Classifications

• • 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
  • C11D1/29—Sulfates of polyoxyalkylene ethers
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
  • A61K8/34—Alcohols
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
  • A61K8/00—Cosmetics or similar toiletry preparations
  • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
  • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
  • A61K8/46—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur
  • A61K8/463—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing sulfur containing sulfuric acid derivatives, e.g. sodium lauryl sulfate
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
  • A61Q19/00—Preparations for care of the skin
  • A61Q19/10—Washing or bathing preparations
• • 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
  • C11D3/02—Inorganic compounds ; Elemental compounds
  • C11D3/04—Water-soluble compounds
  • C11D3/044—Hydroxides or bases
• • 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
  • C11D3/2006—Monohydric alcohols

Definitions

• the present invention relates to a surfactant composition. Specifically, the present invention relates to a surfactant composition containing an alkyl ether sulfate ester salt having a specific structure.
• a polyoxyalkylene alkyl ether sulfate is an anionic surfactant comprising a sulfate of a higher alcohol or an alkylene oxide adduct thereof, has little irritation to the skin, and is a liquid detergent such as dishwashing detergent, shampoo, clothing It is widely used as the main active agent for detergents and the like.
• polyoxyalkylene alkyl ether sulfate salts are not a single substance, and are mainly distributed as compositions containing water because of their general production methods. The content of a general polyoxyalkylene alkyl ether sulfate salt in the composition is less than 30% by mass or around 70% by mass from the solution physical properties.
• JP-A49-15706 discloses that a solution containing ethanol, water, and higher secondary alcohol ethoxylate sulfate in a predetermined ratio can be obtained by a predetermined production method.
• a liquid surfactant composition containing alcohol ethoxyl sulfate at a high concentration and substantially free of lower alcohols such as ethanol and methanol can be obtained by a predetermined production method. It is disclosed.
• GB-A 1428273 discloses that a liquid alcohol ethoxyl sulfate solution having a high concentration and a uniform liquid can be obtained by blending a primary alcohol or isopropanol having 2 to 4 carbon atoms as a liquid detergent composition.
• the present invention comprises (a) a compound represented by the following general formula (1) [hereinafter referred to as component (a)] 40 to 58 mass%, (b) an alcohol having 1 to 6 carbon atoms [hereinafter referred to as (b)
• component relates to a surfactant composition containing 13 to 20% by mass, (c) an alkali agent (hereinafter referred to as component (c)) 0.002 to 0.5% by mass, and water.
• R is a hydrocarbon group having 8 to 24 carbon atoms
• PO and EO are a propyleneoxy group and an ethyleneoxy group, respectively
• m and n represent the number average addition mole number of PO or EO, respectively. (0 ⁇ m ⁇ 5, 0 ⁇ n ⁇ 20, M is a cation (excluding hydrogen ions) PO and EO may be added in blocks or random)
• the present invention provides a surfactant composition comprising a polyoxyalkylene alkyl ether sulfate ester salt having a structure to which propylene oxide has been added at a high concentration and having excellent odor and hue stability under long-term storage conditions.
• R is preferably a linear or branched alkyl group or alkenyl group having 8 to 20 carbon atoms. Furthermore, if the carbon number of R is 10 to 20, the polyoxyalkylene alkyl ether sulfate ester salt has a better balance of surface activity and solubility in water.
• alkyl group and alkenyl group include various decyl groups, various dodecyl groups, various tetradecyl groups, various hexadecyl groups, various octadecyl groups, various icosyl groups, various octadecenyl groups, and the like.
• the component (a) preferably includes a compound in which R in the general formula (1) is an alkyl group. Further, it is preferable to include a compound in which the carbon number of R is 8 to 16, more preferably 10 to 14, and particularly 12 to 14.
• R in the general formula (1) is an alkyl group.
• m in the general formula (1) is the number of moles of PO added, and the number average value in the component (a) is a number that is more than 0 and less than 5, but is used as the main active agent of the liquid detergent.
• the average value is preferably 0.1 to 3, and the basic properties such as detergency, low-temperature stability, physical properties of the detergent composition, biodegradability, etc. are comprehensive.
• the average value is preferably 0.1 to 3, more preferably 0.2 to 2, particularly preferably 0.3 to 0.9.
• “/” in the general formula (1) is a convenient symbol for separating PO and EO.
