(POLY)alkylene glycol-containing compound

Abstract

To provide a compound exhibiting excellent cleaning performance against mud stains and low critical micelle concentration.SOLUTION: A (poly)alkylene glycol-containing compound comprises a hydrophobic structural domain (A), a (poly)alkylene glycol domain (B), and a structural domain with a cyclic structure (C), wherein atoms forming the cyclic structure comprise nitrogen and oxygen atoms.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a (poly)alkylene glycol-containing compound. More specifically, the present invention relates to a (poly)alkylene glycol-containing compound useful in detergent compositions and the like. [Background technology]

[0002] Compounds having a (poly)alkylene glycol chain are endowed with properties such as hydrophilicity or hydrophobicity, flexibility, and steric repulsion by appropriately adjusting the chain length or the constituent alkylene oxides, and are used in various applications such as detergent builders, detergents, water treatment agents, scale inhibitors, and dispersants. It is also known that hydrophobic group-containing alkylene oxides obtained by addition reaction of alkylene oxides such as ethylene oxide with alcohols having hydrophobic groups, such as higher alcohols and benzyl alcohol, are useful in various detergent compositions. For example, Patent Document 1 discloses an alkylene oxide polymer having two types of hydrophobic groups, a hydrocarbon group having 6 to 20 carbon atoms and an aromatic ring, and a hydrocarbon group having 1 to 30 carbon atoms, and having a structural unit derived from polyalkylene oxide. For example, Patent Document 2 discloses a (poly)alkylene glycol-containing compound having a hydrophobic structural portion (A), a (poly)alkylene glycol portion (B), and a structural portion (C) having a ring structure containing a nitrogen atom, the hydrophobic structural portion (A) being located at an end of the compound, and the structural portion (C) having two or more atoms forming the ring structure being heteroatoms and / or having aromaticity. [Prior art documents] [Patent documents]

[0003] [Patent Document 1] JP 2023-57570 A [Patent Document 2] International Publication No. 2021 / 182152 Summary of the Invention [Problem to be solved by the invention]

[0004] As described above, although compounds having a (poly)alkylene glycol structure and a hydrophobic group have been disclosed in the past, there has been a demand for the development of a compound that has excellent detergency against muddy stains and a low critical micelle concentration from the viewpoint of reducing the amount of detergent used.

[0005] The present invention has been made in view of the above-mentioned current situation, and an object of the present invention is to provide a compound that has excellent detergency against muddy stains and a low critical micelle concentration. [Means for solving the problem]

[0006] The present inventors have conducted extensive research into (poly)alkylene glycol-containing compounds and have found that a (poly)alkylene glycol-containing compound having a hydrophobic structural portion, a (poly)alkylene glycol portion, and a structural portion having a ring structure formed by atoms including a nitrogen atom and an oxygen atom has excellent cleaning power against muddy stains and reaches a critical micelle concentration at a low concentration. They have thus come to the conclusion that the above-mentioned problems can be solved in an excellent manner, and have thus arrived at the present invention.

[0007] The present invention includes the following (poly)alkylene glycol-containing compounds, etc. [1] A (poly)alkylene glycol-containing compound having a hydrophobic structural portion (A), a (poly)alkylene glycol portion (B), and a structural portion (C) having a ring structure, the atoms forming the ring structure including a nitrogen atom and an oxygen atom. [2] The (poly)alkylene glycol-containing compound is represented by the following formula (1); [ka] (In the formula, R 1 R represents a hydrophobic group. 4 R represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. 2 R represents a trivalent hydrocarbon group having 1 to 10 carbon atoms which may have a heteroatom. 3are the same or different and each represents an alkylene group having 2 to 20 carbon atoms. A is the same or different and represents a substituent having a ring structure, and the atoms forming the ring structure include a nitrogen atom and an oxygen atom. X 1 , X 2 and m and n are the same or different and represent a direct bond or a divalent linking group. m and n are the same or different and represent numbers from 1 to 100. The (poly)alkylene glycol-containing compound according to the above-mentioned [1], [3] R above 2 are the same or different and are represented by the following formulas (2) to (2''); [ka] (In the formula, x represents 0 or 1. 5 represents a direct bond, or an alkylene group having 1 to 8 carbon atoms which may have a heteroatom. [4] A method for producing the (poly)alkylene glycol-containing compound according to any one of the above [1] to [3], the method comprising any one of the following steps (i) to (iv): (i) a first step of reacting a cyclic compound containing a nitrogen atom and an oxygen atom with a compound having a hydrophobic group, and a second step of reacting the reaction product obtained in the first step with a (poly)alkylene glycol or an alkylene oxide. (ii) A step of reacting a cyclic compound containing a nitrogen atom and an oxygen atom with a compound having a hydrophobic group at one end of a (poly)alkylene glycol. (iii) a first step of reacting a cyclic compound containing a nitrogen atom and an oxygen atom with a (poly)alkylene glycol or an alkylene oxide, and a second step of reacting the reaction product obtained in the first step with a compound having a hydrophobic group. (iv) reacting a cyclic compound containing a hydrophobic group, a nitrogen atom, and an oxygen atom with a (poly)alkylene glycol or an alkylene oxide; [5] A composition comprising the (poly)alkylene glycol-containing compound according to any one of [1] to [3] above and other components other than the compound, wherein the content of the (poly)alkylene glycol-containing compound is 1 to 99% by mass relative to 100% by mass of the composition. [6] A detergent composition comprising the (poly)alkylene glycol-containing compound according to any one of the above [1] to [3] and a detergent additive other than the compound. [7] A detergent composition comprising the (poly)alkylene glycol-containing compound according to any one of [1] to [3] above and a surfactant. Effect of the Invention

[0008] The (poly)alkylene glycol-containing compound of the present invention has the above-mentioned constitution, has excellent detergency against muddy stains, and has a low critical micelle concentration, and therefore can be suitably used in detergents and the like. [Brief description of the drawings]

[0009] [Figure 1] FIG. 1 is a graph in which the static surface tension γ is plotted against each concentration of the polyalkylene glycol-containing compound (1) of Example 1. [Diagram 2] FIG. 2 is a graph in which the static surface tension γ is plotted against each concentration of the comparative polyalkylene glycol-containing compound (2) of Comparative Example 1. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0010] The preferred embodiments of the present invention are specifically described below, but the present invention is not limited to the following description, and can be modified as appropriate within the scope of the present invention. In addition, a combination of two or more of the individual preferred embodiments of the present invention described below also falls within the preferred embodiments of the present invention.

[0011] [(Poly)alkylene glycol-containing compound] The (poly)alkylene glycol-containing compound (hereinafter also referred to as PAG compound) of the present invention has a hydrophobic structural portion (A), a (poly)alkylene glycol portion (B), and a structural portion (C) having a ring structure composed of atoms including a nitrogen atom and an oxygen atom. Since the (poly)alkylene glycol portion (B) in the PAG compound of the present invention is hydrophilic and the structural portion (C) has polarity due to a nitrogen atom and an oxygen atom, it is believed that the interaction with hydrophilic stains such as mud is strengthened, resulting in excellent cleaning power against hydrophilic stains. In addition, the PAG compound of the present invention has a hydrophobic structural portion (A), a hydrophilic (poly)alkylene glycol portion (B), and a polar structural portion (C), and is therefore thought to have an excellent balance of hydrophobicity and hydrophilicity and also excellent micelle forming ability, resulting in a low critical micelle concentration.

[0012] The PAG compound of the present invention is not particularly limited in terms of the positional relationship of the structural moieties (A), (B), and (C) as long as they have these moieties, but examples thereof include form (1) having the structural moieties (A), (B), and (C) in this order, and form (2) having the structural moieties (A), (C), and (B) in this order. Form (2) is preferred. In the case of the above form (2), a wettability gradient that gradually changes from hydrophobic to hydrophilic is formed in the compound, resulting in superior micelle formation ability.

[0013] The theoretical molecular weight of the PAG compound is not particularly limited, but is preferably 340 to 5000, more preferably 700 to 2500, and even more preferably 1000 to 2000. The theoretical molecular weight of the PAG compound can be calculated based on the molecular weight of each structural unit constituting the PAG compound and the number of each structural unit.

