Aliphatic aldehyde composition

Abstract

Provided is a composition capable of suppressing generation of a trimer even when an aliphatic aldehyde at a high concentration of 90 mass% or more is stored at a low temperature. The composition contains 90 mass% or more of an aliphatic aldehyde having 8-16 carbon atoms and 100 ppm or more and 1 mass% or less of an additive with respect to the mass of the aliphatic aldehyde, wherein the additive is one or more selected from the group consisting of polyalkylene glycol derivatives represented by formula (I), sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, amino acids represented by formula (II), anthranilic acid esters represented by formula (III), and pyrazine derivatives represented by formula (IV).

Description

Aliphatic aldehyde composition

[0001] This invention relates to aliphatic aldehyde compositions.

[0002] It has long been known that aliphatic aldehydes are easily oxidized. For example, Japanese Patent Publication No. 40-90 reports a method for stabilizing 36% aqueous formaldehyde by adding guanamine.

[0003] Furthermore, Japanese Patent Publication No. 37-4109 reports a method for stabilizing formalin by adding esters of polyhydric alcohols and higher fatty acids, ethers and acetals of these polyhydric alcohols; higher alcohols; hydroquinone; polyvinyl alcohol and esters and acetals of polyvinyl alcohol and fatty acids, and derivatives made from each thereof.

[0004] Furthermore, Japanese Patent Publication No. 2010-523600 discloses a stable aqueous aldehyde solution comprising (a) an aldehyde comprising at least one of a monoaldehyde (R-CHO), a dialdehyde (OHC-R1-CHO), and a cyclic aldehyde (R3-CHO) in an m / v concentration of 0.001% to 25% (where R is hydrogen and the aldehyde is a straight-chain hydrocarbon having 1 to 12 carbon atoms), (b) a specific surfactant or detergent, (c) a sufficient amount of a pH adjuster to set the pH of the solution in the range of 6.0 to 8.5, and (d) at least one buffering agent.

[0005] Furthermore, Japanese Patent Publication No. 11-246461 describes the addition of alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonates, alkaline earth metal carbonates, or alkaline earth metal carboxylates, which results in aliphatic C3-C3 metals. 14 Methods for stabilizing aldehydes have been reported.

[0006] The present invention relates to a composition containing an aliphatic aldehyde having 8 to 16 carbon atoms and an additive, wherein the content of the aliphatic aldehyde is 90% by mass or more, the additive is one or more selected from the group consisting of the following components (A) to (F), and the content of the additive is 100 ppm or more and 1% by mass or less based on the mass of the aliphatic aldehyde. (A) (Poly)alkylene glycol represented by the following general formula (I) or a derivative thereof

[0007]

[0008] [In the formula (I), R 11 and R 12 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a group of the formula -C(=O)-R 14 ; R 14 is an alkyl group having 1 to 20 carbon atoms; R 13 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms; and n is an integer of 1 to 10. ] (B) Sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) Amino acid represented by the following general formula (II)

[0009]

[0010] [In the formula (II), R 41 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms substituted with a heterocyclic group, an aromatic ring group, COOH, NH2 or OH. ] (E) Anthranilic acid ester represented by the following general formula (III)

[0011]

[0012] [In the formula (III), R 51 is a hydrogen atom, a methyl group or an ethyl group; and R 52 is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. ] (F) Pyrazine derivative represented by the following general formula (IV)

[0013]

[0014] [In formula (IV), R 61 , R 62 , R 63 , and R 64 Each is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64 The total number of carbon atoms in the group is between 1 and 6. Detailed description of the invention

[0015] Patent documents 1 and 2 disclose methods for suppressing the aggregation of formalin at a concentration of 37% at room temperature. Patent document 3 discloses the stability of aliphatic aldehydes at low concentrations up to 25% at room temperature or 40°C. Patent document 4 discloses the long-term storage stability of aliphatic aldehydes at room temperature.

[0016] The present invention aims to provide a composition that can suppress the formation of trimers even when storing a high concentration of aliphatic aldehydes (90% by mass or more) at low temperatures.

[0017] The present invention provides the following (1) to (3): (1) A composition comprising an aliphatic aldehyde having 8 to 16 carbon atoms and an additive, wherein the aliphatic aldehyde content is 90% by mass or more, the additive is one or more selected from the group consisting of the following components (A) to (F), and the content of the additive is 100 ppm to 1% by mass relative to the mass of the aliphatic aldehyde. (A) A (poly)alkylene glycol or derivative thereof represented by the following general formula (I).

[0018]

[0019] [In formula (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the formula -C(=O)-R 14 It is the basis of R 14 R is an alkyl group having 1 to 20 carbon atoms.13 (B) A hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is an integer from 1 to 10. (C) A sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) An amino acid represented by the following general formula (II)

[0020]

[0021] [In formula (II), R 41 (E) Anthranilic acid ester represented by the following general formula (III)

[0022]

[0023] [In formula (III), R 51 R is a hydrogen atom, a methyl group, or an ethyl group. 52 (F) Pyrazine derivatives represented by the following general formula (IV)

[0024]

[0025] [In formula (IV), R 61 , R 62 , R 63 , and R 64 Each is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64 The total number of carbon atoms in the group is between 1 and 6.

[0026] (2) A trimer inhibitor for aliphatic aldehydes having 8 to 16 carbon atoms, comprising one or more selected from the group consisting of the following components (A) to (F): (A) (poly)alkylene glycol or derivative thereof represented by the following general formula (I).

[0027]

[0028] [In formula (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the formula -C(=O)-R 14 It is the basis of R 14 R is an alkyl group having 1 to 20 carbon atoms. 13 (B) A hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is an integer from 1 to 10. (C) A sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) An amino acid represented by the following general formula (II)

[0029]

[0030] [In formula (II), R 41 (E) Anthranilic acid ester represented by the following general formula (III)

[0031]

[0032] [In formula (III), R 51 R is a hydrogen atom, a methyl group, or an ethyl group. 52 (F) Pyrazine derivatives represented by the following general formula (IV)

[0033]

[0034] [In formula (IV), R 61 , R 62 , R 63 , and R 64 Each is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64The total number of carbon atoms in the group is between 1 and 6.

[0035] (3) A method for suppressing the formation of trimers of an aliphatic aldehyde, comprising mixing one or more additives selected from the group consisting of the following components (A) to (F) with an aliphatic aldehyde having 8 to 16 carbon atoms. (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I).

[0036] [In formula (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the formula -C(=O)-R 14 It is the basis of R 14 R is an alkyl group having 1 to 20 carbon atoms. 13 (B) A hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is an integer from 1 to 10. (C) A sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) An amino acid represented by the following general formula (II)

[0037]

[0038] [In formula (II), R 41 (E) Anthranilic acid ester represented by the following general formula (III)

[0039]

[0040] [In formula (III), R 51 R is a hydrogen atom, a methyl group, or an ethyl group. 52 (F) Pyrazine derivatives represented by the following general formula (IV)

[0041]

[0042] [In formula (IV), R 61 , R 62 , R 63 , and R 64 Each is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64 The total number of carbon atoms in the group is between 1 and 6.

[0043] The composition and method of the present invention can suppress trimer formation even when an aliphatic aldehyde with 8 to 16 carbon atoms is stored at a low temperature in a high concentration of 90% by mass or more.

[0044] The inventors of the present invention have discovered that by using a small amount of a specific additive, it is possible to suppress the formation of trimers even when storing a high concentration of 90% by mass of aliphatic aldehydes with 8 to 16 carbon atoms at low temperatures, thereby completing the present invention. This makes it possible to suppress the decrease in purity of aliphatic aldehydes. Furthermore, since trimers are white rather than transparent, the appearance of such aliphatic aldehydes is also excellent when they are returned from low temperatures to room temperature.

[0045] Specifically, aliphatic aldehydes with 8 to 16 carbon atoms have a high freezing point and tend to solidify at low temperatures. Even after solidification, if melted by heating, trimers derived from the aliphatic aldehyde remain as insoluble components. As a result, the purity of the aliphatic aldehyde decreases, and it becomes cloudy at room temperature. However, the inventors have found that adding small amounts of specific additives such as alkylene glycol derivatives, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, polyoxyethylene sorbitol fatty acid esters, amino acids, anthranilic acid esters, and pyrazine derivatives to aliphatic aldehydes can suppress the formation of trimers from the aliphatic aldehyde. This suppresses the decrease in the purity of the aliphatic aldehyde and also improves its appearance. Based on these findings, the inventors have completed the present invention.

[0046] Furthermore, as described in Japanese Patent Publication No. 59-51231, trimmer is a cyclic substance with a six-membered ring composed of three aliphatic aldehydes, and because it is stable, it does not decompose back into the original aliphatic aldehydes by simple heating.

[0047] <Aliphatic aldehydes having 8 to 16 carbon atoms> In the present invention, the aliphatic aldehydes having 8 to 16 carbon atoms may be linear or branched, and may be saturated or unsaturated. The aliphatic aldehydes having 8 to 16 carbon atoms are preferably aliphatic linear saturated primary aldehydes.

[0048] The carbon number of the aliphatic aldehyde is 8 or more, preferably 10 or more, more preferably 11 or more, from the viewpoint of having a high freezing point and being easy to solidify, and from the same viewpoint, 16 or less, preferably 14 or less, more preferably 13 or less. The carbon number of the aliphatic aldehyde is 8 or more and 16 or less, preferably 10 or more and 14 or less, preferably 10 or more and 12 or less, more preferably 11 or more and 13 or less, from the viewpoint of having a high freezing point and being easy to solidify.

[0049] Specifically, examples of aliphatic aldehydes having 8 to 16 carbon atoms include octanal (8 carbon atoms), nonanal (9 carbon atoms), decanal (10 carbon atoms), undecanal (11 carbon atoms), trans-9-undecenal (11 carbon atoms), cis-9-undecenal (11 carbon atoms), dodecanal (12 carbon atoms), trans-3-dodecenal (12 carbon atoms), cis-3-dodecenal (12 carbon atoms), trans-2-dodecenal (12 carbon atoms), cis-2-dodecenal (12 carbon atoms), tridecanal (13 carbon atoms), trans-2-tridecenal (13 carbon atoms), cis-2-tridecenal (13 carbon atoms), tetradecanal (14 carbon atoms), pentadecanal (15 carbon atoms), hexadecanal (16 carbon atoms), and the like. The aliphatic aldehyde is preferably linear. The aliphatic aldehyde is preferably a linear aliphatic aldehyde having 8 to 16 carbon atoms, more preferably 10 to 14 carbon atoms, and even more preferably 11 to 13 carbon atoms.

