Aliphatic aldehyde composition
A composition with specific additives stabilizes high-concentration aliphatic aldehydes by preventing trimer formation, ensuring purity and clarity across temperature variations.
Patent Information
- Authority / Receiving Office
- JP · JP
- Patent Type
- Applications
- Current Assignee / Owner
- KAO CORP
- Filing Date
- 2025-09-26
- Publication Date
- 2026-06-29
AI Technical Summary
Existing methods fail to stabilize aliphatic aldehydes at high concentrations (90% by mass or more) at low temperatures, leading to trimer formation and purity loss.
A composition comprising aliphatic aldehydes with 8 to 16 carbon atoms and specific additives such as (poly)alkylene glycol derivatives, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, amino acids, anthranilic acid esters, and pyrazine derivatives, which suppress trimer formation.
The composition effectively prevents trimer formation in high-concentration aliphatic aldehydes at low temperatures, maintaining purity and clarity upon temperature change.
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Figure 2026106381000003
Abstract
Description
[Technical Field]
[0001] This invention relates to aliphatic aldehyde compositions. [Background technology]
[0002] It has long been known that aliphatic aldehydes are easily oxidized. For example, Patent Document 1 reports a method for stabilizing 36% aqueous formaldehyde by adding guanamine.
[0003] Furthermore, Patent Document 2 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 it and fatty acids, and derivatives made from each thereof.
[0004] Furthermore, Patent Document 3 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, Patent Document 4 describes the addition of alkali metal hydroxides, alkaline earth metal hydroxides, alkali metal carbonates, alkaline earth metal carbonates, or alkaline earth metal carboxylates to aliphatic C3-C3 metals. 14 Methods for stabilizing aldehydes have been reported. [Prior art documents] [Patent Documents]
[0006] [Patent Document 1] Special Public Notice No. 40-90 [Patent Document 2] Special Public Service Publication No. 37-4109 [Patent Document 3] Special Publication 2010-523600 [Patent Document 4] Japanese Patent Publication No. 11-246461 [Overview of the project] [Problems that the invention aims to solve]
[0007] Patent documents 1 and 2 disclose methods for suppressing the aggregation of formalin at a concentration of 37% at room temperature. Furthermore, Patent Document 3 discloses the stability of low concentrations of aliphatic aldehydes up to 25% at room temperature or 40°C. Patent Document 4 discloses the long-term storage stability of aliphatic aldehydes at room temperature.
[0008] The present invention aims to provide a composition that can suppress trimer formation even when storing aliphatic aldehydes at a high concentration of 90% by mass or more at low temperatures. [Means for solving the problem]
[0009] 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, 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): A composition in which the content of the additive is 100 ppm or more and 1% by mass or less relative to the mass of the aliphatic aldehyde. (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I)
[0010] [ka]
[0011] [In formula (I), R 11 and R 12 are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a group of the formula -C(=O)-R 14 where 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 with 7 to 21 carbon atoms (C) A polyoxyethylene sorbitan fatty acid ester or a polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms, (D) An amino acid represented by the following general formula (II)
[0012] [Chemical formula]
[0013] [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)
[0014] [Chemical formula]
[0015] [In formula (III), R 51 is a hydrogen atom, a methyl group or an ethyl group, 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)
[0016] [ka]
[0017] [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.
[0018] (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)
[0019] [ka]
[0020] [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 This is an alkyl group having 1 to 20 carbon atoms. R 13 This is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. n is an integer between 1 and 10 (inclusive). (B) Sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (D) Amino acids represented by the following general formula (II)
[0021] [ka]
[0022] [In formula (II), R 41 This refers to 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. (E) Anthranilate esters represented by the following general formula (III)
[0023] [ka]
[0024] [In formula (III), R 51 is a hydrogen atom, a methyl group, or an ethyl group. R 52 This is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. (F) Pyrazine derivatives represented by the following general formula (IV)
[0025] [ka]
[0026] [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.
[0027] (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 components (A) to (F) below with an aliphatic aldehyde having 8 to 16 carbon atoms. (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I)
[0028] [ka] [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 This is an alkyl group having 1 to 20 carbon atoms. R 13 This is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. n is an integer between 1 and 10 (inclusive). (B) Sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (D) Amino acids represented by the following general formula (II)
[0029] [ka]
[0030] [In formula (II), R 41 This refers to 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. (E) Anthranilate esters represented by the following general formula (III)
[0031] [ka]
[0032] [In formula (III), R 51 is a hydrogen atom, a methyl group, or an ethyl group. R 52 This is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. (F) Pyrazine derivatives represented by the following general formula (IV)
[0033] [ka]
[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 64 The total number of carbon atoms in the group is between 1 and 6. [Effects of the Invention]
[0035] The composition and method of the present invention can suppress trimer formation even when storing aliphatic aldehydes with 8 to 16 carbon atoms at a high concentration of 90% by mass or more at low temperatures. [Modes for carrying out the invention]
[0036] The inventors of this 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.
[0037] 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.
