Novel compounds and methods of use, mixtures, plasticizer compositions, resin compositions, resin molded bodies, and laminates

Abstract

The present application provides a compound represented by the following formula (1). In formula (1), Ax represents an organic group having 3 to 20 carbon atoms, Y 1 , Y 2 , Y 3 , Y 4 each independently represents a single bond, -C(=O)-, or the like, SP 1 , SP 2 , SP 3 , SP 4 each independently represents a prescribed organic group, a, b, c, d each independently represents an integer of 0 to 30, R a , R b , R c , R d each independently represents a chain aliphatic hydrocarbon group having 12 or more and 18 or less carbon atoms which can have a substituent, the chain aliphatic hydrocarbon group can contain 1 or more and 5 or less double bonds, R a , R b , R c , R d In formula (1), at least one chain aliphatic hydrocarbon group contains 1 or more epoxy groups, x, y each independently represents 0 or 1.

Description

Technical Field

[0001] This invention relates to novel compounds and their methods of use, mixtures, plasticizer compositions, resin compositions, resin molded articles, and laminates. Background Technology

[0002] In recent years, resins such as vinyl chloride resin have been used for various applications due to their excellent cold resistance, heat resistance, and oil resistance.

[0003] Specifically, for example, in the formation of automotive interior components such as car dashboards and door trims, automotive interior materials are used such as skins formed from resin molded bodies using resins such as vinyl chloride resin, and laminates formed by lining the skins formed from resin molded bodies with foams such as polyurethane foam.

[0004] Furthermore, techniques have been proposed for manufacturing resin molded bodies that constitute the skin of automotive interior parts such as dashboards by molding a resin composition containing resins such as vinyl chloride resin, plasticizers, and additives using powder molding methods such as powder slush molding (see, for example, Patent Document 1). Specifically, in Patent Document 1, a vinyl chloride resin molded body is manufactured by powder slush molding a vinyl chloride resin composition containing vinyl chloride resin particles, plasticizers such as polyester plasticizers, and additives such as hydrotalcite stabilizers, zeolite stabilizers, and β-diketones.

[0005] Here, compounds derived from cashew phenol have long been used for various applications due to their excellent properties in terms of water resistance, chemical resistance, and heat resistance. For example, Patent Document 2 describes a diester compound obtained by esterification of 3-pentadecanylphenol with dicarboxylic acid acyl chloride as a compound that can be used as a thermochromic modifier for thermochromic inks.

[0006] Existing technical documents

[0007] Patent documents

[0008] Patent Document 1: Japanese Patent Application Publication No. 2012-197394;

[0009] Patent Document 2: Japanese Patent Publication No. 2020-517691. Summary of the Invention

[0010] The problem the invention aims to solve

[0011] The object of this invention is to provide novel compounds, etc., formed by epoxidation of ester compounds.

[0012] Solution for solving the problem

[0013] The inventors have made a new discovery of the above-mentioned novel compound, thereby completing the present invention. Furthermore, the inventors have also completed methods for using the novel compound, mixtures containing the novel compound, plasticizer compositions and resin compositions, and resin molded articles and laminates formed using the thereof.

[0014] That is, according to the present invention, the following compounds [1] to [4], the following mixtures [5] to [9], the following methods of use

[10] to

[11] , the following plasticizer compositions

[12] to

[17] , the following resin compositions

[18] to

[23] , the following resin molded articles

[24] to

[25] , and the following laminates

[26] to

[27] are provided.

[0015] [1] The compound represented by the following formula (1).

[0016] [Chemical Formula 1]

[0017] (1)

[0018] In formula (1),

[0019] Ax represents an organic group with 3 to 20 carbon atoms.

[0020] Y 1 Y 4 Each can independently represent a single bond, -C(=O)-, or -C(=O)-NR. 1 -or-C(=O)-O-,

[0021] R 1 Indicates a hydrogen atom, methyl, or ethyl.

[0022] Y 2 Y 3 Each can independently represent a single bond, -C (=O)-, and -NR. 2 -C(=O)- or -OC(=O)-,

[0023] R 2 Indicates a hydrogen atom, methyl, or ethyl.

[0024] Y 1 Y 4 Y 2 Y 3 Each can be independent and different from the others, or they can be the same.

[0025] SP 1 SP 4Each can be independently represented as -CH2CH2O-, -CH2CH(CH3)O-, -CH(CH3)CH2O-, -CH2CH(CH2CH3)O-, or -CH(CH2CH3)CH2O-.

[0026] SP 2 SP 3 Each can be independently represented as -OCH2CH2-, -OCH(CH3)CH2-, -OCH2CH(CH3)-, -OCH(CH2CH3)CH2-, or -OCH2CH(CH2CH3)-.

[0027] a, b, c, and d each independently represent an integer from 0 to 30.

[0028] R a R b R c R d Each can independently represent a chain-like aliphatic hydrocarbon group having 12 or more but less than 18 carbon atoms that can have substituents.

[0029] The aforementioned chain-like aliphatic hydrocarbon groups may contain one or more but no more than five double bonds.

[0030] R a R b R c R d In the above-mentioned chain aliphatic hydrocarbon groups, at least one chain aliphatic hydrocarbon group contains one or more epoxy groups.

[0031] R a R b R c R d Each can be independent and different from the others, or they can be the same.

[0032] x and y can each independently represent 0 or 1.

[0033] When x is 0, the structure represented by the following equation (1-1) represents a hydrogen atom.

[0034] [Chemical Formula 2]

[0035] (1-1)

[0036] When y is 0, the structure represented by the following equation (1-2) represents a hydrogen atom.

[0037] [Chemical Formula 3]

[0038] (1-2)

[0039] In equations (1-1) and (1-2), * indicates the bonding position with Ax.

[0040] [2] Here, in the compound of [1] above, the above R a R b R c and R d Each can independently represent a chain aliphatic hydrocarbon group having 12 or more and 18 or less carbon atoms that may have substituents, preferably containing 1 or more and 5 or less epoxy groups in the chain aliphatic hydrocarbon group.

[0041] [3] In addition, in the compounds of [1] or [2] above, it is preferred that the above Ax is any one of the organic groups (i), (ii), (iii) and (iv) below:

[0042] (i) may have a chain-like aliphatic hydrocarbon group having 3 to 20 carbon atoms as a substituent;

[0043] (ii) may have cyclic aliphatic hydrocarbon groups with 4 to 12 carbon atoms having substituents;

[0044] (iii) May have aromatic hydrocarbon cyclic groups with 6 to 14 substituents.

[0045] (iv) An organic group having 3 to 20 carbon atoms, wherein at least one single bond in a chain aliphatic hydrocarbon group having substituents is replaced by -O-, -C(=O)-, -OC(=O)- or -C(=O)-O- (excluding cases where two or more -O- groups are consecutive, cases where two or more -C(=O)- groups are consecutive, and cases where -O- or -C(=O)- is located adjacent to the Y group mentioned above). 1 The above Y 2 The above Y 3 Or the above Y 4 The condition of the bonded ends.

[0046] [4] In any of the compounds in [1] to [3] above, it is preferred that Ax is a group represented by any of the following formulas (2-1) to (2-35) that may have substituents.

[0047] [Chemical Formula 4]

[0048]

[0049] [5] A mixture comprising any one of the compounds in [1] to [4] above and a compound represented by the following formula (3).

[0050] [Chemical Formula 5]

[0051] (3)

[0052] In formula (3),

[0053] Bx represents an organic group with 3 to 20 carbon atoms.

[0054] Y 11 Y 41 Each can independently represent a single bond, -C(=O)-, or -C(=O)-NR. 1 -or-C(=O)-O-,

[0055] R 1 Indicates a hydrogen atom, methyl, or ethyl.

[0056] Y 21 Y 31 Each can independently represent a single bond, -C (=O)-, and -NR. 2 -C(=O)- or -OC(=O)-,

[0057] R 2 Indicates a hydrogen atom, methyl, or ethyl.

[0058] Y 11 Y 41 Y 21 Y 31 Each can be independent and different from the others, or they can be the same.

[0059] SP 11 SP 41 Each can be independently represented as -CH2CH2O-, -CH2CH(CH3)O-, -CH(CH3)CH2O-, -CH2CH(CH2CH3)O-, or -CH(CH2CH3)CH2O-.

[0060] SP 21 SP 31 Each can be independently represented as -OCH2CH2-, -OCH(CH3)CH2-, -OCH2CH(CH3)-, -OCH(CH2CH3)CH2-, or -OCH2CH(CH2CH3)-.

[0061] e, f, g, and h each independently represent integers from 0 to 30.

[0062] R a1 R b1 R c1 R d1 Each can independently represent a chain-like aliphatic hydrocarbon group having 12 or more but less than 18 carbon atoms that can have substituents.

[0063] The aforementioned chain-like aliphatic hydrocarbon groups may contain one or more but no more than five double bonds.

[0064] R a1 R b1 R c1 R d1 Each can be independent and different from the others, or they can be the same.

[0065] p and q each independently represent 0 or 1.

[0066] When p is 0, the structure represented by the following equation (3-1) represents a hydrogen atom.

[0067] [Chemical Formula 6]

[0068] (3-1)

[0069] When q is 0, the structure represented by the following equation (3-2) represents a hydrogen atom.

[0070] [Chemical Formula 7]

[0071] (3-2)

[0072] In equations (3-1) and (3-2), * indicates the bonding position with Bx.

[0073] [6] Herein, in the mixture of [5] above, it is preferred that the above Bx is any one of the following organic groups (i), (ii), (iii) and (iv):

[0074] (i) may have a chain-like aliphatic hydrocarbon group having 3 to 20 carbon atoms as a substituent;

[0075] (ii) may have cyclic aliphatic hydrocarbon groups with 4 to 12 carbon atoms having substituents;

[0076] (iii) May have aromatic hydrocarbon cyclic groups with 6 to 14 substituents.

[0077] (iv) An organic group having 3 to 20 carbon atoms, wherein at least one single bond in a chain aliphatic hydrocarbon group having substituents is replaced by -O-, -C(=O)-, -OC(=O)- or -C(=O)-O- (excluding cases where two or more -O- groups are consecutive, cases where two or more -C(=O)- groups are consecutive, and cases where -O- or -C(=O)- is located adjacent to the Y group mentioned above). 11 The above Y 21 The above Y 31 Or the above Y 41 The condition of the bonded ends.

[0078] [7] In addition, in the mixture of [5] or [6] above, it is preferable that the above Bx is a group represented by any of the following formulas (2-1) to (2-35) that may have substituents.

[0079] [Chemical Formula 8]

[0080]

[0081] [8] In any of the mixtures of [5] to [7] above, it is preferred that Ax and Bx have the same structure.

[0082] [9] The mixture of any one of [5] to [8] above preferably contains at least two of the above R. a R b R c and R d Each is a distinct compound represented by formula (1).

[0083]

[10] A method using a compound from any one of [1] to [4] above as a plasticizer.

[0084] If the compounds of the present invention are used as plasticizers, the low-temperature tensile elongation and adhesion to polyurethane, more specifically to foamed polyurethane molded articles formed from resin compositions prepared using the compounds and mixtures of the present invention can be improved, while heat shrinkage resistance and meltability are also improved.

[0085]

[11] A method using a mixture of any one of [5] to [9] above as a plasticizer.

[0086]

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

[0087]

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

[0088]

[14] In the plasticizer compositions of

[12] or

[13] above, the plasticizer is a polyester plasticizer.

[0089]

[15] In the plasticizer composition of

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

[0090]

[16] In any of the plasticizer compositions of

[12] to

[14] above, the content of the above compound is more than 1 part by mass and less than 70 parts by mass relative to 100 parts by mass of the above polyester plasticizer.

[0091]

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

[12] to

[16] above.

[0092]

[18] In the resin composition of

[17] above, the resin contains halogen.

[0093]

[19] In the resin composition of

[17] or

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

[0094]

[20] In any of the resin compositions of

[17] to

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

[0095]

[21] In any of the resin compositions described in

[17] to

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

[0096]

[22] The resin composition of any one of

[17] to

[21] above is used for powder molding.

[0097]

[23] The resin composition of any one of

[17] to

[22] above is used for powder slush molding.

[0098]

[24] A resin molded body is formed by molding the resin composition of any one of

[17] to

[23] above.

[0099]

[25] The resin molded body of

[24] described above is used for automotive dashboard skin.

[0100]

[26] A laminate having a foamed polyurethane molded body and a resin molded body as described in

[24] or

[25] .

[0101]

[27] The laminate described above

[26] is used in automotive dashboards.

[0102] Invention Effects

[0103] According to the present invention, novel compounds formed by epoxidation of ester compounds are provided. Attached Figure Description

[0104] Figure 1 This illustrates the use of "Cardolite NX-2026" (manufactured by Cardolite) in the synthesis example. 1 The spectrum obtained by H-NMR measurement.

[0105] Figure 2 This illustrates the use of "Cardolite NX-2026" (manufactured by Cardolite) in the synthesis example. 13The spectrum obtained by C-NMR measurement.

[0106] Figure 3 This is a graph showing the spectrum obtained by infrared spectroscopy (total reflectance measurement) (hereinafter sometimes simply referred to as "IR (ATR)") using the "Cardolite NX-2026" (Cardolite Corporation) used in the synthesis example.

[0107] Figure 4 This illustrates the use of "Cardolite NX-7507" (manufactured by Cardolite) in the synthesis example. 1 The spectrum obtained by H-NMR measurement.

[0108] Figure 5 This illustrates the use of "Cardolite NX-7507" (manufactured by Cardolite) in the synthesis example. 13 The spectrum obtained by C-NMR measurement.

[0109] Figure 6 This is a graph showing the spectrum obtained by C-HCOSY determination using "Cardolite NX-7507" (Cardolite AG) used in the synthesis example.

[0110] Figure 7 This is a graph showing the spectrum obtained by IR (ATR) measurement using "Cardolite NX-7507" (Cardolite AG) used in the synthesis example.

[0111] Figure 8 This illustrates the diester mixture 1 obtained from Synthesis Example 1. 1 The spectrum obtained by H-NMR measurement.

[0112] Figure 9 This illustrates the diester mixture 1 obtained from Synthesis Example 1. 13 The spectrum obtained by C-NMR measurement.

[0113] Figure 10 This is a graph showing the spectrum obtained by IR (ATR) determination of diester mixture 1 obtained from synthesis example 1.

[0114] Figure 11 This illustrates the diester mixture 2 obtained by synthesis example 2. 1 The spectrum obtained by H-NMR measurement.

[0115] Figure 12 This illustrates the diester mixture 2 obtained by synthesis example 2. 13 The spectrum obtained by C-NMR measurement.

[0116] Figure 13 This is a graph showing the spectrum obtained by IR (ATR) determination of diester mixture 2 obtained from synthesis example 2.

[0117] Figure 14 This illustrates the diester mixture 3 obtained by synthesis example 3. 1 The spectrum obtained by H-NMR measurement.

[0118] Figure 15 This illustrates the diester mixture 3 obtained by synthesis example 3. 13 The spectrum obtained by C-NMR measurement.

[0119] Figure 16 This is a graph showing the spectrum obtained by IR (ATR) determination of diester mixture 3 obtained from synthesis example 3.

[0120] Figure 17 This illustrates the diester mixture 4 obtained by synthesis example 4. 1 The spectrum obtained by H-NMR measurement.

[0121] Figure 18 This illustrates the diester mixture 4 obtained by synthesis example 4. 13 The spectrum obtained by C-NMR measurement.

[0122] Figure 19 This is a graph showing the spectrum obtained by IR (ATR) determination of diester mixture 4 obtained by synthesis example 4.

[0123] Figure 20 This illustrates the diester mixture 5 obtained by synthesis example 5. 1 The spectrum obtained by H-NMR measurement.

[0124] Figure 21 This illustrates the diester mixture 5 obtained by synthesis example 5. 13 The spectrum obtained by C-NMR measurement.

[0125] Figure 22 This is a graph showing the spectrum obtained by IR (ATR) determination of diester mixture 5 obtained by synthesis example 5.

[0126] Figure 23 This illustrates the diester mixture 6 obtained by synthesis example 6. 1 The spectrum obtained by H-NMR measurement.

[0127] Figure 24 This illustrates the diester mixture 6 obtained by synthesis example 6. 13 The spectrum obtained by C-NMR measurement.

[0128] Figure 25 This is a graph showing the spectrum obtained by IR (ATR) determination of diester mixture 6 obtained by synthesis example 6.

[0129] Figure 26 This illustrates the epoxide diester mixture 1 obtained from Synthesis Example 10. 1 The spectrum obtained by H-NMR measurement.

[0130] Figure 27 This illustrates the epoxide diester mixture 1 obtained from Synthesis Example 10. 13 The spectrum obtained by C-NMR measurement.

[0131] Figure 28 This is a graph showing the spectrum obtained by IR (ATR) determination of the epoxide diester mixture 1 obtained by synthesis example 10.

[0132] Figure 29 This illustrates the epoxide diester mixture 2 obtained from synthesis example 11. 1 The spectrum obtained by H-NMR measurement.

[0133] Figure 30 This illustrates the epoxide diester mixture 2 obtained from synthesis example 11. 13 The spectrum obtained by C-NMR measurement.

[0134] Figure 31 This is a graph showing the spectrum obtained by IR (ATR) determination of the epoxide diester mixture 2 obtained by synthesis example 11.

[0135] Figure 32 This illustrates the epoxide diester mixture 3 obtained from synthesis example 12. 1 The spectrum obtained by H-NMR measurement.

[0136] Figure 33 This illustrates the epoxide diester mixture 3 obtained from synthesis example 12. 13 The spectrum obtained by C-NMR measurement.

