Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/04—Saturated ethers
  • C07C43/10—Saturated ethers of polyhydroxy compounds
  • C07C43/11—Polyethers containing —O—(C—C—O—)n units with ≤ 2 n≤ 10
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
  • C07C41/01—Preparation of ethers
  • C07C41/02—Preparation of ethers from oxiranes
  • C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/04—Saturated ethers
  • C07C43/13—Saturated ethers containing hydroxy or O-metal groups
  • C07C43/135—Saturated ethers containing hydroxy or O-metal groups having more than one ether bond
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
  • C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
  • C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
  • C08G65/2609—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aliphatic hydroxyl groups
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/66—Non-ionic compounds
  • C11D1/72—Ethers of polyoxyalkylene glycols
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
  • C11D1/66—Non-ionic compounds
  • C11D1/722—Ethers of polyoxyalkylene glycols having mixed oxyalkylene groups; Polyalkoxylated fatty alcohols or polyalkoxylated alkylaryl alcohols with mixed oxyalkylele groups
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/16—Organic compounds
  • C11D3/20—Organic compounds containing oxygen
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/16—Organic compounds
  • C11D3/20—Organic compounds containing oxygen
  • C11D3/2003—Alcohols; Phenols
  • C11D3/2041—Dihydric alcohols
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/16—Organic compounds
  • C11D3/20—Organic compounds containing oxygen
  • C11D3/2003—Alcohols; Phenols
  • C11D3/2041—Dihydric alcohols
  • C11D3/2044—Dihydric alcohols linear
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
  • C11D3/16—Organic compounds
  • C11D3/20—Organic compounds containing oxygen
  • C11D3/2068—Ethers
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/22—Organic compounds
  • C11D7/26—Organic compounds containing oxygen
  • C11D7/261—Alcohols; Phenols
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D7/00—Compositions of detergents based essentially on non-surface-active compounds
  • C11D7/22—Organic compounds
  • C11D7/26—Organic compounds containing oxygen
  • C11D7/261—Alcohols; Phenols
  • C11D7/262—Alcohols; Phenols fatty or with at least 8 carbon atoms in the alkyl or alkenyl chain
• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
  • C11D2111/00—Cleaning compositions characterised by the objects to be cleaned; Cleaning compositions characterised by non-standard cleaning or washing processes
  • C11D2111/10—Objects to be cleaned
  • C11D2111/12—Soft surfaces, e.g. textile

Definitions

• the present invention relates to a compound and a precursor compound for producing the compound.
• the present invention also relates to a surfactant composition and a detergent composition containing the above compound.
• Nonion surfactants are used in a wide range of fields such as laundry detergents, dishwashing detergents, household detergents, body cleaners, steel cleaners, and precision cleaners.
• the required performance includes high detergency, compoundability in products, and ease of handling.
• nonionic surfactant examples include alkylphenol ethoxylates, higher primary alcohol ethoxylates, higher secondary alcohol ethoxylates, fatty acid ethoxylates, and the like.
• alkylphenol ethoxylates, particularly nonylphenol ethoxylates have poor biodegradability and may have an adverse effect on the environment, and are being regulated.
• Patent Document 1 a higher secondary alcohol alkoxylate addition is obtained by adding an alkylene oxide to a higher secondary alcohol alkoxylate obtained by adding (poly) alkylene glycol to a double bond of a long chain olefin.
• the higher secondary alcohol alkoxylate adduct has a low pour point, is easy to handle, has good penetrating power, has good defoaming power, and has excellent detergency and emulsifying power.
• Patent Document 1 the higher secondary alcohol alkoxylate adduct of Patent Document 1 was not sufficiently satisfactory in terms of detergency and defoaming property.
• the present invention has been made in view of the above circumstances, and provides a compound that exhibits high detergency and is excellent in the speed of foam disappearance, and a precursor compound for producing the compound.
• the present invention also provides a surfactant composition and a detergent composition containing the compound.
• the present invention relates to a compound represented by the following chemical formula (1).
• R 1 and R 2 are aliphatic hydrocarbon groups
• X is a single bond or a hydrocarbon group having 1 or more and 5 or less carbon atoms
• the total carbon atoms of R 1 , R 2 and X are 2 or more.
• a 1 is -O (-A 11 O) l -H
• a 2 is -O-CH 2 -CH (-O (-A 21 O) m -H) (-CH 2 -O ( -A 22 O) n -H) or -O-CH (-CH 2 -O (-A 23 O) s -H) (-CH 2 -O (-A 24 O) t -H)
• a 11 , A 21 , A 22 , A 23 , and A 24 are each independently an alkanediyl group having 2 or more and 8 or less carbon atoms
• l, m, n, s and t are average values and are independently 0.
• the sum of l, m and n, and the sum of l, s and t are independently more than 0 and 200 or less.
• the present invention also relates to a precursor compound for producing a compound represented by the chemical formula (1), which is represented by the following chemical formula (2).
• R 1 and R 2 are aliphatic hydrocarbon groups
• X is a single bond or a hydrocarbon group having 1 or more and 5 or less carbon atoms
• the total carbon atoms of R 1 , R 2 and X are 2 or more. 39 or less, A 1'is -OH, A 2'is -O-CH 2 -CH (OH) -CH 2 OH or -O-CH (-CH 2 OH) 2 .
• the present invention also relates to the use of a precursor compound represented by the chemical formula (2) for producing the compound represented by the chemical formula (1).
• the present invention comprises a step of adding an alkylene oxide having 2 or more and 8 or less carbon atoms to the precursor compound represented by the chemical formula (2), wherein the method for producing the compound represented by the chemical formula (1).
• the method for producing the compound represented by the chemical formula (1) Regarding.
• the compound represented by the chemical formula (1) of the present invention (hereinafter, also referred to as an internal trihydrophilic group-containing compound) has a multi-chain hydrophobic group and a hydrophilic group, and has a structure that is extremely difficult to orient. Excellent in the speed of bubble disappearance. Further, since the long-chain alkyl group and a plurality of hydrophilic groups are compactly integrated into the internal trihydrophilic group-containing compound of the present invention, the compound has high surface activity and exhibits high detergency.
• the detergent composition of the present invention containing the internal 3-hydrophilic group-containing compound is likely to form a D phase (bi-continuous structure), and the concentration of the internal 3-hydrophilic group-containing compound in the composition is considered to be easy. Even when the concentration is low, high detergency is exhibited, gelation and thickening are unlikely to occur in a wide concentration range, and the handling property is excellent.
• the internal 3-hydrophilic group-containing compound of the present invention is a compound represented by the following chemical formula (1).
• R 1 and R 2 are aliphatic hydrocarbon groups
• X is a single bond or a hydrocarbon group having 1 or more and 5 or less carbon atoms
• the total carbon atoms of R 1 , R 2 and X are 2 or more.
• a 1 is -O (-A 11 O) l -H
• a 2 is -O-CH 2 -CH (-O (-A 21 O) m -H) (-CH 2 -O ( -A 22 O) n -H) or -O-CH (-CH 2 -O (-A 23 O) s -H) (-CH 2 -O (-A 24 O) t -H)
• a 11 , A 21 , A 22 , A 23 , and A 24 are each independently an arcandyl group having 2 or more and 8 or less carbon atoms
• l, m, n, s and t are independently numbers of 0 or more.
• the sum of l, m, and n, and the sum of l, s, and t are independently greater than 0 and less than or equal to 200.
• R 1 and R 2 are aliphatic hydrocarbon groups, preferably a linear or branched alkyl group, more preferably a linear alkyl group, and further preferably a primary linear alkyl from the viewpoint of production efficiency and ease of production. It is the basis.
• the carbon atoms of R 1 and R 2 are independently 1 or more and 33 or less, and may have a distribution.
• R 1 and R 2 may be the same aliphatic hydrocarbon group or different aliphatic hydrocarbon groups.