[0038] Furthermore, as described in Japanese Patent Publication No. 59-51231, trimmer is a cyclic substance with a 6-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.
[0039] <Aliphatic aldehydes with 8 to 16 carbon atoms> In the present invention, the aliphatic aldehyde having 8 to 16 carbon atoms may be linear or branched, and may be saturated or unsaturated. The aliphatic aldehyde having 8 to 16 carbon atoms is preferably a linear aliphatic saturated primary aldehyde.
[0040] 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.
[0041] Specifically, the 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), and cis-3-dodecenal. Examples include decenal (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 with 8 to 16 carbon atoms, more preferably 10 to 14 carbon atoms, and even more preferably 11 to 13 carbon atoms.
[0042] <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.
[0043] (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I)
[0044] [ka]
[0045] [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 This is an alkyl group having 1 to 20 carbon atoms. R 13 This is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. n is an integer between 1 and 10 (inclusive). (B) Sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (D) Amino acids represented by the following general formula (II)
[0046] [ka]
[0047] [In formula (II), R 41 This refers to 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. (E) Anthranilate esters represented by the following general formula (III)
[0048] [ka]
[0049] [In formula (III), R 51 is a hydrogen atom, a methyl group, or an ethyl group. R 52 This is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. and (F) Pyrazine derivatives represented by the following general formula (IV)
[0050] [ka]
[0051] [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.
[0052] (A) (Poly)alkylene glycol represented by formula (I) or its derivatives (mono or polyalkylene glycol and their derivatives, hereinafter also simply referred to as polyalkylene glycol derivatives)
[0053] [ka]
[0054] 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 a group of the formula -C(=O)-R 14 It is the basis of R 14 This is an alkyl group having 1 to 20 carbon atoms, preferably a linear or branched alkyl group. R 13 This is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, preferably a linear or branched alkyl group. n is an integer between 1 and 10 (inclusive). However, R 11 , and R 12 Both are -C(=O)-R 14It is preferably excluded that it is a group of. Further, when n is 1, it is preferably excluded that both R 11 and R 12 are hydrogen atoms.
[0055] 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), 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 preferable, 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 preferable, 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 preferably, R 11 and R 12 are each independently a hydrogen atom or a methyl group is even more preferably. However, it is preferably excluded that both R 11 and R 12 are groups of -C(=O)-R 14 . Further, when n is 1, it is preferably excluded that both R 11 and R 12 are hydrogen atoms. However, R11 , R 12 and R 13 are all hydrogen, and it is more preferable to exclude the case where n = 2.
[0056] Here, examples of the (linear or branched) alkyl group 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, icosanyl group, etc.
[0057] Examples of the linear or branched alkyl group 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, etc.
[0058] Examples of the linear or branched alkyl group having 1 to 3 carbon atoms include methyl group; ethyl group; n-propyl group, i-propyl group. The same applies hereinafter.
[0059] In addition, the alkyl group having 5 to 20 carbon atoms and the alkyl group having 10 to 20 carbon atoms can be respectively selected from those corresponding to the carbon number among the alkyl groups exemplified above.
[0060] In formula (I), R 13From the viewpoint of suppressing trimer formation, hydrogen atoms or linear or branched alkyl groups with 1 to 3 carbon atoms are preferred, hydrogen atoms or methyl groups are more preferred, and methyl groups are even more preferred.
[0061] 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.
[0062] 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 base (R 14 (This is a linear or branched alkyl group having 5 to 20 carbon atoms.) R 13 is a hydrogen atom or a C1 alkyl group, It is preferable that n is an integer between 1 and 5, inclusive. 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.
[0063] 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 base (R 14 (This is a linear or branched alkyl group having 10 to 20 carbon atoms.) R 13 is a hydrogen atom or a C1 alkyl group, It is preferable that n is an integer between 1 and 5, inclusive. 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.
[0064] 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 base (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 is a hydrogen atom or a C1 alkyl group, It is preferable that n is an integer between 1 and 5, inclusive.
[0065] 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 base (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 is a hydrogen atom or a C1 alkyl group, It is preferable that n is an integer between 1 and 5, inclusive.
[0066] In equation (I), from the viewpoint of suppressing the generation of trimmers, R 11 and R 12 These are, independently of each other, hydrogen atoms or linear or branched alkyl groups having 1 to 3 carbon atoms. R 13is a hydrogen atom or a C1 alkyl group, It is preferable that n is an integer between 2 and 5, inclusive.
[0067] In equation (I), from the viewpoint of suppressing the generation of trimmers, R 11 and R 12 It is a hydrogen atom, R 13 is a hydrogen atom or a methyl group, It is preferable that n is an integer between 2 and 5, inclusive.
[0068] 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 base (R 14 ( is a linear or branched alkyl group having 15 to 20 carbon atoms), and the other is a hydrogen atom. R 13 is a hydrogen atom or a C1 alkyl group, It is preferable that n is an integer between 1 and 4, inclusive.
[0069] 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 and acyl groups.
[0070] 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.
