Patent Description:
Nonionic surfactants are used in a wide range of fields such as laundry detergents, dishwashing detergents, residential detergents, body cleansers, iron and steel cleaning, and precision cleaning. The required performance of the nonionic surfactants is, for example, high detergency, compatibility with products, and easiness of handling.

General nonionic surfactants have a problem of having a wide gelled region.

Patent Document <NUM> discloses a surfactant that has excellent detergency for general fibers and includes a mixed product including two or more internal vicinal two hydrophilic groups-containing compounds having a specific structure.

Patent Document <NUM> discloses a technique of adding to a detergent composition an addition product obtained by adding ethylene oxide to an internally positioned vicinal alkanediol in order to provide a detergent composition exhibiting a low viscosity at room temperature.

The surfactant of Patent Document <NUM>, however, has a problem of remarkably lowering the detergency when contained at a low concentration in a composition. The detergent composition of Patent Document <NUM> prevents the generation of gel by using a polyoxyethylene alkyl ether and the addition product in combination. However, when only the addition product is used as a surfactant, or when the addition product and another surfactant are used in combination, gel is easily produced at low temperatures, and the detergent composition thus has a problem of having poor handling properties.

The present invention has been made in view of the circumstances described above, and provides: a compound that exhibits high detergency even when contained at a low concentration in a detergent composition, and that has a narrow gelation concentration range at low temperatures and excellent handling properties; and a precursor compound for producing the compound. The present invention also provides a surfactant composition and a detergent composition that include the compound.

As a result of an earnest study, the inventors of the present invention have found that the problems can be solved by a compound having a following specific structure.

The present invention relates to a compound represented by a chemical formula (<NUM>) below:
<CHM>
wherein R<NUM> and R<NUM> are each an aliphatic hydrocarbon group, X is a single bond or a hydrocarbon group having <NUM> or more and <NUM> or less carbon atoms, a total number of carbon atoms of R<NUM>, R<NUM>, and X is <NUM> or more and <NUM> or less, A<NUM> is -O(-A<NUM>O)m-H or -O(-A<NUM>O)p-H, A<NUM> is -O-R<NUM>O(-A<NUM>O)n-H or -O(-A<NUM>O)q+<NUM>-H, R<NUM> is an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms, m pieces of A<NUM> and n pieces of A<NUM> are each independently an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms, p pieces of A<NUM> and q + <NUM> pieces of A<NUM> are each independently an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms, at least one piece of A<NUM> among the q + <NUM> pieces of A<NUM> is a linear alkane-α,ω-diyl group having <NUM> or more and <NUM> or less carbon atoms, m, n, p, and q are an average value and are each independently <NUM> or more, a total of m and n is more than <NUM> and <NUM> or less, and a total of p and q is more than <NUM> and <NUM> or less.

The present invention relates to a method for producing the compound represented by the chemical formula (<NUM>), as disclosed in the appended claims <NUM>-<NUM>.

The compound (hereinafter, also referred to as an internal two hydrophilic groups-containing compound) represented by the chemical formula (<NUM>) of the present invention has a characteristic chemical structure (particularly a pendant hydrophilic group). Therefore, the internal two hydrophilic groups-containing compound according to the present invention has excellent effects of exhibiting high detergency even when contained at a low concentration in a detergent composition, and having a narrow gelation concentration range at low temperatures. A detergent composition according to the present invention that contains the internal two hydrophilic groups-containing compound exhibits high detergency even with a low concentration of the surfactant therein, is less likely to cause gelation in a wide range of concentration at low temperatures, and has excellent handling properties.

Hereinafter, a detailed described is made of the present invention.

The internal two hydrophilic groups-containing compound of the present invention is a compound represented by the chemical formula (<NUM>) below:
<CHM>
wherein R<NUM> and R<NUM> are each an aliphatic hydrocarbon group, X is a single bond or a hydrocarbon group having <NUM> or more and <NUM> or less carbon atoms, a total number of carbon atoms of R<NUM>, R<NUM>, and X is <NUM> or more and <NUM> or less, A<NUM> is -O(-A<NUM>O)m-H or -O(-A<NUM>O)p-H, A<NUM> is -O-R<NUM>O(-A<NUM>O)n-H or -O(-A<NUM>O)q+<NUM>-H, R<NUM> is an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms, m pieces of A<NUM> and n pieces of A<NUM> are each independently an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms, p pieces of A<NUM> and q + <NUM> pieces of A<NUM> are each independently an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms, at least one piece of A<NUM> among the q + <NUM> pieces of A<NUM> is a linear alkane-α,ω-diyl group having <NUM> or more and <NUM> or less carbon atoms, m, n, p, and q are an average value and are each independently <NUM> or more, a total of m and n is more than <NUM> and <NUM> or less, and a total of p and q is more than <NUM> and <NUM> or less.

R<NUM> and R<NUM> are each an aliphatic hydrocarbon group, and are each preferably a linear or branched alkyl group, more preferably a linear alkyl group, further preferably a linear primary alkyl group, from the viewpoints of production efficiency and easiness of production. R<NUM> and R<NUM> each independently have <NUM> or more and <NUM> or less carbon atoms and may each have a carbon number distribution. R<NUM> and R<NUM> may be a same aliphatic hydrocarbon group or different aliphatic hydrocarbon groups.

In the chemical formula (<NUM>), X is a single bond or a hydrocarbon group having <NUM> or more and <NUM> or less carbon atoms, and is preferably a single bond or a hydrocarbon group having <NUM> or more and <NUM> or less carbon atoms, more preferably a single bond or a hydrocarbon group having <NUM> or more and <NUM> or less carbon atoms, further preferably a single bond or a hydrocarbon group having <NUM> carbon atom, still further preferably a single bond, from the viewpoints of production efficiency and easiness of production.

The total number of carbon atoms of R<NUM>, R<NUM>, and X is <NUM> or more and <NUM> or less, is preferably <NUM> or more, more preferably <NUM> or more, further preferably <NUM> or more from the viewpoint of improving detergency, and is preferably <NUM> or less, more preferably <NUM> or less, further preferably <NUM> or less from the viewpoint of improving water solubility.

The total number of carbon atoms of R<NUM>, R<NUM>, and X is preferably even from the viewpoint of easiness of obtaining a raw material.

The internal two hydrophilic groups-containing compound preferably includes two or more compounds that have a same total number of carbon atoms of R<NUM>, R<NUM>, and X, but are different in number of carbon atoms of each of R<NUM> and R<NUM>, from the viewpoints of production efficiency and easiness of production.

The internal two hydrophilic groups-containing compound more preferably includes two or more compounds that have a single bond as X and a same total number of carbon atoms of R<NUM>, R<NUM>, and X, but are different in number of carbon atoms of each of R<NUM> and R<NUM>, from the viewpoints of production efficiency and easiness of production.

When the internal two hydrophilic groups-containing compound includes two or more compounds that have a single bond as X, and are different in total number of carbon atoms of R<NUM> and R<NUM>, the total content of a compound having a total number of carbon atoms of R<NUM> and R<NUM> of <NUM> and a compound having a total number of carbon atoms of R<NUM> and R<NUM> of <NUM> is, in the whole internal two hydrophilic groups-containing compound, preferably <NUM> mass% or more, more preferably <NUM> mass% or more, further preferably <NUM> mass% or more, still further preferably <NUM> mass%, from the viewpoint of improving detergency and narrowing the range of gelation concentration at low temperatures.

