WO2015170637A1 - Agent tensioactif non ionique et procédé de production d'un agent tensioactif non ionique - Google Patents

Agent tensioactif non ionique et procédé de production d'un agent tensioactif non ionique Download PDF

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WO2015170637A1
WO2015170637A1 PCT/JP2015/062775 JP2015062775W WO2015170637A1 WO 2015170637 A1 WO2015170637 A1 WO 2015170637A1 JP 2015062775 W JP2015062775 W JP 2015062775W WO 2015170637 A1 WO2015170637 A1 WO 2015170637A1
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general formula
group
nonionic surfactant
structure represented
alcohol
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PCT/JP2015/062775
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Japanese (ja)
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将基 森田
紗菜 伊藤
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株式会社ニイタカ
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • 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

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  • the present invention relates to a nonionic surfactant and a method for producing a nonionic surfactant.
  • Nonionic surfactants are widely used as materials blended in cleaning compositions for kitchens, bathrooms, kitchens and the like.
  • Patent Document 1 discloses an ether-terminated poly (oxyalkylated) alcohol as a nonionic surfactant.
  • Patent Document 1 describes a method of forming an ether-terminated poly (oxyalkylated) alcohol by reacting an alkoxylated alcohol obtained by adding an oxyalkylene group to an alcohol and an ⁇ -olefin.
  • the hydrophilic group portion becomes an oxyalkylene group portion derived from an alkoxylated alcohol, particularly an oxyethylene group portion.
  • the hydrophobic group portion becomes a carbon chain portion derived from an alkoxylated alcohol and a carbon chain portion derived from an ⁇ -olefin.
  • the alkoxylated alcohol is produced by adding an oxyalkylene group to the hydroxyl group of the alcohol, and the carbon chain portion of the alcohol becomes a carbon chain portion contained in the alkoxylated alcohol, so that the compound having an acetal structure It can become a hydrophobic group part of a nonionic surfactant consisting of
  • a nonionic surfactant consisting of
  • there are several commercially available alkoxylated alcohols but there are not many types of alcohols used as starting materials for alkoxylated alcohols that are easily available. Therefore, the partial structure of the carbon chain contained in the alkoxylated alcohol that can be selected as the hydrophobic group portion of the nonionic surfactant made of a compound having an acetal structure is limited.
  • nonionic surfactant made of a compound having an acetal structure is insufficient, and a method for producing a nonionic surfactant with many choices of structure has been desired.
  • nonionic surfactants having various structures obtained by such a production method have been desired.
  • the present invention has been made to solve the above-described problems, and provides nonionic surfactants having various structures, and production of nonionic surfactants having many structural options. It aims to provide a method.
  • the hydrophilic group portion is an oxyalkylene group portion contained in the alkoxylated alcohol.
  • the present inventors examined using alcohol as it is for acetalization reaction, without adding an oxyalkylene group to alcohol and using it for acetalization reaction. In the process, it was considered to supply the hydrophilic group portion from the ⁇ -olefin side, not from the alcohol side.
  • a hydrophilic vinyl ether in which a hydrophilic group such as an oxyalkylene group is added to the end of a vinyl compound having a hydroxyl group at the end to form a structure that becomes a hydrophilic group portion is prepared, and the hydrophilic vinyl ether and an arbitrary alcohol are prepared.
  • the acetal structure obtained by this reaction is an acetal structure containing an oxygen atom derived from a hydroxyl group of alcohol and an oxygen atom derived from hydrophilic vinyl ether. And when using the compound which has this acetal structure as a nonionic surfactant, a hydrophilic group part turns into an oxyalkylene group part derived from hydrophilic vinyl ether, especially an oxyethylene group part.
  • the carbon chain derived from alcohol is introduced as it is into the nonionic surfactant thus obtained, a number of selectable alcohol structures can be introduced, and various non-ionic surfactants having desired characteristics can be introduced.
  • An ionic surfactant is provided.
  • the nonionic surfactant of the present invention has a structure represented by the following general formula (1), It has an acetal structure formed by reaction of alcohol and hydrophilic vinyl ether.
  • R 1 is a residue derived from alcohol
  • (AO) n is an oxyalkylene group which may be the same or different, derived from a hydrophilic vinyl ether
  • n is an oxyalkylene. Represents the average number of moles of the group added, and is a number from 1 to 400.
  • X is a hydrocarbon group which may have a substituent or a hydrogen atom
  • the nonionic surfactant of the present invention has an acetal structure formed by a reaction between an alcohol and a hydrophilic vinyl ether, and has a residue R 1 derived from the alcohol. Since there are many types of alcohols available and many structures can be selected as R 1 , it can be a nonionic surfactant having various structures.
  • R 1 in the general formula (1) is preferably a hydrocarbon group having 8 to 20 carbon atoms.
  • R 1 is a hydrocarbon group having 8 to 20 carbon atoms, a structure suitable as a hydrophobic group portion is obtained.
  • Alcohols having a hydrocarbon group having 8 to 20 carbon atoms are preferred because they are particularly easily available and can be easily produced at low cost.
  • the oxyalkylene group in the general formula (1) is an oxyethylene group, an oxypropylene group or an oxybutylene group, respectively, and the ratio of the oxyethylene group contained in the oxyalkylene group Is desirably 50 mol% or more.
  • the ratio of the oxyethylene group contained in the oxyalkylene group is 50 mol% or more, the hydrophilicity of the oxyalkylene group portion is increased, and a structure suitable as the structure of the hydrophilic group portion is obtained.
  • X in the general formula (1) is a hydrocarbon group which may have a substituent, and desirably has a structure represented by the following general formula (2). .
