Polyalkylene oxide-containing compound

Abstract

To provide a polyalkylene oxide-containing compound that is highly soluble in water and exhibits superior cleaning performance.SOLUTION: The present invention provides a polyalkylene oxide-containing compound having a substituent (A) represented by the following general formula (1) (where each R1 denotes, identically or differently, a hydrocarbon group having 2 to 6 carbon atoms; s1 denotes an integer from 1 to 300; Y1 denotes a direct bond or a linear or branched hydrocarbon group having 1 to 10 carbon atoms; and T1 denotes an organic group having 4 to 18 carbon atoms), and having a cationic group containing a nitrogen atom, wherein the substituent (A) is bound to at least one of the nitrogen atoms included in the cationic group.SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a polyalkylene oxide-containing compound, and more particularly to a polyalkylene oxide-containing compound useful in detergents and the like. [Background technology]

[0002] Conventionally, a polymer having a polyalkyleneimine as a main chain and ethylene oxide or the like added to the nitrogen atom of the polyalkyleneimine is known as polyalkyleneimine polyalkylene oxide. This polymer is known to act as a polymer builder, and is used as a component of liquid detergents because it has the property of dissolving in liquid detergents. When polyalkyleneimine polyalkylene oxide is contained in detergents together with an activator, it prevents recontamination due to the dirt removed by washing, and exerts high detergency.

[0003] Various studies have been conducted on polyalkyleneimine polyalkyleneoxide. For example, Patent Document 1 discloses a copolymer having a structure in which maleic anhydride is added to a terminal group of a polyalkyleneoxide in a polyalkyleneimine alkyleneoxide copolymer having an alkyleneimine monomer unit having a polyalkyleneoxide.

[0004] Patent Document 2 discloses a polyalkyleneamine alkyleneoxide copolymer containing an alkyleneamine structural unit having a polyalkyleneoxide chain, in which a part or all of the terminal groups of the polyalkyleneoxide chain of the polyalkyleneamine alkyleneoxide copolymer have been subjected to an addition reaction with lauryl glycidyl ether. [Prior art documents] [Patent documents]

[0005] [Patent Document 1] JP 2006-241372 A [Patent Document 2] JP 2012-149185 A Summary of the Invention [Problem to be solved by the invention]

[0006] As described above, conventionally, techniques have been developed in which a cationic group-containing compound containing an alkyleneamine structural unit having a polyalkylene oxide chain is used in a detergent composition, but there is still room for the development of further compounds that have good solubility in water and excellent cleaning performance.

[0007] The present invention has been made in consideration of the above-mentioned current situation, and an object of the present invention is to provide a polyalkylene oxide-containing compound that has good solubility in water and excellent cleaning performance. [Means for solving the problem]

[0008] The present inventors have conducted extensive research into polyalkylene oxide-containing compounds with excellent cleaning performance, and have found that a polyalkylene oxide-containing compound having a substituent of a predetermined structure at a polyalkylene glycol terminal which has an organic group having 4 to 18 carbon atoms and a cationic group having a nitrogen atom, wherein the substituent is bonded to at least one of the nitrogen atoms contained in the cationic group, has good solubility in water and excellent cleaning performance. They have thus come to the conclusion that the above-mentioned problems can be solved admirably, and have arrived at the present invention.

[0009] The present invention includes the following polyalkylene oxide-containing compounds, etc. [1] The following general formula (1); [ka] (In general formula (1), R 1 are the same or different and represent a hydrocarbon group having 2 to 6 carbon atoms. s1 is an integer of 1 to 300. Y 1 represents a direct bond or a linear or branched hydrocarbon group having 1 to 10 carbon atoms. 1represents an organic group having 4 to 18 carbon atoms. The polyalkylene oxide-containing compound has a substituent (A) represented by the following formula (I): and a cationic group having a nitrogen atom, and the substituent (A) is bonded to at least one of the nitrogen atoms contained in the cationic group. [2] T in the substituent (A) described in the above general formula (1) 1 is an alkyl group having 4 to 18 carbon atoms, an alkenyl group having 4 to 18 carbon atoms, an alkynyl group having 4 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a heterocyclic group having 4 to 18 carbon atoms. [3] T in the substituent (A) described in the above general formula (1) 1 is a linear, branched or cyclic alkyl group having 4 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms. [4] Y in the substituent (A) described in the above general formula (1) 1 is a hydrocarbon group having 2 to 4 carbon atoms. [5] The polyalkylene oxide-containing compound is represented by the following general formula (2); [ka] (In general formula (2), R 2 are the same or different and represent a linear alkylene group having 2 to 6 carbon atoms, or a branched alkylene group having 3 to 6 carbon atoms. P is the same or different and represents a hydrogen atom, or a structural unit having another amino group due to branching. a and b are the same or different and represent an integer of 0 to 100, and at least one of a and b is 1 or greater. The polyalkylene oxide-containing compound according to any one of the above-mentioned [1] to [4], having a structure derived from a compound represented by the following formula: [6] The polyalkylene oxide-containing compound may further comprise a compound represented by the following general formula (3); [ka] (Y 2 represents a direct bond or a linear or branched hydrocarbon group having 1 to 10 carbon atoms.2 represents a hydrogen atom, an alkali metal, an alkaline earth metal, an ammonium group, or an organic group having 1 to 30 carbon atoms.), and the substituent (B) is bonded to at least one nitrogen atom contained in the cationic group. [7] A detergent or detergent composition comprising the polyalkylene oxide-containing compound according to any one of [1] to [6] above. Effect of the Invention

[0010] The polyalkylene oxide-containing compound of the present invention has the above-mentioned constitution, has good solubility in water, and has excellent cleaning performance, and therefore can be suitably used in detergents and the like. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0011] 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.

[0012] In the following description, unless otherwise specified, the range "A to B" indicates that the range is from A to B. In addition, in the present invention, "(meth)acrylate" means "acrylate" or "methacrylate", and "(meth)acrylic" means "acrylic" or "methacrylic".

[0013] 1. Polyalkylene oxide-containing compounds The polyalkylene oxide-containing compound of the present invention has the following substituents 1) and 2). 1) Cationic group having a nitrogen atom 2) A substituent (A) represented by the above general formula (1) and bonded to at least one nitrogen atom contained in the cationic group. The polyalkylene oxide-containing compound of the present invention can exhibit excellent detergency by having the above-mentioned substituent. The polyalkylene oxide-containing compound has an organic group having 4 to 18 carbon atoms at the polyalkylene glycol end in the substituent (A), and therefore has excellent affinity for hydrophobic stains such as oil stains while maintaining good solubility in water, and therefore has particularly excellent detergency for hydrophobic stains.

[0014] The cationic group is a group having an amino group. The amino group can be in the form of a primary amine, a secondary amine, a tertiary amine, or a quaternary amine. Specific examples of the cationic group will be described later.

[0015] The polyalkylene oxide-containing compound of the present invention has a structure in which the substituent (A) represented by the above general formula (1) is bonded to a cationic group.