[0014] <Hydrophobic structural portion (A)> The hydrophobic structural portion (A) in the PAG compound is preferably a structure derived from an organic compound exhibiting hydrophobicity. The structural portion (A) derived from an organic compound exhibiting hydrophobicity means a structure obtained by abstracting one or more hydrogen atoms from the organic compound. It is preferable that the organic compound has an insoluble content of 9.5 g or more when 10 g is dissolved in 100 g of water at 25°C. The organic compound is preferably a hydrocarbon compound having 3 to 50 carbon atoms which may have a heteroatom. The number of carbon atoms in the hydrocarbon compound is preferably 4 to 30. More preferably, the number of carbon atoms is 5 to 24, still more preferably 6 to 20, still more preferably 8 to 18, and particularly preferably 10 to 14.

[0015] Examples of the hydrocarbon compound include acyclic hydrocarbon compounds, cyclic saturated hydrocarbon compounds, aromatic compounds, etc. The hydrocarbon compound may have a heteroatom such as a nitrogen atom, a sulfur atom, an oxygen atom, a phosphorus atom, a halogen atom, etc., as long as the hydrophobic structural portion of the PAG compound exhibits hydrophobicity, and may also have a substituent such as a hydroxyl group, an alkoxy group, a carboxyl group, an acyl group, a sulfonic acid group, an amino group, a phosphoric acid group, etc.

[0016] The hydrophobic structural portion (A) in the PAG compound is preferably a structure derived from at least one compound selected from the group consisting of acyclic hydrocarbon compounds having 1 to 50 carbon atoms which may have a heteroatom, cyclic saturated hydrocarbon compounds having 3 to 50 carbon atoms which may have a heteroatom, and aromatic compounds having 6 to 50 carbon atoms which may have a heteroatom.

[0017] Examples of the acyclic hydrocarbon compound include alkanes, alkenes, alkynes, and the like having 1 to 50 carbon atoms. Examples of alkanes having 1 to 50 carbon atoms include linear or branched alkanes such as methane, ethane, propane, butane, pentane, hexane, heptane, octane, nonane, decane, undecane, dodecane, tridecane, tetradecane, pentadecane, hexadecane, heptadecane, octadecane, nonadecane, icosane, henicosane, tetracosane, triacontane, tetracontane, and pentacontane.

[0018] Examples of alkenes having 2 to 50 carbon atoms include linear or branched alkenes such as ethylene, propene, butene, pentene, hexene, heptene, octene, nonene, decene, undecene, dodecene, tridecene, tetradecene, pentadecene, hexadecene, heptadecene, octadecene, nonadecene, icosene, henicosene, tetracosene, triacontene, tetracontene, and pentacontene.

[0019] Examples of alkynes having 2 to 50 carbon atoms include linear or branched alkynes such as acetylene, propyne, butyne, pentyne, hexyne, heptyne, octyne, nonyne, decyne, undecyne, dodecyne, tridecyne, tetradecyne, pentadecyne, hexadecyne, heptadecyne, octadecyne, nonadecyne, icosine, henicosine, tetracosine, triacontine, tetracontine, and pentacontine.

[0020] Examples of the cyclic saturated hydrocarbon compound having 3 to 50 carbon atoms include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, and the like, as well as compounds having one or more alkyl groups, alkenyl groups, or the like.

[0021] Examples of aromatic compounds having 6 to 50 carbon atoms include benzene, naphthalene, anthracene, phenanthrene, biphenyl, terphenyl, toluene, o-xylene, m-xylene, p-xylene, ot-butyltoluene, mt-butyltoluene, pt-butyltoluene, 1-ethyl-4-methylbenzene, 1-ethyl-3-methylbenzene, 1-isopropyl-4-methylbenzene, 1-t-butyl-4-methylbenzene, mesitylene, pseudocumene, durene, methylnaphthalene, dimethylnaphthalene, 1,2,3,4-tetrahydronaphthalene, methylanthracene, 4,4'-dimethylbiphenyl, ethylbenzene, propylbenzene, butylbenzene, 1,4-diethylbenzene, styrene, distyrenated phenyl, quaterphenyl, quinquephenyl, sexiphenyl, septiphenyl, octiphenyl, and the like, as well as compounds having one or more alkyl groups, alkenyl groups, or the like on an aromatic ring.

[0022] <(Poly)alkylene glycol moiety (B)> The PAG compound has a (poly)alkylene glycol moiety (B), and the alkylene groups constituting the moiety (B) may be the same or different and preferably have 2 to 20 carbon atoms. The alkylene groups each preferably have 2 to 20 carbon atoms, and may be the same or different. This means that when a plurality of alkylene groups are present in the (poly)alkylene glycol, the alkylene groups may all have the same number of carbon atoms or may be different. The position of the moiety (B) in the above PAG compound is not particularly limited, but it is preferably located at the end of the PAG compound, and more preferably has a (poly)alkylene glycol chain at the end of the compound. The (poly)alkylene glycol moiety (B) may have a hydrocarbon group which may have a heteroatom at its terminal, and the number of carbon atoms in the hydrocarbon group is preferably smaller than the number of carbon atoms contained in the hydrophobic structural moiety (A).

[0023] The (poly)alkylene glycol moiety (B) in the above PAG compound is represented by the following formula (3); -(R 3 O) n - (3) (In the formula, R 3 and are the same or different and represent an alkylene group having 2 to 20 carbon atoms. n is the same number from 1 to 100. R 3 represents an alkylene group having 2 to 20 carbon atoms, which may be the same or different, and is represented by n R 3 This means that all of the alkylene groups may be the same or different. R 3 The oxyalkylene group represented by O is an alkylene oxide adduct, and examples of such alkylene oxides include alkylene oxides having 2 to 8 carbon atoms, such as ethylene oxide, propylene oxide, butylene oxide, isobutylene oxide, 1-butene oxide, 2-butene oxide, and styrene oxide. From the viewpoint of imparting hydrophilicity to the (poly)alkylene glycol-containing compound, alkylene oxides having 2 to 4 carbon atoms, such as ethylene oxide, propylene oxide, and butylene oxide, are more preferred, and ethylene oxide and propylene oxide are even more preferred. In addition, when the polyalkylene glycol is an adduct of any two or more kinds of alkylene oxides selected from ethylene oxide, propylene oxide, butylene oxide, styrene oxide, etc., it may be in any form of random addition, block addition, alternating addition, etc. In order to ensure a balance between hydrophilicity and hydrophobicity, it is preferable that the oxyalkylene group in the (poly)alkylene glycol has an oxyethylene group as an essential component, more preferably 50 mol % or more of the oxyethylene group, and even more preferably 90 mol % or more of the oxyethylene group.

[0024] In the above formula (3), n is the average number of moles of oxyalkylene groups added, and represents a number from 1 to 100. n is preferably from 2 to 90, more preferably from 3 to 80, even more preferably from 4 to 70, still more preferably from 5 to 60, particularly preferably from 6 to 50, still more preferably from 7 to 45, still more preferably from 8 to 40, and most preferably from 10 to 30.

[0025] <Structural portion (C) having a ring structure composed of atoms including a nitrogen atom and an oxygen atom> The structural portion (C) in the PAG compound has a ring structure formed by atoms including a nitrogen atom and an oxygen atom. The ring structure may be one ring structure or a plurality of condensed rings, as long as it is constituted by atoms including a nitrogen atom and an oxygen atom. A ring structure having one ring structure is preferred. The ring structure may be an alicyclic structure or may have an unsaturated bond, and is preferably an alicyclic structure.

[0026] The number of atoms forming the ring structure is not particularly limited, and is, for example, preferably 3 to 16, more preferably 4 to 12, and further preferably 5 to 10. The ring structure may have at least one nitrogen atom and at least one oxygen atom, and is preferably in a form having at least one nitrogen atom and at least one oxygen atom. Furthermore, the ring structure may contain heteroatoms other than the nitrogen atom and oxygen atom as atoms forming the ring structure, but preferably does not contain other heteroatoms. The atoms forming the ring structure preferably include one nitrogen atom and one oxygen atom, and have 1 to 14 carbon atoms. The number of carbon atoms forming the ring structure is more preferably 2 to 10, and further preferably 3 to 6.