[0071] [Table 1]
[0072] (B) Sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. A sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms is an ester of a fatty acid of RC(=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, a sorbitan fatty acid ester having a fatty acid residue (acyl group) with 8 to 22 carbon atoms.
[0073] 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.
[0074] 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.
[0075] The hydrocarbon group of sorbitan fatty acid esters (monoesters, diesters, triesters) 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 the formation of trimers. 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.
[0076] 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.
[0077] 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.
[0078] (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. A polyoxyethylene sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms is a polyoxyethylene sorbitan fatty acid ester having a fatty acid residue (acyl group) with 8 to 22 carbon atoms. For example, this can be achieved by adding polyoxyethylene to a sorbitan fatty acid ester. A polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms is a polyoxyethylene sorbitol fatty acid ester having a fatty acid residue (acyl group) with 8 to 22 carbon atoms. For example, this can be achieved by adding polyoxyethylene to sorbitol and esterifying it with a fatty acid of RC(=O)OH (where R is a hydrocarbon group with 7 to 21 carbon atoms).
[0079] 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.
[0080] 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 similarly, preferably 120 or less, more preferably 60 or less, and even more preferably 20 or less. From a similar viewpoint, the average number of moles of polyoxyethylene added is preferably 3 to 120, more preferably 3 to 60, even more preferably 4 to 60, and even more preferably 4 to 20.
[0081] 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.
[0082] 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.
[0083] 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.
[0084] 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 values in parentheses represent the average number of moles added. The same applies below.)
[0085] Examples of polyoxyethylene sorbitan trifatty acid esters include polyoxyethylene (20) sorbitan trilaurate, polyoxyethylene (20) sorbitan trimyristate, polyoxyethylene (20) sorbitan tripalmitate, polyoxyethylene (6) sorbitan tristearate, polyoxyethylene (20) sorbitan tristearate, polyoxyethylene (40) sorbitan tristearate, polyoxyethylene (20) sorbitan triisostearate, polyoxyethylene (6) sorbitan trioleate, polyoxyethylene (20) sorbitan trioleate, and polyoxyethylene (40) sorbitan trioleate, with polyoxyethylene (20) sorbitan tristearate and polyoxyethylene (20) sorbitan trioleate being preferred.
[0086] 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.
[0087] 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.
[0088] (D) Amino acids represented by formula (II)
[0089] [ka]
[0090] 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.
[0091] 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.
[0092] 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.
[0093] The amino acids represented by formula (II) include, for example, neutral amino acids such as glycine, alanine, leucine, isoleucine, phenylalanine, valine, threonine, serine, and tryptophan; and basic amino acids such as lysine. Examples include acidic amino acids such as aspartic acid and glutamic acid; however, from the viewpoint of suppressing trimer formation, neutral amino acids and acidic amino acids such as glycine, alanine, phenylalanine, isoleucine, tryptophan, and glutamic acid are preferred.
[0094] [Table 2]
[0095] (E) Anthranilate esters represented by formula (III)
[0096] [ka]
[0097] In formula (III), R 51 is a hydrogen atom, a methyl group, or an ethyl group. R 52 This is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms.
[0098] In equation (III), from the viewpoint of suppressing the generation of trimmers, R 52 Preferably, the alkyl group is a linear or branched alkyl group having 1 to 8 carbon atoms, or a cycloalkyl group having 4 to 8 carbon atoms. A linear or branched alkyl group having 1 to 6 carbon atoms or a cycloalkyl group having 4 to 8 carbon atoms is more preferable. Linear or branched alkyl groups having 1 to 5 carbon atoms, or cycloalkyl groups having 5 to 7 carbon atoms, are more preferred.
[0099] 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.
[0100] [Table 3]
[0101] (F) Pyrazine derivatives represented by formula (IV)
[0102] [ka]
[0103] 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.
[0104] 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.
[0105] [Table 4]
[0106] [Composition] The amount of the 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 trimer formation, 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.
[0107] 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, 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.
[0108] 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.
[0109] 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 less, and 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.
[0110] 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.
[0111] 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.
[0112] [An inhibitor of trimer formation of aliphatic aldehydes with 8 to 16 carbon atoms] The present invention is an inhibitor for suppressing the formation of trimers of aliphatic aldehydes having 8 to 16 carbon atoms, which contains one or more additives selected from the group consisting of the following components (A) to (F). 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 represented by the following general formula (I) or a derivative thereof, and (B) a sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms, or a combination of (B) a sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms and (C) a polyoxyethylene sorbitan fatty acid ester or a polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms.
[0113] (A) A (poly)alkylene glycol represented by the following general formula (I) or a derivative thereof
[0114] [Chemical formula]
[0115] [In formula (I), R 11 and R 12 are, independently of each other, a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, or a group of the formula -C(=O)-R 14 where 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 or more and 10 or less.] (B) A sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms (C) A polyoxyethylene sorbitan fatty acid ester or a polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms (D) An amino acid represented by the following general formula (II)
[0116] [Chemical formula]
[0117] [In formula (II), R 41 This refers to 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. (E) Anthranilate esters represented by the following general formula (III)
[0118] [ka]
[0119] [In formula (III), R 51 is a hydrogen atom, a methyl group, or an ethyl group. R 52 This is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. (F) Pyrazine derivatives represented by the following general formula (IV)
[0120] [ka]
[0121] [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.