[0050] <Additives> The composition of the present invention comprises an aliphatic aldehyde having 8 to 16 carbon atoms and an additive. The additive comprises one or more selected from the group consisting of the following components (A) to (F). The additive may comprise one, two or more selected from the group consisting of the following components (A) to (F). The additive may be a combination of (A) a (poly)alkylene glycol or a derivative thereof represented by the following general formula (I) and (B) a sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms, or (B) a sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms and (C) a polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms.

[0051] (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I)

[0052]

[0053] [In formula (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the formula -C(=O)-R 14 It is the basis of R 14 R is an alkyl group having 1 to 20 carbon atoms. 13 (B) A hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is an integer from 1 to 10. (C) A sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) An amino acid represented by the following general formula (II)

[0054]

[0055] [In formula (II), R 41 (E) Anthranilic acid ester represented by the following general formula (III)

[0056]

[0057] [In formula (III), R 51 R is a hydrogen atom, a methyl group, or an ethyl group. 52 (F) A pyrazine derivative represented by the following general formula (IV).

[0058]

[0059] [In formula (IV), R 61 , R 62 , R 63 , and R 64 Each is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64 The total number of carbon atoms in the group is between 1 and 6.

[0060] (A) (Poly)alkylene glycol represented by formula (I) or its derivatives (mono or polyalkylene glycol and its derivatives, hereinafter also simply referred to as polyalkylene glycol derivatives)

[0061]

[0062] In formula (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, preferably a linear or branched alkyl group, or the formula -C(=O)-R 14 It is the basis of R 14 R is an alkyl group having 1 to 20 carbon atoms, preferably a linear or branched alkyl group. 13 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, preferably a linear or branched alkyl group, and n is an integer from 1 to 10. However, R 11 , and R 12 Both are -C(=O)-R 14 It is preferable to exclude the base of. Also, when n is 1, R11 and R 12 are preferably not both hydrogen atoms.

[0063] In formula (I), from the viewpoint of suppressing the formation of trimers, R 11 and R 12 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or a group of the formula -C(=O)-R 14 (where R 14 is a linear or branched alkyl group having 1 to 20 carbon atoms) is preferred, and R 11 and R 12 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, or a group of the formula -C(=O)-R 14 (where R 14 is a linear or branched alkyl group having 5 to 20 carbon atoms) is more preferred, and R 11 and R 12 are each independently a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms, or a group of the formula -C(=O)-R 14 (where R 14 is a linear or branched alkyl group having 10 to 20 carbon atoms) is even more preferred, and R 11 and R 12 are each independently a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms is even more preferred, and R 11 and R 12 are each independently a hydrogen atom or a methyl group is even more preferred. However, R 11 and R 12 are preferably not both a group of -C(=O)-R 14 . Also, when n = 1, it is preferred that R 11 and R 12 are not both hydrogen atoms. However, it is more preferred to exclude the case where all of R 11 , R 12 and R 13 are hydrogen and n = 2.

[0064] Here, examples of (linear or branched) alkyl groups having 1 to 20 carbon atoms include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, t-butyl group, n-pentyl group, i-pentyl group, sec-pentyl group, t-pentyl group, 2-methylbutyl group, n-hexyl group, 1-methylpentyl group, 1-ethylbutyl group, 2,2-dimethylbutyl group, n-heptyl group, 1-methylhexyl group, 2-ethylpentyl group, n-octyl group, 2-ethylhexyl group, n-nonyl group, n-decyl group, n-undecyl group, n-dodecyl group, n-tridecyl group, n-tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, n-nonadecyl group, eicosanyl group, and the like.

[0065] Examples of linear or branched alkyl groups having 1 to 5 carbon atoms include methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, sec-butyl group, t-butyl group, n-pentyl group, i-pentyl group, sec-pentyl group, t-pentyl group, 2-methylbutyl group, and the like.

[0066] The linear or branched alkyl groups having 1 to 3 carbon atoms are methyl, ethyl, n-propyl, and i-propyl groups. The same applies hereafter.

[0067] Furthermore, alkyl groups with 5 to 20 carbon atoms and alkyl groups with 10 to 20 carbon atoms can be selected from the alkyl groups exemplified above, corresponding to the number of carbon atoms.

[0068] In equation (I), R 13 From the viewpoint of suppressing trimer formation, hydrogen atoms or linear or branched alkyl groups having 1 to 3 carbon atoms are preferred, hydrogen atoms or methyl groups are more preferred, and methyl groups are even more preferred.

[0069] In formula (I), n is preferably an integer between 1 and 6, more preferably an integer between 1 and 5, even more preferably an integer between 1 and 4, or even more preferably an integer between 2 and 5, and even more preferably an integer between 2 and 4.

[0070] In equation (I), from the viewpoint of suppressing the generation of trimmers, R 11 and R 12 These are, independently of each other, a hydrogen atom or a linear or branched alkyl group having 1 to 5 carbon atoms or the formula -C(=O)-R 14 The basis (R 14 ( is a linear or branched alkyl group having 5 to 20 carbon atoms), R 13 is preferably a hydrogen atom or a C1 alkyl group, and n is preferably an integer between 1 and 5. However, when n is 1, R 11 and R 12 It is preferable that both are hydrogen atoms. Also, R 11 and R 12 Both are -C(=O)-R 14 It is preferable that it is not the base of.

[0071] In equation (I), from the viewpoint of suppressing the generation of trimmers, R 11 and R 12 These are, independently of each other, a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, or the formula -C(=O)-R 14 The basis (R 14 ( is a linear or branched alkyl group having 10 to 20 carbon atoms), R 13 is preferably a hydrogen atom or a C1 alkyl group, and n is preferably an integer between 1 and 5. However, when n is 1, R 11 and R 12 It is preferable that both are hydrogen atoms. Also, R 11 and R 12 Both are -C(=O)-R 14 It is preferable that it is not the base of.

[0072] In equation (I), from the viewpoint of suppressing the generation of trimmers, R 11 and R 12 One of them is equation -C(=O)-R 14 The basis (R 14( is a linear or branched alkyl group having 1 to 20 carbon atoms) or a linear or branched alkyl group having 1 to 3 carbon atoms, and the other is a hydrogen atom, R 13 n is preferably a hydrogen atom or an alkyl group having 1 carbon atom, and n is preferably an integer between 1 and 5.

[0073] In equation (I), from the viewpoint of suppressing the generation of trimmers, R 11 and R 12 One of them is equation -C(=O)-R 14 The basis (R 14 ( is a linear or branched alkyl group having 10 to 20 carbon atoms), and the other is a hydrogen atom, or a linear or branched alkyl group having 1 to 3 carbon atoms, R 13 n is preferably a hydrogen atom or an alkyl group having 1 carbon atom, and n is preferably an integer between 1 and 5.

[0074] In equation (I), from the viewpoint of suppressing the generation of trimmers, R 11 and R 12 R is a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, independently of each other. 13 n is preferably a hydrogen atom or an alkyl group having 1 carbon atom, and n is preferably an integer between 2 and 5.

[0075] In equation (I), from the viewpoint of suppressing the generation of trimmers, R 11 and R 12 R is a hydrogen atom. 13 n is preferably a hydrogen atom or a methyl group, and n is preferably an integer between 2 and 5.

[0076] In equation (I), from the viewpoint of suppressing the generation of trimmers, R 11 and R 12 One of them is equation -C(=O)-R 14 The basis (R 14 ( is a linear or branched alkyl group having 15 to 20 carbon atoms), and the other is a hydrogen atom, R 13 n is preferably a hydrogen atom or an alkyl group having 1 carbon atom, and n is preferably an integer between 1 and 4.

[0077] The polyalkylene glycol derivative represented by formula (I) is preferably polyethylene glycol or polypropylene glycol with a total of 5 to 30 carbon atoms, which may have an alkyl group having 1 to 5 carbon atoms and / or an acyl group having 2 to 21 carbon atoms, from the viewpoint of suppressing trimer formation; preferably polyethylene glycol or polypropylene glycol with a total of 5 to 20 carbon atoms, which may have an alkyl group having 1 to 3 carbon atoms; and preferably polyethylene glycol or polypropylene glycol with a total of 5 to 12 carbon atoms, which may have an alkyl group having 1 to 3 carbon atoms. Here, the total number of carbon atoms includes the number of carbon atoms in the alkyl group and acyl group.

[0078] Examples of polyalkylene glycol derivatives represented by formula (I) include triethylene glycol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, diethylene glycol diethyl ether, diethylene glycol monoethyl ether, propylene glycol monolaurate, propylene glycol monostearate, propylene glycol monopalmitate, and propylene glycol monooleate, among which triethylene glycol, dipropylene glycol, and dipropylene glycol monomethyl ether are included. It is preferable to include one or more selected from the group consisting of ether, dipropylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monolaurate, propylene glycol monostearate, and propylene glycol monopalmitate; more preferably to include one or more selected from the group consisting of triethylene glycol, dipropylene glycol, dipropylene glycol monomethyl ether, and diethylene glycol monomethyl ether; and even more preferably to include one or more selected from the group consisting of triethylene glycol and dipropylene glycol.

[0079]

[0080] (B) Sorbitan fatty acid esters having hydrocarbon groups with 7 to 21 carbon atoms. Sorbitan fatty acid esters having hydrocarbon groups with 7 to 21 carbon atoms are esters of a fatty acid of R-C(=O)OH (wherein R is a hydrocarbon group with 7 to 21 carbon atoms) and sorbitan (a mixture obtained by the dehydration reaction of sorbitol), that is, sorbitan fatty acid esters having fatty acid residues (acyl groups) with 8 to 22 carbon atoms.

[0081] The number of carbon atoms in the hydrocarbon group having 7 to 21 carbon atoms is preferably 9 or more, more preferably 11 or more, from the viewpoint of suppressing trimer formation, and similarly preferably 19 or less, more preferably 17 or less. Therefore, the number of carbon atoms in the hydrocarbon group is 7 to 21, preferably 9 to 19, and even more preferably 11 to 17. The number of carbon atoms in the fatty acid residue having 8 to 22 carbon atoms is preferably 10 to 20, more preferably 12 to 18, from the viewpoint of suppressing trimer formation. The hydrocarbon group and fatty acid residue may be linear or branched, and may be saturated or unsaturated.

[0082] Sorbitan fatty acid esters include sorbitan mono fatty acid esters, sorbitan di fatty acid esters, and sorbitan tri fatty acid esters, with the inclusion of sorbitan mono fatty acid esters being preferable. Sorbitan is a mixture of 1,4-anhydrosorbitol, 1,5-anhydrosorbitol, etc.