[0137] Figure 34 This is a graph showing the spectrum obtained by IR (ATR) determination of the epoxide diester mixture 3 obtained by synthesis example 12.

[0138] Figure 35 This illustrates the epoxide diester mixture 4 obtained from synthesis example 13. 1 The spectrum obtained by H-NMR measurement.

[0139] Figure 36This illustrates the epoxide diester mixture 4 obtained from synthesis example 13. 13 The spectrum obtained by C-NMR measurement.

[0140] Figure 37 This is a graph showing the spectrum obtained by IR (ATR) determination of the epoxide diester mixture 4 obtained from Synthesis Example 13.

[0141] Figure 38 This illustrates the epoxide diester mixture 5 obtained from synthesis example 14. 1 The spectrum obtained by H-NMR measurement.

[0142] Figure 39 This illustrates the epoxide diester mixture 5 obtained from synthesis example 14. 13 The spectrum obtained by C-NMR measurement.

[0143] Figure 40 This is a graph showing the spectrum obtained by IR (ATR) determination of the epoxide diester mixture 5 obtained by synthesis example 14.

[0144] Figure 41 This illustrates the epoxide diester mixture 6 obtained by synthesis example 15. 1 The spectrum obtained by H-NMR measurement.

[0145] Figure 42 This illustrates the epoxide diester mixture 6 obtained by synthesis example 15. 13 The spectrum obtained by C-NMR measurement.

[0146] Figure 43 This is a graph showing the spectrum obtained by IR (ATR) determination of the epoxide diester mixture 6 obtained from Synthesis Example 15. Detailed Implementation

[0147] The embodiments of the present invention will now be described in detail. The present invention provides novel compounds formed by epoxidation of ester compounds, and mixtures comprising the compounds.

[0148] The compounds and mixtures of the present invention can be used, for example, in the preparation of the plasticizer compositions of the present invention. Additionally, the plasticizer compositions of the present invention can be used, for example, in the preparation of resin compositions.

[0149] Furthermore, the resin composition of the present invention can be used, for example, in forming the resin molded articles of the present invention. Moreover, the resin molded articles formed using the resin composition of the present invention are preferably used, for example, as automotive interior materials such as the skins of automotive interior parts such as automotive dashboards and door trims.

[0150] Furthermore, the resin molded articles of the present invention can be used, for example, in forming the laminates of the present invention. Moreover, the laminates formed using the resin molded articles of the present invention are preferably used, for example, as automotive interior materials for use in manufacturing automotive interior parts such as dashboards and door trims.

[0151] (compound)

[0152] The compounds of the present invention are those represented by the following formula (1).

[0153] [Chemical Formula 9]

[0154] (1)

[0155] Furthermore, the compounds of the present invention enable the resin molded articles obtained by molding resin compositions prepared using the compounds to have good low-temperature tensile elongation (also known as low-temperature tensile elongation) and good adhesion to polyurethane, while improving heat shrinkage resistance and meltability.

[0156] Hereinafter, resin molded articles obtained by molding resin compositions prepared using the compounds, mixtures or plasticizer compositions of the present invention will also be referred to simply as resin molded articles.

[0157] <x、y>

[0158] In the above formula (1), x and y each independently represent 0 or 1.

[0159] Moreover, when x is 0, the structure represented by the following equation (1-1) represents a hydrogen atom.

[0160] [Chemical Formula 10]

[0161] (1-1)

[0162] Furthermore, when y is 0, the structure represented by (1-2) below represents a hydrogen atom.

[0163] [Chemical Formula 11]

[0164] (1-2)

[0165] In addition, in the above equations (1-1) and (1-2), * indicates the bonding position with Ax.

[0166] Furthermore, x and y can both be 0, both can both be 1, or one can be 0 and the other can be 1. However, 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.

[0167] <ax>

[0168] In the above formula (1), Ax represents an organic group with 3 to 20 carbon atoms.

[0169] Here, the same carbon atom in the organic group constituting Ax can interact with the aforementioned Y. 1 Y 2 Y 3 (wherein, only the case of x = 1) and Y 4 (Whereinin the case is limited to y=1) two or more bonds, the same carbon atom in the organic group constituting Ax may not be bonded to the aforementioned Y. 1 Y 2 Y 3 (wherein, only the case of x = 1) and Y 4 (wherein, only the case where y=1) involves two or more bonds.

[0170] Furthermore, from the viewpoint of further improving the low-temperature tensile elongation of the resin molded article, it is preferable that the same carbon atom in the organic group constituting Ax does not interact with the aforementioned Y. 1 Y 2 Y 3 (wherein, only the case of x = 1) and Y 4 (wherein, only the case where y=1) involves two or more bonds, i.e., bonds with Y 1 Bonded carbon atoms, and Y 2 Bonded carbon atoms, and Y 3 (This applies only to the case where x = 1) the carbon atoms bonded to Y, and the carbon atoms bonded to Y. 4 (In this case, only the case of y=1) the bonded carbon atoms are all different.

[0171] Furthermore, the same carbon atom in the organic group constituting Ax does not interact with the aforementioned Y. 1 Y 2 Y 3 (wherein, only the case of x = 1) and Y 4 (Where, only in the case of y=1) when there are two or more bonds in the organic group constituting Ax, the bonds between the organic group and Y are... 1 Bonded carbon atoms, and Y 2 Bonded carbon atoms, and Y 3 (Where, only the case x = 1 is considered) the carbon atoms bonded to Y, and the carbon atoms bonded to Y. 4 (This applies only to the case where y = 1) Bonded carbon atoms can be adjacent to each other or not.

[0172] Furthermore, from the viewpoint of further improving the low-temperature tensile elongation of the resin molded article, it is preferable that the organic groups constituting Ax are similar to those of Y. 1 Bonded carbon atoms, and Y 2 Bonded carbon atoms, and Y 3 (Where, only the case x = 1 is considered) the carbon atoms bonded to Y, and the carbon atoms bonded to Y. 4 (Where, only the case of y=1) bonded carbon atoms are not adjacent to each other.

[0173] Furthermore, Ax is preferably any one of the organic groups (i), (ii), (iii), and (iv) below, more preferably any one of the organic groups (i) or (iii) below, and even more preferably an organic group (i) below.

[0174] (i) may have a chain-like aliphatic hydrocarbon group having 3 to 20 carbon atoms as a substituent;

[0175] (ii) may have cyclic aliphatic hydrocarbon groups with 4 to 12 carbon atoms having substituents;

[0176] (iii) May have aromatic hydrocarbon cyclic groups with 6 to 14 substituents.

[0177] (iv) An organic group having 3 to 20 carbon atoms, wherein at least one single bond in a chain aliphatic hydrocarbon group having substituents is replaced by -O-, -C(=O)-, -OC(=O)- or -C(=O)-O- (excluding cases where two or more -O- groups are consecutive, cases where two or more -C(=O)- groups are consecutive, and cases where -O- or -C(=O)- is located adjacent to the Y group mentioned above). 1 The above Y 2 The above Y 3 Or the above Y 4 The condition of the bonded ends.

[0178] Furthermore, in this invention, "may have substituents" means "unsubstituted or substituented." Moreover, when the organic group contained in the general formula has substituents, the number of substituents in the organic group can be one or more. Additionally, when the organic group contained in the general formula has substituents, unless otherwise specified, the number of carbon atoms in the organic group having the substituent does not include the number of carbon atoms in the substituent. For example, when a chain aliphatic hydrocarbon cyclic group with 3 to 20 carbon atoms has a substituent, the number of carbon atoms in the chain aliphatic hydrocarbon cyclic group with 3 to 20 carbon atoms does not include the number of carbon atoms in the substituent.

[0179] Here, the chain aliphatic hydrocarbon group with 3 to 20 carbon atoms in (i) above preferably has 3 to 15 carbon atoms, more preferably 3 to 12, even more preferably 3 to 10, and even more preferably 3 to 8.

[0180] Among them, the total number of carbon atoms in (i) above, including the carbon atoms of the chain aliphatic hydrocarbon group with 3 to 20 carbon atoms and the carbon atoms of the substituents, is 3 to 20.

[0181] The chain aliphatic hydrocarbon group with 3 to 20 carbon atoms in (i) above can be straight-chain or branched.

[0182] The chain aliphatic hydrocarbon group with 3 to 20 carbon atoms in (i) above can be an unsaturated aliphatic hydrocarbon group with unsaturated bonds (carbon-carbon double bonds, carbon-carbon triple bonds) or a saturated aliphatic hydrocarbon group without unsaturated bonds. Furthermore, in the case where the chain aliphatic hydrocarbon group with 3 to 20 carbon atoms in (i) above has unsaturated bonds, the number of unsaturated bonds is, for example, one or more and three or fewer.

[0183] The substituents that the chain aliphatic hydrocarbon group with 3 to 20 carbon atoms in (i) above can have are not particularly limited, for example, halogen atoms, etc.

[0184] The cyclic aliphatic hydrocarbon group with 4 to 12 carbon atoms in (ii) above preferably has 4 to 15 carbon atoms, more preferably 4 to 12, even more preferably 4 to 10, even more preferably 4 to 8, and still even more preferably 4 to 6.

[0185] Among them, the total number of carbon atoms in (ii) above, including the carbon atoms of the cyclic aliphatic hydrocarbon group with 4 to 12 carbon atoms and the carbon atoms of the substituents, is 3 to 20.

[0186] The cyclic aliphatic hydrocarbon groups with 4 to 12 carbon atoms in (ii) above can be unsaturated aliphatic hydrocarbon groups with unsaturated bonds (carbon-carbon double bonds, carbon-carbon triple bonds) or saturated aliphatic hydrocarbon groups without unsaturated bonds.

[0187] Substituents that can be present in the cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms as described in (ii) above include, for example, halogen atoms, alkyl groups having 1 to 8 carbon atoms, etc.

[0188] The aromatic hydrocarbon cyclogroup with 6 to 14 carbon atoms in (iii) above preferably has 6 to 12 carbon atoms.

[0189] Among them, the total number of carbon atoms in (iii) above, including the carbon atoms of the aromatic hydrocarbon cyclogroup (6 to 14) and the carbon atoms of the substituents, is 3 to 20.

[0190] The aromatic hydrocarbon cycloalloys with 6 to 14 carbon atoms mentioned above can have substituents such as halogen atoms and alkyl groups with 1 to 6 carbon atoms.

[0191] Here, the number of carbon atoms in the organic group with 3 to 20 carbon atoms in (iv) above is preferably 3 to 15, more preferably 3 to 12, even more preferably 3 to 10, even more preferably 3 to 8, even more preferably 3 to 6, and particularly preferably 3 to 4.

[0192] Furthermore, in the organic groups with 3 to 20 carbon atoms in (iv) above, if at least one single bond in the chain aliphatic hydrocarbon group having a substituent is replaced by -C(=O)-, -OC(=O)-, or -C(=O)-O-, the number of carbon atoms in -C(=O)-, -OC(=O)-, or -C(=O)-O- is included in the number of carbon atoms in the organic groups with 3 to 20 carbon atoms in (iv) above.

[0193] Among them, the total number of carbon atoms of the organic groups with 3 to 20 carbon atoms, including the number of carbon atoms of the substituents, in (iv) above is 3 to 20.

[0194] Substituents that may be present in organic groups having 3 to 20 carbon atoms as described in (iv) above include, for example, halogen atoms.

[0195] Furthermore, as a preferred specific example of Ax, one can cite a group represented by any of the following formulas (2-1) to (2-35) that may have substituents. Here, "having substituents" means that any one of the hydrogen atoms in the group represented by any of the following formulas (2-1) to (2-35) is substituted.

[0196] [Chemical Formula 12]

[0197]

[0198] Furthermore, in the above equations (2-1)~(2-4), (2-20)~(2-26) and (2-30)~(2-33), "-" indicates an extension from any position of the ring, and intersects with Y. 1 Y 2 Y 3 Or Y 4 The bonding sites.

[0199] In addition, in the above equations (2-5)~(2-19), (2-27)~(2-29), (2-34)~(2-35), the "-" at the end of the chain structure indicates that it is related to Y. 1 Y 2 Y 3 Or Y 4 The bonding sites.

[0200] Furthermore, when x is 0, the structure represented by the above formula (1-1) (i.e., the hydrogen atom) can be any one of the hydrogen atoms of the group represented by any one 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., the hydrogen atom) can be any one of the hydrogen atoms of the group represented by any one of the above formulas (2-1) to (2-35).

[0201] Substituents that can be present as the group represented by any of the formulas (2-1) to (2-35) above include, for example, halogen atoms, alkyl groups having 1 to 4 carbon atoms, etc.

[0202] Furthermore, from the viewpoint of achieving excellent low-temperature tensile elongation of the resin molded article, 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), (2-20), and even more preferably a group represented by the above formula (2-6).

[0203] <Y 1 Y 4 >

[0204] In the above formula (1), Y 1 and Y 4 Each can independently represent a single bond, -C(=O)-, or -C(=O)-NR. 1 -or -C(=O)-O-. Additionally, R 1 It represents a hydrogen atom, a methyl group, or an ethyl group.

[0205] Furthermore, from the viewpoint of achieving good tensile elongation at low temperatures and adhesion to polyurethane in the resin molded body, while simultaneously improving heat shrinkage resistance and melt flowability, as Y 1 and Y 4 Each is independently preferred to be a single bond, -C(=O)- or -C(=O)-NR 1 -, more preferably a single bond or -C(=O)-, and even more preferably -C(=O)-.

[0206] <Y 2 Y 3 >

[0207] In the above formula (1), Y 2 and Y 3 Each can independently represent a single bond, -C (=O)-, and -NR. 2 -C(=O)- or -OC(=O)-. Additionally, R 2 It represents a hydrogen atom, a methyl group, or an ethyl group.

[0208] Furthermore, from the viewpoint of achieving good tensile elongation at low temperatures and adhesion to polyurethane in the resin molded body, while simultaneously improving heat shrinkage resistance and melt flowability, as Y 2 and Y 3 Each is independently preferred to be a single bond, -C(=O)-, or -NR. 2 -C(=O)-, more preferably a single bond or -C(=O)-, and even more preferably -C(=O)-.

[0209] Y 1 Y 4 Y 2 and Y 3 They can be independent of each other, or they can be the same.

[0210] <SP 1 SP 4 >

[0211] In the above formula (1), SP 1 and SP 4 Each can be independently represented as -CH2CH2O-, -CH2CH(CH3)O-, -CH(CH3)CH2O-, -CH2CH(CH2CH3)O-, or -CH(CH2CH3)CH2O-.

[0212] Moreover, as an SP 1 and SP 4 Each of them is preferably -CH2CH2O-, -CH2CH(CH3)O- or -CH(CH3)CH2O-, and more preferably -CH2CH2O-.

[0213] <SP 2 SP 3 >

[0214] In the above formula (1), SP 2 and SP 3 Each can be independently represented as -OCH2CH2-, -OCH(CH3)CH2-, -OCH2CH(CH3)-, -OCH(CH2CH3)CH2-, or -OCH2CH(CH2CH3)-.

[0215] Moreover, as an SP 2 and SP 3 Each of them is preferably -OCH2CH2-, -OCH(CH3)CH2- or -OCH2CH(CH3)-, and more preferably -OCH2CH2-.

[0216] <a、b、c、d>

[0217] In the above formula (1), a, b, c and d each independently represent integers from 0 to 30.

[0218] Furthermore, from the viewpoint of achieving good tensile elongation and adhesion to polyurethane at low temperatures in the resin molded body, while simultaneously improving heat shrinkage resistance and meltability, a, b, c, and d are each preferably represented by integers from 0 to 25, more preferably by integers from 2 to 20, even more preferably by integers from 3 to 15, even more preferably by integers from 4 to 12, and even more preferably by integers from 5 to 10.

[0219] <R a R b R c R d >

[0220] In the above formula (1), R a R b R c and R d Each can independently represent a chain-like aliphatic hydrocarbon group with 12 to 18 carbon atoms that can have substituents.

[0221] Composition of R a R b R c and R d The chain aliphatic hydrocarbon group having 12 to 18 carbon atoms of substituents preferably has 13 to 17 carbon atoms, more preferably 14 to 16.

[0222] Composition of R a R b R c and R d The chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms that may have substituents can each be an unsaturated aliphatic hydrocarbon group having unsaturated bonds (carbon-carbon double bonds or carbon-carbon triple bonds) or a saturated aliphatic hydrocarbon group without unsaturated bonds. Furthermore, when the aforementioned chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms have unsaturated bonds, the number of double bonds is, for example, one or more and five or fewer. In addition, the isomers formed through the carbon-carbon double bonds in the aforementioned chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms can be cis-isos, trans-isos, or a mixture of cis-isos and trans-isos.

[0223] As a component of R a R b R c and R d Chain aliphatic hydrocarbons with 12 to 18 carbon atoms can have substituents, such as alkyl groups with 1 to 3 carbon atoms, halogen atoms, etc.

[0224] R a R b R c and R d At least one of them contains more than one epoxy group. Furthermore, the number of epoxy groups is related to R. a R b R c and R d Each epoxy group is preferably one or more, more preferably two or more, more preferably five or fewer, and even more preferably four or fewer. If the number of epoxy groups is within the above range, the low-temperature tensile elongation and adhesion to polyurethane of the resin molded article can be good, while the heat shrinkage resistance and meltability are improved.

[0225] R a R b R c and R d They can be independent of each other, or they can be the same.

[0226] Moreover, R is preferred a R b R c and R d Each can be, for example, any of the following chain aliphatic hydrocarbon groups with 15 carbon atoms.

[0227] [Chemical Formula 13]

[0228]

[0229] (where R) a R b R c and R d At least one of them contains more than one epoxy group. Additionally, in the above formula, * represents a carbon atom bonded to an aromatic ring.