  • R 2 is a hydrocarbon group which may have a substituent
  • That X in the general formula (1) is a hydrocarbon group means that the terminal of the nonionic surfactant is not a hydroxyl group.
  • the terminal of the nonionic surfactant is a hydroxyl group
  • the hydroxyl group of the nonionic surfactant terminal and the chlorine agent In some cases, chlorine reacts to deactivate both the nonionic surfactant and the chlorine agent.
  • the end of the nonionic surfactant By making the end of the nonionic surfactant a hydrocarbon group, the hydroxyl group at the end of the nonionic surfactant and the chlorine of the chlorinating agent are prevented from reacting with each other. It can be an ionic surfactant.
  • the terminal end of the nonionic surfactant is a hydroxyl group
  • the terminal hydroxyl group is oxidized and anionized in an alkaline environment, resulting in a structure similar to that of the anionic surfactant. It may increase.
  • the terminal structure of the nonionic surfactant is prevented from being anionized, and the nonionic surfactant becomes a low-foaming nonionic surfactant.
  • the low-foaming nonionic surfactant is suitable for use in washing with an automatic washing machine.
  • the method for producing the nonionic surfactant of the present invention comprises: A vinyl group of a hydrophilic vinyl ether having a structure represented by the following general formula (3); An acetalization step of forming an acetal bond by reacting a hydroxyl group of an alcohol having a structure represented by the following general formula (4) to produce a nonionic surfactant having a structure represented by the following general formula (1) It is characterized by doing.
  • (AO) p is an oxyalkylene group which may be the same or different, p represents the average number of added moles of the oxyalkylene group, and is a number from 1 to 400.
  • X is A hydrocarbon group which may have a substituent or a hydrogen atom)
  • R 1 is a residue of alcohol
  • R 1 is a residue derived from alcohol
  • (AO) n is an oxyalkylene group which may be the same or different, derived from a hydrophilic vinyl ether, and n is an oxyalkylene. Represents the average number of moles of the group added, and is a number from 1 to 400.
  • X is a hydrocarbon group which may have a substituent or a hydrogen atom
  • nonionic surfactant of the present invention unlike the conventional method for forming an acetal structure, a hydrophilic group portion is supplied from a hydrophilic vinyl ether, and a carbon chain derived from alcohol is introduced as it is. Since there are many kinds of available alcohols and many structures can be selected as R 1 , non-ionic surfactants having various structures can be produced according to the production method of the present invention. A variety of nonionic surfactants can be provided.
  • X in the nonionic surfactant having the structure represented by the general formula (1) obtained by the acetalization step is a hydrogen atom
  • the nonionic surfactant having the structure represented by the formula (1) has a hydroxyl group at its end
  • R 2 is a hydrocarbon group which may have a substituent
  • a nonionic surfactant having high chlorine stability and low foaming property can be produced.
  • the reaction for modifying the hydrogen atom of the hydroxyl group to a hydrocarbon group which may have a substituent is performed by dialkyl sulfate, dialkyl carbonate, alkyl halide, trialkyloxo.
  • a reaction in which the hydrogen atom is substituted with a hydrocarbon group by the action of a nium salt, an alkyl ester of alkane sulfonic acid, or an alkyl ester of arene sulfonic acid is desirable.
  • these alkylating agents are used, the hydrogen atom of the hydroxyl group located at the end of the nonionic surfactant can be replaced with a hydrocarbon group.
  • the reaction for modifying the hydrogen atom of the hydroxyl group to a hydrocarbon group which may have a substituent is carried out by the following general formula (5).
  • a nonionic surfactant having a structure represented by the following general formula (6) is obtained by reacting with a (poly) oxyalkylene alkyl ether having the structure shown to increase the number of oxyalkylene groups added. It is desirable to manufacture.
  • the hydrophilicity of the nonionic surfactant is increased by increasing the number of oxyalkylene groups added.
  • the reaction to be adjusted can be carried out simultaneously in one stage.
  • the hydrophilic vinyl ether having the structure represented by the general formula (3) is:
  • X is a hydrophilic vinyl ether having a structure represented by the following general formula (7), which is a hydrocarbon group which may have a substituent, Performing an acetalization step of reacting the vinyl group of the hydrophilic vinyl ether having the structure represented by the general formula (7) with the hydroxyl group of the alcohol having the structure represented by the general formula (4) to form an acetal bond; It is desirable to produce a nonionic surfactant having a structure represented by the following general formula (2).
  • R 2 is a hydrocarbon group which may have a substituent
  • R 2 is a hydrocarbon group which may have a substituent
  • the acetalization step is performed using a hydrophilic vinyl ether in which a hydrogen atom of a hydroxyl group located at a terminal is previously modified to a hydrocarbon group. Even by such a process, it is possible to obtain a nonionic surfactant in which a hydrocarbon group is modified from the hydroxyl group hydrogen atom located at the end of the nonionic surfactant.
  • the agent has high chlorine stability and becomes a low foaming surfactant.
  • dialkyl sulfate, dialkyl carbonate, alkyl halide, trialkyl are bonded to the hydroxyl group hydrogen atom located at the terminal of the hydrophilic vinyl ether having the structure represented by the following general formula (8).
  • a structure represented by the above general formula (7) is obtained by reacting an oxonium salt, an alkyl ester of alkane sulfonic acid, or an alkyl ester of arene sulfonic acid to replace the hydrogen atom with a hydrocarbon group. Performing a step of obtaining a hydrophilic vinyl ether having It is desirable to use for the acetalization step.
  • the hydroxyl group hydrogen atom located at the end of the hydrophilic vinyl ether is substituted with a hydrocarbon group, and the hydroxyl atom located at the end is hydrophilically modified to a hydrocarbon group in advance.
  • Vinyl ether can be obtained and used in the acetalization step.
