Novel compound and method for using same, mixture, plasticizer composition, resin composition, resin molded article, and laminate

Abstract

A compound represented by formula (1) [in formula (1), Ax represents an organic group having 3-20 carbon atoms, Y1, Y2, Y3, and Y4 each independently represent a single bond, -C (=O)- and the like, SP1, SP2, SP3, and SP4 each independently represent a predetermined organic group, and a, b, c, and d each independently represent an integer of 0-30, Ra, Rb, Rc and Rd are each independently represent a linear aliphatic hydrocarbon group having 12-18 inclusive carbon atoms which may have a substituent, the linear aliphatic hydrocarbon group may contain 1-5 inclusive double bonds, at least one linear aliphatic hydrocarbon group of Ra, Rb, Rc and Rd contains one or more epoxy groups, and x and y each independently represent 0 or 1].

Description

Novel compound and method of use thereof, mixture, plasticizer composition, resin composition, resin molded body, and laminate

[0001] The present invention relates to a novel compound, a method for using the compound, a mixture, a plasticizer composition, a resin composition, a resin molded article, and a laminate.

[0002] In recent years, resins such as vinyl chloride resins have been used in a variety of applications due to their generally excellent properties such as cold resistance, heat resistance, oil resistance, etc. Specifically, for example, automobile interior parts such as automobile instrument panels and door trims are formed using automobile interior materials such as skins made of resin molded products using vinyl chloride resins or laminates made by lining a skin made of such resin molded products with a foam such as polyurethane foam.

[0003] It has been proposed that resin molded articles constituting the skin of automobile interior parts such as automobile instrument panels be produced by molding a resin composition containing a resin such as vinyl chloride resin, a plasticizer, and additives using a powder molding method such as powder slush molding (see, for example, Patent Document 1). Specifically, Patent Document 1 discloses a vinyl chloride resin molded article produced by powder slush molding a vinyl chloride resin composition containing vinyl chloride resin particles, a plasticizer such as a polyester-based plasticizer, and additives such as a hydrotalcite-based stabilizer, a zeolite-based stabilizer, and β-diketones.

[0004] Here, compounds obtained from cardanol have been used in various applications due to their excellent properties such as water resistance, chemical resistance, and heat resistance. For example, Patent Document 2 describes a diester compound obtained by esterifying 3-pentadecylphenol with dicarboxylic acid chloride as a compound that can be used as a thermochromic regulator for thermochromic ink.

[0005] Japanese Patent Application Laid-Open No. 2012-197394 Japanese Patent Application Laid-Open No. 2020-517691

[0006] An object of the present invention is to provide novel compounds obtained by epoxidizing an ester compound.

[0007] The present inventors have newly discovered the above novel compound and have completed the present invention. Furthermore, the present inventors have also completed a method for using the novel compound, a mixture containing the novel compound, a plasticizer composition, and a resin composition, as well as a resin molded article and a laminate formed using the same.

[0008] That is, according to the present invention, there are provided compounds of the following [1] to [4], mixtures of the following [5] to [9], methods of use of the following

[10] to

[11] , plasticizer compositions of the following

[12] to

[17] , resin compositions of the following

[18] to

[23] , resin molded articles of the following

[24] to

[25] , and laminates of the following

[26] to

[27] .

[0009] [1] A compound represented by the following formula (1): ...(1) [In formula (1), Ax represents an organic group having 3 to 20 carbon atoms, and Y １ , Y ４ are each independently a single bond, —C(═O)—, or —C(═O)—NR 1 - or -C(=O)-O-, R １ represents a hydrogen atom, a methyl group, or an ethyl group; Y ２ , Y ３ are each independently a single bond, —C(═O)—, or —NR ２ represents —C(═O)— or —O—C(═O)—, R ２ represents a hydrogen atom, a methyl group, or an ethyl group; Y １ , Y ４ , Y ２ , Y ３ may be independently different from each other or may be the same, and SP １ , SP ４ are each independently —CH ２ CH ２ O-, -CH ２ CH (CH ３ )O-,-CH(CH ３ ) CH ２ O-, -CH ２ CH (CH ２ CH ３ ) O—, or —CH(CH ２ CH ３ ) CH ２O-, SP ２ , SP ３ are each independently —OCH ２ CH ２ -, -OCH(CH ３ ) CH ２ -, -OCH ２ CH (CH ３ )-,-OCH(CH ２ CH ３ ) CH ２ - or -OCH ２ CH (CH ２ CH ３ )-; a, b, c, and d each independently represent an integer of 0 to 30; R ａ , R ｂ , R ｃ , R ｄ each independently represents a chain aliphatic hydrocarbon group having from 12 to 18 carbon atoms which may have a substituent, the chain aliphatic hydrocarbon group may contain from 1 to 5 double bonds, R ａ , R ｂ , R ｃ , R ｄ At least one of the chain aliphatic hydrocarbon groups contains one or more epoxy groups, and ａ , R ｂ , R ｃ , R ｄ may be independently different from each other or may be the same, x and y each independently represent 0 or 1, and when x is 0, the following formula (1-1): represents a hydrogen atom, and when y is 0, the structure represented by the following formula (1-2): represents a hydrogen atom, and * in formulas (1-1) and (1-2) represents the bonding position with Ax.

[0010] [2] In the compound of the above [1], the R ａ , R ｂ , R ｃ and R ｄeach independently represents a chain aliphatic hydrocarbon group having 12 to 18 carbon atoms which may have a substituent, and it is preferable that the number of epoxy groups contained in the chain aliphatic hydrocarbon group is 1 to 5.

[0011] [3] In addition, in the compound of [1] or [2], the Ax is (i) a chain aliphatic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent, (ii) a cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms which may have a substituent, (iii) an aromatic hydrocarbon ring group having 6 to 14 carbon atoms which may have a substituent, or (iv) an organic group having 3 to 20 carbon atoms in which at least one single bond contained in the chain aliphatic hydrocarbon group which may have a substituent is substituted with —O—, —C(═O)—, —O—C(═O)—, or —C(═O)—O— (provided that there are two or more consecutive —O— groups, there are two or more consecutive —C(═O)— groups, and there is no case where —O— or —C(═O)— is the Y １ , the Y ２ , the Y ３ , or the Y ４ and when it is located at the end bonding to (excluding).

[0012] [4] In any of the compounds [1] to [3] above, it is preferable that Ax is a group represented by any of the following formulas (2-1) to (2-35) which may have a substituent:

[0013] [5] A mixture containing any one of the compounds [1] to [4] above and a compound represented by the following formula (3): (3) [In formula (3), Bx represents an organic group having 3 to 20 carbon atoms, and Y １１ , Y ４１ are each independently a single bond, —C(═O)—, or —C(═O)—NR 1 - or -C(=O)-O-, R １ represents a hydrogen atom, a methyl group, or an ethyl group; Y ２１ , Y ３１ are each independently a single bond, —C(═O)—, or —NR ２ represents —C(═O)— or —O—C(═O)—, R２ represents a hydrogen atom, a methyl group, or an ethyl group; Y １１ , Y ４１ , Y ２１ , Y ３１ may be independently different from each other or may be the same, and SP １１ , SP ４１ are each independently —CH ２ CH ２ O-, -CH ２ CH (CH ３ )O-,-CH(CH ３ ) CH ２ O-, -CH ２ CH (CH ２ CH ３ ) O—, or —CH(CH ２ CH ３ ) CH ２ O-, SP ２１ , SP ３１ are each independently —OCH ２ CH ２ -, -OCH(CH ３ ) CH ２ -, -OCH ２ CH (CH ３ )-,-OCH(CH ２ CH ３ ) CH ２ - or -OCH ２ CH (CH ２ CH ３ )-; e, f, g, and h each independently represent an integer of 0 to 30; R ａ１ , R ｂ１ , R ｃ１ , R ｄ１ each independently represents a chain aliphatic hydrocarbon group having from 12 to 18 carbon atoms which may have a substituent, the chain aliphatic hydrocarbon group may contain from 1 to 5 double bonds, R ａ１ , R ｂ１ , R ｃ１ , R ｄ１ may be each independently different from each other or the same, p and q each independently represent 0 or 1, and when p is 0, a compound represented by the following formula (3-1): represents a hydrogen atom, and when q is 0, the structure represented by the following formula (3-2): represents a hydrogen atom, and in formulas (3-1) and (3-2), * represents the bonding position with Bx.

[0014] [6] Here, in the mixture of [5], the Bx is (i) a chain aliphatic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent, (ii) a cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms which may have a substituent, (iii) an aromatic hydrocarbon ring group having 6 to 14 carbon atoms which may have a substituent, or (iv) an organic group having 3 to 20 carbon atoms in which at least one single bond contained in the chain aliphatic hydrocarbon group which may have a substituent is substituted with —O—, —C(═O)—, —O—C(═O)—, or —C(═O)—O— (provided that there are two or more consecutive —O— groups, there are two or more consecutive —C(═O)— groups, and there is no case where —O— or —C(═O)— is the same as the Y １１ , the Y ２１ , the Y ３１ , or the Y ４１ and when it is located at the end bonding to (excluding).

[0015] [7] In the mixture of [5] or [6], it is preferable that Bx is a group represented by any one of the following formulas (2-1) to (2-35) which may have a substituent.

[0016] [8] In the mixture of any one of the above [5] to [7], it is preferable that the Ax and the Bx have the same structure.

[0017] [9] Any mixture of the above [5] to [8] may contain the above R ａ , R ｂ , R ｃ and R ｄ It is preferable that the compound contains at least two or more compounds represented by formula (1), each of which is independently different from the others.

[0018]

[10] A method of using any of the compounds according to the above [1] to [4] as a plasticizer. By using the compound of the present invention as a plasticizer, it is possible to improve the low-temperature tensile elongation and adhesion to polyurethane, more specifically to foamed polyurethane molded products, of a resin composition prepared using the compound or mixture of the present invention, while also improving the heat shrinkage resistance and meltability of the resin molded product.

[0019]

[11] A method in which the mixture of any one of the above [5] to [9] is used as a plasticizer.

[0020]

[12] A plasticizer composition comprising the compound according to any one of [1] to [4] above and a plasticizer.

[0021]

[13] A plasticizer composition comprising the mixture of any one of [5] to [9] above and a plasticizer.

[0022]

[14] The plasticizer composition according to the above

[12] or

[13] , wherein the plasticizer is a polyester-based plasticizer.

[0023]

[15] The plasticizer composition according to the above

[14] , wherein the plasticizer contains an adipic acid-based polyester.

[0024]

[16] The plasticizer composition according to any one of

[12] to

[14] above, wherein the content of the compound is 1 part by mass or more and 70 parts by mass or less per 100 parts by mass of the polyester-based plasticizer.

[0025]

[17] A resin composition comprising a resin and the plasticizer composition according to any one of

[12] to

[16] above.

[0026]

[18] The resin composition according to

[17] above, wherein the resin contains a halogen.

[0027]

[19] The resin composition according to

[17] or

[18] above, wherein the glass transition temperature of the resin is 50°C or higher and 100°C or lower.

[0028]

[20] The resin composition according to any one of

[17] to

[19] above, wherein the resin contains a vinyl chloride resin.

[0029]

[21] The resin composition according to any one of

[17] to

[20] above, wherein the content of the compound is 1 part by mass or more and 50 parts by mass or less per 100 parts by mass of the resin.

[0030]

[22] The resin composition according to any one of

[17] to

[21] above, which is used for powder molding.

[0031]

[23] The resin composition according to any one of

[17] to

[22] above, which is used in powder slush molding.

[0032]

[24] A resin molded product obtained by molding the resin composition according to any one of

[17] to

[23] above.

[0033]

[25] The resin molded article according to the above

[24] , which is for use as an automobile instrument panel skin.

[0034]

[26] A laminate comprising a foamed polyurethane molded product and the resin molded product of

[24] or

[25] above.

[0035]

[27] The laminate according to the above

[26] , which is for an automobile instrument panel.

[0036] According to the present invention, a novel compound obtained by epoxidizing an ester compound is provided.

[0037] "Cardolite NX-2026" (Cardolite Co., Ltd.) used in the synthesis example １ 1 shows a spectrum obtained by H-NMR measurement. １３ 1 shows a spectrum obtained by C-NMR measurement. 2 shows a spectrum obtained by infrared spectroscopy (total reflection measurement method) (hereinafter, sometimes abbreviated as "IR (ATR)") of "Cardolite NX-2026" (manufactured by Cardolite Co., Ltd.) used in Synthesis Examples. 3 shows a spectrum obtained by infrared spectroscopy (total reflection measurement method) (hereinafter, sometimes abbreviated as "IR (ATR)") of "Cardolite NX-7507" (manufactured by Cardolite Co., Ltd.) used in Synthesis Examples. １ 1 shows a spectrum obtained by H-NMR measurement. １３1 is a diagram showing a spectrum obtained by C-NMR measurement. 2 is a diagram showing a spectrum obtained by C-H COSY measurement of "Cardolite NX-7507" (manufactured by Cardolite Co., Ltd.) used in Synthesis Examples. 3 is a diagram showing a spectrum obtained by IR (ATR) measurement of "Cardolite NX-7507" (manufactured by Cardolite Co., Ltd.) used in Synthesis Examples. 4 is a diagram showing a spectrum obtained by IR (ATR) measurement of "Cardolite NX-7507" (manufactured by Cardolite Co., Ltd.) used in Synthesis Examples. １ 1 is a diagram showing a spectrum obtained by H-NMR measurement of diester mixture 1 obtained in Synthesis Example 1. １３ 1 shows a spectrum obtained by C-NMR measurement. 2 shows a spectrum obtained by IR (ATR) measurement of diester mixture 1 obtained in Synthesis Example 1. 3 shows a spectrum obtained by IR (ATR) measurement of diester mixture 2 obtained in Synthesis Example 2. １ 1 shows a spectrum obtained by H-NMR measurement. １３ 1 shows a spectrum obtained by C-NMR measurement. 2 shows a spectrum obtained by IR (ATR) measurement of diester mixture 2 obtained in Synthesis Example 2. 3 shows a spectrum obtained by IR (ATR) measurement of diester mixture 3 obtained in Synthesis Example 3. １ 1 shows a spectrum obtained by H-NMR measurement. １３ 1 shows a spectrum obtained by C-NMR measurement. 2 shows a spectrum obtained by IR (ATR) measurement of diester mixture 3 obtained in Synthesis Example 3. 3 shows a spectrum obtained by IR (ATR) measurement of diester mixture 4 obtained in Synthesis Example 4. １ 1 shows a spectrum obtained by H-NMR measurement. １３ 1 shows a spectrum obtained by C-NMR measurement. 2 shows a spectrum obtained by IR (ATR) measurement of diester mixture 4 obtained in Synthesis Example 4. 3 shows a spectrum obtained by IR (ATR) measurement of diester mixture 5 obtained in Synthesis Example 5. １ 1 shows a spectrum obtained by H-NMR measurement. １３1 shows a spectrum obtained by C-NMR measurement. 2 shows a spectrum obtained by IR (ATR) measurement of diester mixture 5 obtained in Synthesis Example 5. 3 shows a spectrum obtained by IR (ATR) measurement of diester mixture 6 obtained in Synthesis Example 6. １ 1 shows a spectrum obtained by H-NMR measurement. １３ 1 shows a spectrum obtained by C-NMR measurement. 2 shows a spectrum obtained by IR (ATR) measurement of diester mixture 6 obtained in Synthesis Example 6. 3 shows a spectrum obtained by IR (ATR) measurement of epoxidized diester mixture 1 obtained in Synthesis Example 10. １ 1 shows a spectrum obtained by H-NMR measurement of epoxidized diester mixture 1 obtained in Synthesis Example 10. １３ 1 shows a spectrum obtained by C-NMR measurement. 2 shows a spectrum obtained by IR (ATR) measurement of epoxidized diester mixture 1 obtained in Synthesis Example 10. 3 shows a spectrum obtained by IR (ATR) measurement of epoxidized diester mixture 2 obtained in Synthesis Example 11. １ 1 shows a spectrum obtained by H-NMR measurement of epoxidized diester mixture 2 obtained in Synthesis Example 11. １３ 1 shows a spectrum obtained by C-NMR measurement. 2 shows a spectrum obtained by IR (ATR) measurement of epoxidized diester mixture 2 obtained in Synthesis Example 11. 3 shows a spectrum obtained by IR (ATR) measurement of epoxidized diester mixture 3 obtained in Synthesis Example 12. １ 1 shows a spectrum obtained by H-NMR measurement of epoxidized diester mixture 3 obtained in Synthesis Example 12. １３ 1 shows a spectrum obtained by C-NMR measurement. 2 shows a spectrum obtained by IR (ATR) measurement of epoxidized diester mixture 3 obtained in Synthesis Example 12. 3 shows a spectrum obtained by IR (ATR) measurement of epoxidized diester mixture 4 obtained in Synthesis Example 13. １ 1 shows a spectrum obtained by H-NMR measurement of epoxidized diester mixture 4 obtained in Synthesis Example 13. １３1 shows a spectrum obtained by C-NMR measurement. 2 shows a spectrum obtained by IR (ATR) measurement of epoxidized diester mixture 4 obtained in Synthesis Example 13. 3 shows a spectrum obtained by IR (ATR) measurement of epoxidized diester mixture 5 obtained in Synthesis Example 14. １ 1 shows a spectrum obtained by H-NMR measurement of epoxidized diester mixture 5 obtained in Synthesis Example 14. １３ 1 shows a spectrum obtained by C-NMR measurement. 2 shows a spectrum obtained by IR (ATR) measurement of epoxidized diester mixture 5 obtained in Synthesis Example 14. 3 shows a spectrum obtained by IR (ATR) measurement of epoxidized diester mixture 6 obtained in Synthesis Example 15. １ 1 shows a spectrum obtained by H-NMR measurement of epoxidized diester mixture 6 obtained in Synthesis Example 15. １３ 1 shows a spectrum obtained by C-NMR measurement. 2 shows a spectrum obtained by IR (ATR) measurement of epoxidized diester mixture 6 obtained in Synthesis Example 15.

