Composition including cation group-containing compound and polyalkylene glycol compound

Abstract

To provide a composition excellent in compatibility with a surfactant.SOLUTION: A composition contains a cation group-containing compound (α) and a polyalkylene glycol compound (β). The cation group-containing compound (α) has: a substituent (A) represented by the following general formula (1) (in the general formula (1), R1s are identical or different and represent a 2-6C hydrocarbon group, s1 is an integer of 1 to 300, Y1 represents a direct bond or a straight-chained or branched 1-10C hydrocarbon group, and T1 represents a hydrogen atom or a 1-30C organic group); and a cation group having a nitrogen atom. The substituent (A) is bound to at least one of the nitrogen atoms contained in the cation group. A content percentage of the polyalkylene glycol compound (β) is 1 to 30 mass%, based on 100 mass% of a total amount of the cation group-containing compound (α) and the polyalkylene glycol compound (β).SELECTED DRAWING: None

Description

[Technical field]

[0001] The present invention relates to a composition containing a cationic group-containing compound and a polyalkylene glycol compound, more particularly to a composition containing a cationic group-containing compound and a polyalkylene glycol compound that is useful for 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] Meanwhile, through their investigations to date, the present inventors have discovered that the anti-soil redeposition ability can be improved by using a cationic group-containing compound that contains an alkyleneamine structural unit having a polyalkylene oxide chain in a detergent composition.

[0007] In recent years, there has been a trend toward more concentrated liquid detergents (those with a low water content), and consumers have also shown a preference for clear, transparent liquid detergents. Therefore, when using such cationic group-containing compounds as described above in detergent compositions, there was room for further improving their compatibility with surfactants.

[0008] The present invention has been made in consideration of the above-mentioned current situation, and has an object to provide a composition that has excellent compatibility with surfactants. [Means for solving the problem]

[0009] The present inventors have conducted extensive research into compositions containing a polyalkylene oxide copolymer containing an alkyleneamine structural unit having a polyalkylene oxide chain, and have found that a composition containing a cationic group-containing compound having a substituent of a predetermined structure and a cationic group having a nitrogen atom, where the substituent is bonded to at least one of the nitrogen atoms contained in the cationic group, and a polyalkylene glycol compound, wherein the ratio of the polyalkylene glycol compound is within a predetermined range, has excellent compatibility with surfactants. They have thus come to the conclusion that the above-mentioned problems can be admirably solved, and have arrived at the present invention.

[0010] The present invention includes the following compositions, etc. [1] A composition comprising a cationic group-containing compound (α) and a polyalkylene glycol compound (β), wherein the cationic group-containing compound (α) is a compound represented by 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. 1 represents a hydrogen atom or an organic group having 1 to 30 carbon atoms.) and a cationic group having a nitrogen atom, said substituent (A) is bonded to at least one of the nitrogen atoms contained in the cationic group, and the content of said polyalkylene glycol compound (β) is 1 to 30 mass% with respect to 100 mass% of the total amount of the cationic group-containing compound (α) and the polyalkylene glycol compound (β). [2] Y in the substituent (A) described in the above general formula (1) 1 is a hydrocarbon group having 2 to 4 carbon atoms. [3] The cationic group-containing compound (α) 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, at least one of a and b is 1 or greater. The composition according to the above [1] or [2], having a structure derived from a compound represented by the following formula: [4] The cationic group-containing compound (α) may further be represented by the following general formula (3); [ka] (In general formula (3), Y 2represents 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. [5] The polyalkylene glycol compound (β) is represented by the following general formula (4); R 3 -(OR 5 ) s2 -OR 4 General formula (4) (In general formula (4), R 3 , R 4 are the same or different and each represents a hydrogen atom or an organic group having 1 to 18 carbon atoms. 3 , R 4 At least one of R is an organic group having 1 to 18 carbon atoms. 5 and s2 is an integer of 1 to 300. The composition according to any one of the above items [1] to [4], wherein the structure is represented by: [6] A detergent or detergent composition comprising the composition according to any one of [1] to [5] above. Effect of the Invention

[0011] The composition of the present invention has the above-mentioned constitution and has excellent compatibility with surfactants, and therefore can be suitably used in detergents and the like. DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS

[0012] 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.