[0230] The aforementioned chain-like aliphatic hydrocarbon group with 15 carbon atoms can have at least one hydrogen atom replaced.

[0231] The compounds of the present invention include, for the compounds represented by the above formula (1), a compound having a single structure, and a mixture of two or more compounds with different structures combined in any ratio.

[0232] (mixture)

[0233] The mixture of the present invention comprises the compound represented by formula (1) above (the compound of the present invention) and the compound represented by formula (3) below.

[0234] [Chemical Formula 14]

[0235] (3)

[0236] Furthermore, the mixture of the present invention enables the resin molded body obtained by molding the resin composition prepared using the compound to have good low-temperature tensile elongation (also known as low-temperature tensile elongation) and good adhesion to polyurethane, while improving heat shrinkage resistance and meltability.

[0237] <p、q>

[0238] In the above formula (3), p and q each independently represent 0 or 1.

[0239] Moreover, when p is 0, the structure represented by the following equation (3-1) represents a hydrogen atom.

[0240] [Chemical Formula 15]

[0241] (3-1)

[0242] Furthermore, when q is 0, the structure represented by (3-2) below represents a hydrogen atom.

[0243] [Chemical Formula 16]

[0244] (3-2)

[0245] In addition, in the above equations (3-1) and (3-2), * indicates the bonding position with Bx.

[0246] Furthermore, p and q can both be 0, both can both be 1, or one can be 0 and the other can be 1. However, 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.

[0247] <bx>

[0248] In the above formula (3), Bx represents an organic group with 3 to 20 carbon atoms.

[0249] Here, the same carbon atom in the organic group constituting Bx can interact with the aforementioned Y. 11 Y 21 Y 31 (wherein, only the case of p=1) and Y 41 (Whereinin the case is limited to q=1) two or more bonds, the same carbon atom in the organic group constituting Bx may not be bonded to Y as described above. 11 Y 21 Y 31 (wherein, only the case of p=1) and Y 41 (wherein, only the case where q=1) involves two or more bonds.

[0250] Furthermore, from the viewpoint of further improving the low-temperature tensile elongation of the resin molded article, it is preferable that the same carbon atom in the organic group constituting Bx does not interact with the aforementioned Y. 11 Y 21 Y 31 (wherein, only the case of p=1) and Y 41 (wherein, only the case where q=1) involves two or more bonds, i.e., bonds with Y. 11 Bonded carbon atoms, and Y 21 Bonded carbon atoms, and Y 31 (This applies only to the case where p=1) the carbon atoms bonded, and the carbon atoms bonded to Y. 41 (In this case, only the case where q=1) the bonded carbon atoms are all different.

[0251] Furthermore, the same carbon atom in the organic group constituting Bx does not interact with the aforementioned Y. 11 Y 21 Y 31 (wherein, only the case of p=1) and Y 41 (Where, only in the case of q=1) when there are two or more bonds, the organic groups constituting Bx, with Y 11 Bonded carbon atoms, and Y 21 Bonded carbon atoms, and Y 31 (This applies only to the case where p=1) the carbon atoms bonded, and the carbon atoms bonded to Y. 41 (This applies only to the case where q = 1) Bonded carbon atoms can be adjacent to each other or not.

[0252] Furthermore, from the viewpoint of further improving the low-temperature tensile elongation of the resin molded article, it is preferable that the organic groups constituting Bx are similar to those of Y. 11 Bonded carbon atoms, and Y 21 Bonded carbon atoms, and Y 31 (This applies only to the case where p=1) the carbon atoms bonded, and the carbon atoms bonded to Y. 41 (Whereinin the case is limited to q=1) the bonded carbon atoms are not adjacent to each other.

[0253] Furthermore, Bx is preferably any one of the organic groups (i), (ii), (iii), and (iv) below, more preferably any one of the organic groups (i) or (iii) below, and even more preferably an organic group (i) below.

[0254] (i) may have a chain-like aliphatic hydrocarbon group having 3 to 20 carbon atoms as a substituent;

[0255] (ii) may have cyclic aliphatic hydrocarbon groups with 4 to 12 carbon atoms having substituents;

[0256] (iii) May have aromatic hydrocarbon cyclic groups with 6 to 14 substituents.

[0257] (iv) An organic group having 3 to 20 carbon atoms, wherein at least one single bond in a chain aliphatic hydrocarbon group having substituents is replaced by -O-, -C(=O)-, -OC(=O)- or -C(=O)-O- (excluding cases where two or more -O- groups are consecutive, cases where two or more -C(=O) groups are consecutive, and cases where -O- or -C(=O)- is located next to Y-). 11 Y 21 Y 31 Or Y 41 The condition of the bonded ends.

[0258] Furthermore, in this invention, "may have substituents" means "unsubstituted or substituented." Moreover, when the organic group contained in the general formula has substituents, the number of substituents in the organic group can be one or more. Additionally, when the organic group contained in the general formula has substituents, unless otherwise specified, the number of carbon atoms in the organic group having the substituent does not include the number of carbon atoms in the substituent. For example, when a chain aliphatic hydrocarbon cyclic group with 3 to 20 carbon atoms has a substituent, the number of carbon atoms in the chain aliphatic hydrocarbon cyclic group with 3 to 20 carbon atoms does not include the number of carbon atoms in the substituent.

[0259] Here, the preferred number of carbon atoms and structure of the aliphatic hydrocarbon group, aromatic hydrocarbon group or organic group in (i) to (iv) above are the same as those described in the "Ax" section of "Compound" for (i) to (iv) respectively.

[0260] Furthermore, as a preferred specific example of Bx, one can cite a group represented by any of the following formulas (2-1) to (2-35) that may have substituents. Here, "having substituents" means that any one of the hydrogen atoms in the group represented by any of the following formulas (2-1) to (2-35) is substituted.

[0261] In addition, Bx can be the same structure as Ax in the compound represented by the above formula (1), or it can be a different structure from each other.

[0262] [Chemical Formula 17]

[0263]

[0264] Furthermore, in the above equations (2-1)~(2-4), (2-20)~(2-26) and (2-30)~(2-33), "-" indicates an extension from any position of the ring, and intersects with Y. 11 Y 21 Y 31 Or Y 41 The bonding sites.

[0265] In addition, in the above equations (2-5)~(2-19), (2-27)~(2-29), (2-34)~(2-35), the "-" at the end of the chain structure indicates that it is related to Y. 11 Y 21 Y 31 Or Y 41 The bonding sites.

[0266] Furthermore, when p is 0, the structure represented by the above formula (3-1) (i.e., the hydrogen atom) can be any one of the hydrogen atoms of the group represented by any one 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., the hydrogen atom) can be any one of the hydrogen atoms of the group represented by any one of the above formulas (2-1) to (2-35).

[0267] Substituents that can be present as the group represented by any of the formulas (2-1) to (2-35) above include, for example, halogen atoms, alkyl groups having 1 to 4 carbon atoms, etc.

[0268] Furthermore, from the viewpoint of achieving excellent low-temperature tensile elongation of the resin molded article, 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), (2-20), and even more preferably a group represented by the above formula (2-6).

[0269] <Y 11 Y 41 >

[0270] In the above formula (3), Y 11 and Y 41 Each can independently represent a single bond, -C(=O)-, or -C(=O)-NR. 1 -or -C(=O)-O-. Additionally, R 1 It represents a hydrogen atom, a methyl group, or an ethyl group.

[0271] Furthermore, from the viewpoint of achieving good tensile elongation at low temperatures and adhesion to polyurethane in the resin molded body, while simultaneously improving heat shrinkage resistance and melt flowability, as Y 11 and Y 41 Each is independently preferred to be a single bond, -C(=O)- or -C(=O)-NR 1 -, more preferably a single bond or -C(=O)-, and even more preferably -C(=O)-.

[0272] <Y 21 Y 31 >

[0273] In the above formula (3), Y 21 and Y 31 Each can independently represent a single bond, -C (=O)-, and -NR. 2 -C(=O)- or -OC(=O)-. Additionally, R 2 It represents a hydrogen atom, a methyl group, or an ethyl group.

[0274] Furthermore, from the viewpoint of achieving good tensile elongation at low temperatures and adhesion to polyurethane in the resin molded body, while simultaneously improving heat shrinkage resistance and melt flowability, as Y 21 and Y 31 Each is independently preferred to be a single bond, -C(=O)-, or -NR. 2 -C(=O)-, more preferably a single bond or -C(=O)-, and even more preferably -C(=O)-.

[0275] Y 11 Y 41 Y 21 and Y 31 They can be independent of each other, or they can be the same.

[0276] <SP 11 SP 41 >

[0277] In the above formula (3), SP 11 and SP 41 Each can be independently represented as -CH2CH2O-, -CH2CH(CH3)O-, -CH(CH3)CH2O-, -CH2CH(CH2CH3)O-, or -CH(CH2CH3)CH2O-.

[0278] Moreover, as an SP 11 and SP 41 Each of them is preferably -CH2CH2O-, -CH2CH(CH3)O- or -CH(CH3)CH2O-, and more preferably -CH2CH2O-.

[0279] <SP 21 SP 31 >

[0280] In the above formula (3), SP 21 and SP 31 Each can be independently represented as -OCH2CH2-, -OCH(CH3)CH2-, -OCH2CH(CH3)-, -OCH(CH2CH3)CH2-, or -OCH2CH(CH2CH3)-.

[0281] Moreover, as an SP 21 and SP 31 Each of them is preferably -OCH2CH2-, -OCH(CH3)CH2- or -OCH2CH(CH3)-, and more preferably -OCH2CH2-.

[0282] <e、f、g、h>

[0283] In the above formula (3), e, f, g and h each independently represent integers from 0 to 30.

[0284] Furthermore, from the viewpoint of achieving good tensile elongation and adhesion to polyurethane at low temperatures in the resin molded body, while simultaneously improving heat shrinkage resistance and meltability, e, f, g, and h are each preferably represented by integers from 0 to 25, more preferably by integers from 2 to 20, even more preferably by integers from 3 to 15, even more preferably by integers from 4 to 12, and even more preferably by integers from 5 to 10.

[0285] <R a1 R b1 R c1 R d1 >

[0286] In equation (3) above, R a1 R b1 R c1 and R d1 Each can independently represent a chain-like aliphatic hydrocarbon group with 12 to 18 carbon atoms that can have substituents.

[0287] Composition of R a1 R b1 R c1 and R d1 The chain aliphatic hydrocarbon group having 12 to 18 carbon atoms of substituents preferably has 13 to 17 carbon atoms, more preferably 14 to 16.

[0288] Composition of R a1 R b1 R c1 and R d1 The chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms that may have substituents can each be an unsaturated aliphatic hydrocarbon group having unsaturated bonds (carbon-carbon double bonds or carbon-carbon triple bonds) or a saturated aliphatic hydrocarbon group without unsaturated bonds. Furthermore, when the aforementioned chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms have unsaturated bonds, the number of double bonds is, for example, one or more and five or fewer. In addition, the isomers formed through the carbon-carbon double bonds in the aforementioned chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms can be cis-isos, trans-isos, or a mixture of cis-isos and trans-isos.

[0289] As a component of R a1 R b1 R c1 and R d1 Chain aliphatic hydrocarbons with 12 to 18 carbon atoms can have substituents, such as alkyl groups with 1 to 3 carbon atoms, halogen atoms, etc.

[0290] R a1 R b1 R c1 and R d1 None of them contain epoxy groups.

[0291] R a1 R b1 R c1 and R d1 They can be independent of each other, or they can be the same.

[0292] Moreover, R is preferred a1 R b1 R c1 and R d1 Each independently, for example

[0293] -(CH2) 14 CH3

[0294] -(CH2)7CH=CH(CH2)5CH3、

[0295] -(CH2)7CH=CHCH2CH=CH(CH2)2CH3、

[0296] -(CH2)7CH=CHCH2CH=CHCH=CHCH3, or

[0297] -(CH2)7CH=CHCH2CH=CHCH2CH=CH2

[0298] Any one of the 15-carbon chain aliphatic hydrocarbon groups. Furthermore, at least one hydrogen atom of the aforementioned 15-carbon chain aliphatic hydrocarbon group may be substituted.

[0299] In the mixture of the present invention, each of the compounds represented by formula (1) and the compounds represented by formula (3) above comprises a compound having a single structure and a mixture of two or more compounds with different structures combined in any ratio.

[0300] For example, the mixture of the present invention may also contain at least two or more of the above-mentioned R. a R b R c and R d A mixture of compounds that are independent and distinct, as represented by the above formula (1).

[0301] In the mixture of the present invention, the content ratio of the compounds represented by formulas (1) and (3) is not particularly limited, but for example, relative to the total mass of the compounds represented by formulas (1) and (3), the mass ratio of the compound represented by formula (1) is preferably 50% by mass or more, more preferably 60% by mass or more, and even more preferably 65% ​​by mass or more. If the content ratio of the compound represented by formula (1) is at or above the lower limit value, the low-temperature tensile elongation and adhesion to polyurethane of the resin molded body formed from the resin composition prepared using the mixture of the present invention can be good, while the heat shrinkage resistance and meltability are improved.

[0302] There is no particular upper limit to the content ratio of the compound represented by formula (1), and it can also be 99% by mass.

[0303] <Methods for manufacturing compounds>

[0304] The compounds of the present invention (the compounds represented by formula (1) above) are not particularly limited and can be obtained by the following synthesis step (I) and epoxidation step (II), wherein the synthesis step (I) is a step of suitably bonding and / or modifying a plurality of compounds as raw materials to obtain the compound represented by formula (4) below, and the epoxidation step (II) is a step of removing R from the compound represented by formula (4) below obtained in the synthesis step. a2 R b2 R c2 and R d2 The process of epoxidizing at least one chain aliphatic hydrocarbon group.

[0305] <<(I) Synthesis Process>>

[0306] The compounds represented by the following formula (4) are not particularly limited and can be synthesized by combining known synthetic reactions. Examples of literature that describes known synthetic reactions include Sandler Karo's Organic Functional Group Preparations [I], [II] (Hirokawa Shoten), and MARCH'S ADVANCED ORGANICCHEMISTRY SIXTH EDITION (Michael B. Smith, Jerry March; WILEY).

[0307] Typically, compounds represented by the following formula (4) can utilize ether bonds (-O-), ester bonds (-C(=O)-O-, -OC(=O)-), and carbamate bonds (-C(=O)-NR). 1 -、-NR 2 The formation reaction of -C(=O)-) etc. allows for the suitable bonding and / or modification of multiple compounds used as starting materials to produce the product. Additionally, R... 1 and R 2 It means the same thing as above.

[0308] More specifically, the formation of ether bonds can occur, for example, as described below.

[0309] (i) The compound represented by formula D1-hal (hal represents a halogen atom. The same applies below.) is mixed with the compound represented by formula D2-OMet (Met represents an alkali metal (mainly sodium). The same applies below.) and condensed (Williamson synthesis). In addition, D1 and D2 in the formula represent any organic groups (the same applies below).

[0310] (ii) The compound represented by formula D1-hal and the compound represented by formula D2-OH are mixed in the presence of a base such as sodium hydroxide or potassium hydroxide and condensed.

[0311] (iii) The compound represented by formula D1-J (J represents an epoxy group) and the compound represented by formula D2-OH are mixed in the presence of a base such as sodium hydroxide or potassium hydroxide and condensed.

[0312] (iv) The compound represented by formula D1-OFN (OFN represents a group with an unsaturated bond) and the compound represented by formula D2-OMet are mixed in the presence of a base such as sodium hydroxide or potassium hydroxide and subjected to an addition reaction.

[0313] (v) The compound represented by formula D1-hal and the compound represented by formula D2-OMet are mixed in the presence of copper or cuprous chloride and condensed (Ullmann condensation).

[0314] More specifically, ester bond formation can occur, for example, as described below.

[0315] (vi) The compound represented by formula D1-COOH and the compound represented by formula D2-OH are subjected to dehydration condensation in the presence of a dehydrating condensing agent (WSC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride) etc.).

[0316] (vii) After obtaining the compound represented by the formula D1-C(=O)-hal by acting a halogenating agent on the compound represented by the formula D1-COOH, the compound is then reacted with the compound represented by the formula D2-OH in the presence of a base.

[0317] (viii) After obtaining a mixed anhydride by reacting an anhydride with a compound represented by formula: D1-COOH, the mixed anhydride is then reacted with a compound represented by formula: D2-OH.

[0318] (ix) The compound represented by formula D1-COOH and the compound represented by formula D2-OH undergo dehydration condensation in the presence of an acid catalyst or a base catalyst.

[0319] More specifically, the formation of urethane bonds can occur, for example, as described below.

[0320] (x) The compound represented by formula D1-N=C=O reacts with the compound represented by formula D2-OH in the presence of a base catalyst.

[0321] The compound represented by the following formula (4) can be produced, for example, by the reaction shown below.

[0322] [Chemical Formula 18]

[0323]

[0324] (where Ax and Y are in the formula) 1 ~Y 4 SP 1 ~SP 4 a, b, c, d, x, y represent the same meaning as above. Additionally, R... a2 R b2 R c2 R d2 (This refers to the chain-like aliphatic hydrocarbon group described later.)

[0325] [Chemical Formula 19]

[0326] (4)

[0327] That is, by reacting the compound with a carboxyl group represented by formula (A) and the compound with a hydroxyl group represented by formula (B) in a ratio of [moles of carboxyl groups in the compound represented by formula (A): 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, more preferably 1:1.0 to 1:1.5, the compound represented by the target formula (4) can be produced with high selectivity and high yield.

[0328] < <R a2 R b2 R c2 R d2 >>

[0329] In equation (4) above, R a2 R b2 R c2 and R d2 Each can independently represent a chain-like aliphatic hydrocarbon group with 12 to 18 carbon atoms that can have substituents.