[0122] 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.
[0123] [Method for suppressing trimmer generation] The present invention relates to a method for suppressing the formation of trimers of an aliphatic aldehyde, comprising mixing one or more additives selected from the group consisting of components (A) to (F) below 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 components selected from the group consisting of components (A) to (F) below. 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 7 to 21 hydrocarbon groups, or (B) a sorbitan fatty acid ester having 7 to 21 hydrocarbon groups and (C) a polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having 7 to 21 hydrocarbon groups. (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I)
[0124] [ka]
[0125] [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 This is an alkyl group having 1 to 20 carbon atoms. R 13 This is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. n is an integer between 1 and 10 (inclusive). (B) Sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (D) Amino acids represented by the following general formula (II)
[0126] [Chemical formula]
[0127] [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) Anthranilic acid ester represented by the following general formula (III)
[0128] [Chemical formula]
[0129] [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) Pyrazine derivative represented by the following general formula (IV)
[0130] [Chemical formula]
[0131] [In formula (IV), R 61 , R 62 , R 63 , and RinID=56 64 are, independently of each other, 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 or more and 6 or less.]
[0132] The amount of the aforementioned growth inhibitor used is, from the viewpoint of suppressing trimer formation, 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, relative to the mass of an aliphatic aldehyde having 8 to 16 carbon atoms. From the viewpoint of considering the decrease in the purity of the aliphatic aldehyde, it is 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 these viewpoints, it 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. In this specification, ppm refers to mass ppm.
[0133] 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.
[0134] The present invention includes the following embodiments. [1] A composition comprising an aliphatic aldehyde having 8 to 16 carbon atoms and an additive, 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): A composition in which the content of the additive is 100 ppm or more and 1% by mass or less relative to the mass of the aliphatic aldehyde. (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I)
[0135] [ka]
[0136] [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 This is an alkyl group having 1 to 20 carbon atoms. R 13 This is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. n is an integer between 1 and 10 (inclusive). (B) Sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms, (D) Amino acids represented by the following general formula (II)
[0137] [ka]
[0138] [In formula (II), R 41 This refers to 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. (E) Anthranilate esters represented by the following general formula (III)
[0139] [ka]
[0140] [In formula (III), R 51 is a hydrogen atom, a methyl group, or an ethyl group. R52 This is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. (F) Pyrazine derivatives represented by the following general formula (IV)
[0141] [ka]
[0142] [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.
[0143] [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.
[0144] [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.
[0145] [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.
[0146] [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].
[0147] [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.
[0148] [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 base (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.
[0149] [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 base (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.
[0150] [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 base (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.
[0151]
[10] In equation (I), R 11 and R 12 The 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.
[0152]
[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.
[0153]
[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 a group of the formula -C(=O)-R 14 The base (R 14 (This is a linear or branched alkyl group having 5 to 20 carbon atoms.) R 13 is a hydrogen atom or a C1 alkyl group, n is an integer between 1 and 5, However, when n is 1, R 11 and R 12 Except that they are both 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].
[0154]
[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 base (R 14 ( is a linear or branched alkyl group having 10 to 20 carbon atoms), and R 13 is a hydrogen atom or a C1 alkyl group, n is an integer between 1 and 5, However, when n is 1, R 11 and R 12 Except that they are both 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].
[0155]
[14] In equation (I), R 11 and R 12 One of them is equation -C(=O)-R 14 The base (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 is a hydrogen atom or a C1 alkyl group, The composition according to any one of [1] to
[13] , wherein n is an integer between 1 and 5.
[0156]
[15] In equation (I), R 11 and R 12 One of them is equation -C(=O)-R 14 The base (R 14 (one 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. R 13 is a hydrogen atom or a C1 alkyl group, The composition according to any one of [1] to
[14] , wherein n is an integer between 1 and 5.
[0157]
[16] In equation (I), R 11 and R 12 One of them is equation -C(=O)-R 14 The base (R 14 ( is a linear or branched alkyl group having 15 to 20 carbon atoms), and the other is a hydrogen atom. R 13 is a hydrogen atom or a C1 alkyl group, The composition according to any one of [1] to
[15] , wherein n is an integer between 1 and 4.
[0158]
[17] In equation (I), R 11 and R 12These are, independently of each other, hydrogen atoms or linear or branched alkyl groups having 1 to 3 carbon atoms. R 13 is a hydrogen atom or a C1 alkyl group, The composition according to any one of [1] to
[16] , wherein n is an integer between 2 and 5.
[0159]
[18] In equation (I), R 11 and R 12 It is a hydrogen atom, R 13 is a hydrogen atom or a methyl group, The composition according to any one of [1] to
[17] , wherein n is an integer between 2 and 5.
