Compounds, surfactants, and surfactant compositions

Abstract

The present invention provides a non-fluorinated compound, surfactant, and surfactant composition having excellent surface tension reducing ability at the same level as fluorinated surfactants. 【Solution means】 A compound represented by formula (1): R 1 -O-C p H 2p -CR 2 (OH)-C q H 2q -X-C r H 2r -M. In formula (1), R 1 : A branched alkyl group having 9 to 18 carbon atoms, R 2 : A hydrogen atom or an alkyl group having 1 to 6 carbon atoms, p, q, and r: Independently of each other, integers from 1 to 6, X: A group represented by a predetermined formula, R 3 : A hydrogen atom, an alkyl group having 1 to 12 carbon atoms, HOCO-CH2-, or R 4 -O-C x H 2x -CR 5 (OH)-C y H 2y -represented group, R 4 : A branched alkyl group having 9 to 18 carbon atoms, R 5 : A hydrogen atom or an alkyl group having 1 to 6 carbon atoms, x and y: Independently of each other, integers from 1 to 6, R 6 : A hydrogen atom or an alkyl group having 1 to 6 carbon atoms, Y - : Iodide ion, chloride ion, bromide ion, or organic acid ion, M: A group represented by a predetermined formula.

Description

[Technical Field]

[0001] This invention relates to compounds, surfactants, and surfactant compositions. [Background technology]

[0002] Conventionally, fluorinated surfactants containing perfluoroalkyl groups have been known to have excellent surface tension-reducing capabilities. However, in recent years, concerns have arisen regarding the environmental impact of compounds containing perfluoroalkyl groups, and alternatives to fluorinated surfactants are needed. On the other hand, branched alkyl sulfosuccinates having branched alkyl groups are known to be usable as anionic surfactants (for example, Patent Document 1). [Prior art documents] [Patent Documents]

[0003] [Patent Document 1] Japanese Patent Publication No. 2021-147618 [Overview of the project] [Problems that the invention aims to solve]

[0004] However, the only known surfactants containing branched alkyl groups are anionic and nonionic surfactants; amphoteric and cationic surfactants containing branched alkyl groups are not known. When the present inventors examined the branched alkyl sulfosuccinates disclosed in Patent Document 1, they found that the surface tension reduction ability of the above-mentioned branched alkyl sulfosuccinates is lower than that of fluorinated surfactants having a perfluoroalkyl group.

[0005] Therefore, the object of the present invention is to provide a non-fluorinated compound that has excellent surface tension reduction ability equivalent to that of fluorinated surfactants. Another object of the present invention is to provide a surfactant and a surfactant composition.

Means for Solving the Problems

[0006] As a result of intensive studies to solve the above problems, the present inventors have found that the problems can be solved by the following configuration.

[0007] [1] A compound represented by the following formula (1). R , 4 , y , 2x , , 4 , 2 , , 1 , 5 , 2y , , 5 , , x , 3 , -O-C p H 2p -CR 2 (OH)-C q H 2q -X-C r H 2r -M (1) The symbols in formula (1) have the following meanings. R 1 : A branched alkyl group having 9 to 18 carbon atoms R 2 : A hydrogen atom or an alkyl group having 1 to 6 carbon atoms p, q and r: Independently of each other, an integer of 1 to 6 X: A group represented by the following formula (2) or formula (3)

Chemical formula

[0008] In this specification, the compound represented by formula (1) may be simply referred to as "compound (1)" or "(1)". In this specification, the group represented by formula (2) may be simply referred to as "group (2)" or "(2)". The same applies to the groups represented by formulas (3) to (12), etc. [Effects of the Invention]

[0009] According to the present invention, it is possible to provide a non-fluorinated compound that has excellent surface tension reduction ability at a level equivalent to that of fluorinated surfactants. Furthermore, the present invention can also provide surfactants and surfactant compositions. [Modes for carrying out the invention]

[0010] The present invention will be described in detail below. The following description of the constituent elements may be based on typical embodiments of the present invention, but the present invention is not limited to such embodiments. In this specification, a numerical range represented by "~" means a range that includes the numbers written before and after "~" as the lower and upper limits, respectively. In this specification, each component may be used individually or in combination of two or more. In this specification, when two or more ingredients are used in combination, the "content" of those ingredients means the total content of those two or more ingredients unless otherwise specified. In this specification, the method for producing each component is not particularly limited unless otherwise specified. For example, conventionally known methods may be used.

[0011] The compounds of the present invention will be described below. [Compound] The compound of the present invention is a compound represented by the following formula (1). A compound represented by the following formula (1). R 1 -OC p H 2p -CR 2 (OH)-C q H 2q -XC r H 2r -M (1) The symbols in equation (1) have the following meanings: R 1 : Branched alkyl groups with 9 to 18 carbon atoms R 2 : Hydrogen atom or alkyl group having 1 to 6 carbon atoms p, q, and r: Integers from 1 to 6, independent of each other. X: A base represented by the following formula (2) or (3) [ka] TIFF2026083806000011.tif2447 R 3 : Mutually independent of each other, a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a group represented by the following formula (4), or a group represented by the following formula (5) HOCO-CH2- (4) R 4 -OC x H 2x -CR 5 (OH)-C y H 2y - (5) R 4 : Branched alkyl groups with 9 to 18 carbon atoms R 5 : Hydrogen atom or alkyl group having 1 to 6 carbon atoms x and y: Independent integers from 1 to 6 R6 : Hydrogen atom or alkyl group having 1 to 6 carbon atoms Y - : Iodide ions, chloride ions, bromide ions, or organic acid ions M: Base represented by the following formulas (6) to (9) [ka] TIFF2026083806000013.tif2449 TIFF2026083806000014.tif2441 JPEG2026083806000015.jpg2349 R 7 : Mutually independent alkyl groups having 1 to 6 carbon atoms R 8 : Hydrogen atom or alkyl group having 1 to 6 carbon atoms Z - : Iodide ions, chloride ions, bromide ions, or organic acid ions

[0012] The reason why the compound of the present invention having the above configuration can solve the problems of the present invention is not necessarily clear, but the inventors speculate as follows. It should be noted that the following speculation does not limit the mechanism by which the effect is obtained. In other words, even if the effect is obtained by a mechanism other than those described below, it is still within the scope of the present invention. The compounds of the present invention are characterized in formula (1) by R, which represents a branched alkyl group having 9 to 18 carbon atoms. 1 In addition, [-OC p H 2p -CR 2 (OH)-C q H 2q -XC r H 2r It is believed that having the structure [-M] gives it excellent surface tension reduction ability, equivalent to that of fluorine-based surfactants.

[0013] The symbols in equation (1) are explained below. [R 1 ] In formula (1), R 1It is a branched alkyl group having 9 to 18 carbon atoms. R 1 Examples of branched alkyl groups having 9 to 18 carbon atoms include the group represented by formulas (10) to (12) below, isodecyl group, isododecyl group, isotridecyl group, isostearyl group, 2-hexyl-1-dodecyl group, 2,6,8-trimethyl-4-nonyl group, and 8-methyl-2-(4-methylhexyl)decyl group. R 1 The branched alkyl group having 9 to 18 carbon atoms is preferably one of the branched alkyl groups selected from the groups represented by the following formulas (10) to (12) from the viewpoint of achieving superior effects of the present invention. Note that the wavy lines in equation (10) represent the ends of the bonds of the carbon atoms in the "CH2" group represented by letters in equation (10). As shown in equation (1) above, R 1 Where it bonds with the oxygen atom, R 1 The group represented by formula (10) is bonded to the oxygen atom by the above bond. The wavy lines in formulas (11) and (12) have the same meaning. [ka] JPEG2026083806000017.jpg3753 JPEG2026083806000018.jpg3578

[0014] In formula (1), “R 1 " and "-C p H 2p Regarding the "-O-" located between "-", the above "-O-" is "R 1 It just needs to bond to any of the carbon atoms that " " possesses. The above "-O-" is -C p H 2p - It can bond to any of the carbon atoms it possesses.

[0015] [R 2 ] In formula (1), R 2 This is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R2 Examples of C1-C6 alkyl groups include methyl, ethyl, propyl, butyl, pentyl, and hexyl groups. C1-C6 alkyl groups may be linear, and if they have 3-C6 atoms, they may be linear, branched, or cyclic.