[0083] The hydrocarbon group of the sorbitan fatty acid ester (monoester, diester, triester) is an alkyl or alkenyl group having 7 to 21 carbon atoms, preferably 9 to 19 carbon atoms, and more preferably 11 to 17 carbon atoms, from the viewpoint of suppressing trimer formation. It is preferable that the sorbitan fatty acid ester (monoester, diester, triester) is an ester of sorbitan with one or more fatty acids selected from lauric acid, myristic acid, palmitic acid, stearic acid, and oleic acid.

[0084] Examples of sorbitan monofatty acid esters include sorbitan monolaurate, sorbitan monopalmitate, sorbitan monooleate, sorbitan monomyristate, sorbitan monostearate, and sorbitan monoisostearate, with sorbitan monolaurate, sorbitan monopalmitate, and sorbitan monooleate being preferred.

[0085] Examples of sorbitan trifatty acid esters include sorbitan trilaurate, sorbitan tripalmitate, sorbitan trioleate, sorbitan trimyristate, sorbitan trystearate, and sorbitan triisostearate, with sorbitan trystearate, sorbitan tripalmitate, and sorbitan trioleate being preferred.

[0086] (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms. A polyoxyethylene sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms is a polyoxyethylene sorbitan fatty acid ester having a fatty acid residue (acyl group) having 8 to 22 carbon atoms. For example, polyoxyethylene can be added to a sorbitan fatty acid ester. A polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms is a polyoxyethylene sorbitol fatty acid ester having a fatty acid residue (acyl group) having 8 to 22 carbon atoms. For example, sorbitol can be added to polyoxyethylene and esterified with a fatty acid of R-C(=O)OH (wherein R is a hydrocarbon group having 7 to 21 carbon atoms).

[0087] The number of carbon atoms in the hydrocarbon group having 7 to 21 carbon atoms is preferably 9 or more, more preferably 11 or more, and more preferably 19 or less, and more preferably 17 or less, from the viewpoint of suppressing trimer formation, for both polyoxyethylene sorbitan fatty acid esters and polyoxyethylene sorbitol fatty acid esters. Therefore, the number of carbon atoms in the hydrocarbon group is 7 to 21, preferably 9 to 19, and even more preferably 11 to 17. The number of carbon atoms in the fatty acid residue is preferably 8 to 22, more preferably 10 to 20, and even more preferably 12 to 18, from the viewpoint of suppressing trimer formation. The hydrocarbon group may be linear or branched, and may be saturated or unsaturated. The hydrocarbon group is preferably an alkyl group or an alkenyl group.

[0088] From the viewpoint of suppressing trimer formation, the average number of moles of polyoxyethylene added is preferably 3 or more, more preferably 4 or more, and from the same viewpoint, preferably 120 or less, more preferably 60 or less, and even more preferably 20 or less. From the same viewpoint, the average number of moles of polyoxyethylene added is preferably 3 or more and 120 or less, more preferably 3 or more and 60 or less, even more preferably 4 or more and 60 or less, and even more preferably 4 or more and 20 or less.

[0089] Polyoxyethylene sorbitan fatty acid esters include polyoxyethylene sorbitan mono fatty acid esters, polyoxyethylene sorbitan di fatty acid esters, polyoxyethylene sorbitan tri fatty acid esters, and polyoxyethylene sorbitan tetra fatty acid esters. From the viewpoint of suppressing trimer formation and availability, polyoxyethylene sorbitan mono fatty acid esters or polyoxyethylene sorbitan tri fatty acid esters are preferred.

[0090] Polyoxyethylene sorbitol fatty acid esters include polyoxyethylene sorbitol mono fatty acid esters, polyoxyethylene sorbitol di fatty acid esters, polyoxyethylene sorbitol tri fatty acid esters, and polyoxyethylene sorbitol tetra fatty acid esters. From the viewpoint of suppressing trimer formation and availability, polyoxyethylene sorbitol tetra fatty acid esters are preferred.

[0091] From the viewpoint of suppressing trimer formation, the number of carbon atoms in the hydrocarbon group of polyoxyethylene sorbitan fatty acid esters (monoesters, diesters, triesters, tetraesters) and the average number of moles of polyoxyethylene added are preferably 7 to 21 carbon atoms and 3 to 120 average moles added, more preferably 9 to 19 carbon atoms and 3 to 60 average moles added, even more preferably 11 to 17 carbon atoms and 4 to 60 average moles added, and even more preferably 11 to 17 carbon atoms and 4 to 20 average moles added.

[0092] Examples of polyoxyethylene sorbitan fatty acid monoesters include polyoxyethylene (4) sorbitan monolaurate, polyoxyethylene (6) sorbitan monolaurate, polyoxyethylene (20) sorbitan monolaurate (polysorbate 20), polyoxyethylene (40) sorbitan monolaurate, polyoxyethylene (6) sorbitan monomyristate, polyoxyethylene (20) sorbitan monomyristate, polyoxyethylene (40) sorbitan monomyristate, polyoxyethylene (6) sorbitan monopalmitate, polyoxyethylene (20) sorbitan monopalmitate (polysorbate 40), polyoxyethylene (40) sorbitan monopalmitate, polyoxyethylene (6) sorbitan monooleate, polyoxyethylene (20) sorbitan monooleate (polysorbate 80), polyoxyethylene (40) sorbitan monooleate, and polyoxyethylene (6) sorbitan mono Examples include stearate, polyoxyethylene (20) sorbitan monostearate (polysorbate 60), polyoxyethylene (40) sorbitan monostearate, polyoxyethylene (6) sorbitan monoisostearate, polyoxyethylene (20) sorbitan monoisostearate, and polyoxyethylene (40) sorbitan monoisostearate, with polyoxyethylene (4) sorbitan monolaurate, polyoxyethylene (20) sorbitan monolaurate (polysorbate 20), polyoxyethylene (20) sorbitan monopalmitate (polysorbate 40), polyoxyethylene (6) sorbitan monooleate, polyoxyethylene (20) sorbitan monooleate (polysorbate 80), polyoxyethylene (6) sorbitan monostearate, polyoxyethylene (20) sorbitan monostearate (polysorbate 60), and polyoxyethylene (20) sorbitan monoisostearate being preferred. (The number in parentheses is the average number of moles added. The same applies below.)

[0093] Examples of polyoxyethylene sorbitan trifatty acid esters include polyoxyethylene (20) sorbitan trilaurate, polyoxyethylene (20) sorbitan trimyristate, polyoxyethylene (20) sorbitan tripalmitate, polyoxyethylene (6) sorbitan trystearate, polyoxyethylene (20) sorbitan trystearate, polyoxyethylene (40) sorbitan trystearate, polyoxyethylene (20) sorbitan tryisostearate, polyoxyethylene (6) sorbitan trioleate, polyoxyethylene (20) sorbitan trioleate, and polyoxyethylene (40) sorbitan trioleate, with polyoxyethylene (20) sorbitan trystearate and polyoxyethylene (20) sorbitan trioleate being preferred.

[0094] From the viewpoint of suppressing trimer formation, the number of carbon atoms in the hydrocarbon group of polyoxyethylene sorbitol fatty acid esters (monoesters, diesters, triesters, tetraesters) and the average number of moles of polyoxyethylene added are preferably 7 to 21 carbon atoms and 3 to 120 average moles added, more preferably 9 to 19 carbon atoms and 3 to 60 average moles added, even more preferably 11 to 17 carbon atoms and 4 to 60 average moles added, and even more preferably 11 to 17 carbon atoms and 4 to 20 average moles added.

[0095] Examples of polyoxyethylene sorbitol tetra fatty acid esters include polyoxyethylene (60) sorbitol tetralaurate, polyoxyethylene (60) sorbitol tetramyristate, polyoxyethylene (60) sorbitol tetrapalmitate, polyoxyethylene (60) sorbitol tetrastearate, polyoxyethylene (60) sorbitol tetraisostearate, polyoxyethylene (20) sorbitol tetraoleate, polyoxyethylene (30) sorbitol tetraoleate, polyoxyethylene (40) sorbitol tetraoleate, and polyoxyethylene (60) sorbitol tetraoleate, with polyoxyethylene (30) sorbitol tetraoleate, polyoxyethylene (40) sorbitol tetraoleate, and polyoxyethylene (60) sorbitol tetraoleate being preferred.

[0096] (D) Amino acids represented by formula (II)

[0097]

[0098] In formula (II), R 41 This is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a heterocyclic group, an aromatic ring group, a COOH, NH2, or an alkyl group having 1 to 5 carbon atoms substituted with OH.

[0099] R 41 From the viewpoint of suppressing trimer formation, it is more preferable that the alkyl group is a hydrogen atom, a linear or branched alkyl group having 1 to 4 carbon atoms, or an alkyl group having 1 to 4 carbon atoms substituted with an indolyl group, a phenyl group, COOH, NH2, or OH.

[0100] A heterocyclic group is a compound with a cyclic structure containing oxygen, sulfur, nitrogen, etc., in addition to carbon. Examples include pyrrolyl, pyrrolinyl, imidazolyl, pyrazolyl, indolyl, isoindolyl, indolidinyl, benzimidazolyl, quinolyl, isoquinolyl, indazolyl, and benzotriazolylpyridyl.

[0101] Examples of amino acids represented by formula (II) include neutral amino acids such as glycine, alanine, leucine, isoleucine, phenylalanine, valine, threonine, serine, and tryptophan; basic amino acids such as lysine; and acidic amino acids such as aspartic acid and glutamic acid. From the viewpoint of suppressing trimer formation, neutral amino acids such as glycine, alanine, phenylalanine, isoleucine, tryptophan, and glutamic acid, as well as acidic amino acids, are preferred.

[0102]

[0103] (E) Anthranilate ester represented by formula (III)

[0104]

[0105] In formula (III), R 51 R is a hydrogen atom, a methyl group, or an ethyl group. 52 This is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms.

[0106] In equation (III), from the viewpoint of suppressing the generation of trimmers, R 52 The C1 is preferably a linear or branched alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 4 to 8 carbon atoms, more preferably a linear or branched alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 4 to 8 carbon atoms, and even more preferably a linear or branched alkyl group having 1 to 5 carbon atoms or a cycloalkyl group having 5 to 7 carbon atoms.