[0013] In the following description, unless otherwise specified, "%" means "% by mass", and "A to B" indicating a range means A or more and B or less. In addition, in the present invention, "(meth)acrylate" means "acrylate" or "methacrylate", and "(meth)acrylic" means "acrylic" or "methacrylic".

[0014] [Composition Containing a Cationic Group-Containing Compound (α) and a Polyalkylene Glycol Compound (β) (hereinafter also referred to as the Composition of the Present Invention)] The composition of the present invention contains a cationic group-containing compound (α) and a polyalkylene glycol compound (β), and the content of the polyalkylene glycol compound (β) is 1 to 30% by mass relative to 100% by mass of the total amount of the cationic group-containing compound (α) and the polyalkylene glycol compound (β). This makes the composition highly compatible with surfactants and suitable for use in detergent applications. The content of the polyalkylene glycol compound (β) is preferably 1 to 25 mass %, more preferably 2 to 20 mass %, further preferably 3 to 15 mass %, and particularly preferably 4 to 10 mass %.

[0015] The composition of the present invention may contain other components in addition to the cationic group-containing compound (α) and the polyalkylene glycol compound (β). The content of the other components is not particularly limited, but is preferably 1 to 40% by mass, more preferably 1 to 30% by mass, and even more preferably 1 to 20% by mass, relative to 100% by mass of the composition.

[0016] The essential and optional components contained in the composition of the present invention are further described below.

[0017] <Cation group-containing compound (α)> The cationic group-containing compound (α) in the present invention is represented by the following general formula (1); [ka]

[0018] (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 a hydrogen atom or an organic group having 1 to 30 carbon atoms.) and a cationic group having a nitrogen atom, and the substituent (A) has a structure in which the substituent (A) is bonded to at least one of the nitrogen atoms contained in the cationic group.

[0019] The substituent (A) represented by the above general formula (1) is -(R 1 O) s1 a structural portion derived from a polyalkylene oxide represented by -Y 1 The linking group is preferably a group having a linking group represented by -COO-. The linking group is preferably such a group, since it can enhance the storage stability, hydrolysis property and biodegradability after use of the cationic group-containing compound (α). In addition, it is preferable since it tends to improve the mud particle dispersion ability and the redeposition prevention ability of the cationic group-containing compound (α) of the present invention. 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. Biodegradable means that it can be metabolized and broken down by organisms such as bacteria, fungi, and other organisms.

[0020] R in the general formula (1) 1 is 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 at least one selected from an oxyethylene group, an oxypropylene group, and an oxybutylene group. These preferred substituents and atoms improve the water solubility of the cationic group-containing compound (α), and the cationic group-containing compound (α) of the present invention can have better mud dispersibility and compatibility with liquid detergents.

[0021] In the general formula (1), s1 is not particularly limited as long as it is an integer of 1 to 300. It is preferably 2 to 200, more preferably 3 to 100, further preferably 4 to 80, and particularly preferably 5 to 50. When s1 in the general formula (1) is within such a range, the mud dispersibility and the soil redeposition prevention performance of the cationic group-containing compound (α) are further improved. In the general formula (1), s1 may be any number from 1 to 300, but in the cationic group-containing compound (α) of the present invention, the average chain length of the polyalkylene oxide is preferably from 1 to 300. It is more preferably from 2 to 200, even more preferably from 3 to 100, even more preferably from 4 to 80, and particularly preferably from 5 to 50. 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).

[0022] (R 1 O) s1 In one embodiment, the compound represented by the following general formula (5); (R 1’ O) t -(R 1 O) s1-t (5) (In general formula (5), 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 compound (1), the ester group in the general formula (1) is less susceptible to hydrolysis, and the stability of the cationic group-containing compound (α) 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 (5) 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. R in the above general formula (1) 1 is an ethylene group is one of the preferred embodiments of the present invention.

