WO2005111183A1 - PROCÉDÉ SERVANT À PRODUIRE UN TENSIOACTIF ANIONIQUE CONTENANT UN ESTER ALKYLIQUE D'UN α-SULFOACIDE GRAS, TENSIOACTIF ANIONIQUE ET COMPOSITION DÉTERGENTE CONTENANT CELUI-CI - Google Patents

PROCÉDÉ SERVANT À PRODUIRE UN TENSIOACTIF ANIONIQUE CONTENANT UN ESTER ALKYLIQUE D'UN α-SULFOACIDE GRAS, TENSIOACTIF ANIONIQUE ET COMPOSITION DÉTERGENTE CONTENANT CELUI-CI Download PDF

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Publication number
WO2005111183A1
WO2005111183A1 PCT/JP2005/008859 JP2005008859W WO2005111183A1 WO 2005111183 A1 WO2005111183 A1 WO 2005111183A1 JP 2005008859 W JP2005008859 W JP 2005008859W WO 2005111183 A1 WO2005111183 A1 WO 2005111183A1
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alkyl ester
acid alkyl
fatty acid
mass
surfactant
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PCT/JP2005/008859
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English (en)
Japanese (ja)
Inventor
Ai Satoh
Go Ichitani
Kenji Ogawa
Taku Nishio
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Lion Corporation
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Priority to JP2006513575A priority Critical patent/JP4782001B2/ja
Publication of WO2005111183A1 publication Critical patent/WO2005111183A1/fr

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    • 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
    • C11D1/02—Anionic compounds
    • C11D1/12—Sulfonic acids or sulfuric acid esters; Salts thereof
    • C11D1/123—Sulfonic acids or sulfuric acid esters; Salts thereof derived from carboxylic acids, e.g. sulfosuccinates

Definitions

  • the present invention relates to a method for producing an ionic surfactant containing an ⁇ -sulfofatty acid alkyl ester salt, an anionic surfactant, and a detergent composition containing the same.
  • Neutralized salts of sulfonated fatty acid alkyl esters are also generally referred to as ex-sulfo fatty acid alkyl ester salts, which have good hard water resistance, good biodegradability, excellent detergency, and mild skin interface. Since it is an activator, it is a natural raw material that is renewable from the viewpoint of resources and is advantageous in terms of cost. It is also regarded as important in terms of global environmental protection.
  • a Sulfo fatty acid alkyl ester salt is obtained by converting a fatty acid alkyl ester with SO.
  • Ri-CH-COR 2 (a-sulfo fatty acid alkyl ester)
  • bimolecular adducts O bimolecular adducts (hereinafter referred to as “bimolecular adducts”) are produced.
  • reaction scheme the reaction proceeds rapidly up to the step of producing the bimolecular adduct, but the reaction rate is very slow in the step of producing the ⁇ -sulfofatty acid alkyl ester from the bimolecular adduct.
  • an aging step is provided to promote SO desorption.
  • a odor may be a problem in the case of a detergent composition using an a-one surfactant containing a sulfo fatty acid alkyl ester salt as a main component. Therefore, the following means for reducing odor have been proposed.
  • Patent Document 1 Japanese Patent Application Laid-Open No. 62-43499 discloses a detergent composition containing an oc-sulfofatty acid alkyl ester salt, zeolite, and formic acid or a salt thereof. I have.
  • Patent Literature 2 Japanese Patent Application Laid-Open No. 7-97080 discloses a washing method in which an oc-sulfofatty acid alkyl ester salt, a carbonate or bicarbonate, zeolite, acetic acid, and oxalic acid or a salt thereof are mixed. An agent composition is disclosed.
  • Patent Document 3 Japanese Patent Application Laid-Open No. 7-97081 discloses a detergent composition containing an oc-sulfofatty acid alkyl ester salt, wherein the Fe content is set to 200 ppm or less. Is disclosed.
  • Patent Documents 1 to 3 cannot sufficiently reduce the odor.
  • the a-one surfactant containing the ex sulfo fatty acid alkyl ester salt thus obtained as a main component includes ⁇ -sulfofatty acid di-salt having the following structure (hereinafter referred to as “di-sulfo fatty acid di-salt”). "Salt” may be abbreviated).
  • a Sulfofatty acid disalt is formed by neutralizing ⁇ -sulfofatty acid alkylsulfoester, and ⁇ -sulfofatty acid alkylsulfoester is inevitably formed when sulfonated fatty acid alkyl ester is used. Things.
  • alkyl alcohol used for transesterification examples include a short-chain alkyl alcohol having about 1 to 6 carbon atoms.
