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WO2004092314A1 - Tensioactifs oligomeres et compositions detergentes les contenant - Google Patents

Tensioactifs oligomeres et compositions detergentes les contenant Download PDF

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Publication number
WO2004092314A1
WO2004092314A1 PCT/JP2003/004683 JP0304683W WO2004092314A1 WO 2004092314 A1 WO2004092314 A1 WO 2004092314A1 JP 0304683 W JP0304683 W JP 0304683W WO 2004092314 A1 WO2004092314 A1 WO 2004092314A1
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WO
WIPO (PCT)
Prior art keywords
fatty acid
acid
surfactant
oligolactic
mass
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2003/004683
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English (en)
Japanese (ja)
Inventor
Shigeyoshi Uenoyama
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
UENOYAMA GIKEN CO Ltd
Meiwa Corp
Original Assignee
UENOYAMA GIKEN CO Ltd
Meiwa Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
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Application filed by UENOYAMA GIKEN CO Ltd, Meiwa Corp filed Critical UENOYAMA GIKEN CO Ltd
Priority to JP2004570859A priority Critical patent/JPWO2004092314A1/ja
Priority to AU2003236242A priority patent/AU2003236242A1/en
Priority to PCT/JP2003/004683 priority patent/WO2004092314A1/fr
Publication of WO2004092314A1 publication Critical patent/WO2004092314A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • 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
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/34—Higher-molecular-weight carboxylic acid esters
    • 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
    • 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
    • A61K8/37—Esters of carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • 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
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • 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
    • C11D1/04—Carboxylic acids or salts thereof

Definitions

  • the present invention relates to an oligomer type surfactant and a detergent composition containing the same.
  • the present invention relates to an oligomer type surfactant used for a detergent and the like, a surfactant composition containing the same, and uses thereof.
  • detergent compositions include anionic surfactants such as alkyl sulfates, polyoxyalkylene alkyl sulfates, monosulfo fatty acid ester salts, ⁇ -olefin sulfonic acid salts, and the like, and polyoxyethylene alkyl ethers.
  • anionic surfactants such as polyalkyl darcoside and polyoxyethylene glycerin fatty acid ester are used. Since these surfactants have excellent detergency and emulsifying power, they are widely used in detergents, emulsifiers, cosmetics, and the like.
  • surfactants with high safety as well as detergency and emulsifying power have been demanded in consideration of the effects on the environment and the human body.
  • highly safe cleaning agents for example, sucrose fatty acid esters, glycerin mono fatty acid esters, and the like are known.
  • surfactants that are highly safe, mild on the skin, and excellent in detergency, emulsifying power, etc. are required for washing foods that are taken orally and kitchen utensils that are frequently in contact with the human body.
  • a surfactant that can achieve both of them has not been obtained.
  • lactic acid has a bacteriostatic and fungicidal effect, which improves the shelf life of food It is used as a food preservative.
  • Polylactic acid-based polymers are attracting attention as biodegradable polymers.
  • fatty acid lactic acid ester salts are useful as anionic surfactants in applications such as buns, cosmetics, detergents, etc. (Japanese Patent Application Laid-Open Nos. Sho 62-62337, Hei 4_ Publication No. 230900).
  • Japanese Patent Application Laid-Open No. 9-208484 discloses an ester derivative of a fatty acid and a lactic acid or a salt thereof having a cis-l-octadecenoic acid content of 85% or more, with a content of 0.05 to 5%.
  • a cosmetic containing 5% by weight is disclosed.
  • Fatty acid chloride is obtained by reacting a fatty acid with a high content of cis-19-octadecenoic acid with phosphorus oxychloride, and then reacting the fatty acid chloride with lactic acid to synthesize lactic acid octadecane. This improves the moisturizing of the stratum corneum of the skin, keeps the skin young and healthy, and avoids the problem of irritation to the skin due to heavy use.