[0038] Embodiments of the present invention are described in detail below. The present invention provides novel compounds obtained by epoxidizing an ester compound, and mixtures containing the compounds. The compounds and mixtures of the present invention can be used, for example, when preparing the plasticizer composition of the present invention. The plasticizer composition of the present invention can also be used, for example, when preparing a resin composition. The resin composition of the present invention can also be used, for example, when forming the resin molded article of the present invention. The resin molded article formed using the resin composition of the present invention can be suitably used as an automotive interior material, such as the surface of an automotive interior part, such as an automotive instrument panel or door trim. The resin molded article of the present invention can also be used, for example, when forming the laminate of the present invention. The laminate formed using the resin molded article of the present invention can also be suitably used as an automotive interior material used in producing an automotive interior part, such as an automotive instrument panel or door trim.

[0039] (Compound) The compound of the present invention is a compound represented by the following formula (1). ...(1) The compound of the present invention can improve the heat shrinkage resistance and meltability of a resin molded article obtained by molding a resin composition prepared using the compound, while improving the tensile elongation at low temperatures (also referred to as low-temperature tensile elongation) and adhesion to polyurethane. Hereinafter, a resin molded article obtained by molding a resin composition prepared using the compound, mixture, or plasticizer composition of the present invention will also be simply referred to as a resin molded article.

[0040] <x, y> In the above formula (1), x and y each independently represent 0 or 1. When x is 0, the following formula (1-1): represents a hydrogen atom. When y is 0, the following structure (1-2): The structures shown represent hydrogen atoms. In the above formulas (1-1) and (1-2), * represents the bonding position with Ax.

[0041] Furthermore, x and y may both be 0, or both be 1, or one may be 0 and the other 1, but from the viewpoint of further improving the low-temperature tensile elongation and heat shrinkage resistance of the resin molded body, it is preferable that x and y are both 0.

[0042] <Ax> In the above formula (1), Ax represents an organic group having 3 to 20 carbon atoms. Here, the same carbon atom in the organic group constituting Ax is １ , Y ２ , Y ３ (However, this is limited to the case where x=1.) and Y ４ (However, only when y=1), the same carbon atom in the organic group constituting Ax may be bonded to two or more of the above Y １ , Y ２ , Y ３ (However, this is limited to the case where x=1.) and Y ４ (However, this is limited to the case where y=1.) In order to further improve the low-temperature tensile elongation of the resin molded article, the same carbon atom in the organic group constituting Ax may be bonded to two or more of the above Y １ , Y ２ , Y ３(However, this is limited to the case where x=1.) and Y ４ (However, only when y=1) １ the carbon atom bonded to Y ２ the carbon atom bonded to Y ３ (However, this is limited to the case where x=1.) and a carbon atom bonded to Y ４ (However, this is limited to the case where y=1.) It is preferable that the carbon atoms bonded to the organic groups Y and Y are different from each other. １ , Y ２ , Y ３ (However, this is limited to the case where x=1.) and Y ４ (However, only when y=1), in the organic group constituting Ax, Y １ the carbon atom bonded to Y ２ the carbon atom bonded to Y ３ (However, this is limited to the case where x=1.) and a carbon bonded to Y ４ (However, this is limited to the case where y=1.) The carbon atoms bonded to Y may be adjacent to each other, or may not be adjacent to each other. In order to further improve the low-temperature tensile elongation of the resin molded article, among the organic groups constituting Ax, Y １ the carbon atom bonded to Y ２ the carbon atom bonded to Y ３ (However, this is limited to the case where x=1.) and a carbon bonded to Y ４ (However, only when y=1) it is preferred that the carbon atoms bonded to are not adjacent to each other.

[0043] Ax is (i) a chain aliphatic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent, (ii) a cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms which may have a substituent, (iii) an aromatic hydrocarbon ring group having 6 to 14 carbon atoms which may have a substituent, or (iv) an organic group having 3 to 20 carbon atoms in which at least one single bond contained in the chain aliphatic hydrocarbon group which may have a substituent is substituted with —O—, —C(═O)—, —O—C(═O)—, or —C(═O)—O— (provided that there are two or more consecutive —O— groups, there are two or more consecutive —C(═O)— groups, and there is no case where —O— or —C(═O)— is one of the groups represented by Y １ , the Y ２ , the Y ３ , or the Y ４ and when the group is located at the end bonded to the group (excluding the case where the group is located at the end bonded to the group (i).), more preferably the organic group of either the above (i) or (iii), and even more preferably the above organic group (i).

[0044] In the present invention, "may have a substituent" means "unsubstituted or substituted." When the organic group contained in the general formula has a substituent, the number of substituents that the organic group has may be one or two or more. When the organic group contained in the general formula has a substituent, the number of carbon atoms of the substituted organic group does not include the number of carbon atoms of the substituent, unless otherwise specified. For example, when a chain aliphatic hydrocarbon ring group having 3 to 20 carbon atoms has a substituent, the number of carbon atoms of such a substituent is not included in the number of carbon atoms of the chain aliphatic hydrocarbon ring group having 3 to 20 carbon atoms.

[0045] Here, the number of carbon atoms in the above (i) chain aliphatic hydrocarbon group having 3 to 20 carbon atoms is preferably 3 to 15, more preferably 3 to 12, even more preferably 3 to 10, and even more preferably 3 to 8. However, the total number of carbon atoms in the above (i) chain aliphatic hydrocarbon group having 3 to 20 carbon atoms, including the number of carbon atoms in the substituent, is 3 to 20. The above (i) chain aliphatic hydrocarbon group having 3 to 20 carbon atoms may be linear or branched. The above (i) chain aliphatic hydrocarbon group having 3 to 20 carbon atoms may be an unsaturated aliphatic hydrocarbon group having an unsaturated bond (carbon-carbon double bond, carbon-carbon triple bond), or may be a saturated aliphatic hydrocarbon group having no unsaturated bond. Furthermore, when the above (i) chain aliphatic hydrocarbon group having 3 to 20 carbon atoms has an unsaturated bond, the number of unsaturated bonds is, for example, 1 to 3. The substituent that the chain aliphatic hydrocarbon group having 3 to 20 carbon atoms in (i) above may have is not particularly limited, but examples thereof include halogen atoms.

[0046] The number of carbon atoms in the (ii) cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms is preferably 4 to 15, more preferably 4 to 12, even more preferably 4 to 10, still more preferably 4 to 8, and even more preferably 4 to 6. However, the total number of carbon atoms in the (ii) cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms, including the number of carbon atoms in the substituent, is 3 to 20. The (ii) cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms may be an unsaturated aliphatic hydrocarbon group having an unsaturated bond (carbon-carbon double bond, carbon-carbon triple bond), or may be a saturated aliphatic hydrocarbon group having no unsaturated bond. Examples of the substituent that the (ii) cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms may have include a halogen atom and an alkyl group having 1 to 8 carbon atoms.

[0047] The number of carbon atoms in the (iii) aromatic hydrocarbon ring group having 6 to 14 carbon atoms is preferably 6 to 12. However, the total number of carbon atoms in the (iii) aromatic hydrocarbon ring group having 6 to 14 carbon atoms, including the number of carbon atoms in the substituent, is 3 to 20. Examples of the substituent that the (iii) aromatic hydrocarbon ring group having 6 to 14 carbon atoms may have include a halogen atom and an alkyl group having 1 to 6 carbon atoms.

[0048] Here, the number of carbon atoms in the organic group having 3 to 20 carbon atoms in (iv) above is preferably 3 to 15, more preferably 3 to 12, even more preferably 3 to 10, still more preferably 3 to 8, even more preferably 3 to 6, and particularly preferably 3 to 4. In the organic group having 3 to 20 carbon atoms in (iv) above, when at least one single bond contained in the chain aliphatic hydrocarbon group which may have a substituent is substituted with -C(=O)-, -O-C(=O)-, or -C(=O)-O-, the number of carbon atoms of -C(=O)-, -O-C(=O)-, or -C(=O)-O- is included in the number of carbon atoms in the organic group having 3 to 20 carbon atoms in (iv) above. However, the total number of carbon atoms in the organic group having 3 to 20 carbon atoms in (iv) above, including the number of carbon atoms of the substituent, is 3 to 20. Examples of the substituent that the organic group having 3 to 20 carbon atoms in (iv) above may have include halogen atoms.

[0049] Specific preferred examples of Ax include groups represented by any one of the following formulae (2-1) to (2-35) which may have a substituent. Here, "having a substituent" means that any one of the hydrogen atoms of the group represented by any one of the following formulae (2-1) to (2-35) is substituted.

[0050] In the above formulas (2-1) to (2-4), (2-20) to (2-26), and (2-30) to (2-33), "-" extends from any position on the ring, and Y １ , Y ２ , Y ３ , or Y ４In addition, in the above formulas (2-5) to (2-19), (2-27) to (2-29), and (2-34) to (2-35), the "-" at the end of the chain structure represents a bond to Y １ , Y ２ , Y ３ , or Y ４ Represents a bond with .

[0051] When x is 0, the structure represented by the above formula (1-1) (i.e., a hydrogen atom) can be any of the hydrogen atoms contained in the groups represented by any of the above formulas (2-1) to (2-35), and when y is 0, the structure represented by the above formula (1-2) (i.e., a hydrogen atom) can be any of the hydrogen atoms contained in the groups represented by any of the above formulas (2-1) to (2-35).

[0052] Examples of the substituent that may be contained in the group represented by any one of the above formulas (2-1) to (2-35) include a halogen atom and an alkyl group having 1 to 4 carbon atoms.

[0053] From the viewpoint of making the resin molded body excellent in low-temperature tensile elongation, Ax is preferably a group represented by any one of the above formulas (2-1) to (2-22), more preferably a group represented by any one of the above formulas (2-5) to (2-6), (2-8), and (2-20), and even more preferably a group represented by the above formula (2-6).

[0054] <Y １ , Y ４ In the above formula (1), Y １ and Y ４ are each independently a single bond, —C(═O)—, or —C(═O)—NR １ - or -C(=O)-O-. １ represents a hydrogen atom, a methyl group, or an ethyl group. From the viewpoint of improving the tensile elongation at low temperatures of the resin molded body and the adhesiveness to polyurethane, while also improving the heat shrinkage resistance and meltability, Y １ and Y ４ are each independently a single bond, —C(═O)—, or —C(═O)—NR １- is preferred, a single bond or -C(=O)- is more preferred, and -C(=O)- is even more preferred.

[0055] <Y ２ , Y ３ In the above formula (1), Y ２ and Y ３ are each independently a single bond, —C(═O)—, or —NR ２ represents —C(═O)— or —O—C(═O)—. ２ represents a hydrogen atom, a methyl group, or an ethyl group. From the viewpoint of improving the tensile elongation at low temperatures of the resin molded body and the adhesiveness to polyurethane, while also improving the heat shrinkage resistance and meltability, Y ２ and Y ３ are each independently a single bond, —C(═O)—, or —NR ２ —C(═O)— is preferred, a single bond or —C(═O)— is more preferred, and —C(═O)— is even more preferred.

[0056] Y １ , Y ４ , Y ２ , and Y ３ may be independently different from each other or the same.

[0057] <SP １ , SP ４ In the above formula (1), SP １ and SP ４ are each independently —CH ２ CH ２ O-, -CH ２ CH (CH ３ )O-,-CH(CH ３ ) CH ２ O-, -CH ２ CH (CH ２ CH ３ ) O— or —CH(CH ２ CH ３ ) CH ２ O- and SP １ and SP ４ Each of the groups independently represents —CH ２ CH ２ O-, -CH ２ CH (CH３ ) O— or —CH(CH ３ ) CH ２ O— is preferred, and —CH ２ CH ２ O- is more preferred.

[0058] <SP ２ , SP ３ In the above formula (1), SP ２ and SP ３ are each independently —OCH ２ CH ２ -, -OCH(CH ３ ) CH ２ -, -OCH ２ CH (CH ３ )-,-OCH(CH ２ CH ３ ) CH ２ - or -OCH ２ CH (CH ２ CH ３ )- and SP ２ and SP ３ Each of the groups independently represents —OCH ２ CH ２ -, -OCH(CH ３ ) CH ２ - or -OCH ２ CH (CH ３ )- is preferred, and —OCH ２ CH ２ - is more preferable.

[0059] <a, b, c, d> In the above formula (1), a, b, c, and d each independently represent an integer of 0 to 30. From the viewpoint of improving the heat shrinkage resistance and meltability while providing the resin molded article with good tensile elongation at low temperatures and good adhesion to polyurethane, a, b, c, and d each independently preferably represent an integer of 0 to 25, more preferably an integer of 2 to 20, even more preferably an integer of 3 to 15, even more preferably an integer of 4 to 12, and even more preferably an integer of 5 to 10.

[0060] <R ａ , R ｂ , R ｃ , R ｄIn the above formula (1), R ａ , R ｂ , R ｃ , and R ｄ R each independently represents a chain aliphatic hydrocarbon group having 12 to 18 carbon atoms which may have a substituent. ａ , R ｂ , R ｃ , and R ｄ The number of carbon atoms in the chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms, which may have a substituent, that constitute R are each independently preferably 13 to 17, and more preferably 14 to 16. ａ , R ｂ , R ｃ , and R ｄ The chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms, which may have a substituent, constituting R may each independently be an unsaturated aliphatic hydrocarbon group having an unsaturated bond (carbon-carbon double bond, carbon-carbon triple bond), or may be a saturated aliphatic hydrocarbon group having no unsaturated bond. When the chain aliphatic hydrocarbon group having 12 to 18 carbon atoms has an unsaturated bond, the number of double bonds is, for example, 1 to 5. The isomer formed by the carbon-carbon double bond in the chain aliphatic hydrocarbon group having 12 to 18 carbon atoms may be a cis-isomer or a trans-isomer, or a mixture of cis- and trans-isomers may be present. R ａ , R ｂ , R ｃ , and R ｄ Examples of the substituent that the chain aliphatic hydrocarbon group having 12 to 18 carbon atoms that constitutes R include an alkyl group having 1 to 3 carbon atoms and a halogen atom. ａ , R ｂ , R ｃ , and R ｄ At least one of the epoxy groups contains one or more epoxy groups. The number of epoxy groups is determined by the formula R ａ , R ｂ , R ｃ , and R ｄare each independently preferably 1 or more, more preferably 2 or more, and preferably 5 or less, more preferably 4 or less. If the number of epoxy groups is within the above range, the resin molded article can have good low-temperature tensile elongation and adhesion to polyurethane, while improving heat shrinkage resistance and meltability. ａ , R ｂ , R ｃ , and R ｄ may be independently different from each other or the same.

[0061] And R ａ , R ｂ , R ｃ , and R ｄ are each independently, for example, It is preferable that the alkyl group is a chain aliphatic hydrocarbon group having 15 carbon atoms, such as any one of the following: (However, R ａ , R ｂ , R ｃ , and R ｄ At least one of the carbon atoms in the chain aliphatic hydrocarbon group having 15 carbon atoms contains one or more epoxy groups.) In the above formula, * represents a carbon atom bonded to an aromatic ring. At least one hydrogen atom in the chain aliphatic hydrocarbon group having 15 carbon atoms may be substituted.

[0062] The compound of the present invention includes a compound represented by the above formula (1) having a single structure, and a mixture of two or more compounds having different structures combined in any ratio.

[0063] (Mixture) The mixture of the present invention contains a compound represented by the above formula (1) (compound of the present invention) and a compound represented by the following formula (3). (3) The mixture of the present invention can improve the tensile elongation at low temperatures (also referred to as low-temperature tensile elongation) and adhesion to polyurethane of a resin molded product obtained by molding a resin composition prepared using the compound, while also improving the heat shrinkage resistance and meltability.

[0064] <p, q> In the above formula (3), p and q each independently represent 0 or 1. When p is 0, the following formula (3-1): represents a hydrogen atom. When q is 0, the following structure (3-2): represents a hydrogen atom. In the above formulas (3-1) and (3-2), * represents the bonding position with Bx.

[0065] Furthermore, p and q may both be 0, or both be 1, or one may be 0 and the other 1, but from the viewpoint of further improving the low-temperature tensile elongation and heat shrinkage resistance of the resin molded body, it is preferable that p and q are both 0.

[0066] <Bx> In the above formula (3), Bx represents an organic group having 3 to 20 carbon atoms. Here, the same carbon atom in the organic group constituting Bx is １１ , Y ２１ , Y ３１ (However, this is limited to the case where p=1.) and Y ４１ (However, only when q=1), the same carbon atom in the organic group constituting Bx may be bonded to two or more of the above Y １１ , Y ２１ , Y ３１ (However, this is limited to the case where p=1.) and Y ４１ (However, this is limited to the case where q=1.) In order to further improve the low-temperature tensile elongation of the resin molded article, the same carbon atom in the organic group constituting Bx may be bonded to two or more of the above Y １１ , Y ２１ , Y ３１ (However, this is limited to the case where p=1.) and Y ４１ (However, only when q=1), that is, Y １１ the carbon atom bonded to Y ２１ the carbon atom bonded to Y ３１ (However, this is limited to the case where p=1.) and a carbon atom bonded to Y ４１ (However, this is limited to the case where q=1.) It is preferable that the carbon atoms bonded to the organic groups Y and Y are different from each other. １１ , Y ２１ , Y ３１ (However, this is limited to the case where p=1.) and Y４１ (However, only when q=1), in the organic group constituting Bx, Y １１ the carbon atom bonded to Y ２１ the carbon atom bonded to Y ３１ (However, this is limited to the case where p=1.) and a carbon atom bonded to Y ４１ (However, this is limited to the case where q=1) and the carbon atoms bonded to Y may be adjacent to each other, or may not be adjacent to each other. １１ the carbon atom bonded to Y ２１ the carbon atom bonded to Y ３１ (However, this is limited to the case where p=1.) and a carbon atom bonded to Y ４１ (However, this is limited to the case where q=1.) It is preferable that the carbon atoms bonded to are not adjacent to each other.

[0067] Bx is (i) a chain aliphatic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent, (ii) a cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms which may have a substituent, (iii) an aromatic hydrocarbon ring group having 6 to 14 carbon atoms which may have a substituent, or (iv) an organic group having 3 to 20 carbon atoms in which at least one single bond contained in the chain aliphatic hydrocarbon group which may have a substituent is substituted with —O—, —C(═O)—, —O—C(═O)—, or —C(═O)—O— (provided that there are two or more consecutive —O— groups, there are two or more consecutive —C(═O)— groups, and there is no case where —O— or —C(═O)— is Y). １１ , Y ２１ , Y ３１ , or Y ４１ and when the group is located at the end bonded to the group (excluding the case where the group is located at the end bonded to the group (i).), more preferably the organic group of either the above (i) or (iii), and even more preferably the above organic group (i).