  • Patent Document 5 discloses that the reaction solution after the sulfonation is applied to the lower alcohol or the lower alkyl sulfate by using a device such as a thin film evaporator. The step of removing is indispensable. Therefore, there is a problem that this process complicates the process and requires additional equipment.
  • Patent Document 6 Japanese Patent Application Laid-Open No. 58-157762
  • the reaction solution after the sulfonation reaction is aged under reduced pressure to remove excess SO, and thereby the alkyl product as a by-product is removed.
  • Patent Document 7 JP-A-59-25368
  • a bleaching agent in the presence of a lower alcohol
  • an alkyl sulfate is formed, and the a-sulfofatty acid alkyl ester salt is produced. It is described that the hygroscopicity of an a-one surfactant containing is reduced.
  • surplus SO is removed by adding alkylbenzene to the a-sulfo fatty acid ester prior to the bleaching process.
  • Patent Document 1 JP-A-62-43499
  • Patent Document 2 JP-A-07- 197080
  • Patent Document 3 JP-A-07-97081
  • Patent Document 4 JP-A-5-58428
  • Patent Document 5 JP-A-07-247259
  • Patent Document 6 JP-A-58-157762
  • Patent Document 7 JP-A-59-25368
  • the odor stability under the temperature condition of about 60 to 80 ° C is required from the following viewpoints. That is, the temperature condition is a condition under which the OC sulfo fatty acid alkyl ester salt can be handled as a paste containing water. In addition, the surface conditions of overseas transportation and storage conditions must be considered, unless sufficient care is taken.
  • the present invention has been made in view of the above circumstances, and has an improved odor, good long-term storage stability, and is particularly resistant to odor deterioration even under high-temperature storage conditions.
  • An object of the present invention is to provide an anionic surfactant containing a salt and a detergent composition containing the same.
  • the present invention provides the following means.
  • the second invention comprises a step of sulfonating the fatty acid alkyl ester to obtain a sulfonated product, an aromatic compound adding step of adding an aromatic compound to the sulfonated product,
  • a method for producing a surfactant comprising a step of adding an alcohol having 2 or more carbon atoms to the sulfonated product and reacting the alcohol with the alcohol after or simultaneously with the compound-added kneading process. It is.
  • the amount of the aromatic compound is 0.5 to 20 parts by mass with respect to 100 parts by mass of the sulfonide.
  • a method for producing an ionic surfactant characterized in that the amount of alcohol added with several or more alcohols is 1 to 15 parts by mass with respect to 100 parts by mass of a sulfonated product.
  • a fourth invention is an anion surfactant obtained by the method for producing an aion surfactant of the second or third invention.
  • a fifth aspect of the present invention is a cleaning composition comprising the auronic surfactant of the first or fourth aspect.
  • a-one surfactant refers to an alkyl sulfate or an aromatic sulfonide formed mainly in an a-sulfofatty acid alkyl ester salt as an activator component, for example, in other production processes.
  • an anionic surfactant containing an ⁇ -sulfofatty acid alkyl ester salt which has an improved odor, good long-term storage stability, and hardly causes odor deterioration even under high-temperature storage conditions
  • a detergent composition comprising: BEST MODE FOR CARRYING OUT THE INVENTION
  • the process for producing an a-surfactant containing a sulfo fatty acid alkyl ester salt of the present invention comprises the steps of sulfonating a fatty acid alkyl ester to obtain a sulfonated product, and adding an aromatic compound to the sulfonated product.
  • the following steps (A) to (D) are sequentially performed to obtain an a-surfactant containing an a-sulfo fatty acid alkyl ester salt.
  • A a sulfonation step of sulfonating a fatty acid alkyl ester to obtain a sulfonate
  • B an aromatic compound addition step of adding an aromatic compound to the sulfonide and heating to ripen it
  • C an alkyl having 2 or more carbon atoms in the sulfonate.
  • Esterification step of esterification with alcohol (D) Neutralization step of obtaining ⁇ -sulfo fatty acid alkyl ester salt from ⁇ -sulfo fatty acid alkyl ester by neutralization with alkali
  • the sulfonation reaction may be performed by bringing the raw material fatty acid alkyl ester into contact with at least a substance that promotes sulfonation, such as a sulfonated gas.
  • the aging step can be inserted between (1) the above-mentioned steps ( ⁇ ) and ( ⁇ ); and (2) between the steps ( ⁇ ) and (C).