  • Japanese Patent Application Publication No. 2000-530093 discloses stearoyl lactinate as an OZW type emulsifier for the preparation of cosmetic and pharmaceutical preparations such as shampoos for hair, hair lotions and skin creams. It is disclosed that a fatty acid lactic acid ester such as sodium is used. It is described that this improves the emulsifying power and emulsion stability.
  • Japanese Patent Application Laid-Open No. 9-278686 has disclosed that in order to solve the problems of the conventional fatty acid lactate ester salts, fatty acid lactate ester salts having 14 to 22 carbon atoms and 14 to 22 carbon atoms were used.
  • An emulsifier composition comprising a sucrose fatty acid ester of the formula (I), wherein the former has a molar fraction of 0.008 to 0.15.
  • soybean oil and liquid paraffin are emulsified using a mixture of potassium stearate lactate and sucrose fatty acid ester.
  • an emulsifier with high versatility, high safety, gentle to the human body, excellent dispersibility, low foaming property, and excellent emulsion stability was obtained. Therefore, it can be used as an emulsifier for foods and cosmetics.
  • the present invention has been made in view of the above-mentioned conventional problems, and provides an oligomeric surfactant having high safety, less skin irritation, no unnecessary foaming, and excellent emulsifying power and detergency.
  • An object of the present invention is to provide a surfactant composition containing the same, and a detergent composition containing the surfactant composition. Disclosure of the invention
  • esters of oligolactic acid and fatty acids which are dehydration-condensation polymers of lactic acid, have superior detergency compared to fatty acid lactic acid esters, and are of the oligomer type. Because of this, it has low critical micelle concentration (cmc) and exhibits surfactant properties even in a small amount, so it can be used in a smaller amount than conventional surfactants, and also has excellent surfactant properties such as good emulsifying power. And found that the present invention was completed.
  • cmc critical micelle concentration
  • the present invention provides an oligomer type I surfactant comprising an oligolactic acid fatty acid ester represented by the following general formula (1) or a salt thereof.
  • M is at least one selected from a hydrogen atom or an alkali metal, an alkaline earth metal, an alkanolamine, an ammonia, a basic amino acid, and a lower alkylamine.
  • N is 2 to 15.
  • (e) is an alkyl or alkenyl group having 10 to 14 carbon atoms. Further, it is preferable that the average n is 3 to 5.
  • the oligomer type surfactant of the present invention can be obtained by an esterification reaction between a fatty acid having 8 to 24 carbon atoms and oligolactic acid.
  • the present invention provides an oligomer type surfactant composition wherein the content of the oligolactic acid fatty acid ester represented by the above formula (1) or a salt thereof is 30% by mass or more, and the surfactant composition
  • the present invention provides a detergent composition having a content of 0.1 to 60% by mass.
  • a detergent composition containing 0.1 to 60% by mass of the oligomer type surfactant composition, 0.1 to 30% by mass of an anionic surfactant and 0.1 to 30% by mass of a Z or nonionic surfactant. is provided.
  • the cleaning composition of the present invention is suitably used for cleaning foods, dishes, automatic dishwashers, or kitchen utensils. BEST MODE FOR CARRYING OUT THE INVENTION
  • the oligomer type surfactant of the present invention contains an oligolactic acid fatty acid ester represented by the formula (1) or a salt thereof as an essential component.
  • a fatty acid constituting the oligolactic acid fatty acid ester or a salt thereof used in the present invention a fatty acid having 8 to 24 carbon atoms, preferably 10 to 18 carbon atoms, more preferably 10 to 14 carbon atoms is used.
  • the fatty acid chain length is less than 8
  • the affinity of the hydrophobic portion with the oil is reduced, so that the detergency and the emulsion stability are deteriorated. If the fatty acid chain length exceeds 24, the hydrophobicity is strong.
  • the fatty acid chain length is outside the above range, it becomes difficult to obtain raw materials.
  • the fatty acid may be saturated or unsaturated, and may be linear or branched. In the case of a branched chain, the length of the longest chain is preferably 8 or more, more preferably 10 or more. Further, a hydroxyl carboxylic acid having a hydroxyl group may be used.