  • a polyoxy having a structure represented by the following general formula (5) is attached to a hydroxyl group located at the end of a hydrophilic vinyl ether having a structure represented by the following general formula (9).
  • a step of obtaining a hydrophilic vinyl ether having a structure represented by the general formula (7) by modifying the hydrogen atom of the hydroxyl group to a hydrocarbon group which may have a substituent and increasing the number of oxyalkylene groups added And It is desirable to use for the acetalization step.
  • hydrophilicity is increased by increasing the number of oxyalkylene groups added.
  • the reaction for adjusting the hydrophilicity of vinyl ether can be carried out simultaneously in one step. And such hydrophilic vinyl ether can be obtained and used for an acetalization process.
  • the alcohol having the structure represented by the general formula (4) preferably has 8 to 20 carbon atoms.
  • the alcohol has 8 to 20 carbon atoms, it is suitable as the alcohol to be used because it has a structure suitable as a hydrophobic group moiety.
  • nonionic surfactant of the present invention has a structure represented by the following general formula (19), It has an acetal structure formed by the reaction of polyhydric alcohol and hydrophilic vinyl ether.
  • u is an integer of 2 or more
  • Z is a residue derived from a u-valent polyhydric alcohol
  • (AO) n is the same or different derived from a hydrophilic vinyl ether.
  • An oxyalkylene group which may be substituted, n represents the average number of moles added of the oxyalkylene group and is a number from 1 to 400.
  • X is a hydrocarbon group or a hydrogen atom which may have a substituent.
  • the nonionic surfactant has an acetal structure formed by reacting a polyhydric alcohol with a polyhydric alcohol and a hydrophilic vinyl ether, and the acetal structure exists as much as the valence of the polyhydric alcohol. .
  • the hydrophilic group portion becomes an oxyalkylene group portion derived from a hydrophilic vinyl ether, particularly an oxyethylene group portion. Since the carbon chain derived from the polyhydric alcohol is introduced as it is into the nonionic surfactant thus obtained, a large number of selectable alcohol structures can be introduced, and various properties having desired characteristics can be introduced.
  • Nonionic surfactants are provided.
  • the nonionic surfactant of the present invention can be a nonionic surfactant having various structures. Moreover, according to the method for producing a nonionic surfactant of the present invention, nonionic surfactants having various structures can be produced, and various nonionic surfactants having desired characteristics are provided. Can do.
  • FIG. 1 is an NMR spectrum of the nonionic surfactant synthesized in Production Example 1.
  • FIG. 2 is an NMR spectrum of the nonionic surfactant synthesized in Production Example 2.
  • FIG. 3 is an NMR spectrum of the nonionic surfactant synthesized in Production Example 3.
  • the nonionic surfactant of the present invention has a structure represented by the following general formula (1), It has an acetal structure formed by reaction of alcohol and hydrophilic vinyl ether.
  • R 1 is a residue derived from alcohol
  • (AO) n is an oxyalkylene group which may be the same or different, derived from a hydrophilic vinyl ether
  • n is an oxyalkylene. Represents the average number of moles of the group added, and is a number from 1 to 400.
  • X is a hydrocarbon group which may have a substituent or a hydrogen atom
  • the structure represented by the general formula (1) has an acetal structure (—O—CH (CH 3 ) —O—) formed by the reaction of alcohol and hydrophilic vinyl ether. It has a residue R 1 derived from an alcohol represented by (In general formula (4), R 1 is a residue of alcohol)
  • alcohol includes a compound having a phenolic hydroxyl group.
  • R 1 is not particularly limited as long as it is a residue derived from an alcohol, but examples thereof include the following structures in which an OH group is removed from an alcohol.
  • Examples of the alcohol include linear or branched aliphatic alcohols, which may or may not have an unsaturated bond.
  • Desirable examples of the aliphatic alcohol include methanol, ethanol, propanol, butanol, pentanol, hexanol, heptanol, octanol, 2-ethylhexyl alcohol, nonyl alcohol, decyl alcohol, isodecyl alcohol, undecyl alcohol, lauryl alcohol, Dodecyl alcohol, tridecyl alcohol, myristyl alcohol, tetradecyl alcohol, pentadecyl alcohol, cetyl alcohol, hexadecyl alcohol, isohexadecyl alcohol, heptadecyl alcohol, stearyl alcohol, octadecyl alcohol, isostearyl alcohol, elaidyl alcohol, oleyl alcohol , Linoleyl alcohol, elide
  • Examples of the alcohol include alkylphenols, and alkylphenols having a linear or branched alkyl chain. Desirable examples of the alkylphenol include 4-tert-butylphenol, 4-octylphenol, nonylphenol, dodecylphenol, octylcresol and the like.
  • R 1 is preferably a residue derived from an alcohol having 8 to 20 carbon atoms, and more preferable examples of the alcohol having 8 to 20 carbon atoms include octanol, 2-ethylhexyl alcohol, decyl alcohol, Decyl alcohol, lauryl alcohol, dodecyl alcohol, myristyl alcohol, tetradecyl alcohol, cetyl alcohol, hexadecyl alcohol, isohexadecyl alcohol, stearyl alcohol, octadecyl alcohol, isostearyl alcohol, oleyl alcohol, arachidyl alcohol (eicosanol), and 2-octyldodecan-1-ol and the like.
  • R 1 may have a substituent, and the substituent is preferably halogen (F—, Cl—, Br— or I—).
  • R 1 may contain an ether bond.
  • hydrophilic vinyl ether examples include hydrophilic vinyl ethers having a structure represented by the general formula (3).
  • (AO) p is an oxyalkylene group which may be the same or different, p represents the average number of added moles of the oxyalkylene group, and is a number from 1 to 400.