[0107] Examples of anthranilate esters represented by formula (III) include isobutyl anthranilate, dimethyl anthranilate, methyl anthranilate, cyclohexyl anthranilate, ethyl anthranilate, isopropyl anthranilate, menthyl anthranilate, octyl anthranilate, and lauryl anthranilate. From the viewpoint of suppressing trimer formation, isobutyl anthranilate, methyl N-methylanthranilate, methyl anthranilate, and cyclohexyl anthranilate are preferred.

[0108]

[0109] (F) Pyrazine derivative represented by formula (IV)

[0110]

[0111] In formula (IV), R 61 , R 62 , R 63 , and R 64 Each is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64 The total number of carbon atoms in the group is between 1 and 6.

[0112] Examples of pyrazine derivatives represented by formula (IV) include 2-ethyl-3,5-dimethylpyrazine, 2-ethyl-3-methylpyrazine, 2,3,5,6-tetramethylpyrazine, 2,3-dimethylpyrazine, 2,6-dimethylpyrazine, 2,5-dimethylpyrazine, 2,3,5-trimethylpyrazine, 2-ethylpyrazine, 2,3-diethyl-5-methylpyrazine, and 5-ethyl-2-methylpyrazine. From the viewpoint of suppressing trimer formation, 2-ethyl-3,5-dimethylpyrazine, 2-ethyl-3-methylpyrazine, and 2,3,5,6-tetramethylpyrazine are preferred.

[0113]

[0114] [Composition] The amount of additive relative to the mass of the aliphatic aldehyde having 8 to 16 carbon atoms is 100 ppm (mass ppm) or more, preferably 200 ppm or more, more preferably 500 ppm or more, and even more preferably 1,000 ppm or more, from the viewpoint of suppressing the formation of trimers, 1% by mass or less, preferably 6,000 ppm or less, more preferably 3,000 ppm or less, and even more preferably 2,000 ppm or less, from the viewpoint of considering the decrease in the purity of the aliphatic aldehyde, and from these viewpoints, 100 ppm or more and 1% by mass or less, preferably 200 ppm or more and 6,000 ppm or less, even more preferably 500 ppm or more and 3,000 ppm or less, and even more preferably 1,000 ppm or more and 2,000 ppm or less.

[0115] The amount of additive per 100 parts by mass of aliphatic aldehyde is preferably 0.01 parts by mass or more, more preferably 0.02 parts by mass or more, even more preferably 0.05 parts by mass or more, and even more preferably 0.1 parts by mass or more, from the viewpoint of suppressing the formation of trimers, preferably 1 part by mass or less, more preferably 0.6 parts by mass or less, even more preferably 0.3 parts by mass or less, and even more preferably 0.2 parts by mass or less, from the viewpoint of suppressing the decrease in the purity of aliphatic aldehyde, and from these viewpoints, preferably 0.01 parts by mass or more and 1 part by mass or less, more preferably 0.02 parts by mass or more and 0.6 parts by mass or less, even more preferably 0.05 parts by mass or more and 0.3 parts by mass or less, and even more preferably 0.1 parts by mass or more and 0.2 parts by mass or less.

[0116] In the composition, the aliphatic aldehyde content is 90% by mass or more, preferably 95% by mass or more, more preferably 96% by mass or more, and even more preferably 97% by mass or more, from the viewpoint of exhibiting an effect of suppressing trimer formation and from the viewpoint of using aliphatic aldehydes for other purposes. In the composition, the aliphatic aldehyde content is preferably 99.99% by mass or less, more preferably 99.95% by mass or less, even more preferably 99.9% by mass or less, and even more preferably 99.7% by mass or less. In the composition, the aliphatic aldehyde content is 90% by mass or more, preferably 90% by mass or more and 99.99% by mass or less, more preferably 95% by mass or more and 99.95% by mass or less, even more preferably 96% by mass or more and 99.9% by mass or less, and even more preferably 97% by mass or more and 99.7% by mass or less, from the viewpoint of exhibiting an effect of suppressing trimer formation and from the viewpoint of using aliphatic aldehydes for other purposes.

[0117] In the composition of the present invention, the content of the trimer derived from the aliphatic aldehyde is preferably 3% by mass or less, more preferably 1% by mass or less, even more preferably 0.5% by mass or less, and even more preferably 0.1% by mass or less, relative to the mass of the aliphatic aldehyde, from the viewpoint of maintaining transparency of appearance. In the composition of the present invention, the content of the trimer is preferably 0% by mass or more and 3% by mass or less, more preferably 0% by mass or more and 1% by mass or less, even more preferably 0% by mass or more and 0.5% by mass or even more preferably 0% by mass or more and 0.1% by mass or less, relative to the mass of the aliphatic aldehyde, from the viewpoint of maintaining transparency of appearance.

[0118] In the composition of the present invention, other components may be present in addition to the aliphatic aldehyde, the trimer, and the additive, as long as they do not impair the present invention. Examples of other components include aliphatic alcohols that serve as raw materials for producing the aliphatic aldehyde, fatty acids obtained by oxidizing the aliphatic aldehyde, esters, antioxidants, dyes, pH adjusters, and the like.

[0119] In the composition of the present invention, the content of trimer derived from the aliphatic aldehyde per 100 parts by mass of the aliphatic aldehyde is preferably 3 parts by mass or less, more preferably 1 part by mass or less, even more preferably 0.5 parts by mass or less, and even more preferably 0.1 parts by mass or less, from the viewpoint of suppressing the formation of trimer, and may be 0 parts by mass or more. In the composition of the present invention, the content of trimer is preferably 0 parts by mass or more and 3 parts by mass or less per 100 parts by mass of the aliphatic aldehyde, more preferably 0 parts by mass or more and 1 part by mass or less, even more preferably 0 parts by mass or more and 0.5 parts by mass or less, and even more preferably 0 parts by mass or more and 0.1 parts by mass or less.

[0120] [Inhibitor for the Formation of Trimers of Aliphatic Aldehydes Having 8 to 16 Carbon atoms] The present invention is an inhibitor for the formation of trimers of aliphatic aldehydes having 8 to 16 carbon atoms, comprising one or more additives selected from the group consisting of the following components (A) to (F). The additive may comprise one, two or more additives selected from the group consisting of the following components (A) to (F). The additive may be a combination of (A) a (poly)alkylene glycol or a derivative thereof represented by the following general formula (I) and (B) a sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms, or (B) a sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms and (C) a polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms.

[0121] (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I)

[0122]

[0123] [In formula (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the formula -C(=O)-R 14 It is the basis of R 14 R is an alkyl group having 1 to 20 carbon atoms. 13 (B) A hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is an integer from 1 to 10. (C) A sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) An amino acid represented by the following general formula (II)

[0124]

[0125] [In formula (II), R 41(E) Anthranilic acid ester represented by the following general formula (III)

[0126]

[0127] [In formula (III), R 51 R is a hydrogen atom, a methyl group, or an ethyl group. 52 (F) Pyrazine derivatives represented by the following general formula (IV)

[0128]

[0129] [In formula (IV), R 61 , R 62 , R 63 , and R 64 Each is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64 The total number of carbon atoms in the group is between 1 and 6.

[0130] The preferred embodiments of the compounds (A) to (F) described above are the same as the preferred embodiments of the compounds (A) to (F) described in the additive section.

[0131] [Method for suppressing trimmer formation] The present invention is a method for suppressing trimmer formation of an aliphatic aldehyde by mixing one or more additives selected from the group consisting of the following components (A) to (F) with an aliphatic aldehyde having 8 to 16 carbon atoms. Preferred embodiments of the compounds (A) to (F) are the same as preferred embodiments of the compounds (A) to (F) described in the additive section. The additive may contain one, two or more selected from the group consisting of the following components (A) to (F). The additive may be a combination of (A) a (poly)alkylene glycol or a derivative thereof represented by the following general formula (I) and (B) a sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms, or (B) a sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms and (C) a polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms. (A) a (poly)alkylene glycol or a derivative thereof represented by the following general formula (I)

[0132]

[0133] [In formula (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the formula -C(=O)-R 14 It is the basis of R 14 R is an alkyl group having 1 to 20 carbon atoms. 13 (B) A hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is an integer from 1 to 10. (C) A sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) An amino acid represented by the following general formula (II)

[0134]

[0135] [In formula (II), R 41(E) Anthranilic acid ester represented by the following general formula (III)

[0136]

[0137] [In formula (III), R 51 R is a hydrogen atom, a methyl group, or an ethyl group. 52 (F) Pyrazine derivatives represented by the following general formula (IV)

[0138]

[0139] [In formula (IV), R 61 , R 62 , R 63 , and R 64 Each is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64 The total number of carbon atoms in the group is between 1 and 6.

[0140] The amount of the aforementioned growth inhibitor used is, with respect to the mass of an aliphatic aldehyde having 8 to 16 carbon atoms, 100 ppm (mass ppm) or more, preferably 200 ppm or more, more preferably 500 ppm or more, and even more preferably 1000 ppm or more, from the viewpoint of suppressing trimer formation, 1% by mass or less, preferably 6000 ppm or less, more preferably 3000 ppm or less, and even more preferably 2000 ppm or less, from the viewpoint of considering the decrease in the purity of the aliphatic aldehyde, and from these viewpoints, 100 ppm or more and 1% by mass or less, preferably 200 ppm or more and 6000 ppm or less, more preferably 500 ppm or more and 3000 ppm or less, and even more preferably 1000 ppm or more and 2000 ppm or less. In this specification, ppm refers to mass ppm.

[0141] The amount of the growth inhibitor used per 100 parts by mass of the aliphatic aldehyde is preferably 0.01 parts by mass or more, more preferably 0.02 parts by mass or more, even more preferably 0.05 parts by mass or more, and even more preferably 0.1 parts by mass or more, from the viewpoint of suppressing the formation of trimers, preferably 1 part by mass or less, more preferably 0.6 parts by mass or less, even more preferably 0.3 parts by mass or less, and even more preferably 0.2 parts by mass or less, from these viewpoints, preferably 0.01 parts by mass or more and 1 part by mass or less, more preferably 0.02 parts by mass or more and 0.6 parts by mass or less, even more preferably 0.05 parts by mass or more and 0.3 parts by mass or less, and even more preferably 0.1 parts by mass or more and 0.2 parts by mass or less.