  • fatty acids include caprylic acid, capric acid, lauric acid, myristic acid, palmitic acid, stearic acid, araquinic acid, behenic acid, tetradecenoic acid, hexadecenoic acid, oleic acid, and elaidin.
  • Acid linoleic acid, linolenic acid, ricinoleic acid, eicosenoic acid, eicosatetraenoic acid (arachidonic acid), docosenoic acid (eric acid), isostearic acid, hexyldecanoic acid, 'hexyl decanoic acid, octyldecanoic acid, Examples include hydroxytetradecanoic acid, hydroxyhexadecanoic acid, hydroxyoctadecanoic acid, 12-hydroxystearic acid, 10-hydroxyoctadecanoic acid, and 2-hydroxydecanoic acid.
  • lower alkyl (1 to 3 carbon atoms) esters of these fatty acids can also be used.
  • Specific examples of these fatty acid alkyl esters include methyl laurate, methyl myristate, and the like.
  • oligolactic acid fatty acid ester these fatty acids may be a mixture of two or more kinds in an arbitrary ratio, or coconut fatty acids.
  • Oligolactic acid in oligolactic acid fatty acid ester (salt) is lactic acid An oligomer obtained by polymerizing is used, and its synthesis method does not matter. Lactic acid may be produced by either a fermentation method or a synthetic method,
  • Examples of a method for synthesizing oligolactic acid include a method in which lactic acid is directly dehydrated in the presence of a catalyst and polycondensed.
  • the degree of polymerization n of the oligolactic acid in the oligolactic acid fatty acid ester (salt) is in the range of 2 to 15.
  • the degree of polymerization n is less than 2, the cleaning power tends to decrease, and disadvantages such as precipitation of crystals at low temperatures occur.
  • the degree of polymerization exceeds 15, the detergency tends to decrease as in the case where the degree of polymerization is low.
  • the degree of polymerization n in the oligolactic acid fatty acid ester (salt) is more preferably 2 to 10, and even more preferably 2 to 8. In particular, it is preferable that the average value n of the polymerization degree is in the range of 3 to 5.
  • the oligolactic acid fatty acid ester or a salt thereof is usually obtained by reacting a fatty acid or a reactive derivative such as a fatty acid chloride, a fatty acid salt or a fatty acid ester with a lactic acid oligomer or a salt thereof.
  • the reaction is usually carried out at a temperature of 80 to 250 and 2 to 10 hours, and can be performed in the presence or absence of a solvent.
  • fatty acid chloride is used in a basic solvent, 10 to 90,:! It can be done in ⁇ 3 hours.
  • it is obtained by esterifying a lactic acid oligomer and a fatty acid (or an ester thereof).
  • the reaction is performed in the presence of a catalyst (for example, an acid catalyst such as sulfuric acid) using a fatty acid in a ratio of 0.8 to 1.2 moles per mole of the lactic acid oligomer.
  • a catalyst for example, an acid catalyst such as sulfuric acid
  • oligomerization and esterification may be simultaneously performed while mixing 0.3 to 0.6 mol of a fatty acid with respect to 1 mol of lactic acid and dehydrating the mixture under reduced pressure.
  • the reaction is usually carried out at a temperature of 80 to 150 ° C. for 2 to 10 hours.
  • the reaction solution of oligolactic acid fatty acid ester or salt thereof produced by a known method contains, in addition to oligolactic acid fatty acid ester, unreacted fatty acid or salt thereof, lactic acid or salt thereof, fatty acid lactate ester or salt thereof, and solvent. If used, additional solvent is present.
  • the content of the target oligolactic acid fatty acid ester or its salt in the reaction product excluding the solvent varies depending on the ratio of the fatty acid used for the reaction to the oligolactic acid, but the oligolactic acid fatty acid ester or its salt It is about 30 to 70 mol% based on the total amount of unreacted fatty acids or salts thereof, lactic acid or salts thereof, and fatty acid lactic acid esters or salts thereof.