[0068] In the present invention, "may have a substituent" means "unsubstituted or substituted." When the organic group contained in the general formula has a substituent, the number of substituents that the organic group has may be one or two or more. When the organic group contained in the general formula has a substituent, the number of carbon atoms of the substituted organic group does not include the number of carbon atoms of the substituent, unless otherwise specified. For example, when a chain aliphatic hydrocarbon ring group having 3 to 20 carbon atoms has a substituent, the number of carbon atoms of such a substituent is not included in the number of carbon atoms of the chain aliphatic hydrocarbon ring group having 3 to 20 carbon atoms.

[0069] Here, the preferred carbon numbers and structures of the aliphatic hydrocarbon groups, aromatic hydrocarbon groups, or organic groups (i) to (iv) above are the same as those described above for each of (i) to (iv) in the section "Ax" under "Compound."

[0070] Specific preferred examples of Bx include groups represented by any one of the following formulae (2-1) to (2-35), which may have a substituent. Here, "having a substituent" means that one of the hydrogen atoms of the group represented by any one of the following formulae (2-1) to (2-35) is substituted. Bx may have the same structure as Ax in the compound represented by the above formula (1), or may have a structure different from Ax.

[0071] In the above formulas (2-1) to (2-4), (2-20) to (2-26), and (2-30) to (2-33), "-" extends from any position on the ring, and Y １１ , Y ２１ , Y ３１ , or Y ４１ In addition, in the above formulas (2-5) to (2-19), (2-27) to (2-29), and (2-34) to (2-35), the "-" at the end of the chain structure represents a bond to Y １１ , Y ２１ , Y ３１ , or Y ４１ Represents a bond with .

[0072] When p is 0, the structure represented by the above formula (3-1) (i.e., a hydrogen atom) can be any of the hydrogen atoms contained in the group represented by any of the above formulas (2-1) to (2-35), and when q is 0, the structure represented by the above formula (3-2) (i.e., a hydrogen atom) can be any of the hydrogen atoms contained in the group represented by any of the above formulas (2-1) to (2-35).

[0073] Examples of the substituent that may be contained in the group represented by any one of the above formulas (2-1) to (2-35) include a halogen atom and an alkyl group having 1 to 4 carbon atoms.

[0074] From the viewpoint of providing a resin molded body with excellent low-temperature tensile elongation, Bx is preferably a group represented by any one of the above formulas (2-1) to (2-22), more preferably a group represented by any one of the above formulas (2-5) to (2-6), (2-8), and (2-20), and even more preferably a group represented by the above formula (2-6).

[0075] <Y １１ , Y ４１ In the above formula (3), Y １１ and Y ４１ are each independently a single bond, —C(═O)—, or —C(═O)—NR １ - or -C(=O)-O-. １ represents a hydrogen atom, a methyl group, or an ethyl group. From the viewpoint of improving the tensile elongation at low temperatures of the resin molded body and the adhesiveness to polyurethane, while also improving the heat shrinkage resistance and meltability, Y １１ and Y ４１ are each independently a single bond, —C(═O)—, or —C(═O)—NR １ - is preferred, a single bond or -C(=O)- is more preferred, and -C(=O)- is even more preferred.

[0076] <Y ２１ , Y ３１ In the above formula (3), Y ２１ and Y ３１ are each independently a single bond, —C(═O)—, or —NR ２ represents —C(═O)— or —O—C(═O)—.２ represents a hydrogen atom, a methyl group, or an ethyl group. From the viewpoint of improving the tensile elongation at low temperatures of the resin molded body and the adhesiveness to polyurethane, while also improving the heat shrinkage resistance and meltability, Y ２１ and Y ３１ are each independently a single bond, —C(═O)—, or —NR ２ —C(═O)— is preferred, a single bond or —C(═O)— is more preferred, and —C(═O)— is even more preferred.

[0077] Y １１ , Y ４１ , Y ２１ , and Y ３１ may be independently different from each other or the same.

[0078] <SP １１ , SP ４１ In the above formula (3), SP １１ and SP ４１ are each independently —CH ２ CH ２ O-, -CH ２ CH (CH ３ )O-,-CH(CH ３ ) CH ２ O-, -CH ２ CH (CH ２ CH ３ ) O— or —CH(CH ２ CH ３ ) CH ２ O- and SP １１ and SP ４１ Each of the groups independently represents —CH ２ CH ２ O-, -CH ２ CH (CH ３ ) O— or —CH(CH ３ ) CH ２ O— is preferred, and —CH ２ CH ２ O- is more preferred.

[0079] <SP ２１ , SP ３１ In the above formula (3), SP ２１ and SP ３１are each independently —OCH ２ CH ２ -, -OCH(CH ３ ) CH ２ -, -OCH ２ CH (CH ３ )-,-OCH(CH ２ CH ３ ) CH ２ - or -OCH ２ CH (CH ２ CH ３ )- and SP ２１ and SP ３１ Each of the groups independently represents —OCH ２ CH ２ -, -OCH(CH ３ ) CH ２ - or -OCH ２ CH (CH ３ )- is preferred, and —OCH ２ CH ２ - is more preferable.

[0080] <e, f, g, h> In the above formula (3), e, f, g, and h each independently represent an integer of 0 to 30. From the viewpoint of improving the heat shrinkage resistance and meltability while providing the resin molded body with good tensile elongation at low temperatures and good adhesion to polyurethane, e, f, g, and h each independently preferably represent an integer of 0 to 25, more preferably an integer of 2 to 20, even more preferably an integer of 3 to 15, even more preferably an integer of 4 to 12, and even more preferably an integer of 5 to 10.

[0081] <R ａ１ , R ｂ１ , R ｃ１ , R ｄ１ In the above formula (3), R ａ１ , R ｂ１ , R ｃ１ and R ｄ１ R each independently represents a chain aliphatic hydrocarbon group having 12 to 18 carbon atoms which may have a substituent. ａ１ , R ｂ１ , R ｃ１ and R ｄ１The number of carbon atoms in the chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms, which may have a substituent, that constitute R are each independently preferably 13 to 17, and more preferably 14 to 16. ａ１ , R ｂ１ , R ｃ１ and R ｄ１ The chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms, which may have a substituent, constituting R may each independently be an unsaturated aliphatic hydrocarbon group having an unsaturated bond (carbon-carbon double bond, carbon-carbon triple bond), or may be a saturated aliphatic hydrocarbon group having no unsaturated bond. When the chain aliphatic hydrocarbon group having 12 to 18 carbon atoms has an unsaturated bond, the number of double bonds is, for example, 1 to 5. The isomer formed by the carbon-carbon double bond in the chain aliphatic hydrocarbon group having 12 to 18 carbon atoms may be a cis-isomer or a trans-isomer, or a mixture of cis- and trans-isomers may be present. R ａ１ , R ｂ１ , R ｃ１ and R ｄ１ Examples of the substituent that the chain aliphatic hydrocarbon group having 12 to 18 carbon atoms that constitutes R include an alkyl group having 1 to 3 carbon atoms and a halogen atom. ａ１ , R ｂ１ , R ｃ１ and R ｄ１ None of the R groups contains an epoxy group. ａ１ , R ｂ１ , R ｃ１ and R ｄ１ may be independently different from each other or the same.

[0082] And R ａ１ , R ｂ１ , R ｃ１ and R ｄ１ are each independently, for example, -(CH ２ ) １４ CH ３ , -(CH ２ ) ７ CH=CH(CH ２ ) ５ CH ３ , -(CH ２ )７ CH=CHCH ２ CH=CH(CH ２ ) ２ CH ３ , -(CH ２ ) ７ CH=CHCH ２ CH=CHCH=CHCH ３ , or -(CH ２ ) ７ CH=CHCH ２ CH=CHCH ２ CH=CH ２ It is preferable that the chain aliphatic hydrocarbon group having 15 carbon atoms is any one of the following: In addition, at least one hydrogen atom of the chain aliphatic hydrocarbon group having 15 carbon atoms may be substituted.

[0083] The mixture of the present invention includes a mixture of a compound represented by the above formula (1) and a compound represented by the above formula (3) each having a single structure, and a mixture of two or more compounds with different structures combined in any ratio. For example, the mixture of the present invention includes a mixture of a compound represented by the above formula (1) and a compound represented by the above formula (3) each having a single structure, and a mixture of two or more compounds with different structures combined in any ratio. ａ , R ｂ , R ｃ and R ｄ may contain at least two or more compounds represented by the above formula (1), each of which is independently different from the others.

[0084] The content ratio of the compounds represented by formula (1) and formula (3) in the mixture of the present invention is not particularly limited, but for example, the ratio of the mass of the compound represented by formula (1) to the total mass of the compounds represented by formula (1) and formula (3) is preferably 50 mass% or more, more preferably 60 mass% or more, and even more preferably 65 mass% or more. When the content ratio of the compound represented by formula (1) is equal to or greater than the above-mentioned lower limit, the resin molded article formed from the resin composition prepared using the mixture of the present invention can have good low-temperature tensile elongation and adhesion to polyurethane, while also improving heat shrinkage resistance and meltability. The upper limit of the content ratio of the compound represented by formula (1) is not particularly limited, and may be 99 mass%.

[0085] <Method for Producing Compound> The compound of the present invention (compound represented by the above formula (1)) is not particularly limited, and can be produced by (I) a synthesis step of appropriately bonding and / or modifying a plurality of raw material compounds to obtain a compound represented by the following formula (4), and (II) a synthesis step of appropriately bonding and / or modifying a compound represented by the following formula (4) obtained in the synthesis step, wherein R ａ２ , R ｂ２ , R ｃ２ , and R ｄ２ The polyisocyanate can be obtained by an epoxidation step in which at least one linear aliphatic hydrocarbon group of the above is epoxidized.

[0086] <<(I) Synthesis Step>> The compound represented by the following formula (4) is not particularly limited and can be synthesized by combining known synthesis reactions. Examples of literature describing known synthesis reactions include Sandler-Caro, Organic Compound Synthesis by Functional Group, Vol. [I] and Vol. [II] (Hirokawa Publishing), and MARCH'S ADVANCED ORGANIC CHEMISTRY SIXTH EDITION (Michael B. Smith, Jerry March; WILEY). Typically, the compound represented by the following formula (4) can be synthesized by combining known synthesis reactions such as an ether bond (—O—), an ester bond (—C(═O)—O—, —O—C(═O)—), a urethane bond (—C(═O)—NR １ -, -NR ２ It can be produced by appropriately bonding and / or modifying a plurality of raw material compounds using a reaction for forming a compound such as —C(═O)—. １ and R ２has the same meaning as above. More specifically, the formation of an ether bond can be carried out, for example, as follows. (i) A compound represented by the formula: D1-hal (hal represents a halogen atom; the same applies hereinafter) and a compound represented by the formula: D2-OMet (Met represents an alkali metal (mainly sodium); the same applies hereinafter) are mixed and condensed (Williamsson synthesis). In the formula, D1 and D2 represent any organic group (the same applies hereinafter). (ii) A compound represented by the formula: D1-hal and a compound represented by the formula: D2-OH are mixed and condensed in the presence of a base such as sodium hydroxide or potassium hydroxide. (iii) A compound represented by the formula: D1-J (J represents an epoxy group) and a compound represented by the formula: D2-OH are mixed and condensed in the presence of a base such as sodium hydroxide or potassium hydroxide. (Iv) A compound represented by the formula: D1-OFN (OFN represents a group having an unsaturated bond) and a compound represented by the formula: D2-OMet are mixed in the presence of a base such as sodium hydroxide or potassium hydroxide to cause an addition reaction. (v) A compound represented by the formula: D1-hal and a compound represented by the formula: D2-OMet are mixed in the presence of copper or cuprous chloride to cause condensation (Ullmann condensation).

[0087] More specifically, the formation of an ester bond can be carried out, for example, as follows. (vi) A compound represented by the formula: D1-COOH and a compound represented by the formula: D2-OH are subjected to dehydration condensation in the presence of a dehydration condensation agent (WSC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride) or the like). (viii) A halogenating agent is allowed to act on a compound represented by the formula: D1-COOH to obtain a compound represented by the formula: D1-C(═O)-hal, and then this compound is reacted with a compound represented by the formula: D2-OH in the presence of a base. (viii) An acid anhydride is allowed to act on a compound represented by the formula: D1-COOH to obtain a mixed acid anhydride, and then this mixed acid anhydride is reacted with a compound represented by the formula: D2-OH. (ix) A compound represented by the formula: D1-COOH and a compound represented by the formula: D2-OH are subjected to dehydration condensation in the presence of an acid catalyst or a base catalyst.

[0088] More specifically, the formation of a urethane bond can be carried out, for example, as follows: (x) A compound represented by the formula: D1-N=C=O is reacted with a compound represented by the formula: D2-OH in the presence of a base catalyst.

[0089] The compound represented by the following formula (4) can be produced, for example, by the reaction shown below. (In the formula, Ax, Y １ ~Y ４ , SP １ ~SP ４ , a, b, c, d, x, and y have the same meanings as above. ａ２ , R ｂ２ , R ｃ２ , R ｄ２ is a chain aliphatic hydrocarbon group described later.) ...(4) That is, by reacting a compound having a carboxyl group represented by formula (A) with a compound having a hydroxyl group represented by formula (B) in a ratio of [the number of moles of carboxyl groups in the compound represented by formula (A):the number of moles of hydroxyl groups in the compound represented by formula (B)] of 1:2 to 2:1, preferably 1:1.5 to 1.5:1, and more preferably 1:1.0 to 1:1.5, the target compound represented by formula (4) can be produced with high selectivity and high yield.

[0090] <<R ａ２ , R ｂ２ , R ｃ２ , R ｄ２ >> In the above formula (4), R ａ２ , R ｂ２ , R ｃ２ , and R ｄ２ R each independently represents a chain aliphatic hydrocarbon group having 12 to 18 carbon atoms which may have a substituent. ａ２ , R ｂ２ , R ｃ２ , and R ｄ２ The number of carbon atoms in the chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms, which may have a substituent, that constitute R are each independently preferably 13 to 17, and more preferably 14 to 16. ａ２ , R ｂ２ , R ｃ２ , and Rｄ２ The chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms, which may have a substituent, constituting R may each independently be an unsaturated aliphatic hydrocarbon group having an unsaturated bond (carbon-carbon double bond, carbon-carbon triple bond), or may be a saturated aliphatic hydrocarbon group having no unsaturated bond. When the chain aliphatic hydrocarbon group having 12 to 18 carbon atoms has an unsaturated bond, the number of double bonds is, for example, 1 to 5. The isomer formed by the carbon-carbon double bond in the chain aliphatic hydrocarbon group having 12 to 18 carbon atoms may be a cis-isomer or a trans-isomer, or a mixture of cis- and trans-isomers may be present. R ａ２ , R ｂ２ , R ｃ２ , and R ｄ２ Examples of the substituent that the chain aliphatic hydrocarbon group having 12 to 18 carbon atoms that constitutes R include an alkyl group having 1 to 3 carbon atoms and a halogen atom. ａ２ , R ｂ２ , R ｃ２ , and R ｄ２ None of the R groups contains an epoxy group. ａ２ , R ｂ２ , R ｃ２ , and R ｄ２ may be independently different from each other or the same.

[0091] And R ａ２ , R ｂ２ , R ｃ２ , and R ｄ２ are each independently, for example, -(CH ２ ) １４ CH ３ , -(CH ２ ) ７ CH=CH(CH ２ ) ５ CH ３ , -(CH ２ ) ７ CH=CHCH ２ CH=CH(CH ２ ) ２ CH ３ , -(CH ２ ) ７ CH=CHCH ２CH=CHCH=CHCH ３ , or -(CH ２ ) ７ CH=CHCH ２ CH=CHCH ２ CH=CH ２ It is preferable that the chain aliphatic hydrocarbon group having 15 carbon atoms is any one of the following: In addition, at least one hydrogen atom of the chain aliphatic hydrocarbon group having 15 carbon atoms may be substituted.

[0092] In this case, examples of the dehydration condensation agent to be used include carbodiimides such as 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-para-toluenesulfonate, dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, bis(2,6-diisopropylphenyl)carbodiimide, bis(trimethylsilyl)carbodiimide, and bisisopropylcarbodiimide, 2-methyl-6-nitrobenzoic anhydride, 2,2'-carbonylbis-1H-imidazole, 1,1'-oxalyldiimidazole, diphenylphosphoryl azide, and 1-(4-nitrobenzenesulfonyl)-1H-imidazole. H-1,2,4-triazole, 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate, 1H-benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate, N,N,N',N'-tetramethyl-O-(N-succinimidyl) Examples of suitable chloroisothiazolinium compounds include uronium tetrafluoroborate, N-(1,2,2,2-tetrachloroethoxycarbonyloxy)succinimide, N-carbobenzoxysuccinimide, O-(6-chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, O-(6-chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate, 2-bromo-1-ethylpyridinium tetrafluoroborate, 2-chloro-1,3-dimethylimidazolinium chloride, 2-chloro-1,3-dimethylimidazolinium hexafluorophosphate, 2-chloro-1-methylpyridinium iodide, 2-chloro-1-methylpyridinium para-toluenesulfonate, 2-fluoro-1-methylpyridinium para-toluenesulfonate, and trichloroacetic acid pentachlorophenyl ester.In terms of reactivity, cost, and usable solvents, dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, bis(2,6-diisopropylphenyl)carbodiimide, bis(trimethylsilyl)carbodiimide, bisisopropylcarbodiimide, and 2,2'-carbonylbis-1H-imidazole are more preferred. The amount of the dehydration condensation agent added is usually 1 to 1.5 mol, preferably 1 to 1.2 mol, and more preferably 1 to 1.1 mol, relative to the number of moles of carboxyl groups in the compound represented by formula (A). The dehydration condensation agent may be added as is, or may be added as a solution dissolved or dispersed in a suitable solvent.

[0093] In this case, an activator can be used. Examples of the activator include 4-(dimethylamino)pyridine (N,N-dimethyl-4-aminopyridine). The amount of the activator added is usually 0.01 to 1.0 mol, and preferably 0.01 to 0.5 mol, relative to the number of moles of the dehydration condensation agent. The activator may be added as is, or may be added as a solution dissolved or dispersed in an appropriate solvent.