[0142] The present invention includes the following embodiments: [1] A composition comprising an aliphatic aldehyde having 8 to 16 carbon atoms and an additive, wherein the aliphatic aldehyde content is 90% by mass or more, the additive is one or more selected from the group consisting of the following components (A) to (F), and the content of the additive is 100 ppm to 1% by mass relative to the mass of the aliphatic aldehyde. (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I)

[0143]

[0144] [In formula (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the formula -C(=O)-R 14 It is the basis of R 14 R is an alkyl group having 1 to 20 carbon atoms. 13 (B) A hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is an integer from 1 to 10. (C) A sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) An amino acid represented by the following general formula (II)

[0145]

[0146] [In formula (II), R 41 (E) Anthranilic acid ester represented by the following general formula (III)

[0147]

[0148] [In formula (III), R 51 R is a hydrogen atom, a methyl group, or an ethyl group. 52 (F) Pyrazine derivatives represented by the following general formula (IV)

[0149]

[0150] [In formula (IV), R 61 , R 62 , R 63 , and R 64 Each is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64 The total number of carbon atoms in the group is between 1 and 6.

[0151] [2] The composition according to [1], wherein the aliphatic aldehyde preferably has 10 to 14 carbon atoms, more preferably 10 to 12 carbon atoms, and even more preferably 11 to 13 carbon atoms.

[0152] [3] The composition according to [1] or [2], wherein the aliphatic aldehyde content is 90% by mass or more, preferably 95% by mass or more.

[0153] [4] The composition according to any one of [1] to [3], wherein the amount of the additive relative to the mass of the aliphatic aldehyde is 100 ppm or more and 1% by mass or less, preferably 200 ppm or more and 6000 ppm or less, more preferably 500 ppm or more and 3000 ppm or less, and even more preferably 1000 ppm or more and 2000 ppm or less.

[0154] [5] The composition of the present invention, wherein the trimmer content is preferably 3% by mass or less, preferably 3% by mass or less but 0% by mass or more, more preferably 1% by mass or less but 0% by mass or more, even more preferably 0.5% by mass or less but 0% by mass or more, and even more preferably 0.1% by mass or less but 0% by mass or more, according to any one of [1] to [4].

[0155] [6] The composition according to any one of [1] to [5], wherein in formula (I), n is preferably an integer between 1 and 6, more preferably an integer between 1 and 5, even more preferably an integer between 1 and 4 or an integer between 2 and 5, and even more preferably an integer between 2 and 4.

[0156] [7] In equation (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, a linear or branched alkyl group having 1 to 20 carbon atoms, or the formula -C(=O)-R 14 The basis (R 14 The composition according to any one of [1] to [6], wherein is a linear or branched alkyl group having 1 to 20 carbon atoms.

[0157] [8] In equation (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, or the formula -C(=O)-R 14 The basis (R 14 The composition according to any one of [1] to [7], wherein is a linear or branched alkyl group having 5 to 20 carbon atoms.

[0158] [9] In equation (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, a linear or branched alkyl group having 1 to 3 carbon atoms, or the formula -C(=O)-R 14 The basis (R 14 The composition according to any one of [1] to [8], wherein is a linear or branched alkyl group having 10 to 20 carbon atoms.

[0159]

[10] In equation (I), R 11 and R 12The composition according to any one of [1] to [9], wherein each is independently a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms.

[0160]

[11] In equation (I), R 11 and R 12 The composition according to any one of [1] to

[10] , wherein each is independently a hydrogen atom or a methyl group.

[0161]

[12] In equation (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, or the formula -C(=O)-R 14 The basis (R 14 ( is a linear or branched alkyl group having 5 to 20 carbon atoms), R 13 R is a hydrogen atom or an alkyl group having 1 carbon atom, n is an integer between 1 and 5, except when n is 1. 11 and R 12 Except that both are hydrogen atoms, R 11 and R 12 Both are formula -C(=O)-R 14 A composition according to any one of [1] to

[11] , except that it is a base of [1].

[0162]

[13] In equation (I), R 11 and R 12 These are, independently of each other, a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, or the formula -C(=O)-R 14 The basis (R 14 ( is a linear or branched alkyl group having 10 to 20 carbon atoms), R 13 R is a hydrogen atom or an alkyl group having 1 carbon atom, n is an integer between 1 and 5, except when n is 1. 11 and R 12 Except that both are hydrogen atoms, R 11 and R 12 Both are -C(=O)-R 14 A composition according to any one of [1] to

[12] , except that it is a base of [1].

[0163]

[14] In equation (I), R 11 and R 12 One of them is equation -C(=O)-R 14 The basis (R 14 ( is a linear or branched alkyl group having 1 to 20 carbon atoms), or a linear or branched alkyl group having 1 to 3 carbon atoms, and the other is a hydrogen atom, R 13 The composition according to any one of [1] to

[13] , wherein is a hydrogen atom or an alkyl group having 1 carbon atom, and n is an integer between 1 and 5.

[0164]

[15] In equation (I), R 11 and R 12 One of them is equation -C(=O)-R 14 The basis (R 14 (where R is a linear or branched alkyl group having 10 to 20 carbon atoms) or a linear or branched alkyl group having 1 to 3 carbon atoms, and the other is a hydrogen atom. 13 The composition according to any one of [1] to

[14] , wherein is a hydrogen atom or an alkyl group having 1 carbon atom, and n is an integer between 1 and 5.

[0165]

[16] In equation (I), R 11 and R 12 One of them is equation -C(=O)-R 14 The basis (R 14 ( is a linear or branched alkyl group having 15 to 20 carbon atoms), and the other is a hydrogen atom, R 13 The composition according to any one of [1] to

[15] , wherein is a hydrogen atom or an alkyl group having 1 carbon atom, and n is an integer between 1 and 4.

[0166]

[17] In equation (I), R 11 and R 12 R is a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, independently of each other. 13 The composition according to any one of [1] to

[16] , wherein is a hydrogen atom or an alkyl group having 1 carbon atom, and n is an integer between 2 and 5.

[0167]

[18] In equation (I), R 11and R 12 R is a hydrogen atom. 13 The composition according to any one of [1] to

[17] , wherein is a hydrogen atom or a methyl group, and n is an integer between 2 and 5.

[0168]

[19] The composition according to any one of [1] to

[18] , wherein the compound of formula (I) has an alkyl group having 1 to 5 carbon atoms and / or an acyl group having 2 to 21 carbon atoms, and the total number of carbon atoms is 5 to 30 or less, as described in any of [1] to

[18] .

[0169]

[20] The composition according to any one of [1] to

[19] , wherein the compound of formula (I) may have an alkyl group having 1 to 3 carbon atoms, and is polyethylene glycol or polypropylene glycol having a total of 5 to 20 carbon atoms.

[0170]

[21] The composition according to any one of [1] to

[20] , wherein the compound of formula (I) may have an alkyl group having 1 to 3 carbon atoms, and is polyethylene glycol or polypropylene glycol having a total of 5 to 12 carbon atoms.

[0171]

[22] The composition according to any one of [1] to

[21] , wherein the compound of formula (I) is one or more selected from the group consisting of triethylene glycol, dipropylene glycol, dipropylene glycol monomethyl ether, dipropylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monolaurate, propylene glycol monostearate, and propylene glycol monopalmitate.

[0172]

[23] The composition according to any one of [1] to

[22] , wherein the compound of formula (I) is selected from the group consisting of triethylene glycol, dipropylene glycol, diethylene glycol monomethyl ether, and dipropylene glycol monomethyl ether.

[0173] The composition according to any one of [1] to

[23] , wherein the number of carbon atoms in the hydrocarbon group of the sorbitan fatty acid ester of

[24] (B) is 7 or more and 21 or less, preferably 9 or more and 19 or less, and more preferably 11 or more and 17 or less.

[0174] The composition according to any one of [1] to

[24] , wherein the sorbitan fatty acid ester of

[25] (B) is one or more selected from sorbitan mono fatty acid ester, sorbitan di fatty acid ester, and sorbitan tri fatty acid ester, and preferably sorbitan mono fatty acid ester.

[0175] The composition according to any one of [1] to

[25] , wherein the number of carbon atoms in the hydrocarbon group of the polyoxyethylene sorbitan fatty acid ester of

[26] (C) is 7 or more and 21 or less, preferably 9 or more and 19 or less, and more preferably 11 or more and 17 or less.

[0176] The composition according to any one of [1] to

[26] , wherein the average number of moles of oxyethylene added to the polyoxyethylene sorbitan fatty acid ester of

[27] (C) is preferably 3 or more and 120 or less, more preferably 3 or more and 60 or less, even more preferably 4 or more and 60 or less, and even more preferably 4 or more and 20 or less.

[0177] The composition according to any one of [1] to

[27] , wherein the polyoxyethylene sorbitan fatty acid ester of (C) is one or more selected from polyoxyethylene sorbitan mono fatty acid ester, polyoxyethylene sorbitan di fatty acid ester, polyoxyethylene sorbitan tri fatty acid ester, and polyoxyethylene sorbitan tetra fatty acid ester.

[0178] The composition according to any one of [1] to

[28] , wherein the number of carbon atoms in the hydrocarbon group of the polyoxyethylene sorbitol fatty acid ester of

[29] (C) is 7 or more and 21 or less, preferably 9 or more and 19 or less, and more preferably 11 or more and 17 or less.

[0179] The composition according to any one of [1] to

[29] , wherein the average number of moles of oxyethylene added to the polyoxyethylene sorbitol fatty acid ester of

[30] (C) is 3 or more and 120 or less, preferably 3 or more and 60 or less, more preferably 4 or more and 60 or less, and even more preferably 4 or more and 20 or less.

[0180] The composition according to any one of [1] to

[30] , wherein the polyoxyethylene sorbitol fatty acid ester of

[31] (C) is one or more selected from polyoxyethylene sorbitol mono fatty acid ester, polyoxyethylene sorbitol di fatty acid ester, polyoxyethylene sorbitol tri fatty acid ester, and polyoxyethylene sorbitol tetra fatty acid ester.

[0181]

[32] A trimer inhibitor for aliphatic aldehydes having 8 to 16 carbon atoms, comprising one or more additives selected from the group consisting of the following components (A) to (F): (A) (poly)alkylene glycol or derivative thereof represented by the following general formula (I).

[0182]

[0183] [In formula (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the formula -C(=O)-R 14 It is the basis of R 14 R is an alkyl group having 1 to 20 carbon atoms. 13 (B) A hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is an integer from 1 to 10. (C) A sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) An amino acid represented by the following general formula (II)

[0184]

[0185] [In formula (II), R 41(E) Anthranilic acid ester represented by the following general formula (III)

[0186]

[0187] [In formula (III), R 51 R is a hydrogen atom, a methyl group, or an ethyl group. 52 (F) Pyrazine derivatives represented by the following general formula (IV)

[0188]

[0189] [In formula (IV), R 61 , R 62 , R 63 , and R 64 Each is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64 The total number of carbon atoms in the group is between 1 and 6.