[0027] The structural portion (C) is represented by the following formula (4);

[0028] [ka]

[0029] (In the formula, R 2 represents a direct bond or a trivalent hydrocarbon group having 1 to 10 carbon atoms which may have a hetero atom. 1 R represents a ring structure composed of atoms including a nitrogen atom and an oxygen atom. 6 represents a hydrogen atom or an organic group, and a plurality of groups may be bonded to the ring.

[0030] Above A 1 is a ring structure composed of atoms including a nitrogen atom and an oxygen atom, and may have one ring structure or a form in which multiple rings are condensed. A form having one ring structure is preferred.

[0031] Above A 1 is a cyclic compound (A 2 The structure may be derived from the cyclic compound (A 2 ) include, for example, morpholine, oxazole, isoxazole, oxadiazole, oxazolidone, oxazine, furopyrrole, benzisoxazole, benzoxazole, benzoxazine, phenazine, phenoxazine, etc. Among these, morpholine is preferred.

[0032] Above R 6 represents a hydrogen atom or an organic group, and multiple R's may be bonded to the ring. 6 The number of organic groups is preferably 0 to 5, more preferably 0 to 4, further preferably 1 to 3, and particularly preferably 1 to 2.

[0033] Above R 6 The organic group in is not particularly limited, and examples thereof include functional groups such as a thiol group, an epoxy group, a vinyl group, a halogen atom, a hydroxyl group, a carboxyl group, an amino group, a phosphate group, a hypophosphite group, a sulfonic acid group, and an ether group, as well as hydrocarbon groups having 1 to 20 carbon atoms which may have a hetero atom. Specific examples of the hydrocarbon group are as described above, and examples of the group having a hetero atom include those having the above-mentioned functional groups. The hydrocarbon group is preferably an alkyl group or an aryl group, and among these, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, an aryl group having 6 to 20 carbon atoms, etc. are more preferred. The hydrocarbon group preferably has 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, and further preferably 1 to 6 carbon atoms. Above R 6 The hydrocarbon group in may have a heteroatom and may have, for example, the above-mentioned substituents.

[0034] Above R 6 is preferably an alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 20 carbon atoms, more preferably an alkyl group having 1 to 20 carbon atoms, still more preferably an alkyl group having 1 to 10 carbon atoms, and particularly preferably an alkyl group having 1 to 5 carbon atoms, such as a methyl group, an ethyl group, a propyl group, a butyl group, or a pentyl group.

[0035] The structural moiety (C) is more preferably a structural moiety represented by the following formula (4'):

[0036] [ka]

[0037] (In the formula, R 2 represents a direct bond or a trivalent hydrocarbon group having 1 to 10 carbon atoms which may have a heteroatom. p1 and p2 are the same or different and each is an integer of 0 to 3. R 6 are the same or different and represent a hydrogen atom or an organic group, and a plurality of them may be bonded to the ring.

[0038] The above p1 and p2 are the same or different and each is an integer of 0 to 3, preferably 0 to 1, and more preferably 1. Above R 6 Specific and preferred examples of R in formula (4) are 6 is the same as: The above p1 and p2 are 1, and R 6 is a hydrogen atom is one of the preferred embodiments of the present invention.

[0039] R in the above formulas (4) and (4') 2 R represents a direct bond or a trivalent hydrocarbon group having 1 to 10 carbon atoms which may have a heteroatom. 2 The hydrocarbon group in the formula (I) preferably has 2 to 7 carbon atoms, and more preferably has 2 to 5 carbon atoms. Above R 2 represents a direct bond or the following formulae (2) to (2''); [ka]

[0040] (In the formula, x represents 0 or 1. 5 represents a direct bond, or an alkylene group having 1 to 8 carbon atoms which may have a hetero atom. Above R 5 The alkylene group has 1 to 8 carbon atoms, preferably 1 to 4 carbon atoms, and more preferably 1 to 2 carbon atoms. Above R 5 The alkylene group in the formula (I) may have a heteroatom such as an oxygen atom, a sulfur atom or a nitrogen atom, but is preferably in a form that does not have a heteroatom. Above R 5 is preferably a methylene group or an ethylene group, and more preferably a methylene group.

[0041] The (poly)alkylene glycol-containing compound of the present invention is preferably a compound represented by the following formula (1):

[0042] [ka]

[0043] (In the formula, R 1 R represents a hydrophobic group. 4R represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. 2 R are the same or different and represent a direct bond or a trivalent hydrocarbon group having 1 to 10 carbon atoms which may have a hetero atom. 3 are the same or different and each represents an alkylene group having 2 to 20 carbon atoms. A is the same or different and represents a substituent having a ring structure, and the atoms forming the ring structure include a nitrogen atom and an oxygen atom. X 1 , X 2 are the same or different and represent a direct bond or a divalent linking group. m and n are the same or different and represent numbers from 1 to 100.

[0044] The substituent having a ring structure in A is the same as A 1 Preferred are structures derived from the cyclic compounds described in 1.

[0045] Above R 1 The hydrophobic group in is preferably an organic group exhibiting hydrophobicity. Specific examples of the organic group include a hydrocarbon group which may have a substituent and a hydrocarbon group which may have a heteroatom. Specific examples of the substituent and the heteroatom are as described above. The hydrocarbon group preferably has 1 to 50 carbon atoms, more preferably 2 to 30 carbon atoms, further preferably 3 to 24 carbon atoms, even more preferably 4 to 20 carbon atoms, still further preferably 6 to 18 carbon atoms, and particularly preferably 8 to 14 carbon atoms. The number of carbon atoms in the hydrocarbon group includes the number of carbon atoms in the substituent. Examples of the hydrocarbon group include an aliphatic alkyl group, an alicyclic alkyl group, an alkenyl group, an alkynyl group, and an aryl group.

[0046] Examples of the alkyl group having 1 to 50 carbon atoms include a methyl group, an ethyl group, a n-propyl group, a n-butyl group, a n-pentyl group (amyl group), a n-hexyl group, a n-heptyl group, a n-octyl group, a n-nonyl group, a n-decyl group, a n-undecyl group, a n-dodecyl group, a n-tridecyl group, a n-tetradecyl group, a n-pentadecyl group, a n-hexadecyl group, a n-heptadecyl group, a n-octadecyl group, a n-nonadecyl group, a n-eicosanyl group, an i-propyl group, a sec-butyl group, an i-butyl group, a t-butyl group, ethyl, 1-methylbutyl, 1-ethylpropyl, 2-methylbutyl, i-amyl, neopentyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, t-amyl, 1,3-dimethylbutyl, 3,3-dimethylbutyl, 2-ethylbutyl, 2-ethyl-2-methylpropyl, 1-methylheptyl, 2-ethylhexyl, 1,5-dimethylhexyl, t-octyl, 2,6-dimethyloctyl, 2-butyloctyl, branched nonyl, decyl, u aliphatic alkyl groups such as anndecyl group, dodecyl group, tridecyl group, tetradecyl group, pentadecyl group, hexadecyl group, heptadecyl group, stearyl group, icosyl group, henicosyl group, docosyl group, tricosyl group, tetracosyl group, pentacosyl group, hexacosyl group, heptacosyl group, octacosyl group, nonacosyl group, triacontyl group, pentatriacontyl group, tetracontyl group, pentatetracontyl group, and pentacontyl group; a cyclopropyl group, a cyclopropylmethyl group, a cyclobutyl group, Examples of alicyclic alkyl groups include a cyclobutylmethyl group, a cyclopentyl group, a cyclohexyl group, a cyclohexylmethyl group, a cycloheptyl group, a cyclooctyl group, a cyclohexylpropyl group, a cyclododecyl group, a norbornyl group (C7), an adamantyl group (C10), a cyclopentylethyl group, a cyclopropyloctadecyl group, a cyclobutylheptadecyl group, a cyclopentylhexadecyl group, a cyclohexylpentadecyl group, a cycloheptyltetradecyl group, and a cyclooctyltridecyl group.