• X is a single bond or a hydrocarbon group having 1 or more and 5 or less carbon atoms, and is preferably a single bond or a hydrocarbon group having 1 or more and 3 or less carbon atoms from the viewpoint of production efficiency and ease of production. It is more preferably a single bond or a hydrocarbon group having 1 or more carbon atoms and 2 or less, still more preferably a single bond or a hydrocarbon group having 1 carbon atom, and even more preferably a single bond.
• the total number of carbon atoms of R 1 , R 2 and X is 2 or more and 39 or less, and from the viewpoint of improving detergency, it is preferably 10 or more, more preferably 12 or more, still more preferably 14 or more, and improve water solubility. From the viewpoint of making it, it is preferably 20 or less, more preferably 18 or less, and further preferably 16 or less.
• the total carbon number of R 1 , R 2 and X is preferably an even number from the viewpoint of availability of raw materials.
• the internal 3-hydrophilic group-containing compound has the same total carbon number of R 1 , R 2 and X, and has different carbon numbers of R 1 and R 2 . It is preferable to contain the above compounds.
• the internal 3-hydrophilic group-containing compound has a single bond X, has the same total carbon number of R 1 , R 2 and X, and has the same total carbon number of R 1 and R 2 , respectively. It is more preferable to contain two or more kinds of compounds having different carbon atoms.
• the internal 3 hydrophilic group-containing compound contains two or more compounds in which X is a single bond and the total carbon number of R 1 and R 2 is different, from the viewpoint of improving the detergency and the speed of foam disappearance.
• the total content of the compound having a total carbon number of 14 for R 1 and R 2 and the compound having a total carbon number of 16 for R 1 and R 2 is preferable with respect to the entire internal 3 hydrophilic group-containing compound. Is 75% by mass or more, more preferably 85% by mass or more, still more preferably 95% by mass or more, still more preferably 100% by mass.
• the X is a hydrocarbon group, it is preferably a linear or branched alkanediyl group, more preferably a linear alkanediyl group, and even more preferably a linear ⁇ , ⁇ -alkane, from the viewpoint of production efficiency and ease of production. It is a hydroxy group.
• the content ratio of the compound having 5 or more carbon atoms in R 1 and 5 or more carbon atoms in R 2 is preferably 10 with respect to the entire internal 3 hydrophilic group-containing compound. It is mass% or more, more preferably 20% by mass or more, still more preferably 30% by mass or more, preferably 90% by mass or less, more preferably 80% by mass or less, still more preferably 70% by mass or less.
• a 1 is -O (-A 11 O) l -H
• a 2 is -O-CH 2 -CH (-O (-A 21 O) m -H) (-CH 2 ).
• -O (-A 22 O) n -H) or -O-CH (-CH 2 -O (-A 23 O) s -H) (-CH 2 -O (-A 24 O) t -H) be.
• the compound in which A 2 is -O-CH 2 -CH (-O (-A 21 O) m -H) (-CH 2 -O (-A 22 O) n -H) is T1
• the A 2 is
• the compound which is -O-CH (-CH 2 -O (-A 23 O) s -H) (-CH 2 -O (-A 24 O) t -H) is T2
• the molar ratio of T1 to T1 [T1 / (T1 + T2)] is preferably 0.5 or more, more preferably 0.6 or more, still more preferably 0.7 or more, and preferably 0.7 or more, from the viewpoint of ease of production. It is 0.9 or less, more preferably 0.85 or less, still more preferably 0.8 or less.
• the A 11 O, A 21 O, A 22 O, A 23 O, and A 24 O are alkyleneoxy groups, and A 11 , A 21 , A 22 , A 23 , and A 24 each have 2 carbon atoms independently. It is an alkanediyl group of 8 or more and 8 or less.
• the alkanediyl group is preferably a 1,2-alkandyl group from the viewpoint of ease of production, and more preferably an ethanediyl group and 1,2- One or more selected from the propanediyl group, more preferably an ethanediyl group from the viewpoint of detergency.
• the carbon number of the alkanediyl group is preferably 2 or more and 6 or less, more preferably 2 or more and 5 or less, still more preferably 2 or more and 4 or less, from the viewpoint of improving detergency, defoaming property and water solubility. It is even more preferably 2 or 3, even more preferably 2 from the viewpoint of detergency, and even more preferably 3 from the viewpoint of defoaming property. That is, the carbon number of the alkanediyl group is preferably 6 or less, more preferably 5 or less, still more preferably 4 or less, still more preferably 2 or 3, and even more preferably from the viewpoint of detergency. Is 2, and even more preferably 3, from the viewpoint of defoaming property.
• alkyleneoxy group examples include an ethyleneoxy group, a branched alkyleneoxy group having 3 or more and 8 or less carbon atoms, and a linear alkyleneoxy group having 3 or more and 8 or less carbon atoms.
• the alkyleneoxy group is preferably an ethyleneoxy group or a branched alkyleneoxy group having 3 or more and 8 or less carbon atoms.
• l A 11 O, m A 21 O, n A 22 O, s A 23 O, and t A 24 O each independently contain one of the above alkyleneoxy groups. It may contain two or more kinds.
• L, m, n, s, or t represents the average value of the total number of alkyleneoxy groups.
• l A 11 O, m A 21 O, n A 22 O, s A 23 O, or t A 24 O contain two or more of the alkyleneoxy groups, the alkylene.
• the oxy group is preferably one or more of an ethyleneoxy group and a branched alkyleneoxy group having 3 or more and 8 or less carbon atoms, and more preferably an ethyleneoxy group and a branched propyleneoxy group.
• l A 11 O, m A 21 O, n A 22 O, s A 23 O, or t A 24 O are ethyleneoxy groups and branched alkylene with 3 or more and 8 or less carbon atoms.
• the branched alkyleneoxy group (or branched propyleneoxy group) of 8 or more or less is preferably 2/8 or more, more preferably 3/4 or more, and the speed of bubble disappearance from the viewpoint of improving cleanability and water solubility.
• it is preferably 8/2 or less, more preferably 7/3 or less.
• the repeating structure of the oxy group may be a random structure, a block structure, or a combination of a random structure and a block structure, but from the viewpoint of suppressing gelation, a block structure is preferable, and an EO block-PO block structure is more preferable. It includes a PO block-EO block structure, an EO block-PO block-EO block structure, or a PO block-EO block-PO block structure, more preferably an EO block-PO block-EO block structure.
• l, m, n, s and t are average values and are independently 0 or more, and the sum of l, m and n and the sum of l, s and t are independent of each other. It is more than 0 and 200 or less.
• the sum of l, m and n, and the sum of l, s and t are preferably 3 or more, more preferably 5 or more, still more preferably 5 or more, from the viewpoint of improving detergency, speed of foam disappearance, and water solubility. 7 or more, more preferably 9 or more, preferably 40 or less, more preferably 30 or less, still more preferably 25 or less, from the viewpoint of improving detergency and speed of foam disappearance and suppressing gelation. More preferably, it is 20 or less.
• the method for producing the internal 3-hydrophilic group-containing compound is not particularly limited, and for example, the double bond of the internal olefin is oxidized with a peroxide such as hydrogen peroxide or peracetic acid to synthesize an internal epoxide, and the obtained internal epoxide is synthesized. It can be produced by adding glycerin to an epoxide to synthesize an internal alkyl glyceryl ether (hereinafter, also referred to as AGE), and adding an alkylene oxide having 2 to 8 carbon atoms to the obtained internal alkyl glyceryl ether. ..
• AGE internal alkyl glyceryl ether
• the internal 3 hydrophilic group-containing compound obtained by the above-mentioned production method is R. It is a mixture of two or more compounds having the same total carbon number of 1 and R 2 and X, and different carbon numbers of R 1 and R 2 . Further, in the internal 3 hydrophilic group-containing compound obtained by the above-mentioned production method, A 1 is usually ⁇ O (—A 11 O) l —H and A 2 is ⁇ O—CH 2 in the above chemical formula (1).
