Compound, method for using same, plasticizer composition, resin composition, resin molded article, and laminate

Abstract

The purpose of the present invention is to provide a compound which can be used for producing a resin composition capable of forming a resin molded article having excellent low-temperature tensile elongation and heat shrinkage resistance. The present invention is a compound represented by formula (1) (in formula (1), Ax represents an organic group having 3-20 carbon atoms, Y1, Y2, Y3, and Y4 each independently represent a single bond,-C (= O)-or the like, R1 represents a hydrogen atom, a methyl group or the like, SP1, SP2, SP3, and SP4 each independently represent a predetermined organic group, a, b, c, and d each independently represent an integer of 1-30, and n represents an integer of 1-30). Ra, Rb, Rc, and Rd each independently represent a C12-18 chain aliphatic hydrocarbon group which may have a substituent, and x and y each independently represent 0 or 1. # imgabs0 #

Description

Technical Field

[0001] The present invention relates to a compound and a method for using the same, a plasticizer composition, a resin composition, a resin molded body, and a laminate. Background Art

[0002] Resins such as vinyl chloride resin generally have excellent properties such as cold resistance, heat resistance, and oil resistance, and are therefore used in various applications.

[0003] Specifically, for example, in the formation of automobile interior parts such as automobile instrument panels and door trims, automobile interior materials such as a skin formed from a resin molded body using a resin such as vinyl chloride resin, and a laminated body formed by lining the skin formed from the resin molded body with a foamed body such as foamed polyurethane are used.

[0004] Furthermore, resin molded bodies constituting the skin of automobile interior parts such as automobile instrument panels can be produced by molding a resin composition containing a resin such as a vinyl chloride resin, a plasticizer, and additives using a powder molding method such as powder slush molding (e.g., see Patent Document 1).

[0005] Specifically, for example, in Patent Document 1, a vinyl chloride resin molded article is produced by powder slush molding a vinyl chloride resin composition containing vinyl chloride resin particles, a plasticizer such as a polyester plasticizer, and additives such as a hydrotalcite stabilizer, a zeolite stabilizer, and β-diketones.

[0006] Prior art literature

[0007] Patent Literature

[0008] Patent Document 1: Japanese Patent Application Laid-Open No. 2012-197394. Summary of the Invention

[0009] Problems to be solved by the invention

[0010] Here, the resin molded article is required to have excellent tensile elongation at low temperatures (hereinafter sometimes referred to as "low-temperature tensile elongation").

[0011] Furthermore, as automotive interior materials, laminates are sometimes produced by adding a polyurethane foam backing to the aforementioned resin molded body (hereinafter sometimes referred to as "foamed polyurethane molded body"). Furthermore, when laminates used as automotive interior materials are exposed to high temperatures, plasticizers contained in the resin molded body may migrate to the foamed polyurethane molded body, causing thermal shrinkage within the resin molded body. Therefore, the resin molded body used to form a laminate with the foamed polyurethane molded body is required to suppress this thermal shrinkage, that is, to have reduced thermal shrinkage resistance.

[0012] However, when using a resin composition containing the above-mentioned conventional plasticizer, the low-temperature tensile elongation and heat shrinkage resistance of the resulting resin molded article have room for improvement.

[0013] Therefore, an object of the present invention is to provide a compound that can be used to prepare a resin composition capable of forming a resin molded body having excellent low-temperature tensile elongation and heat shrinkage resistance, and a method for using the compound.

[0014] Another object of the present invention is to provide a plasticizer composition that can be used to prepare a resin composition capable of forming a resin molded body having excellent low-temperature tensile elongation and heat shrinkage resistance.

[0015] Furthermore, an object of the present invention is to provide a resin composition capable of forming a resin molded article having excellent low-temperature tensile elongation and heat shrinkage resistance.

[0016] Another object of the present invention is to provide a resin molded article having excellent low-temperature tensile elongation and heat shrinkage resistance.

[0017] Furthermore, an object of the present invention is to provide a laminate having the resin molded article.

[0018] Solutions for solving problems

[0019] The present inventors conducted intensive research with the goal of solving the above-mentioned problems. The inventors discovered that when a compound having a predetermined structure is used to prepare a resin composition, a resin molded article formed using the prepared resin composition exhibits both excellent low-temperature tensile elongation and excellent heat shrinkage resistance, leading to the completion of the present invention.

[0020] That is, the object of the present invention is to advantageously solve the above-mentioned problems. The present invention provides [1] a compound represented by the following formula (1):

[0021] [Chemical Formula 1]

[0022]

[0023] In formula (1),

[0024] Ax represents an organic group having 3 to 20 carbon atoms,

[0025] Y 1 、Y 4 Each independently represents a single bond, -C(=O)-, -C(=O)-NR 1 - or -C(=O)-O-,

[0026] R 1 represents a hydrogen atom, a methyl group or an ethyl group,

[0027] Y 2 、Y 3 Each independently represents a single bond, -C(=O)-, -NR 2 -C(=O)- or -OC(=O)-,

[0028] R 2 represents a hydrogen atom, a methyl group or an ethyl group,

[0029] SP 1 、SP 4 Each independently represents -CH2CH2O-, -CH2CH(CH3)O-, -CH(CH3)CH2O-, -CH2CH(CH2CH3)O- or -CH(CH2CH3)CH2O-,

[0030] SP 2 、SP 3 Each independently represents -OCH2CH2-, -OCH(CH3)CH2-, -OCH2CH(CH3)-, -OCH(CH2CH3)CH2- or -OCH2CH(CH2CH3)-,

[0031] a, b, c, and d each independently represent an integer of 1 to 30,

[0032] R a 、R b 、R c 、R d Each independently represents a chain aliphatic hydrocarbon group having 12 to 18 carbon atoms which may have a substituent,

[0033] x and y each independently represent 0 or 1,

[0034] When x is 0, the structure represented by the following formula (2) represents a hydrogen atom,

[0035] [Chemical Formula 2]

[0036]

[0037] When y is 0, the structure represented by the following formula (3) represents a hydrogen atom,

[0038] [Chemical Formula 3]

[0039]

[0040] In formulae (2) and (3), * represents a bonding position with Ax.

[0041] Thus, by using the compound having the above-mentioned predetermined structure, it is possible to prepare a resin composition capable of forming a resin molded body having excellent low-temperature tensile elongation and heat shrinkage resistance.

[0042] [2] In the compound of [1] above, it is preferred that the above-mentioned Ax is any one of the following organic groups (i), (ii), (iii) and (iv):

[0043] (i) a chain aliphatic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent;

[0044] (ii) a cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms which may have a substituent;

[0045] (iii) an aromatic hydrocarbon ring group having 6 to 14 carbon atoms which may have a substituent;

[0046] (iv) an organic group having 3 to 20 carbon atoms in which at least one of the single bonds contained in a chain aliphatic hydrocarbon group which may have a substituent is replaced by -O-, -C(=O)-, -OC(=O)-, or -C(=O)-O-, excluding the case where two or more -O- groups are consecutive, two or more -C(=O)- groups are consecutive, and -O- or -C(=O)- groups are located adjacent to the Y group. 1 、The above Y 2 、The above Y 3 or the above Y 4 The case of the bonded ends.

[0047] [3] In the compound of [1] or [2] above, it is preferred that the above-mentioned Ax is a group represented by any one of the following formulae (2-1) to (2-35) which may have a substituent.

[0048] [Chemical Formula 4]

[0049]

[0050] Furthermore, the present invention aims to advantageously solve the above-mentioned problems. The present invention is a method [4] using the compound of any one of [1] to [3] as a plasticizer.

[0051] As described above, when any of the above compounds is used as a plasticizer, a resin composition capable of forming a resin molded body having excellent low-temperature tensile elongation and heat shrinkage resistance can be prepared.

[0052] Furthermore, the present invention aims to advantageously solve the above-mentioned problems. The present invention is [5] a plasticizer composition comprising the compound of any one of [1] to [3] above.

[0053] Thus, by using a plasticizer composition containing any of the above-mentioned compounds, a resin composition capable of forming a resin molded body having excellent low-temperature tensile elongation and heat shrinkage resistance can be prepared.

[0054] [6] The plasticizer composition of the above-mentioned [5] may contain two or more of the above-mentioned compounds having different structures.

[0055] [7] The plasticizer composition of [5] or [6] above preferably further contains a polyester plasticizer.

[0056] When the plasticizer composition further contains a polyester plasticizer, the heat shrinkage resistance of a resin molded article formed using the resin composition containing the plasticizer composition can be further improved.

[0057] [8] In the plasticizer composition of [7] above, it is preferred that the polyester plasticizer contains adipic acid polyester.

[0058] When an adipic acid-based polyester is used as a polyester-based plasticizer, the heat shrinkage resistance of a resin molded article formed using a resin composition containing the plasticizer composition can be further improved.

[0059] [9] In the plasticizer composition of [7] or [8], the content of the compound is preferably 1 part by mass or more and 20 parts by mass or less relative to 100 parts by mass of the polyester plasticizer.

[0060] If the content of the compound of the present invention in the plasticizer composition is within the above-specified range, the heat shrinkage resistance of the formed resin molded body can be sufficiently ensured while improving the adhesion of the resin molded body to the foamed polyurethane molded body and further improving the low-temperature tensile elongation of the resin molded body.

[0061] Furthermore, the present invention aims to advantageously solve the above-mentioned problems. The present invention is

[10] a resin composition comprising a resin and the plasticizer composition according to any one of [5] to [9] above.

[0062] As described above, the resin composition comprising a resin and the plasticizer composition can form a resin molded article having excellent low-temperature tensile elongation and heat shrinkage resistance.

[0063]

[11] In the resin composition of

[10] above, the resin preferably contains halogen.

[0064]

[12] In the resin composition of

[10] or

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

[0065] In the present invention, the "glass transition temperature" of the resin can be measured by differential scanning calorimetry (DSC) in accordance with JIS K 7121.

[0066]

[13] In the resin composition according to any one of

[10] to

[12] , the resin preferably contains a vinyl chloride resin.

[0067]

[14] In the resin composition according to any one of

[10] to

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

[0068] If the content of the above-mentioned compound of the present invention in the resin composition is within the above-specified range, it is possible to ensure sufficiently high heat shrinkage resistance of the formed resin molded body while improving the adhesion of the resin molded body to the foamed polyurethane molded body and further improving the low-temperature tensile elongation of the resin molded body.

[0069]

[15] The resin composition according to any one of

[10] to

[14] is preferably used for powder molding.

[0070] When the resin composition is used for powder molding, a resin molded body that can be suitably used as, for example, an automobile interior material such as an automobile instrument panel skin can be easily obtained.

[0071]

[16] The resin composition according to any one of

[10] to

[15] is preferably used for powder slush molding.

[0072] When the resin composition is used for powder slush molding, a resin molded body that can be suitably used as an automobile interior material, such as a surface skin for an automobile instrument panel, can be obtained more easily.

[0073] Furthermore, the object of the present invention is to advantageously solve the above-mentioned problems. The present invention is

[17] a resin molded body formed by molding the resin composition of any one of the above-mentioned

[10] to

[16] .

[0074] As described above, a resin molded article obtained by molding the resin composition has excellent low-temperature tensile elongation and heat shrinkage resistance, and thus can be suitably used as an automobile interior material.

[0075]

[18] The resin molded article of

[17] is preferably used for automobile instrument panel skin.

[0076] When the resin molded article of the present invention is used for a surface skin of an automobile instrument panel, it is possible to produce an automobile instrument panel having a surface skin excellent in low-temperature tensile elongation and heat shrinkage resistance.

[0077] Furthermore, the present invention aims to advantageously solve the above-mentioned problems. The present invention is

[19] a laminate comprising a foamed polyurethane molded body and the resin molded body of

[17] or

[18] above.

[0078] The laminate comprising the foamed polyurethane molded article and the above-mentioned resin molded article has a resin molded article portion having excellent low-temperature tensile elongation and heat shrinkage resistance.

[0079]

[20] The laminate of

[19] is preferably used for automobile instrument panels.

[0080] When the laminate of the present invention is used for an automobile instrument panel, the low-temperature tensile elongation and heat shrinkage resistance of the surface skin of the manufactured automobile instrument panel can be improved.

[0081] Effects of the Invention

[0082] According to the present invention, a compound that can be used for preparing a resin composition capable of forming a resin molded body having excellent low-temperature tensile elongation and heat shrinkage resistance and a method for using the compound can be provided.