[0023] Y in the general formula (1) 1 is a direct bond, or a straight-chain or branched-chain hydrocarbon group having 1 to 10 carbon atoms. Y 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. Furthermore, the hydrocarbon group is preferably an alkylene group, and more preferably an ethylene group or an isopropylene group.

[0024] The cationic group-containing compound (α) of the present invention is preferably one that is decomposed at the linking group portion. In this case, it is preferable that the decomposition portion of the linking group that bonds the cationic group and the structural unit derived from the polyalkylene oxide is not directly bonded to the cationic group, but is 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 decomposition property of the cationic group-containing compound (α).

[0025] T in the general formula (1) above 1is not particularly limited as long as it is a hydrogen atom or an organic group having 1 to 30 carbon atoms, and the structure may be appropriately selected to adjust the hydrophilicity and hydrophobicity. The organic group is preferably a hydrocarbon group. More preferably, it is a linear or branched alkyl group, an alkenyl group, an alkynyl group, or an aryl group. Also preferred are organic groups having a structure in which a carboxyl group, a phosphoric acid group or a sulfonic acid group is bonded to the above-mentioned hydrocarbon group.

[0026] Above T 1 The organic group 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.

[0027] Examples of the linear or branched alkyl group include a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group (an amyl group), 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, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, an n-nonadecyl group, an n-eicosanyl group, an i-propyl group, a sec-butyl group, an i-butyl group, a t-butyl group, a 1-methylbutyl group, a 1-ethylpropyl group, a 2-propyl ... Examples of the alkyl groups include 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, branched nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, stearyl, and icosyl.

[0028] Examples of the alkenyl group include a vinyl group, an allyl group, 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, an octadecenyl group, and an icosenyl group. Examples of the alkynyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a butynyl group, a pentynyl group, a hexynyl group, a heptynyl group, an octynyl group, a nonynyl group, a decynyl group, a dodecynyl group, an octadecynyl group, and an icosynyl group.

[0029] Examples of the aryl group include a phenyl group; a naphthyl group; and aralkyl groups such as a b 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, and a 1,2,3,4-tetrahydronaphthyl group.

[0030] Above T 1 is preferably a straight-chain or branched alkyl group, among which a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, and a tert-butyl group are preferred, and a methyl group and an ethyl group are more preferred.

[0031] The cationic group-containing compound (α) of the present invention further comprises a compound represented by the following general formula (3); [ka] (In general formula (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 preferably 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 cationic group-containing compound (α) contains an ester structure, ester amide exchange with the ester structure or hydrolysis occurs at the primary and secondary amino group parts in the composition, which causes a decrease in the storage stability of the cationic group-containing compound (α). In contrast, 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, such ester amide exchange and hydrolysis can be suppressed, and thus the cationic group-containing compound (α) of the present invention has excellent storage stability in the composition.

[0032] Above Y 2 Specific examples and preferred forms of the hydrocarbon group in the above general formula (1) are 1 Among them, an ethylene group and an isopropylene group are preferred. Above T 2 Specific examples and preferred forms of the organic group in the above general formula (1) are 1 The organic groups are the same as those in the above. Above T 2 The organic group preferably has 1 to 24 carbon atoms, more preferably 1 to 18 carbon atoms, even more preferably 1 to 15 carbon atoms, still more preferably 1 to 10 carbon atoms, still more preferably 1 to 8 carbon atoms, and particularly preferably 1 to 6 carbon atoms. T 1 Among the above organic groups in 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 2is an organic group having 2 to 6 carbon atoms. Above T 2 When R is a methyl group, R 1 O) s1 is a structure represented by general formula (5) is one of the preferred embodiments of the present invention.

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

[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) is preferably a structure represented by any one of the following general formulas (6-1) to (6-3).

