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
  • C11D1/04—Carboxylic acids or salts thereof
  • C11D1/10—Amino carboxylic acids; Imino carboxylic acids; Fatty acid condensates thereof

Definitions

• This invention relates to a detergent composition. More particularly, it relates to a detergent composition which is suitable for washing the body including the hair and the skin and comfortable in its use.
• Body detergent compositions usually comprise common anionic surfactants. Namely, soaps, i.e., higher fatty acid salts are mainly used for cleansing the skin while alkyl sulfates or sulfonates are mainly used for shampooing the hair.
• the soaps used for cleansing the skin are disadvantageous in that the soap scum (calcium salts of higher fatty acids) formed during rinsing would adhere to the skin, which seriously deteriorates the lubricity of the surface of the skin and causes coarseness or tension.
• an oily component such as a higher alcohol or a humectant such as propylene glycol
• an anionic surfactant which never forms any scum.
• the present inventors have conducted extensive studies and thus found out that the aforesaid objects can be achieved by using a specific N-acyl compound as the main base of a detergent composition.
• the present invention which has been completed based on the above finding, provides a liquid detergent composition containing 5 to 60% by weight of a potassium or alkanolamine salt of a secondary amide-type N-acylamino acid represented by the following general formula (I), which will be referred to as the first invention hereinafter.
• RCONH(CH2) n COOH (I) wherein R represents a straight-chain saturated hydrocarbon acyl group having 10 to 14 carbon atoms; and n is a number of 2.
• the present inventors have conducted further studies and thus found out that the above objects can be achieved by using a specific N-acyl compound as the main base of a detergent composition and combining said compound with other surfactant(s) at a specific ratio.
• the present invention which has been completed based on the above finding, provides a detergent composition
• RCONH(CH2) n COOM (II) wherein RCO represents a straight-chain acyl group having 8 to 22 carbon atoms; n is an integer of from 1 to 11; and M represents an alkali metal or an inorganic or organic ammonium.
• Each of the liquid detergent composition and detergent composition of the present invention is highly soluble in water, has good foaming properties during cleansing, shows a rapid foam breaking during rinsing, gives no sliminess, imparts a high lubricity to the surface of the material to be cleansed from the rinsing step to after the drying, is less irritative, causes neither coarseness nor tension after the completion of the use and is excellent in the comfort in its use. Thus it is particularly suitable for cleansing the skin (body and face) or shampooing the hair.
• liquid detergent composition of the first invention will be described in detail.
• the potassium or alkanolamine salt of the N-acylamino acid represented by the above general formula (I) (hereinafter also called the N-acyl compound), which is one of the components of the detergent composition of the first invention, would react with calcium in tap water to form highly lubricant platy crystals.
• RCO in the above general formula (I) of the aforesaid N-acyl compound is a straight-chain saturated hydrocarbon acyl group having 10 to 14 carbon atoms, in particular, a lauroyl group having 12 carbon atoms.
• the carbon atom number thereof exceeds 14
• the lubricity of the formed platy crystals and the foaming properties of the composition are deteriorated.
• the carbon atom number thereof is less than 10
• the foaming properties are deteriorated. Thus both of these cases are undesirable.
• the lubricity of the platy crystals formed by the reaction between the aforesaid N-acyl compound and calcium may be determined by, for example, measuring the coefficient of static friction of the platy crystals on dried pigskin (ALLOASK; a product of Kotai Kasei Kogyo K.K.) which has been reconstituted with physiological saline. Namely, platy crystals showing a coefficient of static friction lower than that of the blank lot throughout the moisture-containing point to after the completion of the drying are rated high.
• ALLOASK dried pigskin
• the aforesaid N-acyl compound has a secondary amide-type structure wherein the N-acyl group consists of the above-mentioned straight-chain acyl.
• the acyl group constituting the N-acyl group is branched or the amide has a tertiary amide type structure, the formation of the platy crystals is suppressed or the formed crystals are poor in lubridity and thus sticky. In these cases, therefore, a desirable texture can be hardly obtained.