[0083] Furthermore, according to the present invention, there can be provided a plasticizer composition that can be used for preparing a resin composition capable of forming a resin molded body having excellent low-temperature tensile elongation and heat shrinkage resistance.

[0084] Furthermore, according to the present invention, it is possible to provide a resin composition capable of forming a resin molded article having excellent low-temperature tensile elongation and heat shrinkage resistance.

[0085] Furthermore, according to the present invention, a resin molded article having excellent low-temperature tensile elongation and heat shrinkage resistance can be provided.

[0086] Furthermore, according to the present invention, a laminated body including the resin molded body can be provided. BRIEF DESCRIPTION OF THE DRAWINGS

[0087] Figure 1 The following table shows the "Cardolite LITE 2020" (manufactured by Cardolite Corporation) used in the synthesis examples. 1 A diagram showing a spectrum obtained by H-NMR measurement.

[0088] Figure 2 The following table shows the "Cardolite LITE 2020" (manufactured by Cardolite Corporation) used in the synthesis examples. 13 A diagram of a spectrum obtained by C-NMR measurement.

[0089] Figure 3This is a diagram showing a spectrum obtained by C-HCOSY measurement using “Cardolite LITE 2020” (manufactured by Cardolite Corporation) used in the synthesis examples.

[0090] Figure 4 This is a diagram showing spectra obtained by infrared spectroscopy (total reflection measurement) (hereinafter sometimes abbreviated as “IR (ATR)”) using “Cardolite LITE 2020” (manufactured by Cardolite Corporation) used in the synthesis examples.

[0091] Figure 5 The following table shows the properties of "Cardolite NX-7507" (manufactured by Cardolite Corporation) used in the synthesis examples. 1 A diagram showing a spectrum obtained by H-NMR measurement.

[0092] Figure 6 The following table shows the "Cardolite NX-7507" (manufactured by Cardolite Corporation) used in the synthesis examples. 13 A diagram of a spectrum obtained by C-NMR measurement.

[0093] Figure 7 This is a diagram showing a spectrum obtained by C-HCOSY measurement of "Cardolite NX-7507" (manufactured by Cardolite Corporation) used in the synthesis examples.

[0094] Figure 8 This is a diagram showing a spectrum obtained by IR (ATR) measurement of “Cardolite NX-7507” (manufactured by Cardolite Corporation) used in the synthesis examples.

[0095] Figure 9 The diester mixture 1 obtained in Synthesis Example 1 is shown. 1 A diagram showing a spectrum obtained by H-NMR measurement.

[0096] Figure 10 The diester mixture 1 obtained in Synthesis Example 1 is shown. 13 A diagram of a spectrum obtained by C-NMR measurement.

[0097] Figure 11 This is a diagram showing a spectrum obtained by IR (ATR) measurement of the diester mixture 1 obtained in Synthesis Example 1.

[0098] Figure 12 The diurethane mixture 1 obtained in Synthesis Example 2 is shown. 1 A diagram showing a spectrum obtained by H-NMR measurement.

[0099] Figure 13The diurethane mixture 1 obtained in Synthesis Example 2 is shown. 13 A diagram of a spectrum obtained by C-NMR measurement.

[0100] Figure 14 This is a diagram showing a spectrum obtained by IR (ATR) measurement of the diurethane mixture 1 obtained in Synthesis Example 2.

[0101] Figure 15 The diether mixture 1 obtained in Synthesis Example 3 is shown. 1 A diagram showing a spectrum obtained by H-NMR measurement.

[0102] Figure 16 This is a diagram showing a spectrum obtained by IR (ATR) measurement of the diether mixture 1 obtained in Synthesis Example 3.

[0103] Figure 17 The diester mixture 2 obtained in Synthesis Example 4 is shown. 1 A diagram showing a spectrum obtained by H-NMR measurement.

[0104] Figure 18 The diester mixture 2 obtained in Synthesis Example 4 is shown. 13 A diagram of a spectrum obtained by C-NMR measurement.

[0105] Figure 19 This is a diagram showing a spectrum obtained by IR (ATR) measurement of the diester mixture 2 obtained in Synthesis Example 4.

[0106] Figure 20 The triester mixture 1 obtained in Synthesis Example 5 is shown. 1 A diagram showing a spectrum obtained by H-NMR measurement.

[0107] Figure 21 The diester mixture 1 obtained in Synthesis Example 5 is shown. 13 A diagram of a spectrum obtained by C-NMR measurement.

[0108] Figure 22 This is a diagram showing a spectrum obtained by IR (ATR) measurement of the diester mixture 1 obtained in Synthesis Example 5.

[0109] Figure 23 The diester mixture 3 obtained in Synthesis Example 6 is shown. 1 A diagram showing a spectrum obtained by H-NMR measurement.

[0110] Figure 24 The diester mixture 3 obtained in Synthesis Example 6 is shown. 13 A diagram of a spectrum obtained by C-NMR measurement.

[0111] Figure 25 This is a diagram showing a spectrum obtained by IR (ATR) measurement of the diester mixture 3 obtained in Synthesis Example 6.

[0112] Figure 26 The diester mixture 4 obtained in Synthesis Example 7 is shown. 1 A diagram showing a spectrum obtained by H-NMR measurement.

[0113] Figure 27 The diester mixture 4 obtained in Synthesis Example 7 is shown. 13 A diagram of a spectrum obtained by C-NMR measurement.

[0114] Figure 28 This is a diagram showing a spectrum obtained by IR (ATR) measurement of the diester mixture 4 obtained in Synthesis Example 7. DETAILED DESCRIPTION

[0115] Hereinafter, embodiments of the present invention will be described in detail.

[0116] The chemical compound of the present invention can be used, for example, in the preparation of the plasticizer composition of the present invention.

[0117] Furthermore, the plasticizer composition of the present invention can be used, for example, when preparing the resin composition of the present invention.

[0118] Furthermore, the resin composition of the present invention can be used, for example, when forming the resin molded body of the present invention. Moreover, the resin molded body formed using the resin composition of the present invention can be preferably used as an automotive interior material such as a skin possessed by automotive interior parts such as automotive instrument panels and door trims.

[0119] In addition, the resin molded body of the present invention can be used, for example, when forming the laminate of the present invention. Moreover, the laminate formed using the resin molded body of the present invention can be preferably used as an automotive interior material used when manufacturing automotive interior parts such as automotive instrument panels and door trims.

[0120] (Compound)

[0121] The compound of the present invention is a compound represented by the following formula (1).

[0122] [Chemical Formula 5]

[0123]

[0124] Furthermore, the compound of the present invention can sufficiently improve the low-temperature tensile elongation and heat shrinkage resistance of a resin molded article obtained by molding a resin composition prepared using the compound.

[0125] <x、y>

[0126] In the above formula (1), x and y each independently represent 0 or 1.

[0127] Furthermore, when x is 0, the structure represented by the following formula (2) represents a hydrogen atom,

[0128] [Chemical Formula 6]

[0129]

[0130] In addition, when y is 0, the structure represented by the following formula (3) represents a hydrogen atom,

[0131] [Chemical Formula 7]

[0132]

[0133] In the above formulae (2) and (3), * represents a bonding position with Ax.

[0134] Furthermore, x and y may both be 0, both may be 1, or one may be 0 and the other 1. From the viewpoint of further improving the low-temperature tensile elongation and heat shrinkage resistance of the resin molded article, it is preferred that both x and y be 0.

[0135] <ax>

[0136] In the above formula (1), Ax represents an organic group having 3 to 20 carbon atoms.

[0137] Here, the same carbon atom in the organic group constituting Ax may be the same as the above-mentioned Y 1 、Y 2 、Y 3 (where x=1 is the limit), and Y 4 (However, only limited to the case where y=1) two or more bonds, the same carbon atom in the organic group constituting Ax may not be bonded to the above Y 1 、Y 2 、Y 3 (where x=1 is the limit), and Y 4 (However, this is limited to the case where y=1) two or more bonds.

[0138] Furthermore, from the viewpoint of further improving the low-temperature tensile elongation of the resin molded article, it is preferred that the same carbon atom in the organic group constituting Ax does not overlap with the above-mentioned Y. 1 、Y 2 、Y 3 (where x=1 is the limit), and Y 4 (wherein, only limited to the case of y=1) two or more bonds, that is, with Y 1 Bonded carbon atoms, and Y 2 Bonded carbon atoms, and Y 3 (However, only when x=1) the carbon atom bonded to Y 4 (This applies only to the case where y=1) The bonded carbon atoms are all different.

[0139] Furthermore, the same carbon atom in the organic group constituting Ax does not overlap with the above-mentioned Y 1 、Y 2 、Y 3 (where x=1 is the limit), and Y 4 (However, only limited to the case where y=1) In the case of two or more bonds, the organic group constituting Ax and Y 1 Bonded carbon atoms, and Y 2 Bonded carbon atoms, and Y 3 (However, only when x=1) the carbon bonded to Y 4 (However, this applies only to the case where y=1) The bonded carbon atoms may or may not be adjacent to each other.

[0140] Furthermore, from the viewpoint of further improving the low-temperature tensile elongation of the resin molded article, it is preferred that the organic group constituting Ax 1 Bonded carbon atoms, and Y 2 Bonded carbon atoms, and Y 3 (However, only when x=1) the carbon bonded to Y 4 (However, this applies only to the case where y=1) The bonded carbon atoms are not adjacent to each other.

[0141] Furthermore, Ax is preferably any one of the following organic groups (i), (ii), (iii) and (iv), more preferably any one of the following organic groups (i) and (iii), and even more preferably the following organic group (i).

[0142] (i) a chain aliphatic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent;

[0143] (ii) a cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms which may have a substituent;

[0144] (iii) an aromatic hydrocarbon ring group having 6 to 14 carbon atoms which may have a substituent;

[0145] (iv) an organic group having 3 to 20 carbon atoms in which at least one of the single bonds contained in a chain aliphatic hydrocarbon group which may have a substituent is replaced by -O-, -C(=O)-, -OC(=O)-, or -C(=O)-O- (excluding cases where two or more -O- are consecutive, two or more -C(=O)- are consecutive, and -O- or -C(=O)- is located adjacent to Y 1 、Y 2 、Y 3 or Y 4 bonded ends).

[0146] In addition, in the present invention, "can have a substituent" means "unsubstituted or substituted." Moreover, when the organic group included in the general formula has a substituent, the number of substituents possessed by the organic group may be one or two or more. Furthermore, when the organic group included in the general formula has a substituent, unless otherwise specified, the number of carbon atoms of the organic group having the substituent does not include the number of carbon atoms of the substituent. For example, when a chain aliphatic hydrocarbon ring group having 3 to 20 carbon atoms has a substituent, the number of carbon atoms of the chain aliphatic hydrocarbon ring group having 3 to 20 carbon atoms does not include the number of carbon atoms of the substituent.

[0147] Here, the carbon number of the chain aliphatic hydrocarbon group having 3 to 20 carbon atoms in (i) is preferably 3 to 15, more preferably 3 to 12, further preferably 3 to 10, further preferably 3 to 8, further preferably 3 to 6, and particularly preferably 3 to 4.

[0148] The chain aliphatic hydrocarbon group having 3 to 20 carbon atoms in (i) above has a total carbon number of 3 to 20, including the carbon number of the substituent.

[0149] The chain aliphatic hydrocarbon group having 3 to 20 carbon atoms in (i) may be linear or branched.

[0150] The chain aliphatic hydrocarbon group having 3 to 20 carbon atoms in (i) may be an unsaturated aliphatic hydrocarbon group having an unsaturated bond (a carbon-carbon double bond or a carbon-carbon triple bond), or a saturated aliphatic hydrocarbon group having no unsaturated bond. Furthermore, when the chain aliphatic hydrocarbon group having 3 to 20 carbon atoms in (i) has an unsaturated bond, the number of unsaturated bonds is, for example, 1 or more and 3 or less.

[0151] The substituent that the chain aliphatic hydrocarbon group having 3 to 20 carbon atoms in (i) above may have is not particularly limited, and examples thereof include halogen atoms.

[0152] The cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms in (ii) above preferably has 4 to 15 carbon atoms, more preferably 4 to 12 carbon atoms, further preferably 4 to 10 carbon atoms, further preferably 4 to 8 carbon atoms, and further preferably 4 to 6 carbon atoms.

[0153] The cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms in (ii) above has a total carbon number of 3 to 20, including the carbon number of the substituent.