• n is the number of EO addition moles, the number average value in the component (a) is more than 0 and 20 or less.
• the number average value is preferably from 0.3 to 12, more preferably from 0.6 to 10, and more preferably from 0 to 10.
• EO and PO may be added in blocks or randomly.
• the order of addition of EO and PO is optionally, for example, EO / PO, PO / EO, EO / PO / EO, etc. are preferred.
• the compound which carried out the block addition in order of PO and EO to RO- is preferable.
• M in the general formula (1) is a cation group that forms a salt, such as an alkali metal ion, an alkaline earth metal ion, an ammonium ion, and an alkanol ammonium ion such as a mono-, di-, or triethanolammonium ion.
• a salt such as an alkali metal ion, an alkaline earth metal ion, an ammonium ion, and an alkanol ammonium ion such as a mono-, di-, or triethanolammonium ion.
• the alkali metal include sodium, potassium, and lithium
• examples of the alkaline earth metal include calcium. Among these, sodium and potassium are more preferable, and sodium is particularly preferable.
• the component (a) a compound represented by the following general formula (1 ′) obtained by adding blocks in the order of PO and EO to RO— of the general formula (1) is preferable.
• R, m, and M in the general formula (1 ′) are the same as those in the general formula (1).
• RO- (PO) m - (EO ) n SO 3 M (1 ') (In the formula, R is a hydrocarbon group having 8 to 24 carbon atoms, PO and EO are a propyleneoxy group and an ethyleneoxy group, respectively, m and n represent the number average addition mole number of PO or EO, respectively. 0 ⁇ m ⁇ 5, 0 ⁇ n ⁇ 20 M is a cation (excluding hydrogen ions).
• the component (a) used in the surfactant composition of the present invention is not particularly limited.
• the alcohol used in the step (I) include natural alcohols derived from coconut oil, palm oil, beef tallow and the like, and synthetic high-grade compounds obtained by the oxo method, the Ziegler method, the paraffin direct oxidation method, and the like. Alcohol etc. are mentioned.
• the alcohol may be saturated or unsaturated, and may be either primary or secondary, but is preferably saturated or primary. Alcohol may be branched.
• the usage-amount of propylene oxide with respect to 1 mol of said alcohol is the quantity which can manufacture the polyoxyalkylene alkyl ether sulfate ester salt represented with general formula (I).
• propylene oxide with respect to 1 mole of the alcohol is a number of more than 0 mole and less than 5 moles, but when used as the main activator of the liquid detergent, the basic performance is cleanability, low temperature stability,
• it is preferably 0.1 to 3 moles, and more preferably 0.2 to 2 moles from the reactivity during production. More preferably, it is 0.3 to 0.9.
• Step (II) is a step of adding ethylene oxide to the propylene oxide adduct obtained in the above step (I) in an average of more than 0 mol and not more than 20 mol.
• the amount of ethylene oxide used relative to 1 mole of the alcohol is preferably an amount capable of producing the component (a).
• the number of ethylene oxide per mole of the alcohol is more than 0 moles and 20 moles or less
• the basic performance as the main activator of the liquid detergent is comprehensively similar to the number of moles of PO added.
• it is preferably 0.3 to 12, more preferably 0.6 to 10, and more preferably 0.8 to 5 mol, more preferably 1 to 2.3 mol, from the viewpoint of detergency and stability. is there.
• a conventionally known method can be used. That is, an autoclave is charged with 0.5 to 1 mol% of potassium hydroxide (KOH) or the like as a catalyst, heated and dehydrated, and at a temperature of 120 to 160 ° C., a predetermined amount of propylene oxide and It can be produced by addition reaction of ethylene oxide. At this time, the addition form is block addition, and propylene oxide addition [step (I)] and ethylene oxide addition [step (II)] are performed in this order.
• the autoclave to be used is preferably provided with a stirring device, a temperature control device, and an automatic introduction device.
• Step (III) is a step of sulfating and then neutralizing the alkoxylate obtained in the above step (II).
• the sulfation method include methods using sulfur trioxide (liquid or gas), sulfur trioxide-containing gas, fuming sulfuric acid, chlorosulfonic acid, and the like, and particularly prevent the generation of waste sulfuric acid and waste hydrochloric acid. From the viewpoint, a method in which sulfur trioxide is continuously supplied in a gaseous or liquid state simultaneously with the alkoxylate is preferable.