  • X is A hydrocarbon group which may have a substituent or a hydrogen atom
  • the average addition mole number of the oxyalkylene group is, as a rule, the average addition mole number of the oxyalkylene group in the produced nonionic surfactant is n, and the oxyalkylene group in the hydrophilic vinyl ether.
  • the average number of moles added is represented by p.
  • the average addition mole number of the oxyalkylene group in the nonionic surfactant represented by the general formula (1) is n
  • the average addition mole number of the oxyalkylene group in the hydrophilic vinyl ether represented by the general formula (3) is p. ing.
  • p does not necessarily indicate a number different from n, and p in the hydrophilic vinyl ether may be the same as the average added mole number n of the nonionic surfactant to be produced.
  • p and n are the same number.
  • AO oxyalkylene group
  • examples of AO include oxyethylene group (EO), oxypropylene group (PO), and oxybutylene group (BO).
  • the hydrophilic vinyl ether may contain only one kind of oxyethylene group, oxypropylene group, or oxybutylene group, or may contain plural kinds of these.
  • the unit of the repeating structure of the oxyethylene group, oxypropylene group, or oxybutylene group is not particularly limited.
  • the ratio of the oxyethylene group contained in the oxyalkylene group is preferably 50 mol% or more, and more preferably 60 mol% or more.
  • the ratio of the oxyethylene group contained in the oxyalkylene group is 50 mol% or more, the hydrophilicity of the oxyalkylene group portion is increased, and a structure suitable as the structure of the hydrophilic group portion is obtained.
  • the average added mole number p of AO in the hydrophilic vinyl ether is 1 to 400, and a preferable range of p is 3 to 100, and a more preferable range is 5 to 50.
  • the hydrophilic vinyl ether is a mixture of a plurality of compounds having different numbers of added moles of AO p
  • the number of moles of AO contained in each of the hydrophilic vinyl ether molecules is an integer value. Since the measured value when measured is measured as an average value of the added mole number of AO contained in each molecule of the hydrophilic vinyl ether, this is used as the average added mole number.
  • the hydrophilic vinyl ether may be a mixture of a plurality of compounds having different types of AO.
  • the addition format of AO may be block addition or random addition, and the addition format is not particularly limited.
  • hydrophilic vinyl ether contained in the general formula (3) examples include a structure in which X is a hydrogen atom in the general formula (3), that is, a (poly) oxyalkylene monovinyl ether having a structure represented by the general formula (8).
  • the structure of the surfactant is a structure represented by the following general formula (10).
  • (poly) oxyalkylene monovinyl ether examples include (poly) oxyethylene monovinyl ether, (poly) oxypropylene monovinyl ether, (poly) oxybutylene monovinyl ether, (poly) oxyethylene (poly) oxypropylene monovinyl ether, (Poly) oxyethylene (poly) oxybutylene monovinyl ether, (poly) oxypropylene (poly) oxybutylene monovinyl ether, and the like.
  • (poly) oxyalkylene monovinyl ether commercially available (poly) oxyethylene monovinyl ether, such as ethylene glycol monovinyl ether, diethylene glycol monovinyl ether, triethylene glycol monovinyl ether, and the like can be used. Moreover, an oxyethylene group or an oxypropylene group may be further added to these commercially available products to produce a polyoxyalkylene monovinyl ether, which may be used for the production of a nonionic surfactant.
  • (poly) of (poly) oxyalkylene monovinyl ether includes both an oxyalkylene chain having one oxyalkylene group addition and a polyoxyalkylene chain having a plurality of additions. Meaning.
  • the hydrophilic vinyl ether contained in the general formula (3) has a structure in which X is a hydrocarbon group which may have a substituent in the general formula (3), that is, the hydrophilicity of the structure represented by the general formula (7). Vinyl ether is mentioned. (In General Formula (7), R 2 is a hydrocarbon group which may have a substituent)
  • the hydrocarbon group R 2 which may have a substituent is an aliphatic alkyl group (methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group).
  • aliphatic alkyl group methyl group, ethyl group, propyl group, butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group, decyl group.
  • the terminal structure of the hydrophilic vinyl ether is a hydrocarbon group which may have a substituent
  • X becomes a hydrocarbon group R 2 which may have a substituent by reacting the alcohol with the hydrophilic vinyl ether.
  • substituent of the hydrocarbon group halogen (F—, Cl—, Br— or I—) is desirable.
  • the hydrocarbon group may contain an ether bond.
  • X is a hydrocarbon group R 2 which may have a substituent
  • the hydroxyl group at the end of the nonionic surfactant is prevented from reacting with chlorine of the chlorinating agent, so that chlorine stability is improved. It can be a high nonionic surfactant.
  • X is a hydrocarbon group R 2 which may have a substituent
  • the terminal structure of the nonionic surfactant is prevented from being anionized, and the low-foaming nonionic surfactant is prevented. It becomes.
  • the low-foaming nonionic surfactant is suitable for use in washing with an automatic washing machine.
  • the method for producing a nonionic surfactant of the present invention includes a vinyl group of a hydrophilic vinyl ether having a structure represented by the following general formula (3) and a hydroxyl group of an alcohol having a structure represented by the following general formula (4). It is characterized in that a nonionic surfactant having a structure represented by the following general formula (1) is produced by carrying out an acetalization step of forming an acetal bond by reacting with the above.
  • (AO) p is an oxyalkylene group which may be the same or different, p represents the average number of added moles of the oxyalkylene group, and is a number from 1 to 400.
  • X is A hydrocarbon group which may have a substituent or a hydrogen atom
  • R 1 is a residue of an alcohol
  • hydrophilic vinyl ether having the structure represented by the general formula (3) and the alcohol having the structure represented by the general formula (4) include those already described.