• the aforesaid N-acyl compound is a potassium (hereinafter sometimes abbreviated as K) or an alkanolamine salt such as monoethanolamine, diethanolamine or triethanolamine (hereinafter sometimes abbreviated as TEA) salt of an N-acylamino acid represented by the above general formula (I). It is undesirable to use a sodium (hereinafter sometimes abbreviated as Na) of the N-acylamino acid since it has a high Krafft point and a low solubility in water and is therefore unsuitable for a liquid detergent.
• K potassium
• TEA triethanolamine
• the content of the aforesaid N-acyl compound may range from 5 to 60% by weight, preferably from 20 to 50% by weight, based on the composition of the first invention.
• the content thereof is less than 5% by weight, the state of feeling refreshed and comfort in its use due to the platy crystals formed during rinsing cannot be obtained.
• it exceeds 60% by weight on the other hand, the liquid composition would set to gel and thus a good liquid detergent composition cannot be obtained.
• the aforesaid N-acyl compound (secondary amide-type N-acylamino acid salt) may be produced by, for example, the following method.
• An amino acid is acylated by commonly known Schotten-Baumann reaction wherein an alkali aqueous solution of the amino acid and sodium hydroxide is reacted with a fatty acid chloride. Then the reaction mixture is acidified by adding hydrochloric acid to thereby give an N-acylamino acid (acid type).
• the obtained product is filtered, dried and then neutralized with potassium hydroxide or an alkanolamine.
• the secondary amide-type N-acylamino acid to be used in the first invention can be obtained.
• the liquid detergent composition of the first invention may be formulated into a paste or a gel by adding a thickener or a binder, if required.
• the liquid detergent composition of the first invention may further contain components commonly employed in detergent compositions, for example, humectants, touch improvers, viscosity modifiers, bactericides, perfumes or colorants, so long as the formation of the highly lubricant platy crystals during the rinsing step is not inhibited thereby.
• components commonly employed in detergent compositions for example, humectants, touch improvers, viscosity modifiers, bactericides, perfumes or colorants, so long as the formation of the highly lubricant platy crystals during the rinsing step is not inhibited thereby.
• the pH value of the liquid detergent composition of the first invention may be 6 or above and preferably range from 7 to 10.
• the liquid detergent composition of the first invention is suitable for cleansing the body including the skin and the hair. It is particularly suitable for cleansing the skin.
• N-acyl compound represented by the above general formula (II), which is the component (A) of the detergent composition of the second invention, would react with calcium in tap water to form highly lubricant platy crystals, similar to the above-mentioned N-acyl compound in the first invention.
• RCO in the above general formula (II) of the aforesaid N-acyl compound is a straight-chain acyl group having 8 to 22 carbon atoms, in particular, a straight-chain acyl group having 10 to 14 carbon atoms such as a caprinoyl, lauroyl or myristoyl group.
• a is an integer of from 1 to 11, preferably from 1 to 5 and still preferably 1 or 2, from the viewpoint of the lubricity of the platy crystals.
• the lubricity of the platy crystals formed by the reaction between the aforesaid N-acyl compound and calcium may be determined and evaluated by the same method as the above-mentioned one employed in the case of the N-acyl compound of the first invention.
• the aforesaid N-acyl compound has a secondary amide-type structure wherein the N-acyl group consists of the above-mentioned straight-chain acyl.
• the acyl group constituting the N-acyl group is branched or the amide has a tertiary amide type structure, the formation of the platy crystals is suppressed or the formed crystals are poor in lubricity and thus sticky. In these cases, therefore, a desirable texture can be hardly obtained.
• alkali metals such as sodium (hereinafter sometimes abbreviated as Na) and potassium (hereinafter sometimes abbreviated as K) and inorganic or organic ammonium may be cited.
• the organic ammonium includes acid salts of organic amine compounds such as alkanolamines such as monoethanolamine, diethanolamine and triethanolamine (hereinafter sometimes abbreviated as TEA), alkylamines and basic amino acids.
• the content of the aforesaid N-acyl compound may be 5% by weight or above, preferably from 20 to 80% by weight, based on the composition of the second invention. When the content thereof is less than 5% by weight, the state of feeling refreshed and comfort in its use due to the platy crystals formed during rinsing cannot be obtained.