[0039] [ka]

[0040] (In general formulas (6-1) to (6-3), 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] In the cationic group-containing compound (α) of the present invention, 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 cationic group-containing compound (α) 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 cationic group-containing compound (α), 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 cationic group-containing compound (α) 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% based on the total moles of nitrogen atoms contained in the cationic group-containing compound (α). It is more preferably 5 to 60 mol%, and even more preferably 10 to 50 mol%. From the viewpoint of improving storage stability, it is preferably 10 to 90 mol%. It is more preferably 20 to 70 mol%, and even more preferably 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 cationic group-containing compound (α) is preferably 1 to 90 mol %, more preferably 5 to 70 mol %, and even more preferably 10 to 50 mol %, based on the total number of moles of nitrogen atoms contained in the cationic group-containing compound (α).

[0046] T in the above general formula (3) 2 is an organic group having 1 to 30 carbon atoms, the amount of the substituent (B) bonded to the cationic group in the cationic group-containing compound (α) 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 cationic group-containing compound (α).

[0047] The ratio of the amount of the substituent (A) represented by the general formula (1) to the amount of the substituent (B) is 1It 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 of the raw materials introduced in the step of introducing the substituents (A) and (B) into the cationic group-containing compound (α) can be quantitatively analyzed using HPLC or the like to determine the reaction amount of each of the raw materials introduced, and the amount introduced into the cationic group-containing compound (α) can be calculated backward.

[0048] The amount of NH groups contained in the cationic group-containing compound (α) of the present invention is not particularly limited, but is preferably 20 mol % or less based on the total number of moles of nitrogen atoms contained in the cationic group-containing compound (α), more preferably 10 mol % or less, even more preferably 5 mol % or less, and most preferably 0 mol %. As described above, the number of NH groups in the cationic group of the cationic group-containing compound (α) 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 acid 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 cationic group-containing compound (α) more excellent in mud dispersibility and soil redeposition prevention performance, it is preferable that the amount of polyalkylene oxide groups introduced into the cationic group-containing compound (α) is large, and it is preferable that the amount of NH groups is small. Also, as described above, in order to make the cationic group-containing compound (α) of the present invention have excellent storage stability in a detergent composition, it is preferable that the amount of NH groups is small.

[0049] As described above, the cationic group contained in the cationic group-containing compound (α) of the present invention can also be expressed 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 cationic group-containing compound (α) 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 cationic group-containing compound (α) 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 cationic group-containing compound (α) 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).

[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 (7), R 2’ It is preferable that the bond to the structure represented by formula (2) is via a group.

[0054] [ka]

[0055] (In general formula (7), a', b', P', R 2’ are a, b, P, and R in general formula (2), respectively. 2 is equivalent to.)

[0056] In the precursors serving as raw materials for structural units having an amino group represented by the above general formula (2) or (7), 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. In the above general formulas (2) and (7), the total number of nitrogen atoms contained in a, b and P is preferably 4 to 100, more preferably 5 to 75, further preferably 10 to 50, 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 (8).

[0058] [ka]

[0059] The amino group unit containing a tertiary amine nitrogen atom is represented, for example, by the following general formula (9).

[0060] [ka]

[0061] (P and R in general formulas (8) and (9) 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 cationic group-containing compound (α), 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] Furthermore, 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 (10).

[0065] [ka]

[0066] (In general formula (10), 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 cationic group-containing compound (α) of the present invention can undergo a decomposition reaction by one or more decomposition methods selected from alkaline hydrolysis, enzymatic decomposition, and activated sludge, thereby reducing the molecular weight. When the cationic group-containing compound (α) of the present invention is subjected to a decomposition test by 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 cationic group-containing compound (α) of the present invention is preferably from 1,000 to 1,000,000, more preferably from 3,000 to 500,000, and further preferably from 5,000 to 200,000. It is preferable that the weight average molecular weight of the cationic group-containing compound (α) 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 cationic group-containing compound (α) 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] <Polyalkylene glycol compound (β)> The polyalkylene glycol compound (β) in the present invention is not particularly limited as long as it has a polyalkylene glycol chain, but is preferably represented by the following general formula (4): R 3 -(OR 5 ) s2 -OR 4 General formula (4) (In general formula (4), R 3 , R 4 are the same or different and each represents a hydrogen atom or an organic group having 1 to 18 carbon atoms. 3 , R 4 At least one of R is an organic group having 1 to 18 carbon atoms. 5 and are the same or different and represent a hydrocarbon group having 2 to 6 carbon atoms. s2 is an integer of 1 to 300.