[0330] Composition of R a2 R b2 R c2 and R d2 The chain aliphatic hydrocarbon group having 12 to 18 carbon atoms of substituents preferably has 13 to 17 carbon atoms, more preferably 14 to 16.

[0331] Composition of R a2 R b2 R c2 and R d2 The chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms that may have substituents can each be an unsaturated aliphatic hydrocarbon group having unsaturated bonds (carbon-carbon double bonds or carbon-carbon triple bonds) or a saturated aliphatic hydrocarbon group without unsaturated bonds. Furthermore, when the aforementioned chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms have unsaturated bonds, the number of double bonds is, for example, one or more and five or fewer. In addition, the isomers formed through the carbon-carbon double bonds in the aforementioned chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms can be cis-isos, trans-isos, or a mixture of cis-isos and trans-isos.

[0332] As a component of R a2 R b2 R c2 and R d2 Chain aliphatic hydrocarbons with 12 to 18 carbon atoms can have substituents, such as alkyl groups with 1 to 3 carbon atoms, halogen atoms, etc.

[0333] R a2 R b2 R c2 and R d2 None of them contain epoxy groups.

[0334] R a2 R b2 R c2 and R d2 They can be independent of each other, or they can be the same.

[0335] Moreover, R is preferred a2 R b2 R c2 and R d2 Each independently, for example

[0336] -(CH2) 14 CH3

[0337] -(CH2)7CH=CH(CH2)5CH3、

[0338] -(CH2)7CH=CHCH2CH=CH(CH2)2CH3、

[0339] -(CH2)7CH=CHCH2CH=CHCH=CHCH3, or

[0340] -(CH2)7CH=CHCH2CH=CHCH2CH=CH2

[0341] Any one of the 15-carbon chain aliphatic hydrocarbon groups. Furthermore, at least one hydrogen atom of the aforementioned 15-carbon chain aliphatic hydrocarbon group may be substituted.

[0342] Examples of dehydrating condensing agents used at this time include 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide p-toluenesulfonate, dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, bis(2,6-diisopropylphenyl)carbodiimide, and bis(trimethylsilyl)carbodiimide. Carbodiimides such as diisopropylcarbodiimide, 2-methyl-6-nitrobenzoic anhydride, 2,2'-carbonylbis-1H-imidazolium, 1,1'-oxodiimidazolium, diphenyl azidophosphate, 1-(4-nitrobenzenesulfonyl)-1H-1,2,4-triazole, 1H-benzotriazol-1-yloxytripyrrolidinylphosphonium hexafluorophosphate, 1H-benzotriazol-1-yloxytris(dimethylamino) Phosphorus hexafluorophosphate, N,N,N',N'-tetramethyl-O-(N-succinimide)urea tetrafluoroborate, N-(1,2,2,2-tetrachloroethoxycarbonyloxy)succinimide, N-benzyloxycarbonylsuccinimide, O-(6-chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethylurea tetrafluoroborate, O-(6-chlorobenzotriazol-1-yl)-N,N N',N'-Tetramethylurea hexafluorophosphate, 2-bromo-1-ethylpyridinium tetrafluoroborate, 2-chloro-1,3-dimethylimidazolinenium chloride, 2-chloro-1,3-dimethylimidazolinenium hexafluorophosphate, 2-chloro-1-methylpyridinium iodide, 2-chloro-1-methylpyridinium p-toluenesulfonate, 2-fluoro-1-methylpyridinium p-toluenesulfonate, pentachlorophenyl trichloroacetate, etc.

[0343] From the perspectives of reactivity, cost, and available 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 preferred.

[0344] The amount of dehydrating condensing agent added is typically 1 to 1.5 moles relative to the number of moles of carboxyl groups in the compound represented by formula (A), preferably 1 to 1.2 moles, and more preferably 1 to 1.1 moles. Furthermore, the dehydrating condensing agent can be added directly or in the form of a solution dissolved or dispersed in a suitable solvent.

[0345] At this point, an activator can be used. Examples of activators include 4-(dimethylamino)pyridine (N,N-dimethyl-4-aminopyridine).

[0346] The amount of activator added relative to the above-mentioned dehydrating condensing agent is usually 0.01 to 1.0 moles, preferably 0.01 to 0.5 moles. Alternatively, the activator can be added directly or in the form of a solution dissolved or dispersed in a suitable solvent.

[0347] The solvent used in this reaction is not particularly limited as long as the reaction is inactive. Examples include: ether solvents such as diethyl ether, tetrahydrofuran, 1,2-dimethoxyethane, 1,4-dioxane, cyclopentyl methyl ether, and methyl tert-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-dimethylimidazolinone, and hexamethylphosphotriamide; sulfur-containing solvents such as dimethyl sulfoxide and sulfolane; halogen solvents such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; and mixed solvents consisting of two or more of these. Among these, ether solvents, ester solvents, amide solvents, and halogen solvents are preferred, with amide solvents being particularly preferred, especially N-methylpyrrolidone, N,N-dimethylacetamide, and N,N-dimethylformamide.

[0348] There is no particular limit to the amount of solvent used. It can be appropriately determined by taking into account the type of compound used, the scale of the reaction, etc. The amount of solvent used is usually 1 to 100 g relative to 1 g of the carboxyl group represented by formula (A).

[0349] The reaction proceeds smoothly in a temperature range from -10°C to the boiling point of the solvent used, but preferably from 10°C to 80°C, more preferably from 15°C to 50°C. The reaction time of each reaction also depends on the scale of the reaction, but is usually from a few minutes to tens of hours, preferably from a few minutes to seventy hours, more preferably from a few hours to thirty hours.

[0350] The compound represented by formula (4) can also be produced, for example, by the reaction shown below.

[0351] [Chemical Formula 20]

[0352]

[0353] (where Ax and Y are in the formula) 1 ~Y 4 R 1 R 2 SP 1 ~SP 4 a, b, c, d, R a2 R b2 R c2 R d2 (x, y represent the same meaning as above.)

[0354] That is, by reacting the compound with an acyl chloride group represented by formula (C) and the compound with 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) to the number of moles of acyl chloride groups in the compound represented by formula (C)] of 1:2 to 2:1, preferably 1:1.5 to 1.5:1, more preferably 1:1.0 to 1:1.2, the target compound represented by formula (4) above can be produced with high selectivity and high yield.

[0355] At this point, examples of organic bases that can be used include triethylamine, diisopropylethylamine, pyridine, 4-(dimethylamino)pyridine (N,N-dimethyl-4-aminopyridine), and 2,6-dimethylpyridine; and inorganic bases such as sodium hydroxide, sodium carbonate, and sodium bicarbonate.

[0356] At this point, an activator can be used. Examples of activators include 4-(dimethylamino)pyridine (N,N-dimethyl-4-aminopyridine).

[0357] The amount of activator added is typically 0.01 to 1.0 moles relative to the compound with an acyl chloride group represented by formula (C) above, preferably 0.01 to 0.5 moles, and more preferably 0.01 to 0.2 moles. Alternatively, the activator can be added directly or in the form of a solution dissolved or dispersed in a suitable solvent.

[0358] The solvent used in this reaction is not particularly limited as long as the reaction is inactive. Examples include: ether solvents such as diethyl ether, tetrahydrofuran, 1,2-dimethoxyethane, 1,4-dioxane, cyclopentyl methyl ether, and methyl tert-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-dimethylimidazolinone, and hexamethylphosphotriamide; sulfur-containing solvents such as dimethyl sulfoxide and sulfolane; halogen solvents such as dichloromethane, 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 tert-butyl ether, chloroform, and 1,2-dichloroethane being particularly preferred.

[0359] There is no particular limit to the amount of solvent used. It can be appropriately determined by taking into account the type of compound used, the scale of the reaction, etc. The amount of solvent used is usually 1 to 100 g relative to 1 g of the carboxyl group represented by formula (A).

[0360] The reaction proceeds smoothly in a temperature range from -20°C to the boiling point of the solvent used, but preferably from -5°C to 50°C, more preferably from 0°C to 40°C. The reaction time of each reaction also depends on the scale of the reaction, but is usually from a few minutes to a dozen hours, preferably from a few minutes to ten hours, more preferably from several tens of minutes to five hours.

[0361] At this point, the compound with an acyl chloride group represented by formula (C) can be a commercially available compound or a compound synthesized from the compound with a carboxyl group represented by formula (A) above.

[0362] The compound with an acyl chloride group represented by formula (C) can be manufactured as described below.

[0363] [Chemical Formula 21]

[0364]

[0365] (In the formula, x and y have the same meaning as above.)

[0366] At this time, chlorinating agents that can be used include thionyl chloride (SOCl2), oxaloyl chloride [(C(=O)Cl)2], sulfonyl chloride (SO2Cl2), phosphorus oxychloride (POCl3), phosphorus trichloride (PCl3), and phosphorus pentachloride (PCl5), with thionyl chloride, oxaloyl chloride, and sulfonyl chloride being preferred. These chlorinating agents can be used alone or in combination of two or more.

[0367] The chlorinating agent used is reacted with the carboxyl compound represented by formula (A) and the chlorinating agent in a ratio of [moles of carboxyl groups in the compound represented by formula (A): chlorinating agent] of 1:2 to 2:1, preferably 1:5 to 1:3, more preferably 1:1.0 to 1:1.5, thereby enabling the production of the acyl chloride compound represented by the target formula (C) with high selectivity and high yield.

[0368] At this point, an activator can be used. Examples of activators include N,N-dimethylformamide, triethylamine, and tetraalkylammonium, with N,N-dimethylformamide and tetraalkylammonium being preferred.

[0369] The amount of activator added is typically 0.01 to 3.0 moles relative to the carboxyl compound represented by formula (A) above, preferably 0.01 to 2.0 moles, and more preferably 0.01 to 0.5 moles.

[0370] The solvent used in this reaction is not particularly limited as long as the reaction is inactive. Examples include: ether solvents such as diethyl ether, tetrahydrofuran, 1,2-dimethoxyethane, 1,4-dioxane, cyclopentyl methyl ether, and methyl tert-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-dimethylimidazolinone, and hexamethylphosphotriamide; sulfur-containing solvents such as dimethyl sulfoxide and sulfolane; halogen solvents such as dichloromethane, 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 tert-butyl ether, chloroform, and 1,2-dichloroethane being particularly preferred.

[0371] There is no particular limit to the amount of solvent used. It can be appropriately determined by taking into account the type of compound used, the scale of the reaction, etc. The amount of solvent used is usually 1 to 100 g relative to 1 g of the carboxyl group represented by formula (A).

[0372] The reaction proceeds smoothly in a temperature range from -20°C to the boiling point of the solvent used, but preferably from -5°C to 150°C, more preferably from 0°C to 110°C. The reaction time of each reaction also depends on the scale of the reaction, but is usually from a few minutes to a dozen hours, preferably from a few minutes to ten hours, more preferably from several tens of minutes to five hours.

[0373] As the compound represented by the above formula (B), cashew phenol and its derivatives, which are made from cashew nut shell oil extracts, are preferably used.

[0374] There are no particular restrictions as long as it is cashew nut shell extract or cashew nut shell extract derivatives containing hydroxyl groups. The following is a specific example from Cardlä Company, but equivalent products from other companies can also be used.

[0375] Cashew nut shell extract and its derivatives are manufactured by companies such as Cardläne. Specific examples of Cardläne products include NX-2021, NX-2022, NX-2023, NX-2023D, NX-2024, NX-2025, NX-2026, NX-5205, UltraLITE2023, UL-2023, NC-510 (hydrogenated derivative), LITE2020 (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), LITE2100, and LITE2100R.

[0376] The preferred compounds are NX-2021, NX-2022, NX-2023, NX-2023D, NX-2024, NX-2025, NX-2026, NX-5205, UltraLITE2023, UL-2023, NC-510 (hydrogenated compound), 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).

[0377] More preferably, NX-2021, NX-2022, NX-2023, NX-2024, NX-2025, NX-2026, UltraLITE2023, NC-510 (hydrogenated compound), 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).

[0378] <<(II) Epoxidation Process>>

[0379] In the epoxidation process, the compound represented by formula (4) obtained in the above (I) synthesis process, R a2 R b2 R c2 and R d2 At least one chain-like aliphatic hydrocarbon group is epoxidized. Epoxidation is not particularly limited and can be carried out by known epoxidation methods. Examples of oxidizing agents include inorganic peroxides such as oxygen-containing gases, hydrogen peroxide, and sodium peroxide; and organic peroxides 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, menthol hydroperoxide, and 1-methylhexane hydroperoxide.

[0380] In epoxidation reactions, catalysts can be used as needed. Examples include metal compounds containing tungsten, molybdenum, vanadium, titanium, rhenium, ruthenium, etc.; aldehydes such as acetaldehyde, isobutyraldehyde, isovaleraldehyde, and trimethylacetaldehyde; α-aminophosphonic acids such as α-aminomethylphosphonic acid and α-aminoethylphosphonic acid; and quaternary onium salts such as trioctylmethylammonium chloride, trioctylethylammonium bromide, dilauryl dimethylammonium iodide, and distearyl dimethyl benzyl ammonium hydrogen phosphate.

[0381] The solvents used in the epoxidation reaction can be solvents that do not react with the aforementioned oxidants. Examples include 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, and dimethylacetamide.

[0382] The reaction temperature of the epoxidation reaction varies depending on the oxidant, catalyst and solvent used, but is preferably 0 to 150°C, more preferably 0 to 60°C.

[0383] <Methods for preparing mixtures>

[0384] <<The method for manufacturing the compound represented by formula (3)>>

[0385] The compound represented by the above formula (3) is not particularly limited and can be synthesized by combining known synthetic reactions. As an example of literature that records known synthetic reactions, the literature described in the section on "methods for the manufacture of compounds" can be cited.

[0386] Typically, the compound represented by formula (3) above can use ether bonds (-O-), ester bonds (-C(=O)-O-, -OC(=O)-), and carbamate bonds (-C(=O)-NR). 1 -、-NR 2 The formation reaction of -C(=O)-) etc. allows for the suitable bonding and / or modification of multiple compounds used as starting materials to produce the product. Additionally, R... 1 and R 2 It means the same thing as above.

[0387] As a specific method for forming ether bonds, ester bonds and urethane bonds, the same method as the method for the compound represented by formula (1) above can be cited in the "Method for manufacturing the compound" section.

[0388] The compound represented by formula (3) can be produced, for example, by the reaction shown below.

[0389] [Chemical Formula 22]

[0390]

[0391] (In the formula, 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 meaning as above.

[0392] That is, by reacting the compound with a carboxyl group represented by formula (D) and the compound with a hydroxyl group represented by formula (E) in a ratio of [moles of carboxyl groups in the compound represented by formula (D): 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, more preferably 1:1.0 to 1:1.5, the compound represented by the target formula (3) can be produced with high selectivity and high yield.

[0393] At this time, as a dehydrating condensing agent and an activator, the same dehydrating condensing agent and activator described in the "Method for Manufacturing Compound" section for the compound represented by the above formula (1) can be used in the above-described addition amount and addition method.

[0394] As for the solvent used in this reaction, there are no particular limitations as long as the reaction is inactive, and the same solvent as that described in the section on "method of manufacturing the compound" for the compound represented by the above formula (1) can be cited.

[0395] There is no particular limit to the amount of solvent used. It can be appropriately determined by considering the type of compound used, the scale of the reaction, etc. The amount of solvent used is usually 1 to 100 g relative to 1 g of the carboxyl group represented by formula (D).

[0396] The reaction proceeds smoothly in a temperature range from -10°C to the boiling point of the solvent used, but preferably from 10°C to 80°C, more preferably from 15°C to 50°C. The reaction time of each reaction also depends on the scale of the reaction, but is usually from a few minutes to tens of hours, preferably from a few minutes to seventy hours, more preferably from a few hours to thirty hours.

[0397] The compound represented by formula (3) can also be produced, for example, by the reaction shown below.

[0398] [Chemical Formula 23]

[0399]

[0400] (In the formula, 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 meaning as above.

[0401] That is, by reacting the compound with an acyl chloride group represented by formula (F) and the compound with 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 acyl chloride groups in the compound represented by formula (F)] of 1:2 to 2:1, preferably 1:1.5 to 1.5:1, more preferably 1:1.0 to 1:1.2, the compound represented by the target formula (3) can be produced with high selectivity and high yield.

[0402] At this point, the same base used can be the same base described in the section "Method for manufacturing the compound" for the compound represented by the above formula (1).

[0403] At this point, an activator can be used. As an activator, the same activator described in the section "Method for manufacturing the compound" for the compound represented by formula (1) above can be used in the above-described amount and method of addition.

[0404] As for the solvent used in this reaction, there are no particular limitations as long as the reaction is inactive, and the same solvent as that described in the section on "method of manufacturing the compound" for the compound represented by the above formula (1) can be cited.

[0405] There is no particular limit to the amount of solvent used. It can be appropriately determined by considering the type of compound used, the scale of the reaction, etc. The amount of solvent used is usually 1 to 100 g relative to 1 g of the carboxyl group represented by formula (D).

[0406] The reaction proceeds smoothly in a temperature range from -20°C to the boiling point of the solvent used, but preferably from -5°C to 50°C, more preferably from 0°C to 40°C. The reaction time of each reaction also depends on the scale of the reaction, but is usually from a few minutes to a dozen hours, preferably from a few minutes to ten hours, more preferably from several tens of minutes to five hours.

[0407] At this point, the compound with an acyl chloride group represented by formula (F) can be a commercially available compound or a compound synthesized from the compound with a carboxyl group represented by formula (D) above.

[0408] The compound with an acyl chloride group represented by formula (F) can be manufactured as described below.