• a 2 is a mixture of compounds in which -O-CH (-CH 2 -O (-A 23 O) s -H) (-CH 2 -O (-A 24 O) t -H).
• the internal olefin used for producing the internal 3-hydrophilic group-containing compound may contain a terminal olefin.
• the content of the terminal olefin contained in the olefin is, for example, 0.1% by mass or more, 0.2% by mass or more, and 5% by mass or less, 3% by mass or less, 2% by mass or less, and 1% by mass. % Or less, 0.5% by mass or less, and the like.
• the precursor compound of the present invention is a compound represented by the following chemical formula (2) for producing the compound represented by the chemical formula (1).
• R 1 and R 2 are aliphatic hydrocarbon groups
• X is a single bond or a hydrocarbon group having 1 or more and 5 or less carbon atoms
• the total carbon atoms of R 1 , R 2 and X are 2 or more. 39 or less, A 1'is -OH, A 2'is -O-CH 2 -CH (OH) -CH 2 OH or -O-CH (-CH 2 OH) 2 .
• R 1 and R 2 and X in the chemical formula (2) are the same as those and preferred embodiments in the chemical formula (1), respectively.
• the precursor compound is two or more compounds having the same total carbon number of R 1 , R 2 and X, and different carbon numbers of R 1 and R 2 . It is preferable to include.
• X is a single bond
• the total carbon number of R1 and R2 is the same
• the carbon number of each of R1 and R2 is different from the viewpoint of production efficiency and ease of production. It is more preferable to contain two or more compounds.
• the precursor compound contains two or more compounds in which X is a single bond and the total carbon numbers of R 1 and R 2 are different
• the compound having a total carbon number of R 1 and R 2 of 14 and the compound having a total carbon number of R 2 are 14.
• the total content of the compounds having 16 carbon atoms in R 1 and R 2 is preferably 75% by mass or more, more preferably 85% by mass or more, still more preferably 95% by mass, based on the total amount of the precursor compound. The above is even more preferably 100% by mass.
• the carbon number of R 1 is high.
• the content of the compound having 5 or more and 5 or more carbon atoms of R 2 is preferably 10% by mass or more, more preferably 20% by mass or more, still more preferably 30% by mass or more, based on the total amount of the precursor compound. It is preferably 90% by mass or less, more preferably 80% by mass or less, and further preferably 70% by mass or less.
• the method for producing the precursor compound is not particularly limited.
• the double bond of the internal olefin is oxidized with a peroxide such as hydrogen peroxide or peracetic acid to synthesize an internal epoxide, and the obtained internal epoxide is glycerin.
• a peroxide such as hydrogen peroxide or peracetic acid
• the obtained internal epoxide is glycerin.
• the precursor compounds obtained by the production method are R 1 and R. It is a mixture of two or more compounds having the same total carbon number of 2 and X and different carbon numbers of R 1 and R 2 .
• a 1' is usually -OH and A 2'is -O-CH 2 -CH (OH) -CH 2 OH in the above chemical formula (2). It is a mixture of a compound (P1) and a compound (P2) in which A 1'is -OH and A 2'is -O-CH (-CH 2 OH) 2 .
• the precursor compound is a mixture of the compound (P1) and the compound (P2)
• the molar ratio of P1 to the total of P1 and P2 [P1 / (P1 + P2)] is preferable from the viewpoint of ease of production.
• the internal olefin used for producing the precursor compound may contain a terminal olefin.
• the content of the terminal olefin contained in the olefin is, for example, 0.1% by mass or more, 0.2% by mass or more, and 5% by mass or less, 3% by mass or less, 2% by mass or less, and 1% by mass. % Or less, 0.5% by mass or less, and the like.
• the surfactant composition of the present invention contains at least the internal 3 hydrophilic group-containing compound.
• the content of the internal 3 hydrophilic group-containing compound in the surfactant composition is not particularly limited, but is preferably 50% by mass or more, more preferably 60% by mass or more, still more preferably, from the viewpoint of reducing transportation and storage costs. Is 70% by mass or more, more preferably 80% by mass or more, and from the viewpoint of suppressing gelation, it is preferably 99% by mass or less, more preferably 95% by mass or less, still more preferably 90% by mass or less.
• the surfactant composition of the present invention preferably contains water from the viewpoint of ease of handling.
• the water is not particularly limited, but is preferably purified water such as ion-exchanged water, distilled water, and reverse osmosis membrane water.
• Water can be used in an amount that is a balance other than the internal 3 hydrophilic group-containing compound and other components. Further, the content of water can be 1% by mass or more, 5% by mass or more and 10% by mass or more in the composition, and is 50% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass. It can be as follows.
• the surfactant composition of the present invention can contain a surfactant and a solvent described later from the viewpoint of storage stability.
• the surfactant composition of the present invention does not limit the content of the solvent described below, but the content of the solvent in the surfactant composition is determined from the viewpoint of sustainability, environmental load, safety and the like. It is preferably 10% by mass or less, more preferably 4% by mass or less, further preferably 1% by mass or less, still more preferably 0.1% by mass or less, still more preferably 0% by mass, that is, it does not contain a solvent. Is preferable.
• the surfactant composition may be an emulsifier composition, a wetting agent composition, or a penetrant composition. That is, the surfactant composition of the present invention may be an emulsifier composition, a wetting agent composition, or a penetrant composition containing at least one compound represented by the chemical formula (1).
• the detergent composition of the present invention contains at least the internal 3 hydrophilic group-containing compound.
• the content of the internal 3 hydrophilic group-containing compound in the cleaning agent composition is not particularly limited, but is preferably 0.1% by mass or more, more preferably 1% by mass, from the viewpoint of improving the cleaning property and the speed of foam disappearance. % Or more, more preferably 10% by mass or more, still more preferably 30% by mass or more, still more preferably 40% by mass or more, and preferably 99% by mass or less from the viewpoint of low concentration detergency and suppression of gelation. It is more preferably 90% by mass or less, still more preferably 80% by mass or less.
• the detergent composition of the present invention is a surfactant, water, solvent, fragrance, dye, defoaming agent, preservative, moisturizing agent different from the internal three hydrophilic group-containing compounds as long as the effect of the present invention is not impaired.
• Antibacterial agents, anti-solvents, pearlizing agents, vitamins, thickeners, pH adjusters, bleaching agents, chelating agents, water-soluble salts, and oils, etc. which may optionally contain ingredients used in detergents. can.
• surfactant different from the internal 3 hydrophilic group-containing compound known ones can be used without particular limitation.
• surfactant include anionic surfactants, nonionic surfactants, amphoteric surfactants, and cationic surfactants.
• the water is not particularly limited, but purified water such as ion-exchanged water, distilled water, and reverse osmosis membrane water is preferable.
• Water can be used in an amount that is a balance other than the internal 3 hydrophilic group-containing compound and other components. Further, the content of water in the composition can be 1% by mass or more, 10% by mass or more, 20% by mass or more, 30% by mass or more, 40% by mass or more, 50% by mass or more, 99.5. Mass% or less, 90% by mass or less, 70% by mass or less, 60% by mass or less, 50% by mass or less, 40% by mass or less, 30% by mass or less, 20% by mass or less, 10% by mass or less, 5% by mass or less, 0 It can be mass%.
• the detergent composition of the present invention can contain a solvent for the purpose of enhancing low temperature stability and cleaning performance.
• the cleaning agent composition of the present invention does not limit the content of the solvent
• the content of the solvent in the cleaning agent composition is preferably from the viewpoint of sustainability, environmental load, safety and the like. It is preferably 10% by mass or less, more preferably 4% by mass or less, still more preferably 1% by mass or less, still more preferably 0.1% by mass or less, still more preferably 0% by mass, that is, it does not contain a solvent.