  • the oligolactic acid fatty acid ester or a salt thereof of the present invention can be obtained by purifying the esterification reaction product by a usual purification technique.
  • Purification methods include, for example, liquid-liquid extraction of the reaction mixture with an aqueous solvent and an organic solvent to generate an organic solvent phase rich in oligolactic acid fatty acid ester and an aqueous solvent phase rich in lactic acid, and the two phases are separated. Then, the oligolactic acid fatty acid ester in the organic solvent phase is separated from the coexisting fatty acid by crystallization, or an aqueous acid solution is added to the reaction mixture to precipitate an oligolactic acid fatty acid ester as an oil. Is obtained by dissolving the resultant in an organic solvent to obtain a solution, and crystallizing and obtaining an oligolactic acid fatty acid ester from the solution.
  • the molar ratio of the basic substance to the oligolactic acid fatty acid ester thus obtained in an aqueous solution or an alcoholic aqueous solution such as ethanol (oligolactic acid fatty acid ester basic substance) 1 / 0.8 to 1Z 1.
  • an oligolactic acid fatty acid ester salt can be obtained.
  • the surface activity can be kept good.
  • the molar ratio of the basic substance is too large, hydrolysis of the oligolactic acid fatty acid ester is caused by an increase in the basic substance.
  • the oligolactic acid fatty acid ester salt decreases, and the ratio of stone and oligolactic acid increases. Therefore, the stability of the oligolactic acid fatty acid ester salt with time in the presence of water is reduced, and the detergency and the emulsifying power are reduced.
  • the molar ratio of the basic substance is too small, the hydrolysis rate of the oligolactic acid fatty acid ester is low, but the performance as an ionic surfactant is reduced due to the small amount of basic ion, and the oligolactic acid fatty acid ester salt Surface activity is reduced.
  • Bases that form salts with oligolactic acid fatty acid esters include alkali metals such as sodium and potassium, alkaline earth metals such as calcium and magnesium, alkanolamines such as monoethanolamine, diethanolamine, and triethanolamine, ammonia,
  • the surfactant composition of the present invention includes a basic amino acid such as arginine and a lower alkylamine such as triptylamine.
  • the surfactant composition of the present invention mainly comprises oligolactic acid fatty acid ester (salt), a trace amount of fatty acid lactate ester, and unreacted fatty acid.
  • the content of the oligolactic acid fatty acid ester (salt) in the surfactant composition is preferably 30% by mass or more.
  • the content of the oligolactic acid fatty acid ester is preferably 30 to 70% by mass, more preferably 35 to 70% by mass, and particularly preferably 40 to 70% by mass.
  • the content of the oligolactic acid fatty acid ester is defined as follows. When the content of the ester is less than 30% by mass, the lactic acid fatty acid ester having low surface activity due to equilibrium between the compositions, fatty acid, This is because the increase in lactic acid or the like causes the oligolactide fatty acid ester to exhibit insufficient surface activity, and the surfactant has a reduced detergency.
  • the total content of oligolactic acid fatty acid ester and fatty acid lactic acid ester is preferably 90% by mass or more. Said The total content is specified because if it is lower than 90% by mass, the unreacted fatty acids increase and the odor worsens. Further, the mass ratio between the oligolactic acid fatty acid ester and the fatty acid lactic acid ester is 50 to 99Z1 to 50, preferably 55 to 95Z5 to 45, more preferably 60 to 90Z10. It is appropriate to set to ⁇ 40.
  • the reason for limiting the mixing ratio in this way is that if the mixing ratio is smaller than 50/50, the ratio of oligolactic acid fatty acid ester decreases, and the detergency decreases due to the increase in lactic acid fatty acid ester having low surface activity.
  • the ratio is larger than 99/1, the distribution of the degree of polymerization of lactic acid is broadened, so that the characteristics of the surfactant are apt to fluctuate. It is.
  • the surfactant composition of the present invention When the surfactant composition of the present invention is used as a detergent, it is usually appropriate to incorporate 0.1 to 60% by mass of an oligolactic acid fatty acid ester (salt) in the detergent composition.