[0094] The solvent used in this reaction is not particularly limited as long as it is inert to the reaction. Examples thereof include ether solvents such as diethyl ether, tetrahydrofuran, 1,2-dimethoxyethane, 1,4-dioxane, cyclopentyl methyl ether, and methyl tertiary butyl ether; ester solvents such as ethyl acetate, propyl acetate, methyl propionate, and γ-butyrolactone; aromatic hydrocarbon solvents such as benzene, toluene, and xylene; aliphatic hydrocarbon solvents such as n-pentane, n-hexane, and n-heptane; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N-dimethylimidazolidinone, and hexamethylphosphoric triamide; sulfur-containing solvents such as dimethyl sulfoxide and sulfolane; halogenated solvents such as methylene chloride, chloroform, 1,2-dichloroethane, and chlorobenzene; and mixed solvents consisting of two or more of these. Among these, ether-based solvents, ester-based solvents, amide-based solvents, and halogen-based solvents are preferred, with amide-based solvents being particularly preferred, and N-methylpyrrolidone, N,N-dimethylacetamide, and N,N-dimethylformamide being particularly preferred.

[0095] The amount of the solvent to be used is not particularly limited and can be determined appropriately taking into consideration the type of compound to be used, the scale of the reaction, and the like, but is usually 1 to 100 g per 1 g of the compound having a carboxyl group represented by Formula (A).

[0096] The reaction proceeds smoothly in a temperature range from −10° C. to the boiling point of the solvent used, preferably 10° C. to 80° C., more preferably 15° C. to 50° C. The reaction time for each reaction varies depending on the reaction scale, but is usually several minutes to several tens of hours, preferably several minutes to 70 hours, more preferably several hours to 30 hours.

[0097] The compound represented by formula (4) can also be produced, for example, by the reaction shown below. (In the formula, Ax, Y １ ~Y ４ , R １ , R ２ , SP １ ~SP ４ , a, b, c, d, Rａ２ , R ｂ２ , R ｃ２ , R ｄ２ , x, and y have the same meanings as defined above.) That is, by reacting a compound having an acid chloride group represented by formula (C) with a compound having a hydroxyl group represented by formula (B) in a ratio of [the number of moles of hydroxyl groups in the compound represented by formula (B):the number of moles of acid chloride groups in the compound represented by formula (C)] of 1:2 to 2:1, preferably 1:1.5 to 1.5:1, and more preferably 1:1.0 to 1:1.2, the target compound represented by formula (4) can be produced with high selectivity and high yield.

[0098] In this case, examples of the base to be used include organic bases such as triethylamine, diisopropylethylamine, pyridine, 4-(dimethylamino)pyridine (N,N-dimethyl-4-aminopyridine), and 2,6-lutidine; and inorganic bases such as sodium hydroxide, sodium carbonate, and sodium hydrogencarbonate.

[0099] In this case, an activator can be used. Examples of the activator include 4-(dimethylamino)pyridine (N,N-dimethyl-4-aminopyridine). The amount of the activator added is usually 0.01 to 1.0 mol, preferably 0.01 to 0.5 mol, and more preferably 0.01 to 0.2 mol, relative to the compound having an acid chloride group represented by formula (C). The activator may be added as is, or may be added as a solution dissolved or dispersed in an appropriate solvent.

[0100] The solvent used in this reaction is not particularly limited as long as it is inert to the reaction. Examples thereof include ether solvents such as diethyl ether, tetrahydrofuran, 1,2-dimethoxyethane, 1,4-dioxane, cyclopentyl methyl ether, and methyl tertiary butyl ether; ester solvents such as ethyl acetate, propyl acetate, methyl propionate, and γ-butyrolactone; aromatic hydrocarbon solvents such as benzene, toluene, and xylene; aliphatic hydrocarbon solvents such as n-pentane, n-hexane, and n-heptane; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N-dimethylimidazolidinone, and hexamethylphosphoric triamide; sulfur-containing solvents such as dimethyl sulfoxide and sulfolane; halogenated solvents such as methylene chloride, chloroform, 1,2-dichloroethane, and chlorobenzene; and mixed solvents consisting of two or more of these. Among these, ether-based solvents, ester-based solvents, and halogen-based solvents are preferred, with ether-based solvents and halogen-based solvents being more preferred, and tetrahydrofuran, 1,2-dimethoxyethane, cyclopentyl methyl ether, methyl tertiary butyl ether, chloroform, and 1,2-dichloroethane being particularly preferred.

[0101] The amount of the solvent to be used is not particularly limited and can be determined appropriately taking into consideration the type of compound to be used, the scale of the reaction, and the like, but is usually 1 to 100 g per 1 g of the compound having a carboxyl group represented by Formula (A).

[0102] The reaction proceeds smoothly in a temperature range from −20° C. to the boiling point of the solvent used, preferably −5° C. to 50° C., more preferably 0° C. to 40° C. The reaction time for each reaction varies depending on the reaction scale, but is usually from several minutes to 10-odd hours, preferably from several minutes to 10 hours, more preferably from several tens of minutes to 5 hours.

[0103] In this case, the compound having an acid chloride group represented by formula (C) may be a commercially available product, or may be synthesized from the compound having a carboxyl group represented by formula (A).

[0104] The compound having an acid chloride group represented by formula (C) can be produced as follows. (In the formula, x and y have the same meanings as above.)

[0105] In this case, the chlorinating agent used is thionyl chloride (SOCl ２ ), oxalyl chloride [(C(═O)Cl) ２ ], sulfuryl chloride (SO ２ Cl ２ ), phosphoryl chloride (POC ｌ３ ), phosphorus trichloride (PCl ３ ), phosphorus pentachloride (PCl ５ ), etc., with thionyl chloride, oxalyl chloride, and sulfuryl chloride being preferred. These chlorinating agents can be used alone or in combination of two or more. The chlorinating agent used is a compound having a carboxyl group represented by formula (A) that is reacted with the chlorinating agent in a ratio of [the number of moles of the carboxyl group in the compound represented by formula (A):the chlorinating agent] of 1:2 to 2:1, preferably 1:5 to 1:3, and more preferably 1:1.0 to 1:1.5, thereby producing the target acid chloride compound represented by formula (C) with high selectivity and high yield.

[0106] In this case, an activator can be used. Examples of the activator include N,N-dimethylformamide, triethylamine, and tetraalkylammonium, with N,N-dimethylformamide and tetraalkylammonium being preferred. The amount of the activator added is usually 0.01 to 3.0 mol, preferably 0.01 to 2.0 mol, and more preferably 0.01 to 0.5 mol, relative to the amount of the compound having a carboxyl group represented by formula (A).

[0107] The solvent used in this reaction is not particularly limited as long as it is inert to the reaction. Examples thereof include ether solvents such as diethyl ether, tetrahydrofuran, 1,2-dimethoxyethane, 1,4-dioxane, cyclopentyl methyl ether, and methyl tertiary butyl ether; ester solvents such as ethyl acetate, propyl acetate, methyl propionate, and γ-butyrolactone; aromatic hydrocarbon solvents such as benzene, toluene, and xylene; aliphatic hydrocarbon solvents such as n-pentane, n-hexane, and n-heptane; amide solvents such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidone, N,N-dimethylimidazolidinone, and hexamethylphosphoric triamide; sulfur-containing solvents such as dimethyl sulfoxide and sulfolane; halogenated solvents such as methylene chloride, chloroform, 1,2-dichloroethane, and chlorobenzene; and mixed solvents consisting of two or more of these. Among these, ether-based solvents, ester-based solvents, and halogen-based solvents are preferred, with ether-based solvents and halogen-based solvents being more preferred, and tetrahydrofuran, 1,2-dimethoxyethane, cyclopentyl methyl ether, methyl tertiary butyl ether, chloroform, and 1,2-dichloroethane being particularly preferred.

[0108] The amount of the solvent to be used is not particularly limited and can be determined appropriately taking into consideration the type of compound to be used, the scale of the reaction, and the like, but is usually 1 to 100 g per 1 g of the compound having a carboxyl group represented by Formula (A).

[0109] The reaction proceeds smoothly in a temperature range from −20° C. to the boiling point of the solvent used, preferably −5° C. to 150° C., more preferably 0° C. to 110° C. The reaction time for each reaction varies depending on the reaction scale, but is usually from several minutes to 10-odd hours, preferably from several minutes to 10 hours, more preferably from several tens of minutes to 5 hours.

[0110] As the compound represented by formula (B), cardanol produced from a cashew nut shell liquid extract component and its derivatives can be suitably used. There are no particular limitations on the compound, as long as it is cardanol or a cardanol derivative having a hydroxyl group. Specific examples from CardRite are listed below, but equivalent products from other companies can also be used. Cardanol and cardanol derivatives are manufactured, for example, by Cardrite Corporation, and specific examples of Cardrite product names include NX-2021, NX-2022, NX-2023, NX-2023D, NX-2024, NX-2025, NX-2026, NX-5205, UltraLITE 2023, UL-2023, NC-510 (hydrogenated product), LITE 2020 (ethylene oxide 1-adduct), NX-7507 (ethylene oxide 7-adduct), GX-5166 (ethylene oxide 7-adduct), GX-5167 (ethylene oxide 9-adduct), GX-5170 (ethylene oxide 12-adduct), LITE 2100, and LITE 2100R. Among these, preferred are NX-2021, NX-2022, NX-2023, NX-2023D, NX-2024, NX-2025, NX-2026, NX-5205, UltraLITE2023, UL-2023, NC-510 (hydrogenated product), LITE2020 (ethylene oxide 1-adduct), NX-7507 (ethylene oxide 7-adduct), GX-5166 (ethylene oxide 7-adduct), GX-5167 (ethylene oxide 9-adduct), and GX-5170 (ethylene oxide 12-adduct), More preferred are NX-2021, NX-2022, NX-2023, NX-2024, NX-2025, NX-2026, UltraLITE 2023, NC-510 (hydrogenated product), LITE 2020 (ethylene oxide 1-adduct), NX-7507 (ethylene oxide 7-adduct), GX-5166 (ethylene oxide 7-adduct), GX-5167 (ethylene oxide 9-adduct), and GX-5170 (ethylene oxide 12-adduct).

[0111] <<(II) Epoxidation Step>> In the epoxidation step, Rａ２ , R ｂ２ , R ｃ２ , and R ｄ２ The epoxidation is carried out by epoxidizing at least one linear aliphatic hydrocarbon group among the above. The epoxidation is not particularly limited and can be carried out by a known epoxidation method. Examples of the oxidizing agent include an oxygen-containing gas, an inorganic peroxide such as hydrogen peroxide or sodium peroxide, and an organic peroxide such as peracetic acid, perbenzoic acid, m-chloroperbenzoic acid, p-nitroperbenzoic acid, magnesium monoperoxyphthalate, peroxymaleic acid, peroxytrifluoroacetic acid, peroxyphthalic acid, peroxylauric acid, tert-butyl hydroperoxide, cumene hydroperoxide, menthyl hydroperoxide, or 1-methylhexane hydroperoxide.

[0112] In the epoxidation reaction, a catalyst can be used if necessary. Examples of the catalyst include metal compounds containing tungsten, molybdenum, vanadium, titanium, rhenium, ruthenium, etc., aldehydes such as acetaldehyde, isobutyraldehyde, isovaleraldehyde, trimethylacetaldehyde, etc., α-aminophosphonic acids such as α-aminomethylphosphonic acid, α-aminoethylphosphonic acid, etc., and quaternary onium salts such as trioctylmethylammonium chloride, trioctylethylammonium bromide, dilauryldimethylammonium iodide, and stearyldimethylbenzylammonium hydrogen phosphate.

[0113] The solvent used in the epoxidation reaction may be one that does not react with the oxidizing agent, such as hexane, heptane, octane, cyclohexane, benzene, toluene, ethylbenzene, xylene, ethyl acetate, butyl acetate, isobutyl acetate, methyl ethyl ketone, methyl isobutyl ketone, cyclohexanone, dichloromethane, chloroform, dimethyl sulfoxide, dimethylformamide, or dimethylacetamide.

[0114] The reaction temperature for the epoxidation reaction varies depending on the oxidizing agent, catalyst and solvent used, but is preferably 0 to 150°C, more preferably 0 to 60°C.

[0115] <Method for producing the mixture> <<Method for producing the compound represented by formula (3)>> The compound represented by formula (3) above can be synthesized by combining known synthesis reactions without any particular limitation. Examples of documents describing known synthesis reactions include the documents mentioned above in the section "Method for producing the compound." Typically, the compound represented by formula (3) above can be synthesized by combining known synthesis reactions such as an ether bond (-O-), an ester bond (-C(=O)-O-, -O-C(=O)-), a urethane bond (-C(=O)-NR １ -, -NR ２ It can be produced by appropriately bonding and / or modifying a plurality of raw material compounds using a reaction for forming a compound such as —C(═O)—. １ and R ２ has the same meaning as above. Specific methods for forming an ether bond, an ester bond, and a urethane bond include the same methods as those described above for the compound represented by formula (1) in the section "Method for producing compounds."

[0116] The compound represented by formula (3) can be produced, for example, by the reaction shown below. (Wherein, Bx, Y １１ ~Y ４１ , SP １１ ~SP ４１ , e, f, g, h, R ａ１ , R ｂ１ , R ｃ１ , R ｄ１ , p, and q have the same meanings as defined above.) That is, by reacting a compound having a carboxyl group represented by formula (D) with a compound having a hydroxyl group represented by formula (E) in a ratio of [the number of moles of carboxyl groups in the compound represented by formula (D):the number of moles of hydroxyl groups in the compound represented by formula (E)] of 1:2 to 2:1, preferably 1:1.5 to 1.5:1, and more preferably 1:1.0 to 1:1.5, the target compound represented by formula (3) can be produced with high selectivity and high yield.

[0117] In this case, as the dehydration condensation agent and the activator, the same dehydration condensation agent and the activator as those described above for the compound represented by the formula (1) in the section "Method for producing the compound" can be used in the amounts and by the addition method described above.

[0118] The solvent used in this reaction is not particularly limited as long as it is inert to the reaction, and examples thereof include the same solvents as those described above for the compound represented by formula (1) in the section "Method for producing the compound."

[0119] The amount of the solvent to be used is not particularly limited and can be determined appropriately taking into consideration the type of compound to be used, the scale of the reaction, and the like, but is usually 1 to 100 g per 1 g of the compound having a carboxyl group represented by formula (D).

[0120] The reaction proceeds smoothly in a temperature range from −10° C. to the boiling point of the solvent used, preferably 10° C. to 80° C., more preferably 15° C. to 50° C. The reaction time for each reaction varies depending on the reaction scale, but is usually several minutes to several tens of hours, preferably several minutes to 70 hours, more preferably several hours to 30 hours.

[0121] The compound represented by formula (3) can also be produced, for example, by the reaction shown below. (Wherein, Bx, Y １１ ~Y ４１ , SP １１ ~SP ４１ , e, f, g, h, R ａ１ , R ｂ１ , R ｃ１ , R ｄ１ , p, and q have the same meanings as defined above.) That is, by reacting a compound having an acid chloride group represented by formula (F) with a compound having a hydroxyl group represented by formula (E) in a ratio of [the number of moles of hydroxyl groups in the compound represented by formula (E) : the number of moles of acid chloride groups in the compound represented by formula (F)] of 1:2 to 2:1, preferably 1:1.5 to 1.5:1, and more preferably 1:1.0 to 1:1.2, the target compound represented by formula (3) can be produced with high selectivity and in high yield.

[0122] In this case, examples of the base to be used include the same bases as those mentioned above for the compound represented by formula (1) in the section "Method for producing the compound."

[0123] In this case, an activator can be used, which can be the same as the activator described above for the compound represented by formula (1) in the section "Method for producing the compound," in the amount and by the method of addition described above.

[0124] The solvent used in this reaction is not particularly limited as long as it is inert to the reaction, and examples thereof include the same solvents as those described above for the compound represented by formula (1) in the section "Method for producing the compound."

[0125] The amount of the solvent to be used is not particularly limited and can be determined appropriately taking into consideration the type of compound to be used, the scale of the reaction, and the like, but is usually 1 to 100 g per 1 g of the compound having a carboxyl group represented by formula (D).

[0126] The reaction proceeds smoothly in a temperature range from −20° C. to the boiling point of the solvent used, preferably −5° C. to 50° C., more preferably 0° C. to 40° C. The reaction time for each reaction varies depending on the reaction scale, but is usually from several minutes to 10-odd hours, preferably from several minutes to 10 hours, more preferably from several tens of minutes to 5 hours.

[0127] In this case, the compound having an acid chloride group represented by formula (F) may be a commercially available product, or may be synthesized from the compound having a carboxyl group represented by formula (D).

[0128] The compound having an acid chloride group represented by formula (F) can be produced as follows. (In the formula, p and q have the same meanings as above.)

[0129] In this case, examples of the chlorinating agent to be used include the same chlorinating agents as those described above for the compound represented by formula (1) in the section "Method for producing a compound." The chlorinating agent to be used is a compound having a carboxyl group represented by formula (D) reacted with the chlorinating agent in a ratio of [number of moles of carboxyl groups in the compound represented by formula (D):chlorinating agent] of 1:2 to 2:1, preferably 1:5 to 1:3, more preferably 1:1.0 to 1:1.5, thereby producing the target acid chloride compound represented by formula (F) with high selectivity and high yield.

[0130] In this case, an activator can be used, and the same activator as described above for the compound represented by formula (1) in the section "Method for producing the compound" can be used in the amount described above.

[0131] The solvent used in this reaction is not particularly limited as long as it is inert to the reaction, and examples thereof include the same solvents as those described above for the compound represented by formula (1) in the section "Method for producing the compound."

[0132] The amount of the solvent to be used is not particularly limited and can be determined appropriately taking into consideration the type of compound to be used, the scale of the reaction, and the like, but is usually 1 to 100 g per 1 g of the compound having a carboxyl group represented by formula (D).

[0133] The reaction proceeds smoothly in a temperature range from −20° C. to the boiling point of the solvent used, preferably −5° C. to 150° C., more preferably 0° C. to 110° C. The reaction time for each reaction varies depending on the reaction scale, but is usually from several minutes to 10-odd hours, preferably from several minutes to 10 hours, more preferably from several tens of minutes to 5 hours.