[0409] [Chemical Formula 24]

[0410]

[0411] (In the formula, p and q have the same meaning as above.)

[0412] At this point, the same chlorinating agent as described in the section "Method for manufacturing the compound" for the compound represented by the above formula (1) can be cited as the chlorinating agent used.

[0413] The chlorinating agent used is reacted with the carboxyl compound represented by formula (D) and the chlorinating agent in a ratio 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 enabling the production of the acyl chloride compound represented by the target formula (F) with high selectivity and high yield.

[0414] At this point, an activator can be used. As an activator, the same activator described in the section "Method for manufacturing the compound" for the compound represented by formula (1) above can be used in the above-described addition amount.

[0415] As for the solvent used in this reaction, there are no particular limitations as long as the reaction is inactive, and the same solvent as that described in the section on "method of manufacturing the compound" for the compound represented by the above formula (1) can be cited.

[0416] There is no particular limit to the amount of solvent used. It can be appropriately determined by considering the type of compound used, the scale of the reaction, etc. The amount of solvent used is usually 1 to 100 g relative to 1 g of the carboxyl group represented by formula (D).

[0417] The reaction proceeds smoothly in a temperature range from -20°C to the boiling point of the solvent used, but preferably from -5°C to 150°C, more preferably from 0°C to 110°C. The reaction time of each reaction also depends on the scale of the reaction, but is usually from a few minutes to a dozen hours, preferably from a few minutes to ten hours, more preferably from several tens of minutes to five hours.

[0418] As the compound represented by the above formula (E), examples can be given of the same compounds as those described in the section "Methods for manufacturing compounds" concerning the compound represented by formula (1) and the compound represented by formula (B).

[0419] The mixture of the present invention can be manufactured by mixing the compound represented by formula (1) manufactured by the above manufacturing method with the compound represented by formula (3) above.

[0420] For the compounds represented by formula (1) and formula (3) above, each can be used alone, and two or more compounds with different structures can be mixed in any ratio. The mixing ratio of the compounds represented by formula (1) and formula (3) above is consistent with the content ratio of the compounds represented by formula (1) and formula (3) above as described in the "mixture" section.

[0421] In the epoxidation step included in the method for manufacturing the compound of the present invention (the compound represented by formula (1) above), when the epoxidation rate is 100%, the pure compound of the present invention is obtained. Alternatively, when the epoxidation rate is less than 100%, a mixture of the compounds represented by formulas (1) and (3) above is obtained. In this mixture, Ax and Y in formula (1) above... 1 Y 2 Y 3 Y 4 SP 1 SP 2 SP 3 SP 4 a, b, c, d, x, y, and R in equation (4) above. a2 R b2 R c2 R d2 respectively with Bx and Y in the above formula (3) 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 Consistent.

[0422] (Instructions for using the compound)

[0423] The compounds and mixtures of the present invention are not particularly limited. For example, they can be used as plasticizers in the preparation of resin compositions for forming resin molded articles, thereby imparting softness and elasticity to the resin molded articles. Moreover, if the compounds and mixtures of the present invention are used as plasticizers, the resin molded articles formed from the resin compositions prepared using the compounds and mixtures of the present invention can exhibit good low-temperature tensile elongation and adhesion to polyurethane, while simultaneously improving heat shrinkage resistance and melt flowability.

[0424] Furthermore, when using the compounds and mixtures of the present invention as plasticizers, for the compound represented by formula (1) above (the compound of the present invention) or the compound represented by formula (3) above, each compound having a single structure can be used alone, or two or more compounds with different structures can be used in any ratio. That is, mixtures containing two or more compounds represented by formula (1) or (3) above with different structures can also be used as plasticizers.

[0425] (Plasticizer composition)

[0426] The plasticizer composition of the present invention (hereinafter, sometimes simply referred to as "plasticizer composition") is characterized in that it contains at least the compounds or mixtures of the present invention described above. When a plasticizer composition containing the compounds or mixtures of the present invention is used in the preparation of a resin composition, it is possible to achieve good low-temperature tensile elongation and adhesion to polyurethane in the resin molded body formed from the prepared resin composition, while simultaneously improving heat shrinkage resistance and melt flowability.

[0427] Here, the plasticizer composition of the present invention may further comprise plasticizers other than the compounds or mixtures of the present invention described above. The plasticizers contained in the plasticizer composition of the present invention, other than the compounds or mixtures of the present invention, are not particularly limited; for example, polyester plasticizers and trimellitate plasticizers can be used. Preferably, the plasticizer composition of the present invention further comprises polyester plasticizers in addition to the compounds or mixtures of the present invention. Furthermore, the plasticizer composition of the present invention may further comprise plasticizers other than the compounds or mixtures of the present invention and polyester plasticizers described above (hereinafter, sometimes referred to as "other plasticizers").

[0428] <Compounds of the present invention>

[0429] The compounds of the present invention used for preparing plasticizer compositions can be used alone, or two or more compounds with different structures can be used in any ratio.

[0430] <The mixture of the present invention>

[0431] As a mixture of the present invention for preparing plasticizer compositions, for the compound represented by formula (1) above (the compound of the present invention) or the compound represented by formula (3) above, each can be used alone as a compound having a single structure, or two or more compounds with different structures can be used in any ratio.

[0432] When the plasticizer composition contains a polyester plasticizer, the content of the compound of the present invention in the plasticizer composition, relative to 100 parts by weight of the polyester plasticizer, is preferably 1 part by weight or more, more preferably 1.5 parts by weight or more, further preferably 2 parts by weight or more, even more preferably 2.5 parts by weight or more, even more preferably 3 parts by weight or more, particularly preferably 6.0 parts by weight or more, preferably 70 parts by weight or less, more preferably 60 parts by weight or less, further preferably 50 parts by weight or less, even more preferably 40 parts by weight or less, particularly preferably 20 parts by weight or less, and may also be 18 parts by weight or less, or may also be 16 parts by weight or less. If the content of the compound of the present invention in the plasticizer composition is at or above the above-mentioned lower limit, the low-temperature tensile elongation and adhesion to polyurethane of the formed resin molded article can be good, while the heat shrinkage resistance and meltability are improved. On the other hand, if the content of the compound of the present invention in the plasticizer composition is at or below the above-mentioned upper limit, the heat shrinkage resistance of the formed resin molded article can be sufficiently ensured.

[0433] <Polyester Plasticizers>

[0434] Polyester plasticizers are components that impart sufficient tensile properties (e.g., elongation at break, tensile strength, etc.) to resin molded articles formed using resin compositions containing plasticizer compositions. Furthermore, when using polyester plasticizers, in the formation of laminates consisting of resin molded articles formed from resin compositions containing plasticizer compositions and lined with foamed polyurethane molded articles, the polyester plasticizer is difficult to transfer from the resin molded article to the foamed polyurethane molded article even at high temperatures, thus further improving the heat shrinkage resistance of the resin molded article.

[0435] As a polyester plasticizer, there are no particular limitations. For example, polyesters containing structural units from adipic acid (adipic acid-based polyesters), polyesters containing structural units from sebacic acid (sebacic acid-based polyesters), and polyesters containing structural units from phthalic acid (phthalic acid-based polyesters) can be used. In addition, these polyesters can be used alone or in any ratio of two or more.

[0436] From the viewpoint of further improving the heat shrinkage resistance of the resin molded body, adipic acid-based polyester (polyester containing structural units derived from adipic acid) is preferred as a polyester plasticizer.

[0437] The viscosity of the polyester plasticizer is preferably 500 mPa·s or more, more preferably 1000 mPa·s or more, more preferably 8000 mPa·s or less, and more preferably 5000 mPa·s or less.

[0438] In addition, "viscosity" can be measured at a temperature of 25°C according to JIS Z8803.

[0439] <Other Plasticizers>

[0440] The plasticizer composition may optionally further include other plasticizers besides the compounds of the present invention and polyester plasticizers described above.

[0441] Specific examples of other plasticizers include those described in International Publication No. 2016 / 098344, such as (b1) polyester plasticizers and (b2) plasticizers other than phenols and their modifiers. From the viewpoint of further improving the low-temperature tensile elongation of the formed resin molded article, epoxidized vegetable oil is preferred, and epoxidized soybean oil is more preferred.

[0442] The content of other plasticizers in the plasticizer composition is not particularly limited, but can be 0 parts by weight or more and 15 parts by weight or less relative to 100 parts by weight of the above-mentioned polyester plasticizer.

[0443] Furthermore, when using epoxidized vegetable oils such as epoxidized soybean oil as other plasticizers, from the viewpoint of further improving the low-temperature tensile elongation of the formed resin molded article while ensuring sufficient heat shrinkage resistance of the resin molded article, the content of the epoxidized vegetable oil as other plasticizer relative to 100 parts by weight of the above-mentioned polyester plasticizer is preferably 2 parts by weight or more, more preferably 3 parts by weight or more, even more preferably 4 parts by weight or more, preferably 10 parts by weight or less, more preferably 7 parts by weight or less, and even more preferably 5 parts by weight or less.

[0444] (Resin Composition)

[0445] One embodiment of the resin composition may comprise (a) a resin and (b) the plasticizer composition of the present invention (hereinafter, sometimes simply referred to as "(b) plasticizer composition"). In other words, the resin composition comprises at least (a) a resin and the compound of the present invention described above, and may optionally further comprise polyester plasticizers and other plasticizers.

[0446] In addition, the resin composition may optionally further include additives other than the resin and plasticizer compositions described above (a) and (b).

[0447] Furthermore, resin molded articles formed using resin compositions containing at least the compounds of the present invention exhibit excellent low-temperature tensile elongation, adhesion to polyurethane, and meltability.

[0448] Furthermore, when manufacturing a laminate consisting of a resin molded body formed using a resin composition and a foamed polyurethane molded body, the thermal shrinkage of the resin molded body in the laminate can be sufficiently suppressed. That is, the resin molded body formed using a resin composition containing at least the compounds of the present invention also exhibits excellent resistance to heat shrinkage.

[0449] Therefore, if a resin composition containing at least the compounds of the present invention is used, resin molded articles suitable for automotive interior materials, such as dashboard skins and door trim skins, which have excellent low-temperature tensile elongation and heat shrinkage resistance, can be obtained.

[0450] Furthermore, for example, from the viewpoint that resin compositions containing at least the compounds of the present invention readily yield resin molded articles that can be well used as automotive interior materials, resin compositions containing at least the compounds of the present invention are preferably used for powder molding, and more preferably for powder slush molding.

[0451] <(a) Resin>

[0452] As for (a) the resin, there are no particular limitations as long as the desired effect of the present invention can be obtained, and any known resin can be used.

[0453] Furthermore, the resin contained in the resin composition (a) is a different component from the compounds of the present invention and the polyester plasticizers contained in the plasticizer composition (b), as well as the additives that are optional components.

[0454] Here, (a) the glass transition temperature of the resin is preferably 50°C or higher and 100°C or lower.

[0455] Furthermore, as (a) resin, a halogen-containing resin is preferred, a fluorine-containing resin or a chlorine-containing resin is more preferred, a chlorine-containing resin is even more preferred, and a vinyl chloride resin is particularly preferred.

[0456] Here, (a) the proportion of vinyl chloride resin in the 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.

[0457] <<vinyl chloride resin>>

[0458] As a vinyl chloride resin, granular vinyl chloride resin is typically used. Furthermore, as a vinyl chloride resin, it may contain one or more types of vinyl chloride resin particles, and may optionally further contain one or more types of vinyl chloride resin microparticles. Preferably, the vinyl chloride resin contains at least vinyl chloride resin particles, and more preferably, it contains both vinyl chloride resin particles and vinyl chloride resin microparticles.

[0459] Moreover, vinyl chloride resin can be manufactured using any of the previously known manufacturing methods, such as suspension polymerization, emulsion polymerization, solution polymerization, and bulk polymerization.

[0460] In addition, in this specification, "resin particles" refers to particles with a diameter of 30 μm or larger, and "resin microparticles" refers to particles with a diameter of less than 30 μm.

[0461] In addition to homopolymers composed of vinyl chloride monomer units, vinyl chloride copolymers containing preferably 50% by mass or more, more preferably 70% by mass or more of vinyl chloride monomer units can also be cited as vinyl chloride resins. Furthermore, as specific examples of monomers (comonomers) capable of forming vinyl chloride copolymers and copolymerizing with vinyl chloride monomers, monomers described in International Publication No. 2016 / 098344 can be used. Moreover, these components can be used alone or in combination of two or more in any ratio.

[0462] [Vinyl chloride resin granules]

[0463] In resin compositions, vinyl chloride resin particles typically function as the matrix resin (substrate). Furthermore, vinyl chloride resin particles are preferably manufactured via suspension polymerization.

[0464] - Average degree of polymerization -

[0465] Furthermore, 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, more preferably 5000 or less, more preferably 3000 or less, and even more preferably 2800 or less. If the average degree of polymerization of the vinyl chloride resin constituting the vinyl chloride resin particles is above the aforementioned lower limit, the physical strength of the resin molded article formed using the resin composition can be sufficiently ensured, while improving, for example, tensile properties, especially tensile elongation. Moreover, resin molded articles with good tensile elongation, for example, will not scatter fragments during airbag inflation and deployment but will crack as designed, and are therefore preferably used as automotive interior materials such as automotive dashboard skins with excellent ductility. On the other hand, if the average degree of polymerization of the vinyl chloride resin constituting the vinyl chloride resin particles is below the aforementioned upper limit, the meltability of the resin composition can be improved.

[0466] In addition, in this invention, the "average degree of polymerization" can be determined according to JIS K6720-2.

[0467] - Average particle size -

[0468] Furthermore, the average particle size of the vinyl chloride resin particles is typically 30 μm or more, preferably 50 μm or more, more preferably 100 μm or more, more preferably 500 μm or less, and even more preferably 200 μm or less. If the average particle size of the vinyl chloride resin particles is at or above the aforementioned lower limit, the powder flowability of the resin composition can be improved. On the other hand, if the average particle size of the vinyl chloride resin particles is below or above the aforementioned upper limit, the meltability of the resin composition can be improved, and the surface smoothness of the formed resin molded article can be enhanced.

[0469] Furthermore, in this invention, the "average particle size" can be determined in the form of volume average particle size by laser diffraction according to JIS Z8825.

[0470] -Contains proportion-

[0471] Furthermore, 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, 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 at or above the aforementioned lower limit, the physical strength of the resin molded article formed using the resin composition can be sufficiently ensured, while the tensile elongation can be improved. On the other hand, if the content of vinyl chloride resin particles in the vinyl chloride resin is at or below the aforementioned upper limit, the powder flowability of the resin composition can be improved.

[0472] [Vinyl chloride resin microparticles]

[0473] In resin compositions, vinyl chloride resin microparticles typically function as a separating agent (powder flowability improver). Furthermore, vinyl chloride resin microparticles are preferably manufactured via emulsion polymerization.

[0474] - Average degree of polymerization -

[0475] Furthermore, 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, more 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 separating agent is at or above the aforementioned lower limit, the powder flowability of the resin composition can be improved, and the tensile elongation of the formed resin molded article 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 at or below the aforementioned upper limit, the meltability of the resin composition can be improved, and the surface smoothness of the formed resin molded article can be improved.

[0476] - Average particle size -

[0477] Furthermore, the average particle size of the vinyl chloride resin particles is typically less than 30 μm, preferably 10 μm or less, more preferably 5 μm or less, more preferably 0.1 μm or more, and even more preferably 1 μm or more. If the average particle size of the vinyl chloride resin particles is at or above the aforementioned lower limit, for example, the size of the separating agent will not be too small, and the powder flowability of the resin composition can be improved. On the other hand, if the average particle size of the vinyl chloride resin particles is at or below the aforementioned upper limit, the meltability of the resin composition can be improved, and the surface smoothness of the formed resin molded article can be improved.

[0478] -Contains proportion-

[0479] Furthermore, the content of vinyl chloride resin particles in the vinyl chloride resin can be 0% by mass, but is preferably 5% by mass or more, more preferably 10% by mass or more, more preferably 30% by mass or less, and more preferably 20% by mass or less. If the content of vinyl chloride resin particles in the vinyl chloride resin is at or above the aforementioned lower limit, the powder flowability of the resin composition can be improved. On the other hand, if the content of vinyl chloride resin particles in the vinyl chloride resin is at or below the aforementioned upper limit, the physical strength of the formed resin molded article can be improved.

[0480] <(b) Plasticizer Composition>

[0481] As (b) the plasticizer composition, a plasticizer composition comprising at least the compounds or mixtures of the present invention described above, and optionally further comprising polyester plasticizers and other plasticizers, is used.

[0482] The content of the compound or mixture of the present invention in the resin composition relative to 100 parts by weight of the above-described (a) resin is preferably 1 part by weight or more, more preferably 1.5 parts by weight or more, further preferably 2 parts by weight or more, even more preferably 2.5 parts by weight or more, even more preferably 3 parts by weight or more, particularly preferably 6.0 parts by weight or more, preferably 70 parts by weight or less, more preferably 60 parts by weight or less, further preferably 50 parts by weight or less, even more preferably 40 parts by weight or less, particularly preferably 20 parts by weight or less, and may also be 18 parts by weight or less, or may also be 16 parts by weight or less. If the content of the compound or mixture of the present invention in the resin composition is at or above the above-described 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 the 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 at or below the above-described upper limit, the heat shrinkage resistance of the formed resin molded article can be sufficiently ensured.