[0016] The substituent (A) represented by the above general formula (1) is (R 1 -O) s1 -T 1 and a polyalkylene oxide-containing moiety represented by -Y 1 It is a substituent containing a linking group represented by -COO-. In recent years, detergent compositions are required to have excellent cleaning ability and also to be easily decomposed in nature from the viewpoint of environmental friendliness. For this reason, the linking group is preferably a hydrolyzable group, particularly a functional group decomposed by an extracellular enzyme, that has an ester group. The linking group having such an ester group structure is preferred because it can improve the storage stability and decomposability after use of the polyalkylene oxide-containing compound, and is also preferred because it tends to improve the mud particle dispersion ability and redeposition prevention ability of the polyalkylene oxide-containing compound of the present invention. Biodegradable means that it can be metabolized and broken down by organisms such as bacteria, fungi, and other organisms.

[0017] R in the general formula (1) 1is not particularly limited as long as it is a hydrocarbon group having 2 to 6 carbon atoms, but is preferably a hydrocarbon group having 2 to 4 carbon atoms. 1 may be hydrocarbon groups having the same number of carbon atoms, or may be a combination of hydrocarbon groups having different numbers of carbon atoms. 1 As the alkylene group, an embodiment having a linear alkylene group having 2 to 6 carbon atoms and a branched alkylene group having 3 to 6 carbon atoms is also one of the preferred embodiments of the present invention. In the general formula (1), -R 1 The --O-- group is preferably one or more groups selected from an oxyethylene group, an oxypropylene group, and an oxybutylene group. These preferred substituents and atoms improve the water solubility of the polyalkylene oxide compound, and the polyalkylene oxide compound of the present invention can have superior mud dispersibility and compatibility with liquid detergents.

[0018] In the general formula (1), s1 is not particularly limited as long as it is an integer of 1 to 300. It is preferably 3 to 200, more preferably 5 to 100, even more preferably 10 to 60, and still more preferably 20 to 40. When s1 in the general formula (1) is within such a range, the mud dispersibility and anti-soil redeposition performance of the polyalkylene oxide compound are further improved. In the general formula (1), s1 may be any number from 1 to 300, but in the polyalkylene oxide compound of the present invention, the average chain length of the polyalkylene oxide is preferably from 1 to 300. It is more preferably from 3 to 200, even more preferably from 5 to 100, particularly preferably from 10 to 60, and even more preferably from 20 to 40. In this specification, the average chain length of a polyalkylene oxide means the average value of the number of moles of oxyalkylene groups contained in the same substituent (A).

[0019] (R 1 -O) s1 is represented by the following general formula (4); (R 1’ -O) t -(R 1 -O)s1-t (4) (In the formula, R 1’ are the same or different and represent a branched alkylene group having 3 to 6 carbon atoms. t is an integer of 1 to 20. R 1 and s1 is R in general formula (1). 1 and s1.) In this case, R 1’ Due to the steric hindrance and hydrophobicity in the above, the ester group in the general formula (1) is less susceptible to hydrolysis, and the stability of the polyalkylene oxide compound is improved. R 1’ is preferably a branched alkylene group having 3 to 4 carbon atoms, and more preferably an isopropylene group or an isobutylene group. t is preferably 1 to 10, more preferably 1 to 5, and further preferably 1 to 3. R in the above general formula (4) 1 Preferably, the alkyl group is an ethylene group, and from the viewpoints of mud dispersibility and prevention of redeposition, it is preferable that the alkyl group contains 80 mol % or more of ethylene groups.

[0020] Y in the general formula (1) 1 Y is a direct bond or a linear or branched hydrocarbon group having 1 to 10 carbon atoms. 1 is preferably a hydrocarbon group having 1 to 10 carbon atoms, more preferably a hydrocarbon group having 2 to 6 carbon atoms, and even more preferably a hydrocarbon group having 2 to 4 carbon atoms. Moreover, the hydrocarbon group is preferably an alkylene group, and more preferably an ethylene group or an isopropylene group.

[0021] The polyalkylene oxide-containing compound of the present invention is preferably decomposable at the linking group portion. In this case, the decomposable portion of the linking group that bonds the cationic group and the structural unit derived from the polyalkylene oxide is preferably not directly bonded to the cationic group but bonded to a position somewhat distant from the cationic group as explained as the preferred structure in the above general formula (1) from the viewpoint of ensuring the decomposability of the polyalkylene oxide compound.

[0022] T in the general formula (1) above 1 are not particularly limited as long as they are the same or different and are a hydrogen atom or an organic group having 4 to 18 carbon atoms, and may have a straight-chain or branched structure, or a ring structure. The organic group is preferably a hydrocarbon group which may have a heteroatom, more preferably an alkyl group, an alkenyl group, an alkynyl group, an aromatic hydrocarbon group, or a heterocyclic group.

[0023] Above T 1 The number of carbon atoms in the organic group is 4 to 18, which provides excellent affinity with hydrophobic stains and excellent cleaning power against hydrophobic stains. The number of carbon atoms in the organic group is preferably 6 to 16, more preferably 8 to 14, and even more preferably 10 to 14. In terms of improving water solubility, T 1 The organic group has 4 to 18 carbon atoms, and the organic group has preferably 4 to 10 carbon atoms, more preferably 4 to 8 carbon atoms, and further preferably 4 to 6 carbon atoms.

[0024] Examples of the alkyl group include straight-chain aliphatic alkyl groups such as n-butyl, n-pentyl (amyl), n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl, n-hexadecyl, n-heptadecyl, and n-octadecyl; sec-butyl, i-butyl, t-butyl, 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, and 2-ethyl-2-methylpropyl. aliphatic alkyl groups having a branched structure such as a branched nonyl group, a branched decyl group, a branched undecyl group, a branched dodecyl group, a branched tridecyl group, a branched tetradecyl group, a branched pentadecyl group, a branched hexadecyl group, a branched heptadecyl group, and a branched stearyl group; and alicyclic alkyl groups such as a cyclopropylmethyl group, a cyclobutyl group, 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), and a cyclopentylethyl group.

[0025] Examples of the alkenyl group include a 1-butenyl group, a 2-butenyl group, a pentenyl group, a hexenyl group, a heptenyl group, an octenyl group, a nonenyl group, a decenyl group, a dodecenyl group, and an octadecenyl group. Examples of the alkynyl group include butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, decynyl, dodecynyl, and octadecynyl groups.

[0026] Examples of the aromatic hydrocarbon group include aryl groups such as a phenyl group, a methylphenyl group, a dimethylphenyl group, an ethylphenyl group, a propylphenyl group, and a naphthyl group; and aralkyl groups such as a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 3-phenylpropyl group, and a 4-phenylbutyl group.