• the batch type in which the sulfate is added and neutralized, and the sulfate and the neutralizer are continuously fed into the pipe are mentioned, in this invention, there is no limitation in the neutralization method.
• the neutralizing agent used here include an aqueous alkali metal solution, aqueous ammonia, and triethanolamine, but an aqueous alkali metal solution is preferred, and sodium hydroxide is more preferred.
• the component (a) obtained as described above is preferably used as an aqueous solution having a concentration of the component (a) of 10 to 70% by mass.
• the components (a) to (c) are finally adjusted so as to have the desired ratio of the present invention.
• neutralizing agent sodium hydroxide etc.
• the usage-amount of this (c) component is obtained by the sulfate which is a precursor compound of (a) component, for example, above-mentioned process (III).
• the content of component (c) in the surfactant composition of the present invention is 0.002 to 0.5% by mass, preferably 0.025 to 0.3% by mass. %, Particularly preferably 0.05 to 0.1% by mass, and the surfactant composition of the present invention has a pH (20 ° C.) of 10 to 13.6, preferably 11 to 13.5, more preferably. By using an amount of 11.5 to 13.4, the surfactant composition of the present invention can be easily obtained. Therefore, according to the present invention, the following steps (i) to (iii) are included, (a) component 40 to 58 mass%, (b) component 13 to 20 mass%, and (c) component 0.002 to 0.5 mass%.
• a method for producing a surfactant composition containing% by mass and water is provided.
• Step (iii): The alkoxylate sulfate obtained in the above step (ii) contains more components (c), (b) and water than are necessary for neutralization of the sulfate.
• Step (i) can be performed in the same manner as the above-described steps (I) and (II). Further, the sulfation in the step (ii) can be performed in the same manner as the above-described step (III). Further, in the step (iii), the excess of the component (c) relative to the amount of neutralization of the sulfate is used as a liquid mixture (preferably an aqueous solution) containing the component (b) and water, together with the neutralization of the sulfate. A predetermined amount of component (c) is supplied.
• (c) component the theoretical value from a raw material can be employ
• Component (c) is used in such an amount that the final surfactant composition has a pH (20 ° C.) of 10 to 13.6, more preferably 11 to 13.5, and even more preferably 11.5 to 13.4. It is preferable.
• the mixture obtained in step (iii) is the surfactant composition of the present invention as long as the content of the components (a) to (c) is within the scope of the present invention, as it is or further within the scope of the present invention. The composition can be adjusted and used.
• the composition of the present invention comprises 40 to 58 mass%, preferably 50 to 58 mass% of the polyoxyalkylene alkyl ether sulfate salt represented by the general formula (1) as the component (a).
• the content is particularly preferably 52 to 56% by mass.
• polyoxyalkylene alkyl ester sulfate ester salt is defined to include those having a structure other than an alkyl group such as an alkenyl group.
• Component (b)] (B) Although it does not specifically limit as a component, Methanol, ethanol, a propanol, a butanol, a pentanol, a hexanol etc. are mentioned, Ethanol is more preferable from a general purpose and good handleability.
• the surfactant composition of the present invention contains the component (b) in an amount of 13 to 20% by mass, preferably 13 to 18% by mass, particularly preferably 13 to 16% by mass.
• the surfactant composition of the present invention contains component (c) in an amount of 0.002 to 0.5% by mass, preferably 0.025 to 0.3% by mass, particularly preferably 0.05 to 0.1% by mass. To do.
• the surfactant composition of the present invention may contain components other than the components (a) to (c) as long as the stability of the composition can be maintained. Preferably, the total of components (a) to (c) is 55% by mass or more in the composition, and more preferably 60 to 99% by mass.
• the surfactant composition of the present invention contains water.
• the content of water is preferably 45% by mass or less, more preferably 25 to 40% by mass in the composition.
• the surfactant composition of the present invention may be an aqueous solution containing the components (a) to (c).
• pH buffer agents such as a phosphate and a citrate, antiseptic
• the polyoxyalkylene alkyl ether remaining after the sulfation reaction, the inorganic sulfate produced as a by-product during neutralization (a) component, and other components incorporated in the production process of other components are within the range that does not impair the effects of the present invention. May be present.