[0016] R 2 From the viewpoint of ease of obtaining and reactivity of the raw materials constituting the compound of the present invention, it is preferable that the atom is a hydrogen atom.

[0017] [p, q, and r] In equation (1), p, q, and r are mutually independent integers between 1 and 6. -C p H 2p - The divalent linking group represented by - may be linear, and when p is an integer between 3 and 6, it may be linear, branched, or a combination thereof. -C r H 2r - is also true.

[0018] [p] In formula (1), p is preferably an integer from 1 to 3, and more preferably 1, from the viewpoint of the availability and reactivity of the raw materials constituting the compound of the present invention.

[0019] [q] In formula (1), q is preferably an integer from 1 to 3, and more preferably 1, from the viewpoint of the availability and reactivity of the raw materials constituting the compound of the present invention. -C q H 2q The divalent linking group represented by - may be linear, and when q is an integer between 3 and 6, it may be linear or branched.

[0020] [r] In formula (1), r is preferably an integer between 1 and 3, and more preferably an integer between 2 and 3, from the viewpoint of the availability and reactivity of the raw materials constituting the compound of the present invention.

[0021] [-CR 2 (OH)-] In formula (1), "-CR 2 (OH)-" may be bonded to any of the carbon atoms of -C p H 2p -. In formula (1), "-CR 2 (OH)-" may be bonded to any of the carbon atoms of -C q H 2q -.

[0022] [-X-] In formula (1), X is a group represented by the following formula (2) or formula (3).

Chemical formula

[0023] In formula (1), "-X-" may be bonded to any of the carbon atoms of -C q H 2q -. In formula (1), "-X-" may be bonded to any of the carbon atoms of -C r H 2r -.

[0024] [R 3 In formula (2) and formula (3), R 3 are, independently of each other, a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a group represented by the following formula (4) or a group represented by the following formula (5). HOCO-CH2- (4) R 4 -O-C x H 2x -CR 5 (OH)-C y H 2y - (5)

[0025] (alkyl group having 1 to 12 carbon atoms) R 3 ​If the alkyl group has 1 to 12 carbon atoms, examples of alkyl groups with 1 to 12 carbon atoms include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, and dodecyl groups. The alkyl group with 1 to 12 carbon atoms may be linear, and if it has 3 to 12 carbon atoms, it may be linear, branched, cyclic, or a combination of these.

[0026] (Base represented by formula (4)) The group represented by formula (4) is HOCO-CH2-. In formula (4), HOCO- represents a carboxyl group.

[0027] (Base represented by formula (5)) The base represented by equation (5) is as follows: R 4 -OC x H 2x -CR 5 (OH)-C y H 2y - (5) R 3 If the base is represented by equation (5), then each symbol in equation (5) will be explained below.

[0028] (R 4 ) In formula (5), R 4 It is a branched alkyl group having 9 to 18 carbon atoms. R 4 The branched alkyl group having 9 to 18 carbon atoms is the R in formula (1) mentioned above. 1 This is similar to a branched alkyl group with 9 to 18 carbon atoms. R 4 The branched alkyl group having 9 to 18 carbon atoms is preferably one of the branched alkyl groups selected from the groups represented by formulas (10) to (12) described above, from the viewpoint of achieving superior effects of the present invention.

[0029] (R 5 ) In formula (5), R 5 This is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 5 The alkyl group having 1 to 6 carbon atoms is the R in formula (1) mentioned above. 2 This is similar to alkyl groups with 1 to 6 carbon atoms. R 5 From the viewpoint of ease of obtaining and reactivity of the raw materials constituting the compound of the present invention, it is preferable that the atom is a hydrogen atom.

[0030] (x and y) In equation (5), x and y are mutually independent integers between 1 and 6. In formula (5), x is the same as p in formula (1) as described above. In formula (5), x is preferably an integer from 1 to 3, and more preferably 1, from the viewpoint of the availability and reactivity of the raw materials constituting the compound of the present invention. In formula (5), y is the same as q in formula (1) as described above. In formula (5), y is preferably an integer from 1 to 3, and more preferably 1, from the viewpoint of the availability and reactivity of the raw materials constituting the compound of the present invention.

[0031] -O- and -C in equation (5) x H 2x -, -CR 5 (OH)-, -C y H 2y - represents -O- and -C in equation (1). p H 2p -, -CR 2 (OH)-, -C q H 2q -These are similar in each respect.

[0032] [R 6 ] In formula (3), R 6 This is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 6 The alkyl group having 1 to 6 carbon atoms is the R in formula (1) mentioned above. 2 This is similar to alkyl groups with 1 to 6 carbon atoms. R 6From the viewpoint of ease of obtaining and reactivity of the raw materials constituting the compound of the present invention, it is preferable that this is a hydrogen atom or a methyl group.

[0033] [Y - ]Y - : Iodide ions, chloride ions, bromide ions, or organic acid ions In formula (3), Y - is an iodide ion (I - ), chloride ions (Cl - ), bromide ions (Br - ) or organic acid ions. Examples of organic acid ions include acetate ions (CH3COO - ) are cited. From the perspective of reactivity, Y - Iodide ions or chloride ions are preferred.

[0034] [M] In formula (1), M is a group represented by the following formulas (6) to (9). In the present invention, M is any of the groups represented by the following formulas (6) to (9). [ka] TIFF2026083806000022.tif2449 TIFF2026083806000023.tif2441 JPEG2026083806000024.jpg2349

[0035] [R 7 ] In formulas (6) to (9), R 7 These are, independently of each other, alkyl groups having 1 to 6 carbon atoms. R 7 The alkyl group having 1 to 6 carbon atoms is the R in formula (1) mentioned above. 2 This is similar to alkyl groups with 1 to 6 carbon atoms. R 7 From the viewpoint of ease of obtaining raw materials and reactivity for the compound of the present invention, it is preferable that the group is a methyl group or an ethyl group.

[0036] [R 8 ] In formula (9), R 8 This is a hydrogen atom or an alkyl group having 1 to 6 carbon atoms. R 8 The alkyl group having 1 to 6 carbon atoms is the R in formula (1) mentioned above. 2 This is similar to alkyl groups with 1 to 6 carbon atoms. R 8 From the viewpoint of ease of obtaining and reactivity of the raw materials constituting the compound of the present invention, it is preferable that this is a hydrogen atom or a methyl group.

[0037] [Z - Iodide ions, chloride ions, bromide ions, or organic acid ions In formula (9), Z - These are iodide ions, chloride ions, bromide ions, or organic acid ions. Examples of organic acid ions include acetate ions (CH3COO). - ) are cited. From the perspective of reactivity, Z - Iodide ions or chloride ions are preferred.

[0038] (Preferred embodiment of the compound represented by formula (1) - Part 1) The compound represented by formula (1) is chosen from the viewpoint of having superior effects according to the present invention, and R in formula (1) 1 or R in equation (5) 4 However, one preferred embodiment is that each group is independently a branched alkyl group selected from the groups represented by formulas (10) to (12) above. In equation (1), X is the base represented by equation (2), and R in equation (2) 3 If is a group represented by formula (5), then R in formula (1) 1 and R in equation (5) 4 However, they may be any branched alkyl group selected independently from the groups represented by formulas (10) to (12) above.

[0039] (Preferred embodiment of the compound represented by formula (1), part 2) From the viewpoint of having superior effects in the present invention, the compound represented by formula (1) is one in which X is the group represented by formula (2), and R in formula (2) 3 It is preferable that the group is represented by formula (4) above, where in formula (1) X is the group represented by formula (2), and in formula (2) R 3 Compounds in which the group is represented by formula (4) and in formula (1) above, M is represented by the group represented by formula (6) are more preferred.

[0040] (Preferred embodiment of the compound represented by formula (1), part 3) From the viewpoint of having superior effects in the present invention, the compound represented by formula (1) is one in which X is the group represented by formula (2), and in formula (2) R 3 Compounds in which is a hydrogen atom or a group represented by formula (5), and in formula (1) above, M is a group represented by formula (8) or formula (9), are preferred.

[0041] Examples of compounds represented by formula (1) include the following amine compound (a), the following amphoteric compound (b), the following amine oxide compound (c), and the following cationic compound (d).