[0027] Examples of the heterocyclic group include a pyrrole group, a furan group, a thiophene group, an imidazole group, a pyrazole group, an oxazole group, an isoxazole group, a thiazole group, an isothiazole group, a tetrazole group, a pyridinyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a 1,2,3-triazinyl group, a quinolinyl group, an isoquinolinyl group, a quinazolinyl group, a phthalazinyl group, a buteridinyl group, a coumarinyl group, a chromonyl group, a 1,4-benzodiazepinyl group, an indole group, a benzimidazole group, a benzofuranyl group, a purinyl group, an acridinyl group, a phenoxazinyl group, a phenothiazinyl group, and the like, as well as groups having the above-mentioned alkyl groups in the heterocyclic ring.

[0028] Above T 1 is preferably a linear or branched alkyl group, or an aromatic hydrocarbon group, more preferably a linear or branched alkyl group, and even more preferably a linear aliphatic alkyl group such as an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, or an n-hexadecyl group; Aliphatic alkyl groups having a branched structure such as a hexyl group, a 1,5-dimethylhexyl group, a t-octyl group, a branched nonyl group, a branched decyl group, a branched undecyl group, a branched dodecyl group, a branched tridecyl group, a branched tetradecyl group, a branched pentadecyl group, and a branched hexadecyl group are particularly preferred, and linear or branched n-octyl groups, n-nonyl groups, n-decyl groups, n-undecyl groups, n-dodecyl groups, n-tridecyl groups, and n-tetradecyl groups are particularly preferred.

[0029] The polyalkylene oxide-containing compound of the present invention further comprises a compound represented by the following general formula (3);

[0030] [ka]

[0031] (Y 2 represents a direct bond or a linear or branched hydrocarbon group having 1 to 10 carbon atoms. 2 represents a hydrogen atom, an alkali metal, an alkaline earth metal, an ammonium group, or an organic group having 1 to 30 carbon atoms.) and it is preferable that the substituent (B) is bonded to at least one of the nitrogen atoms contained in the cationic group. As described above, the cationic group in the present invention has an amino group. If the cationic group has a primary amino group (NH group) or a secondary amino group (NH group), and if the structure of the polyalkylene oxide-containing compound contains an ester structure, then ester-amide exchange or hydrolysis with the ester structure will occur at the primary or secondary amino group portion in the detergent composition, causing a decrease in the storage stability of the polymer. In contrast, such ester amide exchange and hydrolysis can be suppressed by bonding the substituent (A) represented by general formula (1) and the substituent (B) represented by general formula (3) to the NH group in the cationic group, and thus the polyalkylene oxide-containing compound of the present invention has excellent storage stability in a detergent composition.

[0032] Above T 2 The number of carbon atoms in the organic group is preferably 1 to 24, more preferably 1 to 18, even more preferably 1 to 15, still more preferably 1 to 10, still more preferably 1 to 8, particularly preferably 1 to 6, and even more preferably 1 to 4. Above T 2 The organic group in 1and the like. Examples of the organic groups include organic groups having 4 to 18 carbon atoms, alkyl groups having 1 to 3 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, or an isopropyl group, and alkyl groups having 19 to 30 carbon atoms, such as an icosyl group or a pentacosyl group; alkenyl groups having 2 to 3 carbon atoms, such as a vinyl group or an allyl group, and alkenyl groups having 19 to 30 carbon atoms, such as an icosenyl group or a pentacosenyl group; alkynyl groups having 2 to 3 carbon atoms, such as an ethynyl group, a 1-propynyl group, or a 2-propynyl group, and alkynyl groups having 19 to 30 carbon atoms, such as an icosinyl group or a pentacosenyl group. T 2 The organic group in is preferably a linear or branched alkyl group, more preferably a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, or a tert-butyl group, and further preferably a methyl group or an ethyl group.

[0033] In one embodiment, T 2 In one preferred embodiment of the present invention, T 2 is an organic group having 2 to 6 carbon atoms.

[0034] The method for forming the substituent (B) bonded to the cationic group is not particularly limited, but it is preferable to form the substituent (B) by reacting a primary or secondary amino group in the cationic group with an unsaturated ester compound and / or an unsaturated carboxylic acid (salt). The unsaturated ester compound may be any compound having an unsaturated group and an ester group, but is preferably an ester of an unsaturated carboxylic acid and an alcohol having 1 to 30 carbon atoms. Examples of the alcohol having 1 to 30 carbon atoms include alkyl alcohols such as methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, 2-ethylhexanol, nonanol, decanol, lauryl alcohol, and stearyl alcohol; aryl alcohols such as benzyl alcohol; and unsaturated alcohols such as allyl alcohol, methallyl alcohol, propargyl alcohol, crotyl alcohol, pentenol, hexenol, heptenol, octenol, nonenol, decenol, dodecenol, and octadecenol. The alcohol preferably has 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, even more preferably 1 to 10 carbon atoms, still more preferably 1 to 8 carbon atoms, still more preferably 1 to 6 carbon atoms, and particularly preferably 1 to 4 carbon atoms. The alcohol is preferably an alkyl alcohol.

[0035] The ester of the unsaturated carboxylic acid and the alcohol is preferably a (meth)acrylic acid alkyl ester having an alkyl group having 1 to 30 carbon atoms (alkyl (meth)acrylate).

[0036] Specific examples of the unsaturated ester compound include alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, sec-butyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, stearyl (meth)acrylate, and icosyl (meth)acrylate. Among these, preferred are methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, and n-butyl (meth)acrylate, and more preferred are methyl (meth)acrylate and ethyl (meth)acrylate.

[0037] The unsaturated carboxylic acid includes unsaturated monocarboxylic acids such as (meth)acrylic acid, crotonic acid, tiglic acid, 3-methylcrotonic acid, 2-methyl-2-pentenoic acid, itaconic acid, etc.; unsaturated dicarboxylic acids such as maleic acid, itaconic acid, mesaconic acid, citraconic acid, fumaric acid, etc.; and salts, anhydrides, or half esters thereof. The unsaturated carboxylic acid is preferably (meth)acrylic acid. The salt of the unsaturated carboxylic acid is not particularly limited, but examples thereof include alkali metal salts, alkaline earth metal salts, and ammonium salts.

[0038] The substituent (B) formed by the reaction of the primary amino group (NH group) or secondary amino group (NH group) in the cationic group with an unsaturated ester compound and / or an unsaturated carboxylic acid (salt) preferably has a structure represented by any one of the following general formulas (5-1) to (5-3).

[0039] [ka]

[0040] (In general formulas (5-1) to (5-3), Y 2 are the same or different and represent a linear or branched hydrocarbon group having 1 to 10 carbon atoms. 2 R represents a hydrogen atom, an alkali metal, an alkaline earth metal, an ammonium group, an organic ammonium group, an organic amine group, or an organic group having 1 to 30 carbon atoms. 2 represents a linear alkylene group having 2 to 6 carbon atoms or a branched alkylene group having 3 to 6 carbon atoms. Above R 2 is the same as the above general formula (2). Above Y 2 , T 2 is the same as the above general formula (3).