  • the reaction of the vinyl group of the hydrophilic vinyl ether and the hydroxyl group of the alcohol can be carried out by mixing the hydrophilic vinyl ether and the alcohol, and further adding an acid catalyst for reaction. This reaction may be performed in a solvent such as an organic solvent as necessary.
  • the acid catalyst examples include p-toluenesulfonic acid, benzenesulfonic acid, methanesulfonic acid, pyridinium p-toluenesulfonate, trifluoromethanesulfonic acid, sulfuric acid, hydrochloric acid, and an acidic ion exchange resin.
  • p-toluenesulfonic acid or methanesulfonic acid is desirable because it is easy to handle and inexpensive.
  • organic solvent used in the above reaction a general organic solvent can be used, and methylene chloride, chloroform, acetonitrile, tetrahydrofuran (THF), toluene, chlorobenzene, methyl tert-butyl ether and the like can be used.
  • the reaction is completed by neutralization of the acid catalyst.
  • Powder such as sodium hydrogencarbonate, sodium hydroxide, potassium hydroxide, or those solutions etc. can be used.
  • the reaction conditions can be appropriately determined depending on the type and amount of the starting material. For example, 10 mol of hydrophilic vinyl ether and 11 mol of alcohol are mixed, and 1 to 10 mol% of p-toluenesulfonic acid is added as an acid catalyst. Examples include a method of stirring for 1 hour to overnight (10 hours) at room temperature, adding sodium bicarbonate to terminate the reaction, filtering, and then distilling off the solvent and unreacted hydrophilic vinyl ether or alcohol.
  • the method for producing a nonionic surfactant of the present invention includes a vinyl group of a hydrophilic vinyl ether having a structure represented by the general formula (3) and a hydroxyl group of an alcohol having a structure represented by the general formula (4).
  • the acetalization step of forming an acetal bond by reacting is required as an essential step, and before and after this step, at least one step selected from the group consisting of the following (a), (b) and (c) is performed.
  • a nonionic surfactant whose terminal structure is a hydrocarbon group may be obtained, and the number of oxyalkylene groups added to the nonionic surfactant may be adjusted.
  • B A step of increasing the number of oxyalkylene groups added by adding alkylene oxide to a hydroxyl group located at a hydrophilic vinyl ether end or a nonionic surfactant end obtained by an acetalization step.
  • Step (a1) a step of substituting the hydrogen atom of the hydroxyl group located at the end of the hydrophilic vinyl ether with a hydrocarbon group that may have a substituent
  • Step (a2) A step of substituting the hydrogen atom of the hydroxyl group located at the terminal of the nonionic surfactant obtained by the acetalization step with a hydrocarbon group which may have a substituent.
  • the substitution reaction with a hydrocarbon group is a dialkyl sulfate, a dialkyl carbonate, an alkyl halide, a trialkyloxonium salt, an alkyl ester of an alkanesulfonic acid, or an arenesulfonic acid.
  • the reaction is preferably a reaction in which the hydrogen atom is substituted with a hydrocarbon group by the action of an alkyl ester.
  • the hydrocarbon group to be substituted with these alkylating agents is preferably a methyl group, a butyl group or a benzyl group from the viewpoint of easy availability of the alkylating agent.
  • alkylating agents examples include dimethyl sulfate, dibutyl sulfate, dimethyl carbonate, methyl halide (methyl chloride, methyl bromide, methyl iodide), butyl halide (butyl chloride, butyl bromide, butyl iodide), Benzyl halide (benzyl chloride, benzyl bromide, benzyl iodide), trialkyloxonium salt and triethyloxonium salt (trimethyloxonium tetrafluoroborate, triethyloxonium tetrafluoroborate, etc.) as trialkyloxonium salt, alkanesulfone Examples include triflate (methyl triflate, butyl triflate, benzyl triflate) and mesylate as acid alkyl ester, tosylate as alkyl ester of arenesulfonic acid, and the like.
  • the hydrogen atom of the hydroxyl group located at the end of the nonionic surfactant can be replaced with a hydrocarbon group.
  • the conditions for causing these alkylating agents to act may be known alkylation (ether synthesis) conditions, but it is desirable to carry out the reaction under basic conditions to which sodium hydroxide or sodium hydride is added.
  • reaction formula (12) the reaction for substituting the hydrogen atom of the hydroxyl group located at the end of the nonionic surfactant obtained in the acetalization step is represented by the following reaction formula (12).
  • R 2 -Y is an alkylating agent
  • Y is a residue obtained by removing an alkyl group from the alkylating agent.
  • Step (b1) increasing the number of oxyalkylene groups added to the hydrophilic vinyl ether by adding alkylene oxide to the hydroxyl group located at the end of the hydrophilic vinyl ether; and Step (b2): A step of increasing the number of oxyalkylene groups added to the nonionic surfactant by adding alkylene oxide to the hydroxyl group located at the terminal of the nonionic surfactant obtained by the acetalization step.
  • step (b1) for example, (poly) oxyethylene monovinyl ether in which p mol of an oxyethylene group is added as shown in the following reaction formula (13) is prepared, and q mol of ethylene oxide is further added, A step of producing polyoxyethylene monovinyl ether having an average addition mole number of oxyethylene groups of p + q moles may be mentioned.
  • p + q is the average number of moles of oxyethylene group added, and is a number from 1 to 400
  • (poly) oxyethylene monovinyl ether in which p mol of oxyethylene group is added is prepared, and r mol of propylene oxide and / or butylene oxide is further added to obtain an average of oxyethylene groups
  • a polyoxyethylene polyoxyalkylene monovinyl ether having an addition mole number of p mole and an average addition mole number of oxypropylene group and oxybutylene group of r mole can be produced.