[0070] Above R 3 , R 4The organic group in is preferably a hydrocarbon group, more preferably a linear or branched alkyl group, an alkenyl group, an alkynyl group, or an aryl group. The organic group may have a structure in which any one of a carboxyl group, a phosphoric acid group, and a sulfonic acid group is bonded to the hydrocarbon group.

[0071] Above R 3 , R 4 The organic group preferably has 1 to 15 carbon atoms, more preferably 1 to 10 carbon atoms, further preferably 1 to 8 carbon atoms, even more preferably 1 to 6 carbon atoms, and particularly preferably 1 to 4 carbon atoms.

[0072] Specific examples of linear or branched alkyl groups, alkenyl groups, alkynyl groups, and aryl groups are T 1 As stated above. Above R 3 , R 4 The organic group in is preferably a linear or branched alkyl group or an alkenyl group, more preferably a linear or branched alkyl group, and further preferably an alkyl group having 1 to 4 carbon atoms such as a methyl group, an ethyl group, a propyl group, or a butyl group.

[0073] Above R 3 , R 4 At least one of the groups may be an organic group having 1 to 18 carbon atoms, but preferably one is a hydrogen atom and the other is in the form of an organic group having 1 to 18 carbon atoms. More preferably, one is a hydrogen atom and the other is in the form of an alkyl group.

[0074] R in general formula (4) 5 is 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. 5 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. -R in the above general formula (4) 5The O group is preferably at least one selected from the group consisting of an oxyethylene group, an oxypropylene group, and an oxybutylene group. (R 5 O) may be a structure represented by general formula (5). -R in the above general formula (4) 5 An embodiment in which the O group is an oxyethylene group is one of the preferred embodiments of the present invention.

[0075] In the above general formula (4), s2 may be 1-300, preferably 2-200, more preferably 3-100, further preferably 4-80, and particularly preferably 5-50.

[0076] Specific examples of the polyalkylene glycol compound (β) include alkoxypolyalkylene glycols such as methoxypolyethylene glycol, ethoxypolyethylene glycol, methoxy(poly)ethylene glycol (poly)propylene glycol, methoxy(poly)ethylene glycol (poly)butylene glycol, and ethoxy(poly)ethylene glycol (poly)propylene glycol. Preferred are methoxypolyethylene glycol and methoxypolyethylene glycol (poly)propylene glycol.

[0077] <Other components other than the cationic group-containing compound (α) and the polyalkylene glycol compound (β)> The composition of the present invention may contain other components in addition to the cationic group-containing compound (α) and the polyalkylene glycol compound (β). The other components are not particularly limited, but include raw materials and intermediates used in the production of the composition of the present invention, which will be described later. As described below, the composition of the present invention can be produced by carrying out 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. In this case, raw materials and intermediates such as the unsaturated carboxylic acid (salt), the polyalkylene glycol compound, and the product obtained in the first step may remain unreacted, but the composition of the present invention may contain an unsaturated carboxylic acid (salt), an amino group-containing compound, etc. in addition to the cationic group-containing compound (α) and the polyalkylene glycol compound (β).

[0078] The composition of the present invention can also be produced by a production method including a first step of Michael addition of an unsaturated ester compound to an amino group-containing compound, and a second step of introducing a polyalkylene glycol chain into a group derived from the unsaturated ester compound of the product obtained in the first step, as described below. In this case, raw materials and intermediates such as the unsaturated ester compound, the product obtained in the first step, and the polyalkylene glycol compound may remain unreacted, and the composition of the present invention may contain these components.

[0079] [Method for producing a composition containing a cationic group-containing compound (α) and a polyalkylene glycol compound (β)] 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.

[0080] 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.

[0081] 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 the polyalkylene glycol compound (β) described above. An embodiment in which the polyalkylene glycol compound is a compound represented by the general formula (4) is one of the preferred embodiments of the present invention.

[0082] 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 %.