[0483] Furthermore, when the plasticizer composition in (b) contains a polyester plasticizer, the content of the polyester plasticizer in the resin composition relative to 100 parts by weight of the resin in (a) described above is preferably 30 parts by weight or more, more preferably 50 parts by weight or more, even more preferably 70 parts by weight or more, even more preferably 80 parts by weight or more, even more preferably 85 parts by weight or more, preferably 200 parts by weight or less, more preferably 180 parts by weight or less, even more preferably 150 parts by weight or less, even more preferably 130 parts by weight or less, even more preferably 110 parts by weight or less, and particularly preferably 100 parts by weight or less. If the content of the polyester plasticizer in the resin composition is at or above the aforementioned lower limit, the heat shrinkage resistance of the formed resin molded article can be further improved. On the other hand, if the content of the polyester plasticizer in the resin composition is at or below the aforementioned upper limit, the adhesion of the formed resin molded article to the foamed polyurethane molded article can be sufficiently ensured.

[0484] The content of the other plasticizers mentioned above in the resin composition is not particularly limited, but can be more than 0 parts by weight and less than 15 parts by weight relative to 100 parts by weight of the resin (a) mentioned above.

[0485] Furthermore, when using epoxidized vegetable oils such as epoxidized soybean oil as other plasticizers, from the viewpoint of further improving the low-temperature tensile elongation of the formed resin molded article while ensuring sufficient heat shrinkage resistance of the resin molded article, the content of the epoxidized vegetable oil as other plasticizer relative to 100 parts by weight of the above-mentioned (a) resin is preferably 2 parts by weight or more, more preferably 3 parts by weight or more, even more preferably 4 parts by weight or more, preferably 10 parts by weight or less, and more preferably 7 parts by weight or less.

[0486] Furthermore, the total content of the compounds of the present invention, the polyester plasticizer, and other plasticizers in the resin composition (i.e., the content of the plasticizer composition, (b)) relative to 100 parts by weight of resin is preferably 31 parts by weight or more, more preferably 53.5 parts by weight or more, even more preferably 75 parts by weight or more, even more preferably 86.5 parts by weight or more, even more preferably 92 parts by weight or more, preferably 235 parts by weight or less, more preferably 208 parts by weight or less, even more preferably 176 parts by weight or less, even more preferably 154 parts by weight or less, even more preferably 129 parts by weight or less, and particularly preferably 119 parts by weight or less. If the content of the plasticizer composition in the resin composition is within the above-mentioned range, the resin composition can be easily molded (e.g., powder molding), and the low-temperature tensile elongation, heat shrinkage resistance, and adhesion to the foamed polyurethane molded body can be balanced to a high degree.

[0487] <Additives>

[0488] In addition to the above-mentioned components, the resin composition may further contain various additives. There are no particular limitations on the additives, but examples include lubricants; stabilizers such as perchloric acid-treated hydrotalcite, zeolite, β-diketone, and fatty acid metal salts; release agents; other separating agents besides the aforementioned vinyl chloride resin particles; impact modifiers; perchloric acid compounds other than perchloric acid-treated hydrotalcite (sodium perchlorate, potassium perchlorate, etc.); antioxidants; mildew inhibitors; flame retardants; antistatic agents; fillers; light stabilizers; foaming agents; and pigments.

[0489] Furthermore, the additives that may be included in the resin composition, for example, can be those described in International Publication No. 2016 / 098344, and their preferred content can also be the same as that described in International Publication No. 2016 / 098344.

[0490] <Preparation method of resin composition>

[0491] The resin composition can be prepared by mixing the above-mentioned components.

[0492] Here, the mixing method for the above-mentioned (a) resin, (b) plasticizer composition, and various additives further formulated as needed is not particularly limited. For example, a method can be given where the components except the release agent (containing vinyl chloride resin particles) are mixed by dry mixing, and then the release agent is added and mixed. Here, a Henschel mixer is preferably used for dry mixing. In addition, the temperature during dry mixing is not particularly limited, but it is preferably 50°C or higher, more preferably 70°C or higher, and more preferably 200°C or lower.

[0493] <Uses of Resin Compositions>

[0494] Furthermore, the resulting resin composition is preferably used for powder molding, and more preferably for powder slush molding.

[0495] (Resin molded body)

[0496] The resin molded article according to one embodiment is obtained by molding the above-described resin composition using any method. Furthermore, since the resin molded article is formed using the above-described resin composition, it generally contains at least (a) a resin and (b) a plasticizer composition. That is, the resin molded article generally contains at least (a) a resin and the compound of the present invention, and optionally further contains polyester plasticizers, other plasticizers, and additives. Moreover, the resin molded article containing at least the compound of the present invention exhibits excellent low-temperature tensile elongation, adhesion to polyurethane, heat shrinkage resistance, and melt flow properties.

[0497] Therefore, resin molded articles are preferred for use as automotive interior materials such as dashboard panels.

[0498] <Methods for forming resin molded articles>

[0499] Here, when a resin molded body is formed by powder slush molding, there is no particular limitation on the temperature of the metal mold during powder slush molding, but it is preferably 200°C or higher, more preferably 220°C or higher, more preferably 300°C or lower, and more preferably 280°C or lower.

[0500] Furthermore, there are no particular limitations in manufacturing the resin molded body; for example, the following method can be used: The resin composition is poured into a metal mold within the aforementioned temperature range, left for 5 to 30 seconds, then the remaining resin composition is shaken off. The mold is then left at any temperature for 30 to 3 minutes. Afterward, the metal mold is cooled to 10°C to 60°C, and the resulting resin molded body is demolded from the metal mold. A sheet-like molded body shaped to the form of the metal mold is then obtained.

[0501] (Layered structure)

[0502] One embodiment of the laminate includes a foamed polyurethane molded body and the aforementioned resin molded body. Furthermore, the resin molded body typically forms one surface of the laminate.

[0503] Furthermore, the laminate, for example, is a resin molded body formed using the above-described resin composition, exhibiting excellent low-temperature tensile elongation, adhesion to polyurethane, heat shrinkage resistance, and melt flowability. Therefore, the laminate is preferably used as an automotive interior material for forming automotive interior parts, particularly automotive dashboards.

[0504] Here, there is no particular limitation on the lamination method of the polyurethane foam and the resin molded body, and the following methods can be used for example. That is, the following methods can be used: (1) after preparing the polyurethane foam and the resin molded body separately, the two are bonded together by heat fusion, heat bonding or known adhesives; (2) the isocyanate and polyols, which are the raw materials of the polyurethane foam, are reacted on the resin molded body to polymerize, and the polyurethane is foamed by a known method, thereby directly forming the polyurethane foam on the resin molded body. Among these, the latter method (2) is preferred from the perspective of simple process and easy to firmly bond the resin molded body and the polyurethane foam even when a laminate of various shapes is obtained.

[0505] Example

[0506] The present invention will now be specifically described based on embodiments, but the present invention is not limited to these embodiments. Furthermore, in the following description, unless otherwise specified, "%" and "part" to indicate quantity refer to mass.

[0507] Furthermore, the low-temperature tensile properties, heat shrinkage resistance, adhesion to polyurethane foam, and melt properties of the vinyl chloride resin molded sheet (vinyl chloride resin molded body) were determined and evaluated by the following methods.

[0508] <Tensive properties at low temperatures (tensile strength, elongation)>

[0509] The obtained vinyl chloride resin molded sheet was punched using a No. 1 dumbbell cutter as described in JIS K6251. According to JIS K7113, the tensile elongation at break (%) and tensile stress at break (MPa) were measured at a tensile speed of 200 mm / min at -25°C. A higher value for the tensile elongation at break indicates better tensile elongation at low temperatures (low-temperature tensile elongation). Conversely, a higher value for the tensile stress at break indicates better tensile strength at low temperatures.

[0510] <Heat Shrinkage Resistance>

[0511] The length of the short side of the obtained laminated vinyl chloride resin sheet was measured using a three-dimensional measuring instrument (Mitutoyo "Crysta-Plus M443"), and used as the measured value before heating.

[0512] The laminate was then heated in a Geer oven (manufactured by Toyo Seiki Co., Ltd.) at 120°C for 600 hours. Afterward, the laminate was removed from the oven, and the length of the short side of the vinyl chloride resin sheet was measured using the aforementioned three-dimensional measuring instrument. This measured value was taken as the actual value after heating. Using the measured values ​​before and after heating, the heat shrinkage rate (%) was calculated as shown in the following formula.

[0513]

[0514] In addition, the smaller the heat shrinkage rate, the less heat shrinkage the vinyl chloride resin molded sheet has, and the better the heat shrinkage resistance of the vinyl chloride resin molded sheet.

[0515] <Adhesion of polyurethane foam molded parts>

[0516] Using a laminate formed by lining a polyurethane foam with a vinyl chloride resin molded sheet, the vinyl chloride resin molded sheet is peeled off from the polyurethane foam molded sheet. The surfaces of the peeled vinyl chloride resin molded sheet and the surface lined with the polyurethane foam molded sheet are visually inspected to evaluate the adhesion of the vinyl chloride resin molded sheet (vinyl chloride resin molded sheet) to the polyurethane molded sheet.

[0517] The condition where the surface portion of the polyurethane foam remains on the entire vinyl chloride resin molded sheet as visually confirmed is defined as "foam breakage" (Evaluation A in Tables 1 and 2). The condition where the surface portion of the polyurethane foam remains only on a portion of the surface of the vinyl chloride resin molded sheet, and no surface portion of the polyurethane foam remains on other parts, is defined as "partial interface peeling" (Evaluation B in Tables 1 and 2). The condition where the entire surface portion of the vinyl chloride resin molded sheet is free of polyurethane foam remains is defined as "complete interface peeling" (Evaluation C in Tables 1 and 2).

[0518] Furthermore, the more surface areas of the polyurethane foam remaining on the surface of the vinyl chloride resin molded sheet, the higher the adhesion between the vinyl chloride resin molded sheet (vinyl chloride resin molded body) and the polyurethane foam molded body.

[0519] <Meltability>

[0520] A strip-shaped metal mold is placed on a hot plate that is heated at equal intervals within a temperature range of 170°C to 270°C to obtain a metal mold that has undergone staged heating. A vinyl chloride resin composition with a thickness of 1 mm is then poured into the staged-heated metal mold and left to melt for 45 seconds. Next, the remaining vinyl chloride resin composition is shaken off, and the metal mold is cooled with water, thereby demolding the vinyl chloride resin into a strip-shaped vinyl chloride resin sheet. The surface of the demolded vinyl chloride resin sheet is visually observed, and the temperature of the metal mold at the molten portion is taken as the melting temperature of the vinyl chloride resin composition. Furthermore, in the above-mentioned strip-shaped vinyl chloride resin sheet, the portion with a smooth surface without any residual particle shape is defined as the "molten portion". The lower the melting temperature, the better the meltability of the vinyl chloride resin composition.

[0521] (synthesis example)

[0522] The compounds used in each example were prepared as described below.

[0523] Additionally, nuclear magnetic resonance (NMR) using "Cardolite NX-2026" (manufactured by Cardolite) as used in the following synthesis example will be employed. 1 H-NMR, 13 The spectra obtained by C-NMR and IR (ATR) measurements are shown in the figure. Figures 1-3 .

[0524] Additionally, the NMR (Neural Magnetic Resonance) of "Cardolite NX-7507" (manufactured by Cardolite) used in the following synthesis example will be analyzed. 1 H-NMR, 13 The spectra obtained by C-NMR, CH COSY, and IR (ATR) measurements are shown below. Figures 4-7 .Depend on Figure 4 of 1 The H-NMR spectrum shows that the signal position of the hydroxyl group is 3.33 ppm.

[0525] <Synthetic Example 1> Synthesis of Diester Mixture 1

[0526] Diester mixture 1 was synthesized from "Cardolite NX-2026" (Cardolite Company) according to the following synthesis scheme.

[0527] In addition, in the synthetic scheme, R represents any one of the following four hydrocarbon groups with 15 carbon atoms, and * indicates the position of the group bonded to the benzene ring by a single bond (the same applies to synthetic examples 2 to 18 below). Moreover, "Cardolite NX-2026" and diester mixture 1 represent a mixture of compounds in which R is any one of the following four hydrocarbon groups, and the two Rs contained in diester mixture 1 may be the same or different.

[0528] [Chemical Formula 25]

[0529]

[0530] In a three-necked reactor equipped with a thermometer, 80 g (0.27 mol) of Cardolite NX-2026 (manufactured by Cardolite) was dissolved in 150 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. 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 to this solution and dissolved. While adjusting the temperature to below 25°C in a water bath, 53.58 g (0.28 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added to the above solution, and the entire mixture was stirred directly at 25°C for 24 hours.

[0531] After the reaction was complete, the reaction solution was added to 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.

[0532] After removing the solvent by rotary evaporation, the residue was purified by silica gel column chromatography (hexane:ethyl acetate = 90:10 (volume ratio)) to obtain 81 g of diester mixture 1 as a colorless oil. The structure of diester mixture 1 was identified by NMR and infrared absorption spectroscopy.

[0533] 1 H-NMR (500MHz, CDCl3, TMS, δppm): The generation of a signal of 1.90–1.85 ppm from the α-position of the carbonyl carbon was confirmed.

[0534] 13 C-NMR (500MHz, CDCl3, TMS, δppm): The generation of a signal of 171.86ppm from carbonyl carbon was confirmed.

[0535] IR (ATR): A 1761 cm⁻¹ junction from the ester bond was confirmed. -1 Peak generation.

[0536] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in... Figures 8-10 .

[0537] <Synthetic Example 2> Synthesis of Diester Mixture 2

[0538] Diester mixture 2 was synthesized from "Cardolite NX-2026" (Cardolite Corporation) according to the following synthesis scheme.

[0539] In addition, "Cardolite NX-2026" and diester mixture 2 respectively indicate a mixture of compounds in which R is any one of the following four hydrocarbon groups. The two Rs contained in diester mixture 2 may be the same or different.

[0540] [Chemical Formula 26]

[0541]

[0542] In a three-necked reactor equipped with a thermometer, 80 g (0.27 mol) of Cardolite NX-2026 (manufactured by Cardolite) was dissolved in 150 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. 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 to this solution and dissolved. While adjusting the temperature to below 25°C in a water bath, 53.58 g (0.28 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added to the above solution, and the entire mixture was stirred directly at 25°C for 24 hours.

[0543] After the reaction was complete, the reaction solution was added to 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.

[0544] After removing the solvent by rotary evaporation, the residue was purified by silica gel column chromatography (hexane:ethyl acetate = 90:10 (volume ratio)) to obtain 82 g of diester mixture 2 as a colorless oil. The structure of diester mixture 2 was identified by NMR and infrared absorption spectroscopy.

[0545] 1 H-NMR (500MHz, CDCl3, TMS, δppm): The generation of a signal of 1.79–1.73 ppm from the α-position of the carbonyl carbon was confirmed.

[0546] 13 C-NMR (500MHz, CDCl3, TMS, δppm): A signal of 172.38ppm from carbonyl carbon was confirmed.

[0547] IR (ATR): A 1759 cm⁻¹ junction from the ester bond was confirmed. -1 Peak generation.

[0548] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in... Figures 11-13 .

[0549] <Synthetic Example 3> Synthesis of Diester Mixture 3

[0550] Diester mixture 3 was synthesized from "Cardolite NX-2026" (Cardolite Corporation) according to the following synthesis scheme.

[0551] In addition, "Cardolite NX-2026" and diester mixture 3 respectively indicate that R is a mixture of compounds in which any one of the following four hydrocarbon groups is present. The two Rs contained in diester mixture 3 may be the same or different.

[0552] [Chemical Formula 27]

[0553]

[0554] In a three-necked reactor equipped with a thermometer, 80 g (0.27 mol) of Cardolite NX-2026 (manufactured by Cardolite) was dissolved in 150 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. 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 to this solution and dissolved. While adjusting the temperature to below 25°C in a water bath, 53.58 g (0.28 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added to the above solution, and the entire mixture was stirred directly at 25°C for 24 hours.

[0555] After the reaction was complete, the reaction solution was added to 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.

[0556] After removing the solvent by rotary evaporation, the residue was purified by silica gel column chromatography (hexane:ethyl acetate = 90:10 (volume ratio)) to obtain 82 g of diester mixture 3 as a colorless oil. The structure of diester mixture 3 was identified by NMR and infrared absorption spectroscopy.

[0557] 1 H-NMR (500MHz, CDCl3, TMS, δppm): The generation of a signal of 8.33ppm from the new aromatic ring was confirmed.

[0558] 13 C-NMR (500MHz, CDCl3, TMS, δppm): The generation of a signal of 164.45ppm from carbonyl carbon was confirmed.

[0559] IR (ATR): A 1738 cm⁻¹ junction from the ester bond was confirmed. -1 Peak generation.

[0560] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in... Figures 14-16 .

[0561] <Synthetic Example 4> Synthesis of Diester Mixture 4

[0562] Diester mixture 4 was synthesized from "Cardolite NX-7507" (Cardolite Company) according to the following synthesis scheme.

[0563] In addition, "Cardolite NX-7507" and diester mixture 4 respectively indicate a mixture of compounds in which R is any one of the following four hydrocarbon groups. The two Rs contained in diester mixture 4 may be the same or different.

[0564] [Chemical Formula 28]

[0565]

[0566] In a three-necked reactor equipped with a thermometer, 80 g (0.13 mol) of Cardolite NX-7507 (manufactured by Cardolite) was dissolved in 150 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. 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 to this solution and dissolved. While adjusting the temperature to below 25°C in a water bath, 25.24 g (0.13 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added to the above solution, and the entire mixture was stirred directly at 25°C for 24 hours.

[0567] After the reaction was complete, the reaction solution was added to 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.

[0568] After removing the solvent by rotary evaporation, the residue was purified by silica gel column chromatography (chloroform:methanol = 90:10 (volume ratio)) to obtain 84 g of diester mixture 4 as a light brown oil. The structure of diester mixture 4 was identified by NMR and infrared absorption spectroscopy.