[0154] The cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms in (ii) may be an unsaturated aliphatic hydrocarbon group having an unsaturated bond (carbon-carbon double bond, carbon-carbon triple bond) or a saturated aliphatic hydrocarbon group having no unsaturated bond.

[0155] Examples of the substituent that the cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms in (ii) above may have include a halogen atom and an alkyl group having 1 to 8 carbon atoms.

[0156] The aromatic hydrocarbon ring group having 6 to 14 carbon atoms in (iii) above preferably has 6 to 12 carbon atoms.

[0157] The aromatic hydrocarbon ring group having 6 to 14 carbon atoms in (iii) above has a total carbon number of 3 to 20, including the carbon number of the substituent.

[0158] Examples of the substituent that the aromatic hydrocarbon ring group having 6 to 14 carbon atoms in (iii) above may have include a halogen atom and an alkyl group having 1 to 6 carbon atoms.

[0159] Here, the organic group having 3 to 20 carbon atoms in (iv) above preferably has 3 to 15 carbon atoms, more preferably 3 to 12 carbon atoms, further preferably 3 to 10 carbon atoms, further preferably 3 to 8 carbon atoms, further preferably 3 to 6 carbon atoms, and particularly preferably 3 to 4 carbon atoms.

[0160] In addition, in the organic group having 3 to 20 carbon atoms in the above-mentioned (iv), when at least one of the single bonds contained in the chain aliphatic hydrocarbon group which may have a substituent is substituted by -C(=O)-, -OC(=O)- or -C(=O)-O-, the number of carbon atoms of -C(=O)-, -OC(=O)- or -C(=O)-O- is included in the number of carbon atoms of the organic group having 3 to 20 carbon atoms in the above-mentioned (iv).

[0161] The organic group having 3 to 20 carbon atoms in (iv) above has a total carbon number of 3 to 20, including the carbon number of the substituent.

[0162] Examples of the substituent that the organic group having 3 to 20 carbon atoms in (iv) may have include a halogen atom.

[0163] Preferred specific examples of Ax include groups represented by any of the following formulae (2-1) to (2-35) that may have a substituent. Here, "having a substituent" means that any of the hydrogen atoms in the group represented by any of the following formulae (2-1) to (2-35) is substituted.

[0164] [Chemical Formula 8]

[0165]

[0166] In the above formulas (2-1) to (2-4), (2-20) to (2-26), and (2-30) to (2-33), "-" represents extension from any position of the ring and Y 1 、Y 2 、Y 3 or Y 4 The bonding site.

[0167] In the above formulas (2-5) to (2-19), (2-27) to (2-29), and (2-34) to (2-35), the "-" at the end of the chain structure represents the 1 、Y 2 、Y 3 or Y 4 The bonding site.

[0168] In addition, when x is 0, the structure represented by the above formula (2) (i.e., a hydrogen atom) can be any one of the hydrogen atoms possessed by 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 (3) (i.e., a hydrogen atom) can be any one of the hydrogen atoms possessed by the group represented by any one of the above formulas (2-1) to (2-35).

[0169] Examples of the substituent that the group represented by any one of the formulae (2-1) to (2-35) may have include a halogen atom and an alkyl group having 1 to 4 carbon atoms.

[0170] Moreover, from the viewpoint of further improving the low-temperature tensile elongation and heat shrinkage resistance of the resin molded body, Ax is preferably a group represented by any one of the above formulas (2-5) to (2-6), (2-8), (2-20), and (2-27), more preferably a group represented by any one of the above formulas (2-5) to (2-6), (2-8), and (2-20), and even more preferably a group represented by the above formula (2-6).

[0171] <Y 1 、Y 4 >

[0172] In the above formula (1), Y 1 and Y 4 Each independently represents a single bond, -C(=O)-, -C(=O)-NR 1 - or -C(=O)-O-. In addition, R 2 represents a hydrogen atom, a methyl group or an ethyl group.

[0173] Furthermore, from the viewpoint of further improving the low-temperature tensile elongation and heat shrinkage resistance of the resin molded body and improving the adhesion of the resin molded body to the foamed polyurethane molded body, Y 1 and Y 4 , each independently preferably a single bond, -C(=O)- or -C(=O)-NR 1 -, more preferably a single bond or -C(=O)-, further preferably -C(=O)-.

[0174] <Y 2 、Y 3 >

[0175] In the above formula (1), Y 2 and Y 3 Each independently represents a single bond, -C(=O)-, -NR 2 -C(=O)- or -OC(=O)-. In addition, R 2 represents a hydrogen atom, a methyl group or an ethyl group.

[0176] Furthermore, from the viewpoint of further improving the low-temperature tensile elongation and heat shrinkage resistance of the resin molded body and improving the adhesion of the resin molded body to the foamed polyurethane molded body, Y 2 and Y 3 , each independently preferably a single bond, -C(=O)- or -C(=O)-NR 2 -, more preferably a single bond or -C(=O)-, further preferably -C(=O)-.

[0177] <SP 1 、SP 4 >

[0178] In the above formula (1), SP 1 and SP 4 Each independently represents -CH2CH2O-, -CH2CH(CH3)O-, -CH(CH3)CH2O-, -CH2CH(CH2CH3)O- or -CH(CH2CH3)CH2O-.

[0179] Moreover, as SP 1 and SP 4 , each independently preferably is -CH2CH2O-, -CH2CH(CH3)O- or -CH(CH3)CH2O-, more preferably -CH2CH2O-.

[0180] <SP 2 、SP 3 >

[0181] In the above formula (1), SP 2 and SP 3 Each independently represents -OCH2CH2-, -OCH(CH3)CH2-, -OCH2CH(CH3)-, -O(CH3CH2)CHCH2- or -OCH2CH(CH2CH3)-.

[0182] Moreover, as SP 2 and SP 3 , each independently preferably is -OCH2CH2-, -OCH(CH3)CH2- or -OCH2CH(CH3)-, more preferably -OCH2CH2-.

[0183] <a、b、c、d>

[0184] In the above formula (1), a, b, c, and d each independently represent an integer of 1 to 30.

[0185] Moreover, from the viewpoint of further improving the heat shrinkage resistance of the resin molded body and improving the adhesion of the resin molded body to the foamed polyurethane molded body, a, b, c and d each independently preferably represent an integer of 1 to 25, more preferably an integer of 2 to 20, further preferably an integer of 3 to 15, further preferably an integer of 4 to 12, and even more preferably an integer of 5 to 10.

[0186] <R a 、R b 、R c 、R d >

[0187] In the above formula (1), R a 、R b 、R c and R d Each independently represents a chain aliphatic hydrocarbon group having 12 to 18 carbon atoms which may have a substituent.

[0188] Composition R a 、R b 、R c and R d The carbon number of the chain aliphatic hydrocarbon group having 12 to 18 carbon atoms which may have a substituent is preferably 13 to 17, more preferably 14 to 16, each independently.

[0189] Composition R a 、R b 、R c and R d The chain aliphatic hydrocarbon groups having 12 to 18 carbon atoms that may have a substituent may each independently be an unsaturated aliphatic hydrocarbon group having an unsaturated bond (carbon-carbon double bond, carbon-carbon triple bond) or a saturated aliphatic hydrocarbon group having no unsaturated bond. Furthermore, when the chain aliphatic hydrocarbon group having 12 to 18 carbon atoms has an unsaturated bond, the number of unsaturated bonds is, for example, 1 or more and 5 or less. Furthermore, the isomer formed by the carbon-carbon double bond in the chain aliphatic hydrocarbon group having 12 to 18 carbon atoms may be a cis-isomer or a trans-isomer.

[0190] As a component of R a 、R b 、R c and R d Examples of the substituent that the chain aliphatic hydrocarbon group having 12 to 18 carbon atoms may have include an alkyl group having 1 to 3 carbon atoms and a halogen atom.

[0191] Moreover, R a 、R b 、R c and R d Each independently is, for example, -(CH2) 14 A chain aliphatic hydrocarbon group having 15 carbon atoms, any of CH3, -(CH2)7CH=CH(CH2)5CH3, -(CH2)7CH=CHCH2CH=CH(CH2)2CH3, -(CH2)7CH=CHCH2CH=CHCH=CHCH3, and -(CH2)7CH=CHCH2CH=CHCH2CH=CH2. In addition, at least one hydrogen atom of the chain aliphatic hydrocarbon group having 15 carbon atoms may be substituted.

[0192] <Method for producing compound>

[0193] The compounds of the present invention are not particularly limited and can be synthesized by combining known synthetic reactions. Examples of literature describing known synthetic reactions include Sandler Karo's Organic Functional Group Preparations, Volumes I and II (Hirokawa Shoten), and March's Advanced Organic Chemistry Sixth Edition (by Michael B. Smith and Jerry March, Wiley).

[0194] Typically, the compound of the present invention represented by formula (1) can be produced by the following method: using an ether bond (-O-), an ester bond (-C(=O)-O-, -OC(=O)-), a carbamate bond (-C(=O)-NR 1 -、-NR 2 -C(=O)-) etc., and the plurality of compounds as raw materials are appropriately bonded and / or modified. 1 and R 2 Means the same as above.

[0195] More specifically, the formation of the ether bond can be performed, for example, as follows.

[0196] (i) A compound represented by the formula: D1-hal (hal represents a halogen atom, the same applies hereinafter) and a compound represented by the formula: D2-OMet (Met represents an alkali metal (mainly sodium), the same applies hereinafter) are mixed and condensed (Williamson synthesis). In the formula, D1 and D2 represent arbitrary organic groups (the same applies hereinafter).

[0197] (ii) A compound represented by the formula: D1-hal and a compound represented by the formula: D2-OH are mixed in the presence of a base such as sodium hydroxide or potassium hydroxide and condensed.

[0198] (iii) A compound represented by the formula: D1-J (J represents an epoxy group) and a compound represented by the formula: D2-OH are mixed in the presence of a base such as sodium hydroxide or potassium hydroxide and condensed.

[0199] (iv) A compound represented by the formula: D1-OFN (OFN represents a group having an unsaturated bond) and a compound represented by the formula: D2-OMet are mixed in the presence of a base such as sodium hydroxide or potassium hydroxide to allow an addition reaction to proceed.

[0200] (v) A compound represented by the formula: D1-hal and a compound represented by the formula: D2-OMet are mixed in the presence of copper or cuprous chloride and condensed (Ullmann condensation).

[0201] More specifically, the formation of the ester bond can be performed, for example, as follows.

[0202] (vi) A compound represented by the formula: D1-COOH and a compound represented by the formula: D2-OH are subjected to dehydration condensation in the presence of a dehydration condensation agent (such as WSC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride)).

[0203] (vii) After allowing a halogenating agent to act on a compound represented by the formula: D1-COOH to obtain a compound represented by the formula: D1-C(=O)-hal, the compound is reacted with a compound represented by the formula: D2-OH in the presence of a base.

[0204] (viii) After allowing an acid anhydride to act on a compound represented by the formula: D1-COOH to obtain a mixed acid anhydride, the mixed acid anhydride is reacted with a compound represented by the formula: D2-OH.

[0205] (ix) A compound represented by the formula: D1-COOH and a compound represented by the formula: D2-OH are subjected to dehydration condensation in the presence of an acid catalyst or a base catalyst.

[0206] More specifically, the formation of the urethane bond can be performed, for example, as follows.

[0207] (x) A compound represented by the formula: D1-N=C=O is reacted with a compound represented by the formula: D2-OH in the presence of a base catalyst.

[0208] The compound of the present invention can be produced, for example, by the reaction shown below.

[0209] [Chemical Formula 9]

[0210]

[0211] (where Ax, Y 1 ~Y 4 、R 1 、R 2 、SP 1 ~SP 4 , a, b, c, d, R a 、R b 、R c 、R d , x, and y have the same meanings as above.)

[0212] That is, by reacting a compound having a carboxyl group represented by formula (A) with a compound having a hydroxyl group represented by formula (B) at a ratio of [the number of moles of carboxyl groups possessed by the compound represented by formula (A) : the number of moles of hydroxyl groups possessed by the compound represented by formula (B)], usually at a ratio of 1:2 to 2:1, preferably 1:1.5 to 1.5:1, and more preferably 1:1.0 to 1:1.5, the compound represented by formula (1) of the present invention can be produced with high selectivity and high yield.

