2 of the standard sample, and the results of mass spectrometry of the TCDDM composition.

[0318] [Example 3-2] In the hydrogenation-reduction reaction of Example 3-1, 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 reaction solution temperature was changed from 160°C to 180°C. The hydrogenation-reduction reaction was carried out under the same conditions as in Example 3-1 to obtain the reaction product. The yield of TCDDM in the reaction product was 99%. Next, the reaction product obtained was purified by distillation under the same conditions as in Example 3-1, except for the conditions mentioned above, to obtain TCDDM composition (A1). The obtained TCDDM composition (A1) was heated under the same conditions as in Example 3-1 to obtain 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, instead of a batch-type distillation column equivalent to 5 stages of ordered packing, a distillation column equivalent to 20 stages of ordered packing (a 3L four-necked flask) was used. After removing the light-boiling components, mainly solvents, from 1800g of the reaction product after the hydrogenation-reduction reaction, distillation was carried out at a column pressure of 0.6kPa and a column bottom temperature of 185°C until 119g of distillate was obtained from the top of the distillation column. Except as described above, the TCDDM composition was obtained under the same conditions as in Example 3-1. The amount of TCDDM composition recovered as the main distillate by distillation purification was 601 g. The obtained TCDDM composition (A1) was left to stand at room temperature (25°C) for 96 hours (4 days) without heating and evaluated as TCDDM composition (A2). The evaluation results are shown in Table 4.

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

[0321] [Table 4]

[0322] As is clear from the above results, the method for producing organic materials of the present invention successfully produced organic materials (Examples 3-1 to 3-2). In contrast, when heating was not performed (Comparative Example 3-1), the viscosity of the raw material was high, and manufacturing was unsuccessful. 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 the manufacturing process could not be successfully completed.

[0323] Although the present invention has been described in detail using specific embodiments, it will be apparent to those skilled in the art that various modifications are possible without departing from the intent and scope of the invention. [Explanation of symbols]

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

Claims

1. A tricyclodecanedimethanol composition comprising tricyclodecanedimethanol, The 173° backscatter intensity T was measured at a temperature of 25°C using the dynamic light scattering method for the aforementioned tricyclodecanedimethanol composition. １ However, the backscattering intensity of the standard sample is T ２ In that case, T ２ ÷6.0 ≤ T １ ≦T ２ Satisfying ×5.0, The aforementioned standard sample is a particle size standard particle 3300A (D) manufactured by Thermo Fisher Scientific Corporation. ５０ This is an aqueous suspension of latex (with a wavelength of 300 nm) that has been irradiated with ultrasound for 3 minutes in an ultrasonic bath, and then diluted to 0.002 volume percent with pure water filtered through a 0.2 μm filter. Tricyclodecanedimethanol composition.

2. The 173° backward scattering intensity T １ is T ２ ÷5.0 ≤ T １ ≤ T ２ ×2.0, and the tricyclodecane dimethanol composition according to claim 1

3. The tricyclodecanedimethanol contains a chiral compound in which one of its enantiomers is represented by formula (A), The tricyclodecanedimethanol composition according to claim 1, wherein the content of the chiral compound represented by formula (A) is 25 to 34.5% by mass with respect to 100% by mass of the total mass of the tricyclodecanedimethanol. 【Chemistry 1】

4. The tricyclodecanedimethanol contains a chiral compound in which one of its enantiomers is represented by formula (A), The tricyclodecanedimethanol composition according to claim 1, wherein the content of the chiral compound represented by formula (A) is 33 to 38% by mass with respect to 100% by mass of the total mass of the tricyclodecanedimethanol. 【Chemistry 2】

5. The tricyclodecanedimethanol contains a chiral compound in which one of its enantiomers is represented by formula (B). The tricyclodecanedimethanol composition according to claim 1, wherein the content of the chiral compound represented by formula (B) is 1.6 to 4.8% by mass with respect to 100% by mass of the total mass of the tricyclodecanedimethanol. 【Transformation 3】

6. The tricyclodecanedimethanol comprises a chiral compound in which one enantiomer is represented by formula (A), and a chiral compound in which the 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 tricyclodecanedimethanol. 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 tricyclodecanedimethanol. The tricyclodecanedimethanol composition according to claim 1. 【Chemistry 4】 【Transformation 5】

7. The tricyclodecanedimethanol composition according to claim 1, wherein the content of the tricyclodecanedimethanol is 70% by mass or more based on 100% by mass of the total mass of the tricyclodecanedimethanol composition.

8. The amount of fragrance carrier contained in the tricyclodecanedimethanol composition is 1% by mass or less relative to the total mass of the tricyclodecanedimethanol composition. The tricyclodecanedimethanol composition according to claim 1.

9. A UV-curable composition derived from the tricyclodecanedimethanol 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 tricyclodecanedimethanol composition according to any one of claims 1 to 8.

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

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