[0042] (Amine compound (a)) In this specification, amine compound (a) is a compound in which X in formula (1) is formula (2) and R in formula (2) 3 This refers to a compound in which is a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, or a group represented by the following formula (5), and M has the formula (6). For example, the amine compound (a) is R in formula (1). 2 is a hydrogen atom, X in formula (1) is the group represented by formula (2) above, and R in formula (2) 3 Examples of compounds include those in which is a hydrogen atom or a group represented by formula (5), and M in formula (1) is a group represented by formula (6). Specifically, examples of the above amine compound (a) include the compounds represented by the following formulas (a-1) to (a-4). [ka] TIFF2026083806000026.tif16115 TIFF2026083806000027.tif27124 TIFF2026083806000028.tif27126

[0043] (Amphoteric compound (b)) In this specification, amphoteric compound (b) is a compound in which X in formula (1) is formula (2) and R in formula (2) 3 This refers to a group having formula (4), and / or a compound in which M has formula (7). The amphoteric compound (b) has a cation and anion in its constituent skeleton. Examples of amphoteric compounds (b) include R in formula (1). 2 is a hydrogen atom, X in formula (1) is the group represented by formula (2) above, and R in formula (2) 3 The amphoteric compound in which is a group represented by formula (4) and M in formula (1) is a group represented by formula (6), R in equation (1) 2 is a hydrogen atom, X in formula (1) is the group represented by formula (2) above, and R in formula (2) 3 Examples of amphoteric compounds include those in which the group is represented by formula (5) above and M in formula (1) is represented by the group represented by formula (7) above.

[0044] R in equation (1) 2 is a hydrogen atom, X in formula (1) is the group represented by formula (2) above, and R in formula (2) 3 Examples of amphoteric compounds where is the group represented by formula (4) and M in formula (1) is the group represented by formula (6) include the compounds represented by the following formulas (b-1) to (b-4). [ka] TIFF2026083806000030.tif26126 TIFF2026083806000031.tif24121 TIFF2026083806000032.tif26119

[0045] Also, R in equation (1) 2 is a hydrogen atom, X in formula (1) is the group represented by formula (2) above, and R in formula (2) 3 Examples of amphoteric compounds where is the group represented by formula (5) above and M in formula (1) is the group represented by formula (7) above include the compounds represented by the following formulas (b-5) to (b-6). [ka] TIFF2026083806000034.tif27127

[0046] (Amine oxide compound (c)) In this specification, amine oxide compound (c) refers to a compound in formula (1) where M is formula (8). Amine oxide compound (c) is an amine oxide group (N) derived from formula (8) as M. + -O - ) has. For example, the amine oxide compound (c) is R in formula (1). 2 is a hydrogen atom, X in formula (1) is the group represented by formula (2) above, and R in formula (2) 3 The amine oxide compound in which is a hydrogen atom and M in formula (1) is the group represented by formula (8) above, or R in formula (1) 2 is a hydrogen atom, X in formula (1) is the group represented by formula (2) above, and R in formula (2) 3 Examples of amine oxide compounds include those in which the group is represented by formula (5) and M in formula (1) is represented by the group represented by formula (8).

[0047] R in equation (1) 2 is a hydrogen atom, X in formula (1) is the group represented by formula (2) above, and R in formula (2) 3Specific examples of amine oxide compounds where is a hydrogen atom and M in formula (1) is the group represented by formula (8) above include the compounds represented by the following formulas (c-1) to (c-4). [ka] TIFF2026083806000036.tif26130 TIFF2026083806000037.tif18130 TIFF2026083806000038.tif26130

[0048] R in equation (1) 2 is a hydrogen atom, X in formula (1) is the group represented by formula (2) above, and R in formula (2) 3 Examples of amine oxide compounds where is the group represented by formula (5) and M in formula (1) is the group represented by formula (8) include the compounds represented by the following formulas (c-5) to (c-6). [ka] TIFF2026083806000040.tif27126

[0049] (Cationic compound (d)) In this specification, cationic compound (d) refers to a compound in which X in formula (1) is formula (3) and / or M in formula (1) is formula (9). Cationic compound (d) has a cation within its constituent skeleton and an anion outside the skeleton. Examples of cationic compounds (d) include R in formula (1). 2 is a hydrogen atom, X in formula (1) is the group represented by formula (2) above, and R in formula (2) 3 A cationic compound in which is a hydrogen atom and M in formula (1) is a group represented by the above formula (9), R in equation (1) 2 is a hydrogen atom, X in formula (1) is the group represented by formula (2) above, and R in formula (2)3 A cationic compound in which is a group represented by formula (5) and M in formula (1) is a group represented by the above formula (9), R in equation (1) 2 A cationic compound in which is a hydrogen atom, X in formula (1) is the group represented by formula (3) above, and M in formula (1) is the group represented by formula (6) above, R in equation (1) 2 is a hydrogen atom, X in formula (1) is the group represented by formula (3) above, and R in formula (3) 3 A cationic compound in which is a hydrogen atom and M in formula (1) is a group represented by the above formula (9), R in equation (1) 2 is a hydrogen atom, X in formula (1) is the group represented by formula (3) above, and R in formula (3) 3 Examples of cationic compounds include those in which the group is represented by formula (5) and M in formula (1) is represented by the group represented by formula (9).

[0050] R in equation (1) 2 is a hydrogen atom, X in formula (1) is the group represented by formula (2) above, and R in formula (2) 3 Cationic compounds in which is a hydrogen atom and M in formula (1) is the group represented by formula (9) above include, for example, the compounds represented by the following formulas (d-1) to (d-4). [ka] TIFF2026083806000042.tif28141 TIFF2026083806000043.tif21141 TIFF2026083806000044.tif29141

[0051] R in equation (1) 2 is a hydrogen atom, X in formula (1) is the group represented by formula (2) above, and R in formula (2) 3When the group is represented by formula (5) and M in formula (1) is the group represented by formula (9), specific examples of cationic compounds include those represented by the following formulas (d-5) to (d-6). [ka] TIFF2026083806000046.tif28141

[0052] R in equation (1) 2 Cationic compounds in which is a hydrogen atom, X in formula (1) is the group represented by formula (3) above, and M in formula (1) is the group represented by formula (6) above, specifically include the compounds represented by the following formulas (d-7) to (d-10). [ka] TIFF2026083806000048.tif20143 TIFF2026083806000049.tif26144 TIFF2026083806000050.tif26146

[0053] R in equation (1) 2 is a hydrogen atom, X in formula (1) is the group represented by formula (3) above, and R in formula (3) 3 Cationic compounds in which is a hydrogen atom and M in formula (1) is the group represented by formula (9) above include, for example, the compounds represented by the following formulas (d-11) to (d-14). [ka]

[0054] R in equation (1) 2 is a hydrogen atom, X in formula (1) is the group represented by formula (3) above, and R in formula (3) 3When the group is represented by formula (5) above and M in formula (1) is the group represented by formula (9) above, specific examples of cationic compounds include those represented by the following formulas (d-15) to (d-16). [ka]

[0055] (Method for producing the compound of the present invention) The method for producing the compound of the present invention is not particularly limited.

[0056] (Method for producing the compound of the present invention, part 1) When the compound of the present invention is the above-mentioned amine compound (a), a method for producing the above-mentioned amine compound (a) is, for example, a method of producing the amine compound (a) by reacting an epoxy compound represented by the following formula (13) with a diamine compound represented by formula (14) under heating. [ka] NHR 3 -C r H 2r -NR 7 2(14)

[0057] • Epoxy compounds The epoxy compound used in the method for producing the above amine compound (a) is the compound represented by the above formula (13). R in equation (13) 1 , R 2 p and q are R in equation (1). 1 , R 2 It is the same as p and q. Examples of compounds represented by formula (13) include 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane (structure represented by formula (15) below), compounds represented by formula (16) below, compounds in which a glycidyloxy group is bonded to the bond of the group represented by formula (11) above, and compounds in which a glycidyloxy group is bonded to the bond of the group represented by formula (12) above. [ka] TIFF2026083806000055.tif26133

[0058] • Diamine compounds The diamine compound used in the method for producing the above amine compound (a) is a compound represented by the following formula (14). NHR 3 -C r H 2r -NR 7 2(14) R in equation (14) 3 ,r,R 7 R in equation (1) 3 ,r,R 7 It is the same as above. However, R in equation (14) 3 This does not include equation (4). Note that R in equation (14) 7 This is R in equation (6) in equation (1). 7 It corresponds to.

