Polyalkylene oxide-containing compounds

Abstract

A purpose of the present invention is to provide a polyalkylene-oxide-containing compound having excellent dirt particle dispersing ability and resoiling prevention ability, a method for producing the same, and a detergent or a detergent composition containing said compound. The present invention relates to a polyalkylene-oxide-containing compound having a cationic group, a linking group, and a structural unit derived from a polyalkylene oxide.

Description

[Technical Field]

[0001] The present disclosure relates to a polyalkylene oxide-containing compound that has excellent mud particle dispersibility and anti-soil redeposition properties, a method for producing the same, and a detergent composition containing the compound. [Background technology]

[0002] Conventionally, polymers having a polyalkyleneimine main chain and ethylene oxide or the like attached to the nitrogen atom of the polyalkyleneimine have been known as polyalkyleneimine polyalkylene oxides. These polymers are known to act as polymer builders and have the property of dissolving in liquid detergents, so they are used as components of liquid detergents. When polyalkyleneimine polyalkylene oxides are added to detergents together with surfactants, they prevent recontamination by dirt removed by washing and exhibit high detergency.

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

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

[0005] [Patent Document 1] Japanese Patent Application Laid-Open No. 2010-168592 [Patent Document 2] Japanese Patent Application Laid-Open No. 2012-149185 Summary of the Invention [Problem to be solved by the invention]

[0006] Incidentally, through their investigations to date, the present inventors have discovered that the anti-soil redeposition ability can be improved by using in a detergent composition a polymer in which the alkylene terminal group of a polyalkylene polyalkylene oxide copolymer containing an alkylene amine structural unit having a polyalkylene oxide chain has been modified.

[0007] However, the polymers described in Patent Documents 1 and 2, in which the alkylene oxide end groups of the polyalkyleneamine alkylene oxide copolymers containing alkyleneamine structural units having polyalkylene oxide chains, have a problem that there is room for improvement in anti-soil redeposition ability.

[0008] The present disclosure has been made in consideration of the above-mentioned problems, and aims to provide a polyalkylene oxide-containing compound having good anti-soil redeposition properties, a method for producing the same, and a detergent composition containing the compound. [Means for solving the problem]

[0009] That is, the (polyalkylene oxide-containing) compound of the present disclosure is a polyalkylene oxide-containing compound having a cationic group, a linking group, and a structural unit derived from polyalkylene oxide, wherein the linking group is bonded to the structural unit derived from polyalkylene oxide.

[0010] The linking group is preferably one or more substituents selected from an ester group, a thioester group, an amide group, a thioamide group, an acetal group, a hemiacetal group, and a hemiketal group.

[0011] The polyalkylene oxide-containing compound has a substituent 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. X is -C(=α 1 )-β 1 - group, >C=α 1 group, -α 1 -CR 2 R 3 -β 1 -group, -CR 4 (OH)-α 1 -groups, and α 1 , β 1 R may be the same or different and represent a heteroatom or a group in which a hydrogen atom is bonded to a heteroatom. 2 , R 3 , R 4 are the same or different and represent a hydrogen atom or an organic group having 1 to 10 carbon atoms. s is an integer of 1 to 300. Y represents a direct bond, a linear or branched hydrocarbon group having 1 to 10 carbon atoms, or a substituent represented by the following general formula (2). Z represents a direct bond, -(CH2) n -(S) m -(CH2) p -O- group, -(CH2) n -α 2 - group or a group represented by the following general formula (3): 2 represents a heteroatom or a group in which a hydrogen atom is bonded to a heteroatom. m is 0 or 1, and n is an integer of 1 to 10. p is an integer of 1 to 10. T represents a hydrogen atom or an organic group having 1 to 30 carbon atoms. [ka] (In the general formula (2), q is an integer of 1 to 300. R 5 , R 6 are the same or different and represent a hydrocarbon group having 2 to 6 carbon atoms.) [ka] (In general formula (3), n is an integer of 1 to 10.) and a cationic group having two or more nitrogen atoms, The substituent represented by the above general formula (1) is preferably bonded to at least one of the nitrogen atoms contained in the cationic group.

[0012] α of X in the substituents described in the general formula (1) 1 , β 1 The heteroatom is preferably an oxygen atom or a nitrogen atom.

[0013] It is preferable that Y in the substituent group described in the above general formula (1) is a hydrocarbon group having 2 to 4 carbon atoms.

[0014] The polyalkylene oxide-containing compound preferably has a cationic group to which no linking group is bonded, and the unreacted NH groups contained in the cationic group to which no linking group is bonded account for 80 mol % or less of the total number of moles of nitrogen atoms contained in the polyalkylene oxide-containing compound.

[0015] The polyalkylene oxide-containing compound is preferably such that the number average molecular weight of the decomposition product obtained by carrying out a decomposition test in which the polyalkylene oxide-containing compound is decomposed by either alkaline hydrolysis or enzymatic decomposition is 0.5 or less relative to the number average molecular weight of the polyalkylene oxide-containing compound before the decomposition test.

[0016] The present invention is also a composition comprising the polyalkylene oxide-containing compound of the present invention and an acid compound.

[0017] The present invention also provides a method for producing the polyalkylene oxide-containing compound of the present invention, comprising the steps of: The production method is also a method for producing a polyalkylene oxide-containing compound, which includes a step of Michael addition of an α,β-unsaturated carbonyl compound having a polyalkylene oxide chain to an amino group, which is a cationic group.

[0018] The present invention also provides a method for producing the polyalkylene oxide-containing compound of the present invention, comprising the steps of: The production method includes a first step of Michael addition of an α,β-unsaturated carbonyl compound to an amino group, which is a cationic group; The method for producing a polyalkylene oxide-containing compound also includes a second step of introducing a polyalkylene oxide chain into the product obtained in the first step.

[0019] The present invention also provides a method for producing the polyalkylene oxide-containing compound of the present invention, comprising the steps of: The production method includes adding one or more compounds selected from a cyclic lactone compound and a cyclic lactam compound, a step of subjecting an amino group, which is a cationic group, to a ring-opening addition reaction; The method for producing a polyalkylene oxide-containing compound also includes a step of introducing a polyalkylene oxide chain into the active hydrogen generated in the ring-opening addition reaction step.

[0020] The present invention also provides a method for producing the polyalkylene oxide-containing compound of the present invention, comprising the steps of: The production method is also a method for producing a polyalkylene oxide-containing compound, which includes a step of reducing unreacted NH groups contained in the cationic groups not bonded to the linking group by one or more reactions selected from the group consisting of a Michael addition reaction, an acetylation reaction, an amidation reaction with a carboxylic acid anhydride, an amidation reaction with a carboxylic acid halide, and an epoxy compound addition reaction.

[0021] The present invention also provides a method for producing the polyalkylene oxide-containing compound of the present invention, comprising the steps of: The production method is also a method for producing a polyalkylene oxide-containing compound, which includes a step of neutralizing, with an acid compound, unreacted NH groups contained in the cationic groups that do not have a linking group bonded thereto.

[0022] The present invention is also a detergent or detergent composition comprising the polyalkylene oxide-containing compound of the present invention.

[0023] Preferably, the detergent or cleaning composition is selected from the group consisting of laundry detergent compositions, hard surface cleaning compositions, hand dishwashing compositions, and automatic dishwashing compositions, and is a liquid.

[0024] Preferably, the detergent or cleaning composition is selected from the group consisting of laundry detergent compositions, hard surface cleaning compositions, hand dishwashing compositions, and automatic dishwashing compositions, and is in a single-phase or multi-phase unit dose form containing a liquid detergent or cleaning composition enclosed in a single- or multi-compartment water-soluble pouch.

[0025] Preferably, the detergent or cleaning composition further comprises a surfactant selected from the group consisting of anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, zwitterionic surfactants, and mixtures thereof.

[0026] Preferably, in the detergent or cleaning composition, the surfactant is an anionic surfactant selected from the group consisting of alkyl benzene sulfonates, alkoxylated alkyl sulfates, alkyl sulfates, and mixtures thereof.

[0027] Preferably, the detergent or cleaning composition is a liquid laundry detergent composition further comprising one or more cleaning adjunct additives selected from the group consisting of builders, structurants or thickeners, mud soil removal / anti-redeposition agents, polymeric soil release agents, polymeric dispersants, polymeric grease cleaning agents, enzymes, enzyme stabilizing systems, bleaching compounds, bleaches, bleach activators, bleach catalysts, brighteners, dyes, hueing agents, dye transfer inhibitors, chelating agents, suds suppressors, softeners, fragrances, and mixtures thereof.

[0028] Preferably, the detergent or cleaning composition is substantially free of zeolite builder and phosphate builder.

[0029] The present invention is also a softening agent comprising the polyalkylene oxide-containing compound of the present invention.

[0030] The present invention is also a film composition comprising the polyalkylene oxide-containing compound of the present invention.

[0031] The present invention also provides a method for storing the polyalkylene oxide-containing compound of the present invention in an environment where the water concentration is 10% or less. [Effects of the Invention]

[0032] According to the present disclosure, it is possible to provide a polyalkylene oxide-containing compound that has excellent mud particle dispersibility and anti-soil redeposition properties, a method for producing the same, and a detergent composition containing the polyalkylene oxide-containing compound. DETAILED DESCRIPTION OF THE INVENTION

[0033]

[0023] The following detailed description of preferred embodiments of the present disclosure is merely exemplary in nature and is in no way intended to limit the present disclosure, its application, or its uses.

[0034] In the following description, unless otherwise specified, "%" means "% by mass", "parts" means "parts by mass", and the range "A to B" means A or more and B or less. In addition, in this disclosure, "(meth)acrylate" means "acrylate" or "methacrylate", and "(meth)acrylic" means "acrylic" or "methacrylic".

[0035] [Polyalkylene oxide-containing compound] The polyalkylene oxide-containing compound according to the present disclosure has the following substituents and structural units 1) to 3). 1) Cationic group 2) Linking group 3) Structural units derived from polyalkylene oxide

[0036] Cationic groups are groups that contain an amino group, which may be in the form of a primary amine, secondary amine, tertiary amine, or quaternary amine. In the polyalkylene oxide-containing compound of the present disclosure, the cationic group may have one amino group or two or more amino groups, but preferably has two or more amino groups. When the polyalkylene oxide-containing compound has two or more amino groups in its structure, the cationic group may be in the form of a polymer having two or more structural units having amino groups. Specific examples of the cationic group will be described later.

[0037] The polyalkylene oxide-containing compound of the present disclosure is preferably a compound having a structure in which a structural unit derived from polyalkylene oxide and the cationic group (or a structural unit having the cationic group) are linked via the linking group rather than directly bonded. Furthermore, the polyalkylene oxide-containing compound of the present disclosure is preferably a compound having a structure in which the nitrogen atom of the amino group in the cationic group is linked to the linking group. In the present disclosure, a structural unit derived from polyalkylene oxide refers to a structural unit represented by -RO- (R represents an alkylene group).

[0038] The linking group of the present disclosure is preferably one or more groups selected from an ester group, an amide group, a thioester group, a thioamide group, a hemiacetal group, a hemiketal group, and an acetal group. When the linking group is one or more selected from an ester group, an amide group, a thioester group, a thioamide group, a hemiacetal group, a hemiketal group, and an acetal group, the linking group is not particularly limited, but is preferably one or more selected from an ester group, an amide group, a thioester group, a thioamide group, and an acetal group, and more preferably one or more selected from an ester group and an amide group. These linking groups are preferred because they can improve the storage stability and degradability after use of the polyalkylene oxide-containing compound. Furthermore, they are preferred because they tend to improve the mud particle dispersibility and anti-redeposition ability of the polyalkylene oxide-containing compound of the present disclosure. In recent years, detergent compositions are required to have excellent cleaning ability and are also environmentally friendly, and therefore, the linking group is preferably, but not limited to, a hydrolyzable group or a functional group that is decomposed by an extracellular enzyme, and among the above linking groups, an ester group or an amide group is particularly preferred. Biodegradable means that it can be metabolized and broken down by bacteria, fungi, and other organisms.

[0039] The polyalkylene oxide-containing compound of the present disclosure preferably has a substituent represented by the following general formula (1): The substituent represented by the following general formula (1) is (-R 1 -O-) s and a linking group represented by -YXZ-. The polyalkylene oxide-containing compound of the present disclosure preferably has a structure in which a substituent represented by the following general formula (1) is bonded to a cationic group.

[0040] [ka] (In general formula (1), R 1 are the same or different and represent a hydrocarbon group having 2 to 6 carbon atoms. X is -C(=α 1 )-β 1 - group, >C=α 1 group, -α 1 -CR 2 R 3 -β 1 -group, -CR 4 (OH)-α 1 -groups, and α 1 , β 1 R may be the same or different and represent a heteroatom or a group in which a hydrogen atom is bonded to a heteroatom. 2 , R 3 , R 4are the same or different and represent a hydrogen atom or an organic group having 1 to 10 carbon atoms. s is an integer of 1 to 300. Y represents a direct bond, a linear or branched hydrocarbon group having 1 to 10 carbon atoms, or a substituent represented by the following general formula (2). Z represents a direct bond, -(CH2) n -(S) m -(CH2) p -O- group, -(CH2) n -α 2 represents a - group or a substituent represented by the following general formula (3): 2 represents a heteroatom or a group in which a hydrogen atom is bonded to a heteroatom. m is 0 or 1, and n is an integer of 1 to 10. p is an integer of 1 to 10. T represents a hydrogen atom or an organic group having 1 to 30 carbon atoms. [ka] (In the general formula (2), q is an integer of 1 to 300. R 5 , R 6 are the same or different and represent a hydrocarbon group having 2 to 6 carbon atoms.) [ka] (In general formula (3), n is an integer of 1 to 10.)

[0041] X in the general formula (1) is -C(=α 1 )-β 1 - group, >C=α 1 group, -α 1 -CR 2 R 3 -β 1 -group, -CR 4 (OH)-α 1 -groups. 1 , β 1 represents a heteroatom. X is preferably an ester group, a thioester group, an amide group, a thioamide group, an acetal group, or a hemiacetal group, and more preferably an ester group, an amide group, or an acetal group. Also, α 1 , β 1When is a hetero atom, there are no particular limitations as long as it is a hetero atom, and it is preferably at least one selected from an oxygen atom and a sulfur atom. α 1 , β 1 When is a group in which a hydrogen atom is bonded to a heteroatom, it is preferably an NH group. From the viewpoint of achieving both improved storage stability and reduced decomposition of the polyalkylene oxide compound, the above-mentioned substituents and atoms are preferred.

[0042] 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. It 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 mentioned above, the carbon number of is 2 to 4. In addition, -R in the general formula (1) 1 The —O— group may be one or more groups selected from an oxyethylene group, an oxypropylene group, and an oxybutylene group. The above-mentioned substituents and atoms are preferred from the viewpoint of imparting water solubility to the polyalkylene oxide compound and improving mud dispersibility and compatibility with liquid detergents.

[0043] R in the general formula (1) 2 , R 3 , R 4 are the same or different and are not particularly limited as long as they are a hydrogen atom or an organic group having 1 to 10 carbon atoms. They are preferably a hydrogen atom or an organic group having 1 to 6 carbon atoms, more preferably a hydrogen atom or a hydrocarbon group having 1 to 6 carbon atoms. They are further preferably a hydrogen atom or a methyl group.

[0044] In the general formula (1), s is not particularly limited as long as it is an integer of 1 to 300. It is preferably 1 to 200, more preferably 2 to 100, and even more preferably 3 to 50. From the viewpoint of further improving the mud dispersibility and anti-soil redeposition performance of the polyalkylene oxide compound, the content is preferably within the above-mentioned range.

[0045] Y in the general formula (1) is a direct bond, a linear or branched hydrocarbon group having 1 to 10 carbon atoms, or a group represented by the general formula (2). When Y in the general formula (1) is a hydrocarbon group having 1 to 10 carbon atoms, it is preferably a hydrocarbon group having 2 to 6 carbon atoms, and more preferably a hydrocarbon group having 2 to 4 carbon atoms. Furthermore, the hydrocarbon group is preferably an alkylene group.

[0046] In the general formula (2), q is an integer of 1 to 300, and the preferred range is the same as that of s in the general formula (1). R in general formula (2) 5 , R 6 are the same or different and are hydrocarbon groups having 2 to 6 carbon atoms, and preferred hydrocarbon groups are 1 is the same as:

[0047] The polyalkylene oxide-containing compound of the present disclosure is preferably one that is decomposed at the linking group portion. In this case, it is preferable that the decomposable portion of the linking group that bonds the cationic group and the polyalkylene oxide-derived structural unit is not directly bonded to the cationic group but is bonded to a position that is somewhat distant from the cationic group within the above range, in order to ensure the decomposability of the polyalkylene oxide compound.

[0048] Z in the general formula (1) is a direct bond, -(CH2) n -(S) m -(CH2) p -O- group, -(CH2) n -α 2 There are no particular limitations as long as it is a - group or the following general formula (3). α 2 is a heteroatom. n and p are integers of 1 to 10, and m is 0 or 1. α 2 When is a hetero atom, there is no particular limitation, but it is preferably an oxygen atom or a sulfur atom. α 2When is a group in which a hydrogen atom is bonded to a heteroatom, it is preferably an NH group. There are no particular limitations on n and p as long as they are integers of 1 to 10, preferably 1 to 5, and more preferably 1 to 3. There is no particular limitation on m as long as it is 0 or 1. From the viewpoint of ease of synthesis for introducing a linking group into a polyalkylene oxide, the above-mentioned substituents and ranges are preferred.

[0049] In the general formula (1), T may be the same or different and is 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 or 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 hydrocarbon group.

[0050] In the cationic group of the present disclosure, if all amino groups contained in the cationic group are bonded via the linking group, there will be no unreacted amino groups and no NH groups. In this case, the NH groups will be 0 mol%, and the remaining unreacted NH groups will be 0 mol% relative to the total number of moles of nitrogen atoms contained in the polyalkylene oxide-containing compound. On the other hand, unreacted amino groups may be present. In this case, the unreacted NH groups contained in the cationic group not bonded to the linking group are preferably 100 mol% or less relative to the total number of moles of nitrogen atoms contained in the polyalkylene oxide-containing compound. More preferably, it is 80 mol% or less, even more preferably 50 mol% or less, and particularly preferably 20 mol% or less. If there are many unreacted NH groups, the amount of polyalkylene oxide groups introduced into the polyalkylene oxide compound will decrease, resulting in a decrease in mud dispersibility and anti-soil redeposition performance. From this viewpoint, it is preferable that the proportion of unreacted NH groups is within the above range.

[0051] As mentioned above, the cationic group can also be represented as a structural unit having an amino group. Specific examples include structural units derived from compounds such as polyethylene polyamines (PEA) such as diethylenetriamine, triethylenetetramine, and tetraethylenepentamine, tetrabutylenepentamine, polyethyleneimine (PEI), and polyamidoamine.

[0052] The precursor constituting the structural unit having an amino group of the present disclosure can be represented by the following general formula (4).

[0053] [ka] In the formula, R 7 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, b, and c are the same or different and represent an integer of 0 or 1 or more, and at least one of a, b, and c is an integer of 1 to 100. The structural unit having an amino group contains at least two or more -NR 7 -There will be units. When a precursor of the above general formula (4) 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 compound of the present disclosure.

[0054] Regarding the precursor that forms the structural unit having the amino group, the structural formula of the structural unit that constitutes the precursor is, for example, H2N-R 7 -, -NH-R 7 -, -N(-)-R 7 -, etc.

[0055] When P in the general formula (4) is a structural unit having another amino group, the structural unit having another amino group is preferably represented by the following general formula (5), and R 7’ It is preferred that the bond to the structure represented by general formula (4) is via a group.

[0056] [ka] In the formula, a', b', c', P', R 7’ are a, b, c, P, and R in general formula (4), respectively. 7 is the same as:

[0057] The structural formula of the precursor forming the amino group-containing structural unit is R 7 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. 7 When is a branched alkylene group having 3 to 6 carbon atoms, a 1,2-propylene group is preferred. In the structural formula of the precursor that forms the structural unit having an amino group, a, b, and c may be the same or different and may be an integer of 0 or 1 or greater, but each is preferably an integer of 0 to 100. Furthermore, a+b+c may be a number of 1 or greater, but a+b+c of 1 to 4, 1 to 3, or 1 or 2 are all preferred embodiments of the precursor that forms the structural unit having an amino group. Furthermore, a+b+c of 5 or greater is also a preferred embodiment of the precursor that forms the structural unit having an amino group.

[0058] Examples of the polyalkylene oxide-containing compound of the present disclosure (having a substituent represented by the above general formula (1)) include compounds in which a linking group is bonded to the nitrogen atom of the amino group of a (poly)alkyleneamine having at least one selected from the group consisting of a structural unit containing a primary amine nitrogen atom, a structural unit containing a secondary amine nitrogen atom, and a structural unit containing a tertiary amine nitrogen atom, and further a structural unit derived from polyalkylene oxide is bonded to the other side of the linking group. The constitutional unit containing a primary amine nitrogen atom is represented by, for example, the following formula: (H2-NR 7 )- R 7 is the same as general formula (4). In some cases, it also contains a structural unit represented by the following formula: -NH2 The structural unit containing a secondary amine nitrogen atom is represented, for example, by the following general formula (6).

[0059] [ka]

[0060] The structural unit containing a tertiary amine nitrogen atom is represented, for example, by the following general formula (7).

[0061] [ka]

[0062] P and R in general formulas (6) and (7) 7 is the same as general formula (4).

[0063] In the structural unit having the cationic group, the form of the structural unit is not particularly limited, and for example, the structural unit may be present randomly. Note that the nitrogen atom derived from the amino group contained in the cationic group may be quaternized or oxidized.

[0064] Furthermore, one example of a precursor constituting the structural unit having a cation group of the present disclosure represented by the general formula (4) can be represented by the following general formula (8).

[0065] [ka] In general formula (8), R 8 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. r represents an integer of 0 to 10. Specific examples will be described in detail below using an amine compound having two primary amines as an example, but it is not necessary to limit the scope to an amine compound having two primary amines.

[0066] In addition to the general formulae (6) and (7), the structural unit having a cationic group of the present disclosure can also be represented by the following general formula (9).

[0067] [ka] In general formula (9), R 8 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. The diamine compound serves as a precursor of the structural unit of the general formula (9).

[0068] When a diamine compound reacts with a (meth)acrylic acid compound, a compound represented by the following general formula (10) is produced, and when the diamine compound further reacts with the compound, a polyamine compound represented by the following general formula (11) is produced.

[0069] [ka]

[0070] [ka] R in general formula (10) and general formula (11) 8 is the same as in general formula (8) and general formula (9). 9 are the same or different and represent a hydrogen atom or an organic group having 1 to 30 carbon atoms; R 10 represents a hydrogen atom or a methyl group.

[0071] R 9 are not particularly limited as long as they are the same or different and are a hydrogen atom or an organic group having 1 to 30 carbon atoms. They may be selected appropriately to adjust the hydrophilicity or hydrophobicity. The organic group is preferably a hydrocarbon group.

[0072] The compound represented by the general formula (10) is produced by a Michael addition reaction of a (meth)acrylic acid compound with a diamine compound, which is a precursor of the compound represented by the general formula (9).

[0073] Moreover, the compound of the general formula (11) is produced by subjecting the compound of the general formula (10) to an ester-amide exchange reaction with a diamine compound.

[0074] The polyalkylene oxide-containing compound of the present disclosure can be obtained by adding a glycidyl ether compound having a polyalkylene oxide structure to the general formula (11).

[0075] Furthermore, the polyalkylene oxide-containing compound of the present disclosure can be obtained by subjecting the general formula (11) to a Michael addition reaction with a (meth)acrylic acid compound having a polyalkylene oxide structure.

[0076] Furthermore, the polyalkylene oxide-containing compound of the present disclosure can be obtained by addition polymerization of an alkylene oxide to the compound of general formula (11).

[0077] [Physical Properties of the Polyalkylene Oxide-Containing Compound of the Present Disclosure] The polyalkylene oxide-containing compound of the present disclosure can undergo a decomposition reaction to reduce the molecular weight by one or more decomposition methods selected from alkaline hydrolysis, enzymatic decomposition, and activated sludge. When the polyalkylene oxide-containing compound of the present disclosure 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 polyalkylene oxide-containing compound of the present disclosure is used, for example, as a detergent or detergent composition, the environmental burden caused by the compound discharged after washing is reduced.

[0078] The weight-average molecular weight of the polyalkylene oxide-containing compound of the present disclosure is preferably 1,000 to 1,000,000, more preferably 3,000 to 500,000, and even more preferably 5,000 to 200,000. When the weight-average molecular weight of the polyalkylene oxide-containing compound of the present disclosure is within the above-mentioned range, the compound has excellent anti-soil redeposition ability and reduces the environmental burden due to the decomposition reaction, which is preferable. The weight average molecular weight of the polyalkylene oxide-containing compound can be measured by the method described in the Examples.

[0079] [Polyalkylene oxide-containing compound composition of the present disclosure] The polyalkylene oxide-containing compound of the present disclosure may have NH groups contained in unreacted cationic groups treated with an acid compound by the production method described below. Such a composition containing a polyalkylene oxide-containing compound and an acid compound for treating the NH groups also constitutes one aspect of the present invention. The content of the acid compound is preferably 30% by mass or less, more preferably 20% by mass or less, and even more preferably 10% by mass or less, when the total amount of the polyalkylene oxide-containing compound composition is taken as 100% by mass. The content of the acid compound within the above range is preferable because the stability of the polyalkylene oxide-containing compound of the present disclosure is improved. Examples of acid compounds include acetic acid, citric acid, hydrochloric acid, phosphoric acid, nitric acid, sulfuric acid, p-toluenesulfonic acid, etc. There are no particular limitations on the acid compounds as long as they can react with an amino group.

[0080] [Method for producing polyalkylene oxide-containing compounds of the present disclosure] Examples of the method (I) for producing a polyalkylene oxide-containing compound of the present disclosure include a method for producing the compound by condensing a polyalkylene oxide compound having a carboxyl group with a hydrogen atom of an amino group of a (poly)alkyleneamine, or by esterifying a polyalkylene oxide compound having a carboxylic acid halide group.

[0081] The (poly)alkyleneamine used in the production method (I) is a compound having the structural formula represented by the above-mentioned general formula (4). The polyalkylene oxide compound having a carboxyl group or the polyalkylene oxide compound having a carboxylic acid halide group used in the production method (I) can be represented by the following general formula (12).