• the detergent composition of the present invention can be prepared, for example, by mixing the internal 3 hydrophilic group-containing compound and other components.
• the order of preparation is not particularly limited, but for example, after preparing the detergent composition containing the internal 3 hydrophilic group-containing compound, the other components are blended. You may.
• the temperature to stand is preferably 10 ° C. or higher, more preferably 15 ° C. or higher, still more preferably 20 ° C. or higher, still more preferably 25 ° C. or higher, from the viewpoint of obtaining a uniformly dissolved detergent composition. From the viewpoint of economic efficiency, it is preferably 80 ° C. or lower, more preferably 70 ° C. or lower, still more preferably 60 ° C. or lower, still more preferably 50 ° C. or lower, still more preferably 40 ° C. or lower, still more preferably 30 ° C. or lower. ..
• the standing time varies depending on the temperature, but from the viewpoint of sufficient uniform dissolution, it is preferably 1 hour or longer, more preferably 5 hours or longer, still more preferably 12 hours or longer, still more preferably 18 hours or longer, still more preferably. Is 24 hours or more, more preferably 2 days or more, still more preferably 3 days or more, preferably January or less, more preferably 20 days or less, still more preferably 10 days or less from the viewpoint of economic efficiency.
• the surfactant composition or detergent composition of the present invention includes, for example, liquid detergents for clothing, detergents for dishes, detergents for hair, detergents for bodies, detergents for precision parts, detergents for hard surfaces, and the like. Used as a cleaning agent.
• the surfactant composition or detergent composition of the present invention can be used for each of the above-mentioned cleaning applications by adding and dissolving it in water.
• R 1 and R 2 are aliphatic hydrocarbon groups
• X is a single bond or a hydrocarbon group having 1 or more and 5 or less carbon atoms
• the total carbon atoms of R 1 , R 2 and X are 2 or more.
• a 1 is -O (-A 11 O) l -H
• a 2 is -O-CH 2 -CH (-O (-A 21 O) m -H) (-CH 2 -O ( -A 22 O) n -H) or -O-CH (-CH 2 -O (-A 23 O) s -H) (-CH 2 -O (-A 24 O) t -H)
• a 11 , A 21 , A 22 , A 23 , and A 24 are each independently an alkanediyl group having 2 or more and 8 or less carbon atoms
• l, m, n, s and t are average values and are independently 0.
• the sum of l, m and n, and the sum of l, s and t are independently more than 0 and 200 or less.
• R 1 and R 2 are preferably a linear or branched alkyl group, more preferably a linear alkyl group, and further preferably a primary linear alkyl group.
• R 3> The compound according to ⁇ 1> or ⁇ 2>, wherein the carbon atoms of R 1 and R 2 are independently 1 or more and 33 or less.
• ⁇ 4> The compound according to any one of ⁇ 1> to ⁇ 3>, wherein R 1 and R 2 are the same aliphatic hydrocarbon group or different aliphatic hydrocarbon groups.
• the X is preferably a single bond or a hydrocarbon group having 1 or more and 3 or less carbon atoms, more preferably a single bond or a hydrocarbon group having 1 or more and 2 or less carbon atoms, and further preferably a single bond or a hydrocarbon group having 1 or less carbon atoms.
• ⁇ 7> The compound according to any one of ⁇ 1> to ⁇ 4>, wherein X is a hydrocarbon group having 1 or more and 5 or less carbon atoms.
• the total carbon number of R 1 , R 2 and X is preferably 10 or more, more preferably 12 or more, still more preferably 14 or more, and preferably 20 or less, more preferably 18 or less, still more preferably 16.
• the compound according to any one of ⁇ 1> to ⁇ 8> which is as follows.
• ⁇ 10> The compound according to any one of ⁇ 1> to ⁇ 8>, wherein the total carbon number of R 1 , R 2 and X is 10 or more and 20 or less.
• ⁇ 11> The compound according to any one of ⁇ 1> to ⁇ 8>, wherein the total carbon number of R 1 , R 2 and X is 12 or more and 18 or less.
• ⁇ 12> The compound according to any one of ⁇ 1> to ⁇ 8>, wherein the total carbon number of R 1 , R 2 and X is 14 or more and 16 or less.
• ⁇ 13> The compound according to any one of ⁇ 1> to ⁇ 12>, wherein the total carbon number of R 1 , R 2 and X is an even number.
• the compound represented by the chemical formula (1) contains two or more compounds having the same total carbon number of R 1 , R 2 and X, and different carbon numbers of R 1 and R 2 . 1> The compound according to any one of ⁇ 13>.
• X is a single bond or a hydrocarbon group having 1 or more and 5 or less carbon atoms, the total carbon atoms of R 1 , R 2 and X are the same, and R 1 and The compound according to any one of ⁇ 1> to ⁇ 13>, which comprises two or more kinds of compounds having different carbon atoms of R2 .
• the compound represented by the chemical formula (1) has X as a single bond or a hydrocarbon group having 1 or more and 3 or less carbon atoms, has the same total carbon number of R 1 and R 2 and X, and has the same total carbon atoms as R 1 .
• the compound represented by the chemical formula (1) is a hydrocarbon group in which X is a single bond or has 1 or more and 2 or less carbon atoms, has the same total carbon number of R 1 and R 2 and X, and has the same total carbon atoms as R 1 .
• the compound according to any one of ⁇ 1> to ⁇ 13> which comprises two or more kinds of compounds having different carbon atoms of R2 .
• X is a single bond or a hydrocarbon group having 1 carbon atom, the total carbon atoms of R 1 and R 2 and X are the same, and R 1 and R 2 have the same total carbon number.
• X is a single bond, the total carbon numbers of R 1 , R 2 and X are the same, and the carbon numbers of R 1 and R 2 are different.
• the compound according to any one of ⁇ 1> to ⁇ 13> which comprises the above compounds.
• the compound represented by the chemical formula (1) contains two or more compounds in which X is a single bond and the total carbon numbers of R 1 and R 2 are different, the total carbon number of R 1 and R 2 is high.
• the total content of the compound having 14 and the compound having 16 carbon atoms in R 1 and R 2 is preferably 75% by mass or more, more preferably 85% by mass or more, still more preferably 95% by mass or more, and more.
• the compound according to any one of ⁇ 1> to ⁇ 13> which is more preferably 100% by mass.
• the compound represented by the chemical formula (1) contains two or more compounds having the same total carbon number of R 1 , R 2 and X, and having different carbon numbers of R 1 and R 2 .
• the content of the compound having 5 or more carbon atoms in R 1 and 5 or more carbon atoms in R 2 is preferably 10% by mass or more, more preferably 20% by mass, based on the total amount of the compound represented by the chemical formula (1).
• the content ratio of the compound having 5 or more carbon atoms in R 1 and 5 or more carbon atoms in R 2 is 20% by mass or more and 80% by mass or less with respect to the entire compound represented by the chemical formula (1).
• ⁇ 24> When the compound represented by the chemical formula (1) contains two or more compounds having the same total carbon number of R 1 , R 2 and X, and having different carbon numbers of R 1 and R 2 .
• the content ratio of the compound having 5 or more carbon atoms in R 1 and 5 or more carbon atoms in R 2 is 30% by mass or more and 70% by mass or less with respect to the entire compound represented by the chemical formula (1).
• the alkanediyl group is preferably one or more selected from a 1,2-alkandyl group, more preferably an ethanediyl group, and a 1,2-propanediyl group, and more preferably an ethanediyl group, ⁇ 1> to ⁇ . 28> The compound according to any one of.
• the number of carbon atoms of the alkanediyl group is preferably 2 or more and 6 or less, more preferably 2 or more and 5 or less, still more preferably 2 or more and 4 or less, still more preferably 2 or 3, ⁇ 1> to ⁇ 28>.