When being a hydrocarbon group, X is preferably a linear or branched alkanediyl group, more preferably a linear alkanediyl group, further preferably a linear α,ω-alkanediyl group, from the viewpoints of production efficiency and easiness of production.

When the internal two hydrophilic groups-containing compound includes two or more compounds that have a same total number of carbon atoms of R<NUM>, R<NUM>, and X, but are different in number of carbon atoms of each of R<NUM> and R<NUM>, the content proportion of a compound in which R<NUM> has <NUM> or more carbon atoms and R<NUM> has <NUM> or more carbon atoms is, in the whole internal two hydrophilic groups-containing compound, preferably <NUM> mass% or more, more preferably <NUM> mass% or more, further preferably <NUM> mass% or more, and preferably <NUM> mass% or less, more preferably <NUM> mass% or less, further preferably <NUM> mass% or less, from the viewpoint of improving detergency and narrowing the range of gelation concentration at low temperatures.

In the chemical formula (<NUM>), A<NUM> is -O(-A<NUM>O)m-H or - O(-A<NUM>O)p-H, and A<NUM> is -O-R<NUM>O(-A<NUM>O)n-H or -O(-A<NUM>O)q+<NUM>-H.

R<NUM> is an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms, from the viewpoint of detergency at low concentrations. The alkanediyl group is preferably a linear alkanediyl group, more preferably a linear alkane-α,ω-diyl group from the viewpoint of improving detergency and water solubility, and is further preferably a butane-<NUM>,<NUM>-diyl group or a hexane-<NUM>,<NUM>-diyl group from the viewpoint of easiness of production. The alkanediyl group has preferably <NUM> or more and <NUM> or less carbon atoms, more preferably <NUM> or more and <NUM> or less carbon atoms, further preferably <NUM> or more and <NUM> or less carbon atoms, from the viewpoint of improving detergency at low concentrations and water solubility.

A<NUM>O and A<NUM>O are each an alkyleneoxy group, and A<NUM> and A<NUM> are each independently an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms, preferably each independently an alkanediyl group having <NUM> or <NUM> carbon atoms from the viewpoint of improving detergency and water solubility. The alkanediyl group is preferably a <NUM>,<NUM>-alkanediyl group from the viewpoint of easiness of production, is more preferably one or more selected from an ethanediyl group, and a <NUM>,<NUM>-propanediyl group from the viewpoint of improving detergency and water solubility, and is further preferably an ethanediyl group from the viewpoint of detergency. The alkyleneoxy group is specifically an ethyleneoxy group, a branched propyleneoxy group, or a linear propyleneoxy group. The alkyleneoxy group is preferably an ethyleneoxy group or a branched propyleneoxy group. m pieces of A<NUM>O and n pieces of A<NUM>O may each independently include one type of the alkyleneoxy group or two or more types of the alkyleneoxy groups. Even when the internal two hydrophilic groups-containing compound includes two or more compounds that are different in number of pieces of A<NUM>O or A<NUM>O, m or n in the chemical formula (<NUM>) represents the average value of the total number of alkyleneoxy groups.

When m pieces of A<NUM>O or n pieces of A<NUM>O include two or more types of the alkyleneoxy groups, the alkyleneoxy groups are preferably an ethyleneoxy group and a branched propyleneoxy group. When m pieces of A<NUM>O or n pieces of A<NUM>O include an ethyleneoxy group and a branched propyleneoxy group, the molar ratio (ethyleneoxy group/branched propyleneoxy group) of the ethyleneoxy group to the branched propyleneoxy group is preferably <NUM>/<NUM> or more, more preferably <NUM>/<NUM> or more from the viewpoint of improving detergency and water solubility, and is preferably <NUM>/<NUM> or less, more preferably <NUM>/<NUM> or less, further preferably <NUM>/<NUM> or less from the viewpoint of prevention of gelation. The molar ratio (ethyleneoxy group/branched propyleneoxy group) is preferably <NUM>/<NUM> to <NUM>/<NUM>, more preferably <NUM>/<NUM> to <NUM>/<NUM>, further preferably <NUM>/<NUM> to <NUM>/<NUM>, still further preferably <NUM>/<NUM> to <NUM>/<NUM>, from the viewpoint of improving detergency and water solubility, and the viewpoint of prevention of gelation.

A<NUM>O and A<NUM>O are each an alkyleneoxy group, and A<NUM> and A<NUM> are each independently an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms from the viewpoint of improving detergency and water solubility. The alkanediyl group is preferably a <NUM>,<NUM>-alkanediyl group from the viewpoint of easiness of production, is more preferably one or more selected from an ethanediyl group or a <NUM>,<NUM>-propanediyl group from the viewpoint of improving detergency and water solubility, and is further preferably an ethanediyl group from the viewpoint of detergency. The alkanediyl group has preferably <NUM> or more and <NUM> or less carbon atoms, more preferably <NUM> or more and <NUM> or less carbon atoms, further preferably <NUM> or more and <NUM> or less carbon atoms, from the viewpoint of improving detergency and water solubility. Examples of the alkyleneoxy group include an ethyleneoxy group, a branched alkyleneoxy group having <NUM> or more and <NUM> or less carbon atoms, and a linear alkyleneoxy group having <NUM> or more and <NUM> or less carbon atoms. The alkyleneoxy group is preferably an ethyleneoxy group or a branched alkyleneoxy group having <NUM> or more and <NUM> or less carbon atoms. p pieces of A<NUM>O and q + <NUM> pieces of A<NUM>O may each independently include one type of the alkyleneoxy group or two or more types of the alkyleneoxy groups. Even when the internal two hydrophilic groups-containing compound includes two or more compounds that are different in number of pieces of A<NUM>O or A<NUM>O, p or q in the chemical formula (<NUM>) represents the average value of the total number of alkyleneoxy groups.

When p pieces of A<NUM>O or q + <NUM> pieces of A<NUM>O include two or more types of the alkyleneoxy groups, the alkyleneoxy groups are preferably an ethyleneoxy group and one or more types of branched alkyleneoxy groups having <NUM> or more and <NUM> or less carbon atoms, more preferably an ethyleneoxy group and a branched propyleneoxy group. When p pieces of A<NUM>O or q + <NUM> pieces of A<NUM>O include an ethyleneoxy group and one or more types of branched alkyleneoxy groups having <NUM> or more and <NUM> or less carbon atoms (or a branched propyleneoxy group), the molar ratio (ethyleneoxy group/branched alkyleneoxy group having <NUM> or more and <NUM> or less carbon atoms (or branched propyleneoxy group) of the ethyleneoxy group to the branched alkyleneoxy group having <NUM> or more and <NUM> or less carbon atoms (or the branched propyleneoxy group) is preferably <NUM>/<NUM> or more, more preferably <NUM>/<NUM> or more from the viewpoint of improving detergency and water solubility, and is preferably <NUM>/<NUM> or less, more preferably <NUM>/<NUM> or less, further preferably <NUM>/<NUM> or less from the viewpoint of prevention of gelation. The molar ratio (ethyleneoxy group/branched alkyleneoxy group having <NUM> or more and <NUM> or less carbon atoms (or branched propyleneoxy group)) is preferably <NUM>/<NUM> to <NUM>/<NUM>, more preferably <NUM>/<NUM> to <NUM>/<NUM>, further preferably <NUM>/<NUM> to <NUM>/<NUM>, still further preferably <NUM>/<NUM> to <NUM>/<NUM>, from the viewpoint of improving detergency and water solubility, and the viewpoint of prevention of gelation.