[0160]
[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 above.
[0161]
[20] The composition according to any one of [1] to
[19] , wherein the compound of formula (I) has 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.
[0162]
[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 the total number of carbon atoms is 5 to 12, polyethylene glycol or polypropylene glycol.
[0163]
[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.
[0164]
[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.
[0165] 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 to 21, preferably 9 to 19, and more preferably 11 to 17.
[0166] 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 esters, sorbitan di fatty acid esters, and sorbitan tri fatty acid esters, and preferably sorbitan mono fatty acid esters.
[0167] 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 to 21, preferably 9 to 19, and more preferably 11 to 17.
[0168] 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 to 120, more preferably 3 to 60, even more preferably 4 to 60, and even more preferably 4 to 20.
[0169] The composition according to any one of [1] to
[27] , wherein the polyoxyethylene sorbitan fatty acid ester of
[28] (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.
[0170] 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 to 21, preferably 9 to 19, and more preferably 11 to 17.
[0171] 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.
[0172] 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.
[0173]
[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)
[0174] [ka]
[0175] [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 This is an alkyl group having 1 to 20 carbon atoms. R 13 This is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. n is an integer between 1 and 10 (inclusive). (B) Sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (D) Amino acids represented by the following general formula (II)
[0176] [ka]
[0177] [In formula (II), R 41 This refers to 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. (E) Anthranilate esters represented by the following general formula (III)
[0178] [ka]
[0179] [In formula (III), R 51 is a hydrogen atom, a methyl group, or an ethyl group. R 52 This is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. (F) Pyrazine derivatives represented by the following general formula (IV)
[0180] [ka]
[0181] [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.
[0182]
[33] A method for suppressing trimer formation, comprising mixing one or more additives selected from the group consisting of the components (A) to (F) below with an aliphatic aldehyde having 8 to 16 carbon atoms. (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I)
[0183] [ka]
[0184] [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 This is an alkyl group having 1 to 20 carbon atoms. R 13 This is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. n is an integer between 1 and 10 (inclusive). (B) Sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (D) Amino acids represented by the following general formula (II)
[0185] [ka]
[0186] [In formula (II), R 41 This refers to 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. (E) Anthranilate esters represented by the following general formula (III)
[0187] [ka]
[0188] [In formula (III), R 51 is a hydrogen atom, a methyl group, or an ethyl group. R 52 This is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. (F) Pyrazine derivatives represented by the following general formula (IV)
[0189] [ka]
[0190] [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.
[34] A method for suppressing the formation of trimers of an aliphatic aldehyde having 8 to 16 carbon atoms, according to
[33] , wherein the additive is mixed in an amount of 100 ppm to 1% by mass, preferably 200 ppm to 6000 ppm, more preferably 500 ppm to 3000 ppm, and even more preferably 1000 ppm to 2000 ppm, relative to the mass of an aliphatic aldehyde having 8 to 16 carbon atoms.
[0191]
[35] Use of one or more additives selected from the group consisting of the following components (A) to (F) as an inhibitor of 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)
[0192] [ka]
[0193] [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 This is an alkyl group having 1 to 20 carbon atoms. R 13 This is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. n is an integer between 1 and 10 (inclusive). (B) Sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (D) Amino acids represented by the following general formula (II)
[0194] [ka]
[0195] [In formula (II), R41 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)
[0196] [Chemical formula]
[0197] [In formula (III), R 51 is a hydrogen atom, a methyl group or an ethyl group, 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)
[0198] [Chemical formula]
[0199] [In formula (IV), R 61 、R 62 、R 63 、and R 64 are, independently of each other, 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 or more and 6 or less.
[0200] The present invention will be described more specifically by way of examples and the like below. In the following examples and the like, the measurement and evaluation of each physical property were carried out by the following methods.
[0201] [NMR apparatus and analysis conditions] NMR apparatus: ASCEND manufactured by Bruker TM 400
[0202] Under the conditions of deuterated chloroform solvent, 400 MHz, 8 integration cycles, and 10-second relaxation time. 1 1H NMR measurements were performed.