[0134] Examples of the compound represented by formula (E) include the same compounds as those described above for the compound represented by formula (B) in the section "Method for producing the compound" for the compound represented by formula (1).

[0135] The mixture of the present invention can be produced by mixing the compound represented by formula (1) and the compound represented by formula (3) produced by the above production method. For each of the compound represented by formula (1) and the compound represented by formula (3), one compound having a single structure and two or more compounds having different structures can be mixed in any ratio. The mixing ratio of the compounds represented by formula (1) and formula (3) corresponds to the content ratio of the compounds represented by formula (1) and formula (3) described above in the "Mixture" section.

[0136] In the epoxidation step included in the method for producing the compound of the present invention (the compound represented by the above formula (1)), when the epoxidation rate is 100%, a pure compound of the present invention is obtained. On the other hand, when the epoxidation rate is less than 100%, a mixture of the compounds represented by the above formulas (1) and (3) is obtained. In this mixture, Ax and Y in the above formula (1) １ , Y ２ , Y ３ , Y ４ , SP １ , SP ２ , SP ３ , SP ４ , a, b, c, d, x, y, and R in the above formula (4) ａ２ , R ｂ２ , R ｃ２ , R ｄ２ are Bx and Y in the above formula (3), respectively. １１ , Y ２１ , Y ３１ , Y ４１ , SP １１ , SP ２１ , SP ３１ , SP ４１ , e, f, g, h, p, q, R ａ１ , R ｂ１ , R ｃ１ , R ｄ１ Matches.

[0137] (Method of Use of Compound) The compound and mixture of the present invention are not particularly limited and can be used, for example, as a plasticizer when preparing a resin composition for forming a resin molded body, thereby imparting flexibility and elasticity to the resin molded body. Furthermore, when the compound and mixture of the present invention are used as a plasticizer, the resin molded body formed from the resin composition prepared using the compound and mixture of the present invention can be formed with good low-temperature tensile elongation and adhesion to polyurethane, while improving heat shrinkage resistance and melting properties. When the compound and mixture of the present invention are used as a plasticizer, the compound represented by formula (1) (compound of the present invention) or the compound represented by formula (3) may each be used alone as a single compound having a single structure, or two or more compounds having different structures may be used in combination in any ratio. That is, a mixture containing two or more compounds having different structures represented by formula (1) or (3) may also be used as a plasticizer.

[0138] (Plasticizer Composition) The plasticizer composition of the present invention (hereinafter sometimes abbreviated as "plasticizer composition") is characterized by containing at least the compound or mixture of the present invention described above. When a plasticizer composition containing the compound or mixture of the present invention is used in preparing a resin composition, the resin molded body formed from the prepared resin composition can have good low-temperature tensile elongation and adhesion to polyurethane, while improving heat shrinkage resistance and meltability. Here, the plasticizer composition of the present invention may further contain a plasticizer other than the compound or mixture of the present invention described above. The plasticizer other than the compound or mixture of the present invention contained in the plasticizer composition of the present invention is not particularly limited, and for example, polyester-based plasticizers and trimellitate-based plasticizers can be used. In particular, it is preferable that the plasticizer composition of the present invention further contains a polyester-based plasticizer in addition to the compound or mixture of the present invention. Furthermore, the plasticizer composition of the present invention may further contain a plasticizer other than the compound or mixture of the present invention and the polyester-based plasticizer described above (hereinafter sometimes referred to as "other plasticizers").

[0139] <Compound of the Present Invention> As the compound of the present invention used in preparing the plasticizer composition, one type of compound having a single structure may be used alone, or two or more types of compounds having different structures may be used in combination at any ratio.

[0140] <Mixture of the Present Invention> As the mixture of the present invention used for preparing the plasticizer composition, for the compound represented by the above formula (1) (compound of the present invention) or the compound represented by the above formula (3), one type of compound having a single structure may be used alone, or two or more types of compounds having different structures may be used in combination at any ratio.

[0141] When the plasticizer composition contains a polyester-based plasticizer, the content of the compound of the present invention in the plasticizer composition is preferably 1 part by mass or more, more preferably 1.5 parts by mass or more, even more preferably 2 parts by mass or more, even more preferably 2.5 parts by mass or more, still more preferably 3 parts by mass or more, particularly preferably 6.0 parts by mass or more, and preferably 70 parts by mass or less, more preferably 60 parts by mass or less, even more preferably 50 parts by mass or less, even more preferably 40 parts by mass or less, particularly preferably 20 parts by mass or less, and may be 18 parts by mass or less, or may be 16 parts by mass or less. When the content of the compound of the present invention in the plasticizer composition is equal to or greater than the above-mentioned lower limit, the formed resin molded article can have good low-temperature tensile elongation and adhesion to polyurethane, while improving heat shrinkage resistance and meltability. On the other hand, when the content of the compound of the present invention in the plasticizer composition is equal to or less than the above-mentioned upper limit, the formed resin molded article can have sufficiently high heat shrinkage resistance.

[0142] <Polyester-based plasticizer> The polyester-based plasticizer is a component that can impart sufficient tensile properties (e.g., tensile elongation, tensile strength, etc.) to a resin molded product formed using a resin composition containing the plasticizer composition. When a polyester-based plasticizer is used, when a laminate is formed by backing a polyurethane foam molded product on a resin molded product formed from a resin composition containing the plasticizer composition, the polyester-based plasticizer is unlikely to migrate from the resin molded product to the polyurethane foam molded product even at high temperatures, and the heat shrinkage resistance of the resin molded product can be further improved.

[0143] The polyester-based plasticizer is not particularly limited, and examples thereof include polyesters containing structural units derived from adipic acid (adipic acid-based polyesters), polyesters containing structural units derived from sebacic acid (sebacic acid-based polyesters), and polyesters containing structural units derived from phthalic acid (phthalic acid-based polyesters). These polyesters may be used alone or in combination of two or more in any ratio. Among these, from the viewpoint of further improving the heat shrinkage resistance of the resin molded article, it is preferable to use adipic acid-based polyesters (polyesters containing structural units derived from adipic acid) as the polyester-based plasticizer.

[0144] The viscosity of the polyester plasticizer is preferably 500 mPa·s or more, more preferably 1000 mPa·s or more, and is preferably 8000 mPa·s or less, more preferably 5000 mPa·s or less. The viscosity can be measured in accordance with JIS Z8803 at a temperature of 25°C.

[0145] <Other Plasticizers> The plasticizer composition may optionally further contain other plasticizers in addition to the compound of the present invention and the polyester-based plasticizer described above.

[0146] Specific examples of other plasticizers include the plasticizers described in WO 2016 / 098344, such as the above-mentioned (b1) polyester plasticizers and (b2) plasticizers other than phenols and modified products thereof. Among these, from the viewpoint of further improving the low-temperature tensile elongation of the resin molded body to be formed, it is preferable to use epoxidized vegetable oil, and it is more preferable to use epoxidized soybean oil.

[0147] The content of the other plasticizer in the plasticizer composition is not particularly limited, but can be from 0 to 15 parts by mass relative to 100 parts by mass of the polyester-based plasticizer. When an epoxidized vegetable oil such as epoxidized soybean oil is used as the other plasticizer, from the viewpoint of further improving the low-temperature tensile elongation of the formed resin molded body while ensuring sufficiently high heat shrinkage resistance of the resin molded body, the content of the epoxidized vegetable oil as the other plasticizer is preferably 2 parts by mass or more, more preferably 3 parts by mass or more, and even more preferably 4 parts by mass or more, and preferably 10 parts by mass or less, more preferably 7 parts by mass or less, and even more preferably 5 parts by mass or less, relative to 100 parts by mass of the polyester-based plasticizer.

[0148] (Resin Composition) An example of a resin composition may include (a) a resin and (b) a plasticizer composition of the present invention (hereinafter sometimes abbreviated as "(b) plasticizer composition"). In other words, the resin composition includes at least the (a) resin and the above-described compound of the present invention, and may optionally further include a polyester-based plasticizer and other plasticizers. The resin composition may optionally further include additives other than the above-described (a) resin and (b) plasticizer composition.

[0149] Furthermore, a resin molded article formed using a resin composition containing at least the compound of the present invention has excellent low-temperature tensile elongation, adhesion to polyurethane, and meltability. Furthermore, when a laminate is produced by backing a foamed polyurethane molded article with a resin molded article formed using the resin composition, the thermal shrinkage of the resin molded article in the laminate can be sufficiently suppressed. That is, a resin molded article formed using a resin composition containing at least the compound of the present invention also has excellent heat shrinkage resistance.

[0150] Therefore, by using a resin composition containing at least the compound of the present invention, it is possible to obtain a resin molded article suitable for use as an automobile interior material, such as an automobile instrument panel skin and a door trim skin, which has excellent low-temperature tensile elongation and heat shrinkage resistance.

[0151] From the viewpoint of easily obtaining a resin molded article that can be favorably used as an automobile interior material, for example, using a resin composition containing at least the compound of the present invention, the resin composition containing at least the compound of the present invention is preferably used for powder molding, more preferably for powder slush molding.

[0152] <(a) Resin> The (a) resin is not particularly limited as long as it can achieve the desired effects of the present invention, and any known resin can be used. Note that the (a) resin contained in the resin composition is a component different from the compound of the present invention, the plasticizer such as a polyester-based plasticizer, and the optional additives contained in the (b) plasticizer composition.

[0153] Here, the glass transition temperature of the resin (a) is preferably 50°C or higher and 100°C or lower.

[0154] As the (a) resin, it is preferable to use a resin containing halogen, more preferably a resin containing fluorine or a resin containing chlorine, even more preferably a resin containing chlorine, and particularly preferably a vinyl chloride resin.

[0155] Here, the content of vinyl chloride resin in (a) resin is not particularly limited, but is preferably 50% by mass or more, more preferably 70% by mass or more, even more preferably 90% by mass or more, and particularly preferably 100% by mass.

[0156] <<Vinyl Chloride Resin>> As the vinyl chloride resin, a particulate vinyl chloride resin is usually used. The vinyl chloride resin may contain, for example, one or more types of vinyl chloride resin particles, and may optionally further contain one or more types of vinyl chloride resin microparticles. Among these, the vinyl chloride resin preferably contains at least vinyl chloride resin particles, and more preferably contains vinyl chloride resin particles and vinyl chloride resin microparticles. The vinyl chloride resin may be produced by any conventionally known production method, such as suspension polymerization, emulsion polymerization, solution polymerization, or bulk polymerization. In this specification, "resin particles" refers to particles having a particle diameter of 30 μm or more, and "resin microparticles" refers to particles having a particle diameter of less than 30 μm.

[0157] Examples of vinyl chloride resins include homopolymers composed of vinyl chloride monomer units, as well as vinyl chloride copolymers containing preferably 50% by mass or more, more preferably 70% by mass or more, of vinyl chloride monomer units. Specific examples of monomers (comonomers) copolymerizable with vinyl chloride monomers that can constitute vinyl chloride copolymers include those described in International Publication No. WO 2016 / 098344. These components may be used alone or in combination of two or more in any ratio.

[0158] [Vinyl chloride resin particles] In the resin composition, the vinyl chloride resin particles usually function as a matrix resin (substrate). The vinyl chloride resin particles are preferably produced by a suspension polymerization method.

[0159] -Average Degree of Polymerization- The average degree of polymerization of the vinyl chloride resin constituting the vinyl chloride resin particles is preferably 800 or more, more preferably 1000 or more, and preferably 5000 or less, more preferably 3000 or less, and even more preferably 2800 or less. When the average degree of polymerization of the vinyl chloride resin constituting the vinyl chloride resin particles is above the above-mentioned lower limit, the physical strength of a resin molded article formed using the resin composition can be sufficiently ensured while, for example, improving tensile properties, particularly tensile elongation. Resin molded articles with good tensile elongation can be suitably used, for example, as automotive interior materials such as the surface of an automobile instrument panel, which has excellent ductility and breaks as designed without scattering fragments when an airbag is inflated and deployed. On the other hand, when the average degree of polymerization of the vinyl chloride resin constituting the vinyl chloride resin particles is below the above-mentioned upper limit, the meltability of the resin composition can be improved. In the present invention, the "average degree of polymerization" can be measured in accordance with JIS K6720-2.

[0160] -Average particle size- The average particle size of the vinyl chloride resin particles is usually 30 μm or more, preferably 50 μm or more, more preferably 100 μm or more, and preferably 500 μm or less, more preferably 200 μm or less. If the average particle size of the vinyl chloride resin particles is equal to or greater than the above-mentioned lower limit, the powder fluidity of the resin composition can be improved. On the other hand, if the average particle size of the vinyl chloride resin particles is equal to or less than the above-mentioned upper limit, the meltability of the resin composition can be improved, and the surface smoothness of the formed resin molded article can be improved. In the present invention, the "average particle size" can be measured as the volume average particle size by laser diffraction in accordance with JIS Z8825.

[0161] -Content- The content of vinyl chloride resin particles in the vinyl chloride resin is preferably 70% by mass or more, more preferably 80% by mass or more, and can be 100% by mass, and is preferably 95% by mass or less, and more preferably 90% by mass or less. If the content of vinyl chloride resin particles in the vinyl chloride resin is equal to or greater than the above-mentioned lower limit, the tensile elongation of a resin molded product formed using the resin composition can be improved while ensuring sufficient physical strength. On the other hand, if the content of vinyl chloride resin particles in the vinyl chloride resin is equal to or less than the above-mentioned upper limit, the powder flowability of the resin composition can be improved.

[0162] [Vinyl chloride resin fine particles] In the resin composition, vinyl chloride resin fine particles usually function as a dusting agent (powder flowability improver). The vinyl chloride resin fine particles are preferably produced by emulsion polymerization.

[0163] -Average Degree of Polymerization- The average degree of polymerization of the vinyl chloride resin constituting the vinyl chloride resin microparticles is preferably 500 or more, more preferably 700 or more, and preferably 2600 or less, and more preferably 2400 or less. If the average degree of polymerization of the vinyl chloride resin constituting the vinyl chloride resin microparticles as a dusting agent is equal to or greater than the above-mentioned lower limit, the powder fluidity of the resin composition can be improved and the tensile elongation of the resin molded article formed can be improved. On the other hand, if the average degree of polymerization of the vinyl chloride resin constituting the vinyl chloride resin microparticles is equal to or less than the above-mentioned upper limit, the meltability of the resin composition can be improved, and the surface smoothness of the resin molded article formed can be improved.

[0164] -Average particle size- Furthermore, the average particle size of the vinyl chloride resin fine particles is usually less than 30 μm, preferably 10 μm or less, more preferably 5 μm or less, preferably 0.1 μm or more, and more preferably 1 μm or more. If the average particle size of the vinyl chloride resin fine particles is equal to or greater than the above-mentioned lower limit, the powder fluidity of the resin composition can be improved, for example, without excessively reducing the size of the particles used as a dusting agent. On the other hand, if the average particle size of the vinyl chloride resin fine particles is equal to or less than the above-mentioned upper limit, the meltability of the resin composition can be improved, thereby improving the surface smoothness of the resulting resin molded article.

[0165] -Content- The content of vinyl chloride resin microparticles in the vinyl chloride resin may be 0% by mass, but is preferably 5% by mass or more, more preferably 10% by mass or more, and preferably 30% by mass or less, and more preferably 20% by mass or less. If the content of vinyl chloride resin microparticles in the vinyl chloride resin is equal to or greater than the above-mentioned lower limit, the powder fluidity of the resin composition can be improved. On the other hand, if the content of vinyl chloride resin microparticles in the vinyl chloride resin is equal to or less than the above-mentioned upper limit, the physical strength of the resin molded product formed can be increased.

[0166] <(b) Plasticizer Composition> As the (b) plasticizer composition, a plasticizer composition containing at least the compound or mixture of the present invention described above and optionally further containing a polyester-based plasticizer and other plasticizers is used.

[0167] The content of the compound or mixture of the present invention in the resin composition is preferably 1 part by mass or more, more preferably 1.5 parts by mass or more, even more preferably 2 parts by mass or more, even more preferably 2.5 parts by mass or more, still more preferably 3 parts by mass or more, particularly preferably 6.0 parts by mass or more, preferably 70 parts by mass or less, more preferably 60 parts by mass or less, even more preferably 50 parts by mass or less, even more preferably 40 parts by mass or less, particularly preferably 20 parts by mass or less, and may be 18 parts by mass or less, or may be 16 parts by mass or less. If the content of the compound or mixture of the present invention in the resin composition is equal to or greater than the above-mentioned lower limit, the low-temperature tensile elongation of the formed resin molded article can be further improved, and the adhesion of the resin molded article to a foamed polyurethane molded article can be improved. On the other hand, if the content of the compound of the present invention in the resin composition is equal to or less than the above-mentioned upper limit, the heat shrinkage resistance of the formed resin molded article can be ensured to be sufficiently high.

[0168] Furthermore, when the (b) plasticizer composition contains a polyester-based plasticizer, the content of the polyester-based plasticizer in the resin composition is preferably 30 parts by mass or more, more preferably 50 parts by mass or more, even more preferably 70 parts by mass or more, even more preferably 80 parts by mass or more, even more preferably 85 parts by mass or more, and preferably 200 parts by mass or less, more preferably 180 parts by mass or less, even more preferably 150 parts by mass or less, even more preferably 130 parts by mass or less, even more preferably 110 parts by mass or less, and particularly preferably 100 parts by mass or less, relative to 100 parts by mass of the (a) resin. If the content of the polyester-based plasticizer in the resin composition is equal to or greater than the above-mentioned lower limit, the heat shrinkage resistance of the formed resin molded product can be further improved. On the other hand, if the content of the polyester-based plasticizer in the resin composition is equal to or less than the above-mentioned upper limit, the formed resin molded product can have sufficiently high adhesion to a polyurethane foam molded product.

[0169] The content of the other plasticizer in the resin composition is not particularly limited, but can be from 0 to 15 parts by mass per 100 parts by mass of the (a) resin. When an epoxidized vegetable oil such as epoxidized soybean oil is used as the other plasticizer, from the viewpoint of further improving the low-temperature tensile elongation of the formed resin molded body while ensuring sufficiently high heat shrinkage resistance of the resin molded body, the content of the epoxidized vegetable oil as the other plasticizer is preferably 2 parts by mass or more, more preferably 3 parts by mass or more, and even more preferably 4 parts by mass or more, and preferably 10 parts by mass or less, and more preferably 7 parts by mass or less, per 100 parts by mass of the (a) resin.