Among the q + <NUM> pieces of A<NUM>, at least one piece of A<NUM> is a linear alkane-α,ω-diyl group having <NUM> or more and <NUM> or less carbon atoms. The linear alkane-α,ω-diyl group has preferably <NUM> or more and <NUM> or less carbon atoms, more preferably <NUM> or more and <NUM> or less carbon atoms, further preferably <NUM> or <NUM> carbon atoms, from the viewpoint of improving detergency and water solubility. The linear alkane-α,ω-diyl group may be A<NUM> at any position in a repeating structure of q + <NUM> pieces of A<NUM>O.

A<NUM> is preferably -O-A<NUM>O(-A<NUM>O)q-H from the viewpoint of improving low-temperature stability and detergency, and the viewpoint of easiness of production, and at least A<NUM> is a linear alkane-α,ω-diyl group having <NUM> or more and <NUM> or less carbon atoms.

The content of the linear alkane-α,ω-diyl group having <NUM> or more and <NUM> or less carbon atoms is, on average per molecule, preferably <NUM> mol or more, and preferably <NUM> mol or less, more preferably <NUM> mol or less, further preferably <NUM> mol or less, from the viewpoint of improving detergency and water solubility, and the viewpoint of prevention of gelation.

When m pieces of A<NUM>O, n pieces of A<NUM>O, p pieces of A<NUM>O, or q + <NUM> pieces of A<NUM>O include two or more types of the alkyleneoxy groups, the repeating structure of the alkyleneoxy groups may include a random structure, a block structure, or a combination of a random structure and a block structure. The repeating structure, however, includes preferably a block structure, more preferably an EO block-PO block structure, a PO block-EO block structure, an EO block-PO block-EO block structure, or a PO block-EO block-PO block structure, further preferably an EO block-PO block-EO block structure, from the viewpoint of prevention of gelation.

In the chemical formula (<NUM>), m, n, p, and q are an average value and are each independently <NUM> or more, the total of m and n is more than <NUM> and <NUM> or less, and the total of p and q is more than <NUM> and <NUM> or less. The total of m and n, or the total of p and q is preferably <NUM> or more, more preferably <NUM> or more, further preferably <NUM> or more, still further preferably <NUM> or more from the viewpoint of improving detergency and water solubility, and is preferably <NUM> or less, more preferably <NUM> or less, further preferably <NUM> or less, still further preferably <NUM> or less from the viewpoints of preventing gelation and improving detergency.

The method for producing the internal two hydrophilic groups-containing compound in which A<NUM> is -O(-A<NUM>O)m-H, and A<NUM> is -O-R<NUM>O(-A<NUM>O)n-H is not particularly limited, and the internal two hydrophilic groups-containing compound can be produced, for example, by oxidizing a double bond of an internal olefin with a peroxide such as hydrogen peroxide and peracetic acid to synthesize an internal epoxide, adding to the obtained internal epoxide glycol having <NUM> or more and <NUM> or less carbon atoms to synthesize an internal diol, and adding to the obtained internal diol an alkylene oxide having <NUM> or more and <NUM> or less carbon atoms. When the internal olefin is a mixed product of two or more internal olefins that have a same total number of carbon atoms but a double bond at different positions therebetween, the internal two hydrophilic groups-containing compound obtained by the above-described production method is a mixed product of two or more compounds that have a same total number of carbon atoms of R<NUM> and R<NUM>, but are different in number of carbon atoms of each of R<NUM> and R<NUM>.

The method for producing the internal two hydrophilic groups-containing compound in which A<NUM> is -O(-A<NUM>O)p-H, and A<NUM> is -O(-A<NUM>O)q+<NUM>-H is not particularly limited, and the internal two hydrophilic groups-containing compound can be produced, for example, by oxidizing a double bond of an internal olefin with a peroxide such as hydrogen peroxide and peracetic acid to synthesize an internal epoxide, hydrolyzing the obtained internal epoxide or adding to the internal epoxide a both-terminal alkanediol having <NUM> or more and <NUM> or less carbon atoms to synthesize an internal diol, and adding to the obtained internal diol an alkylene oxide having <NUM> or more and <NUM> or less carbon atoms. The method for introducing a linear alkane-α,ω-diyl group having <NUM> or more and <NUM> or less carbon atoms into a repeating structure of A<NUM>O and/or A<NUM>O is, for example, reacting the compound having an alkylene oxide added thereto with X-(CH<NUM>)n-OH (X: halogen group, n: integer of <NUM> or more and <NUM> or less) (for example, <NUM>-chloro-<NUM>-propanol) under alkaline conditions, or with a both-terminal alkanediol (for example, <NUM>,<NUM>-propanediol) having <NUM> or more and <NUM> or less carbon atoms under acid catalyst conditions, and further adding to the obtained internal diol an alkylene oxide having <NUM> or more and <NUM> or less carbon atoms. When the internal olefin is a mixed product of two or more internal olefins that have a same total number of carbon atoms but a double bond at different positions therebetween, the internal two hydrophilic groups-containing compound obtained by the above-described production method is a mixed product of two or more compounds that have a same total number of carbon atoms of R<NUM> and R<NUM>, but are different in number of carbon atoms of each of R<NUM> and R<NUM>.

The internal olefin used for the production of the internal two hydrophilic groups-containing compound may contain a terminal olefin. In such a case, the content of the terminal olefin included in the olefin is, for example, <NUM> mass% or more, <NUM> mass% or more, and <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less.

A precursor compound is a compound, represented by a chemical formula (<NUM>) below in which A<NUM>' is -O-R<NUM>OH, for producing the compound represented by the chemical formula (<NUM>) in which A<NUM> is -O-R<NUM>O(-A<NUM>O)n-H, or
a compound, represented by the chemical formula (<NUM>) below in which A<NUM>' is -O-A<NUM>OH, for producing the compound represented by the chemical formula (<NUM>) in which A<NUM> is -O-A<NUM>O(-A<NUM>O)q-H. <CHM>
<CHM>
(In the chemical formula, R<NUM> and R<NUM> is an aliphatic hydrocarbon group, X is a single bond or a hydrocarbon group having <NUM> or more and <NUM> or less carbon atoms, the total number of carbon atoms of R<NUM>, R<NUM>, and X is <NUM> or more and <NUM> or less, A<NUM>' is -OH, A<NUM>' is -O-R<NUM>OH or -O-A<NUM>OH, R<NUM> is an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms, and A<NUM> is a linear alkane-α,ω-diyl group having <NUM> or more and <NUM> or less carbon atoms.

The aspects and suitable aspect of R<NUM> and R<NUM>, and X in the chemical formula (<NUM>) are the same as the aspects and suitable aspects of R<NUM> and R<NUM>, and X in the chemical formula (<NUM>).

R<NUM> is an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms, the alkanediyl group may be either a linear or branched alkanediyl group, but is preferably a linear alkanediyl group. The alkanediyl group has preferably <NUM> or more and <NUM> or less carbon atoms, more preferably <NUM> or more and <NUM> or less carbon atoms, further preferably <NUM> or more and <NUM> or less carbon atoms.

A<NUM> has <NUM> or more and <NUM> or less carbon atoms, preferably <NUM> or more and <NUM> or less carbon atoms, more preferably <NUM> or more and <NUM> or less carbon atoms, further preferably <NUM> or <NUM> carbon atoms.

The precursor compound preferably includes two or more compounds that have a same total number of carbon atoms of R<NUM>, R<NUM>, and X, but are different in number of carbon atoms of each of R<NUM> and R<NUM>, from the viewpoints of production efficiency and easiness of production.