  • the order of the ( ⁇ ) aromatic addition step and the (C) esterification step may be the same, but the step (C) may be carried out after the step ( ⁇ ). It is preferable from the viewpoint of adjusting the amount of alkyl sulfate having 2 or more carbon atoms.
  • the sulfonation reaction is carried out by bringing the fatty acid alkyl ester as a raw material into contact with at least a substance that promotes sulfonation such as a sulfonation gas. It is particularly preferable that after the sulfonated product (reaction liquid containing ⁇ -sulfofatty acid ester as a main component) obtained by the sulfonidation reaction, a ( ⁇ ′) aging step is performed.
  • the term “sulfonated compound” as used herein refers to the entire reaction solution after the sulfonation reaction.
  • a substance that promotes sulfonation is preferably a sulfonated gas.
  • Examples of the sulfonide gas include SO gas and fuming sulfuric acid.
  • SO gas is usually a concentration of 1-40% by volume of dehumidified air or an inert gas such as nitrogen.
  • the fatty acid alkyl ester is typically a compound represented by the following general formula (I).
  • R'CH COOR 2 ⁇ (I) (wherein, R 1 is a linear or branched alkyl group having 6 to 24 carbon atoms or
  • R 2 represents a linear or branched alkyl group having 1 to 6 carbon atoms.
  • fatty acid methyl esters are often used.
  • the fatty acid alkyl ester is preferably a saturated fatty acid alkyl ester.
  • saturated fatty acid alkyl esters examples include animal fats and oils derived from power such as beef tallow and fish oil lanolin; vegetable fats and oils derived from coconut oil, palm oil, soybean oil, etc .; There is no particular limitation on the deviation of the synthetic fatty acid alkyl ester or the like that can be induced.
  • the iodine value is preferably 0.5 or less, more preferably 0.1 or less.
  • the reaction temperature may be a temperature at which the fatty acid alkyl ester has fluidity.
  • the temperature range is not less than the melting point of the fatty acid alkyl ester and is 100 ° C higher than the melting point, and preferably the temperature range is not less than the melting point and 70 ° C higher than the melting point.
  • the sulfonation method may be any one of a thin film type sulfonation method, a batch type sulfonation method and the like.
  • a sulfonation reaction method a tank-type reaction, a film reaction, a tube-type gas-liquid multiphase reaction and the like are used.
  • reaction time of the sulfonidation step varies depending on the sulfonidation method employed, but is generally about 5 to 120 seconds for the thin film type sulfonation method and about 10 to 240 minutes for the batch type sulfonation method. .
  • the (A) sulfonation step is preferably performed in the presence of a coloring inhibitor.
  • coloring inhibitor various agents that have been proposed in the past can be used.
  • coloring inhibitors refer to Japanese Patent Application Nos. 08-024433, 08-3360, 08-340149, 08-340148, 08-340147 and 08-340147. It is disclosed in Japanese Patent Application No. 08-342244, Japanese Patent Application Laid-Open No. 09-216861, Japanese Patent Application Laid-Open No. 09-216862, Japanese Patent Application Laid-Open No. 09-216863, and the like.
  • inorganic sulfate having a monovalent metal ion described in JP-A-09-216863 and having an average particle size of 250 / zm or less.
  • Inorganic sulfate wears Many are inexpensive and have high color suppression effects, and are components to be added to detergents, so there is no need to remove them from ⁇ - sulfo fatty acid alkyl ester salts.
  • the inorganic sulfate is not particularly limited as long as it is a powdered anhydrous salt having a monovalent metal ion, and examples thereof include sodium sulfate, potassium sulfate, and lithium sulfate.
  • the inorganic sulfate those having an average particle size of 250 ⁇ m or less, preferably 50 ⁇ m or less are used. During the reaction, the inorganic sulfate hardly dissolves in the reaction solution to the extent that its surface is slightly dissolved, and is dispersed in the reaction solution.
  • the dispersibility can be improved with a large contact area, and the effect can be further enhanced.
  • the coloring inhibitors can be used alone or in combination of two or more.
  • the addition amount of the coloring inhibitor is 0.1 to 20% by mass, and preferably 2 to 10% by mass, based on the fatty acid alkyl ester as the raw material. If the amount is less than 0.1% by mass, the effect of addition may not be obtained.
  • the temperature of the aging step is 70 ⁇ : LOO ° C is appropriate. If the temperature is lower than 70 ° C, the elimination reaction does not proceed rapidly. If the temperature is higher than 100 ° C, coloring may be remarkable.
  • the time required for the aging step is usually in the range of 1 to 120 minutes.
  • the step (B) of adding an aromatic compound is a step of adding an aromatic compound to the sulfonide obtained at least through the step (A).