[0213] In this case, examples of the dehydration condensation agent 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, bis(trimethylsilyl)carbodiimide, diimide, diisopropylcarbodiimide and other carbodiimides; 2-methyl-6-nitrobenzoic anhydride, 2,2'-carbonylbis-1H-imidazole, 1,1'-oxalyldiimidazole, diphenylphosphoryl azide, 1-(4-nitrobenzenesulfonyl)-1H-1,2,4-triazole, 1H-benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate, 1H-benzotriazol-1-yloxytris(dimethyl)phosphonium Amino)phosphonium hexafluorophosphate, N,N,N',N'-tetramethyl-O-(N-succinimidyl)uronium tetrafluoroborate, N-(1,2,2,2-tetrachloroethoxycarbonyloxy)succinimide, N-benzyloxycarbonylsuccinimide, O-(6-chlorobenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate, O-(6-chlorobenzotriazol-1-yl)-N, N,N',N'-Tetramethyluronium hexafluorophosphate, 2-bromo-1-ethylpyridinium tetrafluoroborate, 2-chloro-1,3-dimethylimidazolinium chloride, 2-chloro-1,3-dimethylimidazolinium hexafluorophosphate, 2-chloro-1-methylpyridinium iodide, 2-chloro-1-methylpyridinium p-toluenesulfonate, 2-fluoro-1-methylpyridinium p-toluenesulfonate, pentachlorophenyl trichloroacetate, etc.

[0214] In terms of reactivity, cost, and usable solvents, dicyclohexylcarbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide, 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, bis(2,6-diisopropylphenyl)carbodiimide, bis(trimethylsilyl)carbodiimide, diisopropylcarbodiimide, and 2,2′-carbonylbis-1H-imidazole are more preferred.

[0215] The amount of the dehydration condensation agent added is usually 1 to 1.5 mol, preferably 1 to 1.2 mol, and more preferably 1 to 1.1 mol relative to the molar number of carboxyl groups possessed by the compound represented by formula (A). In addition, the dehydration condensation agent can be added directly or in the form of a solution dissolved or dispersed in an appropriate solvent.

[0216] In this case, an activator can be used. Examples of the activator include 4-(dimethylamino)pyridine (N,N-dimethyl-4-aminopyridine).

[0217] The amount of the activator added is usually 0.01 to 1.0 mol, preferably 0.01 to 0.5 mol, relative to the molar number of the dehydration condensation agent. The activator may be added directly or in the form of a solution dissolved or dispersed in an appropriate solvent.

[0218] The solvent used in the reaction is not particularly limited as long as it is inactive to the reaction. 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-dimethylimidazolidinone, and hexamethylphosphoric acid triamide; sulfur-containing solvents such as dimethyl sulfoxide and sulfolane; halogen solvents such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; and mixed solvents composed of two or more of these. Among these, ether solvents, ester solvents, amide solvents, and halogen solvents are preferred, and amide solvents, N-methylpyrrolidone, N,N-dimethylacetamide, and N,N-dimethylformamide are particularly preferred.

[0219] The amount of the solvent used is not particularly limited and can be appropriately set in consideration of the type of compound used, reaction scale, etc., and is usually 1 to 100 g per 1 g of the compound having a carboxyl group represented by formula (A).

[0220] The reaction proceeds smoothly within a temperature range of -10°C to the boiling point of the solvent used, preferably 10°C to 80°C, more preferably 15°C to 50°C. The reaction time for each reaction, although depending on the reaction scale, is generally from several minutes to several tens of hours, preferably from several minutes to seventy hours, and more preferably from several hours to thirty hours.

[0221] The compound of the present invention can also be produced by, for example, the reaction shown below.

[0222] [Chemical Formula 10]

[0223]

[0224] (where Ax, Y 1 ~Y 4 、R 1 、R 2 、SP 1 ~SP 4 , a, b, c, d, R a 、R b 、R c 、R d , x, and y have the same meanings as above.)

[0225] That is, by reacting a compound having an acyl chloride group represented by formula (C) with a compound having a hydroxyl group represented by formula (B) at a ratio of [the number of moles of hydroxyl groups possessed by the compound represented by formula (B) : the number of moles of acyl chloride groups possessed by the compound represented by formula (C)], usually at a ratio of 1:2 to 2:1, preferably 1:1.5 to 1.5:1, and more preferably 1:1.0 to 1:1.2, the compound represented by formula (1) of the present invention can be produced with high selectivity and high yield.

[0226] In this case, examples of the base include organic bases such as triethylamine, diisopropylethylamine, pyridine, 4-(dimethylamino)pyridine (N,N-dimethyl-4-aminopyridine), and 2,6-lutidine; and inorganic bases such as sodium hydroxide, sodium carbonate, and sodium hydrogen carbonate.

[0227] In this case, an activator can be used. Examples of the activator include 4-(dimethylamino)pyridine (N,N-dimethyl-4-aminopyridine).

[0228] The amount of the activator added is usually 0.01 to 1.0 mol, preferably 0.01 to 0.5 mol, and more preferably 0.01 to 0.2 mol relative to the compound having an acyl chloride group represented by the above formula (C). The activator may be added directly or in the form of a solution dissolved or dispersed in an appropriate solvent.

[0229] The solvent used in the reaction is not particularly limited as long as it is inactive to the reaction. 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-dimethylimidazolidinone, and hexamethylphosphoric acid triamide; sulfur-containing solvents such as dimethyl sulfoxide and sulfolane; halogen solvents such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; and mixed solvents composed of two or more of these. Among these, ether solvents, ester solvents, and halogen solvents are preferred, ether solvents and halogen solvents are more preferred, and tetrahydrofuran, 1,2-dimethoxyethane, cyclopentyl methyl ether, methyl tert-butyl ether, chloroform, and 1,2-dichloroethane are particularly preferred.

[0230] The amount of the solvent used is not particularly limited and can be appropriately set in consideration of the type of compound used, reaction scale, etc., and is usually 1 to 100 g per 1 g of the compound having a carboxyl group represented by formula (A).

[0231] The reaction proceeds smoothly within a temperature range of -20°C to the boiling point of the solvent used, preferably -5°C to 50°C, more preferably 0°C to 40°C. The reaction time for each reaction, although depending on the reaction scale, is generally from several minutes to more than ten hours, preferably from several minutes to ten hours, and more preferably from several tens of minutes to five hours.

[0232] In this case, the compound having an acyl chloride group represented by formula (C) may be a commercially available compound or may be a compound synthesized from the compound having a carboxyl group represented by the above formula (A).

[0233] The compound having an acyl chloride group represented by formula (C) can be produced as follows.

[0234] [Chemical Formula 11]

[0235]

[0236] (In the formula, x and y have the same meanings as above.)

[0237] At this time, as the chlorinating agent used, there can be mentioned thionyl chloride (SOCl2), oxalyl chloride [(C(=O)Cl)2], sulfuryl chloride (SO2Cl2), phosphorus oxychloride (POCl3), phosphorus trichloride (PCl3), phosphorus pentachloride (PCl5) and the like, preferably thionyl chloride, oxalyl chloride, and sulfuryl chloride. These chlorinating agents can be used alone or in combination of two or more.

[0238] The chlorinating agent used is reacted with the compound having a carboxyl group represented by formula (A) and the chlorinating agent at a ratio of [number of moles of carboxyl groups possessed by the compound represented by formula (A) : chlorinating agent] of usually 1:2 to 2:1, preferably 1:5 to 1:3, more preferably 1:1.0 to 1:1.5, thereby producing the target acid chloride compound represented by formula (C) with high selectivity and high yield.

[0239] In this case, an activator can be used. Examples of the activator include N,N-dimethylformamide, triethylamine, and tetraalkylammonium, with N,N-dimethylformamide and tetraalkylammonium being preferred.

[0240] The amount of the activator added is usually 0.01 to 3.0 mol, preferably 0.01 to 2.0 mol, and more preferably 0.01 to 0.5 mol, relative to the compound having a carboxyl group represented by the above formula (A).

[0241] The solvent used in the reaction is not particularly limited as long as it is inactive to the reaction. 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-dimethylimidazolidinone, and hexamethylphosphoric acid triamide; sulfur-containing solvents such as dimethyl sulfoxide and sulfolane; halogen solvents such as dichloromethane, chloroform, 1,2-dichloroethane, and chlorobenzene; and mixed solvents composed of two or more of these. Among these, ether solvents, ester solvents, and halogen solvents are preferred, ether solvents and halogen solvents are more preferred, and tetrahydrofuran, 1,2-dimethoxyethane, cyclopentyl methyl ether, methyl tert-butyl ether, chloroform, and 1,2-dichloroethane are particularly preferred.

[0242] The amount of the solvent used is not particularly limited and can be appropriately set in consideration of the type of compound used, reaction scale, etc., and is usually 1 to 100 g per 1 g of the compound having a carboxyl group represented by formula (A).

[0243] The reaction proceeds smoothly within a temperature range of -20°C to the boiling point of the solvent used, preferably -5°C to 150°C, more preferably 0°C to 110°C. The reaction time for each reaction, although depending on the reaction scale, is generally from several minutes to more than ten hours, preferably from several minutes to ten hours, and more preferably from several tens of minutes to five hours.

[0244] As the compound represented by the above formula (B), cardanol produced from cashew nut shell liquid extract and its derivatives can be preferably used.

[0245] There are no particular limitations on the cardanol and its derivatives as long as they have a hydroxyl group. Specific examples of the cardanol derivatives are listed below from Cardolite, and equivalent products from other companies can also be used.

[0246] Cardanol and cardanol derivatives are manufactured by, for example, Cardolite Corporation. Specific examples thereof include Cardolite's product names such as NX-2021, NX-2022, NX-2023, NX-2023D, NX-2024, NX-2025, NX-2026, NX-5205, UltraLITE2023, UL-2023, NC-510 (hydrogenated product), LITE2020 (ethylene oxide 1 adduct), NX-7507 (ethylene oxide 7 adduct), GX-5166 (ethylene oxide 7 adduct), GX-5167 (ethylene oxide 9 adduct), GX-5170 (ethylene oxide 12 adduct), LITE2100, and LITE2100R.

[0247] Among them, NX-2021, NX-2022, NX-2023, NX-2023D, NX-2024, NX-2025, NX-2026, NX-5205, UltraLITE2023, UL-2023, NC-510 (hydrogenated product), LITE2020 (ethylene oxide 1 adduct), NX-7507 (ethylene oxide 7 adduct), GX-5166 (ethylene oxide 7 adduct), GX-5167 (ethylene oxide 9 adduct), GX-517 0 (ethylene oxide 12 adduct), more preferably NX-2021, NX-2022, NX-2023, NX-2024, NX-2025, NX-2026, UltraLITE2023, NC-510 (hydrogenated product), LITE2020 (ethylene oxide 1 adduct), NX-7507 (ethylene oxide 7 adduct), GX-5166 (ethylene oxide 7 adduct), GX-5167 (ethylene oxide 9 adduct), and GX-5170 (ethylene oxide 12 adduct).

[0248] (How to use the compound)

[0249] The compound of the present invention is not particularly limited. For example, it can be used as a plasticizer when preparing a resin composition for forming a resin molded body, thereby imparting flexibility and elasticity to the resin molded body. Furthermore, when the compound of the present invention is used as a plasticizer, the low-temperature tensile elongation and heat shrinkage resistance of the resin molded body obtained by molding the resin composition can be substantially improved.

[0250] Furthermore, when the compound of the present invention is used as a plasticizer, two or more compounds of the present invention having different structures may be combined. In other words, a mixture containing two or more compounds of the present invention having different structures may be used as a plasticizer.

[0251] (Plasticizer composition)

[0252] The plasticizer composition of the present invention (hereinafter sometimes referred to simply as "plasticizer composition") is characterized by comprising at least the compound of the present invention. When a plasticizer composition comprising the compound of the present invention is used in the preparation of a resin composition, the low-temperature tensile elongation and heat shrinkage resistance of a resin molded article formed from the prepared resin composition can be substantially improved.

[0253] The plasticizer composition of the present invention may further contain a plasticizer other than the compound of the present invention. In particular, the plasticizer composition of the present invention preferably further contains a polyester plasticizer in addition to the compound of the present invention. Furthermore, the plasticizer composition of the present invention may further contain a plasticizer other than the compound of the present invention and the polyester plasticizer (hereinafter sometimes referred to as "other plasticizer").

[0254] <Compounds of the Present Invention>

[0255] As the compound of the present invention used for preparing the plasticizer composition, one compound having a single structure may be used alone, or two or more compounds having different structures may be used in combination at any ratio.