[0047] Examples of alkenyl groups having 2 to 50 carbon atoms include vinyl groups, allyl groups, 1-butenyl groups, 2-butenyl groups, pentenyl groups, hexenyl groups, heptenyl groups, octenyl groups, nonenyl groups, decenyl groups, dodecenyl groups, octadecenyl groups, icosenyl groups, eicosenyl groups, henicosenyl groups, docosenyl groups, tricosenyl groups, tetracosenyl groups, pentacosenyl groups, hexacosenyl groups, heptacosenyl groups, octacosenyl groups, nonacosenyl groups, triacontenyl groups, pentatriacontenyl groups, tetracontenyl groups, pentatetracontenyl groups, and pentacontenyl groups.

[0048] Examples of alkynyl groups having 2 to 50 carbon atoms include ethynyl, 1-propynyl, 2-propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, dodecynyl, octadecynyl, icosinyl, eicosinyl, henicosinyl, docosinyl, tricosinyl, tetracosinyl, pentacosinyl, hexacosinyl, heptacosinyl, octacosinyl, nonacosinyl, triacontinyl, pentatriacontinyl, tetracontinyl, pentatetracontinyl, and pentacontinyl groups.

[0049] Examples of the aryl group having 6 to 50 carbon atoms include a phenyl group; a naphthyl group; a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 3-phenylpropyl group, a 4-phenylbutyl group, a styryl group (Ph-CH=C- group), a cinnamyl group (Ph-CH=CHCH2- group), a 1-benzocyclobutenyl group, a 1,2,3,4-tetrahydronaphthyl group, a quaterphenyl group, a quinquephenyl group, and the like, as well as these groups, a phenyl group, a naphthyl group, a fluorenyl group, an anthracenyl group, a phenanthryl group, a biphenyl group, a terphenyl group, a distyrenated phenyl group, and the like, as well as groups in which an alkyl group or the like is bonded to an aromatic ring such as benzene or naphthalene.

[0050] The hydrophobic group is preferably an alkyl group which may have a substituent, more preferably an aliphatic alkyl group which may have a substituent, and further preferably an unsubstituted linear or branched aliphatic alkyl group, among which an undecyl group, a dodecyl group, or a tridecyl group is preferred, and a dodecyl group is more preferred.

[0051] R in the above formula (1) 2 Specific and preferred examples are as described for formulae (4) and (4'). R in the above formula (1) 3 Specific and preferred examples of and the preferred range of n are as described for formula (2). Above R 4 represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms, preferably a hydrogen atom, a methyl group, an ethyl group, or a propyl group, more preferably a methyl group or a hydrogen atom, and particularly preferably a hydrogen atom.

[0052] X in the above formula (1) 1 , X 2 are the same or different and represent a direct bond or a divalent linking group. The divalent linking group is not particularly limited, and examples thereof include polar groups such as an ether group (bond), a urethane group (bond), an ester group (bond), a carbonyl group, a carbonate group (bond), a thioether group (bond), an isocyanate group, and an amide group, as well as divalent hydrocarbon groups which may have these polar groups or other substituents. Among these, preferred are an ether group, a urethane group, an ester group, a carbonyl group, a carbonate group, a divalent organic group containing a sulfur atom, an isocyanate group, and an amide group. Examples of the other substituents include a hydroxyl group, an alkoxy group, a carboxyl group, an acyl group, a sulfonic acid group, an amino group, and a phosphoric acid group. The hydrocarbon group preferably has 1 to 5 carbon atoms.

[0053] X in the above formula (1) 1The alkyl group may be a direct bond, an ether group (bond), a urethane group (bond), an ester group (bond), a carbonyl group, or a group represented by the following formula (5);

[0054] [ka]

[0055] (In the formula, Z 1 , Z 2 represents a hydrogen atom or a hydroxyl group, Z 1 , Z 2 one of which is a hydrogen atom and the other is a hydroxyl group. Above X 1 More preferably, R is an ether group (oxygen atom). 2 is preferably a structure represented by the above formula (2').

[0056] Above X 2 is more preferably a direct bond, an ether group (bond), or a group represented by the above formula (5), and further preferably a direct bond, an ether group (bond), or an ester group (bond). Also, X 1 is an ether group, R 2 is a structure represented by the above formula (2'), X 2 is a direct bond is one of the preferred embodiments of the present invention. Also, X 1 is a direct bond, R 2 is a structure represented by the above formula (2), X 2 is a direct bond is one of the preferred embodiments of the present invention.

[0057] In the above formula (1), m represents the number of structural moieties (C) in the PAG compound and is 1 to 100. It is preferably 1 to 50, more preferably 1 to 25, even more preferably 1 to 10, still more preferably 1 to 5, particularly preferably 1 to 3, and most preferably 1.

[0058] In the PAG compounds of the present invention, R 1The number of carbon atoms in R in the above formula (1) is preferably within the above range. 1 , X 1 , R 2 , X 2 The total number of carbon atoms is preferably 1 to 50, more preferably 3 to 30, and further preferably 5 to 25.

[0059] Above R 1 , X 1 , R 2 , X 2 When the total number of carbon atoms of R is within the above range, 1 The number of carbon atoms is preferably 1 to 48, more preferably 3 to 30, further preferably 4 to 21, even more preferably 6 to 18, and particularly preferably 8 to 14.

[0060] [Method for producing the PAG compound of the present invention] The present invention also relates to a method for producing the above-mentioned (poly)alkylene glycol-containing compound, the method including any one of the following steps (i) to (iv): (i) a first step of reacting a cyclic compound containing a nitrogen atom and an oxygen atom with a compound having a hydrophobic group (hydrophobic group-containing compound); A second step of reacting the reaction product obtained in the first step with a (poly)alkylene glycol or an alkylene oxide. (ii) A step of reacting a cyclic compound containing a nitrogen atom and an oxygen atom with a compound having a hydrophobic group at one end of a (poly)alkylene glycol (a hydrophobic group-containing (poly)alkylene glycol) (iii) a first step of reacting a cyclic compound containing a nitrogen atom and an oxygen atom with a (poly)alkylene glycol or an alkylene oxide; A second step of reacting the reaction product obtained in the first step with a compound having a hydrophobic group. (iv) reacting a cyclic compound containing a hydrophobic group, a nitrogen atom, and an oxygen atom with a (poly)alkylene glycol or an alkylene oxide; Hereinafter, the above hydrophobic group-containing (poly)alkylene glycol and the (poly)alkylene glycol having no hydrophobic group are also simply referred to as (poly)alkylene glycol compounds.

[0061] <Cyclic Compound Containing Nitrogen Atom and Oxygen Atom> The nitrogen- and oxygen-atom-containing cyclic compound used in the method for producing the PAG compound of the present invention is not particularly limited as long as it has a ring structure composed of atoms including nitrogen and oxygen atoms and can react with the hydrophobic group-containing compound in (i) above, the hydrophobic group-containing (poly)alkylene glycol in (ii) above, or the (poly)alkylene glycol or alkylene oxide in (iii) and (iv) above. The cyclic compound may be, for example, the cyclic compound (A 2 ) and compounds having reactive functional groups thereto. Examples of the reactive functional group include polymerizable unsaturated groups such as epoxy groups and vinyl groups, halogen atoms, hydroxyl groups, carboxyl groups, amino groups, etc. Preferred are epoxy groups, vinyl groups, and hydroxyl groups, and more preferred are epoxy groups, hydroxyl groups, and amino groups.

[0062] The above-mentioned nitrogen atom- and oxygen atom-containing cyclic compound may have a reactive functional group as described above in addition to the ring structure composed of atoms including a nitrogen atom and an oxygen atom. In this case, the reactive functional group in the above-mentioned cyclic compound can be reacted with a hydrophobic group-containing compound, a (poly)alkylene glycol compound, or an alkylene oxide. In addition, when there is no reactive functional group other than the ring structure composed of atoms including a nitrogen atom and an oxygen atom, the nitrogen atom in the ring structure can be reacted with a hydrophobic group-containing compound, a (poly)alkylene glycol compound, or an alkylene oxide. For example, when the cyclic compound is morpholine, the NH group in morpholine can be reacted with a hydrophobic group-containing compound, a (poly)alkylene glycol compound, or an alkylene oxide.