[0041] When the polyalkylene oxide-containing compound of the present invention has a substituent (B), the above-mentioned substituent (A) and substituent (B) may each be bonded to at least one of the nitrogen atoms contained in the cationic group, and one nitrogen atom may be bonded to one substituent (A) or one substituent (B), or the same nitrogen atom may be bonded to two substituents (A), two substituents (B), or one each of a substituent (A) and a substituent (B).

[0042] The amount of the substituent (A) represented by the general formula (1) in the polyalkylene oxide-containing compound of the present invention is not particularly limited, but is preferably 5 to 90 mol % based on the total number of moles of nitrogen atoms contained in the polyalkylene oxide-containing compound, more preferably 10 to 90 mol %, and even more preferably 20 to 90 mol %. In one embodiment, the amount of the substituent (A) may be 5 to 50 mol %, preferably 10 to 45 mol %, more preferably 15 to 40 mol %, and even more preferably 20 to 35 mol %.

[0043] The amount of the substituent (A) represented by the general formula (1) is preferably 5 to 99 mol % based on the total amount of the substituent (A) and the substituent (B), more preferably 10 to 99 mol %, and further preferably 30 to 99 mol %. In one embodiment, the amount of the substituent (A) relative to the total amount of the substituent (A) and the substituent (B) may be 5 to 50 mol %, preferably 10 to 45 mol %, more preferably 15 to 40 mol %, and even more preferably 20 to 35 mol %.

[0044] The amount of the substituent (B) bonded to the cationic group in the polyalkylene oxide-containing compound of the present invention is not particularly limited, but from the viewpoint of mud dispersibility and anti-soil redeposition performance, it is preferably 1 to 90 mol% relative to the total moles of nitrogen atoms contained in the polyalkylene oxide-containing compound. More preferably, it is 5 to 60 mol%, and even more preferably, it is 10 to 50 mol%. From the viewpoint of improving storage stability, it is preferably 10 to 90 mol%. More preferably, it is 20 to 70 mol%, and even more preferably, it is 30 to 60 mol%.

[0045] T in the above general formula (3) 2 When is a hydrogen atom, an alkali metal, an alkaline earth metal, or an ammonium group, the amount of the substituent (B) bonded to the cationic group in the polyalkylene oxide-containing compound is preferably 1 to 90 mol %, more preferably 5 to 70 mol %, still more preferably 10 to 50 mol %, and particularly preferably 10 to 30 mol %, based on the total number of moles of nitrogen atoms contained in the polyalkylene oxide-containing compound.

[0046] T in the above general formula (3) 2 When is an organic group having 1 to 30 carbon atoms, the amount of the substituent (B) bonded to the cationic group in the polyalkylene oxide-containing compound is preferably 10 to 90 mol %, more preferably 20 to 70 mol %, and even more preferably 30 to 60 mol %, based on the total number of moles of nitrogen atoms contained in the polyalkylene oxide-containing compound.

[0047] The ratio of the amount of the substituent (A) represented by the above general formula (1) to the amount of the substituent (B) represented by the above general formula (3) of the polyalkylene oxide-containing compound is 1 It can be calculated from the H NMR spectrum. The substituent (A) has a polyalkylene oxide ester, and the substituent (B) has an ester structure or a carboxyl group, and the ratio of (A) to (B) can be calculated by calculating the peak integral ratio. In addition, the reaction of each raw material introduced in the process of introducing the substituents (A) and (B) into the polyalkylene oxide-containing compound can be quantitatively analyzed using HPLC or the like to determine the reaction amount of each raw material introduced, and the amount introduced into the polyalkylene oxide-containing compound can be calculated backward.

[0048] The amount of NH groups contained in the polyalkylene oxide-containing compound of the present invention is not particularly limited, but is preferably 20 mol% or less based on the total mole number of nitrogen atoms contained in the polyalkylene oxide-containing compound. More preferably, it is 10 mol% or less, even more preferably, it is 5 mol% or less, and most preferably, it is 0 mol%. In one embodiment, it may be more than 0 mol%. As described above, the number of NH groups in the cationic group of the polyalkylene oxide-containing compound of the present invention is reduced by bonding the substituent (A) represented by the general formula (1) and the substituent (B) represented by the general formula (3). In addition, the number of unreacted NH groups can be reduced by amidation reaction with carboxylic anhydrides such as acetic anhydride, succinic anhydride, and maleic anhydride, and carboxylic acid halides such as acetic acid chloride and propionic acid chloride, Michael addition of acrylic acid alkyl esters such as methyl acrylate, or addition of epoxy compounds such as ethylene oxide and propylene oxide. In order to make the polyalkylene oxide-containing compound more excellent in mud dispersibility and soil redeposition prevention performance, it is preferable that the amount of polyalkylene oxide groups introduced into the polyalkylene oxide-containing compound is large, and it is preferable that the amount of NH groups is small. Also, as described above, in order to make the polyalkylene oxide-containing compound of the present invention have excellent storage stability in the detergent composition, it is preferable that the amount of NH groups is small.

[0049] As described above, the cationic group contained in the polyalkylene oxide-containing compound of the present invention can also be represented as a structural unit having an amino group. Specific examples of the structural unit include those derived from compounds such as polyethylene polyamines (PEA) such as diethylenetriamine, triethylenetetramine, and tetraethylenepentamine, tetrabutylenepentamine, polyethyleneimine (PEI), and polyamidoamine. Preferred is polyethyleneimine obtained by ring-opening polymerization of ethyleneimine.

[0050] The precursor serving as a raw material for the structural unit having an amino group can be represented by the following general formula (2).

[0051] [ka]

[0052] (In general formula (2), R 2 are the same or different and each represents a linear alkylene group having 2 to 6 carbon atoms or a branched alkylene group having 3 to 6 carbon atoms. P is the same or different and represents a hydrogen atom or a structural unit having another amino group due to branching. a and b are the same or different and each represents an integer of 0 to 100, and at least one of a and b is 1 or greater. The cationic group (structural unit having an amino group) contained in the polyalkylene oxide-containing compound of the present invention preferably has a form in which three other amino groups are bonded to the nitrogen atom of at least one amino group. An embodiment in which the above-mentioned a and b are 1 or more and P has a structural unit having another amino group due to branching is one of the preferred embodiments of the present invention. When a precursor represented by the above general formula (2) is used, the group formed by removing the hydrogen atom bonded to the nitrogen atom from the precursor becomes the cationic group possessed by the polyalkylene oxide-containing compound of the present invention. In addition, regarding the precursor serving as a raw material for the structural unit having an amino group, the structural formula of the amino group constituting the precursor is, for example, H2N-R 2 -, -NH-R 2 -, -N(-)-R 2 -, etc. The structure derived from the compound represented by the general formula (2) refers to a structure in which one or more hydrogen atoms bonded to a nitrogen atom in the compound represented by the general formula (2) have been removed. The polyalkylene oxide-containing compound may contain only one structure derived from the compound represented by the general formula (2) in one molecule, or may contain two or more structures derived from the compound represented by the general formula (2) in one molecule.