• the surfactant composition of the present invention has a viscosity at ordinary temperature (20 ° C.) of preferably 1000 mPa ⁇ s or less, more preferably 500 mPa ⁇ s or less, more preferably 200 mPa ⁇ s or less, particularly preferably 100 mPa ⁇ s. It is as follows. This viscosity was measured at 20 ° C. using a Brookfield type (B type) viscometer. From the viewpoint of long-term storage stability, the surfactant composition of the present invention preferably has a pH (20 ° C.) of weakly alkaline to alkaline (preferably pH 10 to 13.6), preferably pH 11 to 13.5. It is more preferable that the pH is 11.5 to 13.4.
• the surfactant composition of the present invention can be suitably used as a component of a liquid detergent composition.
• auxiliary agents such as pigments, fragrances, solubilizers, and builders can be appropriately added to the liquid detergent composition as necessary.
• other anionic surfactants, cationic surfactants, amphoteric surfactants, amide type nonionic surfactants and the like can be added for the purpose of adjusting detergency and foaming.
• a liquid detergent composition is used, for example, in shampoos, body shampoos, kitchen detergents, liquid soaps and the like.
• Examples 1 to 5 Comparative Examples 1 and 2 A stirrer, a temperature controller, 3447 g of alcohol having 12 carbon atoms (Kao Corporation, product name: Calcoal 2098), 1341 g of alcohol having 14 carbon atoms (Kao Corporation, product name: Calcoal 4098), and 6.8 g of KOH.
• the mixture was charged into an autoclave equipped with an automatic introduction device and dehydrated at 110 ° C. and 1.3 kPa for 30 minutes. After dehydration, nitrogen substitution was performed, and after raising the temperature to 120 ° C., 575 g of propylene oxide was charged.
• the obtained alkoxylate was sulfated in a thin-film sulfation reactor using SO 3 gas.
• Sodium hydroxide aqueous solution containing ethanol is added to the obtained sulfate, and polyoxyalkylene alkyl ether sulfate ester salt [(a) component], ethanol [component (b)] and sodium hydroxide [component (c)] ] was obtained at a concentration shown in Table 1.
• the aqueous sodium hydroxide solution containing ethanol was used so that the concentrations of ethanol and sodium hydroxide in the surfactant composition were as shown in Table 1.
• the composition analysis of the surfactant composition was performed by the following method.
• a surfactant composition is collected so as to be 10 g as a component, and water is added to make a total volume of 100 mL to obtain a sample solution.
• the polyoxyethylene alkyl ether sulfate ester salt is a compound obtained by adding a block in the order of PO and EO to RO- in the general formula (1), and R in the general formula (1) is an alkyl group having 12 carbon atoms. And a mixed alkyl group of 14 alkyl groups, m is 0.4, n is 1.5, and M is sodium.
• Comparative Example 2 in consideration of the hue change after 5 days of standing, the hue after 15 days of standing was not evaluated.
• Examples 6 to 8, Comparative Examples 3 and 4 A surfactant composition having the composition shown in Table 2 was obtained in the same manner as Example 1 except that the compound shown in Table 2 was used as the polyoxyalkylene alkyl ether sulfate salt (component (a)).
• the polyoxyalkylene alkyl ether sulfate ester salt (component (a)) in Table 2 was obtained according to the production method of Example 1 and the like, and after adding 1 mol of ethylene oxide to alcohol in number average. , Obtained from an ethoxylate sulfate added with 2.5 moles of propylene oxide in number average. Table 2 shows the results of the same evaluation as in Example 1 and the like.
• the polyoxyethylene alkyl ether sulfate ester salt is a compound obtained by adding a block of EO and PO to RO- in the general formula (1) in this order, and R in the general formula (1) is an alkyl group having 12 carbon atoms. And a mixed alkyl group of 14 alkyl groups, m is 2.5, n is 1, and M is sodium.
• Comparative Example 4 in consideration of the hue change after 5 days of standing, the hue after 15 days of standing was not evaluated.

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• 2009
  • 2009-12-16 JP JP2009284895A patent/JP5571367B2/ja not_active Expired - Fee Related
  • 2009-12-25 US US13/142,063 patent/US20110266496A1/en not_active Abandoned
  • 2009-12-25 CN CN2009801524266A patent/CN102264885A/zh active Pending
  • 2009-12-25 EP EP09835123.2A patent/EP2371938B1/en not_active Not-in-force
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