[0190]

[33] A method for suppressing trimer formation, comprising mixing one or more additives selected from the group consisting of the following components (A) to (F) with an aliphatic aldehyde having 8 to 16 carbon atoms. (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I).

[0191]

[0192] [In formula (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the formula -C(=O)-R 14 It is the basis of R 14 R is an alkyl group having 1 to 20 carbon atoms. 13(B) A hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is an integer from 1 to 10. (C) A sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) An amino acid represented by the following general formula (II)

[0193]

[0194] [In formula (II), R 41 (E) Anthranilic acid ester represented by the following general formula (III)

[0195]

[0196] [In formula (III), R 51 R is a hydrogen atom, a methyl group, or an ethyl group. 52 (F) Pyrazine derivatives represented by the following general formula (IV)

[0197]

[0198] [In formula (IV), R 61 , R 62 , R 63 , and R 64 Each is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64 The total number of carbon atoms in the group is 1 or more and 6 or less.

[34] A method for suppressing the formation of trimers of an aliphatic aldehyde having 8 or more carbon atoms according to

[33] , comprising mixing the additive in an amount of 100 ppm or more and 1% by mass or less, preferably 200 ppm or more and 6000 ppm or less, more preferably 500 ppm or more and 3000 ppm or less, and even more preferably 1000 ppm or more and 2000 ppm or less, relative to the mass of an aliphatic aldehyde having 8 or more carbon atoms.

[0199]

[35] Use of one or more additives selected from the group consisting of the following components (A) to (F) to suppress the formation of trimers of aliphatic aldehydes having 8 to 16 carbon atoms. (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I).

[0200]

[0201] [In formula (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the formula -C(=O)-R 14 It is the basis of R 14 R is an alkyl group having 1 to 20 carbon atoms. 13 (B) A hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is an integer from 1 to 10. (C) A sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) An amino acid represented by the following general formula (II)

[0202]

[0203] [In formula (II), R 41 (E) Anthranilic acid ester represented by the following general formula (III)

[0204]

[0205] [In formula (III), R 51 R is a hydrogen atom, a methyl group, or an ethyl group. 52 (F) Pyrazine derivatives represented by the following general formula (IV)

[0206]

[0207] [In formula (IV), R 61 , R 62 , R 63 , and R 64 Each is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64 The total number of carbon atoms in the group is between 1 and 6.

[0208] The present invention will be described in more detail below with reference to examples. In the following examples, the measurement and evaluation of each physical property was performed by the following methods.

[0209] <NMR equipment and analytical conditions> NMR equipment: Bruker ASCEND TM 400

[0210] Under the conditions of deuterated chloroform solvent, 400 MHz, 8 integration cycles, and 10-second relaxation time. 1 1H NMR measurements were performed.

[0211] [Examples and Comparative Examples] In the following examples and comparative examples, "%" refers to "mass%" unless otherwise specified. Also, "trimer" refers to 2,4,6-triundecyl-1,3,5-trioxane. The following raw materials were used in the reaction: ALDEHYDE C-12L (dodecanal purity 99%, no trimer, or dodecanal purity 97%, trimer 2.5%): Manufactured by Kao Corporation, containing 500 ppm α-tocopherol ALDEHYDE C-10 (Decanal purity 99%, no trimer): Manufactured by Kao Corporation Isopropyl myristate: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade Triethyl citrate: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade Triethylene glycol: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade Dipropylene glycol: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade Diethylene glycol dimethyl ether: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade Propylene glycol monostearate: Manufactured by Tokyo Chemical Industry Co., Ltd., reagent grade Diethylene glycol monomethyl ether: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade Sorbitan monolaurate: Manufactured by Kao Corporation, product name "Emazol L-10V" Sorbitan monopalmitate: Manufactured by Kao Corporation, product name "Emazol P-10V" Sorbitan monooleate: Manufactured by Kao Corporation, product name "Emazol O-10V" Sorbitan trioleate: Manufactured by Kao Corporation, product name "Leodol SP-O30V" Sorbitan tristearate: Manufactured by Kao Corporation, product name "Leodol SP-S30V" Polyoxyethylene (4) sorbitan monolaurate: Manufactured by Kao Corporation, product name "Leodol TW-L106" Polyoxyethylene (20) sorbitan monolaurate: Manufactured by Kao Corporation, product name "Leodol TW-L120" Polyoxyethylene (20) sorbitan monopalmitate: Manufactured by Kao Corporation, product name "Leodol TW-P120" Polyoxyethylene (6) sorbitan monostearate: Manufactured by Kao Corporation, product name "Leodol TW-S106V" Polyoxyethylene (20) sorbitan monostearate: Manufactured by Kao Corporation, product name "Leodol TW-S120V"Polyoxyethylene (20) sorbitan tristearate: Manufactured by Kao Corporation, product name "Leodol TW-S320V" Polyoxyethylene (6) sorbitan monooleate: Manufactured by Kao Corporation, product name "Leodol TW-O106V" Polyoxyethylene (20) sorbitan monooleate: Manufactured by Kao Corporation, product name "Leodol TW-O120V" Polyoxyethylene (20) sorbitan trioleate: Manufactured by Kao Corporation, product name "Leodol TW-O320V" Polyoxyethylene (20) sorbitan monoisostearate: Manufactured by Fujifilm Wako Chemical Co., Ltd. Polyoxyethylene (30) sorbitol tetraoleate: Manufactured by Kao Corporation, product name "Leodol 430V" Polyoxyethylene (40) sorbitol tetraoleate: Manufactured by Kao Corporation, product name "Leodol 440V" Polyoxyethylene (60) sorbitol tetraoleate: Manufactured by Kao Corporation, product name "Leodol 460V" Glycine: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade DL-alanine: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade DL-phenylalanine: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade DL-isoleucine: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade L-tryptophan: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade L-glutamic acid: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade Methyl anthranilate: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade N-methylanthranilate methyl: Manufactured by Tokyo Chemical Industry Co., Ltd., reagent grade Isobutyl anthranilate: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade Cyclohexyl anthranilate: Manufactured by Matrix Scientific 2-Ethyl-3-methylpyrazine: Manufactured by Fujifilm Wako Chemical Co., Ltd., reagent grade 2,3,5,6-tetramethylpyrazine: Manufactured by Tokyo Chemical Industry Co., Ltd., reagent grade 2-Ethyl-3,5-dimethylpyrazine: Manufactured by Tokyo Chemical Industry Co., Ltd., reagent grade

[0212] [Additives: None, Aldehyde: Dodecanal, Raw material aldehyde purity 99%, Solvent: Isopropyl myristate] <Test method 1> ALDEHYDE C-12L (dodecanal purity 99%, no trimer content) and isopropyl myristate, if necessary, were added to a 50 mL screw-cap tube to a total volume of 40 g, and the mixture was shaken to dissolve. The resulting composition was filled into a 9 mL screw-cap tube. This was placed in a plastic case and stored in a 5°C constant temperature bath for a specified time. After that, the composition was stored in a 60°C constant temperature bath for about 30 minutes to confirm that the entire mixture had melted and become liquid, then shaken to mix, and compositional analysis was performed by NMR analysis.

[0213] <Evaluation Method 1> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0214] The amounts of ALDEHYDE C-12L and isopropyl myristate used, the 5°C holding time, the composition of the composition before testing, and the mass ratio of dodecanal to trimer in the composition after testing are shown in Table 5 below.

[0215]

[0216] As can be seen from the comparison between Reference Example 1 and Comparative Example 1 in Table 5, it is clear that trimer formation is suppressed when the purity of the aliphatic aldehyde is low.

[0217] [Additives: None, Aldehyde: Dodecanal, Raw material aldehyde purity 97%, Solvent: Isopropyl myristate] <Test method 2> ALDEHYDE C-12L (containing 97% pure dodecanal and 2.5% trimer) and, if necessary, isopropyl myristate, were added to a 50 mL screw-cap tube to a total volume of 40 g, and the mixture was shaken to dissolve. The resulting composition was filled into a 9 mL screw-cap tube. This was placed in a plastic case and stored in a 5°C constant temperature bath for 72 hours. After that, the composition was stored in a 60°C constant temperature bath for about 30 minutes to confirm that the entire mixture had melted and become liquid, then shaken to mix, and the composition was analyzed by NMR analysis.

[0218] <Evaluation Method 2> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0219] The amounts of ALDEHYDE C-12L and isopropyl myristate used, the composition of the composition before testing, and the mass ratio of dodecanal to trimer in the composition after testing are shown in Table 6 below.

[0220]

[0221] From the comparison of Comparative Example 2 and Reference Example 2 in Table 6, it can be seen that a higher amount of trimmer before the test (before storage at 5°C) leads to an increase in the amount of trimmer after the test. Also, similar to Reference Example 1, it can be seen that lower purity of the aliphatic aldehyde suppresses the formation of trimmer.

[0222] As shown in Tables 5 and 6, it was confirmed that trimers are formed when dodecanal is stored at low temperatures for a long period of time and then melted, and that the amount of trimers formed increases with higher aliphatic aldehyde concentrations.

[0223] [Additives: Polyalkylene glycol derivative of formula (I), Aldehyde: Dodecanal, Raw material aldehyde purity 97%] <Test method 3> 40 g of ALDEHYDE C-12L (dodecanal purity 97%, containing 2.5% trimer) and the polyalkylene glycol derivative of formula (I) as an additive were placed in a 50 mL screw tube and shaken to dissolve. The resulting composition was packed into a 9 mL screw tube. This was placed in a plastic case and stored in a constant temperature bath at 5°C for 72 hours. After that, the composition was stored in a constant temperature bath at 60°C for about 30 minutes to confirm that the entire mixture had melted and become liquid, then shaken to mix, and compositional analysis was performed by NMR analysis.

[0224] <Evaluation Method 3> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0225] Table 7 below shows the types of additives used, the amount of additive relative to the mass of dodecanal, and the mass ratio of dodecanal to trimer in the composition after testing.

[0226]

[0227] As shown in Table 7, it was confirmed that the composition containing dodecanal and a polyalkylene glycol derivative of formula (I) suppresses trimer formation even when stored at low temperatures for a long period of time and then melted.