[0059] Examples of diamine compounds represented by formula (14) include 3-(diethylamino)propylamine and 3-(dimethylamino)propylamine.

[0060] • Amount of epoxy compounds used in relation to diamine compounds In the method for producing the above amine compound (a), the amount of the epoxy compound represented by formula (13) used relative to the diamine compound represented by formula (14) can be, for example, 0.2 to 3 molar equivalents of the epoxy compound per 1 molar equivalent of the diamine compound. As the amine compound (a), R in formula (2) 3 When synthesizing a compound in which is the above hydrogen atom or the above C1-C12 alkyl group, for example, it is represented by the above formula (14), and R in formula (14) 3For every molar equivalent of a diamine compound in which R is a hydrogen atom or an alkyl group having 1 to 12 carbon atoms, theoretically 0.2 to 1 molar equivalent of the epoxy compound can be used. 3 In the case of hydrogen atoms, it is preferable to use 0.2 to 0.5 molar equivalents of the epoxy compound per 1 molar equivalent of the diamine compound in order to reduce the by-products resulting from the reaction of 2 equivalents of the epoxy compound. As the amine compound (a), R in formula (2) 3 When synthesizing a compound in which is the group represented by formula (5), for example, the above formula (14) is used, and R in formula (14) 3 Theoretically, two molar equivalents of the epoxy compound should be reacted with one molar equivalent of the diamine compound, where the hydrogen atom is present.

[0061] Method for producing amine compound (a) Amine compound (a) can be obtained, for example, by raising the temperature of the diamine compound represented by formula (14) to 30-100°C and reacting the epoxy compound represented by formula (14) with the diamine compound represented by formula (14) under conditions of 30-100°C. In the above reaction, in order to suppress the heat of reaction, a water-soluble organic solvent (for example, 2-propanol, etc.) that can dissolve the diamine compound and the epoxy compound may be used. After the above reaction, the obtained amine compound (a) may be purified as needed. The method of purification is not particularly limited. As described above, for example, the amine compound (a) of the present invention can be produced by the manufacturing method described above.

[0062] (Method for producing the compound of the present invention, part 2) If the compound of the present invention is a compound other than the amine compound (a) described above (for example, if the compound of the present invention is an amphoteric compound (b), an amine oxide compound (c), or a cationic compound (d)), a method for producing the compound other than the amine compound (a) described above includes, for example, a method of producing the compound other than the amine compound (a) described above by reacting the amine compound (a) produced as described above with various reactants.

[0063] • Method for producing the amphoteric compound (b) When the compound of the present invention is an amphoteric compound (b), the amphoteric compound (b) can be produced by using an alkali metal monochloroacetate, such as potassium monochloroacetate, as a reactant, and reacting the reactant with an amine compound (a) in the presence of a water-soluble organic solvent, such as 2-propanol, under conditions of 30 to 100°C. In this case, a commercially available alkali metal monochloroacetate may be used as the reactant, or monochloroacetate and an alkali metal hydroxide such as potassium hydroxide may be used. After the reaction, impurities such as chlorides produced can be removed by filtration, and the obtained amphoteric compound (b) can be purified.

[0064] The R of the amine compound (a) used in the above manufacturing method 3 When is a hydrogen atom, alkali metal monochloroacetates such as potassium monochloroacetate add to the secondary amine (the nitrogen atom in formula (2) in formula (1)) of amine compound (a), where X is the group represented by formula (2) in formula (1), and R 3 A compound in which is the group represented by formula (4) and M is the group represented by formula (6), i.e., a compound represented by the following formula (18), is obtained as the amphoteric compound (b). R 1 -OC p H 2p -CR 2 (OH)-C q H 2q -N(CH2COOH)-C r H 2r -NR 7 2(18) R in equation (18) 1 , R 2 , R 7 p, q, and r are R in equation (1). 1 , R 2 , R 7 This is the same as p, q, and r. Note that R in equation (18) 7 This is R in equation (6) of equation (1). 7 It corresponds to. Examples of amphoteric compounds (b) that can be produced by the above manufacturing method include, for example, the compounds represented by formulas (b-1) to (b-4) above.

[0065] The R of the amine compound (a) used in the above manufacturing method 3 When is the group represented by formula (5), alkali metal monochloroacetates such as potassium monochloroacetate add to the terminal tertiary amine (the nitrogen atom in formula (6) in formula (1)) of amine compound (a), where X is the group represented by formula (2) and R in formula (2) 3 The compound represented by the following formula (19), in which is the group represented by formula (5) and M is represented by formula (7), is obtained as the amphoteric compound (b). [ka] R in equation (19) 1 , R 2 , R 4 , R 5 , R 7 p, q, r, x, y are R in equation (1). 1 , R 2 , R 4 , R 5 , R 7 The same applies to p, q, r, x, and y. Note that R in equation (19) 7 R in equation (7) of equation (1) is 7 It corresponds to. Examples of amphoteric compounds (b) that can be produced by the above manufacturing method include, for example, the compounds represented by formulas (b-5) to (b-6) above.

[0066] • Amount of alkali metal monochloroacetate used relative to amine compound (a) In the method for producing the above-mentioned amphoteric compound (b), the amount of alkali metal monochloroacetate (e.g., potassium monochloroacetate, etc.) used relative to the amine compound (a) can be, for example, 1 to 3 molar equivalents of alkali metal monochloroacetate per 1 molar equivalent of amine compound (a). To reduce by-products, it is preferable to use 1 to 1.5 molar equivalents of alkali metal monochloroacetate per 1 molar equivalent of amine compound (a). When using monochloroacetic acid as an alkali metal monochloroacetate, for example, one molar equivalent of a hydroxide such as potassium hydroxide can be used relative to the monochloroacetic acid.

[0067] Method for producing amine oxide compound (c) Amine oxide compound (c) can be produced, for example, by reacting amine compound (a) with hydrogen peroxide water as a reactant under conditions of 30 to 100°C. In this reaction, a water-soluble organic solvent such as 2-propanol or water can be used as a solvent to suppress the heat of reaction and dissolve the raw materials and products.

[0068] • Amount of hydrogen peroxide used for amine compound (a) In the method for producing the amine oxide compound (c), the amount of hydrogen peroxide used relative to the amine compound (a) can be, for example, 1 to 3 molar equivalents of hydrogen peroxide per 1 molar equivalent of the amine compound (a). To reduce by-products, it is preferable to use 1 to 1.5 molar equivalents of hydrogen peroxide per 1 molar equivalent of amine compound (a). Examples of amine oxide compounds (c) that can be produced by the above manufacturing method include those represented by formulas (c-1) to (c-6) above.

[0069] Method for producing cationic compound (d) The cationic compound (d) can be produced by using an alkyl halide, such as methyl iodide, as a reactant and reacting the alkyl halide with the amine compound (a) under conditions of 20 to 50°C. In this reaction, a water-soluble organic solvent such as 2-propanol or water can be used as a solvent to suppress the heat of reaction and dissolve the raw materials and products.

[0070] • Amount of alkyl halogen used relative to amine compound (a) In the method for producing the cationic compound (d), the amount of alkyl halide used relative to the amine compound (a) can be, for example, 1 to 2 molar equivalents of alkyl halide per 1 molar equivalent of amine compound (a). To reduce by-products, it is preferable to use 1 to 1.1 molar equivalents of alkyl halide per 1 molar equivalent of amine compound (a).

[0071] Examples of cationic compounds (d) that can be produced by the above manufacturing method include the compounds represented by formulas (d-1) to (d-10) above.