[0053] When P in the general formula (2) is a structural unit having another amino group, the structural unit having another amino group is preferably represented by the following general formula (6), R 2’ It is preferable that the bond to the structure represented by the general formula (2) is via a group.

[0054] [ka]

[0055] (In general formula (6), a', b', P', R 2’ are a, b, P, and R in general formula (2), respectively. 2 is equivalent to.)

[0056] In the precursor that is the raw material of the structural unit having an amino group represented by the above general formula (2) or (6), R 2 The alkylene group in R may be one type or two or more types, but it is preferably one type, and an ethylene group is preferred. 2 When is a branched alkylene group having 3 to 6 carbon atoms, a 1,2-propylene group is preferred. The number of nitrogen atoms contained in a, b and P in the above general formulae (2) and (6) is not particularly limited, but the total number of nitrogen atoms is preferably 3 to 100, more preferably 4 to 75, even more preferably 5 to 65, still more preferably 8 to 60, still more preferably 10 to 55, and particularly preferably 12 to 45. In one aspect, the number of nitrogen atoms contained in the cationic group may be 5 to 60, and an embodiment in which the number is 7 to 50 is also one of the preferred embodiments of the present invention.

[0057] The amino group unit containing a primary amine nitrogen atom is represented, for example, by the following formula: (H2-NR 2 )- R 2 is the same as general formula (2). In some cases, it also contains a structural unit represented by the following formula: -NH2 The amino group unit containing a secondary amine nitrogen atom is represented, for example, by the following general formula (7).

[0058] [ka]

[0059] The amino group unit containing a tertiary amine nitrogen atom is represented, for example, by the following general formula (8).

[0060] [ka]

[0061] (P and R in general formulas (7) and (8) 2 is the same as general formula (2).

[0062] In the structural unit having an amino group, the form of the amino group unit is not particularly limited, and for example, the amino group unit (i) containing a primary amine nitrogen atom, the amino group unit (ii) containing a secondary amine nitrogen atom, and the amino group unit (iii) containing a tertiary amine nitrogen atom may be randomly present. The nitrogen atom constituting the amino group may be quaternized or oxidized.

[0063] In the cationic group of the polyalkylene oxide-containing compound, the molar ratio of the amino group units (i), (ii), and (iii) is preferably (i):(ii):(iii)=10-80 / 10-80 / 10-80, and more preferably (i):(ii):(iii)=20-50 / 20-50 / 20-50.

[0064] Moreover, one example of a precursor serving as a raw material for the structural unit having a cationic group of the present invention represented by the general formula (2) is an amine compound represented by the following general formula (9).

[0065] [ka]

[0066] (In general formula (9), R 6 are the same or different and each represents a linear alkylene group having 2 to 6 carbon atoms or a branched alkylene group having 3 to 6 carbon atoms. In addition, r represents an integer of 1 to 10.

[0067] The polyalkylene oxide-containing compound of the present invention undergoes a decomposition reaction by one or more decomposition methods selected from alkaline hydrolysis, enzymatic decomposition, and activated sludge, and the molecular weight can be reduced. When the polyalkylene oxide-containing compound of the present invention is subjected to a decomposition test using one or more decomposition methods selected from alkaline hydrolysis, enzymatic decomposition, and activated sludge, the number average molecular weight after the decomposition test is preferably 0.5 or less, more preferably 0.4 or less, and even more preferably 0.2 or less, relative to the number average molecular weight before the decomposition test. It is preferable that the number average molecular weight after the decomposition test is smaller than the number average molecular weight before the decomposition test, because when the composition of the present invention, for example, is used as a detergent or detergent composition, the burden on the environment caused by the compounds discharged after washing is reduced.

[0068] The weight average molecular weight of the polyalkylene oxide-containing compound of the present invention is preferably 1,000 to 1,000,000, more preferably 3,000 to 500,000, and further preferably 5,000 to 200,000. It is preferable that the weight average molecular weight of the polyalkylene oxide-containing compound of the present invention is within the above-mentioned range, since it has excellent anti-soil redeposition ability while reducing the burden on the environment due to the decomposition reaction. The weight average molecular weight of the polyalkylene oxide-containing compound can be measured by GPC under the following conditions. <Gel filtration chromatography (GPC) measurement conditions> Equipment: Tosoh EcoSEC HLC-8320GPC Detector: Differential Refractometer (RI) detector Column: Tosoh TSKgel α-M, α-2500 Column temperature: 40℃ Flow rate: 0.8mL / min Injection volume: 100μL Calibration curve: Polyethylene glycol manufactured by GL Sciences, Mw = 194, 410, 615, 1020, 1450, 3860, 8160, 16100, 21160, 49930, 67600, 96100, 205500, 542500, 942000, the order of the calibration curve is third order. GPC software: Tosoh EcoSEC-WS Eluent: 0.5M acetic acid + 0.2M Na nitrate / acetonitrile = 50 / 50 (v / v)

[0069] 2. Method for producing polyalkylene oxide-containing compound The method for producing the composition of the present invention is not particularly limited, and examples of the production method (I) include a production method including a first step of reacting an unsaturated carboxylic acid (salt) with a polyalkylene glycol compound, and a second step of reacting the product obtained in the first step with an amino group-containing compound.

[0070] The unsaturated carboxylic acid (salt) used in the first step of the production method (I) may be any one having an unsaturated group and a carboxyl group or a salt thereof, and specifically includes the unsaturated carboxylic acid (salt) described in the method for forming the substituent (B). Among them, (meth)acrylic acid is preferred.

[0071] The polyalkylene glycol compound used in the first step of the production method (I) may be any compound having a polyalkylene glycol chain and capable of reacting with an unsaturated carboxylic acid (salt), but is preferably one having a hydroxyl group at the end. In this case, the polyalkylene glycol compound reacts with the unsaturated carboxylic acid (salt) to form an ester bond. The polyalkylene glycol compound is preferably a compound represented by the following general formula (10): HO-(R 1 O) s1 -T 1 General formula (10) (In general formula (10), R 1 , s1, T 1 is the same as general formula (1).

[0072] Specific examples of the polyalkylene glycol compound include linear or branched butoxypolyethylene glycol, pentyloxypolyethylene glycol, hexyloxypolyethylene glycol, heptyloxypolyethylene glycol, octoxypolyethylene glycol, dodecyloxypolyethylene glycol, tetradecyloxypolyethylene glycol, hexadecyloxypolyethylene glycol, octadecyloxypolyethylene glycol, butoxy(poly)ethylene glycol (poly)propylene glycol, pentyloxy(poly)ethylene glycol (poly)propylene glycol, hexyloxy(poly)ethylene glycol (poly)propylene glycol, heptyloxy(poly)ethylene glycol (poly)propylene glycol, octoxy(poly)ethylene glycol (poly)propylene glycol, dodecyloxy(poly)ethylene glycol (poly)propylene glycol, tetradecyloxy(poly)ethylene glycol (poly)propylene glycol, hexadecyloxypolyethylene glycol, and octadecyloxypolyethylene glycol, and other alkoxypolyalkylene glycols. Preferred are butoxypolyethylene glycol, hexyloxypolyethylene glycol, dodecyloxypolyethylene glycol, hexadecyloxypolyethylene glycol, butoxypolyethylene glycol (poly)propylene glycol, hexyloxypolyethylene glycol (poly)propylene glycol, dodecyloxypolyethylene glycol (poly)propylene glycol, and hexadecyloxypolyethylene glycol (poly)propylene glycol.