[0203] [Examples, 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%, containing 2.5% trimer): Manufactured by Kao Corporation, contains 500 ppm α-tocopherol. ALDEHYDE C-10 (Decanal 99% purity, no trimmer): Manufactured by Kao Corporation Isopropyl myristate: Manufactured by Fujifilm Wako Pure Chemical Corporation, reagent grade. Triethyl citrate: Manufactured by Fujifilm Wako Pure Chemical Corporation, reagent grade. Triethylene glycol: Manufactured by Fujifilm Wako Pure Chemical Corporation, reagent grade. Dipropylene glycol: Manufactured by Fujifilm Wako Pure Chemical Corporation, reagent grade. Diethylene glycol dimethyl ether: Manufactured by Fujifilm Wako Pure Chemical Corporation, 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 "Leodor SP-O30V" Sorbitan tristearate: Manufactured by Kao Corporation, product name "Leodor SP-S30V" Polyoxyethylene (4) sorbitan monolaurate: Manufactured by Kao Corporation, product name "Leodor TW-L106" Polyoxyethylene (20) sorbitan monolaurate: Manufactured by Kao Corporation, product name "Leodor TW-L120" Polyoxyethylene (20) sorbitan monopalmitate: Manufactured by Kao Corporation, product name "Leodor TW-P120" Polyoxyethylene (6) sorbitan monostearate: Manufactured by Kao Corporation, product name "Leodor TW-S106V" Polyoxyethylene (20) sorbitan monostearate: Manufactured by Kao Corporation, product name "Leodor TW-S120V" Polyoxyethylene (20) sorbitan tristearate: Manufactured by Kao Corporation, product name "Leodor TW-S320V" Polyoxyethylene(6) sorbitan monooleate: Manufactured by Kao Corporation, product name "Leodor TW-O106V" Polyoxyethylene (20) sorbitan monooleate: Manufactured by Kao Corporation, product name "Leodor TW-O120V" Polyoxyethylene (20) sorbitan trioleate: Manufactured by Kao Corporation, product name "Leodor 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 Corporation, reagent grade. DL-Alanine: Manufactured by Fujifilm Wako Pure Chemical Corporation, reagent grade. DL-Phenylalanine: Manufactured by Fujifilm Wako Pure Chemical Corporation, reagent grade. DL-Isoleucine: Manufactured by Fujifilm Wako Pure Chemical Corporation, reagent grade. L-tryptophan: Manufactured by Fujifilm Wako Pure Chemical Corporation, reagent grade. L-Glutamic Acid: Manufactured by Fujifilm Wako Pure Chemical Corporation, Reagent Grade Methyl anthranilate: Manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., reagent grade. Methyl N-methylanthranilate: Manufactured by Tokyo Chemical Industry Co., Ltd., reagent grade. Isobutyl anthranilate: Manufactured by Fujifilm Wako Pure Chemical Corporation, 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.
[0204] [Additives: None, Aldehyde: Dodecanal, Raw material aldehyde purity 99%, Solvent: Isopropyl myristate] <Test Method 1> ALDEHYDE C-12L (dodecanal purity 99%, no trimer) 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 then packed 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 into a liquid state, then shaken to mix, and the composition was analyzed by NMR spectroscopy.
[0205] <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).
[0206] 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.
[0207] [Table 5]
[0208] As can be seen from the comparison between Reference Example 1 and Comparative Example 1 in Table 5, it is evident that trimer formation is suppressed when the purity of the aliphatic aldehyde is low.
[0209] [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 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 packed 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 into a liquid state, then shaken to mix, and the composition was analyzed by NMR spectroscopy.
[0210] <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).
[0211] 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.
[0212] [Table 6]
[0213] 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.
[0214] 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.
[0215] [Additives: Polyalkylene glycol derivative of formula (I), Aldehyde: Dodecanal, Starting material aldehyde purity 97%] <Test Method 3> 40 g of ALDEHYDE C-12L (containing 97% dodecanal purity and 2.5% trimer) and a polyalkylene glycol derivative of formula (I) as an additive were placed in a 50 mL screw-cap tube and shaken to dissolve. The resulting composition was packed 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 into a liquid state, then shaken and mixed, and the composition was analyzed by NMR spectroscopy.
[0216] <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).
[0217] 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 7 below.
[0218] [Table 7]
[0219] 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.
[0220] [Additives: Polyalkylene glycol derivative of formula (I), Aldehyde: Dodecanal, Starting material aldehyde purity 99%] <Test Method 4> 40 g of ALDEHYDE C-12L (99% dodecanal purity, no trimer) and a polyalkylene glycol derivative of formula (I) as an additive were placed in a 50 mL screw-cap tube and shaken to dissolve. The resulting composition was packed 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. In some examples, it was 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 into a liquid state, then shaken and mixed, and the composition was analyzed by NMR analysis.
[0221] <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).
[0222] 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 8 below.
[0223] [Table 8]
[0224] 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.
[0225] [Additives: Sorbitan fatty acid ester, Aldehyde: Dodecanal, Raw material aldehyde purity 97%] <Test Method 5> 40 g of ALDEHYDE C-12L (containing 97% pure dodecanal and 2.5% trimer) and sorbitan fatty acid ester as an additive were placed in a 50 mL screw-cap tube and shaken to dissolve. The resulting composition was packed 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 into a liquid state, then shaken and mixed, and the composition was analyzed by NMR spectroscopy.
[0226] <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).
[0227] 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.
[0228] [Table 9]
[0229] 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.
[0230] [Additives: Sorbitan fatty acid ester, Aldehyde: Dodecanal, Raw material aldehyde purity 99%] <Test Method 6> 40 g of ALDEHYDE C-12L (99% pure dodecanal, no trimer) and sorbitan fatty acid ester as an additive were placed in a 50 mL screw-cap tube and shaken to dissolve. The resulting composition was packed into a 9 mL screw-cap 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 into a liquid state, then shaken to mix, and the composition was analyzed by NMR spectroscopy.