[0072] • Another method for producing cationic compounds (d) Another method for producing cationic compound (d) is to use a compound having a group represented by formula (2) and / or a group represented by formula (6) in formula (1) as a starting material, and react the starting material with an acid (e.g., hydrochloric acid, bromic acid, hydrogen iodide; an organic acid such as acetic acid) to cationize the nitrogen atom in formula (2) and / or formula (6) with the acid, thereby producing cationic compound (d). The above reaction may be carried out in a water-soluble organic solvent. Examples of the above raw materials include compounds in which X has a group represented by formula (2) in formula (1), and M has any of the groups represented by formulas (6) to (9). Examples include compounds in which X has a group represented by formula (3) and M has a group represented by formula (6) in formula (1). The amount of the above acid used for a compound in which X is a group represented by formula (2) and / or M is a group represented by formula (6) in formula (1) can be set so that the molar equivalent ratio of the above acid (acid / (total of formulas (2) and (6))) to the total molar equivalents of formulas (2) and (6) in the compound is 0.5 to 2. According to the above manufacturing method, for example, in equation (1), X is expressed in equation (3) and R in equation (3) 6 The group is a hydrogen atom and / or M is represented by formula (9) and R in formula (9) 8 Compounds having a group in which the atom is a hydrogen atom can be produced. Examples of cationic compounds (d) that can be produced by the above manufacturing method include the compounds represented by formulas (d-11) to (d-16) above.

[0073] • Water-soluble organic solvents Examples of water-soluble organic solvents that can be used in the above-mentioned method for producing the compound of the present invention include alcohols such as methanol, ethanol, isopropanol (isopropyl alcohol), and tert-butanol; ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate and ethyl acetate; polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, sulfolane, and N-methylpyrrolidone; glycol ethers such as diethylene glycol monomethyl ether and propylene glycol monomethyl ether acetate; and glycols such as ethylene glycol and propylene glycol.

[0074] • Amount of water and water-soluble organic solvents used The amount of water used in the above manufacturing method is not particularly limited. The same applies to the amount of water-soluble organic solvents used.

[0075] (use) When using the compound of the present invention, examples of the compound of the present invention include the compound alone and a mixture of the compound of the present invention and an aqueous medium.

[0076] ·Aqueous medium Examples of the aqueous media mentioned above include water, water-soluble organic solvents, or mixtures of water and water-soluble organic solvents. Examples of water-soluble organic solvents include alcohols such as methanol, ethanol, isopropanol, and tert-butanol; ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate and ethyl acetate; polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, sulfolane, and N-methylpyrrolidone; glycol ethers such as diethylene glycol monomethyl ether and propylene glycol monomethyl ether acetate; and glycols such as ethylene glycol and propylene glycol. If the compound of the present invention is a mixture with an aqueous medium, the aqueous medium contained in the mixture may include water and a water-soluble organic solvent used in the production of the compound of the present invention.

[0077] • Content of aqueous media When the compound of the present invention is in the form of a mixture with an aqueous medium, the content of the aqueous medium is not particularly limited.

[0078] (Application) The compounds of the present invention can be used, for example, as surfactants.

[0079] [Surfactants] The surfactant of the present invention is a surfactant that contains the compound of the present invention. [Compounds as essential components] The compound contained as an essential component in the surfactant of the present invention is not particularly limited as long as it is a compound of the present invention. The surfactant of the present invention contains one or more compounds of the present invention. The surfactant of the present invention contains two or more compounds of the present invention, and the combination thereof is not particularly limited. For example, the above combination includes R in formula (1). 1 Combinations of compounds with different branched alkyl groups represented by formula (2), and R 3 Compounds in which is a hydrogen atom and R in formula (2)3 Examples include combinations with compounds in which the group is represented by formula (5).

[0080] In the present invention, the compound of the present invention may be used as it is as the surfactant of the present invention.

[0081] [Surfactant composition] The surfactant composition of the present invention is a surfactant composition containing the surfactant of the present invention and an aqueous medium.

[0082] [Surfactant] The surfactant contained as an essential component in the surfactant composition of the present invention is not particularly limited as long as it is the surfactant of the present invention.

[0083] (Concentration of the surfactant of the present invention) The concentration of the surfactant of the present invention (one or more of the compounds of the present invention. When there are two or more of the compounds of the present invention, the total concentration thereof.) in the surfactant composition of the present invention is not particularly limited, and the concentration of the surfactant of the present invention in the surfactant composition of the present invention may be more than 0% by mass and less than 1 hundred% by mass in the total amount of the surfactant composition of the present invention. In addition, from the following viewpoints, the concentration of the surfactant of the present invention in the surfactant composition of the present invention is preferably 10 to 70% by mass, and particularly preferably 15 to 60% by mass. When it is within the above range, since the amount of the solvent (including the aqueous medium) in the surfactant composition of the present invention is small, when the surfactant composition of the present invention is used as an additive, it is easy to make the amount of the surfactant of the present invention an appropriate amount, which is preferable. In addition, when it is within the above range, the viscosity of the surfactant composition of the present invention does not become too high and the handling property is good, and it is preferable that the surfactant of the present invention is not easily precipitated during storage.

[0084] [Aqueous medium] Examples of the aqueous medium contained as an essential component in the surfactant composition of the present invention include water, a water-soluble organic solvent, or a mixture of water and a water-soluble organic solvent. Examples of the water-soluble organic solvents include alcohols such as methanol, ethanol, isopropanol, and tertiary butanol; ketones such as acetone and methyl ethyl ketone; esters such as methyl acetate and ethyl acetate; polar solvents such as N,N-dimethylformamide, dimethyl sulfoxide, sulfolane, and N-methylpyrrolidone; glycol ethers such as diethylene glycol monomethyl ether and propylene glycol monomethyl ether acetate; and glycols such as ethylene glycol and propylene glycol. When the aqueous medium is a mixture of water and a water-soluble organic solvent, the mass ratio of water to the water-soluble organic solvent is not particularly limited.

[0085] (Additive) The surfactant composition of the present invention can further contain, for example, other surfactants, pH adjusters, rust inhibitors, dyes, dye stabilizers, flame retardants, antifoaming agents, and antistatic agents, as long as the effects of the present invention are not impaired. The type and content of the additives can be appropriately selected.

[0086] (Other surfactants) The surfactant composition of the present invention may further contain a surfactant other than the compound of the present invention (other surfactants). The other surfactants are not particularly limited. For example, conventionally known ones can be mentioned. It is possible not to use a fluorine-based surfactant as the other surfactant.

[0087] (Production method) Examples of the production method of the surfactant composition of the present invention include a method of producing the surfactant composition of the present invention by mixing the surfactant of the present invention, an aqueous medium, and additives that can be used as necessary.

[0088] (Use) The surfactant composition of the present invention can exhibit sufficient surface tension reduction ability even at low concentrations, making it suitable for use as an additive in various applications. For example, the surfactant composition of the present invention can be used as a leveling agent for waxes, a foaming aid, an additive for stable foam generation and improved fire extinguishing performance for foam fire extinguishing, a cleaning agent, a mold release agent, an emulsifier, a rust inhibitor, a latex stabilizer, an antifogging agent for agricultural films, a pigment dispersant, an improver of wettability and penetration of inks, paints, resists, etc., to impart water and oil repellency to curable resins, an antifogging agent for agricultural films, an antifouling agent, a flotation agent, a smoothing agent, a deinking agent, and so on. Furthermore, the surfactant composition of the present invention can be used in a wide range of applications, such as cleaning and gravure printing. Furthermore, the surfactants and surfactant compositions of the present invention can lower the surface tension of various liquids without being limited by the solvent composition by adding the surfactant or surfactant composition of the present invention to the liquids. The amount of the surfactant or surfactant composition of the present invention to be added is set appropriately depending on the purpose and usage conditions, but it is preferable that the mixture contains compound (1) in an amount of 0.001 to 5% by mass in the state in which it is actually used (in the mixture after adding the surfactant or surfactant composition of the present invention to various liquids), and more preferably 0.005 to 1% by mass. When it is within the above range, it is preferable because it can fully exhibit its surface tension lowering ability without canceling out the functionality of the main component (the liquid before adding the surfactant or surfactant composition of the present invention). If the surfactant or surfactant composition of the present invention contains two or more types of compound (1), it is preferable that the total amount is within the above range. In addition, its surface tension lowering ability can impart functions such as leveling, permeability, foaming, cleaning, and emulsification to the added liquid. [Examples]

[0089] The present invention will be described in more detail below based on examples. The materials, quantities, proportions, processing details, and processing procedures shown in the following examples can be modified as appropriate without departing from the spirit of the present invention. Therefore, the scope of the present invention should not be interpreted as being limited by the following examples. In the following, unless otherwise specified, "parts" and "%" refer to "parts by mass" and "% by mass," respectively.