[0063] The cyclic compound containing a nitrogen atom and an oxygen atom includes A in the above formula (4). 1 Cyclic compounds (A 2 ) and derivatives thereof having an organic group bonded thereto. Specific examples include morpholine, oxazole, isoxazole, oxadiazole, oxazolidone, oxazine, furopyrrole, benzisoxazole, benzoxazole, benzoxazine, phenazine, phenoxazine, and the like and derivatives thereof, and more preferably morpholine and derivatives thereof having an alkyl group having 1 to 20 carbon atoms bonded thereto.

[0064] <Hydrophobic group-containing compound> The hydrophobic group-containing compound used in the first step of the above method (i) and the second step of the above method (iii) is not particularly limited as long as it has a hydrophobic group and can react with the reaction product of a cyclic compound containing a nitrogen atom and an oxygen atom and a (poly)alkylene glycol compound. R 1’ -X 1’ (6) (In the formula, R 1’ represents a hydrophobic group. 1’ represents a reactive functional group. R in the above formula (6) 1’ Specific and preferred examples of R 1 The specific and preferred examples are the same as those of the above. X in the above formula (6) 1’ is not particularly limited as long as it is a functional group reactive with the functional group in the reaction product obtained in the first step (i) above, the cyclic compound containing a nitrogen atom and an oxygen atom, and examples of X include a halogen atom, an epoxy group, a glycidyl group, a hydroxyl group, a carboxyl group, an amino group, and an isocyanate group. 1’ is preferably a halogen atom, a glycidyl group, or an epoxy group. The halogen atom includes fluorine, chlorine, bromine, iodine, etc., and is preferably chlorine or iodine.

[0065] Specific examples of the hydrophobic group-containing compound represented by the above formula (6) include hydrophobic group-containing compounds having a hydroxyl group, such as alkyl alcohols, alkenyl alcohols, and aryl alcohols having 1 to 50 carbon atoms; hydrophobic group-containing compounds having a halogen atom, such as alkyl halides having 1 to 50 carbon atoms; hydrophobic group-containing compounds having a glycidyl ether group, such as alkyl glycidyl ethers having 4 to 50 carbon atoms; hydrophobic group-containing compounds having an epoxy group, such as epoxy alkanes having 2 to 50 carbon atoms; hydrophobic group-containing compounds having an isocyanate group, such as alkyl isocyanates having 2 to 50 carbon atoms; hydrophobic group-containing compounds having an amino group, such as alkyl amines, aryl amines, and N-alkyl-N-aryl amines having 1 to 50 carbon atoms; and carboxylic acids having 2 to 50 carbon atoms. Among these, preferred are hydrophobic group-containing compounds having an epoxy group, hydrophobic group-containing compounds having a hydroxyl group, hydrophobic group-containing compounds having a halogen atom, and carboxylic acids, and more preferred are hydrophobic group-containing compounds having an epoxy group, and hydrophobic group-containing compounds having a glycidyl ether group. The hydrophobic group-containing compound preferably has 1 to 50 carbon atoms, more preferably 3 to 30, further preferably 4 to 21, even more preferably 8 to 18, and particularly preferably 10 to 16 carbon atoms.

[0066] The alkyl alcohol having 1 to 50 carbon atoms is preferably methyl alcohol, ethyl alcohol, propyl alcohol, butyl alcohol, pentyl alcohol, hexyl alcohol, heptyl alcohol, octyl alcohol, nonyl alcohol, decyl alcohol, undecyl alcohol, dodecyl alcohol (lauryl alcohol), tridecyl alcohol, tetradecyl alcohol, pentadecyl alcohol, hexadecyl alcohol, heptadecyl alcohol, octadecyl alcohol, nonadecyl alcohol, eicosyl alcohol, and the like.

[0067] Preferred examples of alkenyl alcohols having 2 to 50 carbon atoms include vinyl alcohol, propenyl alcohol, isopropenyl alcohol, 3-butenyl alcohol, 2-pentenyl alcohol, 3-pentenyl alcohol, 4-pentenyl alcohol, 2-methyl-2-butenyl alcohol, 2-methyl-3-butenyl alcohol, 4-hexenyl alcohol, 6-heptenyl alcohol, 2-methyl-5-hexenyl alcohol, 7-octenyl alcohol, cis-3-octen-1-ol, 2-methyl-7-octenyl alcohol, 8-nonenyl alcohol, 9-decenyl alcohol, and oleyl alcohol.

[0068] Preferred examples of the aryl alcohol having 6 to 50 carbon atoms include phenyl alcohol, methylphenyl alcohol (o-cresol, m-cresol, p-cresol), creosol, ethylphenyl alcohol, propylphenyl alcohol, butylphenyl alcohol, butylmethylphenyl alcohol, dimethylphenyl alcohol, diethylphenyl alcohol, dibutylphenyl alcohol, hydroxybiphenyl, 4-hydroxymethylbiphenyl, 3-hydroxymethylbiphenyl, 4-hydroxyethylbiphenyl, 3-hydroxyethylbiphenyl, naphthol, 1-hydroxymethyl-naphthalene, 1-hydroxyethyl-naphthalene, 2-hydroxymethyl-naphthalene, and 2-hydroxyethyl-naphthalene.

[0069] The alkyl halide having 1 to 50 carbon atoms is preferably a butyl halide, a pentyl halide, a hexyl halide, a heptyl halide, an octyl halide, a nonyl halide, a decyl halide, an undecyl halide, a dodecyl halide, a tridecyl halide, a tetradecyl halide, a pentadecyl halide, a hexadecyl halide, a heptadecyl halide, an octadecyl halide, a nonadecyl halide, an icosyl halide, or the like.

[0070] Preferred examples of the alkyl glycidyl ether having 4 to 50 carbon atoms include methyl glycidyl ether, ethyl glycidyl ether, propyl glycidyl ether, butyl glycidyl ether, pentyl glycidyl ether, hexyl glycidyl ether, heptyl glycidyl ether, octyl glycidyl ether, nonyl glycidyl ether, decyl glycidyl ether, undecyl glycidyl ether, dodecyl glycidyl ether (lauryl glycidyl ether), tridecyl glycidyl ether, tetradecyl glycidyl ether, pentadecyl glycidyl ether, hexadecyl glycidyl ether, heptadecyl glycidyl ether, octadecyl glycidyl ether, nonadecyl glycidyl ether, and icosyl glycidyl ether.

[0071] Preferable examples of the epoxyalkane having 2 to 50 carbon atoms include the above-mentioned ethylene oxide, propylene oxide, butylene oxide, butylene oxide; 1,2-epoxyhexane, 1,2-epoxyheptane, 1,2-epoxyoctane, 1,2-epoxynonane, 1,2-epoxydecane, 1,2-epoxyundecane, 1,2-epoxydodecane, 1,2-epoxytetradecane, 1,2-epoxypentadecane, 1,2-epoxyhexadecane, 1,2-epoxyheptadecane, 1,2-epoxyoctadecane, 1,2-epoxynonadecane, and 1,2-epoxyeicosane.

[0072] Preferred examples of the alkyl isocyanate having 2 to 50 carbon atoms include methyl isocyanate, ethyl isocyanate, propyl isocyanate, butyl isocyanate, pentyl isocyanate, hexyl isocyanate, heptyl isocyanate, octyl isocyanate, nonyl isocyanate, decyl isocyanate, undecyl isocyanate, dodecyl isocyanate, tridecyl isocyanate, tetradecyl isocyanate, pentadecyl isocyanate, hexadecyl isocyanate, heptadecyl isocyanate, octadecyl isocyanate, nonadecyl isocyanate, and eicosyl isocyanate.