[0170] The total content of the compound of the present invention, the polyester plasticizer, and the other plasticizers in the resin composition (i.e., the content of the (b) plasticizer composition) is preferably 31 parts by mass or more, more preferably 53.5 parts by mass or more, even more preferably 75 parts by mass or more, even more preferably 86.5 parts by mass or more, even more preferably 92 parts by mass or more, and preferably 235 parts by mass or less, more preferably 208 parts by mass or less, even more preferably 176 parts by mass or less, even more preferably 154 parts by mass or less, even more preferably 129 parts by mass or less, and particularly preferably 119 parts by mass or less. If the content of the plasticizer composition in the resin composition is within the above-mentioned specified range, molding of the resin composition (e.g., powder molding) can be easily performed, and the formed resin molded product can simultaneously achieve high levels of low-temperature tensile elongation, heat shrinkage resistance, and adhesion to foamed polyurethane molded products.

[0171] <Additives> The resin composition may further contain various additives in addition to the components described above. The additives are not particularly limited, and examples thereof include lubricants; stabilizers such as perchloric acid-treated hydrotalcite, zeolite, β-diketone, and fatty acid metal salts; mold release agents; dusting agents other than the above-mentioned vinyl chloride resin fine particles; impact resistance modifiers; perchloric acid compounds other than perchloric acid-treated hydrotalcite (e.g., sodium perchlorate and potassium perchlorate); antioxidants; mildew inhibitors; flame retardants; antistatic agents; fillers; light stabilizers; foaming agents; and pigments.

[0172] The additives that may be contained in the resin composition include, for example, those described in WO 2016 / 098344, and the preferred content thereof may be the same as that described in WO 2016 / 098344.

[0173] <Method for preparing resin composition> The resin composition can be prepared by mixing the above-mentioned components. Here, the method for mixing the (a) resin, (b) plasticizer composition, and various additives further blended as necessary is not particularly limited, and for example, a method can be used in which the components excluding the dusting agent (including vinyl chloride resin fine particles) are mixed by dry blending, and then the dusting agent is added and mixed. Here, it is preferable to use a Henschel mixer for dry blending. In addition, the temperature during dry blending is not particularly limited, and is preferably 50°C or higher, more preferably 70°C or higher, and preferably 200°C or lower.

[0174] <Uses of Resin Composition> The obtained resin composition can be suitably used for powder molding, and more suitably used for powder slush molding.

[0175] (Resin Molded Article) An example of a resin molded article can be obtained by molding the above-described resin composition by any method. Since the resin molded article is formed using the above-described resin composition, it typically contains at least (a) a resin and (b) a plasticizer composition. That is, the resin molded article typically contains at least (a) a resin and the compound of the present invention, and optionally further contains a polyester-based plasticizer, other plasticizers, and additives. A resin molded article containing at least the compound of the present invention has excellent low-temperature tensile elongation, adhesion to polyurethane, heat shrinkage resistance, and meltability. Therefore, the resin molded article can be suitably used as an automotive interior material, such as the skin of an automotive instrument panel.

[0176] <Method for forming resin molded body> When a resin molded body is formed by powder slush molding, the mold temperature during powder slush molding is not particularly limited, but is preferably 200°C or higher, more preferably 220°C or higher, and is preferably 300°C or lower, and more preferably 280°C or lower.

[0177] The resin molded article can be produced by any method, including, but not limited to, the following method. Specifically, the resin composition is sprinkled onto a mold at the temperature range described above, left for 5 to 30 seconds, the excess resin composition is shaken off, and the mold is further left at a given temperature for 30 seconds to 3 minutes. The mold is then cooled to 10 to 60°C, and the resulting resin molded article is removed from the mold. A sheet-like molded article conforming to the shape of the mold is then obtained.

[0178] (Laminate) An example of a laminate includes a polyurethane foam molded body and the above-described resin molded body. The resin molded body usually constitutes one surface of the laminate. The laminate is formed, for example, using the above-described resin composition, and includes a resin molded body that has excellent low-temperature tensile elongation, adhesion to polyurethane, heat shrinkage resistance, and meltability. Therefore, the laminate is suitable for use as an automobile interior part, particularly as an automobile interior material that forms an automobile instrument panel.

[0179] Here, the method for laminating the polyurethane foam molded body and the resin molded body is not particularly limited, and the following methods can be used, for example. That is, (1) a method in which a polyurethane foam molded body and a resin molded body are separately prepared and then bonded together by heat fusion, heat adhesion, or using a known adhesive, etc.; (2) a method in which isocyanates and polyols, which are raw materials for the polyurethane foam molded body, are reacted on the resin molded body to polymerize, and polyurethane is foamed by a known method, thereby directly forming a polyurethane foam molded body on the resin molded body; etc. Among these, the latter method (2) is preferred because of its simple process and the ease with which the resin molded body and the polyurethane foam molded body can be firmly bonded together even when laminates of various shapes are obtained.

[0180] The present invention will be described in detail below based on examples, but the present invention is not limited to these examples. In the following description, "%" and "parts" representing amounts are based on mass unless otherwise specified. The tensile properties at low temperatures of the vinyl chloride resin molded sheet (vinyl chloride resin molded product), heat shrinkage resistance, adhesion to a polyurethane foam molded product, and meltability of the vinyl chloride resin composition were measured and evaluated by the following methods.

[0181] <Tensile Properties (Tensile Strength, Tensile Elongation) at Low Temperatures> The obtained vinyl chloride resin molded sheet was punched out with a No. 1 dumbbell as defined in JIS K6251, and the tensile elongation at break (%) and tensile stress at break (MPa) were measured at a low temperature of -25°C at a pulling rate of 200 mm / min in accordance with JIS K7113. The larger the tensile elongation at break value, the better the vinyl chloride resin molded sheet's tensile elongation at low temperatures (low-temperature tensile elongation). Also, the larger the tensile stress at break value, the better the vinyl chloride resin molded sheet's tensile strength at low temperatures.

[0182] <Heat Shrinkage Resistance> The length of the short side of the vinyl chloride resin molded sheet of the obtained laminate was measured using a three-dimensional measuring machine ("Crysta-Plus M443" manufactured by Mitutoyo Corporation), and this was recorded as the actual measured value before heating. The laminate was then stored and heated in a gear oven ("Gear Oven" manufactured by Toyo Seiki Seisaku-sho, Ltd.) at 120°C. After 600 hours, the laminate was removed from the oven, and the length of the short side of the vinyl chloride resin molded sheet of the laminate was measured using the above three-dimensional measuring machine, and this was recorded as the actual measured value after heating. Using the actual measured values ​​before and after heating, the heat shrinkage rate (%) shown in the following formula was calculated: Heat shrinkage rate [%] = 100 × (actual measured value before heating - actual measured value after heating) / actual measured value before heating. Note that the smaller the heat shrinkage rate value, the smaller the heat shrinkage of the vinyl chloride resin molded sheet, indicating that the vinyl chloride resin molded sheet has excellent heat shrinkage resistance.

[0183] <Adhesion to Polyurethane Foam Molded Product> Using a laminate comprising a vinyl chloride resin molded sheet backed by a polyurethane foam molded product, the vinyl chloride resin molded sheet was peeled off from the polyurethane foam molded product. After peeling, the surface of the vinyl chloride resin molded sheet backed by the polyurethane foam molded product was visually inspected to evaluate the adhesion of the vinyl chloride resin molded sheet (vinyl chloride resin molded product) to the polyurethane molded product. Visual inspection of the vinyl chloride resin molded sheet to determine whether the surface of the polyurethane foam molded product remained over the entire surface was evaluated as "foam failure" (evaluated as A in Tables 1 and 2). Visual inspection of the vinyl chloride resin molded sheet to determine whether the surface of the polyurethane foam molded product remained over only a portion of the surface of the vinyl chloride resin molded sheet and not over other portions was evaluated as "partial interfacial peeling" (evaluated as B in Tables 1 and 2). Visual inspection of the vinyl chloride resin molded sheet to determine whether the surface of the polyurethane foam molded product remained over only a portion of the surface of the vinyl chloride resin molded sheet and not over other portions was evaluated as "complete interfacial peeling" (evaluated as C in Tables 1 and 2). The more areas on the surface of the vinyl chloride resin molded sheet that have the surface portion of the polyurethane foam remaining, the higher the adhesion of the vinyl chloride resin molded sheet (vinyl chloride resin molded product) to the polyurethane foam.

[0184] <Melting Properties> A belt-shaped mold was placed on a hot plate heated in stages at equal intervals from 170°C to 270°C to obtain a stepwise heated mold. The obtained vinyl chloride resin composition was then sprinkled onto the stepwise heated mold to a thickness of 1 mm and allowed to melt by leaving it for 45 seconds. Next, excess vinyl chloride resin composition was shaken off, and the mold was cooled with water to remove a vinyl chloride resin molded sheet in which the vinyl chloride resin was molded into a belt shape from the mold. The surface of the demolded vinyl chloride resin molded sheet was visually observed, and the temperature of the mold at the melted portion was recorded as the melting temperature of the vinyl chloride resin composition. In the belt-shaped vinyl chloride resin molded sheet, a portion having a smooth surface without any particulate residue was determined as the "melted portion." The lower the melting temperature, the better the melting property of the vinyl chloride resin composition.

[0185] (Synthesis Examples) The compounds used in the examples were prepared as follows. The nuclear magnetic resonance (NMR) analysis of "Cardolite NX-2026" (Cardolite Co., Ltd.) used in the following synthesis examples was carried out. １ H-NMR, １３ The NMR (C-NMR) and IR (ATR) spectra obtained by the respective measurements are shown in Figures 1 to 3. The NMR ( １ H-NMR, １３ The spectra obtained by the measurements of C-NMR, C-H COSY, and IR (ATR) are shown in Figures 4 to 7. １ From the H-NMR spectrum, it was found that the signal position of the hydroxyl group was 3.33 ppm.

[0186] Synthesis Example 1 Synthesis of Diester Mixture 1 Diester mixture 1 was synthesized from "Cardolite NX-2026" (manufactured by Cardolite Co., Ltd.) according to the following synthesis scheme. In the synthesis scheme, R represents any one of the four hydrocarbon groups having 15 carbon atoms shown below, and * represents the position at which the group is bonded to the benzene ring via a single bond (the same applies to Synthesis Examples 2 to 18 below). "Cardolite NX-2026" and diester mixture 1 each represent a mixture of compounds in which R is any one of the four hydrocarbon groups shown below, and the two R groups contained in diester mixture 1 may be the same or different. In a three-neck reactor equipped with a thermometer, 80 g (0.27 mol) of Cardolite NX-2026 (Cardolite) was dissolved in 150 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. To this solution, 18.57 g (0.13 mol) of adipic acid and 6.83 g (0.056 mol) of N,N-dimethyl-4-aminopyridine (DMAP) were added and dissolved. 53.58 g (0.28 mol mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added while adjusting the temperature to 25°C or below in a water bath, and the entire mixture was stirred at 25°C for 24 hours. After completion of the reaction, the reaction solution was poured into 2500 mL of distilled water and extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off. The solvent was removed by evaporation using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 (volume ratio)) to obtain 81 g of a colorless oil of diester mixture 1. The structure of diester mixture 1 was identified by NMR and infrared absorption spectroscopy. １ H-NMR (500MHz, CDCl ３ , TMS, δ ppm): the generation of a signal at 1.90-1.85 ppm derived from the α-position of the carbonyl carbon was confirmed. １３ C-NMR (500MHz, CDCl ３, TMS, δ ppm): The generation of a signal at 171.86 ppm originating from the carbonyl carbon was confirmed. IR (ATR): The generation of a signal at 1761 cm originating from the ester bond －１ The generation of the peak was confirmed. １ H-NMR, １３ The C-NMR and IR (ATR) spectra are shown in FIGS. 8 to 10.

[0187] Synthesis Example 2 Synthesis of Diester Mixture 2 Diester mixture 2 was synthesized from "Cardolite NX-2026" (manufactured by Cardolite Co., Ltd.) according to the following synthesis scheme. Note that "Cardolite NX-2026" and diester mixture 2 each represent a mixture of compounds in which R is any of the following four hydrocarbon groups, and the two Rs contained in diester mixture 2 may be the same or different. In a three-neck reactor equipped with a thermometer, 80 g (0.27 mol) of Cardolite NX-2026 (Cardolite) was dissolved in 150 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. To this solution, 25.69 g (0.13 mol) of sebacic acid and 6.83 g (0.056 mol) of N,N-dimethyl-4-aminopyridine (DMAP) were added and dissolved. 53.58 g (0.28 mol mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added while adjusting the temperature to 25°C or below in a water bath, and the entire mixture was stirred at 25°C for 24 hours. After completion of the reaction, the reaction solution was poured into 2500 mL of distilled water and extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off. The solvent was removed by evaporation using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 (volume ratio)) to obtain 82 g of a colorless oil of diester mixture 2. The structure of diester mixture 2 was identified by NMR and infrared absorption spectroscopy. １ H-NMR (500MHz, CDCl ３, TMS, δ ppm): the generation of a signal at 1.79-1.73 ppm derived from the α-position of the carbonyl carbon was confirmed. １３ C-NMR (500MHz, CDCl ３ , TMS, δ ppm): The generation of a signal at 172.38 ppm originating from the carbonyl carbon was confirmed. IR (ATR): The generation of a signal at 1759 cm originating from the ester bond －１ The generation of the peak was confirmed. １ H-NMR, １３ The C-NMR and IR (ATR) spectra are shown in FIGS. 11 to 13.

[0188] Synthesis Example 3 Synthesis of Diester Mixture 3 Diester mixture 3 was synthesized from "Cardolite NX-2026" (manufactured by Cardolite Co., Ltd.) according to the following synthesis scheme. Note that "Cardolite NX-2026" and diester mixture 3 each represent a mixture of compounds in which R is any of the following four hydrocarbon groups, and the two Rs contained in diester mixture 3 may be the same or different. In a three-neck reactor equipped with a thermometer, 80 g (0.27 mol) of Cardolite NX-2026 (Cardolite) was dissolved in 150 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. To this solution, 21.10 g (0.13 mol) of terephthalic acid and 6.83 g (0.056 mol) of N,N-dimethyl-4-aminopyridine (DMAP) were added and dissolved. 53.58 g (0.28 mol mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added while adjusting the temperature to 25°C or below in a water bath, and the entire mixture was stirred at 25°C for 24 hours. After completion of the reaction, the reaction solution was poured into 2500 mL of distilled water and extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off. The solvent was removed by evaporation using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 (volume ratio)) to obtain 82 g of a colorless oil of diester mixture 3. The structure of diester mixture 3 was identified by NMR and infrared absorption spectroscopy. １ H-NMR (500MHz, CDCl ３ , TMS, δ ppm): the generation of a signal at 8.33 ppm derived from a new aromatic ring was confirmed. １３ C-NMR (500MHz, CDCl ３ , TMS, δ ppm): The generation of a signal at 164.45 ppm originating from the carbonyl carbon was confirmed. IR (ATR): The generation of a signal at 1738 cm originating from the ester bond －１ The generation of the peak was confirmed. １ H-NMR, １３ The C-NMR and IR (ATR) spectra are shown in FIGS. 14 to 16.

[0189] Synthesis Example 4 Synthesis of Diester Mixture 4 Diester mixture 4 was synthesized from "Cardolite NX-7507" (manufactured by Cardolite Co., Ltd.) according to the following synthesis scheme. Note that "Cardolite NX-7507" and diester mixture 4 each represent a mixture of compounds in which R is any of the following four hydrocarbon groups, and the two Rs contained in diester mixture 4 may be the same or different. In a three-neck reactor equipped with a thermometer, 80 g (0.13 mol) of Cardolite NX-7507 (Cardolite) was dissolved in 150 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. To this solution, 9.13 g (0.062 mol) of adipic acid and 3.22 g (0.026 mol) of N,N-dimethyl-4-aminopyridine (DMAP) were added and dissolved. 25.24 g (0.13 mol mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added while adjusting the temperature to 25°C or below in a water bath, and the entire volume was stirred at 25°C for 24 hours. After completion of the reaction, the reaction solution was poured into 2500 mL of distilled water and extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off. The solvent was removed by evaporation using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=90:10 (volume ratio)) to obtain 84 g of a pale brown oil of diester mixture 4. The structure of diester mixture 4 was identified by NMR and infrared absorption spectroscopy. １ H-NMR (500MHz, CDCl ３ , TMS, δ ppm): disappearance of the signal at 3.33 ppm derived from the hydroxyl group of Cardolite NX-7507 (manufactured by Cardolite Co., Ltd.) was confirmed. １３ C-NMR (500MHz, CDCl ３ , TMS, δ ppm): The generation of signals at 175.03 ppm and 173.23 ppm due to carbonyl carbon was confirmed. IR (ATR): The generation of signals at 1736 cm due to an ester bond was confirmed. －１ , 1685 cm －１The generation of the peak was confirmed. １ H-NMR, １３ The C-NMR and IR (ATR) spectra are shown in FIGS. 17 to 19.

[0190] Synthesis Example 5 Synthesis of Diester Mixture 5 Diester mixture 5 was synthesized from "Cardolite NX-7507" (manufactured by Cardolite Co., Ltd.) according to the following synthesis scheme. Note that "Cardolite NX-7507" and diester mixture 5 each represent a mixture of compounds in which R is any of the following four hydrocarbon groups, and the two Rs contained in diester mixture 5 may be the same or different. In a three-neck reactor equipped with a thermometer, 80 g (0.13 mol) of Cardolite NX-7507 (Cardolite) was dissolved in 150 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. To this solution, 13.30 g (0.066 mol) of sebacic acid and 5.30 g (0.043 mol) of N,N-dimethyl-4-aminopyridine (DMAP) were added and dissolved. 27.74 g (0.15 mol mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added while adjusting the temperature to 25°C or below in a water bath, and the entire volume was stirred at 25°C for 24 hours. After completion of the reaction, the reaction solution was poured into 2500 mL of distilled water and extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off. The solvent was removed by evaporation using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=90:10 (volume ratio)) to obtain 81 g of a pale brown oil of diester mixture 5. The structure of diester mixture 5 was identified by NMR and infrared absorption spectroscopy. １ H-NMR (500MHz, CDCl ３ , TMS, δ ppm): disappearance of the signal at 3.33 ppm derived from the hydroxyl group of Cardolite NX-7507 (manufactured by Cardolite Co., Ltd.) was confirmed. １３ C-NMR (500MHz, CDCl ３, TMS, δ ppm): The generation of signals at 175.01 ppm and 173.69 ppm due to carbonyl carbon was confirmed. IR (ATR): The generation of signals at 1734 cm due to an ester bond was confirmed. －１ , 1684 cm －１ The generation of the peak was confirmed. １ H-NMR, １３ The C-NMR and IR (ATR) spectra are shown in FIGS. 20 to 22.