The precursor compound more preferably includes two or more compounds that have a single bond as X and a same total number of carbon atoms of R<NUM> and R<NUM>, but are different in number of carbon atoms of each of R<NUM> and R<NUM>, from the viewpoints of production efficiency and easiness of production.

When the precursor compound includes two or more compounds that have a single bond as X, and are different in total number of carbon atoms of R<NUM> and R<NUM>, the total content of a compound having a total number of carbon atoms of R<NUM> and R<NUM> of <NUM> and a compound having a total number of carbon atoms of R<NUM> and R<NUM> of <NUM> is, in the whole precursor compound, preferably <NUM> mass% or more, more preferably <NUM> mass% or more, further preferably <NUM> mass% or more, still further preferably <NUM> mass%.

When the precursor compound includes two or more compounds that have a same total number of carbon atoms of R<NUM>, R<NUM>, and X, but are different in number of carbon atoms of each of R<NUM> and R<NUM>, the content proportion of a compound in which R<NUM> has <NUM> or more carbon atoms and R<NUM> has <NUM> or more carbon atoms is, in the whole precursor compound, preferably <NUM> mass% or more, more preferably <NUM> mass% or more, further preferably <NUM> mass% or more, and preferably <NUM> mass% or less, more preferably <NUM> mass% or less, further preferably <NUM> mass% or less.

The method for producing the precursor compound is not particularly limited, and the precursor compound can be produced, for example, by oxidizing a double bond of an internal olefin with a peroxide such as hydrogen peroxide and peracetic acid to synthesize an internal epoxide, and adding to the obtained internal epoxide glycol having <NUM> or more and <NUM> or less carbon atoms, or a both-terminal alkanediol having <NUM> or more and <NUM> or less carbon atoms. When the internal olefin is a mixed product of two or more internal olefins that have a same total number of carbon atoms but a double bond at different positions therebetween, the precursor compound obtained by the above-described production method is a mixed product of two or more compounds that have a same total number of carbon atoms of R<NUM>, R<NUM>, and X, but are different in number of carbon atoms of each of R<NUM> and R<NUM>.

The internal olefin used for the production of the precursor compound may contain a terminal olefin. In such a case, the content of the terminal olefin included in the olefin is, for example, <NUM> mass% or more, <NUM> mass% or more, and <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less.

A surfactant composition according to the present invention contains at least the internal two hydrophilic groups-containing compound.

The content of the internal two hydrophilic groups-containing compound in the surfactant composition is not particularly limited, but is preferably <NUM> mass% or more, more preferably <NUM> mass% or more, further preferably <NUM> mass% or more, still further preferably <NUM> mass% or more from the viewpoint of reducing transportation and storage costs, and is preferably <NUM> mass% or less, more preferably <NUM> mass% or less, further preferably <NUM> mass% or less from the viewpoint of prevention of gelation.

The surfactant composition according to the present invention preferably contains water from the viewpoint of easiness of handling. The water is not particularly limited, but is preferably purified water such as ion-exchanged water, distilled water, and reverse osmosis water.

The water can be used in the amount corresponding to the balance other than the internal two hydrophilic groups-containing compound and the other components. The content of the water in the composition can be set to <NUM> mass% or more, <NUM> mass% or more, <NUM> mass% or more, and can be set to <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less.

The surfactant composition according to the present invention can contain a surfactant or a solvent described below from the viewpoint of storage stability.

The addition of the solvent described below to the surfactant composition according to the present invention is not limited. From the viewpoints of sustainability, environmental burden, safety, and the like, however, the content of the solvent in the surfactant composition is preferably <NUM> mass% or less, more preferably <NUM> mass% or less, further preferably <NUM> mass% or less, still further preferably <NUM> mass% or less, still further preferably <NUM> mass %. That is, the surfactant composition preferably contains no solvent.

The surfactant composition may be an emulsifier composition, a wetting agent composition, or a penetrant composition. That is, the surfactant composition according to the present invention may be an emulsifier composition, a wetting agent composition, or a penetrant composition containing one or more compounds represented by the chemical formula (<NUM>).

A detergent composition according to the present invention contains at least the internal two hydrophilic groups-containing compound.

The content of the internal two hydrophilic groups-containing compound in the detergent composition is not particularly limited, but is preferably <NUM> mass% or more, more preferably <NUM> mass% or more, further preferably <NUM> mass% or more, still further preferably <NUM> mass% or more from the viewpoint of improving detergency, and is preferably <NUM> mass% or less, more preferably <NUM> mass% or less, further preferably <NUM> mass% or less from the viewpoint of low-concentration detergency and prevention of gelation.

The detergent composition according to the present invention can contain any component used for detergents, such as a surfactant different from the internal two hydrophilic groups-containing compound, water, a solvent, fragrance, a dye, a defoamer, a preservative, a moisturizing agent, an antibacterial agent, an antidandruff agent, a pearlizing agent, a vitamin compound, a thickener, a pH adjuster, a bleacher, a chelating agent, a watersoluble salt, and an oil solution, as long as the component does not inhibit the effects of the present invention.

As the surfactant different from the internal two hydrophilic groups-containing compound, known surfactants can be used without any limitation. Examples of the surfactant include an anionic surfactant, a nonionic surfactant, an amphoteric surfactant, and a cationic surfactant.

The water is not particularly limited, but is preferably purified water such as ion-exchanged water, distilled water, and reverse osmosis water.

The water can be used in the amount corresponding to the balance other than the internal two hydrophilic groups-containing compound and the other components. The content of the water in the composition can be set to <NUM> mass% or more, <NUM> mass% or more, <NUM> mass% or more, <NUM> mass% or more, <NUM> mass% or more, <NUM> mass% or more, and can be set to <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less, <NUM> mass% or less, <NUM> mass%.

The detergent composition according to the present invention can contain a solvent in order to, for example, increase low-temperature stability and washing performance.

The addition of the solvent described above to the detergent composition according to the present invention is not limited. From the viewpoints of sustainability, environmental burden, safety, and the like, however, the content of the solvent in the detergent composition is preferably <NUM> mass% or less, more preferably <NUM> mass% or less, further preferably <NUM> mass% or less, still further preferably <NUM> mass% or less, still further preferably <NUM> mass %. That is, the detergent composition preferably contains no solvent.

The detergent composition according to the present invention can be prepared, for example, by mixing the internal two hydrophilic groups-containing compound and a component other than the compound.

When the detergent composition containing another component is prepared, the preparation order is not particularly limited, and the detergent composition may be prepared by preparing a detergent composition containing the internal two hydrophilic groups-containing compound and then blending the other component in the detergent composition.

From the viewpoint of obtaining the detergent composition having the components uniformly dissolved therein, the detergent composition is preferably left to stand still at a prescribed temperature for a prescribed time after mixing. The temperature at which the detergent composition is left to stand still is preferably <NUM> or more, more preferably <NUM> or more, further preferably <NUM> or more, still further preferably <NUM> or more from the viewpoint of obtaining the detergent composition having the components uniformly dissolved therein, and is preferably <NUM> or less, more preferably <NUM> or less, further preferably <NUM> or less, still further preferably <NUM> or less, still further preferably <NUM> or less, still further preferably <NUM> or less from the viewpoint of economic efficiency. The time during which the detergent composition is left to stand still depends on the temperature, but is preferably <NUM> hour or more, more preferably <NUM> hours or more, further preferably <NUM> hours or more, still further preferably <NUM> hours or more, still further preferably <NUM> hours or more, still further preferably <NUM> days or more, still further preferably <NUM> days or more from the viewpoint of sufficiently uniformly dissolving the components, and is preferably <NUM> month or less, more preferably <NUM> days or less, further preferably <NUM> days or less from the viewpoint of economic efficiency.