[0073] The amount of the unsaturated carboxylic acid (salt) used in the first step of the above production method (I) is not particularly limited, but is preferably 100 to 500 mol % relative to 100 mol % of the polyalkylene glycol compound, and more preferably 200 to 300 mol %.

[0074] The reaction temperature of the unsaturated carboxylic acid (salt) and the polyalkylene glycol compound in the first step of the above production method (I) is not particularly limited, but is preferably 80 to 150°C, and more preferably 100 to 130°C.

[0075] The product obtained in the first step is, for example, a compound represented by the following formula (11):

[0076] [ka] (In general formula (11), R 1 , s1, T 1 is the same as in general formula (1). 7 are the same or different and are a hydrogen atom or a methyl group. The compound represented by the above formula (11) is preferably a linear or branched butoxypolyethylene glycol (meth)acrylate, a pentyloxypolyethylene glycol (meth)acrylate, a hexyloxypolyethylene glycol (meth)acrylate, a heptyloxypolyethylene glycol (meth)acrylate, an octoxypolyethylene glycol (meth)acrylate, a dodecyloxypolyethylene glycol (meth)acrylate, a tetradecyloxypolyethylene glycol (meth)acrylate, a hexadecyloxypolyethylene glycol (meth)acrylate, an octadecyloxypolyethylene glycol (meth)acrylate, a butoxy(poly)ethylene glycol (poly)propylene glycol (meth)acrylate, or a pentyloxy(poly)ethylene Examples of the alkoxy polyalkylene glycol (meth)acrylate include glycol (poly)propylene glycol (meth)acrylate, hexyloxy (poly)ethylene glycol (poly)propylene glycol (meth)acrylate, heptyloxy (poly)ethylene glycol (poly)propylene glycol (meth)acrylate, octoxy (poly)ethylene glycol (poly)propylene glycol (meth)acrylate, dodecyloxy (poly)ethylene glycol (poly)propylene glycol (meth)acrylate, tetradecyloxy (poly)ethylene glycol (poly)propylene glycol (meth)acrylate, hexadecyloxy polyethylene glycol (meth)acrylate, and octadecyloxy polyethylene glycol (meth)acrylate. Preferred are butoxypolyethylene glycol (meth)acrylate, hexyloxypolyethylene glycol (meth)acrylate, dodecyloxypolyethylene glycol (meth)acrylate, hexadecyloxypolyethylene glycol (meth)acrylate, butoxypolyethylene glycol (poly)propylene glycol (meth)acrylate, hexyloxypolyethylene glycol (poly)propylene glycol (meth)acrylate, dodecyloxypolyethylene glycol (poly)propylene glycol (meth)acrylate, and hexadecyloxypolyethylene glycol (poly)propylene glycol (meth)acrylate.

[0077] The amino group-containing compound used in the second step of the above production method (I) may be any compound having an amino group, but is preferably a polyalkyleneamine. The polyalkyleneamine is a compound having the structural formula represented by the above-mentioned general formula (2), and specific examples and preferred forms are as described in the precursor that serves as the raw material of the structural unit having an amino group.

[0078] The amount of the product obtained in the first step used in the second step of the production method (I) is not particularly limited, but is preferably 5 to 100 mol % relative to the total moles of nitrogen atoms in the amino group-containing compound (100 mol %). The amount of the polyalkylene glycol compound used is more preferably 10 to 70 mol %, and even more preferably 20 to 50 mol %. The amount of the compound represented by the above formula (11) used is preferably within the above range.

[0079] In the second step of the above-mentioned production method (I), it is preferable to carry out a Michael addition reaction between the product obtained in the first step and the above-mentioned amino group-containing compound. In this case, the reaction temperature is preferably 20 to 100°C, and more preferably 40 to 80°C. The reaction time is preferably 1 hour or more, more preferably 5 hours or more, and even more preferably 10 hours or more. When the reaction temperature and reaction time are within the above-mentioned ranges, the reaction proceeds almost quantitatively and is improved, and the amount of unreacted raw materials is reduced, which is preferable.

[0080] The product obtained in the first step of the above-mentioned production method (I) may contain an unsaturated carboxylic acid (salt) as an unreacted raw material, and in the second step, the above-mentioned unsaturated carboxylic acid (salt) may undergo Michael addition to the above-mentioned amino group-containing compound. In this case, a group derived from the unsaturated carboxylic acid (salt) becomes the substituent (B).

[0081] Another example of the production method (II) is a production method including a first step of subjecting an unsaturated ester compound to a compound containing an amino group by Michael addition, and a second step of introducing a polyalkylene oxide chain into the group derived from the unsaturated ester compound of the product obtained in the first step. The unsaturated ester compound used in the first step may be any compound having an unsaturated group and an ester group, and specific examples and preferred forms are as described above. The amino group-containing compound used in the first step may be any compound having an amino group, but is preferably the same amino group-containing compound as in the production method (I) above.

[0082] The amount of the unsaturated ester compound used in the first step of the above-mentioned production method (II) is not particularly limited, but is preferably 80 to 150 mol% relative to the total moles of nitrogen atoms in the amino group-containing compound (100 mol%). This allows the amount of NH groups in the cationic groups of the polyalkylene oxide-containing compound of the present invention to be more sufficiently reduced. The amount of the unsaturated ester compound used is more preferably 90 to 140 mol%, and even more preferably 100 to 130 mol%.

[0083] In the above first step, the double bond of the unsaturated ester compound can be subjected to Michael addition with the amino group of the amino group-containing compound to bond the substituent (B) to the amino group.

[0084] The reaction temperature for the Michael addition reaction in the first step is not particularly limited, but is preferably 20 to 100°C, and more preferably 25 to 80°C. The reaction time is preferably 1 hour or more, more preferably 5 hours or more, and even more preferably 10 hours or more. 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 materials is reduced, which is preferable.

[0085] The second step of the above-mentioned production method (II) is not particularly limited as long as a polyalkylene oxide chain is introduced into at least a part of the group derived from the unsaturated ester compound of the product obtained in the above-mentioned first step, but it is preferable to introduce the polyalkylene oxide chain by reacting a polyalkylene glycol compound as a polyalkylene oxide raw material with the group derived from the above-mentioned unsaturated ester compound to carry out ester exchange. In this case, the group derived from the unsaturated ester compound is bonded to the nitrogen atom of the amino group, i.e., -Y in general formula (1) or (3), 1 -COO- or -Y 2 It becomes a linking group represented by -COO-. In one embodiment, in the method for producing a composition of the present invention, in the second step, a polyalkylene oxide chain (polyalkylene glycol compound) may be introduced into all of the groups derived from the unsaturated ester compound of the product obtained in the first step. In the second step, the group derived from the unsaturated ester compound to which no polyalkylene oxide chain has been introduced becomes the substituent (B).