  • the esterification step using methanol is not performed, but when fatty acid methyl ester is used as a raw material, a very small amount of methanol may be left in the system. May exist. Even in such a case, by performing the step (B), the excess SO can be reduced after the (A) sulfonation reaction step, and the production of methyl sulfate can be suppressed.
  • the aromatic sulfonide has a low SO content and a low methyl sulfate content.
  • the aromatic compound means an aromatic compound that causes a sulfonation reaction, that is, an aromatic compound having an aromatic cyclic structure such as a benzene ring, a naphthalene ring, and an anthracene ring.
  • an aromatic compound having an aromatic cyclic structure such as a benzene ring, a naphthalene ring, and an anthracene ring.
  • at least one alkyl group is bonded to the aromatic ring.
  • the alkyl group may be linear or branched and has 1 to 24, preferably 3 to 16 carbon atoms.
  • those having one or two or more benzene rings are preferable, and those having one benzene ring are particularly preferable.
  • the aromatic compound is represented by the following general formula ( ⁇ ).
  • R to R represent H or a linear or branched alkyl group having 1 to 24 carbon atoms.
  • R to R are H, and R is 1 to 2 carbon atoms.
  • Specific preferred examples include tamen and linear alkylbenzene.
  • One or more aromatic compounds can be used.
  • a disulfide compound (an aromatic sulfonide salt) obtained by neutralizing a sulfonated aromatic compound is used as a surfactant in a detergent composition such as a linear alkylbenzene sulfonate. Used! / It is intended to be used for cleaning effect!
  • the amount of the aromatic compound added is 0.5 to 20 parts by mass based on 100 parts by mass of the sulfonide. It is preferably 0.7 to 15 parts by mass, and more preferably 1 to LO parts by mass. If the amount is less than 0.5 part by mass, a sufficient effect cannot be obtained, and if it exceeds 20 parts by mass, a large amount of the aromatic compound remains unreacted and may not be preferable.
  • 100 parts by mass of the sulfonide is based on 100 parts by mass of the reaction solution immediately after the sulfonation reaction.
  • step (B) after the addition of the aromatic compound, the reaction is carried out by heating to a predetermined temperature.
  • the reaction temperature is preferably 40 to 90 ° C! / ,.
  • the temperature is less than 0 ° C, a mixture containing sulfofatty acid alkyl ester solidifies, making it difficult to handle.On the other hand, if the temperature exceeds 90 ° C, color deterioration may be promoted, which may be undesirable. is there.
  • the reaction time holds the time required for the aromatic compound to react sufficiently with the excess SO.
  • the time is about 1 to 120 minutes. If the time is less than 1 minute, the added aromatic compound may not sufficiently react with excess SO in the system, and the effect may not be obtained. 1
  • the alkyl group may be either linear or branched. Preferably, it is an alcohol having 2 to 4 carbon atoms. Particularly preferred are ethyl alcohol and isopropyl alcohol.
  • the alkyl alcohol having 2 or more carbon atoms can be used alone or in combination of two or more.
  • the added amount of the alkyl alcohol having 2 or more carbon atoms is preferably 1 to 15 parts by mass, more preferably 1.5 to 10 parts by mass, and particularly preferably 2 to 6 parts by mass based on 100 parts by mass of the sulfonated product.
  • “100 parts by mass of the sulfonated product” is the same as the standard for the amount of the aromatic compound added in the above step (B).
  • the reaction temperature is 50 to 100 ° C, preferably 50 to 90 ° C, and the reaction time is 5 to 120 minutes.
  • the esterification step does not include the bleaching step performed in the presence of alcohol, and is distinguished therefrom.
  • an aqueous solution of an alkali metal, an alkaline earth metal, ammonia, or ethanolamine is used as the alkali.
  • a paste of an ionic surfactant containing a monosulfo fatty acid alkyl ester salt is obtained.
  • the aromatic sulfonidious compound obtained in the step (B) is also neutralized here to obtain an aromatic sulfonidious salt.
  • the ⁇ -sulfofatty acid alkyl ester salt is strongly alkaline and may easily break the ester bond. Therefore, ⁇ of the neutralized solution of the sulfonide and the alkali is acidic or acidic. It is preferable to adjust to a weak alkaline range ( ⁇ 4-9, more preferably ⁇ 5-8).
  • the concentration of the aqueous alkali solution is 2 to 50% by mass, the neutralization temperature is 30 to 140 ° C, and the neutralization time is 10 to 60 minutes.