The surfactant composition or the detergent composition according to the present invention is used as a detergent such as a laundry liquid detergent, a dishwashing detergent, shampoo, a body cleanser, a detergent for precision components, and a detergent for hard surfaces. The surfactant composition or the detergent composition according to the present invention can be added and dissolved in water and thereby applied to various washing uses described above.

The present invention and preferred embodiments of the present invention are described below.

Hereinafter, the present invention is specifically described on the basis of examples. The content(%) of the components in tables is represented in mass% unless otherwise described. The measurement methods are as follows.

The position of a double bond in a prepared internal olefin was measured by gas chromatography (hereinafter, abbreviated as GC). Specifically, the internal olefin was reacted with dimethyl sulfide into a dithionate derivative, and the components were then separated by GC. The position of a double bond in the internal olefin was obtained from the peak areas of the components. The apparatus used for the measurement and the analysis conditions are as follows.

To <NUM> of a reaction refined product was added <NUM> of TMS-I (manufactured by GL Sciences Inc. ), and the mixture was stirred and left to stand still for <NUM> minutes. Then, <NUM> of hexane was added, and the mixture was filtered and then measured by GC. The measurement conditions are as follows.

Into a flask equipped with a stirrer were charged <NUM> (<NUM> mol) of <NUM>-hexadecanol (product name: KALCOL <NUM>, manufactured by Kao Corporation) and <NUM> (<NUM> wt% relative to raw material alcohol) of γ-alumina (STREM Chemicals, Inc. ) as a solid acid catalyst, and the mixture was reacted under stirring at <NUM> for <NUM> hours with a flow of nitrogen (<NUM>/min) through the system. After the completion of the reaction, the alcohol conversion rate was <NUM>% and the C16 olefin purity was <NUM>%. The obtained crude C16 internal olefin was transferred to a distiller, and was distilled at <NUM> to <NUM>/<NUM> mmHg to give a C16 internal olefin having an olefin purity of <NUM>%. The double bond distribution in the C16 obtained internal olefin was <NUM>% at the C1 position, <NUM>% at the C2 position, <NUM>% at the C3 position, <NUM>% at the C4 position, <NUM>% at the C5 position, <NUM>% at the C6 position, and <NUM>% at the C7 position and the C8 position in total.

Into a reactor equipped with a stirrer were charged <NUM> (<NUM> kmol) of <NUM>-hexadecanol (product name: KALCOL <NUM>, manufactured by Kao Corporation) and <NUM> (<NUM> wt% relative to raw material alcohol) of activated alumina GP-<NUM> (Mizusawa Industrial Chemicals, Ltd. ) as a solid acid catalyst, and the mixture was reacted under stirring at <NUM> for <NUM> hours with a flow of nitrogen (<NUM>/min) through the system. After the completion of the reaction, the alcohol conversion rate was <NUM>% and the C16 olefin purity was <NUM>%. The obtained crude C16 internal olefin was transferred to a distiller, and was distilled at <NUM> to <NUM>/<NUM> mmHg to give a C16 internal olefin having an olefin purity of <NUM>%. The double bond distribution in the obtained C16 internal olefin was <NUM>% at the C1 position, <NUM>% at the C2 position, <NUM>% at the C3 position, <NUM>% at the C4 position, <NUM>% at the C5 position, <NUM>% at the C6 position, and <NUM>% at the C7 position and the C8 position in total.

Into a reactor equipped with a stirrer were charged <NUM> (<NUM> kmol) of <NUM>-octadecanol (product name: KALCOL <NUM>, manufactured by Kao Corporation) and <NUM> (<NUM> wt% relative to raw material alcohol) of activated alumina GP-<NUM> (Mizusawa Industrial Chemicals, Ltd. ) as a solid acid catalyst, and the mixture was reacted under stirring at <NUM> for <NUM> hours with a flow of nitrogen (<NUM>/min) through the system. After the completion of the reaction, the alcohol conversion rate was <NUM>% and the C18 olefin purity was <NUM>%. The obtained crude C18 internal olefin was transferred to a distiller, and was distilled at <NUM> to <NUM>/<NUM> mmHg to give a C18 internal olefin having an olefin purity of <NUM>%. The double bond distribution in the obtained C18 internal olefin was <NUM>% at the C1 position, <NUM>% at the C2 position, <NUM>% at the C3 position, <NUM>% at the C4 position, <NUM>% at the C5 position, <NUM>% at the C6 position, <NUM> at the C7 position, and <NUM>% at the C8 position and the C9 position in total.

Into a flask equipped with a stirrer were charged <NUM> (<NUM> mol) of the C16 internal olefin obtained in Production Example A1 or Production Example A1', <NUM> (<NUM> mol) of acetic acid (manufactured by Wako Pure Chemical Industries, Ltd. ), <NUM> (<NUM> mol) of sulfuric acid (manufactured by Wako Pure Chemical Industries, Ltd. ), <NUM> (<NUM> mol) of <NUM>% hydrogen peroxide (manufactured by Wako Pure Chemical Industries, Ltd. ), and <NUM> (<NUM> mol) of sodium sulfate (manufactured by Wako Pure Chemical Industries, Ltd. ), and the mixture was reacted at <NUM> for <NUM> hours. Thereafter, the mixture was heated to <NUM> and further reacted for <NUM> hours. After the reaction, the mixture was separated into layers, an aqueous layer was removed, and an oil layer was washed with ion-exchanged water, a saturated aqueous sodium carbonate solution (manufactured by Wako Pure Chemical Industries, Ltd. ), a saturated aqueous sodium sulfite solution (manufactured by Wako Pure Chemical Industries, Ltd. ), and <NUM>% saline (manufactured by Wako Pure Chemical Industries, Ltd. ), and concentrated in an evaporator to give <NUM> of a C16 internal epoxide.

Into a flask equipped with a stirrer were charged <NUM> (<NUM> mol) of the C18 internal olefin obtained in Production Example A2, <NUM> (<NUM> mol) of acetic acid (manufactured by Wako Pure Chemical Industries, Ltd. ), <NUM> (<NUM> mol) of sulfuric acid (manufactured by Wako Pure Chemical Industries, Ltd. ), and <NUM> (<NUM> mol) of <NUM>% hydrogen peroxide (manufactured by Wako Pure Chemical Industries, Ltd. ), and the mixture was reacted at <NUM> for <NUM> hours. Thereafter, the mixture was heated to <NUM> and further reacted for <NUM> hours. After the reaction, the mixture was separated into layers, an aqueous layer was removed, and an oil layer was washed with ion-exchanged water, a saturated aqueous sodium carbonate solution (manufactured by Wako Pure Chemical Industries, Ltd. ), a saturated aqueous sodium sulfite solution (manufactured by Wako Pure Chemical Industries, Ltd. ), and ion-exchanged water, and concentrated in an evaporator to give <NUM> of a C18 internal epoxide.