[0256] When the plasticizer composition includes a polyester plasticizer, the content of the compound of the present invention in the plasticizer composition is preferably 1 part by mass or more relative to 100 parts by mass of the polyester plasticizer, more preferably 1.5 parts by mass or more, further preferably 2 parts by mass or more, even more preferably 2.5 parts by mass or more, even more preferably 3 parts by mass or more, yet even more preferably 8 parts by mass or more, preferably 20 parts by mass or less, more preferably 18 parts by mass or less, even more preferably 16 parts by mass or less, even more preferably 12 parts by mass or less. If the content of the compound of the present invention in the plasticizer composition is above the above lower limit, the low-temperature tensile elongation of the formed resin molded body can be further improved, and the adhesion of the resin molded body to the foamed polyurethane molded body can be improved. On the other hand, if the content of the compound of the present invention in the plasticizer composition is below the above upper limit, the heat shrinkage resistance of the formed resin molded body can be fully ensured.

[0257] <Polyester plasticizer>

[0258] Polyester plasticizers are components that can impart sufficient tensile properties (e.g., tensile elongation, tensile strength, etc.) to a resin molded article formed using a resin composition containing the plasticizer composition. Furthermore, when a polyester plasticizer is used, when a laminate is formed by lining a resin molded article formed from a resin composition containing the plasticizer composition with a foamed polyurethane molded article, the polyester plasticizer is less likely to migrate from the resin molded article to the foamed polyurethane molded article even at high temperatures, thereby further improving the heat shrinkage resistance of the resin molded article.

[0259] The polyester plasticizer is not particularly limited, and examples thereof include polyesters containing structural units derived from adipic acid (adipic acid-based polyesters), polyesters containing structural units derived from sebacic acid (sebacic acid-based polyesters), and polyesters containing structural units derived from phthalic acid (phthalic acid-based polyesters). These polyesters may be used alone or as a mixture of two or more at any ratio.

[0260] In particular, from the viewpoint of further improving the heat shrinkage resistance of the resin molded article, it is preferable to use adipic acid-based polyester (a polyester containing a structural unit derived from adipic acid) as the polyester-based plasticizer.

[0261] The viscosity of the polyester plasticizer is preferably 500 mPa·s or more, more preferably 1000 mPa·s or more, and is preferably 8000 mPa·s or less, more preferably 5000 mPa·s or less.

[0262] In addition, "viscosity" can be measured at a temperature of 25°C according to JIS Z8803.

[0263] <Other plasticizers>

[0264] The plasticizer composition may optionally contain other plasticizers in addition to the compound of the present invention and the polyester plasticizer described above.

[0265] Specific examples of other plasticizers include those described in International Publication No. 2016 / 098344, excluding the aforementioned (b1) polyester plasticizers and (b2) phenols and their modified products. In particular, from the perspective of further improving the low-temperature tensile elongation of the resulting resin molded article, epoxidized vegetable oils are preferably used, and epoxidized soybean oil is more preferably used.

[0266] The content of other plasticizers in the plasticizer composition is not particularly limited, but can be 0 parts by mass or more and 15 parts by mass or less relative to 100 parts by mass of the polyester plasticizer.

[0267] Moreover, when an epoxidized vegetable oil such as epoxidized soybean oil is used as another plasticizer, from the viewpoint of further improving the low-temperature tensile elongation of the formed resin molded body while ensuring a sufficiently high heat shrinkage resistance of the resin molded body, the content of the epoxidized vegetable oil as another plasticizer is preferably 2 parts by mass or more, more preferably 3 parts by mass or more, further preferably 4 parts by mass or more, and preferably 10 parts by mass or less, more preferably 7 parts by mass or less, and further preferably 5 parts by mass or less relative to 100 parts by mass of the above-mentioned polyester plasticizer.

[0268] (Resin composition)

[0269] The resin composition of the present invention is characterized by comprising (a) a resin and (b) a plasticizer composition of the present invention (hereinafter sometimes referred to simply as "(b) plasticizer composition"). Specifically, the resin composition of the present invention comprises at least (a) a resin and the compound of the present invention, and optionally further comprises a polyester plasticizer and other plasticizers.

[0270] Furthermore, the resin composition of the present invention may optionally contain additives other than the above-mentioned (a) resin and (b) plasticizer composition.

[0271] Furthermore, a resin molded article formed using the resin composition of the present invention is excellent in low-temperature tensile elongation.

[0272] Furthermore, when a laminate is produced by lining a resin molded article formed using the resin composition of the present invention with a foamed polyurethane molded article, thermal shrinkage of the resin molded article in the laminate can be sufficiently suppressed. In other words, the resin molded article formed using the resin composition of the present invention also has excellent resistance to thermal shrinkage.

[0273] Therefore, by using the resin composition of the present invention, it is possible to obtain a resin molded body which is suitable as an automobile interior material such as an automobile instrument panel skin and a door trim skin having excellent low-temperature tensile elongation and heat shrinkage resistance.

[0274] Furthermore, for example, from the viewpoint of easily obtaining a resin molded body that can be suitably used as an automobile interior material using the resin composition of the present invention, the resin composition of the present invention is preferably used for powder molding, more preferably for powder slush molding.

[0275] <(a) Resin>

[0276] The (a) resin is not particularly limited as long as the desired effects of the present invention can be obtained, and known resins can be used.

[0277] The (a) resin contained in the resin composition of the present invention is a component different from the compound of the present invention, a plasticizer such as a polyester plasticizer, and additives as optional components contained in the (b) plasticizer composition.

[0278] Here, the glass transition temperature of the (a) resin is preferably 50° C. or higher and 100° C. or lower.

[0279] As the resin (a), a halogen-containing resin is preferably used, a fluorine-containing resin or a chlorine-containing resin is more preferably used, a chlorine-containing resin is further preferably used, and a vinyl chloride resin is particularly preferably used.

[0280] The content of the vinyl chloride resin in the resin (a) is not particularly limited, but is preferably 50% by mass or more, more preferably 70% by mass or more, further preferably 90% by mass or more, and particularly preferably 100% by mass.

[0281] <<Vinyl Chloride Resin>>

[0282] The vinyl chloride resin is generally used in the form of granules. Furthermore, the vinyl chloride resin may contain, for example, one or more types of vinyl chloride resin granules, and optionally one or more types of vinyl chloride resin microparticles. The vinyl chloride resin preferably contains at least vinyl chloride resin granules, and more preferably contains both vinyl chloride resin granules and vinyl chloride resin microparticles.

[0283] Furthermore, the vinyl chloride resin can be produced by any conventionally known production method such as suspension polymerization, emulsion polymerization, solution polymerization, or bulk polymerization.

[0284] In this specification, “resin particles” refer to particles having a particle size of 30 μm or larger, and “resin microparticles” refer to particles having a particle size of less than 30 μm.

[0285] In addition, as a vinyl chloride resin, in addition to homopolymers formed from 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 mentioned. Moreover, as specific examples of monomers (comonomers) that can constitute vinyl chloride copolymers and can be copolymerized with vinyl chloride monomers, for example, monomers described in International Publication No. 2016 / 098344 can be used. In addition, these components can be used alone or in combination of two or more in any ratio.

[0286] [Vinyl chloride resin pellets]

[0287] In a resin composition, vinyl chloride resin particles generally function as a base resin (substrate). In addition, vinyl chloride resin particles are preferably produced by a suspension polymerization method.

[0288] -Average degree of polymerization-

[0289] Furthermore, the average degree of polymerization of the vinyl chloride resin constituting the vinyl chloride resin pellets is preferably 800 or greater, more preferably 1000 or greater, 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 pellets is above the aforementioned lower limit, the physical strength of the resin molded article formed using the resin composition can be sufficiently ensured, and tensile properties, particularly tensile elongation, can be improved. Furthermore, a resin molded article with excellent tensile elongation can be preferably used as an automotive interior material, such as the surface of an automobile instrument panel, which exhibits excellent ductility and breaks as designed during airbag inflation and deployment without scattering fragments. On the other hand, if the average degree of polymerization of the vinyl chloride resin constituting the vinyl chloride resin pellets is below the aforementioned upper limit, the meltability of the resin composition can be improved.

[0290] In the present invention, the "average degree of polymerization" can be measured in accordance with JIS K6720-2.

[0291] - Average particle size -

[0292] Furthermore, the average particle size of the vinyl chloride resin particles is generally 30 μm or greater, preferably 50 μm or greater, more preferably 100 μm or greater, and preferably 500 μm or less, more preferably 200 μm or less. When the average particle size of the vinyl chloride resin particles is greater than or equal to the lower limit, the powder flowability of the resin composition can be improved. On the other hand, when the average particle size of the vinyl chloride resin particles is less than or equal to the upper limit, the meltability of the resin composition can be improved, thereby improving the surface smoothness of the resulting resin molded article.

[0293] In the present invention, the “average particle size” can be measured as a volume average particle size by a laser diffraction method in accordance with JIS Z8825.

[0294] - Content ratio -

[0295] Furthermore, the content of the vinyl chloride resin particles in the vinyl chloride resin is preferably 70% by mass or greater, more preferably 80% by mass or greater, and can be 100% by mass, preferably 95% by mass or less, and more preferably 90% by mass or less. If the content of the vinyl chloride resin particles in the vinyl chloride resin is greater than the lower limit, the physical strength of the resin molded article formed using the resin composition can be sufficiently ensured, and the tensile elongation can be improved. On the other hand, if the content of the vinyl chloride resin particles in the vinyl chloride resin is less than the upper limit, the powder flowability of the resin composition can be improved.

[0296] [Vinyl chloride resin particles]

[0297] In a resin composition, vinyl chloride resin fine particles generally function as a release agent (powder flowability improver). In addition, vinyl chloride resin fine particles are preferably produced by emulsion polymerization.

[0298] -Average degree of polymerization-

[0299] Furthermore, the average degree of polymerization of the vinyl chloride resin constituting the vinyl chloride resin microparticles is preferably 500 or higher, more preferably 700 or higher, and preferably 2600 or lower, more preferably 2400 or lower. If the average degree of polymerization of the vinyl chloride resin constituting the vinyl chloride resin microparticles serving as the release agent is above the aforementioned lower limit, the powder flowability of the resin composition can be improved, and the tensile elongation of the resulting 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 below the aforementioned upper limit, the meltability of the resin composition can be improved, and the surface smoothness of the resulting resin molded article can be improved.

[0300] - Average particle size -

[0301] Furthermore, the average particle size of the vinyl chloride resin microparticles is generally less than 30 μm, preferably 10 μm or less, more preferably 5 μm or less, preferably 0.1 μm or more, and more preferably 1 μm or more. When the average particle size of the vinyl chloride resin microparticles is above the lower limit, the particles are prevented from becoming too small, for example, as a release agent, and the powder flowability of the resin composition can be improved. On the other hand, when the average particle size of the vinyl chloride resin microparticles is below the upper limit, the meltability of the resin composition can be improved, thereby enhancing the surface smoothness of the resulting resin molded article.

[0302] - Content ratio -

[0303] Furthermore, the content of the vinyl chloride resin microparticles in the vinyl chloride resin may be 0% by mass, preferably 5% by mass or greater, more preferably 10% by mass or greater, preferably 30% by mass or less, and more preferably 20% by mass or less. If the content of the vinyl chloride resin microparticles in the vinyl chloride resin is at least the lower limit, the powder flowability of the resin composition can be improved. On the other hand, if the content of the vinyl chloride resin microparticles in the vinyl chloride resin is at most the upper limit, the physical strength of the resulting resin molded article can be improved.

[0304] <(b) Plasticizer Composition>

[0305] As the (b) plasticizer composition, a plasticizer composition containing at least the compound of the present invention and optionally further containing a polyester plasticizer and other plasticizers is used.

[0306] The content of the compound of the present invention in resin composition is preferably more than 1 mass part relative to the above-mentioned (a) resin of 100 mass parts, more preferably more than 1.5 mass parts, more preferably more than 2 mass parts, more preferably more than 2.5 mass parts, more preferably more than 3 mass parts, more preferably more than 8 mass parts again, preferably less than 20 mass parts, more preferably less than 18 mass parts, more preferably less than 16 mass parts, more preferably less than 12 mass parts.If the content of the compound of the present invention in resin composition is more than the above-mentioned lower limit, it is possible to further improve the low-temperature tensile elongation of the resin molded body formed and improve the adhesion of the resin molded body to foamed polyurethane molded body.On the other hand, if the content of the compound of the present invention in resin composition is below the above-mentioned upper limit, it is possible to fully highly ensure the heat shrinkage resistance of the resin molded body formed.