• surfactant which is the component (B) of the determent composition of the second invention
• various surfactants including the following ones may be used.
• anionic surfactants include sulfate and sulfonate surfactants such as alkyl sulfates and polyokyethylene alkyl sulfates and sulfosuccinic acid, taurate, isethionate and ⁇ -olefinsulfonate surfactants; carboxylate surfactants such as fatty acid soaps, fatty acid salts, ether carboxylic acid surfactants and acylated amino acid surfactants; and phosphate ones such as alkyl phosphate surfactants.
• fatty acid, phosphate and isethionate surfactants are particularly preferable from the viewpoint of foaming properties.
• ampholytic surfactants examples include carbobetaine, sulfobetaine and imidazoliniumbetaine surfactants. It is preferable to use hydroxypropylsulfobetaine and desalted secondary imidazoliniumbetaine.
• nonionic surfactants include polyhydric alcohols such as polyoxyalkylene addition type, polyoxypropylene/polyoxyethylene addition type, amine oxide and mono- or diethanoloamide as well as sorbitan fatty acid esters, glycerol fatty acid esters, sucrose fatty acid esters and alkyl saccharide and N-poylhydroxyalkyl fatty acid amide surfactants. It is particularly preferable to use amine oxide, diethanolamide and alkyl saccharide surfactants.
• cationic surfactants include mono- or dialkyl-addition type quaternary ammonium salts having a straight-chain or branched alkyl group and those obtained by adding an alkylene oxide to the alkyl group thereof. It is particularly preferable to use straight-chain monoalkyl quaternary ammonium salts having 12 to 16 carbon atoms and quaternary ammonium salts having a branched alkyl group having 20 to 28 carbon atoms.
• Either one of these surfactants or a mixture thereof may be used depending on the performance of the target product.
• the content of the surfactant(s) may preferably range from 0.1 to 45% by weight based on the composition of the second invention.
• the detergent composition of the second invention may comprise the aforesaid N-acyl compound, i.e., the component (A) and the aforesaid surfactant, i.e., the component (B) at a weight ratio of (A)/(B) of from 99/1 to 1/1 (preferably from 95/5 to 60/40).
• a weight ratio of (A)/(B) of from 99/1 to 1/1 (preferably from 95/5 to 60/40).
• the detergent composition of the second invention may be formulated into any form, for example, liquid, paste, solid or powder, without restriction.
• the detergent composition of the second invention may further contain various foaming aids and foam improvers to improve the foaming and foam qualities, so long as the formation of the highly lubricant platy crystals during the rinsing step is not inhibited thereby.
• the detergent composition of the second invention may further contain components commonly employed in detergent compositions, for example, humectants, touch improvers, viscosity modifiers, perfumes or colorants, so long as the effects of the present invention are not deteriorated thereby.
• foaming aids foam improvers and common additives may be appropriately varied depending on the form of the detergent composition.
• the pH value of the detergent composition of the second invention may be 6 or above and preferably range from 7 to 10.
• the detergent composition of the second invention which has been described in detail above, is suitable for cleansing the body including the skin and the hair, though the application range thereof is not particularly limited.
• Examples 1 to 4 show each an embodiment of the first invention, whereas Examples 5 to 7 show each an embodiment of the second invention.
• the foam volume was measured by the following method and thus the foaming properties were evaluated in accordance with the criteria as specified below.
• Each liquid detergent composition was diluted 10-fold with water.
• 100 ml of the aqueous solution (liquid temperature: 20°C) thus obtained was poured into a volumetric cylinder.
• stirring blades were placed in the solution and the volume (ml) of the foam formed 30 seconds after the initiation of stirring was measured. The value thus determined was referred to as the foam volume.
• the stirring blades were rotated at 1,000 rpm and the rotation was reversed every 5 seconds.
• Each liquid detergent composition was diluted 10-fold with ion-exchanged water. 1 ml of the obtained aqueous solution was poured into 50 ml of 4° DH hard water at 20°C. After 10 seconds, the formation of crystals was observed with the naked eye and thus evaluated in accordance with the criteria as specified below.
• secondary amide-type N-acylamino acid salts K salts and TEA salts
• solubility, formation of lubricant platy crystals and comfort in the use were evaluated in accordance with the criteria as specified below.