  • the amount is more preferably from 1 to 45% by mass, and even more preferably from 5 to 30% by mass.
  • the reason for limiting the mixing ratio in this manner is that if the blending amount in the detergent composition is too small, the detergency decreases, and if it is too large, the handleability deteriorates, and in some cases, the detergency decreases and the surfactant In some cases.
  • any one of the commonly used additive components for detergents can be selected and added as long as the object of the present invention is not impaired.
  • additional components include surfactants such as anionic surfactants, nonionic surfactants, surfactants such as carboxybetaine-type, imidazolidinum-type or sulfobetaine-type amphoteric surfactants, carrageenan, Natural bean gum, guar gum, evening malin gum, gum arabic, xanthan gum, pectin, pullulan, casein, gelatin, albumin, casein, soy protein, dartene, etc.
  • surfactants such as anionic surfactants, nonionic surfactants, surfactants such as carboxybetaine-type, imidazolidinum-type or sulfobetaine-type amphoteric surfactants, carrageenan, Natural bean gum, guar gum, evening malin gum, gum arabic, xanthan gum, pectin, pullulan, casein, gelatin, albumin
  • Natural viscosity stabilizers methylcellulose, sodium caseinate, polyacrylic acid which synthetic thickeners, chelating agents such as citric acid, builders such as inorganic salts, hydrotropes such as aromatic sulfonates, viscosity modifiers, fragrances, coloring agents, antioxidants, preservatives, and disinfectants , Anti-inflammatory agents, medicinal ingredients, enzymes and the like.
  • the solvent of the detergent composition is usually water, but may further contain another liquid solvent such as a lower alcohol, glycol or the like.
  • anionic surfactant for example, one or more anionic functional groups selected from the group consisting of a carboxylic acid group, a sulfonic acid group, a sulfate group, and a phosphate group as a polar group are particularly preferred.
  • polyoxyethylene alkyl ether sulfate, a-olefin sulfonic acid salt, alkyl ether carboxylate, fatty acid soap, acyl taurate, alkyl phosphate ester salt and the like are particularly preferable.
  • anionic surfactants can be used alone or in combination of two or more.
  • the amount is preferably in the range of 0.1 to 30% by mass, particularly preferably in the range of 1 to 15% by mass, in the detergent composition.
  • nonionic surfactant examples include polyoxyethylene alkyl ethers, polyglycerin fatty acid esters, glycerin monofatty acid esters, glycerin difatty acid esters, pull-mouth nicks, sorbitan fatty acid esters, and polyoxyethylene sorbitan. Evening fatty acid esthetic Sucrose fatty acid ester, polyoxyethylene acyl ester, alkyl polyglycoside, fatty acid methyl daricoside ester, alkylmethyl glucamide, fatty acid alkanolamide and the like.
  • fatty acid esters of polyhydric alcohols such as polyglycerin fatty acid ester, glycerin mono, difatty acid ester, sorbitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester and sucrose fatty acid ester are safe. It is more preferred because it has high potency and is approved as a food additive.
  • nonionic surfactants can be used alone or in combination of two or more. When the nonionic surfactant is blended, the blending amount is preferably in the range of 0.1 to 30% by mass, particularly preferably in the range of 1 to 15% by mass in the detergent composition.
  • the compounding ratio (oligomer type surfactant composition / other surfactant)
  • the amount of the agent is 10 to 99Z1 to 90, preferably 15 to 90710 to 85, and more preferably 20 to 80/20 to 80 by mass ratio.
  • the reason for limiting the combination ratio in this manner is that if the ratio is less than 10 90, the detergency decreases, and if it is greater than 991, the solubility of the oligolactic acid fatty acid ester in water decreases.
  • the lipophilic oligolactic acid fatty acid ester is solubilized and the whole becomes an aqueous solution.
  • the stability of the aqueous surfactant solution is also improved.
  • the detergency against oil stains is significantly greater than when only other anionic surfactants and nonionic surfactants are used. improves.