Into a flask equipped with a stirrer were charged <NUM> (<NUM> mol) of <NUM>,<NUM>-butanediol (manufactured by Wako Pure Chemical Industries, Ltd. ) and <NUM> (<NUM> mmol) of <NUM>% sulfuric acid (manufactured by Wako Pure Chemical Industries, Ltd. ), and the mixture was heated to <NUM>. Thereafter, <NUM> (<NUM> mol) of the C16 internal epoxide obtained in Production Example B1 were added dropwise over <NUM> hour, and then the mixture was reacted at <NUM>/<NUM> minutes. Hexane was added to the liquid obtained by this reaction, and the mixture was washed with ion-exchanged water and then concentrated under reduced pressure in an evaporator to give <NUM> of a C16-<NUM>,<NUM>-butanediol condensation product. The diol positional distribution (positional distribution of carbon atoms having -OH and - OCH<NUM>CH(C<NUM>H<NUM>)OH) in the obtained C16-<NUM>,<NUM>-butanediol condensation product was <NUM>% at the C1,<NUM> position, <NUM>% at the C2,<NUM> position, <NUM>% at the C3,<NUM> position, <NUM>% at the C4,<NUM> position, and <NUM>% at the C5,<NUM> position, the C6,<NUM> position, the C7,<NUM> position, and the C8,<NUM> position in total.

A C16-<NUM>,<NUM>-butanediol condensation product (<NUM>) was obtained by the same method as in Production Example C1 except that <NUM>,<NUM>-butanediol (manufactured by Wako Pure Chemical Industries, Ltd. ) was used in place of <NUM>,<NUM>-butanediol (manufactured by Wako Pure Chemical Industries, Ltd. The diol positional distribution (positional distribution of carbon atoms having -OH and - O(CH<NUM>)<NUM>CH(CH<NUM>)OH) in the obtained C16-<NUM>,<NUM>-butanediol condensation product was <NUM>% at the C1,<NUM> position, <NUM>% at the C2,<NUM> position, <NUM>% at the C3,<NUM> position, <NUM>% at the C4,<NUM> position, and <NUM>% at the C5,<NUM> position, the C6,<NUM> position, the C7,<NUM> position, and the C8,<NUM> position in total.

Into a flask equipped with a stirrer were charged <NUM> (<NUM> mol) of <NUM>,<NUM>-butanediol (manufactured by Wako Pure Chemical Industries, Ltd. ) and <NUM> (<NUM> mmol) of <NUM>% sulfuric acid (manufactured by Wako Pure Chemical Industries, Ltd. ), and the mixture was heated to <NUM>. Thereafter, <NUM> (<NUM> mol) of the C16 internal epoxide obtained in Production Example B1 were added dropwise over <NUM> hour, and then the mixture was reacted at <NUM>/<NUM> minutes. Hexane was added to the liquid obtained by this reaction, and the mixture was washed with ion-exchanged water and then concentrated under reduced pressure in an evaporator to give <NUM> of a C16-<NUM>,<NUM>-butanediol condensation product. The diol positional distribution (positional distribution of carbon atoms having -OH and - O(CH<NUM>)<NUM>OH) in the obtained C16-<NUM>,<NUM>-butanediol condensation product was <NUM>% at the C1,<NUM> position, <NUM>% at the C2,<NUM> position, <NUM>% at the C3,<NUM> position, <NUM>% at the C4,<NUM> position, and <NUM>% at the C5,<NUM> position, the C6,<NUM> position, the C7,<NUM> position, and the C8,<NUM> position in total.

Into a flask equipped with a stirrer were charged <NUM> (<NUM> mol) of <NUM>,<NUM>-hexanediol (manufactured by Wako Pure Chemical Industries, Ltd. ) and <NUM> (<NUM> mmol) of <NUM>% sulfuric acid (manufactured by Wako Pure Chemical Industries, Ltd. ), and the mixture was heated to <NUM>. Thereafter, <NUM> (<NUM> mol) of the C16 internal epoxide obtained in Production Example B1 were added dropwise over <NUM> minutes, and then the mixture was reacted at <NUM>/<NUM> hour. Hexane was added to the liquid obtained by this reaction, and the mixture was washed with ion-exchanged water and then concentrated under reduced pressure in an evaporator to give <NUM> of a C16-<NUM>,<NUM>-hexanediol condensation product. The diol positional distribution (positional distribution of carbon atoms having -OH and - O(CH<NUM>)<NUM>OH) in the obtained C16-<NUM>,<NUM>-hexanediol condensation product was <NUM>% at the C1,<NUM> position, <NUM>% at the C2,<NUM> position, <NUM>% at the C3,<NUM> position, <NUM>% at the C4,<NUM> position, and <NUM>% at the C5,<NUM> position, the C6,<NUM> position, the C7,<NUM> position, and the C8,<NUM> position in total.

<NUM>,<NUM>-Butanediol (manufactured by Wako Pure Chemical Industries, Ltd. ) in an amount of <NUM> (<NUM> mol) was charged into a flask equipped with a stirrer and heated to <NUM>. Thereafter, <NUM> (<NUM> mol) of the C18 internal epoxide obtained in Production Example B2 were added dropwise over <NUM> hour, and then the mixture was reacted at <NUM>/<NUM> hours. Hexane was added to the liquid obtained by this reaction, and the mixture was washed with ion-exchanged water and then concentrated under reduced pressure in an evaporator to give <NUM> of a C18-<NUM>,<NUM>-butanediol condensation product. The diol positional distribution (positional distribution of carbon atoms having -OH and -O(CH<NUM>)<NUM>OH) in the obtained C18-<NUM>,<NUM>-butanediol condensation product was <NUM>% at the C1,<NUM> position, <NUM>% at the C2,<NUM> position, <NUM>% at the C3,<NUM> position, <NUM>% at the C4,<NUM> position, <NUM>% at the C5,<NUM> position, and <NUM>% at the C6,<NUM> position, the C7,<NUM> position, the C8,<NUM> position, and the C9,<NUM> in total.

Ethylene glycol (manufactured by Wako Pure Chemical Industries, Ltd. ) in an amount of <NUM> (<NUM> mol) was charged into a flask equipped with a stirrer and heated to <NUM>. Thereafter, <NUM> (<NUM> mol) of the C16 internal epoxide obtained in Production Example B1 were added dropwise over <NUM> hour, and then the mixture was reacted at <NUM>/<NUM> hours. Hexane was added to the liquid obtained by this reaction, and the mixture was washed with ion-exchanged water and then concentrated under reduced pressure in an evaporator to give <NUM> of a C16-ethylene glycol condensation product. The diol positional distribution (positional distribution of carbon atoms having -OH and O(CH<NUM>)<NUM>OH) in the obtained C16-ethylene glycol condensation product was <NUM>% at the C1,<NUM> position, <NUM>% at the C2,<NUM> position, <NUM>% at the C3,<NUM> position, <NUM>% at the C4,<NUM> position, <NUM>% at the C5,<NUM> position, and <NUM>% at the C6,<NUM> position, the C7,<NUM> position, and the C8,<NUM> position in total.

Into a flask equipped with a stirrer were charged <NUM> (<NUM> mol) of <NUM>,<NUM>-propanediol (manufactured by Wako Pure Chemical Industries, Ltd. ), <NUM> (<NUM> mmol) of <NUM>% sulfuric acid (manufactured by Wako Pure Chemical Industries, Ltd. ), and <NUM> (<NUM> mol) of the C16 internal epoxide obtained in Production Example B1, and the mixture was reacted at <NUM>/<NUM> hour. Hexane was added to the liquid obtained by this reaction, and the mixture was washed with ion-exchanged water and then concentrated under reduced pressure in an evaporator to give <NUM> of a C16-<NUM>,<NUM>-propanediol condensation product. The diol positional distribution (positional distribution of carbon atoms having -OH and -O(CH<NUM>)<NUM>OH) in the obtained C16-<NUM>,<NUM>-propanediol condensation product was <NUM>% at the C1,<NUM> position, <NUM>% at the C2,<NUM> position, <NUM>% at the C3,<NUM> position, <NUM>% at the C4,<NUM> position, and <NUM>% at the C5,<NUM> position, the C6,<NUM> position, the C7,<NUM> position, and the C8,<NUM> position in total.