• the compound described in any. ⁇ 31> The compound according to any one of ⁇ 1> to ⁇ 28>, wherein the alkanediyl group has preferably 6 or less, more preferably 5 or less, still more preferably 4 or less, still more preferably 2 or 3. ..
• the A 11 O, A 21 O, A 22 O, A 23 O, and A 24 O are alkyleneoxy groups, and the alkyleneoxy group is preferably an ethyleneoxy group or a branched alkylene having 3 or more and 8 or less carbon atoms.
• the alkylene The oxy group is preferably one or more of an ethylene oxy group and a branched alkylene oxy group having 3 or more and 8 or less carbon atoms, and more preferably one of ⁇ 1> to ⁇ 32>, which is an ethylene oxy group and a branched propylene oxy group.
• the compound described in. ⁇ 34> The l A 11 O, m A 21 O, n A 22 O, s A 23 O, or t A 24 O are branched with ethyleneoxy groups having 3 or more and 8 or less carbon atoms.
• the branched alkyleneoxy group (or branched propyleneoxy group) of 3 or more and 8 or less is preferably 2/8 or more, more preferably 3/7 or more, and preferably 8/2 or less, more preferably 7 /.
• l A 11 O, m A 21 O, n A 22 O, s A 23 O, or t A 24 O are branched from ethyleneoxy groups with 3 or more and 8 or less carbon atoms.
• the mol ratio of the ethyleneoxy groups and the branched alkyleneoxy groups (or branched propyleneoxy groups) having 3 or more and 8 or less carbon atoms [ethyleneoxy group / carbon number].
• ⁇ 36> The l A 11 O, m A 21 O, n A 22 O, s A 23 O, or t A 24 O are branched from ethyleneoxy groups with 3 or more and 8 or less carbon atoms.
• the repeating structure of the alkyleneoxy group is 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.
• the total of l, m and n, and the total of l, s and t are independently, preferably 3 or more, more preferably 5 or more, still more preferably 7 or more, still more preferably 9 or more, and preferably 9 or more.
• ⁇ 39> The compound according to any one of ⁇ 1> to ⁇ 37>, wherein the total of l, m and n, and the total of l, s and t are independently 3 or more and 40 or less.
• ⁇ 40> The compound according to any one of ⁇ 1> to ⁇ 37>, wherein the total of l, m and n, and the total of l, s and t are independently 5 or more and 30 or less.
• ⁇ 41> The compound according to any one of ⁇ 1> to ⁇ 37>, wherein the total of l, m and n, and the total of l, s and t are independently 7 or more and 25 or less.
• ⁇ 42> The compound according to any one of ⁇ 1> to ⁇ 37>, wherein the total of l, m and n, and the total of l, s and t are independently 9 or more and 20 or less.
• R 1 and R 2 are aliphatic hydrocarbon groups
• X is a single bond or a hydrocarbon group having 1 or more and 5 or less carbon atoms
• the total carbon atoms of R 1 , R 2 and X are 2 or more. 39 or less, A 1'is -OH, A 2'is -O-CH 2 -CH (OH) -CH 2 OH or -O-CH (-CH 2 OH) 2 .
• R 1 and R 2 are preferably a linear or branched alkyl group, more preferably a linear alkyl group, and further preferably a primary linear alkyl group.
• R 1 and R 2 are preferably a linear or branched alkyl group, more preferably a linear alkyl group, and further preferably a primary linear alkyl group.
• R 1 and R 2 are preferably a linear or branched alkyl group, more preferably a linear alkyl group, and further preferably a primary linear alkyl group.
• the carbon atoms of R 1 and R 2 are independently 1 or more and 33 or less.
• ⁇ 46> The precursor compound according to any one of ⁇ 43> to ⁇ 45>, wherein R 1 and R 2 are the same aliphatic hydrocarbon group or different aliphatic hydrocarbon groups.
• the X is preferably a single bond or a hydrocarbon group having 1 or more and 3 or less carbon atoms, more preferably a single bond or a hydrocarbon group having 1 or more and 2 or less carbon atoms, and further preferably a single bond or a hydrocarbon group having 1 or less carbon atoms. , More preferably a single bond, according to any of ⁇ 43> to ⁇ 46>.
• ⁇ 48> The precursor compound according to any one of ⁇ 43> to ⁇ 46>, wherein X is a single bond.
• X is a hydrocarbon group having 1 or more and 5 or less carbon atoms.
• the total carbon number of R 1 , R 2 and X is preferably 10 or more, more preferably 12 or more, still more preferably 14 or more, and preferably 20 or less, more preferably 18 or less, still more preferably 16.
• ⁇ 52> The precursor compound according to any one of ⁇ 43> to ⁇ 50>, wherein the total carbon number of R 1 , R 2 and X is 10 or more and 20 or less.
• ⁇ 53> The precursor compound according to any one of ⁇ 43> to ⁇ 50>, wherein the total carbon number of R 1 , R 2 and X is 12 or more and 18 or less.
• ⁇ 54> The precursor compound according to any one of ⁇ 43> to ⁇ 50>, wherein the total carbon number of R 1 , R 2 and X is 14 or more and 16 or less.
• ⁇ 55> The compound according to any one of ⁇ 43> to ⁇ 54>, wherein the total carbon number of R 1 , R 2 and X is an even number.
• the compound represented by the chemical formula (2) contains two or more compounds having the same total carbon number of R 1 , R 2 and X, and different carbon numbers of R 1 and R 2 . 43> The precursor compound according to any one of ⁇ 55>. ⁇ 57> The compound represented by the chemical formula (2) has X as a single bond or a hydrocarbon group having 1 or more and 5 or less carbon atoms, has the same total carbon number of R 1 and R 2 and X, and has the same total carbon atoms as R 1 .
• X is a single bond or a hydrocarbon group having 1 or more and 3 or less carbon atoms, the total carbon atoms of R 1 , R 2 and X are the same, and R 1 and The precursor compound according to any one of ⁇ 43> to ⁇ 55>, which comprises two or more kinds of compounds having different carbon atoms of R2 .
• the compound represented by the chemical formula (2) has X as a single bond or a hydrocarbon group having 1 or more carbon atoms and 2 or less carbon atoms, has the same total carbon number of R 1 and R 2 and X, and has the same total carbon atoms as R 1 .
• the precursor compound according to any one of ⁇ 43> to ⁇ 55> which comprises two or more kinds of compounds having different carbon atoms of R2 .
• X is a single bond or a hydrocarbon group having 1 carbon atom, the total carbon atoms of R 1 and R 2 and X are the same, and R 1 and R 2 have the same total carbon number.
• the precursor compound according to any one of ⁇ 43> to ⁇ 55> which comprises two or more kinds of compounds having different carbon atoms.
• X is a single bond, the total carbon number of R1 and R2 and X is the same, and the carbon number of each of R1 and R2 is different.
• the precursor compound according to any one of ⁇ 43> to ⁇ 55> which comprises the above compounds.
• the compound represented by the chemical formula (2) contains two or more compounds in which X is a single bond and the total carbon numbers of R 1 and R 2 are different, the total carbon number of R 1 and R 2 is high.
• the total content of the compound having 14 and the compound having 16 carbon atoms in R 1 and R 2 is preferably 75% by mass or more, more preferably 85% by mass or more, still more preferably 95% by mass or more, and more.
• the precursor compound according to any one of ⁇ 43> to ⁇ 55> which is more preferably 100% by mass.
• the compound represented by the chemical formula (2) contains two or more compounds having the same total carbon number of R 1 , R 2 and X, and having different carbon numbers of R 1 and R 2 respectively.
• the content of the compound having 5 or more carbon atoms in R 1 and 5 or more carbon atoms in R 2 is preferably 10% by mass or more, more preferably 20% by mass, based on the total amount of the compound represented by the chemical formula (2).
• Precursor compound is preferably 10% by mass or more, more preferably 20% by mass, based on the total amount of the compound represented by the chemical formula (2).