[0082] [ka] In general formula (12), R 1 , s are the same as those in the general formula (1). 11 represents a hydrogen atom or an organic group having 1 to 20 carbon atoms, and R 12 represents an organic group having 1 to 6 carbon atoms. 11 is preferably hydrogen, a linear or branched alkyl group having 1 to 20 carbon atoms, an alkenyl group, an alkynyl group, or an aryl group. 12 is preferably an alkyl group having a carbon number of 1 to 6. Q represents OH, Cl, Br or I.

[0083] Among the compounds represented by general formula (12), R 12 is an organic group having a terminal carbonyl group, the compound represented by the following general formula (12') is preferred.

[0084] [ka] In general formula (12'), R 1 ,s,R 11 , Q is the same as in general formula (12). 12’ represents an organic group having 1 to 5 carbon atoms.

[0085] R in general formula (12) 11 , R in general formula (12') 12’ The organic group is preferably a saturated or unsaturated hydrocarbon group.

[0086] Specific examples of the polyalkylene oxide compound having a carboxyl group include an esterification reaction product of an alkoxypolyalkylene glycol with a dicarboxylic acid anhydride such as succinic anhydride or maleic anhydride; a reaction product of an alkoxypolyalkylene glycol with a carboxylic acid halide; and a compound in which the terminal hydroxyl group of an alkoxypolyalkylene glycol is oxidized and carboxylated with an oxidizing agent.

[0087] The temperature at which the (poly)alkyleneamine represented by the general formula (4) is reacted with the polyalkylene oxide compound having a carboxyl group represented by the general formula (12) is preferably 50 to 200° C., and more preferably 100 to 200° C. When the reaction temperature and reaction time are within the above-mentioned ranges, the reaction proceeds almost quantitatively, improving reactivity and reducing unreacted raw materials, which is preferable because the mud particle dispersibility and anti-redeposition ability of the polyalkylene oxide-containing compound of the present disclosure tend to be improved.

[0088] Another example of production method (II) is a method in which one or more compounds selected from cyclic lactone compounds and cyclic lactam compounds are subjected to a ring-opening addition reaction with an amino group contained in a cationic group, and then a polyalkylene oxide chain is introduced into the active hydrogen generated by the ring-opening addition reaction to obtain the polyalkylene oxide-containing compound of the present disclosure. More specifically, an ester bond or an amide bond can be introduced by subjecting a caprolactone compound or a caprolactam compound to a ring-opening addition reaction with the hydrogen atom of the amino group of a (poly)alkyleneamine. The terminal residue resulting from the ring-opening addition reaction of a caprolactone compound or a caprolactam compound is a hydroxyl group or an NH group. The polyalkylene oxide-containing compound of the present disclosure can be produced by subjecting this hydroxyl group or NH group to a ring-opening addition reaction with an epoxy compound such as ethylene oxide.

[0089] The (poly)alkyleneamine used in the production method (II) is a compound having the structural formula represented by the above-mentioned general formula (4). The lactone compound used in the production method (II) may be α-lactone (three-membered ring), β-lactone (four-membered ring), γ-lactone (five-membered ring), δ-lactone (six-membered ring), ε-lactone (seven-membered ring), or a derivative thereof. Specific examples include α-acetolactone, β-propiolactone, γ-butyrolactone, δ-valerolactone, and ε-caprolactone. The lactam compound may be one or more of α-lactam (three-membered ring), β-lactam (four-membered ring), γ-lactam (five-membered ring), δ-lactam (six-membered ring), ε-lactam (seven-membered ring), or a derivative thereof.

[0090] In the production method (II), the lactone compound and / or lactam compound is bonded to the hydrogen atom of the amino group of the (poly)alkyleneamine of the general formula (4) through a ring-opening addition reaction of the lactone compound and / or lactam compound to the (poly)alkyleneamine of the general formula (4), thereby obtaining a (poly)alkyleneamine-lactone adduct and / or a (poly)alkyleneamine-lactam adduct. An example of this reaction is shown in the following scheme.

[0091] [ka] R in general formula (13), general formula (14), and general formula (15) 8 , r is the same as in the general formula (8).

[0092] In the production method (II), the reaction temperature for the ring-opening addition reaction between the (poly)alkyleneamine of the general formula (4) and the lactone compound and / or lactam compound is preferably 0 to 100°C, more preferably 20 to 80°C. The reaction time is preferably 1 hour or longer.

[0093] In the (poly)alkyleneamine-lactone adduct and (poly)alkyleneamine-lactam adduct obtained as intermediates in the production method (II), the terminal residues resulting from the addition reaction of the lactone compound and the lactam compound are hydroxyl groups. The polyalkylene oxide-containing compound of the present disclosure can be obtained by subjecting this hydroxyl group to a ring-opening addition reaction with an alkylene oxide such as ethylene oxide or propylene oxide. The reaction conditions for the ring-opening addition reaction of the alkylene oxide are the same as those for conventional methods.

[0094] As another production method (III), a method can be used in which the double bond of an (alkoxy)polyalkylene oxide (meth)acrylate is subjected to Michael addition with the amino group of a polyalkylene amine to produce a compound in which a polyamine and an alkylene oxide are bonded via an ester bond.

[0095] The (poly)alkyleneamine used in the production method (III) can be a compound having the structural formula represented by the above-mentioned general formula (4). The (alkoxy)polyalkylene oxide (meth)acrylate compound or (alkoxy)polyalkylene glycol (meth)acrylamide used in the production method (III) can be represented by the following general formula (16).

[0096] [ka] In general formula (16), R 1 , s, and T are the same as in general formula (1). 13 are the same or different and are a hydrogen atom or a methyl group. G represents O, N, or NH, and d is 1 or 2. When G is N, d is 2, and when G is O or NH, d is 1.

[0097] The general formula (16) can also be expressed as the following general formula (17).

[0098] [ka] In general formula (17), R 13 , G, T, and d are the same as in general formula (16). m 1 , n 1 are integers between 0 and 300, and m 1 +n 1 is the same as s in general formula (1). R 14 , R 15 are the same or different and represent a hydrocarbon group having 2 to 6 carbon atoms.

[0099] R 14 is a hydrocarbon group having 2 to 6 carbon atoms, preferably a hydrocarbon group having 2 to 4 carbon atoms, more preferably a hydrocarbon group having 2 to 3 carbon atoms, and even more preferably a hydrocarbon group having 2 carbon atoms.

[0100] R 15 is a hydrocarbon group having 3 to 6 carbon atoms, preferably a hydrocarbon group having 3 to 4 carbon atoms.

[0101] m 1 is not particularly limited as long as it is an integer of 0 to 300, and is preferably 1 to 10, more preferably 1 to 5, and even more preferably 1 to 3. m 1 If is 1 or more, R 13 is preferably a hydrogen atom. m 1 Specific examples of general formula (17) when is 1 or more are (meth)acrylic acid esters in which an alkylene glycol having 3 or more carbon atoms is bonded to the ester bond moiety, such as (alkoxy)polyethylene glycol (poly)propylene glycol (meth)acrylic acid esters and (alkoxy)polyethylene glycol (poly)butylene glycol (meth)acrylic acid esters. Particularly preferred are (alkoxy)polyethylene glycol (poly)propylene glycol acrylic acid esters, (alkoxy)polyethylene glycol (poly)butylene glycol acrylic acid esters, methoxypolyethylene glycol (poly)propylene glycol acrylic acid esters, and methoxypolyethylene glycol (poly)butylene glycol acrylic acid esters. m1 When is 0, (alkoxy)polyethylene glycol methacrylate and methoxypolyethylene glycol methacrylate are preferred. m 1 When the value of is within the above-mentioned range, hydrophobicity and steric hindrance can be imparted to the ester bond moiety, which is preferable in that the stability of the ester bond can be improved when stored in a protic solvent such as water, methanol, or ethanol.

[0102] n 1 is not particularly limited as long as it is an integer of 0 to 300, and is preferably 1 to 200, more preferably 5 to 100, and even more preferably 10 to 50. n 1 It is preferable that the value is within the above range, since this improves the dispersibility of mud particles, the anti-resoiling performance of mud, and the compounding stability in liquid detergents.

[0103] Also, R 14 is a hydrocarbon group having 2 carbon atoms, -R 15 -O- group, -R 14 When the total amount of -O- groups is 100 mol%, -R 14 The content of —O— groups is preferably 70 mol or more, more preferably 75 mol or more, and even more preferably 80 mol or more. R 14 is a hydrocarbon group having 2 carbon atoms, -R in the general formula (17) 14 If the content of -O- groups is within the above range, the hydrophilicity of the polyalkylene oxide chain is improved, which is preferable in that the dispersibility of mud particles and the ability to prevent mud re-soiling are improved.

[0104] In the production method (III), the (poly)alkyleneamine of the general formula (4) and the (alkoxy)polyalkyleneoxide (meth)acrylate of the general formula (16) or the general formula (17) are bonded to the hydrogen atom of the amino group of the general formula (4) by a Michael addition reaction, thereby obtaining a (poly)alkyleneamine-(alkoxy)polyalkyleneoxide (meth)acrylate adduct.

[0105] In the production method (III), the reaction temperature for the Michael addition reaction of the (poly)alkyleneamine of the general formula (4) and the (alkoxy)polyalkyleneoxide (meth)acrylate of the general formula (16) or (17) is preferably 20 to 100°C, more preferably 40 to 80°C. The reaction time is preferably 1 hour or longer, more preferably 5 hours or longer, and even more preferably 10 hours or longer. When the reaction temperature and reaction time are within the above ranges, the reaction proceeds almost quantitatively, improving the reaction rate and reducing the amount of unreacted raw materials, which is preferable.

[0106] In the production process of the (alkoxy)polyalkylene oxide (meth)acrylate used in production method (III), if a step of esterification between (meth)acrylic acid and (alkoxy)polyalkylene oxide is included, (meth)acrylic acid may remain. In this case, the Michael addition reaction of the (alkoxy)polyalkylene oxide (meth)acrylate proceeds more easily than that of (meth)acrylic acid. Therefore, by carrying out the reaction of the (poly)alkylene amine of general formula (4) with the (alkoxy)polyalkylene oxide (meth)acrylate at a low temperature, the (alkoxy)polyalkylene oxide (meth)acrylate can be preferentially added to the (poly)alkylene amine of general formula (4). Furthermore, by increasing the reaction temperature or extending the reaction time, (meth)acrylic acid can also be Michael added to the (poly)alkylene amine of general formula (4).

[0107] Furthermore, a production method similar to production method (III) includes a method in which an α,β-unsaturated carbonyl compound having a polyalkylene oxide chain is subjected to Michael addition to an amino group contained in a cationic group to obtain the polyalkylene oxide-containing compound of the present disclosure. Another production method similar to Production Method (III) is a method in which an α,β-unsaturated carbonyl compound is subjected to Michael addition to an amino group contained in a cationic group, and then a polyalkylene oxide chain is introduced to obtain the polyalkylene oxide-containing compound of the present disclosure.

[0108] In the production method (III), the (poly)alkyleneamine of the general formula (4) may be reacted with the (alkoxy)polyalkyleneoxide (meth)acrylate of the general formula (16) or (17) without a solvent. When the reaction is carried out using a reaction solvent, alcohols such as methanol and ethanol, alkanes such as pentane, hexane, and cyclohexane, ethers such as diethyl ether and tetrahydrofuran, polar solvents such as dimethyl sulfoxide and dimethylformamide, water, or a mixture of water and an organic solvent may be used.

[0109] Another example of production method (IV) is a method of producing a polyalkylene oxide-containing compound of the present disclosure by introducing an amide bond by Michael addition of the double bond of acrylamide to the amino group of a (poly)alkyleneamine, and then subjecting the amino group or hydroxyl group, which is the terminal residue resulting from the Michael addition reaction, to a ring-opening addition reaction with an epoxy compound such as ethylene oxide.

[0110] Another example of production method (V) is a method for producing the polyalkylene oxide-containing compound of the present disclosure by acetalizing a (poly)alkyleneamine alkoxylate obtained by subjecting an epoxy compound such as ethylene oxide to a ring-opening addition reaction with the hydrogen atom of the amino group of a (poly)alkyleneamine using an (alkoxy)polyalkylene oxide, an acetalizing agent, and an acid catalyst.

[0111] Another example of production method (VI) is a method for producing the polyalkylene oxide-containing compound of the present disclosure by Michael addition of the double bond of an alkyl(meth)acrylate to the amino group of a (poly)alkyleneamine to obtain an ester-containing compound, and then ester-amide exchange of the ester-containing compound with an (alkoxy)polyalkylene oxide-containing terminal amine compound.

[0112] Furthermore, as another production method (VII), there is mentioned a method of producing the polyalkylene oxide-containing compound of the present disclosure by reacting an ester-containing compound obtained by Michael addition of the double bond of an alkyl (meth)acrylate to the amino group of a (poly)alkylene amine with an (alkoxy)polyalkylene glycol to effect transesterification.

[0113] Furthermore, the production methods (I) to (VII) preferably include, in addition to the above-mentioned steps, a step of reducing the number of unreacted NH groups by subjecting unreacted NH groups contained in the cationic group that are not bonded to a linking 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 with an epoxy compound. More specifically, the unreacted NH groups that are not bonded to a linking group contained in the cationic group can be reduced by Michael addition of an alkyl acrylate ester such as methyl acrylate, or by 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 addition of an epoxy compound such as ethylene oxide or propylene oxide. The amount of unreacted NH groups is preferably 80 mol or less, preferably 50 mol% or less, and more preferably 20 mol% or less, relative to the total NH of the polyalkylene oxide-containing compound, from the viewpoint of improving mud dispersibility, anti-soil redeposition performance, and storage stability.

[0114] The above-mentioned production method preferably further comprises a step of neutralizing with an acid compound as another method for reducing the number of NH groups. More specifically, it is preferable to reduce the number of NH groups by neutralizing unreacted NH groups contained in the cationic group that are not bound to a linking group with an acid compound such as acetic acid, citric acid, hydrochloric acid, phosphoric acid, nitric acid, sulfuric acid, p-toluenesulfonic acid, or other common acid compounds. The amount of unreacted NH groups is preferably 80 mol or less, preferably 50 mol or less, and more preferably 20 mol or less, relative to the total NH of the polyalkylene oxide-containing compound, from the viewpoint of improving mud dispersibility, anti-soil redeposition performance, and storage stability. The amount of the acid compound added is preferably 50 to 300 mol % based on the NH groups contained in the cationic groups before the acid compound is added.

[0115] [Uses of polyalkylene oxide-containing compounds] The polyalkylene oxide-containing compound of the present disclosure (also simply referred to as the "compound of the present disclosure") can be suitably used in detergent builders, detergents, water treatment agents, dispersants, fiber treatment agents, scale inhibitors (scale inhibitors), cement additives, metal ion sequestering agents, thickeners, various binders, etc. In particular, it can be suitably used in detergent builders, detergents, water treatment agents, and dispersants.

[0116] The present disclosure also relates to a detergent builder, detergent, water treatment agent, or dispersant containing, as an essential component, the polyalkylene oxide-containing compound of the present disclosure or a polyalkylene oxide-containing compound produced by the production method of the present disclosure.

[0117] <Detergent or cleaning composition> Detergent or cleaning compositions containing polyalkylene oxide-containing compounds of the present disclosure Provided are detergent or cleaning compositions, preferably laundry detergent compositions, more preferably liquid laundry detergent compositions, containing the polyalkylene oxide-containing compounds of the present disclosure and, optionally, other adjunct ingredients.

[0118] The terms "detergent composition," "cleaning composition," and "detergent or cleaning composition" are broadly defined above and are used interchangeably below. Specifically, the detergent or cleaning composition may be in any solid or liquid product form, including laundry detergent compositions, hard surface cleaning compositions, hand dishwashing compositions, and automatic dishwashing compositions. The detergent or cleaning composition is preferably liquid, and even more preferably in a single-phase or multi-phase unit dose form. That is, the liquid detergent or cleaning composition is contained in a single- or multi-compartment water-soluble pouch. In certain embodiments, the detergent or cleaning composition is a single- or multi-phase unit dose form containing either a liquid automatic dishwashing composition or a liquid laundry detergent composition enclosed in a single- or multi-compartment water-soluble pouch formed of a water-soluble polymer, such as polyvinyl alcohol (PVA) and / or polyvinylpyrrolidone (PVP).

[0119] The amount of the polyalkylene oxide-containing compound of the present disclosure contained in the detergent or cleaning composition is not particularly limited. To achieve high builder performance, the polyalkylene oxide-containing compound of the present disclosure is contained in an amount ranging from about 0.1% by mass to about 15% by mass, more preferably from about 0.3% by mass to about 10% by mass, and even more preferably from about 0.5% by mass to about 5% by mass, based on the total amount of the detergent or cleaning composition.

[0120] When the detergent or cleaning composition is in the form of a liquid laundry detergent composition, the polyalkylene oxide-containing compounds of the present disclosure may further comprise one or more organic solvents, which may be present in an amount ranging from about 1% to about 80%, preferably from about 10% to about 60%, more preferably from about 15% to about 50%, and even more preferably from about 20% to about 45% by weight of the total weight of the composition.

[0121] Because phase separation is always a challenge for liquid laundry detergent compositions, especially when such compositions contain high salt content, the detergent or cleaning compositions of the present disclosure comprise a solvent system specifically designed to stabilize the polyalkylene oxide-containing compounds of the present disclosure and minimize the risk of phase separation. Specifically, the detergent or cleaning compositions of the present disclosure preferably comprise a solvent system consisting primarily of diols such as ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, butylene glycol, pentanediol, and combinations thereof. Preferably, the diol is present in the liquid laundry detergent compositions of the present disclosure in a total amount ranging from about 2% to about 50% by weight. More preferably, the compositions contain ethylene, diethylene glycol, and / or propylene glycol in a total amount ranging from about 5% to about 40% by weight. Even more preferably, the compositions contain propylene glycol in an amount ranging from about 15% to about 35% by weight.

[0122] The detergent or cleaning compositions of the present disclosure may further comprise other solvents, including, but not limited to, methanol, ethanol, glycerin, sodium cumene sulfonate, potassium cumene sulfonate, ammonium cumene sulfonate, sodium toluene sulfonate, potassium toluene sulfonate, sodium xylene sulfonate, potassium xylene sulfonate, ammonium xylene sulfonate, or mixtures thereof, and other organic solvents may also be present. Other lower alcohols, such as C1-C4 alkanolamines, such as monoethanolamine and / or triethanolamine, may also be used. In particularly preferred embodiments of the present disclosure, the liquid laundry detergent compositions of the present disclosure also contain, in addition to the diol, from about 5% to about 20% by weight, preferably from 6% to 18% by weight, and more preferably from 8% to 16% by weight of glycerin.

[0123] The liquid laundry detergent compositions of the present disclosure preferably contain water as a carrier in combination with the organic solvents described above. In some embodiments, water is present in the liquid laundry detergent compositions of the present disclosure in an amount ranging from about 20% to about 70% by weight, preferably from about 25% to 60% by weight, and more preferably from about 30% to about 50% by weight. In other embodiments, water is absent, and the compositions are anhydrous. Highly preferred compositions provided by the present disclosure are clear, isotropic liquids.

[0124] The detergent or cleaning composition of the present disclosure preferably contains one or more surfactants and one or more cleaning auxiliary additives. The specific forms of the surfactants and cleaning auxiliary additives are not particularly limited and are appropriately selected based on common knowledge in the detergent field.

[0125] <Anionic surfactants> The detergent or cleaning compositions of the present disclosure may comprise one or more anionic surfactants. The detergent or cleaning compositions of the present disclosure may essentially comprise one or more anionic surfactants and may further comprise another surfactant system.

[0126] The anionic surfactant may be any known anionic surfactant, including, but not limited to, sulfate detersive surfactants for alkoxylated and / or non-alkoxylated alkyl sulfate materials, and / or sulfonic acid-based detersive surfactants, alkyl benzene sulfonates.

[0127] Alkoxylated alkyl sulfates include ethoxylated alkyl sulfate surfactants, also known as alkyl ether sulfates or alkyl polyethoxylate sulfates. Ethoxylated alkyl sulfates include the water-soluble salts of organic sulfuric acid reaction products having alkyl groups containing from about 8 to 30 carbon atoms in their molecular structure, particularly the alkali metal, ammonium, and alkylolammonium salts, as well as sulfonic acids and their salts. The term "alkyl" includes the alkyl portion of an acyl group, for example, an alkyl group having 15 to 30 carbon atoms. The alkyl ether sulfate surfactant may be a mixture of alkyl ether sulfates having an average (arithmetic mean) carbon chain length of about 12 to 30, and in another example, an average carbon chain length of about 25. The average (arithmetic mean) number of moles of EO added is about 1 to 4, and in another example, an average (arithmetic mean) number of moles of EO added is 1.8. In yet another example, the alkyl ether sulfate surfactant may have a carbon chain length of from about 10 carbon atoms to about 18 carbon atoms and a degree of ethoxylation of from about 1 to about 6 moles of ethylene oxide. In yet a further example, the alkyl ether sulfate surfactant may comprise a peaked ethoxylation distribution, as described in WO 1995011212 A1, U.S. Patent Nos. 5,120,697, 5,210,325, 4,946,984, 4,902,658, and WO 2010099303 A1.

[0128] Examples of non-alkoxylated alkyl sulfates include non-ethoxylated alkyl sulfates. Non-ethoxylated alkyl sulfates may also be added to the disclosed cleaning compositions and used as anionic surfactant components. Examples of non-alkoxylated, e.g., non-ethoxylated, alkyl sulfate surfactants include those produced by sulfation of higher C8-C20 fatty alcohols. In some examples, primary alkyl sulfate surfactants have the general formula: ROSO3 - M + where R is typically a linear C8-C20 hydrocarbyl group (which may be straight or branched), and M is a water-solubilizing cation. In some examples, R is a C10-C15 alkyl and M is an alkali metal. In other examples, R is a C12-C14 alkyl and M is sodium.

[0129] Other useful anionic surfactants include alkali metal salts of alkylbenzene sulfonates in which the alkyl group contains from about 9 to about 15 carbon atoms in a straight (linear) or branched chain arrangement, such as those described in U.S. Pat. Nos. 2,220,099 and 2,477,383. In some instances, the alkyl group is linear. Such linear alkylbenzene sulfonic acids are known as "LAS." In other instances, the linear alkylbenzene sulfonate may have an average of about 11 to 14 carbon atoms in the alkyl group. In a specific example, the linear straight-chain alkylbenzene sulfonate may have an average of about 11.8 carbon atoms in the alkyl group, sometimes abbreviated as C11.8 LAS. Such surfactants and their preparation are described, for example, in U.S. Pat. Nos. 2,220,099 and 2,477,383.

[0130] Suitable alkylbenzene sulfonates (LAS) may be obtained by sulfonating commercially available linear alkylbenzenes (LAB), suitable LABs include low 2-phenyl LABs such as those supplied by Sasol under the trade name Isochem® or by Petresa under the trade name Petrelab®, other suitable LABs are high 2-phenyl LABs such as those supplied by Sasol under the trade name Hyblene®. Preferred anionic detersive surfactants are alkylbenzene sulfonates obtained by a DETAL-catalyzed process, although other synthetic routes, such as HF, may also be suitable. In one embodiment, the magnesium salt of LAS is used.

[0131] The detersive surfactant may be a mid-chain branched detersive surfactant, in one embodiment a mid-chain branched anionic detersive surfactant, in one embodiment a mid-chain branched alkyl sulfate and / or mid-chain branched alkyl benzene sulfonate having a chain derived from a polyalkylene oxide-containing compound of the present disclosure, for example, a mid-chain branched alkyl sulfate. In one embodiment, the mid-chain branch is a C1-4 alkyl group, typically a methyl and / or ethyl group.

[0132] Other anionic surfactants useful in the present disclosure include water-soluble salts of paraffin sulfonates and secondary alkane sulfonates containing from about 8 to about 24 carbon atoms (in some instances, from about 12 to 18 carbon atoms); alkyl glyceryl ether sulfonates, particularly ethers of C8-18 alcohols (e.g., those derived from tallow and coconut oil). Mixtures of alkyl benzene sulfonates with the above-mentioned paraffin sulfonates, secondary alkane sulfonates, and alkyl glyceryl ether sulfonates are also useful. Additional suitable anionic surfactants include methyl ester sulfonates and alkyl ether carboxylates. Further suitable anionic surfactants useful in the present disclosure can be found in U.S. Pat. Nos. 4,285,841 (Barrat et al., issued August 25, 1981) and 3,919,678 (Laughlin et al., issued December 30, 1975), both of which are incorporated herein by reference.

[0133] Anionic surfactants may exist in acidic form and may be neutralized to form surfactant salts. Typical neutralizing agents include hydroxides, such as metal counterion bases, such as NaOH or KOH. Further suitable neutralizing agents for acidic anionic surfactants include ammonia, amines, or alkanolamines. Non-limiting examples of alkanolamines include monoethanolamine, diethanolamine, triethanolamine, and other linear or branched alkanolamines known in the art. Suitable alkanolamines include 2-amino-1-propanol, 1-aminopropanol, monoisopropanolamine, or 1-amino-3-propanol. Amine neutralization may be complete or partial; for example, a portion of the anionic surfactant mixture may be neutralized with sodium or potassium, and a portion of the anionic surfactant mixture may be neutralized with amines or alkanolamines.

[0134] <Nonionic surfactants> In some embodiments, the detergent or cleaning compositions of the present disclosure comprise one or more nonionic surfactants. In certain embodiments, the detergent or cleaning compositions comprise from about 0.1% to about 40%, preferably from about 0.2% to about 15%, and more preferably from about 0.3% to about 10% by weight of one or more nonionic surfactants.

[0135] Nonionic surfactants useful in the present disclosure include any conventional nonionic surfactant. These may include, for example, alkoxylated fatty alcohols and amine oxide surfactants. In some examples, the cleaning composition may contain ethoxylated nonionic surfactants. These materials are described in U.S. Pat. No. 4,285,841 (Barrat et al., issued August 25, 1981). Nonionic surfactants are those having the formula R(OC2H4) n The surfactants may be selected from ethoxylated alcohols and ethoxylated alkylphenols of the formula: OH, where R is selected from the group consisting of aliphatic hydrocarbon groups containing from about 8 to about 15 carbon atoms and alkylphenyl groups in which the alkyl group contains from about 8 to about 12 carbon atoms, and the average value of n is from about 5 to about 15. These surfactants are described in more detail in U.S. Pat. No. 4,284,532, issued Aug. 18, 1981 to Leikhim et al. In one example, the nonionic surfactant is selected from ethoxylated alcohols having an average of about 24 carbon atoms in the alcohol and an average degree of ethoxylation of about 9 moles of ethylene oxide per mole of alcohol.