[0086] The polyalkylene glycol compound used in the second step may be any compound having a polyalkylene oxide chain and capable of undergoing an ester exchange reaction with a group derived from the unsaturated ester compound. In one preferred embodiment of the present invention, the compound is represented by the general formula (10).

[0087] The amount of the polyalkylene glycol compound used in the second step is not particularly limited, but is preferably 1 to 100 mol% relative to the total moles of nitrogen atoms in the amino group-containing compound (100 mol%). The amount of the polyalkylene glycol compound used is more preferably 5 to 90 mol%, even more preferably 10 to 80 mol%, and still more preferably 20 to 50 mol%. The amount of the polyalkylene glycol compound used is preferably 1 to 100 mol % relative to 100 mol % of the groups derived from the unsaturated ester compound of the product obtained in the first step, more preferably 5 to 90 mol %, further preferably 10 to 80 mol %, and particularly preferably 20 to 50 mol %.

[0088] The above-mentioned production methods (I) and (II) may include, in addition to the above-mentioned steps, a step of reducing the number of unreacted NH groups contained in the cationic group and not bonded to the substituent (A) or (B), by subjecting the unreacted NH groups to one or more of Michael addition reaction, acetylation reaction, amidation reaction with a carboxylic acid anhydride, amidation reaction with a carboxylic acid halide, and epoxy compound addition reaction. More specifically, the unreacted NH groups to which the substituent (A) or (B) contained in the cationic group is not bonded can be reduced by subjecting an unsaturated ester compound such as an acrylic acid alkyl ester to a Michael addition reaction, or by subjecting the unreacted NH groups to an amidation reaction with a carboxylic acid anhydride such as acetic anhydride, succinic anhydride, or maleic anhydride, or a carboxylic acid halide such as acetic acid chloride or propionic acid chloride, or by adding an epoxy compound such as ethylene oxide or propylene oxide. In the above production method (I), an embodiment including a step of reducing unreacted NH groups after the first step and the second step is one of the preferred embodiments of the present invention. From the viewpoint of improving mud dispersibility, anti-soil redeposition performance, and storage stability, it is preferable that the unreacted NH groups be 80 mol % or less, more preferably 50 mol % or less, and even more preferably 20 mol % or less, based on the total NH of the polyalkylene oxide-containing compound.

[0089] 3. Composition containing a polyalkylene oxide-containing compound A composition containing the polyalkylene oxide-containing compound of the present invention and an ingredient other than the polyalkylene oxide-containing compound also constitutes the present invention. The other components are not particularly limited, but may include raw materials and intermediates used in the production of the polyalkylene oxide-containing compound of the present invention. In the case of the above-mentioned production method (I), raw materials and intermediates such as the unsaturated carboxylic acid (salt), the polyalkylene glycol compound, the product obtained in the first step, and the amino group-containing compound may remain unreacted. In the case of the above-mentioned production method (II), raw materials and intermediates such as the unsaturated ester compound, the amino group-containing compound, the product obtained in the first step, and the polyalkylene glycol compound may remain unreacted. Other components in the composition include raw materials and intermediates such as unsaturated ester compounds, unsaturated carboxylic acids (salts), amino group-containing compounds, and polyalkylene glycol compounds in the production of the polyalkylene oxide-containing compound. The total content of the other components in the composition is preferably 50% by mass or less, more preferably 30% by mass or less, and even more preferably 10% by mass or less, when the total amount of the composition is 100% by mass.

[0090] The composition 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 sequestering agent, a thickener, various binders, etc. Among them, the composition of the present invention can be suitably used as a detergent builder, a detergent, a water treatment agent, and a dispersant.

[0091] The present invention further relates to a detergent builder, a detergent, a detergent composition, a water treatment agent, or a dispersant, which contains the composition of the present invention as an essential component. The detergent and detergent composition of the present invention may be in a solid or liquid form. The detergent and detergent composition may be for use in dishes or for use in washing clothes and the like.

[0092] The content of the polyalkylene oxide-containing compound of the present invention in the detergent or detergent composition of the present invention is preferably 0.1 to 15 mass %, more preferably 0.3 to 10 mass %, and even more preferably 0.5 to 5 mass %, based on the total amount of the detergent or cleaning composition.

[0093] The detergent and detergent composition of the present invention may contain, in addition to the polyalkylene oxide-containing compound of the present invention, one or more other components such as a solvent, a surfactant, a cleaning auxiliary additive, and an encapsulating agent. Examples of cleaning auxiliary additives include builders, surfactants or thickeners, mud stain removal / redeposition prevention agents, polymer stain release agents, polymer dispersants, polymer grease cleaning agents, enzymes, enzyme stabilizing systems, bleaching compounds, bleaching agents, bleach activators, bleaching catalysts, brighteners, dyes, hueing agents, dye transfer inhibitors, chelating agents, foam suppressors, fabric softeners, fragrances, and the like, and these may be used alone or in combination of two or more.

[0094] The content of other components in the detergent or detergent composition is not particularly limited, but is preferably 1 to 30% by mass, more preferably 2 to 20% by mass, and even more preferably 3 to 10% by mass, relative to 100% by mass of the detergent or detergent composition. EXAMPLES

[0095] 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, "%" means "% by mass".

[0096] <Production Example 1> A glass reaction vessel equipped with a nitrogen inlet tube, a reflux condenser, and a stirrer was charged with 40.00 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600, nitrogen atom number 14) and 120.00 g of ethanol (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.), and the atmosphere in the reaction vessel was replaced with nitrogen. Then, 116.82 g of ethyl acrylate (manufactured by Nippon Shokubai) was added dropwise over 30 minutes while stirring at 25°C, and the reaction was continued for 19 hours. The consumption of ethyl acrylate was confirmed by liquid chromatography, and the reaction solution was collected in a recovery flask. Ethanol and remaining ethyl acrylate were distilled off under reduced pressure from the reaction solution using a rotary evaporator, and an ethyl acrylate adduct intermediate of polyethyleneimine (1) was obtained.