  • the oligolactic acid fatty acid ester of the present invention is itself C ⁇ D, BOD, It is a highly safe surfactant with low fish toxicity. Therefore, the cleaning composition of the present invention can be used for cleaning foods, fibers, skin, hair, hard surfaces, etc., but foods, dishes, kitchen utensils, kitchen utensils, and the like, in which safety is particularly required. Suitable for cleaning of types. In particular, it can be safely used as a detergent for removing contaminants, extra fat, protein, etc. from fruits, vegetables, meat, and fish. It can also be used as a rinse agent except for water spots on commercial dishes in the restaurant industry.
  • the body since it acts gently on the body, it can be used in household cleaners such as shampoos, body soaps, kitchen cleaners, and baby bottle cleaners. It can also be used to clean kitchen and kitchen utensils such as home and commercial refrigerators (inside and outside), microwave ovens (inside and outside), sinks, countertops, and cooking utensils. Furthermore, it can be used as a detergent for automatic dishwashers.
  • Lactic acid 53 g, 0.5 mol
  • toluene 80 ml
  • 50 g (0.25 mol) of lauric acid and 0.5 ml (0.01 mol) of sulfuric acid were added, and the mixture was reacted while being dehydrated at 100 ° (: up to 130 ° C for 3 hours).
  • the reaction product was cooled to room temperature, and water was added to the obtained reaction product to add water 3 Om1.
  • the aqueous phase and the toluene phase were separated, and the remaining toluene phase was concentrated at a temperature of 125 ° C or lower to obtain 85.9 g of a reaction purified product.
  • the yield was 99.88%.
  • the resulting reaction product is subjected to gel permeation chromatography (G (PC).
  • G gel permeation chromatography
  • Mw mass average molecular weight
  • Mw mass average molecular weight
  • hexamers a lauroyl oligolactic acid ester having a mass average molecular weight (Mw) of 509 and an average degree of polymerization of lactic acid of 4 was obtained.
  • dimers, trimers, pentamers, and hexamers were present together with the tetramers.
  • GPC analysis confirmed that the base peak (molecular ion peak) was a hexamer.
  • Lauroyl oligolactic acid ester (LL-5) was neutralized using an aqueous sodium hydroxide solution to prepare lauroyl oligolactic acid ester Na (LL-5-Na).
  • the stability of the aqueous solution was evaluated by storing a 1% aqueous solution (pH 7.0) of L L-5-Na at room temperature for 52 days.
  • a 1% aqueous solution (pH 7.0) of L L-5-Na at room temperature for 52 days.
  • the surface tension and critical micelle concentration (cmc) of the LL_5-Na aqueous solution were measured by the ring method.
  • the measurement temperature was 2 Ot :.
  • a 0.2 mm thick, 1 x 1 cm square cotton cloth (Daiwabo, canvas # 6) was used as a test piece. Place 20 cc of the sample aqueous solution in a 50 cc volume beaker, hold the test piece kept at 30 ⁇ 1 C and 60% relative humidity at both ends of the tweezers, gently drop it on the liquid surface, and drop it on the sample solution surface. From the moment the cloth touched, the stopwatch was pressed and timed, and the number of seconds until the cloth completely separated from the liquid surface due to natural settling and settled was read.
  • C a C l 2 6 0 % and Mg C l 2 and 40% mixed C a C_ ⁇ 3 hard water was adjusted to a total of 0.1% in terms of (C a C l 2 - 2 H 2 0 8 8 2 1 g and Mg C 1 2 ⁇ 6 H 2 ⁇ 0.81 32 g were added to make 100 cc). Precipitation occurred immediately when no sample was added or when soaps such as sodium laurate were added.
  • Lauroyl oligolactic acid ester Na (LL-5-Na) was diluted with ion-exchanged water to obtain aqueous solutions of 0.05 wt%, 0.1 wt% and 0.2 wt%, respectively, in terms of solid content. Prepared.