  • the (D) neutralization step can also be performed by reacting with a solid carbonate or bicarbonate.
  • neutralization with solid carbonate is cheaper than other bases and is preferred.
  • the water content in the reaction mixture decreases, It does not become Lucari.
  • the heat of neutralization at the time of neutralization is lower than that of the metal hydroxide, it is advantageous.
  • Examples of the carbonate or bicarbonate include sodium carbonate, potassium carbonate, ammonium carbonate, sodium bicarbonate, potassium bicarbonate, ammonium bicarbonate, etc. A mixture or the like can be used.
  • the treatment for improving color tone includes, for example, a bleaching treatment using a bleaching agent such as hydrogen peroxide, and is preferably performed after the neutralization step.
  • a bleaching treatment using a bleaching agent such as hydrogen peroxide
  • the bimolecular adduct can be reduced by performing (C) the esterification step, and can be produced without performing the operation of removing the alkyl sulfate, the reduction of the bimolecular adduct and the reduction of the odor can be achieved. It is possible to provide a technology that can be realized by a simple process and a simple apparatus.
  • the major feature of the production method of the present invention is that, by performing both ( ⁇ ) an aromatic compound addition step and (C) an esterification step produced by using an alcohol having 2 or more carbon atoms, the above-mentioned Patent Document As described in 5, conventional sulphate is believed to be the cause of odor, and even in the case of alkyl sulphate, it should be removed in an amount as small as possible in terms of odor reduction. In the case of alkyl sulfates having 2 or more carbon atoms, the odor is not deteriorated even if it is present in the product. Long term stability (especially long term stability under high temperature storage) ) Has been found to be preferable.
  • an aromatic sulfonide salt having a relatively small content of methyl sulfate and a C 2 -C 2 As described above, since an ionic surfactant containing an alkyl sulfate can be obtained, it is possible to suppress the generation of a substance causing an odor component due to methyl sulfate, which is generated by long-term storage at a high temperature, and to reduce aromatic sulfonide salt and carbon. It is presumed that the odor masking is not synergistic with the alkyl sulfate in synergy with the number 2 or more!
  • a-sulfofatty acid alkyl ester salt is 50 to 95% by mass, methyl sulfate is 3% by mass or less, carbon number
  • An ionic surfactant comprising 0.5 to 8% by mass of two or more alkyl sulfates and 0.1 to 20% by mass of an aromatic sulfonide salt.
  • the effect of improving odor can be enhanced. Since less methyl sulfate is preferred, there is no technical significance in defining the lower limit. However, in the present invention, the effect is obtained even if methyl sulfate is present, for example, 3% by mass or more. be able to. For example, when a methyl ester is used as a fatty acid alkyl ester as a raw material, an effect can be obtained even in the case of a force that naturally produces methyl sulfate.
  • the content of the alkyl sulfate having 2 or more carbon atoms is 0.5 to 8% by mass, preferably 1 to 8% by mass.
  • the effect of improving odor can be enhanced. Also, long-term storage It has good qualitative properties and has an effect that odor deterioration hardly occurs particularly under high-temperature storage conditions. A sufficient effect can be obtained by setting the lower limit or more. If it exceeds the upper limit, the physical properties of the ionic surfactant may not be favorable.
  • the effect of improving odor can be enhanced.
  • long-term storage stability is good, and odor deterioration hardly occurs even under high-temperature storage conditions!
  • a sufficient effect can be obtained by setting the lower limit or more. If the value exceeds the upper limit, the effect may not be obtained any more.
  • the method for producing such a surfactant surfactant is not particularly limited.
  • an operation of reducing methyl sulfate for a reaction product containing a large amount of an ⁇ -sulfofatty acid alkyl ester salt, an aromatic sulfonate, or the like can be obtained by adjusting the composition by performing an operation of adding a dandelion salt or an alkyl sulfate having 2 or more carbon atoms or the like, but it is convenient to produce it by the production method of the present invention.
  • the content of the aromatic sulfonide salt can be changed by adjusting the reaction conditions in the step (ii) in the production method of the present invention.
  • the content of the alkyl sulfate having 2 or more carbon atoms can be changed by adjusting the reaction conditions in the step (C) in the production method of the present invention.
  • the content of methyl sulfate can be adjusted by not performing the transesterification reaction using methanol.
  • the preferred embodiments are the preferred raw materials and the additives described in the above-mentioned production method of the present invention. This is the same as that obtained by using an agent.
  • a second embodiment is an iron surfactant obtained by the method for producing an iron surfactant of the present invention.
  • the same effect as in the first embodiment can be obtained.