• secondary amide-type N-acylamino acid Na salts and tertiary amide-type N-alkyl-N-acylamino acid salts were evaluated in the same manner.
• Table 2 shows the results and the Krafft points of these amino acid salts.
• a 5% by weight aqueous solution of each amino acid salt was prepared and 1 ml of the obtained solution was poured into 50 ml of 4°DH hard water at 20°C. After 10 seconds, the formation of crystals was determined and evaluated in accordance with the criteria as specified below.
• a 5% by weight aqueous solution of each amino acid salt was prepared and a subject washed the body with the obtained solution. Then the slippage from the rinsing step to after drying was evaluated in accordance with the criteria as specified below.
• the component (1) was dissolved in hot water. After cooling, the components (2) to (4) were added thereto. Thus a transparent liquid detergent composition was prepared.
• the product When the skin and the hair were washed with the liquid detergent composition obtained above, the product showed good foaming properties, good foam breaking, good slippage from the rinsing step to after drying and an excellent comfort in the use.
• the component (2) was added to hot water followed by the addition of the component (1), and the components were neutralized and dissolved. After cooling, the components (3) to (5) were added thereto. Thus a transparent liquid detergent composition was prepared.
• the product When the skin and the hair were washed with the liquid detergent composition obtained above, the product showed good foaming properties, good foam breaking, good slippage from the rinsing step to after drying and an excellent comfort in the use.
• Detergent compositions of the formulations as specified in Table 3 were prepared.
• the foam volume of each detergent composition was determined by the following method. Further, the formation of lubricant platy crystals and the comfort in the use thereof were evaluated in accordance with the criteria as specified below. Tables 3 and 4 show the results.
• the detergent compositions No. 27 to No. 33 are comparative products.
• Each detergent composition was diluted 20-fold with water. 100 ml of the aqueous solution (liquid temperature: 40°C) thus obtained was poured into a volumetric cylinder. Next, stirring blades were placed in the solution and the volume (ml) of the foam formed 30 seconds after the initiation of stirring was measured. The value thus determined was referred to as the foam volume. The stirring blades were rotated at 1,000 rpm and the rotation was reversed every 5 seconds.
• Each liquid detergent composition was diluted 20-fold with ion-exchanged water. 1 ml of the obtained aqueous solution was poured into 40 ml of 4° DH hard water at 40°C. After 10 seconds, the formation of crystals was observed with the naked eye aid thus observed in accordance with the criteria as specified below.
• the components (1) to (3) were dissolved in hot water. After cooling, the components (4) and (5) were added thereto. Thus a liquid detergent composition was prepared.
• the product When the skin and the hair were washed with the liquid detergent composition obtained above, the product showed good foaming properties, good foam breaking, good slippage from the rinsing step to after drying and an excellent comfort in the use.
• the components (1) to (3) were dissolved in hot water. After cooling, the components (4) to (6) were added thereto. Thus a liquid detergent composition was prepared.
• the product When the skin and the hair were washed with the liquid detergent composition obtained above, the product showed good foaming properties, good foam breaking, good slippage from the rinsing step to after drying and an excellent comfort in the use.
• the components (1) to (5) were mixed uniformly at 60°C. After cooling, the obtained mixture was subjected to kneading, extrusion and stamping in the conventional manner. Thus a solid detergent composition was prepared.
• the product When the skin and the hair were washed with the solid detergent composition obtained above, the product showed good foaming properties, good foam breaking, good slippage from the rinsing step to after drying and an excellent comfort in the use.

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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)
• Cosmetics (AREA)

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Cited By (19)

Citations (8)

• 1991
  • 1991-05-27 MY MYPI91000923A patent/MY107820A/en unknown
  • 1991-06-03 EP EP91109015A patent/EP0460566B1/de not_active Expired - Lifetime
  • 1991-06-03 DE DE69112712T patent/DE69112712T2/de not_active Expired - Lifetime
• 1997
  • 1997-02-27 HK HK23097A patent/HK23097A/xx not_active IP Right Cessation

Patent Citations (8)

Non-Patent Citations (7)

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