[0136] Other non-limiting examples of nonionic surfactants useful in the present disclosure include C8-C18 alkyl ethoxylates (such as NEODOL® nonionic surfactants from Shell); C6-C12 alkyl phenol alkoxylates (wherein the alkoxylate units can be ethyleneoxy units, propyleneoxy units, or mixtures thereof); C12-C18 alcohol and C6-C12 alkyl phenol condensates with ethylene oxide / propylene oxide block polymers (such as Pluronic® from BASF); C14-C22, mid-chain branched alcohols (BA) as discussed in U.S. Pat. No. 6,150,322; and C14-C22, mid-chain branched alcohols (BA) as discussed in U.S. Pat. Nos. 6,153,577, 6,020,303, and 6,093,856. BAEx, which are C14 to C22 medium-chain branched alkyl alkoxylates (where x is 1 to 30), as discussed; alkyl polysaccharides, as discussed in U.S. Pat. No. 4,565,647 (Llenado, issued Jan. 26, 1986); alkyl polyglycosides, particularly those discussed in U.S. Pat. Nos. 4,483,780 and 4,483,779; polyhydroxy fatty acid amides, as discussed in U.S. Pat. No. 5,332,528, WO 92 / 06162, WO 93 / 19146, WO 93 / 19038, and WO 94 / 09099; and ether-capped poly(oxyalkylated) alcohol surfactants, as discussed in U.S. Pat. No. 6,482,994 and WO 01 / 42408.

[0137] Suitable nonionic detersive surfactants also include alkyl polyglucosides and alkyl alkoxylated alcohols. Suitable nonionic surfactants also include those sold by BASF under the trade name Lutensol®.

[0138] In some embodiments, the nonionic surfactant is selected from alkyl alkoxylated alcohols, such as C8-18 alkyl alkoxylated alcohols, including the polyalkylene oxide-containing compounds of the present disclosure, such as C8-18 alkyl ethoxylated alcohols. The alkyl alkoxylated alcohols may have an average degree of alkoxylation of from about 1 to about 50, or from about 1 to about 30, or from about 1 to about 20, or from about 1 to about 10. In certain embodiments, the alkyl alkoxylated alcohol is a C8-18 alkyl ethoxylated alcohol having an average degree of ethoxylation of from about 1 to about 10, or from about 1 to about 7, or from about 1 to about 5, or from about 3 to about 7. The alkyl alkoxylated alcohol can be linear or branched, substituted or unsubstituted.

[0139] <Cationic surfactants> In some embodiments, the detergent or cleaning compositions of the present disclosure comprise one or more cationic surfactants.

[0140] In some embodiments, the detergent or cleaning compositions of the present disclosure comprise from about 0.1% to about 10%, preferably from about 0.2% to about 7%, and more preferably from about 0.3% to about 5% by weight of one or more cationic surfactants. In other aspects, the detergent or cleaning compositions of the present disclosure are substantially free of cationic surfactants and surfactants that become cationic at a pH below 7 or below 6.

[0141] Non-limiting examples of cationic surfactants include quaternary ammonium surfactants, which can have up to 26 carbon atoms, such as alkoxylate quaternary ammonium (AQA) surfactants, as discussed in U.S. Pat. No. 6,136,769; dimethylhydroxyethyl quaternary ammonium, as discussed in U.S. Pat. No. 6,004,922; dimethylhydroxyethyl lauryl ammonium chloride, as discussed in WO 98 / 35002, WO 98 / 35003, WO 98 / 35004, WO 98 / 35005, WO 98 / 35006, WO 98 / 35007, WO 98 / 35009 ... 98 / 35006; cationic ester surfactants such as those discussed in U.S. Pat. Nos. 4,228,042, 4,239,660, 4,260,529, and 6,022,844; and amino surfactants (specifically, amidopropyldimethylamine (APA)) such as those discussed in U.S. Pat. No. 6,221,825 and WO 00 / 47708.

[0142] Suitable cationic detersive surfactants also include alkyl pyridinium compounds, alkyl quaternary ammonium compounds, alkyl quaternary phosphonium compounds, alkyl tertiary sulfonium compounds, and mixtures thereof.

[0143] Suitable cationic cleansing surfactants have the general formula: (R)(R a )(R b )(R c )N + X - wherein R is a linear or branched, substituted or unsubstituted C alkyl or alkenyl moiety; and R a and R b are independently selected from a methyl or ethyl moiety; R cis a hydroxyl, hydroxymethyl, or hydroxyethyl moiety, and X is an anion that provides charge neutrality; suitable anions include halides, such as chloride, sulfate, and sulfonate. A suitable cationic detersive surfactant is mono-C6-18 alkyl mono-hydroxyethyldi-methyl quaternary ammonium chloride. Highly suitable cationic detersive surfactants are mono-C8-10 alkyl mono-hydroxyethyldi-methyl quaternary ammonium chloride, mono-C10-12 alkyl mono-hydroxyethyldi-methyl quaternary ammonium chloride, and mono-C10 alkyl mono-hydroxyethyldi-methyl quaternary ammonium chloride.

[0144] <Zwitterionic surfactants> Examples of zwitterionic surfactants include secondary and tertiary amine derivatives, heterocyclic secondary and tertiary amine derivatives, or derivatives of quaternary ammonium compounds, quaternary phosphonium compounds, or tertiary sulfonium compounds. For examples of zwitterionic surfactants, including betaines (e.g., alkyl dimethyl betaines and coconut dimethylamidopropyl betaines, C8-C18 (e.g., C12-C18) amine oxides, and sulfo- and hydroxyl betaines (e.g., N-alkyl-N,N-dimethylamino-1-propanesulfonic acid, where the alkyl group can be C8-C18, or in some embodiments, C10-C14), see U.S. Pat. No. 3,929,678, column 19, line 38 to column 22, line 48.

[0145] <Amphoteric surfactant> Examples of amphoteric surfactants include aliphatic derivatives of heterocyclic secondary and tertiary amines, in which the aliphatic group may be linear or branched, and one of the aliphatic substituents contains at least about 8 carbon atoms, typically about 8 to about 18 carbon atoms, and at least one of the aliphatic substituents contains an anionic water-dissolving group, such as carboxy, sulfonate, or sulfate. Examples of compounds that fall within this definition include sodium 3-(dodecylamino)propionate, sodium 3-(dodecylamino)propane-1-sulfonate, sodium 2-(dodecylamino)ethyl sulfate, sodium 2-(dimethylamino)octadecanoate, disodium 3-(N-carboxymethyldodecylamino)propane-1-sulfonate, disodium octadecyl iminodiacetate, sodium 1-carboxymethyl-2-undecylimidazole, and sodium N,N-bis(2-hydroxyethyl)-2-sulfato-3-dodecoxypropylamine. For examples of amphoteric surfactants, see U.S. Patent No. 3,929,678 (Laughlin et al., issued December 30, 1975), column 19, lines 18-35. Suitable amphoteric surfactants also include sarcosinates, glycosinates, taurinates, and mixtures thereof.

[0146] <Branched surfactants> In some embodiments, the detergent or cleaning compositions of the present disclosure comprise one or more branched surfactants. Suitable branched surfactants include anionic branched surfactants selected from branched sulfate or sulfonate surfactants, such as branched alkyl sulfates, branched alkyl alkoxylated sulfates, and branched alkyl benzene sulfonates, and including one or more random alkyl branches, e.g., C1-4 alkyl groups, typically methyl and / or ethyl groups.

[0147] In some embodiments, the branched detersive surfactant is a mid-chain branched detersive surfactant, typically a mid-chain branched anionic detersive surfactant such as a mid-chain branched alkyl sulfate and / or a mid-chain branched alkyl benzene sulfonate. In some embodiments, the detersive surfactant is a mid-chain branched alkyl sulfate. In some embodiments, the mid-chain branch is a C1-4 alkyl group, typically a methyl group and / or an ethyl group.

[0148] In some embodiments, the branched surfactant has the formula: A b -XB longer alkyl chain, mid-chain branched surfactant compounds, During the ceremony, (a)A b has (1) a longest linear carbon chain attached to the -XB moiety ranging from 8 to 21 carbon atoms; and (2) one or more C1-C3 alkyl moieties branching from the longest linear carbon chain, (3) at least one of the branched alkyl moieties is directly attached to a carbon of the longest linear carbon chain at a position ranging from the second carbon (counting from the first carbon attached to the -XB moiety) to the ω-2 carbon (the carbon two away from the terminal carbon, i.e., the third carbon from the end of the longest linear carbon chain), and (4) the surfactant composition has an A in the above formula ranging from 14.5 to about 17.5 (typically about 15 to about 17). b - a hydrophobic C9 to C22 mid-chain branched alkyl moiety having an average total number of carbon atoms in the X moiety (total carbons in the moiety), typically about C12 to about C18; (b) B is a carboxylic acid salt selected from the group consisting of sulfates, sulfonates, amine oxides, polyoxyalkylenes (such as polyoxyethylene and polyoxypropylene), alkoxylated sulfates, polyhydroxy moieties, phosphate esters, glycerol sulfonates, polygluconates, polyphosphate esters, phosphonates, sulfosuccinates, sulfosuccaminates, polyalkoxylated carboxylates, glucamides, taurinates, sarcosinates, glycinates, isethionates, dialkanolamides, monoalkanolamides, monoalkanolamide sulfates, diglycolamides, sulfuric acid salts, and the like. and a hydrophobic moiety selected from acid diglycolamides, glycerol esters, glycerol sulfate esters, glycerol ethers, glycerol sulfate ethers, polyglycerol ethers, polyglycerol sulfates, sorbitan esters, polyalkoxylated sorbitan esters, ammoniacal alkane sulfonic acids, amidopropyl betaines, alkylated quats, alkylated / polyhydroxyalkylated quats, alkylated / polyhydroxylated oxypropyl quats, imidazolines, 2-yl-succinates, sulfonated alkyl esters, and sulfonated fatty acids (e.g., (A b -X) z -Note that one or more hydrophobic moieties may be attached to B, such as in B, to give a dimethyl quat. (c) X is selected from —CH— and —C(O)—.

[0149] Generally, A in the above formula b The moiety does not have any quaternary substituted carbon atoms (i.e., four carbon atoms directly bonded to one carbon atom). Depending on the hydrophilic moiety (B) selected, the resulting surfactant may be anionic, nonionic, cationic, zwitterionic, amphoteric, or ampholyte. In some embodiments, B is a sulfate salt and the resulting surfactant is anionic.

[0150] In some embodiments, the branched surfactant comprises a longer alkyl chain, mid-chain branched surfactant compound of the formula above, wherein A b The moiety has the formula:

[0151] [ka] and the branched primary alkyl moiety (R d , R e , and R f The total number of carbon atoms in the R d , R e , and R f If all are not hydrogen, then R d , R e , and R f are each independently selected from hydrogen and C1-C3 alkyl (typically methyl), and when z is 0, at least R d or R e is not hydrogen, w is an integer of 0 to 13, x is an integer of 0 to 13, y is an integer of 0 to 13, z is an integer of 0 to 13, and w+x+y+z is 7 to 13.

[0152] In some embodiments, the branched surfactant comprises a longer alkyl chain, mid-chain branched surfactant compound of the formula above, A b The part is

[0153] [ka] or a branched primary alkyl moiety having a formula selected from a combination thereof, wherein e, f, g, and h are integers, e+f is 10 to 16, and g+h is 8 to 14; and If e+f=10, e is an integer between 2 and 9, and f is an integer between 1 and 8. If e+f=11, e is an integer between 2 and 10, and f is an integer between 1 and 9; If e+f=12, e is an integer between 2 and 11, and f is an integer between 1 and 10; If e+f=13, e is an integer between 2 and 12, and f is an integer between 1 and 11; If e+f=14, e is an integer between 2 and 13, and f is an integer between 1 and 12, If e+f=15, e is an integer between 2 and 14, and f is an integer between 1 and 13; If e+f=16, e is an integer from 2 to 15, and f is an integer from 1 to 14; When g+h=8, g is an integer from 2 to 7, and h is an integer from 1 to 6; When g+h=9, g is an integer from 2 to 8, and h is an integer from 1 to 7; When g+h=10, g is an integer from 2 to 9, and h is an integer from 1 to 8; When g+h=11, g is an integer from 2 to 10, and h is an integer from 1 to 9; When g+h=12, g is an integer from 2 to 11, and h is an integer from 1 to 10; When g+h=13, g is an integer from 2 to 12, and h is an integer from 1 to 11; When g+h=14, g is an integer from 2 to 13, and h is an integer from 1 to 12.

[0154] In the above mid-chain branched surfactant compound, a specific branching point (for example, R d , R e , and / or R f The following formula represents a mono-methyl branched alkyl A b For moieties, the mid-chain branching range (ie, where the branching points occur), the preferred mid-chain branching range, and the more preferred mid-chain branching range are given.

[0155] [ka]

[0156] For mono-methyl substituted surfactants, these ranges exclude the two terminal carbon atoms of the chain and the carbon atom immediately adjacent to the -XB group.

[0157] The formula below is a dimethyl-substituted linear alkyl group A bThe mid-chain branching range of the moiety, the preferred mid-chain branching range, and the more preferred mid-chain branching range are shown.

[0158] [ka]

[0159] Additional suitable branched surfactants are disclosed in U.S. Patent Nos. 6,008,181, 6,060,443, 6,020,303, 6,153,577, 6,093,856, 6,015,781, 6,133,222, 6,326,348, 6,482,789, 6,677,289, 6,903,059, 6,660,711, 6,335,312, and WO 9918929. Still other suitable branched surfactants include those described in WO 9738956, WO 9738957, and WO 0102451.

[0160] In some embodiments, the branched anionic surfactant comprises a branched modified alkylbenzene sulfonate (MLAS), as discussed in WO 99 / 05243, WO 99 / 05242, WO 99 / 05244, WO 99 / 05082, WO 99 / 05084, WO 99 / 05241, WO 99 / 07656, WO 00 / 23549, and WO 00 / 23548.

[0161] In some embodiments, the branched anionic surfactant comprises a C12 / 13 alcohol-based surfactant containing methyl branches randomly arranged along the hydrophobe chain, e.g., Safol®, Marlipal® available from Sasol.

[0162] Other suitable branched surfactants include those disclosed in U.S. Pat. No. 6,037,313 (P&G), WO 9521233 (P&G), U.S. Pat. No. 3,480,556 (Atlantic Richfield), US Patent Application No. 6683224 (Cognis), US Patent Application No. 20030225304A1 (Kao), US Patent Application No. 2004236158A1 (R&H), US Patent Application No. 6818700 (Atofina), US Patent Application No. 2004154640 (Smith et al.), European Patent No. 128 No. 0746 (Shell), No. 1025839 (L'Oreal), US Patent No. 6765119 (BASF), European Patent No. 1080084 (Dow), US Patent No. 6723867 (Cognis), European Patent Application No. AG), U.S. Patent Application Publication No. 2004048766 (Raths et al.), U.S. Patent No. 6,596,675 (L'Oreal), European Patent Nos. 1,136,471 (Kao), 961,765 (Albemarle), U.S. Patent No. 6,580,009 (BASF), U.S. Patent Application Publication No. 2003,105,352 (Dado et al.), U.S. Patent No. 6,573,345 (Cryovac), German Patent No. 1015 5520 (BASF), US Patent No. 6534691 (duPont), US Patent No. 6407279 (ExxonMobil), US Patent No. 5831134 (Peroxid-Chemie), US Patent No. 58 No. 11617 (Amoco), No. 5463143 (Shell), No. 5304675 (Mobil), No. 5227544 (BASF), No. 5446213A (MITSUBISHI) KASEICORPORATION), European Patent Application Publication No. 1230200A2 (BASF), European Patent No. 1159237B1 (BASF), U.S. Patent Application Publication No. 20040006250A1 (NONE), European Patent No. 1230200B1 (BASF), International Publication No. 2004014826A1 (SHELL), U.S. Patent No. 6703535B2 (CHEVRON), European Patent No. 1140741B1 (BASF), International Publication No. 2003095402A1 (OXEN No. 6,765,106B2 (SHELL), U.S. Patent Application Publication No. 20040167355A1 (NONE), U.S. Patent No. 6,700,027B1 (CHEVRON), U.S. Patent Application Publication No. 20040242946A1 (NONE), WO 2005037751A2 (SHELL), WO 2005037752A1 (SHELL), U.S. Patent No. 6,906,230B1 (BASF), and WO 2005037747A2 (SHELL OIL COMPANY).

[0163] Further suitable branched anionic detersive surfactants include surfactant derivatives of isoprenoid-based hyperbranched detergent alcohols, as described in U.S. Patent Application Publication No. 2010 / 0137649. Isoprenoid-based surfactants and isoprenoid derivatives are also described in the publication "Comprehensive Natural Products Chemistry: Isoprenoids Including Carotenoids and Steroids (Vol. two)" by Barton and Nakanishi, © 1999, Elsevier Science Ltd, and are included in Structure E, which is incorporated herein by reference.

[0164] Further suitable branched anionic detersive surfactants include those derived from anteiso and iso-alcohols. Such surfactants are disclosed in WO2012009525.

[0165] Additional suitable branched anionic detersive surfactants include those described in U.S. Patent Application Publication Nos. 2011 / 0171155(A1) and 2011 / 0166370(A1).

[0166] Suitable branched anionic surfactants also include Guerbet alcohol surfactants. Guerbet alcohols are branched primary monofunctional alcohols with two linear carbon chains, the branch point always being at the second carbon position. Chemically, Guerbet alcohols are described as 2-alkyl-1-alkanols. Guerbet alcohols generally have between 12 carbon atoms and 36 carbon atoms. Guerbet alcohols have the formula: (R g )(R h )CHCHOH, where R g is a straight chain alkyl group, and R h is a straight chain alkyl group, and R g and R h The total number of carbon atoms in R is 10 to 34. g and R h Guerbet alcohols are commercially available from Sasol under the trade name Isofol® alcohols and from Cognis under the trade name Guerbetol.

[0167] Each of the above branched surfactants may comprise a bio-based content, hi some embodiments, the branched surfactant has at least about 50%, at least about 60%, at least about 70%, at least about 80%, at least about 90%, at least about 95%, at least about 97%, or about 100% bio-based content.

[0168] <Combination of surfactants> In some embodiments, the detergent or cleaning compositions of the present disclosure include an anionic surfactant and a nonionic surfactant, such as a C12-C18 alkyl ethoxylate. In other embodiments, the detergent or cleaning compositions of the present disclosure include a C10-C15 alkyl benzelsulfonate (LAS) and another anionic surfactant, such as a C10-C18 alkyl alkoxy sulfate (AExS), where x is 1-30. In some embodiments, the detergent or cleaning compositions of the present disclosure include an anionic surfactant and a cationic surfactant, such as dimethylhydroxyethyl lauryl ammonium chloride. In other embodiments, the detergent or cleaning compositions of the present disclosure include an anionic surfactant and an amphoteric surfactant, such as a C12-C14 dimethylamine oxide.

[0169] When the detergent or cleaning compositions of the present disclosure include a combination of anionic and nonionic surfactant materials, the weight ratio of anionic surfactant to nonionic surfactant is preferably at least about 1.5:1, more preferably at least about 2:1 or 5:1 or 25:1, and most preferably at least about 100:1.

[0170] <Cleaning additives> The detergent or cleaning compositions of the present disclosure may also contain cleaning adjunct additives. Suitable cleaning adjunct additives include builders, surfactants or thickeners, mud soil removal / anti-redeposition agents, polymeric soil release agents, polymeric dispersants, polymeric grease cleaning agents, enzymes, enzyme stabilizing systems, bleaching compounds, bleaches, bleach activators, bleach catalysts, brighteners, dyes, hueing agents, dye transfer inhibitors, chelating agents, suds suppressors, softeners, fragrances, and mixtures thereof.

[0171] <Enzyme> The detergent or cleaning composition of the present disclosure may contain one or more enzymes that provide cleaning performance and / or fabric care benefits.Examples of suitable enzymes include, but are not limited to, hemicellulase, peroxidase, protease, cellulase, xylanase, lipase, phospholipase, esterase, cutinase, pectinase, mannanase, pectate lyase, keratinase, reductase, oxidase, phenoloxidase, lipoxygenase, ligninase, pullulanase, tannase, pentosanase, malanase, β-glucanase, arabinosidase, hyaluronidase, chondroitinase, laccase, and amylase, or mixtures thereof.A typical combination is an enzyme cocktail, which may include, for example, protease and lipase together with amylase. When present in a detergent or cleaning composition, the additional enzymes may be present at a concentration of from about 0.00001% to about 2%, from about 0.0001% to about 1%, or even from about 0.001% to about 0.5% enzyme protein by weight of the detergent or cleaning composition.

[0172] In one aspect, preferred enzymes include proteases. Suitable proteases include serine proteases, such as neutral or alkaline microbial serine proteases, such as metalloproteases and subtilisins (EC 3.4.21.62). Suitable proteases include those of animal, plant, or microbial origin. In one aspect, such suitable proteases may be of microbial origin. Suitable proteases include chemically or genetically modified variants of the suitable proteases listed above. In one aspect, suitable proteases may be serine proteases, such as alkaline microbial proteases and / or trypsin-type proteases. Examples of suitable neutral or alkaline proteases include:

[0173] (a) subtilisins (EC 3.4.21.62), including those derived from Bacillus, such as Bacillus lentus, B. alkalophilus, B. subtilis, B. amyloliquefaciens, Bacillus pumilus, and Bacillus gibsonii, as described in U.S. Pat. Nos. 6,312,936 B1, 5,679,630, 4,760,025, and 7,262,042, and WO 09 / 021867; (b) trypsin- or chymotrypsin-type proteases, such as trypsin (e.g., of porcine or bovine origin) (including the Fusarium proteases described in WO 89 / 06270 and the chymotrypsin proteases from Cellumonas described in WO 05 / 052161 and WO 05 / 052146); (c) Metalloproteases, including those derived from Bacillus amyloliquefaciens, as described in WO 07 / 044993 A2.

[0174] Preferred proteases include those derived from Bacillus gibsonii or Bacillus lentus.

[0175] Suitable commercially available protease enzymes include those sold under the trade names Alcalase®, Savinase®, Primase®, Durazym®, Polarzyme®, Kannase®, Liquanase®, Liquanase Ultra®, Savinase Ultra®, Ovozyme®, Neutrase®, Everlase® and Esperase® by Novozymes A / S (Denmark); those sold under the trade names Maxatase®, Maxacal®, Maxapem®, Properase®, Purafect®, Purafect Prime®, Purafect Ox®, FN3®, FN4®, Excellase® and Purafect OXP® by Genencor International; Enzymes under the trade names Opticlean® and Optimase®, and those available from Henkel / Kemira, namely BLAP (having the following mutations S99D+S101 R+S103A+V104I+G159S, the sequence shown in Figure 29 of U.S. Pat. No. 5,352,604, hereinafter referred to as BLAP), BLAP R (BLAP having S3T+V4I+V199M+V205I+L217D), BLAP X (BLAP having S3T+V4I+V205I), and BLAP F49 (BLAP with S3T+V4I+A194P+V199M+V205I+L217D) (all available from Henkel / Kemira), and Kao's KAP (a subtilisin from Bacillus alcalophilus with mutations A230V+S256G+S259N).

[0176] Suitable α-amylases include those of bacterial or fungal origin, including chemically or genetically modified mutants. Preferred alkaline α-amylases are derived from Bacillus species, such as Bacillus licheniformis, Bacillus amyloliquefaciens, Bacillus stearothermophilus, Bacillus subtilis, or other Bacillus species, such as Bacillus sp. NCIB 12289, NCIB 12512, NCIB 12513, DSM 9375 (U.S. Pat. No. 7,153,818), DSM 12368, DSM Z no. 12649, KSM AP1378 (WO 97 / 00324), KSM K36, or KSM K38 (EP 1,022,334). Preferred amylases include:

[0177] (a) variants described in WO 94 / 02597, WO 94 / 18314, WO 96 / 23874 and WO 97 / 43424, in particular variants in which one or more of the following positions have been substituted relative to the enzyme set forth in WO 96 / 23874 as SEQ ID NO: 2: 15, 23, 105, 106, 124, 128, 133, 154, 156, 181, 188, 190, 197, 202, 208, 209, 243, 264, 304, 305, 391, 408 and 444; (b) variants described in U.S. Pat. No. 5,856,164 and WO 99 / 23211, WO 96 / 23873, WO 00 / 60060, and WO 06 / 002643, in particular the AA560 enzyme described in WO 06 / 002643 as SEQ ID NO: 12, at positions: 26, 30, 33, 82, 37, 106, 118, 128, 133, 149, 150, 160, 178, 182, 186, 193, 203, 214, 231, 256, 257, 258, 269, 270, 272, 283, 295, 296, 298, 299, 303, 304, 305, 311, 314, 315, 318, 319, 339, 345, 361, 378, 383, 419, 421, 437, 441, 444, 445, 446, 447, 450, 461, 471, 482, 484, preferably containing deletions of D183* and G184*; (c) SEQ ID NO: 4 in WO 06 / 002643, variants exhibiting at least 90% identity with the wild-type enzyme from Bacillus sp722, in particular variants with deletions at positions 183 and 184 and variants described in WO 00 / 60060, which are incorporated herein by reference; (d) Variants exhibiting at least 95% identity to the wild-type enzyme from Bacillus sp. 707 (SEQ ID NO: 7 of U.S. Pat. No. 6,093,562), in particular those comprising one or more of the mutations M202, M208, S255, R172 and / or M261. Preferably, the amylase comprises one or more of the mutations M202L, M202V, M202S, M202T, M202I, M202Q, M202W, S255N and / or R172Q. Particularly preferred are those comprising the M202L or M202T mutants. (e) A variant described in WO 09 / 149130, preferably a variant exhibiting at least 90% identity to SEQ ID NO: 1 or SEQ ID NO: 2 in WO 09 / 149130, the wild-type enzyme from Geobacillus Stearophermophilus or a truncated variant thereof.