[0090] (Synthesis of 2-(((3,5,5-trimethylhexyl)oxymethyl)oxirane) Epichlorohydrin (384.81g, 4159 mmol), 3,5,5-trimethyl-1-hexanol (400.00g, 2773 mmol), sodium hydroxide (166.40g, 4160 mmol), and tetrabutylammonium bromide (44.69g, 139 mmol) were charged into a 2000 ml glass flask. The mixture was heated to 30°C and the reaction was carried out at that temperature for 11 hours to react epichlorohydrin with 3,5,5-trimethyl-1-hexanol. Gas chromatography analysis of the reaction solution revealed that the reaction rate of 3,5,5-trimethyl-1-hexanol was over 88%. The reaction mixture was transferred to a separatory funnel, deionized water and ethyl acetate were added, and after separation and filtration, the ethyl acetate was removed by distillation using an evaporator. By distillation of this distillate, 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane (356.96 g, purity 98%, yield 63%; structure represented by formula (15) below) was obtained. [ka]

[0091] <Gas chromatography analysis> The measurement conditions for the gas chromatography analysis described above are as follows: Equipment: GC-2014 (manufactured by Shimadzu Corporation) Column: DB-5msUI (manufactured by Agilent Technologies, Inc.) (inner diameter 0.25 mm, length 30 m, film thickness 0.25 μm) Inlet temperature: 250℃ Injection method: Split Split ratio: 50 Column temperature program: Hold at 50°C for 5 minutes, increase the temperature at 10°C / min to 250°C, and hold at 250°C for 10 minutes.

[0092] [Example 1] Synthesis of amine compound (a-1) [ka]

[0093] Diethylaminopropylamine (236.41g, 1815 mmol) and isopropyl alcohol (164.01g, 2723 mmol) are placed in a 1000 ml glass flask, and the temperature is raised to 65°C. The 2-(((3,5,5-trimethylhexyl)oxymethyl)oxirane (184.52 g, 908 mmol) represented by the above formula (15) was added dropwise over 2 hours, and the reaction was carried out at the same temperature for 4 hours. Gas chromatography analysis of the reaction solution revealed that the reaction rate of 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane was over 98%. The reaction mixture was transferred to a 2000 ml round-bottom flask, and the isopropyl alcohol was removed by distillation using an evaporator to obtain amine compound (a-1) (282.37 g, purity 96.4%, yield 91%).

[0094] The compound synthesized as described above 1 H-NMR and 13 The 1C-NMR spectral data was as follows: 11H-NMR (400 MHz, solvent: acetone-d6, standard substance: TMS), δ (ppm): 0.91 (s, 9H), 0.94 (d, J = 6.4 Hz, 3H), 0.98 (t, J = 6.8 Hz, 7.2 Hz, 6H), 1.04 - 1.09 (m, 1H), 1.25 - 1.29 (m, 1H), 1.33 - 1.42 (m, 1H), 1.51 - 1.62 (m, 1H), 1.63 - 1.75 (m, 1H), 2.43 - 2.49 (m, 6H), 2.51 - 2.70 (m, 4H), 3.37 - 3.39 (m, 2H), 3.44 - 3.48 (m, 2H), 3.72 - 3.85 (m, 1H) 13 13C-NMR (100 MHz, solvent: acetone-d6), δ (ppm): 12.5, 23.2, 26.8, 28.5, 29.3, 31.6, 40.0, 47.0, 47.6, 49.2, 51.9, 53.8, 69.7, 70.1, 74.7

[0095] As described above, for the compound synthesized 1 1H-NMR and 13 From the results of the 13C-NMR spectral data, it was confirmed that the compound obtained by the above reaction was the compound represented by the above formula (a-1). The amine compound (a-1) produced as described above was used as surfactant 1.

[0096] [Example 2] Synthesis of amine compound (a-3) [Chemical formula]

[0097] A 50 ml glass flask was charged with diethylaminopropylamine (6.13 g, 47 mmol) and isopropyl alcohol (8.49 g, 141 mmol), and after heating to 65°C, 2-(((3,5,5-Trimethylhexyl)oxy)methyl)oxirane (19.11 g, 94 mmol) represented by the above formula (15) was added dropwise over 2 hours and reacted at the same temperature for 4 hours. Gas chromatography analysis of the reaction solution revealed that the reaction rate of 2-(((3,5,5-trimethylhexyl)oxy)methyl)oxirane was over 99%. The reaction mixture was transferred to a 200 ml round-bottom flask, and the isopropyl alcohol was removed by distillation using an evaporator to obtain the amine compound (a-3) (22.36 g, purity 83.0%, yield 74%).

[0098] The compound synthesized as described above 1 H-NMR and 13 The 1C-NMR spectral data was as follows: 1 H-NMR (400MHz, solvent: acetone-d6, standard material: TMS), δ(ppm): 0.91(s, 18H), 0.93(d, J=6.8Hz, 6H), 0.99(t, J=7.6Hz, 6.8Hz, 6H), 1.25-1.29(m, 2H), 1.25-1.29( m, 2H), 1.52-1.62(m, 2H), 1.64-1.72(m, 2H), 2.40-2.51(m, 8H), 2.53-2. 71(m, 4H), 3.37(d, J=5.6Hz, 4H), 3.46(t, J=6.4Hz, 4H), 3.72-3.85(m, 2H) 13 ¹¹C-NMR (100 MHz, solvent: acetone-d6), δ (ppm): 11.7, 23.2, 25.4, 26.8, 29.3, 31.6, 40.0, 47.0, 47.6, 51.0, 51.9, 54.2, 69.6, 70.1, 74.4

[0099] The compound synthesized as described above 1 H-NMR and 13 From the 1C-NMR spectral data, it was confirmed that the compound obtained by the above reaction is the compound represented by formula (a-3) above. The amine compound (a-3) produced as described above was used as surfactant 2.

[0100] [Example 3] Synthesis of amphoteric compound (b-1) [ka]

[0101] In a 50 ml glass flask, add amine compound (a-1) (10.21 g, 31 mmol) and isopropyl alcohol (4.33 g, 72 mmol), and after raising the temperature to 40°C, The pre-mixed monochloroacetic acid (4.38 g, 46 mmol) and isopropyl alcohol (4.11 g, 68 mmol) were added dropwise over 30 minutes, and the reaction was carried out at 60°C for 2 hours. After cooling the reaction mixture to 40°C, 48% potassium hydroxide (5.42 g, 46 mmol) was added dropwise over 1 hour, and the reaction was carried out at 65°C for 18 hours. Gas chromatography analysis of the reaction solution revealed that the reaction rate of amine compound (a-1) was over 93%. After adding isopropyl alcohol (9.84 g, 164 mmol) to the reaction mixture, it was stirred for more than 15 hours. The inorganic salts, which are by-products, were removed by filtration, and the concentration was adjusted with deionized water to obtain a water / isopropyl alcohol solution containing 40% of the amphoteric compound (b-1) (39.12 g, yield 97.8%).

[0102] The compound synthesized as described above 1 H-NMR and 13 The 1C-NMR spectral data was as follows: 1 H-NMR (400MHz, solvent: acetone-d6, standard material: TMS), δ (ppm): 0.91 (s, 9H), 0.93 (d, J=6.8Hz, 3H), 1.04-1. 09(m, 1H), 1.12-1.22(m, 1H), 1.27(t, J=7.2Hz, 7.6Hz, 6H), 1.34-1.48(m, 2H), 1.52-1.61(m, 1H), 1.63-1.68(m, 1H), 1.88-1.93(m, 1H), 2.52-2.68(m, 2H), 2.71-2.97(m, 3H), 3.11-3.20( m, 4H), 3.22-3.25(m, 1H), 3.29-3.43(m, 2H), 3.47(t, J=6.8Hz, 6.4Hz, 2H), 3.65-3.95(m, 3H) 13 ¹³C-NMR (100 MHz, solvent: acetone-d6), δ (ppm): 9.0, 22.2, 23.4, 26.7, 29.3, 31.6, 40.0, 45.0, 46.5, 50.9, 51.9, 53.4, 59.4, 68.3, 70.2, 74.6, 176.0

[0103] The compound synthesized as described above 1 H-NMR and 13 From the 1C-NMR spectral data, it was confirmed that the compound obtained by the above reaction is an amphoteric compound represented by formula (b-1) above. The amphoteric compound (b-1) produced as described above was used as surfactant 3.