[0191] Synthesis Example 6 Synthesis of Diester Mixture 6 Diester mixture 6 was synthesized from "Cardolite NX-7507" (manufactured by Cardolite Co., Ltd.) according to the following synthesis scheme. Note that "Cardolite NX-7507" and diester mixture 6 each represent a mixture of compounds in which R is any of the following four hydrocarbon groups, and the two Rs contained in diester mixture 6 may be the same or different. In a three-neck reactor equipped with a thermometer, 84.58 g (0.139 mol) of Cardolite NX-7507 (Cardolite) was dissolved in 250 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. To this solution, 11.0 g (0.066 mol) of terephthalic acid and 3.74 g (0.031 mol) of N,N-dimethyl-4-aminopyridine (DMAP) were added and dissolved. 29.32 g (0.153 mol mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added while adjusting the temperature to 25°C or below in a water bath, and the entire volume was stirred at 25°C for 22 hours. After completion of the reaction, the reaction solution was poured into 2500 mL of distilled water and extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off. The solvent was removed using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 85:15 (volume ratio)) to obtain 82 g of diester mixture 6 as a pale brown oil. The structure of diester mixture 6 was identified by NMR and infrared absorption spectroscopy. １ H-NMR (500MHz, CDCl ３, TMS, δ ppm): The disappearance of the signal at 3.33 ppm derived from the hydroxyl group of Cardolite NX-7507 (manufactured by Cardolite Co., Ltd.) was confirmed. The production of aromatic hydrogen of terephthalic acid was confirmed at 8.11 ppm. １３ C-NMR (500MHz, CDCl ３ , TMS, δ ppm): The generation of signals at 174.96 ppm and 165.62 ppm due to carbonyl carbon was confirmed. IR (ATR): The generation of signals at 1720 cm due to an ester bond was confirmed. －１ , 1689 cm －１ The generation of the peak was confirmed. １ H-NMR, １３ The C-NMR and IR (ATR) spectra are shown in FIGS. 23 to 25.

[0192] Synthesis Example 7 Synthesis of Diester Mixture 7 The same operations as in Synthesis Example 1 were performed, except that the amount of “Cardolite NX-2026” (manufactured by Cardolite Co., Ltd.) was changed from 80 g to 85.3 g, the amount of adipic acid was changed from 18.57 g to 16.0 g of succinic acid, the amount of N,N-dimethylamino-4-pyridine (DMAP) was changed from 6.83 g to 7.28 g, and the amount of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was changed from 53.58 g to 57.0 g, to obtain 83 g of diester mixture 7 as a colorless oil.

[0193] Synthesis Example 8 Synthesis of diester mixture 8 The same operations as in Synthesis Example 1 were performed, except that 80 g of "Cardolite NX-2026" (manufactured by Cardolite Co., Ltd.) was changed to 83.3 g, 18.57 g of adipic acid was changed to 27.0 g of 1,3,5-pentatricarboxylic acid, 6.83 g of N,N-dimethylamino-4-pyridine (DMAP) was changed to 7.11 g, and 53.58 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was changed to 83.48 g, to obtain 83 g of diester mixture 8 as a colorless oil.

[0194] Synthesis Example 9 Synthesis of diester mixture 9 The same operations as in Synthesis Example 1 were performed, except that 80 g of "Cardolite NX-2026" (manufactured by Cardolite Co., Ltd.) was changed to 83.1 g, 18.57 g of adipic acid was changed to 23.0 g of 3-ethyl-3-methylglutaric acid, 6.83 g of N,N-dimethylamino-4-pyridine (DMAP) was changed to 7.10 g, and 53.58 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was changed to 55.57 g, to obtain 83 g of diester mixture 9 as a colorless oil.

[0195] Synthesis Example 10: Synthesis of epoxidized diester mixture 1 According to the following synthesis scheme, epoxidized diester mixture 1 was synthesized from diester mixture 1 synthesized in Synthesis Example 1. Note that diester mixture 1 and epoxidized diester mixture 1 each represent a mixture of compounds in which R is any of the following four hydrocarbon groups, and the two Rs contained in epoxidized diester mixture 1 may be the same or different. In a three-neck reactor equipped with a thermometer, 80 g of the diester mixture 1:1 was dissolved in 200 mL of toluene under a nitrogen stream. To this solution, 140 g (2.33 mol) of acetic acid and 11.4 g (0.11 mol) of phosphoric acid were added and dissolved. The solution was heated to 50°C, and 182.2 ml (2.33 mol; specific gravity 1.45) of 30 wt% hydrogen peroxide was slowly added dropwise over 30 minutes. The entire solution was stirred at 50°C for 6 hours. After completion of the reaction, 30 wt% aqueous sodium bisulfite solution was slowly added to the reaction solution under vigorously stirring while cooling in an ice bath. While checking with potassium iodide starch paper, the solution was added until the potassium iodide starch paper no longer discolored, and then extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was then collected and cooled in an ice bath. A saturated aqueous sodium bicarbonate solution was slowly added to the solution to make it weakly basic (pH = 8). The ethyl acetate layer collected after separation was washed with 300 ml of saturated brine. The ethyl acetate layer collected after separation was dried over anhydrous sodium sulfate, and then the sodium sulfate was filtered off. The solvent was removed by evaporation using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50 (volume ratio)) to obtain 80 g of epoxidized diester mixture 1 as a pale yellow oil. The structure of epoxidized diester mixture 1 was identified by NMR and infrared absorption spectroscopy. １ H-NMR (500MHz, CDCl ３ , TMS, δ ppm): A decrease in the signal at 6.60 to 4.70 ppm attributable to double bonds was confirmed. In addition, the generation of peaks at 3.22 to 2.78 ppm attributable to epoxy groups was confirmed. The conversion rate calculated from the decrease in the signal attributable to double bonds was 85.6%. １３ C-NMR (500MHz, CDCl ３ , TMS, δ ppm): the generation of signals at 57.27-46.42 ppm derived from epoxy groups was confirmed. １ H-NMR, １３ The C-NMR and IR (ATR) spectra are shown in FIGS. 26 to 28.

[0196] Synthesis Example 11 Synthesis of Epoxidized Diester Mixture 2 Epoxidized diester mixture 2 was synthesized from diester mixture 2 synthesized in Synthesis Example 2 according to the following synthesis scheme. Note that diester mixture 2 and epoxidized diester mixture 2 each represent a mixture of compounds in which R is any of the following four hydrocarbon groups, and the two Rs contained in epoxidized diester mixture 2 may be the same or different. In a three-neck reactor equipped with a thermometer, 80 g of diester mixture 2 was dissolved in 200 mL of toluene under a nitrogen stream. To this solution, 132.5 g (2.21 mol) of acetic acid and 10.8 g (0.11 mol) of phosphoric acid were added and dissolved. This solution was heated to 50°C, and 172.5 ml (2.21 mol; specific gravity 1.45) of 30 wt% hydrogen peroxide was slowly added dropwise over 30 minutes. The entire solution was stirred at 50°C for 6 hours. After completion of the reaction, 30 wt% aqueous sodium bisulfite solution was slowly added to the reaction solution under vigorously stirring while cooling in an ice bath. While checking with potassium iodide starch paper, the solution was added until the potassium iodide starch paper no longer discolored, and then extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was then collected and cooled in an ice bath. A saturated aqueous sodium bicarbonate solution was slowly added to the solution to make it weakly basic (pH = 8). The ethyl acetate layer collected after separation was washed with 300 ml of saturated brine. The ethyl acetate layer collected after separation was dried over anhydrous sodium sulfate, and then the sodium sulfate was filtered off. The solvent was removed by evaporation using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50 (volume ratio)) to obtain 80 g of epoxidized diester mixture 2 as a pale yellow oil. The structure of epoxidized diester mixture 2 was identified by NMR and infrared absorption spectroscopy. １ H-NMR (500MHz, CDCl ３ , TMS, δ ppm): A decrease in the signal at 6.00-4.70 ppm attributable to double bonds was confirmed. Also, the generation of a peak at 3.22-2.78 ppm attributable to epoxy groups was confirmed. The conversion rate calculated from the decrease in the signal attributable to double bonds was 87.6%.１３ C-NMR (500MHz, CDCl ３ , TMS, δ ppm): the generation of signals at 57.27-46.33 ppm derived from epoxy groups was confirmed. １ H-NMR, １３ The C-NMR and IR (ATR) spectra are shown in FIGS. 29 to 31.

[0197] Synthesis Example 12 Synthesis of Epoxidized Diester Mixture 3 Epoxidized diester mixture 3 was synthesized from diester mixture 3 synthesized in Synthesis Example 3 according to the following synthesis scheme. Note that diester mixture 3 and epoxidized diester mixture 3 each represent a mixture of compounds in which R is any of the following four hydrocarbon groups, and the two Rs contained in epoxidized diester mixture 3 may be the same or different. In a three-neck reactor equipped with a thermometer, 80 g of the diester mixture (3:3) was dissolved in 200 mL of toluene under a nitrogen stream. To this solution, 137.2 g (2.28 mol) of acetic acid and 11.2 g (0.11 mol) of phosphoric acid were added and dissolved. This solution was heated to 50°C, and 178.6 ml (2.28 mol; specific gravity: 1.45) of 30 wt% hydrogen peroxide was slowly added dropwise over 30 minutes. The entire solution was stirred at 50°C for 6 hours. After completion of the reaction, 30 wt% aqueous sodium bisulfite solution was slowly added to the reaction solution under vigorously stirring while cooling in an ice bath. While checking with potassium iodide starch paper, the solution was added until the potassium iodide starch paper no longer discolored, and then extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was then collected and cooled in an ice bath. A saturated aqueous sodium bicarbonate solution was slowly added to the solution to make it weakly basic (pH = 8). The ethyl acetate layer collected after separation was washed with 300 ml of saturated brine. The ethyl acetate layer collected after separation was dried over anhydrous sodium sulfate, and then the sodium sulfate was filtered off. The solvent was removed by evaporation using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50 (volume ratio)) to obtain 81 g of epoxidized diester mixture 3 as a pale brown oil. The structure of epoxidized diester mixture 3 was identified by NMR and infrared absorption spectroscopy. １ H-NMR (500MHz, CDCl ３ , TMS, δ ppm): A decrease in the signal at 6.00-4.70 ppm attributable to double bonds was confirmed. Also, the generation of a peak at 3.22-2.78 ppm attributable to epoxy groups was confirmed. The conversion rate calculated from the decrease in the signal attributable to double bonds was 88.4%. １３ C-NMR (500MHz, CDCl ３ , TMS, δ ppm): the generation of signals at 57.36-46.43 ppm derived from epoxy groups was confirmed. １ H-NMR, １３ The C-NMR and IR (ATR) spectra are shown in FIGS. 32 to 34.

[0198] Synthesis Example 13 Synthesis of Epoxidized Diester Mixture 4 According to the following synthesis scheme, epoxidized diester mixture 4 was synthesized from diester mixture 4 synthesized in Synthesis Example 4. Note that diester mixture 4 and epoxidized diester mixture 4 each represent a mixture of compounds in which R is any of the following four hydrocarbon groups, and the two Rs contained in epoxidized diester mixture 4 may be the same or different. In a three-neck reactor equipped with a thermometer, 80 g (0.06 mol) of the diester mixture 4 was dissolved in 500 mL of methylene chloride under a nitrogen stream. 1.93 g (0.018 mol) of sodium carbonate was added to this solution, which was then cooled in an ice bath. While cooling this solution in an ice bath, 370.1 g (0.44 mol as peracetic acid) of 9% peracetic acid in acetic acid (manufactured by Aldrich) was slowly added dropwise over 1 hour, and the entire mixture was stirred for 1 hour while still in the ice bath. The reaction solution was then returned to room temperature and stirred for 18 hours. The reaction solution was again cooled in an ice bath, and 185 g (0.22 mol) of 9% peracetic acid in acetic acid (manufactured by Aldrich) was slowly added dropwise over 30 minutes. The entire mixture was returned to room temperature and stirred for an additional 20 hours. After completion of the reaction, 1 mol / L aqueous sodium thiosulfate solution was slowly added to the reaction solution under vigorously stirring while cooling it in an ice bath. While checking with potassium iodide starch paper, the mixture was added until the potassium iodide starch paper no longer discolored, and then extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was then collected and cooled in an ice bath. A saturated aqueous solution of sodium bicarbonate was slowly added to make the mixture weakly basic (pH = 8). The collected ethyl acetate layer was separated and washed with 300 mL of saturated saline. The collected ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off. The solvent was removed by evaporation using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 85:15 (volume ratio)) to obtain 80 g of epoxidized diester mixture 4 as a pale brown oil. The structure of epoxidized diester mixture 1 was identified by NMR and infrared absorption spectroscopy. 　１ H-NMR (500MHz, CDCl ３, TMS, δ ppm): The conversion rate of the double bond calculated from the remaining amount of the signal at 6.60 to 5.20 ppm derived from the double bond was 90.2%. １ H-NMR, １３ The C-NMR and IR (ATR) spectra are shown in FIGS. 35 to 37.

[0199] Synthesis Example 14 Synthesis of Epoxidized Diester Mixture 5 Epoxidized diester mixture 5 was synthesized from diester mixture 5 synthesized in Synthesis Example 5 according to the following synthesis scheme. Note that diester mixture 5 and epoxidized diester mixture 5 each represent a mixture of compounds in which R is any of the following four hydrocarbon groups, and the two Rs contained in epoxidized diester mixture 5 may be the same or different. In a three-neck reactor equipped with a thermometer, 80 g (0.06 mol) of the diester mixture 5 was dissolved in 500 mL of methylene chloride under a nitrogen stream. 1.86 g (0.017 mol) of sodium carbonate was added to this solution, which was then cooled in an ice bath. While cooling this solution in an ice bath, 355.3 g (0.42 mol as peracetic acid) of 9% peracetic acid in acetic acid (manufactured by Aldrich) was slowly added dropwise over 1 hour, and the entire mixture was stirred for 1 hour while still in the ice bath. The reaction solution was then returned to room temperature and stirred for 18 hours. The reaction solution was again cooled in an ice bath, and 177.7 g (0.21 mol) of 9% peracetic acid in acetic acid (manufactured by Aldrich) was slowly added dropwise over 30 minutes. The entire mixture was returned to room temperature and stirred for an additional 24 hours. After completion of the reaction, 1 mol / L aqueous sodium thiosulfate solution was slowly added to the reaction solution under vigorously stirring while cooling in an ice bath. While checking with potassium iodide starch paper, the mixture was added until the potassium iodide starch paper no longer discolored, and then extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was then collected and cooled in an ice bath. A saturated aqueous solution of sodium bicarbonate was slowly added to make the mixture weakly basic (pH = 8). The collected ethyl acetate layer was separated and washed with 300 mL of saturated saline. The collected ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off. The solvent was removed by evaporation using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 85:15 (volume ratio)) to obtain 81 g of epoxidized diester mixture 5 as a pale brown oil. The structure of epoxidized diester mixture 2 was identified by NMR and infrared absorption spectroscopy. １ H-NMR (500MHz, CDCl ３ , TMS, δ ppm): The conversion rate of the double bond calculated from the remaining amount of the signal at 6.60 to 5.20 ppm derived from the double bond was 81.8%. １ H-NMR, １３ The C-NMR and IR (ATR) spectra are shown in FIGS. 38 to 40.

[0200] Synthesis Example 15 Synthesis of Epoxidized Diester Mixture 6 Epoxidized diester mixture 6 was synthesized from diester mixture 6 synthesized in Synthesis Example 6 according to the following synthesis scheme. Note that diester mixture 6 and epoxidized diester mixture 6 each represent a mixture of compounds in which R is any of the following four hydrocarbon groups, and the two Rs contained in epoxidized diester mixture 6 may be the same or different. In a three-neck reactor equipped with a thermometer, 80 g (0.06 mol) of the diester mixture 6 was dissolved in 500 mL of methylene chloride under a nitrogen stream. 1.91 g (0.018 mol) of sodium carbonate was added to this solution, which was then cooled in an ice bath. While cooling this solution in an ice bath, 364.7 g (0.43 mol as peracetic acid) of 9% peracetic acid in acetic acid (manufactured by Aldrich) was slowly added dropwise over 1 hour, and the entire mixture was stirred for 1 hour while still in the ice bath. The reaction solution was then returned to room temperature and stirred for 20 hours. The reaction solution was again cooled in an ice bath, and 182.4 g (0.22 mol) of 9% peracetic acid in acetic acid (manufactured by Aldrich) was slowly added dropwise over 30 minutes. The entire mixture was returned to room temperature and stirred for an additional 20 hours. After completion of the reaction, 1 mol / L aqueous sodium thiosulfate solution was slowly added to the reaction solution under vigorously stirring while cooling in an ice bath. While checking with potassium iodide starch paper, the mixture was added until the potassium iodide starch paper no longer discolored, and then extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was then collected and cooled in an ice bath. A saturated aqueous solution of sodium bicarbonate was slowly added to make the mixture weakly basic (pH = 8). The collected ethyl acetate layer was separated and washed with 300 mL of saturated saline. The collected ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off. The solvent was removed by evaporation using a rotary evaporator, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 85:15 (volume ratio)) to obtain 80 g of epoxidized diester mixture 6 as a pale brown oil. The structure of epoxidized diester mixture 1 was identified by NMR and infrared absorption spectroscopy. 　１ H-NMR (500MHz, CDCl ３, TMS, δ ppm): The conversion rate of the double bond calculated from the remaining amount of the signal at 6.60 to 5.20 ppm derived from the double bond was 82.0%. １ H-NMR, １３ The C-NMR and IR (ATR) spectra are shown in FIGS. 41 to 43.