• % Or more more, more preferably 30% by mass or more, preferably 90% by mass or less, more preferably 80% by mass or less, still more preferably 70% by mass or less, according to any one of ⁇ 43>
• the content ratio of the compound having 5 or more carbon atoms in R 1 and 5 or more carbon atoms in R 2 is 20% by mass or more and 80% by mass or less with respect to the entire compound represented by the chemical formula (2).
• ⁇ 66> When the compound represented by the chemical formula (2) contains two or more compounds having the same total carbon number of R 1 , R 2 and X, and having different carbon numbers of R 1 and R 2 respectively.
• the content ratio of the compound having 5 or more carbon atoms in R 1 and 5 or more carbon atoms in R 2 is 30% by mass or more and 70% by mass or less with respect to the entire compound represented by the chemical formula (2).
• the compounds represented by the chemical formula (2) are the compound (P1) in which A 1'is -OH and A 2'is -O-CH 2 -CH (OH) -CH 2 OH, and the compound (P1).
• P1 When'is a mixture of -OH and A 2'is -O-CH (-CH 2 OH) 2 compound (P2), the molar ratio of P1 to the sum of P1 and P2 [P1 / (P1 + P2)].
• the compounds represented by the chemical formula (2) are the compound (P1) in which A 1'is -OH and A 2'is -O-CH 2 -CH (OH) -CH 2 OH, and the compound (P1).
• P1 When'is a mixture of -OH and A 2'is -O-CH (-CH 2 OH) 2 compound (P2), the molar ratio of P1 to the sum of P1 and P2 [P1 / (P1 + P2)].
• the compounds represented by the chemical formula (2) are the compound (P1) in which A 1'is -OH and A 2'is -O-CH 2 -CH (OH) -CH 2 OH, and the compound (P1).
• P1 When'is a mixture of -OH and A 2'is -O-CH (-CH 2 OH) 2 compound (P2), the molar ratio of P1 to the sum of P1 and P2 [P1 / (P1 + P2)].
• the compounds represented by the chemical formula (2) are the compound (P1) in which A 1'is -OH and A 2'is -O-CH 2 -CH (OH) -CH 2 OH, and the compound (P1).
• P1 When'is a mixture of -OH and A 2'is -O-CH (-CH 2 OH) 2 compound (P2), the molar ratio of P1 to the sum of P1 and P2 [P1 / (P1 + P2)].
• the content of the compound represented by the chemical formula (1) in the surfactant composition is preferably 50% by mass or more, more preferably 60% by mass or more, still more preferably 70% by mass or more, still more preferably 70% by mass or more.
• the surfactant composition according to ⁇ 71> which is 80% by mass or more, preferably 99% by mass or less, more preferably 95% by mass or less, still more preferably 90% by mass or less.
• ⁇ 74> The surfactant composition according to ⁇ 71>, wherein the content of the compound represented by the chemical formula (1) in the surfactant composition is 60% by mass or more and 95% by mass or less.
• ⁇ 75> The surfactant composition according to ⁇ 71>, wherein the content of the compound represented by the chemical formula (1) in the surfactant composition is 70% by mass or more and 90% by mass or less.
• ⁇ 76> The surfactant composition according to ⁇ 71>, wherein the content of the compound represented by the chemical formula (1) in the surfactant composition is 80% by mass or more and 90% by mass or less.
• ⁇ 77> The surfactant composition according to any one of ⁇ 71> to ⁇ 76>, wherein the surfactant composition contains water.
• the surfactant composition according to ⁇ 77> wherein the water is preferably purified water, more preferably ion-exchanged water, distilled water, or reverse osmosis membrane water.
• the content of the water in the surfactant composition is 1% by mass or more, 5% by mass or more, or 10% by mass or more, and 50% by mass or less, 40% by mass or less, 30% by mass or less, or 20.
• ⁇ 80> The surfactant composition according to any one of ⁇ 71> to ⁇ 79>, wherein the surfactant composition contains a surfactant or a solvent different from the compound represented by the chemical formula (1).
• the content of the solvent in the surfactant composition is preferably 10% by mass or less, more preferably 4% by mass or less, still more preferably 1% by mass or less, still more preferably 0.1% by mass or less.
• the content of the compound represented by the chemical formula (1) in the cleaning agent composition is preferably 0.1% by mass or more, more preferably 1% by mass or more, still more preferably 10% by mass or more, still more preferably. Is 30% by mass or more, more preferably 40% by mass or more, and preferably 99% by mass or less, more preferably 90% by mass or less, still more preferably 80% by mass or less, according to ⁇ 83>.
• Cleaning agent composition. ⁇ 85> The cleaning agent composition according to ⁇ 83>, wherein the content of the compound represented by the chemical formula (1) in the cleaning agent composition is 0.1% by mass or more and 99% by mass or less.
• the cleaning agent composition according to ⁇ 83> wherein the content of the compound represented by the chemical formula (1) in the cleaning agent composition is 1% by mass or more and 90% by mass or less.
• the cleaning agent composition according to ⁇ 83> wherein the content of the compound represented by the chemical formula (1) in the cleaning agent composition is 10% by mass or more and 80% by mass or less.
• the cleaning agent composition according to ⁇ 83> wherein the content of the compound represented by the chemical formula (1) in the cleaning agent composition is 30% by mass or more and 80% by mass or less.
• ⁇ 89> The cleaning agent composition according to ⁇ 83>, wherein the content of the compound represented by the chemical formula (1) in the cleaning agent composition is 40% by mass or more and 80% by mass or less.
• ⁇ 90> The detergent composition according to any one of ⁇ 83> to ⁇ 89>, wherein the detergent composition contains a surfactant different from the compound represented by the chemical formula (1).
• the water is preferably purified water, more preferably ion-exchanged water, distilled water, or reverse osmosis membrane water.
• the content of the water in the cleaning agent composition is 1% by mass or more, 10% by mass or more, 20% by mass or more, 30% by mass or more, 40% by mass or more, 50% by mass or more, and 99.5% by mass.
• the content of the solvent in the detergent composition is preferably 10% by mass or less, more preferably 4% by mass or less, still more preferably 1% by mass or less, still more preferably 0.1% by mass or less.
• R 1 and R 2 are aliphatic hydrocarbon groups
• X is a single bond or a hydrocarbon group having 1 or more and 5 or less carbon atoms
• the total carbon atoms of R 1 , R 2 and X are 2 or more. 39 or less, A 1'is -OH, A 2'is -O-CH 2 -CH (OH) -CH 2 OH or -O-CH (-CH 2 OH) 2 .
• ⁇ 97> The method for producing a compound according to any one of ⁇ 1> to ⁇ 42>, which comprises a step of adding an alkylene oxide having 2 or more and 8 or less carbon atoms to the precursor compound represented by the following chemical formula (2).
• R 1 and R 2 are aliphatic hydrocarbon groups
• X is a single bond or a hydrocarbon group having 1 or more and 5 or less carbon atoms
• the total carbon atoms of R 1 , R 2 and X are 2 or more. 39 or less, A 1'is -OH, A 2'is -O-CH 2 -CH (OH) -CH 2 OH or -O-CH (-CH 2 OH) 2 .
• GC gas chromatography
• GC device Product name HP6890 (manufactured by HEWLETT PACKARD) Column: Product name Ultra-Alloy-1HT Capillary column 30m x 250 ⁇ m x 0.15 ⁇ m (manufactured by Frontier Lab Co., Ltd.)
• Detector Hydrogen flame ion detector (FID) Injection temperature: 300 ° C Detector temperature: 350 ° C Oven: 60 ° C (0 min.) ⁇ 2 ° C / min. ⁇ 225 ° C ⁇ 20 ° C / min. ⁇ 350 ° C ⁇ 350 ° C (5.2 min.)
• the measurement conditions are as follows.