Into a flask equipped with a stirrer were charged <NUM> (<NUM> mol) of <NUM>,<NUM>-propanediol (manufactured by Wako Pure Chemical Industries, Ltd. ), <NUM> (<NUM> mmol) of <NUM>% sulfuric acid (manufactured by Wako Pure Chemical Industries, Ltd. ), and <NUM> (<NUM> mol) of the C18 internal epoxide obtained in Production Example B2, and the mixture was reacted at <NUM>/<NUM> hour. Hexane was added to the liquid obtained by this reaction, and the mixture was washed with ion-exchanged water and then concentrated under reduced pressure in an evaporator to give <NUM> of a C18-<NUM>,<NUM>-propanediol condensation product. The diol positional distribution (positional distribution of carbon atoms having -OH and -O(CH<NUM>)<NUM>OH) in the obtained C18-<NUM>,<NUM>-propanediol condensation product was <NUM>% at the C1,<NUM> position, <NUM>% at the C2,<NUM> position, <NUM>% at the C3,<NUM> position, <NUM>% at the C4,<NUM> position, <NUM>% at the C5,<NUM> position, and <NUM>% at the C6,<NUM> position, the C7,<NUM> position, the C8,<NUM> position, and the C9,<NUM> in total.

<NUM>,<NUM>-Butanediol (manufactured by Wako Pure Chemical Industries, Ltd. ) in an amount of <NUM> (<NUM> mol) was charged into a flask equipped with a stirrer and heated to <NUM>. Then, <NUM> (<NUM> mol) of the C18 internal epoxide obtained in Production Example B2 were added dropwise over <NUM> hour. Thereafter, the mixture was reacted at <NUM>/<NUM> hours. Hexane was added to the liquid obtained by this reaction, and the mixture was washed with ion-exchanged water and then concentrated under reduced pressure in an evaporator to give <NUM> of a C18-<NUM>,<NUM>-butanediol condensation product. The diol positional distribution (positional distribution of carbon atoms having -OH and - O(CH<NUM>)<NUM>OH) in the obtained C18-<NUM>,<NUM>-butanediol condensation product was <NUM>% at the C1,<NUM> position, <NUM>% at the C2,<NUM> position, <NUM>% at the C3,<NUM> position, <NUM>% at the C4,<NUM> position, <NUM>% at the C5,<NUM> position, and <NUM>% at the C6,<NUM> position, the C7,<NUM> position, the C8,<NUM> position, and the C9,<NUM> in total.

Into a <NUM>-L autoclave equipped with a stirrer, a thermometer, and an AO inlet tube were charged <NUM> (<NUM> mol, raw material) of the C16-<NUM>,<NUM>-butanediol condensation product obtained in Production Example C1 and <NUM> (<NUM> mol) of <NUM>% KOH, and after nitrogen substitution was performed, the mixture was subjected to dehydration at <NUM> and -<NUM> MPa for <NUM> hour. Thereafter, <NUM> (<NUM> mol) of EO were fed to the mixture and thus added at an initial nitrogen pressure of <NUM> MPa and <NUM> ± <NUM>. Thereafter, <NUM> (<NUM> mol) of acetic acid were added and the mixture was thereby neutralized to give C16-<NUM>,2BD-EO14). The average number of added moles of EO in the obtained product was confirmed by <NUM>H-NMR.

The products shown in Tables <NUM> and <NUM> were obtained in the same manner as in Example <NUM> unless otherwise described, except that the raw material, the type of AO, KOH, and acetic acid shown in Table <NUM> were used in the usage amounts shown in Table <NUM>. The compounds shown in Tables <NUM> and <NUM> are as follows. AO shown in Table <NUM> represents alkylene oxide, EO represents ethylene oxide, and PO represents propylene oxide. AO shown in Table <NUM> represents alkyleneoxy group, EO represents ethyleneoxy group, PO represents propyleneoxy group, branched BO represents branched butyleneoxy group, linear BO represents linear butyleneoxy group, and linear HO represents linear hexyleneoxy group.

Into a <NUM>-L autoclave equipped with a stirrer, a thermometer, and an AO inlet tube were charged <NUM> (<NUM> mol) of the C16-<NUM>,<NUM>-butanediol condensation product obtained in Production Example C3 and <NUM> (<NUM> mol) of <NUM>% KOH, and after nitrogen substitution was performed, the mixture was subjected to dehydration at <NUM> and - <NUM> MPa for <NUM> hour. Thereafter, <NUM> (<NUM> mol) of EO were fed to the mixture and thus added at an initial nitrogen pressure of <NUM> MPa and <NUM> ± <NUM>. Subsequently, <NUM> (<NUM> mol) of PO were fed to the mixture and thus added at <NUM> ± <NUM> and then <NUM> (<NUM> mol) of EO were fed and thus added at <NUM> ± <NUM>. Thereafter, <NUM> (<NUM> mol) of acetic acid were added and the mixture was thereby neutralized to give C16-<NUM>,4BD-EO6-PO2-EO6. The average numbers of added moles of EO and PO in the obtained product were confirmed by <NUM>H-NMR.

Into a <NUM>-L autoclave equipped with a stirrer, a thermometer, and an AO inlet tube were charged <NUM> (<NUM> mol) of the C16-<NUM>,<NUM>-butanediol condensation product obtained in Production Example C3 and <NUM> (<NUM> mol) of <NUM>% KOH, and after nitrogen substitution was performed, the mixture was subjected to dehydration at <NUM> and - <NUM> MPa for <NUM> hour. Thereafter, <NUM> (<NUM> mol) of EO were fed to the mixture and thus added at an initial nitrogen pressure of <NUM> MPa and <NUM> ± <NUM>. Subsequently, <NUM> (<NUM> mol) of PO were fed to the mixture and thus added at <NUM> ± <NUM> and then <NUM> (<NUM> mol) of EO were fed and thus added at <NUM> ± <NUM>. Thereafter, <NUM> (<NUM> mol) of acetic acid were added and the mixture was thereby neutralized to give C16-<NUM>,4BD-EO8-PO2-EO9. The average numbers of added moles of EO and PO in the obtained product were confirmed by <NUM>H-NMR.

Into a <NUM>-L autoclave equipped with a stirrer, a thermometer, and an AO inlet tube were charged <NUM> (<NUM> mol, raw material) of the C16-<NUM>,<NUM>-propanediol condensation product obtained in Production Example C7 and <NUM> (<NUM> mol) of <NUM>% KOH, and after nitrogen substitution was performed, the mixture was subjected to dehydration at <NUM> and -<NUM> MPa for <NUM> hour. Thereafter, <NUM> (<NUM> mol) of EO were fed to the mixture and thus added at an initial nitrogen pressure of <NUM> MPa and <NUM> ± <NUM>. Thereafter, <NUM> (<NUM> mol) of acetic acid were added and the mixture was thereby neutralized to give C16-<NUM>,3PD-EO9. The average number of added moles of EO in the obtained product was confirmed by <NUM>H-NMR.