[0073] Preferred alkylamines having 1 to 50 carbon atoms include methylamine, ethylamine, propylamine, butylamine, pentylamine, hexylamine, heptylamine, octylamine, nonylamine, decylamine, undecylamine, dodecylamine (laurylamine), tridecylamine, tetradecylamine, pentadecylamine, hexadecylamine, heptadecylamine, octadecylamine, nonadecylamine, and icosylamine. Preferred examples of the arylamine having 6 to 50 carbon atoms include aniline and benzylamine. Preferred examples of the N-alkyl-N-arylamine having 7 to 50 carbon atoms include N-methylaniline, N-ethylaniline, N-propylaniline, N-butylaniline, N-pentylaniline, N-hexylaniline, N-heptylaniline, N-octylaniline, N-nonylaniline, N-decylaniline, N-undecylaniline, N-dodecylaniline, N-tridecylaniline, N-tetradecylaniline, N-pentadecylaniline, N-tert-butyl-3,5-dimethylaniline, N-methylbenzylamine, N-butylbenzylamine, and N-tert-butyl-benzylamine.

[0074] Examples of carboxylic acids having 2 to 50 carbon atoms include saturated fatty acids such as acetic acid, propionic acid, butyric acid, valeric acid, pivalic acid, caproic acid, enanthic acid, caprylic acid, 2-ethylhexanoic acid, pelargonic acid, capric acid, undecylic acid, lauric acid, tridecylic acid, myristic acid, pentadecylic acid, palmitic acid, margaric acid, stearic acid, nonadecylic acid, and arachidic acid; and acrylic acid, methacrylic acid, crotonic acid, myristoleic acid, palmitoleic acid, sapienic acid, oleic acid, elaidic acid, vaccenic acid, gadoleic acid, eicosenoic acid (paulic acid), erucic acid, and nervonic acid. diunsaturated fatty acids such as linoleic acid, eicosadienoic acid, and docosadienoic acid; triunsaturated fatty acids such as α-linolenic acid, γ-linolenic acid, pinoleic acid, eleostearic acid, mead acid, dihomo-γ-linolenic acid, and eicosatrienoic acid; tetraunsaturated fatty acids such as stearidonic acid, arachidonic acid, eicosatetraenoic acid, and adrenic acid; pentaunsaturated fatty acids such as bosseopentaenoic acid, eicosapentaenoic acid, docosapentaenoic acid, osbondoic acid, sardine acid, and tetracosapentaenoic acid; and hexaunsaturated fatty acids such as docosahexaenoic acid and herring acid.

[0075] The method for producing the PAG compound of the present invention is preferably method (i), and it is more preferable to add an epoxy compound having a hydrophobic group to the nitrogen atom of a cyclic compound containing a nitrogen atom and an oxygen atom, and then add an alkylene oxide to the hydroxyl group produced by the addition reaction. More specifically, there is a method in which morpholine is reacted with a hydrophobic epoxy compound (a hydrophobic group-containing compound having an epoxy group) such as epoxytetradecane, or a hydrophobic glycidyl ether (a hydrophobic group-containing compound having a glycidyl ether group) such as dodecyl glycidyl ether, and ethylene oxide is added to the obtained reaction product.

[0076] <Amount of each compound used and reaction conditions in the method for producing the PAG compound of the present invention> The amount of the hydrophobic group-containing compound used in the methods (i) and (iii) is preferably 5 to 5,000 mol % relative to 100 mol % of the amount of the cyclic compound containing a nitrogen atom and an oxygen atom (the reaction product obtained in the first step in (iii)). It is more preferably 7 to 1,000 mol %, even more preferably 10 to 500 mol %, and particularly preferably 20 to 300.

[0077] In the methods (i), (iii) and (iv), when an alkylene oxide is used, the amount of the alkylene oxide used is preferably 100 to 10,000 mol % relative to 100 mol % of the cyclic compound containing a nitrogen atom and an oxygen atom (the reaction product obtained in the first step in (i) and the cyclic compound containing a hydrophobic group, a nitrogen atom and an oxygen atom in (iv)). It is more preferably 300 to 8,000 mol %, further preferably 500 to 6,000 mol %, and particularly preferably 1,000 to 3,000 mol %.

[0078] The amount of the cyclic compound containing a nitrogen atom and an oxygen atom used in the above method (ii) is preferably 100 to 10,000 mol %, more preferably 100 to 7,500 mol %, further preferably 100 to 5,000 mol %, and particularly preferably 100 to 1,000 mol %, based on 100 mol % of the (poly)alkylene glycol compound. In the methods (i), (iii) and (iv), when a (poly)alkylene glycol compound is used, the preferred range of the amount of the cyclic compound containing a nitrogen atom and an oxygen atom (the reactant obtained in the first step in (iii) and the cyclic compound containing a hydrophobic group, a nitrogen atom and an oxygen atom in (iv)) used is the same as the preferred range of the amount of the cyclic compound containing a nitrogen atom and an oxygen atom used in the above (ii).

[0079] In the reaction steps of the above methods (i) to (iv), it is preferable to use a catalyst from the viewpoint of reaction rate. Examples of the catalyst include acid catalysts such as mineral acids such as sulfuric acid and phosphoric acid, Lewis acids such as tin tetrachloride and boron trifluoride, basic catalysts such as alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, amine catalysts such as triethylamine, pyridine and dimethylaminopyridine, and polymerization catalysts.

[0080] The amount of the catalyst used in the reaction using the (poly)alkylene glycol compound is preferably 0.5 to 10 mol %, more preferably 1 to 5 mol %, based on 100 mol % of the (poly)alkylene glycol compound. The amount of the catalyst used in the reaction using a cyclic compound containing a nitrogen atom and an oxygen atom (having a hydrophobic group) is preferably 1 to 200 mol %, more preferably 2 to 100 mol %, based on 100 mol % of the cyclic compound containing a nitrogen atom and an oxygen atom (having a hydrophobic group). The amount of the catalyst used in the second step of the above methods (i) and (iii) is preferably 0.01 to 200 mol % relative to 100 mol % of the reactant obtained in the first step, and more preferably 0.02 to 200 mol %.

[0081] The reaction temperature in each reaction step in the production method of the present invention is not particularly limited, but is preferably 20 to 180° C., more preferably 30 to 160° C., even more preferably 50 to 150° C., and particularly preferably 80 to 140° C. In addition, when carrying out the addition reaction of an alkylene oxide, the reaction pressure is from normal pressure to 20 kg / cm. 2 G or less, and more preferably 1 to 10 kg / cm 2 It's G.

[0082] In the above methods (i) and (iii), the addition reaction of alkylene oxide is carried out using a catalyst such as sodium hydroxide or potassium hydroxide, and if necessary, using a pressurized reactor such as an autoclave, at a reaction temperature from room temperature to about 150° C., which is one of the preferred embodiments of the present invention.

[0083] The reaction time in each reaction step in the production method of the present invention is not particularly limited, but is preferably 30 minutes to 5 hours. More preferably, it is 40 minutes to 3 hours. When the reaction temperature and reaction time are within the above-mentioned ranges, the reaction proceeds almost quantitatively and is improved, so that the amount of unreacted raw material is reduced, and the cleaning performance of the (poly)alkylene glycol-containing compound is further improved.

[0084] The reaction step is preferably carried out under an atmosphere of an inert gas such as nitrogen gas. After the reaction, the reaction product may be stored under an atmosphere of an inert gas such as nitrogen gas.

[0085] After the reaction step in the above method (i), if necessary, the reactant may be reacted with a compound similar to the compound represented by the above formula (15).

[0086] In the method for producing a PAG compound of the present invention, if necessary, a purification step may be provided after or during the reaction steps of the above methods (ii) and (iv) and the first and second steps of the above methods (i) and (iii). Examples of the purification step include a step of removing remaining raw materials, by-products, moisture, catalyst residues, etc., and a step of neutralizing the catalyst. For example, it is preferable to purify the solution after the reaction step by dialysis using a dialysis membrane with a molecular weight cutoff according to the molecular weight of the target compound.

[0087] [Composition containing a (poly)alkylene glycol-containing compound] The present invention also relates to a composition comprising the above-mentioned (poly)alkylene glycol-containing compound and other components other than the compound, wherein the content of the (poly)alkylene glycol-containing compound is 1 to 99 mass % relative to 100 mass % of the composition. The other components are not particularly limited, but examples thereof include detergent additives described below.