  • lauroyl lactate An aqueous solution of the same concentration was prepared using steal. The detergency of these aqueous solutions
  • Polyoxetylene lauryl sulfate Na (average number of moles added) 3 20% LL-5-Na 5% Polyoxyethylene lauryl ether (average number of moles added 5) 5% Coconut fatty acid diethanolamide 3% lauryl dimethyl Aminoxide 3% paratoluenesulfonic acid Na 2% Benzoic acid Na
  • the potassium salt of lauroyl oligolactic acid ester (LL-5-K) obtained in Production Example 1 the following body soap composition was prepared (pH 7.0).
  • the composition exhibited creamy lather, fast rinsing, good refreshing feeling after rinsing, and no irritation to the skin.
  • oligomer type surfactant having high safety, low skin irritation, excellent performance as a surfactant, particularly excellent in detergency and emulsifying power, and having low foaming property Agent can be provided. Since this surfactant has high safety and excellent detergency, it can be used as various cleaning agents for foods, fibers, skin, hair, hard surfaces, etc., as well as for electronic parts, metals, It can be widely used as industrial detergents such as ceramics. It can also be used as an emulsifier, dispersant, antistatic agent, fiber treatment agent, and the like.

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Abstract

L'invention porte sur des tensioactifs oligomères qui ne présentent aucun risque, n'irritent quasiment pas la peau, sont exempts de mousse inutile et présentent un excellent pouvoir émulsifiant. L'invention porte également sur des compositions de tensioactifs comprenant ces caractéristiques et sur des compositions détergentes contenant ces compositions de tensioactifs. Les tensioactifs oligomères contiennent des esters d'acide gras d'acide oligolactique représentés par la formule générale (I) ou des sels de ceux-ci et des tensioactifs contenant au moins 30 % en poids de ceux-ci et pouvant être utilisés comme détergents pour fibres, peau, cheveux, surfaces dures, etc. Dans cette formule, R1 représente alkyle ou alcényle C7-23 ; M représente hydrogène ou au moins un élément sélectionné parmi des métaux alcalins, des métaux alcalino-terreux, des alcanolamines, de l'hydroxyde d'ammonium, es amino-acides basiques et des alkylamines inférieurs ; et n vaut entre 2 et 15.
PCT/JP2003/004683 2003-04-14 2003-04-14 Tensioactifs oligomeres et compositions detergentes les contenant Ceased WO2004092314A1 (fr)

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Application Number Priority Date Filing Date Title
JP2004570859A JPWO2004092314A1 (ja) 2003-04-14 2003-04-14 オリゴマー型界面活性剤及びそれを含有する洗浄剤組成物
AU2003236242A AU2003236242A1 (en) 2003-04-14 2003-04-14 Oligomeric surfactants and detergent compositions containing the same
PCT/JP2003/004683 WO2004092314A1 (fr) 2003-04-14 2003-04-14 Tensioactifs oligomeres et compositions detergentes les contenant

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PCT/JP2003/004683 Ceased WO2004092314A1 (fr) 2003-04-14 2003-04-14 Tensioactifs oligomeres et compositions detergentes les contenant

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JP (1) JPWO2004092314A1 (fr)
AU (1) AU2003236242A1 (fr)
WO (1) WO2004092314A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54134711A (en) * 1978-04-12 1979-10-19 Lion Corp Shampoo composition
EP0278370A2 (fr) * 1987-02-12 1988-08-17 Kao Corporation Ester d'acide gras - acide lactique
JPH0423900A (ja) * 1990-05-16 1992-01-28 Kao Corp 洗浄剤組成物

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54134711A (en) * 1978-04-12 1979-10-19 Lion Corp Shampoo composition
EP0278370A2 (fr) * 1987-02-12 1988-08-17 Kao Corporation Ester d'acide gras - acide lactique
JPH0423900A (ja) * 1990-05-16 1992-01-28 Kao Corp 洗浄剤組成物

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JPWO2004092314A1 (ja) 2006-07-06
AU2003236242A8 (en) 2004-11-04
AU2003236242A1 (en) 2004-11-04

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