  • the ar-one surfactant containing the sulfosulfo fatty acid alkyl ester salt of the present invention can be made into a detergent composition by a conventional method.
  • the detergent composition is suitable for clothing and the like.
  • the detergent composition may contain ordinary detergent components such as a chelate builder, an alkali agent, a re-staining inhibitor, a bleaching agent, a fluorescent agent, an enzyme, and other surfactants.
  • ordinary detergent components such as a chelate builder, an alkali agent, a re-staining inhibitor, a bleaching agent, a fluorescent agent, an enzyme, and other surfactants.
  • Examples of materials that can be blended include the following. Needless to say, detergent-use components other than those exemplified below can be used as needed.
  • Surfactant 'a-ionic surfactant a straight-chain alkylbenzene sulfonate having an alkyl group having an average of 10 to 16 carbon atoms, a linear or branched alkyl group having an average of 10 to 20 carbon atoms.
  • Alkyl ethoxy sulphate with an average of 0.5 to 10 moles of ethylene oxide added per molecule alkyl sulphate with an alkyl group with an average of 10 to 20 carbon atoms, and an average of 10 to 20 carbon atoms
  • Olefin sulfonic acid salts in one molecule, fatty acid salts having an average carbon number of 10 to 20 and the like can be mentioned.
  • Nonionic surfactants polyoxyethylene alkyl ethers having an alkyl group having an average number of carbon atoms of 10 to 20 and added with 1 to 20 moles of ethylene oxide, higher fatty acid alcohol amides or alkylene oxide adducts thereof And the like.
  • surfactants include betaine-type amphoteric surfactants, sulfonic acid-type amphoteric surfactants, phosphate ester-based surfactants, and cationic surfactants.
  • alkyl is a concept including an alkyl containing an unsaturated bond.
  • Chelate builders are divalent metal ion scavengers.
  • zeolites Specifically, zeolites, orthophosphates, pyrophosphates, tripolyphosphates, nitrite triacetates, ethylenediaminetetraacetates, citrates, isoquates, polyacrylates, polyacetal carboxylates And the like.
  • Recontamination inhibitor examples include polyethylene glycol, polyvinyl alcohol, polyvinyl pyrrolidone, carboxymethyl cellulose and the like.
  • Additives such as bleach, optical brightener, and enzyme
  • bleaching agent examples include sodium percarbonate, sodium perborate, sodium sulfate, sodium chloride and sodium hydrogen peroxide.
  • fluorescent whitening agent a commercially available fluorescent dye can be blended.
  • enzymes examples include protease, cellulase, amylase, lipase and the like.
  • An ⁇ -sulfofatty acid alkyl ester salt-containing surfactant was prepared by the following method under the conditions shown in Tables 1 to 4, and the change in odor with time was tested by the following evaluation method.
  • the sulfonidation reaction was carried out in a tank reactor (made of SUS316L having a capacity of 200 L and equipped with a jacket cooling and stirrer) as follows.
  • the aging process was performed for 40 minutes while maintaining the temperature at 80 ° C.
  • the addition amount of the aromatic compound is shown by the addition amount (parts by mass) relative to 100 parts by mass of the sulfonate.
  • the esterified reaction solution was continuously neutralized with an aqueous sodium hydroxide solution (by the neutralization method described in JP-A-2001-64248), and the pH was 5 to 7; Neutralized product with 50% to 70% by mass of alkyl ester salt was obtained.
  • the neutralization temperature was controlled at 70 to 80 ° C, and the residence time of the neutralized product was 15 to 30 minutes.
  • the neutralization method described in Japanese Patent Application Laid-Open No. 2001-64248 refers to a method in which a reaction solution before neutralization is supplied to a loop formed with a line force capable of circulating the reaction solution, and circulated. This is a method of gradually neutralizing while supplying. In the loop, the mixture of the reaction solution before neutralization and the neutralized product begins to circulate as the alkali is supplied and circulated, initially circulating the reaction solution before neutralization. Then, alkali is gradually supplied to the mixture. By such an operation, neutralization can be performed under mild conditions.
  • this neutralized product was charged into a 200 L stirred tank equipped with a jacket, and 1 to 2% by mass of a pure content with respect to the ⁇ -sulfofatty acid alkyl ester salt was sufficiently added using 35% hydrogen peroxide solution.
  • the mixture was added with mixing, and a bleaching reaction was carried out at a bleaching temperature of 80 ° C. and a bleaching time of 6 to 24 hours to obtain an ionic surfactant paste containing a sulfofatty acid alkyl ester salt.