[0307] In addition, when the (b) plasticizer composition contains a polyester plasticizer, the content of the polyester plasticizer in the resin composition is preferably 30 parts by mass or more, more preferably 50 parts by mass or more, further preferably 70 parts by mass or more, even more preferably 80 parts by mass or more, and even more preferably 85 parts by mass or more, preferably 200 parts by mass or less, more preferably 180 parts by mass or less, further preferably 150 parts by mass or less, even more preferably 130 parts by mass or less, even more preferably 110 parts by mass or less, and particularly preferably 100 parts by mass or less. If the content of the polyester plasticizer in the resin composition is above the lower limit, the heat shrinkage resistance of the formed resin molded body can be further improved. On the other hand, if the content of the polyester plasticizer in the resin composition is below the upper limit, the adhesion of the formed resin molded body to the foamed polyurethane molded body can be sufficiently high.

[0308] The content of the other plasticizer in the resin composition is not particularly limited, but can be 0 parts by mass or more and 15 parts by mass or less relative to 100 parts by mass of the (a) resin.

[0309] Moreover, when an epoxidized vegetable oil such as epoxidized soybean oil is used as another plasticizer, from the viewpoint of further improving the low-temperature tensile elongation of the formed resin molded body while ensuring a sufficiently high heat shrinkage resistance of the resin molded body, the content of the epoxidized vegetable oil as another plasticizer is preferably 2 parts by mass or more, more preferably 3 parts by mass or more, further preferably 4 parts by mass or more, and preferably 10 parts by mass or less, more preferably 7 parts by mass or less, relative to 100 parts by mass of the above-mentioned (a) resin.

[0310] In addition, the total content of the compound of the present invention, the polyester plasticizer, and other plasticizers in the resin composition (i.e., the content of the (b) plasticizer composition) is preferably 31 parts by mass or more, more preferably 53.5 parts by mass or more, further preferably 75 parts by mass or more, further preferably 86.5 parts by mass or more, and even more preferably 92 parts by mass or more, preferably 235 parts by mass or less, more preferably 208 parts by mass or less, further preferably 176 parts by mass or less, further preferably 154 parts by mass or less, further preferably 129 parts by mass or less, and particularly preferably 119 parts by mass or less. If the content of the plasticizer composition in the resin composition is within the above-specified range, the resin composition can be easily molded (e.g., powder molding) and the resulting resin molded article can achieve high levels of low-temperature tensile elongation, heat shrinkage resistance, and adhesion to a foamed polyurethane molded article.

[0311] <Additives>

[0312] The resin composition of the present invention may contain various additives in addition to the above-mentioned components. Examples of such additives include, but are not particularly limited to, lubricants; stabilizers such as perchloric acid-treated hydrotalcite, zeolite, β-diketone, and fatty acid metal salts; mold release agents; release agents other than the vinyl chloride resin microparticles described above; impact modifiers; perchloric acid compounds other than perchloric acid-treated hydrotalcite (such as sodium perchlorate and potassium perchlorate); antioxidants; mildew inhibitors; flame retardants; antistatic agents; fillers; light stabilizers; foaming agents; and pigments.

[0313] Furthermore, as the additives that may be contained in the resin composition of the present invention, for example, additives described in International Publication No. 2016 / 098344 may be used, and the preferred content thereof may also be the same as that described in International Publication No. 2016 / 098344.

[0314] <Method for Preparing Resin Composition>

[0315] The resin composition of the present invention can be prepared by mixing the above-mentioned components.

[0316] The method for mixing the resin (a), the plasticizer composition (b), and any additional additives as needed is not particularly limited. Examples of such methods include dry blending the components other than the release agent (including the vinyl chloride resin fine particles), followed by adding the release agent and mixing. A Henschel mixer is preferably used for dry blending. The temperature during dry blending is not particularly limited, but is preferably 50°C or higher, more preferably 70°C or higher, and preferably 200°C or lower.

[0317] <Application of resin composition>

[0318] Furthermore, the obtained resin composition can be preferably used for powder molding, and more preferably for powder slush molding.

[0319] (Resin molded body)

[0320] The resin molded article of the present invention is characterized by being obtained by molding the above-mentioned resin composition using any method. Furthermore, since the resin molded article of the present invention is formed using the above-mentioned resin composition, it generally comprises at least (a) a resin and (b) a plasticizer composition. That is, the resin molded article of the present invention generally comprises at least (a) a resin and the compound of the present invention, and optionally further comprises a polyester plasticizer, other plasticizers, and additives. Furthermore, the resin molded article of the present invention exhibits excellent low-temperature tensile elongation and heat shrinkage resistance.

[0321] Therefore, the resin molded article of the present invention can be preferably used as an automobile interior material such as the surface skin of an automobile instrument panel.

[0322] <Method for Forming Resin Molded Body>

[0323] Here, when the resin molded body is formed by powder slush molding, the metal mold temperature during powder slush molding is not particularly limited, but is preferably 200°C or higher, more preferably 220°C or higher, and preferably 300°C or lower, more preferably 280°C or lower.

[0324] Furthermore, when producing a resin molded article, there are no particular limitations, and the following method can be used, for example. Specifically, the resin composition of the present invention is sprinkled into a metal mold within the above-mentioned temperature range, left for a period of 5 seconds to 30 seconds, and then the remaining resin composition is shaken off. Furthermore, the mold is left for a period of 30 seconds to 3 minutes at an arbitrary temperature. Thereafter, the mold is cooled to a temperature of 10°C to 60°C, and the resulting resin molded article of the present invention is demolded from the mold. A sheet-like molded article shaped in the shape of the mold is then obtained.

[0325] (Laminated body)

[0326] The laminate of the present invention comprises a foamed polyurethane molded body and the above-mentioned resin molded body.

[0327] Furthermore, the laminate of the present invention has a resin molded body having excellent low-temperature tensile elongation and heat shrinkage resistance, for example, formed using the resin composition of the present invention. Therefore, the laminate of the present invention can be preferably used as an automotive interior material for forming automotive interior parts, particularly automotive instrument panels.

[0328] Here, the method for laminating the foamed polyurethane molded body and the resin molded body is not particularly limited, and the following methods can be used, for example. Specifically, the following methods can be used: (1) a method in which the foamed polyurethane molded body and the resin molded body are prepared separately and then laminated using heat welding, thermal bonding, or a known adhesive; (2) a method in which isocyanates, which are raw materials for the foamed polyurethane molded body, are reacted with polyols, etc. on the resin molded body to polymerize, and polyurethane is foamed using a known method, thereby directly forming the foamed polyurethane molded body on the resin molded body. The latter method (2) is particularly preferred because it simplifies the process and makes it easy to firmly bond the resin molded body and the foamed polyurethane molded body even when obtaining laminates of various shapes.

[0329] Example

[0330] Hereinafter, the present invention will be specifically described based on Examples, but the present invention is not limited to these Examples. In addition, in the following description, "%" and "parts" showing amounts are based on mass unless otherwise specified.

[0331] Then, the tensile properties under low temperature conditions, heat shrinkage resistance, and adhesion to the foamed polyurethane molded product of the vinyl chloride resin molded sheet (vinyl chloride resin molded product) were measured and evaluated by the following methods.

[0332] <Tensile properties at low temperatures (tensile strength, tensile elongation)>

[0333] The vinyl chloride resin molded sheet, punched out using a No. 1 dumbbell cutter described in JIS K6251, was measured for tensile elongation at break (%) and tensile stress at break (MPa) at a low temperature of -25°C at a tensile speed of 200 mm / min in accordance with JIS K7113. A higher value for tensile elongation at break indicates superior tensile elongation (low-temperature tensile elongation) of the vinyl chloride resin molded sheet in its initial (unheated) low-temperature state. Furthermore, a higher value for tensile stress at break indicates superior tensile strength of the vinyl chloride resin molded sheet in its initial (unheated) low-temperature state.

[0334] <Heat shrinkage resistance>

[0335] The length of the vinyl chloride resin molded sheet of the obtained laminate in the short-side direction was measured using a three-dimensional measuring instrument ("Crysta-Plus M443" manufactured by Mitutoyo Corporation) as the actual measured value before heating.

[0336] The laminate was then heated in a Geer oven (manufactured by Toyo Seiki Seisaku-sho, Ltd.) at 120°C. After 600 hours, the laminate was removed from the oven and the length of the vinyl chloride resin molded sheet in the laminate in the short-side direction was measured using the three-dimensional measuring instrument. This was used as the measured value after heating. The heat shrinkage (%) was calculated using the measured values before and after heating, as shown in the following formula.

[0337] Thermal shrinkage [%] = 100 × (measured value before heating - measured value after heating) / measured value before heating

[0338] In addition, the smaller the value of the heat shrinkage ratio is, the smaller the heat shrinkage of the vinyl chloride resin molded sheet is, and the better the heat shrinkage resistance of the vinyl chloride resin molded sheet is.

[0339] <Adhesion to Polyurethane Foam Molded Articles>

[0340] Using a laminate formed by backing the obtained vinyl chloride resin molded sheet with the foamed polyurethane molded article, the vinyl chloride resin molded sheet was peeled off from the foamed polyurethane molded article. The adhesion of the vinyl chloride resin molded sheet (vinyl chloride resin molded article) to the polyurethane molded article was evaluated by visually inspecting the surface of the peeled vinyl chloride resin molded sheet that was backed with the foamed polyurethane molded article.

[0341] The case where the surface portion of the foamed polyurethane molded article remained on the entire surface of the vinyl chloride resin molded sheet as visually confirmed was deemed "foam collapse" (evaluation A in Table 1). The case where the surface portion of the foamed polyurethane molded article remained only at a portion of the surface of the vinyl chloride resin molded sheet and no surface portion of the foamed polyurethane molded article remained at other portions was deemed "partial interface peeling" (evaluation B in Table 1). The case where the surface portion of the foamed polyurethane molded article remained at no portion of the entire surface of the vinyl chloride resin molded sheet was deemed "complete interface peeling" (evaluation C in Table 1).

[0342] The more areas where the surface portion of the polyurethane foam molded article remains on the surface of the vinyl chloride resin molded sheet, the higher the adhesion of the vinyl chloride resin molded sheet (vinyl chloride resin molded article) to the polyurethane foam molded article.

[0343] (synthesis example)

[0344] The compounds used in each example were prepared as described below.

[0345] In addition, the nuclear magnetic resonance (NMR) method ( 1 H-NMR, 13 The spectra obtained by respective measurements of C-NMR, CH COSY) and IR (ATR) are shown in FIG. Figures 1 to 4 .pass Figure 1 of 1 The H-NMR spectrum showed that the signal position of the hydroxyl group was 2.15 ppm.

[0346] In addition, the NMR ( 1 H-NMR, 13 The spectra obtained by respective measurements of C-NMR, CH COSY) and IR (ATR) are shown in FIG. Figures 5 to 8 .pass Figure 5 of 1 The H-NMR spectrum showed that the signal position of the hydroxyl group was 3.33 ppm.

[0347] <Synthesis Example 1> Synthesis of Diester Mixture 1

[0348] According to the following synthesis scheme, the diester mixture 1 was synthesized from "Cardolite LITE 2020" (manufactured by Cardolite Corporation).

[0349] In the synthesis scheme, R represents any of the following four hydrocarbon groups having 15 carbon atoms, and * indicates the position of the single bond to the benzene ring (the same applies to Synthesis Examples 2 to 7 below). Furthermore, "Cardolite LITE 2020" and Diester Mixture 1 each represent a mixture of compounds in which R represents any of the following four hydrocarbon groups. The two R groups in Diester Mixture 1 may be the same or different.

[0350] [Chemical Formula 12]

[0351]

[0352] In a three-necked reactor equipped with a thermometer, 80 g (0.23 mol) of "Cardolite LITE 2020" (manufactured by Cardolite Corporation) was dissolved in 250 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. 16.15 g (0.11 mol) of adipic acid and 2.8 g (0.023 mol) of N,N-dimethyl-4-aminopyridine (DMAP) were added and dissolved in this solution. While maintaining the temperature below 25°C in a water bath, 44.5 g (0.23 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added to the solution. The entire mixture was stirred at 25°C for 18 hours.