[0228] [Additives: Polyalkylene glycol derivative of formula (I), Aldehyde: Dodecanal, Raw material aldehyde purity 99%] <Test method 4> 40 g of ALDEHYDE C-12L (dodecanal purity 99%, no trimer) and the polyalkylene glycol derivative of formula (I) as an additive were placed in a 50 mL screw tube and shaken to dissolve. The obtained composition was filled into a 9 mL screw tube. This was placed in a plastic case and stored in a constant temperature bath at 5°C for 72 hours. In some examples, it was stored in a constant temperature bath at 5°C for 240 hours. After that, the composition was stored in a constant temperature bath at 60°C for about 30 minutes to confirm that the entire mixture had melted and become liquid, then shaken to mix, and compositional analysis was performed by NMR analysis.

[0229] <Evaluation Method 4> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0230] Table 8 below shows the types of additives used, the amount of additive relative to the mass of dodecanal, and the mass ratio of dodecanal to trimer in the composition after testing.

[0231]

[0232] As shown in Table 8, it was confirmed that the composition containing dodecanal and a polyalkylene glycol derivative of formula (I) suppresses trimer formation even when stored at low temperatures for a long period of time and then melted.

[0233] [Additives: Sorbitan fatty acid ester, Aldehyde: Dodecanal, Raw material aldehyde purity 97%] <Test method 5> 40 g of ALDEHYDE C-12L (containing 97% dodecanal purity and 2.5% trimer) and sorbitan fatty acid ester as an additive were placed in a 50 mL screw tube and shaken to dissolve. The resulting composition was filled into a 9 mL screw tube. This was placed in a plastic case and stored in a 5°C constant temperature bath for 72 hours. After that, the composition was stored in a 60°C constant temperature bath for about 30 minutes to confirm that the entire mixture had melted and become liquid, then shaken to mix, and compositional analysis was performed by NMR analysis.

[0234] <Evaluation Method 5> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0235] The types of additives used, the amount of additive relative to the mass of dodecanal, and the mass ratio of dodecanal to trimer in the composition after testing are shown in Table 9 below.

[0236]

[0237] As shown in Table 9, it was confirmed that the composition containing dodecanal and sorbitan fatty acid ester suppresses trimer formation even when stored at low temperatures for a long period of time and then melted.

[0238] [Additives: Sorbitan fatty acid ester, Aldehyde: Dodecanal, Raw material aldehyde purity 99%] <Test method 6> 40 g of ALDEHYDE C-12L (dodecanal purity 99%, no trimer content) and sorbitan fatty acid ester as an additive were placed in a 50 mL screw tube and shaken to dissolve. The resulting composition was filled into a 9 mL screw tube. This was placed in a plastic case and stored in a 5°C constant temperature bath for 240 hours. After that, the composition was stored in a 60°C constant temperature bath for about 30 minutes to confirm that the entire mixture had melted and become liquid, then shaken to mix, and compositional analysis was performed by NMR analysis.

[0239] <Evaluation Method 6> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0240] The types of additives used, the amount of additive relative to the mass of dodecanal, and the mass ratio of dodecanal to trimer in the composition after testing are shown in Table 10 below.

[0241]

[0242] As shown in Table 10, it was confirmed that the composition containing dodecanal and sorbitan fatty acid ester suppresses trimer formation even when stored at low temperatures for a long period of time and then melted.

[0243] [Additives: Polyoxyethylene sorbitan fatty acid ester, Aldehyde: Dodecanal, Raw material aldehyde purity 97%] <Test method 7> 40 g of ALDEHYDE C-12L (dodecanal purity 97%, containing 2.5% trimer) and polyoxyethylene sorbitan fatty acid ester as an additive were placed in a 50 mL screw tube and shaken to dissolve. The resulting composition was filled into a 9 mL screw tube. This was placed in a plastic case and stored in a 5°C constant temperature bath for 72 hours. After that, the composition was stored in a 60°C constant temperature bath for about 30 minutes to confirm that the entire mixture had melted and become liquid, then shaken to mix, and compositional analysis was performed by NMR analysis.

[0244] <Evaluation Method 7> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0245] The types of additives used, the amount of additive relative to the mass of dodecanal, and the mass ratio of dodecanal to trimer in the composition after testing are shown in Table 11 below.

[0246]

[0247] As shown in Table 11, it was confirmed that a composition containing dodecanal and a polyoxyethylene sorbitan fatty acid ester can suppress the formation of trimers even when stored at a low temperature for a long time and then melted.

[0248] [Additive: polyoxyethylene sorbitan fatty acid ester, polyoxyethylene sorbitol fatty acid ester, Aldehyde: dodecanal, raw material aldehyde purity 99%] <Test Method 8> 40 g of ALDEHYDE C-12L (dodecanal purity 99%, no trimer contained) and polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester as an additive were placed in a 50 mL screw tube and shaken to dissolve. The obtained composition was filled into a 9 mL screw tube. This was placed in a plastic case and stored in a constant temperature bath at 5°C for a predetermined time. Then, the composition was stored in a constant temperature bath at 60°C for about 30 minutes, and it was confirmed that the whole had melted and became liquid. It was shaken and mixed, and compositional analysis was performed by NMR analysis.

[0249] <Evaluation Method 8> 1 The composition after the test was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton (9.76 ppm, singlet) of dodecanal and the proton on the trioxane ring of the trimer (4.83 ppm, triplet).

[0250] The types of additives used, the amount of the additive relative to the mass of dodecanal, and the mass ratio of dodecanal to trimer in the composition after the test are shown in Tables 12 and 13 below.

[0251]

[0252]

[0253] As shown in Tables 12 and 13, it was confirmed that a composition containing dodecanal and a polyoxyethylene sorbitan fatty acid ester can suppress the formation of trimers even when stored at a low temperature for a long time and then melted.

[0254] [Additives: Amino acid represented by formula (II), Aldehyde: Dodecanal, Raw material aldehyde purity 97%] <Test method 9> 40 g of ALDEHYDE C-12L (dodecanal purity 97%, containing 2.5% trimer) and the amino acid represented by formula (II) as an additive were placed in a 50 mL screw tube and shaken to dissolve. The resulting composition was packed into a 9 mL screw tube. This was placed in a plastic case and stored in a 5°C constant temperature bath for 72 hours. After that, the composition was stored in a 60°C constant temperature bath for about 30 minutes to confirm that the entire mixture had melted and become liquid, then shaken to mix, and compositional analysis was performed by NMR analysis.

[0255] <Evaluation Method 9> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0256] The types of additives used, the amount of additive relative to the mass of dodecanal, and the mass ratio of dodecanal to trimer in the composition after testing are shown in Table 14 below.

[0257]

[0258] As shown in Table 14, it was confirmed that the composition containing dodecanal and the amino acid represented by formula (II) suppresses trimer formation even when stored at low temperatures for a long period of time and then melted.

[0259] [Additives: Amino acid represented by formula (II), Aldehyde: Dodecanal, Raw material aldehyde purity 99%] <Test method 10> 40 g of ALDEHYDE C-12L (dodecanal purity 99%, no trimer content) and the amino acid represented by formula (II) as an additive were placed in a 50 mL screw tube and shaken to dissolve. The resulting composition was packed into a 9 mL screw tube. This was placed in a plastic case and stored in a 5°C constant temperature bath for 72 hours and 240 hours. After that, the composition was stored in a 60°C constant temperature bath for about 30 minutes to confirm that the entire mixture had melted and become liquid, then shaken to mix, and compositional analysis was performed by NMR analysis.

[0260] <Evaluation Method 10> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0261] The types of additives used, the amount of additive relative to the mass of dodecanal, and the mass ratio of dodecanal to trimer in the composition after testing are shown in Table 15 below.

[0262]

[0263] As shown in Table 15, it was confirmed that the composition containing dodecanal and the amino acid represented by formula (II) suppresses trimer formation even when stored at low temperatures for a long period of time and then melted.

[0264] [Additives: Anthranilic acid ester represented by formula (III), Aldehyde: Dodecanal, Raw material aldehyde purity 97%] <Test method 11> 40 g of ALDEHYDE C-12L (dodecanal purity 97%, containing 2.5% trimer) and the anthranilic acid ester represented by formula (III) as an additive were placed in a 50 mL screw tube and shaken to dissolve. The resulting composition was packed into a 9 mL screw tube. This was placed in a plastic case and stored in a constant temperature bath at 5°C for 72 hours. After that, the composition was stored in a constant temperature bath at 60°C for about 30 minutes to confirm that the entire mixture had melted and become liquid, then shaken to mix, and compositional analysis was performed by NMR analysis.

[0265] <Evaluation Method 11> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0266] The types of additives used, the amount of additive relative to the mass of dodecanal, and the mass ratio of dodecanal to trimer in the composition after testing are shown in Table 16 below.

[0267]

[0268] As shown in Table 16, it was confirmed that the composition containing dodecanal and the anthranilic acid ester represented by formula (III) suppresses trimer formation even when stored at low temperatures for a long period of time and subsequently melted.

[0269] [Additives: Anthranilic acid ester represented by formula (III), Aldehyde: Dodecanal, Raw material aldehyde purity 99%] <Test method 12> 40 g of ALDEHYDE C-12L (dodecanal purity 99%, no trimer content) and the anthranilic acid ester represented by formula (III) as an additive were placed in a 50 mL screw tube and dissolved by shaking. The obtained composition was packed into a 9 mL screw tube. This was placed in a plastic case and stored in a 5°C constant temperature bath for 72 hours or 240 hours. After that, the composition was stored in a 60°C constant temperature bath for about 30 minutes to confirm that the entire mixture had melted and become liquid, mixed by shaking, and compositional analysis was performed by NMR analysis.

[0270] <Evaluation Method 12> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0271] Table 17 below shows the types of additives used, the amount of additive relative to the mass of dodecanal, and the mass ratio of dodecanal to trimer in the composition after testing.

[0272]

[0273] As shown in Table 17, it was confirmed that the composition containing dodecanal and the anthranilic acid ester represented by formula (III) suppresses trimer formation even when stored at low temperatures for a long period of time and then melted.

[0274] [Additives: Pyrazine derivative represented by formula (IV), Aldehyde: Dodecanal, Raw material aldehyde purity 97%] <Test method 13> 40 g of ALDEHYDE C-12L (dodecanal purity 97%, containing 2.5% trimer) and the pyrazine derivative represented by formula (IV) as an additive were placed in a 50 mL screw tube and shaken to dissolve. The obtained composition was packed into a 9 mL screw tube. This was placed in a plastic case and stored in a constant temperature bath at 5°C for 72 hours. After that, the composition was stored in a constant temperature bath at 60°C for about 30 minutes to confirm that the entire mixture had melted and become liquid, then shaken to mix, and compositional analysis was performed by NMR analysis.