[0104] [Example 4] Synthesis of amphoteric compound (b-5) [ka]

[0105] In a 50 ml glass flask, add amine compound (a-3) (10.83 g, 20 mmol) and isopropyl alcohol (4.60 g, 77 mmol), and after raising the temperature to 40°C, A pre-mixed solution of monochloroacetic acid (2.89 g, 31 mmol) and isopropyl alcohol (4.34 g, 72 mmol) was added dropwise over 30 minutes, and the reaction was carried out at 60°C for 2 hours. After cooling the reaction mixture to 40°C, a 48% potassium hydroxide aqueous solution (3.58 g, 31 mmol) was added dropwise over 1 hour, and the reaction was carried out at 65°C for 18 hours. Gas chromatography analysis of the reaction solution revealed that the reaction rate of amine compound (a-3) was over 97%. After adding isopropyl alcohol (9.44 g, 157 mmol) to the reaction mixture, it was stirred for more than 15 hours. By filtration, the inorganic salt, a by-product, was removed to obtain a water / isopropyl alcohol solution (33.00 g, yield 82.5%) containing 40% of the amphoteric compound (b-5).

[0106] The compound synthesized as described above 1 H-NMR and 13 The 1C-NMR spectral data was as follows: 1 H-NMR (400MHz, solvent: acetone-d6, standard material: TMS), δ (ppm): 0.91 (s, 18H), 0.93 (d, J=6.8Hz, 6 H), 1.04-1.09(m, 2H), 1.19-1.33(m, 8H), 1.34-1.47(m, 2H), 1.52-1.60(m, 2H), 1.6 2-1.70(m, 2H), 1.82-2.04(m, 2H) 2.49-2.70(m, 4H), 2.72-2.80(m, 2H), 3.06-3.17 (m, 4H), 3.20-3.34(m, 2H), 3.35-3.44(m, 4H), 3.45-3.49(m, 4H), 3.78-3.94(m, 4H) 13 ¹³C-NMR (100 MHz, solvent: acetone-d6), δ (ppm): 9.1, 23.0, 23.2, 26.9, 29.3, 31.6, 39.9, 44.9, 46.8, 50.6, 52.1, 53.7, 62.0, 67.8, 70.2, 74.5, 177.3

[0107] The compound synthesized as described above 1 H-NMR and 13 From the 1C-NMR spectral data, it was confirmed that the compound obtained by the above reaction is an amphoteric compound represented by formula (b-5) above. The amphoteric compound (b-5) produced as described above was used as surfactant 4.

[0108] [Example 5] Synthesis of amine oxide compound (c-1) [ka]

[0109] In a 50 ml glass flask, amine compound (a-1) (10.00 g, 30 mmol), isopropyl alcohol (10.50 g, 175 mmol), and deionized water (5.26 g, 292 mmol) were charged. After raising the temperature to 65°C, 35% hydrogen peroxide solution (4.41 g, 45 mmol) was added dropwise over 2 hours, and the reaction was carried out at 67°C for 4 hours. Gas chromatography analysis of the reaction solution revealed that the reaction rate of amine compound (a-1) was over 93%. A water / isopropyl alcohol solution containing 32% of the amine oxide compound (c-1) was obtained (28.47 g, yield 81%).

[0110] The compound synthesized as described above 1 H-NMR and 13 The 1C-NMR spectral data was as follows: 1 H-NMR (400MHz, solvent: acetone-d6, standard material: TMS), δ (ppm): 0.91 (s, 9H), 0.94 (d, J=6.4Hz, 3H), 0.98-1.09 (m, 2H), 1.17-1.30 (m, 7H), 1.33-1.40 (m, 1H), 1.51 -1.59(m, 1H), 1.61-1.70(m, 1H), 1.86-2.02(m, 1H), 2.41-3.03(m, 4H), 3 .04-3.34(m, 4H), 3.36-3.41(m, 2H), 3.44-3.49(m, 4H), 3.94-4.04(m, 1H) 13 ¹³C-NMR (100 MHz, solvent: acetone-d6), δ (ppm): 8.6, 21.1, 23.2, 26.9, 29.3, 31.6, 39.9, 46.9, 51.9, 55.1, 62.3, 64.9, 68.6, 70.1, 74.6

[0111] The compound synthesized as described above 1 H-NMR and 13 From the 1C-NMR spectral data, it was confirmed that the compound obtained by the above reaction is an amine oxide compound represented by formula (c-1) above. The amine oxide compound (c-1) produced as described above was used as surfactant 5.

[0112] [Example 6] Synthesis of a mixture of cationic compounds (d-1) and (d-7) [ka] TIFF2026083806000064.tif20142

[0113] In a 50 ml glass flask, amine compound (a-1) (10.00 g, 30 mmol), isopropyl alcohol (11.90 g, 198 mmol), and deionized water (2.99 g, 166 mmol) were charged. After raising the temperature to 30°C, methyl iodide (4.51 g, 32 mmol) was added dropwise over 10 minutes, and the reaction was carried out at 37°C for 3 hours. Gas chromatography analysis of the reaction solution revealed that the reaction rate of amine compound (a-1) was over 93%. As a result of the above synthesis, a water / isopropyl alcohol solution containing 50% of the cationic compounds (d-1) and (d-7) was obtained (47.65 g, yield 78%).

[0114] The compound synthesized as described above 1 H-NMR and 13 The 1C-NMR spectral data was as follows: 1 H-NMR (400MHz, solvent: acetone-d6, standard material: TMS), δ (ppm): 0.91 (s, 9H), 0.94 (d, J=6.4Hz, 3H), 1. 11-1.16(m, 1H), 1.25-1.29(m, 2H), 1.34-1.40(m, 1H), 1.42-1.49(m, 6H), 1.52-1.60(m, 1H), 1.63-1.71(m, 1H), 2.52-3.16(m, 4H), 3.26-3.27(m, 4H), 3.39-3.44(m, 1H), 3.45- 3.50(m, 3H), 3.53-3.56(m, 1H), 3.63-3.69(m, 2H), 3.73-3.83(m, 1H), 3.97-4.16(m, 2H) 13 13C-NMR (100 MHz, solvent: acetone-d6), δ (ppm): 8.3, 9.3, 20.8, 21.4, 22.3, 23.2, 25.7, 26.8, 29.8, 31.6, 39.9, 42.3, 47.5, 50.3, 51.8, 52.9, 53.6, 57.4, 61.4, 67.3, 68.2, 70.1, 74.4

[0115] As described above, for the compound synthesized 1 1H-NMR and 13 from the results of the 13C-NMR spectral data, it was confirmed that the compound obtained by the above reaction was a cationic compound represented by the above formulas (d-1) and (d-7). A mixture containing the cationic compounds (d-1) and (d-7) produced as described above was used as surfactant 6.

[0116] (Analysis) In the present invention, for the above-mentioned 1 1H-NMR, 13 13C-NMR, a part of the obtained solution was dried, and for the solid content, NMR analysis ( 1 1H-NMR, 13 13C-NMR) was performed using FT / IR-4600 (manufactured by JASCO Corporation) and JNM-ECZ400R / S1 (manufactured by JEOL Ltd.).

[0117] <Measurement of NMR> Regarding the measurement of NMR ( 1 1H-NMR, 13 13C-NMR), it is shown below. The measurement target substance was dissolved in the heavy solvent acetone-d6, and it was prepared so that the concentration of the measurement target substance became about 5% by mass. The prepared solution was transferred to a measurement tube for NMR. In addition, a small amount of a reference substance was added for the measurement of each nuclide. The measurement conditions are shown below. Apparatus: JNM-ECZ400R / S1 (manufactured by JEOL Ltd., 400 MHz) Nuclide: 1 1H-NMR (standard: TMS), 13 13C-NMR

[0118] [Manufacturing of surfactant compositions] Next, ion-exchanged water was added to water / isopropyl alcohol solutions containing surfactants 3-6, which were manufactured as described above, to obtain water / isopropyl alcohol solutions containing 30% of each surfactant. A water / isopropyl alcohol solution containing 30% of each of the above-mentioned surfactants corresponds to the surfactant composition of the present invention. A water / isopropyl alcohol solution containing surfactant 3 will also be referred to as "surfactant composition 3" below. A water / isopropyl alcohol solution containing surfactants 4 to 6 will also be referred to as "surfactant composition 4," "surfactant composition 5," and "surfactant composition 6" below.