• the obtained crude C16 internal olefin was transferred to a distiller and distilled at 136 to 160 ° C./4.0 mmHg to obtain an internal olefin 1 having an olefin purity of 100%.
• the double bond distribution of the obtained internal olefin 1 was 0.2% at the C1 position, 15.8% at the C2 position, 14.5% at the C3 position, 15.7% at the C4 position, 17.3% at the C5 position, and 16 at the C6 position.
• the total of 5.5%, C7th and 8th was 20.0%.
• Manufacturing example A2 Manufacturing of an internal olefin having 18 carbon atoms (internal olefin 2)) 1-Octadecanol (product name: Calcol 8098, manufactured by Kao Co., Ltd.) 800 kg (3.0 kilomol) for a reactor with a stirrer, activated alumina GP-20 (Mizusawa Chemical Industry Co., Ltd.) 80 kg (raw material) as a solid acid catalyst 10 wt% with respect to alcohol) was charged, and the reaction was carried out at 280 ° C. at 280 ° C. for 16 hours while circulating nitrogen (15 L / min) in the system.
• the obtained crude C18 internal olefin was transferred to a still and distilled at 163 to 190 ° C./4.6 mmHg to obtain an internal olefin 2 having an olefin purity of 100%.
• the double bond distribution of the obtained internal olefin 2 was 0.3% at the C1 position, 13.3% at the C2 position, 12.6% at the C3 position, 13.9% at the C4 position, 14.8% at the C5 position, and 13 at the C6 position.
• the total of 0.7%, C7th place 12.6, C8th place, and 9th place was 18.8%.
• Production example B1 Manufacturing of internal epoxide with 16 carbon atoms (internal epoxide 1)) 800 g (3.56 mol) of internal olefin 1 obtained in Production Example A1, 107 g (1.78 mol) of acetic acid (manufactured by Wako Pure Chemical Industries, Ltd.), and sulfuric acid (manufactured by Wako Pure Chemical Industries, Ltd.) in a flask equipped with a stirrer.
• acetic acid manufactured by Wako Pure Chemical Industries, Ltd.
• sulfuric acid manufactured by Wako Pure Chemical Industries, Ltd.
• the aqueous layer is separated and the aqueous layer is extracted, and the oil layer is ion-exchanged water, saturated sodium carbonate aqueous solution (manufactured by Wako Pure Chemical Industries, Ltd.), saturated sodium sulfite aqueous solution (manufactured by Wako Pure Chemical Industries, Ltd.), 1% saline solution.
• the mixture was washed with (Wako Pure Chemical Industries, Ltd.) and concentrated with an evaporator to obtain 820 g of internal epoxide 1.
• Production example B2 Manufacturing of internal epoxide with 18 carbon atoms (internal epoxide 2)) 595 g (2.38 mol) of internal olefin 2 obtained in Production Example A2, 71.7 g (1.20 mol) of acetic acid (manufactured by Wako Pure Chemical Industries, Ltd.), sulfuric acid (Wako Pure Chemical Industries, Ltd.) in a flask equipped with a stirrer. 9.8 g (0.10 mol) (manufactured by Wako Pure Chemical Industries, Ltd.) and 324 g (4.00 mol) of 35% hydrogen peroxide (manufactured by Wako Pure Chemical Industries, Ltd.) were charged and reacted at 50 ° C.
• alkyl glyceryl ether AGE
• AGE1 AGE2
• Production example C1 (Production of reaction product (AGE1) of internal epoxide 1 and glycerin) Add 2298 g (25.0 mol) of glycerin (manufactured by Wako Pure Chemical Industries, Ltd.) and 0.122 g (1.25 mmol) of 98% sulfuric acid (manufactured by Wako Pure Chemical Industries, Ltd.) into a flask with a stirrer and raise the temperature to 130 ° C. It was warm. Then, 300 g (1.25 mol) of the internal epoxide 1 obtained in Production Example B1 was added dropwise over 1 hour, and then the reaction was carried out at 130 ° C. for 8 hours.
• AGE1 reaction product of internal epoxide 1 and glycerin
• R 1 and R 2 each independently contain an alkyl group having 1 to 13 carbon atoms, the total carbon atoms of R 1 and R 2 are 14, and X is a single bond.
• a 1'or A 2' is -OH and the other is -O-CH 2 -CH (OH) -CH 2 OH or -O-CH (-CH 2 -OH) 2 .
• a 1'or A 2'is -O-CH 2 -CH (OH) -CH 2 OH ether alcohol (AGE obtained by reacting the hydroxyl group at the 1-position of glycerin with an epoxy group), A. It contained 27% of ether alcohol (AGE obtained by reacting the hydroxyl group at the 2 -position of glycerin with an epoxy group) in which 1'or A 2'is -O-CH (-CH 2 -OH) 2 .
• Production example C2 (Production of reaction product (AGE2) of internal epoxide 2 and glycerin) The same production method as in Production Example C1 was used except that the internal epoxide 2 (1.25 mol) obtained in Production Example B2 was used instead of the internal epoxide 1 (1.25 mol) obtained in Production Example B1. Obtained AGE2.
• R 1 and R 2 each independently contain an alkyl group having 1 to 15 carbon atoms, the total carbon number of R 1 and R 2 is 16, and X is simple.
• a 1'or A 2' is -OH and the other is -O-CH 2 -CH (OH) -CH 2 OH or -O-CH (-CH 2 -OH) 2
• Manufacturing example 2 Manufacturing of EO14 mol adduct of AGE1 (implemented product 2)
• the product 2 was obtained by the same production method as in Production Example 1 except that the feed amount of EO was 372 g (8.41 mol).
• the average number of moles of EO added to the obtained product was confirmed by 1 H-NMR.
• Production example 3 Manufacturing of EO5 mol adduct of AGE2 (implemented product 3)
• AGE2 obtained in Production Example C2 was used, and 5 mol of EO was fed to 1 mol of AGE2.
• Got The average number of moles of EO added to the obtained product was confirmed by 1 H-NMR.
• Production example 4 Manufacturing of EO7 mol adduct of AGE2 (implemented product 4)
• the product 4 was obtained by the same production method as in Production Example 3 except that 7 mol of EO was fed to 1 mol of AGE2.
• the average number of moles of EO added to the obtained product was confirmed by 1 H-NMR.
• Production Example 5 Manufacturing of EO9 mol adduct of AGE2 (implemented product 5)
• the product 5 was obtained by the same production method as in Production Example 3 except that 9 mol of EO was fed to 1 mol of AGE2.
• the average number of moles of EO added to the obtained product was confirmed by 1 H-NMR.
• Production Example 6 Manufacturing of 3 mol of EO and 5.4 mol of PO of AGE2 (Implemented product 6)
• the same production method as in Production Example 3 was carried out except that after feeding 3 mol of EO to 1 mol of AGE2, 5.4 mol of PO (propylene oxide) was fed to 1 mol of AGE2. Good 6 was obtained.
• the average number of moles of EO and PO added to the obtained product was confirmed by 1 H-NMR.
• Production example 7 Manufacturing of EO5 mol and PO9 mol adduct of AGE2 (implemented product 7)
• the product 7 was obtained by the same production method as in Production Example 3 except that 5 mol of EO was fed to 1 mol of AGE2 and then 9 mol of PO was fed to 1 mol of AGE2.
• the average number of moles of EO and PO added to the obtained product was confirmed by 1 H-NMR.
• Production Example 8 Manufacturing of EO7 mol and PO12.6 mol adduct of AGE2 (Implemented product 8)
• the product 8 was obtained by the same production method as in Production Example 3 except that 7 mol of EO was fed to 1 mol of AGE2 and then 12.6 mol of PO was fed to 1 mol of AGE2. rice field.
• the average number of moles of EO and PO added to the obtained product was confirmed by 1 H-NMR.
• Production Example 9 Manufacturing of EO5 mol adduct of AGE1 (implemented product 9)
• the product 9 was obtained by the same production method as in Production Example 1 except that 5 mol of EO was fed to 1 mol of AGE1.