  • reaction Formula (14) shows propylene oxide as a representative of propylene oxide and / or butylene oxide.
  • step (b2) for example, after producing a nonionic surfactant having an acetal structure in which p mol of an oxyethylene group is added as shown in the following reaction formula (15), q mol of ethylene oxide is further added.
  • a step of producing a nonionic surfactant having an average addition mole number of oxyethylene groups of p + q mole by addition is exemplified.
  • p + q is the average number of moles of oxyethylene group added, and is a number from 1 to 400
  • other alkylene oxides such as propylene oxide and butylene oxide may be used instead of ethylene oxide.
  • Step (c1) Hydrocarbon group which may increase the number of added oxyalkylene groups by reacting (poly) oxyalkylene alkyl ether at the end of hydrophilic vinyl ether and may have a hydrogen atom of hydroxyl group as a substituent Step to denature.
  • Step (c2) The nonionic surfactant terminal obtained by the acetalization step is reacted with (poly) oxyalkylene alkyl ether to increase the number of oxyalkylene groups added and to replace the hydroxyl group hydrogen atom.
  • a step of modifying to a hydrocarbon group which may have a group.
  • step (c1) for example, (poly) oxyethylene monovinyl ether in which p mol of oxyethylene group is added as shown in the following reaction formula (16) is prepared, and q mol of oxyethylene group is added (poly )
  • a step of reacting oxyethylene alkyl ether to produce a hydrophilic vinyl ether having an average addition mole number of oxyethylene groups of p + q mol and a terminal being a hydrocarbon group is mentioned.
  • p + q is the average number of moles of oxyethylene group added, and is a number from 1 to 400
  • step (c1) a hydroxyl group at the terminal of (poly) oxyethylene alkyl ether to which q mole of oxyethylene group has been added is modified to easily remove a tosyl group, mesyl group, trifuryl group, etc. Then, the reaction may be carried out as shown in the following reaction formula (17) to produce a hydrophilic vinyl ether having an average addition mole number of oxyethylene groups of p + q mole and a terminal being a hydrocarbon group.
  • the step of reacting after modifying the hydroxyl group at the terminal of (poly) oxyethylene alkyl ether also reacts with (poly) oxyalkylene alkyl ether having the structure represented by formula (5) in step (c). Included in the process.
  • p + q is the average number of moles of oxyethylene group added and is a number from 1 to 400. W is a substituent that can be easily removed.
  • step (c2) for example, after producing a nonionic surfactant having an acetal structure in which p mol of an oxyethylene group is added as shown in the following reaction formula (18), q mol of the oxyethylene group is Examples include a step of reacting the added polyoxyethylene alkyl ether to produce a nonionic surfactant having an average addition mole number of oxyethylene groups of p + q mol and a terminal being a hydrocarbon group.
  • p + q is the average number of moles of oxyethylene group added and is a number from 1 to 400
  • the hydroxyl group at the terminal of the (poly) oxyethylene alkyl ether to which q mole of oxyethylene group is added may be reacted.
  • the oxyethylene group in the reaction formulas (16) to (18) may be another oxyalkylene group such as an oxypropylene group or an oxybutylene group.
  • X in the nonionic surfactant having the structure represented by the general formula (1) obtained by the acetalization step is a hydrogen atom.
  • the nonionic surfactant having the structure represented by the general formula (1) has a hydroxyl group at its terminal, and the hydrocarbon group which may have a substituent on the hydrogen atom of the hydroxyl group
  • a nonionic surfactant having a structure represented by the following general formula (2) is produced.
  • R 2 is a hydrocarbon group which may have a substituent
  • This form is a form in which the hydrogen atom at the terminal of the nonionic surfactant obtained by the acetalization step is modified with a hydrocarbon group, and the step (a2) is carried out after the acetalization step, the step after the acetalization step (
  • the form in which the step (a2) is performed after performing the b2), the form in which the step (c2) is performed after the acetalization process, and the form in which the process (c2) is performed after performing the step (b2) after the acetalization process are applicable. .
  • hydrophilic vinyl ether having the structure represented by the general formula (3) is a hydrocarbon group in which X may have a substituent.
  • a nonionic surfactant having a structure represented by the following general formula (2) is produced by carrying out an acetalization step in which an acetal bond is formed by reacting a hydroxyl group of an alcohol having the same.
  • R 2 is a hydrocarbon group which may have a substituent
  • This form is a form in which the hydrogen atom at the end of the hydrophilic vinyl ether is modified with a hydrocarbon group before the acetalization process and used in the acetalization process.
  • the form in which the step (a1) is performed before the acetalization process, the acetalization process A mode in which the step (a1) is performed after the step (b1) is performed before, a mode in which the step (c1) is performed before the acetalization step, and a step (c1) after the step (b1) is performed before the acetalization step. This corresponds to the form of performing.
  • the nonionic surfactant of the present invention has a structure represented by the following general formula (19), It may be a nonionic surfactant characterized by having an acetal structure formed by the reaction of a polyhydric alcohol and a hydrophilic vinyl ether.
  • u is an integer of 2 or more
  • Z is a residue derived from a u-valent polyhydric alcohol
  • (AO) n is the same or different derived from a hydrophilic vinyl ether.
  • An oxyalkylene group which may be substituted, n represents the average number of moles added of the oxyalkylene group and is a number from 1 to 400.
  • X is a hydrocarbon group or a hydrogen atom which may have a substituent.
  • the nonionic surfactant is the same as the nonionic surfactant described above except that the polyhydric alcohol is used as the alcohol and the molar ratio of the hydrophilic vinyl ether is changed according to the valence of the alcohol. It can be manufactured by the same method.
  • the polyhydric alcohol include ethylene glycol, glycerin, trimethylolpropane, pentaerythritol, dipentaerythritol and the like.