[0178] Suitable commercially available α-amylases include DURAMYL®, LIQUEZYME®, TERMAMYL®, TERMAMYL ULTRA®, NATALASE®, SUPRAMYL®, STAINZYME®, STAINZYME PLUS®, FUNGAMYL®, and BAN® (Novozymes A / S, Bagsvaerd, Denmark), KEMZYM® AT 9000 (Biozym Biotech Trading GmbH, Wehlistrasse 27b A-1200, Wien, Austria), RAPIDASE®, PURASTAR®, ENZYSIZE®, OPTISIZE HT PLUS®, POWERASE®, and PURASTAR OXAM® (Genencor International Inc., Palo Alto, CA). Alto, California), and KAM® (Kao, 14-10 Nihonbashi Kayabacho, 1-chome, Chuo-ku, Tokyo 103-8210, Japan). In one aspect, suitable amylases include NATALASE®, STAINZYME®, and STAINZYME PLUS®, and mixtures thereof.

[0179] In one aspect, such enzymes may be selected from the group consisting of lipases, including "first cycle lipases," such as those described in U.S. Pat. No. 6,939,702 B1 and U.S. Patent Application Publication No. 2009 / 0217464. In one aspect, the lipase is a first wash lipase, preferably a variant of a wild-type lipase from Thermomyces lanuginosus, containing the T231R and N233R mutations. The wild-type sequence is the 269 amino acids (amino acids 23-291) of Thermomyces lanuginosus (from Humicola lanuginosa) under Swissprot accession number Swiss-Prot O59952. Preferred lipases include those sold under the trade names Lipex® and Lipolex®.

[0180] In one aspect, other preferred enzymes include endoglucanases of microbial origin exhibiting endo-β-1,4-glucanase activity (EC 3.2.1.4), including bacterial polypeptides endogenous to members of the genus Bacillus having a sequence identity of at least 90%, preferably 94%, more preferably 97%, and even more preferably 99% to the amino acid sequence SEQ ID NO:2 in U.S. Patent No. 7,141,403 (B2), and mixtures thereof. Suitable endoglucanases are sold under the trade names Celluclean® and Whitezyme® (Novozymes A / S, Bagsvaerd, Denmark).

[0181] Other preferred enzymes include pectate lyases sold under the trade names Pectawash®, Pectaway®, Xpect® and mannases sold under the trade names Mannaway® (all from Novozymes A / S, Bagsvaerd, Denmark), and Purabrite® (Genencor International Inc., Palo Alto, California).

[0182] <Enzyme stabilization system> The enzyme-containing compositions described herein may optionally comprise from about 0.001% to about 10% by weight of the composition of an enzyme stabilizing system, in some instances from about 0.005% to about 8% by weight, and in other instances from about 0.01% to about 6% by weight of the composition. The enzyme stabilizing system can be any stabilizing system compatible with the detergent enzymes. Such systems may be inherently provided by other formulation actives or may be added separately, for example, by the formulator or detergent enzyme manufacturer. Such stabilizing systems may include, for example, calcium ions, boric acid, propylene glycol, short-chain carboxylic acids, boronic acids, chlorine bleach scavengers, and mixtures thereof, and are designed to address different stabilization issues depending on the type and physical form of the cleaning composition. See U.S. Pat. No. 4,605,783 for a review of borate stabilizers. In the case of aqueous detergent or cleaning compositions containing proteases, reversible protease inhibitors such as boron compounds including borate, 4-formylphenylboronic acid, phenylboronic acid and their derivatives, or compounds such as calcium formate, sodium formate and 1,2-propanediol may be added to further improve stability.

[0183] <Builder> The detergent or cleaning compositions of the present disclosure may optionally contain a builder in addition to the sulfonic acid group-containing copolymer described above. Built cleaning compositions typically contain at least about 1 wt. % builder, based on the total weight of the composition. Liquid cleaning compositions may contain up to about 10 wt. % builder, and in some instances up to 8 wt. % builder, based on the total weight of the composition. Granular cleaning compositions may contain up to about 30 wt. % builder, and in some instances up to 5 wt. % builder, based on the total weight of the composition.

[0184] Builders selected from aluminosilicates (e.g., zeolite builders such as zeolite A, zeolite P, and zeolite MAP) and silicates help control mineral hardness, especially calcium and / or magnesium, in wash water and remove particulate soils from surfaces. Suitable builders may be selected from the group consisting of: polyphosphates (e.g., sodium tripolyphosphate), especially phosphates such as the sodium salt; carbonates, bicarbonates, sesquicarbonates, and mineral carbonates other than sodium carbonate or sodium sesquicarbonate; organic mono-, di-, tri-, and tetracarboxylates, especially water-soluble non-surfactant carboxylates in the form of their acid, sodium, potassium, or alkanolammonium salts, and water-soluble low-molecular-weight polymeric carboxylates of aliphatic and aromatic types; and phytic acid. These may be supplemented with borates, for example, for pH buffering purposes, or sulfates, especially sodium sulfate, as well as any other fillers or carriers that may be important for the mass production of stable surfactant- and / or builder-containing cleaning compositions. Further suitable detergent builders may be selected from citric acid, lactic acid, fatty acids, polycarboxylate builders such as copolymers of acrylic acid, copolymers of acrylic acid and maleic acid, and copolymers of acrylic acid and / or maleic acid and other suitable ethylenic monomers with various types of additional functional groups. Also suitable for use as builders in the present disclosure are synthetic crystalline ion exchange materials or hydrates thereof having a chain structure and a composition represented by the general anhydrous form x(MO)·ySiO·zMO, where M is Na and / or K, M' is Ca and / or Mg, y / x is 0.5 to 2.0, and z / x is 0.005 to 1.0, as taught in U.S. Patent No. 5,427,711.

[0185] Preferably, the detergent or cleaning compositions of the present disclosure are substantially free of other builders, particularly inorganic builders, more particularly zeolite builders and phosphate builders.

[0186] <Structuring agent / thickener> When the detergent or cleaning composition of the present disclosure is in fluid form, for example, a liquid laundry detergent composition, it may contain from about 0.01% to about 1%, or from about 0.05% to about 0.8%, or from about 0.1% to about 0.6%, or even from about 0.3% to about 0.5% by weight of a dibenzylidene polyol acetal derivative (DBPA). Non-limiting examples of suitable DBPA molecules are disclosed in U.S. Patent Application No. 61 / 167,604. In one embodiment, the DBPA derivative may include a dibenzylidene sorbitol acetal derivative (DBS). The DBS derivative may be selected from the group consisting of 1,3:2,4-dibenzylidene sorbitol, 1,3:2,4-di(p-methylbenzylidene) sorbitol, 1,3:2,4-di(p-chlorobenzylidene) sorbitol, 1,3:2,4-di(2,4-dimethyldibenzylidene) sorbitol, 1,3:2,4-di(p-ethylbenzylidene) sorbitol, and 1,3:2,4-di(3,4-dimethyldibenzylidene) sorbitol, or mixtures thereof. These and other suitable DBS derivatives are disclosed in U.S. Patent No. 6,102,999, column 2, line 43 to column 3, line 65.

[0187] The liquid laundry detergent compositions of the present disclosure may also contain about 0.005% to about 1% by weight of bacterial cellulose network. The term "bacterial cellulose" includes any type of cellulose produced via fermentation of bacteria of the genus Acetobacter, such as CELLULON® by CPKelco US, including materials commonly referred to as microfibrillated cellulose, reticulated bacterial cellulose, and the like. Some examples of suitable bacterial cellulose can be found in U.S. Patent Nos. 6,967,027, 5,207,826, 4,487,634, 4,373,702, 4,863,565, and U.S. Patent Application Publication No. 2007 / 0027108. In one embodiment, the cross-sectional dimensions of the fibers are 1.6 nm to 3.2 nm by 5.8 nm to 133 nm. Additionally, the bacterial cellulose fibers have an average microfiber length of at least about 100 nm, or from about 100 to about 1,500 nm. In one embodiment, the bacterial cellulose microfibers have an aspect ratio, i.e., the average microfiber length divided by the maximum cross-sectional width of the microfiber, of about 100:1 to about 400:1, or even about 200:1 to about 300:1.

[0188] In one embodiment, the bacterial cellulose is at least partially coated with a polymeric thickener. The at least partially coated bacterial cellulose can be made according to the method disclosed in U.S. Patent Application Publication No. 2007 / 0027108, columns 8-19. In one aspect, the at least partially coated bacterial cellulose comprises about 0.1% to about 5%, or even about 0.5% to about 3% by weight of bacterial cellulose, and about 10% to about 90% by weight of a polymeric thickener. Suitable bacterial celluloses include those described above, and suitable polymeric thickeners include carboxymethyl cellulose, cationic hydroxymethyl cellulose, and mixtures thereof.

[0189] In one embodiment, the composition may further comprise from about 0.01 to about 5% by weight of the composition of cellulose fibers. The cellulose fibers may be extracted from vegetables, fruits or wood. Commercially available examples are Avicel® from FMC, Citri-Fi from Fiberstar or Betafib from Cosun.

[0190] In one embodiment, the composition may further comprise from about 0.01 to about 1% by weight of the composition of a non-polymeric crystalline hydroxyl-functional structurant. The non-polymeric crystalline hydroxyl-functional structurant may generally comprise a crystallizable glyceride that can be pre-emulsified to aid dispersion in the final liquid detergent or cleaning composition. In one aspect, the crystallizable glyceride includes hydrogenated castor oil, or "HCO," or a derivative thereof, as long as it can be crystallized in the liquid detergent or cleaning composition.

[0191] The fluid laundry detergent compositions of the present disclosure may comprise from about 0.01% to about 5% by weight of naturally occurring and / or synthetic polymeric structuring agents. Examples of naturally occurring polymeric structuring agents for use in the present disclosure include hydroxyethyl cellulose, hydrophobically modified hydroxyethyl cellulose, carboxymethyl cellulose, polysaccharide derivatives, and mixtures thereof. Suitable polysaccharide derivatives include pectin, alginate, arabinogalactan (gum arabic), carrageenan, gellan gum, xanthan gum, guar gum, and mixtures thereof. Examples of synthetic polymeric structurants for use in the present disclosure include polycarboxylates, polyacrylates, hydrophobically modified ethoxylated urethanes, hydrophobically modified nonionic polyols, and mixtures thereof. In one embodiment, the polycarboxylate polymer is a polyacrylate, polymethacrylate, or mixtures thereof. In another embodiment, the polyacrylate is a copolymer of an unsaturated mono- or dicarbonic acid and a C1-C30 alkyl ester of (meth)acrylic acid. Such copolymers are available from Noveon Inc. under the trade name Carbopol Aqua 30.

[0192] In one embodiment, the external structuring system may comprise a diamide gellant having a molecular weight of from about 150 g / mol to about 1,500 g / mol, or even from about 500 g / mol to about 900 g / mol. Such diamide gelling agents may contain at least two nitrogen atoms, at least two of which form amide functional substituents. In one embodiment, the amide groups are different. In another embodiment, the amide functional groups are the same. Diamide gelling agents have the following formula:

[0193] [ka] wherein R 16 and R 17 is an amino-functional end group, or even an amide-functional end group, and in one aspect, R 16 and R 17may comprise a pH-adjustable group, and the pH-adjustable amide gellant may have a pKa of from about 1 to about 30, or even from about 2 to about 10. In one aspect, the pH-adjustable group may comprise pyridine. In one aspect, R 16 and R 17 may be different. Alternatively, they may be the same.

[0194] L is a linking moiety with a molecular weight of 14 to 500 g / mol. In one embodiment, L can include a carbon chain containing 2 to 20 carbon atoms. In another embodiment, L can include a pH-adjustable group. In one embodiment, the pH-adjustable group is a secondary amine.

[0195] In one aspect, R 16 , R 17 , or at least one of L may include a pH-adjustable group.

[0196] Non-limiting examples of diamide gelling agents are as follows: N,N'-(2S,2'S)-1,1'-(dodecane-1,12-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)diisonicotinamide

[0197] [ka] Dibenzyl (2S,2'S)-1,1'-(propane-1,3-diylbis(azanediyl))bis(3-methyl-1-oxobutane-2,1-diyl)dicarbamate

[0198] [ka] Dibenzyl (2S,2'S)-1,1'-(dodecane-1,12-diylbis(azanediyl))bis(1-oxo-3-phenylpropane-2,1-diyl)dicarbamate

[0199] [ka]

[0200] <Polymer dispersant> The detergent or cleaning composition may contain one or more polymeric dispersants. Examples are carboxymethyl cellulose, poly(vinylpyrrolidone), poly(ethylene glycol), poly(vinyl alcohol), poly(vinylpyridine-N-oxide), poly(vinylimidazole), polycarboxylates such as polyacrylates, maleic acid / acrylic acid copolymers, and lauryl methacrylate / acrylic acid copolymers.

[0201] The detergent or cleaning composition may comprise a compound having the following general structure: bis((C2H5O)(C2H4O) n )(CH3)-N + -C x H 2x -N + -(CH3)-bis((C2H5O)(C2H4O) n ) where n=20-30 and x=3-8, or sulfated or sulfonated versions thereof.

[0202] Detergent or cleaning compositions may comprise amphiphilic alkoxylated grease-cleaning polymers that have balanced hydrophilic and hydrophobic properties to remove grease particles from fabrics and surfaces. Specific embodiments of the amphiphilic alkoxylated grease-cleaning polymers of the present disclosure comprise a core structure with multiple alkoxylate groups attached to the core structure. These may include, for example, alkoxylated polyalkyleneimines having an inner polyethylene oxide block and an outer polypropylene oxide block. Such materials include, but are not limited to, ethoxylated polyethyleneimines, ethoxylated hexamethylenediamines, and sulfated versions thereof. Polypropoxylated derivatives may also be included. A wide variety of amines and polyalkyleneimines can be alkoxylated to various degrees. A useful example is a 600 g / mole polyethyleneimine core ethoxylated to 20 EO groups per NH, available from BASF. The cleaning compositions described herein may comprise from about 0.1% to about 10%, in some examples from about 0.1% to about 8%, and in other examples from about 0.1% to about 6%, of an alkoxylated polyamine, by weight of the cleaning composition.

[0203] Alkoxylated polycarboxylates, such as those made from polyacrylates, are useful in this disclosure to provide additional grease removal performance. Such materials are described in WO 91 / 08281 and WO 90 / 01815. Chemically, these materials comprise polyacrylates with one ethoxy side chain per 7-8 acrylate units. The side chains have the formula -(CH2CHO) m (CH2) n It has the formula CH3, where m is 2 to 3 and n is 6 to 12. The side chains are ester-linked to the polyacrylate "backbone" resulting in a "comb" polymer type structure. The molecular weight can vary, but is typically in the range of about 2000 to about 50,000. The detergent or cleaning compositions described herein may comprise from about 0.1% to about 10%, in some examples from about 0.25% to about 5%, and in other examples from about 0.3% to about 2%, by weight of the cleaning composition, of an alkoxylated polycarboxylate.

[0204] Suitable and preferred amphiphilic graft copolymers include those comprising (i) a polyethylene glycol backbone and (ii) at least one pendant moiety selected from polyvinyl acetate, polyvinyl alcohol, and mixtures thereof. A preferred amphiphilic graft copolymer is Sokalan® HP22 supplied by BASF. Suitable polymers include random graft copolymers, preferably polyvinyl acetate-grafted polyethylene oxide copolymers having a polyethylene oxide backbone and multiple polyvinyl acetate side chains. The molecular weight of the polyethylene oxide backbone is typically about 6000, the weight ratio of polyethylene oxide to polyvinyl acetate is about 40 to 60, and there is not more than one grafting point per 50 ethylene oxide units.

[0205] Carboxylate Polymers - The detergent or cleaning compositions of the present disclosure may also include one or more carboxylate polymers, such as maleate / acrylate random copolymers or polyacrylate homopolymers. In one embodiment, the carboxylate polymer is a polyacrylate homopolymer having a molecular weight of 4,000 Da to 9,000 Da, or 6,000 Da to 9,000 Da.

[0206] Soil Release Polymers - The detergent or cleaning compositions of the present disclosure also include a polymer having the following structure (I), (II) or (III): (I)-[(OCHR 18 -CHR 19 ) i -O-OC-Ar-CO-] o (II)-[(OCHR 20 -CHR 21 ) j -O-OC-sAr-CO-] q (III)-[(OCHR 22 -CHR 23 ) k -OR 24 ] t The composition may comprise one or more soil release polymers having a structure defined by one of the following formulas: i, j, and k are 1 to 200; p, o, and t are 1 to 50; Ar is 1,4-substituted phenylene; sAr is 1,3-substituted phenylene substituted at the 5-position by SO3Me; Me is Li, K, Mg / 2, Ca / 2, Al / 3, ammonium, mono-, di-, tri-, or tetra-alkylammonium (wherein the alkyl group is C1-C18 alkyl or C2-C10 hydroxyalkyl), or a mixture thereof; R 18 , R 19 , R 20 , R 21 , R 22 , and R 23 are independently selected from H or C1-C18 n- or iso-alkyl; R 24 is a linear or branched C1 to C18 alkyl, or a linear or branched C2 to C30 alkenyl, or a cycloalkyl group having 5 to 9 carbon atoms, or a C8 to C30 aryl group, or a C6 to C30 arylalkyl group.

[0207] Suitable soil release polymers are polyester soil release polymers such as Repel-o-tex polymers (e.g., Repel-o-tex SF, SF-2, and SRP6 supplied by Rhodia). Other suitable soil release polymers include Texcare polymers (e.g., Texcare SRA100, SRA300, SRN100, SRN170, SRN240, SRN300, and SRN325 supplied by Clariant). Other suitable soil release polymers are Marloquest polymers (e.g., Marloquest SL supplied by Sasol).

[0208] Cellulosic Polymers - The consumer products of the present disclosure may also include one or more cellulosic polymers, such as those selected from alkyl celluloses, alkyl alkoxyl celluloses, carboxyalkyl celluloses, alkyl carboxyalkyl celluloses, etc. In one embodiment, the cellulosic polymer is selected from the group including carboxymethyl cellulose, methyl cellulose, methylhydroxyethyl cellulose, methylcarboxymethyl cellulose, and mixtures thereof. In one embodiment, the carboxymethyl cellulose has a degree of carboxymethyl substitution of 0.5 to 0.9 and a molecular weight of 100,000 Da to 300,000 Da.

[0209] Examples of polymeric dispersants can be found in U.S. Pat. No. 3,308,067, European Patent Applications Nos. 66915, 193,360, and 193,360.

[0210] <amine> Various amines may be used in the detergent or cleaning compositions described herein to remove grease and particles from soiled materials. The detergent or cleaning compositions described herein may contain from about 0.1% to about 10%, in some examples from about 0.1% to about 4%, and in other examples from about 0.1% to about 2% of additional amines by weight of the cleaning composition. Non-limiting examples of amines include, but are not limited to, polyamines, oligoamines, triamines, diamines, pentaamines, tetraamines, polyetheramines, or combinations thereof. Specific examples of suitable additional amines include tetraethylenepentamine, triethylenetetraamine, diethylenetriamine, polyetheramines, or mixtures thereof.

[0211] <Bleach> The detergent or cleaning compositions of the present disclosure may include one or more bleaching agents. Suitable bleaching agents other than bleach catalysts include photocatalysts, bleach activators, hydrogen peroxide, hydrogen peroxide sources, pre-formed peracids, and mixtures thereof. Generally, when a bleaching agent is used, the detergent or cleaning compositions of the present disclosure may include from about 0.1% to about 50%, or even from about 0.1% to about 25%, by weight of the detergent or cleaning composition of the present disclosure. Examples of suitable bleaching agents include: (1) Photobleaches, such as sulfonated zinc phthalocyanine, sulfonated aluminum phthalocyanine, xanthene dyes, and mixtures thereof. (2) Preformed Peracids: Suitable preformed peracids include, but are not limited to, compounds selected from the group consisting of percarboxylic acids and salts, percarbonic acids and salts, perimidic acids and salts, peroxymonosulfuric acids and salts (such as Oxone®), and mixtures thereof. Suitable percarboxylic acids include compounds of the formula R 25 -(C=O)OOM(where R 25 is an alkyl group, optionally branched, having 6 to 14 carbon atoms, or 8 to 12 carbon atoms if the peracid is hydrophobic, or less than 6 carbon atoms, or even less than 4 carbon atoms if the peracid is hydrophilic, and M is a counterion (e.g., sodium, potassium, or hydrogen). (3) Hydrogen peroxide source: for example, inorganic perhydrate salts, including alkali metal salts such as sodium perborate (usually monohydrate or tetrahydrate), sodium percarbonate, sodium persulfate, sodium perphosphate, sodium persilicate, and mixtures thereof. In one embodiment of the present disclosure, the inorganic perhydrate salt is selected from the group consisting of sodium perborate, sodium percarbonate, and mixtures thereof. When used, the inorganic perhydrate salt is typically present in an amount of 0.05 to 40% or 1 to 30% by weight of the total fabric care and home care product, and is typically incorporated into the fabric care and home care product as a crystalline solid that can be coated. Suitable coatings include inorganic salts (such as alkali metal silicates, carbonates, or borates, or mixtures thereof), or organic materials (such as water-soluble or dispersible polymers, waxes, oils, or fatty soaps). (4)R 26 -(C=O)-L 1 a bleach activator having the formula 26 is an alkyl group, optionally branched, having 6 to 14 carbon atoms, or 8 to 12 carbon atoms, if the bleach activator is hydrophobic, or less than 6 carbon atoms, or even less than 4 carbon atoms, if the bleach activator is hydrophilic; L 1is a leaving group). An example of a suitable leaving group is benzoic acid and its derivatives, particularly benzenesulfonate. Suitable bleach activators include dodecanoyloxybenzenesulfonate, decanoyloxybenzenesulfonate, decanoyloxybenzoic acid or its salts, 3,5,5-trimethylhexanoyloxybenzenesulfonate, tetraacetylethylenediamine (TAED), and nonanoyloxybenzenesulfonate (NOBS). Suitable bleach activators are also disclosed in WO 98 / 17767. While any suitable bleach activator may be used, in one embodiment of the present disclosure, the subject detergent or cleaning composition may include NOBS, TAED, or a mixture thereof.

[0212] When present, peracids and / or bleach activators are generally present in detergent or cleaning compositions in an amount of from about 0.1 to about 60%, from about 0.5 to about 40%, or even from about 0.6 to about 10% by weight of the fabric care and home care product. One or more hydrophobic peracids or precursors thereof may be used in combination with one or more hydrophilic peracids or precursors thereof.

[0213] The amounts of hydrogen peroxide source and peracid or bleach activator may be selected to provide a molar ratio of available oxygen (from the peroxide source) to peracid of from 1:1 to 35:1, or even from 2:1 to 10:1.

[0214] <Bleach catalyst> The detergent or cleaning composition of the present disclosure may also contain one or more bleach catalysts capable of accepting an oxygen atom from a peroxyacid and / or its salt and transferring the oxygen atom to an oxidizable substrate. Suitable bleach catalysts include, but are not limited to, iminium cations and polyions; iminium zwitterions; modified amines; modified amine oxides; N-sulfonylimines; N-phosphonylimines; N-acylimines; thiadiazole dioxides; perfluoroimines; cyclic sugar ketones, and mixtures thereof, as described in U.S. Patent Application Publication No. 2007 / 0173430 A1.

[0215] In another embodiment, the laundry detergent composition comprises a bleaching component, wherein the bleaching component has a logPo / w of 0 or less, −0.5 or less, −1.0 or less, −1.5 or less, −2.0 or less, −2.5 or less, −3.0 or less, or even −3.5 or less. Methods for determining logPo / w are described in further detail below.

[0216] Typically, the bleaching component is capable of generating bleaching species having an XSO of 0.01 to about 0.30, 0.05 to about 0.25, or even about 0.10 to 0.20. Methods for determining the XSO are described in further detail below. For example, a bleaching component having an isoquinolinium structure is capable of generating bleaching species having an oxaziridinium structure. In this example, the XSO is that of an oxaziridinium bleaching species.

[0217] Without being bound by theory, the present inventors believe that controlling the electrophilicity and hydrophobicity as described above allows for delivery of bleaching ingredients substantially only to the more hydrophobic areas of the fabric, which contain electron-rich soils containing visible chromophores that are susceptible to bleaching by the highly electrophilic oxidizing agent.

[0218] In one embodiment, the bleach catalyst has the following general formula:

[0219] [ka] wherein R 27 is selected from the group consisting of 2-ethylhexyl, 2-propylheptyl, 2-butyloctyl, 2-pentylnonyl, 2-hexyldecyl, n-dodecyl, n-tetradecyl, n-hexadecyl, n-octadecyl, iso-nonyl, iso-decyl, iso-tridecyl and iso-pentadecyl.

[0220] LogPo / w is determined according to the method found in Brooke, DN, Dobbs, AJ, Williams, N, Ecotoxicology and Environmental Safety (1986) 11(3):251-260. The parameter XSO is determined according to the method found in Adam, W., Haas, W., Lohray, BB, Journal of the American Chemical Society (1991) 113(16) 6202-6208.

[0221] <Whitening agent> Fluorescent brighteners or other brightening or whitening agents may be incorporated into the cleaning compositions described herein at a concentration of about 0.01% to about 1.2% by weight of the composition. Commercially available fluorescent brighteners suitable for the present disclosure can be classified into subgroups, including, but not limited to, derivatives of stilbenes, pyrazolines, coumarins, benzoxazoles, carboxylic acids, methine cyanines, dibenzothiophene-5,5-dioxide, azoles, 5- and 6-membered heterocycles, and various other substances. Examples of such brighteners are disclosed in "The Production and Application of Fluorescent Brightening Agents," M. Zahradnik, Published by John Wiley & Sons, New York (1982). Specific, non-limiting examples of fluorescent brighteners useful in the compositions of the present disclosure are those identified in U.S. Pat. Nos. 4,790,856, 3,646,015, 7,863,236, and their corresponding Chinese patents.

[0222] In some examples, the optical brightener of the present disclosure has the formula (a):

[0223] [ka] wherein X 1 , X 2 , X 3 , and X 4 -N(R 28 )R 29and R 28 and R 29 are independently selected from hydrogen, phenyl, hydroxyethyl, or unsubstituted or substituted C1-C8 alkyl, or -N(R 28 )R 29 forms a heterocyclic ring, preferably R 28 and R 29 are independently selected from hydrogen or phenyl, or —N(R 28 )R 29 forms an unsubstituted or substituted monophorin ring, M 1 is hydrogen or a cation, preferably M 1 is sodium or potassium, more preferably M 1 is sodium.