[0275] <Evaluation Method 13> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0276] The types of additives used, the amount of additive relative to the mass of dodecanal, and the mass ratio of dodecanal to trimer in the composition after testing are shown in Table 18 below.

[0277]

[0278] As shown in Table 18, it was confirmed that the composition containing dodecanal and the pyrazine derivative represented by formula (IV) suppresses trimer formation even when stored at low temperatures for a long period of time and then melted.

[0279] [Additive: pyrazine derivative represented by formula (IV), Aldehyde: dodecanal, Raw material aldehyde purity 99%] <Test method 14> 40 g of ALDEHYDE C-12L (dodecanal purity 99%, no trimer contained) and a pyrazine derivative represented by formula (IV) as an additive were placed in a 50 mL screw tube and shaken to dissolve. The resulting composition was filled into a 9 mL screw tube. This was placed in a plastic case and stored in a constant temperature bath at 5°C for 72 hours or 240 hours. Then, the composition was stored in a constant temperature bath at 60°C for about 30 minutes, confirmed that the whole had melted and became liquid, shaken and mixed, and subjected to composition analysis by NMR analysis.

[0280] <Evaluation method 14> 1 The composition after the test was measured by 1H NMR analysis, and the mass ratio of dodecanal to the trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of the trimer (4.83 ppm, triplet).

[0281] The type of additive used, the amount of the additive relative to the mass of dodecanal, and the mass ratio of dodecanal to the trimer in the composition after the test are shown in Table 19 below.

[0282]

[0283] As shown in Table 19, it was confirmed that the composition containing dodecanal and the pyrazine derivative represented by formula (IV) could suppress trimer formation even when stored at a low temperature for a long time and then melted.

[0284] [Additives: Polyalkylene glycol derivative of formula (I), sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, aldehyde: dodecanal, raw material aldehyde purity 99%] <Test method 15> 40 g of ALDEHYDE C-12L (dodecanal purity 99%, no trimer) and the additives of a polyalkylene glycol derivative of formula (I) and sorbitan fatty acid ester, a polyalkylene glycol derivative of formula (I) and polyoxyethylene sorbitan fatty acid ester, or sorbitan fatty acid ester and polyoxyethylene sorbitan fatty acid ester were placed in a 50 mL screw tube and dissolved by shaking. The obtained composition was filled into a 9 mL screw tube. This was placed in a plastic case and stored in a constant temperature bath at 5°C for 240 hours. After that, the composition was stored in a constant temperature bath at 60°C for about 30 minutes to confirm that the entire mixture had melted and become liquid, mixed by shaking, and compositional analysis was performed by NMR analysis.

[0285] <Evaluation Method 15> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of dodecanal to trimer was determined from the area ratio of the aldehyde proton of dodecanal (9.76 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0286] The types of additives used, the amount of additive relative to the mass of dodecanal, and the mass ratio of dodecanal to trimer in the composition after testing are shown in Table 20 below.

[0287]

[0288] As shown in Table 20, it was confirmed that the composition containing dodecanal and multiple additives suppressed trimer formation even when stored at low temperatures for a long period of time and then melted.

[0289] [Additives: Sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, Aldehyde: Decanal, Raw material aldehyde purity 99%] <Test method 16> 40 g of ALDEHYDE C-10 (decanal purity 99%, no trimer content) and sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester as an additive were placed in a 50 mL screw tube and shaken to dissolve. The resulting composition was filled into a 9 mL screw tube. This was placed in a plastic case and stored in a -20°C constant temperature bath for 240 hours. After that, the composition was stored in a 60°C constant temperature bath for about 30 minutes to confirm that the entire mixture had melted and become liquid, then shaken to mix, and compositional analysis was performed by NMR analysis.

[0290] <Evaluation Method 16> 1 The composition after testing was measured by 1H NMR analysis, and the mass ratio of decanal to trimer was determined from the area ratio of the aldehyde proton of decanal (9.77 ppm, singlet) and the proton on the trioxane ring of trimer (4.83 ppm, triplet).

[0291] The types of additives used, the amount of additive relative to the mass of decanal, and the mass ratio of decanal to trimer in the composition after testing are shown in Table 21 below.

[0292]

[0293] As shown in Table 21, it was confirmed that the composition containing decanal and additives suppressed trimer formation even when stored at low temperatures for a long period of time and then melted.

[0294] As shown above, it has been confirmed that the aliphatic aldehyde contained in the composition of the present invention is stable.

Claims

1. A composition comprising an aliphatic aldehyde having 8 to 16 carbon atoms and an additive, wherein the content of the aliphatic aldehyde is 90% by mass or more, the additive is one or more selected from the group consisting of the following components (A) to (F), and the content of the additive is 100 ppm or more and 1% by mass or less based on the mass of the aliphatic aldehyde. (A) (Poly)alkylene glycol represented by the following general formula (I) or a derivative thereof [In formula (I), R 11 and R 12 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a group of the formula -C(=O)-R 14 , R 14 is an alkyl group having 1 to 20 carbon atoms, R 13 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is an integer of 1 to 10. ] (B) A sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms, (C) A polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) An amino acid represented by the following general formula (II) [In formula (II), R 41 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms substituted with a heterocyclic group, an aromatic ring group, COOH, NH2 or OH. ] (E) An anthranilic acid ester represented by the following general formula (III) [In formula (III), R 51 is a hydrogen atom, a methyl group or an ethyl group, and R 52 is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. ] (F) A pyrazine derivative represented by the following general formula (IV) [In formula (IV), R 61 , R 62 , R 63 , and R 64 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64 The total number of carbon atoms in the group is between 1 and 6.

2. In equation (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, a linear or branched alkyl group having 1 to 5 carbon atoms, or the formula -C(=O)-R 14 The basis (R 14 ( is a linear or branched alkyl group having 5 to 20 carbon atoms), R 13 R is a hydrogen atom or an alkyl group having 1 carbon atom, n is an integer between 1 and 5, except when n is 1. 11 and R 12 Except that both are hydrogen atoms, R 11 and R 12 Both are formula -C(=O)-R 14 The composition according to claim 1, except that it is a base of 3. In equation (I), R 11 and R 12 One of them is equation -C(=O)-R 14 The basis (R 14 ( is a linear or branched alkyl group having 1 to 20 carbon atoms) or a linear or branched alkyl group having 1 to 3 carbon atoms, and the other is a hydrogen atom, R 13 The composition according to claim 1, wherein is a hydrogen atom or an alkyl group having 1 carbon atom, and n is an integer between 1 and 5.

4. In equation (I), R 11 and R 12 R is a hydrogen atom or a linear or branched alkyl group having 1 to 3 carbon atoms, independently of each other. 13 The composition according to claim 1, wherein n is a hydrogen atom or an alkyl group having 1 carbon atom, and n is an integer between 2 and 5.

5. The composition according to any one of claims 1 to 4, wherein the compound of formula (I) comprises one or more selected from the group consisting of triethylene glycol, dipropylene glycol, diethylene glycol monomethyl ether, and dipropylene glycol monomethyl ether.

6. The composition according to claim 1, wherein the sorbitan fatty acid ester of (B) comprises a sorbitan mono fatty acid ester.

7. The composition according to claim 1, wherein the sorbitan fatty acid ester of (B) has a hydrocarbon group having 11 or more carbon atoms and 17 or fewer carbon atoms.

8. The composition according to claim 1, wherein the average number of moles of oxyethylene added to the polyoxyethylene sorbitan fatty acid ester and polyoxyethylene sorbitol fatty acid ester of (C) is 3 or more and 120 or less.

9. The composition according to claim 1, wherein the content of the additive is 200 ppm or more and 6,000 ppm or less relative to the mass of the aliphatic aldehyde.

10. The composition according to claim 1, wherein the aliphatic aldehyde content is 95% by mass or more.

11. The composition according to claim 1, wherein the amount of trimer derived from the aliphatic aldehyde is 3 parts by mass or less per 100 parts by mass of the aliphatic aldehyde.

12. The composition according to claim 1, wherein the aliphatic aldehyde has 10 or more carbon atoms and 12 or fewer carbon atoms.

13. An inhibitor for suppressing the formation of a trimer of an aliphatic aldehyde having 8 to 16 carbon atoms, which contains one or more additives selected from the group consisting of the following components (A) to (F). (A) (Poly)alkylene glycol represented by the following general formula (I) or a derivative thereof [In the formula (I), R 11 and R 12 are each independently a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a group of the formula -C(=O)-R 14 , R 14 is an alkyl group having 1 to 20 carbon atoms, R 13 is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is an integer of 1 to 10. ] (B) Sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) Amino acid represented by the following general formula (II) [In the formula (II), R 41 is a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or an alkyl group having 1 to 5 carbon atoms substituted with a heterocyclic group, an aromatic ring group, COOH, NH2 or OH. ] (E) Anthranilic acid ester represented by the following general formula (III) [In the formula (III), R 51 is a hydrogen atom, a methyl group or an ethyl group, and R 52 is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. ] (F) Pyrazine derivative represented by the following general formula (IV) [In the formula (IV), R 61 , R 62 , R 63 , and R 64 are each independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that the total number of carbon atoms of the groups of R 61 , R 62 , R 63 , and R 64 is 1 to 6. ] 14. A method for suppressing the formation of trimers of an aliphatic aldehyde, comprising mixing one or more additives selected from the group consisting of the following components (A) to (F) with an aliphatic aldehyde having 8 to 16 carbon atoms. (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I). [In formula (I), R 11 and R 12 These are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or the formula -C(=O)-R 14 It is the basis of R 14 R is an alkyl group having 1 to 20 carbon atoms. 13 (B) A hydrogen atom or an alkyl group having 1 to 3 carbon atoms, and n is an integer from 1 to 10. (C) A sorbitan fatty acid ester having a hydrocarbon group having 7 to 21 carbon atoms (D) An amino acid represented by the following general formula (II) [In formula (II), R 41 (E) Anthranilic acid ester represented by the following general formula (III) [In formula (III), R 51 R is a hydrogen atom, a methyl group, or an ethyl group. 52 (F) Pyrazine derivatives represented by the following general formula (IV) [In formula (IV), R 61 , R 62 , R 63 , and R 64 Each is independently a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, provided that R 61 , R 62 , R 63 , and R 64 The total number of carbon atoms in the group is between 1 and 6.

15. The method for suppressing trimer formation according to claim 14, wherein the additive is mixed with an aliphatic aldehyde having 8 to 16 carbon atoms in an amount of 100 ppm to 1% by mass.

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