[0083] 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.

[0084] The product obtained in the first step is, for example, a compound represented by the following formula (11):

[0085] [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 an alkoxypolyalkylene glycol (meth)acrylate such as methoxypolyethylene glycol (meth)acrylate, ethoxypolyethylene glycol (meth)acrylate, methoxy(poly)ethylene glycol (poly)propylene glycol (meth)acrylate, methoxy(poly)ethylene glycol (poly)butylene glycol (meth)acrylate, or ethoxy(poly)ethylene glycol (poly)propylene glycol (meth)acrylate. More preferably, it is methoxypolyethylene glycol (meth)acrylate or methoxy(poly)ethylene glycol (poly)propylene glycol (meth)acrylate.

[0086] 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 serving as the raw material of the structural unit having an amino group.

[0087] 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.

[0088] 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.

[0089] 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).

[0090] 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. Such a production method of a composition is also one aspect of the present invention. 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.

[0091] 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 mole number of nitrogen atoms in the amino group-containing compound (100 mol%). This allows the amount of NH groups in the cationic groups of the polycationic group-containing compound (α) 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%.

[0092] 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.

[0093] 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.

[0094] 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).

[0095] The polyalkylene glycol compound used in the second step may be any compound that has a polyalkylene oxide chain and undergoes an ester exchange reaction with the group derived from the unsaturated ester compound, and is preferably a polyalkylene glycol compound (β). An embodiment in which the polyalkylene glycol compound is a compound represented by the general formula (4) is one of the preferred embodiments of the present invention.

[0096] 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 %, more preferably 5 to 90 mol %, still more preferably 10 to 80 mol %, and still more preferably 20 to 50 mol %, based on 100 mol % of the groups derived from the unsaturated ester compound of the product obtained in the first step.

[0097] 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 by subjecting unreacted NH groups, which are not bonded to a linking group contained in the cationic group, to one or more of the following reactions: Michael addition reaction, acetylation reaction, amidation reaction with a carboxylic acid anhydride, amidation reaction with a carboxylic acid halide, and addition reaction of an epoxy compound. More specifically, the unreacted NH groups to which no linking group contained in the cationic group is bonded can be reduced by subjecting the unsaturated ester compound such as an acrylic acid alkyl ester to a Michael addition reaction, or by subjecting the unsaturated ester compound 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 viewpoints of improving mud dispersibility, anti-soil redeposition performance, and storage stability, it is preferable that the amount of unreacted NH groups is 80 mol or less, preferably 50 mol % or less, and more preferably 20 mol % or less, based on the total NH of the cationic group-containing compound (α).

[0098] By carrying out the steps of the production method (I) or (II), a composition containing the cationic group-containing compound (α) and the polyalkylene glycol compound (β) can be obtained. The production methods (I) and (II) may further include a step of adding the polyalkylene glycol compound (β).

[0099] [Uses of the composition of the present invention] 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.

[0100] 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.

[0101] The content of the cationic group-containing compound (α) 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.

[0102] The content of the polyalkylene glycol compound (β) of the present invention in the detergent or detergent composition of the present invention is preferably 0.05 to 7 mass %, more preferably 0.15 to 5 mass %, and further preferably 0.25 to 3 mass %, based on the total amount of the detergent or cleaning composition.

[0103] The detergent and detergent composition of the present invention may contain, in addition to the cationic group-containing compound (α) and polyalkylene glycol compound (β) 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.

[0104] 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

[0105] 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".

[0106] <Production Example 1> In a glass reaction vessel equipped with a nitrogen inlet tube, a reflux condenser, and a stirrer, 1.50 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600, number of nitrogen atoms 14) and 9.59 g of NK Ester AM-230G (manufactured by Shin-Nakamura Chemical, methoxypolyethylene glycol acrylate) were charged, and the atmosphere in the reaction vessel was replaced with nitrogen. After that, the mixture was heated to 60°C and stirred for 1 hour, and then 2.62 g of ethyl acrylate (manufactured by Fujifilm Wako Pure Chemical Industries) was dropped into the reaction system. The reaction of NK Ester AM-230G and ethyl acrylate was confirmed by liquid chromatography, and product (1) was obtained. The ratio of the substituent (A) to the total mole number of nitrogen atoms contained in product (1) (100 mol%) was 25 mol%, and the ratio of the substituent (B) was 75 mol%.