[0224] In some examples, the optical brightener is selected from the group consisting of disodium 4,4'-bis{[4-anilino-6-morpholino-s-triazin-2-yl]-amino}-2,2'-stilbenedisulfonate (brightener 15, commercially available under the trade name Tinopal AMS-GX by Ciba-Geigy Corporation), disodium 4,4'-bis{[4-anilino-6-(N-2-bis-hydroxyethyl)-s-triazin-2-yl]-amino}-2,2'-stilbenedisulfonate (commercially available under the trade name Tinopal UNPA-GX by Ciba-Geigy Corporation), and disodium 4,4'-bis{[4-anilino-6-(N-2-hydroxyethyl-N-methylamino)-s-triazin-2-yl]-amino}-2,2'-stilbenedisulfonate (commercially available under the trade name Tinopal 5BM-GX by Ciba-Geigy Corporation). More preferably, the optical brightener is disodium 4,4'-bis{[4-anilino-6-morpholino-s-triazin-2-yl]-amino}-2,2'-stilbenedisulfonate.

[0225] The whitening agent may be added in particulate form or as a premix with a suitable solvent, such as a non-ionic surfactant, monoethanolamine, propanediol.

[0226] <Fabric hueing agent> The composition may include a fabric hueing agent (sometimes referred to as a tinting agent, bluing agent, or whitening agent). Typically, a hueing agent imparts a blue or purple hue to a fabric. The hueing agents can be used alone or in combination to create a specific shade and / or to tint different types of fabric. This can be achieved, for example, by mixing a red and a green-blue dye to produce a blue or purple shade. The hueing agent may be selected from any known chemical class of dyes, including, but not limited to, acridines, anthraquinones (including polycyclic quinones), azines, azos including metal-containing azos (e.g., monoazos, diazos, trisazos, tetrakisazos, polyazos), benzodifurans and benzodifuranones, carotenoids, coumarins, cyanines, diazahemicyanines, diphenylmethanes, formasans, hemicyanines, indigoids, methanes, naphthalimides, naphthoquinones, nitro and nitroso, oxazines, phthalocyanines, pyrazoles, stilbenes, styryls, triarylmethanes, triphenylmethanes, xanthenes, and mixtures thereof.

[0227] Suitable fabric hueing agents include dyes, dye-clay complexes, and organic and inorganic pigments. Suitable dyes include small molecule dyes and polymeric dyes. Suitable small molecule dyes include those selected from the group consisting of dyes classified under the Color Index (CI) classification of direct dyes, basic dyes, reactive dyes or hydrolyzed reactive dyes, solvent dyes, or disperse dyes, for example, classified as blue, violet, red, green, or black, which alone or in combination produce the desired shade. In another aspect, suitable small molecule dyes include dyes classified under the Color Index (CI) classification of the Society of Dyes and Disperse or solvent dyes such as those described in European Patent Nos. 1794275 or 1794276, including dyes designated by the Trademark Office of Colourists (Bradford, UK) as Direct Violet dyes 9, 35, 48, 51, 66, and 99, etc.; Direct Blue dyes 1, 71, 80, and 279, etc.; Acid Red dyes 17, 73, 52, 88, and 150, etc.; Acid Violet dyes 15, 17, 24, 43, 49, and 50, etc.; Acid Blue dyes 15, 17, 25, 29, 40, 45, 75, 80, 83, 90, and 113, etc.; Acid Black dye 1, etc.; Basic Violet dyes 1, 3, 4, 10, and 35, etc.; Basic Blue dyes 3, 16, 22, 47, 66, 75, and 159, etc.; or U.S. Patent No. 7,208,459 B2, and mixtures thereof. In another aspect, suitable small molecule dyes include those having CI numbers selected from the group consisting of Acid Violet 17, Direct Blue 71, Direct Violet 51, Direct Blue 1, Acid Red 88, Acid Red 150, Acid Blue 29, Acid Blue 113, or mixtures thereof.

[0228] Suitable polymeric dyes include those selected from the group consisting of polymers containing covalently attached (sometimes called conjugated) chromogens, such as those copolymerized into the polymer backbone (dye-polymer conjugates), and mixtures thereof, including those described in WO 2011 / 98355, WO 2011 / 47987, U.S. Patent Application Publication No. 2012 / 090102, WO 2010 / 145887, WO 2006 / 055787, and WO 2010 / 142503.

[0229] In another aspect, suitable polymeric dyes include those fabric substantive colorants sold under the name Liquitint® (Milliken, Spartanburg, South Carolina, USA) and polymeric dyes selected from the group consisting of dye-polymer conjugates formed from at least one reactive dye and a polymer selected from the group consisting of polymers comprising a moiety selected from the group consisting of hydroxyl moieties, primary amine moieties, secondary amine moieties, thiol moieties, and mixtures thereof. In yet another aspect, suitable polymeric dyes include those polymeric dyes selected from the group consisting of Liquitint® Violet CT, carboxymethyl cellulose (CMC) covalently bonded to a reactive blue, reactive violet, or reactive red dye, such as CMC conjugated to CI Reactive Blue 19 sold under the trade name AZO-CM-Cellulose, product code S-ACMC by Megazyme, Wicklow, Ireland, alkoxylated triphenyl-methane polymeric colorants, alkoxylated thiophene polymeric colorants, and mixtures thereof.

[0230] Preferred hueing dyes include the brighteners found in WO 08 / 87497 A1, WO 2011 / 011799, and WO 2012 / 054835. Suitable hueing agents for use in the present disclosure may be any suitable dye disclosed in these references, such as the dyes selected from Examples 1-42 in Table 5 of WO 2011 / 011799. Other suitable dyes are disclosed in U.S. Pat. No. 8,138,222. Other suitable dyes are disclosed in WO 2009 / 069077.

[0231] Suitable dye clay complexes include those selected from the group consisting of at least one cationic / basic dye and a smectite clay, and mixtures thereof. In another embodiment, suitable dye clay complexes include those selected from the group consisting of one cationic / basic dye selected from the group consisting of CI Basic Yellow 1-108, CI Basic Orange 1-69, CI Basic Red 1-118, CI Basic Violet 1-51, CI Basic Blue 1-164, CI Basic Green 1-14, CI Basic Brown 1-23, and CI Basic Black 1-11, and a clay selected from the group consisting of montmorillonite clay, hectorite clay, saponite clay, and combinations thereof. In yet another embodiment, suitable dye clay complexes include Montmorillonite Basic Blue B7 CI 42595 Complex, Montmorillonite Basic Blue B9 CI 52015 Complex, Montmorillonite Basic Violet V3 CI 42555 Complex, Montmorillonite Basic Green G1 CI 42040 Complex, Montmorillonite Basic Red R1 CI 45160 Complex, Montmorillonite CI Basic Black 2 Complex, Hectorite Basic Blue B7 CI 42595 Complex, Hectorite Basic Blue B9 CI 52015 Complex, Hectorite Basic Violet V3 CI 42555 Complex, Hectorite Basic Green G1 CI 42040 Complex, Hectorite Basic Red R1 CI 45160 Complex, Hectorite CI Basic Black 2 Complex, Saponite Basic Blue B7 CI 42595 Complex, Saponite Basic Blue B9 CI 52015 Complex, Saponite Basic Violet V3 CI 42555 Complex, Saponite Basic Green G1 CI 42040 Complex, Saponite Basic Red R1 CI 45160 Complex, Saponite CI Basic Black 2 Complex, and mixtures thereof.

[0232] Suitable pigments include those selected from the group consisting of flavanthrone, indanthrone, chlorinated indanthrones containing 1 to 4 chlorine atoms, pyranthrone, dichloropyranthrone, monobromodichloropyranthrone, dibromodichloropyranthrone, tetrabromopyranthrone, perylene-3,4,9,10-tetracarboxylic acid diimide (the imide group may be unsubstituted or substituted by a C1-C3 alkyl group, a phenyl group, or a heterocyclic group, and the phenyl group and the heterocyclic group may further have substituents that do not impart water solubility), anthrapyrimidinecarboxylic acid amide, violanthrone, isoviolanthrone, dioxazine pigments, copper phthalocyanines which may contain up to two chlorine atoms per molecule, polychloro- or polybromochloro-copper phthalocyanines containing up to 14 bromine atoms per molecule, and mixtures thereof.

[0233] In another embodiment, suitable pigments include pigments selected from the group consisting of Ultramarine Blue (CI Pigment Blue 29), Ultramarine Violet (CI Pigment Violet 15), and mixtures thereof.

[0234] The above fabric hueing agents can be used in combination (any mixture of fabric hueing agents can be used).

[0235] <Encapsulating agent> The composition may include an encapsulating agent, hi some aspects, the encapsulating agent comprises a core and a shell having an inner surface and an outer surface, the shell encapsulating the core.

[0236] In some embodiments, the encapsulating agent comprises a core and a shell, wherein the core comprises a material selected from fragrances, whitening agents, dyes, insect repellents, silicones, waxes, flavors, vitamins, fabric softeners, skin care agents (e.g., paraffin), enzymes, antibacterial agents, bleaching agents, sensates, or mixtures thereof, and the shell comprises a material selected from polyethylene, polyamide, polyvinyl alcohol optionally containing other comonomers, polystyrene, polyisoprene, polycarbonate, polyester, polyacrylate, polyolefin, polysaccharide (e.g., alginate and / or chitosan), gelatin, shellac, epoxy resin, vinyl polymer, water-soluble inorganic material, silicone, aminoplast, or mixtures thereof. In some embodiments where the shell comprises an aminoplast, the aminoplast comprises polyurea, polyurethane, and / or polyureaurethane. The polyurea may comprise polyoxymethylene urea and / or melamine formaldehyde.

[0237] In some embodiments, the encapsulant encapsulates a core, and the core comprises a fragrance. In certain embodiments, the encapsulant comprises a shell, and the shell comprises melamine formaldehyde and / or crosslinked melamine formaldehyde. In some embodiments, the encapsulant comprises a core comprising a fragrance and a shell comprising melamine formaldehyde and / or crosslinked melamine formaldehyde.

[0238] Suitable encapsulants comprise a core material and a shell, where the shell at least partially surrounds the core material. At least 75%, or at least 85%, or even at least 90% of the encapsulants may have a breaking strength of from about 0.2 MPa to about 10 MPa, from about 0.4 MPa to about 5 MPa, from about 0.6 MPa to about 3.5 MPa, or even from about 0.7 MPa to about 3 MPa, and a benefit agent leakage of 0% to about 30%, 0% to about 20%, or even 0% to about 5%.

[0239] In some embodiments, at least 75%, 85%, or even 90% of the encapsulating agent may have a particle size of about 1 micrometer to about 80 micrometers, about 5 micrometers to 60 micrometers, about 10 micrometers to about 50 micrometers, or even about 15 micrometers to about 40 micrometers.

[0240] In some embodiments, at least 75%, 85%, or even 90% of the capsules may have a particle wall thickness of about 30 nm to about 250 nm, about 80 nm to about 180 nm, or even about 100 nm to about 160 nm.

[0241] In some embodiments, the encapsulant core comprises a material selected from flavor raw materials, and / or optionally vegetable oils, including straight and / or blended vegetable oils, including castor oil, coconut oil, cottonseed oil, grape oil, rapeseed oil, soybean oil, corn oil, palm oil, linseed oil, safflower oil, olive oil, peanut oil, coconut oil, palm kernel oil, castor oil, lemon oil, and mixtures thereof; esters of vegetable oils (esters include dibutyl adipate, dibutyl phthalate, butyl benzyl adipate, benzyl octyl adipate, butyl benzoate, butyl octyl benzoate, butyl ... straight or branched chain hydrocarbons, including straight or branched chain hydrocarbons having a boiling point above about 80°C; petroleum spirits, including partially hydrogenated terphenyls, dialkyl phthalates, alkyl diphenyls, including monoisopropyl biphenyls, alkylated naphthalenes, including dipropyl naphthalene, kerosene, mineral oil, and mixtures thereof; aromatic solvents, including benzene, toluene, and mixtures thereof; silicone oils; or combinations thereof.

[0242] In some embodiments, the capsule body wall comprises a suitable resin, such as a reaction product of an aldehyde and an amine. Suitable aldehydes include formaldehyde. Suitable amines include melamine, urea, benzoguanamine, glycoluril, or mixtures thereof. Suitable melamines include methylolmelamine, methylated methylolmelamine, iminomelamine, and mixtures thereof. Suitable ureas include dimethylolurea, methylated dimethylolurea, urea-resorcinol, and mixtures thereof.

[0243] In some embodiments, a suitable formaldehyde scavenger may be used in conjunction with the encapsulating agent, e.g., in the capsule slurry, and / or added to the composition before, during, or after the encapsulating agent is added to the composition of the present disclosure.

[0244] Suitable capsules are disclosed in U.S. Patent Application Publication Nos. 2008 / 030598 A1 and / or 2009 / 0247449 A1. Alternatively, suitable capsules can be purchased from Appleton Papers Inc. (Appleton, Wisconsin USA).

[0245] In addition, materials for making the above encapsulants are available from Solutia Inc. (St. Louis, Missouri, USA), Cytec Industries (West Paterson, New Jersey, USA), Sigma-Aldrich (St. Louis, Missouri, USA), CP Kelco Corp. (San Diego, California, USA); BASF AG (Ludwigshafen, Germany); Rhodia Corp. (Cranbury, New Jersey, USA); Hercules Corp. (Wilmington, Delaware, USA); Agrium Inc. (Calgary, Alberta, Canada), ISP (New Jersey, USA), Akzo Nobel (Chicago, IL, USA); Stroever Shellac Bremen (Bremen, Germany); Dow Chemical Company (Midland, MI, USA); Bayer AG (Leverkusen, Germany); Sigma-Aldrich Corp. (St. Louis, Missouri, USA).

[0246] <Fragrance> Fragrances and fragrance ingredients may be used in the cleaning compositions described herein. Non-limiting examples of fragrances and fragrance ingredients include, but are not limited to, aldehydes, ketones, esters, and the like. Other examples include various natural extracts and natural essences, which may contain complex mixtures of ingredients such as orange oil, lemon oil, rose extract, lavender, musk, patchouli, balsam extract, sandalwood oil, pine oil, cedar, and the like. The final fragrance may contain a highly complex mixture of such ingredients. The final fragrance may be present at a concentration ranging from about 0.01% to about 2% by weight of the cleaning composition.

[0247] <Dye transfer inhibitor> The cleaning composition may also contain one or more materials effective in inhibiting the transfer of dyes from one fabric to another during the washing process. Generally, such dye transfer inhibitors may include polyvinylpyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrrolidone and N-vinylimidazole, manganese phthalocyanine, peroxidase, and mixtures thereof. When used, these agents may be used at a concentration of from about 0.0001% to about 10% by weight of the composition, in some instances from about 0.01% to about 5% by weight of the composition, and in other instances from about 0.05% to about 2% by weight of the composition.

[0248] <Chelating agent> The detergent or cleaning compositions described herein may also contain one or more metal ion chelating agents. Suitable molecules include copper chelating agents, iron chelating agents, and / or manganese chelating agents, and mixtures thereof. Such chelating agents can be selected from the group consisting of phosphonates, aminocarboxylates, aminophosphonates, succinates, polyfunctionally substituted aromatic chelating agents, 2-pyridinol-N-oxide compounds, hydroxamic acids, carboxymethyl inulin, and mixtures thereof. The chelating agents can be present in acid or salt form, such as alkali metal, ammonium, and substituted ammonium salts thereof, and mixtures thereof. Non-limiting examples of chelating agents for use in the present disclosure can be found in U.S. Patent Nos. 7,445,644, 7,585,376, and U.S. Patent Application Publication No. 2009 / 0176684 A1.

[0249] Aminocarboxylates useful as chelating agents include, but are not limited to, ethylenediaminetetraacetate (EDTA); N-(hydroxyethyl)ethylenediaminetriacetate (HEDTA); nitrilotriacetate (NTA); ethylenediaminetetrapropionates; triethylenetetraaminehexacetates, diethylenetriaminepentaacetic acid (DTPA); methylglycinediacetate (MGDA); glutamic acid diacetate (GLDA); ethanoldiglycine; triethylenetetraaminehexaacetic acid (TTHA); N-hydroxyethyliminodiacetic acid (HEIDA); dihydroxyethylglycine (DHEG); ethylenediaminetetrapropionic acid (EDTP) and its derivatives.

[0250] Phosphorus containing chelating agents include diethylenetriaminepenta(methylenephosphonic acid) (DTPMP CAS 15827-60-8); ethylenediaminetetra(methylenephosphonic acid) (EDTMP CAS 1429-50-1); 2-phosphonobutane 1,2,4-tricarboxylic acid (BAYHIBIT® AM); hexamethylenediaminetetra(methylenephosphonic acid) (CAS 56744-47-9); hydroxyloxyethanediphosphonic acid (HEDP CAS 2809-21-4); hydroxyloxyethanedimethylenephosphonic acid; 2-phosphono-1,2,4-butanetricarboxylic acid (CAS 37971-36-1); 2-hydroxy-2-phosphono-acetic acid (CAS 23783-26-8); aminotri(methylenephosphonic acid) (ATMP CAS 6419-19-8); P,P'-(1,2-ethanediyl)bis-phosphonane (CAS 6145-31-9); P,P'-methylenebis-phosphonane (CAS 1984-15-2); triethylenediaminetetra(methylenephosphonane) (CAS 28444-52-2); P-(1-hydroxy-1-methylethyl)-phosphonane (CAS 4167-10-6); bis(hexamethylenetriaminepenta(methylenephosphonane)) (CAS 34690-00-1); N2,N2,N6,N6-tetrakis(phosphonomethyl)-lysine (CAS 194933-56-7, CAS 172780-03-9), salts thereof, and mixtures thereof. Preferably, these aminophosphonic acids do not contain alkyl or alkenyl groups with more than about 6 carbon atoms.

[0251] A biodegradable chelating agent that can also be used in the present disclosure is ethylenediaminedisuccinic acid ("EDDS"). In some instances (although certainly not limited to this specific example), the [S,S] isomer, as described in U.S. Pat. No. 4,704,233, can also be used. In other instances, the trisodium salt of EDDA can be used, although other forms, such as the magnesium salt, can also be useful. Polymeric chelating agents, such as BASF's Trilon P®, can also be useful.

[0252] Polyfunctionally substituted aromatic chelating agents may also be used in cleaning compositions. See U.S. Pat. No. 3,812,044 (Connor et al., issued May 21, 1974). A preferred compound in the acid form of this type is a dihydroxydisulfobenzene, such as 1,2-dihydroxy-3,5-disulfobenzene, also known as tiron. Other sulfonated catechols may also be used. In addition to disulfonic acids, the term "tiron" may also include mono- or disulfonic acid salts of this acid, such as disodium sulfonate, which share the same core molecular structure as the disulfonic acid.

[0253] The detergent or cleaning composition of the present disclosure may contain a substituted or unsubstituted 2-pyridinol-N-oxide compound or a salt thereof as a chelating agent. Tautomers of this compound, such as 1-hydroxy-2(1H)-pyridinone, are also included within the scope of the present disclosure as chelating agents. In some embodiments, the detergent or cleaning composition comprises a 2-pyridinol-N-oxide compound selected from the group consisting of 2-hydroxypyridine-1-oxide; 3-pyridinecarboxylic acid, 2-hydroxy-1-oxide; 6-hydroxy-3-pyridinecarboxylic acid, 1-oxide; 2-hydroxy-4-pyridinecarboxylic acid, 1-oxide; 2-pyridinecarboxylic acid, 6-hydroxy-1-oxide; 6-hydroxy-3-pyridine sulfonic acid, 1-oxide; and mixtures thereof.In some embodiments, the detergent or cleaning composition may comprise 1-hydroxy-2(1H)-pyridinone (CAS 822-89-9); 1,6-dihydro-1-hydroxy-6-oxo-3-pyridinecarboxylic acid (CAS 677763-18-7); 1,2-dihydro-1-hydroxy-2-oxo-4-pyridinecarboxylic acid (CAS 119736-22-0); 1,6-dihydro-1-hydroxy-6-oxo-2-pyridinecarboxylic acid (CAS 94781-89-2); 1-hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2(1H)-pyridinone (CAS 50650-76-5); 6-(cyclohexylmethyl)-1-hydroxy-4-methyl-2(1H)-pyridinone (CAS 29342-10-7; 1-Hydroxy-4,6-dimethyl-2(1H)-pyridinone (CAS 29342-02-7); 1-Hydroxy-4-methyl-6-(2,4,4-trimethylpentyl)-2-pyridone monoethanolamine (CAS 68890-66-4); 1-Hydroxy-6-(octyloxy)-2(1H)-pyridinone (CAS 162912-64-3); 1-Hydroxy-4-methyl-6-cyclohexyl-2-pyridinone ethanolamine salt (CAS 41621-49-2); 1-Hydroxy-4-methyl-6-cyclohexyl-2-pyridinone (CAS 29342-05-0); 6-Ethoxy-1,2-dihydro-1-hydroxy-2-oxo-4-pyridinecarboxylic acid, methyl ester (CAS 36979-78-9); 1-hydroxy-5-nitro-2(1H)-pyridinone (CAS 45939-70-6); and mixtures thereof. These compounds are commercially available from, for example, Sigma-Aldrich (St. Louis, MO), Princeton Building Blocks (Monmouth Junction, NJ), 3B Scientific Corporation (Libertyville, IL), SynFine Research (Richmond Hill, ON), Ryan Scientific, Inc. (Mt. Pleasant, SC), and / or Aces Pharma (Branford, CT).

[0254] Hydroxamic acids are a class of chemical compounds in which a hydroxylamine is inserted into a carboxylic acid and are used as chelating agents. The general structure of a hydroxamic acid is:

[0255] [ka]

[0256] Preferred hydroxamates are R 30 is a C4-C14 alkyl, preferably normal alkyl, most preferably their saturated salts, and mixtures thereof. When a C8 material is used, it is called octylhydroxamic acid.

[0257] Suitable chelating agents for use in the present disclosure are commercially available DEQUEST series and chelating agents from Monsanto, Akzo-Nobel, DuPont, Dow, Trilon® series from BASF and Nalco.

[0258] The chelating agent may be present in the detergent or cleaning compositions of the present disclosure from about 0.005% to about 15%, from about 0.01% to about 5%, from about 0.1% to about 3.0%, from about 0.2% to about 0.7%, or from about 0.3% to about 0.6% by weight of the detergent or cleaning compositions of the present disclosure.

[0259] <Foam suppressor> The detergent or cleaning compositions described herein may incorporate compounds that reduce or inhibit suds formation. Suds suppression can be particularly important in so-called "high concentration wash processes," as described in U.S. Patent Nos. 4,489,455 and 4,489,574, and in front-loading washing machines.

[0260] A wide variety of materials may be used as suds suppressors, and suds suppressors are well known to those skilled in the art. See, for example, Kirk Othmer Encyclopedia of Chemical Technology, Third Edition, Volume 7, pages 430-447 (John Wiley & Sons, Inc., 1979). Examples of suds suppressors include monocarboxylic fatty acids and soluble salts thereof, high molecular weight hydrocarbons such as paraffin, fatty acid esters (e.g., fatty acid triglycerides), fatty acid esters of monohydric alcohols, aliphatic C18-C40 ketones (e.g., stearone), N-alkylated aminotriazines, waxy hydrocarbons preferably having a melting point below about 100°C, silicone suds suppressors, and secondary alcohols. Foam suppressors are described in U.S. Pat. Nos. 2,954,347, 4,265,779, 4,265,779, 3,455,839, 3,933,672, 4,652,392, 4,978,471, 4,983,316, 5,288,431, 4,639,489, 4,749,740, 4,798,679, 4,075,118, 8,492,325, European Patent Application Publication No. 89307851.9, European Patent No. 150,872, and DOS 2,124,526.

[0261] Further suitable antifoam agents are those derived from phenylpropylmethyl substituted polysiloxanes.

[0262] In one example, a laundry or cleaning composition contains a suds suppressor selected from an organo-modified silicone polymer with aryl or alkylaryl substituents in combination with a primary filler that is a silicone resin and a modified silica. The detergent or cleaning composition may contain from about 0.001% to about 4.0% of such a suds suppressor, by weight of the composition. In a further example, the detergent or cleaning composition contains a suds suppressor selected from a) a mixture of about 80 to about 92% ethylmethyl, methyl(2-phenylpropyl)siloxane, about 5 to about 14% MQ resin in octyl stearate, and about 3 to about 7% modified silica; b) a mixture of about 78 to about 92% ethylmethyl, methyl(2-phenylpropyl)siloxane, about 3 to about 10% MQ resin in octyl stearate, and about 4 to about 12% modified silica; or c) mixtures thereof (% is the weight % of the antifoam agent).

[0263] The detergent or cleaning compositions described herein may contain from 0.1% to about 10% by weight of the composition of a suds suppressor. When used as a suds suppressor, aliphatic monocarboxylic acids and their salts may be present in an amount up to about 5% by weight of the cleaning composition, and in some examples, from about 0.5% to about 3% by weight of the detergent or cleaning composition. Silicone suds suppressors may be used in an amount up to about 2.0% by weight of the cleaning composition, although higher amounts can be used. Monostearyl phosphate suds suppressors may be used in an amount ranging from about 0.1% to about 2% by weight of the cleaning composition. Hydrocarbon suds suppressors may be used in an amount ranging from about 0.01% to about 5.0% by weight of the cleaning composition, although higher amounts can be used. Alcohol suds suppressors may be used at concentrations ranging from about 0.2% to about 3% by weight of the detergent or cleaning composition.

[0264] <Unit dose product form using water-soluble film> The composition of the present disclosure may also be encapsulated in a unit dose product form. That is, the pouch made of water-soluble film has either a single compartment or multiple compartments. The preferred film material is preferably a polymer material. The film material can be obtained, for example, by casting, blow molding, extrusion, or blow-extrusion of a polymer material, as is known in the art.