[0088] [Uses of the (poly)alkylene glycol-containing compound of the present invention] The (poly)alkylene glycol-containing compound of the present invention can be suitably used as a detergent builder, a detergent, a water treatment agent, a dispersant, a fiber treatment agent, a scale inhibitor (scale inhibitor), a cement additive, a metal ion sealant, a thickener, various binders, and the like. The (poly)alkylene glycol-containing compound of the present invention has excellent detergency against muddy soils and a low critical micelle concentration, and therefore can be suitably used, inter alia, in detergent builders and detergents. The present invention also relates to a detergent builder or detergent containing the above-mentioned (poly)alkylene glycol-containing compound. The present invention also relates to a detergent composition containing the above-mentioned (poly)alkylene glycol-containing compound and a detergent additive other than the compound. The embodiment in which a surfactant is contained as the detergent additive is one of the preferred embodiments of the present invention.

[0089] The detergent additives other than the (poly)alkylene glycol-containing compound in the above-mentioned detergent composition or detergent builder and their blending ratios can be appropriately set based on various components that can be used in conventionally known detergent compositions or detergent builders and their blending ratios, within a range that does not impair the action and effect of the present invention.

[0090] The detergent may be a powder detergent or a liquid detergent, but a liquid detergent is preferred because the (poly)alkylene glycol-containing compound has excellent solubility in the liquid detergent. In addition to the (poly)alkylene glycol-containing compound, additives that are usually used in detergents can be used in the detergent.

[0091] Suitable examples of the detergent additives include surfactants, alkali builders, chelate builders, redeposition inhibitors for preventing redeposition of contaminants such as sodium carboxymethylcellulose, stain inhibitors such as benzotriazole and ethylene-thiourea, soil release agents, color transfer inhibitors, fabric softeners, alkaline substances for adjusting pH, fragrances, solubilizers, fluorescent agents, colorants, foaming agents, foam stabilizers, gloss agents, disinfectants, bleaching agents, bleaching aids, enzymes, dyes, solvents, etc. In the case of powder detergents, it is preferable to add zeolite.

[0092] In the detergent composition, the content of the (poly)alkylene glycol-containing compound of the present invention is preferably 0.1 to 20% by mass relative to 100% by mass of the detergent composition. If the content is 0.1% by mass or more, the detergency of the detergent will be more sufficient, and if it is 20% by mass or less, the cost efficiency will be excellent. It is more preferably 0.5 to 10% by mass, and even more preferably 1 to 5% by mass.

[0093] The above detergents include synthetic detergents for household use, detergents for the textile and other industrial uses, and hard surface cleaners, as well as detergents used for specific purposes only, such as bleaching detergents, which enhance the function of one of their ingredients.

[0094] The surfactant is at least one selected from anionic surfactants, nonionic surfactants, cationic surfactants and amphoteric surfactants, and these surfactants can be used alone or in combination.

[0095] Suitable examples of the anionic surfactant include alkylbenzenesulfonates, alkyl ether sulfates, alkenyl ether sulfates, alkyl sulfates, alkenyl sulfates, α-olefinsulfonates, α-sulfofatty acids or ester salts, alkanesulfonates, saturated fatty acid salts, unsaturated fatty acid salts, alkyl ether carboxylates, alkenyl ether carboxylates, amino acid surfactants, N-acylamino acid surfactants, alkyl phosphates or their salts, alkenyl phosphates or their salts, etc. The alkyl and alkenyl groups in the anionic surfactants may have a branched alkyl group such as a methyl group.

[0096] Suitable examples of the nonionic surfactant include polyoxyalkylene alkyl ethers, polyoxyalkylene alkenyl ethers, polyoxyethylene alkylphenyl ethers, higher fatty acid alkanolamides or their alkylene oxide adducts, sucrose fatty acid esters, alkyl glycoxides, fatty acid glycerin monoesters, alkylamine oxides, etc. The alkyl and alkenyl groups in the nonionic surfactants may have branched alkyl groups such as methyl groups. As the cationic surfactant, a quaternary ammonium salt or the like is preferable. As the amphoteric surfactant, a carboxyl type amphoteric surfactant, a sulfobetaine type amphoteric surfactant, etc. are preferable. In the above cationic surfactants and amphoteric surfactants, the alkyl group and the alkenyl group may be a branched alkyl group such as a methyl group.

[0097] The blending ratio of the surfactant is usually preferably 10 to 60% by mass relative to the total amount of the detergent composition (100% by mass). More preferably, it is 15% by mass or more and 50% by mass or less, even more preferably, it is 20% by mass or more and 45% by mass or less, and particularly preferably, it is 25% by mass or more and 40% by mass or less. If the blending ratio of the surfactant is 10% by mass or more, sufficient detergency can be exhibited, and if it is 60% by mass or less, it is also excellent in economical efficiency. When two or more surfactants are used, the combined amount of the anionic surfactant and the nonionic surfactant is preferably 50% by mass or more, more preferably 60% by mass or more, even more preferably 70% by mass or more, and particularly preferably 80% by mass or more, based on 100% by mass of the total surfactants.

[0098] The detergent is preferably a liquid detergent. The blending ratio of the liquid detergent builder in the liquid detergent is usually preferably 0.1 to 20% by mass relative to 100% by mass of the liquid detergent. More preferably, it is 0.2% by mass or more and 15% by mass or less, more preferably, it is 0.3% by mass or more and 10% by mass or less, even more preferably, it is 0.4% by mass or more and 8% by mass or less, and particularly preferably, it is 0.5% by mass or more and 5% by mass or less. If the blending ratio of the liquid detergent builder is 0.1% by mass, sufficient detergent performance can be exhibited, and if it is 20% by mass or less, it is also excellent in economy.

[0099] The water content in the liquid detergent is preferably 0.1 to 75% by mass relative to 100% by mass of the liquid detergent, more preferably 0.2% by mass or more and 70% by mass or less, even more preferably 0.5% by mass or more and 65% by mass or less, particularly preferably 0.7% by mass or more and 60% by mass or less, even more particularly preferably 1% by mass or more and 55% by mass or less, and most preferably 1.5% by mass or more and 50% by mass or less.

[0100] Suitable enzymes that can be added to the detergent include proteases, lipases, cellulases, etc. Among them, proteases, alkaline lipases, and alkaline cellulases, which are highly active in alkaline cleaning solutions, are preferred. The amount of the enzymes added is preferably 5% by mass or less relative to 100% by mass of the detergent. If the amount is 5% by mass or less, the detergent will exhibit sufficient cleaning power while also being economical.

[0101] The alkali builder is preferably a silicate, a carbonate, a sulfate, etc. The chelating builder is preferably a diglycolic acid, an oxycarboxylic acid, EDTA (ethylenediaminetetraacetic acid), DTPA (diethylenetriaminepentaacetic acid), citric acid, MGDA (methylglycinediacetic acid), HIDS (hydroxyiminodiacetic acid), etc. A water-soluble polycarboxylic acid polymer may also be used. EXAMPLES

[0102] The present invention will be described in more detail below with reference to examples, but the present invention is not limited to these examples. In addition, unless otherwise specified, "parts" means "parts by weight" and "%" means "% by mass".

[0103] <Synthesis example of intermediate (1)> Synthesis of (1,2-epoxytetradecane-morpholine) 189.95g of morpholine and 17.44g of sodium hydroxide were charged into a 500mL glass four-necked eggplant flask reaction vessel equipped with a thermometer, a stirrer, and a nitrogen inlet tube, and heated to 120°C with stirring. Then, 92.61g of 1,2-epoxytetradecane was dropped into the reaction vessel using a dropping funnel over 70 minutes, and the temperature was maintained for 3 hours under a nitrogen atmosphere to obtain a crude reaction product. Then, unreacted morpholine was removed by evaporation to obtain an alkylene alcohol compound having morpholine (hereinafter, intermediate (1)).

[0104] <Example 1> In a 1L SUS autoclave reaction vessel equipped with a thermometer, a stirrer, a raw material introduction tube and a nitrogen introduction tube, 77.97 g of intermediate (1) and 0.28 g of potassium hydroxide as a catalyst were charged, and the reaction vessel was replaced with nitrogen while stirring, and heated to 130 ° C under a nitrogen atmosphere. Thereafter, the reaction vessel was reduced in pressure to 2.9 kPa using a vacuum pump, and dehydration was carried out for 1 hour while stirring. Then, 137.6 g of ethylene oxide was introduced into the reaction vessel over 2 hours while maintaining the temperature at 150 ± 5 ° C under a safe pressure. Finally, the reaction vessel was replaced with nitrogen while stirring, and cooled to room temperature. In this way, a polyalkylene glycol-containing compound (1) was obtained in which an average of 21 moles of ethylene oxide was added to the intermediate (1).