[0201] Synthesis Example 16 Synthesis of epoxidized diester mixture 7

[0123] The same operation as in Synthesis Example 10 was performed, except that 80 g of diester mixture 1 was changed to 80 g of diester mixture 7, 140 g (2.33 mol) of acetic acid was changed to 142 g (2.36 mol), 11.4 g (0.11 mol) of phosphoric acid was changed to 11.6 g (0.12 mol), and 182.2 ml (2.33 mol) of 30 wt% hydrogen peroxide was changed to 184.9 ml (2.36 mol), to obtain 77 g of epoxidized diester mixture 7.

[0202] Synthesis Example 17 Synthesis of epoxidized diester mixture 8

[0123] The same operations as in Synthesis Example 10 were performed, except that 80 g of diester mixture 1 was changed to 80 g of diester mixture 8, 140 g (2.33 mol) of acetic acid was changed to 107 g (1.78 mol), 11.4 g (0.11 mol) of phosphoric acid was changed to 8.7 g (0.09 mol), and 182.2 ml (2.33 mol) of 30 wt% hydrogen peroxide was changed to 139.4 ml (1.78 mol), to obtain 79 g of epoxidized diester mixture 8.

[0203] Synthesis Example 18 Synthesis of epoxidized diester mixture 9

[0136] The same operations as in Synthesis Example 10 were performed, except that 80 g of diester mixture 1 was changed to 80 g of diester mixture 9, 140 g (2.33 mol) of acetic acid was changed to 136 g (2.27 mol), 11.4 g (0.11 mol) of phosphoric acid was changed to 11.1 g (0.11 mol), and 182.2 ml (2.33 mol) of 30 wt% hydrogen peroxide was changed to 177.2 ml (2.27 mol), to obtain 75 g of epoxidized diester mixture 9.

[0204] Example 1 Preparation of Vinyl Chloride Resin Composition The ingredients listed in Table 2, excluding the plasticizer composition (polyester-based plasticizer, compound, and other plasticizers) and the vinyl chloride resin fine particles serving as a dusting agent, were mixed in a Henschel mixer. When the mixture reached 80°C, the entire plasticizer composition was added, and the mixture was allowed to dry (referring to a state in which the plasticizer was absorbed by the vinyl chloride resin particles, making the mixture smooth). Mixing was continued until the maximum temperature reached 100°C or higher and 200°C or lower. When the dried mixture cooled to less than 100°C, the vinyl chloride resin fine particles serving as a dusting agent were added to prepare a vinyl chloride resin composition. The meltability of the resulting vinyl chloride resin composition was evaluated. The results are shown in Table 2. Formation of a Vinyl Chloride Resin Sheet The resulting vinyl chloride resin composition was sprinkled onto a textured mold heated to 250°C and left to melt for a desired period of time, after which the excess vinyl chloride resin composition was shaken off. The textured mold onto which the vinyl chloride resin composition had been sprinkled was then placed in an oven set at 200°C. After 60 seconds of standing, the textured mold was cooled with cooling water. When the mold temperature had cooled to 40°C, a 200mm x 150mm x 1mm vinyl chloride resin molded sheet was removed from the mold as a vinyl chloride resin molded article. The resulting vinyl chloride resin molded sheet was used to evaluate its initial (unheated) tensile properties (tensile strength, tensile elongation) at low temperatures. The resulting vinyl chloride resin molded sheet was also laminated with urethane foam and heated at 130°C for 100 hours, after which the urethane foam was peeled off and the tensile properties were similarly evaluated again at low temperatures. The results are shown in Table 2. <Laminate Formation> Two of the resulting vinyl chloride resin molded sheets (dimensions: 200mm x 150mm x 1mm) were placed, textured side down, in a 200mm x 300mm x 10mm mold.Separately, a polyol mixture consisting of 50 parts by mass of a propylene oxide-ethylene oxide (PO-EO) block adduct of propylene glycol (hydroxyl value 28, terminal EO unit content=10%, internal EO unit content 4%), 50 parts by mass of a PO-EO block adduct of glycerin (hydroxyl value 21, terminal EO unit content=14%), 2.5 parts by mass of water, 0.2 parts by mass of an ethylene glycol solution of triethylenediamine (manufactured by Tosoh Corporation, trade name: "TEDA-L33"), 1.2 parts by mass of triethanolamine, 0.5 parts by mass of triethylamine, and 0.5 parts by mass of a foam stabilizer (manufactured by Shin-Etsu Chemical Co., Ltd., trade name: "F-122"), and polymethylene polyphenylene polyisocyanate (polymeric MDI) were mixed in a ratio such that the index was 98 to prepare a mixed liquid. The prepared mixture was then poured onto two vinyl chloride resin molded sheets placed in the mold as described above. The mold was then sealed by covering it with an aluminum plate measuring 348 mm x 255 mm x 10 mm. The mold was then left for 5 minutes after sealing to form a laminate consisting of a vinyl chloride resin molded sheet (thickness: 1 mm) as a skin backed by a polyurethane foam molded body. The formed laminate was removed from the mold, and the vinyl chloride resin molded sheet in the laminate was evaluated for adhesion to the polyurethane foam molded body and heat shrinkage resistance. The results are shown in Table 2.

[0205] (Examples 2 to 11, Comparative Examples 1 to 5) Vinyl chloride resin compositions, vinyl chloride resin molded sheets, and laminates were produced in the same manner as in Example 1, except that the blending ratios used in preparing the vinyl chloride resin compositions were changed as shown in Tables 1 and 2. The resulting vinyl chloride resin compositions, vinyl chloride resin molded sheets, and laminates were then used to evaluate the meltability of the vinyl chloride resin compositions, and the tensile properties of the vinyl chloride resin molded sheets at low temperatures, heat shrinkage resistance, and adhesion to foamed polyurethane molded products. The results are shown in Tables 1 and 2.

[0206] In Tables 1 and 2, "EO modified" means "ethylene oxide modified", and "n" means "the number of repeating ethylene oxide units, n".

[0207]

[0208]

[0209] 1) Shin-Dai-Ichi Vinyl Corporation, product name "ZEST (registered trademark) 1300SI" (prepared by suspension polymerization, average degree of polymerization: 1300, average particle size: 115 μm) 2) Shin-Dai-Ichi Vinyl Corporation, product name "ZEST PQLTX" (prepared by emulsion polymerization, average degree of polymerization: 800, average particle size: 1.8 μm) 3) ADEKA Corporation, product name "ADEKA Cizer HPN-3130" (adipic acid-based polyester, viscosity (25°C): 3,000 mPa·s) 4) Cardrite Co., Ltd., product name "Cardolite NX-2026" (unmodified cardanol) 5) Cardolite Co., Ltd., product name "Cardolite NX-7507" (ethylene oxide-modified cardanol, number of repeating ethylene oxide units n=7) 6) ADEKA Corporation, product name "ADEKA CIZER O-130S" 7) Kyowa Chemical Industry Co., Ltd., product name "ALCAMIZER (registered trademark) 5" 8) Mizusawa Industrial Chemicals Co., Ltd., product name "MIZUKALIZER DS" 9) Sakai Chemical Industry Co., Ltd., product name "SAKAI SZ2000" 10) ADEKA Corporation, product name "ADEKA STAB LA-72" 11) ADEKA Corporation, product name "ADEKA STAB LS-12" 12) Dainichiseika Color & Chemicals Co., Ltd., product name "DA P 4720 Black"

[0210] Tables 1 and 2 show that the resin compositions of Examples 1-11, which were prepared using a compound having a predetermined structure as a plasticizer, were capable of forming resin molded articles that exhibited good low-temperature tensile elongation and adhesion to polyurethane, as well as excellent heat shrinkage resistance and meltability. The resin compositions prepared in Examples 10 and 11, which used two compounds having a predetermined structure in combination and contained a higher amount of the compound than the other Examples 1-9, were slightly inferior in heat shrinkage resistance compared to the other Examples 1-9, but were significantly superior in terms of low-temperature tensile elongation. On the other hand, the resin molded article formed from the resin composition of Comparative Example 1, which was prepared without using a compound having a predetermined structure, was found to have poor meltability and adhesion to polyurethane. Furthermore, the resin molded article formed from the resin composition of Comparative Example 2, which was prepared using unmodified cardanol instead of the compound having a predetermined structure, was found to have poor low-temperature tensile elongation and heat shrinkage resistance. Furthermore, the resin molded article formed from the resin composition of Comparative Example 3, which was prepared using ethylene oxide-modified cardanol instead of the compound having a predetermined structure, was found to have poor heat shrinkage resistance. Furthermore, it is clear that the resin molded article formed from the resin composition of Comparative Example 4, which was prepared using unmodified cardanol instead of the compound having a predetermined structure, was inferior in heat shrinkage resistance and meltability. Also, it is clear that the resin molded article formed from the resin composition of Comparative Example 5, which was prepared using a diester compound of ethylene oxide-modified cardanol and adipic acid instead of the compound having a predetermined structure, was inferior in heat shrinkage resistance and meltability.

[0211] According to the present invention, a novel compound obtained by epoxidizing an ester compound is provided.

Claims

1. A compound represented by the following formula (1): ...(1) [In formula (1), Ax represents an organic group having 3 to 20 carbon atoms, and Y １ , Y ４ are each independently a single bond, —C(═O)—, or —C(═O)—NR 1 - or -C(=O)-O-, R １ represents a hydrogen atom, a methyl group, or an ethyl group; Y ２ , Y ３ are each independently a single bond, —C(═O)—, or —NR ２ represents —C(═O)— or —O—C(═O)—, R ２ represents a hydrogen atom, a methyl group, or an ethyl group; Y １ , Y ４ , Y ２ , Y ３ may be independently different from each other or may be the same, and SP １ , SP ４ are each independently —CH ２ CH ２ O-, -CH ２ CH (CH ３ )O-,-CH(CH ３ ) CH ２ O-, -CH ２ CH (CH ２ CH ３ ) O—, or —CH(CH ２ CH ３ ) CH ２ O-, SP ２ , SP ３ are each independently —OCH ２ CH ２ -, -OCH(CH ３ ) CH ２ -, -OCH ２ CH (CH ３ )-,-OCH(CH ２ CH ３ ) CH ２ - or -OCH ２ CH (CH ２ CH ３ )-; a, b, c, and d each independently represent an integer of 0 to 30; R ａ , R ｂ , R ｃ , R ｄ each independently represents a chain aliphatic hydrocarbon group having from 12 to 18 carbon atoms which may have a substituent, the chain aliphatic hydrocarbon group may contain from 1 to 5 double bonds, R ａ , R ｂ , R ｃ , R ｄ At least one of the chain aliphatic hydrocarbon groups contains one or more epoxy groups, and ａ , R ｂ , R ｃ , R ｄ may be independently different from each other or may be the same, x and y each independently represent 0 or 1, and when x is 0, the following formula (1-1): represents a hydrogen atom, and when y is 0, the structure represented by the following formula (1-2): represents a hydrogen atom, and in formulas (1-1) and (1-2), * represents the bonding position with Ax.

2. The above R ａ , R ｂ , R ｃ and R ｄ each independently represent a chain aliphatic hydrocarbon group having from 12 to 18 carbon atoms which may have a substituent, and the chain aliphatic hydrocarbon group contains from 1 to 5 epoxy groups.

3. The Ax is (i) a chain aliphatic hydrocarbon group having 3 to 20 carbon atoms, which may have a substituent; (ii) a cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms, which may have a substituent; (iii) an aromatic hydrocarbon ring group having 6 to 14 carbon atoms, which may have a substituent; or (iv) an organic group having 3 to 20 carbon atoms, in which at least one single bond contained in the chain aliphatic hydrocarbon group, which may have a substituent, is substituted with —O—, —C(═O)—, —O—C(═O)—, or —C(═O)—O— (provided that there are two or more consecutive —O— groups, there are two or more consecutive —C(═O)— groups, and —O— or —C(═O)— is not one of the groups represented by the Y １ , the Y ２ , the Y ３ , or the Y ４ and (iii) when the aryl group is an alkyl group or an alkyl group, and ...

4. The compound according to claim 1, wherein Ax is a group represented by any one of the following formulas (2-1) to (2-35), which may have a substituent.

5. A mixture comprising the compound according to claim 1 and a compound represented by the following formula (3): ...(3) [In formula (3), Bx represents an organic group having 3 to 20 carbon atoms, and Y １１ , Y ４１ are each independently a single bond, —C(═O)—, or —C(═O)—NR 1 - or -C(=O)-O-, R １ represents a hydrogen atom, a methyl group, or an ethyl group; Y ２１ , Y ３１ are each independently a single bond, —C(═O)—, or —NR ２ represents —C(═O)— or —O—C(═O)—, R ２ represents a hydrogen atom, a methyl group, or an ethyl group; Y １１ , Y ４１ , Y ２１ , Y ３１ may be independently different from each other or may be the same, and SP １１ , SP ４１ are each independently —CH ２ CH ２ O-, -CH ２ CH (CH ３ )O-,-CH(CH ３ ) CH ２ O-, -CH ２ CH (CH ２ CH ３ ) O—, or —CH(CH ２ CH ３ ) CH ２ O-, SP ２１ , SP ３１ are each independently —OCH ２ CH ２ -, -OCH(CH ３ ) CH ２ -, -OCH ２ CH (CH ３ )-,-OCH(CH ２ CH ３ ) CH ２ - or -OCH ２ CH (CH ２ CH ３ )-; e, f, g, and h each independently represent an integer of 0 to 30; R ａ１ , R ｂ１ , R ｃ１ , R ｄ１ each independently represents a chain aliphatic hydrocarbon group having from 12 to 18 carbon atoms which may have a substituent, the chain aliphatic hydrocarbon group may contain from 1 to 5 double bonds, R ａ１ , R ｂ１ , R ｃ１ , R ｄ１ may be each independently different from each other or the same, p and q each independently represent 0 or 1, and when p is 0, a compound represented by the following formula (3-1): represents a hydrogen atom, and when q is 0, the structure represented by the following formula (3-2): represents a hydrogen atom, and in formulas (3-1) and (3-2), * represents the bonding position with Bx.

6. The Bx is (i) a chain aliphatic hydrocarbon group having 3 to 20 carbon atoms, which may have a substituent; (ii) a cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms, which may have a substituent; (iii) an aromatic hydrocarbon ring group having 6 to 14 carbon atoms, which may have a substituent; or (iv) an organic group having 3 to 20 carbon atoms, in which at least one single bond contained in the chain aliphatic hydrocarbon group, which may have a substituent, is substituted with —O—, —C(═O)—, —O—C(═O)—, or —C(═O)—O— (provided that there are two or more consecutive —O— groups, there are two or more consecutive —C(═O)— groups, and —O— or —C(═O)— is not one of the groups represented by the Y １１ , the Y ２１ , the Y ３１ , or the Y ４１ and (iii) when the group is located at the end bonded to the group (i.e., the end bonded to the group (ii)), the organic group is any one of the following:

7. The mixture according to claim 5, wherein Bx is a group represented by any one of the following formulas (2-1) to (2-35), which may have a substituent.

8. The mixture of claim 5, wherein Ax and Bx have the same structure.

9. The above R ａ , R ｂ , R ｃ and R ｄ The mixture according to claim 8, comprising at least two or more compounds represented by formula (1), each of which is independently different.

10. A method of using the compound according to any one of claims 1 to 4 as a plasticizer.

11. Use of the mixture according to any one of claims 5 to 9 as a plasticizer.

12. A plasticizer composition comprising the compound according to any one of claims 1 to 4 and a plasticizer.

13. A plasticizer composition comprising the mixture according to any one of claims 5 to 9 and a plasticizer.

14. The plasticizer composition of claim 12, wherein the plasticizer is a polyester-based plasticizer.

15. The plasticizer composition of claim 13, wherein the plasticizer is a polyester-based plasticizer.

16. The plasticizer composition of claim 14, wherein the plasticizer comprises an adipic acid-based polyester.

17. The plasticizer composition of claim 15, wherein the plasticizer comprises an adipic acid-based polyester.

18. The plasticizer composition according to claim 14, wherein the content of the compound is 1 part by mass or more and 70 parts by mass or less per 100 parts by mass of the polyester-based plasticizer.

19. The plasticizer composition according to claim 15, wherein the content of the compound is 1 part by mass or more and 70 parts by mass or less per 100 parts by mass of the polyester-based plasticizer.

20. A resin composition comprising a resin and the plasticizer composition of claim 12.

21. A resin composition comprising a resin and the plasticizer composition of claim 13.

22. The resin composition of claim 20, wherein the resin contains a halogen.

23. The resin composition of claim 21, wherein the resin contains a halogen.

24. The resin composition according to claim 20, wherein the glass transition temperature of the resin is 50°C or higher and 100°C or lower.

25. The resin composition according to claim 21, wherein the glass transition temperature of the resin is 50°C or higher and 100°C or lower.

26. The resin composition according to claim 20, wherein the resin contains a vinyl chloride resin.

27. The resin composition of claim 21, wherein the resin contains a vinyl chloride resin.

28. The resin composition according to claim 20, wherein the content of the compound is 1 part by mass or more and 50 parts by mass or less per 100 parts by mass of the resin.

29. The resin composition according to claim 21, wherein the content of the compound is 1 part by mass or more and 50 parts by mass or less per 100 parts by mass of the resin.

30. The resin composition according to claim 20, which is used in powder molding.

31. The resin composition according to claim 21, which is used in powder molding.

32. The resin composition according to claim 20, which is used in powder slush molding.

33. The resin composition according to claim 21, which is used in powder slush molding.

34. A resin molded product obtained by molding the resin composition according to claim 20.

35. A resin molded product obtained by molding the resin composition according to claim 21.

36. The resin molding according to claim 34, which is used for the surface of an automobile instrument panel.

37. The resin molding according to claim 35, which is used for the surface of an automobile instrument panel.

38. A laminate comprising a foamed polyurethane molded product and the resin molded product according to claim 34.

39. A laminate comprising a foamed polyurethane molded product and the resin molded product according to claim 35.

40. The laminate of claim 38, which is for an automobile instrument panel.

41. The laminate of claim 39, which is for an automobile instrument panel.

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