[0265] Preferred polymers, copolymers or derivatives thereof suitable for use as pouch materials are selected from polyvinyl alcohol, polyvinylpyrrolidone, polyalkylene oxides, acrylamide, acrylic acid, cellulose, cellulose ethers, cellulose esters, cellulose amides, polyvinyl acetate, polycarboxylic acids and salts, polyamino acids or peptides, polyamides, polyacrylamides, maleic / acrylic acid copolymers, polysaccharides including starch and gelatin, natural gums such as xanthan and carrageenan. More preferred polymers are selected from polyacrylates and water-soluble acrylate copolymers, methylcellulose, sodium carboxymethylcellulose, dextrin, ethylcellulose, hydroxyethylcellulose, hydroxypropylmethylcellulose, maltodextrin, polymethacrylates, and most preferably polyvinyl alcohol, polyvinyl alcohol copolymers and hydroxypropylmethylcellulose (HPMC), and combinations thereof. Preferably, the concentration of the polymer in the pouch material, e.g., the concentration of the PVA polymer, is at least 60%. The polymer may have any weight-average molecular weight, preferably about 1,000 to 1,000,000, more preferably about 10,000 to 300,000, and even more preferably about 20,000 to 150,000. Polymer mixtures can also be used as pouch materials.

[0266] Of course, different film materials and / or different thicknesses may also be selected to create the compartments of the present disclosure. An advantage of selecting different films is that the resulting compartments may exhibit different solubility, i.e., release, profiles.

[0267] The most preferred film materials are the PVA films known as MonoSol Reference Nos. M8630, M8900, H8779 (described in Applicant's co-pending application Reference Nos. 44528 and 11599), and those described in U.S. Pat. Nos. 6,166,117 and 6,787,512, and PVA films having comparable solubility and deformation properties.

[0268] The film material of the present disclosure may also contain one or more additive components. For example, the addition of plasticizers such as glycerol, ethylene glycol, diethylene glycol, propylene glycol, sorbitol, and mixtures thereof may be beneficial. Other additives include functional detergent additives, such as organic polymer dispersants, delivered to the wash water.

[0269] <Foaming promoter> If high sudsing is desired, suds boosters such as C10-C16 alkanolamides may be incorporated into the cleaning composition at concentrations ranging from about 1% to about 10% by weight of the cleaning composition. Some examples include C10-C14 monoethanol and diethanolamides. If desired, water-soluble magnesium and / or calcium salts, such as MgCl2, MgSO4, CaCl2, and CaSO4, may be added at concentrations of about 0.1% to about 2% by weight of the cleaning composition to provide additional suds and enhance grease removal.

[0270] <Conditioning agent> The compositions of the present disclosure may contain a high-melting-point fatty compound. High-melting-point fatty compounds useful in the present disclosure have a melting point of 25°C or higher and are selected from the group consisting of fatty alcohols, fatty acids, fatty alcohol derivatives, fatty acid derivatives, and mixtures thereof. Low-melting-point fatty compounds are not included in this section. Non-limiting examples of high-melting-point fatty compounds can be found in the International Cosmetic Ingredient Dictionary, Fifth Edition, 1993, and the CTFA Cosmetic Ingredient Handbook, Second Edition, 1992.

[0271] The high melting point fatty compound is included in the composition at a concentration of about 0.1% by weight to about 40% by weight, preferably about 1% by weight to about 30% by weight, more preferably about 1.5% by weight to about 16% by weight, and more preferably about 1.5% by weight to about 8% by weight, in consideration of providing improved conditioning effects, such as a smooth feeling during application to wet hair and a soft and moist feeling on dry hair.

[0272] The compositions of the present disclosure may contain a cationic polymer. The concentration of the cationic polymer in the composition typically ranges from about 0.05% to about 3%, from about 0.075% to about 2.0%, and from about 0.1% to about 1.0%. Suitable cationic polymers will have a cationic charge density of at least about 0.5 meq / gm, in another embodiment at least about 0.9 meq / gm, in another embodiment at least about 1.2 meq / gm, and in yet another embodiment at least about 1.5 meq / gm, but also in one embodiment less than about 7 meq / gm, and in another embodiment less than about 5 meq / gm, at a pH of from about pH 3 to about pH 9, in one embodiment from about pH 4 to about pH 8, at the intended use of the composition. In this disclosure, the "cationic charge density" of a polymer refers to the ratio of the number of positive charges on the polymer to the molecular weight of the polymer. The average molecular weight of such suitable cationic polymers is generally from about 10,000 to 10,000,000, in one embodiment from about 50,000 to about 5,000,000, and in another embodiment from about 100,000 to about 3,000,000.

[0273] Cationic polymers suitable for use in the compositions of the present disclosure contain cationic nitrogen-containing moieties, such as quaternary ammonium, or cationic protonated amino moieties. Any anionic counterion can be used in conjunction with the cationic polymer, provided that the polymer remains dissolved in water, the composition, or the coacervate phase of the composition, and the counterion is physically and chemically compatible with the essential components of the compositions of the present disclosure or does not otherwise unduly impair product performance, stability, or aesthetics. Non-limiting examples of such counterions include halides (e.g., chloride, fluoride, bromide, iodide), sulfate, and methylsulfate.

[0274] Non-limiting examples of such polymers are described in the CTFA Cosmetic Ingredient Dictionary, 3rd edition, edited by Estrin, Crosley, and Haynes, (The Cosmetic, Toiletry, and Fragrance Association, Inc., Washington, DC (1982)).

[0275] Other cationic polymers suitable for use in the composition include polysaccharide polymers, cationic guar gum derivatives, quaternary nitrogen-containing cellulose ethers, synthetic polymers, copolymers of etherified cellulose, guar, and starch. When used, the cationic polymers in the present disclosure are either soluble in the composition of the present disclosure or soluble in a complex coacervate phase formed in the composition of the present disclosure by the above-mentioned cationic polymer and anionic, amphoteric, and / or zwitterionic surfactant components. Complex coacervates of cationic polymers can also be formed with other charged substances in the composition of the present disclosure.

[0276] Suitable cationic polymers are described in U.S. Patent Nos. 3,962,418, 3,958,581, and U.S. Patent Application Publication No. 2007 / 0207109A1.

[0277] The compositions of the present disclosure may include a nonionic polymer as a conditioning agent. Polyalkylene glycols having a molecular weight greater than about 1000 are useful in the present invention.

[0278] [ka] Useful are those having the formula 31is selected from the group consisting of H, methyl, and mixtures thereof. Conditioning agents, specifically silicones, may be included in the compositions of the present disclosure. Conditioning agents useful in the compositions of the present disclosure typically comprise water-insoluble, water-dispersible, non-volatile liquids that form emulsified liquid particles. Conditioning agents suitable for use in the compositions of the present disclosure are generally those characterized by silicones (e.g., silicone oils, cationic silicones, silicone gums, high refractive index silicones, and silicone resins), organic conditioning oils (e.g., hydrocarbon oils, polyolefins, and fatty acid esters), or combinations thereof, or conditioning agents that otherwise form liquid dispersed particles in the aqueous surfactant matrix described herein. Such conditioning agents should be physically and chemically compatible with the essential components of the composition and should not otherwise unduly impair product stability, aesthetics, or performance.

[0279] The concentration of conditioning agent in the composition should be sufficient to provide the desired conditioning benefit, and such concentration may vary depending on the conditioning agent, the desired conditioning performance, the average particle size of the conditioning agent particles, the type and concentration of other ingredients, and other similar factors.

[0280] The concentration of the silicone conditioning agent typically ranges from about 0.01% to about 10%. Non-limiting examples of suitable silicone conditioning agents, and optional suspending agents for silicones, are described in U.S. Reissue Patent No. 34,584, U.S. Patent Nos. 5,104,646, 5,106,609, 4,152,416, 2,826,551, 3,964,500, 4,364,837, 6,607,717, 6,482,969, 5,807,956, 5,981, and the like. Nos. 6,681, 6,207,782, 7,465,439, 7,041,767, 7,217,777, U.S. Patent Application Publication Nos. 2007 / 0286837(A1), 2005 / 0048549(A1), 2007 / 0041929(A1), British Patent No. 849,433, German Patent No. 10036533 (all of which are incorporated herein by reference), "Chemistry and Technology of Silicones" (New York: Academic Press (1968)), General Electric Silicone Rubber Product Data Sheets SE 30, SE 33, SE 54, and SE 76, "Silicon Compounds" (Petrarch Systems, Inc. (1984)), and "Encyclopedia of Polymer Science and Engineering" (vol. 15, 2nd ed., pp. 204-308, John Wiley & Sons, Inc. (1989)).

[0281] The compositions of the present disclosure may also contain from about 0.05% to about 3% of at least one organic conditioning oil as a conditioning agent, either alone or in combination with other conditioning agents, such as silicones (described herein). Suitable conditioning oils include hydrocarbon oils, polyolefins, and fatty acid esters. Conditioning agents described in U.S. Patent Nos. 5,674,478 and 5,750,122 to Procter & Gamble Company are also suitable for use in the compositions described herein. Also suitable for use in the present disclosure are conditioning agents described in U.S. Patent Nos. 4,529,586, 4,507,280, 4,663,158, 4,197,865, 4,217,914, 4,381,919, and 4,422,853.

[0282] <Hygiene and deodorization> The compositions of the present disclosure also contain zinc ricinoleate, thymol, quaternary ammonium salts such as Bardac®, polyethyleneimine (such as Lupasol® from BASF) and its zinc complexes, silver and silver compounds, particularly Ag + or may include one or more of those designed to slowly release the nanosilver dispersion.

[0283] <Probiotics> The composition may include probiotics as described in WO 2009 / 043709.

[0284] <Fillers and carriers> Fillers and carriers may be used in the cleaning compositions described in this disclosure. As used in this disclosure, the terms "filler" and "carrier" have the same meaning and can be used interchangeably.

[0285] Liquid cleaning compositions, and other forms of cleaning compositions containing liquid components (such as liquid-containing unit dose cleaning compositions), may contain water and other solvents as fillers or carriers. Suitable solvents also include lipophilic fluids, including siloxanes, other silicones, hydrocarbons, glycol ethers, glycerin derivatives such as glycerin ethers, perfluorinated amines, perfluorinated and hydrofluoroether solvents, low volatility non-organic solvents, diol solvents, and mixtures thereof.

[0286] Low molecular weight primary or secondary alcohols, such as methanol, ethanol, propanol, and isopropanol, are suitable. In some instances, monohydric alcohols may be used to solubilize surfactants, and polyols, such as those containing 2 to about 6 carbon atoms and 2 to about 6 hydroxy groups (e.g., 1,3-propanediol, ethylene glycol, glycerin, and 1,2-propanediol), may also be used. Amine-containing solvents, such as monoethanolamine, diethanolamine, and triethanolamine, may also be used.

[0287] Detergent cleaning compositions may contain from about 5% to about 90%, and in some examples from about 10% to about 50%, by weight of the composition, of such carriers. For compact or supercompact heavy-duty liquid or other forms of cleaning compositions, the use of water may be less than about 40%, or less than about 20%, or less than about 5%, or less than about 4%, or less than about 3%, or less than about 2% free water by weight of the composition, or may be substantially free of free water (i.e., anhydrous).

[0288] For powder or bar cleaning compositions, or forms containing solid or powder components (e.g., powder-containing unit dose cleaning compositions), suitable fillers include, but are not limited to, sodium sulfate, sodium chloride, mud, or other inert solid components. Fillers may also include biomass or bleached biomass. Fillers in granules, bars, or other solid cleaning compositions may comprise less than about 80%, and in some instances less than 50%, by weight of the cleaning composition. Compact or supercompact powder or solid cleaning compositions may contain less than about 40%, less than about 20%, or less than about 10% fillers by weight of the cleaning composition.

[0289] For compact or supercompact liquid or powder cleaning compositions, or any other form, the concentration of liquid or solid filler in the product may be reduced, resulting in the same amount of active chemical delivered to the cleaning liquor compared to a non-compacted cleaning composition, or in some instances, the cleaning composition may be more efficient, resulting in a lower amount of active chemical delivered compared to a non-compacted composition. For example, the cleaning liquor may be formed by contacting the cleaning composition with water in an amount such that the concentration of the cleaning composition in the cleaning liquor is greater than 0 g / L to about 6 g / L. In some instances, the concentration may be from about 0.5 g / L to about 5 g / L, or from about 3.0 g / L, or from about 2.5 g / L, or from about 2.0 g / L, or from about 1.5 g / L, or from about 0 g / L to about 1.0 g / L, or from about 0 g / L to about 0.5 g / L. These dosage amounts are not intended to be limiting, and it will be apparent to one skilled in the art that other dosage amounts may also be used.

[0290] <Buffer system> The detergent or cleaning compositions described herein may be formulated so that, when used in aqueous cleaning operations, the wash water has a pH of about 7.0 to about 12, and in some examples, about 7.0 to 11. Techniques for adjusting pH at recommended usage levels include the use of buffers, alkalis, acids, and the like, and are well known to those skilled in the art. These techniques include, but are not limited to, the use of sodium carbonate, citric acid or sodium citrate, lactic acid or lactate salts, monoethanolamine or other amines, boric acid or borate salts, and other pH-adjusting compounds known in the art.

[0291] The detergent or cleaning compositions of the present disclosure may include a dynamic in-wash pH profile using waxed citric acid along with other pH adjusters to provide: (i) a wash liquor pH greater than 10 after about 3 minutes of contact with water, (ii) a wash liquor pH less than 9.5 after about 10 minutes of contact with water, (iii) a wash liquor pH less than 9.0 after about 20 minutes of contact with water, and (iv) optionally, an equilibrium pH of the wash liquor ranging from about 7.0 to about 8.5.

[0292] <Catalytic metal complex> The detergent or cleaning composition may contain a catalytic metal complex. One type of metal-containing bleach catalyst is a catalyst system containing a transition metal cation with a defined bleach catalytic activity, such as a cation of copper, iron, titanium, ruthenium, tungsten, molybdenum, or manganese, an auxiliary metal cation with little or no bleach catalytic activity, such as a cation of zinc or aluminum, and a sequestrate with a defined stability constant for the catalytic metal and the auxiliary metal cation, particularly ethylenediaminetetraacetic acid, ethylenediaminetetra(methylenephosphonic acid), and their water-soluble salts. Such catalysts are disclosed in U.S. Pat. No. 4,430,243. If desired, the compositions described herein can be catalyzed by manganese compounds. Such compounds and levels of use are well known in the art and include, for example, the manganese-based catalysts disclosed in U.S. Patent No. 5,576,282. Cobalt bleach catalysts useful in the present disclosure are known and are described, for example, in U.S. Patent Nos. 5,597,936 and 5,595,967. Such cobalt catalysts are readily prepared by known procedures, such as those taught in U.S. Patent Nos. 5,597,936 and 5,595,967. The compositions described herein may also suitably include transition metal complexes with ligands such as bispidone (WO 05 / 042532 A1) and / or transition metal complexes of macropolycyclic rigid ligands (abbreviated "MRLs"). The compositions and processes described herein can be tailored to provide active MRL species in aqueous wash media on the order of at least parts per billion, providing from about 0.005 ppm to about 25 ppm, from about 0.05 ppm to about 10 ppm, or even from about 0.1 ppm to about 5 ppm MRLs in wash solutions. Suitable transition metals in transition metal bleach catalysts include, for example, manganese, iron, and chromium. Suitable MRLs include 5,12-diethyl-1,5,8,12-tetraazabicyclo[6.6.2]hexadecane. Suitable transition metal MRLs are readily prepared by known procedures, such as those taught in WO 00 / 32601 and US Pat. No. 6,225,464.

[0293] <Other supplementary ingredients> The detergent or cleaning compositions described herein may contain other active ingredients, carriers, hydrotropes, processing aids, dyes or pigments, solvents for liquid formulations, and solid or other liquid fillers, erythrosine, colloidal silica, waxes, probiotics, surfactin, aminocellulose polymers, zinc ricinoleate, perfume microcapsules, rhamnolipids, sophorolipids, glycopeptides, methyl ester sulfonates, methyl ester ethoxylates, sulfonated estolides, degradable surfactants, biopolymers, silicones, modified silicones, aminosilicones, deposition aids, locust bean gum, cationic hydroxyethyl cellulose polymers, cationic guar, hydrotropes (particularly cumene sulfonates, toluene sulfonates, xylene sulfonates, and naphthalene salts), and the like. A wide variety of other ingredients may be used, such as antioxidants, BHT, PVA particle encapsulated dyes or fragrances, pearlizing agents, foaming agents, color change systems, silicone polyurethanes, opacifiers, tablet disintegrants, biomass fillers, fast-drying silicones, glycol distearate, hydroxyethyl cellulose polymers, hydrophobically modified cellulose polymers or hydroxyethyl cellulose polymers, starch fragrance encapsulants, emulsified oils, bisphenol antioxidants, microfibrous cellulose structure couples, fragrance precursors, styrene / acrylate polymers, triazines, soaps, superoxide dismutase, benzophenone protease inhibitors, functionalized TiO, dibutyl phosphate, silica fragrance capsules, and other adjunct ingredients, silicates (e.g., sodium silicate, potassium silicate), choline oxidase, pectate lyase, mica, titanium dioxide coated mica, bismuth oxychloride, and other active agents.

[0294] The detergent or cleaning compositions described herein may also contain vitamins and amino acids, such as water-soluble vitamins and their derivatives, water-soluble amino acids and their salts and / or derivatives, water-insoluble amino acid viscosity modifiers, dyes, non-volatile solvents or diluents (water-soluble and water-insoluble), pearlizing aids, foam boosters, additional surfactants or non-ionic co-surfactants, pediculicides, pH adjusters, fragrances, preservatives, chelating agents, proteins, skin active agents, sunscreens, UV absorbers, vitamins, niacinamide, caffeine, and minoxidil.

[0295] The detergent or cleaning compositions described herein may also contain pigment materials such as nitroso, monoazo, disazo, carotenoid, triphenylmethane, triarylmethane, xanthene, quinoline, oxazine, azine, anthraquinone, indigoid, thioindigoid, quinacridone, phthalocyanine, botanical, including water-soluble components such as those with CI names, and natural colors. The cleaning compositions of the present disclosure may also contain antimicrobial agents.

[0296] <Process for making detergent or cleaning composition> The detergent or cleaning compositions of the present disclosure can be formulated in any suitable form and prepared by any method selected by the formulator, non-limiting examples of which include U.S. Pat. No. 4,990,280, U.S. Patent Application Publication Nos. 20030087791A1, 20030087790A1, 20050003983A1, 20040048764A1, U.S. Pat. No. 4,762,626 36, 6,291,412, U.S. Patent Application Publication No. 20050227891A1, European Patent Application Publication No. 1070115A2, U.S. Patent Nos. 5,879,584, 5,691,297, 5,574,005, 5,569,645, 5,565,422, 5,516,448, 5,489,392, and 5,486,303.

[0297] <Method of using detergent or cleaning composition> The present disclosure includes methods of using the above-described detergent or cleaning compositions to clean soiled materials. As will be appreciated by those skilled in the art, the detergent or cleaning compositions of the present disclosure are suitable for use in laundry pre-treatment applications, laundry cleaning applications, and home care applications.

[0298] Such methods include, but are not limited to, contacting a detergent or cleaning composition, either neat or diluted in a wash liquor, with at least a portion of the soiled material, and then optionally rinsing the soiled material, which may be subjected to a washing step prior to the optional rinsing step.

[0299] For use in laundry pretreatment applications, the method may comprise contacting soiled fabrics with a detergent or cleaning composition described herein. After pretreatment, the soiled fabrics may be laundered in a washing machine or otherwise rinsed.

[0300] A machine laundry method may include treating soiled laundry with an aqueous wash solution in a washing machine having an effective amount of the machine laundry cleaning composition of the present disclosure dissolved or dispersed therein. An "effective amount" of cleaning composition means about 20 g to about 300 g of product dissolved or dispersed in a volume of about 5 L to about 65 L of wash solution. The water temperature may range from about 5°C to about 10°C. The ratio of water to soiled material (e.g., fabric) may be from about 1:1 to about 30:1. The compositions may be used at concentrations of from about 500 ppm to about 15,000 ppm in solution. In the context of fabric laundering compositions, the use concentration may also vary depending on the type and severity of soils and stains, as well as the temperature of the wash water, the amount of wash water, and the type of washing machine (e.g., top-loading, front-loading, top-loading, vertical-axis Japanese-type automatic washing machine).

[0301] The cleaning compositions described herein may be used to launder fabrics at low wash temperatures. These methods of laundering fabrics include delivering the laundry cleaning composition to water to form a wash liquor and adding fabrics to be laundered to the wash liquor, the wash liquor having a temperature of about 0° C. to about 20° C., or about 0° C. to about 15° C., or about 0° C. to about 9° C. The fabrics may be contacted with water before, after, or simultaneously with contacting the laundry detergent composition with water.

[0302] Another method involves contacting a nonwoven substrate impregnated with an embodiment of the detergent or cleaning composition with the soiled material. As used in this disclosure, "nonwoven substrate" can include any conventionally shaped nonwoven sheet or web having suitable basis weight, caliper (thickness), absorbency, and strength characteristics. Non-limiting examples of suitable commercially available nonwoven substrates include those sold under the tradename SONTARA® by DuPont and POLYWEB® by James River Corp.

[0303] This includes hand washing / soaking methods and hand washing in combination with semi-automatic washing machines.

[0304] <Water treatment agent> The polyalkylene oxide-containing compound of the present disclosure can be used in applications other than detergent or cleaning compositions, such as water treatment agents, which may contain other additives such as polymerized phosphates, phosphonates, anticorrosives, slime control agents, and chelating agents, as needed.

[0305] The water treatment agent is useful for preventing scale formation in cooling water circulation systems, boiler water circulation systems, seawater desalination plants, pulp digesters, black liquor concentration pots, etc. In addition, the water treatment agent may contain any appropriate water-soluble polymer as long as it does not affect the performance and effect.

[0306] <Textile treatment agent> The detergent or cleaning composition of the present disclosure can be used in a textile treatment agent, which contains at least one selected from the group consisting of a dye, a peroxide, and a surfactant, and the polymer (or polymer composition) of the present disclosure.

[0307] The content of the compound of the present disclosure in the fiber treatment agent is preferably 1 to 100 wt %, more preferably 5 to 100 wt %, based on the total weight of the fiber treatment agent. The fiber treatment agent may also contain any appropriate water-soluble compound within a range that does not affect the performance and effects of the fiber treatment agent.

[0308] The following is an example of a fiber treatment formulation that is closer to the embodiment. This fiber treatment can be used in the scouring, dyeing, bleaching, and soaping processes of fiber treatment. The dyes, peroxides, and surfactants used in fiber treatments include those typically used in fiber treatments.

[0309] The compounding ratio of the compound of the present disclosure to at least one selected from the group consisting of dyes, peroxides, and surfactants is preferably 0.1 to 100 parts by weight of at least one selected from the group consisting of dyes, peroxides, and surfactants, calculated as the pure content of the fiber treatment agent, for example, in order to improve the whiteness, color unevenness, and dye waxiness of fibers.

[0310] The fiber treatment agent can be used with any suitable fiber, including, for example, cellulosic fibers such as cotton and hemp, chemical fibers such as nylon and polyester, animal fibers such as wool and silk, semi-synthetic fibers such as rayon, and woven fabrics and blends thereof.

[0311] When the fiber treatment agent is used in a scouring process, it is preferable to combine the compound of the present disclosure with an alkaline agent and a surfactant.When the fiber treatment agent is used in a bleaching process, it is preferable to combine the compound of the present disclosure with a peroxide and a silicic acid-based agent such as sodium silicate as a decomposition inhibitor for alkaline bleaching agents.

[0312] <Inorganic pigment dispersant> The compound of the present disclosure can be used in an inorganic pigment dispersant, which may contain other additives, such as condensed phosphoric acid and its salts, phosphonic acid and its salts, and polyvinyl alcohol, as needed.

[0313] The content of the compound of the present disclosure in the inorganic pigment dispersant is preferably 5 to 100 wt % based on the total weight of the inorganic pigment dispersant, and may contain any appropriate water-soluble compound within a range that does not affect the performance and effects.

[0314] The inorganic pigment dispersant can exhibit excellent performance as a dispersant for inorganic pigments such as heavy or light calcium carbonate and clay used in paper coating. For example, by adding a small amount of the inorganic pigment dispersant to an inorganic pigment and dispersing the pigment in water, a high-concentration inorganic pigment slurry such as a high-concentration calcium carbonate slurry can be produced, which has low viscosity and high fluidity and exhibits good stability of these properties over time.

[0315] When the inorganic pigment dispersant is used as a dispersant for an inorganic pigment, the amount of the inorganic pigment dispersant used is preferably 0.05 to 2.0 parts by weight per 100 parts by weight of the inorganic pigment. When the amount of the inorganic pigment dispersant used is within the above range, a sufficient dispersing effect can be obtained, and an effect commensurate with the amount added can be obtained, which can be economically advantageous. [Example]

[0316] <Molecular weight measurement conditions> The molecular weights described in the Production Examples were measured by gel permeation chromatography (GPC) under the following conditions: Equipment: Tosoh HLC-8320GPC Detector: RI Column: Tosoh TSKgel α-2500 + TSKgel α-M + TSK guardcolumn α Column temperature: 40℃ Flow rate: 0.8ml / min Calibration curve: GL Sciences Polyethylene Glycol, Polyethylene Oxide Eluent: 0.2 M sodium nitrate, 0.5 M aqueous acetic acid solution / acetonitrile = 50 / 50 vol%

[0317] <Production Example 1> A glass reactor equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 0.90 g of polyethyleneimine (Nippon Shokubai, average molecular weight 600) and 20.6 g of methoxypolyethylene glycol #1000 acrylate (Shin-Nakamura Chemical), and the atmosphere inside the reactor was replaced with nitrogen. The temperature was then raised to 60°C with stirring, and the reaction was continued for 40 hours. After completion of the reaction, liquid chromatography was used to confirm that all of the methoxypolyethylene glycol #1000 acrylate had been consumed, yielding a polyethyleneimine-methoxypolyethylene glycol #1000 acrylate adduct (polymer (1)) as a polyalkylene oxide-containing compound. The number-average molecular weight of polymer (1) measured by GPC was 8930.

[0318] <Production Example 2> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 0.72 g of polyethyleneimine (Nippon Shokubai, average molecular weight 600) and 13.39 g of methoxypolyethylene glycol #1000 acrylate (Shin-Nakamura Chemical), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 60°C with stirring, and the reaction was continued for 20 hours. After completion of the reaction, liquid chromatography was used to confirm that all of the methoxypolyethylene glycol #1000 acrylate had been consumed, yielding a polyethyleneimine-methoxypolyethylene glycol #1000 acrylate adduct (polymer (2)) as a polyalkylene oxide-containing compound.