[0231] <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).
[0232] 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.
[0233] [Table 10]
[0234] 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.
[0235] [Additives: Polyoxyethylene sorbitan fatty acid ester, Aldehyde: Dodecanal, Raw material aldehyde purity 97%] <Test Method 7> 40 g of ALDEHYDE C-12L (containing 97% pure dodecanal and 2.5% trimer) and polyoxyethylene sorbitan fatty acid ester as an additive were placed in a 50 mL screw-cap tube and shaken to dissolve. The resulting composition was packed 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 into a liquid state, then shaken and mixed, and the composition was analyzed by NMR spectroscopy.
[0236] <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).
[0237] 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.
[0238] [Table 11]
[0239] As shown in Table 11, it was confirmed that the composition containing dodecanal and polyoxyethylene sorbitan fatty acid ester suppresses trimer formation even when stored at low temperatures for a long period of time and then melted.
[0240] [Additives: 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 (99% pure dodecanal, no trimer) and polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester as an additive were placed in a 50 mL screw-cap tube and shaken to dissolve. The resulting composition was packed 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 into a liquid, then shaken to mix, and compositional analysis was performed by NMR analysis.
[0241] <Evaluation Method 8> 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).
[0242] 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 Tables 12 and 13 below.
[0243] [Table 12]
[0244] [Table 13]
[0245] As shown in Tables 12 and 13, it was confirmed that the composition containing dodecanal and polyoxyethylene sorbitan fatty acid ester suppressed trimer formation even when stored at low temperatures for a long period of time and then melted.
[0246] [Additives: Amino acids represented by formula (II), Aldehyde: Dodecanal, Raw material aldehyde purity 97%] <Test Method 9> 40 g of ALDEHYDE C-12L (containing 97% dodecanal purity and 2.5% trimer) and the amino acid represented by formula (II) as an additive were placed in a 50 mL screw-cap tube and shaken to dissolve. The resulting composition was packed 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 into a liquid state, then shaken and mixed, and the composition was analyzed by NMR spectroscopy.
[0247] <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).
[0248] 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.
[0249] [Table 14]
[0250] 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.
[0251] [Additives: Amino acids represented by formula (II), Aldehyde: Dodecanal, Raw material aldehyde purity 99%] <Test Method 10> 40 g of ALDEHYDE C-12L (99% pure dodecanal, no trimer) and the amino acid represented by formula (II) as an additive were placed in a 50 mL screw-cap tube and shaken to dissolve. The resulting composition was packed 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 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 into a liquid state, then shaken and mixed, and the composition was analyzed by NMR spectroscopy.
[0252] <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).
[0253] 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.
[0254] [Table 15]
[0255] 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.
[0256] [Additives: Anthranilic acid ester represented by formula (III), Aldehyde: Dodecanal, Raw material aldehyde purity 97%] <Test Method 11> 40 g of ALDEHYDE C-12L (containing 97% pure dodecanal and 2.5% trimer) and an anthranilate ester represented by formula (III) as an additive were placed in a 50 mL screw-cap tube and shaken to dissolve. The resulting composition was packed 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 into a liquid, then shaken and mixed, and the composition was analyzed by NMR spectroscopy.
[0257] <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).
[0258] 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.
[0259] [Table 16]
[0260] 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.
[0261] [Additives: Anthranilic acid ester represented by formula (III), Aldehyde: Dodecanal, Raw material aldehyde purity 99%] <Test Method 12> 40 g of ALDEHYDE C-12L (99% pure dodecanal, no trimer) and an anthranilate ester represented by formula (III) as an additive were placed in a 50 mL screw-cap tube and shaken to dissolve. The resulting composition was packed 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 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, then shaken to mix, and the composition was analyzed by NMR spectroscopy.
[0262] <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).
[0263] 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 17 below.
[0264] [Table 17]
[0265] 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.
[0266] [Additives: Pyrazine derivative represented by formula (IV), Aldehyde: Dodecanal, Raw material aldehyde purity 97%] <Test Method 13> 40 g of ALDEHYDE C-12L (containing 97% dodecanal purity and 2.5% trimer) and a pyrazine derivative represented by formula (IV) as an additive were placed in a 50 mL screw-cap tube and shaken to dissolve. The resulting composition was packed 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 into a liquid state, then shaken and mixed, and the composition was analyzed by NMR spectroscopy.
[0267] <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).
[0268] 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.
[0269] [Table 18]
[0270] 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.
[0271] [Additives: Pyrazine derivative represented by formula (IV), Aldehyde: Dodecanal, Raw material aldehyde purity 99%] <Test Method 14> 40 g of ALDEHYDE C-12L (99% pure dodecanal, no trimer) and a pyrazine derivative represented by formula (IV) as an additive were placed in a 50 mL screw-cap tube and shaken to dissolve. The resulting composition was packed 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 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 into a liquid state, then shaken and mixed, and the composition was analyzed by NMR spectroscopy.