  • an odor test was performed at this stage.
  • Example 9 after that, a sulfone fatty acid alkyl ester salt-containing a-one surfactant paste was rotated at a rotational speed of 1060 rpm and a blade tip speed of about 11 lmZsec. , Heat transfer surface: 0.5m 2 , inner diameter: 205mm, clearance between heat transfer surface and blade tip: 2-4mm, introduced by Shinko Pantech Co., Ltd. at 50-90kgZhr, and inner wall heating temperature 120- Concentration was performed at 140 ° C and a degree of vacuum of 0.007 to 0.014 MPa, and the concentrated product was cooled to 20 to 30 ° C using a drum flaker (manufactured by Kusunoki Kikai Seisakusho).
  • Fitzmill product name, manufactured by Hosokawa Micron Co., Ltd., DKA-3 type, first stage screen diameter 8mm ⁇ , second stage screen diameter: 3.5mm ⁇ , blade rotation speed first stage: 4700rpm, second stage: 2820rpm) and pulverized with high concentration oc-sulfo fatty acid alkyl ester salt-containing surfactant powder Got.
  • an ionic surfactant paste containing a sulfo fatty acid alkyl ester salt was obtained in the same manner as in Examples 1 to 8, and an odor test was similarly performed. .
  • An a-one surfactant paste containing a sulfo fatty acid alkyl ester salt was obtained in the same manner as in Examples 1 to 8 except that the aromatic compound was not added and methanol was used in the esterification reaction, and similarly, An odor test was performed.
  • the ⁇ -sulfofatty acid alkyl ester salt was prepared in the same manner as in Examples 1 to 8 under the conditions of the aromatic compound addition process and the esterification process shown in the table. A -on surfactant paste was obtained and similarly odor tested.
  • components other than the main components shown in the table are disalts, sodium sulfate, fatty acid alkyl esters, alkylbenzenes or turmeric, moisture, and the like.
  • ⁇ -SF′Na is “ ⁇ -sulfofatty acid methyl ester sodium salt”
  • LAS-NaJ is “straight chain alkylbenzene sodium having an alkyl group having 10 to 14 carbon atoms (aromatic sulfonamide) Salt) ”.
  • Noun surfactant (25% by mass based on pure a-sulfofatty acid ester sodium salt) is added and flash concentrated.
  • Water heating tube product name SFC-300 (heat transfer area 0.5 m 2 ) manufactured by Sakuma Seisakusho Co., Ltd.) at a heating tube temperature of 130 ° C (using pressurized steam as a heating medium).
  • Recycle flash concentration was carried out to 10% to obtain a mixed concentrate of oc sulfo fatty acid alkyl ester sodium salt and Noon surfactant.
  • non-ionic surfactant and optional components except for some zeolites are dissolved or dispersed in tap water (Edogawa-ku, Tokyo), and a slurry (solid content: 60% by mass) is prepared under the following conditions. Spray drying was performed under the following spray drying conditions to obtain dried particles.
  • Spray drying conditions ⁇ Spray drying equipment: countercurrent type, tower diameter 2.0 m, effective length 5.0 m, atomization method: pressurized nozzle method, spray pressure: 30 kgZcm 2 , hot air inlet temperature: 260 ° C, hot air outlet temperature: 90 ° C, discharge method: Zeolite (1.5% by mass vs. dry particles) is introduced at the bottom of the tower together with cold air And then discharged after cooling + improving flowability.
  • a non-ionic surfactant (10% by mass of water) and a small amount of tap water (Edogawa-ku, Tokyo) are continuously kneaded (KRC, manufactured by Kurimoto Iron Works, Ltd.). (S4 type) and continuously kneaded at a temperature of 50 to 65 ° C. to obtain a dough. Kneader jacket Warm or cold water or an aqueous solution of ethylene glycol was flowed so as to maintain the above-mentioned kneading temperature.
  • zeolite 2.0 mass% vs. crushing
  • a rolling drum 0.6 m in diameter, 0.48 m in length, with 4 baffles of thickness Imm x 12 cm x width 48 cm, rotation speed 20 rpm. Particles) and coat the resulting detergent particles with a non-ionic surfactant (0.5% by mass vs. crushed particles: added to prevent dusting), enzyme (1.0% by mass vs. crushed particles) , A fragrance (0.1% by mass to ground particles) and a pigment (0.01% by mass to ground particles) were added to obtain a high bulk density granular detergent composition.
  • the odor test of the obtained detergent composition was performed by the following test method.
  • Potassium carbonate Asahi Glass Co., Ltd., food grade.