[0105] <Comparative Example 1> In a 1L SUS autoclave reaction vessel equipped with a thermometer, a stirrer, a raw material introduction tube, and a nitrogen introduction tube, 99.1 g of 1-dodecanol (FUJIFILM Wako Pure Chemical Industries, Ltd.) and 0.56 g of potassium hydroxide as a catalyst were charged, and the reaction vessel was replaced with nitrogen under stirring, and heated to 130°C under a nitrogen atmosphere. Thereafter, the reaction vessel was reduced in pressure to 2.9 kPa using a vacuum pump, and dehydration was carried out for 1 hour under stirring. Then, 491.7 g of ethylene oxide was introduced into the reaction vessel over 5 hours while maintaining the temperature at 150±5°C under a safe pressure, and the temperature was maintained for another 1 hour after the introduction. Finally, the reaction vessel was replaced with nitrogen under stirring, and cooled to room temperature. Thus, a comparative polyalkylene glycol-containing compound (2) in which an average of 21 moles of ethylene oxide was added to 1-dodecanol was obtained.

[0106] <Mud stain cleaning power evaluation test> (1) The whiteness of 140KC (5 cm Black Todd Clay-Knitted Cotton, manufactured by Warwick Equest) was measured in advance in terms of reflectance using a spectrophotometer SE6000 manufactured by Nippon Denshoku Industries Co., Ltd. (2) In a 10 mL screw tube, 5 g of a 1.5% aqueous solution of a polyalkylene glycol-containing compound as an evaluation sample was prepared. (3) 5.68 g of calcium chloride dihydrate and 2.61 g of magnesium chloride hexahydrate were mixed with pure water to make 100 g to prepare hardness water liquor. (4) As a detergent component, 4.62 g of Neopelex G-65 (linear alkylbenzene sulfonate sodium (LAS)) was measured out and diluted with pure water to 100 g to prepare a 3% LAS aqueous solution. (5) 21.0 g of the hardness water mother liquor prepared in (3), 56.0 g of the 3% LAS aqueous solution prepared in (4), and 4,123.0 g of pure water were placed in a 5 L mug and thoroughly stirred to prepare a cleaning solution. (6) The tergotometer was set to 25°C, and 1000 mL of the cleaning solution (5) and 2.67 g of the evaluation sample solution (2) were added to each pot, and stirred at 100 rpm for 1 minute. Then, three soiled cloths and 39 g of cotton cloth (Test fabrics, 5 cm x 5 cm, Style #460) for adjusting the liquor ratio were added, and soaked for 1 minute. (As a reference, pure water was added instead of the sample solution (3), and evaluation was also performed.) Then, stirring was performed for 10 minutes at 150 rpm. (7) The contaminated cloth was removed from each pot, the water was drained by hand, and 5 g of the hardness water mother liquor from (3) and 1,000 mL of pure water were added to the pots, the temperature was adjusted to 25°C, and the pots were stirred at 150 rpm for 5 minutes. (8) and (7) were repeated once more, after which the stained cloth was taken out of each pot, the water was squeezed off by hand, and the cloth was dried overnight at room temperature. The whiteness of the stained cloth was then measured again in terms of reflectance using the above-mentioned spectrophotometer. (9) From the above measurement results, the cleaning rate (cleaning power) was calculated using the following formula. Cleaning rate (%) = ((reflectance Z of soiled cloth after cleaning) - (reflectance Z of soiled cloth before cleaning)) / ((reflectance Z of white cloth) - (reflectance Z of soiled cloth before cleaning)) x 100 The higher the value of the cleaning rate, the better the cleaning power. The evaluations (1) to (9) were repeated three times, and the average value of each cleaning rate was taken as the cleaning rate of this test. The results are shown in Table 1.

[0107] [Table 1]

[0108] <Static surface tension measurement> The static surface tension was measured by the Wilhelmy plate method using a Kruss K122 tensionmeter (Kruss). A polyalkylene glycol-containing compound was mixed with pure water to prepare an aqueous solution of the polyalkylene glycol-containing compound so that the concentration of the polyalkylene glycol-containing compound was 0.0030 mM to 2.0 mM. The prepared aqueous solution was measured at a temperature of 25°C and three trials were performed. The measurement results of Example 1 and Comparative Example 1 are shown in Tables 2 and 3.

[0109] [Table 2]

[0110] [Table 3]

[0111] <How to calculate critical micelle concentration (CMC)> For each polyalkylene glycol-containing compound, the concentration [mM] was plotted against the vertical axis of static surface tension γ [mN / m]. The results of Example 1 are shown in FIG. 1, and the results of Comparative Example 1 are shown in FIG. 2. Next, the average value γave of γ when γ became constant with respect to the surfactant concentration was calculated. A logarithmic approximation was performed on the plot of the surfactant concentration region lower than the constant with respect to the surfactant concentration to obtain an approximation formula. The surfactant concentration at which the obtained approximation formula takes γave was determined as the CMC. The results are shown in Table 4.

[0112] [Table 4]

[0113] From the above, it has become clear that the (poly)alkylene glycol-containing compound of the present invention has high detergency against muddy stains and can reach the critical micelle concentration (CMC) at a low concentration.

Claims

1. having a hydrophobic structural portion (A), a (poly)alkylene glycol portion (B), and a structural portion (C) having a ring structure; The (poly)alkylene glycol-containing compound, wherein the atoms forming the ring structure include a nitrogen atom and an oxygen atom.

2. The (poly)alkylene glycol-containing compound is represented by the following formula (1): 【Chemistry 1】 (In the formula, R １ represents a hydrophobic group. ４ represents a hydrogen atom or an alkyl group having 1 to 3 carbon atoms. ２ R represents a trivalent hydrocarbon group having 1 to 10 carbon atoms which may have a heteroatom. ３ are the same or different and each represents an alkylene group having 2 to 20 carbon atoms. A is the same or different and represents a substituent having a ring structure, and the atoms forming the ring structure include a nitrogen atom and an oxygen atom. X １ , X ２ and m and n are the same or different and each represents a direct bond or a divalent linking group.

3. The R ２ are the same or different and are represented by the following formulas (2) to (2″); 【Chemistry 2】 (In the formula, x represents 0 or 1. ５ represents a direct bond, or an alkylene group having 1 to 8 carbon atoms which may have a heteroatom.

4. A method for producing the (poly)alkylene glycol-containing compound according to any one of claims 1 to 3, comprising the steps of: The production method is a method for producing a (poly)alkylene glycol-containing compound, comprising any one of the following steps (i) to (iv): (i) a first step of reacting a cyclic compound containing a nitrogen atom and an oxygen atom with a compound having a hydrophobic group; A second step of reacting the reaction product obtained in the first step with a (poly)alkylene glycol or an alkylene oxide. (ii) reacting a cyclic compound containing a nitrogen atom and an oxygen atom with a compound having a hydrophobic group at one end of a (poly)alkylene glycol; (iii) a first step of reacting a cyclic compound containing a nitrogen atom and an oxygen atom with a (poly)alkylene glycol or an alkylene oxide; A second step of reacting the reaction product obtained in the first step with a compound having a hydrophobic group. (iv) reacting a cyclic compound containing a hydrophobic group, a nitrogen atom, and an oxygen atom with a (poly)alkylene glycol or an alkylene oxide;

5. A composition comprising the (poly)alkylene glycol-containing compound according to any one of claims 1 to 3 and other components other than the compound, A composition, wherein the content of the (poly)alkylene glycol-containing compound is 1 to 99% by mass, based on 100% by mass of the composition.

6. A detergent composition comprising the (poly)alkylene glycol-containing compound according to any one of claims 1 to 3 and a detergent additive other than said compound.

7. A detergent composition comprising the (poly)alkylene glycol-containing compound according to any one of claims 1 to 3 and a surfactant.

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