[0319] <Production Example 3> A glass reactor equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 1.5 g of polyethyleneimine (Nippon Shokubai, average molecular weight 600) and 19.17 g of methoxypolyethylene glycol #1000 acrylate (Shin-Nakamura Chemical), and the atmosphere inside the reactor was replaced with nitrogen. The temperature was then raised to 60°C with stirring, and the reaction was continued for 20 hours. After completion of the reaction, liquid chromatography was used to confirm that all of the methoxypolyethylene glycol #1000 acrylate had been consumed, yielding a polyethyleneimine-methoxypolyethylene glycol #1000 acrylate adduct (polymer (3)) as a polyalkylene oxide-containing compound. The number-average molecular weight of polymer (3) measured by GPC was 8630.

[0320] <Production Example 4> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 55.09 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600), and the atmosphere inside the reaction vessel was replaced with nitrogen at 60°C while stirring. Subsequently, 97.90 g of ε-caprolactone (manufactured by Tokyo Chemical Industry Co., Ltd.) was slowly added dropwise from the dropping funnel to the reaction vessel over 60 minutes while stirring. After completion of the addition, the reaction was continued for 28 hours. The reaction solution was then heated to 80°C and the reaction was continued for 12 hours. After completion of the reaction, it was confirmed by liquid chromatography that all ε-caprolactone had been consumed, yielding a polyethyleneimine-ε-caprolactone condensate. Next, 98.3 g of the resulting polyethyleneimine-ε-caprolactone condensate and 2.25 g of potassium hydroxide (Fujifilm Wako Pure Chemical Industries, Ltd.) were charged into an autoclave and heated to 120 °C. The autoclave was purged with nitrogen, and the pressure was reduced to 1.8 kPa using a vacuum pump, followed by dehydration for 1 hour. After dehydration was complete, the autoclave was adjusted to 0.3 MPa with nitrogen, and 181.8 g of ethylene oxide (Air Water Co., Ltd.) was slowly poured in and reacted. The reactant was removed, and 101.8 g of the reactant and 1.59 g of potassium hydroxide were charged into the autoclave again, and 198.1 g of ethylene oxide was reacted in the same manner. After the reaction was complete, the reactant was removed, and an ethylene oxide adduct of polyethyleneimine-ε-caprolactone condensate (polymer (4)) was obtained as a polyalkylene oxide-containing compound.

[0321] <Production Example 5> A glass reaction vessel equipped with a nitrogen inlet tube and a stirrer was charged with 10.0 g of ethylenediamine (Tokyo Chemical Industry Co., Ltd.) and 100 ml of methanol (Fujifilm Wako Pure Chemical Industries Co., Ltd.). The reaction vessel was then ice-cooled and placed under a nitrogen atmosphere. Under ice cooling, 94.6 g of methyl acrylate (Tokyo Chemical Industry Co., Ltd.) containing 0.01 g of methoquinone was added dropwise over 1 hour. After the addition was complete, the mixture was allowed to return to room temperature and stirred for 24 hours. The remaining methyl acrylate and methanol were removed by distillation under reduced pressure to obtain a polyamidoamine precursor. Next, 120 g of ethylenediamine and 200 ml of methanol were placed in a glass reaction vessel equipped with a nitrogen inlet tube and a stirrer. Next, polyamidoamine precursor (1) was dissolved in 20 ml of methanol and added dropwise to the reaction vessel over 30 minutes. After the dropwise addition was completed, the mixture was stirred for 3 hours. After that, the mixture was returned to room temperature and stirred for 2 to 7 days, after which the remaining methanol and ethylenediamine were distilled off under reduced pressure to obtain polyamidoamine.

[0322] <Production Example 6> Synthesis of a glycidyl ether compound having a polyethylene oxide structure A glass reaction vessel equipped with a nitrogen inlet tube and a stirrer was charged with 5.8 g of methoxypolyethylene glycol (25 mol ethylene oxide) (Nippon Shokubai Co., Ltd.) and 166 ml of tetrahydrofuran (Fujifilm Wako Pure Chemical Industries, Ltd.). The mixture was heated to 50 °C under a nitrogen atmosphere and stirred until a homogeneous solution was obtained. Next, 5.27 g of sodium hydride (Fujifilm Wako Pure Chemical Industries, Ltd.) was slurried in 5 to 10 ml of tetrahydrofuran and gradually added to the reaction vessel, followed by stirring for 30 minutes. Next, 44.3 g of epichlorohydrin (Tokyo Chemical Industry Co., Ltd.) was gradually added dropwise to the reaction vessel. The mixture was heated to 66 °C and refluxed for 5 hours, then cooled to room temperature. 2 g of water was added to quench the reaction. The tetrahydrofuran in the reaction mixture was then distilled off under reduced pressure to obtain a glycidyl ether compound having a polyethylene oxide structure (Compound (1)).

[0323] <Production Example 7> A glass reaction vessel was charged with 1.00 g of the polyamidoamine produced in Production Example 5 and 9.20 g of a glycidyl ether compound having a polyethylene oxide structure (compound (1)), and the mixture was heated to 60°C and stirred for 21 hours. After completion of the reaction, it was confirmed by liquid chromatography that the glycidyl ether compound having a polyethylene oxide structure had reacted, yielding an adduct of compound (1) to polyamidoamine (polymer (5)).

[0324] <Production Example 8> 70.0 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) was charged into a glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer, and the atmosphere inside the reaction vessel was replaced with nitrogen at 60°C while stirring. Then, 93.7 g of N-(hydroxyethyl)acrylamide (manufactured by Tokyo Chemical Industry Co., Ltd.) was slowly added dropwise from the dropping funnel to the reaction vessel over 120 minutes while stirring. After the addition was completed, the reaction was continued for 9 hours. After the reaction was completed, it was confirmed by liquid chromatography that all of the N-(hydroxyethyl)acrylamide had been consumed, yielding a polyethyleneimine-N-(hydroxyethyl)acrylamide adduct. Next, 100.9 g of the resulting polyethyleneimine-N-(hydroxyethyl)acrylamide adduct and 2.40 g of potassium hydroxide (Fujifilm Wako Pure Chemical Industries, Ltd.) were charged into an autoclave and heated to 120 °C. The autoclave was purged with nitrogen, and the pressure was reduced to 1.8 kPa using a vacuum pump, followed by dehydration for 1 hour. After dehydration was complete, the autoclave was adjusted to 0.3 MPa with nitrogen, and 199.1 g of ethylene oxide (Air Water Co., Ltd.) was slowly poured in and reacted. The reactant was removed, and 103.0 g of the reactant and 1.71 g of potassium hydroxide were charged into the autoclave again, and 203.1 g of ethylene oxide was reacted using the same procedure. After the reaction was complete, the reactant was removed, and an ethylene oxide adduct of polyethyleneimine-N-(hydroxyethyl)acrylamide adduct (polymer (6)) was obtained as a polyalkylene oxide-containing compound.

[0325] <Production Example 9> 8.0 g of polymer (2) was placed in a glass reaction vessel equipped with a reflux condenser and a stirrer, and the temperature was raised to 40°C while stirring. After the temperature was raised, 1.98 g of methyl acrylate was added dropwise over 30 minutes, and the mixture was stirred at 40°C for 15 hours. After the reaction, the mixture was placed in a reduced pressure state at 40°C via a trap tube, and the remaining methyl acrylate was removed. In this way, a polymer (polymer (7)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by Michael addition.

[0326] <Production Example 10> 10.0 g of polymer (2) was placed in a glass reaction vessel equipped with a reflux condenser and a stirrer, and the temperature was raised to 50°C with stirring. After the temperature was raised, 0.74 g of acetic anhydride was added dropwise over 34 minutes, and the mixture was stirred at 50°C for 6 hours. In this way, a polymer (polymer (8)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group were reduced by acetylation.

[0327] <Production Example 11> 3.0 g of polymer (2) was placed in a glass reaction vessel equipped with a reflux condenser and a stirrer, and the temperature was raised to 50°C while stirring. After the temperature was raised, 0.28 g of citric acid was added, and the mixture was stirred at 50°C for 3 hours. In this way, a polymer (polymer (9)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group were reduced by neutralization with an acid compound.

[0328] <Production Example 12> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 1.3 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 10.1 g of methoxypolyethylene glycol #1000 methacrylate (manufactured by Shin-Nakamura Chemical), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 80°C with stirring, and the reaction was continued for 40 hours. After completion of the reaction, consumption of methoxypolyethylene glycol #1000 methacrylate was confirmed by liquid chromatography, and a methoxypolyethylene glycol #1000 methacrylate adduct of polyethyleneimine (polymer (10)) was obtained as a polyalkylene oxide-containing compound.

[0329] <Production Example 13> 4.0 g of polymer 10 was placed in a glass reaction vessel equipped with a nitrogen inlet tube, a reflux condenser, and a stirrer, and the temperature was raised to 50°C with stirring. After the temperature was raised, 1.18 g of acetic anhydride was added dropwise over 55 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (11)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation.

[0330] <Production Example 14> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 7.0 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 89.78 g of methoxypolyethylene glycol #1000 acrylate (manufactured by Shin-Nakamura Chemical), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 80°C with stirring, and the reaction was continued for 6 hours. After completion of the reaction, it was confirmed by liquid chromatography that all of the methoxypolyethylene glycol #1000 acrylate had been consumed, and a methoxypolyethylene glycol #1000 acrylate adduct of polyethyleneimine (polymer (12)) was obtained as a polyalkylene oxide-containing compound.

[0331] <Production Example 15> 10.0 g of polymer (12) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer, and the temperature was raised to 40°C with stirring. After the temperature was raised, 0.36 g of methyl acrylate was added dropwise over 30 minutes, and the mixture was stirred at 50°C for 10 hours. After the reaction, the mixture was placed in a reduced pressure state at 40°C via a trap tube, and the remaining methyl acrylate was removed. In this way, a polymer (polymer (13)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by Michael addition.

[0332] <Production Example 16> 4.0 g of polymer (13) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, a reflux condenser, and a stirrer, and the temperature was raised to 50°C with stirring. After the temperature was raised, 0.33 g of acetic anhydride was added dropwise over 31 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (14)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation.

[0333] <Production Example 17> A glass reactor equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 5.0 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600). The atmosphere inside the reactor was replaced with nitrogen, and the temperature was raised to 90°C with stirring. After the temperature was raised, 5.86 g of 1,2-epoxyhexane was added dropwise over 84 minutes, and the mixture was stirred for 3 hours. A polymer (polymer (15)) in which the NH groups contained in the cationic groups had been reduced was obtained.

[0334] <Production Example 18> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 1.5 g of polymer (15) and 8.9 g of methoxypolyethylene glycol #1000 acrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 80°C with stirring, and the reaction was continued for 13 hours. After completion of the reaction, it was confirmed by liquid chromatography that all of the methoxypolyethylene glycol #1000 acrylate had been consumed, and a methoxypolyethylene glycol #1000 acrylate adduct of polyethyleneimine (polymer (16)) was obtained as a polyalkylene oxide-containing compound.

[0335] <Production Example 19> 4.0 g of polymer (16) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, a reflux condenser, and a stirrer, and the temperature was raised to 50°C with stirring. After the temperature was raised, 0.31 g of acetic anhydride was added dropwise over 30 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (17)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation.

[0336] <Production Example 20> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 1.1 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 10.6 g of methoxypolyethylene glycol #2000 methacrylate (manufactured by Shin-Nakamura Chemical), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 100°C with stirring, and the reaction was continued for 17 hours. After completion of the reaction, it was confirmed by liquid chromatography that the methoxypolyethylene glycol #1000 methacrylate had been consumed, and a polyethyleneimine-methoxypolyethylene glycol #2000 methacrylate adduct (polymer (18)) was obtained as a polyalkylene oxide-containing compound.

[0337] <Production Example 21> 4.0 g of polymer (18) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, a reflux condenser, and a stirrer, and the temperature was raised to 60°C with stirring. After the temperature was raised, 1.02 g of acetic anhydride was added dropwise over 45 minutes, and the mixture was stirred at 60°C for 5 hours. In this way, a polymer (polymer (19)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation.

[0338] <Production Example 22> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 0.5 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 9.5 g of methoxypolyethylene glycol #4000 methacrylate (manufactured by NOF Corp.), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 100°C with stirring, and the reaction was continued for 20 hours. After completion of the reaction, it was confirmed by liquid chromatography that the methoxypolyethylene glycol #4000 methacrylate had been consumed, and a polyethyleneimine-methoxypolyethylene glycol #4000 methacrylate adduct (polymer (20)) was obtained as a polyalkylene oxide-containing compound.

[0339] <Production Example 23> 4.0 g of polymer (20) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, a reflux condenser, and a stirrer, and the temperature was raised to 50°C with stirring. After the temperature was raised, 0.58 g of acetic anhydride was added dropwise over 27 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (21)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation.

[0340] <Production Example 24> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 1.5 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 1200) and 9.7 g of methoxypolyethylene glycol #1000 methacrylate (manufactured by Shin-Nakamura Chemical), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 100°C with stirring, and the reaction was continued for 30 hours. After completion of the reaction, it was confirmed by liquid chromatography that the methoxypolyethylene glycol #1000 methacrylate had been consumed, and a polyethyleneimine-methoxypolyethylene glycol #1000 methacrylate adduct (polymer (22)) was obtained as a polyalkylene oxide-containing compound.

[0341] <Production Example 25> 4.0 g of polymer (22) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, a reflux condenser, and a stirrer, and the temperature was raised to 50°C with stirring. After the temperature was raised, 1.43 g of acetic anhydride was added dropwise over 66 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (23)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation.

[0342] <Production Example 26> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 2.5 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 1200) and 48.1 g of methoxypolyethylene glycol #1000 acrylate (manufactured by Shin-Nakamura Chemical), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 70°C with stirring, and the reaction was continued for 10 hours. After completion of the reaction, it was confirmed by liquid chromatography that the methoxypolyethylene glycol #1000 acrylate had been consumed, and a methoxypolyethylene glycol #1000 acrylate adduct of polyethyleneimine (polymer (24)) was obtained as a polyalkylene oxide-containing compound.

[0343] <Production Example 27> A glass reaction vessel equipped with a nitrogen inlet tube, a reflux condenser, and a stirrer was charged with 15.0 g of polymer (24), and the temperature was raised to 50°C with stirring. After the temperature was raised, 1.34 g of acetic anhydride was added dropwise over 61 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (25)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation.

[0344] <Production Example 28> An autoclave equipped with a thermometer, pressure gauge, and stirrer was charged with 504.0 g of methoxypoly(n=25)ethylene glycol and 0.50 g of potassium hydroxide (Fujifilm Wako Pure Chemical Industries, Ltd.), and the temperature was raised to 100 °C while stirring. The autoclave was purged with nitrogen, and the pressure was reduced to 1.2 kPa using a vacuum pump, followed by dehydration for 1 hour. After dehydration was complete, the pressure inside the autoclave was adjusted to 0.3 MPa with nitrogen, and 96.4 g of 1,2-butylene oxide (Tokyo Chemical Industry Co., Ltd.) was gradually added over 120 minutes, and the mixture was maintained at 100 °C for an additional 40 minutes. The reaction system was then heated to 120 °C and maintained for 150 minutes for aging, after which the pressure inside the system was returned to normal. Furthermore, with the system temperature at 60 °C, a cold trap and vacuum pump were connected, and unreacted butylene oxide was distilled off under reduced pressure. The remaining product was collected to obtain methoxypoly(n=25)ethylene glycol-poly(n=3)butylene glycol (compound (2)). A jacketed glass reactor (capacity: 1 L) equipped with a thermometer, a stirrer, a product water separator, a reflux condenser (condenser), and a nitrogen inlet tube was charged with 538.93 g of compound (2), 35.48 g of acrylic acid, 19.06 g of paratoluenesulfonic acid monohydrate, 0.14 g of phenothiazine, 0.03 g of 4-hydroxyTEMPO, and 57.44 g of cyclohexane. The esterification reaction was carried out at a reaction temperature of 115 °C. After 60 hours, the esterification rate reached 97%. To the resulting esterification reaction solution (655.75 g), 8.61 g of 49% aqueous sodium hydroxide and 98.50 g of water were added to neutralize the paratoluenesulfonic acid. The mixture was then heated to 105 °C, and the cyclohexane was distilled off azeotropically with water. When the internal temperature of the jacketed glass reactor reached 98 °C, nitrogen was introduced into the reaction solution to expel the dissolved cyclohexane. Then, adjusting water was added to obtain an 80% aqueous solution of the esterified product (compound (3)).

[0345] <Production Example 29> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 0.90 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 9.10 g of compound (3), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 40°C with stirring, and the reaction was continued for 8 hours. After completion of the reaction, it was confirmed by liquid chromatography that the esterification product had been consumed, yielding a methoxypoly(n=25)ethylene glycol-poly(n=3)butylene glycol acrylate adduct of polyethyleneimine (polymer (26)).

[0346] <Production Example 30> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 0.47 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 9.52 g of compound (3), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 40°C with stirring, and the reaction was continued for 8 hours. After completion of the reaction, it was confirmed by liquid chromatography that the esterification product had been consumed, yielding a methoxypoly(n=25)ethylene glycol-poly(n=3)butylene glycol acrylate adduct of polyethyleneimine (polymer (27)).

[0347] <Production Example 31> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 0.32 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 9.68 g of compound (3), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 40°C with stirring, and the reaction was continued for 8 hours. After completion of the reaction, it was confirmed by liquid chromatography that the esterification product had been consumed, yielding a methoxypoly(n=25)ethylene glycol-poly(n=3)butylene glycol acrylate adduct of polyethyleneimine (polymer (28)).

[0348] <Production Example 32> An autoclave equipped with a thermometer, pressure gauge, and stirrer was charged with 730.3 g of methoxypoly(n = 25)ethylene glycol and 0.64 g of potassium hydroxide (Fujifilm Wako Pure Chemical Industries, Ltd.), and the temperature was raised to 120 °C while stirring. The autoclave was purged with nitrogen, and the pressure was reduced to 1.2 kPa using a vacuum pump, allowing dehydration for 1 hour. After dehydration was complete, the pressure inside the autoclave was adjusted to 0.3 MPa with nitrogen, and 69.7 g of 1,2-butylene oxide (Tokyo Chemical Industry Co., Ltd.) was gradually added over 80 minutes. The mixture was then maintained at 120 °C for 300 minutes for aging, after which the pressure inside the system was returned to normal. The system was then heated to 60 °C, and a cold trap and vacuum pump were connected, and unreacted butylene oxide was distilled off under reduced pressure. The remaining product was recovered, yielding methoxypoly(n = 25)ethylene glycol-poly(n = 1.5)butylene glycol (compound (4)). A jacketed glass reactor (capacity: 1 L) equipped with a thermometer, a stirrer, a product water separator, a reflux condenser (condenser), and a nitrogen inlet tube was charged with 691.40 g of compound (4), 60.19 g of acrylic acid, 35.62 g of a 70% aqueous solution of paratoluenesulfonic acid monohydrate, 0.19 g of phenothiazine, 0.04 g of 4-hydroxyTEMPO, and 75.16 g of cyclohexane. The esterification reaction was carried out at a reaction temperature of 110 °C. After 76 hours, an esterification rate of 89% was confirmed. To the resulting 862.60 g of esterification reaction solution, 13.02 g of a 48% aqueous solution of sodium hydroxide and 28.18 g of water were added to neutralize the paratoluenesulfonic acid. The mixture was then heated to 105 °C, and cyclohexane was distilled off azeotropically with water. When the internal temperature of the jacketed glass reactor reached 98 °C, nitrogen was introduced into the reaction solution to expel the dissolved cyclohexane. Then, adjusting water was added to obtain a 90% aqueous solution of the esterified product (compound (5)).

[0349] <Production Example 33> An autoclave equipped with a thermometer, pressure gauge, and stirrer was charged with 664.8 g of methoxypoly(n = 25)ethylene glycol and 0.60 g of potassium hydroxide (Fujifilm Wako Pure Chemical Industries, Ltd.), and the mixture was heated to 120 °C with stirring. The autoclave was purged with nitrogen, and the pressure was reduced to 1.2 kPa using a vacuum pump, allowing the mixture to dehydrate for 1 hour. After dehydration was complete, the pressure inside the autoclave was adjusted to 0.3 MPa with nitrogen, and 85.2 g of propylene oxide (Fujifilm Wako Pure Chemical Industries, Ltd.) was gradually added over 60 minutes. The mixture was then maintained at 120 °C for 240 minutes for aging, after which the pressure inside the system was returned to normal. Furthermore, with the system temperature at 60 °C, a cold trap and vacuum pump were connected, and unreacted propylene oxide was distilled off under reduced pressure. The remaining product was recovered, yielding methoxypoly(n = 25)ethylene glycol-poly(n = 2.5)propylene glycol (compound (6)). A jacketed glass reactor (capacity: 1 L) equipped with a thermometer, a stirrer, a product water separator, a reflux condenser (condenser), and a nitrogen inlet tube was charged with 691.30 g of compound (6), 58.56 g of acrylic acid, 35.54 g of a 70% aqueous solution of paratoluenesulfonic acid monohydrate, 0.19 g of phenothiazine, 0.04 g of 4-hydroxyTEMPO, and 74.99 g of cyclohexane. The esterification reaction was carried out at a reaction temperature of 110 °C. After 76 hours, the esterification rate was confirmed to have reached 90%. To the resulting esterification reaction solution (860.61 g), 12.80 g of a 48% aqueous solution of sodium hydroxide and 30.88 g of water were added to neutralize the paratoluenesulfonic acid. The mixture was then heated to 105 °C, and the cyclohexane was distilled off azeotropically with water. When the internal temperature of the jacketed glass reactor reached 98 °C, nitrogen was introduced into the reaction solution to expel the dissolved cyclohexane. Then, adjusted water was added to obtain a 90% aqueous solution of the esterified product (compound (7)).

[0350] <Production Example 34> An autoclave equipped with a thermometer, pressure gauge, and stirrer was charged with 597.0 g of methoxypoly(n = 25)ethylene glycol and 0.62 g of potassium hydroxide (Fujifilm Wako Pure Chemical Industries, Ltd.), and the mixture was heated to 120 °C with stirring. The autoclave was purged with nitrogen, and the pressure was reduced to 1.2 kPa using a vacuum pump, allowing the mixture to dehydrate for 1 hour. After dehydration was complete, the pressure in the autoclave was adjusted to 0.3 MPa with nitrogen, and 152.9 g of propylene oxide (Fujifilm Wako Pure Chemical Industries, Ltd.) was gradually added over 120 minutes. The mixture was then maintained at 120 °C for 180 minutes for aging, after which the pressure in the system was returned to normal. The system was then heated to 60 °C, and a cold trap and vacuum pump were connected, and unreacted propylene oxide was distilled off under reduced pressure. The remaining product was recovered, yielding methoxypoly(n = 25)ethylene glycol-poly(n = 5.0)propylene glycol (compound (8)). A jacketed glass reactor (volume: 1 L) equipped with a thermometer, a stirrer, a product water separator, a reflux condenser (condenser), and a nitrogen inlet tube was charged with 694.08 g of compound (8), 52.88 g of acrylic acid, 35.40 g of a 70% aqueous solution of paratoluenesulfonic acid monohydrate, 0.19 g of phenothiazine, 0.04 g of 4-hydroxyTEMPO, and 74.70 g of cyclohexane. The esterification reaction was carried out at a reaction temperature of 110 °C. After 76 hours, the esterification rate reached 94%. To the resulting 857.29 g of esterification reaction solution, 12.52 g of a 48% aqueous solution of sodium hydroxide and 31.87 g of water were added to neutralize the paratoluenesulfonic acid. The mixture was then heated to 105 °C, and the cyclohexane was distilled off azeotropically with water. When the internal temperature of the jacketed glass reactor reached 98 °C, nitrogen was introduced into the reaction solution to expel the dissolved cyclohexane. Then, adjusting water was added to obtain a 90% aqueous solution of the esterified product (compound (9)).

[0351] <Production Example 35> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 1.10 g of polyethyleneimine (Nippon Shokubai, average molecular weight 600) and 8.83 g of compound (5), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 40°C with stirring, and the reaction was continued for 2 hours. After completion of the reaction, it was confirmed by liquid chromatography that the esterification product of compound (5) had been consumed, yielding a methoxypoly(n=25)ethylene glycol-poly(n=1.5)butylene glycol acrylate adduct of polyethyleneimine (polymer (29)). A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 3.02 g of polymer (29), and the temperature was raised to 50°C with stirring. After the temperature was raised, 0.70 g of acetic anhydride was added dropwise over 10 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (30)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation. The polymer (30) accounted for 69% by weight of the resulting reaction solution. The number average molecular weight of polymer (30) measured by GPC was 6,640. 2.01 g of polymer (29) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer, and the temperature was raised to 50°C while stirring. After the temperature was raised, 0.78 g of citric acid (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at 50°C for 2 hours. In this way, a polymer (polymer (31)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group were reduced by neutralization with an acid compound. The polymer (31) accounted for 55 wt% of the resulting reaction solution. The number average molecular weight of polymer (31) measured by GPC was 6,490.

[0352] <Production Example 36> A glass reactor equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 0.61 g of polyethyleneimine (Nippon Shokubai, average molecular weight 600) and 9.65 g of compound (5), and the atmosphere inside the reactor was replaced with nitrogen. The temperature was then raised to 40°C with stirring, and the reaction was continued for 5 hours. After completion of the reaction, it was confirmed by liquid chromatography that the esterified product of compound (5) had been consumed, yielding a methoxypoly(n=25)ethylene glycol-poly(n=1.5)butylene glycol acrylate adduct of polyethyleneimine (polymer (32)). 3.02 g of polymer (32) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, a reflux condenser, and a stirrer, and the temperature was raised to 50°C with stirring. After the temperature was raised, 0.28 g of acetic anhydride was added dropwise over 10 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (33)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation. The polymer (33) accounted for 71 wt% of the reaction solution. The number average molecular weight of polymer (33) measured by GPC was 7510. 2.00 g of polymer (32) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer, and the temperature was raised to 50°C while stirring. After the temperature was raised, 0.31 g of citric acid (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at 50°C for 2 hours. In this way, a polymer (polymer (34)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group were reduced by neutralization with an acid compound. The polymer (34) accounted for 64 wt% of the reaction solution. The number average molecular weight of polymer (34) measured by GPC was 7,460.