  • the nonionic surfactant of this invention is suitable as a material mix
  • a cleaning composition using the nonionic surfactant of the present invention will be described.
  • a chlorine agent can be blended in addition to (A) the nonionic surfactant of the present invention.
  • an alkali agent can be contained.
  • the concentration of the nonionic surfactant (A) of the present invention in the cleaning composition is not particularly limited, but is desirably 0.1 to 30% by weight, preferably 0.5 to 25% by weight. % Is more desirable, and 0.5 to 20% by weight is even more desirable.
  • chlorinating agent (B) for example, chlorinated isocyanurate (sodium chlorinated isocyanurate, potassium chlorinated isocyanurate, etc.), trichloroisocyanuric acid, hypochlorite (sodium hypochlorite, Potassium hypochlorite, calcium hypochlorite, etc.).
  • hypochlorite sodium hypochlorite, Potassium hypochlorite, calcium hypochlorite, etc.
  • 1 type in these chlorine agents may be used, and 2 or more types may be used together.
  • the concentration of the chlorine agent (B) in the cleaning composition is not particularly limited, but it is desirable that it be blended so that the effective chlorine concentration is 0 to 45% by weight.
  • the concentration of the chlorine agent is preferably 0 to 50% by weight, and more preferably 2 to 50% by weight. When a plurality of types of chlorinating agents are used, the concentration of the chlorinating agent is determined as a total value of the concentration of each chlorinating agent.
  • the content of the chlorinating agent (B) with respect to the content of the nonionic surfactant (A) of the present invention is the same or greater, and the content of the chlorinating agent with respect to the content of the nonionic surfactant
  • the ratio of chlorinating agent / nonionic surfactant is preferably 1 to 100, more preferably 1 to 20, and further preferably 1 to 6.
  • a detergent composition containing a relatively large amount of chlorine agent can exhibit high bleaching and bactericidal properties.
  • an alkali metal or alkaline earth metal salt can be used, and the kind thereof is not particularly limited, but sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, hydrogen carbonate. Sodium, potassium hydrogen carbonate, sodium metasilicate, sodium sesquisilicate, sodium orthosilicate, potassium metasilicate, potassium sesquisilicate, potassium orthosilicate and the like are desirable. These alkaline agents may be hydrated. Among these, at least one selected from the group consisting of sodium hydroxide, potassium hydroxide, sodium orthosilicate, potassium orthosilicate, sodium metasilicate, potassium metasilicate, and hydrates thereof is desirable.
  • an alkali cleaner having a high detergency can be obtained.
  • 1 type in these alkaline agents may be used and 2 or more types may be used together.
  • the concentration of the alkaline agent (C) is not particularly limited, but is preferably 2 to 90% by weight, more preferably 5 to 80% by weight, and 12 to 80% by weight. More desirable. When a plurality of types of alkali agents are used, the concentration of the alkali agent is determined as a total value of the concentrations of the respective alkali agents.
  • the pH of the detergent composition is not particularly limited, but from the viewpoint of the stability of the terminal acetal structure of the nonionic surfactant (A) of the present invention, it should be in a neutral to alkaline range. Is desirable.
  • the pH is desirably 6 or more and less than 9, and in the case of a weakly alkaline detergent composition, the pH is desirably 9 or more and less than 12, and is strongly alkaline.
  • it is set as a cleaning composition it is desirable that pH is 12 or more.
  • the pH may be measured using a commercially available pH meter or the like. For example, the pH can be measured using a model D-21 manufactured by Horiba, Ltd.
  • a chlorinating agent When a chlorinating agent is blended in the cleaning composition, both the cleaning effect by the nonionic surfactant, the bleaching by the chlorinating agent, and the bactericidal effect can be exhibited.
  • a cleaning composition that is made alkaline by adding an alkali agent can further exert a cleaning effect on oil stains and the like due to the alkali agent.
  • the above-mentioned detergent composition is blended with a detergent composition such as a polymer dispersant (D), a chelating agent (E), a solvent / process agent (F), a solubilizer (G), etc., as necessary.
  • a detergent composition such as a polymer dispersant (D), a chelating agent (E), a solvent / process agent (F), a solubilizer (G), etc.
  • Other components may be contained.
  • the polymer dispersant (D) include polyacrylic acid, polyaconitic acid, polyitaconic acid, polycitraconic acid, polyfumaric acid, polymaleic acid, polymethaconic acid, poly- ⁇ -hydroxyacrylic acid, polyvinylphosphonic acid, and sulfonated polymaleic acid.
  • Olefin-maleic acid copolymer maleic anhydride diisobutylene copolymer, maleic anhydride styrene copolymer, maleic anhydride methyl vinyl ether copolymer, maleic anhydride ethylene copolymer, maleic anhydride ethylene crosslink copolymer Polymer, maleic anhydride vinyl acetate copolymer, maleic anhydride acrylonitrile copolymer, maleic anhydride acrylic ester copolymer, maleic anhydride butadiene copolymer, maleic anhydride isoprene copolymer, maleic anhydride and Derived from carbon monoxide Poly- ⁇ -ketocarboxylic acid, itaconic acid, ethylene copolymer, itaconic acid aconitic acid copolymer, itaconic acid maleic acid copolymer, itaconic acid acrylic acid copolymer, malonic acid methylene copolymer, itaconic acid
  • Examples of the chelating agent (E) include ethylenediaminetetraacetic acid (EDTA), hydroxyethylethylenediaminetriacetic acid (HEDTA), nitrilotriacetic acid (NTA), diethylenetriaminepentaacetic acid (DTPA), 2-phosphonobutane-1,2,4-tricarboxylic acid, Ethylenediaminesuccinic acid (EDDS), hydroxyethyliminodiacetic acid (HIDA), glutamic acid diacetic acid (GLDA), methylglycine diacetic acid (MGDA), aspartic acid diacetic acid (ASDA), tripolyphosphoric acid, polyacrylic acid and their salts ( Sodium salts, potassium salts, etc.), polyaspartic acid compounds represented by the following formula (20), iminodisuccinic acid compounds represented by the following formula (21), and iminodiacetic acid represented by the following formula (22) System compounds.