[0107] <Production Example 2> 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 Fujifilm Wako Pure Chemical Industries, Ltd.) 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 of polyethyleneimine (intermediate 1) was obtained. Furthermore, 7.87 g of methoxypoly(n=25)ethylene glycol (manufactured by Nippon Shokubai, hereinafter also referred to as MPEG25) and 0.18 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, 1.70 g of intermediate (1) was dropped into the system, and the transesterification reaction was carried out by stirring at 120°C for 13 hours. The reaction of MPEG25 was confirmed by liquid chromatography, and product (2) was obtained. (Reaction rate: 73%, remaining MPEG25: 22 wt%) The ratio of the substituent (A) to the total mole number of nitrogen atoms contained in product (2) of 100 mol% was 43 mol%, and the ratio of the substituent (B) was 57 mol%.

[0108] (Examples 1 to 3, Comparative Example 1: Preparation of the composition of the present invention) The product (1) obtained in Production Example 1, methoxypolyethylene glycol (manufactured by Nippon Shokubai Co., Ltd., hereinafter also referred to as MPEG25), pure water, and a 30% aqueous solution of linear alkylbenzene sulfonic acid (manufactured by Fujifilm Wako Pure Chemical Industries, Ltd., hereinafter also referred to as LAS) were added to a screw vial to prepare a mixed solution. The concentrations of each component in the mixed solution were 1% for product (1) and 27% for LAS, and the ratio of MPEG25 to the total amount of the cationic group-containing compound (α) and MPEG25 in product (1), 100% by mass, was the concentration shown in Table 1. Example 4: Preparation of a composition of the present invention The product (2) obtained in Production Example 2, pure water, and a 30% LAS aqueous solution were added to a screw vial to prepare a mixed solution such that the product (2) was 1%, the LAS was 27%, and the concentration of MPEG25 remaining in the product (2) (ratio relative to the total amount of the cationic group-containing compound (α) and MPEG25, 100% by mass) was 21.88% by mass. (Compatibility evaluation with surfactants) The mixed aqueous solutions prepared in Examples 1 to 4 and Comparative Example 1 were thoroughly stirred in 10 ml screw vials, the temperature was adjusted to 28° C., and the turbidity was observed. Solutions with high transparency were rated as ◎, ◯, or △, while cloudy solutions were rated as ×.

[0109] [Table 1]

Claims

1. A composition comprising a cationic group-containing compound (α) and a polyalkylene glycol compound (β), The cationic group-containing compound (α) is represented by 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 a hydrogen atom or an organic group having 1 to 30 carbon atoms; and a cationic group having a nitrogen atom, the substituent (A) is bonded to at least one of the nitrogen atoms contained in the cationic group, The content of the polyalkylene glycol compound (β) is 1 to 30% by mass relative to 100% by mass of the total amount of the cationic group-containing compound (α) and the polyalkylene glycol compound (β).

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

3. The cationic group-containing compound (α) 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, at least one of a and b is 1 or greater. The composition according to claim 1, having a structure derived from a compound represented by the following formula:

4. The cationic group-containing compound (α) may further be represented by the following general formula (3): 【Chemistry 3】 (In general formula (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.

5. The polyalkylene glycol compound (β) is represented by the following general formula (4): R ３ -(OR ５ ) ｓ２ -O-R ４ General formula (4) (In general formula (4), R ３ , R ４ are the same or different and each represents a hydrogen atom or an organic group having 1 to 18 carbon atoms. ３ , R ４ At least one of R is an organic group having 1 to 18 carbon atoms. ５ and are the same or different and represent a hydrocarbon group having 2 to 6 carbon atoms. s2 is an integer of 1 to 300.

6. A detergent or detergent composition comprising a composition according to any one of claims 1 to 5.

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