  • Sodium sulfite Anhydrous sulfite, manufactured by Shinshu Chemical Co., Ltd.
  • Polymer a copolymer of maleic acid and atalylic acid (Nippon Shokubai Co., Ltd., product name Aqualic TL 400).
  • Fluorescent agent Chino Pearl CBS—X, manufactured by Ciba Specialty Chemicals.
  • Bleaching components such as enzymes, fragrances, dyes, and organic peracid precursors.
  • the present invention can be applied to the production of an anionic surfactant containing an ⁇ -sulfofatty acid alkyl ester salt and a detergent composition containing the same.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Detergent Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Il est exposé un procédé servant à produire un ester alkylique d'un α-sulfoacide gras comprenant une étape servant à obtenir un produit sulfoné en sulfonant un ester alkylique d'un acide gras, une étape d'ajout d'un composé aromatique dans laquelle un composé aromatique est ajouté au produit sulfoné et une étape d'estérification dans laquelle un alcool ayant 2 ou plus de deux atomes de carbone y est ajouté pour faire en sorte que le produit sulfoné réagisse avec l'alcool. L'étape d'estérification est effectuée après ou en même temps que l'étape d'ajout d'un composé aromatique.
PCT/JP2005/008859 2004-05-19 2005-05-16 PROCÉDÉ SERVANT À PRODUIRE UN TENSIOACTIF ANIONIQUE CONTENANT UN ESTER ALKYLIQUE D'UN α-SULFOACIDE GRAS, TENSIOACTIF ANIONIQUE ET COMPOSITION DÉTERGENTE CONTENANT CELUI-CI WO2005111183A1 (fr)

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JP2006513575A JP4782001B2 (ja) 2004-05-19 2005-05-16 α―スルホ脂肪酸アルキルエステル塩を含むアニオン界面活性剤の製造方法、アニオン界面活性剤及びこれを含む洗浄剤組成物

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010168375A (ja) * 2008-12-26 2010-08-05 Lion Corp α−スルホ脂肪酸アルキルエステル含有組成物の製造方法
CN102216262A (zh) * 2008-11-21 2011-10-12 狮王株式会社 α-磺基脂肪酸烷基酯盐水溶液的制造方法
JP5489996B2 (ja) * 2008-06-02 2014-05-14 ライオン株式会社 脂肪酸アルキルエステルスルホナート金属塩フレーク及びその製造方法

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08170094A (ja) * 1994-12-20 1996-07-02 Lion Corp α−スルホ脂肪酸アルキルエステル塩高濃度スラリーおよびその製造方法
JPH10175940A (ja) * 1996-12-16 1998-06-30 Lion Corp 淡色α−スルホ脂肪酸アルキルエステル塩とその製造方法
JP2000128852A (ja) * 1998-10-21 2000-05-09 Lion Corp 淡色α−スルホ脂肪酸アルキルエステル塩の製造方法
JP2000191627A (ja) * 1998-12-28 2000-07-11 Lion Corp スルホン化反応方法および装置
JP2001011040A (ja) * 1999-06-25 2001-01-16 Lion Corp α−スルホ脂肪酸アルキルエステル塩の製造方法

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH08170094A (ja) * 1994-12-20 1996-07-02 Lion Corp α−スルホ脂肪酸アルキルエステル塩高濃度スラリーおよびその製造方法
JPH10175940A (ja) * 1996-12-16 1998-06-30 Lion Corp 淡色α−スルホ脂肪酸アルキルエステル塩とその製造方法
JP2000128852A (ja) * 1998-10-21 2000-05-09 Lion Corp 淡色α−スルホ脂肪酸アルキルエステル塩の製造方法
JP2000191627A (ja) * 1998-12-28 2000-07-11 Lion Corp スルホン化反応方法および装置
JP2001011040A (ja) * 1999-06-25 2001-01-16 Lion Corp α−スルホ脂肪酸アルキルエステル塩の製造方法

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5489996B2 (ja) * 2008-06-02 2014-05-14 ライオン株式会社 脂肪酸アルキルエステルスルホナート金属塩フレーク及びその製造方法
CN102216262A (zh) * 2008-11-21 2011-10-12 狮王株式会社 α-磺基脂肪酸烷基酯盐水溶液的制造方法
CN102216262B (zh) * 2008-11-21 2013-11-27 狮王株式会社 α-磺基脂肪酸烷基酯盐水溶液的制造方法
JP2010168375A (ja) * 2008-12-26 2010-08-05 Lion Corp α−スルホ脂肪酸アルキルエステル含有組成物の製造方法

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