The products shown in Tables <NUM> and <NUM> were obtained in the same manner as in Example <NUM> unless otherwise described, except that the raw material, the type of AO, KOH, and acetic acid shown in Table <NUM> were used in the usage amounts shown in Table <NUM>. The compounds shown in Tables <NUM> and <NUM> are as follows. AO shown in Table <NUM> represents alkylene oxide, EO represents ethylene oxide, and PO represents propylene oxide. AO shown in Table <NUM> represents alkyleneoxy group, EO represents ethyleneoxy group, PO represents propyleneoxy group, linear PO represents linear propyleneoxy group, linear BO represents linear butyleneoxy group, and linear HO represents linear hexyleneoxy group.

Into a <NUM>-L autoclave equipped with a stirrer, a thermometer, and an AO inlet tube were charged <NUM> (<NUM> mol) of the C16-<NUM>,<NUM>-propanediol condensation product obtained in Production Example C7 and <NUM> (<NUM> mol) of <NUM>% KOH, and after nitrogen substitution was performed, the mixture was subjected to dehydration at <NUM> and - <NUM> MPa for <NUM> hour. Thereafter, <NUM> (<NUM> mol) of EO were fed to the mixture and thus added at an initial nitrogen pressure of <NUM> MPa and <NUM> ± <NUM>. Subsequently, <NUM> (<NUM> mol) of PO were fed to the mixture and thus added at <NUM> ± <NUM>. Thereafter, <NUM> (<NUM> mol) of acetic acid were added and the mixture was thereby neutralized to give C16-<NUM>,3PD-EO12-PO2. The average numbers of added moles of EO and PO in the obtained product were confirmed by <NUM>H-NMR.

Into a <NUM>-L autoclave equipped with a stirrer, a thermometer, and an AO inlet tube were charged <NUM> (<NUM> mol) of the C16-<NUM>,<NUM>-propanediol condensation product obtained in Production Example C7 and <NUM> (<NUM> mol) of <NUM>% KOH, and after nitrogen substitution was performed, the mixture was subjected to dehydration at <NUM> and - <NUM> MPa for <NUM> hour. Thereafter, <NUM> (<NUM> mol) of EO were fed to the mixture and thus added at an initial nitrogen pressure of <NUM> MPa and <NUM> ± <NUM>. Subsequently, <NUM> (<NUM> mol) of PO were fed to the mixture and thus added at <NUM> ± <NUM> and then <NUM> (<NUM> mol) of EO were fed and thus added at <NUM> ± <NUM>. Thereafter, <NUM> (<NUM> mol) of acetic acid were added and the mixture was thereby neutralized to give C16-<NUM>,3PD-EO6-PO2-EO6. The average numbers of added moles of EO and PO in the obtained product were confirmed by <NUM>H-NMR.

The internal two hydrophilic groups-containing compounds produced in the examples and the comparative examples were evaluated as follows.

The internal two hydrophilic groups-containing compound produced in each of the examples and the comparative examples was taken into a beaker, ion-exchanged water was added to give a <NUM> or <NUM> mass% solution, and the solution was heated to uniformly dissolve the compound. A detergent composition was thus obtained. Thereafter, the detergent composition was cooled to <NUM>, left for <NUM> day, then heated to the temperature shown in Table <NUM> or <NUM>, and left to stand still for <NUM> days. Thereafter, the phase state of the detergent composition was observed. The phase state was determined as follows according to the presence or absence of flowability and the presence or absence of optical anisotropy determined by observation with a polarizer.

Further, after the determination of the phase state, the detergent composition in a micelle state was evaluated as ○ (passed) and the detergent in a liquid crystal or solid state as × (not passed) in terms of low-temperature stability/flowability.

Model-sebum artificially soiled fabric was prepared by applying a model-sebum artificially soiling liquid having the following composition to fabric (cotton <NUM> (manufactured by Senshoku shizai K. Tanigashira shouten)). The application of the model-sebum artificially soiling liquid to the fabric was carried out by performing gravure-roll-coater printing on the fabric with the artificially soiling liquid. The step of applying the model-sebum artificially soiling liquid to the fabric and thus preparing the model-sebum artificially soiled fabric was performed at a gravure-roll cell volume of <NUM><NUM>/m<NUM>, an application rate of <NUM>/min, a drying temperature of <NUM>, and a drying time of <NUM>. Thereafter, the fabric was cut into a size of <NUM> × <NUM>.

The composition of the model-sebum artificially soiling liquid: <NUM> mass% of lauric acid, <NUM> mass% of myristic acid, <NUM> mass% of pentadecanoic acid, <NUM> mass% of palmitic acid, <NUM> mass% of heptadecanoic acid, <NUM> mass% of stearic acid, <NUM> mass% of oleic acid, <NUM> mass% of triolein, <NUM> mass% of n-hexadecyl palmitate, <NUM> mass% of squalene, <NUM> mass% of egg-white lecithin liquid crystal, <NUM> mass% of Kanuma red soil, <NUM> mass% of carbon black, and the balance water (total <NUM> mass%).

The washing operation was performed using a tergotometer (manufactured by Ueshima Seisakusho Co. Washing water was obtained by charging calcium chloride and magnesium chloride at a mass ratio of <NUM> : <NUM> into ion-exchanged water and adjusting the hardness of the mixture to <NUM>°dH (see <CIT> for the method for measuring German hardness). A washing liquid was obtained by mixing the internal two hydrophilic groups-containing compound prepared in each example or each comparative example with the washing water so that the concentration of the washing liquid was <NUM>, <NUM>, or <NUM> ppm. Into a <NUM>-L washing test stainless-steel beaker were charged <NUM> of the washing liquid and <NUM> pieces of the model-sebum artificially soiled fabric. The temperature of the washing liquid was <NUM>. The model-sebum artificially soiled fabric was washed by the tergotometer at <NUM> rpm for <NUM> minutes. After the washing, the fabric was dehydrated and dried for <NUM> hours in an environment of <NUM> and <NUM>% RH.

The detergency rate (%) of the model-sebum artificially soiled fabric was measured by the following method, and the average value of the <NUM> pieces of the fabric was obtained. Table <NUM> or <NUM> shows the results. The reflectance at <NUM> of unsoiled original fabric and the soiled fabric before and after washing was measured by a chromometer (manufactured by NIPPON DENSHOKU INDUSTRIES CO. , Z-300A), and the detergency rate (%) was obtained by the following equation.

As understood from Tables <NUM> and <NUM>, the internal two hydrophilic groups-containing compound according to the present invention has high detergency even when contained at a low concentration in the detergent composition, is less likely to cause gelation at low temperatures, and has excellent low-temperature stability and flowability.

Claim 1:
A compound represented by a chemical formula (<NUM>) below:
<CHM>
wherein R<NUM> and R<NUM> are each an aliphatic hydrocarbon group, X is a single bond or a hydrocarbon group having <NUM> or more and <NUM> or less carbon atoms, a total number of carbon atoms of R<NUM>, R<NUM>, and X is <NUM> or more and <NUM> or less, A<NUM> is -O(-A<NUM>O)m-H or -O(-A<NUM>O)p-H, A<NUM> is -O-R<NUM>O(-A<NUM>O)n-H or - O(-A<NUM>O)q+<NUM>-H, R<NUM> is an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms, m pieces of A<NUM> and n pieces of A<NUM> are each independently an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms, p pieces of A<NUM> and q + <NUM> pieces of A<NUM> are each independently an alkanediyl group having <NUM> or more and <NUM> or less carbon atoms, at least one piece of A<NUM> among the q + <NUM> pieces of A<NUM> is a linear alkane-α,ω-diyl group having <NUM> or more and <NUM> or less carbon atoms, m, n, p, and q are an average value and are each independently <NUM> or more, a total of m and n is more than <NUM> and <NUM> or less, and a total of p and q is more than <NUM> and <NUM> or less.