• the average number of moles of EO added to the obtained product was confirmed by 1 H-NMR.
• Production Example 10 Manufacturing of EO7 mol adduct of AGE1 (implemented product 10)
• the product 10 was obtained by the same production method as in Production Example 1 except that 7 mol of EO was fed to 1 mol of AGE1.
• the average number of moles of EO added to the obtained product was confirmed by 1 H-NMR.
• Production Example 11 Manufacturing of EO4 mol adduct of AGE2 (implemented product 11) The product 11 was obtained by the same production method as in Production Example 3 except that 4 mol of EO was fed to 1 mol of AGE2. The average number of moles of EO added to the obtained product was confirmed by 1 H-NMR.
• Production Example 12 Manufacturing of PO3 mol and EO5 mol adduct of AGE2 (Implemented product 12)
• the product 12 was obtained by the same production method as in Production Example 3 except that 3 mol of PO was fed to 1 mol of AGE2 and then 5 mol of EO was fed to 1 mol of AGE2.
• the average number of moles of EO and PO added to the obtained product was confirmed by 1 H-NMR.
• Production Example 13 Manufacturing of 5.4 mol of EO of AGE2 and 3 mol of PO adduct (implemented product 13)
• the product 13 was obtained by the same production method as in Production Example 3 except that 5.4 mol of EO was fed to 1 mol of AGE2 and then 3 mol of PO was fed to 1 mol of AGE2. rice field.
• the average number of moles of EO and PO added to the obtained product was confirmed by 1 H-NMR.
• Production Example 14 Manufacturing of EO14 mol adduct of AGE2 (implemented product 14) The product 14 was obtained by the same production method as in Production Example 3 except that 14 mol of EO was fed to 1 mol of AGE2. The average number of moles of EO added to the obtained product was confirmed by 1 H-NMR.
• Table 1 shows the correspondence with the chemical formula (1) for each of the products 1 to 14.
• Production Example 15 (Production of Polyoxyethylene (10) Alkyl (Mixed with Lauryl and Myristyl) Ether (Comparative Product 1))
• 10 mol of EO ethylene oxide
• a mixed alcohol mass ratio 72:28
• lauryl alcohol Kao Corporation, Calcol 2098
• myristyl alcohol Kao Corporation, Calcol 4098
• Comparative product 2 Polyoxyethylene (7) alkyl (mixed with secondary dodecyl and secondary tetradecyl) ether (Nippon Shokubai Co., Ltd., Softanol 70) was used as Comparative Product 2.
• Comparative product 3 Polyoxyethylene (9) alkyl (mixed with secondary dodecyl and secondary tetradecyl) ether (Nippon Shokubai Co., Ltd., Sophanol 90) was used as Comparative Product 3.
• Table 1 shows the implemented products 1 to 14.
• Example 1 (Examples 1-1 to 1-8, Comparative Example 1-1) The detergency was evaluated by the following method using the implemented product and the comparative product shown in Table 2, respectively. The results are shown in Table 2.
• model sebum artificially contaminated cloth having the following composition was adhered to a cloth (cotton 2003 (manufactured by Tanito Shoten Co., Ltd.)) to prepare a model sebum artificially contaminated cloth.
• the model sebum artificial contaminants were attached to the cloth by printing the artificial contaminants on the cloth using a gravure roll coater.
• the cell capacity of the gravure roll is 58 cm 3 / m 2
• the coating speed is 1.0 m / min
• the drying temperature is 100 ° C
• the drying time is 1 min. gone.
• the model sebum artificially contaminated cloth was washed with a turgotometer at 85 rpm for 10 minutes. After washing, it was dehydrated and dried in an environment of 23 ° C. and 45% RH for 24 hours.
• the cleaning rate (%) of the model sebum artificially contaminated cloth was measured by the following method, and the average value of 5 sheets was obtained. The results are shown in Table 1.
• Example 2 (Examples 2-1 to 2-6, Comparative Examples 2-1 to 2-3) Take 1.5 g of each of the implemented product and the comparative product shown in Table 3 in a 500 mL beaker, add an appropriate amount of ion-exchanged water, heat to 60 ° C. and mix to obtain a uniform aqueous solution, and then ion-exchange. Water was replenished to prepare a surfactant composition having a concentration of 0.5% by mass. The prepared surfactant composition was heated to 60 ° C., stirred and homogenized, and then 0 minutes and 1 minute based on the synthetic detergent test method (Rosmiles method) of JIS K 3362 (2008). The foam height (cm) was measured after 2, 3, and 5 minutes. The results are shown in Table 3. The smaller the foam height value, the better the defoaming property.
• Example 3 (Examples 3-1 to 3-8, Comparative Example 3-1) 50 mL of a surfactant aqueous solution (20 ° C.) containing 0.1% by mass of each of the implementation products and comparative products shown in Table 4 was placed in a 100 mL beaker, bubbles on the surface were removed using a dropper, and the mixture was allowed to stand for 3 minutes.
• a cotton canvas cloth (raw machine, knitted fabric, 2.0 ⁇ 2.0 cm) was gently floated on the aqueous solution using a tweezers, and the time until the cotton canvas cloth completely settled under the surface of the water was measured.
• the aqueous surfactant solution was exchanged and measurements were taken a total of 5 times, and the average value was taken as the sedimentation time (s). The results are shown in Table 4. The smaller the settling time value, the better the permeability.
• Example 4 (Examples 4-1 to 4-25, Comparative Examples 4-1 to 4-4) In a glass 50 mL sample bottle, put 0.5 g of each of the products shown in Table 5 (however, not used in Comparative Examples 4-1 to 4-4), 10 mL of ion-exchanged water, and 10 mL of various oils, and shake for 30 seconds. After that, one droplet was placed on a slide glass, sandwiched between cover glasses, and observed with a digital microscope VHX-6000 (manufactured by Keyence) at a magnification of 500 times. The particle size of the droplets was measured and evaluated according to the following criteria. The results are shown in Table 5. 1: Average particle size is less than 1 ⁇ m 2: Average particle size is 1 to 100 ⁇ m 3: Average particle size exceeds 100 ⁇ m 4: Separated and no droplets are observed
• Example 5 (Examples 5-1 to 5-9, Comparative Examples 5-1 to 5-2)
• a slide glass 76 mm ⁇ 26 mm ⁇ 1 mm
• a polypropylene substrate 80 mm ⁇ 30 mm ⁇ 1 mm
• the glass substrate or PP substrate was horizontally installed on the stage of a contact angle meter (DM-701 manufactured by Kyowa Interface Science Co., Ltd.), and 2 ⁇ L of a 1% by mass aqueous solution of the product shown in Table 6 was placed on each of the installed substrates.
• DM-701 manufactured by Kyowa Interface Science Co., Ltd.
• 2 ⁇ L of a 1% by mass aqueous solution of the product shown in Table 6 was placed on each of the installed substrates.
• the contact angle was measured 10 seconds later.
• Table 6 In Comparative Examples 5-1 and 5-2 in Table 6, the contact angle was measured in the same manner using ion-exchanged water instead of the aqueous solution. The results are shown in Table 6.
• Example 6 (Examples 6-1 to 6-5, Comparative Example 6-1) A total of 30 g of carbon black (MA-100, manufactured by Mitsubishi Chemical Corporation), each product (No Comparative Example 6-1), and ion-exchanged water were placed in a 50 mL screw tube at the ratio shown in Table 7. The screw tube was shaken for 30 seconds, and the appearance after 10 minutes was observed. The results are shown in Table 7. In Examples 6-1 to 6-5, the appearance was uniform and the dispersibility was good, and in Comparative Example 6-1 the carbon black was precipitated and separated, resulting in poor dispersibility.
• the surfactant composition and the detergent composition of the present invention are useful as detergents for various purposes.

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