[0353] After the reaction was completed, the reaction solution was poured into 2500 mL of distilled water and extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off.

[0354] After the solvent was evaporated by a rotary evaporator, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=85:15 (volume ratio)), thereby obtaining 58 g of diester mixture 1 as a pale yellow oil. The structure of diester mixture 1 was determined by NMR ( 1 H-NMR, 13 C-NMR) and IR (ATR) were used for identification.

[0355] 1 H-NMR (500 MHz, CDCl 3 , TMS, δ ppm): The disappearance of the 2.15 ppm signal derived from the hydroxyl group of "Cardolite LITE 2020" (manufactured by Cardolite Corporation) was confirmed.

[0356] 13 C-NMR (500 MHz, CDCl 3 , TMS, δ ppm): Generation of a 173.27 ppm signal derived from carbonyl carbon was confirmed.

[0357] IR (ATR): 1736 cm-1 derived from the ester bond was confirmed -1 Peak generation.

[0358] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in Figures 9 to 11 .

[0359] <Synthesis Example 2> Synthesis of diurethane mixture 1

[0360] According to the following synthesis scheme, diurethane mixture 1 was synthesized from "Cardolite LITE 2020" (manufactured by Cardolite Corporation).

[0361] In addition, "Cardolite LITE 2020" and diurethane mixture 1 each represent a mixture of compounds in which R is any one of the following four hydrocarbon groups. The two Rs contained in diurethane mixture 1 may be the same or different.

[0362] [Chemical Formula 13]

[0363]

[0364] In a three-necked reactor equipped with a thermometer, 92 g (0.27 mol) of Cardolite LITE 2020 (manufactured by Cardolite Corporation) was dissolved in 200 mL of tetrahydrofuran (THF) under a nitrogen stream and cooled to 5°C in an ice bath. 2.0 g (0.013 mol) of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was slowly added to this solution. A solution of 22.5 g (0.13 mol) of hexamethylene diisocyanate dissolved in 130 mL of THF, adjusted to below 10°C in an ice bath, was slowly added dropwise to this solution. The mixture was then slowly returned to room temperature, then heated to 50°C and stirred for 2 hours. After the reaction was complete, the reaction mixture was poured into 2500 mL of dilute hydrochloric acid 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 out.

[0365] After removing the solvent by evaporation using a rotary evaporator, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate = 80:20 (volume ratio)) to obtain 54 g of diurethane mixture 1 as a pale yellow solid. The melting point was 94-96°C. The structure of diurethane mixture 1 was determined by NMR ( 1 H-NMR, 13 C-NMR) and IR (ATR) were used for identification.

[0366] 1 H-NMR (500 MHz, CDCl 3 , TMS, δ ppm): The disappearance of the 2.15 ppm signal derived from the hydroxyl group of "Cardolite LITE 2020" (manufactured by Cardolite Corporation) was observed. The generation of the 4.79 ppm signal derived from the NH group of the carbamate was observed.

[0367] 13 C-NMR (500 MHz, CDCl 3 , TMS, δ ppm): generation of a 155.99 ppm signal derived from carbonyl carbon was confirmed.

[0368] IR (ATR): 1685 cm-1 derived from the urethane bond was confirmed -1 、1718cm -1 The peak generated by NH at 3327 cm -1 Peak generation.

[0369] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in Figures 12 to 14 .

[0370] <Synthesis Example 3> Synthesis of Diether Mixture 1

[0371] According to the following synthesis scheme, diether mixture 1 was synthesized from "Cardolite LITE 2020" (manufactured by Cardolite Corporation).

[0372] In addition, "Cardolite LITE 2020" and diether mixture 1 each represent a mixture of compounds in which R is any one of the following four hydrocarbon groups. The two Rs contained in diether mixture 1 may be the same or different.

[0373] [Chemical Formula 14]

[0374]

[0375] In a three-necked reactor equipped with a thermometer, 35.5 g (net weight 19.5 g (0.81 mol)) of 55% sodium hydride and 250 ml of cyclopentyl methyl ether (CPME) were added under ice-bath cooling in a nitrogen stream. While maintaining the ice bath, a solution of 80 g (0.23 mol) of "Cardolite LITE 2020" (manufactured by Cardolite) dissolved in 50 ml of CPME was slowly added dropwise to the slurry solution, adjusting the internal temperature to around 10°C. The reaction solution was returned to room temperature and stirred at 23°C for 30 minutes. The reaction solution was then heated to 80°C, and a solution of 19.9 g (0.082 mol) of dibromohexane dissolved in 10 ml of CPME was slowly added dropwise. The mixture was then heated to reflux at 110°C for 11 hours. After the reaction is completed, the mixture is cooled in an ice bath. A mixed solution of 100 ml of tetrahydrofuran and 50 ml of water is slowly added dropwise while still in the ice bath. Furthermore, the solution is acidified by adding a predetermined amount of 300 ml of hydrochloric acid, and then extracted twice with 300 ml of ethyl acetate. The ethyl acetate layer is dried over anhydrous sodium sulfate, and the sodium sulfate is filtered off.

[0376] After the solvent was evaporated by a rotary evaporator, the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10 (volume ratio)), thereby obtaining 57 g of diether mixture 1 as a light yellow oil. The structure of diether mixture 1 was determined by NMR ( 1 The products were identified by H-NMR) and IR (ATR).

[0377] 1 H-NMR (500 MHz, CDCl 3 , TMS, δ ppm): The disappearance of the 2.15 ppm signal derived from the hydroxyl group of "Cardolite LITE 2020" (manufactured by Cardolite Corporation) was confirmed.

[0378] IR (ATR): 1124 cm-1 derived from the ether bond was confirmed -1 Peak generation.

[0379] 1 The respective spectra of H-NMR and IR (ATR) are shown in Figures 15 and 16 .

[0380] <Synthesis Example 4> Synthesis of Diester Mixture 2

[0381] According to the following synthesis scheme, the diester mixture 2 was synthesized from "Cardolite NX-7505" (manufactured by Cardolite Corporation).

[0382] In addition, "Cardolite NX-7505" and diester mixture 2 each represent a mixture of compounds in which R is any one of the following four hydrocarbon groups having 15 carbon atoms. The two Rs contained in diester mixture 2 may be the same or different.

[0383] [Chemical Formula 15]

[0384]

[0385] In a three-necked reactor equipped with a thermometer, 80 g (0.13 mol) of "Cardolite NX-7505" (manufactured by Cardolite Corporation) 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 and dissolved in this solution. While maintaining the temperature below 25°C on a water bath, 25.24 g (0.13 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added to the solution. The entire mixture was stirred at 25°C for 24 hours.

[0386] After the reaction was completed, the reaction solution was poured into 2500 mL of distilled water and extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off.

[0387] After removing the solvent by rotary evaporation, the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 90:10 (volume ratio)) to obtain 84 g of diester mixture 2 as a pale yellow oil. The structure of diester mixture 2 was identified by NMR and IR (ATR).

[0388] 1 H-NMR (500 MHz, CDCl 3 , TMS, δ ppm): The disappearance of the 3.33 ppm signal derived from the hydroxyl group of Cardolite NX-7507 (manufactured by Cardolite Corporation) was confirmed.

[0389] 13 C-NMR (500 MHz, CDCl 3 , TMS, δ ppm): Generation of signals at 175.03 ppm and 173.23 ppm derived from carbonyl carbon was confirmed.

[0390] IR (ATR): 1736 cm-1 derived from the ester bond was confirmed -1 、1685cm -1 Peak generation.

[0391] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in Figures 17 to 19 .

[0392] <Synthesis Example 5> Synthesis of Trisester Mixture 1

[0393] According to the following synthesis scheme, triester mixture 1 was synthesized from "Cardolite NX-7505" (manufactured by Cardolite Corporation).

[0394] In addition, "Cardolite NX-7505" and triester mixture 1 each represent a mixture of compounds in which R is any one of the following four hydrocarbon groups. The three Rs contained in triester mixture 1 may be the same as or different from each other.

[0395] [Chemical Formula 16]

[0396]

[0397] In a three-necked reactor equipped with a thermometer, 81.8 g (0.134 mol) of "Cardolite NX-7505" (manufactured by Cardolite Corporation) was dissolved in 200 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. 9.0 g (0.044 mol) of 1,3,5-pentanetricarboxylic acid and 3.6 g (0.029 mol) of N,N-dimethyl-4-aminopyridine (DMAP) were added to this solution and dissolved. While maintaining the temperature below 25°C on a water bath, 28.3 g (0.148 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added to the solution. The mixture was stirred at 25°C for 18 hours.

[0398] After the reaction was completed, the reaction solution was poured into 2500 mL of distilled water and extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off.

[0399] 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 triester mixture 1 as a pale yellow oil. The structure of triester mixture 1 was identified by NMR and IR (ATR).

[0400] 1 H-NMR (500 MHz, CDCl 3 , TMS, δ ppm): The disappearance of the 3.33 ppm signal derived from the hydroxyl group of "Cardolite NX-7507" (manufactured by Cardolite Corporation) was confirmed.

[0401] 13 C-NMR (500 MHz, CDCl 3 , TMS, δ ppm): Generation of a 175.05 ppm signal derived from carbonyl carbon was confirmed.

[0402] IR (ATR): 1734 cm-1 derived from ester bond was confirmed -1 、1685cm -1 Peak generation.

[0403] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in Figures 20 to 22 .

[0404] <Synthesis Example 6> Synthesis of Diester Mixture 3

[0405] According to the following synthesis scheme, the diester mixture 3 was synthesized from "Cardolite NX-7505" (manufactured by Cardolite Corporation).

[0406] In addition, "Cardolite NX-7505" and diester mixture 3 each represent a mixture of compounds in which R is any one of the following four hydrocarbon groups. The two Rs contained in diester mixture 3 may be the same or different.

[0407] [Chemical Formula 17]

[0408]

[0409] In a three-necked reactor equipped with a thermometer, 73.3 g (0.121 mol) of "Cardolite NX-7507" (manufactured by Cardolite Corporation) was dissolved in 200 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. To this solution, 10 g (0.057 mol) of 3-ethyl-3-methylglutaric acid and 3.24 g (0.027 mol) of N,N-dimethyl-4-aminopyridine (DMAP) were added and dissolved. While adjusting the temperature to below 25°C on a water bath, 25.4 g (0.132 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added to the solution. The entire contents were stirred at 25°C for 18 hours. After the reaction, the reaction mixture was poured into 2500 mL of distilled water and extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off. The solvent was removed by rotary evaporation, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 90:10 to 85:15 gradient (volume ratio)) to obtain 81 g of diester mixture 3 as a pale yellow oil. The structure of diester mixture 3 was identified by NMR and IR (ATR).

[0410] 1 H-NMR (500 MHz, CDCl 3 , TMS, δ ppm): The disappearance of the 3.33 ppm signal derived from the hydroxyl group of "Cardolite NX-7507" (manufactured by Cardolite Corporation) was confirmed.

[0411] 13 C-NMR (500 MHz, CDCl 3 , TMS, δ ppm): Generation of signals at 175.11 ppm and 166.39 ppm derived from carbonyl carbon was confirmed.

[0412] IR (ATR): 1730 cm-1 derived from ester bond was confirmed -1 、1685cm -1 、1672cm -1 Peak generation.

[0413] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in Figures 23 to 25 .

[0414] <Synthesis Example 7> Synthesis of Diester Mixture 4

[0415] According to the following synthesis scheme, the diester mixture 4 was synthesized from "Cardolite NX-7505" (manufactured by Cardolite Corporation).

[0416] In addition, "Cardolite NX-7505" and diester mixture 4 each represent 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.

[0417] [Chemical Formula 18]

[0418]

[0419] In a three-necked reactor equipped with a thermometer, 84.58 g (0.139 mol) of Cardolite NX-7507 (manufactured by Cardolite Corporation) was dissolved in 250 mL of N-methylpyrrolidone (NMP) under a nitrogen stream. To this solution, 11.0 g (0.066 mol) of terephthalic acid and 3.74 g (0.031 mol) of N,N-dimethyl-4-aminopyridine (DMAP) were added and dissolved. While adjusting the temperature to below 25°C on a water bath, 29.32 g (0.153 mol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (WSC) was slowly added to the solution. The entire contents were stirred at 25°C for 22 hours. After the reaction was completed, the reaction mixture was poured into 2500 mL of distilled water and extracted twice with 300 mL of ethyl acetate. The ethyl acetate layer was dried over anhydrous sodium sulfate, and the sodium sulfate was filtered off. After removing the solvent by rotary evaporation, the resulting residue was purified by silica gel column chromatography (chloroform:methanol=85:15 (volume ratio)) to obtain 82 g of diester mixture 4 as a pale yellow oil. The structure of diester mixture 4 was identified by NMR and IR (ATR).