[0097] <Example 1> 9.78 g of Softanol 200 (manufactured by Nippon Shokubai, 20 mole ethylene oxide adduct of C12-14 secondary alcohol) and 0.25 g of potassium hydroxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were charged into a glass reaction vessel equipped with a thermometer, a stirrer tip, and a nitrogen inlet tube, and the mixture was stirred at 120°C for 1 hour while nitrogen was flowing into the system. Then, 2.50 g of the intermediate (1) obtained in Production Example 1 was dropped into the system, and the mixture was stirred at 120°C for 18 hours to carry out an ester exchange reaction. The reaction of Softanol 200 was confirmed by liquid chromatography, and a reaction product (1) (polymer (1)) was obtained. (Reaction rate: 65.0%, ratio of groups derived from Softanol 200: 33.7 mol%, ratio of groups derived from ethyl acrylate: 66.3 mol%)

[0098] <Example 2> 13.76 g of Softanol 300 (manufactured by Nippon Shokubai, an ethylene oxide 30 mole adduct of C12-14 secondary alcohol) and 0.25 g of potassium hydroxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were charged into a glass reaction vessel equipped with a thermometer, a stirrer tip, and a nitrogen inlet tube, and the mixture was stirred at 120°C for 1 hour while nitrogen was flowing into the system. Thereafter, 2.50 g of the intermediate (1) obtained in Production Example 1 was dropped into the system, and the mixture was stirred at 120°C for 18 hours to carry out an ester exchange reaction. The reaction of Softanol 300 was confirmed by liquid chromatography, and a reaction product (2) (polymer (2)) was obtained. (Reaction rate: 65.0%, ratio of groups derived from Softanol 300: 33.7 mol%, ratio of groups derived from ethyl acrylate: 66.3 mol%)

[0099] <Example 3> 11.30 g of Softanol 500 (manufactured by Nippon Shokubai, 50 mole ethylene oxide adduct of C12-14 secondary alcohol) and 0.13 g of potassium hydroxide (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd.) were charged into a glass reaction vessel equipped with a thermometer, a stirrer tip, and a nitrogen inlet tube, and the mixture was stirred at 120°C for 1 hour while nitrogen was flowed into the system. Thereafter, 1.30 g of the intermediate (1) obtained in Production Example 1 was dropped into the system, and the mixture was stirred at 120°C for 18 hours to carry out an ester exchange reaction. The reaction of Softanol 500 was confirmed by liquid chromatography, and a reaction product (3) (polymer (3)) was obtained. (Reaction rate: 50.7%, ratio of groups derived from Softanol 500: 26.3 mol%, ratio of groups derived from ethyl acrylate: 73.7 mol%)

[0100] <Measurement of anti-redeposition ability> The following washing process, rinsing process, and drying process were carried out in this order, and the ability to prevent soil redeposition on the fabric was measured. Washing process: The following two types of cotton cloth were used for washing. Cotton cloth (1): Five pieces of cotton knit cloth (manufactured by Tanigashira Shoten) measuring 5 cm x 5 cm were prepared as recontamination judgment cloths. Cotton cloth (2): Cotton cloth obtained from Testfabrics was combined with cotton cloth (1) to give a total weight of 30 g. As a surfactant, a 3% aqueous solution of LAS and a 0.1% by mass aqueous solution of the reaction product obtained in Production Example were prepared. In a 1L pot for a Tergot-o-meter (manufactured by Daiei Scientific Co., Ltd., product name: TM-4), 876 g of pure water at 25°C was added, followed by 4.5 g of 1.5 mass% sodium bicarbonate aqueous solution and stirring. Then, 4.5 g of 3000° DH hard water (prepared with calcium chloride and magnesium chloride, Ca / Mg=3 (mass ratio)) was added, followed by 7.5 g of 3% LAS aqueous solution and 7.5 g of 0.1% aqueous solutions of the reaction products (1) to (3) and stirring. Then, 0.9 g of plain red clay was added and stirred, followed by adding cotton cloths (1) and (2) and washing for 10 minutes at 25°C with a stirring speed of 120 rpm. Rinse step: After the washing step, the washed items were dehydrated for 1.5 minutes, and then rinsed in 900 mL of 15° DH hard water at 25° C. for 3 minutes at 120 rpm and 25° C. This operation (dehydration and rinsing) was repeated twice. Drying process: After the rinsing step, the washed items were dehydrated for 1.5 minutes, and then only the cotton cloth (1) was taken out, sandwiched between two cotton cloths, and dried with an iron. The reflectance (Z value) of the cotton fabric (1) that had been subjected to the above-mentioned washing treatment and the cotton fabric (1) before the washing treatment was measured using a reflectometer (spectrophotometer, product name: SE6000, manufactured by Nippon Denshoku Industries Co., Ltd.), and the anti-redeposition rate was calculated using the following formula. Redeposition prevention rate = (Z value of cotton cloth (1) after washing) / (Z value of cotton cloth (1) before washing) x 100

[0101] The redeposition prevention rate of the cotton fabric (1) after the above washing treatment is shown in Table 1.

[0102] [Table 1]

Claims

1. The following general formula (1): 【Chemistry 1】 (In general formula (1), R １ are the same or different and represent a hydrocarbon group having 2 to 6 carbon atoms. s1 is an integer of 1 to 300. Y １ represents a direct bond or a linear or branched hydrocarbon group having 1 to 10 carbon atoms. １ represents an organic group having 4 to 18 carbon atoms; and a cationic group having a nitrogen atom, The polyalkylene oxide-containing compound, wherein the substituent (A) is bonded to at least one of the nitrogen atoms contained in the cationic group.

2. T in the substituent (A) in the general formula (1) １ is an alkyl group having 4 to 18 carbon atoms, an alkenyl group having 4 to 18 carbon atoms, an alkynyl group having 4 to 18 carbon atoms, an aromatic hydrocarbon group having 6 to 18 carbon atoms, or a heterocyclic group having 4 to 18 carbon atoms.

3. T in the substituent (A) in the general formula (1) １ The polyalkylene oxide-containing compound according to claim 1, wherein is a linear, branched or cyclic alkyl group having 4 to 18 carbon atoms, or an aromatic hydrocarbon group having 6 to 18 carbon atoms.

4. Y in the substituent (A) in the general formula (1) １ The polyalkylene oxide-containing compound according to claim 1, wherein is a hydrocarbon group having 2 to 4 carbon atoms.

5. The polyalkylene oxide-containing compound is represented by the following general formula (2): 【Chemistry 2】 (In general formula (2), R ２ are the same or different and represent a linear alkylene group having 2 to 6 carbon atoms, or a branched alkylene group having 3 to 6 carbon atoms. P is the same or different and represents a hydrogen atom, or a structural unit having another amino group due to branching. a and b are the same or different and represent an integer of 0 to 100, and at least one of a and b is 1 or greater. The polyalkylene oxide-containing compound according to claim 1, having a structure derived from a compound represented by the following formula:

6. The polyalkylene oxide-containing compound may further be represented by the following general formula (3): 【Chemistry 3】 (Y ２ represents a direct bond or a linear or branched hydrocarbon group having 1 to 10 carbon atoms. ２ represents a hydrogen atom, an alkali metal, an alkaline earth metal, an ammonium group, or an organic group having 1 to 30 carbon atoms, and the substituent (B) is bonded to at least one nitrogen atom contained in the cationic group.

7. A detergent or detergent composition comprising the polyalkylene oxide-containing compound according to any one of claims 1 to 6.

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