  • EDTA ethylenediaminetetraacetic acid
  • M is the same or different and -H, -Na, -K or -NH 4.
  • s and t are integers] [In formula (21), M is the same or different and is —H, —Na, —K or —NH 4 . ]
  • the concentration of the chelating agent in the cleaning composition is not particularly limited, but is preferably 0 to 80% by weight, more preferably 0 to 70% by weight, and 15 to 50% by weight. It is further desirable that Examples of the solvent (F) include water and commonly used organic solvents.
  • the process agent (F) is an extender in the case where the dosage form is solid, and preferably has a neutral pH, and examples thereof include sodium sulfate and powdered silica.
  • the solubilizer (G) include xylene sulfonic acid, cumene sulfonic acid, caprylic acid, octylic acid and salts thereof, alkyl diphenyl ether disulfonate, and the like.
  • nonionic surfactant comprises a vinyl group of hydrophilic vinyl ether in which the average addition mole number p of oxyethylene group is 4 in the general formula (3) and X is a methyl group, and 2-ethylhexyl alcohol. It is a nonionic surfactant having an acetal structure obtained by reacting with a hydroxyl group of
  • nonionic surfactant (A-4).
  • the obtained nonionic surfactant has an average addition mole number p of oxyethylene group of 6 in the above general formula (3), X is a methyl group, a vinyl group of hydrophilic vinyl ether, and tetradecyl alcohol. It is a nonionic surfactant having an acetal structure obtained by reacting with a hydroxyl group.
  • the obtained nonionic surfactant has an average addition mole number p of oxyalkylene group of 5 in the above general formula (3) (average addition mole number of oxyethylene group is 2, average addition mole number of oxypropylene group is 3)
  • a nonionic surfactant having an acetal structure obtained by reacting a vinyl group of a hydrophilic vinyl ether in which X is a hydrogen atom with a hydroxyl group of decyl alcohol.
  • nonionic surfactant (A-6).
  • the obtained nonionic surfactant has an average addition mole number p of oxyalkylene group of 2 in the above general formula (3), X is an octyl group, vinyl group of hydrophilic vinyl ether, and ethanol hydroxyl group.
  • Is a nonionic surfactant having an acetal structure obtained by reacting This residue in the formula (19) Z is derived from glycerin, u 3, the (AO) n is (EO) 2, X corresponds to the non-ionic surfactant of structure a hydrogen atom.
  • Nonionic surfactant (Production Example 8) To a THF solution (10 ml) of 1.3 g of the nonionic surfactant (A-2) produced in Production Example 2, 0.7 g of 1-bromobutane and 0.6 g of potassium t-butoxy were added overnight (10 hours). The mixture was refluxed and stirred at 70 ° C. Sulfuric acid was added to terminate the reaction, filtration was performed, and the solvent was distilled off to obtain a nonionic surfactant (A-8).
  • the obtained nonionic surfactant comprises a vinyl group of hydrophilic vinyl ether in which the average addition mole number p of the oxyalkylene group in the above general formula (3) is 2, and 2-ethylhexyl alcohol. It is a nonionic surfactant having an acetal structure obtained by reacting with a hydroxyl group of
  • nonionic surfactant has an average addition mole number p of oxyethylene group of 19 in the above general formula (3), and a vinyl group of hydrophilic vinyl ether in which X is a methyl group, and a hydroxyl group of octadecyl alcohol. It is a nonionic surfactant having an acetal structure obtained by reacting with a group.
  • a mixed solution was prepared by mixing 0.1 part by weight of the nonionic surfactant (A-3) and 99.9 parts by weight of water, and the surface tension of this mixed solution was measured using an automatic surface tension meter K100 manufactured by KRUSS. As a result, it was 28 mN / m at 25 ° C.

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Abstract

La présente invention concerne un agent tensioactif non ionique qui est caractérisé en ce qu'il possède une structure représentée par la formule générale (1) et en ce qu'il possède une structure d'acétal formée par une réaction entre un alcool et un éther vinylique hydrophile. (Dans la formule générale (1), R1 représente un résidu dérivé d'un alcool, (AO)n représentent des groupes oxyalkylène dérivés d'éthers vinyliques hydrophiles et sont identiques ou différents, n représente le nombre moyen de moles de groupes oxyalkylène ajoutés et est un nombre de 1 à 400. X représente un atome d'hydrogène ou un groupe hydrocarbure comprenant éventuellement un substituant).
PCT/JP2015/062775 2014-05-08 2015-04-28 Agent tensioactif non ionique et procédé de production d'un agent tensioactif non ionique WO2015170637A1 (fr)

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CN115725288A (zh) * 2021-08-26 2023-03-03 中国石油化工股份有限公司 表面活性剂组合物、润湿性调控剂及其制备方法和应用

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CN108623807B (zh) * 2018-04-28 2020-12-29 温州大学 一种基于肉桂醛的响应型聚合物纳米粒子及其制备方法
CN115725288A (zh) * 2021-08-26 2023-03-03 中国石油化工股份有限公司 表面活性剂组合物、润湿性调控剂及其制备方法和应用
CN115725288B (zh) * 2021-08-26 2024-03-26 中国石油化工股份有限公司 表面活性剂组合物、润湿性调控剂及其制备方法和应用

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