[0420] 1 H-NMR (500 MHz, CDCl 3 , TMS, δ ppm): The disappearance of the 3.33 ppm signal derived from the hydroxyl group of Cardolite NX-7507 (manufactured by Cardolite Corporation) was observed. The generation of aromatic hydrogen of terephthalic acid was observed at 8.11 ppm.

[0421] 13 C-NMR (500 MHz, CDCl 3 , TMS, δ ppm): Generation of signals at 174.96 ppm and 165.62 ppm derived from carbonyl carbon was confirmed.

[0422] IR (ATR): 1720 cm-1 derived from the ester bond was confirmed -1 、1689cm -1 Peak generation.

[0423] 1 H-NMR, 13 The respective spectra of C-NMR and IR (ATR) are shown in Figures 26 to 28 .

[0424] (Example 1)

[0425] <Preparation of Vinyl Chloride Resin Composition>

[0426] The ingredients listed in Table 1, excluding the plasticizer composition (polyester plasticizer, compound, and other plasticizers) and vinyl chloride resin microparticles as a release agent, were mixed in a Henschel mixer. When the mixture reached a temperature of 80°C, the entire plasticizer composition was added. The mixture was allowed to dry completely (meaning the plasticizer was absorbed by the vinyl chloride resin particles, resulting in a dry, crisp mixture). Mixing was continued until the maximum temperature reached 100°C to 200°C. After the dried mixture was cooled to a temperature below 100°C, the vinyl chloride resin microparticles as a release agent were added to prepare a vinyl chloride resin composition.

[0427] <Formation of Vinyl Chloride Resin Molded Sheet>

[0428] The resulting vinyl chloride resin composition was poured into a textured mold heated to 250°C and allowed to melt for an arbitrary period of time, after which the excess vinyl chloride resin composition was shaken off. The textured mold containing the vinyl chloride resin composition was then placed in an oven set at 200°C and allowed to stand. After 60 seconds had passed since the start of the standstill, the textured mold was cooled with cooling water. When the mold cooled to 40°C, a 200 mm × 150 mm × 1 mm vinyl chloride resin molded sheet was removed from the mold.

[0429] The obtained vinyl chloride resin molded sheet was used to evaluate its initial (unheated) low-temperature tensile properties (tensile strength, tensile elongation).

[0430] <Formation of Laminated Body>

[0431] Two obtained vinyl chloride resin molded sheets (size: 200 mm×150 mm×1 mm) were placed in a metal mold of 200 mm×300 mm×10 mm with the textured surface facing downward.

[0432] Separately, a polyol mixture consisting of 50 parts by mass of a propylene oxide / ethylene oxide (PO·EO) block adduct of propylene glycol (hydroxyl value 28, terminal EO unit content = 10%, internal EO unit content = 4%), 50 parts by mass of a PO·EO block adduct of glycerol (hydroxyl value 21, terminal EO unit content = 14%), 2.5 parts by mass of water, 0.2 parts by mass of an ethylene glycol solution of triethylenediamine (trade name: "TEDA-L33" manufactured by Tosoh Corporation), 1.2 parts by mass of triethanolamine, 0.5 parts by mass of triethylamine, and 0.5 parts by mass of a foam stabilizer (trade name: "F-122" manufactured by Shin-Etsu Chemical Co., Ltd.) was mixed with polymethylene polyphenylene polyisocyanate (polymeric MDI) at a ratio to give an index of 98 to prepare a mixed solution. The prepared mixed solution was then poured onto the two vinyl chloride resin molded sheets placed in the above-mentioned metal mold. The mold was then sealed by covering it with a 348 mm x 255 mm x 10 mm aluminum plate and left to stand for 5 minutes after sealing the mold to form a laminated body having a polyurethane foam molded body lined with a vinyl chloride resin molded sheet (thickness: 1 mm) as the skin.

[0433] The formed laminate was removed from the mold, and the adhesion of the vinyl chloride resin molded sheet in the laminate to the foamed polyurethane molded article was evaluated. The results are shown in Table 1.

[0434] (Examples 2 to 10, Comparative Examples 1 to 4)

[0435] A vinyl chloride resin composition, a vinyl chloride resin molded sheet, and a laminate were produced in the same manner as in Example 1, except that the blending composition during preparation of the vinyl chloride resin composition was changed as shown in Table 1. The resulting vinyl chloride resin molded sheet and laminate were then used to evaluate the low-temperature tensile properties, heat shrinkage resistance, and adhesion to a foamed polyurethane molded article of the vinyl chloride resin molded sheet. The results are shown in Table 1.

[0436] In addition, in Table 1,

[0437] "EO modified" means "ethylene oxide modified";

[0438] "n" means "the number of repeating units n of ethylene oxide units".

[0439] [Table 1]

[0440]

[0441] 1) ZEST (registered trademark) 1300SI, manufactured by Shin-Daiichi Chloro Vinyl Co., Ltd. (produced using a suspension polymerization method, average degree of polymerization: 1300, average particle size: 115 μm)

[0442] 2) ZEST PQLTX manufactured by Shin-Daiichi Chloro Vinyl Co., Ltd. (produced by emulsion polymerization, average degree of polymerization: 800, average particle size: 1.8 μm)

[0443] 3) ADK CIZER HPN-3130 (Adipate polyester, viscosity (25°C): 3000 mPa·s) manufactured by ADK Co., Ltd.

[0444] 4) Cardolite LITE 2020 (ethylene oxide-modified cardanol, number of repeating ethylene oxide units n = 1)

[0445] 5) Cardolite NX-7507 (ethylene oxide-modified cardanol, number of repeating ethylene oxide units n = 7)

[0446] 6) Made by Taoka Industry Co., Ltd., product name "DODN"

[0447] 7) ADK CIZER O-130S, manufactured by ADK Co., Ltd.

[0448] 8) Kyowa Chemical Industry Co., Ltd., product name "ALCAMAIZER (registered trademark) 5"

[0449] 9) Mizusawa Chemical Industry Co., Ltd., product name "MIZUKALIZER DS"

[0450] 10) Made by Sakai Chemical Industry Co., Ltd., product name "SAKAI SZ2000"

[0451] 11) ADK STAB LA-72 manufactured by ADK Co., Ltd.

[0452] 12) ADK STAB LS-12 manufactured by ADK Co., Ltd.

[0453] 13) Made by Dainichi Seika Co., Ltd., product name "DAP 4720BLACK"

[0454] As apparent from Table 1, the resin compositions of Examples 1 to 10 prepared by using a compound having a predetermined structure as a plasticizer can form resin molded articles having excellent low-temperature tensile elongation and heat shrinkage resistance.

[0455] On the other hand, it was found that the resin molded article formed from the resin composition of Comparative Example 1 prepared without using the compound having a predetermined structure had poor low-temperature tensile elongation.

[0456] Furthermore, it was found that the resin molded article formed from the resin composition of Comparative Example 2, which was prepared using di(2-ethylhexyl) dodecanedioate instead of the compound having a predetermined structure, had poor resistance to heat shrinkage.

[0457] Furthermore, it was found that the resin molded articles formed from the resin compositions of Comparative Examples 3 and 4, which were prepared using ethylene oxide-modified cardanol instead of the compound having a predetermined structure, had poor heat shrinkage resistance.

[0458] Industrial applicability

[0459] According to the present invention, a compound that can be used for preparing a resin composition capable of forming a resin molded body having excellent low-temperature tensile elongation and heat shrinkage resistance and a method for using the compound can be provided.

[0460] Furthermore, according to the present invention, there can be provided a plasticizer composition that can be used for preparing a resin composition capable of forming a resin molded body having excellent low-temperature tensile elongation and heat shrinkage resistance.

[0461] Furthermore, according to the present invention, it is possible to provide a resin composition capable of forming a resin molded article having excellent low-temperature tensile elongation and heat shrinkage resistance.

[0462] Furthermore, according to the present invention, a resin molded article having excellent low-temperature tensile elongation and heat shrinkage resistance can be provided.

[0463] Furthermore, according to the present invention, a laminated body including the resin molded body can be provided.< / ax>

Claims

1. 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 4 Each independently represents a single bond, -C(=O)-, -C(=O)-NR 1 - or -C(=O)-O-, R 1 represents a hydrogen atom, a methyl group or an ethyl group, Y 2 、Y 3 Each independently represents a single bond, -C(=O)-, -NR 2 -C(=O)- or -OC(=O)-, R 2 represents a hydrogen atom, a methyl group or an ethyl group, SP 1 、SP 4 Each independently represents -CH2CH2O-, -CH2CH(CH3)O-, -CH(CH3)CH2O-, -CH2CH(CH2CH3)O- or -CH(CH2CH3)CH2O-, SP 2 、SP 3 each independently represents -OCH2CH2-, -OCH(CH3)CH2-, -OCH2CH(CH3)-, -OCH(CH2CH3)CH2- or -OCH2CH(CH2CH3)-, a, b, c, and d each independently represent an integer of 1 to 30, R a 、R b 、R c 、R d Each independently represents a chain aliphatic hydrocarbon group having 12 to 18 carbon atoms which may have a substituent, x and y each independently represent 0 or 1, When x is 0, the structure represented by the following formula (2) represents a hydrogen atom, When y is 0, the structure represented by the following formula (3) represents a hydrogen atom, In formulae (2) and (3), * represents a bonding position with Ax.

2. The compound according to claim 1, wherein Ax is any one of the following organic groups (i), (ii), (iii) and (iv): (i) a chain aliphatic hydrocarbon group having 3 to 20 carbon atoms which may have a substituent; (ii) a cyclic aliphatic hydrocarbon group having 4 to 12 carbon atoms which may have a substituent; (iii) an aromatic hydrocarbon ring group having 6 to 14 carbon atoms which may have a substituent; (iv) an organic group having 3 to 20 carbon atoms in which at least one of the single bonds contained in a chain aliphatic hydrocarbon group which may have a substituent is replaced by -O-, -C(=O)-, -OC(=O)-, or -C(=O)-O-, excluding the case where two or more -O- groups are consecutive, two or more -C(=O)- groups are consecutive, and -O- or -C(=O)- groups are located adjacent to the Y group. 1 、the Y 2 、the Y 3 or the Y 4 The case of the bonded ends.

3. The compound according to claim 1 or 2, wherein Ax is a group represented by any one of the following formulae (2-1) to (2-35) which may have a substituent, 4. A method comprising using the compound according to any one of claims 1 to 3 as a plasticizer. 5 . A plasticizer composition comprising the compound according to claim 1 .

6. The plasticizer composition according to claim 5, wherein The plasticizer composition comprises two or more compounds having different structures.

7. The plasticizer composition according to claim 5 or 6, wherein The plasticizer composition further comprises a polyester plasticizer.

8. The plasticizer composition according to claim 7, wherein The polyester plasticizer contains adipic acid-based polyester.

9. The plasticizer composition according to claim 7 or 8, wherein The content of the compound is 1 part by mass or more and 20 parts by mass or less relative to 100 parts by mass of the polyester plasticizer. 10 . A resin composition comprising a resin and the plasticizer composition according to claim 5 .

11. The resin composition according to claim 10, wherein The resin contains halogen.

12. The resin composition according to claim 10 or 11, wherein The glass transition temperature of the resin is 50° C. or higher and 100° C. or lower.

13. The resin composition according to any one of claims 10 to 12, wherein The resin contains vinyl chloride resin.

14. The resin composition according to any one of claims 10 to 13, wherein The content of the compound is 1 part by mass or more and 20 parts by mass or less relative to 100 parts by mass of the resin.

15. The resin composition according to any one of claims 10 to 14, wherein The resin composition is used for powder molding.

16. The resin composition according to any one of claims 10 to 15, wherein The resin composition is used for powder slush molding. 17 . A resin molded product obtained by molding the resin composition according to claim 10 .

18. The resin molded article according to claim 17, wherein The resin molded body is used for the surface skin of automobile instrument panels. 19 . A laminate comprising a foamed polyurethane molded product and the resin molded product according to claim 17 .

20. The laminate according to claim 19, wherein The laminate is for automobile instrument panels.

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