[0119] [evaluation] The following evaluations were performed using each of the evaluation solutions obtained as described below. The results are shown in Tables 1 and 2.

[0120] [Preparation of evaluation solution] (Examples 7-10) As described above, surfactant compositions 3 to 6 were prepared by diluting each with deionized water to a surfactant concentration of 0.1% by mass, and evaluation solutions 1 to 4 were prepared (see Examples 7 to 10 and Table 1).

[0121] (Examples 11-16) Using the surfactants 1 and 2 and surfactant compositions 3 to 6 manufactured as described above, each surfactant or surfactant composition was diluted with 0.1 mol / l hydrochloric acid to prepare evaluation solutions 5 to 10, such that the surfactant concentration of each surfactant or surfactant composition after dilution was 0.1% by mass (see Examples 11 to 16 and Table 2).

[0122] [Example 11] The surfactant contained in evaluation solution 5 obtained in Example 11 includes a compound in which one or both of the secondary and tertiary amines of the amine compound (a-1) having the following structure are cationized with hydrochloric acid. [ka] The compound in which both the secondary and tertiary amines of the amine compound (a-1) are cationized with hydrochloric acid is a cationic compound represented by the following formula (d-11). [ka]

[0123] [Example 12] The surfactant contained in evaluation solution 6 obtained in Example 12 includes a compound in which one or both of the two tertiary amines of the amine compound (a-3) having the structure shown below are cationized with hydrochloric acid. [ka] The compound in which both tertiary amines of amine compound (a-3) are cationized with hydrochloric acid is a cationic compound represented by the following formula (d-16). [ka]

[0124] [Example 13] The surfactant contained in evaluation solution 7 obtained in Example 13 includes a cationic compound in which one or both of the two tertiary amines of the amphoteric compound (b-1) having the structure shown below are cationized with hydrochloric acid. [ka]

[0125] [Example 14] The surfactant contained in evaluation solution 8 obtained in Example 14 includes a cationic compound in which the tertiary amine of the amphoteric compound (b-5) having the following structure is cationized with hydrochloric acid. [ka]

[0126] [Example 15] The surfactant contained in evaluation solution 9 obtained in Example 15 includes a cationic compound in which the tertiary amine of the amine oxide compound (c-1) having the following structure is cationized with hydrochloric acid. [ka]

[0127] [Example 16] The surfactant contained in evaluation solution 5 obtained in Example 16 includes a cationic compound in which the secondary amine of the cationic compound (d-1) having the structure below is further cationized with hydrochloric acid, and / or a cationic compound in which the tertiary amine of the cationic compound (d-7) is further cationized with hydrochloric acid. [ka] TIFF2026083806000073.tif20142

[0128] (Comparative Example 1) As a surfactant, 3-(dodecyldimethylammonio)propanesulfonate (manufactured by Tokyo Chemical Industry Co., Ltd., structure shown below; the above compound is also referred to as "comparative compound 1") was used. The dodecyl group in 3-(dodecyldimethylammonio)propanesulfonate is not a branched alkyl group. [ka] Deionized water was added to the above comparative compound 1 to prepare evaluation solution 11 containing the above comparative compound 1 as a surfactant (see Comparative Example 1, Table 1). The concentration of comparative compound 1 in the total volume of evaluation solution 11 was 0.1% by mass.

[0129] (Comparative Example 2) Hexadecyltrimethylammonium bromide (manufactured by Tokyo Chemical Industry Co., Ltd., structure shown below; the above compound is also referred to as "comparative compound 2") was used as the surfactant. The hexadecyl group in hexadecyltrimethylammonium bromide is not a branched alkyl group. [ka] Deionized water was added to the above comparative compound 2 to prepare evaluation solution 12 containing the above comparative compound 2 as a surfactant (see Comparative Example 2, Table 1). The concentration of comparative compound 2 in the total volume of evaluation solution 12 was 0.1% by mass.

[0130] (Method for measuring surface tension) The static surface tension (mN / m) of each of the above-mentioned evaluation solutions was measured using the Wilhelmy method (platinum plate) at 25°C using a multi-functional automatic surface tension meter K100 (manufactured by KRUSS). In this invention, the ability to reduce surface tension was evaluated using the static surface tension measured as described above.

[0131] (Static surface tension of fluorinated surfactants) Generally, the static surface tension of fluorinated surfactants containing perfluoroalkyl groups is required to be approximately 15 to 27 mN / m at 0.1% by mass.

[0132] (Evaluation criteria for surface tension reduction ability in the present invention) In this invention, when the static surface tension measured as described above was 27 mN / m or less, the surface tension-reducing ability of the non-fluorinated compound contained in the surfactant composition was evaluated to be at a level equivalent to or better than that of a fluorinated surfactant. The lower the static surface tension is compared to 27 mN / m, the better the surface tension reduction ability, and therefore preferable. On the other hand, when the static surface tension exceeded 27 mN / m, it was evaluated that the surface tension-reducing ability of the non-fluorinated compound contained in the surfactant composition was insufficient compared to the surface tension-reducing ability of the fluorinated surfactant.

[0133] [Table 1] [Table 2]

[0134] The results in Table 1 confirm that the compound of the present invention exhibits the desired effect. On the other hand, the surface tension reduction ability of Comparative Examples 1 and 2, which did not contain the compound of the present invention but instead contained Comparative Compound 1 or Comparative Compound 2, was insufficient compared to the surface tension reduction ability of fluorinated surfactants.

Claims

1. A compound represented by the following formula (1). R １ -O-C ｐ H ２ｐ -CR ２ (OH)-C ｑ H ２ｑ -X-C ｒ H ２ｒ -M (1) The symbols in equation (1) have the following meanings: R １ : A branched alkyl group having 9 to 18 carbon atoms R ２ : Hydrogen atom or alkyl group having 1 to 6 carbon atoms p, q, and r: Integers from 1 to 6, independent of each other. X: A base represented by the following formula (2) or formula (3) 【Chemistry 1】 【change】 R ３ : Mutually independent of each other, a hydrogen atom, an alkyl group having 1 to 12 carbon atoms, a group represented by the following formula (4), or a group represented by the following formula (5) HOCO-CH ２ - (4) R ４ -O-C ｘ H ２ｘ -CR ５ (OH)-C ｙ H ２ｙ - (5) R ４ : Branched alkyl groups with 9 to 18 carbon atoms R ５ : Hydrogen atom or alkyl group having 1 to 6 carbon atoms x and y: Independent integers from 1 to 6 R ６ : Hydrogen atom or alkyl group having 1 to 6 carbon atoms Y - : Iodide ions, chloride ions, bromide ions, or organic acid ions M: The base represented by the following formulas (6) to (9) 【Chemistry 2】 【change】 【change】 【change】 R ７ : A C1-C6 alkyl group, independently of each other. R ８ : Hydrogen atom or alkyl group having 1 to 6 carbon atoms Z - : Iodide ions, chloride ions, bromide ions, or organic acid ions

2. In the above formula (1), R ２ The compound according to claim 1, wherein is a hydrogen atom.

3. In formula (1), X is the group represented by formula (2), and in formula (2), R ３ The compound according to claim 1, wherein is a group represented by formula (4), and in formula (1), M is a group represented by formula (6).

4. In formula (1), X is the group represented by formula (2), and in formula (2), R ３ The compound according to claim 1, wherein is a hydrogen atom or a group represented by formula (5), and in formula (1), M is a group represented by formula (8) or formula (9).

5. R in formula (1) １ or R in formula (5) above ４ The compound according to claim 1, wherein each group is independently a branched alkyl group selected from the groups represented by the following formulas (10) to (12). 【Transformation 3】 【change】 【change】

6. A surfactant containing the compound described in any one of claims 1 to 5.

7. A surfactant composition comprising the surfactant described in claim 6 and an aqueous medium.

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