[0569] 1 ¹H-NMR (500MHz, CDCl₃, TMS, δppm): The disappearance of the hydroxyl signal of 3.33ppm from Cardolite NX-7507 (manufactured by Cardolite) was confirmed.

[0570] 13 C-NMR (500MHz, CDCl3, TMS, δppm): The generation of signals from carbonyl carbon at 175.03ppm and 173.23ppm was confirmed.

[0571] IR (ATR): A 1736 cm⁻¹ junction from the ester bond was confirmed. -1 1685cm -1 Peak generation.

[0572] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in... Figures 17-19 .

[0573] <Synthetic Example 5> Synthesis of Diester Mixture 5

[0574] Diester mixture 5 was synthesized from "Cardolite NX-7507" (Cardolite Company) according to the following synthesis scheme.

[0575] In addition, "Cardolite NX-7507" and diester mixture 5 respectively indicate that R is a mixture of compounds in which any one of the following four hydrocarbon groups is present. The two Rs contained in diester mixture 5 may be the same or different.

[0576] [Chemical Formula 29]

[0577]

[0578] In a three-necked reactor equipped with a thermometer, 80 g (0.13 mol) of Cardolite NX-7507 (manufactured by Cardolite) was dissolved in 150 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. 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 to this solution and dissolved. While adjusting the temperature to below 25°C in a water bath, 27.74 g (0.15 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added to the above solution, and the entire mixture was stirred directly at 25°C for 24 hours.

[0579] After the reaction was complete, the reaction solution was added to 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.

[0580] After removing the solvent by rotary evaporation, the residue was purified by silica gel column chromatography (chloroform:methanol = 90:10 (volume ratio)) to obtain 81 g of diester mixture 5 as a light brown oil. The structure of diester mixture 5 was identified by NMR and infrared absorption spectroscopy.

[0581] 1 ¹H-NMR (500MHz, CDCl₃, TMS, δppm): The disappearance of the hydroxyl signal of 3.33ppm from Cardolite NX-7507 (manufactured by Cardolite) was confirmed.

[0582] 13 C-NMR (500MHz, CDCl3, TMS, δppm): The generation of signals from carbonyl carbon at 175.01ppm and 173.69ppm was confirmed.

[0583] IR (ATR): A 1734 cm⁻¹ junction from the ester bond was confirmed. -1 1684cm -1 Peak generation.

[0584] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in... Figures 20-22 .

[0585] <Synthetic Example 6> Synthesis of Diester Mixture 6

[0586] Diester mixture 6 was synthesized from "Cardolite NX-7507" (Cardolite Company) according to the following synthesis scheme.

[0587] In addition, "Cardolite NX-7507" and diester mixture 6 respectively indicate a mixture of compounds in which R is any one of the following four hydrocarbon groups. The two Rs contained in diester mixture 6 may be the same or different.

[0588] [Chemical Formula 30]

[0589]

[0590] In a three-necked reactor equipped with a thermometer, 84.58 g (0.139 mol) of Cardolite NX-7507 (manufactured by Cardolite) was dissolved in 250 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. 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 to this solution and dissolved. While adjusting the temperature to below 25°C in a water bath, 29.32 g (0.153 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added to the above solution, and the entire mixture was stirred directly at 25°C for 22 hours. After the reaction was complete, the reaction solution was added to 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. After removing the solvent by rotary evaporation, the residue was purified by silica gel column chromatography (chloroform:methanol = 85:15 (volume ratio)) to obtain 82 g of diester mixture 6 as a light brown oil. The structure of diester mixture 6 was identified by NMR and infrared absorption spectroscopy.

[0591] 1 ¹H-NMR (500MHz, CDCl₃, TMS, δppm): The disappearance of the hydroxyl signal from Cardolite NX-7507 (manufactured by Cardolite) at 3.33 ppm was confirmed. The formation of aromatic hydrogens from terephthalic acid was confirmed at 8.11 ppm.

[0592] 13 C-NMR (500MHz, CDCl3, TMS, δppm): The generation of signals from carbonyl carbon at 174.96ppm and 165.62ppm was confirmed.

[0593] IR (ATR): Confirmed at 1720 cm⁻¹ from the ester bond. -1 1689cm -1 Peak generation.

[0594] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in... Figures 23-25 .

[0595] <Synthetic Example 7> Synthesis of Diester Mixture 7

[0596] In Synthesis Example 1, 80 g of "Cardolite NX-2026" (manufactured by Cardolite) was changed to 85.3 g, 18.57 g of adipic acid was changed to 16.0 g of succinic acid, 6.83 g of N,N-dimethylamino-4-pyridine (DMAP) was changed to 7.28 g, and 53.58 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was changed to 57.0 g. Otherwise, the same operation was performed, thereby obtaining 83 g of diester mixture 7 in the form of colorless oil.

[0597] <Synthetic Example 8> Synthesis of Diester Mixture 8

[0598] In Synthesis Example 1, 80 g of "Cardolite NX-2026" (manufactured by Cardolite) was changed to 83.3 g, 18.57 g of adipic acid was changed to 27.0 g of 1,3,5-pentanetricarboxylic 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. Otherwise, the same operation was performed, thereby obtaining 83 g of diester mixture 8 in the form of colorless oil.

[0599] <Synthetic Example 9> Synthesis of Diester Mixture 9

[0600] In Synthesis Example 1, 80 g of "Cardolite NX-2026" (manufactured by Cardolite) 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. Otherwise, the same operation was performed, thereby obtaining 83 g of diester mixture 9 in the form of colorless oil.

[0601] <Synthetic Example 10> Synthesis of Epoxidized Diester Mixture 1

[0602] According to the following synthesis scheme, epoxide diester mixture 1 was synthesized from diester mixture 1 synthesized in Synthesis Example 1.

[0603] In addition, diester mixture 1 and epoxidized diester mixture 1 respectively represent mixtures of compounds in which R is any one of the following four hydrocarbon groups. The two Rs contained in epoxidized diester mixture 1 may be the same or different.

[0604] [Chemical Formula 31]

[0605]

[0606] In a three-necked reactor equipped with a thermometer, 80 g of diester mixture 1 was dissolved in 200 mL of toluene under a nitrogen stream. 140 g (2.33 mol) of acetic acid and 11.4 g (0.11 mol) of phosphoric acid were added to the solution and dissolved. The solution was heated to 50 °C, and 182.2 mL (2.33 mol; specific gravity 1.45) of 30% hydrogen peroxide was slowly added dropwise over 30 minutes. The entire mixture was then stirred directly at 50 °C for 6 hours.

[0607] After the reaction was complete, a 30% (w / w) aqueous solution of sodium bisulfite was slowly added under vigorous stirring while cooling the reaction solution in an ice bath. The solution was added until the potassium iodide starch paper no longer changed color, and then extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was then collected, and a saturated aqueous solution of sodium bicarbonate was slowly added while cooling in an ice bath to make it weakly alkaline (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 the sodium sulfate was filtered off.

[0608] After removing the solvent by rotary evaporation, the 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.

[0609] 1 ¹H-NMR (500MHz, CDCl₃, TMS, δppm): A decrease in signal intensity from the double bond (6.60–4.70 ppm) was confirmed. Additionally, a peak from the epoxy group (3.22–2.78 ppm) was observed. The conversion rate calculated from this decrease in double bond signal was 85.6%.

[0610] 13 C-NMR (500MHz, CDCl3, TMS, δppm): The generation of signals from epoxy groups in the range of 57.27–46.42 ppm was confirmed.

[0611] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in... Figures 26-28 .

[0612] <Synthetic Example 11> Synthesis of Epoxidized Diester Mixture 2

[0613] According to the following synthesis scheme, epoxidized diester mixture 2 was synthesized from diester mixture 2 synthesized in Synthesis Example 2.

[0614] In addition, diester mixture 2 and epoxidized diester mixture 2 respectively represent mixtures of compounds in which R is any one of the following four hydrocarbon groups. The two Rs contained in epoxidized diester mixture 2 may be the same or different.

[0615] [Chemical Formula 32]

[0616]

[0617] In a three-necked reactor equipped with a thermometer, 80 g of diester mixture 2 was dissolved in 200 mL of toluene under a nitrogen stream. 132.5 g (2.21 mol) of acetic acid and 10.8 g (0.11 mol) of phosphoric acid were added to the solution and dissolved. The solution was heated to 50 °C, and 172.5 mL (2.21 mol; specific gravity 1.45) of 30% hydrogen peroxide was slowly added dropwise over 30 minutes. The entire mixture was then stirred directly at 50 °C for 6 hours.

[0618] After the reaction was complete, a 30% (w / w) aqueous solution of sodium bisulfite was slowly added under vigorous stirring while cooling the reaction solution in an ice bath. The solution was added until the potassium iodide starch paper no longer changed color, and then extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was then collected, and a saturated aqueous solution of sodium bicarbonate was slowly added while cooling in an ice bath to make it weakly alkaline (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 the sodium sulfate was filtered off.

[0619] After removing the solvent by rotary evaporation, the 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.

[0620] 1 ¹H-NMR (500MHz, CDCl₃, TMS, δppm): A decrease in signal intensity from the double bond (6.00–4.70 ppm) was confirmed. Additionally, a peak from the epoxy group (3.22–2.78 ppm) was observed. The conversion rate calculated from this decrease in double bond signal was 87.6%.

[0621] 13 C-NMR (500MHz, CDCl3, TMS, δppm): The generation of signals from epoxy groups in the range of 57.27–46.33 ppm was confirmed.

[0622] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in... Figures 29-31 .

[0623] <Synthetic Example 12> Synthesis of Epoxidized Diester Mixture 3

[0624] According to the following synthesis scheme, epoxidized diester mixture 3 was synthesized from diester mixture 3 synthesized in Synthesis Example 3.

[0625] In addition, diester mixture 3 and epoxidized diester mixture 3 respectively represent mixtures of compounds in which R is any one of the following four hydrocarbon groups. The two Rs contained in epoxidized diester mixture 3 may be the same or different.

[0626] [Chemical Formula 33]

[0627]

[0628] In a three-necked reactor equipped with a thermometer, 80 g of diester mixture 3 was dissolved in 200 mL of toluene under a nitrogen stream. 137.2 g (2.28 mol) of acetic acid and 11.2 g (0.11 mol) of phosphoric acid were added to this solution and dissolved. The solution was heated to 50 °C, and 178.6 mL (2.28 mol; specific gravity 1.45) of 30% hydrogen peroxide was slowly added dropwise over 30 minutes. The entire mixture was then stirred directly at 50 °C for 6 hours.

[0629] After the reaction was complete, a 30% (w / w) aqueous solution of sodium bisulfite was slowly added under vigorous stirring while cooling the reaction solution in an ice bath. The solution was added until the potassium iodide starch paper no longer changed color, and then extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was then collected, and a saturated aqueous solution of sodium bicarbonate was slowly added while cooling in an ice bath to make it weakly alkaline (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 the sodium sulfate was filtered off.

[0630] After removing the solvent by rotary evaporation, the 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 light brown oil. The structure of epoxidized diester mixture 3 was identified by NMR and infrared absorption spectroscopy.

[0631] 1 ¹H-NMR (500MHz, CDCl₃, TMS, δppm): A decrease in signal intensity from the double bond (6.00–4.70 ppm) was confirmed. Additionally, a peak from the epoxy group (3.22–2.78 ppm) was observed. The conversion rate calculated from this decrease in double bond signal was 88.4%.

[0632] 13 C-NMR (500MHz, CDCl3, TMS, δppm): The generation of signals from epoxy groups in the range of 57.36–46.43 ppm was confirmed.

[0633] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in... Figures 32-34 .

[0634] <Synthetic Example 13> Synthesis of Epoxidized Diester Mixture 4

[0635] According to the following synthesis scheme, epoxidized diester mixture 4 was synthesized from diester mixture 4 synthesized in Synthesis Example 4.

[0636] In addition, diester mixture 4 and epoxidized diester mixture 4 respectively represent mixtures of compounds in which R is any one of the following four hydrocarbon groups. The two Rs contained in epoxidized diester mixture 4 may be the same or different.

[0637] [Chemical Formula 34]

[0638]

[0639] In a three-necked reactor equipped with a thermometer, 80 g (0.06 mol) of diester mixture 4 was dissolved in 500 mL of dichloromethane under a nitrogen stream. 1.93 g (0.018 mol) of sodium carbonate was added to the solution, and the mixture was cooled in an ice bath. While cooling the solution in an ice bath, 370.1 g (0.44 mol) of a 9% peracetic acid solution (Aldrich) was slowly added dropwise over 1 hour, and the mixture was stirred directly in an ice bath for 1 hour. The reaction mixture was then brought to room temperature and stirred for 18 hours. The reaction mixture was then cooled in an ice bath again, and 185 g (0.22 mol) of a 9% peracetic acid solution (Aldrich) was slowly added dropwise over 30 minutes. The mixture was then brought to room temperature and stirred for another 20 hours.

[0640] After the reaction was complete, a 1 mol / L sodium thiosulfate aqueous solution was slowly added under vigorous stirring while cooling the reaction solution in an ice bath. The solution was added until the potassium iodide starch paper no longer changed color, and then extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was then collected, and a saturated sodium bicarbonate aqueous solution was slowly added under ice bath to make it weakly alkaline (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 the sodium sulfate was filtered off.

[0641] After removing the solvent by rotary evaporation, the 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 light brown oil. The structure of epoxidized diester mixture 1 was identified by NMR and infrared absorption spectroscopy.

[0642] 1 H-NMR (500MHz, CDCl3, TMS, δppm): The double bond conversion was 90.2% calculated from the residual signal from the double bond in the range of 6.60–5.20 ppm. 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in... Figures 35-37 .

[0643] <Synthetic Example 14> Synthesis of Epoxidized Diester Mixture 5

[0644] According to the following synthesis scheme, epoxidized diester mixture 5 was synthesized from diester mixture 5 synthesized in Synthesis Example 5.

[0645] In addition, diester mixture 5 and epoxidized diester mixture 5 respectively represent mixtures of compounds in which R is any one of the following four hydrocarbon groups. The two Rs contained in epoxidized diester mixture 5 may be the same or different.

[0646] [Chemical Formula 35]

[0647]

[0648] In a three-necked reactor equipped with a thermometer, 80 g (0.06 mol) of diester mixture 5 was dissolved in 500 mL of dichloromethane under a nitrogen stream. 1.86 g (0.017 mol) of sodium carbonate was added to the solution, and the mixture was cooled in an ice bath. While cooling the solution in an ice bath, 355.3 g (0.42 mol) of a 9% peracetic acid solution (Aldrich) was slowly added dropwise over 1 hour, and the entire mixture was stirred directly in an ice bath for 1 hour. The reaction mixture was then brought to room temperature and stirred for 18 hours. The reaction mixture was then cooled in an ice bath again, and 177.7 g (0.21 mol) of a 9% peracetic acid solution (Aldrich) was slowly added dropwise over 30 minutes.

[0649] Return all contents to room temperature and stir for another 24 hours.

[0650] After the reaction was complete, a 1 mol / L sodium thiosulfate aqueous solution was slowly added under vigorous stirring while cooling the reaction solution in an ice bath. The solution was added until the potassium iodide starch paper no longer changed color, and then extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was then collected, and a saturated sodium bicarbonate aqueous solution was slowly added under ice bath to make it weakly alkaline (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 the sodium sulfate was filtered off.

[0651] After removing the solvent by rotary evaporation, the 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 light brown oil. The structure of epoxidized diester mixture 2 was identified by NMR and infrared absorption spectroscopy.

[0652] 1 H-NMR (500MHz, CDCl3, TMS, δppm): The double bond conversion was 81.8% calculated from the residual amount of the signal from the double bond in the range of 6.60–5.20 ppm. 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in... Figures 38-40 .

[0653] <Synthetic Example 15> Synthesis of Epoxidized Diester Mixture 6

[0654] According to the following synthesis scheme, epoxidized diester mixture 6 was synthesized from diester mixture 6 synthesized in Synthesis Example 6.

[0655] In addition, diester mixture 6 and epoxidized diester mixture 6 respectively represent mixtures of compounds in which R is any one of the following four hydrocarbon groups. The two Rs contained in epoxidized diester mixture 6 may be the same or different.

[0656] [Chemical Formula 36]

[0657]

[0658] In a three-necked reactor equipped with a thermometer, 80 g (0.06 mol) of diester mixture 6 was dissolved in 500 mL of dichloromethane under a nitrogen stream. 1.91 g (0.018 mol) of sodium carbonate was added to the solution, and the mixture was cooled in an ice bath. While cooling the solution in an ice bath, 364.7 g (0.43 mol) of a 9% peracetic acid solution (Aldrich) was slowly added dropwise over 1 hour, and the mixture was stirred directly in an ice bath for 1 hour. The reaction mixture was then brought to room temperature and stirred for 20 hours. The reaction mixture was then cooled in an ice bath again, and 182.4 g (0.22 mol) of a 9% peracetic acid solution (Aldrich) was slowly added dropwise over 30 minutes. The mixture was then brought to room temperature and stirred for another 20 hours.

[0659] After the reaction was complete, a 1 mol / L sodium thiosulfate aqueous solution was slowly added under vigorous stirring while cooling the reaction solution in an ice bath. The solution was added until the potassium iodide starch paper no longer changed color, and then extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was then collected, and a saturated sodium bicarbonate aqueous solution was slowly added under ice bath to make it weakly alkaline (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 the sodium sulfate was filtered off.

[0660] After removing the solvent by rotary evaporation, the 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 light brown oil. The structure of epoxidized diester mixture 1 was identified by NMR and infrared absorption spectroscopy.