[0272] <Evaluation Method 14> 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).
[0273] 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 19 below.
[0274] [Table 19]
[0275] As shown in Table 19, 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.
[0276] [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 (99% dodecanal purity, no trimer) and an additive consisting 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 a sorbitan fatty acid ester and polyoxyethylene sorbitan fatty acid ester were placed in a 50 mL screw-cap tube and dissolved by shaking. The resulting composition was packed into a 9 mL screw-cap 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 mixed by shaking, and the composition was analyzed by NMR analysis.
[0277] <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).
[0278] 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.
[0279] [Table 20]
[0280] 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.
[0281] [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) and sorbitan fatty acid ester or polyoxyethylene sorbitan fatty acid ester as an additive were placed in a 50 mL screw-cap tube and dissolved by shaking. The resulting composition was packed into a 9 mL screw-cap 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 into a liquid state, mixed by shaking, and the composition was analyzed by NMR analysis.
[0282] <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).
[0283] 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.
[0284] [Table 21]
[0285] 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.
[0286] 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, 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): A composition in which the content of the additive is 100 ppm or more and 1% by mass or less relative to the mass of the aliphatic aldehyde. (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I) 【Chemistry 45】 [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 This is an alkyl group having 1 to 20 carbon atoms. R 13 This is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. n is an integer between 1 and 10 (inclusive). (B) Sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms, (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (D) Amino acids represented by the following general formula (II) 【Chemistry 46】 [In formula (II), R 41 This includes hydrogen atoms, alkyl groups having 1 to 5 carbon atoms, or heterocyclic groups, aromatic ring groups, COOH, and NH. 2 Alternatively, it is an alkyl group having 1 to 5 carbon atoms substituted with an OH group. (E) Anthranilate esters represented by the following general formula (III) 【Chemistry 47】 [In formula (III), R 51 is a hydrogen atom, a methyl group, or an ethyl group. R 52 is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. (F) Pyrazine derivatives represented by the following general formula (IV) 【Chemistry 48】 [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.
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 (This is a linear or branched alkyl group having 5 to 20 carbon atoms.) R 13 is a hydrogen atom or a C1 alkyl group, n is an integer between 1 and 5, However, when n is 1, R 11 and R 12 Except that they are both 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 for [a certain substance].
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 is a hydrogen atom or a C1 alkyl group, The composition according to claim 1, wherein n is an integer between 1 and 5.
4. In equation (I), R 11 and R 12 These are, independently of each other, hydrogen atoms or linear or branched alkyl groups having 1 to 3 carbon atoms. R 13 is a hydrogen atom or a C1 alkyl group, The composition according to claim 1, wherein 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 content of the aliphatic aldehyde 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 the formation of trimers of aliphatic aldehydes having 8 to 16 carbon atoms, comprising one or more additives selected from the group consisting of components (A) to (F) below. (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I) 【Chemistry 49】 [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 This is an alkyl group having 1 to 20 carbon atoms. R 13 This is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. n is an integer between 1 and 10 (inclusive). (B) Sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (D) Amino acids represented by the following general formula (II) [Transformation 50] [In formula (II), R 41 This includes hydrogen atoms, alkyl groups having 1 to 5 carbon atoms, or heterocyclic groups, aromatic ring groups, COOH, and NH. 2 Alternatively, it is an alkyl group having 1 to 5 carbon atoms substituted with an OH group. (E) Anthranilate esters represented by the following general formula (III) 【Chemistry 51】 [In formula (III), R 51 is a hydrogen atom, a methyl group, or an ethyl group. R 52 This is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. (F) Pyrazine derivatives represented by the following general formula (IV) 【Chemistry 52】 [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.
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 components (A) to (F) below with an aliphatic aldehyde having 8 to 16 carbon atoms. (A) (Poly)alkylene glycol or derivative thereof represented by the following general formula (I) 【Chemistry 53】 [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 This is an alkyl group having 1 to 20 carbon atoms. R 13 This is a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. n is an integer between 1 and 10 (inclusive). (B) Sorbitan fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (C) Polyoxyethylene sorbitan fatty acid ester or polyoxyethylene sorbitol fatty acid ester having a hydrocarbon group with 7 to 21 carbon atoms. (D) Amino acids represented by the following general formula (II) 【Chemistry 54】 [In formula (II), R 41 This includes hydrogen atoms, alkyl groups having 1 to 5 carbon atoms, or heterocyclic groups, aromatic ring groups, COOH, and NH. 2 Alternatively, it is an alkyl group having 1 to 5 carbon atoms substituted with an OH group. (E) Anthranilate esters represented by the following general formula (III) 【Transformation 55】 [In formula (III), R 51 is a hydrogen atom, a methyl group, or an ethyl group. R 52 This is an alkyl group having 1 to 8 carbon atoms or a cycloalkyl group having 3 to 8 carbon atoms. (F) Pyrazine derivatives represented by the following general formula (IV) 【Transformation 56】 [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.