[0353] <Production Example 37> A glass reactor equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 0.40 g of polyethyleneimine (Nippon Shokubai, average molecular weight 600) and 9.64 g of compound (5), and the atmosphere inside the reactor was replaced with nitrogen. The temperature was then raised to 40°C with stirring, and the reaction was continued for 12 hours. After completion of the reaction, it was confirmed by liquid chromatography that the esterified product of compound (5) had been consumed, yielding a methoxypoly(n=25)ethylene glycol-poly(n=1.5)butylene glycol acrylate adduct of polyethyleneimine (polymer (35)). 3.00 g of polymer (35) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, a reflux condenser, and a stirrer, and the temperature was raised to 50°C with stirring. After the temperature was raised, 0.11 g of acetic anhydride was added dropwise over 10 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (36)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation. The resulting reaction solution contained 64 wt% of polymer (36). The number average molecular weight of polymer (36) measured by GPC was 8630. 2.00 g of polymer (35) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer, and the temperature was raised to 50°C while stirring. After the temperature was raised, 0.13 g of citric acid (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at 50°C for 2 hours. In this way, a polymer (polymer (37)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by neutralization with an acid compound. The polymer (37) accounted for 67% by weight in the resulting reaction solution. The number average molecular weight of polymer (37) measured by GPC was 8,440.

[0354] <Production Example 38> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 1.50 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 10.67 g of compound (7), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 40°C with stirring, and the reaction was continued for 3 hours. After completion of the reaction, it was confirmed by liquid chromatography that the esterified product of compound (7) had been consumed, yielding a methoxypoly(n=25)ethylene glycol-poly(n=2.5)propylene glycol acrylate adduct of polyethyleneimine (polymer (38)). A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 4.00 g of polymer (38), and the temperature was raised to 50°C with stirring. After the temperature was raised, 1.06 g of acetic anhydride was added dropwise over 10 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (39)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation. The polymer (39) accounted for 72 wt% of the reaction solution. The number average molecular weight of polymer (39) measured by GPC was 6,530. 2.51 g of polymer (38) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer, and the temperature was raised to 50°C while stirring. After the temperature was raised, 1.12 g of citric acid (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at 50°C for 2 hours. In this way, a polymer (polymer (40)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by neutralization with an acid compound. The polymer (40) accounted for 56 wt% of the reaction solution. The number average molecular weight of polymer (40) measured by GPC was 6,360.

[0355] <Production Example 39> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 0.80 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 11.37 g of compound (7), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 40°C with stirring, and the reaction was continued for 5 hours. After completion of the reaction, it was confirmed by liquid chromatography that the esterified product of compound (7) had been consumed, yielding a methoxypoly(n=25)ethylene glycol-poly(n=2.5)propylene glycol acrylate adduct of polyethyleneimine (polymer (41)). A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 4.01 g of polymer (41), and the temperature was raised to 50°C with stirring. After the temperature was raised, 0.42 g of acetic anhydride was added dropwise over 10 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (42)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation. The polymer (42) accounted for 76% by weight of the resulting reaction solution. The number average molecular weight of polymer (42) measured by GPC was 7,300. 2.51 g of polymer (41) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer, and the temperature was raised to 50°C while stirring. After the temperature was raised, 0.46 g of citric acid (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at 50°C for 2 hours. In this way, a polymer (polymer (43)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group were reduced by neutralization with an acid compound. The polymer (43) accounted for 68 wt% of the resulting reaction solution. The number average molecular weight of polymer (43) measured by GPC was 7070.

[0356] <Production Example 40> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 0.56 g of polyethyleneimine (Nippon Shokubai, average molecular weight 600) and 11.73 g of compound (7), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 40°C with stirring, and the reaction was continued for 8 hours. After completion of the reaction, it was confirmed by liquid chromatography that the esterified product of compound (7) had been consumed, yielding a methoxypoly(n=25)ethylene glycol-poly(n=2.5)propylene glycol acrylate adduct of polyethyleneimine (polymer (44)). A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 4.00 g of polymer (44), and the temperature was raised to 50°C with stirring. After the temperature was raised, 0.21 g of acetic anhydride was added dropwise over 10 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (45)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation. The resulting reaction solution contained 77% by weight of polymer (45). The number average molecular weight of polymer (45) measured by GPC was 8,150. 2.53 g of polymer (44) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer, and the temperature was raised to 50°C while stirring. After the temperature was raised, 0.22 g of citric acid (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at 50°C for 2 hours. In this way, a polymer (polymer (46)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by neutralization with an acid compound. The polymer (46) accounted for 73 wt% of the reaction solution. The number average molecular weight of polymer (46) measured by GPC was 7920.

[0357] <Production Example 41> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 1.30 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 11.25 g of compound (9), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 40°C with stirring, and the reaction was continued for 2 hours. After completion of the reaction, it was confirmed by liquid chromatography that the esterified product of compound (9) had been consumed, yielding a methoxypoly(n=25)ethylene glycol-poly(n=5)propylene glycol acrylate adduct of polyethyleneimine (polymer (47)). A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 4.00 g of polymer (47), and the temperature was raised to 50°C with stirring. After the temperature was raised, 0.89 g of acetic anhydride was added dropwise over 10 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (48)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation. The resulting reaction solution contained 65 wt% of polymer (48). The number average molecular weight of polymer (48) measured by GPC was 7,030. 2.50 g of polymer (47) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer, and the temperature was raised to 50°C while stirring. After the temperature was raised, 0.94 g of citric acid (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at 50°C for 2 hours. In this way, a polymer (polymer (49)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by neutralization with an acid compound. The polymer (49) accounted for 52 wt% of the resulting reaction solution. The number average molecular weight of polymer (49) measured by GPC was 6,960.

[0358] <Production Example 42> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 0.70 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 12.14 g of compound (9), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 40°C with stirring, and the reaction was continued for 2 hours. After completion of the reaction, it was confirmed by liquid chromatography that the esterified product of compound (9) had been consumed, yielding a methoxypoly(n=25)ethylene glycol-poly(n=5)propylene glycol acrylate adduct of polyethyleneimine (polymer (50)). 4.00 g of polymer (50) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, a reflux condenser, and a stirrer, and the temperature was raised to 50°C with stirring. After the temperature was raised, 0.37 g of acetic anhydride was added dropwise over 10 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (51)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation. The polymer (51) accounted for 67% by weight of the resulting reaction solution. The number average molecular weight of polymer (51) measured by GPC was 7,750. 2.50 g of polymer (50) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer, and the temperature was raised to 50°C while stirring. After the temperature was raised, 0.39 g of citric acid (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at 50°C for 2 hours. In this way, a polymer (polymer (52)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group were reduced by neutralization with an acid compound. The polymer (52) accounted for 61 wt% of the resulting reaction solution. The number average molecular weight of polymer (52) measured by GPC was 7640.

[0359] <Production Example 43> A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 0.44 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 11.71 g of compound (9), and the atmosphere inside the reaction vessel was replaced with nitrogen. The temperature was then raised to 50°C with stirring, and the reaction was continued for 7 hours. After completion of the reaction, it was confirmed by liquid chromatography that the esterified product of compound (9) had been consumed, yielding a methoxypoly(n=25)ethylene glycol-poly(n=5)propylene glycol acrylate adduct of polyethyleneimine (polymer (53)). A glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer was charged with 4.00 g of polymer (53), and the temperature was raised to 50°C with stirring. After the temperature was raised, 0.16 g of acetic anhydride was added dropwise over 10 minutes, and the mixture was stirred at 50°C for 5 hours. In this way, a polymer (polymer (54)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by acetylation. The polymer (54) accounted for 69% by weight of the resulting reaction solution. The number average molecular weight of polymer (54) measured by GPC was 8970. 2.50 g of polymer (53) was placed in a glass reaction vessel equipped with a nitrogen inlet tube, reflux condenser, and stirrer, and the temperature was raised to 50°C while stirring. After the temperature was raised, 0.16 g of citric acid (Fujifilm Wako Pure Chemical Industries, Ltd.) was added, and the mixture was stirred at 50°C for 2 hours. In this way, a polymer (polymer (55)) was obtained in which the NH groups contained in cationic groups not bonded to a linking group had been reduced by neutralization with an acid compound. The polymer (55) accounted for 66 wt% of the reaction solution. The number average molecular weight of polymer (55) measured by GPC was 8650.

[0360] <Comparative composition (1)> A mixture of 0.90 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 20.6 g of methoxypolyethylene glycol #1000 acrylate (manufactured by Shin-Nakamura Chemical Co., Ltd.) was used as a comparative composition (1).

[0361] <Comparative composition (2)> A mixture of 0.10 g of polyethyleneimine (manufactured by Nippon Shokubai, average molecular weight 600) and 2.29 g of polyethylene glycol monomethyl ether 1000 (manufactured by Tokyo Chemical Industry Co., Ltd.) was used as comparative composition (2).

[0362] <Measurement of mud particle dispersibility> Mud dispersibility was measured using the following method. First, a sodium bicarbonate aqueous solution, a 3% linear alkylbenzene sulfonate sodium aqueous solution (hereinafter referred to as 3% LAS aqueous solution), and a 0.1% polymer (polyalkylene oxide-containing compound) aqueous solution were prepared. The sodium bicarbonate aqueous solution was prepared by adding pure water to 15.4 g of sodium bicarbonate and 100 g of 0.1 M hydrochloric acid to make a total of 1000 g. The 3% LAS aqueous solution was prepared by diluting linear alkylbenzene sulfonate with an appropriate amount of water to a solids concentration of 3% by mass. The 0.1% polyalkylene oxide-containing compound aqueous solution was prepared by diluting a polyalkylene oxide-containing compound with an appropriate amount of water to a solids concentration of 0.1% by mass. In a beaker, 0.5 g of sodium bicarbonate solution was mixed with 25°C 15°DH hard water (prepared with calcium chloride and magnesium chloride, Ca / Mg = 3 (mass ratio)) to make a 100 g solution. 0.025 g of Nariso red clay was added and stirred for 10 minutes, followed by ultrasonic irradiation for 10 minutes to prepare a mud dispersion. While stirring the dispersion, 0.83 g of a 3% LAS solution and 0.83 g of a 0.1% polymer solution were added and stirred for 10 minutes. The resulting mud dispersion was transferred to a 100 mL colorimetric tube and allowed to stand for 1 hour. 4 mL of the sample was then sampled from the center of the tube. The sampled solution was placed in a 1 cm quartz cell and the absorbance at 420 nm was measured using a Shimadzu UV-1800 spectrophotometer. Note that a higher absorbance indicates better dispersion of the mud particles.

[0363] <Measurement of anti-redeposition ability> The following washing process, which involves washing, rinsing, and drying, was repeated three times to measure the ability to prevent redeposition of the fabric. First, soiled fabric to be used in the washing process was prepared. Mud stained cloth preparation: Muddy water was prepared by adding pure water to 50g of ordinary red clay to make 500g and stirring. While stirring the prepared muddy water, cotton Kanakin No. 3 cut to 12 x 18cm was dipped into the muddy water three times, and then dried at 80°C for 10 minutes. After drying, the mud-stained cloth was shaken until no mud dust was visible, and the surface was brushed with a sponge. The mud-stained cloth obtained in this way was cut into 5 x 5cm pieces and used in the washing process (hereinafter referred to as mud-stained cloth). Cleaning process: The following two types of cotton cloth were used as the items to be washed. Cotton cloth (1): Five 5cm x 5cm cotton knit cloths (manufactured by Tanigashira Shoten) were prepared as recontamination test cloths. Cotton cloth (2): Cotton cloth obtained from Testfabrics was prepared so that the total weight of the cotton cloth (2) and the cotton cloth (1) was 30 g. As surfactants, a 3% aqueous solution of LAS, and 0.1% by mass aqueous solutions of the polyalkylene oxide-containing compound obtained in the Production Example and the comparative composition (1) were prepared. A Tergot-o-meter (manufactured by Daiei Scientific Co., Ltd., product name: TM-4) was charged with 900 mL of 15°DH hard water (prepared from calcium chloride and magnesium chloride, Ca / Mg=3 (mass ratio)) at 25°C, 7.5 g of the 3% LAS aqueous solution, 7.5 g of a 0.1% aqueous solution of the polyalkylene oxide-containing compounds polymers (1) to (8) and comparative composition (1), five 5 x 5 cm mud-stained cloths prepared above, and cotton cloths (1) and (2). The mixture was then washed for 10 minutes at a stirring speed of 120 rpm at 25°C. Rinse step: After the washing process, the washed items and mud-stained fabrics 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 and the mud-stained cloth 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 washed 1 to 3 times as described above and the cotton fabric (1) before the washing treatment was measured using a reflectometer (spectrophotometric colorimeter, manufactured by Nippon Denshoku Industries Co., Ltd., product name: SE6000), and the anti-redeposition rate was calculated using the following formula. Redeposition prevention rate = (Z value of cotton fabric (1) after 1 to 3 washings) / (Z value of cotton fabric (1) before washing) x 100 The anti-redeposition rate of the cotton cloth (1) after the third washing treatment is shown in Table 1.

[0364] <Measurement of anti-redeposition ability (2)> The following washing process, rinsing process and drying process were carried out in this order, and the ability to prevent redeposition on the fabric was measured. Cleaning process: The following two types of cotton cloth were used as the items to be washed. Cotton cloth (1): Five 5cm x 5cm cotton knit cloths (manufactured by Tanigashira Shoten) were prepared as recontamination test cloths. Cotton cloth (2): Cotton cloth obtained from Testfabrics was prepared so that the total weight of the cotton cloth (2) and the cotton cloth (1) was 30 g. As a surfactant, a 3% aqueous solution of LAS, and 0.1% by mass aqueous solutions of the polyalkylene oxide-containing compound obtained in the Production Example and the comparative composition (2) were prepared. A 1-L pot for a Tergot-o-meter (manufactured by Daiei Scientific Co., Ltd., product name: TM-4) was charged with 876 g of pure water at 25°C, followed by 4.5 g of a 1.5% by weight aqueous solution of sodium bicarbonate and stirring. Next, 4.5 g of 3000°DH hard water (prepared with calcium chloride and magnesium chloride, Ca / Mg = 3 (by mass)) was added, followed by 7.5 g of a 3% aqueous solution of LAS, 7.5 g of the polyalkylene oxide-containing polymers (10) to (19), and 7.5 g of a 0.1% aqueous solution of comparative composition (2). Next, 0.9 g of ordinary red clay was added and stirred. After stirring, cotton cloths (1) and (2) were added, and the mixture was washed 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 reflectance meter (spectrophotometric color difference meter, manufactured by Nippon Denshoku Industries Co., Ltd., product name: SE6000), and the anti-redeposition rate was calculated using the following formula. Redeposition prevention rate = (Z value of cotton cloth (1) after washing treatment) ÷ (Z value of cotton cloth (1) before washing treatment) × 100 The anti-redeposition rate (2) of the cotton fabric (1) after the above washing treatment is shown in Table 2.

[0365] <Biodegradability test> The biodegradability test of the obtained polyalkylene oxide-containing compound was carried out in accordance with OECD301F. Preparation of medium: Stock medium solutions A to D were prepared by the following method. Solution A: 0.850 g of potassium dihydrogen phosphate (KH2PO4), 2.175 g of dipotassium hydrogen phosphate (K2HPO4), 6.7217 g of disodium hydrogen phosphate dodecahydrate (Na2HPO4 12H2O), and 0.050 g of ammonium chloride (NH4Cl) were weighed into a 50 ml sample bottle, dissolved in an appropriate amount of water, and transferred to a 100 ml measuring flask, followed by addition of water up to the mark. Solution B: 3.640 g of calcium chloride dihydrate (CaCl2·2H2O) was dissolved in an appropriate amount of water and transferred to a 100 ml measuring flask, after which water was added up to the mark. Solution C: 2.250 g of magnesium sulfate heptahydrate (MgSO4·7H2O) was dissolved in an appropriate amount of water and transferred to a 100 ml measuring flask, after which water was added up to the mark. Solution D: 0.025 g of iron(III) chloride hexahydrate (FeCl3·6H2O) was dissolved in an appropriate amount of water and transferred to a 100 ml measuring flask, after which water was added up to the mark. The above stock medium solutions A to D were adjusted to 25°C, and 10 ml of A was added to a 1 L volumetric flask using a volumetric pipette and diluted with approximately 800 ml of water. Then, 1 ml each of B, C, and D was added using a volumetric pipette and diluted to the mark with water adjusted to 25°C. Multiple batches of the above medium were prepared according to the amount required for the test. The prepared medium was transferred to a 5 L beaker, mixed, and bubbled for at least 1 hour while stirring. Preparation of sludge solution: The sludge used in the biodegradability test was obtained from the Minami Suita Sewage Treatment Plant. First, the concentration of the obtained sludge was measured using the following method. The obtained sludge was bubbled while stirring, and 5 ml was taken using a whole pipette and suction filtered using filter paper. Five sheets of filter paper containing the sludge were prepared in this way and dried in a dryer at 105°C for 1 hour. The sludge concentration was calculated from the average weight loss of the five sheets. This sludge was diluted with the medium prepared above to prepare a 1000 ppm sludge solution. Preparation of aqueous polymer solutions: The polymer (1) obtained in Production Example (1) was diluted with pure water to obtain a 2% by mass aqueous polymer solution. As a standard substance, sodium benzoate was diluted with pure water to obtain a 2% by mass aqueous sodium benzoate solution. BOD Test: A pressure sensor-type BOD meter was used to measure BOD. 144.75 g of the prepared medium was weighed into a furnace bottle, and 0.75 g of a 2% polymer aqueous solution was added. For the blank measurement, 0.75 g of pure water was added, and for the standard measurement, 0.75 g of a 2% sodium benzoate aqueous solution was added. The pH of the solution was then measured and adjusted to 7.4 ± 0.2 with 0.1 M hydrochloric acid. 4.5 ml of 1000 ppm sludge solution was then added to the test solution. A stir bar was placed in the furnace bottle, and 1.8 g of CO2 absorbent (Yabasil lime) was placed in the CO2 absorbent holder and set, and a BOD sensor was attached. The furnace bottle with the BOD sensor attached was stirred in a constant temperature bath at 24 °C, and the BOD value was calculated from the pressure sensor. Calculation of decomposition rate: The theoretical oxygen demand (ppm) of the polymer was calculated, and the degradation rate was calculated from the difference between the BOD value of the blank measurement and the BOD value measured using a polyalkylene oxide-containing compound. The degradation rate 28 days after the start of the test was taken as the biodegradation rate. The degradation rate of polymer (1) after 28 days was 71%. Formula Decomposition rate (%) = (biochemical oxygen consumption derived from polymer) / (theoretical oxygen demand of polymer) × 100

[0366] <Alkali decomposition test> A glass test tube equipped with a thermometer and a stirrer tip was charged with 0.180 g of polymer, and 5.820 g of 0.1 M NaOH aqueous solution (Fujifilm Wako Pure Chemical Industries, Ltd.) was added to prepare a 3% polymer solution. The polymer solution was then heated to 80°C with stirring and maintained for 2 hours. After heating, the polymer solution was diluted 10-fold with the eluent described in the molecular weight measurement conditions above, and molecular weight measurement was performed. The number average molecular weights before and after alkaline decomposition, as well as the ratio of the molecular weight after alkaline decomposition to the molecular weight before alkaline decomposition, are shown in Table 3.

[0367] [Table 1]

[0368] The results in Table 1 reveal that the polymers (1) to (5), which are polyalkylene oxide-containing compounds of the present disclosure, exhibit excellent mud dispersibility and excellent anti-soil redeposition properties.

[0369] [Table 2]

[0370] The results in Table 2 reveal that the polymers (10) to (55), which are polyalkylene oxide-containing compounds of the present disclosure, exhibit excellent anti-soil redeposition properties.

[0371] [Table 3]

[0372] The results in Table 3 reveal that polymers (8), (11), (30), (39), and (48), which are polyalkylene oxide-containing compounds of the present disclosure, exhibit excellent alkali decomposition properties.

Claims

1. A polyalkylene oxide-containing compound having a cationic group, a linking group, and a structural unit derived from polyalkylene oxide, a substituent in which the linking group and a structural unit derived from polyalkylene oxide are bonded, The substituent is represented by the following general formula (1): 【Chemical 1】 (In general formula (1), R １ are the same or different and represent a hydrocarbon group having 2 to 6 carbon atoms. X is -C(=α １ ) -β １ - group, -α １ -CR ２ R ３ -β １ represents one or more selected from the group consisting of - groups, and α １ , β １ are the same or different and represent a heteroatom or a group in which a hydrogen atom is bonded to a heteroatom. ２ , R ３ are the same or different and represent a hydrogen atom or an organic group having 1 to 10 carbon atoms. s is an integer of 1 to 300. Y represents a linear or branched hydrocarbon group having 1 to 10 carbon atoms, or a substituent represented by the following general formula (2). Z represents a direct bond, -(CH ２ ) ｎ - (S) ｍ - (CH ２ ) ｐ -O- group, -(CH ２ ) ｎ -α ２ represents a - group or a substituent represented by the following general formula (3): ２ represents a heteroatom or a group in which a hydrogen atom is bonded to a heteroatom. m is 0 or 1, and n is an integer from 1 to 10. p is an integer from 1 to 10. T represents a hydrogen atom or an organic group having 1 to 30 carbon atoms. 【Chemistry 2】 (In general formula (2), q is an integer of 1 to 300. R ５ , R ６ are the same or different and represent a hydrocarbon group having 2 to 6 carbon atoms. 【Chemistry 3】 (In general formula (3), n is an integer of 1 to 10.) The cationic group is represented by the following general formula (4): 【Chemistry 4】 (In the formula, R ７ 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, b, and c are the same or different and represent 0 or an integer of 1 or more, at least one of a, b, and c is an integer of 1 to 100, and a+b+c is a number of 5 or more. The structural unit having an amino group contains at least two or more -N-R ７ -units will exist.) is a group obtained by removing a hydrogen atom bonded to a nitrogen atom from a precursor constituting a structural unit having an amino group, represented by having a structure in which a substituent represented by general formula (1) is bonded to a cationic group; Polyalkylene oxide-containing compounds.

2. α of X in the substituents described in the general formula (1) １ , β １ 2. The polyalkylene oxide-containing compound according to claim 1, wherein the heteroatom is an oxygen atom or a nitrogen atom.

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

4. In the polyalkylene oxide-containing compound, an unreacted NH group that is not bonded to a linking group contained in the cationic group is relative to the total number of moles of nitrogen atoms contained in the polyalkylene oxide-containing compound, 80 mol % or less The polyalkylene oxide-containing compound according to claim 1 or 2.

5. a number-average molecular weight of a decomposition product obtained by carrying out a decomposition test in which a polyalkylene oxide-containing compound is decomposed by either alkaline hydrolysis or enzymatic decomposition is 0.5 or less relative to the number-average molecular weight of the polyalkylene oxide-containing compound before the decomposition test; The polyalkylene oxide-containing compound according to claim 1 or 2.

6. A composition comprising the polyalkylene oxide-containing compound according to claim 1 or 2 and an acid compound.

7. A method for producing the polyalkylene oxide-containing compound according to claim 1 or 2, comprising: The production method includes a step of subjecting an α,β-unsaturated carbonyl compound having a polyalkylene oxide chain to a Michael addition reaction to an amino group contained in a cationic group. A method for producing a polyalkylene oxide-containing compound.

8. A method for producing the polyalkylene oxide-containing compound according to claim 1 or 2, comprising: The production method includes a first step of Michael addition of an α,β-unsaturated carbonyl compound to an amino group, which is a cationic group; a second step of introducing a polyalkylene oxide chain into the product obtained in the first step; A method for producing a polyalkylene oxide-containing compound.

9. A method for producing the polyalkylene oxide-containing compound according to claim 1 or 2, comprising: The production method includes a step of reducing unreacted NH groups contained in the cationic group not bonded to the linking group by one or more reactions selected from the group consisting of a Michael addition reaction, an acetylation reaction, an amidation reaction with a carboxylic acid anhydride, an amidation reaction with a carboxylic acid halide, and an epoxy compound addition reaction. A method for producing a polyalkylene oxide-containing compound.

10. A method for producing the polyalkylene oxide-containing compound according to claim 1 or 2, comprising: The production method includes a step of neutralizing, with an acid compound, an unreacted NH group contained in the cationic group not bonded to the linking group. A method for producing a polyalkylene oxide-containing compound.

11. A detergent or cleaning composition comprising the polyalkylene oxide-containing compound of claim 1 or claim 2.

12. 12. The detergent or cleaning composition of claim 11, wherein the detergent or cleaning composition is selected from the group consisting of laundry detergent compositions, hard surface cleaning compositions, hand dishwashing compositions, and automatic dishwashing compositions, and is a liquid.

13. 12. The detergent or cleaning composition of claim 11, wherein the detergent or cleaning composition is selected from the group consisting of laundry detergent compositions, hard surface cleaning compositions, hand dishwashing compositions, and automatic dishwashing compositions, and is in a single-phase or multi-phase unit dose form containing a liquid detergent or cleaning composition enclosed in a single- or multi-compartment water-soluble pouch.

14. 12. The detergent or cleaning composition of claim 11, further comprising a surfactant selected from the group consisting of anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, zwitterionic surfactants, and mixtures thereof.

15. 15. The detergent or cleaning composition of claim 14, wherein the surfactant is an anionic surfactant selected from the group consisting of alkyl benzene sulfonates, alkoxylated alkyl sulfates, alkyl sulfates, and mixtures thereof.

16. 12. The detergent or cleaning composition of claim 11, wherein the detergent or cleaning composition is a liquid laundry detergent composition further comprising one or more cleaning adjunct additives selected from the group consisting of builders; structurants or thickeners; mud soil removers; mud soil anti-redeposition agents; polymeric soil release agents; polymeric dispersants; polymeric grease cleaning agents; enzymes; enzyme stabilizing systems selected from calcium ions, boric acid, propylene glycol, short chain carboxylic acids, boronic acids, chlorine bleach scavengers and mixtures thereof, borates, 4-formylphenylboronic acid, phenylboronic acid and derivatives thereof, calcium formate, sodium formate, 1,2-propanediol; bleaching compounds; bleaching agents; bleach activators; bleach catalysts; brighteners; dyes; hueing agents; dye transfer inhibitors; chelating agents; suds suppressors; softeners; fragrances; and mixtures thereof.

17. 12. The detergent or cleaning composition of claim 11, wherein the detergent or cleaning composition is substantially free of zeolite builder and phosphate builder.

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