[0661] 1 H-NMR (500MHz, CDCl3, TMS, δppm): The double bond conversion was 82.0% calculated from the residual amount of the signal from the double bond in the range of 6.60–5.20 ppm. 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in... Figures 41-43 .

[0662] <Synthetic Example 16> Synthesis of Epoxidized Diester Mixture 7

[0663] In Synthesis Example 10, the diester mixture 1:80 g was changed to a diester mixture 7:80 g, acetic acid 140 g (2.33 mol) was changed to 142 g (2.36 mol), phosphoric acid 11.4 g (0.11 mol) was changed to 11.6 g (0.12 mol), and 30% by weight hydrogen peroxide 182.2 mL (2.33 mol) was changed to 184.9 mL (2.36 mol). The same operation was performed otherwise to obtain an epoxidized diester mixture 7.77 g.

[0664] <Synthetic Example 17> Synthesis of Epoxidized Diester Mixture 8

[0665] In Synthesis Example 10, the diester mixture 1:80g was changed to diester mixture 8:80g, acetic acid 140g (2.33mol) was changed to 107g (1.78mol), phosphoric acid 11.4g (0.11mol) was changed to 8.7g (0.09mol), and 30% by weight hydrogen peroxide 182.2mL (2.33mol) was changed to 139.4mL (1.78mol). The same operation was performed otherwise to obtain 79g of epoxidized diester mixture 8.

[0666] <Synthetic Example 18> Synthesis of Epoxidized Diester Mixture 9

[0667] In Synthesis Example 10, the diester mixture 1:80g was changed to diester mixture 9:80g, acetic acid 140g (2.33mol) was changed to 136g (2.27mol), phosphoric acid 11.4g (0.11mol) was changed to 11.1g (0.11mol), and 30% by weight hydrogen peroxide 182.2mL (2.33mol) was changed to 177.2mL (2.27mol). The same operation was performed otherwise to obtain 75g of epoxidized diester mixture 9.

[0668] (Example 1)

[0669] <Preparation of Vinyl Chloride Resin Compositions>

[0670] The components shown in Table 2, excluding the plasticizer composition (polyester-based plasticizer, compounds, and other plasticizers) and the vinyl chloride resin microparticles as a release agent, were placed in a Henschel mixer and mixed. Then, when the temperature of the mixture reached 80°C, all of the aforementioned plasticizer composition was added, and the mixture was allowed to dry completely (meaning the plasticizer was absorbed by the vinyl chloride resin particles, and the mixture became dry). Mixing continued until the maximum temperature reached 100°C or higher and 200°C or lower. Afterwards, when the dried mixture was cooled to a temperature below 100°C, the vinyl chloride resin microparticles as a release agent were added to prepare the vinyl chloride resin composition.

[0671] The melt properties of the obtained vinyl chloride resin compositions were evaluated. The results are shown in Table 2.

[0672] <Formation of Vinyl Chloride Resin Molded Sheets>

[0673] The obtained vinyl chloride resin composition was poured into a textured metal mold heated to 250°C and left to melt for an arbitrary time. The remaining vinyl chloride resin composition was then shaken off. Next, the textured metal mold containing the vinyl chloride resin composition was placed in an oven set to 200°C. After 60 seconds, the textured metal mold was cooled with cooling water. When the metal mold temperature cooled to 40°C, a 200mm × 150mm × 1mm vinyl chloride resin sheet, serving as the vinyl chloride resin molded body, was demolded from the metal mold.

[0674] The tensile properties (tensile strength and elongation) at low temperatures were evaluated using the obtained vinyl chloride resin molded sheets in their initial (unheated state). Furthermore, the obtained vinyl chloride resin molded sheets were laminated with polyurethane foam and heated at 130°C for 100 hours. After peeling off the polyurethane foam, the tensile properties at low temperatures were evaluated again. The results are shown in Table 2.

[0675] <Formation of Layered Structures>

[0676] Two vinyl chloride resin molding sheets (size: 200mm×150mm×1mm) were laid in a 200mm×300mm×10mm metal mold with the textured side facing down.

[0677] A mixture of polyols consisting of 50 parts by mass of a propylene glycol propylene oxide-ethylene oxide (PO·EO) block adduct (hydroxyl value 28, terminal EO unit content = 10%, internal EO unit content = 4%), 50 parts by mass of a glycerol PO·EO block adduct (hydroxyl value 21, terminal EO unit content = 14%), 2.5 parts by mass of water, 0.2 parts by mass of a triethylenediamine ethylene glycol solution (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 Industry Co., Ltd., trade name: "F-122") was mixed with polymethylene polyphenylene isocyanate (polymeric MDI) at an index of 98 to prepare a mixture. The prepared mixture was then injected onto two vinyl chloride resin molding sheets that were laid in a metal mold as described above. Next, a 348mm×255mm×10mm aluminum plate is used to cover the metal mold, thereby sealing the metal mold. By leaving the sealed metal mold for 5 minutes, a laminate is formed by adding a foamed polyurethane molded body to a polyvinyl chloride resin molded sheet (thickness: 1mm) as the skin.

[0678] The resulting laminate was removed from the metal mold, and the adhesion and heat shrinkage resistance of the vinyl chloride resin sheet in the laminate to the foamed polyurethane molded body were evaluated. The results are shown in Table 2.

[0679] (Examples 2-11, Comparative Examples 1-5)

[0680] The formulation of the vinyl chloride resin composition was modified as shown in Tables 1 and 2. Otherwise, the vinyl chloride resin composition, vinyl chloride molded sheet, and laminate were prepared in the same manner as in Example 1. The melt properties of the vinyl chloride resin composition, the low-temperature tensile properties of the vinyl chloride molded sheet, the heat shrinkage resistance, and the adhesion to the foamed polyurethane molded body were then evaluated using the obtained vinyl chloride resin composition, vinyl chloride molded sheet, and laminate. The results are shown in Tables 1 and 2.

[0681] In addition, in Tables 1 and 2,

[0682] "EO modification" refers to "ethylene oxide modification".

[0683] "n" refers to "the number of repeating units n of the ethylene oxide unit".

[0684] [Table 1]

[0685]

[0686] [Table 2]

[0687]

[0688] 1) New First Chloride Company manufactured product "ZEST (registered trademark) 1300SI" (prepared by suspension polymerization, average degree of polymerization: 1300, average particle size: 115μm).

[0689] 2) New First Chloride Company manufactured product "ZEST PQLTX" (prepared by emulsion polymerization, average degree of polymerization: 800, average particle size: 1.8μm).

[0690] 3) Manufactured by ADEKA, product name "ADEKA CIZER HPN-3130" (adipic acid-based polyester, viscosity (25℃): 3000mPa·s)

[0691] 4) Cardolite NX-2026 (unmodified cashew nut shell powder), manufactured by Cardolite Company.

[0692] 5) Cardolite NX-7507 (ethylene oxide modified cashew nut shell, with n=7 repeating units of the ethylene oxide unit) manufactured by Cardolite Company.

[0693] 6) Manufactured by ADEKA, product name "ADEKA CIZER O-130S"

[0694] 7) Manufactured by Kyowa Chemical Industry Co., Ltd., product name "ALCAMAIZER (registered trademark) 5"

[0695] 8) Manufactured by Mizusawa Chemical Industry Co., Ltd., product name "MIZUKALIZER DS"

[0696] 9) Manufactured by Sakai Chemical Industry Co., Ltd., product name "SAKAI SZ2000"

[0697] 10) Manufactured by ADEKA, product name "ADEKA STAB LA-72"

[0698] 11) Manufactured by ADEKA, product name "ADEKA STAB LS-12"

[0699] 12) Made by Dai Nippon Seika Co., Ltd., product name "DA P 4720 BLACK"

[0700] As shown in Tables 1 and 2, the resin compositions of Examples 1-11, prepared by using compounds with specified structures as plasticizers, can form resin molded articles with good low-temperature tensile elongation, good adhesion to polyurethane, and excellent heat shrinkage resistance and melt flowability. Furthermore, it is evident that the resin compositions prepared in Examples 10 and 11, which use two compounds with specified structures in greater quantities than those in Examples 1-9, exhibit slightly inferior heat shrinkage resistance compared to Examples 1-9, but significantly superior low-temperature tensile elongation.

[0701] On the other hand, it can be seen that the resin molded body formed from the resin composition of Comparative Example 1, which is prepared without using a compound having a specified structure, has poor meltability and adhesion to polyurethane.

[0702] Furthermore, it is known that the resin molded body formed from the resin composition of Comparative Example 2, prepared by using unmodified cashew nut shell phenol instead of a compound having a specified structure, exhibits poor low-temperature tensile elongation and heat shrinkage resistance. It is also known that the resin molded body formed from the resin composition of Comparative Example 3, prepared by using ethylene oxide-modified cashew nut shell phenol instead of a compound having a specified structure, exhibits poor heat shrinkage resistance.

[0703] Furthermore, it can be seen that the resin molded body formed from the resin composition of Comparative Example 4, which uses unmodified cashew phenol instead of a compound with a specified structure, has poor heat shrinkage resistance and melt flow properties. Additionally, it can be seen that the resin molded body formed from the resin composition of Comparative Example 5, which uses an ethylene oxide-modified diester compound of cashew phenol and adipic acid instead of a compound with a specified structure, has poor heat shrinkage resistance and melt flow properties.

[0704] Industrial availability

[0705] According to the present invention, novel compounds formed by epoxidation of ester compounds are provided.< / bx> < / ax>

Claims

1. A compound represented by the following formula (1), (1) In equation (1), Ax represents an organic group with 3 to 20 carbon atoms. Y 1 Y 4 Each can independently represent a single bond, -C(=O)-, or -C(=O)-NR. 1 -or-C(=O)-O-, R 1 Indicates a hydrogen atom, methyl, or ethyl. Y 2 Y 3 Each can independently represent a single bond, -C (=O)-, and -NR. 2 -C(=O)- or -OC(=O)-, R 2 Indicates a hydrogen atom, methyl, or ethyl. Y 1 Y 4 Y 2 Y 3 Each can be independent and different from the others, or they can be the same. SP 1 SP 4 Each can be independently represented as -CH2CH2O-, -CH2CH(CH3)O-, -CH(CH3)CH2O-, -CH2CH(CH2CH3)O-, or -CH(CH2CH3)CH2O-. SP 2 SP 3 Each can be independently represented as -OCH2CH2-, -OCH(CH3)CH2-, -OCH2CH(CH3)-, -OCH(CH2CH3)CH2-, or -OCH2CH(CH2CH3)-. a, b, c, and d each independently represent an integer from 0 to 30. R a R b R c R d Each can independently represent a chain-like aliphatic hydrocarbon group with 12 or more but less than 18 carbon atoms that can have substituents. The chain-like aliphatic hydrocarbon group can contain one or more but no more than five double bonds. R a R b R c R d In the aforementioned chain aliphatic hydrocarbon group, at least one chain aliphatic hydrocarbon group contains one or more epoxy groups. R a R b R c R d Each can be independent and different from the others, or they can be the same. x and y can each independently represent 0 or 1. When x is 0, the structure represented by the following equation (1-1) represents a hydrogen atom. (1-1) When y is 0, the structure represented by the following equation (1-2) represents a hydrogen atom. (1-2) In equations (1-1) and (1-2), * indicates the bonding position with Ax.

2. The compound according to claim 1, wherein, The R a R b R c and R d Each of the above refers independently to a chain aliphatic hydrocarbon group having 12 or more and 18 or less carbon atoms capable of having substituents, wherein the chain aliphatic hydrocarbon group contains 1 or more and 5 or less epoxy groups.

3. The compound according to claim 1, wherein, The Ax is any one of the organic groups described in (i), (ii), (iii), and (iv) below: (i) A chain-like aliphatic hydrocarbon group having 3 to 20 carbon atoms capable of having substituents; (ii) Cyclic aliphatic hydrocarbon groups having 4 to 12 carbon atoms that can have substituents; (iii) Aromatic hydrocarbon cyclogroups with 6 to 14 carbon atoms capable of having substituents, (iv) An organic group having 3 to 20 carbon atoms, wherein at least one single bond in a chain aliphatic hydrocarbon group having substituents is replaced by -O-, -C(=O)-, -OC(=O)-, or -C(=O)-O-, excluding cases where two or more -O- groups are consecutive, cases where two or more -C(=O)- groups are consecutive, and cases where -O- or -C(=O)- is located adjacent to the Y group. 1 The Y 2 The Y 3 Or the Y 4 The situation at the bonded ends.

4. The compound according to claim 1, wherein, The Ax is a group represented by any of the following formulas (2-1) to (2-35) that can have substituents: 。 5. A mixture comprising the compound of claim 1 and the compound represented by formula (3) below, (3) In equation (3), Bx represents an organic group with 3 to 20 carbon atoms. Y 11 Y 41 Each can independently represent a single bond, -C(=O)-, or -C(=O)-NR. 1 -or-C(=O)-O-, R 1 Indicates a hydrogen atom, methyl, or ethyl. Y 21 Y 31 Each can independently represent a single bond, -C (=O)-, and -NR. 2 -C(=O)- or -OC(=O)-, R 2 Indicates a hydrogen atom, methyl, or ethyl. Y 11 Y 41 Y 21 Y 31 Each can be independent and different from the others, or they can be the same. SP 11 SP 41 Each can be independently represented as -CH2CH2O-, -CH2CH(CH3)O-, -CH(CH3)CH2O-, -CH2CH(CH2CH3)O-, or -CH(CH2CH3)CH2O-. SP 21 SP 31 Each can be independently represented as -OCH2CH2-, -OCH(CH3)CH2-, -OCH2CH(CH3)-, -OCH(CH2CH3)CH2-, or -OCH2CH(CH2CH3)-. e, f, g, and h each independently represent integers from 0 to 30. R a1 R b1 R c1 R d1 Each can independently represent a chain-like aliphatic hydrocarbon group with 12 or more but less than 18 carbon atoms that can have substituents. The chain-like aliphatic hydrocarbon group can contain one or more but no more than five double bonds. R a1 R b1 R c1 R d1 Each can be independent and different from the others, or they can be the same. p and q each independently represent 0 or 1. When p is 0, the structure represented by the following equation (3-1) represents a hydrogen atom. (3-1) When q is 0, the structure represented by the following equation (3-2) represents a hydrogen atom. (3-2) In equations (3-1) and (3-2), * indicates the bonding position with Bx.

6. The mixture according to claim 5, wherein, The Bx is any one of the organic groups described in (i), (ii), (iii), and (iv) below: (i) A chain-like aliphatic hydrocarbon group having 3 to 20 carbon atoms capable of having substituents; (ii) Cyclic aliphatic hydrocarbon groups having 4 to 12 carbon atoms that can have substituents; (iii) Aromatic hydrocarbon cyclogroups with 6 to 14 carbon atoms capable of having substituents, (iv) An organic group having 3 to 20 carbon atoms, wherein at least one single bond in a chain aliphatic hydrocarbon group having substituents is replaced by -O-, -C(=O)-, -OC(=O)-, or -C(=O)-O-, excluding cases where two or more -O- groups are consecutive, cases where two or more -C(=O)- groups are consecutive, and cases where -O- or -C(=O)- is located adjacent to the Y group. 11 The Y 21 The Y 31 Or the Y 41 The situation at the bonded ends.

7. The mixture according to claim 5, wherein, The Bx is a group represented by any of the following formulas (2-1) to (2-35) that can have substituents: 。 8. The mixture according to claim 5, wherein, Ax and Bx have the same structure.

9. The mixture according to claim 8, wherein, The mixture contains at least two of the R... a R b R c and R d Each is a distinct compound represented by formula (1).

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

11. A method using the mixture of any one of claims 5 to 9 as a plasticizer.

12. A plasticizer composition comprising the compound and plasticizer as described in any one of claims 1 to 4.

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

14. The plasticizer composition according to claim 12, wherein, The plasticizer is a polyester-based plasticizer.

15. The plasticizer composition according to claim 13, wherein, The plasticizer is a polyester-based plasticizer.

16. The plasticizer composition according to claim 14, wherein, The plasticizer contains adipic acid-based polyester.

17. The plasticizer composition according to claim 15, wherein, The plasticizer contains adipic acid-based polyester.

18. The plasticizer composition according to claim 14, wherein, The content of the compound is more than 1 part by weight and less than 70 parts by weight relative to 100 parts by weight of the polyester plasticizer.

19. The plasticizer composition according to claim 15, wherein, The content of the compound is more than 1 part by weight and less than 70 parts by weight relative to 100 parts by weight of the polyester 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 according to claim 20, wherein, The resin contains halogens.

23. The resin composition according to claim 21, wherein, The resin contains halogens.

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

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

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

27. The resin composition according to claim 21, wherein, The resin contains vinyl chloride resin.

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

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

30. The resin composition according to claim 20, wherein, The resin composition is used for powder molding.

31. The resin composition according to claim 21, wherein, The resin composition is used for powder molding.

32. The resin composition according to claim 20, wherein, The resin composition is used for powder slush molding.

33. The resin composition according to claim 21, wherein, The resin composition is used for powder slush molding.

34. A resin molded article formed by molding the resin composition of claim 20.

35. A resin molded article formed by molding the resin composition of claim 21.

36. The resin molded article according to claim 34, wherein, The resin molded body is used for the surface of an automotive dashboard.

37. The resin molded article according to claim 35, wherein, The resin molded body is used for the surface of an automotive dashboard.

38. A laminate comprising a foamed polyurethane molded body and a resin molded body as claimed in claim 34.

39. A laminate comprising a foamed polyurethane molded body and a resin molded body as claimed in claim 35.

40. The laminate according to claim 38, wherein, The laminate is used for automotive dashboards.

41. The laminate according to claim 39, wherein, The laminate is used for automotive dashboards.

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